Liquid crystalline compound having dibenzothiophene ring, liquid crystal composition, and liquid crystal display element

文档序号：1122348 发布日期：2020-10-02 浏览：38次中文

阅读说明：本技术 具有二苯并噻吩环的液晶性化合物、液晶组合物及液晶显示元件 (Liquid crystalline compound having dibenzothiophene ring, liquid crystal composition, and liquid crystal display element ) 是由奥村一雄木村敬二于 2020-03-24 设计创作，主要内容包括：本发明的问题在于提供一种具有二苯并噻吩环的液晶性化合物、含有所述化合物的液晶组合物、包含所述组合物的液晶显示元件,所述液晶性化合物充分满足对热或光的稳定性高、透明点高(或上限温度高)、液晶相的下限温度低、粘度小、光学各向异性适当、介电各向异性为负且大、弹性常数适当、与其他液晶性化合物的相容性良好等物性的至少一种。本发明的手段为式(1)所表示的化合物、含有所述化合物的液晶组合物等。<Image he="168" wi="700" file="DDA0002423418150000011.GIF" imgContent="drawing" imgFormat="GIF" orientation="portrait" inline="no"></Image>此处,R1及R2为碳数1至16的烷基等；A1及A2为1,4-亚环己基、1,4-亚苯基、2,3-二氟-1,4-亚苯基等；Z1及Z2为单键等；m1及n1为0、1或2；W为-S-等；X为氢或氟；Y1至Y4为氢或甲基。(The present invention addresses the problem of providing a liquid crystalline compound having a dibenzothiophene ring, which sufficiently satisfies at least one of the physical properties of high stability to heat or light, a high transparency point (or a high upper limit temperature), a low lower limit temperature of a liquid crystal phase, a low viscosity, an appropriate optical anisotropy, a negative and large dielectric anisotropy, an appropriate elastic constant, and good compatibility with other liquid crystalline compounds, a liquid crystal composition containing the compound, and a liquid crystal display element including the composition. The means of the present invention is a compound represented by the formula (1), a liquid crystal composition containing the compound, and the like. Here, R 1 And R 2 Alkyl having 1 to 16 carbon atoms, etc.; a. the 1 And A 2 1, 4-cyclohexylene, 1, 4-phenylene, 2, 3-difluoro-1, 4-phenylene, etc.; z 1 And Z 2 Is a single bond, etc.; m is 1 And n 1 Is 0,1 or 2; w is-S-, etc.; x is hydrogen or fluorine; y is 1 To Y 4 Is hydrogen or methyl.)

1. A compound represented by formula (1);

in the formula (1), the reaction mixture is,

R¹and R²Independently hydrogen, fluorine, chlorine or an alkyl group of carbon number 1 to 16, in which at least one-CH₂May be substituted by-O-, -CO-, -COO-, -OCO-, -OCOO-or-Si (CH)₃)₂-substituted, at least one-CH₂CH₂-may be substituted by-CH ═ CH-or-C ≡ C-, at least one of these groups being hydrogen which may be fluorine, chlorine, -CF₃or-C ≡ N substitution;

A¹and A²Independently 1, 2-cyclopropylene, 1, 3-cyclobutylene, 1, 3-cyclopentylene, 1, 4-cyclohexylene, 1, 4-cyclohexenylene, 1, 4-cycloheptylene, 1, 5-cyclooctylene, tetrahydropyran-2, 5-diyl, 1, 3-dioxane-2, 5-diyl, 1, 4-phenylene, pyridine-2, 5-diyl, pyrimidine-2, 5-diyl, decahydronaphthalene-2, 6-diyl, tetrahydronaphthalene-2, 6-diyl or naphthalene-2, 6-diyl, in which at least one hydrogen on the aromatic ring may be fluorine, chlorine, -CF₃、-CHF₂、-CH₂F、-OCF₃、-OCHF₂、-OCH₂F or-C ≡ N substitution;

Z¹and Z²Independently a single bond or alkylene of 1 to 6 carbon atoms, a-CH₂-may be substituted by-O-, -CO-, -COO-or-OCO-, one-CH₂CH₂-may be substituted by-CH ═ CH-or-C ≡ C-, at least one of these divalent radicals may be substituted by fluorine or chlorine;

m¹and n¹Independently 0,1 or 2, m¹And n¹The sum of (1) is 3 or less;

w is-CH₂-、-CF₂-, -CO-, -O-, -S-or-SO₂-；

X is hydrogen or fluorine;

Y¹、Y²、Y³and Y⁴Independently is hydrogen or methyl, Y¹、Y²、Y³And Y⁴At least one of (a) is methyl; when W is-O-, Y¹、Y²、Y³And Y⁴At least two of (a) are methyl groups.

2. The compound according to claim 1, wherein in the formula (1) according to claim 1,

R¹and R²Independently hydrogen or C1-14 alkyl, one or two-CH in the alkyl₂-may be substituted by-O-and-CH₂CH₂-may be substituted by-CH ═ CH-, where at least one hydrogen may be substituted by fluorine;

A¹and A²Independently 1, 4-cyclohexylene, 1, 4-cyclohexenylene, tetrahydropyran-2, 5-diyl, 1, 3-dioxane-2, 5-diyl, 1, 4-phenylene, pyridine-2, 5-diyl, pyrimidine-2, 5-diyl, or naphthalene-2, 6-diyl, wherein at least one hydrogen on the aromatic ring may be substituted with fluorine;

Z¹and Z²Independently a single bond, -COO-, -OCO-, -CH₂O-、-OCH₂-、-CF₂O-、-OCF₂-、-CH₂CH₂-、-CF₂CF₂-、-CH＝CH-、-CF＝CF-、-C≡C-、-(CH₂)₄-or-CH₂CH＝CHCH₂-；

m¹And n¹Independently 0,1 or 2, m¹And n¹The sum of (1) is 3 or less;

w is-CH₂-, -CO-, -S-or-SO₂-；

X is hydrogen or fluorine;

Y¹、Y²、Y³and Y⁴Independently is hydrogen or methyl, Y¹、Y²、Y³And Y⁴At least one of (a) is methyl.

3. The compound according to claim 1 or 2, wherein in the formula (1) according to claim 1,

R¹and R²Independently hydrogen or alkyl of carbon number 1 to 14,in the alkyl group, one or two-CH₂-may be substituted by-O-and-CH₂CH₂-may be substituted by-CH ═ CH-, where at least one hydrogen may be substituted by fluorine;

Z¹and Z²Independently a single bond, -COO-, -OCO-, -CH₂O-、-OCH₂-、-CF₂O-、-OCF₂-、-CH₂CH₂-、-CF₂CF₂-、-CH＝CH-、-CF＝CF-、-C≡C-、-(CH₂)₄-or-CH₂CH＝CHCH₂-；

m¹And n¹Independently 0,1 or 2, m¹And n¹The sum of (1) is 3 or less;

w is-S-;

x is fluorine;

Y¹、Y²、Y³and Y⁴Independently is hydrogen or methyl, Y¹、Y²、Y³And Y⁴At least one of (a) is methyl.

4. The compound according to claim 1 or 2, wherein in the formula (1) according to claim 1,

R¹and R²Independently an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, or an alkenyl group having 2 to 8 carbon atoms;

A¹and A²Independently 1, 4-cyclohexylene, 1, 4-cyclohexenylene, tetrahydropyran-2, 5-diyl, 1, 3-dioxane-2, 5-diyl, 1, 4-phenylene in which one or two hydrogens are substituted by fluorine, pyridine-2, 5-diyl or pyrimidine-2, 5-diyl;

Z¹and Z²Independently a single bond, -COO-, -OCO-, -CH₂O-、-OCH₂-、-CF₂O-、-OCF₂-、-CH₂CH₂-, -CH-, -C.ident.C-or- (CH)₂)₄-；

m¹And n¹Independently 0,1 or 2, m¹And n¹The sum of (1) is 3 or less;

w is-CH₂-, -CO-or-S-;

x is hydrogen or fluorine;

Y¹、Y²、Y³and Y⁴Independently is hydrogen or methyl, Y¹、Y²、Y³And Y⁴At least one of (a) is methyl.

5. The compound according to claim 1 or 2, wherein in the formula (1) according to claim 1,

R¹and R²Independently an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, or an alkenyl group having 2 to 8 carbon atoms;

Z¹and Z²Independently a single bond, -COO-, -OCO-, -CH₂O-、-OCH₂-、-CF₂O-、-OCF₂-、-CH₂CH₂-, -CH-, -C.ident.C-or- (CH)₂)₄-；

m¹And n¹Independently 0,1 or 2, m¹And n¹The sum of (1) is 3 or less;

w is-S-;

x is fluorine;

Y¹、Y²、Y³and Y⁴Independently is hydrogen or methyl, Y¹、Y²、Y³And Y⁴At least one of (a) is methyl.

6. The compound according to claim 1 or 2, wherein in the formula (1) according to claim 1,

R¹and R²Independently an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms;

A¹and A²Independently 1, 4-cyclohexylene, tetrahydropyran-2, 5-diyl, 1, 4-phenylene, 2-fluoro-1, 4-phenylene or 2, 3-difluoro-1, 4-phenylene;

Z¹and Z²Independently a single bond, -CH₂O-、-OCH₂-、-CH₂CH₂-or-CH ═ CH-;

m¹and n¹Independently 0,1 or 2, m¹And n¹The sum of (1) is 3 or less;

w is-S-;

x is hydrogen or fluorine;

Y¹、Y²、Y³and Y⁴Independently is hydrogen or methyl, Y¹、Y²、Y³And Y⁴At least one of (a) is methyl.

7. The compound according to claim 1 or 2, wherein in the formula (1) according to claim 1,

R¹and R²Independently an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms;

A¹and A²Independently 1, 4-cyclohexylene, tetrahydropyran-2, 5-diyl, 1, 4-phenylene, 2-fluoro-1, 4-phenylene or 2, 3-difluoro-1, 4-phenylene;

Z¹and Z²Independently a single bond, -CH₂O-、-OCH₂-、-CH₂CH₂-or-CH ═ CH-;

m¹and n¹Independently 0,1 or 2, m¹And n¹The sum of (1) is 3 or less;

w is-S-;

x is fluorine;

Y¹、Y²、Y³and Y⁴Independently is hydrogen or methyl, Y¹、Y²、Y³And Y⁴At least one of (a) is methyl.

8. The compound according to claim 1, which is represented by any one of formula (1a) to formula (1 i);

in the formulae (1a) to (1i), R¹And R²Independently an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms; y is¹、Y²、Y³And Y⁴Independently is hydrogen or methyl, Y¹、Y²、Y³And Y⁴At least one of (a) is methyl.

9. The compound according to claim 1, which is represented by formula (1j) or formula (1 k);

in the formula (1j) or the formula (1k), R¹And R²Independently an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms.

10. A liquid crystal composition containing at least one compound according to any one of claims 1 to 9.

11. The liquid crystal composition according to claim 10, further comprising at least one compound selected from the group consisting of compounds represented by formulae (2) to (4);

in the formulae (2) to (4),

R¹¹and R¹²Independently an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms, at least one-CH group being present in the alkyl group or the alkenyl group₂May be substituted by-O-in these radicals, toOne hydrogen at a time may be substituted with fluorine;

ring B¹Ring B²Ring B³And ring B⁴Independently 1, 4-cyclohexylene, 1, 4-phenylene, 2-fluoro-1, 4-phenylene, 2, 5-difluoro-1, 4-phenylene or pyrimidin-2, 5-diyl;

Z¹¹、Z¹²and Z¹³Independently a single bond, -COO-, -CH₂CH₂-, -CH-or-C.ident.C-.

12. The liquid crystal composition according to claim 10 or 11, further comprising at least one compound selected from the group consisting of compounds represented by formulae (5) to (11);

in the formulae (5) to (11),

R¹³、R¹⁴and R¹⁵Independently an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms, at least one-CH group being present in the alkyl group or the alkenyl group₂-may be substituted by-O-, of which groups at least one hydrogen may be substituted by fluorine, and R¹⁵Can be hydrogen or fluorine;

ring C¹Ring C²Ring C³And ring C⁴Independently 1, 4-cyclohexylene, 1, 4-cyclohexenylene, 1, 4-phenylene in which at least one hydrogen is substituted by fluorine, tetrahydropyran-2, 5-diyl or decahydronaphthalene-2, 6-diyl;

ring C⁵And ring C⁶Independently 1, 4-cyclohexylene, 1, 4-cyclohexenylene, 1, 4-phenylene, tetrahydropyran-2, 5-diyl, or decahydronaphthalene-2, 6-diyl;

Z¹⁴、Z¹⁵、Z¹⁶and Z¹⁷Independently a single bond, -COO-, -CH₂O-、-OCF₂-、-CH₂CH₂-or-OCF₂CH₂CH₂-；

L¹¹And L¹²Independently fluorine or chlorine;

S¹¹is hydrogen or methyl;

x is-CHF-or-CF₂-；

j. k, m, n, p, q, r and s are independently 0 or 1, the sum of k, m, n and p is 1 or 2, the sum of q, r and s is 0,1, 2 or 3, and t is 1,2 or 3.

13. The liquid crystal composition according to claim 10 or 11, further comprising at least one compound selected from the group consisting of compounds represented by formulae (12) to (14);

in the formulae (12) to (14),

R¹⁶is C1-10 alkyl or C2-10 alkenyl, at least one-CH in the alkyl and alkenyl₂-may be substituted by-O-, in which groups at least one hydrogen may be substituted by fluorine;

X¹¹is fluorine, chlorine, -CF₃、-CHF₂、-CH₂F、-OCF₃、-OCHF₂、-OCF₂CHF₂or-OCF₂CHFCF₃；

Ring D¹Ring D²And ring D³Independently 1, 4-cyclohexylene, 1, 4-phenylene in which at least one hydrogen is substituted by fluorine, tetrahydropyran-2, 5-diyl, 1, 3-dioxane-2, 5-diyl or pyrimidine-2, 5-diyl;

Z¹⁸、Z¹⁹and Z²⁰Independently a single bond, -COO-, -CH₂O-、-CF₂O-、-OCF₂-、-CH₂CH₂-, -CH-, -C.ident.C-or- (CH)₂)₄-；

L¹³And L¹⁴Independently hydrogen or fluorine.

14. The liquid crystal composition according to claim 10 or 11, further comprising at least one compound selected from the group consisting of compounds represented by formula (15);

in the formula (15), the reaction mixture is,

R¹⁷is C1-10 alkyl or C2-10 alkenyl, at least one-CH in the alkyl and alkenyl₂-may be substituted by-O-, in which groups at least one hydrogen may be substituted by fluorine;

X¹²is-C.ident.N or-C.ident.C-C.ident.N;

ring E¹Is 1, 4-cyclohexylene, 1, 4-phenylene in which at least one hydrogen is substituted by fluorine, tetrahydropyran-2, 5-diyl, 1, 3-dioxane-2, 5-diyl or pyrimidine-2, 5-diyl;

Z²¹is a single bond, -COO-, -CH₂O-、-CF₂O-、-OCF₂-、-CH₂CH₂-or-C ≡ C-;

L¹⁵and L¹⁶Independently hydrogen or fluorine;

i is 1,2,3 or 4.

15. A liquid crystal display element comprising the liquid crystal composition according to any one of claims 10 to 14.

Technical Field

The present invention relates to a liquid crystal compound, a liquid crystal composition, and a liquid crystal display element. More specifically, the present invention relates to a liquid crystalline compound having a dibenzothiophene ring and negative dielectric anisotropy, a liquid crystal composition containing the compound, and a liquid crystal display element including the composition.

Background

In the liquid crystal display device, the operation modes based on liquid crystal molecules are classified into Phase Change (PC), Twisted Nematic (TN), Super Twisted Nematic (STN), Electrically Controlled Birefringence (ECB), Optically Compensated Bend (OCB), in-plane switching (IPS), Vertical Alignment (VA), Fringe Field Switching (FFS), field-induced photo-reactive alignment (FPA), and the like. The driving methods of the elements are classified into Passive Matrix (PM) and Active Matrix (AM). The PM is classified into a static type (static), a multiplexing type (multiplex), etc., and the AM is classified into a Thin Film Transistor (TFT), a Metal Insulator Metal (MIM), etc.

A liquid crystal composition is encapsulated in the element. The physical properties of the composition are correlated with the characteristics of the element. Examples of the physical properties of the composition include stability to heat or light, temperature range of nematic phase, viscosity, optical anisotropy, dielectric anisotropy, specific resistance, and elastic constant. The composition is prepared by mixing a plurality of liquid crystalline compounds. The physical properties required for the compound include high stability to environments such as water, air, heat, and light, a wide temperature range of a liquid crystal phase, a small viscosity, an appropriate optical anisotropy, a large dielectric anisotropy, an appropriate elastic constant, and good compatibility with other liquid crystalline compounds. Preferred are compounds having a high upper temperature limit of the nematic phase. Preferred are compounds having a low lower limit temperature in a liquid crystal phase such as a nematic phase or a smectic phase. Compounds with a small viscosity contribute to a short response time of the element. The appropriate value of the optical anisotropy differs depending on the mode of the element. When the element is driven at a low voltage, a compound having positive or negative and large dielectric anisotropy is preferable. In the preparation of the composition, a compound having good compatibility with other liquid crystalline compounds is preferable. The element is sometimes used also at temperatures below freezing point, and therefore compounds having good compatibility at low temperatures are preferred.

Many liquid crystalline compounds have been synthesized so far. The development of new liquid crystalline compounds is continuing. The reason is that: among novel compounds, good physical properties which are not present in conventional compounds can be expected. The reason is that: sometimes the novel compounds also impart an appropriate balance of at least two physical properties to the composition.

Liquid crystalline compounds having a dibenzothiophene ring are known. Refer to patent documents 1 and 2. The compounds of the present case differ from these compounds in having a methyl-substituted dibenzothiophene ring.

[ Prior art documents ]

[ patent document ]

[ patent document 1] Japanese patent laid-open No. 2015-206042

[ patent document 2] Japanese patent laid-open No. 2016-199543

Disclosure of Invention

[ problems to be solved by the invention ]

A first problem is to provide a liquid crystalline compound that sufficiently satisfies at least one of physical properties such as high stability to heat or light, high transparency (or high upper limit temperature of a nematic phase), low lower limit temperature of a liquid crystal phase, low viscosity, appropriate optical anisotropy, negative and large dielectric anisotropy, appropriate elastic constant, and good compatibility with other liquid crystalline compounds. And to provide a compound having good compatibility compared with similar compounds. A second problem is to provide a liquid crystal composition containing the above-mentioned compound and sufficiently satisfying at least one of physical properties such as high stability to heat or light, high upper limit temperature of a nematic phase, low lower limit temperature of a nematic phase, low viscosity, appropriate optical anisotropy, negative and large dielectric anisotropy, large specific resistance, and appropriate elastic constant. The problem is to provide a liquid crystal composition having an appropriate balance between at least two of these physical properties. A third problem is to provide a liquid crystal display element which comprises the composition and has a wide temperature range in which the element can be used, a short response time, a large voltage holding ratio, a low threshold voltage, a large contrast ratio, a small flicker rate, and a long life.

[ means for solving problems ]

The present invention relates to a compound represented by formula (1), a liquid crystal composition containing the compound, a liquid crystal display element comprising the composition, and the like.

In the formula (1), the reaction mixture is,

m¹and n¹Independently 0,1 or 2, m¹And n¹The sum of (1) is 3 or less;

w is-CH₂-、-CF₂-, -CO-, -O-, -S-or-SO₂-；

X is hydrogen or fluorine;

Y¹、Y²、Y³and Y⁴Independently is hydrogen or methyl, Y¹、Y²、Y³And Y⁴At least one of (a) is methyl; when W is-O-, Y¹、Y²、Y³And Y⁴At least two of (a) are methyl groups.

[ Effect of the invention ]

A first advantage is to provide a liquid crystalline compound that sufficiently satisfies at least one of physical properties such as high stability to heat or light, a high transparency point (or a high upper limit temperature of a nematic phase), a low lower limit temperature of a liquid crystal phase, a low viscosity, an appropriate optical anisotropy, a negative and large dielectric anisotropy, an appropriate elastic constant, and good compatibility with other liquid crystalline compounds. And to provide a compound having good compatibility compared with similar compounds. A second advantage is to provide a liquid crystal composition containing the compound and sufficiently satisfying at least one of physical properties such as high stability to heat or light, high upper limit temperature of a nematic phase, low lower limit temperature of a nematic phase, low viscosity, appropriate optical anisotropy, negative and large dielectric anisotropy, large specific resistance, and appropriate elastic constant. The advantage is to provide a liquid crystal composition having an appropriate balance between at least two of these physical properties. A third advantage is to provide a liquid crystal display element which comprises the composition and has a wide temperature range in which the element can be used, a short response time, a large voltage holding ratio, a low threshold voltage, a large contrast ratio, a small flicker rate, and a long life.

Detailed Description

The usage of the terms in the present specification is as follows. The terms "liquid crystalline compound", "liquid crystal composition" and "liquid crystal display element" may be simply referred to as "compound", "composition" and "element", respectively. The "liquid crystalline compound" is a general term for compounds having a liquid crystal phase such as a nematic phase or a smectic phase and compounds having no liquid crystal phase and added for the purpose of adjusting physical properties of the composition such as an upper limit temperature, a lower limit temperature, viscosity, and dielectric anisotropy. The compound has a six-membered ring such as 1, 4-cyclohexylene or 1, 4-phenylene, and the molecular structure is rod-like (rod like). The term "liquid crystal display element" is a generic term for liquid crystal display panels and liquid crystal display modules. The "polymerizable compound" is a compound added for the purpose of producing a polymer in the composition.

The liquid crystal composition can be prepared by mixing a plurality of liquid crystalline compounds. Additives are added to the composition for the purpose of further adjusting physical properties. If necessary, additives such as a polymerizable compound, a polymerization initiator, a polymerization inhibitor, an optically active compound, an antioxidant, an ultraviolet absorber, a light stabilizer, a heat stabilizer, a coloring matter, and an antifoaming agent are added. The liquid crystalline compound or the additive is mixed in this order. Even in the case where an additive is added, the proportion (content) of the liquid crystalline compound is represented by a weight percentage (wt%) based on the weight of the liquid crystal composition containing no additive. The proportion (addition amount) of the additive is represented by a weight percentage (wt%) based on the weight of the liquid crystal composition containing no additive. Parts per million (ppm) by weight are also sometimes used. The proportions of the polymerization initiator and the polymerization inhibitor are exceptionally expressed based on the weight of the polymerizable compound.

The "clearing point" is a transition temperature of a liquid crystal phase-isotropic phase of the liquid crystalline compound. The "lower limit temperature of the liquid crystal phase" is a transition temperature of a solid-liquid crystal phase (smectic phase, nematic phase, etc.) of the liquid crystalline compound. The "upper limit temperature of the nematic phase" is a transition temperature of a mixture of a liquid crystalline compound and a mother liquid crystal or a nematic phase-isotropic phase of a liquid crystal composition, and may be simply referred to as "upper limit temperature". The "lower limit temperature of the nematic phase" may be simply referred to as "lower limit temperature". The expression "to improve the dielectric anisotropy" means that the value thereof increases positively in the case of a composition having a positive dielectric anisotropy and increases negatively in the case of a composition having a negative dielectric anisotropy. The term "high voltage holding ratio" means that the device has a large voltage holding ratio not only at room temperature but also at a temperature close to the upper limit temperature in the initial stage, and also has a large voltage holding ratio not only at room temperature but also at a temperature close to the upper limit temperature after long-term use. In some cases, the properties of the composition or the device are examined before and after a time-dependent change test (including an accelerated deterioration test).

The compound represented by formula (1) may be simply referred to as compound (1). At least one compound selected from the group of compounds represented by formula (1) is sometimes simply referred to as compound (1). "Compound (1)" means one compound or two compounds represented by the formula (1)Mixtures or mixtures of three or more compounds. These rules apply to compounds represented by other formulae. In the formulae (1) to (15), A is surrounded by a hexagon¹、B¹、C¹The marks respectively corresponding to the rings A¹Ring B¹Ring C¹And (3) waiting for a ring. The hexagons represent six-membered rings such as cyclohexane or benzene. The hexagon may represent a condensed ring such as naphthalene or a crosslinked ring such as adamantane.

In the chemical formula of the component compound, the end group R¹¹The notation of (a) is used for a variety of compounds. In these compounds, any two R¹¹The two radicals indicated may be identical or may also be different. For example, R of the compound (2)¹¹Is ethyl, and R of the compound (3)¹¹In the case of ethyl. Also R of the compound (2)¹¹Is ethyl, and R of the compound (3)¹¹In the case of propyl. The rule also applies to R¹²、R¹³、Z¹¹And the like. In the compound (15), when i is 2, two rings E are present¹. In the compounds, two rings E¹The two radicals indicated may be identical or may also be different. When i is greater than 2, the same applies to any two rings E¹. The rules apply to other tokens as well.

The expression "at least one 'a' means that the number of 'a's is arbitrary. The expression "at least one 'a' may be substituted with 'B' means that when the number of 'a' is one, the position of 'a' is arbitrary, and when the number of 'a' is two or more, the positions of these may also be selected without limitation. The rules also apply to the expression "at least one 'a' is substituted with 'B'. The expression "at least one 'a' may be substituted with 'B', 'C' or 'D' is meant to include any substitution of 'a' with 'B', any substitution of 'a' with 'C' and any substitution of 'a' with 'D', as well as a plurality of substitutions of at least two of 'a' with 'B', 'C' and/or 'D'. For example, "at least one-CH₂Examples of the "alkyl group which may be substituted by — O-or-CH ═ CH-include alkyl, alkoxy, alkoxyalkyl, alkenyl, alkoxyalkenyl, and alkenyloxyalkyl. Furthermore, connectTwo successive-CH₂The case where the group is substituted with-O-to form-O-is not preferred. Alkyl, etc., methyl moiety (-CH)₂-CH of- (O-H)₂The case where the-O-is substituted with-O-H is also not preferable.

Sometimes using "R¹¹And R¹²Independently an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms, at least one-CH group being present in the alkyl group or the alkenyl group₂-may be substituted by-O-, and of these groups at least one hydrogen may be substituted by fluorine ". In the expression, "in these groups" may be interpreted in accordance with sentence meaning. In the expression, "these groups" means alkyl groups, alkenyl groups, alkoxy groups, alkenyloxy groups, and the like. That is, "these groups" means all the groups before the term described in "these groups". The common sense interpretation also applies to the terms "in these monovalent radicals" or "in these divalent radicals". For example, "these monovalent radicals" means all radicals before the term "in these monovalent radicals".

In the liquid crystalline compound, the alkyl group is linear or branched and does not contain a cyclic alkyl group. Straight chain alkyls are generally preferred over branched alkyls. The same applies to the terminal group such as an alkoxy group or an alkenyl group. For the configuration (configuration) related to the 1, 4-cyclohexylene group, the trans form is preferred to the cis form in order to increase the upper limit temperature. 2-fluoro-1, 4-phenylene refers to the following two divalent radicals. In the formula, fluorine may be either to the left (L) or to the right (R). The rules may also apply to unsymmetrical divalent radicals generated by the removal of two hydrogens from the ring, such as tetrahydropyran-2, 5-diyl.

The present invention is as follows.

Item 1. a compound represented by formula (1).

In the formula (1), the reaction mixture is,

m¹and n¹Independently 0,1 or 2, m¹And n¹The sum of (1) is 3 or less;

w is-CH₂-、-CF₂-, -CO-, -O-, -S-or-SO₂-；

X is hydrogen or fluorine;

Y¹、Y²、Y³and Y⁴Independently is hydrogen or methyl, Y¹、Y²、Y³And Y⁴At least one of (a) is methyl; when W is-O-, Y¹、Y²、Y³And Y⁴At least two of (a) are methyl groups.

Item 2. the compound according to item 1, wherein in the formula (1) according to item 1,

R¹and R²Independently of the number of carbons or hydrogen1 to 14 alkyl, wherein one or two-CH₂-may be substituted by-O-and-CH₂CH₂-may be substituted by-CH ═ CH-, where at least one hydrogen may be substituted by fluorine;

Z¹and Z²Independently a single bond, -COO-, -OCO-, -CH₂O-、-OCH₂-、-CF₂O-、-OCF₂-、-CH₂CH₂-、-CF₂CF₂-、-CH＝CH-、-CF＝CF-、-C≡C-、-(CH₂)₄-or-CH₂CH＝CHCH₂-；

m¹And n¹Independently 0,1 or 2, m¹And n¹The sum of (1) is 3 or less;

w is-CH₂-, -CO-, -S-or-SO₂-；

X is hydrogen or fluorine;

Y¹、Y²、Y³and Y⁴Independently is hydrogen or methyl, Y¹、Y²、Y³And Y⁴At least one of (a) is methyl.

Item 3. the compound according to item 1 or item 2, wherein in the formula (1) according to item 1,

A¹and A²Independently 1, 4-cyclohexylene, 1, 4-cyclohexenylene, tetrahydropyran-2, 5-diyl, 1, 3-dioxane-2, 5-diyl, 1, 4-phenylene, pyridine-2, 5-diyl, pyrimidine-2, 5-diyl or naphthalene-2, 6-diyl, wherein at least one hydrogen on the aromatic ring may be substituted by fluorine；

Z¹And Z²Independently a single bond, -COO-, -OCO-, -CH₂O-、-OCH₂-、-CF₂O-、-OCF₂-、-CH₂CH₂-、-CF₂CF₂-、-CH＝CH-、-CF＝CF-、-C≡C-、-(CH₂)₄-or-CH₂CH＝CHCH₂-；

m¹And n¹Independently 0,1 or 2, m¹And n¹The sum of (1) is 3 or less;

w is-S-;

x is fluorine;

Y¹、Y²、Y³and Y⁴Independently is hydrogen or methyl, Y¹、Y²、Y³And Y⁴At least one of (a) is methyl.

Item 4. the compound according to item 1 or item 2, wherein in the formula (1) according to item 1,

R¹and R²Independently an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, or an alkenyl group having 2 to 8 carbon atoms;

Z¹and Z²Independently a single bond, -COO-, -OCO-, -CH₂O-、-OCH₂-、-CF₂O-、-OCF₂-、-CH₂CH₂-, -CH-, -C.ident.C-or- (CH)₂)₄-；

m¹And n¹Independently 0,1 or 2, m¹And n¹The sum of (1) is 3 or less;

w is-CH₂-, -CO-or-S-;

x is hydrogen or fluorine;

Y¹、Y²、Y³and Y⁴Independently is hydrogen or methyl, Y¹、Y²、Y³And Y⁴At least one of (a) is methyl.

Item 5. the compound according to item 1 or item 2, wherein in the formula (1) according to item 1,

R¹and R²Independently an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, or an alkenyl group having 2 to 8 carbon atoms;

Z¹and Z²Independently a single bond, -COO-, -OCO-, -CH₂O-、-OCH₂-、-CF₂O-、-OCF₂-、-CH₂CH₂-, -CH-, -C.ident.C-or- (CH)₂)₄-；

m¹And n¹Independently 0,1 or 2, m¹And n¹The sum of (1) is 3 or less;

w is-S-;

x is fluorine;

Y¹、Y²、Y³and Y⁴Independently is hydrogen or methyl, Y¹、Y²、Y³And Y⁴At least one of (a) is methyl.

Item 6. the compound according to item 1 or item 2, wherein in the formula (1) according to item 1,

R¹and R²Independently an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms;

A¹and A²Independently 1, 4-cyclohexylene, tetrahydropyran-2, 5-diyl, 1, 4-phenylene, 2-fluoro-1, 4-phenylene or 2, 3-difluoro-1, 4-phenylene;

Z¹and Z²Independently a single bond, -CH₂O-、-OCH₂-、-CH₂CH₂-or-CH ═ CH-;

m¹and n¹Independently 0,1 or 2, m¹And n¹The sum of (1) is 3 or less;

w is-S-;

x is hydrogen or fluorine;

Y¹、Y²、Y³and Y⁴Independently is hydrogen or methyl, Y¹、Y²、Y³And Y⁴At least one of (a) is methyl.

Item 7. the compound according to item 1 or item 2, wherein in the formula (1) according to item 1,

R¹and R²Independently an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms;

A¹and A²Independently 1, 4-cyclohexylene, tetrahydropyran-2, 5-diyl, 1, 4-phenylene, 2-fluoro-1, 4-phenylene or 2, 3-difluoro-1, 4-phenylene;

Z¹and Z²Independently a single bond, -CH₂O-、-OCH₂-、-CH₂CH₂-or-CH ═ CH-;

m¹and n¹Independently 0,1 or 2, m¹And n¹The sum of (1) is 3 or less;

w is-S-;

x is fluorine;

Y¹、Y²、Y³and Y⁴Independently is hydrogen or methyl, Y¹、Y²、Y³And Y⁴At least one of (a) is methyl.

The compound according to item 1, which is represented by any one of formula (1a) to formula (1 i).

In the formulae (1a) to (1i), R¹And R²Independently an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms; y is¹、Y²、Y³And Y⁴Independently is hydrogen or methyl, Y¹、Y²、Y³And Y⁴At least one of (a) is methyl.

Item 9. the compound according to item 1, which is represented by formula (1j) or formula (1 k).

In the formula (1j) or the formula (1k), R¹And R²Independently an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms.

Item 10.

A liquid crystal composition containing at least one compound according to any one of items 1 to 9.

Item 11. the liquid crystal composition according to item 10, further comprising at least one compound selected from the group consisting of the compounds represented by formulae (2) to (4).

In the formulae (2) to (4),

R¹¹and R¹²Independently an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms, at least one-CH group being present in the alkyl group or the alkenyl group₂-may be substituted by-O-, in which groups at least one hydrogen may be substituted by fluorine;

ring B¹Ring B²Ring B³And ring B⁴Independently 1, 4-cyclohexylene, 1, 4-phenylene, 2-fluoro-1, 4-phenylene, 2, 5-difluoro-1, 4-phenylene or pyrimidin-2, 5-diyl;

Z¹¹、Z¹²and Z¹³Independently a single bond, -COO-, -CH₂CH₂-, -CH-or-C.ident.C-.

Item 12. the liquid crystal composition according to item 10 or item 11, further comprising at least one compound selected from the group consisting of the compounds represented by formulae (5) to (11).

In the formulae (5) to (11),

ring C⁵And ring C⁶Independently 1, 4-cyclohexylene, 1, 4-cyclohexenylene, 1, 4-phenylene, tetrahydropyran-2, 5-diyl, or decahydronaphthalene-2, 6-diyl;

Z¹⁴、Z¹⁵、Z¹⁶and Z¹⁷Independently a single bond, -COO-, -CH₂O-、-OCF₂-、-CH₂CH₂-or-OCF₂CH₂CH₂-；

L¹¹And L¹²Independently fluorine or chlorine;

S¹¹is hydrogen or methyl;

x is-CHF-or-CF₂-；

j. k, m, n, p, q, r and s are independently 0 or 1, the sum of k, m, n and p is 1 or 2, the sum of q, r and s is 0,1, 2 or 3, and t is 1,2 or 3.

Item 13. the liquid crystal composition according to any one of item 10 to item 12, further comprising at least one compound selected from the group consisting of the compounds represented by formula (12) to formula (14).

In the formulae (12) to (14),

R¹⁶is C1-10 alkyl or C2-10 alkenyl, at least one-CH in the alkyl and alkenyl₂-may be substituted by-O-, in which groups at least one hydrogen may be substituted by fluorine;

X¹¹is fluorine, chlorine, -CF₃、-CHF₂、-CH₂F、-OCF₃、-OCHF₂、-OCF₂CHF₂or-OCF₂CHFCF₃；

Z¹⁸、Z¹⁹and Z²⁰Independently a single bond, -COO-, -CH₂O-、-CF₂O-、-OCF₂-、-CH₂CH₂-, -CH-, -C.ident.C-or- (CH)₂)₄-；

L¹³And L¹⁴Independently hydrogen or fluorine.

Item 14. the liquid crystal composition according to any one of item 10 to item 13, further comprising at least one compound selected from the compounds represented by formula (15).

In the formula (15), the reaction mixture is,

R¹⁷is C1-10 alkyl or C2-10 alkenyl, at least one-CH in the alkyl and alkenyl₂-may be substituted by-O-, in which groups at least one hydrogen may be substituted by fluorine;

X¹²is-C.ident.N or-C.ident.C-C.ident.N;

ring E¹Is 1, 4-cyclohexylene, 1, 4-phenylene in which at least one hydrogen is substituted by fluorine, tetrahydropyran-2, 5-diyl, 1, 3-dioxane-2, 5-diyl or pyrimidine-2, 5-diyl;

Z²¹is a single bond, -COO-, -CH₂O-、-CF₂O-、-OCF₂-、-CH₂CH₂-or-C ≡ C-;

L¹⁵and L¹⁶Independently hydrogen or fluorine;

i is 1,2,3 or 4.

An item 15. a liquid crystal display element comprising the liquid crystal composition according to any one of items 10 to 14.

The present invention also includes the following items. (a) The composition further contains at least one optically active compound and/or polymerizable compound. (b) The composition, in turn, contains at least one antioxidant and/or ultraviolet absorber.

The present invention also includes the following items. (c) The composition further contains one, two or at least three additives selected from the group consisting of a polymerizable compound, a polymerization initiator, a polymerization inhibitor, an optically active compound, an antioxidant, an ultraviolet absorber, a light stabilizer, a heat stabilizer, a pigment and an antifoaming agent. (d) The composition has an upper limit temperature of a nematic phase of 70 ℃ or higher, an optical anisotropy (measured at 25 ℃) of 0.08 or higher at a wavelength of 589nm, and a dielectric anisotropy (measured at 25 ℃) of-2 or lower at a frequency of 1 kHz.

The present invention also includes the following items. (e) An element comprising said composition and having a PC, TN, STN, ECB, OCB, IPS, VA, FFS, field-induced photo-reactive alignment (FPA) or PSA mode. (f) An AM element comprising the composition. (g) A transmissive element comprising the composition. (h) Use of the composition as a composition having a nematic phase. (i) Use as an optically active composition by adding an optically active compound to said composition.

The form of compound (1), the synthesis of compound (1), the liquid crystal composition, and the liquid crystal display element will be described in order.

1. Forms of Compound (1)

The compound (1) has a dibenzothiophene skeleton. Y is¹、Y²、Y³And Y⁴Independently hydrogen (-H) or methyl (-CH)₃)，Y¹、Y²、Y³And Y⁴At least one of (a) is methyl. That is, the compound (1) has a dibenzothiophene ring substituted with a methyl group. Further, the symbols of the compound (1) are defined as described in the above item 1.

The compound has negative dielectric anisotropy. The compound is extremely stable physically and chemically under the conditions under which the device is usually used, and has good compatibility with other liquid crystalline compounds. The compositions containing the compounds are stable under the conditions in which the components are normally used. When the composition is stored at a low temperature, the compound has a small tendency to precipitate as crystals (or smectic phases). The compound has general physical properties required for the components of the composition, appropriate optical anisotropy, and large dielectric anisotropy.

Terminal group (R) of Compound (1)¹And R²) Ring (A)¹And A²) A bonding group (Z)¹And Z²) A crosslinking group (W) and substituents (X and Y)¹To Y⁴) Preferred examples of (c) are as follows. The examples also apply to the lower formula of compound (1). In the compound (1), the physical properties can be arbitrarily adjusted by appropriately combining these groups. Since there is no great difference in physical properties of the compounds, the compound (1) may be contained in an amount larger than that of the naturally occurring one²H (deuterium),¹³C is an isotope.

In the formula (1), R¹And R²Independently hydrogen, fluorine, chlorine or an alkyl group of carbon number 1 to 16, in which at least one-CH₂May be substituted by-O-, -CO-, -COO-, -OCO-, -OCOO-or-Si (CH)₃)₂-substituted, at least one-CH₂CH₂-may be substituted by-CH ═ CH-or-C ≡ C-, at least one of these groups being hydrogen which may be fluorine, chlorine, -CF₃or-C ≡ N substitution.

Preferred R¹Or R²Is hydrogen, alkyl, alkoxy, alkoxyalkyl, alkoxyalkoxy, alkylthio, alkylthioalkoxy, acyl, acylalkyl, acyloxy, acyloxyalkyl, alkoxycarbonyl, alkoxycarbonylalkyl, alkenyl, alkenyloxy, alkenyloxyalkyl, alkoxyalkenyl, alkynyl, alkynyloxy, silalkyl (silaakyl) or disilaheteroalkyl. In these radicalsAt least one hydrogen may be substituted by fluorine or chlorine. The examples include groups in which at least two hydrogens are substituted with both fluorine and chlorine. Further preferred is a group in which at least one hydrogen is substituted with only fluorine. Among these groups, straight chain is preferable to branched chain. Even if R is¹Or R²Are branched chains, also have asymmetric centers, and are preferred when optically active.

When R is¹Or R²Having a methyl group (-CH)₃) When the methyl group is substituted by a group represented by the formulae (G1) to (G4).

In the formulae (G1) to (G4), R³Is an alkyl group having 1 to 12 carbon atoms, in which one or two-CH₂-may be substituted by-O-and-CH₂CH₂-may be substituted by-CH ═ CH-, where at least one hydrogen may be substituted by fluorine or chlorine. Preferred R³Is an alkyl group. Specific R³Is methyl or ethyl. The compound having such a group may be optically active or may be racemic.

Further preferred is R¹Or R²Is alkyl, alkoxy, alkoxyalkyl, alkenyl, monofluoroalkyl, polyfluoroalkyl, monofluoroalkoxy or polyfluoroalkoxy. Further, the polyfluoroalkyl group or polyfluoroalkoxy group may contain a perfluoroalkyl group or a perfluoroalkoxy group, respectively. Particularly preferred R¹Or R²Is alkyl, alkoxy or alkenyl.

The preferred steric configuration of-CH ═ CH-in the alkenyl group depends on the position of the double bond. Among alkenyl groups such as 1-propenyl, 1-butenyl, 1-pentenyl, 1-hexenyl, 3-pentenyl, 3-hexenyl, the trans configuration is preferred. Among alkenyl groups such as 2-butenyl, 2-pentenyl, 2-hexenyl, the cis configuration is preferred.

Specific R¹Or R²Is methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, heptyloxy, methoxymethyl, methoxyethyl, methoxypropyl, ethoxymethylEthoxyethyl, ethoxypropyl, propoxymethyl, butoxymethyl, pentyloxymethyl, vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 2-propenyloxy, 2-butenyloxy, 2-pentenyloxy, 1-propynyl or 1-pentenyl.

Specific R¹Or R²Also 2-fluoroethyl, 3-fluoropropyl, 2,2, 2-trifluoroethyl, 2-fluorovinyl, 2, 2-difluorovinyl, 2-fluoro-2-vinyl, 3-fluoro-1-propenyl, 3,3, 3-trifluoro-1-propenyl, 4-fluoro-1-propenyl or 4, 4-difluoro-3-butenyl.

Further preferred is R¹Or R²Is methyl, ethyl, propyl, butyl, pentyl, methoxy, ethoxy, propoxy, butoxy, pentyloxy, methoxymethyl, ethoxymethyl, propoxymethyl, ethenyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 2-propenyloxy, 2-butenyloxy or 2-pentenyloxy. Most preferred R¹Or R²Is methyl, ethyl, propyl, butyl, pentyl, methoxy, ethoxy, propoxy, methoxymethyl, ethenyl, 1-propenyl, 3-butenyl or 3-pentenyl.

In the formula (1), A¹And A²Independently 1, 2-cyclopropylene, 1, 3-cyclobutylene, 1, 3-cyclopentylene, 1, 4-cyclohexylene, 1, 4-cyclohexenylene, 1, 4-cycloheptylene, 1, 5-cyclooctylene, tetrahydropyran-2, 5-diyl, 1, 3-dioxane-2, 5-diyl, 1, 4-phenylene, pyridine-2, 5-diyl, pyrimidine-2, 5-diyl, decahydronaphthalene-2, 6-diyl, tetrahydronaphthalene-2, 6-diyl or naphthalene-2, 6-diyl, in which at least one hydrogen on the aromatic ring may be fluorine, chlorine, -CF₃、-CHF₂、-CH₂F、-OCF₃、-OCHF₂、-OCH₂F or-C ≡ N substitution.

Preferred A¹Or A²Is 1, 4-cyclohexylene, 1, 4-cyclohexenylene, tetrahydropyran-2, 5-diyl, 1, 3-dioxane-2, 5-diyl, 1, 4-phenylene, 2-fluoro-1, 4-phenylene, 2, 3-difluoro-1, 4-phenylene, 2,5-Difluoro-1, 4-phenylene, 2, 6-difluoro-1, 4-phenylene, 2,3, 5-trifluoro-1, 4-phenylene, pyridine-2, 5-diyl, 3-fluoropyridine-2, 5-diyl, pyrimidine-2, 5-diyl, decahydronaphthalene-2, 6-diyl, 1,2,3, 4-tetrahydronaphthalene-2, 6-diyl, or naphthalene-2, 6-diyl. For the stereoconfiguration of 1, 4-cyclohexylene and 1, 3-dioxane-2, 5-diyl, the trans form is preferred over the cis form.

Further preferred is A¹Or A²Is 1, 4-cyclohexylene, tetrahydropyran-2, 5-diyl, 1, 3-dioxane-2, 5-diyl, 1, 4-phenylene, 2-fluoro-1, 4-phenylene, 2, 3-difluoro-1, 4-phenylene, 2, 5-difluoro-1, 4-phenylene, 2, 6-difluoro-1, 4-phenylene, pyridine-2, 5-diyl or pyrimidine-2, 5-diyl. Particularly preferred is A¹Or A²Is 1, 4-cyclohexylene or 1, 4-phenylene.

In the formula (1), Z¹And Z²Independently a single bond or alkylene of 1 to 6 carbon atoms, a-CH₂-may be substituted by-O-, -CO-, -COO-or-OCO-, one-CH₂CH₂-may be substituted by-CH ═ CH-or-C ≡ C-, at least one of these divalent radicals being substituted by fluorine or chlorine.

Z¹Or Z²Specific examples thereof are a single bond, -O-, -COO-, -OCO-, -CH₂O-、-OCH₂-、-CF₂O-、-OCF₂-、-CH₂CH₂-、-CH＝CH-、-CF＝CH-、-CH＝CF-、-CF＝CF-、-C≡C-、-CH₂CO-、-COCH₂-、-(CH₂)₄-、-CH₂CH＝CHCH₂-、-(CH₂)₂COO-、-(CH₂)₂OCO-、-OCO(CH₂)₂-、-COO(CH₂)₂-、-(CH₂)₂CF₂O-、-(CH₂)₂OCF₂-、-OCF₂(CH₂)₂-、-CF₂O(CH₂)₂-、-(CH₂)₃O-or-O (CH)₂)₃-. For the radicals and-CH-, -CF-, -CH₂O-and-OCH₂The double bond of a bonding group such as-CH-has a configuration in which trans is preferred to cis.

Preferred Z¹Or Z²Is a single bond, -O-, -COO-, -OCO-, -CH₂O-、-OCH₂-、-CF₂O-、-OCF₂-、-CH₂CH₂-, -CH-, -CF-, -C.ident.C-or- (CH ≡ C-)₂)₄-. Further preferred is Z¹Or Z²Is a single bond, -COO-, -OCO-, -CF₂O-、-OCF₂-、-CH＝CH-、-CH₂CH₂-or-C ≡ C-. Most preferred Z¹Or Z²Is a single bond.

In the formula (1), m¹And n¹Independently 0,1 or 2, m¹And n¹The sum of (1) is 3 or less. When the dibenzothiophene rings are counted as one ring, the compounds have one to four rings. m is¹And n¹The compound (2) has a good compatibility with other liquid crystalline compounds and a low viscosity. m is¹And n¹The upper limit temperature of the compound having a sum of (2) or (3) is high, and the temperature range of the liquid crystal phase is wide.

In the formula (1), W is-CH₂-、-CF₂-, -CO-, -O-, -S-or-SO₂-. Preferred W is-CF₂-, -O-, -S-. Further, W is preferably-O-, -S-. Particularly preferred W is-S-.

In the formula (1), X is hydrogen or fluorine. Preferably X is fluorine.

In the formula (1), Y¹、Y²、Y³And Y⁴Independently is hydrogen or methyl, Y¹、Y²、Y³And Y⁴At least one of (a) is methyl; when W is-O-, Y¹、Y²、Y³And Y⁴At least two of (a) are methyl groups.

By appropriately selecting the terminal group, ring, bonding group, substituent, ring number and the like of the compound (1), physical properties such as optical anisotropy, dielectric anisotropy and the like can be arbitrarily adjusted. The effects of the types of these groups on the physical properties of the compound (1) will be described below.

In the compound (1), when the terminal group (R)¹Or R²) In the case of a linear chain, the liquid crystal phase has a wide temperature range and a low viscosity. When R is¹Or R²When branched, with other liquid-crystalline compoundsThe compatibility is good. Compounds whose terminal groups are optically active groups are effective as chiral dopants (chiral dopants). By adding the compound to the composition, reverse twisted domains (reverse twisted domains) generated in the element can be prevented. Compounds in which the terminal group is not an optically active group are effective as components of the composition. When the terminal group is an alkenyl group, the preferred configuration depends on the position of the double bond. The alkenyl compound having a preferred steric configuration has a high upper limit temperature or a wide temperature range of a liquid crystal phase. In mol.crystal.liq.crystal.), 1985,131,109, and 1985,131,327, mol.crystal.liq.crystal ″.

When ring A¹Or ring A²When the compound is a 1, 4-phenylene group, pyridine-2, 5-diyl group, pyrimidine-2, 5-diyl group or pyridazine-3, 6-diyl group, at least one of which hydrogen may be substituted by fluorine or chlorine, the optical anisotropy is large. When the ring is 1, 4-cyclohexylene, 1, 4-cyclohexenylene or 1, 3-dioxane-2, 5-diyl, optical anisotropy is small.

When at least one ring is a 1, 4-cyclohexylene group, the upper limit temperature is high and the optical anisotropy is small. When at least one ring is a 1, 4-phenylene group, the optical anisotropy is large and the orientation order parameter (orientational order parameter) is large. When at least two rings are 1, 4-phenylene, the optical anisotropy is large, the temperature range of the liquid crystal phase is wide, and the upper limit temperature is high.

When bonding group Z¹Or a bonding group Z²Is a single bond, -O-, -CH₂O-、-CF₂O-、-OCF₂-、-CH₂CH₂-, -CH-, -CF-or- (CH)₂)₄When-it is small. When the bonding group is a single bond, -OCF₂-、-CF₂O-、-CH₂CH₂-or-CH ═ CH-, the viscosity is less. When the bonding group is-CH-, the liquid crystal phase has a wide temperature range and an elastic constant ratio of K₃₃/K₁₁(K₃₃: flexural elastic constant (bend elastic constant), K₁₁: a large splay elastic constant). When the bonding group is-C.ident.C-, the optical anisotropy is large.

When the compound (1) has one ring or two rings, the viscosity is small. When the compound (1) has a tetracyclic or pentacyclic ring, the upper limit temperature is high. As described above, by appropriately selecting the types of the terminal group, the ring and the bonding group, and the number of rings, a compound having desired physical properties can be obtained. Therefore, the compound (1) is effectively used as a component of a composition used for devices having modes such as PC, TN, STN, ECB, OCB, IPS, and VA. The compound (1) is suitable for devices having VA, IPS, PSA, or other modes.

2. Synthesis of Compound (1)

The synthesis method of the compound (1) will be described. The compound (1) can be synthesized by appropriately combining the methods of organic synthetic chemistry. Methods for introducing desired terminal groups, rings and bonding groups into starting materials are described in "Organic Synthesis (Organic Synthesis)", (John Wiley & Sons, Inc.), "Organic reactions (Organic reactions)", (John Wiley & Sons, Inc.), "" Integrated Organic chemistry (Comprehensive Organic Synthesis) "," (Pergamman Press), "New Experimental chemistry lecture (Takayama)", and the like.

2-1 formation of the radical Z

With respect to the formation of the bonding group Z¹And a bonding group Z²First, the flow is shown. Next, the reactions described in the flow of the methods (1) to (11) will be described. In the process, MSG¹(or MSG)²) Is a monovalent organic group. Multiple MSGs for use in a process¹(or MSG)²) The monovalent organic groups represented may be the same or different. The compounds (1A) to (1J) correspond to the compound (1).

(1) Formation of single bonds

The compound (1A) is synthesized by reacting an arylboronic acid (21) synthesized by a known method with a halide (22) in the presence of a catalyst such as carbonate and tetrakis (triphenylphosphine) palladium. The compound (1A) can also be synthesized by reacting a halide (23) synthesized by a known method with n-butyllithium, then with zinc chloride, and with a halide (22) in the presence of a catalyst such as dichlorobis (triphenylphosphine) palladium.

(2) -COO-generation

The halide (23) is reacted with n-butyllithium, and then reacted with carbon dioxide to obtain a carboxylic acid (24). Compound (1B) is synthesized by dehydrating compound (25) synthesized by a known method and carboxylic acid (24) in the presence of 1,3-Dicyclohexylcarbodiimide (DCC) and 4-Dimethylaminopyridine (DMAP).

(3)-CF₂Formation of O-

Compound (1B) is treated with a sulfurizing agent such as Lawesson's reagent to obtain a sulfur monoester (thioester) (26). Compound (1C) was synthesized by fluorinating the sulfur monoester (26) with hydrogen fluoride pyridine complex and N-bromosuccinimide (NBS). See, e.g., chem.lett, 1992,827, of M.Puxing (M.Kuroboshi), et al. Compound (1C) can also be synthesized by fluorinating sulfur monoester (26) with (Diethylamino) sulfur trifluoride (DAST). Reference is made to journal of organic chemistry (j.org.chem.) 1990,55,768, by w.h. bonnelle (w.h.bunnelle), et al. The linking group can also be generated using the method described in International edition of applied chemistry (English), 2001,40,1480, of Pierch, et al, Angew. chem. int. Ed.).

(4) -CH-generation

The halide (22) is treated with N-butyllithium and then reacted with N, N-Dimethylformamide (DMF) to obtain an aldehyde (28). Phosphonium salt (27) synthesized by a known method is treated with a base such as potassium tert-butoxide to produce a phosphonium ylide. The phosphorus ylide is reacted with an aldehyde (28) to synthesize a compound (1D). Since the cis-isomer is produced according to the reaction conditions, the cis-isomer is isomerized to the trans-isomer by a known method as required.

(5)-CH₂CH₂Generation of

Compound (1E) is synthesized by hydrogenating compound (1D) in the presence of a catalyst such as palladium on carbon.

(6)-(CH₂)₄Generation of

The phosphonium salt (29) is used in place of the phosphonium salt (27), and the compound having- (CH) is obtained according to the process of the process (4)₂)₂-CH ═ CH-compounds. The compound (1F) is synthesized by contact hydrogenation of the compound.

(7)-CH₂CH＝CHCH₂Generation of

Compound (1G) was synthesized according to the method of method (4) using phosphonium salt (30) in place of phosphonium salt (27) and aldehyde (31) in place of aldehyde (28). The trans-isomer is isomerized to the cis-isomer by a known method as needed, because the trans-isomer is produced according to the reaction conditions.

(8) Production of-C.ident.C-

The compound (32) is obtained by reacting a halide (23) with 2-methyl-3-butyn-2-ol in the presence of a catalyst of palladium dichloride and copper halide and then deprotecting under basic conditions. Compound (1H) is synthesized by reacting compound (32) with halide (22) in the presence of a catalyst of palladium dichloride and copper halide.

(9) Formation of-CF ═ CF-

The halide (23) is treated with n-butyllithium, and then tetrafluoroethylene is reacted to obtain a compound (33). Compound (1I) is synthesized by treating halide (22) with n-butyllithium and then reacting the treated halide with compound (33).

(10)-OCH₂Generation of

Aldehyde (28) is reduced with a reducing agent such as sodium borohydride to obtain compound (34). Compound (34) is brominated with hydrobromic acid or the like to obtain bromide (35). Compound (1J) is synthesized by reacting compound (36) with bromide (35) in the presence of a base such as potassium carbonate.

(11)-(CF₂)₂Generation of

According to the method described in J.Am.chem.Soc.), (2001,123,5414), diketone (-COCO-) is fluorinated with sulfur tetrafluoride in the presence of a hydrogen fluoride catalyst to obtain a compound having the formula- (CF)₂)₂-a compound of (a).

2-2. Ring Generation

Then, the ring A is aligned¹And ring A²The following describes a method of generating the same. With respect to the ring such as 1, 4-cyclohexylene, 1, 3-dioxane-2, 5-diyl, 1, 4-phenylene, 2-fluoro-1, 4-phenylene, 2, 3-difluoro-1, 4-phenylene, pyridine-2, 5-diyl, pyrimidine-2, 5-diyl, the starting material is commercially available or widely known. Therefore, the compound (64), the compound (67) and the compound (71) shown below will be described.

Decahydronaphthalene-2, 6-dione (64) is the starting material for compounds having decahydronaphthalene-2, 6-diyl. The compound (64) can be obtained by: according to the method described in Japanese patent laid-open No. 2000-239564, a diol (63) is reduced by contacting hydrogen in the presence of ruthenium oxide, and further oxidized by chromium oxide. The compound is converted into the compound (1) by a usual method.

The structural unit of 2,3- (bistrifluoromethyl) benzene was synthesized by the method described in "org. lett., (2000, 2 (21)), 3345. Aniline (66) is synthesized by Diels-Alder (Diels-Alder) type reaction of furan (65) with 1,1,1,4,4, 4-hexafluoro-2-butyne at high temperature. Iodide (67) was obtained by Sandmeyer type reaction of the compound according to methods described in overview of organic synthesis (org. synth. col.), vol.2,1943, 355. The compound is converted into the compound (1) by a usual method.

The structural unit of 2-difluoromethyl-3-fluorobenzene was synthesized by the following method. The hydroxyl group of compound (68) is protected with an appropriate protecting group to obtain compound (69). P is a protecting group. Sec-butyllithium was allowed to act on compound (69), followed by reaction with N, N-Dimethylformamide (DMF) to obtain aldehyde (70). The compound was fluorinated using diethylaminosulfur trifluoride (DAST), followed by deprotection to obtain phenol (71). The compound is converted into the compound (1) by a usual method.

2-3 formation of dibenzothiophene rings substituted with methyl groups

The method for producing a methyl-substituted dibenzothiophene ring is described in synthesis example 1.

3. Liquid crystal composition

3-1. component (A)

The liquid crystal composition of the present invention will be explained. The composition contains at least one compound (1) as component (a). The composition may also contain two or more compounds (1). The component of the composition may be only compound (1). In order to exhibit good physical properties, the composition preferably contains at least one compound (1) in a range of 1 to 99% by weight. In the composition having negative dielectric anisotropy, the preferable proportion of the compound (1) is in the range of 5 to 60% by weight. In the composition having positive dielectric anisotropy, the preferable proportion of the compound (1) is 30% by weight or less.

The composition contains a compound (1) as a component (a). The composition preferably further contains a liquid crystalline compound selected from the components (b) to (e) shown in table 1. When the composition is prepared, it is preferably selected from the components (b) to (e) in consideration of the positive, negative and magnitude of the dielectric anisotropy. The composition may also contain a liquid crystalline compound different from the compounds (1) to (15). The composition may also be free of such liquid crystalline compounds.

The component (b) is a compound having an alkyl group or the like at both terminal groups. Preferred examples of the component (b) include: compounds (2-1) to (2-11), compounds (3-1) to (3-19), and compounds (4-1) to (4-7). In these compounds, R¹¹And R¹²Independently an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms, at least one-CH group being present in the alkyl group or the alkenyl group₂-may be substituted by-O-, of which groups at least one hydrogen may be substituted by fluorine.

The component (b) has a small dielectric anisotropy. The dielectric anisotropy of component (b) is close to zero. The compound (2) has an effect of lowering viscosity or adjusting optical anisotropy. The compound (3) and the compound (4) have an effect of expanding the temperature range of the nematic phase or adjusting the optical anisotropy by increasing the upper limit temperature.

With increasing the proportion of component (b), the viscosity of the composition decreases, but the dielectric anisotropy decreases. Therefore, the more the content, the more preferable, as long as the required value of the threshold voltage of the element is satisfied. In the case of producing a composition for IPS, VA, or other modes, the proportion of the component (b) is preferably 30% by weight or more, and more preferably 40% by weight or more.

The component (c) is a compound (5) to a compound (11). These compounds have phenylene radicals which are substituted laterally by two halogens, as in 2, 3-difluoro-1, 4-phenylene. Preferred examples of the component (c) include: the compound (5-1) to the compound (5-8), the compound (6-1) to the compound (6-17), the compound (7-1), the compound (8-1) to the compound (8-3), the compound (9-1) to the compound (9-11), the compound (10-1) to the compound (10-3), and the compound (11-1) to the compound (11-3). In these compounds, R¹³、R¹⁴And R¹⁵Independently an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms, at least one-CH group being present in the alkyl group or the alkenyl group₂May be substituted by-O-, at least one of these radicalsHydrogen may be substituted by fluorine, and R¹⁵And may also be hydrogen or fluorine.

The dielectric anisotropy of the component (c) is negative and large. Component (c) is used in the case of producing a composition for IPS, VA, PSA, or other modes. As the proportion of the component (c) is increased, the dielectric anisotropy of the composition becomes negative and large, but the viscosity becomes large. Therefore, as long as the required value of the threshold voltage of the element is satisfied, the smaller the content, the more preferable. When the dielectric anisotropy is about-5, the ratio is preferably 40 wt% or more for sufficient voltage driving.

In the component (c), the compound (5) is a bicyclic compound, and therefore has the effects of reducing viscosity, adjusting optical anisotropy, or improving dielectric anisotropy. Since the compound (5) and the compound (6) are tricyclic compounds, they have the effect of increasing the upper limit temperature, increasing the optical anisotropy, or increasing the dielectric anisotropy. The compounds (8) to (11) have an effect of improving the dielectric anisotropy.

In the case of producing a composition for IPS, VA, PSA, or other modes, the proportion of the component (c) is preferably 40% by weight or more, and more preferably in the range of 50% by weight to 95% by weight. When the component (c) is added to a composition having positive dielectric anisotropy, the proportion of the component (c) is preferably 30% by weight or less. By adding the component (c), the elastic constant of the composition can be adjusted, and the voltage-transmittance curve of the element can be adjusted.

The component (d) is a compound having a halogen or a fluorine-containing group at the right terminal. Preferred examples of the component (d) include: compound (12-1) to compound (12-16), compound (13-1) to compound (13-116), compound (14-1) to compound (14-59). In these compounds, R¹⁶Is alkyl with 1-10 carbon atoms or alkenyl with 2-10 carbon atoms, at least one of the alkyl and alkenyl-CH₂-may be substituted by-O-, of which groups at least one hydrogen may be substituted by fluorine. X¹¹Is fluorine, chlorine, -OCF₃、-OCHF₂、-CF₃、-CHF₂、-CH₂F、-OCF₂CHF₂or-OCF₂CHFCF₃。

Since the component (d) has positive dielectric anisotropy and very good stability to heat or light, it is used in the case of producing a composition for IPS, FFS, OCB, or other modes. The proportion of the component (d) is suitably in the range of 1 to 99% by weight, preferably in the range of 10 to 97% by weight, and more preferably in the range of 40 to 95% by weight. When the component (d) is added to a composition having negative dielectric anisotropy, the proportion of the component (d) is preferably 30% by weight or less. By adding the component (d), the elastic constant of the composition can be adjusted, and the voltage-transmittance curve of the element can be adjusted.

Component (e) is a compound (15) having the right terminal group-C.ident.N or-C.ident.C-C.ident.N. Preferred examples of the component (e) include compounds (15-1) to (15-64).In these compounds, R¹⁷Is C1-10 alkyl or C2-10 alkenyl, at least one-CH in the alkyl and alkenyl₂-may be substituted by-O-, of which groups at least one hydrogen may be substituted by fluorine. X¹²is-C.ident.N or-C.ident.C-C.ident.N.

Since the component (e) has positive dielectric anisotropy and a large value, it is used in the case of producing a composition for a TN or the like mode. By adding the component (e), the dielectric anisotropy of the composition can be improved. The component (e) has the effect of expanding the temperature range of the liquid crystal phase, adjusting the viscosity, or adjusting the optical anisotropy. The component (e) is also useful for adjusting the voltage-transmittance curve of the element.

In the case of producing a composition for TN or the like mode, the proportion of the component (e) is suitably in the range of 1 to 99% by weight, preferably in the range of 10 to 97% by weight, and more preferably in the range of 40 to 95% by weight. When the component (e) is added to a composition having negative dielectric anisotropy, the proportion of the component (e) is preferably 30% by weight or less. By adding the component (e), the elastic constant of the composition can be adjusted, and the voltage-transmittance curve of the element can be adjusted.

By combining an appropriately selected compound from the components (b) to (e) with the compound (1), a liquid crystal composition can be prepared which sufficiently satisfies at least one of physical properties such as high stability to heat or light, high upper limit temperature, low lower limit temperature, low viscosity, appropriate optical anisotropy (i.e., large optical anisotropy or small optical anisotropy), positive or negative and large dielectric anisotropy, large specific resistance, and appropriate elastic constant (i.e., large elastic constant or small elastic constant). The device containing the composition has a wide temperature range in which the device can be used, a short response time, a large voltage holding ratio, a low threshold voltage, a large contrast ratio, a small flicker rate, and a long life.

When the element is used for a long time, flickering (flicker) may occur on a display screen. The flicker rate (%) may be represented by (| luminance when a positive voltage is applied-luminance | average luminance when a negative voltage is applied) × 100. With respect to the element having the flicker rate in the range of 0% to 1%, flicker (flicker) is less likely to occur on the display screen even if the element is used for a long time. The flicker is presumed to be associated with an afterimage of an image, and is generated due to a potential difference between the positive frame and the negative frame when driven with alternating current. Compositions containing compound (1) are also useful for reducing the generation of flicker.

3-2. additives

The liquid crystal composition is prepared by a known method. For example, the component compounds are mixed and dissolved in each other by heating. Additives may be added to the composition according to the use. Examples of the additives are polymerizable compounds, polymerization initiators, polymerization inhibitors, optically active compounds, antioxidants, ultraviolet absorbers, light stabilizers, heat stabilizers, pigments, antifoaming agents, and the like. Such additives are well known to those skilled in the art and are described in the literature.

In a liquid crystal display element having a Polymer Stabilized Alignment (PSA) mode, a composition contains a polymer. The polymerizable compound is added for the purpose of producing a polymer in the composition. The polymerizable compound is polymerized by irradiating ultraviolet rays with a voltage applied between the electrodes, thereby forming a polymer in the composition. By the method, a proper pretilt angle can be achieved, so that an element with shortened response time and improved image retention can be manufactured.

Preferable examples of the polymerizable compound are acrylate, methacrylate, vinyl compound, vinyloxy compound, propylene ether, epoxy compound (oxetane ) and vinyl ketone. Further preferable examples are a compound having at least one acryloyloxy group and a compound having at least one methacryloyloxy group. Further preferred examples include compounds having both an acryloyloxy group and a methacryloyloxy group.

Further preferred examples are the compounds (M-1) to (M-18). In these compounds, R²⁵To R³¹Is hydrogen or methyl; r³²、R³³And R³⁴Independently hydrogen or C1-5 alkyl, R³²、R³³And R³⁴At least one of (a) is an alkyl group having a carbon number of 1 to 5; v, w and x are independently 0 or 1; u and y are independently integers from 1 to 10. L is²¹To L²⁶Is hydrogen or fluorine; l is²⁷And L²⁸Independently hydrogen, fluorine or methyl.

The polymerizable compound can be rapidly polymerized by adding a polymerization initiator. By optimizing the reaction conditions, the amount of the residual polymerizable compound can be reduced. Examples of photoradical polymerization initiators are TPO 1173 and 4265 from the Darocur (Darocur) series of Basf corporation, 184, 369, 500, 651, 784, 819, 907, 1300, 1700, 1800, 1850 and 2959 from the Irgacure (Irgacure) series.

Additional examples of photo radical polymerization initiators are 4-methoxyphenyl-2, 4-bis (trichloromethyl) triazine, 2- (4-butoxystyryl) -5-trichloromethyl-1, 3, 4-oxadiazole, 9-phenylacridine, 9, 10-benzophenazine, benzophenone/MILL's ketone mixture, hexaarylbiimidazole/mercaptobenzimidazole mixture, 1- (4-isopropylphenyl) -2-hydroxy-2-methylpropan-1-one, benzyldimethylketal, 2-methyl-1- [4- (methylthio) phenyl ] -2-morpholinopropan-1-one, 2, 4-diethylxanthone/p-dimethylaminobenzoic acid (benzonic acid) methyl ester mixture, benzophenone/methyl triethanolamine mixtures.

Polymerization can be performed by adding a photo radical polymerization initiator to the liquid crystal composition and then irradiating ultraviolet rays in a state where an electric field is applied. However, there is a possibility that the unreacted polymerization initiator or the decomposition product of the polymerization initiator causes display defects such as image sticking in the device. In order to prevent this, photopolymerization may be performed without adding a polymerization initiator. The preferred wavelength of the light to be irradiated is in the range of 150nm to 500 nm. Further, the preferred wavelength is in the range of 250nm to 450nm, and the most preferred wavelength is in the range of 300nm to 400 nm.

When the polymerizable compound is stored, a polymerization inhibitor may be added to prevent polymerization. The polymerizable compound is usually added to the composition without removing the polymerization inhibitor. Examples of the polymerization inhibitor are hydroquinone, hydroquinone derivatives such as methyl hydroquinone, 4-t-butyl catechol, 4-methoxyphenol, phenothiazine and the like.

The optically active compound has an effect of preventing reverse twist by imparting a desired twist angle (torsion angle) to the liquid crystal molecules by inducing a helical structure. The helix pitch can be adjusted by adding an optically active compound. Two or more optically active compounds may be added for the purpose of adjusting the temperature dependence of the helical pitch. Preferable examples of the optically active compound include the following compounds (Op-1) to (Op-18). In the compound (Op-18), the ring J is 1, 4-cyclohexylene or 1, 4-phenylene, R²⁸Is an alkyl group having 1 to 10 carbon atoms. The + label indicates asymmetric carbon.

The antioxidant is effective in maintaining a large voltage holding ratio. Preferred examples of the antioxidant include: the following compound (AO-1) and compound (AO-2); irganox 415, Irganox 565, Irganox 1010, Irganox 1035, Irganox 3114, and Irganox 1098 (trade name; BASF corporation). The ultraviolet absorber is effective in preventing a decrease in the upper limit temperature. Preferable examples of the ultraviolet absorber include benzophenone derivatives, benzoate (benzoate) derivatives, triazole derivatives and the like, and specific examples thereof include: the following compound (AO-3) and compound (AO-4); bin (Tinuvin)329, Bin (Tinuvin) P, Bin (Tinuvin)326, Bin (Tinuvin)234, Bin (Tinuvin)213, Bin (Tinuvin)400, Bin (Tinuvin)328, and Bin (Tinuvin)99-2 (trade name; BASF corporation); and 1,4-Diazabicyclo [2.2.2] octane (1,4-Diazabicyclo [2.2.2] octane, DABCO).

Light stabilizers such as hindered amines are preferred because they maintain a large voltage holding ratio. Preferred examples of the light stabilizer include: the following compound (AO-5), compound (AO-6) and compound (AO-7); dennubin (Tinuvin)144, Dennubin (Tinuvin)765 and Dennubin (Tinuvin)770DF (trade name; BASF corporation); LA-77Y and LA-77G (trade name; Adeka). The heat stabilizer is effective for maintaining a large voltage holding ratio, and preferable examples thereof include Irgafos 168 (trade name; BASF corporation). In order to be suitable for a guest host (guest host) mode element, a dichroic dye (dichroicdye) such as an azo dye or an anthraquinone dye is added to the composition. The antifoaming agent is effective in preventing foaming. Preferable examples of the defoaming agent are dimethyl silicone oil, methylphenyl silicone oil and the like.

In the compound (AO-1), R⁴⁰Is alkyl with 1 to 20 carbon atoms, alkoxy with 1 to 20 carbon atoms, -COOR⁴¹or-CH₂CH₂COOR⁴¹Here, R⁴¹Is an alkyl group having 1 to 20 carbon atoms. In the compound (AO-2) and the compound (AO-5), R⁴²Is an alkyl group having 1 to 20 carbon atoms. In the compound (AO-5), R⁴³Is hydrogen, methyl or O' (oxygen radical); ring G¹Is 1, 4-cyclohexylene or 1, 4-phenylene; in the compound (AO-7), ring G²Is 1, 4-cyclohexylene, 1, 4-phenylene or 1, 4-phenylene in which at least one hydrogen is substituted by fluorine; in the compound (AO-5) and the compound (AO-7), z is 1,2 or 3.

4. Liquid crystal display element

The liquid crystal composition can be used for liquid crystal display elements having operation modes such as PC, TN, STN, OCB, and PSA and driven by an active matrix system. The composition can also be used for liquid crystal display elements having operation modes such as PC, TN, STN, OCB, VA, IPS and the like and driven by a passive matrix method. These elements can be applied to any of reflection type, transmission type, and semi-transmission type.

The compositions are also suitable for Nematic Curvilinear Aligned Phase (NCAP) elements, where the compositions are microencapsulated. The composition can also be used for Polymer Dispersed Liquid Crystal Display (PDLCD) or Polymer Network Liquid Crystal Display (PNLCD). These compositions contain a large amount of a polymerizable compound. On the other hand, when the ratio of the polymerizable compound is 10 wt% or less based on the weight of the liquid crystal composition, a PSA mode liquid crystal display element is produced. The preferred ratio is in the range of 0.1 to 2% by weight. Further, the preferable ratio is in the range of 0.2 to 1.0% by weight. The PSA mode element can be driven by a driving method such as an active matrix method or a passive matrix method. Such an element can be applied to any of a reflection type, a transmission type, and a semi-transmission type.

99页详细技术资料下载

上一篇：一种医用注射器针头装配设备

下一篇：具有抗病毒活性的咪唑啉酮及其合成方法和应用

Liquid crystalline compound having dibenzothiophene ring, liquid crystal composition, and liquid crystal display element

相关技术

网友询问留言