阅读说明：本技术 聚合性化合物、组合物、聚合物、光学各向异性体、液晶显示元件和有机el元件 (Polymerizable compound, composition, polymer, optically anisotropic body, liquid crystal display element, and organic EL element ) 是由 野濑清香 大桥裕二 间宫纯一 小矶彰宏 山崎龙史 于 2015-12-01 设计创作，主要内容包括：本发明的课题为,提供一种聚合性化合物、包含上述聚合性化合物的组合物、使用了上述聚合性化合物的树脂等、使上述聚合性化合物聚合而得到的聚合物、由上述聚合物构成的光学各向异性体、以及具备上述光学各向异性体的液晶显示元件、有机EL元件,上述聚合性化合物的液晶性良好,取向性良好,具有充分的溶剂溶解性,溶液状态下的保存稳定性高,光学稳定性高。并且,为了解决该课题而进行了积极研究,结果开发了通式(I)所表示的化合物。(The present invention addresses the problem of providing a polymerizable compound, a composition containing the polymerizable compound, a resin or the like using the polymerizable compound, a polymer obtained by polymerizing the polymerizable compound, an optically anisotropic body composed of the polymer, and a liquid crystal display element and an organic EL element each having the optically anisotropic body, wherein the polymerizable compound has good liquid crystallinity, good alignment properties, sufficient solvent solubility, high storage stability in a solution state, and high optical stability. Further, as a result of active studies to solve the problem, compounds represented by the general formula (I) have been developed.)

1. A polymerizable compound represented by the general formula (1),

[ solution 1]

In the formula, P¹And P²Which represents a polymerizable functional group, and a polymerizable functional group,

Sp¹and Sp²Represents a divalent spacer group or a single bond,

A¹and A²Each independently represents a divalent alicyclic hydrocarbon group or aromatic hydrocarbon group having 3 to 20 carbon atoms which is unsubstituted or may be substituted with one or more substituents, any carbon atom of the alicyclic hydrocarbon group or aromatic hydrocarbon group may be substituted with a hetero atom,

Z¹、Z²、Z³and Z⁴Each independently represents a divalent linking group or a single bond,

u represents a trivalent aromatic group which is unsubstituted or may be substituted by one or more substituents,

and Z present and directly linked to U¹And Z present²One or both of them are independently an acyclic aliphatic group having 2 to 20 carbon atoms which is unsubstituted or may be substituted with one or more substituents, one-CH group in the acyclic aliphatic group₂-each independently is substituted by-O-,

t represents a group selected from the following formula (T-1) or formula (T-2),

[ solution 2]

In the formula, Q¹Represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, which is unsubstituted or substituted with one or more substituents,

W¹represents an organic group having 2 to 30 carbon atoms and having an aromatic hydrocarbon group, any carbon atom of which may be substituted with a hetero atom, the aromatic hydrocarbon group being unsubstituted or substituted with one or more substituents,

Y¹an alkane representing a hydrogen atom or a carbon atom number of 1 to 20A group, an alkenyl group having 2 to 20 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, an organic group having 2 to 30 carbon atoms and having an aromatic hydrocarbon group, or- (Z)⁵-A³)q-Z⁶-Sp³-P³Any carbon atom of the aromatic hydrocarbon group may be substituted with a hetero atom, the alkyl group, the alkenyl group and the cycloalkyl group may be unsubstituted or may be substituted with one or more substituents, one-CH in the alkyl group₂-or two or more-CH's which are not contiguous₂May each be independently substituted by-O-, -S-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -SO₂-, -O-CO-O-, -CO-NH-, -NH-CO-, -CH ═ CH-COO-, -CH ═ CH-OCO-, -COO-CH ═ CH-, -OCO-CH ═ CH-, -CF ═ CF-, or-C ≡ C-substitution, Z ≡ CO-O-, -CO-NH-, -NH-CO-, -CH ═ CH-, -CH ≡ CH-, -CF ≡ CF-, or-C ≡ C-substitution, Z-⁵～Z⁶、A³、Sp³、P³Respectively represent the same as Z¹～Z⁴、A¹～A²、Sp¹～Sp²、P¹～P²The same groups as defined, q represents an integer of 0 to 4,

in addition, the W¹And Y¹Can be combined to form a ring,

m and n each independently represent an integer of 0 to 4, wherein m + n is an integer of 1 or more,

A¹、A²、A³、Z¹、Z²、Z⁵when plural, each may be the same or different.

2. The polymerizable compound according to claim 1, wherein in the formula (1), Z³And Z⁴One or both of which are independently-OCO-CH- ＊, -OCO-CH₂CH₂-＊、-COO-CH₂CH₂-＊、-O-CH＝CH-＊、-O-CH₂CH₂- ＊, the radical being bound to A on the side ＊¹Or A²And (4) combining.

3. The polymerizable compound according to claim 1 or 2, wherein in the general formula (1), all A's are present¹And/or all A present²Is unsubstituted or may be substituted by more than oneA divalent alicyclic hydrocarbon group substituted with a substituent.

4. The polymerizable compound according to claim 1 or 2, wherein in the general formula (1), either one of m and n is 0.

5. The polymerizable compound according to claim 1 or 2, wherein in the general formula (1), one or both of m and n are an integer of 2 to 4, and two or more A's are¹And/or more than two A²Each independently represents a divalent aromatic hydrocarbon group which may be substituted by one or more substituents and connects the two or more A' s¹And/or more than two A²Z of (A)¹And/or Z²Not a single bond.

6. The polymerizable compound according to claim 1 or 2, wherein m + n in the general formula (1) is 3.

7. The polymerizable compound according to claim 1 or 2, wherein Sp is represented by the general formula (1)¹And/or Sp²Represents a single bond.

8. The polymerizable compound according to claim 1 or 2, wherein in the formula (1), P is¹And P²Represents a group selected from the following formulae (P-1) to (P-20),

[ solution 3]

9. The polymerizable compound according to claim 1 or 2, wherein in the general formula (1), U represents the following formulae (U-1) to (U-6),

[ solution 4]

More than one hydrogen atom bound to these rings may be replaced by F, Cl, CF₃、OCF₃Cyano, C1-8 alkyl, C1-8 alkoxy, C1-8 alkanoyl, C1-8 alkanoyloxy, C2-8 alkenyl, C2-8 alkenyloxy, C2-8 alkenoyl or C2-8 alkenoyloxy.

10. The polymerizable compound according to claim 1 or 2, wherein W in the formula (1)¹Represented by general formulae (W-1) to (W-20),

[ solution 5]

Wherein these groups may have a bond at any position, Q²represents-O-, -S-, -NR⁴-or-CO-, of formula-NR⁴In, R⁴Represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms; each of-CH ═ in these groups may be independently substituted with-N ═ CH, -CH₂Each independently may be substituted by-O-, -S-, -NR-⁵-, -SO-, or-SO₂-or-CO-substitution, with the exception of the case where the oxygen atoms are bonded directly to one another, of the formula-NR⁵In (A) R⁵Represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms; in addition, these radicals are unsubstituted or may be substituted by more than one L^WSubstituted, L^WRepresents a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfanyl group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, an isothiocyanato group, or an alkyl group having 1 to 20 carbon atoms, which may be linear or branched, any hydrogen atom may be substituted by a fluorine atom, and one-CH group in the alkyl group₂-or two or more-CH's which are not contiguous₂-each independently may be substituted by a group selected from-O-, -S-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -CH ═ CH-COO-, -CH ═ CH-OCO-, -COO-CH ═ CH-, -OCO-CH ═ CH-, -CF ═ CF-, or-C ≡ C-)。

11. A composition comprising the polymerizable compound according to claim 1.

12. A polymer obtained by polymerizing the composition of claim 11.

13. An optically anisotropic body using the polymer according to claim 12.

14. A liquid crystal display element using the optically anisotropic body according to claim 13.

15. An organic EL element using the optically anisotropic body according to claim 13.

16. A resin, a resin additive, an oil, a color filter, an adhesive, a fat or oil, an ink, a pharmaceutical product, a cosmetic product, a detergent, a building material, a packaging material, a liquid crystal material, an organic EL material, an organic semiconductor material, an electronic material, an automobile part, an airplane part, a machine part, an agricultural chemical, a food, and a product using the same, each of which uses the polymerizable compound according to any one of claims 1 to 10.

Technical Field

The present invention relates to a polymerizable compound, a composition, a polymer, an optically anisotropic body, a liquid crystal display device, and an organic EL device.

Background

Optically anisotropic materials such as retardation films and polarizing plates used in liquid crystal displays can be produced as follows: on a substrate subjected to rubbing treatment or on a substrate having a photo-alignment film formed thereonIn order to achieve the above-described optical characteristics of a retardation film, it is required to make the wavelength dispersion of the birefringence (△ n) small or reverse the wavelength dispersion in order to improve the viewing angle of a liquid crystal display, and a development of a reverse dispersion type polymerizable compound (for example, patent document 1) is described in which, in general, when the wavelength λ of incident light to the retardation film is taken as the abscissa and the birefringence (△ n ═ the refractive index n with respect to extraordinary rays) is taken as the abscissa_e-refractive index n with respect to ordinary light₀) When the slope of the curve plotted on the vertical axis is positive (continuously rising), the wavelength dispersion of the birefringence is reversed, or the polymerizable compound constituting the material of the retardation film is of the reverse dispersion type.

In order to make the polymerizable compound constituting the retardation film a reverse dispersion type, there is a method comprising: a site (vertical unit) having a large birefringence in a direction perpendicular to the long axis of the molecule is introduced into the molecule. However, since the introduction of the homeotropic element tends to deteriorate liquid crystallinity and deteriorate orientation, a large number of trial and error are required to obtain a polymerizable compound that does not disturb orientation.

In addition, when the polymerizable compound is applied to the substrate, it is necessary to dissolve an appropriate amount of the polymerizable compound in a solvent which does not attack the substrate. However, the introduction of the vertical unit may lower the solubility in a solvent, which may cause problems such as failure to obtain a solution of a sufficient concentration and precipitation of crystals during storage.

Further, the absorption spectrum of the polymerizable compound changes due to the introduction of the vertical units, and in many cases, the absorption becomes longer. This may cause a decrease in optical stability, and may cause yellowing, cracking, and the like of the retardation film.

Disclosure of Invention

Problems to be solved by the invention

The present invention has been made in view of the above circumstances, and an object thereof is to provide a polymerizable compound having good liquid crystallinity, good orientation, sufficient solvent solubility, high storage stability in a solution state, and high optical stability; a composition containing the polymerizable compound; a resin, a resin additive, oil, a color filter, an adhesive, a pressure-sensitive adhesive, grease, ink, a pharmaceutical product, a cosmetic product, a detergent, a building material, a packaging material, a liquid crystal material, an organic EL material, an organic semiconductor material, an electronic material, an automobile part, an airplane part, a mechanical part, an agricultural chemical, a food, and a product using the same, each using the polymerizable compound; a polymer obtained by polymerizing the polymerizable compound; an optically anisotropic body composed of the polymer; and a liquid crystal display element and an organic EL element each comprising the optically anisotropic body.

Means for solving the problems

The present inventors have conducted intensive studies to solve the above problems, and as a result, have developed a compound represented by the following general formula (I). Namely, the present invention provides a polymerizable compound represented by the general formula (1),

[ solution 1]

(in the formula, P¹And P²Which represents a polymerizable functional group, and a polymerizable functional group,

Sp¹and Sp²Represents a divalent spacer group or a single bond,

A¹and A²Each independently represents a divalent alicyclic hydrocarbon group or aromatic hydrocarbon group having 3 to 20 carbon atoms which is unsubstituted or may be substituted with one or more substituents, any carbon atom of the alicyclic hydrocarbon group or aromatic hydrocarbon group may be substituted with a hetero atom,

Z¹、Z²、Z³and Z⁴Each independently represents a divalent linking group or a single bond,

u represents a trivalent aromatic group which is unsubstituted or may be substituted by one or more substituents,

t represents a group of the formula (T-1) or (T-2) selected from,

[ solution 2]

(in the formula, wherein,

Q¹represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, which is unsubstituted or substituted with one or more substituents,

W¹represents an organic group having 2 to 30 carbon atoms and having an aromatic hydrocarbon group which is unsubstituted or substituted with one or more substituents, any carbon atom of the aromatic hydrocarbon group may be substituted with a hetero atom,

Y¹represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, an organic group having 2 to 30 carbon atoms and having an aromatic hydrocarbon group in which any carbon atom may be substituted with a hetero atom, or- (Z)⁵-A³)q-Z⁶-Sp³-P³The alkyl, alkenyl and cycloalkyl groups being unsubstituted or substituted by more than one substituent, one-CH of the alkyl groups₂-or two or more-CH's which are not contiguous₂Each independently may be substituted by-O-, -S-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, SO₂-, -O-CO-O-, -CO-NH-, -NH-CO-, -CH ═ CH-COO-, -CH ═ CH-OCO-, -COO-CH ═ CH-, -OCO-CH ═ CH-, -CF ═ CF-, or-C ≡ C-substitution, Z ≡ CO-O-, -CO-NH-, -NH-CO-, -CH ═ CH-, -CH ≡ CH-, -CF ≡ CF-, or-C ≡ C-substitution, Z-⁵～Z⁶、A³、Sp³、P³Respectively represent the same as Z¹～Z⁴、A¹～A²、Sp¹～Sp²、P¹～P²The same groups as defined, q represents an integer of 0 to 4,

further, W is as defined above¹And Y¹May be combined to form a ring. )

m and n each independently represent an integer of 0 to 4 (wherein m + n is an integer of 1 or more),

A¹、A²、A³、Z¹、Z²、Z⁵when plural, each may be the same or different. )

Also disclosed is a composition containing such a polymerizable compound; a resin, a resin additive, oil, a color filter, an adhesive, grease, ink, a pharmaceutical, a cosmetic, a detergent, a building material, a packaging material, a liquid crystal material, an organic EL material, an organic semiconductor material, an electronic material, an automobile part, an airplane part, a mechanical part, an agricultural chemical, and a food each using the polymerizable compound, and a product using the same; a polymer obtained by polymerizing the composition, and an optically anisotropic body, a liquid crystal display device, and an organic EL device each using the polymer.

Effects of the invention

By using the polymerizable compound of the present invention, an optically anisotropic body having excellent optical properties can be produced. In addition, a liquid crystal display element and an organic EL element with improved viewing angles can be manufactured.

Detailed Description

The present invention will be described below based on preferred embodiments, but the present invention is not limited to these embodiments.

Polymerizable Compound

The polymerizable compound of the present invention is a compound represented by the following general formula (1).

The compound represented by the general formula (1) may or may not exhibit liquid crystallinity alone. When the compound represented by the general formula (1) alone does not exhibit liquid crystallinity, it is preferable that the compound is mixed with other components exhibiting liquid crystallinity to exhibit liquid crystallinity. The compound represented by the general formula (1) more preferably has liquid crystallinity before polymerization. That is, the compound represented by the general formula (1) is preferably a polymerizable liquid crystal compound.

<P¹And P²>

P in the general formula (1)¹And P²The polymerizable functional group can be a conventional polymerizable liquid crystal compound without limitationGroups used in (A) to (B).

Polymerizable functional group P¹And P²Each independently preferably represents a group selected from the following formulae (P-1) to (P-20),

[ solution 3]

These polymerizable groups are polymerized by radical polymerization, radical addition polymerization, cationic polymerization, and anionic polymerization. In particular, when ultraviolet polymerization is carried out as the polymerization method, the compound of the formula (P-1), the formula (P-2), the formula (P-3), the formula (P-4), the formula (P-5), the formula (P-7), the formula (P-11), the formula (P-13), the formula (P-15) or the formula (P-18) is preferable, the compound of the formula (P-1), the formula (P-2), the formula (P-7), the formula (P-11) or the formula (P-13) is more preferable, the compound of the formula (P-1), the formula (P-2) or the formula (P-3) is further preferable, and the compound of the formula (P-1) or the formula (P-2) is particularly preferable.

<Sp¹And Sp²>

Sp in the general formula (1)¹And Sp²Is a divalent spacer or a single bond. The spacer is a functional group P capable of linking with the polymerizable group¹And Z³Or P²And Z⁴The 2-valent linking group (2) is preferably a linking group which does not impair the liquid crystallinity of the polymerizable compound represented by the general formula (1).

As appropriate represents Sp¹And Sp²Examples of the divalent spacer in (2) include a linear alkylene group having 1 to 20 carbon atoms. One CH present in the alkylene radical₂Radicals or two or more non-adjacent CH₂The radicals may each, independently of one another, be-O-, -S-, -NH-, -N (CH) in the form of oxygen atoms which are bonded to one another, sulfur atoms which are bonded to one another, and oxygen atoms which are not bonded to sulfur atoms which are bonded directly to one another₃) -, -CO-, -COO-, -OCO-, -OCOO-, -SCO-, -COS-, -CH-or-C.ident.C-are substituted in P¹-Sp¹、Sp¹-Z³、Z⁴-Sp²、Sp²-P²In the bond(s) of (a), an-O-bond is not formed. The alkylene group preferably has 2 to 10, more preferably 3 to 8, and still more preferably has 2 to 10 carbon atoms from the viewpoint of improving liquid crystallinityAnd selecting 3-6.

In addition, Sp is suitable¹And Sp²，Sp¹And/or Sp²Single bonds may also be mentioned. Will use Sp¹And/or Sp²Since the optical stability of the polymer obtained by polymerizing the composition of the compound represented by the general formula (1) of the present invention, which is a single bond, can be improved, when the optical stability needs to be improved, at least Sp is preferably used¹And Sp²One of them is a single bond, more preferably Sp¹And Sp²Are all single bonds.

<A¹And A²>

A in the general formula (1)¹And A²Each independently represents a divalent alicyclic hydrocarbon group or aromatic hydrocarbon group having 3 to 20 carbon atoms which is unsubstituted or may be substituted with one or more substituents, any carbon atom of the alicyclic hydrocarbon group or aromatic hydrocarbon group may be substituted with a hetero atom, and more specifically, any carbon atom of the alicyclic hydrocarbon group or aromatic hydrocarbon group may be substituted with an oxygen atom, a sulfur atom or a nitrogen atom. The aromatic hydrocarbon group may be an aromatic heterocyclic group, may have a condensed ring structure, or may be a structure obtained by condensing an alicyclic hydrocarbon group and an aromatic hydrocarbon group. In the specification, A is¹And/or A²When plural, each may be the same or different.

Examples of the alicyclic hydrocarbon group and the aromatic hydrocarbon group include a 1, 4-phenylene group, a 1, 4-cyclohexylene group, a 1, 4-cyclohexenylene group, a tetrahydropyran-2, 5-diyl group, and a 1, 3-diyl groupAlkane-2, 5-diyl, tetrahydrothiopyran-2, 5-diyl, 1, 4-bicyclo (2,2,2) octylene, decahydronaphthalene-2, 6-diyl, pyridine-2, 5-diyl, pyrimidine-2, 5-diyl, pyrazine-2, 5-diyl, 1,2,3, 4-tetrahydronaphthalene-2, 6-diyl, naphthalene-2, 6-diyl, phenanthrene-2, 7-diyl, 9, 10-dihydrophenanthrene-2, 7-diyl, 1,2,3,4,4a,9,10 a-octahydrophenanthrene-2, 7-diyl, or fluorene 2, 7-diyl, and the like, and the above alicyclic hydrocarbon group and aromatic hydrocarbon group are unsubstituted or may be substituted with one or more substituents L.

The substituent L represents a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfanyl group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, an isothiocyanato group, or a-CH group₂-or two or more-CH's which are not contiguous₂-a linear or branched alkyl group having 1 to 20 carbon atoms which may be independently substituted with-O-, -S-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -CH ═ CH-COO-, -CH ═ CH-OCO-, -COO-CH ═ CH-, -OCO-CH ═ CH-, -CF ≡ CF-, or-C ≡ C-, any hydrogen atom in the alkyl group may be substituted with a fluorine atom, or L may represent P ≡ C-, or L may represent P ≡ C-, or a pharmaceutically acceptable salt thereof^L-(Sp^L-X^L)_kL-a group represented by, wherein P^LRepresents a polymerizable group Sp^LRepresents a spacer group or a single bond, and examples of the spacer group include the groups exemplified as the divalent spacer group, Sp^LWhen plural, they may be the same or different, X^Lrepresents-O-, -S-, -OCH₂-、-CH₂O-、-CO-、-COO-、-OCO-、-CO-S-、-S-CO-、-O-CO-O-、-CO-NH-、-NH-CO-、-SCH₂-、-CH₂S-、-CF₂O-、-OCF₂-、-CF₂S-、-SCF₂-、-CH＝CH-COO-、-CH＝CH-OCO-、-COO-CH＝CH-、-OCO-CH＝CH-、-COO-CH₂CH₂-、-OCO-CH₂CH₂-、-CH₂CH₂-COO-、-CH₂CH₂-OCO-、-COO-CH₂-、-OCO-CH₂-、-CH₂-COO-、-CH₂-OCO-, -CH ═ CH-, -N ═ N-, -CH ═ N-N ═ CH-, -CF ═ CF-, -C ≡ C-, or a single bond, X ≡ C-, or^LWhen plural, they may be the same or different (wherein P is^L-(Sp^L-X^L)_kL-does not comprise an-O-bond. ) kL represents an integer of 0 to 10, and when a plurality of L's are present in the compound, they may be the same or different. From the viewpoint of liquid crystallinity and ease of synthesis, L preferably represents a fluorine atom, a chlorine atom, a pentafluorosulfanyl group, a nitro group, a methylamino group, a dimethylamino group, a diethylamino group, or a di-amino groupIsopropylamino, or any hydrogen atom may be substituted by fluorine atoms and one-CH₂-or two or more-CH's which are not contiguous₂-a linear or branched alkyl group having 1 to 20 carbon atoms which may be independently substituted by a group selected from-O-, -S-, -CO-, -COO-, -OCO-, -O-CO-O-, -CH ═ CH-, -CF ═ CF-and-C ≡ C-, more preferably a fluorine atom, a chlorine atom or an arbitrary hydrogen atom which may be substituted by a fluorine atom and one-CH-may be mentioned₂-or two or more-CH's which are not contiguous₂-a linear or branched alkyl group having 1 to 12 carbon atoms which may be independently substituted by a group selected from-O-, -COO-and-OCO-, more preferably a linear or branched alkyl group having 1 to 12 carbon atoms which may be substituted by a fluorine atom, a chlorine atom or an arbitrary hydrogen atom, and an alkoxy group, and particularly preferably a fluorine atom, a chlorine atom or a linear alkyl group having 1 to 8 carbon atoms or a linear alkoxy group.

A in the general formula (1)¹And A²Each independently is preferably a 1, 4-phenylene, naphthalene-2, 6-diyl or 1, 4-cyclohexylene group which is unsubstituted or may be substituted by one or more of the above-mentioned substituents L, and more preferably a 1, 4-phenylene or 1, 4-cyclohexylene group. These groups can easily improve the liquid crystallinity of the polymerizable compound of the present embodiment, and improve the orientation of the polymer.

In addition, all A's present in the general formula (1)¹And/or all A present²Also preferred is a divalent alicyclic hydrocarbon group which may have a substituent (for example, A)¹When a plurality of occurrences occur, all A's of the plurality occur¹Divalent alicyclic hydrocarbon groups are preferred. ) Specifically, it is preferably selected from the group consisting of 1, 4-cyclohexylene group, 1, 4-cyclohexenylene group, tetrahydropyran-2, 5-diyl group and 1, 3-diyl groupAlkyl-2, 5-diyl radical, more preferably A¹And A²Are each selected from 1, 4-cyclohexylene, 1, 4-cyclohexenylene, tetrahydropyran-2, 5-diyl or 1, 3-diylAlk-2, 5-diylA group of (1). These groups are preferable because the solubility of the polymerizable compound of the present embodiment and the reverse dispersibility of the polymer can be easily improved, and particularly when 1, 4-cyclohexylene is used, the solubility of the polymerizable compound of the present embodiment and the reverse dispersibility of the polymer can be easily improved. From this viewpoint, A is¹And A²When a plurality of them are present, for example, when m and n each represents 2 as described later, the presence of two A's is more preferable¹Both represent 1, 4-cyclohexylene, and/or two A's present²Both represent 1, 4-cyclohexylene.

<Z¹、Z²、Z³And Z⁴>

Z in the general formula (1)¹、Z²、Z³And Z⁴Each independently represents a divalent linking group or a single bond. It is to be noted that Z¹And/or Z²When plural, each may be the same or different.

Z¹、Z²、Z³And Z⁴Each independently preferably is a non-cyclic aliphatic group having 1 to 20 carbon atoms (one-CH in the non-cyclic aliphatic group)₂-or two or more-CH's which are not contiguous₂Each independently may be substituted by-O-, -S-, -COO-, -OCO-, -CO-S-, -S-CO-, -OCF₂-、-CF₂O-、-SCF₂-、-CF₂S-、-CF＝CF-、-O-COO-、-NR³-CO-、-CO-NR³-、-NR³-COO-、-OCO-NR³-or-OCO-COO-substituted, where R is³Represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. ) C ≡ C-, -N ═ N-, -C ═ N-, -N ═ C-, -C ═ N ═ C-, -CH ═ CH-COO-, -OCO-CH ═ C-, -OCO-COO-, or a single bond. The acyclic aliphatic group having 1 to 20 carbon atoms includes an alkylene group having 1 to 20 carbon atoms, an alkenylene group having 2 to 20 carbon atoms, and the like. Wherein, when the acyclic aliphatic group having 1 to 20 carbon atoms is an alkylene group having 1 carbon atom, the group represents-CH when unsubstituted₂-, for example, when substituted by-O-, denotes-O-. As Z¹And Z²More, moreSpecifically, from the viewpoint of liquid crystallinity, availability of raw materials and ease of synthesis, a plurality of the units may be the same or different, and each of the units independently preferably represents-OCH₂-、-CH₂O-、-COO-、-OCO-、-CF₂O-、-OCF₂-、-CH₂CH₂-、-CF₂CF₂-、-CH＝CH-COO-、-CH＝CH-OCO-、-COO-CH＝CH-、-OCO-CH＝CH-、-COO-CH₂CH₂-、-OCO-CH₂CH₂-、-CH₂CH₂-COO-、-CH₂CH₂-OCO-, -CH ═ CH-, -CF ═ CF-, -C ≡ C-, or a single bond, more preferably-OCH₂-、-CH₂O-、-COO-、-OCO-、-CF₂O-、-OCF₂-、-CH₂CH₂-、-COO-CH₂CH₂-、-OCO-CH₂CH₂-、-CH₂CH₂-COO-、-CH₂CH₂-OCO-, -CH-, -C.ident.C-or a single bond, and further preferably represents-OCH₂-、-CH₂O-、-COO-、-OCO-、-CF₂O-、-OCF₂-or a single bond, even more preferably-OCH₂-、-CH₂O-, -COO-, -OCO-or a single bond, particularly preferably-OCH₂-、-CH₂O-, -COO-or-OCO-.

As Z³And Z⁴More specifically, each independently preferably represents-O-, -S-, -OCH₂-、-CH₂O-、-COO-、-OCO-、-CO-S-、-S-CO-、-O-CO-O-、-CO-NH-、-NH-CO-、-COO-CH₂CH₂-、-OCO-CH₂CH₂-、-CH₂CH₂-COO-、-CH₂CH₂A plurality of-OCO-or single bonds, each of which may be the same or different, each independently represents-O-, -OCH₂-、-CH₂O-、-COO-、-OCO-、-COO-CH₂CH₂-、-OCO-CH₂CH₂-、-CH₂CH₂-COO-、-CH₂CH₂A plurality of-OCO-or single bonds, each of which may be the same or different, each independently represent-O-, -,-COO-, -OCO-or a single bond.

<<Z directly bound to U¹And Z²>>

Z in the general formula (1)¹、Z²、Z³And Z⁴Z represents a divalent linking group or a single bond selected from the above groups, Z is present and is directly linked to U¹And Z present²Is preferably selected from-CH₂A non-cyclic aliphatic group having 2 to 20 carbon atoms (one-CH group in the non-cyclic aliphatic group) which is unsubstituted or may be substituted with one or more substituents₂-or two or more-CH's which are not contiguous₂Each independently may be substituted by-O-, -S-, -COO-, -OCO-, -CO-S-, -S-CO-, -OCF₂-、-CF₂O-、-SCF₂-、-CF₂S-、-CF＝CF-、-O-COO-、-NR³-CO-、-CO-NR³-、-NR³-COO-、-OCO-NR³-or-OCO-COO-substituted but with at least one-CH₂-. Where R is³Represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. ) A linking group selected from-C.ident.C-, -N-, -C-N-, -N-C-, -C-N-C-, -CH-COO-, -OCO-CH-C-and-OCO-COO-. More specifically, Z present and directly linked to U¹And Z present²One or both of them independently preferably represent-OCH₂-、-CH₂O-、-CH₂CH₂-、-CH＝CH-COO-、-OCO-CH＝CH-、-COO-CH₂CH₂-、-OCO-CH₂CH₂-、-CH₂CH₂-COO-、-CH₂CH₂-OCO-, -C.ident.C-or a single bond, more preferably-OCH₂-、-CH₂O-、-COO-CH₂CH₂-、-CH₂CH₂-OCO-。

Z present directly linked to U¹And Z present²When one or both of them are the above-mentioned preferable linking groups, the orientation of the polymer can be easily improved without impairing the liquid crystal property of the polymerizable compound of the present embodiment. Presumably through sites (vertical cells) having a large volume in the direction perpendicular to the long axis of the moleculeThe linking group is introduced laterally to contribute to the improvement of the orientation. When m and n, which will be described later, are each an integer of 2 or more, Z directly bonded to U¹And Z²Has the above-mentioned specific linking group, a plurality of Z's are present¹And Z²The other group(s) may be selected from any of the above-mentioned divalent linking groups or single bonds.

<<Z³And Z⁴>>

Z in the general formula (1)³And Z⁴Represents a group selected from the divalent linking groups or single bonds described above,

Z³and Z⁴One or both of which are independently selected from-OCO-CH ═ CH- ＊, -OCO-CH₂CH₂-＊、-COO-CH₂CH₂-＊、-O-CH＝CH-＊、-O-CH₂CH₂- ＊ (the group is on side ＊ from A)¹Or A²In the case where m is 0 or n is 0, the group is preferably bonded to a at the ＊ side¹Or A²The bond is to the U-ring.

In addition, Z is as defined above³And Z⁴When one or both of them are the above-mentioned specific linking group, Sp is preferably used¹And/or Sp²Not a single bond but an arbitrary spacer. Further, Z is more preferably Z³And Z⁴One or both of which are independently selected from-OCO-CH ═ CH-, -OCO-CH₂CH₂-, -CH ═ CH-COO-or-CH₂CH₂-COO-or a linker group.

<m、n>

M and n in the general formula (1) independently represent an integer of 0 to 4, and m + n is an integer of 1 or more.

When importance is attached to the solvent solubility and the storage stability of the polymerizable compound of the present embodiment, either one of m and n is preferably 0.

When importance is attached to liquid crystallinity and orientation, one or both of m and n are preferably an integer of 2 to 4, more preferably both of m and n are an integer of 2 to 4, and further more preferably both of m and n are an integer of 2 to 4Preferably, both m and n are 2. When one or both of m and n are integers of 2 to 4, two or more of A are mentioned¹And/or more than two A²Each independently represents a divalent aromatic hydrocarbon group which may be substituted by one or more substituents, and preferably connects the two or more A' s¹And/or more than two A²Z of (A)¹And/or Z²Not a single bond. That is, for example, when m is 2, -A¹²-Z¹²-A¹¹-Z¹¹In the linking moiety represented by-U-, A is preferred¹²、A¹¹Represents a divalent aromatic hydrocarbon group which is unsubstituted or may be substituted by one or more substituents, and Z¹²Is a linking group other than a single bond.

When importance is attached to liquid crystallinity, a high liquid crystal phase temperature, and storage stability when dissolved in a solvent, one or both of m and n are preferably 1 or 2, and m + n is particularly preferably 3. More specifically, compounds represented by the following general formula (1-k) are preferred.

[ solution 4]

(in the formula, P¹、P²、Sp¹、Sp²、Z³、Z⁴、U、Q¹、W¹And Y¹Represents the same meaning as in the general formula (1), A¹⁹、A²⁹And A²¹⁰Each independently represents 1, 4-cyclohexylene or 1, 4-phenylene, the 1, 4-phenylene being unsubstituted or may be substituted by more than one substituent L¹¹Substituted, L¹¹Represents a fluorine atom, a chlorine atom, or a-CH₂-or two or more-CH's which are not contiguous₂-a linear or branched alkyl group having 1 to 20 carbon atoms which may be independently substituted with-O-, -CO-, -COO-or-OCO-, wherein any hydrogen atom in the alkyl group may be substituted with a fluorine atom, and wherein a plurality of L's are present in the compound¹¹When they are the same or different, Z¹⁹、Z²⁹And Z²¹⁰Each independently represents-OCH₂-、-CH₂O-、-COO-、-OCO-、-CF₂O-、-OCF₂-、-CH₂CH₂-、-CF₂CF₂-、-CH＝CH-COO-、-CH＝CH-OCO-、-COO-CH＝CH-、-OCO-CH＝CH-、-COO-CH₂CH₂-、-OCO-CH₂CH₂-、-CH₂CH₂-COO-、-CH₂CH₂-OCO-, -CH ═ CH-, -CF ═ CF-, -C ≡ C-, or a single bond. ) In the compound represented by the above formula (1-k), Z is Z from the viewpoint of ease of synthesis²⁹More preferably represents-OCH₂-、-CH₂O-、-CF₂O-、-OCF₂-、-CH₂CH₂-、-CF₂CF₂-、-COO-CH₂CH₂-、-CH₂CH₂-OCO-, -CH ═ CH-, -CF ═ CF-, -C ≡ C-, or a single bond, with a single bond being particularly preferred. In addition, A¹⁹And A²¹⁰More preferably represents an unsubstituted or optionally substituted substituent L¹¹Substituted 1, 4-phenylene.

<U>

In the general formula (1), the U ring represents a trivalent aromatic group which may have a substituent. The aromatic group is preferably a group selected from the following formulae (U-1) to (U-6),

[ solution 5]

More preferably a group selected from the group of formula (U-1) or formula (U-2). More than one hydrogen atom bound to these rings may be replaced by F, Cl, CF₃、OCF₃Cyano, nitro, amino, methylamino, dimethylamino, alkyl with 1-8 carbon atoms, alkoxy with 1-8 carbon atoms, alkanoyl with 1-8 carbon atoms, alkanoyloxy with 1-8 carbon atoms, alkenyl with 2-8 carbon atoms, alkenyloxy with 2-8 carbon atoms, alkenoyl with 2-8 carbon atoms or alkenoyloxy with 2-8 carbon atoms.

<Q¹>

In the general formula (1), Q¹Represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, which is unsubstituted or may be substitutedOne or more substituents may be substituted, and one or more hydrogen atoms bonded to the alkyl group may be replaced by F, Cl or CF₃、OCF₃Cyano group, an aromatic hydrocarbon group having 3 to 20 carbon atoms, Q¹Preferably a hydrogen atom, or an alkyl group having 1 to 6 carbon atoms which is unsubstituted or substituted with one or more F, Q¹More preferably a hydrogen atom.

<W¹>

W¹The organic group has 2-30 carbon atoms and at least one aromatic ring selected from the group consisting of aromatic hydrocarbon rings and aromatic heterocyclic rings. The aromatic ring is preferably a group selected from the following formulae (W-1) to (W-20).

[ solution 6]

These groups may have a bond at any position. Q²represents-O-, -S-, -NR⁴- (in the formula, R⁴Represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms. ) or-CO-, in which each-CH independently may be substituted by-N, -CH₂Each independently may be substituted by-O-, -S-, -NR-⁵- (in the formula, R⁵Represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms. ) -SO-, or-SO₂-or-CO-substitution (with the exception of the case where the oxygen atoms are bonded directly to each other). More than one hydrogen atom bound to these rings may be replaced by L^WSubstituted, substituent L^WRepresents a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfanyl group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, an isothiocyanato group, or an alkyl group having 1 to 20 carbon atoms, which may be linear or branched, any hydrogen atom may be substituted by a fluorine atom, and one-CH group in the alkyl group₂-or two or more-CH's which are not contiguous₂Each independently may be selected from-O-, -S-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -CH ═ CH-COO-, -CH ═ CH-OCO-, -COO-CH ═ CH-, -OCO-CH ═ CH-, -CF ═ CF-, or-C ≡ C-. Examples of the alkyl group and the alkyl group constituting the alkoxy group include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, and a hexyl group. The alkyl group preferably has 1 to 4 carbon atoms, more preferably 1 or 2 carbon atoms, and still more preferably 1 carbon atom.

The group represented by the formula (W-1) preferably represents an unsubstituted or optionally substituted group represented by one or more L^WA substituted group selected from the following formulas (W-1-1) to (W-1-8),

[ solution 7]

These groups may have a bond at any position.

The group represented by the formula (W-7) is preferably unsubstituted or may be substituted by one or more L^WA substituted group selected from the following formulae (W-7-1) to (W-7-7),

[ solution 8]

These groups may have a bond at any position.

The group represented by the formula (W-10) preferably represents an unsubstituted or optionally substituted group represented by one or more L^WSubstituted groups selected from the following formulae (W-10-1) to (W-10-8).

[ solution 9]

(in the formula, R^TRepresents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. These groups may have a bond at any position. )

The group represented by the formula (W-11) preferably represents an unsubstituted or optionally substituted group represented by one or more L^WSubstituted is selected fromA group of the following formulae (W-11-1) to (W-11-12).

[ solution 10]

(in the formula, R^TRepresents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. These groups may have a bond at any position. )

The group represented by the formula (W-13) is preferably unsubstituted or may be substituted by one or more L^WSubstituted groups selected from the following formulae (W-13-1) to (W-13-19).

[ solution 11]

(in the formula, R^TRepresents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. These groups may have a bond at any position. )

The group represented by the formula (W-14) is preferably unsubstituted or may be substituted by one or more L^WSubstituted groups selected from the following formulae (W-14-1) to (W-14-10).

[ solution 12]

(in the formula, R^TRepresents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. These groups may have a bond at any position. )

The group represented by the formula (W-15) preferably represents an unsubstituted or optionally substituted group represented by one or more L^WSubstituted groups selected from the following formulae (W-15-1) to (W-15-4).

[ solution 13]

(in the formula, R^TRepresents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. TheseThe group may have a bond at any position. )

The group represented by the formula (W-16) preferably represents an unsubstituted or optionally substituted group represented by one or more L^WSubstituted groups selected from the following formulae (W-16-1) to (W-16-16).

[ solution 14]

(in the formula, R^TRepresents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. These groups may have a bond at any position. )

The group represented by the formula (W-17) preferably represents an unsubstituted or optionally substituted group represented by one or more L^WSubstituted groups selected from the following formulae (W-17-1) to (W-17-4).

[ solution 15]

(in the formula, R^TRepresents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. These groups may have a bond at any position. )

The group represented by the formula (W-18) preferably represents an unsubstituted or optionally substituted group represented by one or more L^WSubstituted groups selected from the following formulae (W-18-1) to (W-18-6).

[ solution 16]

(in the formula, R^TRepresents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. These groups may have a bond at any position. )

The group represented by the formula (W-19) preferably represents an unsubstituted or optionally substituted group represented by one or more L^WSubstituted groups selected from the following formulae (W-19-1) to (W-19-6).

[ solution 17]

(in the formula, R^TRepresents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. These groups may have a bond at any position. )

The group represented by the formula (W-20) preferably represents an unsubstituted or optionally substituted group represented by one or more L^WSubstituted groups selected from the following formulae (W-20-1) to (W-20-9).

[ solution 18]

(in the formula, R^TRepresents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. These groups may have a bond at any position. )

W¹The aromatic group contained more preferably represents unsubstituted or may be substituted by one or more L^WSubstituted groups selected from the above-mentioned formula (W-1-1), formula (W-7-2), formula (W-7-7), formula (W-8), formula (W-10-6), formula (W-10-7), formula (W-10-8), formula (W-11-9), formula (W-11-10), formula (W-11-11) or formula (W-11-12), particularly preferably represent unsubstituted or may be substituted by more than one L^WSubstituted groups selected from the group consisting of formula (W-1-1), formula (W-7-2), formula (W-7-7), formula (W-10-6), formula (W-10-7) or formula (W-10-8). Further, W¹Particularly preferably represents a group of the formula (W-a-1) to (W-a-6) selected from the group consisting of the following.

[ solution 19]

(wherein r represents an integer of 0 to 5, s represents an integer of 0 to 4, and t represents an integer of 0 to 3.)

<Y¹>

Y¹Represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, or an aromatic hydrocarbon group (any carbon atom of the aromatic hydrocarbon group may be substituted with a hetero atom)) An organic group having 2 to 30 carbon atoms or- (Z)⁵-A³)q-Z⁶-Sp³-P³The alkyl, alkenyl and cycloalkyl groups being unsubstituted or substituted by more than one substituent, one-CH of the alkyl groups₂-or two or more-CH's which are not contiguous₂Each independently may be substituted by-O-, -S-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -SO₂-, -O-CO-O-, -CO-NH-, -NH-CO-, -CH ═ CH-COO-, -CH ═ CH-OCO-, -COO-CH ═ CH-, -OCO-CH ═ CH-, -CF ═ CF-, or-C ≡ C-substitution. Here, Z⁵～Z⁶、A³、Sp³、P³Respectively represent the same as Z¹～Z⁴、A¹～A²、Sp¹～Sp²、P¹～P²The same groups as defined above, and q represents an integer of 0 to 4. Further, W is as defined above¹And Y¹A combination may be made.

When importance is attached to the reverse dispersibility and the liquid crystallinity, Y¹Preferably a hydrogen atom.

When importance is attached to the stability of retardation when the composition is dissolved in an organic solvent and hardly undergoes deterioration during long-term storage, or when the composition is added to the composition and hardly undergoes deterioration during long-term storage or when the composition is formed into a film, Y is¹Preferably means that any hydrogen atom in the group may be replaced by a fluorine atom and one-CH₂-or two or more-CH's which are not contiguous₂-a linear or branched alkyl group having 1 to 20 carbon atoms which may be independently substituted with-O-, -CO-, -COO-, -OCO-, or- (Z)⁵-A³)q-Z⁶-Sp³-P³The group shown. In the above groups, Y¹Even more preferably represents a-CH₂-or two or more-CH's which are not contiguous₂-a linear alkyl group having 1 to 12 carbon atoms which may be independently substituted with-O-, or- (Z)⁵-A³)q-Z⁶-Sp³-P³The group shown. Z⁵～Z⁶、A³And P³Are each as defined above for Z¹～Z⁴、A¹～A²、P¹～P²In the same way, the first and second,sp from the viewpoint of reducing curing shrinkage during film formation³Preferably a spacer group, more preferably represents a-CH₂-or two or more-CH's which are not contiguous₂An alkylene group having 1 to 20 carbon atoms which may be independently substituted by-O-, -COO-, -OCO-O-, -CO-NH-, -NH-CO-, -CH ≡ CH-or-C.ident.C-, and more preferably represents one-CH group from the viewpoint of ease of synthesis₂-or two or more-CH's which are not contiguous₂An alkylene group having 1 to 20 carbon atoms each independently being optionally substituted with-O-, and q preferably represents an integer of 0 to 4, more preferably an integer of 0 to 2, further preferably 0 or 1, and particularly preferably 0. More specifically, from the viewpoint of ease of synthesis, Y¹More preferably represents a-CH₂-or two or more-CH's which are not contiguous₂-a linear or branched alkyl group having 1 to 20 carbon atoms which may be independently substituted by-O-, or-Z⁶¹-Sp³¹-P³¹Group (in the formula, P)³¹Represents a group selected from the above-mentioned formulae (P-1) to (P-20), Sp³¹Represents a-CH₂-or two or more-CH's which are not contiguous₂A linear alkylene group having 1 to 20 carbon atoms which may be independently substituted with-O-, -COO-, -OCO-O-, Z⁶¹represents-O-, -S-, -CO-, -COO-, -OCO-, -O-CO-O-, -CO-NH-, -NH-CO-, -CF₂O-、-OCF₂-or a single bond. ) Y is¹Further preferably represents a-CH₂-or two or more-CH's which are not contiguous₂-a linear alkyl group having 1 to 12 carbon atoms which may be independently substituted with-O-, or-Sp³¹¹-P³¹¹Group (in the formula, P)³¹¹Represents a group selected from the above-mentioned formula (P-1) or formula (P-2), Sp³¹¹Represents a-CH₂-or two or more-CH's which are not contiguous₂-a linear alkylene group having 1 to 10 carbon atoms which may each independently be substituted by-O-. ).

When importance is attached to the balance among the inverse dispersibility, the low refractive index anisotropy, and the liquid crystallinity, the following general formula (1-f-i) and general formula (1-f-ii) are preferable.

[ solution 20]

(in the formula, P¹、P²、Sp¹、Sp²、Z³、Z⁴、U、Q¹、W¹And Y¹Represents the same meaning as in the general formula (1), A¹¹、A¹²、A²¹、A²²、A¹³And A²³Represents 1, 4-cyclohexylene, Z¹¹And Z²²Each independently represents-OCH₂-、-CH₂O-, -COO-, -OCO-or a single bond, Z¹²、Z²¹、Z¹³And Z²³Each independently represents-OCH₂-、-CH₂O-, -COO-or-OCO-. )

When importance is attached to the balance of the reverse dispersibility, the high refractive index anisotropy, and the high liquid crystallinity when added to the composition, the following general formula (1-c-i) and general formula (1-c-ii) are preferable,

[ solution 21]

(in the formula, P¹、P²、Sp¹、Sp²、Z³、Z⁴、U、Q¹、W¹And Y¹Represents the same meaning as in the general formula (1), A¹⁴、A²⁵、A¹⁶And A²⁶Each independently represents a 1, 4-phenylene group which is unsubstituted or may be substituted by more than one substituent L¹¹Substituted, L¹¹Represents a fluorine atom, a chlorine atom, or a-CH₂-or two or more-CH's which are not contiguous₂-a linear or branched alkyl group having 1 to 20 carbon atoms which may be independently substituted with-O-, -CO-, -COO-or-OCO-, wherein any hydrogen atom in the alkyl group may be substituted with a fluorine atom, and wherein a plurality of L's are present in the compound¹¹When they are the same or different, A¹⁵And A²⁴Represents 1, 4-cyclohexylene, Z¹⁴And Z²⁵Each independently represents-OCH₂-、-CH₂O-, -COO-, -OCO-or a single bond, Z¹⁵、Z²⁴、Z¹⁶And Z²⁶Each independently represents-OCH₂-、-CH₂O-、-COO-CH₂CH₂-、-CH₂CH₂-OCO-, -COO-or-OCO-, Z¹⁵And Z²⁴At least one of the above and Z¹⁶And Z²⁶At least one of them is selected from-OCH₂-、-CH₂O-、-COO-CH₂CH₂-or-CH₂CH₂-a group of OCO-. ) More preferably represented by the following general formula (1-cm).

[ solution 22]

(in the formula, P¹、P²、Sp¹、Sp²、Z³、Z⁴、U、Q¹、W¹And Y¹Represents the same meaning as in the general formula (1), A¹⁷And A²⁸Each independently represents a 1, 4-phenylene group which is unsubstituted or may be substituted by more than one substituent L¹¹Substituted, L¹¹Represents a fluorine atom, a chlorine atom, or a-CH₂-or two or more-CH's which are not contiguous₂-a linear or branched alkyl group having 1 to 20 carbon atoms which may be independently substituted with-O-, -CO-, -COO-or-OCO-, wherein any hydrogen atom in the alkyl group may be substituted with a fluorine atom, and wherein a plurality of L's are present in the compound¹¹When they are the same or different, A¹⁸And A²⁷Represents 1, 4-cyclohexylene, Z¹⁷And Z²⁸Each independently represents-OCH₂-、-CH₂O-, -COO-, -OCO-or a single bond, Z¹⁸And Z²⁷Each independently represents-OCH₂-or-CH₂O-。)

When importance is attached to the balance of the reverse dispersibility, the high refractive index anisotropy, the high liquid crystallinity when added to the composition, the resistance to deterioration when dissolved in an organic solvent and stored for a long period of time, the resistance to deterioration when added to the composition and stored for a long period of time, or the stability of the retardation when formed into a film, the compound represented by the following general formula (1-cmn) is preferable.

[ solution 23]

(in the formula, P¹、P²、Sp¹、Sp²、Z³、Z⁴、U、Q¹And W¹Represents the same meaning as in the general formula (1), A¹⁷、A²⁸、A¹⁸、A²⁷、Z¹⁷、Z²⁸、Z¹⁸And Z²⁷Represents the same meaning as in the general formula (1-cm), Y¹¹Represents a group selected from-CH₂-or two or more-CH's which are not contiguous₂-a linear or branched alkyl group having 1 to 20 carbon atoms which may be independently substituted with-O-, or-Sp³¹²-P³¹²Group of the group (wherein, P³¹²Represents a group selected from the above-mentioned formulae (P-1) to (P-20), Sp³¹²Represents a-CH₂-or two or more-CH's which are not contiguous₂A linear alkylene group having 1 to 20 carbon atoms which may be independently substituted with-O-, -COO-, -OCO-O-. ). )

As the compound represented by the general formula (1), specifically, compounds represented by the following formulae (1-1) to (1-172) are preferable.

[ solution 24]

[ solution 25]

[ solution 26]

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[ solution 28]

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[ solution 30]

[ solution 31]

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[ chemical 34]

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[ solution 51]

[ solution 52]

[ Hua 53]

[ solution 54]

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[ solution 58]

[ chemical 59]

[ solution 60]

[ solution 61]

[ solution 62]

The compound of the present invention can be produced by the following method.

(preparation method 1) production of halogen from Compound represented by the following formula (S-9)

[ solution 63]

(in the formula, W¹、Y¹Each independently represents the same group as defined in the general formula (1), and P represents the same group as P in the general formula (1)¹Or P²The same groups as defined above, L represents a group identical to the substituent LThe same or different defined groups, L's being more than one and the same or different, Sp-COO or Sp-COOCH₂CH₂Corresponds to Sp in the general formula (1)¹-Z³Or Sp²-Z⁴When a group is defined, s represents an integer of 0 to 4, t represents an integer of 0 to 3, and "halogen" represents a halogen atom or a halogen equivalent. )

The compound represented by the formula (S-2) can be obtained by formylating the compound represented by the formula (S-1). As an example of the reaction, there is a method of reacting paraformaldehyde in the presence of magnesium chloride and a base. As the base, for example, triethylamine and the like can be used.

The compound represented by the formula (S-4) can be obtained by reacting the compound represented by the formula (S-2) with the compound represented by the formula (S-3). Examples of the reaction conditions include a method using a condensing agent; or a method in which the compound represented by the formula (S-3) is converted into an acid chloride, a mixed acid anhydride or a carboxylic acid anhydride, and then the compound is reacted with the compound represented by the general formula (S-2) in the presence of a base. When a condensing agent is used, examples of the condensing agent include N, N '-dicyclohexylcarbodiimide, N' -diisopropylcarbodiimide, and 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride. Examples of the base include triethylamine and diisopropylethylamine.

The compound represented by the formula (S-6) can be obtained by reacting the compound represented by the formula (S-5) with, for example, hydrazine monohydrate.

The compound represented by the formula (S-8) can be obtained by reacting the compound represented by the formula (S-6) with the compound represented by the formula (S-7) in the presence of a base. Examples of the base include potassium carbonate and cesium carbonate.

The compound represented by the formula (S-9) can be obtained by reacting the compound represented by the formula (S-8) with the compound represented by the formula (S-4) in the presence of an acid catalyst. Examples of the acid include p-toluenesulfonic acid and p-toluenesulfonic acid pyridineSalts, 10-camphorsulfonic acid, and the like.

(preparation method 2) production of Compound represented by the following formula (S-15)

[ solution 64]

(in the formula, P¹、P²、Sp¹、Sp²、Z³、Z⁴、W¹、Y¹Each independently represents the same group as that defined in the general formula (1), L represents the same group as that defined in the substituent L, L may be the same or different when a plurality of L's are present, v represents an integer of 0 to 4, t represents an integer of 0 to 3, and "halogen" represents a halogen atom or a halogen equivalent. )

The compound represented by the formula (S-12) can be obtained by reacting the compound represented by the formula (S-10) with the compound represented by the formula (S-11). As a reaction example, there is a method of performing cross-coupling in the presence of a metal catalyst and a base, for example. Examples of the metal catalyst include [1, 1' -bis (diphenylphosphino) ferrocene ] dichloropalladium (II), palladium (II) acetate, and tetrakis (triphenylphosphine) palladium (0). Examples of the base include triethylamine. Examples of reaction conditions include Metal-Catalyzed Cross-Coupling Reactions (Armin DeMeijere, Francois Diedirich, Wiley-VCH), Palladium Reagents and Catalysts: new perspectives for the21st Century (Palladium reagent and catalyst: New prospect of the21st Century) (Jiro Tsuji, Wiley & Sons, Ltd.), Cross-Coupling Reactions: a Practical Guide (Topicsin Current chemistry) (Cross coupling reaction: Practical Guide (topic in chemistry today)) (S.L. Buchwald, K.Fugami, T.Hiyama, M.Kosugi, M.Miura, N.Miyaura, A.R. Muci, M.Nomura, E.Shirakawa, K.Tamao, Springer) and the like.

The compound represented by the formula (S-14) can be obtained by reacting the compound represented by the formula (S-12) with the compound represented by the formula (S-13) in the same manner as in the production process 1.

The compound represented by the formula (S-15) can be obtained by reacting the compound represented by the formula (S-14) with the compound represented by the formula (S-8) in the same manner as in the production process 1.

(preparation method 3) production of Compound represented by the following formula (S-23)

[ solution 65]

(in the formula, P¹、P²、Sp¹、Sp²、Z³、Z⁴、W¹、Y¹Each independently represents the same group as that defined in the general formula (1), L represents the same group as that defined in the substituent L, L may be the same or different when a plurality of L's are present, v represents an integer of 0 to 4, t represents an integer of 0 to 3,

PG represents a protecting group. )

The hydroxyl group of the compound represented by the formula (S-16) is protected with a Protecting Group (PG). The Protecting Group (PG) is not particularly limited as long as it is a group which can be stably protected until the deprotection step, and is preferably a Protecting Group (PG) exemplified IN green's sport group IN ORGANIC SYNTHESIS (fourth edition), peterg.m.wuts, theodola w.green, John Wiley & Sons, inc., Publication) and the like. Specific examples of the protecting group include tetrahydropyranyl groups.

The compound represented by the formula (S-18) can be obtained by formylating the compound represented by the formula (S-17) in the same manner as in the production process 1.

The compound represented by the formula (S-19) can be obtained by reacting the compound represented by the formula (S-18) with the compound represented by the formula (S-13) in the same manner as in the production process 2.

Deprotecting a Protecting Group (PG) of a compound represented by the formula (S-19). The reaction conditions for deprotection are not particularly limited as long as the compound represented by the formula (S-20) is obtained, and the conditions listed in the above-mentioned documents are preferred.

The compound represented by the formula (S-22) can be obtained by reacting the compound represented by the formula (S-20) with the compound represented by the formula (S-13) in the same manner as in the production process 2.

The compound represented by the formula (S-23) can be obtained by reacting the compound represented by the formula (S-22) with the compound represented by the formula (S-8) in the same manner as in the production process 1.

Reaction conditions other than those described in the respective steps of the production methods 1 to 3 include, for example, those described in the literature of experimental Chemistry lectures (edited by japan chemical society, issued by bobble corporation), Organic Syntheses (Organic Synthesis) (John Wiley & Sons, Inc., Publication), Beilstein Handbook of Organic Chemistry (Beilstein Organic Chemistry manual) (Beilstein-Institut fur der Organic Chemistry, Springer-VerlagBerlin and Heidelberg GmbH & co.k), Fiesers 'Reagents for Organic Synthesis (fisher's reagent for Organic Synthesis) (John Wiley & Sons, Inc.), or those provided by the search of scienders (chemical abstractor, american chemical society) or online services.

In addition, a reaction solvent can be suitably used in each step. The solvent is not limited as long as the target compound is obtained, and examples thereof include t-butanol, isobutanol, isopropanol, isoamyl alcohol, cyclohexanol, 1-butanol, 2-butanol, 1-octanol, 2-methoxyethanol, ethylene glycol, diethylene glycol, methanol, methylcyclohexanol, ethanol, propanol, chloroform, carbon tetrachloride, methylene chloride, 1, 2-dichloroethane, 1, 2-dichloroethylene, 1,2, 2-tetrachloroethane, trichloroethylene, 1-chlorobutane, carbon disulfide, acetone, acetonitrile, benzonitrile, N-dimethylformamide, N-dimethylacetamide, dimethyl sulfoxide, 1, 3-dimethyl-2-imidazolidinone, diethyl ether, ethylene glycol monoethylether acetate, ethylene glycol monobutyl ether, ethylene glycol, ethylene glycol monomethyl ether, diethylene glycol diethyl ether, o-dichlorobenzene, xylene, o-xylene, p-xylene, m-xylene, chlorobenzene, isobutyl acetate, isopropyl acetate, isoamyl acetate, ethyl acetate, butyl acetate, propyl acetate, amyl acetate, methyl acetate, 2-methoxyethyl acetate, hexamethylphosphoric triamide, tris (dimethylamino) phosphine, cyclohexanone, 1, 4-bis (hydroxymethyl) phosphonium, hexamethylphosphoric triamide, tris (dimethylamino) phosphonium, or mixtures thereofAlkane, methylene chloride, styrene, tetrachloroethylene, tetrahydrofuran, pyridine, 1-methyl-2-pyrrolidone, 1,1, 1-trichloroethane, toluene, hexane, pentane, cyclohexane, cyclopentane, heptane, benzene, methyl isobutyl ketone, t-butyl methyl ether, methyl ethyl ketone, methyl cyclohexanone, methyl butyl ketone, diethyl ketone, gasoline, coal tar naphtha, petroleum spirit, petroleum naphtha, petroleum ether, turpentine, mineral spirit and the like. When the reaction is carried out in a two-phase system of an organic solvent and water, a phase transfer catalyst may be added. Examples of the phase transfer catalyst include benzyltrimethylammonium chloride and polyoxyethylene (20) sorbitan monolaurate [ Tween 20]]Sorbitan monooleate [ span 80]]And the like.

Further, in each step, purification may be performed as necessary. Examples of the purification method include chromatography, recrystallization, distillation, sublimation, reprecipitation, adsorption, liquid separation treatment, and the like. When a refining agent is used, examples of the refining agent include silica gel, alumina, activated carbon, activated clay, diatomaceous earth, zeolite, mesoporous silica, carbon nanotubes, carbon nanohorns, binchotan, charcoal, graphene, ion exchange resins, acid clay, silica, diatomaceous earth, perlite, cellulose, organic polymers, and porous gels.

< composition >

The compounds of the invention of the present application are preferably used in nematic liquid crystal compositions, smectic liquid crystal compositions, chiral smectic liquid crystal compositions and cholesteric liquid crystal compositions. Compounds other than those of the present invention may be added to the liquid crystal composition using the reactive compound of the present invention.

As another polymerizable compound to be used in combination with the polymerizable compound of the present invention, specifically, compounds represented by the general formula (II-1) and/or the general formula (II-2) are preferable,

[ solution 66]

[ solution 67]

(in the formula, P¹、P²And P³Each independently represents a polymerizable group, S¹、S²And S³Each independently represents a single bond or an alkylene group having 1 to 20 carbon atoms, a-CH₂-or two or more-CH's which are not contiguous₂May be substituted by-O-, -COO-, -OCO-, -OCOO-, X¹、X²And X³Each independently represents-O-, -S-, -OCH₂-、-CH₂O-、-CO-、-COO-、-OCO-、-CO-S-、-S-CO-、-O-CO-O-、-CO-NH-、-NH-CO-、-SCH₂-、-CH₂S-、-CF₂O-、-OCF₂-、-CF₂S-、-SCF₂-、-CH＝CH-COO-、-CH＝CH-OCO-、-COO-CH＝CH-、-OCO-CH＝CH-、-COO-CH₂CH₂-、-OCO-CH₂CH₂-、-CH₂CH₂-COO-、-CH₂CH₂-OCO-、-COO-CH₂-、-OCO-CH₂-、-CH₂-COO-、-CH₂-OCO-, -CH ═ CH-, -CF ═ CF-, -C ≡ C-, or a single bond, Z ≡ C-³And Z⁴Each independently represents-O-, -S-, -OCH₂-、-CH₂O-、-COO-、-OCO-、-CO-、-CO-S-、-S-CO-、-O-CO-O-、-CO-NH-、-NH-CO-、-SCH₂-、-CH₂S-、-CF₂O-、-OCF₂-、-CF₂S-、-SCF₂-、-CH₂CH₂-、-CH₂CF₂-、-CF₂CH₂-、-CF₂CF₂-、-CH＝CH-COO-、-CH＝CH-OCO-、-COO-CH＝CH-、-OCO-CH＝CH-、-COO-CH₂CH₂-、-OCO-CH₂CH₂-、-CH₂CH₂-COO-、-CH₂CH₂-OCO-、-COO-CH₂-、-OCO-CH₂-、-CH₂-COO-、-CH₂-OCO-, -CH ═ CH-, -CF ═ CF-, -C ≡ C-, or a single bond, a ≡ C-³、A⁴、A⁵And A⁶Each independently of the otherRespectively represents 1, 4-phenylene, 1, 4-cyclohexylene, pyridine-2, 5-diyl, pyrimidine-2, 5-diyl, naphthalene-2, 6-diyl, naphthalene-1, 4-diyl, tetrahydronaphthalene-2, 6-diyl or 1, 3-diylAlk-2, 5-diyl, A³、A⁴、A⁵And A⁶Each independently unsubstituted or substituted by alkyl, haloalkyl, alkoxy, haloalkoxy, halogen atom, cyano or nitro, R⁵Represents a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfanyl group, a cyano group, a nitro group, an isocyano group, an isothiocyanato group, or a-CH group₂-or two or more-CH's which are not contiguous₂-a linear or branched alkyl group of 1 to 20 carbon atoms which may each be independently substituted by-O-, -S-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -CH-COO-, -CH-OCO-, -COO-CH-, -OCO-CH-, -CH-, -CF-or-C.ident.C-, m3 and m4 represent 0, 1,2 or 3, m3 and/or m4 represent 2 or 3, in which case two or three of A are present.³、A⁵、Z³And/or Z⁴May be the same or different. ) P¹、P²And P³It is particularly preferred when it is an acryloyl group or a methacryloyl group. As the compound represented by the general formula (II-1), specifically, a compound represented by the general formula (II-1A) is preferable,

[ solution 68]

(in the formula, W³And W⁴Each independently represents hydrogen or methyl, S⁴And S⁵Each independently represents an alkylene group having 2 to 18 carbon atoms, X⁴And X⁵Each independently represents-O-, -COO-, -OCO-or a single bond, Z⁵And Z⁶Each independently represents-COO-or-OCO-, A⁷、A⁸And A⁹Each independently represents a straight or branched chain which is unsubstituted or may be substituted by a fluorine atom, a chlorine atom or a carbon atom having 1 to 4 carbon atomsA linear alkyl group, a linear or branched alkoxy group having 1 to 4 carbon atoms, and a 1, 4-phenylene group. ) Particularly preferred are compounds represented by the following formulae (II-1A-1) to (II-1A-4).

[ solution 69]

(in the formula, W³And W⁴Each independently represents hydrogen or methyl, S⁴Represents S in the general formula (II-1A)⁴Same meaning, S⁵Represents S in the general formula (II-1A)⁵The same meaning is used. ) Among the above-mentioned formulas (II-1A-1) to (II-1A-4), S is particularly preferable⁴And S⁵Each independently an alkylene group having 2 to 8 carbon atoms.

Other preferable 2-functional polymerizable compounds include compounds represented by the following general formulae (II-1B-1) to (II-1B-3).

[ solution 70]

(in the formula, W⁵And W⁶Each independently represents hydrogen or methyl, S⁶And S⁷Each independently represents an alkylene group having 2 to 18 carbon atoms. ) Among the above-mentioned formulas (II-1B-1) to (II-1B-3), S is particularly preferable⁶And S⁷Each independently an alkylene group having 2 to 8 carbon atoms.

Specific examples of the compounds represented by the general formula (II-2) include compounds represented by the following general formulae (II-2-1) to (II-2-7).

[ solution 71]

(in the formula, P⁴Represents the same meaning as P in the general formula (I), S⁸Represents a single bond or an alkylene group of 1 to 20 carbon atoms, one-CH₂-or not adjacentMore than two-CH₂May be substituted by-O-, -COO-, -OCO-, -O-CO-O-, X⁶Represents a single bond, -O-, -COO-, or-OCO-, Z⁷Represents a single bond, -COO-or-OCO-, L¹Represents a fluorine atom, a chlorine atom, a-CH₂-or two or more-CH's which are not contiguous₂-a linear or branched alkyl group having 1 to 10 carbon atoms which may be independently substituted with-O-, -COO-, -OCO-, s represents an integer of 0 to 4, R³Represents a hydrogen atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group, a-CH₂-or two or more-CH's which are not contiguous₂-a linear or branched alkyl group having 1 to 20 carbon atoms which may be independently substituted with-O-, -S-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -CH ═ CH-COO-, -CH ═ CH-OCO-, -COO-CH ═ CH-, -OCO-CH ═ CH-, -CF ≡ CF-, or-C ≡ C-. )

In the polymerizable composition containing the compound of the present invention, a polymerizable compound which does not exhibit liquid crystallinity may be added to the composition to such an extent that liquid crystallinity of the composition is not impaired. Specifically, any compound that is considered to be a polymer-forming monomer or a polymer-forming oligomer in the technical field may be used without particular limitation. Specific examples thereof include those described in "Table of data on photo-curing technique and materials (monomer, oligomer, and photopolymerization initiator)" (the product of Katsumadai Kagaku Co., Ltd.).

The compound of the present invention may be polymerized without using a photopolymerization initiator, but a photopolymerization initiator may be added according to the purpose. In this case, as for the concentration of the photopolymerization initiator, it is preferably 0.1 to 15% by mass, more preferably 0.2 to 10% by mass, and further preferably 0.4 to 8% by mass, relative to the compound of the invention of the present application. Examples of the photopolymerization initiator include benzoin ethers, benzophenones, acetophenones, benzil ketals, and acylphosphine oxides. Specific examples of the photopolymerization initiator include 2-methyl-1- (4-methylthiophenyl) -2-morpholinopropan-1-one (IRGACURE 907), benzoic acid [1- [4- (phenylthio) benzoyl ] heptylidene ] urethane (IRGACURE OXE01), and the like. Examples of the thermal polymerization initiator include azo compounds and peroxides. Specific examples of the thermal polymerization initiator include 2,2 '-azobis (4-methoxy-2, 4-dimethylvaleronitrile), 2' -azobis (isobutyronitrile), and the like. One polymerization initiator may be used, or two or more polymerization initiators may be used in combination.

In addition, a stabilizer may be added to the liquid crystal composition of the present invention in order to improve the storage stability. Examples of the stabilizer that can be used include hydroquinones, hydroquinone monoalkyl ethers, t-butyl catechol, pyrogallol, thiophenol, nitro compounds, β -naphthylamine, β -naphthol, and nitroso compounds. The amount of the stabilizer added when used is preferably in the range of 0.005 to 1% by mass, more preferably 0.02 to 0.8% by mass, and further preferably 0.03 to 0.5% by mass, relative to the composition. One kind of stabilizer may be used, or two or more kinds of stabilizers may be used in combination. As the stabilizer, specifically, compounds represented by the formulae (III-1) to (III-40) are preferable.

[ chemical formula 72]

[ solution 73]

[ chemical formula 74]

[ solution 75]

[ 76]

[ solution 77]

[ solution 78]

[ solution 79]

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

When the polymerizable composition containing the compound of the present invention is used for applications such as films, optical elements, functional pigments, pharmaceuticals, cosmetics, coating agents, and synthetic resins, a metal complex, a dye, a pigment, a dye, a fluorescent material, a phosphorescent material, a surfactant, a leveling agent, a thixotropic agent, a gelling agent, polysaccharides, an ultraviolet absorber, an infrared absorber, an antioxidant, an ion exchange resin, and a metal oxide such as titanium oxide may be added according to the purpose.

A polymer obtained by polymerizing a polymerizable composition containing the compound of the present invention can be used for various applications. For example, a polymer obtained by polymerizing a polymerizable composition containing the compound of the present invention without orientation can be used as a light diffusion plate, a depolarizing plate, or a moire preventing plate. Further, a polymer obtained by polymerization after orientation has optical anisotropy, and thus is useful. Such an optically anisotropic body can be produced, for example, by supporting a polymerizable composition containing the compound of the present invention on a substrate subjected to a rubbing treatment with a cloth or the like, a substrate having an organic thin film formed thereon, or a substrate having an obliquely evaporated SiO layer₂Or by sandwiching the alignment film between substrates and then polymerizing the polymerizable composition.

Examples of the method for supporting the polymerizable composition on the substrate include spin coating, die coating, extrusion coating, roll coating, wire bar coating, gravure coating, spray coating, dipping, and printing methods. In addition, an organic solvent may be added to the polymerizable composition at the time of coating. Examples of the organic solvent include hydrocarbon solvents, halogenated hydrocarbon solvents, ether solvents, alcohol solvents, ketone solvents, ester solvents, and aprotic solvents, and examples of the hydrocarbon solvents include toluene or hexane, the halogenated hydrocarbon solvents include dichloromethane, the ether solvents include tetrahydrofuran, acetoxy-2-ethoxyethane, and propylene glycol monomethyl ether acetate, the alcohol solvents include methanol, ethanol, and isopropanol, the ketone solvents include acetone, methyl ethyl ketone, cyclohexanone, γ -butyrolactone, and N-methylpyrrolidone, the ester solvents include ethyl acetate and cellosolve, and the aprotic solvents include dimethylformamide and acetonitrile. These may be used alone or in combination, and may be appropriately selected in consideration of the vapor pressure and solubility of the polymerizable composition. As a method for volatilizing the added organic solvent, natural drying, heat drying, reduced pressure drying, or reduced pressure heat drying can be used. In order to further improve the coatability of the polymerizable material, it is also effective to provide an intermediate layer such as a polyimide film on the substrate and to add a leveling agent to the polymerizable material. A method of providing an intermediate layer such as a polyimide film on a substrate is effective for improving adhesion between a polymer obtained by polymerizing a polymerizable material and the substrate.

Examples of the alignment treatment other than the above-described alignment treatment include use of a flow alignment of a liquid crystal material, and use of an electric field or a magnetic field. These orientation means may be used alone or in combination. Further, as an alignment treatment method instead of rubbing, a photo-alignment method may be used. The substrate may have a curved surface as a constituent part in addition to a flat plate. The material constituting the substrate may be any of organic materials and inorganic materials. Examples of the organic material to be used as the substrate material include polyethylene terephthalate, polycarbonate, polyimide, polyamide, polymethyl methacrylate, polystyrene, polyvinyl chloride, polytetrafluoroethylene, polychlorotrifluoroethylene, polyarylate, polysulfone, triacetyl cellulose, and polyether ether ketone, and examples of the inorganic material include silicon, glass, and calcite.

When polymerizing a polymerizable composition containing the compound of the present invention, it is desired to rapidly perform polymerization, and therefore a method of polymerizing by irradiation with active energy rays such as ultraviolet rays or electron rays is preferred. When ultraviolet light is used, either a polarized light source or an unpolarized light source may be used. In addition, when the polymerization is performed in a state where the liquid crystal composition is sandwiched between two substrates, at least the substrate on the irradiation surface side must have appropriate transparency to the active energy ray. In addition, a means of polymerizing only a specific portion by using a mask at the time of light irradiation, changing the orientation state of an unpolymerized portion by changing the conditions such as an electric field, a magnetic field, or temperature, and further irradiating an active energy ray to polymerize the same may be used. The temperature during irradiation is preferably within a temperature range in which the liquid crystal state of the polymerizable composition of the present invention can be maintained. In particular, when the optically anisotropic body is intended to be produced by photopolymerization, it is preferable to carry out the polymerization at a temperature as close to room temperature as possible, that is, typically at a temperature of 25 ℃ from the viewpoint of avoiding causing unnecessary thermal polymerization. The intensity of the active energy ray is preferably 0.1mW/cm²～2W/cm². The intensity is 0.1mW/cm²In the following cases, a large amount of time is required to complete photopolymerization, and the productivity is deteriorated, namely, 2W/cm²In the above case, there is a risk that the polymerizable compound or the polymerizable composition deteriorates.

The optically anisotropic body obtained by polymerization may be subjected to heat treatment in order to reduce initial characteristic change and realize stable characteristic expression. The heat treatment temperature is preferably 50 to 250 ℃, and the heat treatment time is preferably 30 seconds to 12 hours.

The optically anisotropic body produced by such a method may be used alone by peeling it from a substrate or may be used without peeling it. The optically anisotropic body thus obtained may be laminated or bonded to another substrate.

The present invention will be described in further detail with reference to examples, but the present invention is not limited to these examples. Unless otherwise specified, "part(s)" and "%" are based on mass.