Compound, liquid crystal composition and liquid crystal display element

文档序号：93699 发布日期：2021-10-12 浏览：44次中文

阅读说明：本技术 化合物、液晶组合物和液晶显示元件 (Compound, liquid crystal composition and liquid crystal display element ) 是由杉山典幸林正直门本丰井之上雄一野吕大树于 2021-03-15 设计创作，主要内容包括：本发明提供一种化合物、液晶组合物和液晶显示元件。本发明所要解決的课题在于,提供能够实现高速响应性和高电压保持率(VHR)的液晶显示元件,并且提供能够同时实现快聚合速度、适当的倾斜形成、高倾斜稳定性、高电压保持率(VHR)的含有聚合性化合物的液晶组合物和使用其的烧屏(IS)被充分抑制或不发生的PSA型或PSVA型的液晶显示元件以及适合调制上述含有聚合性化合物的液晶组合物的化合物。解决课题的方法在于,本发明提供分子中具有式(K-1)所表示的结构的化合物,并且提供含有该化合物的液晶组合物以及使用该液晶组合物的元件。[化1](The invention provides a compound, a liquid crystal composition and a liquid crystal display element. The problem to be solved by the present invention IS to provide a liquid crystal display device capable of realizing high-speed response and high Voltage Holding Ratio (VHR), and to provide a liquid crystal composition containing a polymerizable compound capable of simultaneously realizing a fast polymerization rate, appropriate tilt formation, high tilt stability, and high Voltage Holding Ratio (VHR), a PSA-type or PSVA-type liquid crystal display device using the same in which the occurrence of burn-In (IS) IS sufficiently suppressed or not, and a compound suitable for preparing the liquid crystal composition containing a polymerizable compound. The present invention provides a compound having a structure represented by formula (K-1) in a molecule, a liquid crystal composition containing the compound, and an element using the liquid crystal composition. [ formula 1])

1. A liquid crystal composition comprising a compound having a structure represented by the formula (K-1) in a molecule,

[ solution 1]

In the formula, the black dots represent bond bonds,

Yⁱ¹each independently represents a linear or branched alkyl group having 1 to 20 carbon atoms, and at least 1 or more-CH in the alkyl groups₂is-SO₂-substituted, the hydrogen atoms of these alkyl groups being possibly substituted by halogen atoms, cyano groups or phenyl groups, and, furthermore, -CH-of these alkyl groups₂-may be substituted by-CH ═ CH-, -C ≡ C-, -O-, -NH-, -C (═ O) -, -CH (-CN) -, -COO or-OCO-in such a way that oxygen atoms are not directly adjacent, and furthermore, the hydrogen atoms in these alkyl groups may be substituted by Pⁱ¹-Spⁱ¹-substituted, wherein the hydrogen atoms present in the phenyl groups may be substituted by cyano groups, halogen atoms, alkyl groups having 1 to 8 carbon atoms, alkoxy groups having 1 to 8 carbon atoms, alkenyl groups having 1 to 8 carbon atoms or nitro groups,

Sⁱ¹and Sⁱ³Each independently representAn alkylene group having 1 to 6 carbon atoms or a single bond, wherein-CH in the alkylene group₂May be substituted by-CH-, -C.ident.C-, -C (═ CH) in such a way that the oxygen atoms are not directly adjacent₂) -, -O-, -NH-, -C (═ O) -, -COO-or-OCO-,

Sⁱ²represents a carbon atom, a nitrogen atom or a silicon atom,

Rⁱ²each independently represents a hydrogen atom, a linear or branched alkyl group having 1 to 20 carbon atoms, the hydrogen atom in the alkyl group may be substituted by a halogen atom or a cyano group, and-CH in the group₂-may be substituted, in such a way that the oxygen atoms are not directly adjacent, -CH ═ CH-, -C ≡ C-, -O-, -NH-, -C (═ O) -, -CH (-CN) -, -COO-or-OCO-,

Pⁱ¹each independently represents a polymerizable group,

Spⁱ¹each independently represents a spacer or a single bond,

nⁱ¹represents an integer of 1 to 3, nⁱ²And nⁱ³Each independently represents an integer of 0 to 2, in Sⁱ²When it represents a carbon atom or a silicon atom, nⁱ¹+nⁱ²+nⁱ³Is 3 at Sⁱ²When it represents a nitrogen atom, nⁱ¹+nⁱ²+nⁱ³Is 2, in the general formula (K-1), Rⁱ²、Yⁱ¹、Sⁱ³、Pⁱ¹And Spⁱ¹When a plurality of the compounds exist, they may be the same or different.

2. The liquid crystal composition according to claim 1, wherein the compound having a structure represented by formula (K-1) in a molecule comprises a compound represented by the following general formula (Y-1),

[ solution 2]

In the formula, R^y1And R^y2Each independently represents a hydrogen atom, a halogen atom, a cyano group, P^y1-S^y1Linear or branched C1-30A group of alkyl group in which hydrogen atom may be substituted with halogen atom, cyano group or nitro group, or-CH group₂-may be substituted with-CH-, -C.ident.C-, -CO-, -COO-, -OCO-, -OCOO-, -O-, -NH-or-S-but 2 or more-O-may not be consecutive to cause adjacency,

S^y3is a single bond or a linear or branched alkylene group having 1 to 12 carbon atoms, wherein hydrogen atoms in the alkylene group may be substituted with a halogen atom, a cyano group or a nitro group, and-CH in the alkylene group₂-may be substituted with-CH-, -C.ident.C-, -CO-, -COO-, -OCO-, -OCOO-, -O-, -NH-or-S-but 2 or more-O-may not be consecutive to cause adjacency,

Z^y1and Z^y2Each independently represents a single bond, -C₂H₄-、-C₄H₈-、-C₃H₆-、-OCH₂-、-CH₂O-、-CO-、-COO-、-OCO-、-OCOOCH₂-、-CH₂OCOO-、-OCH₂CH₂O-、-CH＝CRa-COO-、-CH＝CRa-OCO-、-COO-CRa＝CH-、-OCO-CRa＝CH-、-COO-CRa＝CH-COO-、-COO-CRa＝CH-OCO-、-OCO-CRa＝CH-COO-、-OCO-CRa＝CH-OCO-、-COOC₂H₄-、-OCOC₂H₄-、-C₂H₄OCO-、-CH₂OCO-、-COOCH₂-、-OCOCH₂-、-CH＝CH-、-CF＝CF-、-CF＝CH-、-CH＝CF-、-CF₂O-、-OCF₂-、-CF₂CH₂-、-CH₂CF₂-、-CF₂CF₂-or-C.ident.C-, wherein Ra each independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms,

M^y2each independently represents a 3-valent aromatic group, a 3-valent cycloaliphatic group, a 3-valent heterocyclic compound group, a 3-valent condensed ring or a 3-valent condensed polycyclic ring, and a hydrogen atom in these ring structures may be replaced by L^y1The substitution is carried out by the following steps,

M^y1and M^y3Each independently represents a 2-valent aromatic group, a 2-valent cycloaliphatic group, a 2-valent heterocyclic compound group, a 2-valent condensed ring or a 2-valent condensed polycyclic group, and hydrogen atoms in these ring structures may beTo be L^y1Substituted, L^y1Represents K^y1、P^y2-S^y2A halogen atom, a cyano group, a nitro group, a C1-30 linear or branched alkyl group, wherein the hydrogen atom in the alkyl group may be replaced by a halogen atom, a cyano group, a nitro group or K^y1Structural substitution of-CH in the alkyl group₂-may be substituted with-CH ═ CH-, -C ≡ C-, -CO-, -COO-, -OCO-, -OCOO-, -O-, -NH-or-S-but 2 or more-O-S are not continuous and adjacent to each other, and L is a group represented by^y1In the case where there are plural, they may be the same or different,

P^y1and P^y2Each independently represents a polymerizable group,

S^y1and S^y2Each independently is a single bond or a linear or branched alkylene group having 1 to 12 carbon atoms, a hydrogen atom in the alkylene group may be substituted with a halogen atom, a cyano group or a nitro group, and-CH in the alkylene group₂-may be substituted with-CH-, -C.ident.C-, -CO-, -COO-, -OCO-, -OCOO-, -O-, -NH-or-S-but 2 or more-O-may not be consecutive to cause adjacency,

K^y1a group represented by the formula (K-1),

m and n each independently represent an integer of 0 to 4, wherein the total number of m + n is 0 to 6,

wherein P contained in the structure represented by the general formula (Y-1)ⁱ¹、P^y1And P^y2The total number of (2) is at least 1 or more.

3. A liquid crystal composition according to claim 2, wherein M is represented by the general formula (Y-1)^y1、M^y2And M^y3Each independently represents a group selected from the group consisting of the following formulae (T-1) to (T-21), and these groups may be represented by L^y1The substitution is carried out by the following steps,

[ solution 3]

Wherein the compound may have at any positionIn a bond, any-CH may be independently substituted by-N, -CH₂Each independently may be substituted by-O-, -S-, -NR-⁰-, -CS-or-CO-substituted but not comprising a-O-bond, wherein R⁰Represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms.

4. A liquid crystal composition according to claim 2 or 3, P in the general formula (Y-1)ⁱ¹、P^y1And P^y2Each independently represents a substituent selected from the group represented by the following formulae (P-1) to (P-14),

[ solution 4]

In the formula, the black dots represent^y1Or S^y2The bond of (3).

5. The liquid crystal composition according to any one of claims 2 to 4, wherein P contained in the structure in the general formula (Y-1)ⁱ¹、P^y1And P^y2The total number of (2) or more.

6. The liquid crystal composition according to any one of claims 2 to 5, wherein in the general formula (Y-1), R^y1And R^y2Each independently comprises P^y2-S^y2-the structure represented.

7. The liquid crystal composition according to any one of claims 1 to 6, which contains 1 or 2 or more polymerizable compounds A having a structure different from that of the compound having the structure represented by the formula (K-1) in the molecule.

8. The liquid crystal composition according to claim 7, wherein the polymerizable compound A is a compound represented by the general formula (P),

[ solution 5]

In the formula, R^p1Represents a hydrogen atom, a fluorine atom, a cyano group, an alkyl group having 1 to 15 carbon atoms or-Sp^p2-P^p21 or 2 or more-CH not adjacent in the alkyl group₂-each independently may be substituted by-CH- ═ CH-, -C.ident.C-, -O-, -CO-, -COO-or-OCO-, 1 or more hydrogen atoms in the alkyl group each independently may be substituted by a cyano group, a fluorine atom or a chlorine atom,

P^p1and P^p2Each independently represents formula (P)^p1-1) to the general formula (P)^p1-9) of:

[ solution 6]

In the formula, R^p11And R^p12Each independently represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms or a haloalkyl group having 1 to 5 carbon atoms, W^p11Represents a single bond, -O-, -COO-, an alkylene group having 1 to 5 carbon atoms, t^p11Represents 0, 1 or 2, R being in the molecule^p11、R^p12、W^p11And/or t^p11In the case where there are plural, they may be the same or different,

Sp^p1and Sp^p2Each independently represents a single bond or a spacer,

Z^p1and Z^p2Each independently represents a single bond, -O-, -S-, -CH₂-、-OCH₂-、-CH₂O-、-CO-、-C₂H₄-、-COO-、-OCO-、-OCOOCH₂-、-CH₂OCOO-、-OCH₂CH₂O-、-CO-NR^ZP1-、-NR^ZP1-CO-、-SCH₂-、-CH₂S-、-CH＝CR^ZP1-COO-、-CH＝CR^ZP1-OCO-、-COO-CR^ZP1＝CH-、-OCO-CR^ZP1＝CH-、-COO-CR^ZP1＝CH-COO-、-COO-CR^ZP1＝CH-OCO-、-OCO-CR^ZP1＝CH-COO-、-OCO-CR^ZP1＝CH-OCO-、-(CH₂)_z-COO-、-(CH₂)_z-OCO-、-OCO-(CH₂)_z-、-(C＝O)-O-(CH₂)_z-、-CH＝CH-、-CF＝CF-、-CF＝CH-、-CH＝CF-、-CF₂-、-CF₂O-、-OCF₂-、-CF₂CH₂-、-CH₂CF₂-、-CF₂CF₂-or-C.ident.C-, wherein z each independently represents an integer of 1 to 4, R^ZP1Each independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, R in the molecule^ZP1When there are plural, they may be the same or different, and in the formula, it is represented by the formula^p1Or Sp^p2The point of attachment of (a) to (b),

A^p1and A^p2Each independently represents a group selected from the group consisting of:

(a^p)1, 4-cyclohexylene radical, 1-CH present in this radical₂-or non-adjacent 2 or more-CH₂-may be substituted by-O-;

(b^p)1, 4-phenylene, 1-CH ═ present in the radical or not adjacent 2 or more-CH ═ can be substituted by-N ═ s; and

(c^p) Naphthalenediyl, 1,2,3, 4-tetrahydronaphthalenediyl, decahydronaphthalenediyl, phenanthrene-2, 7-diyl or anthracene-2, 6-diyl, 1-CH or not adjacent 2 or more-CH present in these groups being optionally substituted by-N-,

A^p3represents a group selected from the group consisting of (a)^p) Group (b)^p) And a group (c)^p) And a single bond,

the group (a)^p) Group (b)^p) And a group (c)^p) Wherein each hydrogen atom present in the group may be independently substituted by a cyano group, a halogen atom, an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkenyl group having 1 to 8 carbon atoms or-Sp^p2-P^p2The substitution is carried out by the following steps,

m^p1represents 0, 1,2 or 3, and Z is in the molecule^p1、A^p2、Sp^p2And/or P^p2When a plurality of the compounds exist, they may be the same or different.

9. A liquid crystal display element using the liquid crystal composition according to any one of claims 1 to 8.

10. A liquid crystal display element for active matrix driving, which uses the liquid crystal composition according to any one of claims 1 to 8.

11. A liquid crystal display element for PSA mode, PSVA mode, PS-IPS mode, or PS-FFS mode, which uses the liquid crystal composition according to any one of claims 1 to 8.

12. A compound represented by the general formula (Y-1),

[ solution 7]

In the formula, R^y1And R^y2Each independently represents a hydrogen atom, a halogen atom, a cyano group, P^y1-S^y1A linear or branched alkyl group having 1 to 30 carbon atoms, wherein a hydrogen atom in the alkyl group may be substituted with a halogen atom, a cyano group or a nitro group, and-CH in the alkyl group₂-may be substituted with-CH- ═ CH-, -C.ident.C-, -CO-, -COO-, -OCO-, -OCOO-, -O-, -NH-or-S-but 2 or more-O-may not be consecutive to cause adjacency,

S^y3is a single bond or a linear or branched alkylene group having 1 to 12 carbon atoms, wherein hydrogen atoms in the alkylene group may be substituted with a halogen atom, a cyano group or a nitro group, and-CH in the alkylene group₂-may be substituted with-CH- ═ CH-, -C.ident.C-, -CO-, -COO-, -OCO-, -OCOO-, -O-, -NH-or-S-but 2 or more-O-may not be consecutive to cause adjacency,

Z^y1and Z^y2Each independently represents a single bond、-C₂H₄-、-C₄H₈-、-C₃H₆-、-OCH₂-、-CH₂O-、-CO-、-COO-、-OCO-、-OCOOCH₂-、-CH₂OCOO-、-OCH₂CH₂O-、-CH＝CRa-COO-、-CH＝CRa-OCO-、-COO-CRa＝CH-、-OCO-CRa＝CH-、-COO-CRa＝CH-COO-、-COO-CRa＝CH-OCO-、-OCO-CRa＝CH-COO-、-OCO-CRa＝CH-OCO-、-COOC₂H₄-、-OCOC₂H₄-、-C₂H₄OCO-、-CH₂OCO-、-COOCH₂-、-OCOCH₂-、-CH＝CH-、-CF＝CF-、-CF＝CH-、-CH＝CF-、-CF₂O-、-OCF₂-、-CF₂CH₂-、-CH₂CF₂-、-CF₂CF₂-or-C.ident.C, wherein Ra independently of one another represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms,

M^y1and M^y3Each independently represents a 2-valent aromatic group, a 2-valent cycloaliphatic group, a 2-valent heterocyclic compound group, a 2-valent condensed ring or a 2-valent condensed polycyclic group, and a hydrogen atom in these ring structures may be replaced by L^y1Substituted, L^y1Represents K^y1、P^y2-S^y2A halogen atom, a cyano group, a nitro group, a C1-30 linear or branched alkyl group, wherein the hydrogen atom in the alkyl group may be replaced by a halogen atom, a cyano group, a nitro group or K^y1Structural substitution of-CH in the alkyl group₂-may be substituted with-CH ═ CH-, -C ≡ C-, -CO-, -COO-, -OCO-, -OCOO-, -O-, -NH-or-S-but 2 or more-O-may not be continuous and may be adjacent to each other, in L^y1In the case where there are plural, they may be the same or different,

P^y1and P^y2Each independently represents a polymerizable group,

S^y1and S^y2Each independently a single bond or carbonA linear or branched alkylene group having 1 to 12 atoms, wherein hydrogen atoms in the alkylene group may be substituted with a halogen atom, a cyano group or a nitro group, and-CH in the alkylene group₂-may be substituted with-CH- ═ CH-, -C.ident.C-, -CO-, -COO-, -OCO-, -OCOO-, -O-, -NH-or-S-but 2 or more-O-may not be consecutive to cause adjacency,

K^y1a group represented by the formula (K-1),

[ solution 8]

In the formula, the black dots represent bond bonds,

Yⁱ¹each independently represents a linear or branched alkyl group having 1 to 20 carbon atoms, and at least 1 or more-CH in the alkyl groups₂is-SO₂-substituted, the hydrogen atoms of these alkyl groups being possibly substituted by halogen atoms, cyano groups or phenyl groups, and, furthermore, -CH-of these alkyl groups₂-may be substituted by-CH ═ CH-, -C ≡ C-, -O-, -NH-, -C (═ O) -, -CH (-CN) -, -COO or-OCO-in such a way that oxygen atoms are not directly adjacent, and furthermore, the hydrogen atoms in these alkyl groups may be substituted by Pⁱ¹-Spⁱ¹-substituted, the hydrogen atoms present in the phenyl groups being possibly substituted by cyano groups, halogen atoms, alkyl groups having 1 to 8 carbon atoms, alkoxy groups having 1 to 8 carbon atoms, alkenyl groups having 1 to 8 carbon atoms or nitro groups,

Sⁱ¹and Sⁱ³Each independently represents an alkylene group having 1 to 6 carbon atoms or a single bond, wherein-CH in the alkylene group₂May be substituted by-CH-, -C.ident.C-, -C (═ CH) in such a way that the oxygen atoms are not directly adjacent₂) -, -O-, -NH-, -C (═ O) -, -COO-or-OCO-,

Sⁱ²represents a carbon atom, a nitrogen atom or a silicon atom,

Rⁱ²each independently represents a hydrogen atom, a linear or branched alkyl group having 1 to 20 carbon atoms, the hydrogen atom in the alkyl group may be substituted by a halogen atom or a cyano group, and-CH in the group₂May be not directly adjacent to an oxygen atomby-CH-, -C.ident.C-, -O-, -NH-, -C (═ O) -, -CH (-CN) -, -COO-or-OCO-,

Pⁱ¹each independently represents a polymerizable group,

Spⁱ¹each independently represents a spacer or a single bond,

nⁱ¹represents an integer of 1 to 3, nⁱ²And nⁱ³Each independently represents an integer of 0 to 2, in Sⁱ²When it represents a carbon atom or a silicon atom, nⁱ¹+nⁱ²+nⁱ³Is 3 at Sⁱ²When it represents a nitrogen atom, nⁱ¹+nⁱ²+nⁱ³Is 2, in the general formula (K-1), Rⁱ²、Yⁱ¹、Sⁱ³、Pⁱ¹And Spⁱ¹In the case where there are plural, they may be the same or different,

m and n each independently represent an integer of 0 to 4, wherein the total number of m + n is 0 to 6,

wherein P contained in the structure represented by the general formula (Y-1)ⁱ¹、P^y1And P^y2The total number of (2) is at least 1 or more.

Technical Field

The present invention relates to a liquid crystal composition, a liquid crystal display element using the same, and a polymerizable compound.

Background

Liquid crystal display devices using liquid crystal compositions having a negative dielectric anisotropy Δ ∈ have been widely used, such as PSA and PSVA liquid crystal TVs and liquid crystal monitors, and as liquid crystal compositions suitable for these applications, various polymerizable compounds and liquid crystal compositions containing the same are disclosed in patent document 1, patent document 2, patent document 3, patent document 4, and patent document 5.

However, the characteristics of the liquid crystal compositions containing polymerizable compounds which have been conventionally used are not sufficient for high-definition liquid crystal TVs such as 4K and 8K. Specifically, the 4K and 8K liquid crystal display elements require high-definition pixels, and a considerable amount of UV light is cut off due to an increase in the area of wiring and light shielding portions. Therefore, in the UV irradiation step in the production of PSA-type or PSVA-type liquid crystal display devices, the polymerizable compound is not sufficiently polymerized, and a large amount of the polymerizable compound remains. This confirmed insufficient formation of tilt, deterioration of response speed, and afterimage due to deterioration of orientation, and also confirmed that the residual polymerizable compound polymerized slowly during driving and changed the tilt, resulting in a display failure called burn-In (IS).

Based on the above, PSA or PSVA type liquid crystal display elements such as high definition liquid crystal televisions and liquid crystal monitors require extremely high characteristics distinguished from the prior art, and require a liquid crystal composition that can be stably produced with weaker or less UV light than the prior art.

Documents of the prior art

Patent document

Patent document 1: japanese laid-open patent publication 2016 (Japanese patent application laid-open) No. 216747

Patent document 2: japanese patent No. 4803320

Patent document 3: japanese patent No. 6008065

Patent document 4: japanese patent No. 6233550

Patent document 5: japanese patent No. 5743132

Disclosure of Invention

Problems to be solved by the invention

The liquid crystal composition has the following problems: deterioration is likely to occur due to light emitted from a backlight, active energy rays such as ultraviolet rays irradiated in the process of manufacturing a liquid crystal display element, and a Voltage Holding Ratio (VHR) of a liquid crystal panel is lowered due to impurities generated by the light deterioration of a liquid crystal composition. Therefore, a liquid crystal display element capable of realizing both high-speed response and high VHR is required.

An object to be solved by the present invention IS to provide a liquid crystal display device capable of realizing high-speed response and high Voltage Holding Ratio (VHR), and to provide a liquid crystal composition containing a polymerizable compound, which can simultaneously realize a high polymerization rate, appropriate tilt formation, high tilt stability, and high Voltage Holding Ratio (VHR), a PSA-type or PSVA-type liquid crystal display device using the same, in which occurrence of burn-In (IS) IS sufficiently suppressed or prevented, and a compound suitable for preparing the liquid crystal composition containing a polymerizable compound.

Means for solving the problems

As a result of intensive studies, the present inventors have found that the above problems can be solved by a liquid crystal composition containing one or more compounds having a specific chemical structure, and have completed the present invention.

Effects of the invention

The liquid crystal composition of the present invention contains one or more compounds having a specific chemical structure, which are excellent in solubility in the liquid crystal composition and low-temperature storage stability, and thus can achieve a high polymerization rate, appropriate tilt formation, high tilt stability, and a high VHR at the same time. Further, by using the liquid crystal composition of the present invention, a PSA-type or PSVA-type liquid crystal display element which exhibits excellent display quality with sufficiently suppressed or no occurrence of burn-In (IS) and in which high-definition pixels are formed can be provided.

Detailed Description

First, the liquid crystal composition of the present invention will be described. In the following description, "total amount" means "total mass", and the unit "%" of the content of each compound means "% by mass".

(polar Compound)

The liquid crystal composition of the present invention contains a polar compound, and has a function of adsorbing and trapping polar impurities such as ionic compounds and radical compounds present in the liquid crystal composition. Further, since the polar compound has a polar group in its structure, the polar group is adsorbed on the surface of the substrate sandwiching the liquid crystal composition (liquid crystal layer) and is biased to be concentrated in the vicinity of the surface of the substrate. In particular, since the polar compound is a polymerizable polar compound having a polymerizable group together with the structure thereof, the resistivity and VHR of the liquid crystal composition and the liquid crystal layer can be improved by the effect of the polymer obtained by polymerization of the polymerizable polar compound.

Factors concerning the decrease in resistivity and VHR are considered to be caused by the dispersion (diffusion) of impurities in the liquid crystal layer. In the present invention, it is presumed that the polar group of the polymer obtained by the polymerization of the polymerizable polar compound binds to the impurity or forms a polar attraction corresponding to the binding, and the impurity is fixed to the polymer obtained by the polymerization of the polymerizable polar compound. In this way, the impurities are adsorbed and trapped by the polymer obtained from the polymerizable polar compound, and the impurities can be immobilized in the vicinity of the substrate surface without diffusing throughout the liquid crystal layer, so that the decrease in resistivity and VHR due to the impurities can be suppressed. The polar group may be a structure capable of functioning as, for example, a donor or an acceptor of a proton having a hydrogen bond, and may function as either one of the donor and the acceptor, or may function as both of them.

Further, the polymerizable polar compound also interacts with the substrate surface of the liquid crystal display element, and easily moves from the liquid crystal composition to the substrate surface, and is locally present. Therefore, it is considered that the monomer is efficiently polymerized in a state of being accumulated on the surface of the substrate during UV irradiation, and the polymerizable compound remaining in the liquid crystal layer can be effectively reduced, thereby also exhibiting an effect of improving the specific resistance and VHR of the liquid crystal composition and the liquid crystal layer.

According to the present invention, the polar compound having the structure represented by the formula (K-1) is excellent in solubility in a liquid crystal composition and is less precipitated, and when the polar compound is added to a liquid crystal composition containing a polymerizable compound, the polymerization rate is sufficiently high and the polymerization reaction sufficiently proceeds, so that a polymerizable compound-containing liquid crystal composition having a small amount of unreacted polymerizable compound remaining after polymerization can be obtained.

The polar compound of the present invention is preferably a compound having a structure represented by the formula (K-1) in the molecule.

[ solution 1]

(in the formula, the black dots represent bond bonds,

Yⁱ¹each independently represents a linear or branched alkyl group having 1 to 20 carbon atoms, and at least 1 or more-CH in the alkyl groups₂is-SO₂-substituted, the hydrogen atoms of the alkyl groups may be substituted by halogen atoms, cyano groups or phenyl groups (the hydrogen atoms present in the phenyl groups may be substituted by cyano groups, halogen atoms, alkyl groups having 1 to 8 carbon atoms, alkoxy groups having 1 to 8 carbon atoms, alkenyl groups having 1 to 8 carbon atoms or nitro groups), and furthermore-CH of the alkyl groups₂-may be substituted by-CH ═ CH-, -C ≡ C-, -O-, -NH-, -C (═ O) -, -CH (-CN) -, -COO or-OCO-in such a way that oxygen atoms are not directly adjacent, and furthermore, the hydrogen atoms in these alkyl groups may be substituted by Pⁱ¹-Spⁱ¹-a substitution of a group of formula (I),

Sⁱ²represents a carbon atom, a nitrogen atom or a silicon atom,

Pⁱ¹each independently represents a polymerizable group,

Spⁱ¹each independently represents a spacer or a single bond,

nⁱ¹represents an integer of 1 to 3, nⁱ²And nⁱ³Each independently represents an integer of 0 to 2, but in Sⁱ²When it represents a carbon atom or a silicon atom, nⁱ¹+nⁱ²+nⁱ³Is 3 at Sⁱ²When it represents a nitrogen atom, nⁱ¹+nⁱ²+nⁱ³Is 2. General formula (K)R in (1)ⁱ²、Yⁱ¹、Sⁱ³、Pⁱ¹And Spⁱ¹When a plurality of the compounds exist, they may be the same or different. ).

Yⁱ¹Preferably represents a C1-12 linear or branched alkyl group, and at least 1 or more of these alkyl groups is-CH₂is-SO₂-substituted, the hydrogen atoms in the alkyl groups may be substituted by halogen atoms, cyano groups or phenyl groups (the hydrogen atoms present in the phenyl group may be substituted by cyano groups, halogen atoms, methyl groups or nitro groups), furthermore-CH in the alkyl groups₂-may be substituted by-CH ═ CH-, -C ≡ C-, -O-, -NH-, -C (═ O) -, -COO or-OCO-in such a way that the oxygen atoms are not directly adjacent, and furthermore, the hydrogen atoms in these alkyl groups may be substituted by Pⁱ¹-Spⁱ¹-substitution. More preferably, the alkyl group is a C1-12 linear or branched alkyl group, and at least 1 or more of these alkyl groups is-CH₂is-SO₂-substituted, the hydrogen atoms in the alkyl groups may be substituted by fluorine atoms, chlorine atoms, cyano groups or phenyl groups (the hydrogen atoms present in the phenyl group may be substituted by cyano groups, fluorine atoms, chlorine atoms, methyl groups or nitro groups), furthermore-CH in the alkyl groups₂-may be substituted by-CH ═ CH-, -O-, -NH-, -C (═ O) -, -COO or-OCO-in such a way that the oxygen atoms are not directly adjacent. Furthermore, Yⁱ¹More preferably represents a C1-6 linear or branched alkyl group, and at least 2 or more of these alkyl groups are-CH₂is-SO₂-substituted, the hydrogen atoms in the alkyl groups may be substituted by fluorine atoms or by phenyl groups (the hydrogen atoms present in the phenyl group may be substituted by methyl or nitro groups), furthermore-CH in the alkyl groups₂-may be substituted by-CH-, -O-, -C- (O) -, -COO or-OCO-in such a way that the oxygen atoms are not directly adjacent. Of these preferable structures, the compound is particularly preferably-SO from the viewpoint of ease of production and improvement in reliability of the liquid crystal composition₂Adjacent to the substituted position-CH₂By substitution with-O-to form-OSO₂-。

Sⁱ¹And Sⁱ³Each independently preferably represents an alkylene group having 1 to 6 carbon atoms or a single bond,in the alkylene group, -CH₂May be substituted by-CH-, -C.ident.C-, -C (═ CH) in such a way that the oxygen atoms are not directly adjacent₂) -, -O-, -NH-, -C (═ O) -, -COO-or-OCO-substitution. Further, each independently more preferably represents an alkylene group having 1 to 4 carbon atoms or a single bond, in which-CH in the alkylene group₂-may be substituted by-CH ═ CH-, -O-, -NH-, -C (═ O) -, -COO or-OCO-in such a way that the oxygen atoms are not directly adjacent. Further, each independently preferably represents an alkylene group having 1 to 3 carbon atoms or a single bond, and-CH in the alkylene group₂-may be substituted by-CH-, -O-, -C- (O) -, -COO or-OCO-in such a way that the oxygen atoms are not directly adjacent.

Sⁱ²Preferably, it represents a carbon atom or a nitrogen atom, and particularly preferably represents a carbon atom.

Rⁱ²Preferably represents a hydrogen atom, a linear or branched alkyl group having 1 to 12 carbon atoms, wherein the hydrogen atom in the alkyl group may be substituted by a fluorine atom, a chlorine atom or a cyano group, and-CH in the group₂-may be substituted by-CH ═ CH-, -C ≡ C-, -O-, -NH-, -C (═ O) -, -CH (-CN) -, -COO or-OCO-in such a way that the oxygen atoms are not directly adjacent. More preferably, the alkyl group is a hydrogen atom, a linear or branched alkyl group having 1 to 6 carbon atoms, wherein the hydrogen atom in the alkyl group may be substituted with a fluorine atom, a chlorine atom or a cyano group, and-CH in the group₂-may be substituted by-CH ═ CH-, -C ≡ C-, -O-, -C (═ O) -, -COO or-OCO-in such a way that the oxygen atoms are not directly adjacent.

Pⁱ¹Preferably, each independently represents a substituent selected from the group represented by the formulae (P-1) to (P-14) (wherein the black dots represent Spⁱ¹The bond of (3). ),

[ solution 2]

More preferably (P-1), (P-2), (P-4), (P-5), (P-7), (P-9), (P-11), (P-12) and (P-13), and still more preferably (P-1), (P-2), (P-7), (P-12) and (P-13).

Spⁱ¹Each independently preferably represents a spacer or a single bond. Here, the spacer preferably represents an alkylene group having 1 to 6 carbon atoms or a single bond, in which-CH is present in the alkylene group₂May be substituted by-CH-, -C.ident.C-, -C (═ CH) in such a way that the oxygen atoms are not directly adjacent₂) -, -O-, -NH-, -C (═ O) -, -COO-or-OCO-substitution. Further, each independently more preferably represents an alkylene group having 1 to 4 carbon atoms or a single bond, in which-CH in the alkylene group₂-may be substituted by-CH ═ CH-, -O-, -NH-, -C (═ O) -, -COO or-OCO-in such a way that the oxygen atoms are not directly adjacent. Further, each independently preferably represents an alkylene group having 1 to 3 carbon atoms or a single bond, and-CH in the alkylene group₂-may be substituted by-CH-, -O-, -C- (O) -, -COO or-OCO-in such a way that the oxygen atoms are not directly adjacent.

nⁱ¹Preferably represents an integer of 1 to 3, more preferably an integer of 1 to 2, and particularly preferably an integer of 2. n isⁱ²And nⁱ³Each independently preferably represents an integer of 0 to 2, more preferably 0 to 1, and particularly preferably 1. At Sⁱ²When it represents a carbon atom or a silicon atom, nⁱ¹+nⁱ²+nⁱ³Preferably 3, at Sⁱ²When it represents a nitrogen atom, nⁱ¹+nⁱ²+nⁱ³Preferably 2. Especially in nⁱ¹Is 2 and nⁱ²In the case of 1, the effect of the polar group is sufficiently exhibited, and since the polar group and the polymerizable group are in close positions, a crosslinked polymer can be formed in a position close to the substrate surface, and the effect of raising VHR is further improved, which is particularly preferable.

The polar compound having the structure represented by the formula (K-1) is preferably a polymerizable polar compound. The polymerizable polar compound is preferably a compound represented by the following general formula (Y-1).

[ solution 3]

(in the formula, R^y1And R^y2Each independently of the otherIs selected from hydrogen atom, halogen atom, cyano group, P^y1-S^y1A C1-30 linear or branched alkyl group, wherein the hydrogen atom in the alkyl group may be substituted with a halogen atom, a cyano group or a nitro group, and the-CH group in the alkyl group₂-may be substituted with-CH- ═ CH-, -C.ident.C-, -CO-, -COO-, -OCO-, -OCOO-, -O-, -NH-or-S-but 2 or more-O-may not be consecutive to cause adjacency,

S^y3a single bond or a linear or branched alkylene group having 1 to 12 carbon atoms, wherein hydrogen atoms in the alkylene group may be substituted with a halogen atom, a cyano group or a nitro group, and-CH in the alkylene group₂-may be substituted with-CH- ═ CH-, -C.ident.C-, -CO-, -COO-, -OCO-, -OCOO-, -O-, -NH-or-S-but 2 or more-O-may not be consecutive to cause adjacency,

Z^y1and Z^y2Each independently represents a single bond, -C₂H₄-、-C₄H₈-、-C₃H₆-、-OCH₂-、-CH₂O-、-CO-、-COO-、-OCO-、-OCOOCH₂-、-CH₂OCOO-、-OCH₂CH₂O-、-CH＝CRa-COO-、-CH＝CRa-OCO-、-COO-CRa＝CH-、-OCO-CRa＝CH-、-COO-CRa＝CH-COO-、-COO-CRa＝CH-OCO-、-OCO-CRa＝CH-COO-、-OCO-CRa＝CH-OCO-、-COOC₂H₄-、-OCOC₂H₄-、-C₂H₄OCO-、-CH₂OCO-、-COOCH₂-、-OCOCH₂-、-CH＝CH-、-CF＝CF-、-CF＝CH-、-CH＝CF-、-CF₂O-、-OCF₂-、-CF₂CH₂-、-CH₂CF₂-、-CF₂CF₂-or-C.ident.C- (wherein Ra each independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms),

M^y1and M^y3Each independently represents a 2-valent aromatic group and a 2-valent cycloaliphatic groupA subgroup, a 2-valent heterocyclic group, a 2-valent condensed ring or a 2-valent condensed polycyclic ring, the hydrogen atoms in these ring structures may be replaced by L^y1Substituted, L^y1Represents K^y1、P^y2-S^y2A halogen atom, a cyano group, a nitro group, a C1-30 linear or branched alkyl group, wherein the hydrogen atom in the alkyl group may be replaced by a halogen atom, a cyano group, a nitro group or K^y1Structural substitution represented by the formula, in the alkyl group, -CH₂-may be substituted with-CH ═ CH-, -C ≡ C-, -CO-, -COO-, -OCO-, -OCOO-, -O-, -NH-or-S-but 2 or more-O-may not be continuous and may be adjacent to each other, in L^y1In the case where there are plural, they may be the same or different,

P^y1and P^y2Each independently represents a polymerizable group,

S^y1and S^y2Each independently a single bond or a linear or branched alkylene group having 1 to 12 carbon atoms, wherein a hydrogen atom in the alkylene group may be substituted with a halogen atom, a cyano group or a nitro group, and-CH in the alkylene group₂-may be substituted with-CH- ═ CH-, -C.ident.C-, -CO-, -COO-, -OCO-, -OCOO-, -O-, -NH-or-S-but 2 or more-O-may not be consecutive to cause adjacency,

K^y1a group represented by the formula (K-1),

m and n each independently represent an integer of 0 to 4, wherein the total number of m + n is 0 to 6,

wherein P contained in the structure represented by the general formula (Y-1)ⁱ¹、P^y1And P^y2The total number of (2) is at least 1 or more. ).

R^y1And R^y2Preferably each independently selected from hydrogen atom, halogen atom, cyano group, P^y1-S^y1A straight or branched alkyl group having 1 to 30 carbon atoms, wherein the hydrogen atom in the alkyl group may be replaced by a halogen atom, a cyano group, a nitro group or P^y1-S^y1-or a structural substitution represented by the formula (K-1) — CH in the alkyl group₂May be substituted with-CH- ═ CH-, -C.ident.C-, -CO-, -COO-, -OCO-, -OCOO-, -O-, -NH-or-S- (2 or more-O-Not consecutive but causing adjacency), more preferably each independently is selected from the group consisting of a hydrogen atom, a fluorine atom, a chlorine atom, a cyano group, P^y1-S^y1Or a C1-12 linear or branched alkyl group, wherein the hydrogen atom in the alkyl group may be replaced by a halogen atom or P^y1-S^y1-or cyano, in which alkyl the-CH group is present₂-may be substituted with-CH-, -C.ident.C-, -CO-, -COO-, -OCO-, -O-or-S- (2 or more-O-groups are not consecutive but may be adjacent to each other), and are preferably each independently selected from the group consisting of a hydrogen atom, a fluorine atom, a chlorine atom, and P^y1-S^y1Or a C1-12 linear or branched alkyl group, wherein the hydrogen atom in the alkyl group may be replaced by a fluorine atom, a chlorine atom or P^y1-S^y1-substituted, -CH in the alkyl group₂-may be substituted with-CH ═ CH-, -CO-, -COO-, -OCO-, -O-, or-S- (2 or more-O-may not be consecutive to cause adjacency). Particularly, from the viewpoint of pretilt angle stability, R is particularly preferable^y1And R^y2Both independently of one another are P^y1-S^y1-the structure represented.

S^y3Preferably a single bond or a linear or branched alkylene group having 1 to 30 carbon atoms, wherein hydrogen atoms in the alkylene group may be substituted with a halogen atom, a cyano group or a nitro group, and-CH in the alkylene group₂May be substituted with-CH- ═ CH-, -C.ident.C-, -CO-, -COO-, -OCO-, -OCOO-, -O-, -NH-or-S- (2 or more-O-may not be continuous but may be adjacent to each other), and is more preferably a single bond or a linear or branched alkylene group having 1 to 12 carbon atoms, in which a hydrogen atom may be substituted with a halogen atom, a cyano group or a nitro group, and in which-CH-is₂May be substituted with-CH- ═ CH-, -C.ident.C-, -CO-, -COO-, -OCO-, -O-or-S- (2 or more-O-S are not continuous and may be adjacent to each other), and is more preferably a single bond or a linear or branched alkylene group having 1 to 6 carbon atoms, in which a hydrogen atom may be replaced by a fluorine atom, a chlorine atom or a cyano group, and in which-CH-in the alkylene group₂-may be substituted by-CH ═ CH-, -C ≡ C-, -CO-, -COO-, -OCO-, -O-, or-S-but 2 or more-O-may not be consecutive to cause adjacency.

S^y2Preferably a single bond or a linear or branched alkylene group having 1 to 12 carbon atoms, wherein hydrogen atoms in the alkylene group may be substituted with a halogen atom, a cyano group or a nitro group, and-CH in the alkylene group₂May be substituted with-CH- ═ CH-, -C.ident.C-, -CO-, -COO-, -OCO-, -OCOO-, -O-, -NH-or-S- (2 or more-O-may not be continuous but may be adjacent to each other), and is more preferably a single bond or a linear or branched alkylene group having 1 to 6 carbon atoms, in which a hydrogen atom may be substituted with a halogen atom, a cyano group or a nitro group, and in which-CH-is₂May be substituted with-CH- ═ CH-, -C.ident.C-, -CO-, -COO-, -OCO-, -O-, -NH-or-S- (2 or more-O-S are not consecutive and may be adjacent to each other), and is more preferably a single bond or a linear or branched alkylene group having 1 to 6 carbon atoms, in which a hydrogen atom may be substituted with a fluorine atom, a chlorine atom or a cyano group, and in which-CH-in the alkylene group₂-may be substituted with-CH ═ CH-, -C ≡ C-, -COO-, -OCO-, -O-, or-S- (2 or more-O-may not be consecutive to cause adjacency).

Z^y1And Z^y2Each independently preferably being a single bond, -C₂H₄-、-C₄H₈-、-C₃H₆-、-OCH₂-、-CH₂O-、-CO-、-COO-、-OCO-、-OCOOCH₂-、-CH₂OCOO-、-OCH₂CH₂O-、-CH＝CRa-COO-、-CH＝CRa-OCO-、-COO-CRa＝CH-、-OCO-CRa＝CH-、-COO-CRa＝CH-COO-、-COO-CRa＝CH-OCO-、-OCO-CRa＝CH-COO-、-OCO-CRa＝CH-OCO-、-COOC₂H₄-、-OCOC₂H₄-、-C₂H₄OCO-、-CH₂OCO-、-COOCH₂-、-OCOCH₂-、-CH＝CH-、-CF＝CF-、-CF＝CH-、-CH＝CF-、-CF₂O-、-OCF₂-、-CF₂CH₂-、-CH₂CF₂-、-CF₂CF₂-or-C ≡ C- (wherein Ra independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms), more preferably a single bond, -C₂H₄-、-C₄H₈-、-OCH₂-、-CH₂O-、-COO-、-OCO-、-OCOOCH₂-、-CH₂OCOO-、-OCH₂CH₂O-、-CH＝CRa-COO-、-CH＝CRa-OCO-、-COO-CRa＝CH-、-OCO-CRa＝CH-、-COO-CRa＝CH-COO-、-COO-CRa＝CH-OCO-、-OCO-CRa＝CH-COO-、-OCO-CRa＝CH-OCO-、-COOC₂H₄-、-OCOC₂H₄-、-C₂H₄OCO-、-CH＝CH-、-CF＝CF-、-CF＝CH-、-CH＝CF-、-CF₂O-、-OCF₂-、-CF₂CH₂-、-CH₂CF₂-、-CF₂CF₂-or-C ≡ C- (wherein Ra independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms), more preferably a single bond, -C₂H₄-、-C₄H₈-、-OCH₂-、-CH₂O-、-COO-、-OCO-、-OCH₂CH₂O-、-CH＝CRa-COO-、-CH＝CRa-OCO-、-COO-CRa＝CH-、-OCO-CRa＝CH-、-COOC₂H₄-、-OCOC₂H₄-、-C₂H₄OCO-、-CH＝CH-、-CF＝CF-、-CF₂O-、-OCF₂-、-CF₂CF₂-or-C.ident.C- (wherein Ra each independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms).

M^y1、M^y2And M^y3Each independently preferably represents a group selected from the group consisting of the following formulae (T-1) to (T-21),

[ solution 4]

When importance is attached to the solubility in the liquid crystal composition, (T-1), (T-2), (T-3), (T-4) and (T-7) are preferable, in the case where high reactivity is regarded as important, (T-4), (T-11), (T-16) and (T-20) are preferable, in the case where good pretilt formation is important, (T-2), (T-4), (T-7), (T-8), (T-10) and (T-11) are preferable, when the effect of improving VHR is emphasized, it is preferably (T-2), (T-4) or (T-11), when importance is attached to the balance of these components, (T-2), (T-4), (T-10) and (T-11) are more preferable.

From the viewpoints of easiness of raw material acquisition and easiness of synthesis, M^y2Particularly preferably a group represented by the following formula (T-4-1) or formula (T-4-2),

[ solution 5]

(wherein the bond is each independently S^y3、Z^y1、Z^y2、R^y1And R^y2Any combination of (a).

In addition, from the viewpoint of ease of acquisition of raw materials and ease of synthesis, M is^y1And M^y3Each independently preferably represents unsubstituted or may be substituted by 1 or more L^y1Substituted 1, 4-phenylene, 1, 4-cyclohexylene or naphthalene-2, 6-diyl, each independently more preferably represents a group selected from the following formulae (A-1) to (A-11),

[ solution 6]

Further preferably represents a group selected from the group consisting of the formulae (A-1) to (A-8), each independently particularly preferably represents a group selected from the formulae (A-1) to (A-4).

L^y1Preferably represents P^y2-S^y2A halogen atom, a cyano group, a nitro group, a C1-30 linear or branched alkyl group, or a structure represented by the formula (K-1), wherein a hydrogen atom in the alkyl group may be replaced by a halogen atom, a cyano group, a nitro group, or P^y2-S^y2-or a structural substitution represented by the formula (K-1) — CH in the alkyl group₂May be substituted by-CH ═ CH--C.ident.C-, -CO-, -COO-, -OCO-, -OCOO-, -O-, -NH-or-S-substituted (2 or more-O-are not consecutive but cause adjacency), and more preferably represents P^y2-S^y2A fluorine atom, a chlorine atom, a cyano group, a C1-12 linear or branched alkyl group, or a structure represented by the formula (K-1), wherein a hydrogen atom in the alkyl group may be replaced by a fluorine atom, a chlorine atom, a cyano group, or P^y2-S^y2-or a structural substitution represented by the formula (K-1) — CH in the alkyl group₂-may be substituted with-CH ═ CH-, -COO-, -OCO-, -O-, or-S- (2 or more-O-S are not continuous and cause adjacency), and more preferably represents P^y2-S^y2A fluorine atom, a chlorine atom, a C1-6 linear or branched alkyl group, or a structure represented by the formula (K-1), wherein the hydrogen atom in the alkyl group may be replaced by a fluorine atom, a chlorine atom, P^y2-S^y2-or a structure represented by the formula (K-1) — CH in the alkyl group₂-may be substituted with-CH ═ CH-, -COO-, -OCO-, or-O- (2 or more-O-s are not consecutive and result in adjacency).

m and n are each independently an integer of preferably 0 to 4, more preferably 0 to 3, and further preferably 0 to 2. Among them, from the viewpoint of solubility when added to the composition and volatility when used in a liquid crystal display element, the total number of m + n is preferably 0 to 6, more preferably 0 to 4, and still more preferably 1 to 3.

P^y1And P^y2Preferably each independently represents a substituent selected from the group represented by the formulae (P-1) to (P-14),

[ solution 7]

(in the formula, black dots represent^y1Or S^y2The bond of (3). ) More preferably (P-1), (P-2), (P-4), (P-5), (P-7), (P-9), (P-11), (P-12) and (P-13), and still more preferably (P-1), (P-2), (P-7), (P-12) and (P-13).

Wherein P contained in the structure represented by the general formula (Y-1)ⁱ¹、P^y1And P^y2The total number of (a) is preferably at least 1, more preferably at least 2. P contained in the structure represented by the general formula (Y-1)ⁱ¹、P^y1And P^y2The total number of (a) is preferably 1 to 4, more preferably 2 to 4, and still more preferably 2 to 3. Especially in Pⁱ¹、P^y1And P^y2When the total number of (a) to (b) is 2 to 3, the polymer obtained by polymerization is a crosslinked polymer, and thus is preferable in view of stabilization of the three-dimensional structure of the polymer and improvement of the tilt stability.

As the structure represented by the general formula (Y-1), the following formula (Y-1-A1) can be preferably mentioned.

[ solution 8]

(in the formula, K^y1aRepresents a group K^y1The same meaning is given to the same person,

R^y1aand R^y2aEach independently represents a hydrogen atom, a halogen atom, a cyano group, P^y1a-S^y1aOr a linear or branched alkyl group having 1 to 12 carbon atoms, wherein a hydrogen atom in the alkyl group may be replaced by a fluorine atom, a chlorine atom, a cyano group or P^y1a-S^y1a-substituted, -CH in the alkyl group₂-may be substituted with-CH ═ CH-, -CO-, -COO-, -OCO-, -O-or-S-but 2 or more-O-are not consecutive to cause adjacency,

S^y3aa single bond or a linear or branched alkylene group having 1 to 12 carbon atoms, wherein hydrogen atoms in the alkylene group may be substituted by fluorine atoms, chlorine atoms or cyano groups, and-CH in the alkylene group₂-may be substituted with-CH ═ CH-, -CO-, -COO-, -OCO-, -O-or-S-but 2 or more-O-are not consecutive to cause adjacency,

Z^y1aand Z^y2aEach independently represents a single bond, -C₂H₄-、-C₄H₈-、-OCH₂-、-CH₂O-、-COO-、-OCO-、-OCOOCH₂-、-CH₂OCOO-、-OCH₂CH₂O-、-CH＝CRa-COO-、-CH＝CRa-OCO-、-COO-CRa＝CH-、-OCO-CRa＝CH-、-COO-CRa＝CH-COO-、-COO-CRa＝CH-OCO-、-OCO-CRa＝CH-COO-、-OCO-CRa＝CH-OCO-、-COOC₂H₄-、-OCOC₂H₄-、-C₂H₄OCO-、-CH＝CH-、-CF＝CF-、-CF＝CH-、-CH＝CF-、-CF₂O-、-OCF₂-、-CF₂CH₂-、-CH₂CF₂-、-CF₂CF₂-or-C.ident.C- (wherein Ra each independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms),

M^y1a、M^y2aand M^y3aEach independently represents a group selected from the group consisting of the following formulae (T-1) to (T-21),

[ solution 9]

(wherein any of the above-mentioned groups may have a bond at any position, and any of-CH-s may be independently substituted with-N-CH₂May each independently be-O-, -S-, -NR-⁰- (in the formula, R⁰Represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms. ) -CS-or-CO-but does not include an-O-O-bond. ) The hydrogen atoms in these ring structures may be replaced by L^y1aSubstituted, L^y1aRepresents P^y2a-S^y2a-, fluorine atom, chlorine atom, cyano group, C1-30 linear or branched alkyl group or a structure represented by the general formula (K-1), wherein a hydrogen atom in the alkyl group may be replaced by fluorine atom, chlorine atom, P^y2a-S^y2a-or cyano, in which alkyl the-CH group is present₂-may be substituted by-CH ═ CH-, -CO-, -COO-, -OCO-, -O-or-S-but not 2 or more-O-groups are continuous and result in adjacency, in L^y1aIn the case where there are plural, they may be the same or different,

P^y1aand P^y2aEach independently represents a substituent selected from the group represented by the formulae (P-1) to (P-14),

[ solution 10]

(in the formula, black dots represent^y1aOr S^y2aThe bond of (3). ),

S^y1aand S^y2aEach independently a single bond or a linear or branched alkylene group having 1 to 8 carbon atoms, wherein a hydrogen atom in the alkylene group may be substituted with a fluorine atom, a chlorine atom or a cyano group, and wherein-CH in the alkylene group₂-may be substituted with-CH ═ CH-, -CO-, -COO-, -OCO-, -O-or-S-but 2 or more-O-are not consecutive to cause adjacency,

m^aand n^aEach independently represents an integer of 0 to 3, wherein the total number of m + n is 0 to 4,

wherein P contained in the structure represented by the general formula (Y-1-A1)ⁱ¹、P^y1aAnd P^y2aThe total number of (2) is at least 1 or more. )

More preferred examples of the structure represented by the general formula (Y-1) include the following formulae (Y-1-A2) and (Y-1-A3).

[ solution 11]

[ solution 12]

(in the formula, K^y1a、R^y2a、S^y2a、S^y3a、P^y1a、P^y2a、Z^y1a、Z^y2a、M^y1a、M^y2a、M^y3a、m^aAnd n^aIs represented by the formula (Y-1-A1)^y1、R^y2a、S^y2a、S^y3a、P^y1a、P^y2a、Z^y1a、Z^y2a、M^y1a、M^y2a、M^y3a、m^aAnd n^aSame meaning of P^y4aRepresents a group of formulae and P^y2aSame meaning, S^y4aIs represented by the formula^y2aThe same meaning is used. )

In particular, in the structure represented by the formula (Y-1-A3), since the polymeric groups are located at both ends of the ring structure, it is preferable from the viewpoint of increasing the rigidity and improving the tilt stability of the crosslinked polymer obtained by polymerization.

More preferred examples of the structure represented by the general formula (Y-1) include the following formulae (Y-1-B1) and (Y-1-B2).

[ solution 13]

[ solution 14]

(in the formula, K^y1bRepresents a structure represented by the formula (K-1b-1) or the formula (K-1b-2),

[ solution 15]

(in the formula, the black dots represent bond bonds,

Y^i1band Y^i2bEach independently represents a linear or branched alkyl group having 1 to 12 carbon atoms, and at least 1 or more-CH in the alkyl groups₂is-SO₂A hydrogen atom in the alkyl groups may be substituted by a fluorine atom, a chlorine atom, a cyano group or a phenyl group (the hydrogen atom present in the phenyl group may be substituted by a cyano group, a fluorine atom, a chlorine atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, an alkenyl group having 2 to 5 carbon atoms or a nitro group), and furthermore, a-CH group in the alkyl groups₂-may be substituted, in such a way that the oxygen atoms are not directly adjacent, -CH-, -C.ident.C-, -O-, -NH-, -C (═ O) -, -COO-or-OCO-,

S^i1b、S^i3band S^i4bEach independently represents an alkylene group having 1 to 6 carbon atoms or a single bond, wherein-CH in the alkylene group₂-may be substituted, in such a way that the oxygen atoms are not directly adjacent, -CH-, -C.ident.C-, -O-, -NH-, -C (═ O) -, -COO-or-OCO-,

R^i2beach independently represents a hydrogen atom, a linear or branched alkyl group having 1 to 12 carbon atoms, the hydrogen atom in the alkyl group may be substituted by a fluorine atom, a chlorine atom or a cyano group, or-CH in the group₂-may be substituted, in such a way that the oxygen atoms are not directly adjacent, -CH-, -C.ident.C-, -O-, -NH-, -C (═ O) -, -COO-or-OCO-,

P^i1brepresents a formula (P-1) or a formula (P-2),

[ solution 16]

(wherein, black dots represent the same as Sp^i1bThe bond of (3). ),

Sp^i1brepresents an alkylene group having 1 to 6 carbon atoms or a single bond, the alkylene group having a-CH group₂-may be substituted, in such a way that the oxygen atoms are not directly adjacent, -CH-, -C ≡ C-, -O-, -NH-, -C (═ O) -, -COO or-OCO-. ),

R^y2beach independently represents a hydrogen atom, a halogen atom, a cyano group, or a C1-6 linear or branched alkyl group, wherein-CH in the alkyl group₂May be substituted by-COO-, -OCO-or-O-but not 2 or more-O-are consecutive to cause adjacency,

S^y3ba single bond or a linear or branched alkylene group having 1 to 12 carbon atoms, wherein hydrogen atoms in the alkylene group may be substituted with fluorine atoms and-CH in the alkylene group₂May be substituted by-COO-, -OCO-or-O-but not 2 or more-O-are consecutive to cause adjacency,

P^y2band P^y4bEach independently represents formula (P-1) or formula (P-2),

[ solution 17]

(in the formula, black dots represent^y2bOr S^y4bThe bond of (3). ),

S^y2band S^y4bEach independently a single bond or a linear alkylene group having 1 to 6 carbon atoms, wherein hydrogen atoms in the alkylene group may be replaced by fluorine atoms and-CH in the alkylene group₂May be substituted by-COO-, -OCO-or-O-but not 2 or more-O-are consecutive to cause adjacency,

Z^y1band Z^y2bEach independently represents a single bond, -C₂H₄-、-OCH₂-、-CH₂O-、-COO-、-OCO-、-OCH₂CH₂O-、-CH＝CRa-COO-、-CH＝CRa-OCO-、-COO-CRa＝CH-、-OCO-CRa＝CH-、-COOC₂H₄-、-OCOC₂H₄-、-C₂H₄OCO-、-CH＝CH-、-CF₂O-、-OCF₂-, or-C.ident.C- (wherein, Ra each independently represents a hydrogen atom or an alkyl group having 1 to 2 carbon atoms), M^y2bIs a group represented by the formula (T-4-1) or the formula (T-4-2),

[ solution 18]

(wherein the bond is each independently S^y3b、Z^y1b、Z^y2b、R^y2b、S^y2bOr S^y4bAny one of which is combined),

M^y1band M^y3bEach independently represents a group selected from the following formulae (A-1) to (A-8),

[ solution 19]

L^y1bRepresents P^y2b-S^y2b-, fluorine atom, chlorine atom, cyano groupA C1-6 linear or branched alkyl group, wherein-CH is present in the alkyl group₂May be substituted by-COO-, -OCO-or-O-but not 2 or more-O-are consecutive to cause adjacency,

m^band n^bEach independently represents an integer of 0 to 2, wherein the total number of m + n is 0 to 2,

wherein P contained in the structure represented by the formula (Y-1-B1) or the formula (Y-1-B2)^y2bAnd P^y4bThe total number of (a) is 1 to 3. )

More preferred examples of the structure represented by the general formula (Y-1) include the following formulae (Y-1-B3) to (Y-1-B6).

[ solution 20]

(in the formula, K^y1b、S^y3b、S^y2b、S^y4b、Z^y1b、Z^y2b、M^y1b、M^y3b、m^bAnd n^bEach represents a group represented by the formula (Y-1-B1) or K in the formula (Y-1-B2)^y1b、S^y3b、S^y2b、S^y4b、Z^y1b、Z^y2b、M^y1b、M^y3b、m^bAnd n^bThe same meaning is used. )

Furthermore, the polymerizable compound represented by the general formula (Y-1) is also preferably represented by the formula (K-1) or S^y3bHaving a polymeric group thereon. This is because the structure represented by the general formula (Y) is located close to the polymerizable group, so that a crosslinked polymer can be formed at a position close to the substrate surface, and the effect of enhancing VHR can be further enhanced.

As the polymerizable compound represented by the general formula (Y-1) according to the present invention, compounds represented by the general formulae (Y-1-1) to (Y-41-35) are particularly preferable. Of the compounds represented by the general formulae (Y-1-1) to (Y-41-35), the general formulae (Y-28-1) to (Y-39-10) are preferred.

[ solution 21]

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[ chemical formula 72]

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[ 76]

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[ solution 92]

Hereinafter, when the content in the liquid crystal composition of the present invention is denoted by "%", the content means wt% unless otherwise noted.

In the liquid crystal composition of the present invention, the lower limit of the content of the compound having a structure represented by formula (K-1) in the molecule is preferably 0.01 mass%, preferably 0.02 mass%, preferably 0.03 mass%, preferably 0.04 mass%, preferably 0.05 mass%, preferably 0.06 mass%, preferably 0.07 mass%, preferably 0.08 mass%, preferably 0.09 mass%, preferably 0.1 mass%, preferably 0.12 mass%, preferably 0.15 mass%, preferably 0.17 mass%, preferably 0.2 mass%, preferably 0.22 mass%, preferably 0.25 mass%, preferably 0.27 mass%, preferably 0.3 mass%, preferably 0.32 mass%, preferably 0.35 mass%, preferably 0.37 mass%, preferably 0.4 mass%, preferably 0.42 mass%, preferably 0.45 mass%, preferably 0.5 mass%, preferably 0.55 mass%.

In the liquid crystal composition of the present invention, the upper limit of the content of the compound having a structure represented by formula (K-1) in the molecule is preferably 5 mass%, preferably 4.5 mass%, preferably 4 mass%, preferably 3.5 mass%, preferably 3 mass%, preferably 2.5 mass%, preferably 2 mass%, preferably 1.5 mass%, preferably 1 mass%, preferably 0.95 mass%, preferably 0.9 mass%, preferably 0.85 mass%, preferably 0.8 mass%, preferably 0.75 mass%, preferably 0.7 mass%, preferably 0.65 mass%, preferably 0.6 mass%, preferably 0.55 mass%, preferably 0.5 mass%, preferably 0.45 mass%, preferably 0.4 mass%.

More specifically, the content is preferably 0.2 to 1.5% by mass in order to obtain a sufficient pretilt angle or a residual amount of a polymerizable compound or a high Voltage Holding Ratio (VHR), and when suppression of precipitation at low temperatures is considered important, the content is preferably 0.01 to 1.0% by mass. Further, in the case where a plurality of compounds each having a structure represented by the formula (K-1) in the molecule are contained, the content of each is preferably 0.01 to 0.6% by mass. Therefore, in order to solve all of these problems, it is particularly desirable to adjust the compound having a structure represented by the formula (K-1) in the molecule to a range of 0.1 to 1.0% by mass, and from the viewpoint of low-temperature storage stability, the preparation is particularly preferably performed in a range of 0.1 to 0.5% by mass.

The liquid crystal composition of the present invention preferably contains 1 or 2 or more compounds represented by the general formula (L). The compound represented by the general formula (L) corresponds to a compound having a substantially neutral dielectric property (Δ ε has a value of-2 to 2). Therefore, the number of polar groups such as halogen contained in the molecule is preferably 2 or less, preferably 1 or less, and preferably none.

[ solution 93]

(in the formula, R^L1And R^L2Each independently represents an alkyl group having 1 to 8 carbon atoms, 1 or 2 or more-CH groups which are not adjacent to each other in the alkyl group₂-may each be independently substituted by-CH ═ CH-, -C ≡ C-, -O-, -CO-, -COO-or-OCO-,

n^L1represents 0, 1,2 or 3,

A^L1、A^L2and A^L3Each independently represents a group selected from the group consisting of:

(a)1, 4-cyclohexylene (1-CH present in the radical)₂-or non-adjacent 2 or more-CH₂-may be substituted by-O-. ) And

(b)1, 4-phenylene (1-CH-or non-adjacent 2 or more-CH-present in the radical may be substituted by-N-

(c) Naphthalene-2, 6-diyl, 1,2,3, 4-tetrahydronaphthalene-2, 6-diyl or decahydronaphthalene-2, 6-diyl (1-CH ═ or non-adjacent 2 or more-CH ═ present in naphthalene-2, 6-diyl or 1,2,3, 4-tetrahydronaphthalene-2, 6-diyl may be substituted by-N ═ and.)

The above-mentioned group (a), group (b) and group (c) may each independently be substituted with a cyano group, a fluorine atom or a chlorine atom,

Z^L1and Z^L2Each independently represents a single bond, -CH₂CH₂-、-(CH₂)₄-、-OCH₂-、-CH₂O-、-COO-、-OCO-、-OCF₂-、-CF₂O-, -CH-N-CH-, -CH-, -CF-or-C ≡ C-,

at n^L1A plurality of A's being present for 2 or 3^L2In the case of (2), they may be the same or different, in n^L1A plurality of Z s being 2 or 3^L2In the case where the compounds represented by the general formulae (N-1), (N-2) and (N-3) are not included, they may be the same or different. )

The compounds represented by the general formula (L) may be used alone or in combination. The type of the combinable compound is not particularly limited, and it is suitably used in combination according to desired properties such as solubility at low temperature, transition temperature, electrical reliability, birefringence, and the like. The kind of the compound used is, for example, 1 in one embodiment of the present invention. Or 2,3,4, 5, 6, 7, 8, 9, 10 or more in other embodiments of the present invention.

In the composition of the present invention, the content of the compound represented by the general formula (L) is required to be appropriately adjusted depending on required performances such as solubility at low temperature, transition temperature, electrical reliability, birefringence, process suitability, dropping marks, burn-in, dielectric anisotropy, and the like.

The lower limit of the preferable content of the compound represented by the formula (L) is 1%, 10%, 20%, 30%, 40%, 50%, 55%, 60%, 65%, 70%, 75%, 80% relative to the total amount of the composition of the present invention. The upper limit of the content is preferably 95%, 85%, 75%, 65%, 55%, 45%, 35%, 25%.

When a composition having a high response speed is required by keeping the viscosity of the composition of the present invention low, the lower limit value is preferably high and the upper limit value is preferably high. Further, when a composition having good temperature stability is required to keep Tni of the composition of the present invention high, it is preferable that the lower limit value is high and the upper limit value is high. In order to increase the dielectric anisotropy while keeping the driving voltage low, the lower limit value and the upper limit value are preferably low.

In the case where reliability is important, R is preferably selected^L1And R^L2Are all alkyl groups. When importance is attached to reduction in volatility of the compound, an alkoxy group is preferable, and when importance is attached to reduction in viscosity, at least one of the groups is preferably an alkenyl group.

The number of halogen atoms present in the molecule is preferably 0, 1,2 or 3, preferably 0 or 1, and when importance is attached to compatibility with other liquid crystal molecules, 1 is preferred.

R^L1And R^L2When the ring structure to which the compound is bonded is a phenyl group (aromatic group), the compound is preferably a linear alkyl group having 1 to 5 carbon atoms, a linear alkoxy group having 1 to 4 carbon atoms, or an alkenyl group having 4 to 5 carbon atoms, and the ring structure to which the compound is bonded is cyclohexane, pyran, or bisIn the case of a saturated ring structure such as an alkane, a linear alkyl group having 1 to 5 carbon atoms, a linear alkoxy group having 1 to 4 carbon atoms, and a linear alkenyl group having 2 to 5 carbon atoms are preferable. In order to stabilize the nematic phase, the total of carbon atoms and oxygen atoms when present is preferably 5 or less, and is preferably linear.

The alkenyl group is preferably selected from groups represented by any one of the formulae (R1) to (R5). (Black dots in each formula represent carbon atoms in the ring structure.)

[ solution 94]

n^L1Preferably 0 when importance is attached to the response speed, in order to improve the nematic phaseThe upper limit temperature is preferably 2 or 3, and in order to achieve the balance, it is preferably 1. In addition, in order to satisfy the characteristics required as a composition, it is preferable to combine compounds of different values.

A^L1、A^L2And A^L3In the case where an increase in Δ n is required, it is preferably aromatic, and in order to improve the response speed, it is preferably aliphatic, and each of them independently represents trans-1, 4-cyclohexylene, 1, 4-phenylene, 2-fluoro-1, 4-phenylene, 3, 5-difluoro-1, 4-phenylene, 1, 4-cyclohexenylene, or 1, 4-bicyclo [2.2.2 ] p]Octylene, piperidine-1, 4-diyl, naphthalene-2, 6-diyl, decahydronaphthalene-2, 6-diyl or 1,2,3, 4-tetrahydronaphthalene-2, 6-diyl, more preferably represents the following structure,

[ solution 95]

More preferably, it represents trans-1, 4-cyclohexylene or 1, 4-phenylene.

With respect to Z^L1And Z^L2When importance is attached to the response speed, a single bond is preferable.

The compound represented by the general formula (L) preferably has 0 or 1 halogen atom in the molecule.

The compound represented by the general formula (L) is preferably a compound selected from the group consisting of compounds represented by the general formulae (L-1) to (L-7).

The compound represented by the general formula (L-1) is the following compound.

[ solution 96]

(in the formula, R^L11And R^L12Each independently represents R in the general formula (L)^L1And R^L2The same meaning is used. )

R^L11And R^L12Preferably a linear alkyl group having 1 to 5 carbon atoms, a linear alkoxy group having 1 to 4 carbon atoms and a linear carbon atomAlkenyl groups having a seed number of 2 to 5.

The compounds represented by the general formula (L-1) may be used alone or 2 or more compounds may be used in combination. The type of the combinable compound is not particularly limited, and it is suitably used in combination according to the required properties such as solubility at low temperature, transition temperature, electrical reliability, birefringence, and the like. The kind of the compound to be used is, for example, 1 kind, 2 kinds, 3 kinds, 4 kinds, 5 kinds or more in one embodiment of the present invention.

The lower limit of the content is preferably 1%, 2%, 3%, 5%, 7%, 10%, 15%, 20%, 25%, 30%, 35%, 40%, 45%, 50%, 55% with respect to the total amount of the composition of the present invention. The upper limit of the content is preferably 95%, 90%, 85%, 80%, 75%, 70%, 65%, 60%, 55%, 50%, 45%, 40%, 35%, 30%, 25% with respect to the total amount of the composition of the present invention.

When a composition having a high response speed is required by keeping the viscosity of the composition of the present invention low, the lower limit value is preferably high and the upper limit value is preferably high. Further, when a composition having high temperature stability is required by keeping Tni of the composition of the present invention high, the lower limit value is preferably medium and the upper limit value is preferably medium. In order to increase the dielectric anisotropy while keeping the driving voltage low, the lower limit value and the upper limit value are preferably low.

The compound represented by the general formula (L-1) is preferably a compound selected from the group of compounds represented by the general formula (L-1-1).

[ solution 97]

(in the formula, R^L12Represents the same meaning as in the general formula (L-1). )

The compound represented by the general formula (L-1-1) is preferably a compound selected from the group consisting of compounds represented by the formulae (L-1-1.1) to (L-1-1.3), preferably a compound represented by the formula (L-1-1.2) or (L-1-1.3), and particularly preferably a compound represented by the formula (L-1-1.3).

[ solution 98]

The lower limit of the preferable content of the compound represented by the formula (L-1-1.3) is 1%, 2%, 3%, 5%, 7%, 10% with respect to the total amount of the composition of the present invention. The upper limit of the content is preferably 20%, 15%, 13%, 10%, 8%, 7%, 6%, 5%, 3% with respect to the total amount of the composition of the present invention.

The compound represented by the general formula (L-1) is preferably a compound selected from the group of compounds represented by the general formula (L-1-2).

[ solution 99]

(in the formula, R^L12Represents the same meaning as in the general formula (L-1). )

The lower limit of the preferable content of the compound represented by the formula (L-1-2) is 1%, 5%, 10%, 15%, 17%, 20%, 23%, 25%, 27%, 30%, 35% with respect to the total amount of the composition of the present invention. The upper limit of the content is preferably 60%, 55%, 50%, 45%, 42%, 40%, 38%, 35%, 33%, 30% with respect to the total amount of the composition of the present invention.

Further, the compound represented by the general formula (L-1-2) is preferably a compound selected from the group consisting of compounds represented by the formulae (L-1-2.1) to (L-1-2.4), and is preferably a compound represented by the formulae (L-1-2.2) to (L-1-2.4). In particular, the compounds represented by the formula (L-1-2.2) are preferable because they improve the response speed of the composition of the present invention. When higher Tni is required than the response speed, it is preferable to use a compound represented by the formula (L-1-2.3) or the formula (L-1-2.4). In order to obtain good solubility at low temperatures, the content of the compounds represented by the formulae (L-1-2.3) and (L-1-2.4) is not preferably 30% or more.

[ solution 100]

The lower limit of the preferable content of the compound represented by the formula (L-1-2.2) is 10%, 15%, 18%, 20%, 23%, 25%, 27%, 30%, 33%, 35%, 38%, 40% with respect to the total amount of the composition of the present invention. The upper limit of the content is preferably 60%, 55%, 50%, 45%, 43%, 40%, 38%, 35%, 32%, 30%, 27%, 25%, 22% with respect to the total amount of the composition of the present invention.

The lower limit of the preferable content of the compound represented by the formula (L-1-1.3) and the compound represented by the formula (L-1-2.2) is 10%, 15%, 20%, 25%, 27%, 30%, 35%, 40% based on the total amount of the composition of the present invention. The upper limit of the content is preferably 60%, 55%, 50%, 45%, 43%, 40%, 38%, 35%, 32%, 30%, 27%, 25%, 22% with respect to the total amount of the composition of the present invention.

The compound represented by the general formula (L-1) is preferably a compound selected from the group of compounds represented by the general formula (L-1-3).

[ solution 101]

(in the formula, R^L13And R^L14Each independently represents an alkyl group having 1 to 8 carbon atoms or an alkoxy group having 1 to 8 carbon atoms. )

R^L13And R^L14Preferably, the alkyl group has 1 to 5 carbon atoms and the alkoxy group has 1 to 4 carbon atoms.

The lower limit of the preferable content of the compound represented by the formula (L-1-3) is 1%, 5%, 10%, 13%, 15%, 17%, 20%, 23%, 25%, 30% with respect to the total amount of the composition of the present invention. The upper limit of the content is preferably 60%, 55%, 50%, 45%, 40%, 37%, 35%, 33%, 30%, 27%, 25%, 23%, 20%, 17%, 15%, 13%, 10% relative to the total amount of the composition of the present invention.

Further, the compound represented by the general formula (L-1-3) is preferably a compound selected from the group consisting of compounds represented by the formulae (L-1-3.1) to (L-1-3.13), and is preferably a compound represented by the formula (L-1-3.1), the formula (L-1-3.3) or the formula (L-1-3.4). In particular, the compounds represented by the formula (L-1-3.1) are preferable because they improve the response speed of the composition of the present invention. When higher Tni is required than the response speed, it is preferable to use compounds represented by the formulae (L-1 to 3.3), (L-1 to 3.4), (L-1 to 3.11) and (L-1 to 3.13). In order to improve the solubility at low temperatures, the total content of the compounds represented by the formulae (L-1-3.3), (L-1-3.4), (L-1-3.11) and (L-1-3.13) is not preferably 20% or more.

[ solution 102]

The lower limit of the preferable content of the compound represented by the formula (L-1-3.1) is 1%, 2%, 3%, 5%, 7%, 10%, 13%, 15%, 18%, 20% with respect to the total amount of the composition of the present invention. The upper limit of the content is preferably 20%, 17%, 15%, 13%, 10%, 8%, 7%, 6% with respect to the total amount of the composition of the present invention.

The compound represented by the general formula (L-1) is preferably a compound selected from the group of compounds represented by the general formulae (L-1-4) and/or (L-1-5).

[ solution 103]

(in the formula, R^L15And R^L16Each independently represents an alkyl group having 1 to 8 carbon atoms or an alkoxy group having 1 to 8 carbon atoms. )

R^L15And R^L16Preferably, the alkyl group has 1 to 5 carbon atoms and the alkoxy group has 1 to 4 carbon atoms.

The lower limit of the preferable content of the compound represented by the formula (L-1-4) is 1%, 5%, 10%, 13%, 15%, 17%, 20% with respect to the total amount of the composition of the present invention. The upper limit of the content is preferably 25%, 23%, 20%, 17%, 15%, 13%, 10% with respect to the total amount of the composition of the present invention.

The lower limit of the preferable content of the compound represented by the formula (L-1-5) is 1%, 5%, 10%, 13%, 15%, 17%, 20% with respect to the total amount of the composition of the present invention. The upper limit of the content is preferably 25%, 23%, 20%, 17%, 15%, 13%, 10% with respect to the total amount of the composition of the present invention.

Further, the compounds represented by the general formulae (L-1-4) and (L-1-5) are preferably compounds selected from the group of compounds represented by the formulae (L-1-4.1) to (L-1-5.3), and are preferably compounds represented by the formulae (L-1-4.2) or (L-1-5.2).

[ solution 104]

The lower limit of the preferable content of the compound represented by the formula (L-1-4.2) is 1%, 2%, 3%, 5%, 7%, 10%, 13%, 15%, 18%, 20% with respect to the total amount of the composition of the present invention. The upper limit of the content is preferably 20%, 17%, 15%, 13%, 10%, 8%, 7%, 6% with respect to the total amount of the composition of the present invention.

Preferably 2 or more compounds selected from the group consisting of the compounds represented by the formulae (L-1-1.3), (L-1-2.2), (L-1-3.1), (L-1-3.3), (L-1-3.4), (L-1-3.11) and (L-1-3.12), preferably 2 or more compounds selected from the group consisting of the compounds represented by the formulae (L-1-1.3), (L-1-2.2), (L-1-3.1), (L-1-3.3), (L-1-3.4) and (L-1-4.2), and the lower limit of the total content of these compounds is 1%, 2%, 3%, or 3% relative to the total amount of the composition of the present invention, 5%, 7%, 10%, 13%, 15%, 18%, 20%, 23%, 25%, 27%, 30%, 33%, 35%, with respect to the total amount of the composition of the present invention, the upper limit being 80%, 70%, 60%, 50%, 45%, 40%, 37%, 35%, 33%, 30%, 28%, 25%, 23%, 20%. When importance is attached to the reliability of the composition, it is preferable to combine 2 or more compounds selected from the group consisting of the compounds represented by the formulae (L-1-3.1), (L-1-3.3) and (L-1-3.4), and when importance is attached to the response speed of the composition, it is preferable to combine 2 or more compounds selected from the group consisting of the compounds represented by the formulae (L-1-1.3) and (L-1-2.2).

The compound represented by the general formula (L-1) is preferably a compound selected from the group of compounds represented by the general formula (L-1-6).

[ solution 105]

(in the formula, R^L17And R^L18Each independently represents a methyl group or a hydrogen atom. )

The lower limit of the preferable content of the compound represented by the formula (L-1-6) is 1%, 5%, 10%, 15%, 17%, 20%, 23%, 25%, 27%, 30%, 35% with respect to the total amount of the composition of the present invention. The upper limit of the content is preferably 60%, 55%, 50%, 45%, 42%, 40%, 38%, 35%, 33%, 30% with respect to the total amount of the composition of the present invention.

Further, the compound represented by the general formula (L-1-6) is preferably a compound selected from the group of compounds represented by the formulae (L-1-6.1) to (L-1-6.3).

[ solution 106]

The compound represented by the general formula (L-2) is the following compound.

[ solution 107]

(in the formula, R^L21And R^L22Each independently represents R in the general formula (L)^L1And R^L2The same meaning is used. )

R^L21Preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, R^L22Preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms.

The compound represented by the general formula (L-2) may be used alone, or 2 or more compounds may be used in combination. The type of the combinable compound is not particularly limited, and it is suitably used in combination according to the required properties such as solubility at low temperature, transition temperature, electrical reliability, birefringence, and the like. The kind of the compound to be used is, for example, 1 kind, 2 kinds, 3 kinds, 4 kinds, 5 kinds or more in one embodiment of the present invention.

When the solubility at low temperature is important, the effect is good when the content is set to be high, and conversely, when the response speed is important, the effect is good when the content is set to be low. Further, when the dropping mark and the burn-in characteristic are improved, it is preferable to set the range of the content to be centered.

The lower limit of the preferable content of the compound represented by the formula (L-2) is 1%, 2%, 3%, 5%, 7%, 10% with respect to the total amount of the composition of the present invention. The upper limit of the content is preferably 20%, 15%, 13%, 10%, 8%, 7%, 6%, 5%, 3% with respect to the total amount of the composition of the present invention.

Further, the compound represented by the general formula (L-2) is preferably a compound selected from the group of compounds represented by the formulae (L-2.1) to (L-2.6), and is preferably a compound represented by the formulae (L-2.1), (L-2.3), (L-2.4) and (L-2.6).

[ solution 108]

The compound represented by the general formula (L-3) is the following compound.

[ solution 109]

(in the formula, R^L31And R^L32Each independently represents R in the general formula (L)^L1And R^L2The same meaning is used. )

R^L31And R^L32Each independently preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms.

The compounds represented by the general formula (L-3) may be used alone or 2 or more compounds may be used in combination. The type of the combinable compound is not particularly limited, and it is suitably used in combination according to the required properties such as solubility at low temperature, transition temperature, electrical reliability, birefringence, and the like. The kind of the compound to be used is, for example, 1 kind, 2 kinds, 3 kinds, 4 kinds, 5 kinds or more in one embodiment of the present invention.

The lower limit of the preferable content of the compound represented by the formula (L-3) is 1%, 2%, 3%, 5%, 7%, 10% with respect to the total amount of the composition of the present invention. The upper limit of the content is preferably 20%, 15%, 13%, 10%, 8%, 7%, 6%, 5%, 3% with respect to the total amount of the composition of the present invention.

In the case of obtaining a high birefringence, it is effective when the content is set high, and conversely, in the case of giving importance to a high Tni, it is effective when the content is set low. Further, in the case of improving the dropping mark and the burn-in characteristic, it is preferable to set the range of the content to be centered.

Further, the compound represented by the general formula (L-3) is preferably a compound selected from the group of compounds represented by the formulae (L-3.1) to (L-3.7), and is preferably a compound represented by the formulae (L-3.2) to (L-3.5).

[ solution 110]

The compound represented by the general formula (L-4) is the following compound.

[ solution 111]

(in the formula, R^L41And R^L42Each independently represents R in the general formula (L)^L1And R^L2The same meaning is used. )

R^L41Preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, R^L42Preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms. )

The compounds represented by the general formula (L-4) may be used alone or 2 or more compounds may be used in combination. The type of the combinable compound is not particularly limited, and it is suitably used in combination according to the required properties such as solubility at low temperature, transition temperature, electrical reliability, birefringence, and the like. The kind of the compound to be used is, for example, 1 kind, 2 kinds, 3 kinds, 4 kinds, 5 kinds or more in one embodiment of the present invention.

In the composition of the present invention, the content of the compound represented by the general formula (L-4) is required to be appropriately adjusted depending on the required performances such as solubility at low temperature, transition temperature, electrical reliability, birefringence, process suitability, dropping marks, burn-in, dielectric anisotropy, and the like.

The lower limit of the preferable content of the compound represented by the formula (L-4) is 1%, 2%, 3%, 5%, 7%, 10%, 14%, 16%, 20%, 23%, 26%, 30%, 35%, 40% with respect to the total amount of the composition of the present invention. The upper limit of the preferable content of the compound represented by the formula (L-4) is 50%, 40%, 35%, 30%, 20%, 15%, 10%, 5% with respect to the total amount of the composition of the present invention.

The compound represented by the general formula (L-4) is preferably a compound represented by, for example, the formulae (L-4.1) to (L-4.3).

[ solution 112]

The compound represented by the formula (L-4.1), the compound represented by the formula (L-4.2), both the compound represented by the formula (L-4.1) and the compound represented by the formula (L-4.2) may be contained, or the compounds represented by the formulae (L-4.1) to (L-4.3) may be contained in the composition, depending on the required performance such as solubility at low temperature, transition temperature, electrical reliability, birefringence, and the like. The lower limit of the preferred content of the compound represented by formula (L-4.1) or formula (L-4.2) is 3%, 5%, 7%, 9%, 11%, 12%, 13%, 18%, 21%, and the upper limit thereof is 45%, 40%, 35%, 30%, 25%, 23%, 20%, 18%, 15%, 13%, 10%, 8% with respect to the total amount of the composition of the present invention.

When both the compound represented by the formula (L-4.1) and the compound represented by the formula (L-4.2) are contained, the lower limit of the preferable content of both compounds is 15%, 19%, 24%, 30%, and the upper limit thereof is 45%, 40%, 35%, 30%, 25%, 23%, 20%, 18%, 15%, 13%, relative to the total amount of the composition of the present invention.

The compound represented by the general formula (L-4) is preferably a compound represented by, for example, formulae (L-4.4) to (L-4.6), and is preferably a compound represented by formula (L-4.4).

[ solution 113]

The compound represented by the formula (L-4.4), the compound represented by the formula (L-4.5), or both the compound represented by the formula (L-4.4) and the compound represented by the formula (L-4.5) may be contained in accordance with the required performance such as solubility at low temperature, transition temperature, electrical reliability, birefringence, and the like.

The lower limit of the preferable content of the compound represented by the formula (L-4.4) or the formula (L-4.5) is 3%, 5%, 7%, 9%, 11%, 12%, 13%, 18%, 21% with respect to the total amount of the composition of the present invention. Preferred upper limits are 45%, 40%, 35%, 30%, 25%, 23%, 20%, 18%, 15%, 13%, 10%, 8%.

When both the compound represented by the formula (L-4.4) and the compound represented by the formula (L-4.5) are contained, the lower limit of the preferable content of both compounds is 15%, 19%, 24%, 30%, and the upper limit thereof is 45%, 40%, 35%, 30%, 25%, 23%, 20%, 18%, 15%, 13%, relative to the total amount of the composition of the present invention.

The compound represented by the general formula (L-4) is preferably a compound represented by the formulae (L-4.7) to (L-4.10), and particularly preferably a compound represented by the formula (L-4.9).

[ chemical formula 114]

The compound represented by the general formula (L-5) is the following compound.

[ solution 115]

(in the formula, R^L51And R^L52Each independently represents R in the general formula (L)^L1And R^L2The same meaning is used. )

R^L51Preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, R^L52Preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms.

The compound represented by the general formula (L-5) may be used alone, or 2 or more compounds may be used in combination. The type of the combinable compound is not particularly limited, and it is suitably used in combination according to the required properties such as solubility at low temperature, transition temperature, electrical reliability, birefringence, and the like. The kind of the compound to be used is, for example, 1 kind, 2 kinds, 3 kinds, 4 kinds, 5 kinds or more in one embodiment of the present invention.

In the composition of the present invention, the content of the compound represented by the general formula (L-5) is required to be appropriately adjusted depending on the required performances such as solubility at low temperature, transition temperature, electrical reliability, birefringence, process suitability, dropping marks, burn-in, dielectric anisotropy and the like.

The lower limit of the preferable content of the compound represented by the formula (L-5) is 1%, 2%, 3%, 5%, 7%, 10%, 14%, 16%, 20%, 23%, 26%, 30%, 35%, 40% with respect to the total amount of the composition of the present invention. The upper limit of the preferable content of the compound represented by the formula (L-5) is 50%, 40%, 35%, 30%, 20%, 15%, 10%, 5% with respect to the total amount of the composition of the present invention.

The compound represented by the general formula (L-5) is preferably a compound represented by the formula (L-5.1) or the formula (L-5.2), and particularly preferably a compound represented by the formula (L-5.1).

The lower limit of the preferred content of these compounds is 1%, 2%, 3%, 5%, 7% relative to the total amount of the composition of the present invention. The upper limit of the preferable content of these compounds is 20%, 15%, 13%, 10%, 9%.

[ solution 116]

The compound represented by the general formula (L-5) is preferably a compound represented by the formula (L-5.3) or the formula (L-5.4).

[ solution 117]

The compound represented by the general formula (L-5) is preferably a compound selected from the group consisting of compounds represented by the formulae (L-5.5) to (L-5.7), and particularly preferably a compound represented by the formula (L-5.7).

[ chemical formula 118]

The compound represented by the general formula (L-6) is the following compound.

[ solution 119]

(in the formula, R^L61And R^L62Each independently represents R in the general formula (L)^L1And R^L2Same meaning as X^L61And X^L62Each independently represents a hydrogen atom or a fluorine atom. )

R^L61And R^L62Each independently preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, preferably X^L61And X^L62One of them is a fluorine atom and the other is a hydrogen atom.

The compound represented by the general formula (L-6) may be used alone, or 2 or more compounds may be used in combination. The type of the combinable compound is not particularly limited, and it is suitably used in combination according to the required properties such as solubility at low temperature, transition temperature, electrical reliability, birefringence, and the like. The kind of the compound to be used is, for example, 1 kind, 2 kinds, 3 kinds, 4 kinds, 5 kinds or more in one embodiment of the present invention.

The lower limit of the preferable content of the compound represented by the formula (L-6) is 1%, 2%, 3%, 5%, 7%, 10%, 14%, 16%, 20%, 23%, 26%, 30%, 35%, 40% with respect to the total amount of the composition of the present invention. The upper limit of the preferable content of the compound represented by the formula (L-6) is 50%, 40%, 35%, 30%, 20%, 15%, 10%, 5% with respect to the total amount of the composition of the present invention. When increasing Δ n, the content is preferably large, and when the deposition is performed at a low temperature, the content is preferably small.

The compound represented by the general formula (L-6) is preferably a compound represented by the formula (L-6.1) to the formula (L-6.9).

[ chemical formula 120]

The type of the combinable compounds is not particularly limited, and 1 to 3 of these compounds are preferably contained, and 1 to 4 are more preferably contained. Further, since the selected compound has a wide molecular weight distribution and is effective for solubility, it is preferable to select 1 compound from the compounds represented by the formula (L-6.1) or (L-6.2), 1 compound from the compounds represented by the formula (L-6.4) or (L-6.5), 1 compound from the compounds represented by the formula (L-6.6) or (L-6.7), 1 compound from the compounds represented by the formula (L-6.8) or (L-6.9), and appropriately combine them. Among them, preferred are compounds represented by the formula (L-6.1), the formula (L-6.3), the formula (L-6.4), the formula (L-6.6) and the formula (L-6.9).

Further, the compound represented by the general formula (L-6) is preferably a compound represented by, for example, formulae (L-6.10) to (L-6.17), and among them, a compound represented by formula (L-6.11) is preferable.

[ solution 121]

The compound represented by the general formula (L-7) is the following compound.

[ chemical formula 122]

(in the formula, R^L71And R^L72Each independently represents R in the general formula (L)^L1And R^L2Same meaning as A^L71And A^L72Each independently represents a group represented by the general formula (L)^L2And A^L3Same meaning, except that A^L71And A^L72Each hydrogen atom in (A) may independently be substituted by a fluorine atom, Z^L71Is represented by Z in the general formula (L)^L2Same meaning as X^L71And X^L72Each independently represents a fluorine atom or a hydrogen atom. )

In the formula, R^L71And R^L72Each independently preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, A^L71And A^L72Each independently of the others is preferably 1, 4-cyclohexylene or 1, 4-phenylene, A^L71And A^L72Each hydrogen atom in (A) may independently be substituted by a fluorine atom, Z^L71Preferably a single bond or-COO-, preferably a single bond, X^L71And X^L72Preferably a hydrogen atom.

The types of the combinable compounds are not particularly limited, and are combined according to the required properties such as solubility at low temperature, transition temperature, electrical reliability, birefringence, and the like. The types of the compounds used are, for example, 1,2,3, or 4 in one embodiment of the present invention.

In the composition of the present invention, the content of the compound represented by the general formula (L-7) is required to be appropriately adjusted depending on the required performances such as solubility at low temperature, transition temperature, electrical reliability, birefringence, process suitability, dropping marks, burn-in, dielectric anisotropy, and the like.

The lower limit of the preferable content of the compound represented by the formula (L-7) is 1%, 2%, 3%, 5%, 7%, 10%, 14%, 16%, 20% with respect to the total amount of the composition of the present invention. The upper limit of the preferable content of the compound represented by the formula (L-7) is 30%, 25%, 23%, 20%, 18%, 15%, 10%, 5% with respect to the total amount of the composition of the present invention.

In the case of an embodiment in which the composition of the present invention is desired to have a high Tni, the content of the compound represented by the formula (L-7) is preferably large, and in the case of an embodiment in which a low viscosity is desired, the content is preferably small.

Further, the compound represented by the general formula (L-7) is preferably a compound represented by the formulae (L-7.1) to (L-7.4), preferably a compound represented by the formula (L-7.2).

[ solution 123]

Further, the compound represented by the general formula (L-7) is preferably a compound represented by the formulae (L-7.11) to (L-7.13), preferably a compound represented by the formula (L-7.11).

[ solution 124]

Further, the compounds represented by the general formula (L-7) are compounds represented by the formulae (L-7.21) to (L-7.23). Preferred is a compound represented by the formula (L-7.21).

[ solution 125]

Further, the compound represented by the general formula (L-7) is preferably a compound represented by the formulae (L-7.31) to (L-7.34), preferably a compound represented by the formula (L-7.31) or/and (L-7.32).

[ solution 126]

Further, the compound represented by the general formula (L-7) is preferably a compound represented by the formulae (L-7.41) to (L-7.44), preferably a compound represented by the formula (L-7.41) or/and (L-7.42).

[ solution 127]

Further, the compounds represented by the general formula (L-7) are preferably compounds represented by the formulae (L-7.51) to (L-7.53).

[ solution 128]

The composition of the present invention preferably contains 1 or 2 or more compounds selected from the group consisting of the compounds represented by the general formulae (N-1), (N-2) and (N-3). These compounds correspond to compounds with negative dielectricity (Δ ∈ negative in sign and having an absolute value greater than 2.).

[ solution 129]

(in the formula, R^N11、R^N12、R^N21、R^N22、R^N31And R^N32Each independently represents an alkyl group having 1 to 8 carbon atoms, 1 or 2 or more-CH groups which are not adjacent to each other in the alkyl group₂-each independently may be substituted by-CH ═ CH-, -C ≡ C-, -O-, -CO-, -COO-or-OCO-,

A^N11、A^N12、A^N21、A^N22、A^N31and A^N32Each independently represents a group selected from the group consisting of:

(a)1, 4-cyclohexylene (1-CH present in the radical)₂-or non-adjacent 2 or more-CH₂-may be substituted by-O-. )、

(b)1, 4-phenylene (1-CH-or not adjacent 2 or more-CH-present in the radical may be substituted by-N-),

(c) naphthalene-2, 6-diyl, 1,2,3, 4-tetrahydronaphthalene-2, 6-diyl or decahydronaphthalene-2, 6-diyl (1-CH ═ or non-adjacent 2 or more-CH ═ present in naphthalene-2, 6-diyl or 1,2,3, 4-tetrahydronaphthalene-2, 6-diyl may be substituted by-N ═ and)

(d) A1, 4-cyclohexenylene group,

the above-mentioned group (a), group (b), group (c) and group (d) may each independently be substituted with a cyano group, a fluorine atom or a chlorine atom,

Z^N11、Z^N12、Z^N21、Z^N22、Z^N31and Z^N32Each independently represents a single bond, -CH₂CH₂-、-(CH₂)₄-、-OCH₂-、-CH₂O-、-COO-、-OCO-、-OCF₂-、-CF₂O-, -CH-N-CH-, -CH-, -CF-or-C ≡ C-,

X^N21represents a hydrogen atom or a fluorine atom,

T^N31represents-CH₂-or an oxygen atom,

n^N11、n^N12、n^N21、n^N22、n^N31and n^N32Each independently represents an integer of 0 to 3, provided that n^N11+n^N12、n^N21+n^N22And n^N31+n^N32Each independently is 1,2 or 3, in A^N11～A^N32、Z^N11～Z^N32When a plurality of the compounds exist, they may be the same or different. )

The compounds represented by the general formulae (N-1), (N-2) and (N-3) are preferably those in which. DELTA.. di-elect cons.is negative and the absolute value thereof is greater than 3.

In the general formulae (N-1), (N-2) and (N-3), R^N11、R^N12、R^N21、R^N22、R^N31And R^N32Each independently preferably an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms or an alkenyloxy group having 2 to 8 carbon atomsThe group is preferably an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms or an alkenyloxy group having 2 to 5 carbon atoms, more preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, still more preferably an alkyl group having 2 to 5 carbon atoms or an alkenyl group having 2 to 3 carbon atoms, and particularly preferably an alkenyl group having 3 carbon atoms (propenyl group).

When the ring structure to which the compound is bonded is a phenyl group (aromatic group), the compound is preferably a linear alkyl group having 1 to 5 carbon atoms, a linear alkoxy group having 1 to 4 carbon atoms, or an alkenyl group having 4 to 5 carbon atoms, and the ring structure to which the compound is bonded is a cyclohexane, pyran, or bisIn the case of a saturated ring structure such as an alkane, a linear alkyl group having 1 to 5 carbon atoms, a linear alkoxy group having 1 to 4 carbon atoms, and a linear alkenyl group having 2 to 5 carbon atoms are preferable. In order to stabilize the nematic phase, the total of carbon atoms and oxygen atoms when present is preferably 5 or less, and is preferably linear.

The alkenyl group is preferably selected from groups represented by any one of the formulae (R1) to (R5). (Black dots in each formula represent carbon atoms in the ring structure.)

[ solution 130]

A^N11、A^N12、A^N21、A^N22、A^N31And A^N32Each independently is preferably aromatic when an increase in Δ n is required, is preferably aliphatic for improving the response speed, and preferably represents trans-1, 4-cyclohexylene, 1, 4-phenylene, 2-fluoro-1, 4-phenylene, 3, 5-difluoro-1, 4-phenylene, 2, 3-difluoro-1, 4-phenylene, 1, 4-cyclohexenylene, 1, 4-bicyclo [2.2.2 ] phenylene]Octylene, piperidine-1, 4-diyl, naphthalene-2, 6-diyl, decahydronaphthalene-2, 6-diyl or 1,2,3, 4-tetrahydronaphthalene-2, 6-diyl, more preferably represents the following structure,

[ solution 131]

More preferably, it represents trans-1, 4-cyclohexylene, 1, 4-cyclohexenylene or 1, 4-phenylene.

Z^N11、Z^N12、Z^N21、Z^N22、Z^N31And Z^N32Each independently preferably represents-CH₂O-、-CF₂O-、-CH₂CH₂-、-CF₂CF₂-or a single bond, more preferably-CH₂O-、-CH₂CH₂-or a single bond, particularly preferably-CH₂O-or a single bond.

X^N21Preferably a fluorine atom.

T^N31Preferably an oxygen atom.

n^N11+n^N12、n^N21+n^N22And n^N31+n^N32Preferably 1 or 2, preferably n^N11Is 1 and n^N12A combination of 0, n^N11Is 2 and n^N12A combination of 0, n^N11Is 1 and n^N12Is a combination of 1, n^N11Is 2 and n^N12Is a combination of 1, n^N21Is 1 and n^N22A combination of 0, n^N21Is 2 and n^N22A combination of 0, n^N31Is 1 and n^N32A combination of 0, n^N31Is 2 and n^N32Is a combination of 0.

The lower limit of the preferable content of the compound represented by the formula (N-1) is 1%, 10%, 20%, 30%, 40%, 50%, 55%, 60%, 65%, 70%, 75%, 80% relative to the total amount of the composition of the present invention. The upper limit of the content is preferably 95%, 85%, 75%, 65%, 55%, 45%, 35%, 25%, 20%.

The lower limit of the preferable content of the compound represented by the formula (N-2) is 1%, 10%, 20%, 30%, 40%, 50%, 55%, 60%, 65%, 70%, 75%, 80% relative to the total amount of the composition of the present invention. The upper limit of the content is preferably 95%, 85%, 75%, 65%, 55%, 45%, 35%, 25%, 20%.

The lower limit of the preferable content of the compound represented by the formula (N-3) is 1%, 10%, 20%, 30%, 40%, 50%, 55%, 60%, 65%, 70%, 75%, 80% relative to the total amount of the composition of the present invention. The upper limit of the content is preferably 95%, 85%, 75%, 65%, 55%, 45%, 35%, 25%, 20%.

When a composition having a high response speed is required by keeping the viscosity of the composition of the present invention low, the lower limit value is preferably low and the upper limit value is preferably low. Further, when the Tni of the composition of the present invention is kept high and a composition having good temperature stability is required, it is preferable that the lower limit value is low and the upper limit value is low. In order to increase the dielectric anisotropy while keeping the driving voltage low, the lower limit value is preferably high and the upper limit value is preferably high.

The compounds represented by the general formula (N-1) include compounds represented by the following general formulae (N-1a) to (N-1 g).

[ solution 132]

(in the formula, R^N11And R^N12R in the general formula (N-1)^N11And R^N12Same meaning, n^Na11Represents 0 or 1, n^Nb11Represents 1 or 2, n^Nc11Represents 0 or 1, n^Nd11Represents 1 or 2, n^Ne11Represents 1 or 2, n^Nf12Represents 1 or 2, n^Ng11Represents 1 or 2, A^Ne11Represents trans-1, 4-cyclohexylene or 1, 4-phenylene, A^Ng11Represents trans-1, 4-cyclohexylene, 1, 4-cyclohexenylene or 1, 4-phenylene and at least 1 represents 1, 4-cyclohexenylene, Z^Ne11Represents a single bond or an ethylene group, at least 1 of which represents an ethylene group, and a plurality of A's present in the molecule^Ne11、Z^Ne11And/or A^Ng11May be the same or different. )

More specifically, the compound represented by the general formula (N-1) is preferably a compound selected from the group of compounds represented by the general formulae (N-1-1) to (N-1-22).

The compound represented by the general formula (N-1-1) is the following compound.

[ solution 133]

(in the formula, R^N111And R^N112Each independently represents R in the general formula (N-1)^N11And R^N12The same meaning is used. )

R^N111Preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, preferably a propyl group, a pentyl group or a vinyl group. R^N112Preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, and preferably an ethoxy group or a butoxy group.

The compounds represented by the general formula (N-1-1) may be used alone or 2 or more compounds may be used in combination. The type of the combinable compound is not particularly limited, and it is suitably used in combination according to the required properties such as solubility at low temperature, transition temperature, electrical reliability, birefringence, and the like. The kind of the compound to be used is, for example, 1 kind, 2 kinds, 3 kinds, 4 kinds, 5 kinds or more in one embodiment of the present invention.

When importance is attached to improvement of Δ ∈, it is preferable to set the content high, and when importance is attached to solubility at low temperature, it is effective when the content is set high, and when importance is attached to T_NIIn the case of (3), the effect is good when the content is set to be low. Further, in the case of improving the dropping mark and the burn-in characteristic, it is preferable to set the range of the content to be centered.

The lower limit of the preferable content of the compound represented by the formula (N-1-1) is 5%, 10%, 13%, 15%, 17%, 20%, 23%, 25%, 27%, 30%, 33%, 35% with respect to the total amount of the composition of the present invention. The upper limit of the content is preferably 50%, 40%, 38%, 35%, 33%, 30%, 28%, 25%, 23%, 20%, 18%, 15%, 13%, 10%, 8%, 7%, 6%, 5%, 3% relative to the total amount of the composition of the present invention.

Further, the compound represented by the general formula (N-1-1) is preferably a compound selected from the group consisting of compounds represented by the formulae (N-1-1.1) to (N-1-1.25), preferably a compound represented by the formulae (N-1-1.1) to (N-1-1.4), preferably a compound represented by the formulae (N-1-1.1) and (N-1-1.3).

[ solution 134]

The compounds represented by the formulae (N-1-1.1) to (N-1-1.25) may be used alone or in combination, and the lower limit of the preferable content of these compounds alone or in combination with respect to the total amount of the composition of the present invention is 5%, 10%, 13%, 15%, 17%, 20%, 23%, 25%, 27%, 30%, 33%, 35%. The upper limit of the content is preferably 50%, 40%, 38%, 35%, 33%, 30%, 28%, 25%, 23%, 20%, 18%, 15%, 13%, 10%, 8%, 7%, 6%, 5%, 3% relative to the total amount of the composition of the present invention.

The compound represented by the general formula (N-1-2) is the following compound.

[ solution 135]

(in the formula, R^N121And R^N122Each independently represents R in the general formula (N-1)^N11And R^N12The same meaning is used. )

R^N121Preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, preferably an ethyl group, a propyl group, a butyl group or a pentyl group. R^N122Preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, preferably a methyl group, a propyl group, a methoxy group, an ethoxy group or a propoxy group.

The compounds represented by the general formula (N-1-2) may be used alone or 2 or more compounds may be used in combination. The type of the combinable compound is not particularly limited, and it is suitably used in combination according to the required properties such as solubility at low temperature, transition temperature, electrical reliability, birefringence, and the like. The kind of the compound to be used is, for example, 1 kind, 2 kinds, 3 kinds, 4 kinds, 5 kinds or more in one embodiment of the present invention.

When importance is attached to improvement of Δ ∈, it is preferable to set the content high, and when importance is attached to solubility at low temperatures, it is effective when the content is set low, and when importance is attached to T_NIIn the case of (3), the effect is good when the content is set to be high. Further, in the case of improving the dropping mark and the burn-in characteristic, it is preferable to set the range of the content to be centered.

The lower limit of the preferable content of the compound represented by the formula (N-1-2) is 5%, 7%, 10%, 13%, 15%, 17%, 20%, 23%, 25%, 27%, 30%, 33%, 35%, 37%, 40%, 42% with respect to the total amount of the composition of the present invention. The upper limit of the content is preferably 50%, 48%, 45%, 43%, 40%, 38%, 35%, 33%, 30%, 28%, 25%, 23%, 20%, 18%, 15%, 13%, 10%, 8%, 7%, 6%, 5% relative to the total amount of the composition of the present invention.

Further, the compound represented by the general formula (N-1-2) is preferably a compound selected from the group consisting of the compounds represented by the formulae (N-1-2.1) to (N-1-2.25), preferably a compound represented by the formulae (N-1-2.3) to (N-1-2.7), a compound represented by the formula (N-1-2.10), a compound represented by the formula (N-1-2.11), a compound represented by the formula (N-1-2.13) or a compound represented by the formula (N-1-2.20), preferably a compound represented by the formula (N-1-2.3) to (N-1-2.7) when an improvement in Δ ε is important, or T is important_NIThe compounds represented by the formulae (N-1-2.10), (N-1-2.11) and (N-1-2.13) are preferable for the improvement of (4), and the compounds represented by the formulae (N-1-2.20) are preferable for the improvement of the response speed.

[ solution 136]

The compounds represented by the formulae (N-1-2.1) to (N-1-2.25) may be used alone or in combination, and the lower limit of the preferable content of these compounds alone or in combination with respect to the total amount of the composition of the present invention is 5%, 10%, 13%, 15%, 17%, 20%, 23%, 25%, 27%, 30%, 33%, 35%. The upper limit of the content is preferably 50%, 40%, 38%, 35%, 33%, 30%, 28%, 25%, 23%, 20%, 18%, 15%, 13%, 10%, 8%, 7%, 6%, 5%, 3% relative to the total amount of the composition of the present invention.

The compound represented by the general formula (N-1-3) is the following compound.

[ solution 137]

(in the formula, R^N131And R^N132Each independently represents R in the general formula (N-1)^N11And R^N12The same meaning is used. )

R^N131Preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, preferably an ethyl group, a propyl group or a butyl group. R^N132Preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 3 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, preferably a 1-propenyl group, an ethoxy group, a propoxy group or a butoxy group.

The compounds represented by the general formula (N-1-3) may be used alone or 2 or more compounds may be used in combination. The type of the combinable compound is not particularly limited, and it is suitably used in combination according to the required properties such as solubility at low temperature, transition temperature, electrical reliability, birefringence, and the like. The kind of the compound to be used is, for example, 1 kind, 2 kinds, 3 kinds, 4 kinds, 5 kinds or more in one embodiment of the present invention.

When importance is attached to improvement of Δ ∈, it is preferable to set the content high, and when importance is attached to solubility at low temperature, it is effective when the content is set high, and when importance is attached to T_NIIn the case of (1), willThe effect is good when the content is set to be higher. Further, in the case of improving the dropping mark and the burn-in characteristic, it is preferable to set the range of the content to be centered.

The lower limit of the preferable content of the compound represented by the formula (N-1-3) is 5%, 10%, 13%, 15%, 17%, 20% with respect to the total amount of the composition of the present invention. The upper limit of the content is preferably 35%, 30%, 28%, 25%, 23%, 20%, 18%, 15%, 13% with respect to the total amount of the composition of the present invention.

Further, the compound represented by the general formula (N-1-3) is preferably a compound selected from the group consisting of compounds represented by the formulae (N-1-3.1) to (N-1-3.21), preferably compounds represented by the formulae (N-1-3.1) to (N-1-3.7) and (N-1-3.21), and preferably compounds represented by the formulae (N-1-3.1), (N-1-3.2), (N-1-3.3), (N-1-3.4) and (N-1-3.6).

[ 138]

The compounds represented by the formulae (N-1-3.1) to (N-1-3.4), (N-1-3.6) and (N-1-3.21) may be used alone or in combination, and preferably are a combination of 2 or 3 selected from the group consisting of the formulae (N-1-3.3), (N-1-3.4) and (N-1-3.6) and the formula (N-1-3.2). The lower limit of the preferred amounts of these compounds alone or in combination is 5%, 10%, 13%, 15%, 17%, 20% relative to the total amount of the composition of the invention. The upper limit of the content is preferably 35%, 30%, 28%, 25%, 23%, 20%, 18%, 15%, 13% with respect to the total amount of the composition of the present invention.

The compound represented by the general formula (N-1-4) is the following compound.

[ solution 139]

(in the formula, R^N141And R^N142Each independently of the other is represented by the general formula (R in N-1)^N11And R^N12The same meaning is used. )

R^N141And R^N142Each independently preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, preferably a methyl group, a propyl group, an ethoxy group or a butoxy group.

The compounds represented by the general formula (N-1-4) may be used alone or 2 or more compounds may be used in combination. The type of the combinable compound is not particularly limited, and it is suitably used in combination according to the required properties such as solubility at low temperature, transition temperature, electrical reliability, birefringence, and the like. The kind of the compound to be used is, for example, 1 kind, 2 kinds, 3 kinds, 4 kinds, 5 kinds or more in one embodiment of the present invention.

The lower limit of the preferable content of the compound represented by the formula (N-1-4) is 3%, 5%, 7%, 10%, 13%, 15%, 17%, 20% with respect to the total amount of the composition of the present invention. The upper limit of the content is preferably 35%, 30%, 28%, 25%, 23%, 20%, 18%, 15%, 13%, 11%, 10%, 8% with respect to the total amount of the composition of the present invention.

Further, the compound represented by the general formula (N-1-4) is preferably a compound selected from the group consisting of compounds represented by the formulae (N-1-4.1) to (N-1-4.24), preferably a compound represented by the formulae (N-1-4.1) to (N-1-4.4), preferably a compound represented by the formulae (N-1-4.1), (N-1-4.2) and (N-1-4.4).

[ solution 140]

The compounds represented by the formulae (N-1-4.1) to (N-1-4.24) may be used alone or in combination, and the lower limit of the content of these compounds alone or in combination is 3%, 5%, 7%, 10%, 13%, 15%, 17%, 20% based on the total amount of the composition of the present invention. The upper limit of the content is preferably 35%, 30%, 28%, 25%, 23%, 20%, 18%, 15%, 13%, 11%, 10%, 8% with respect to the total amount of the composition of the present invention.

The compound represented by the general formula (N-1-5) is the following compound.

[ solution 141]

(in the formula, R^N151And R^N152Each independently represents R in the general formula (N-1)^N11And R^N12The same meaning is used. )

R^N151And R^N152Each independently preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, preferably an ethyl group, a propyl group or a butyl group.

The compounds represented by the general formula (N-1-5) may be used alone or 2 or more compounds may be used in combination. The type of the combinable compound is not particularly limited, and it is suitably used in combination according to the required properties such as solubility at low temperature, transition temperature, electrical reliability, birefringence, and the like. The kind of the compound to be used is, for example, 1 kind, 2 kinds, 3 kinds, 4 kinds, 5 kinds or more in one embodiment of the present invention.

The lower limit of the preferable content of the compound represented by the formula (N-1-5) is 5%, 8%, 10%, 13%, 15%, 17%, 20% with respect to the total amount of the composition of the present invention. The upper limit of the content is preferably 35%, 33%, 30%, 28%, 25%, 23%, 20%, 18%, 15%, 13% with respect to the total amount of the composition of the present invention.

Further, the compound represented by the general formula (N-1-5) is preferably a compound selected from the group consisting of compounds represented by the formulae (N-1-5.1) to (N-1-5.12), and is preferably a compound represented by the formulae (N-1-5.1), (N-1-5.2) and (N-1-5.4).

[ solution 142]

The compounds represented by the formulae (N-1-5.1), (N-1-5.2) and (N-1-5.4) may be used alone or in combination, and the lower limit of the preferable content of these compounds alone or in combination is 5%, 8%, 10%, 13%, 15%, 17%, 20% with respect to the total amount of the composition of the present invention. The upper limit of the content is preferably 35%, 33%, 30%, 28%, 25%, 23%, 20%, 18%, 15%, 13% with respect to the total amount of the composition of the present invention.

The compound represented by the general formula (N-1-10) is the following compound.

[ solution 143]

(in the formula, R^N1101And R^N1102Each independently represents R in the general formula (N-1)^N11And R^N12The same meaning is used. )

R^N1101Preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, preferably an ethyl group, a propyl group, a butyl group, a vinyl group or a 1-propenyl group. R^N1102Preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, and preferably an ethoxy group, a propoxy group or a butoxy group.

The compounds represented by the general formula (N-1-10) may be used alone or 2 or more compounds may be used in combination. The type of the combinable compound is not particularly limited, and it is suitably used in combination according to the required properties such as solubility at low temperature, transition temperature, electrical reliability, birefringence, and the like. The kind of the compound to be used is, for example, 1 kind, 2 kinds, 3 kinds, 4 kinds, 5 kinds or more in one embodiment of the present invention.

The lower limit of the preferable content of the compound represented by the formula (N-1-10) is 5%, 10%, 13%, 15%, 17%, 20% with respect to the total amount of the composition of the present invention. The upper limit of the content is preferably 35%, 30%, 28%, 25%, 23%, 20%, 18%, 15%, 13% with respect to the total amount of the composition of the present invention.

Further, the compound represented by the general formula (N-1-10) is preferably a compound selected from the group consisting of compounds represented by the formulae (N-1-10.1) to (N-1-10.14), preferably a compound represented by the formulae (N-1-10.1) to (N-1-10.5), preferably a compound represented by the formulae (N-1-10.1) and (N-1-10.2).

[ solution 144]

The compounds represented by the formulae (N-1 to 10.1) and (N-1 to 10.2) may be used alone or in combination, and the lower limit of the preferred content of these compounds alone or in combination with respect to the total amount of the composition of the present invention is 5%, 10%, 13%, 15%, 17%, 20%. The upper limit of the content is preferably 35%, 30%, 28%, 25%, 23%, 20%, 18%, 15%, 13% with respect to the total amount of the composition of the present invention.

The compound represented by the general formula (N-1-11) is the following compound.

[ solution 145]

(in the formula, R^N1111And R^N1112Each independently represents R in the general formula (N-1)^N11And R^N12The same meaning is used. )

R^N1111Preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, preferably an ethyl group, a propyl group, a butyl group, a vinyl group or a 1-propenyl group. R^N1112Preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, and preferably an ethoxy group, a propoxy group or a butoxy group.

The compounds represented by the general formula (N-1-11) may be used alone or 2 or more compounds may be used in combination. The type of the combinable compound is not particularly limited, and it is suitably used in combination according to the required properties such as solubility at low temperature, transition temperature, electrical reliability, birefringence, and the like. The kind of the compound to be used is, for example, 1 kind, 2 kinds, 3 kinds, 4 kinds, 5 kinds or more in one embodiment of the present invention.

The lower limit of the preferable content of the compound represented by the formula (N-1-11) is 5%, 10%, 13%, 15%, 17%, 20% with respect to the total amount of the composition of the present invention. The upper limit of the content is preferably 35%, 30%, 28%, 25%, 23%, 20%, 18%, 15%, 13% with respect to the total amount of the composition of the present invention.

Further, the compound represented by the general formula (N-1-11) is preferably a compound selected from the group consisting of compounds represented by the formulae (N-1-11.1) to (N-1-11.14), preferably a compound represented by the formulae (N-1-11.2) and (N-1-11.4).

[ solution 146]

The compounds represented by the formulae (N-1 to 11.2) and (N-1 to 11.4) may be used alone or in combination, and the lower limit of the preferred content of these compounds alone or in combination with respect to the total amount of the composition of the present invention is 5%, 10%, 13%, 15%, 17%, 20%. The upper limit of the content is preferably 35%, 30%, 28%, 25%, 23%, 20%, 18%, 15%, 13% with respect to the total amount of the composition of the present invention.

The compound represented by the general formula (N-1-12) is the following compound.

[ solution 147]

(in the formula, R^N1121And R^N1122Each independently represents R in the general formula (N-1)^N11And R^N12The same meaning is used. )

R^N1121Preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, preferably an ethyl group, a propyl group or a butyl group. R^N1122Preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, and preferably an ethoxy group, a propoxy group or a butoxy group.

The compounds represented by the general formula (N-1-12) may be used alone or 2 or more compounds may be used in combination. The type of the combinable compound is not particularly limited, and it is suitably used in combination according to the required properties such as solubility at low temperature, transition temperature, electrical reliability, birefringence, and the like. The kind of the compound to be used is, for example, 1 kind, 2 kinds, 3 kinds, 4 kinds, 5 kinds or more in one embodiment of the present invention.

Attach importance toWhen the amount of epsilon is increased, it is preferable to set the content high, and when the solubility at low temperature is important, the effect is good when the content is set high, and when T is important_NIIn the case of (3), the effect is good when the content is set to be low. Further, in the case of improving the dropping mark and the burn-in characteristic, it is preferable to set the range of the content to be centered.

The lower limit of the preferable content of the compound represented by the formula (N-1-12) is 5%, 10%, 13%, 15%, 17%, 20% with respect to the total amount of the composition of the present invention. The upper limit of the content is preferably 35%, 30%, 28%, 25%, 23%, 20%, 18%, 15%, 13% with respect to the total amount of the composition of the present invention.

The compound represented by the general formula (N-1-13) is the following compound.

[ solution 148]

(in the formula, R^N1131And R^N1132Each independently represents R in the general formula (N-1)^N11And R^N12The same meaning is used. )

R^N1131Preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, preferably an ethyl group, a propyl group or a butyl group. R^N1132Preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, and preferably an ethoxy group, a propoxy group or a butoxy group.

The compounds represented by the general formula (N-1-13) may be used alone or 2 or more compounds may be used in combination. The type of the combinable compound is not particularly limited, and it is suitably used in combination according to the required properties such as solubility at low temperature, transition temperature, electrical reliability, birefringence, and the like. The kind of the compound to be used is, for example, 1 kind, 2 kinds, 3 kinds, 4 kinds, 5 kinds or more in one embodiment of the present invention.

When importance is attached to improvement of Δ ∈, it is preferable to set the content high, and when importance is attached to solubility at low temperatures, the content is set highWhen the setting is higher, the effect is good, and T is considered to be important_NIIn the case of (3), the effect is good when the content is set to be high. Further, in the case of improving the dropping mark and the burn-in characteristic, it is preferable to set the range of the content to be centered.

The lower limit of the preferable content of the compound represented by the formula (N-1-13) is 5%, 10%, 13%, 15%, 17%, 20% with respect to the total amount of the composition of the present invention. The upper limit of the content is preferably 35%, 30%, 28%, 25%, 23%, 20%, 18%, 15%, 13% with respect to the total amount of the composition of the present invention.

The compound represented by the general formula (N-1-14) is the following compound.

[ 149]

(in the formula, R^N1141And R^N1142Each independently represents R in the general formula (N-1)^N11And R^N12The same meaning is used. )

R^N1141Preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, preferably an ethyl group, a propyl group or a butyl group. R^N1142Preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, and preferably an ethoxy group, a propoxy group or a butoxy group.

The compounds represented by the general formula (N-1-14) may be used alone or 2 or more compounds may be used in combination. The type of the combinable compound is not particularly limited, and it is suitably used in combination according to the required properties such as solubility at low temperature, transition temperature, electrical reliability, birefringence, and the like. The kind of the compound to be used is, for example, 1 kind, 2 kinds, 3 kinds, 4 kinds, 5 kinds or more in one embodiment of the present invention.

When importance is attached to improvement of Δ ∈, it is preferable to set the content high, and when importance is attached to solubility at low temperature, it is effective when the content is set high, and when importance is attached to T_NIIn the case of (3), the effect is good when the content is set to be low. Go toIn the case of improving the dropping mark and the screen burn-in characteristic, the range of the content is preferably set to be centered.

The lower limit of the preferable content of the compound represented by the formula (N-1-14) is 5%, 10%, 13%, 15%, 17%, 20% with respect to the total amount of the composition of the present invention. The upper limit of the content is preferably 35%, 30%, 28%, 25%, 23%, 20%, 18%, 15%, 13% with respect to the total amount of the composition of the present invention.

The compound represented by the general formula (N-1-15) is the following compound.

[ solution 150]

(in the formula, R^N1151And R^N1152Each independently represents R in the general formula (N-1)^N11And R^N12The same meaning is used. )

R^N1151Preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, preferably an ethyl group, a propyl group or a butyl group. R^N1152Preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, and preferably an ethoxy group, a propoxy group or a butoxy group.

The compounds represented by the general formula (N-1-15) may be used alone or 2 or more compounds may be used in combination. The type of the combinable compound is not particularly limited, and it is suitably used in combination according to the required properties such as solubility at low temperature, transition temperature, electrical reliability, birefringence, and the like. The kind of the compound to be used is, for example, 1 kind, 2 kinds, 3 kinds, 4 kinds, 5 kinds or more in one embodiment of the present invention.

When importance is attached to improvement of Δ ∈, it is preferable to set the content high, and when importance is attached to solubility at low temperature, it is effective when the content is set high, and when importance is attached to T_NIIn the case of (3), the effect is good when the content is set to be high. Further, in the case of improving the dropping mark and the burn-in characteristic, it is preferable to set the range of the content to be centered.

The lower limit of the preferable content of the compound represented by the formula (N-1-15) is 5%, 10%, 13%, 15%, 17%, 20% with respect to the total amount of the composition of the present invention. The upper limit of the content is preferably 35%, 30%, 28%, 25%, 23%, 20%, 18%, 15%, 13% with respect to the total amount of the composition of the present invention.

The compounds represented by the general formula (N-1-16) are the following compounds.

[ solution 151]

(in the formula, R^N1161And R^N1162Each independently represents R in the general formula (N-1)^N11And R^N12The same meaning is used. )

R^N1161Preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, preferably an ethyl group, a propyl group or a butyl group. R^N1162Preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, and preferably an ethoxy group, a propoxy group or a butoxy group.

The compounds represented by the general formula (N-1-16) may be used alone or 2 or more compounds may be used in combination. The type of the combinable compound is not particularly limited, and it is suitably used in combination according to the required properties such as solubility at low temperature, transition temperature, electrical reliability, birefringence, and the like. The kind of the compound to be used is, for example, 1 kind, 2 kinds, 3 kinds, 4 kinds, 5 kinds or more in one embodiment of the present invention.

When importance is attached to improvement of Δ ∈, it is preferable to set the content high, and when importance is attached to solubility at low temperature, it is effective when the content is set high, and when importance is attached to T_NIIn the case of (3), the effect is good when the content is set to be high. Further, in the case of improving the dropping mark and the burn-in characteristic, it is preferable to set the range of the content to be centered.

The lower limit of the preferable content of the compound represented by the formula (N-1-16) is 5%, 10%, 13%, 15%, 17%, 20% with respect to the total amount of the composition of the present invention. The upper limit of the content is preferably 35%, 30%, 28%, 25%, 23%, 20%, 18%, 15%, 13% with respect to the total amount of the composition of the present invention.

The compound represented by the general formula (N-1-17) is the following compound.

[ solution 152]

(in the formula, R^N1171And R^N1172Each independently represents R in the general formula (N-1)^N11And R^N12The same meaning is used. )

R^N1171Preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, preferably an ethyl group, a propyl group or a butyl group. R^N1172Preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, and preferably an ethoxy group, a propoxy group or a butoxy group.

The compounds represented by the general formula (N-1-17) may be used alone or 2 or more compounds may be used in combination. The type of the combinable compound is not particularly limited, and it is suitably used in combination according to the required properties such as solubility at low temperature, transition temperature, electrical reliability, birefringence, and the like. The kind of the compound to be used is, for example, 1 kind, 2 kinds, 3 kinds, 4 kinds, 5 kinds or more in one embodiment of the present invention.

When importance is attached to improvement of Δ ∈, it is preferable to set the content high, and when importance is attached to solubility at low temperature, it is effective when the content is set high, and when importance is attached to T_NIIn the case of (3), the effect is good when the content is set to be high. Further, in the case of improving the dropping mark and the burn-in characteristic, it is preferable to set the range of the content to be centered.

The lower limit of the preferable content of the compound represented by the formula (N-1-17) is 5%, 10%, 13%, 15%, 17%, 20% with respect to the total amount of the composition of the present invention. The upper limit of the content is preferably 35%, 30%, 28%, 25%, 23%, 20%, 18%, 15%, 13% with respect to the total amount of the composition of the present invention.

The compounds represented by the general formula (N-1-18) are the following compounds.

[ solution 153]

(in the formula, R^N1181And R^N1182Each independently represents R in the general formula (N-1)^N11And R^N12The same meaning is used. )

R^N1181Preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, preferably a methyl group, an ethyl group, a propyl group or a butyl group. R^N1182Preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, and preferably an ethoxy group, a propoxy group or a butoxy group.

The compounds represented by the general formula (N-1-18) may be used alone or 2 or more compounds may be used in combination. The type of the combinable compound is not particularly limited, and it is suitably used in combination according to the required properties such as solubility at low temperature, transition temperature, electrical reliability, birefringence, and the like. The kind of the compound to be used is, for example, 1 kind, 2 kinds, 3 kinds, 4 kinds, 5 kinds or more in one embodiment of the present invention.

When importance is attached to improvement of Δ ∈, it is preferable to set the content high, and when importance is attached to solubility at low temperature, it is effective when the content is set high, and when importance is attached to T_NIIn the case of (3), the effect is good when the content is set to be high. Further, in the case of improving the dropping mark and the burn-in characteristic, it is preferable to set the range of the content to be centered.

The lower limit of the preferable content of the compound represented by the formula (N-1-18) is 5%, 10%, 13%, 15%, 17%, 20% with respect to the total amount of the composition of the present invention. The upper limit of the content is preferably 35%, 30%, 28%, 25%, 23%, 20%, 18%, 15%, 13% with respect to the total amount of the composition of the present invention.

Further, the compound represented by the general formula (N-1-18) is preferably a compound selected from the group consisting of the compounds represented by the formulae (N-1-18.1) to (N-1-18.5), preferably a compound represented by the formulae (N-1-18.1) to (N-1-18.3), preferably a compound represented by the formulae (N-1-18.2) and (N-1-18.3).

[ solution 154]

The compound represented by the general formula (N-1-20) is the following compound.

[ solution 155]

(in the formula, R^N1201And R^N1202Each independently represents R in the general formula (N-1)^N11And R^N12The same meaning is used. )

R^N1201And R^N1202Each independently preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, preferably an ethyl group, a propyl group or a butyl group.

The compounds represented by the general formula (N-1-20) may be used alone or 2 or more compounds may be used in combination. The type of the combinable compound is not particularly limited, and it is suitably used in combination according to the required properties such as solubility at low temperature, transition temperature, electrical reliability, birefringence, and the like. The kind of the compound to be used is, for example, 1 kind, 2 kinds, 3 kinds, 4 kinds, 5 kinds or more in one embodiment of the present invention.

When importance is attached to improvement of Δ ∈, it is preferable to set the content high, and when importance is attached to solubility at low temperature, it is effective when the content is set high, and when importance is attached to T_NIIn the case of (3), the effect is good when the content is set to be high. Further, in the case of improving the dropping mark and the burn-in characteristic, it is preferable to set the range of the content to be centered.

The lower limit of the preferable content of the compound represented by the formula (N-1-20) is 5%, 10%, 13%, 15%, 17%, 20% with respect to the total amount of the composition of the present invention. The upper limit of the content is preferably 35%, 30%, 28%, 25%, 23%, 20%, 18%, 15%, 13% with respect to the total amount of the composition of the present invention.

The compound represented by the general formula (N-1-21) is the following compound.

[ solution 156]

(in the formula, R^N1211And R^N1212Each independently represents R in the general formula (N-1)^N11And R^N12The same meaning is used. )

R^N1211And R^N1212Each independently preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, preferably an ethyl group, a propyl group or a butyl group.

The compounds represented by the general formula (N-1-21) may be used alone or 2 or more compounds may be used in combination. The type of the combinable compound is not particularly limited, and it is suitably used in combination according to the required properties such as solubility at low temperature, transition temperature, electrical reliability, birefringence, and the like. The kind of the compound to be used is, for example, 1 kind, 2 kinds, 3 kinds, 4 kinds, 5 kinds or more in one embodiment of the present invention.

When importance is attached to improvement of Δ ∈, it is preferable to set the content high, and when importance is attached to solubility at low temperature, it is effective when the content is set high, and when importance is attached to T_NIIn the case of (3), the effect is good when the content is set to be high. Further, in the case of improving the dropping mark and the burn-in characteristic, it is preferable to set the range of the content to be centered.

The lower limit of the preferable content of the compound represented by the formula (N-1-21) is 5%, 10%, 13%, 15%, 17%, 20% with respect to the total amount of the composition of the present invention. The upper limit of the content is preferably 35%, 30%, 28%, 25%, 23%, 20%, 18%, 15%, 13% with respect to the total amount of the composition of the present invention.

The compound represented by the general formula (N-1-22) is the following compound.

[ chemical formula 157]

(in the formula, R^N1221And R^N1222Each independently represents R in the general formula (N-1)^N11And R^N12The same meaning is used. )

R^N1221And R^N1222Each independently preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, preferably an ethyl group, a propyl group or a butyl group.

The compounds represented by the general formula (N-1-22) may be used alone or 2 or more compounds may be used in combination. The type of the combinable compound is not particularly limited, and it is suitably used in combination according to the required properties such as solubility at low temperature, transition temperature, electrical reliability, birefringence, and the like. The kind of the compound to be used is, for example, 1 kind, 2 kinds, 3 kinds, 4 kinds, 5 kinds or more in one embodiment of the present invention.

When importance is attached to improvement of Δ ∈, it is preferable to set the content high, and when importance is attached to solubility at low temperature, it is effective when the content is set high, and when importance is attached to T_NIIn the case of (3), the effect is good when the content is set to be high. Further, in the case of improving the dropping mark and the burn-in characteristic, it is preferable to set the range of the content to be centered.

The lower limit of the preferable content of the compound represented by the formula (N-1-21) is 1%, 5%, 10%, 13%, 15%, 17%, 20% with respect to the total amount of the composition of the present invention. The upper limit of the content is preferably 35%, 30%, 28%, 25%, 23%, 20%, 18%, 15%, 13%, 10%, 5% with respect to the total amount of the composition of the present invention.

Further, the compound represented by the general formula (N-1-22) is preferably a compound selected from the group consisting of the compounds represented by the formulae (N-1-22.1) to (N-1-22.12), preferably a compound represented by the formulae (N-1-22.1) to (N-1-22.5), and preferably a compound represented by the formulae (N-1-22.1) to (N-1-22.4).

[ solution 158]

The compound represented by the general formula (N-3) is preferably a compound selected from the group of compounds represented by the general formula (N-3-2).

[ chemical formula 159]

(in the formula, R^N321And R^N322Each independently represents R in the general formula (N-3)^N11And R^N12The same meaning is used. )

R^N321And R^N322Preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and preferably a propyl group or a pentyl group.

The compounds represented by the general formula (N-3-2) may be used alone or 2 or more compounds may be used in combination. The type of the combinable compound is not particularly limited, and it is suitably used in combination according to the required properties such as solubility at low temperature, transition temperature, electrical reliability, birefringence, and the like. The kind of the compound to be used is, for example, 1 kind, 2 kinds, 3 kinds, 4 kinds, 5 kinds or more in one embodiment of the present invention.

When importance is attached to improvement of Δ ∈, it is preferable to set the content high, and when importance is attached to solubility at low temperature, it is effective when the content is set high, and when importance is attached to T_NIIn the case of (3), the effect is good when the content is set to be high. Further, in the case of improving the dropping mark and the burn-in characteristic, it is preferable to set the range of the content to be centered.

The lower limit of the preferable content of the compound represented by the formula (N-3-2) is 3%, 5%, 10%, 13%, 15%, 17%, 20%, 23%, 25%, 27%, 30%, 33%, 35% with respect to the total amount of the composition of the present invention. The upper limit of the content is preferably 50%, 40%, 38%, 35%, 33%, 30%, 28%, 25%, 23%, 20%, 18%, 15%, 13%, 10%, 8%, 7%, 6%, 5% relative to the total amount of the composition of the present invention.

Further, the compound represented by the general formula (N-3-2) is preferably a compound selected from the group of compounds represented by the formulae (N-3-2.1) to (N-3-2.3).

[ solution 160]

The composition of the present invention preferably contains 1 or 2 or more compounds represented by the general formula (J). These compounds correspond to compounds with positive dielectric properties (. DELTA.. di-elect cons.greater than 2.).

[ solution 161]

(in the formula, R^J1Represents an alkyl group having 1 to 8 carbon atoms, 1 or 2 or more-CH groups which are not adjacent to each other in the alkyl group₂-each independently may be substituted by-CH ═ CH-, -C ≡ C-, -O-, -CO-, -COO-or-OCO-,

n^J1represents 0, 1,2,3 or 4,

A^J1、A^J2and A^J3Each independently represents a group selected from the group consisting of:

(a)1, 4-cyclohexylene (1-CH present in the radical)₂-or non-adjacent 2 or more-CH₂-may be substituted by-O-. )

(b)1, 4-phenylene (1-CH-or nonadjacent 2 or more-CH-present in the radical may be substituted by-N.) and

The above-mentioned group (a), group (b) and group (c) may each independently be substituted with a cyano group, a fluorine atom, a chlorine atom, a methyl group, a trifluoromethyl group or a trifluoromethoxy group,

Z^J1and Z^J2Each independently represents a single bond, -CH₂CH₂-、-(CH₂)₄-、-OCH₂-、-CH₂O-、-OCF₂-、-CF₂O-, -COO-, -OCO-or-C ≡ C-,

at n^J1Is 2,3 or 4 and A^J2When there are plural, they may be the same or different, and n is^J1Is 2,3 or 4 and Z^J1In the case where there are plural, they may be the same or different,

X^J1represents a hydrogen atom, a fluorine atom, a chlorine atom, a cyano group, a trifluoromethyl group, a fluoromethoxy group, a difluoromethoxy group, a trifluoromethoxy group or a2, 2, 2-trifluoroethyl group. )

In the general formula (J), R^J1Preferably an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms or an alkenyloxy group having 2 to 8 carbon atoms, preferably an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms or an alkenyloxy group having 2 to 5 carbon atoms, more preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, still more preferably an alkyl group having 2 to 5 carbon atoms or an alkenyl group having 2 to 3 carbon atoms, and particularly preferably an alkenyl group having 3 carbon atoms (propenyl group).

In case reliability is important, R^J1The alkyl group is preferable, and the alkenyl group is preferable when importance is attached to reduction in viscosity.

When the ring structure to which the compound is bonded is a phenyl group (aromatic group), the compound is preferably a linear alkyl group having 1 to 5 carbon atoms, a linear alkoxy group having 1 to 4 carbon atoms, or an alkenyl group having 4 to 5 carbon atoms, and the ring structure to which the compound is bonded is a cyclohexane, pyran, or bisIn the case of saturated ring structures such as alkanesThe alkyl group preferably includes a linear alkyl group having 1 to 5 carbon atoms, a linear alkoxy group having 1 to 4 carbon atoms, and a linear alkenyl group having 2 to 5 carbon atoms. In order to stabilize the nematic phase, the total of carbon atoms and oxygen atoms when present is preferably 5 or less, and is preferably linear.

The alkenyl group is preferably selected from groups represented by any one of the formulae (R1) to (R5). (Black dots in each formula represent carbon atoms in the ring structure to which the alkenyl group is bonded.)

[ chemical 162]

A^J1、A^J2And A^J3Each independently is preferably aromatic when an increase in Δ n is required, is preferably aliphatic for improving the response speed, and preferably represents trans-1, 4-cyclohexylene, 1, 4-phenylene, 1, 4-cyclohexenylene, or 1, 4-bicyclo [2.2.2]Octylene, piperidine-1, 4-diyl, naphthalene-2, 6-diyl, decahydronaphthalene-2, 6-diyl or 1,2,3, 4-tetrahydronaphthalene-2, 6-diyl, which may be substituted with a fluorine atom, more preferably represents the following structure,

[ chemical 163]

More preferably, the following structure is shown.

[ 164]

Z^J1And Z^J2Each independently preferably represents-CH₂O-、-OCH₂-、-CF₂O-、-CH₂CH₂-、-CF₂CF₂-or a single bond, more preferably-OCH₂-、-CF₂O-、-CH₂CH₂-or a single bond, particularly preferably-OCH₂-、-CF₂O-Or a single bond.

X^J1Preferably a fluorine atom or a trifluoromethoxy group, preferably a fluorine atom.

n^J1Preferably 0, 1,2 or 3, preferably 0, 1 or 2, and preferably 0 or 1 when emphasis is placed on improvement of Δ ∈, and importance is placed on T_NIIn the case of (2), it is preferably 1 or 2.

The type of the combinable compound is not particularly limited, and it is used in combination according to desired properties such as solubility at low temperature, transition temperature, electrical reliability, birefringence, and the like. The types of the compounds used are, for example, 1,2, or 3 in one embodiment of the present invention. In other embodiments of the present invention, the number of the cells is 4, 5, 6, 7 or more.

In the composition of the present invention, the content of the compound represented by the general formula (J) is required to be appropriately adjusted depending on required performances such as solubility at low temperature, transition temperature, electrical reliability, birefringence, process suitability, dropping marks, burn-in, dielectric anisotropy, and the like.

The lower limit of the preferable content of the compound represented by the general formula (J) is 1%, 10%, 20%, 30%, 40%, 50%, 55%, 60%, 65%, 70%, 75%, 80% with respect to the total amount of the composition of the present invention. The upper limit of the content relative to the total amount of the composition of the present invention is, for example, 95%, 85%, 75%, 65%, 55%, 45%, 35%, 25% in one embodiment of the present invention.

When a composition having a high response speed is required by keeping the viscosity of the composition of the present invention low, it is preferable to set the lower limit value and the upper limit value low. Further, in the composition of the present invention, T_NIWhen a composition having high temperature stability is required because of high holding, it is preferable to set the lower limit value and the upper limit value to low values. In order to increase the dielectric anisotropy while keeping the driving voltage low, it is preferable to set the lower limit to a high value and set the upper limit to a high value.

In case reliability is important, R^J1Preferably an alkyl group, and is preferable when importance is attached to the reduction of viscosityAnd is selected as alkenyl.

The compound represented by the general formula (J) is preferably a compound represented by the general formula (M).

The composition of the present invention preferably contains 1 or 2 or more compounds represented by the general formula (M). These compounds correspond to compounds with positive dielectric properties (. DELTA.. di-elect cons.greater than 2.).

[ solution 165]

(in the formula, R^M1Represents an alkyl group having 1 to 8 carbon atoms, 1 or 2 or more-CH groups which are not adjacent to each other in the alkyl group₂-each independently may be substituted by-CH ═ CH-, -C ≡ C-, -O-, -CO-, -COO-or-OCO-,

n^M1represents 0, 1,2,3 or 4,

A^M1and A^M2Each independently represents a group selected from the group consisting of:

(a)1, 4-cyclohexylene (1-CH present in the radical)₂-or non-adjacent 2 or more-CH₂-may be substituted by-O-or-S-. ) And

(b)1, 4-phenylene (1-CH-or non-adjacent 2 or more-CH-present in the radical may be substituted by-N-

The hydrogen atoms on the above-mentioned group (a) and group (b) may each independently be substituted by a cyano group, a fluorine atom or a chlorine atom,

Z^M1and Z^M2Each independently represents a single bond, -CH₂CH₂-、-(CH₂)₄-、-OCH₂-、-CH₂O-、-OCF₂-、-CF₂O-, -COO-, -OCO-or-C ≡ C-,

at n^M1Is 2,3 or 4 and A^M2When there are plural, they may be the same or different, and n is^M1Is 2,3 or 4 and Z^M1When a plurality of the monomers are present, they may be the same or different,

X^M1And X^M3Each independently represents a hydrogen atom, a chlorine atom or a fluorine atom,

X^M2represents a hydrogen atom, a fluorine atom, a chlorine atom, a cyano group, a trifluoromethyl group, a fluoromethoxy group, a difluoromethoxy group, a trifluoromethoxy group or a2, 2, 2-trifluoroethyl group.

In the general formula (M), R^M1Preferably an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms or an alkenyloxy group having 2 to 8 carbon atoms, preferably an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms or an alkenyloxy group having 2 to 5 carbon atoms, more preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, still more preferably an alkyl group having 2 to 5 carbon atoms or an alkenyl group having 2 to 3 carbon atoms, and particularly preferably an alkenyl group having 3 carbon atoms (propenyl group).

In case reliability is important, R^M1The alkyl group is preferable, and the alkenyl group is preferable when importance is attached to reduction in viscosity.

[ solution 166]

A^M1And A^M2Each independently is preferably aromatic when an increase in Δ n is required, is preferably aliphatic for improving the response speed, and preferably represents trans-1, 4-cyclohexylene, 1, 4-phenylene, 2-fluoro-1, 4-phenylene, 3, 5-difluoro-1, 4-phenylene, 2, 3-difluoro-1, 4-phenylene, 1, 4-cyclohexenylene, 1, 4-bicyclo [2.2.2 ] phenylene]Octylene, piperidine-1, 4-diyl, naphthalene-2, 6-diyl, decahydronaphthalene-2, 6-diyl or 1,2,3, 4-tetrahydronaphthalene-2, 6-diyl, more preferably represents the following structure,

[ 167]

More preferably, the following structure is shown.

[ solution 168]

Z^M1And Z^M2Each independently preferably represents-CH₂O-、-CF₂O-、-CH₂CH₂-、-CF₂CF₂-or a single bond, more preferably-CF₂O-、-CH₂CH₂-or a single bond, particularly preferably-CF₂O-or a single bond.

n^M1Preferably 0, 1,2 or 3, preferably 0, 1 or 2, and preferably 0 or 1 when emphasis is placed on improvement of Δ ∈, and importance is placed on T_NIIn the case of (2), it is preferably 1 or 2.

In the composition of the present invention, the content of the compound represented by the general formula (M) is required to be appropriately adjusted depending on required performances such as solubility at low temperature, transition temperature, electrical reliability, birefringence, process suitability, dropping marks, burn-in, dielectric anisotropy, and the like.

The lower limit of the preferable content of the compound represented by the formula (M) is 1%, 10%, 20%, 30%, 40%, 50%, 55%, 60%, 65%, 70%, 75%, 80% relative to the total amount of the composition of the present invention. The upper limit of the content relative to the total amount of the composition of the present invention is, for example, 95%, 85%, 75%, 65%, 55%, 45%, 35%, 25% in one embodiment of the present invention.

The liquid crystal composition of the present invention contains the compound having a structure represented by the formula (K-1) in the molecule, but other polymerizable compounds may be used in combination. By using another polymerizable compound in combination, the polymerization rate and the formation of a pretilt angle of the polymerizable compound can be further increased. Further, the pretilt angle can be sufficiently obtained, the residual amount of the polymerizable compound is small, a high Voltage Holding Ratio (VHR) can be obtained, and burn-in of the liquid crystal display element can be suppressed. The other polymerizable compound is preferably a compound represented by the following general formula (P).

[ 169]

(in the above general formula (P), R^p1Represents a hydrogen atom, a fluorine atom, a cyano group, an alkyl group having 1 to 15 carbon atoms or-Sp^p2-P^p21 or not adjacent 2 or more-CH in the alkyl group₂-each independently may be substituted by-CH- ═ CH-, -C.ident.C-, -O-, -CO-, -COO-or-OCO-, 1 or more hydrogen atoms in the alkyl group each independently may be substituted by cyano groups, fluorine atoms or chlorine atoms,

P^p1and P^p2Each independently represents formula (P)^p1-1) to formula (P)^p1-any one of the above-mentioned-9),

[ solution 170]

(in the formula, R^p11And R^p12Each independently represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms or a haloalkyl group having 1 to 5 carbon atoms, W^p11Represents a single bond, -O-, -COO-or methylene, t^p11Represents 0, 1 or 2, but R is in the molecule^p11、R^p12、W^p11And/or t^p11When a plurality of the compounds exist, they may be the same or different. )

Sp^p1And Sp^p2Each independently represents a single bond or a spacer,

Z^p1and Z^p2Each independently represents a single bond, -O-, -S-, -CH₂-、-OCH₂-、-CH₂O-、-CO-、-C₂H₄-、-COO-、-OCO-、-OCOOCH₂-、-CH₂OCOO-、-OCH₂CH₂O-、-CO-NR^ZP1-、-NR^ZP1-CO-、-SCH₂-、-CH₂S-、-CH＝CR^ZP1-COO-、-CH＝CR^ZP1-OCO-、-COO-CR^ZP1＝CH-、-OCO-CR^ZP1＝CH-、-COO-CR^ZP1＝CH-COO-、-COO-CR^ZP1＝CH-OCO-、-OCO-CR^ZP1＝CH-COO-、-OCO-CR^ZP1＝CH-OCO-、-(CH₂)_z-COO-、-(CH₂)₂-OCO-、-OCO-(CH₂)₂-、-(C＝O)-O-(CH₂)₂-、-CH＝CH-、-CF＝CF-、-CF＝CH-、-CH＝CF-、-CF₂-、-CF₂O-、-OCF₂-、-CF₂CH₂-、-CH₂CF₂-、-CF₂CF₂-or-C ≡ C- (wherein, z independently represents an integer of 1 to 4, and R is^ZP1Each independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, R in the molecule^ZP1When a plurality of the compounds exist, they may be the same or different. ),

A^p1、A^p2and A^p3Each independently represents a group selected from the group consisting of:

(a^p)1, 4-cyclohexylene (1-CH present in the radical)₂-or non-adjacent 2 or more-CH₂-may be substituted by-O-. )

(b^p)1, 4-phenylene (1-CH ═ present in the radical or not adjacent 2 or more-CH ═ can be substituted by-N ═ s. ) And

(c^p) Naphthalene-2, 6-diyl, 1,2,3, 4-tetrahydronaphthalene-2, 6-diyl, decahydronaphthalene-2, 6-diyl, phenanthrene-2, 7-diyl, or anthracene-2, 6-diyl (1-CH ═ or 2 or more-CH ═ which are not adjacent to each other in these groups may be substituted with — N ═ and hydrogen atoms present in these groups may be substituted with a halogen atom, an alkyl group having 1 to 8 carbon atoms, or an alkenyl group having 1 to 8 carbon atoms. )

With respect to the above group (a)^p) Group (b)^p) And a group (c)^p) Each hydrogen atom in the group may be independently substituted by a halogen atom, an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkenyl group having 1 to 8 carbon atoms, a cyano group or-Sp^p2-P^p2The substitution is carried out by the following steps,

m^p1represents 0, 1,2 or 3, and Z is in the molecule^p1、A^p2、Sp^p2And/or P^p2When a plurality of the compounds exist, they may be the same or different. ).

The polymerizable compound preferably contains 1 or 2 or more species.

In the general formula (P) related to the invention, R^p1Is preferably-Sp^p2-P^p2。

P^p1And P^p2Are each independently preferably of the formula (P)^p1-1) to formula (P)^p1-3), preferably (P)^p1-1)。

R^p11And R^p12Each independently is preferably a hydrogen atom or a methyl group.

t^p11Preferably 0 or 1.

W^p11Preferably a single bond, methylene or ethylene.

m^p1Preferably 0, 1 or 2, preferably 0 or 1.

Z^p1And Z^p2Each independently preferably being a single bond, -OCH₂-、-CH₂O-、-CO-、-C₂H₄-、-COO-、-OCO-、-COOC₂H₄-、-OCOC₂H₄-、-C₂H₄OCO-、-C₂H₄COO-、-CH＝CH-、-CF₂-、-CF₂O-、-(CH₂)₂-COO-、-(CH₂)₂-OCO-、-OCO-(CH₂)₂-、-CH＝CH-COO-、-COO-CH＝CH-、-OCOCH＝CH-、-COO-(CH₂)₂-、-OCF₂-or-C ≡ C, preferably a single bond, -OCH₂-、-CH₂O-、-C₂H₄-、-COO-、-OCO-、-COOC₂H₄-、-OCOC₂H₄-、-C₂H₄OCO-、-C₂H₄COO-、-CH＝CH-、-(CH₂)₂-COO-、-(CH₂)₂-OCO-、-OCO-(CH₂)₂-、-CH＝CH-COO-、-COO-CH＝CH-、-OCOCH＝CH-、-COO-(CH₂)₂-or-C.ident.C-, preferably only 1 present in the molecule is-OCH₂-、-CH₂O-、-C₂H₄-、-COO-、-OCO-、-COOC₂H₄-、-OCOC₂H₄-、-C₂H₄OCO-、-C₂H₄COO-、-CH＝CH-、-(CH₂)₂-COO-、-(CH₂)₂-OCO-、-OCO-(CH₂)₂-、-CH＝CH-COO-、-COO-CH＝CH-、-OCOCH＝CH-、-COO-(CH₂)₂-or-C ≡ C-, all others being single bonds, preferablySelecting only 1 present in the molecule as-OCH₂-、-CH₂O-、-C₂H₄-, -COO-or-OCO-, the others being all single bonds, preferably all single bonds.

In addition, Z present in the molecule^p1And Z^p2Only 1 of which is selected from the group consisting of-CH-COO-, -COO-CH-, - (CH)₂)₂-COO-、-(CH₂)₂-OCO-、-O-CO-(CH₂)₂-、-COO-(CH₂)₂-a linking group of the group, other being preferably a single bond.

Sp^p1And Sp^p2Each independently represents a single bond or a spacer, the spacer is preferably an alkylene group having 1 to 30 carbon atoms, the-CH group in the alkylene group₂The alkylene group may be substituted with-O-, -CO-, -COO-, -OCO-, -CH-or-C.ident.C-, and the hydrogen atom in the alkylene group may be substituted with a halogen atom, and is preferably a linear alkylene group having 1 to 10 carbon atoms or a single bond.

A^p1、A^p2And A^p3Independently of one another, preferably 1, 4-phenylene or 1, 4-cyclohexylene, preferably 1, 4-phenylene. In order to improve the compatibility with the liquid crystal compound, the 1, 4-phenylene group is preferably substituted with 1 fluorine atom, 1 methyl group or 1 methoxy group.

The total content of the compounds represented by the general formula (P) is preferably 0.05 to 10%, preferably 0.1 to 8%, preferably 0.1 to 5%, preferably 0.1 to 3%, preferably 0.2 to 2%, preferably 0.2 to 1.3%, preferably 0.2 to 1%, preferably 0.2 to 0.56% with respect to the composition containing the compounds represented by the general formula (P) of the present application.

The preferable lower limit of the total content of the compounds represented by the general formula (P) is 0.01%, 0.03%, 0.05%, 0.08%, 0.1%, 0.15%, 0.2%, 0.25%, 0.3% with respect to the composition containing the compounds represented by the general formula (P) of the present application.

The preferable upper limit of the total content of the compounds represented by the general formula (P) is 10%, 8%, 5%, 3%, 1.5%, 1.2%, 1%, 0.8%, 0.5% with respect to the composition containing the compounds represented by the general formula (P) of the present application.

If the content is small, the effect of adding the compound represented by the general formula (P) is difficult to be exhibited, and the liquid crystal composition has a weak orientation constraint or becomes weak with time. Therefore, the content is set in consideration of their balance.

The total content of the compound represented by the general formula (I) and the compound represented by the general formula (P) is preferably 0.05 to 10%, preferably 0.1 to 8%, preferably 0.1 to 5%, preferably 0.1 to 3%, preferably 0.2 to 2%, preferably 0.2 to 1.3%, preferably 0.2 to 1%, preferably 0.2 to 0.56% of the composition containing these compounds.

The lower limit of the total content of the compound represented by the general formula (I) and the compound represented by the general formula (P) is preferably 0.01%, 0.03%, 0.05%, 0.08%, 0.1%, 0.15%, 0.2%, 0.25%, 0.3% of a composition containing these compounds.

The preferable upper limit of the total content of the compound represented by the general formula (I) and the compound represented by the general formula (P) is 10%, 8%, 5%, 3%, 1.5%, 1.2%, 1%, 0.8%, 0.5% with respect to the composition containing these compounds.

If the content is small, the effect of adding the compound having a structure represented by the formula (K-1) and the compound represented by the general formula (P) to the molecule is hardly exhibited, and the orientation constraint force of the liquid crystal composition is weak or weakened with time, and if the content is too large, the amount remaining after curing becomes large, the curing time is long, and the reliability of the liquid crystal is deteriorated. Therefore, the content is set in consideration of their balance.

Preferred examples of the compound represented by the general formula (P) according to the present invention include polymerizable compounds represented by the following formulae (P-1-1) to (P-1-46).

[ solution 171]

[ solution 172]

[ chemical formula 173]

[ solution 174]

[ chemical 175]

(in the formula, P^p11、P^p12、Sp^p11And Sp^p12Respectively represent P in the general formula (P)^p1、P^p2、Sp^p1And Sp^p2The same meaning is used. )

Preferable examples of the compound represented by the general formula (P) according to the present invention include polymerizable compounds represented by the following formulae (P-2-1) to (P-2-14).

[ solution 176]

(in the formula, P^p21、P^p22、Sp^p21And Sp^p22Respectively represent P in the general formula (P)^p1、P^p2、Sp^p1And Sp^p2The same meaning is used. )

[ solution 177]

[ solution 178]

(in the formula, P^p31、P^p32、Sp^p31And Sp^p32Represents P in the general formula (P)^p1、P^p2、Sp^p1And Sp^p2The same meaning is used. )

[ chemical 179]

[ solution 180]

[ solution 181]

[ solution 182]

(in the formula, P^p41、P^p42、Sp^p41And Sp^p42Represents P in the general formula (P)^p1、P^p2、Sp^p1And Sp^p2The same meaning is used. In the formulaA plurality of P^p41、P^p42、Sp^p41And Sp^p42Each may be the same or different. )

When the polymerizable compound is added to the composition of the present invention, polymerization proceeds even in the absence of a polymerization initiator, but a polymerization initiator may be contained to promote polymerization. Examples of the polymerization initiator include benzoin ethers, benzophenones, acetophenones, benzil ketals, acylphosphine oxides, and the like.

The composition of the present invention may further contain a compound represented by the general formula (Q).

[ solution 183]

(in the formula, R^QRepresents a straight-chain or branched alkyl group of 1 to 22 carbon atoms, 1 or 2 or more CH in the alkyl group₂The radicals may be substituted by-O-, -CH ═ CH-, -CO-, -OCO-, -COO-, -C.ident.C-, -CF-in such a way that the oxygen atoms are not directly adjacent to one another₂O-、-OCF₂-substituted, M^QRepresents trans-1, 4-cyclohexylene, 1, 4-phenylene or a single bond. )

R^QRepresents a straight-chain or branched alkyl group of 1 to 22 carbon atoms, 1 or 2 or more CH in the alkyl group₂The radicals may be substituted by-O-, -CH ═ CH-, -CO-, -OCO-, -COO-, -C.ident.C-, -CF-in such a way that the oxygen atoms are not directly adjacent to one another₂O-、-OCF₂-substituted, preferably linear alkyl, linear alkoxy, 1 CH with 1 to 10 carbon atoms₂Linear alkyl, branched alkoxy, 1 CH substituted by-OCO-or-COO-group₂The branched alkyl group substituted with-OCO-or-COO-is more preferably a linear alkyl group having 1 to 20 carbon atoms or 1 CH₂Linear alkyl, branched alkoxy, 1 CH substituted by-OCO-or-COO-group₂Branched alkyl groups substituted with-OCO-or-COO-. M^QRepresents trans-1, 4-cyclohexylene, 1, 4-phenylene or a single bond, preferably trans-1, 4-cyclohexylene or 1, 4-phenylene.

The compounds represented by the general formula (Q) are more preferably compounds represented by the following general formulae (Q-a) to (Q-d).

[ solution 184]

In the formula, R^Q1Preferably a linear or branched alkyl group of 1 to 10 carbon atoms, R^Q2Preferably a linear or branched alkyl group of 1 to 20 carbon atoms, R^Q3Preferably a linear alkyl group, a branched alkyl group, a linear alkoxy group or a branched alkoxy group having 1 to 8 carbon atoms, L^QPreferably a linear alkylene group or a branched alkylene group having 1 to 8 carbon atoms. Among the compounds represented by the general formulae (Q-a) to (Q-d), the compounds represented by the general formulae (Q-c) and (Q-d) are more preferable.

The composition of the present invention preferably contains 1 or 2 compounds represented by the general formula (Q), more preferably 1 to 5 compounds, and the content thereof is preferably 0.001% to 1%, more preferably 0.001% to 0.1%, and particularly preferably 0.001% to 0.05%.

The liquid crystal composition of the present invention may contain, in addition to the above-mentioned compounds, a conventional nematic liquid crystal, a smectic liquid crystal, a cholesteric liquid crystal, an antioxidant, an ultraviolet absorber, a light stabilizer, an infrared absorber, or the like.

Further, as the antioxidant or light stabilizer usable in the present invention, more specifically, compounds represented by the following (III-1) to (III-40) are preferable.

[ solution 185]

[ solution 186]

[ solution 187]

[ solution 188]

[ formulation 189]

[ solution 190]

[ solution 191]

[ solution 192]

[ solution 193]

(wherein n represents an integer of 0 to 20.)

The composition of the present invention preferably contains 1 or 2 or more compounds selected from the compounds represented by the general formula (Q) and the compounds of the general formulae (III-1) to (III-40), more preferably 1 to 5, and the content thereof is preferably 0.001% to 1%, more preferably 0.001% to 0.1%, and particularly preferably 0.001% to 0.05%.

The liquid crystal composition of the present invention preferably has a dielectric anisotropy (. DELTA.. di-elect cons.) of from-2.0 to-8.0, more preferably from-2.0 to-5.0, and particularly preferably from-2.5 to-5.0 at 20 ℃.

The refractive index anisotropy (. DELTA.n) of the liquid crystal composition of the present invention at 20 ℃ is preferably 0.08 to 0.14, more preferably 0.09 to 0.13, and particularly preferably 0.09 to 0.12. Further detailed, it is preferably 0.10 to 0.13 in correspondence with a thin cell gap, and 0.08 to 0.10 in correspondence with a thick cell gap.

The viscosity (. eta.) of the liquid crystal composition of the present invention at 20 ℃ is preferably 10 to 50 mPas, preferably 10 to 40 mPas, preferably 10 to 35 mPas, preferably 10 to 30 mPas, more preferably 10 to 25 mPas, and particularly preferably 10 to 22 mPas.

The liquid crystal composition of the present invention has a rotational viscosity (. gamma.) at 20 ℃₁) Preferably from 50 to 160 mPas, preferably from 60 to 150 mPas, preferably from 60 to 140 mPas, preferably from 60 to 130 mPas, preferably from 60 to 125 mPas, more preferably from 60 to 120 mPas, more preferably from 60 to 115 mPas, more preferably from 60 to 110 mPas, and particularly preferably from 60 to 100 mPas.

Nematic phase-isotropic liquid phase transition temperature (T) of liquid crystal composition of the present invention_ni) Preferably 60 ℃ to 120 ℃, more preferably 70 ℃ to 100 ℃, and particularly preferably 70 ℃ to 85 ℃.

Preferred embodiments of the liquid crystal composition according to the present invention are preferably classified into a case where the entire liquid crystal composition exhibits positive dielectric anisotropy and a case where the entire liquid crystal composition exhibits negative dielectric anisotropy.

For example, when the liquid crystal composition according to the present invention exhibits positive dielectric anisotropy as a whole, the liquid crystal composition preferably contains a compound having a structure represented by the formula (K-1) in the molecule, 1 or 2 or more compounds selected from the group consisting of the compounds represented by the general formula (J), and the compound represented by the general formula (L).

In the entire liquid crystal composition according to the present invention, the upper limit value of the proportion of the component composed only of the compound having the structure represented by formula (K-1) in the molecule, the compound represented by general formula (J) and the compound represented by general formula (L) is preferably 100 mass%, 99 mass%, 98 mass%, 97 mass%, 96 mass%, 95 mass%, 94 mass%, 93 mass%, 92 mass%, 91 mass%, 90 mass%, 89 mass%, 88 mass%, 87 mass%, 86 mass%, 85 mass% and 84 mass%.

In the liquid crystal composition of the present invention as a whole, the lower limit value of the proportion of the component composed only of the compound having the structure represented by formula (K-1) in the molecule, the compound represented by general formula (J) and the compound represented by general formula (L) is preferably 78 mass%, 80 mass%, 81 mass%, 83 mass%, 85 mass%, 86 mass%, 87 mass%, 88 mass%, 89 mass%, 90 mass%, 91 mass%, 92 mass%, 93 mass%, 94 mass%, 95 mass%, 96 mass%, 97 mass%, 98 mass%, 99 mass%.

In the entire liquid crystal composition according to the present invention, the upper limit value of the proportion of the component composed only of the compound having the structure represented by formula (K-1), the compound represented by general formula (P), and the compound represented by general formula (L) in the molecule is preferably 100 mass%, 99 mass%, 98 mass%, 97 mass%, 96 mass%, 95 mass%, 94 mass%, 93 mass%, 92 mass%, 91 mass%, 90 mass%, 89 mass%, 88 mass%, 87 mass%, 86 mass%, 85 mass%, and 84 mass%.

In the liquid crystal composition of the present invention as a whole, the lower limit of the proportion of the component composed only of the compounds represented by the general formulae (I), (P) and (L) is preferably 78 mass%, 80 mass%, 81 mass%, 83 mass%, 85 mass%, 86 mass%, 87 mass%, 88 mass%, 89 mass%, 90 mass%, 91 mass%, 92 mass%, 93 mass%, 94 mass%, 95 mass%, 96 mass%, 97 mass%, 98 mass% or 99 mass%.

For example, when the liquid crystal composition of the present invention exhibits negative dielectric anisotropy as a whole, it preferably contains 1 or 2 or more compounds selected from the group consisting of compounds represented by the general formulae (N-1), (N-2) and (N-3) and a compound represented by the general formula (L) in addition to the compound having a structure represented by the formula (K-1) in the molecule.

In the entire liquid crystal composition according to the present invention, the upper limit of the proportion of the component composed only of the compound having the structure represented by the formula (K-1), the compound represented by the general formula (N-1), the general formula (N-2), the general formula (N-3), and the compound represented by the general formula (L) in the molecule is preferably 100 mass%, 99 mass%, 98 mass%, 97 mass%, 96 mass%, 95 mass%, 94 mass%, 93 mass%, 92 mass%, 91 mass%, 90 mass%, 89 mass%, 88 mass%, 87 mass%, 86 mass%, 85 mass%, 84 mass%.

In the liquid crystal composition of the present invention as a whole, the lower limit of the proportion of the component composed only of the compound having the structure represented by the formula (K-1), the compound represented by the general formula (N-1), the general formula (N-2), the general formula (N-3) and the compound represented by the general formula (L) in the molecule is preferably 78 mass%, 80 mass%, 81 mass%, 83 mass%, 85 mass%, 86 mass%, 87 mass%, 88 mass%, 89 mass%, 90 mass%, 91 mass%, 92 mass%, 93 mass%, 94 mass%, 95 mass%, 96 mass%, 97 mass%, 98 mass% and 99 mass%.

In the liquid crystal composition of the present invention, the upper limit of the proportion of the component composed of only the compound having the structure represented by the formula (K-1) in the molecule, the compound represented by the general formula (N-1a), the general formula (N-1b), the general formula (N-1c), the general formula (N-1d), the general formula (N-1e) and the general formula (L) is preferably 100 mass%, 99 mass%, 98 mass%, 97 mass%, 96 mass%, 95 mass%, 94 mass%, 93 mass%, 92 mass%, 91 mass%, 90 mass%, 89 mass%, 88 mass%, 87 mass%, 86 mass%, 85 mass% and 84 mass%.

In addition, the lower limit value of the proportion of the component composed of only the compound having the structure represented by the formula (K-1) in the molecule, and the compounds represented by the general formulae (N-1a), (N-1b), (N-1c), (N-1d), (N-1e) and (L) is preferably 78 mass%, 80 mass%, 81 mass%, 83 mass%, 85 mass%, 86 mass%, 87 mass%, 88 mass%, 89 mass%, 90 mass%, 91 mass%, 92 mass%, 93 mass%, 94 mass%, 95 mass%, 96 mass%, 97 mass%, 98 mass% or 99 mass% in the entire liquid crystal composition according to the present invention.

In the liquid crystal composition of the present invention, the upper limit of the proportion of the component composed of only the compound having the structure represented by the formula (K-1) in the molecule, and the compounds represented by the general formulae (N-1-4), (N-1b), (N-1c), (N-1d), (N-1e) and (L) is preferably 100 mass%, 99 mass%, 98 mass%, 97 mass%, 96 mass%, 95 mass%, 94 mass%, 93 mass%, 92 mass%, 91 mass%, 90 mass%, 89 mass%, 88 mass%, 87 mass%, 86 mass%, 85 mass% and 84 mass%.

In addition, the lower limit value of the proportion of the component composed of only the compound having the structure represented by the formula (K-1) in the molecule and the compounds represented by the general formulae (N-1-4), (N-1b), (N-1c), (N-1d), (N-1e) and (L) is preferably 78 mass%, 80 mass%, 81 mass%, 83 mass%, 85 mass%, 86 mass%, 87 mass%, 88 mass%, 89 mass%, 90 mass%, 91 mass%, 92 mass%, 93 mass%, 94 mass%, 95 mass%, 96 mass%, 97 mass%, 98 mass% or 99 mass% in the entire liquid crystal composition according to the present invention.

The upper limit of the proportion of the component composed of only the compound having the structure represented by the formula (K-1) in the molecule, the compounds represented by the general formulae (N-1a), (N-1b), (N-1c), (N-1d), (N-1e), (L-1), (L-3), (L-4), (L-5) and (L-6) in the whole liquid crystal composition according to the present invention is preferably 100 mass%, 99 mass%, 98 mass%, 97 mass%, 96 mass%, 95 mass%, 94 mass%, 93 mass%, 92 mass%, 91 mass%, 90 mass%, 89 mass%, 88 mass%, 87 mass%, 86 mass%, 85 mass%, 84 mass%, 83 mass%, 82 mass%, 81 mass%, and 80 mass%.

In addition, the lower limit value of the proportion of the component composed of only the compound having the structure represented by the formula (K-1) in the molecule, the compounds represented by the general formulae (N-1a), (N-1b), (N-1c), (N-1d), (N-1e), (L-1), (L-3), (L-4), (L-5) and (L-6) is preferably 68 mass%, 70 mass%, 71 mass%, 73 mass%, 75 mass%, 78 mass%, 80 mass%, 81 mass%, 83 mass%, 85 mass%, 86 mass%, 87 mass%, 88 mass%, 89 mass%, 90 mass%, 91 mass%, 92 mass%, or the like, 93 mass%, 94 mass%, 95 mass%, 96 mass%, 97 mass%, 98 mass%, 99 mass%.

The upper limit of the proportion of the compound having a structure represented by the formula (K-1) in the molecule, the compound represented by the general formula (N-1a), the general formula (L-1), the general formula (L-3), the general formula (L-4), the general formula (L-5) and the general formula (L-6) in the entire liquid crystal composition according to the present invention is preferably 100 mass%, 99 mass%, 98 mass%, 97 mass%, 96 mass%, 95 mass%, 94 mass%, 93 mass%, 92 mass%, 91 mass%, 90 mass%, 89 mass%, 88 mass%, 87 mass%, 86 mass%, 85 mass%, 84 mass%, 83 mass%, 82 mass%, 81 mass%, 80 mass%, 79 mass%, 78 mass%, 77 mass%, 76 mass%, 75 mass%, 74 mass%, 73 mass%, 72 mass%, 71 mass%, 70 mass%, 69 mass%, 68 mass%, 67 mass%, 66 mass%, 65 mass%, 64 mass%, 63 mass%, 62 mass%.

In addition, in the liquid crystal composition of the present invention as a whole, the lower limit value of the proportion of the component composed of only the compound having the structure represented by the formula (K-1) in the molecule, and the compounds represented by the general formulae (N-1a), (L-1), (L-3), (L-4), (L-5) and (L-6) is preferably 38 mass%, 40 mass%, 41 mass%, 43 mass%, 45 mass%, 48 mass%, 50 mass%, 61 mass%, 63 mass%, 65 mass%, 66 mass%, 67 mass%, 68 mass%, 69 mass%, 70 mass%, 72 mass%, 74 mass%, 76 mass%, 78 mass%, 80 mass%, 82 mass%, 84 mass%, 86 mass%, 88 mass%, 90 mass% and 92 mass%.

The upper limit of the proportion of the compound having a structure represented by the formula (K-1) in the molecule, the compound represented by the general formula (N-1d), the general formula (L-1), the general formula (L-3), the general formula (L-4), the general formula (L-5) and the general formula (L-6) in the entire liquid crystal composition according to the present invention is preferably 100 mass%, 99 mass%, 98 mass%, 97 mass%, 96 mass%, 95 mass%, 94 mass%, 93 mass%, 92 mass%, 91 mass%, 90 mass%, 89 mass%, 88 mass%, 87 mass%, 86 mass%, 85 mass%, 84 mass%, 83 mass%, 82 mass%, 81 mass%, 80 mass%, 79 mass%, 78 mass%, 77 mass%, 76 mass%, 75 mass%, 74 mass%, 73 mass%, 72 mass%, 71 mass%, 70 mass%, 69 mass%, 68 mass%, 67 mass%, 66 mass%, 65 mass%, 64 mass%, 63 mass%, 62 mass%.

In addition, in the liquid crystal composition of the present invention as a whole, the lower limit value of the proportion of the component composed of only the compound having the structure represented by the formula (K-1) in the molecule, and the compounds represented by the general formulae (N-1d), (L-1), (L-3), (L-4), (L-5) and (L-6) is preferably 38 mass%, 40 mass%, 41 mass%, 43 mass%, 45 mass%, 48 mass%, 50 mass%, 61 mass%, 63 mass%, 65 mass%, 66 mass%, 67 mass%, 68 mass%, 69 mass%, 70 mass%, 72 mass%, 74 mass%, 76 mass%, 78 mass%, 80 mass%, 82 mass%, 84 mass%, 86 mass%, 88 mass%, 90 mass% and 92 mass%.

The composition of the present invention preferably does not contain a compound having a structure in which oxygen atoms are bonded to each other, such as a peroxy (-CO-OO-) structure, in the molecule.

When importance is attached to the reliability and long-term stability of the composition, the content of the compound having a carbonyl group is preferably 5% or less, more preferably 3% or less, still more preferably 1% or less, and most preferably substantially none, based on the total mass of the composition.

When importance is attached to the stability after UV irradiation, the content of the compound substituted with a chlorine atom is preferably 15% or less, preferably 10% or less, preferably 8% or less, more preferably 5% or less, preferably 3% or less, and further preferably substantially not contained, with respect to the total mass of the composition.

The content of the compound having all ring structures of 6-membered rings in the molecule is preferably increased, and the content of the compound having all ring structures of 6-membered rings in the molecule is preferably 80% or more, more preferably 90% or more, further preferably 95% or more, and most preferably the composition is substantially composed of only the compound having all ring structures of 6-membered rings in the molecule, based on the total mass of the composition.

In order to suppress deterioration due to oxidation of the composition, the content of the compound having a cyclohexenylene group as a ring structure is preferably reduced, and the content of the compound having a cyclohexenylene group is preferably 10% or less, preferably 8% or less, more preferably 5% or less, preferably 3% or less, and further preferably substantially not contained, with respect to the total mass of the composition.

Emphasis is placed on viscosity improvement and T_NIIn the case of the improvement of (3), the content of the 2-methylbenzene-1, 4-diyl compound having a hydrogen atom in the molecule which may be substituted with a halogen is preferably reduced, and the content of the 2-methylbenzene-1, 4-diyl compound in the molecule is preferably 10% or less, preferably 8% or less, more preferably 5% or less, preferably 3% or less, and further preferably substantially not contained, with respect to the total mass of the composition.

The term "substantially free" in the present application means not containing substances other than substances not intentionally contained.

(liquid Crystal display element)

The liquid crystal display element using the liquid crystal composition of the present invention has a remarkable feature of high-speed response, and in addition thereto, tilt formation can sufficiently proceed, there is no unreacted polymerizable compound or little to no problem, and the Voltage Holding Ratio (VHR) is high, and therefore, there is no problem or sufficiently suppressed such as defective alignment or defective display. Further, the tilt angle and the residual amount of the polymerizable compound can be easily controlled, and therefore, the energy cost for production can be easily optimized and reduced, and therefore, the method is most suitable for improvement of production efficiency and stable mass production.

The liquid crystal display element using the liquid crystal composition of the present invention is particularly useful for a liquid crystal display element for active matrix driving, and can be used for liquid crystal display elements for PSA mode, PSVA mode, VA mode, PS-IPS mode, PS-FFS mode, IPS mode, and FFS mode.

As an example of the liquid crystal display element according to the present invention, it is preferable that: a first substrate and a second substrate disposed opposite to each other; a common electrode provided on the first substrate or the second substrate; a pixel electrode provided on the first substrate or the second substrate and having a thin film transistor; and a liquid crystal layer containing a liquid crystal composition and provided between the first substrate and the second substrate. An alignment film for controlling the alignment direction of the liquid crystal molecules may be provided on the side of the first substrate or/and the second substrate opposite to the liquid crystal layer so as to be in contact with the liquid crystal layer. As the alignment film, a vertical alignment film, a horizontal alignment film, or the like can be appropriately selected according to the driving mode of the liquid crystal display element, and a known alignment film such as a rubbing alignment film (for example, polyimide), a photo alignment film (for example, decomposed polyimide), or the like can be used. Further, a color filter may be provided on the first substrate or the second substrate as appropriate, and a color filter may be provided on the pixel electrode or the common electrode.

The 2 substrates of the liquid crystal cell used in the liquid crystal display device according to the present invention may be made of a transparent material having flexibility such as glass or plastic, or may be made of an opaque material such as silicon. The transparent substrate having the transparent electrode layer can be obtained by, for example, sputtering Indium Tin Oxide (ITO) on a transparent substrate such as a glass plate.

The color filter can be produced by, for example, a pigment dispersion method, a printing method, an electrodeposition method, a dyeing method, or the like. A method for manufacturing a color filter by a pigment dispersion method will be described as an example, in which a curable coloring composition for a color filter is applied to the transparent substrate, subjected to patterning treatment, and then cured by heating or light irradiation. This process is performed for 3 colors of red, green, and blue, respectively, so that a pixel portion for a color filter can be manufactured. In addition, a pixel electrode provided with an active element such as a TFT, a thin film diode, or a metal insulator metal resistivity element may be provided on the substrate.

Preferably, the first substrate and the second substrate are opposed to each other so that the common electrode and the pixel electrode layer are located inside.

The interval between the first substrate and the second substrate may be adjusted by the spacer. In this case, the thickness of the light control layer is preferably adjusted to 1 to 100 μm. More preferably 1.5 to 10 μm, and in the case of using a polarizing plate, the product of the refractive index anisotropy Δ n of the liquid crystal and the cell thickness d is preferably adjusted so as to maximize the contrast. In addition, in the case of having two polarizing plates, the viewing angle and the contrast can be adjusted to be good by adjusting the polarizing axes of the respective polarizing plates. Further, a retardation film for enlarging a viewing angle may also be used. Examples of the spacer include glass particles, plastic particles, alumina particles, and a photoresist material. Then, a sealant such as an epoxy thermosetting composition is screen-printed on the substrates in such a manner that a liquid crystal injection port is provided, the substrates are bonded to each other, and the sealant is thermally cured by heating.

As a method for sandwiching the liquid crystal composition between 2 substrates, a general vacuum injection method, ODF method, or the like can be used.

As a method of polymerizing the polymerizable compound contained in the liquid crystal composition of the present invention, a suitable polymerization rate is desired in order to obtain good alignment performance of the liquid crystal, and therefore, a method of polymerizing by irradiating active energy rays such as ultraviolet rays or electron rays alone or in combination or in sequence is preferable. In the case of using ultraviolet rays, either a polarized light source or an unpolarized light source may be used. In addition, in the case of polymerizing the liquid crystal composition in a state of being held between 2 substrates, at least the substrate on the irradiation surface side must have appropriate transparency to the active energy ray. Further, the following method may also be used: after polymerizing only a specific portion using a mask at the time of light irradiation, the orientation state of the unpolymerized portion is changed by changing the conditions such as an electric field, a magnetic field, or temperature, and further, the polymerization is performed by irradiation with an active energy ray. In particular, when ultraviolet exposure is performed, it is preferable to perform ultraviolet exposure while applying an alternating-current electric field to the liquid crystal composition. The applied alternating electric field is preferably alternating at a frequency of 10Hz to 10kHz, more preferably at a frequency of 60Hz to 10kHz, the voltage being selected in accordance with the desired pretilt angle of the liquid crystal display element. That is, the pretilt angle of the liquid crystal display element can be controlled by the applied voltage. In a liquid crystal display element such as a PSVA mode liquid crystal display element in which the alignment of liquid crystal molecules in the absence of an applied voltage, that is, the initial alignment of liquid crystals is substantially perpendicular to the substrates, the pretilt angle is preferably controlled to 80 degrees to 89.9 degrees from the viewpoints of alignment stability and contrast. The substantially perpendicular state includes an angle having a pretilt angle as described above, and the angle between the long axis direction of the liquid crystal molecules and the substrate is preferably 70 degrees or more, more preferably 75 degrees or more, and still more preferably 80 degrees or more.

The temperature at the time of irradiation with active energy rays such as ultraviolet rays or electron rays used for polymerizing the polymerizable compound contained in the liquid crystal composition of the present invention is not particularly limited. For example, when the liquid crystal composition of the present invention is applied to a liquid crystal display element having a substrate with an alignment film, the liquid crystal composition is preferably in a temperature range in which the liquid crystal state of the liquid crystal composition can be maintained. The polymerization is preferably carried out at a temperature close to room temperature, typically 15 to 35 ℃.

On the other hand, for example, when the liquid crystal composition of the present invention is applied to a liquid crystal display element having a substrate without an alignment film, the temperature range may be wider than the above-described temperature range when the liquid crystal composition is applied to a liquid crystal display element having a substrate with an alignment film.

As the lamp for generating ultraviolet rays, a metal halide lamp, a high pressure mercury lamp, an ultra high pressure mercury lamp, or the like can be used. Further, as the wavelength of the ultraviolet rays to be irradiated, it is preferable that the wavelength region of the irradiation is not in the liquid crystal compositionThe ultraviolet rays in the absorption wavelength range are preferably used after being cut off as necessary. The intensity of the ultraviolet ray to be irradiated is preferably 0.1mW/cm²～100W/cm²More preferably 2mW/cm²～50W/cm². The energy of the ultraviolet ray to be irradiated may be appropriately adjusted, and is preferably 10mJ/cm²To 500J/cm²More preferably 100mJ/cm²To 200J/cm². The intensity may be changed when ultraviolet rays are irradiated. The time for irradiating ultraviolet rays is suitably selected depending on the intensity of the ultraviolet rays to be irradiated, and is preferably 10 seconds to 3600 seconds, and more preferably 10 seconds to 600 seconds.

Although an example of the liquid crystal display element and the method for manufacturing the liquid crystal display element of the present invention has been described above, the present invention is not limited to the above embodiment.

For example, the liquid crystal display element of the present invention may have a part of its structure replaced with another structure that exhibits the same function, or may have an arbitrary structure added thereto. The method for manufacturing a liquid crystal display element of the present invention may have additional steps for any purpose, or may be replaced with any steps for obtaining the same operation and effect.

Examples

The present invention will be described in further detail with reference to the following examples, but the present invention is not limited to these examples. In the compositions of examples and comparative examples below, "%" means "% by mass". In the examples, the compounds are described below.

The physical property values were measured by the methods described in the institute of electronic and information technology industry standard JEITA ED-2521B, 3.2009, revised society of electronic and information technology industries, unless otherwise specified.

(side chain)

(linking group)

(Ring structure)

[ solution 194]

In the examples, the measured characteristics are as follows.

Tni: nematic phase-isotropic liquid phase transition temperature (. degree.C.)

Δ n: refractive index anisotropy at 20 DEG C

Δ ε: anisotropy of dielectric constant at 20 DEG C

γ₁: rotational tack at 20 ℃ (mPa. multidot.s)

(Synthesis of a Compound having a Structure represented by the formula (K-1) in the molecule)

(Synthesis of RM-1)

21.6g of 4-pentylphenylboronic acid, 32.0g of 4-bromo-2- (3-hydroxypropyl) phenol, 38.3g of potassium carbonate, 500mg of palladium tetratriphenylphosphine, and 128ml of ethanol were placed in a reaction vessel equipped with a stirrer, a condenser, and a thermometer, and reacted at 90 ℃ for 5 hours. After completion of the reaction, the reaction mixture was cooled, 256ml of ethyl acetate was added, and the organic layer was washed with water and saturated brine, and the solvent was distilled off and recrystallized from toluene to obtain 35.1g of the compound represented by (1).

[ solution 195]

20g of Compound (1) and 5- (bromomethyl) -2, 2-dimethyl-1, 3-di-methyl ester were charged in a reaction vessel equipped with a stirrer, a condenser and a thermometerAlk-5-yl) methanol 21g, potassium carbonate 13.9g, and N, N-dimethylformamide 150ml, and reacted at 90 ℃ for 5 hours. After the reaction is finished, cooling, and adding ethyl acetate200ml of the organic layer was washed with water and saturated brine, and the solvent was distilled off. Thereafter, the reaction mixture was subjected to dispersion washing with toluene and purification by an alumina column to obtain 24.5g of a compound represented by the formula (2).

[ solution 196]

13g of the above-mentioned compound (2), 7.5g of triethylamine and 80ml of methylene chloride were placed in a reaction vessel equipped with a stirrer, a condenser and a thermometer, and the reaction vessel was cooled to 10 ℃ or lower. Thereafter, 7.2g of methacryloyl chloride was slowly added dropwise. After completion of the dropwise addition, the reaction vessel was returned to room temperature and reacted for 3 hours. After completion of the reaction, the reaction mixture was washed with water and saturated brine, and the solvent was distilled off. Subsequently, the extract and THF160ml were added together in a reaction vessel equipped with a stirrer and a thermometer, and 16ml of 10% hydrochloric acid was slowly added dropwise. After the reaction, the reaction mixture was cooled, and the target product was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and the solvent was distilled off. Thereafter, purification was performed by means of a silica gel column to obtain 14g of the compound represented by the compound (3).

[ solution 197]

Into a reaction vessel equipped with a stirrer, a condenser and a thermometer were charged 3g of the above-mentioned compound (3), 1.10g (14.1mmol) of pyridine and 12ml of dichloromethane, and 1.50g (13.3mmol) of methanesulfonyl chloride was slowly added dropwise under a nitrogen atmosphere while keeping the temperature of the reaction vessel at 5 ℃ or lower with an ice-cold bath. After completion of the dropwise addition, the reaction vessel was returned to room temperature and reacted for 4 hours. To the reaction mixture was added 60ml of dichloromethane, which was washed with aqueous hydrochloric acid, then with water, and further with saturated brine, and the organic layer was dried over anhydrous sodium sulfate. After the solvent was distilled off, the residue was purified by a 2-fold (by weight) amount of silica gel column to obtain 1.8g of the compound represented by (RM-1).

[ chemical formula 198]

¹H-NMR (solvent: deuterated chloroform): δ: 0.89(t, 3H), 1.23-1.41(m, 5H), 1.59-1.67(m, 2H), 1.92-2.04(m, 9H), 2.62(t, 2H), 2.75(t, 2H), 3.05(s, 6H), 4.08-4.25(m, 4H), 4.38-4.47(m, 6H), 5.52-5.63(m, 2H), 6.06-6.15(m, 2H), 6.88(d, 1H), 7.21(d, 2H), 7.35-7.45(m, 4H)

(Synthesis of RM-2)

42g of 3-fluoro-4- (4-pentyl (cyclohexyl)) phenylboronic acid, 30g of 4-bromo-5-ethyl-2- (3-hydroxypropyl) phenol, 27g of potassium carbonate, 1.5g of palladium tetratriphenylphosphine, and 300ml of ethanol were charged into a reaction vessel equipped with a stirrer, a condenser, and a thermometer, and reacted at 70 ℃ for 5 hours. After completion of the reaction, the reaction mixture was cooled, 300ml of ethyl acetate was added thereto, and the organic layer was washed with water and saturated brine, and after the solvent was distilled off, the mixture was recrystallized from toluene to obtain 48g of the compound represented by (4).

[ solution 199]

30g of Compound (4) and 5- (bromomethyl) -2, 2-dimethyl-1, 3-di-methyl ester were charged into a reaction vessel equipped with a stirrer, a condenser and a thermometerAlk-5-yl) methanol 18g, potassium carbonate 21g, and N, N-dimethylformamide 150ml, and reacted at 90 ℃ for 5 hours. After completion of the reaction, the reaction mixture was cooled, 200ml of ethyl acetate was added thereto, and the organic layer was washed with water and saturated brine, and the solvent was distilled off. Thereafter, the reaction mixture was subjected to dispersion washing with toluene and purification with an alumina column to obtain 40g of a compound represented by formula (5).

[ solution 200]

16g of the above-mentioned compound (5), 7.5g of triethylamine and 80ml of methylene chloride were placed in a reaction vessel equipped with a stirrer, a condenser and a thermometer, and the reaction vessel was cooled to 10 ℃ or lower. Thereafter, 7.6g of methacryloyl chloride was slowly added dropwise. After completion of the dropwise addition, the reaction vessel was returned to room temperature and reacted for 3 hours. After completion of the reaction, the reaction mixture was washed with water and saturated brine, and the solvent was distilled off. Subsequently, the extract and THF160ml were added together in a reaction vessel equipped with a stirrer and a thermometer, and 16ml of 10% hydrochloric acid was slowly added dropwise. After the reaction, the reaction mixture was cooled, and the target product was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and the solvent was distilled off. Thereafter, purification was performed by means of a silica gel column to obtain 16g of the compound represented by the compound (6).

[ solution 201]

The same procedure as used for the synthesis of (RM-1) was used for the compound represented by (6), whereby 1.6g of the compound represented by (RM-2) was obtained.

[ solution 202]

1H-NMR (solvent: deuterated chloroform): δ: 0.88(t, 3H), 1.18-1.63(m, 16H), 1.76-1.91(m, 6H), 2.01(s, 6H), 2.63-2.75(m, 5H), 3.16(s, 6H), 3.80(s, 2H), 3.95(s, 4H), 4.00(s, 2H), 4.20(t, 2H), 5.74-6.12(m, 2H), 6.47-6.59(m, 2H), 6.91-7.03(m, 2H), 7.31-7.42(m, 3H)

(Synthesis of RM-3)

The same procedure as used in the synthesis of (4) was used for (2-ethyl-2 ' -fluoro-4 ' - (4-pentylcyclohexyl) - [1,1' -biphenyl ] -4-yl) boronic acid to obtain 25.7g of the compound represented by (7).

[ solution 203]

20g of Compound (7) and 5- (bromomethyl) -2, 2-dimethyl-1, 3-di-methyl ester were charged in a reaction vessel equipped with a stirrer, a condenser and a thermometerAlk-5-yl) methanol 12.4g, potassium carbonate 8.3g, and N, N-dimethylformamide 140ml, and reacted at 90 ℃ for 5 hours. After completion of the reaction, the reaction mixture was cooled, 210ml of ethyl acetate was added thereto, and the organic layer was washed with water and saturated brine, and the solvent was distilled off. Thereafter, the reaction mixture was subjected to dispersion washing with toluene and purification by an alumina column to obtain 22.4g of a compound represented by the formula (8).

[ 204]

13g of the above-mentioned compound (8), 5.2g of triethylamine and 65ml of methylene chloride were placed in a reaction vessel equipped with a stirrer, a condenser and a thermometer, and the reaction vessel was cooled to 10 ℃ or lower. Thereafter, 4.9g of methacryloyl chloride was slowly added dropwise. After completion of the dropwise addition, the reaction vessel was returned to room temperature and reacted for 3 hours. After completion of the reaction, the reaction mixture was washed with water and saturated brine, and the solvent was distilled off. Subsequently, the extract was added together with THF130ml in a reaction vessel equipped with a stirrer and a thermometer, and 13ml of 10% hydrochloric acid was slowly added dropwise. After the reaction, the reaction mixture was cooled, and the target product was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and the solvent was distilled off. Thereafter, purification by silica gel column was carried out to obtain 12.7g of the compound represented by the compound (9).

[ formulation 205]

The same procedure as used in the synthesis of (RM-1) was used for the compound represented by (9), whereby 2.8g of the compound represented by (RM-3) was obtained.

[ solution 206]

1H-NMR (solvent: deuterated chloroform): δ: 0.88(t, 3H), 1.18-1.63(m, 16H), 1.76-1.91(m, 6H), 2.01(s, 6H), 2.44-2.80(m, 5H), 3.05(s, 6H), 3.80(s, 2H), 3.95(s, 4H), 4.00(s, 2H), 4.22(t, 2H), 5.53-5.62(m, 2H), 6.07-6.12(m, 2H), 6.90-7.04(m, 3H), 7.13-7.25(m, 2H), 7.36-7.46(m, 4H)

(Synthesis of RM-4)

The same procedures as used in the synthesis of (1) were applied to (2-ethyl-2 ' -fluoro-4 ' - (4-pentylcyclohexyl) - [1,1' -biphenyl ] -4-yl) boronic acid and 4-bromo-3- (3-hydroxypropyl) phenol to obtain 12.1g of the compound represented by (10).

[ solution 207]

The same procedure as used in the synthesis of (2) was used for the compound represented by (10), whereby 5.4g of the compound represented by (11) was obtained.

[ solution 208]

The same procedure as used in the synthesis of (3) was used for the compound represented by (11), whereby 3.4g of the compound represented by (12) was obtained.

[ solution 209]

The same procedure as used in the synthesis of (RM-1) was used for the compound represented by (12), whereby 3.1g of the compound represented by (RM-4) was obtained.

[ solution 210]

1H-NMR (solvent: deuterated chloroform): δ: 0.88(t, 3H), 1.18-1.63(m, 16H), 1.72-1.94(m, 6H), 2.01(s, 6H), 2.63-2.74(m, 5H), 3.08(s, 6H), 3.80(s, 2H), 3.95(s, 4H), 4.01(s, 2H), 4.21(t, 2H), 5.93-6.02(m, 2H), 6.37-6.48(m, 2H), 6.93-7.15(m, 3H), 7.23-7.35(m, 2H), 7.63-7.94(m, 4H)

(Synthesis of RM-5)

30.6g of 4- (tetrahydro-2H-pyran-2-yloxy) phenylboronic acid, 25.0g of 4-bromo-2-fluorophenol, 36.2g of potassium carbonate, 500mg of palladium tetratriphenylphosphine, and 128ml of ethanol were charged into a reaction vessel equipped with a stirrer, a condenser, and a thermometer, and reacted at 90 ℃ for 5 hours. After completion of the reaction, the reaction mixture was cooled, 256ml of ethyl acetate was added, and the organic layer was washed with water and saturated brine, and the solvent was distilled off to obtain 32.7g of the compound represented by (13) which was recrystallized from toluene.

[ solution 211]

23.0g of Compound (13) and 5- (bromomethyl) -2, 2-dimethyl-1, 3-di-n-ethyl were charged into a reaction vessel equipped with a stirrer, condenser and thermometerAlk-5-yl) methanol 24.8g, potassium carbonate 16.6g, and N, N-dimethylformamide 115ml, and reacted at 90 ℃ for 5 hours. After completion of the reaction, the reaction mixture was cooled, 161ml of ethyl acetate was added thereto, and the organic layer was washed with water and saturated brine, and the solvent was distilled off. Thereafter, the reaction mixture was subjected to dispersion washing with toluene and purification by an alumina column to obtain 32.1g of a compound represented by formula (14).

[ solution 212]

19.0g of the compound represented by (14), 190ml of acetone, 85ml of ethanol, and pyridine p-toluenesulfonate were charged in a reaction vessel equipped with a stirrer, a condenser, and a thermometer1.1g of the salt was reacted at 60 ℃ for 5 hours under a nitrogen atmosphere. To the reaction mixture was added 200ml of ethyl acetate, which was washed with water and further with saturated brine, and the organic layer was dried over anhydrous sodium sulfate. The solvent was distilled off, and the residue was purified by a 2-fold (by weight) amount of silica gel column to obtain 12.4g of the compound represented by (15).

[ solution 213]

12.4g of the above-mentioned compound (15), 9.0g of triethylamine and 72ml of methylene chloride were placed in a reaction vessel equipped with a stirrer, a condenser and a thermometer, and the reaction vessel was cooled to 10 ℃ or lower. Thereafter, 8.5g of methacryloyl chloride was slowly added dropwise. After completion of the dropwise addition, the reaction vessel was returned to room temperature and reacted for 3 hours. After completion of the reaction, the reaction mixture was washed with water and saturated brine, and the solvent was distilled off. Subsequently, the extract was added together with THF144ml in a reaction vessel equipped with a stirrer and a thermometer, and 15ml of 10% hydrochloric acid was slowly added dropwise. After the reaction, the reaction mixture was cooled, and the target product was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and the solvent was distilled off. Thereafter, purification by silica gel column was carried out to obtain 12.9g of the compound represented by the compound (16).

[ solution 214]

The same procedure as used in the synthesis of (RM-1) was used for the compound represented by (16), whereby 2.9g of the compound represented by (RM-5) was obtained.

[ solution 215]

¹H-NMR (solvent: deuterated chloroform): δ: 1.95(s, 3H), 2.07(s, 3H), 3.05(s, 6H), 4.14(s, 2H), 4.40(s, 2H), 4.43(s, 4H), 5.62-5.77(m, 2H), 6.12(s, 1H), 6.36(s, 1H), 7.01-7.06(m, 1H), 7.16-7.20(m, 2H), 7.25-7.32(m, 2H), 7.50-7.53(m, 2H)

(Synthesis of RM-6)

14.7g of 4- (benzoyloxy) phenylboronic acid, 17.0g of 2-benzoyloxy-4-bromophenol, 16.9g of potassium carbonate, 220mg of palladium tetratriphenylphosphine, and 88ml of ethanol were charged into a reaction vessel equipped with a stirrer, a condenser, and a thermometer, and reacted at 90 ℃ for 5 hours. After completion of the reaction, the reaction mixture was cooled, 176ml of ethyl acetate was added, and the organic layer was washed with water and saturated brine, and the solvent was distilled off to obtain 16.7g of the compound represented by (17) which was recrystallized from toluene.

[ 216]

12.0g of Compound (17) and 5- (bromomethyl) -5-ethyl-2, 2-dimethyl-1, 3-di-methyl ester were charged in a reaction vessel equipped with a stirrer, condenser and thermometer9.7g of an alkane, 6.5g of potassium carbonate and 60ml of N, N-dimethylformamide were reacted at 90 ℃ for 5 hours. After completion of the reaction, the reaction mixture was cooled, 84ml of ethyl acetate was added thereto, and the organic layer was washed with water and saturated brine, and the solvent was distilled off. Thereafter, the reaction mixture was subjected to dispersion washing with toluene and purification by an alumina column to obtain 14.4g of a compound represented by formula (18).

[ solution 217]

11.4g of the above-mentioned compound (18), 68.4ml of THF68, and 1.1g of palladium carbonate were charged into a pressure-resistant reaction vessel, and reacted for 10 hours under a hydrogen pressure of 0.5 MPa. After the reaction, the reaction mixture was cooled, and the target product was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and the solvent was distilled off. Thereafter, purification by silica gel column was carried out to obtain 6.1g of the compound represented by the formula (19).

[ solution 1]

6.1g of the above-mentioned compound (19), 4.5g of triethylamine and 30.5ml of methylene chloride were placed in a reaction vessel equipped with a stirrer, a condenser and a thermometer, and the reaction vessel was cooled to 10 ℃ or lower. Thereafter, 4.3g of methacryloyl chloride was slowly added dropwise. After completion of the dropwise addition, the reaction vessel was returned to room temperature and reacted for 3 hours. After completion of the reaction, the reaction mixture was washed with water and saturated brine, and the solvent was distilled off. Subsequently, the extract was added together with THF61ml in a reaction vessel equipped with a stirrer and a thermometer, and 6.1ml of 10% hydrochloric acid was slowly added dropwise. After the reaction, the reaction mixture was cooled, and the target product was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and the solvent was distilled off. Thereafter, purification by silica gel column was carried out to obtain 6.9g of the compound represented by the compound (20).

[ solution 219]

The same procedure as used in the synthesis of (RM-1) was used for the compound represented by (20), whereby 3.4g of the compound represented by (RM-6) was obtained.

[ solution 220]

¹H-NMR (solvent: deuterated chloroform): δ: 0.83(t, 3H), 1.69(q, 2H), 2.01(s, 6H), 3.16(s, 6H), 3.39(s, 4H), 3.80(s, 2H), 6.18(m, 2H), 6.43(m, 2H), 6.97(d, 1H), 7.10-7.20(m, 2H), 7.48-7.52(m, 2H), 7.67-7.74(m, 2H)

(Synthesis of RM-7)

By using the same method as that used for the synthesis of (RM-5), 3.1g of the compound represented by (RM-7) was obtained.

[ solution 221]

GC-MS：m/z＝626.15

¹H-NMR (solvent: deuterated chloroform): δ: 2.00(s, 3H), 2.05(s, 3H), 3.05(s, 6H), 3.39(s, 4H), 3.80(s, 2H), 3.92(s, 3H), 4.01(s, 2H), 6.18(s, 1H), 6.40(s, 1H), 6.43(s, 1H), 6.48(s, 1H), 6.86-6.94(m, 2H), 7.15(m, 2H), 7.39(m, 1H), 7.71(m, 2H)

(preparation of liquid Crystal composition and evaluation results)

(method of manufacturing liquid Crystal display element)

First, a liquid crystal composition containing a polymerizable compound described later was injected by a vacuum injection method into a liquid crystal cell having a cell gap of 3.5 μm with an ITO-equipped substrate, which was coated with a polyimide alignment film that induces vertical alignment and subjected to rubbing treatment. Then, the liquid crystal cell into which the liquid crystal composition containing the polymerizable compound was injected was irradiated with ultraviolet light for 90 minutes using a fluorescent UV lamp, to obtain a liquid crystal display element. At this time, the illuminance measured under the condition of the central wavelength of 313nm was 3.0mW/cm²The fluorescent UV lamp was adjusted in the manner described.

(method of evaluating Voltage holding ratio)

The liquid crystal cell into which the liquid crystal composition containing the polymerizable compound was injected was irradiated with UV under the above irradiation conditions for 90 minutes, and the Voltage Holding Ratio (VHR) was measured under the conditions of 1V, 0.6Hz, and 60 ℃. A is represented by a value of 95% or more, B is represented by a value of less than 95% and 90% or more, C is represented by a value of less than 90% and 80% or more, and D is represented by a value of less than 80%.

(method of evaluating Tilt formation (amount of Change in pretilt))

The change in pretilt angle [ ° ] of the liquid crystal display element before and after irradiation with ultraviolet light for 200 seconds under the above irradiation conditions was measured by the following method. First, the pretilt angle of the liquid crystal display element was measured and set to the pretilt angle (initial stage). The liquid crystal display element was irradiated with ultraviolet light for 200 seconds while applying a voltage of 10V at a frequency of 100 Hz. Then, the pretilt angle was measured and set to the pretilt angle (after UV). The value obtained by subtracting the pretilt angle (after UV) from the measured pretilt angle (initial value) was defined as the pretilt angle variation amount [ ° ]. The pretilt angle is measured by using OPTIPRO manufactured by Shintec. A is a when the value of the pretilt angle variation [ ° ] is 2.0 ° or more, B is B when less than 2.0 ° and 1.5 ° or more, C is C when less than 1.5 ° and 1.0 ° or more, and D is D when less than 1.0 °.

(evaluation method of Low-temperature storage Property)

A sample having low-temperature storage stability was obtained by weighing 0.5g of the liquid crystal composition containing the polymerizable compound into a test tube, degassing for 15 minutes, and purging with nitrogen. The resulting mixture was stored in a freezer at-20 ℃ and evaluated to good quality when no precipitation occurred for 10 days, Δ when precipitation was gradual within 5 to 9 days, and x when precipitation was gradual within 5 days.

(preparation of liquid Crystal composition and evaluation results)

Base compositions (LC-001) to (LC-008) were prepared, and physical property values thereof were measured. The component ratios and physical property values of these base compositions are shown in table 1.

[ Table 1]

	LC-001	LC-002	LC-003	LC-004	LC-005	LC-006	LC-007	LC-008
									3-Cy-Cy-2	18		20	20		18.5	20
3-Cy-Cy-4	8		4	4
									3-Cy-Cy-5						6.75	7
3-Cy-Cy-V		29			23			29
									3-Cy-Cy-V1					10	10.25
3-Cy-Ph-O1			6	4			3
									3-Ph-Ph-1	13	17	12	10	9
3-Cy-Cy-Ph-1						6	7	7
									3-Cy-Cy-Ph-3							4	4
3-Cy-Ph-Ph-1		7	5	5
									3-Cy-Ph-Ph-2	6	4			5
5-Cy-Ph-Ph-2	4
									1V2-Ph-Ph-1						3.75
3-Cy-Ph5-O2						11.5
									3-Ph-Ph5-O2				12	5	12	10	10
3-Cy-Cy-Ph5-1						2.5
									3-Cy-Cy-Ph5-O1						12
3-Cy-Cy-Ph5-O2							15	15
									3-Cy-Cy-Ph5-O4							15	15
4-Cy-Cy-Ph5-O2							10	13
									3-Cy-1O-Ph5-O1	6
3-Cy-1O-Ph5-O2	7	6	9		5
									1V-Cy-1O-Ph5-O2					6
2-Cy-Cy-1O-Ph5-O2	14	12
									3-Cy-Cy-1O-Ph5-O2	3	15	10	12	12
V-Cy-Cy-1O-Ph5-O2					4
									1V-Cy-Cy-1O-Ph5-O2		5	5	5	6
2-Cy-Ph-Ph5-O2			7	10		6	5	5
									3-Cy-Ph-Ph5-O2			8	10	5	10.75	4	2
3-Cy-Ph-Ph5-O3	6
									3-Cy-Ph-Ph5-O4	7		9
4-Cy-Ph-Ph5-O3	8
									3-Ph-Ph5-Ph-2					5
2-Ph-2-Ph-Ph5-O2					5
									3-Ph-2-Ph-Ph5-O2		5	5	8
Total (wt%)	100	100	100	100	100	100	100	100
									Tni[℃]	73.8	74.4	76.7	76.2	72.8	74.7	111.2	110.2
Δn	0.111	0.112	0.118	0.128	0.114	0.103	0.098	0.098
									Δε	-3.2	-2.8	-3.3	-3.4	-3.3	-3.1	-3.1	-3.1
γ¹[mPa·s]	125	105	132	134	104	99	154	135

These base compositions (LC-001) to (LC-008) were mixed with compounds represented by the following formulae (RM-1) to (RM-7) and formulae (RM-11) to (RM-12) to prepare liquid crystal compositions.

[ solution 222]

[ solution 223]

[ 224]

(examples 1 to 23)

A polymerizable compound-containing liquid crystal composition was prepared by adding 0.4 part by mass of the formula (RM-1) and 0.3 part by mass of the formula (RM-12) to 100 parts by mass of the base composition LC-001, and the voltage holding ratio, the pretilt angle variation amount, and the low-temperature storage property were evaluated as in example 1. Examples 2 to 23 were carried out in the same manner. The results are shown in table 2 below.

Comparative examples 1 to 9

A liquid crystal composition containing a polymerizable compound was prepared by adding 0.3 part by mass of the formula (RM-11) as a polymerizable compound to 100 parts by mass of the base composition LC-001, and the voltage holding ratio, the pretilt angle change amount, and the low-temperature storage property were evaluated to obtain comparative example 1. Comparative examples 2 to 9 were prepared in the same manner. The results are shown in table 2 below.

[ Table 2]

Examples 1 to 23 confirmed that the voltage holding ratio was sufficiently high, the pretilt angle variation was large, and the low-temperature storage property was also sufficient. From the above results, it was confirmed that the embodiments solve the problems of the present invention.

In contrast, comparative example 1 has a lower voltage holding ratio and a smaller pretilt angle variation than example 1 using the same base liquid crystal (LC-001). This is considered to be because comparative example 1 does not contain the polar compound of the present invention, and thus the voltage holding ratio is lowered by the influence of the polar impurities present in the liquid crystal cell, and the polymerizable compound of the second component is less likely to locally concentrate on the substrate surface than the polar compound of the present invention, and as a result, polymerization becomes insufficient, and the tilt formability is lowered.

In comparative example 2, the voltage holding ratio and the pretilt angle variation were significantly deteriorated as compared with example 2 using the same base liquid crystal (LC-002). This is considered to be because comparative example 2 is a base liquid crystal (LC-002) which tends to easily generate polar impurities, and therefore, the voltage holding ratio is lowered by the influence of the polar impurities present in the liquid crystal cell, and the polymerizable compound of the second component is less likely to be locally concentrated on the substrate surface than the polar compound of the present invention, and as a result, polymerization becomes insufficient, and the tilt formability is lowered.

From the above results, it was confirmed that these comparative examples could not solve the problems of the present invention.

It was further confirmed that the liquid crystal compositions of comparative examples 3 to 9 also had insufficient voltage holding ratio and inadequate pretilt angle variation, and the problem of the present invention could not be solved.

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