JP2019011467A - Polymerizable compound, method for producing polymerizable compound, polymerizable composition, optically anisotropic film, optical film, polarizing plate, and image display device - Google Patents

Abstract

To provide a polymerizable compound that is used for the formation of an optically anisotropic film having excellent durability and has excellent solubility and a method for producing the same, and a polymerizable composition, an optically anisotropic film, an optical film, a polarizing plate and an image display device.SOLUTION: A polymerizable compound is represented by the following formula (I-1-1).SELECTED DRAWING: None

Description

  The present invention relates to a polymerizable compound, a method for producing the polymerizable compound, a polymerizable composition, an optically anisotropic film, an optical film, a polarizing plate, and an image display device.

A polymerizable compound exhibiting reverse wavelength dispersion has features such as being able to accurately convert the light wavelength in a wide wavelength range and being able to reduce the thickness of the retardation film because it has a high refractive index. Therefore, it has been actively researched.
In general, T-type molecular design guidelines have been adopted for polymerizable compounds exhibiting reverse wavelength dispersion, and the wavelength of the major axis is shortened and the wavelength of the minor axis located at the center of the molecule is lengthened. Is required to do.
For this reason, it is known to use a cycloalkylene skeleton having no absorption wavelength for the connection between the short-axis skeleton located in the center of the molecule (hereinafter also referred to as “reverse wavelength dispersion expression part”) and the molecular long axis. ing.
For example, Patent Document 1 describes a composition comprising a polymerizable liquid crystal compound having one reverse wavelength dispersion developing part, a polymerizable liquid crystal compound having two or more reverse wavelength dispersion developing parts, and a solvent. ([Claim 1] [0152] etc.).

JP 2006-121339 A

  The present inventors examined a polymerizable liquid crystal compound having two or more reverse wavelength dispersion expressing parts described in Patent Document 1, and may have poor solubility depending on the structure of the compound. Depending on the type of polymerizable liquid crystal compound having one chromatic dispersion developing part and the polymerization conditions such as the curing temperature, the birefringence changes when the formed optically anisotropic film is exposed to high temperature and high humidity. It was clarified that there was a problem of durability that it would end up.

  Accordingly, the present invention provides a polymerizable compound having excellent solubility used for forming an optically anisotropic film having excellent durability and a method for producing the same, as well as a polymerizable composition, an optically anisotropic film, an optical film, It is an object to provide a polarizing plate and an image display device.

As a result of intensive studies to achieve the above-mentioned problems, the present inventors have two reverse wavelength dispersion expressing portions in the molecule, and the aromatic ring constituting the reverse wavelength dispersion expressing portion has a steric hindrance group. As a result, it was found that the solubility was improved and the durability of the formed optically anisotropic film was improved, and the present invention was completed.
That is, it has been found that the above-described problem can be achieved by the following configuration.

[1] A polymerizable compound represented by the following formula (1).
[2] The polymerizable compound according to [1], wherein m in formula (1) described later is 1.
[3] As described in [1] or [2], Z ¹ in formulas (Ar-1) to (Ar-8) described later represents a monovalent aliphatic hydrocarbon group having 3 to 20 carbon atoms. Polymerizable compound.
[4] The polymerizable compound according to any one of [1] to [3], wherein Z ¹ in formulas (Ar-1) to (Ar-8) described later represents a tert-butyl group.
[5] The polymerizable compound according to any one of [1] to [4], which has liquid crystallinity.

[6] A method for producing a polymerizable compound for synthesizing the polymerizable compound according to [1],
A first esterification step of reacting a compound represented by the formula (2) described later with a compound represented by the formula (3) described later to produce a first phenol compound;
A second esterification step in which the first phenol reactant obtained in the first esterification step and a compound represented by the formula (4) described below are reacted to obtain the polymerizable compound described in [1]. A method for producing a polymerizable compound.
[7] A method for producing a polymerizable compound for synthesizing the polymerizable compound according to [1],
A first esterification step of reacting a compound represented by the formula (2) described later with a compound represented by the formula (4) described later to produce a second phenol compound;
A second esterification step of reacting the second phenol reactant obtained in the first esterification step with a compound represented by the formula (3) described below to obtain the polymerizable compound described in [1]. A method for producing a polymerizable compound.

[8] A polymerizable composition containing the polymerizable compound according to any one of [1] to [5].
[9] The polymerizable composition according to [8], further comprising a polymerizable compound having two or more polymerizable groups, which is different from the polymerizable compound.
[10] An optically anisotropic film obtained by curing the polymerizable composition according to [8] or [9].
[11] An optical film having the optically anisotropic film according to [10].
[12] A polarizing plate comprising the optical film according to [11] and a polarizer.
[13] An image display device having the optical film according to [11] or the polarizing plate according to [12].

  According to the present invention, a polymerizable compound having excellent solubility used for forming an optically anisotropic film having excellent durability and a method for producing the same, and a polymerizable composition, an optically anisotropic film, an optical film, A polarizing plate and an image display device can be provided.

FIG. 1A is a schematic cross-sectional view showing an example of the optical film of the present invention. FIG. 1B is a schematic cross-sectional view showing an example of the optical film of the present invention. FIG. 1C is a schematic cross-sectional view showing an example of the optical film of the present invention.

Hereinafter, the present invention will be described in detail.
The description of the constituent elements described below may be made based on typical embodiments of the present invention, but the present invention is not limited to such embodiments.
In the present specification, a numerical range expressed using “to” means a range including numerical values described before and after “to” as a lower limit value and an upper limit value.
In this specification, the bonding direction of a divalent group (for example, —O—CO—) represented is not particularly limited, and for example, D ¹ in the formula (1) described later is —O—CO—. In this case, assuming that the position bonded to the G ¹ side is * 1, and the position bonded to the Ar ² side is * 2, D ¹ may be * 1-O—CO— * 2. * 1-CO-O- * 2.

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

In the present invention, as described above, in the molecule, Ar ¹ and Ar ² in the above formula (1) corresponding to the reverse wavelength dispersion developing part are contained, and Ar ¹ and Ar ² are sterically hindered groups ( By using a polymerizable compound having Z ¹ ) in formulas (Ar-1) to (Ar-8) described later, the solubility is improved and the durability of the formed optically anisotropic film is improved. .
Although this is not clear in detail, the present inventors presume as follows.
That is, it is presumed that by introducing a steric hindrance group into two aromatic rings corresponding to the reverse wavelength dispersion developing part, the melting point of the polymerizable compound was lowered and the solubility of the polymerizable compound in the organic solvent was improved.
In addition, the presence of a sterically hindered group introduced into two aromatic rings corresponding to the reverse wavelength dispersion developing portion inhibits water from approaching the central portion of the polymerizable compound, thereby suppressing the hydrolysis reaction, As a result, it is estimated that the durability of the optically anisotropic film is improved.
Hereinafter, the structure of said Formula (1) is demonstrated in detail about the polymeric compound of this invention.

As described above, the polymerizable compound of the present invention is a polymerizable compound represented by the following formula (1).

The above formula (1) D ¹ , D ² , D ³ and D ⁴ are each independently a single bond, —O—, —CO—O—, —C (═S) O—, —CR ¹ R ² —. ^{, -CR 1 R 2 -CR 3 R} 4 -, - O-CR 1 R 2 -, - CR 1 R 2 -O-CR 3 R 4 -, - CO-O-CR 1 R 2 -, - O- ^{CO-CR 1 R 2 -,} - CR 1 R 2 -O-CO-CR 3 R 4 -, - CR 1 R 2 -CO-O-CR 3 R 4 -, - NR 1 -CR 2 R 3 -, Or, -CO-NR < ¹ >-is represented. R ¹ , R ² , R ³ and R ⁴ each independently represent a hydrogen atom, a fluorine atom, or an alkyl group having 1 to 4 carbon atoms.
In the above formula (1), G ¹ represents ^AG or SP ^G.
In the formula (1), A ¹ , A ² and ^AG each independently represent an aromatic ring having 6 or more carbon atoms or a cycloalkane ring having 6 or more carbon atoms, and constitutes the cycloalkane ring. One or more of —CH ₂ — may be substituted with —O—, —S—, or —NH—.
In the formula (1), SP ¹ , SP ² and SP ^G are each independently a single bond, a linear or branched alkylene group having 1 to 20 carbon atoms, or a linear chain having 1 to 20 carbon atoms. Or one or more of —CH ₂ — constituting the alkylene group, the alkenylene group or the alkynylene group, or a linear or branched alkenylene group, a linear or branched alkynylene group having 1 to 20 carbon atoms, Represents a divalent linking group substituted with O-, -S-, -NH-, -N (Q)-or -CO-, and Q represents a substituent.
In the above formula (1), L ¹ and L ² each independently represent a monovalent organic group, and at least one of L ¹ and L ² represents a polymerizable group. However, when at least one of Ar ¹ and Ar ² is an aromatic ring represented by the formula (Ar-4) described later, L ¹ and L ² and L ³ in the formula (Ar-4) described later and At least one of L ⁴ represents a polymerizable group.
In the above formula (1), m represents an integer of 0 to 2, and when m is 2, a plurality of G ¹ may be the same or different, and a plurality of D ¹ are each They may be the same or different.
In the above formula (1), l and n each independently represent 0 or an integer of 1 or more. When l is an integer of 2 or more, a plurality of A ¹ are the same or different. The plurality of D ³ may be the same or different. When n is an integer of 2 or more, the plurality of D ⁴ may be the same or different, and the plurality of A ² may be the same or different.

In the above formula (1), examples of the aromatic ring having 6 or more carbon atoms represented by A ¹ , A ² and ^AG include aromatic hydrocarbon rings such as a benzene ring, a naphthalene ring, an anthracene ring, and a phenanthrolin ring. An aromatic heterocycle such as a furan ring, a pyrrole ring, a thiophene ring, a pyridine ring, a thiazole ring, a benzothiazole ring; Of these, a benzene ring (for example, a 1,4-phenyl group and the like) is preferable.
In the above formula (1), examples of the cycloalkane ring having 6 or more carbon atoms represented by A ¹ , A ² and ^AG include a cyclohexane ring and a cyclohexene ring. Among them, a cyclohexane ring (for example, Cyclohexane-1,4-diyl group, etc.) are preferred.

In the above formula (1), the linear or branched alkylene group having 1 to 20 carbon atoms represented by SP ¹ , SP ² and SP ^G is preferably an alkylene group having 1 to 12 carbon atoms, 10 alkylene groups are more preferable, for example, methylene group, ethylene group, propylene group, butylene group, pentylene group, hexylene group and the like are preferable.
Further, in the above formula ^(1), as the linear or branched alkenylene group SP 1, SP ² and SP carbon atoms ^G represents 20, preferably an alkenylene group having 2 to 10 carbon atoms, carbon atoms 2-4 alkenylene groups are more preferable, for example, ethenylene group etc. are mentioned suitably.
Further, in the above formula ^(1), as the linear or branched alkynylene group SP 1, SP ² and SP carbon atoms ^G represents 20, preferably an alkynylene group having 2 to 10 carbon atoms, carbon atoms 2-4 alkynylene groups are more preferable, for example, an ethynylene group etc. are mentioned suitably.

In the above formula (1), examples of the monovalent organic group represented by L ¹ and L ² include an alkyl group, an aryl group, and a heteroaryl group. The alkyl group may be linear, branched or cyclic, but is preferably linear. 1-30 are preferable, as for carbon number of an alkyl group, 1-20 are more preferable, and 1-10 are still more preferable. The aryl group may be monocyclic or polycyclic but is preferably monocyclic. 6-25 are preferable and, as for carbon number of an aryl group, 6-10 are more preferable. The heteroaryl group may be monocyclic or polycyclic. The number of heteroatoms constituting the heteroaryl group is preferably 1 to 3. The hetero atom constituting the heteroaryl group is preferably a nitrogen atom, a sulfur atom or an oxygen atom. 6-18 are preferable and, as for carbon number of heteroaryl group, 6-12 are more preferable. The alkyl group, aryl group and heteroaryl group may be unsubstituted or may have a substituent. Examples of the substituent include the same substituents as those which Y ^{1 in} formula (Ar-1) may have.
On the other hand, the polymerizable group represented by at least one of L ¹ and L ² is not particularly limited, but is preferably a polymerizable group capable of radical polymerization or cationic polymerization.
As the radical polymerizable group, a generally known radical polymerizable group can be used, and preferable examples include an acryloyl group or a methacryloyl group. In this case, it is known that the acryloyl group is generally fast in the polymerization rate, and the acryloyl group is preferable from the viewpoint of productivity improvement. However, the methacryloyl group is also used as the polymerizable group of the highly birefringent liquid crystal. Can do.
As the cationic polymerizable group, generally known cationic polymerizable can be used, and specifically, an alicyclic ether group, a cyclic acetal group, a cyclic lactone group, a cyclic thioether group, a spiro orthoester group, and And vinyloxy groups. Among these, an alicyclic ether group or a vinyloxy group is preferable, and an epoxy group, an oxetanyl group, or a vinyloxy group is particularly preferable.
Examples of particularly preferred polymerizable groups include the following.

In said formula (1), m represents the integer of 0-2, l and n represent 0 or an integer greater than or equal to 1 each independently.
Here, m is preferably 0 or 1, and more preferably 1 from the viewpoint of synthesis.
About l and n, it is preferable that it is an integer of 0-2 from a soluble viewpoint and compatibility viewpoint with another liquid crystal compound.

On the other hand, in the above formula (1), Ar ¹ and Ar ² are each independently any aromatic ring selected from the group consisting of groups represented by the following formulas (Ar-1) to (Ar-8) Represents. In the following formulas (Ar-1) to (Ar-8), * 1 represents a bonding position with D ¹ or D ^3, and * 2 represents a bonding position with D ² or D ⁴ .

Here, in the above formulas (Ar-1) and (Ar-2), Q ¹ represents N or CH, and Q ² represents —S—, —O—, or —N (R ⁵ ) —. R ⁵ represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, Y ¹ represents an aromatic hydrocarbon group having 6 to 12 carbon atoms which may have a substituent, or 3 carbon atoms. Represents an aromatic heterocyclic group of ˜12.
Specific examples of the alkyl group having 1 to 6 carbon atoms represented by R ⁵ include, for example, a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, and a tert-butyl group. Group, n-pentyl group, n-hexyl group and the like.
Examples of the aromatic hydrocarbon group having 6 to 12 carbon atoms represented by Y ¹ include aryl groups such as a phenyl group, a 2,6-diethylphenyl group, and a naphthyl group.
Examples of the aromatic heterocyclic group having 3 to 12 carbon atoms represented by Y ¹ include heteroaryl groups such as a thienyl group, a thiazolyl group, a furyl group, and a pyridyl group.
Examples of the substituent that Y ¹ may have include an alkyl group, an alkoxy group, and a halogen atom.
As the alkyl group, for example, a linear, branched or cyclic alkyl group having 1 to 18 carbon atoms is preferable, and an alkyl group having 1 to 8 carbon atoms (for example, a methyl group, an ethyl group, a propyl group, an isopropyl group). N-butyl group, isobutyl group, sec-butyl group, t-butyl group, cyclohexyl group, etc.), more preferably an alkyl group having 1 to 4 carbon atoms, and a methyl group or an ethyl group. Is particularly preferred.
As an alkoxy group, a C1-C18 alkoxy group is preferable, for example, a C1-C8 alkoxy group (for example, a methoxy group, an ethoxy group, n-butoxy group, a methoxyethoxy group etc.) is more preferable, and carbon More preferably, it is an alkoxy group of 1 to 4, and particularly preferably a methoxy group or an ethoxy group.
Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. Among them, a fluorine atom and a chlorine atom are preferable.

Further, in the above formula (Ar-1) ~ (Ar -8), Z 1 is a group represented by sterically hindered groups described above, a monovalent aliphatic hydrocarbon group having 3 to 20 carbon atoms, 6 carbon atoms Represents a monovalent aromatic hydrocarbon group of ˜20, a halogen atom, —OR ⁶ , —NR ⁷ R ⁸ , or —SR ⁹ , wherein R ^{6 to} R ⁹ each independently has 3 to 20 carbon atoms. It represents a monovalent aliphatic hydrocarbon group or a monovalent aromatic hydrocarbon group having 6 to 20 carbon atoms.
The monovalent aliphatic hydrocarbon group having 3 to 20 carbon atoms represented by Z ¹ is preferably an alkyl group having 3 to 15 carbon atoms, more preferably an alkyl group having 3 to 8 carbon atoms, specifically, isopropyl Group, tert-pentyl group (1,1-dimethylpropyl group), tert-butyl group, 1,1-dimethyl-3,3-dimethyl-butyl group are more preferable, and tert-butyl group is particularly preferable.
Specific examples of the monovalent aromatic hydrocarbon group having 6 to 20 carbon atoms represented by Z ¹ include a phenyl group, a 2,6-diethylphenyl group, a naphthyl group, a biphenyl group, and the like. An aryl group of 6 to 12 (particularly a phenyl group) is preferred.
Examples of the halogen atom represented by Z ¹ include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom, and among them, a fluorine atom, a chlorine atom, and a bromine atom are preferable.
On the other hand, the monovalent aliphatic hydrocarbon group having 3 to 20 carbon atoms represented by R ^{6 to} R ⁹ is preferably an alkyl group having 3 to 15 carbon atoms, more preferably an alkyl group having 3 to 8 carbon atoms. Specifically, isopropyl group, tert-pentyl group (1,1-dimethylpropyl group), tert-butyl group, 1,1-dimethyl-3,3-dimethyl-butyl group are more preferable, and tert-butyl group is particularly preferable. preferable.
Specific examples of the monovalent aromatic hydrocarbon group having 6 to 20 carbon atoms represented by R ^{6 to} R ⁹ include a phenyl group, a 2,6-diethylphenyl group, a naphthyl group, and a biphenyl group. A C6-C12 aryl group (especially phenyl group) is preferable.

Further, in the above formula (Ar-5) ~ (Ar -8), Z 2 is a hydrogen atom, a monovalent aliphatic hydrocarbon group having 1 to 20 carbon atoms, a monovalent alicyclic of 3 to 20 carbon atoms Represents a formula hydrocarbon group, a monovalent aromatic hydrocarbon group having 6 to 20 carbon atoms, a halogen atom, a cyano group, a nitro group, —OR ¹⁰ , —NR ¹¹ R ¹² , or —SR ¹³ , and R ¹⁰ to R < ¹³ > represents a hydrogen atom or a C1-C6 alkyl group each independently.
The monovalent aliphatic hydrocarbon group having 1 to 20 carbon atoms represented by Z ² is preferably an alkyl group having 1 to 15 carbon atoms, more preferably an alkyl group having 1 to 8 carbon atoms, specifically, methyl Group, ethyl group, isopropyl group, tert-pentyl group (1,1-dimethylpropyl group), tert-butyl group, 1,1-dimethyl-3,3-dimethyl-butyl group are more preferable, methyl group, ethyl group A tert-butyl group is particularly preferred.
Examples of the monovalent alicyclic hydrocarbon group having 3 to 20 carbon atoms represented by Z ² include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, a cyclodecyl group, and a methylcyclohexyl group. Group, monocyclic saturated hydrocarbon group such as ethylcyclohexyl group; cyclobutenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, cyclooctenyl group, cyclodecenyl group, cyclopentadienyl group, cyclohexadienyl group, cyclooctadienyl group Groups, monocyclic unsaturated hydrocarbon groups such as cyclodecadiene; bicyclo [2.2.1] heptyl group, bicyclo [2.2.2] octyl group, tricyclo [5.2.1.0 ^2,6 ] decyl, tricyclo [3.3.1.1 ^3,7] decyl group, tetracyclo [ .2.1.1 ^3,6. 0 ^2,7 ] dodecyl group, polycyclic saturated hydrocarbon group such as adamantyl group, and the like.
Specific examples of the monovalent aromatic hydrocarbon group having 6 to 20 carbon atoms represented by Z ² include a phenyl group, a 2,6-diethylphenyl group, a naphthyl group, and a biphenyl group. An aryl group of 6 to 12 (particularly a phenyl group) is preferred.
Examples of the halogen atom represented by Z ² include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom, and among them, a fluorine atom, a chlorine atom, and a bromine atom are preferable.
On the other hand, specific examples of the alkyl group having 1 to 6 carbon atoms represented by R ^{10 to} R ¹³ include, for example, methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl. Group, tert-butyl group, n-pentyl group, n-hexyl group and the like.

In the above formulas (Ar-3) and (Ar-4), A ³ and A ⁴ are each independently from —O—, —N (R ¹⁴ ) —, —S—, and —CO—. R ¹⁴ represents a group selected from the group consisting of: a hydrogen atom or a substituent.
Examples of the substituent represented by R ¹⁴ include the same substituents as those which Y ¹ in the above formula (Ar-1) may have.

In the formula (Ar-3), X represents a hydrogen atom or a nonmetallic atom belonging to Groups 14 to 16 to which a substituent may be bonded.
In addition, examples of the nonmetal atoms belonging to Groups 14 to 16 represented by X include an oxygen atom, a sulfur atom, a nitrogen atom having a substituent, and a carbon atom having a substituent. Specific examples of the substituent include Is, for example, an alkyl group, an alkoxy group, an alkyl-substituted alkoxy group, a cyclic alkyl group, an aryl group (eg, a phenyl group, a naphthyl group, etc.), a cyano group, an amino group, a nitro group, an alkylcarbonyl group, a sulfo group, a hydroxyl group, etc. Is mentioned.

In the formula (Ar-4), D ⁵ and D ⁶ each independently represent a single bond, —O—CO—, —C (═S) O—, —CR ¹ R ² —, —CR ^{1. R 2 -CR 3 R 4 -,} - O-CR 1 R 2 -, - CR 1 R 2 -O-CR 3 R 4 -, - CO-O-CR 1 R 2 -, - O-CO-CR 1 ^{R 2 -, - CR 1 R} 2 -O-CO-CR 3 R 4 -, - CR 1 R 2 -CO-O-CR 3 R 4 -, - NR 1 -CR 2 R 3 -, or, -CO -NR < ¹ >-is represented. R ¹ , R ² , R ³ and R ⁴ each independently represent a hydrogen atom, a fluorine atom, or an alkyl group having 1 to 4 carbon atoms.

In the above formula (Ar-4), SP ³ and SP ⁴ each independently represent a single bond, a linear or branched alkylene group having 1 to 12 carbon atoms, or a straight chain having 1 to 12 carbon atoms. A divalent group in which one or more of —CH ₂ — constituting a chain or branched alkylene group is substituted with —O—, —S—, —NH—, —N (Q) —, or —CO—. Q represents a substituent. Examples of the substituent include the same substituents as those which Y ^{1 in} formula (Ar-1) may have.

In the formula (Ar-4), L ³ and L ⁴ each independently represent a monovalent organic group, and at least one of L ³ and L ⁴ and L ¹ and L ^{2 in} the formula (1) Represents a polymerizable group.
Examples of the monovalent organic group include the same monovalent organic groups as those represented by L ¹ and L ² in the above formula (1), and examples of the polymerizable group include those in the above formula (1). It includes the same as those described in L ¹ and L ^2.

In the above formulas (Ar-5) to (Ar-8), Ax has at least one aromatic ring selected from the group consisting of an aromatic hydrocarbon ring and an aromatic heterocyclic ring, and has 2 to 30 carbon atoms. Represents an organic group.
In the formulas (Ar-5) to (Ar-8), Ay is a hydrogen atom, an alkyl group having 1 to 12 carbon atoms (preferably 1 to 6) which may have a substituent, or An organic group having 2 to 30 carbon atoms and having at least one aromatic ring selected from the group consisting of an aromatic hydrocarbon ring and an aromatic heterocyclic ring.
Here, the aromatic ring in Ax and Ay may have a substituent, and Ax and Ay may combine to form a ring.
Q ³ represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms which may have a substituent.
Examples of Ax and Ay include those described in paragraphs [0039] to [0095] of International Publication No. 2014/010325.
The alkyl group having 1 to 6 carbon atoms represented by ^{Q 3,} specifically, for example, a methyl group, an ethyl group, a propyl group, an isopropyl group, n- butyl group, isobutyl group, sec- butyl group, tert -Butyl group, n-pentyl group, n-hexyl group and the like are mentioned, and examples of the substituent are the same as those which Y ¹ in the above formula (Ar-1) may have. Can be mentioned.

Examples of the polymerizable compound represented by the above formula (1) include compounds represented by the following formulas (I) to (XII), specifically, D in the following formulas (I) to (VI). ^1, the ^{G 1} and ^{D 2} and K, a compound having a group shown in the following table 1-8 can be mentioned, respectively, ^{D 1,} G 1 in formula (VII) ~ (XII), G 1 and ^{D 2} and Examples of K include compounds having groups shown in Table 9 below.
In Tables 1 to 8 below, “*” shown in a group such as D ¹ represents a bonding position.
In the following description, a compound represented by the following formula (I) and having a group shown in 1-1 in the following Table 1 is referred to as “compound (I-1-1)”, and the other A compound having a structural formula and a group is represented by the same method. For example, a compound represented by the following formula (II) and having the group indicated by 2-3 in the following Table 2 can be represented as “compound (II-2-3)”.
In the compound (I-1-1) and the like, a group adjacent to the acryloyloxy group represents a propylene group (a group in which a methyl group is substituted with an ethylene group), and represents a mixture of positional isomers having different methyl group positions. .

In the present invention, with respect to the steric hindrance group possessed by Ar in the above formula (1), the durability of the formed optically anisotropic film is further improved, so that the above formulas (Ar-1) to (Ar-8) are used. Z ¹ is preferably a monovalent aliphatic hydrocarbon group having 3 to 20 carbon atoms, more preferably an alkyl group having 3 to 8 carbon atoms, and a branched alkyl group having 3 to 8 carbon atoms ( For example, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, and the like are more preferable, and a tert-butyl group is particularly preferable.

Further, the polymerizable compound of the present invention is a polymerizable compound (polymerizable liquid crystal compound) having liquid crystallinity because it can be more easily aligned when used alone or when mixed with other liquid crystal compounds. It is preferable.
Here, the liquid crystal property means thermotropic liquid crystal property or lyotropic liquid crystal property, and the thermotropic liquid crystal property has one or more intermediate phases between the crystal phase and the isotropic phase in the temperature rising or cooling process. Means. In lyotropic liquid crystallinity, it means having a phase separation state with some self-organizing power in water or an organic solvent.

[Production Method of Polymerizable Compound (Part 1)]
The first production method of the polymerizable compound of the present invention (hereinafter also abbreviated as “the first production method of the present invention”) includes a compound represented by the following formula (2) and a compound represented by the following formula (3). And a first esterification step for producing a first phenol compound,
A second esterification step of reacting the first phenol reactant obtained in the first esterification step with a compound represented by the following formula (4) to obtain the polymerizable compound of the present invention.

Here, Ar in the above formula (2), L, SP, A and D in the above formula (3), and G ¹ and D ¹ in the above formula (4) are each represented by the above formula (1). The same as Ar ¹ , L ¹ , SP ¹ , A ¹ , D ³ , G ¹ and D ¹ described in the above. Particularly, in the first esterification step in which the compound represented by the above formula (2) and the compound represented by the above formula (3) are reacted, the above formula ( Ar in 2) is Z ¹ in the above formulas (Ar-1) to (Ar-8) is a monovalent aliphatic hydrocarbon group having 3 to 20 carbon atoms, as in the above formula (1). It is preferable.
In the above formula (3), p represents 0 or an integer of 1 or more, and when p is an integer of 2 or more, the plurality of A may be the same or different, and a plurality of D May be the same or different.
Further, q in the formula (4) represents an integer of 0 to 2, q is 2, each of the plurality in G ¹ may be the same or different and a plurality of D ¹ each They may be the same or different.

[First esterification step]
The first esterification step is a step of reacting the compound represented by the above formula (2) with the compound represented by the above formula (3) to produce a first phenol compound. Specifically, This is a step of producing a phenol compound represented by the formula (5).
Here, L, SP, A, D and Ar and l in the above formula (5) are all L ¹ , SP ¹ , A ¹ , D ³ and Ar ¹ and l described in the above formula (1). It is the same.

The reaction conditions for the compound represented by the above formula (2) and the compound represented by the above formula (3) are not particularly limited, and conventionally known reaction conditions for esterification can be appropriately employed.
For example, the reaction temperature is preferably -10 to 40 ° C, more preferably -5 to 30 ° C, and still more preferably 0 to 20 ° C.
The reaction time is preferably 10 minutes to 24 hours, more preferably 1 hour to 10 hours, and still more preferably 1 hour to 8 hours.

[Second esterification step]
The second esterification step is a step of obtaining the polymerizable compound of the present invention by reacting the first phenol compound obtained in the first esterification step with the compound represented by the above formula (4). Specifically, the first phenol compound represented by the above formula (5) and the compound represented by the above formula (4) are reacted to obtain a polymerizable compound represented by the following formula (1A). is there.
Here, L, SP, A, D, Ar, G ¹ and D ¹ and l in the above formula (1A) are all L ¹ , SP ¹ , A ¹ , D described in the above formula (1). ³ , Ar ¹ , G ¹ and D ¹ and 1 are the same, and q in the above formula (1A) represents an integer of 0 to 2, and when q is 2, a plurality of G ¹ are the same Or a plurality of D ¹ may be the same or different from each other.

The reaction conditions for the first phenol compound represented by the above formula (5) and the compound represented by the above formula (4) are not particularly limited, and conventionally known reaction conditions for esterification can be appropriately employed.
For example, the reaction temperature is preferably -10 to 40 ° C, more preferably -5 to 30 ° C, and still more preferably 0 to 20 ° C.
The reaction time is preferably 10 minutes to 24 hours, more preferably 1 hour to 10 hours, and still more preferably 1 hour to 8 hours.

[Method for producing polymerizable compound (2)]
The second production method of the polymerizable compound of the present invention (hereinafter also referred to as “second production method of the present invention”) is a compound represented by the following formula (2) and a compound represented by the following formula (4). And a first esterification step for producing a second phenol compound,
A second esterification step of reacting the second phenol reactant obtained in the first esterification step with a compound represented by the following formula (3) to obtain a polymerizable compound of the present invention.
Here, Ar in the above formula (2), L, SP, A and D in the above formula (3), and G ¹ and D ¹ in the above formula (4) are respectively the first of the present invention. This is the same as described in the manufacturing method.

[First esterification step]
The first esterification step is a step of reacting the compound represented by the above formula (2) with the compound represented by the above formula (4) to produce a second phenol compound. Specifically, This is a step of producing a phenol compound represented by formula (6).
Here, Ar, D ² , G ¹ and D ¹ and m in the above formula (6) are all the same as Ar ¹ , D ² , G ¹ and D ¹ and m described in the above formula (1). It is.

The reaction conditions for the compound represented by the above formula (2) and the compound represented by the above formula (4) are not particularly limited, and conventionally known reaction conditions for esterification can be appropriately employed.
For example, the reaction temperature is preferably -10 to 40 ° C, more preferably -5 to 30 ° C, and still more preferably 0 to 20 ° C.
The reaction time is preferably 10 minutes to 24 hours, more preferably 1 hour to 10 hours, and still more preferably 1 hour to 8 hours.

[Second esterification step]
The second esterification step is a step of obtaining the polymerizable compound of the present invention by reacting the second phenol compound obtained in the first esterification step with the compound represented by the above formula (3). Specifically, the second phenol compound represented by the above formula (6) is reacted with the compound represented by the above formula (3) to obtain a polymerizable compound represented by the following formula (1B). is there.
Here, L, SP, A, D, Ar, D ² , G ^1, D ¹ and m in the above formula (1B) are all L ¹ , SP ¹ , A described in the above formula (1). ¹ , D ³ , Ar ¹ , D ² , G ¹ and D ¹ and m, and p in the above formula (1B) represents 0 or an integer of 1 or more.

The reaction conditions for the second phenol compound represented by the above formula (6) and the compound represented by the above formula (3) are not particularly limited, and conventionally known reaction conditions for esterification can be appropriately employed.
For example, the reaction temperature is preferably -10 to 40 ° C, more preferably -5 to 30 ° C, and still more preferably 0 to 20 ° C.
The reaction time is preferably 10 minutes to 24 hours, more preferably 1 hour to 10 hours, and still more preferably 1 hour to 8 hours.

[Polymerizable composition]
The polymerizable composition of the present invention is a polymerizable composition containing the above-described polymerizable compound of the present invention, and in addition to the polymerizable compound of the present invention, other polymerizable compounds, polymerization initiators, and A solvent etc. can be contained.

[Other polymerizable compounds]
The polymerizable composition of the present invention may contain other polymerizable compound in addition to the above-described polymerizable compound of the present invention.
Here, the polymerizable group that the other polymerizable compound has is not particularly limited, and examples thereof include an acryloyl group, a methacryloyl group, a vinyl group, a styryl group, and an allyl group. Of these, an acryloyl group or a methacryloyl group is preferable.

  The other polymerizable compound is preferably another polymerizable compound having 2 to 4 polymerizable groups because the durability of the formed optically anisotropic film is further improved. More preferably, it is another polymerizable compound having two.

  Examples of such other polymerizable compounds include compounds represented by the formulas (M1), (M2), and (M3) described in paragraphs [0030] to [0033] of JP2014-077068A. More specifically, specific examples described in paragraphs [0046] to [0055] of the same publication can be given.

  In addition, specific examples of the other polymerizable compounds include liquid crystal compounds described below. In addition, all the 1,4-cyclohexylene groups in the following formula are trans-1,4-cyclohexylene groups.

In the above formula, “*” represents a bonding position.

In addition, the group adjacent to the acryloyloxy group in the above formulas II-2-8 and II-2-9 represents a propylene group (a group in which a methyl group is substituted with an ethylene group), and the positional isomerism in which the position of the methyl group is different. Represents a mixture of bodies.

(Polymerization initiator)
The polymerizable composition of the present invention preferably contains a polymerization initiator.
The polymerization initiator to be used is preferably a photopolymerization initiator capable of initiating a polymerization reaction by ultraviolet irradiation.
Examples of the photopolymerization initiator include α-carbonyl compounds (described in US Pat. Nos. 2,367,661 and 2,367,670), acyloin ether (described in US Pat. No. 2,448,828), α-hydrocarbon substituted aromatics, and the like. Group acyloin compounds (described in US Pat. No. 2,722,512), polynuclear quinone compounds (described in US Pat. Nos. 3,046,127 and 2,951,758), combinations of triarylimidazole dimers and p-aminophenyl ketone (US patents) No. 3549367), acridine and phenazine compounds (JP-A-60-105667, US Pat. No. 4,239,850) and oxadiazole compounds (US Pat. No. 4,221,970), acylphosphine Oxide compounds (Japanese Patent Publication No. 6) No. 3-40799, JP-B-5-29234, JP-A-10-95788, JP-A-10-29997) and the like.

〔solvent〕
The polymerizable composition of the present invention preferably contains a solvent from the viewpoint of workability for forming an optically anisotropic film.
Specific examples of the solvent include ketones (eg, acetone, 2-butanone, methyl isobutyl ketone, cyclohexanone, cyclopentanone, etc.), ethers (eg, dioxane, tetrahydrofuran, etc.), aliphatic hydrocarbons. (For example, hexane), alicyclic hydrocarbons (for example, cyclohexane), aromatic hydrocarbons (for example, toluene, xylene, trimethylbenzene), halogenated carbons (for example, dichloromethane, dichloroethane, dichlorobenzene) , Chlorotoluene, etc.), esters (eg, methyl acetate, ethyl acetate, butyl acetate, etc.), water, alcohols (eg, ethanol, isopropanol, butanol, cyclohexanol, etc.), cellosolves (eg, methyl cellosolve, ethyl cello) Rub etc.), cellosolve acetates, sulfoxides (eg dimethyl sulfoxide etc.), amides (eg dimethylformamide, dimethylacetamide etc.) and the like. These may be used alone or in combination of two or more. You may use together.

[Optically anisotropic film]
The optically anisotropic film of the present invention is an optically anisotropic film obtained by curing the above-described polymerizable composition of the present invention.
Examples of the method for forming the optically anisotropic film include a method in which the above-described polymerizable composition of the present invention is used to obtain a desired alignment state and then fixed by polymerization.
Here, the polymerization conditions are not particularly limited, but it is preferable to use ultraviolet rays in polymerization by light irradiation. Irradiation amount ^is preferably ^{10mJ / cm 2 ~50J / cm 2} , more preferably ^{20mJ / cm 2 ~5J / cm 2} , more preferably 30mJ ^/ cm ² ~3J ^/ cm 2 50 to 1000 mJ / cm ² is particularly preferable. Moreover, in order to accelerate | stimulate a polymerization reaction, you may implement on heating conditions.
In the present invention, the optically anisotropic film can be formed on any support in the optical film of the present invention described later or on the polarizer in the polarizing plate of the present invention described later.

In the present invention, for the reason that the contrast ratio in an image display device, particularly a liquid crystal display device is improved, the optically anisotropic film is polymerized (aligned) after the polymerizable liquid crystal composition of the present invention is aligned in the smectic phase. A membrane obtained by immobilization is preferred.
This is presumably because the smectic phase has a higher degree of order than the nematic phase, and the scattering due to the disordered orientation of the optically anisotropic layer is suppressed. Whether or not the optically anisotropic film exhibits a smectic phase can be determined by whether or not it has a periodic structure by X-ray diffraction. For example, the presence or absence of a periodic structure can be confirmed by analyzing a diffraction pattern with a thin film X-ray diffraction apparatus ATXG (manufactured by Rigaku Corporation).

  The optically anisotropic film of the present invention is preferably a positive A plate or a positive C plate, and more preferably a positive A plate.

Here, the positive A plate (positive A plate) and the positive C plate (positive C plate) are defined as follows.
The refractive index in the slow axis direction in the film plane (direction in which the refractive index in the plane is maximum) is nx, the refractive index in the direction perpendicular to the slow axis in the plane is ny, and the refractive index in the thickness direction. When the rate is nz, the positive A plate satisfies the relationship of the formula (A1), and the positive C plate satisfies the relationship of the formula (C1). The positive A plate shows a positive value for Rth, and the positive C plate shows a negative value for Rth.
Formula (A1) nx> ny≈nz
Formula (C1) nz> nx≈ny
The above “≈” includes not only the case where both are completely the same, but also the case where both are substantially the same.
“Substantially the same” means that, for a positive A plate, for example, (ny-nz) × d (where d is the thickness of the film) is −10 to 10 nm, preferably −5 to 5 nm. It is included in “ny≈nz”, and (nx−nz) × d is also included in “nx≈nz” when −10 to 10 nm, preferably −5 to 5 nm. In the positive C plate, for example, (nx−ny) × d (where d is the thickness of the film) is included in “nx≈ny” in the case of 0 to 10 nm, preferably 0 to 5 nm.

When the optically anisotropic film of the present invention is a positive A plate, from the viewpoint of functioning as a λ / 4 plate, Re (550) is preferably 100 to 180 nm, more preferably 120 to 160 nm, More preferably, it is 130-150 nm, and it is especially preferable that it is 130-140 nm.
Here, the “λ / 4 plate” is a plate having a λ / 4 function, and specifically, a function of converting linearly polarized light having a specific wavelength into circularly polarized light (or circularly polarized light into linearly polarized light). It is a board which has.

[Optical film]
The optical film of the present invention is an optical film having the optical anisotropic film of the present invention.
FIG. 1A, FIG. 1B, and FIG. 1C (hereinafter, these drawings are abbreviated as “FIG. 1” unless they need to be distinguished in particular) are schematic cross-sectional views showing examples of the optical film of the present invention.
Note that FIG. 1 is a schematic diagram, and the thickness relationship and positional relationship of each layer do not necessarily match the actual ones, and the support, alignment film, and hard coat layer shown in FIG. It is a member.
The optical film 10 shown in FIG. 1 has a support 16, an alignment film 14, and an optical anisotropic film 12 in this order.
1B, the optical film 10 may have a hard coat layer 18 on the side opposite to the side on which the alignment film 14 of the support 16 is provided. As shown in FIG. 1C, The optically anisotropic film 12 may have a hard coat layer 18 on the side opposite to the side where the alignment film 14 is provided.
Hereinafter, various members used in the optical film of the present invention will be described in detail.

(Optically anisotropic film)
The optically anisotropic film included in the optical film of the present invention is the optically anisotropic film of the present invention described above.
In the optical film of the present invention, the thickness of the optically anisotropic film is not particularly limited, but is preferably 0.1 to 10 μm, and more preferably 0.5 to 5 μm.

[Support]
As described above, the optical film of the present invention may have a support as a base material for forming the optically anisotropic film.
Such a support is preferably transparent, and specifically has a light transmittance of 80% or more.

Examples of such a support include a glass substrate and a polymer film, and examples of the material of the polymer film include a cellulose polymer; an acrylic polymer having an acrylate polymer such as a polymethyl methacrylate and a lactone ring-containing polymer. Polymers; Thermoplastic norbornene polymers; Polycarbonate polymers; Polyester polymers such as polyethylene terephthalate and polyethylene naphthalate; Styrene polymers such as polystyrene and acrylonitrile / styrene copolymers (AS resin); Polyethylene, polypropylene, ethylene / propylene copolymers Polyolefin polymers such as polymers; vinyl chloride polymers; amide polymers such as nylon and aromatic polyamide; imide polymers; sulfone polymers; Phon polymers; Polyether ether ketone polymers; Polyphenylene sulfide polymers; Vinylidene chloride polymers; Vinyl alcohol polymers; Vinyl butyral polymers; Arylate polymers; Polyoxymethylene polymers; Epoxy polymers; A mixed polymer may be mentioned.
Moreover, the mode which the polarizer mentioned later serves also as such a support body may be sufficient.

  In the present invention, the thickness of the support is not particularly limited, but is preferably 5 to 60 μm, and more preferably 5 to 30 μm.

(Alignment film)
When the optical film of the present invention has the above-mentioned arbitrary support, it is preferable to have an alignment film between the support and the optically anisotropic film. Note that the above-described support may also serve as an alignment film.

The alignment film generally contains a polymer as a main component. The polymer material for alignment film is described in many documents, and many commercially available products can be obtained.
The polymer material used in the present invention is preferably polyvinyl alcohol or polyimide, and derivatives thereof. In particular, modified or unmodified polyvinyl alcohol is preferred.
With respect to the alignment film that can be used in the present invention, for example, alignment film described in WO 01/88574, page 43, line 24 to page 49, line 8; Japanese Patent No. 3907735, paragraphs [0071] to [0095] Modified liquid alcohol described in JP-A-2012-155308, a liquid crystal alignment film formed by a liquid crystal alignment agent described in JP 2012-155308 A, and the like.

In the present invention, it is also preferable to use a photo-alignment film as the alignment film because it is possible to prevent the deterioration of the surface state by not contacting the alignment film surface when forming the alignment film.
Although it does not specifically limit as a photo-alignment film | membrane, Polymer materials, such as a polyamide compound and a polyimide compound described in the paragraphs [0024]-[0043] of international publication 2005/096041; As described in Unexamined-Japanese-Patent No. 2012-155308 A liquid crystal alignment film formed from a liquid crystal aligning agent having a photo-alignable group, such as trade name LPP-JP265CP manufactured by Rollic Technologies, Inc. can be used.

  In the present invention, the thickness of the alignment film is not particularly limited. However, from the viewpoint of forming an optically anisotropic film having a uniform thickness by reducing surface irregularities that may exist on the support. The thickness is preferably 01 to 10 μm, more preferably 0.01 to 1 μm, and still more preferably 0.01 to 0.5 μm.

[Hard coat layer]
The optical film of the present invention preferably has a hard coat layer in order to impart the physical strength of the film. Specifically, the support may have a hard coat layer on the side opposite to the side on which the alignment film is provided (see FIG. 1B), and the side on which the alignment film of the optical anisotropic film is provided; May have a hard coat layer on the opposite side (see FIG. 1C).
As the hard coat layer, those described in paragraphs [0190] to [0196] of JP-A-2009-98658 can be used.

[Other optically anisotropic films]
The optical film of the present invention may have another optical anisotropic film in addition to the optical anisotropic film of the present invention.
That is, the optical film of the present invention may have a laminated structure of the optical anisotropic film of the present invention and another optical anisotropic film.
Such other optically anisotropic film does not contain the polymerizable compound represented by the above formula (1), and is optically anisotropic obtained by using the above-described other polymerizable compound (particularly, a liquid crystal compound). There is no particular limitation as long as it is a conductive film.
Here, in general, liquid crystal compounds can be classified into a rod type and a disk type from the shape. In addition, there are low and high molecular types, respectively. Polymer generally refers to a polymer having a degree of polymerization of 100 or more (Polymer Physics / Phase Transition Dynamics, Masao Doi, 2 pages, Iwanami Shoten, 1992). In the present invention, any liquid crystal compound can be used, but a rod-like liquid crystal compound or a discotic liquid crystal compound (discotic liquid crystal compound) is preferably used. Two or more kinds of rod-like liquid crystal compounds, two or more kinds of disk-like liquid crystal compounds, or a mixture of a rod-like liquid crystal compound and a disk-like liquid crystal compound may be used. In order to fix the liquid crystal compound described above, it is more preferable to use a rod-like liquid crystal compound or a discotic liquid crystal compound having a polymerizable group, and the liquid crystal compound has two or more polymerizable groups in one molecule. Further preferred. When the liquid crystal compound is a mixture of two or more, it is preferable that at least one liquid crystal compound has two or more polymerizable groups in one molecule.
As the rod-shaped liquid crystal compound, for example, those described in claim 1 of JP-T-11-53019 and paragraphs [0026] to [0098] of JP-A-2005-289980 can be preferably used. As the liquid crystal compound, for example, those described in paragraphs [0020] to [0067] of JP-A-2007-108732 and paragraphs [0013] to [0108] of JP-A-2010-244038 can be preferably used. However, it is not limited to these.

[Polarizer]
The polarizing plate of the present invention has the above-described optical film of the present invention and a polarizer.
The polarizing plate of the present invention can be used as a circularly polarizing plate when the above-described optically anisotropic film of the present invention is a λ / 4 plate (positive A plate).
In the polarizing plate of the present invention, when the above-described optically anisotropic film of the present invention is a λ / 4 plate (positive A plate), the slow axis of the λ / 4 plate and the absorption axis of the polarizer described later Is preferably 30 to 60 °, more preferably 40 to 50 °, still more preferably 42 to 48 °, and particularly preferably 45 °.
Here, the “slow axis” of the λ / 4 plate means the direction in which the refractive index is maximum in the plane of the λ / 4 plate, and the “absorption axis” of the polarizer means the direction having the highest absorbance. To do.

[Polarizer]
The polarizer which the polarizing plate of this invention has is not specifically limited if it is a member which has a function which converts light into specific linearly polarized light, A conventionally well-known absorption type polarizer and reflection type polarizer can be utilized. .
As the absorption polarizer, an iodine polarizer, a dye polarizer using a dichroic dye, a polyene polarizer, and the like are used. Iodine polarizers and dye polarizers include coating polarizers and stretchable polarizers, both of which can be applied. Polarized light produced by adsorbing iodine or dichroic dye to polyvinyl alcohol and stretching. A child is preferred.
Further, as a method for obtaining a polarizer by stretching and dyeing in the state of a laminated film in which a polyvinyl alcohol layer is formed on a substrate, Patent No. 5048120, Patent No. 5143918, Patent No. 4691205, Patent No. 4751481 and Japanese Patent No. 4751486 can be cited, and known techniques relating to these polarizers can also be preferably used.
As the reflective polarizer, a polarizer in which thin films having different birefringence are stacked, a wire grid polarizer, a polarizer in which a cholesteric liquid crystal having a selective reflection region and a quarter wavelength plate are combined, or the like is used.
Among them, a polyvinyl alcohol resin (a polymer containing —CH ₂ —CHOH— as a repeating unit. In particular, at least one selected from the group consisting of polyvinyl alcohol and an ethylene-vinyl alcohol copolymer in terms of better adhesion. Are preferably included.

  In the present invention, the thickness of the polarizer is not particularly limited, but is preferably 3 μm to 60 μm, more preferably 5 μm to 30 μm, and still more preferably 5 μm to 15 μm.

(Adhesive layer)
In the polarizing plate of the present invention, an adhesive layer may be disposed between the optically anisotropic film and the polarizer in the optical film of the present invention.
As the pressure-sensitive adhesive layer used for laminating the optically anisotropic film and the polarizer, for example, the ratio of the storage elastic modulus G ′ and the loss elastic modulus G ″ measured with a dynamic viscoelasticity measuring apparatus (tan δ = G ″ / G ′) represents a material having a ratio of 0.001 to 1.5, and includes a so-called pressure-sensitive adhesive, a substance that easily creeps, and the like. Examples of the adhesive that can be used in the present invention include, but are not limited to, a polyvinyl alcohol-based adhesive.

[Image display device]
The image display device of the present invention is an image display device having the optical film of the present invention or the polarizing plate of the present invention.
The display element used in the image display device of the present invention is not particularly limited, and examples thereof include a liquid crystal cell, an organic electroluminescence (hereinafter abbreviated as “EL”) display panel, a plasma display panel, and the like.
Among these, a liquid crystal cell and an organic EL display panel are preferable, and a liquid crystal cell is more preferable. That is, the image display device of the present invention is preferably a liquid crystal display device using a liquid crystal cell as a display element, and an organic EL display device using an organic EL display panel as a display element, and is a liquid crystal display device. More preferred.

[Liquid Crystal Display]
The liquid crystal display device which is an example of the image display device of the present invention is a liquid crystal display device having the above-described polarizing plate of the present invention and a liquid crystal cell.
In the present invention, among the polarizing plates provided on both sides of the liquid crystal cell, the polarizing plate of the present invention is preferably used as the polarizing plate on the front side, and the polarizing plate of the present invention is used as the polarizing plate on the front side and the rear side. Is more preferable.
Below, the liquid crystal cell which comprises a liquid crystal display device is explained in full detail.

<Liquid crystal cell>
The liquid crystal cell used in the liquid crystal display device is preferably in a VA (Vertical Alignment) mode, an OCB (Optically Compensated Bend) mode, an IPS (In-Plane-Switching) mode, or a TN (Twisted Nematic). It is not limited to.
In a TN mode liquid crystal cell, rod-like liquid crystal molecules are substantially horizontally aligned when no voltage is applied, and are twisted and aligned at 60 to 120 °. The TN mode liquid crystal cell is most frequently used as a color TFT liquid crystal display device, and is described in many documents.
In a VA mode liquid crystal cell, rod-like liquid crystalline molecules are aligned substantially vertically when no voltage is applied. The VA mode liquid crystal cell includes (1) a narrowly defined VA mode liquid crystal cell in which rod-like liquid crystalline molecules are aligned substantially vertically when no voltage is applied, and substantially horizontally when a voltage is applied (Japanese Patent Laid-Open No. Hei 2-). 176625) (2) Liquid crystal cell (SID97, Digest of tech. Papers (Preliminary Proceed) 28 (1997) 845 in which the VA mode is converted into a multi-domain (MVA mode) for widening the viewing angle. ), (3) A liquid crystal cell in a mode (n-ASM mode) in which rod-like liquid crystalline molecules are substantially vertically aligned when no voltage is applied and twisted multi-domain alignment is applied when a voltage is applied (Preliminary collections 58-59 of the Japan Liquid Crystal Society) (1998)) and (4) SURVIVAL mode liquid crystal cells (announced at LCD International 98). Moreover, any of PVA (Patterned Vertical Alignment) type, optical alignment type (Optical Alignment), and PSA (Polymer-Stained Alignment) may be used. Details of these modes are described in JP-A-2006-215326 and JP-T-2008-538819.
In an IPS mode liquid crystal cell, rod-like liquid crystal molecules are aligned substantially parallel to the substrate, and the liquid crystal molecules respond in a planar manner when an electric field parallel to the substrate surface is applied. The IPS mode displays black when no electric field is applied, and the absorption axes of the pair of upper and lower polarizing plates are orthogonal. JP-A-10-54982, JP-A-11-202323, and JP-A-9-292522 are methods for reducing leakage light at the time of black display in an oblique direction and improving a viewing angle using an optical compensation sheet. No. 11-133408, No. 11-305217, No. 10-307291, and the like.

[Organic EL display device]
As an organic EL display device which is an example of the image display device of the present invention, for example, from the viewing side, a polarizer, a λ / 4 plate (positive A plate) made of the optically anisotropic film of the present invention, and an organic EL device. An embodiment having the display panel in this order is preferable.
The organic EL display panel is a display panel configured using an organic EL element in which an organic light emitting layer (organic electroluminescence layer) is sandwiched between electrodes (between a cathode and an anode). The configuration of the organic EL display panel is not particularly limited, and a known configuration is adopted.

  Hereinafter, the present invention will be described in more detail based on examples. The materials, amounts used, ratios, processing details, processing procedures, and the like shown in the following examples can be changed as appropriate without departing from the spirit of the present invention. Therefore, the scope of the present invention should not be construed as being limited by the following examples.

[Example 1]
<Synthesis of Compound (Ic)>

  As shown in the above scheme, compound (Ic) was synthesized according to the method described in paragraph [0175] of JP-A-2006-081035 (Example 17).

<Synthesis of Compound (I-1c)>

  Next, as shown in the above scheme, 1.72 g (8.21 mmol) of compound (I-1b) and 5.0 g (16.4 mmol) of compound (Ic) were added in tetrahydrofuran (THF) (50 mL). The mixture was stirred at 0 ° C., and 2.65 g (20.5 mmol) of N, N-diisopropylethylamine (DIPEA) was added dropwise thereto. After stirring at 0 ° C. for 1 hour, ethyl acetate (60 mL) and 1N aqueous hydrochloric acid (100 mL) were added at 0 ° C. Thereafter, the aqueous layer was removed, and the organic layer was washed with brine. The organic layer was dried over sodium sulfate and the desiccant was filtered, and then the solvent was distilled off under reduced pressure. Methanol was added and the precipitated solid was filtered to obtain 4.03 g of Compound (I-1c) (yield 65%).

<Synthesis of Compound (I-1-1)>

Then, as shown in the above scheme, 1.15 g (2.27 mmol) of compound (I-1-1a), 7.5 mL of ethyl acetate (EA), 2.3 mL of N, N-dimethylacetamide (DMAc), and 30 mg of 2,6-di-t-butyl-4-methylphenol was mixed at room temperature (23 ° C.), and the internal temperature was cooled to 5 ° C. To the mixture, 0.19 ml (2.66 mmol) of thionyl chloride (SOCl ₂ ) was added dropwise so that the internal temperature did not rise above 10 ° C. After stirring at 5 ° C. for 1 hour, 0.7 g (0.95 mmol) of Compound (I-1c) was added. N, N-diisopropylethylamine (DIPEA) 0.73 g (5.68 mmol) was added dropwise so that the internal temperature did not exceed 5 ° C., and the mixture was stirred at room temperature for 3 hours. After stirring, methanol and water were added, and the precipitated solid was filtered to obtain 0.99 g of compound (I-1-1) (yield 60%).
¹ H-NMR (Nuclear Magnetic Resonance) of the obtained compound (I-1-1) is shown below.
¹ H-NMR (solvent: CDCl ₃ ) δ (ppm): 1.3 (m, 6H), 1.4 (s, 18H), 1.7-1.8 (m, 12H), 2.4 ( m, 14H), 2.6-2.7 (m, 12H), 2.9 (t, 4H), 4.1-4.3 (m, 8H), 5.2 (m, 2H), 5 .8 (dd, 2H), 6.1 (dd, 2H), 6.4 (dd, 2H), 7.0 (d, 4H), 7.2 (d, 4H), 7.4 (s, 2H)

[Example 2]
<Synthesis of Compound (I-2b)>

  As shown in the above scheme, triphosgene (12.06 g) was stirred in THF (40 mL) at 0 ° C., where it was added compound (I-2a) (5 g), N, N-diethylaniline (20.5 mL). And a solution prepared by previously mixing THF (20 mL) was added dropwise over 30 minutes and stirred at room temperature for 2 hours. Ethyl acetate (60 mL) and 1N aqueous hydrochloric acid (128 mL) were added at 0 ° C., the aqueous layer was removed, and the organic layer was washed with brine. The organic layer was dried over sodium sulfate and the desiccant was filtered, and then the solvent was distilled off under reduced pressure. The obtained solid was washed with hexane and filtered to obtain compound (I-2b).

<Synthesis of Compound (I-2c)>

Next, as shown in the above scheme, 0.19 g (0.838 mmol) of compound (I-2b) and 0.51 g (1.68 mmol) of compound (Ic) were stirred in THF (15 mL) at room temperature, Thereto, 20 mg (0.168 mmol) of N, N-dimethylaminopyridine (DMAP) was added, and 0.35 ml (2.52 mmol) of triethylamine (NEt ₃ ) was added dropwise. After stirring at room temperature for 4 hours, methanol was added and the precipitated solid was filtered to obtain 0.47 g (0.628 mmol) of Compound (I-2c) (yield 75%).

<Synthesis of Compound (I-2-1)>

Then, as shown in the above scheme, 0.5 g (0.67 mmol) of compound (I-2c), 0.85 g (1.67 mmol) of compound (I-1-1a), and 2,6-di-t 7 mg of butyl-4-methylphenol are stirred in THF (15 mL) at room temperature, and there is 0.38 g (2.01 mmol) of 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride (EDCl). ), 8 mg (0.067 mmol) of DMAP was added. After stirring at room temperature for 4 hours, 10 ml of 1M aqueous hydrochloric acid and 15 ml of ethyl acetate were added, and the mixture was extracted with ethyl acetate. The organic layer was washed with 10% brine, methanol was added, and the precipitated solid was filtered to obtain 1.23 g of compound (I-2-1) (yield 70%).
¹ H-NMR of the obtained compound (I-2-1) is shown below.
¹ H-NMR (solvent: CDCl ₃ ) δ (ppm): 1.3 (m, 6H), 1.4 (s, 18H), 1.7-1.8 (m, 8H), 2.4 ( m, 8H), 2.6-2.7 (m, 12H), 2.9 (t, 4H), 3.7-3.9 (m, 8H), 4.1-4.3 (m, 8H), 5.2 (m, 2H), 5.8 (dd, 2H), 6.1 (dd, 2H), 6.4 (dd, 2H), 7.0 (d, 4H), 7. 2 (d, 4H), 7.4 (s, 2H)

Example 3
<Synthesis of Compound (I-2-5)>

In the above scheme, the compound (I-1-5a) was synthesized by the method described in JP-A-2006-53149.
Then, as shown in the above scheme, 0.47 g (0.629 mmol) of compound (I-2c), 0.47 g (1.57 mmol) of compound (I-1-5a), and 2,6-di-t 7 mg of butyl-4-methylphenol are stirred in THF (15 mL) at room temperature, and there is 0.37 g (1.89 mmol) of 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride (EDCl). ), 8 mg (0.0629 mmol) of DMAP was added. After stirring at room temperature for 2 hours, 10 ml of 1M aqueous hydrochloric acid and 15 ml of ethyl acetate were added, and the mixture was extracted with ethyl acetate. The organic layer was washed with 10% brine, then the organic layer was dried over magnesium sulfate, and the solvent was distilled off under reduced pressure. 40 ml of methanol was added, and the precipitated solid was filtered to obtain 0.54 g (0.415 mmol) of Compound (I-2-5) (yield 68%).
¹ H-NMR of the obtained compound (I-2-5) is shown below.
¹ H-NMR (solvent: CDCl ₃ ) δ (ppm): 1.3 (s, 18H), 1.6-1.8 (m, 16H), 2.2-2.4 (m, 10H), 2.6 (m, 2H), 3.7-3.9 (m, 8H), 4.1-4.2 (m, 8H), 5.8 (dd, 2H), 6.1 (dd, 2H), 6.4 (dd, 2H), 7.3 (s, 2H)

Example 4
<Synthesis of Compound (I-2-10)>

In the above scheme, compound (I-1-10a) was synthesized by a conventional method using 4-acryloxybutanol and phosgene.
Then, as shown in the above scheme, 0.5 g (0.669 mmol) of compound (I-2c), 0.82 g (4.01 mmol) of compound (I-1-10a), and 2,6-di-t 7 mg of butyl-4-methylphenol was stirred at 0 ° C. in dichloromethane (15 mL), and 8 mg (0.0629 mmol) of DMAP and 0.32 ml (4.01 mmol) of pyridine were added dropwise thereto. After stirring at room temperature for 2 hours, 10 ml of water and 15 ml of ethyl acetate were added, and the mixture was extracted with ethyl acetate. The organic layer was washed sequentially with 1N aqueous hydrochloric acid, saturated aqueous sodium hydrogen carbonate, and 10% brine, then the organic layer was dried over magnesium sulfate, and the solvent was distilled off under reduced pressure. The obtained crude product was purified by silica gel column chromatography to obtain 0.44 g (0.402 mmol) of compound (I-2-10) (yield 60%).
¹ H-NMR of the obtained compound (I-2-10) is shown below.
¹ H-NMR (solvent: CDCl ₃ ) δ (ppm): 1.3 (s, 18H), 1.8-2.0 (m, 8H), 3.7-3.9 (m, 8H), 4.2 (t, 4H), 4.4 (t, 4H), 5.8 (dd, 2H), 6.1 (dd, 2H), 6.4 (dd, 2H), 7.3 (s , 2H)

Example 5
<Synthesis of Compound (I-4c)>

As shown in the above scheme, 5.0 g (16.4 mmol) of compound (Ic) was stirred in THF (50 mL) at 0 ° C., and then DIPEA and 1.26 g of compound (I-4b) ( 8.21 mmol).
Subsequently, after stirring at 0 ° C. for 1 hour, ethyl acetate (60 mL) and 1N aqueous hydrochloric acid (100 mL) were added at 0 ° C. The aqueous layer was removed and the organic layer was washed with brine. The organic layer was dried over sodium sulfate and the desiccant was filtered, and then the solvent was distilled off under reduced pressure. After the obtained crude product was purified by silica gel column chromatography, acetonitrile was added and the precipitated solid was filtered to obtain 2.5 g of Compound (I-4c) (yield 45%).

<Synthesis of Compound (I-4-1)>

As shown in the above scheme, the same method as compound (I-1-1) except that compound (I-1c) was changed to compound (I-4c) in the synthesis method of compound (I-1-1) Thus, compound (I-4-1) was synthesized.
¹ H-NMR of the obtained compound (I-4-1) is shown below.
¹ H-NMR (solvent: CDCl ₃ ) δ (ppm): 1.3 (m, 6H), 1.4 (s, 18H), 1.7-1.8 (m, 8H), 2.4 ( m, 8H), 2.6-2.7 (m, 12H), 2.9 (t, 4H), 4.1-4.3 (m, 8H), 5.2 (m, 2H), 5 .8 (dd, 2H), 6.1 (dd, 2H), 6.4 (dd, 2H), 7.0 (d, 4H), 7.2 (d, 4H), 7.4 (m, 4H)

Example 6
<Synthesis of Compound (I-6c)>

  As shown in the above scheme, 5.0 g (16.4 mmol) of compound (Ic) was stirred in THF (50 mL) at 0 ° C. under a nitrogen atmosphere, and 2.55 g (19.7 mmol) of DIPEA was added thereto. And 1.04 g (8.21 mmol) of the compound (I-6b) were added dropwise in this order. After stirring at room temperature for 1 hour, ethyl acetate (60 mL) and 1N aqueous hydrochloric acid (100 mL) were added at 0 ° C. The aqueous layer was removed and the organic layer was washed with brine. The organic layer was dried over sodium sulfate and the desiccant was filtered, and then the solvent was distilled off under reduced pressure. By adding acetonitrile, the precipitated solid was filtered to obtain 2.7 g of Compound (I-6c) (yield 50%).

<Synthesis of Compound (I-6-1)>

As shown in the above scheme, the same method as compound (I-1-1) except that compound (I-1c) was changed to compound (I-6c) in the synthesis method of compound (I-1-1) Thus, compound (I-6-1) was synthesized.
¹ H-NMR of the obtained compound (I-6-1) is shown below.
¹ H-NMR (solvent: CDCl ₃ ) δ (ppm): 1.3 (m, 6H), 1.4 (s, 18H), 1.7-1.8 (m, 8H), 2.4 ( m, 8H), 2.6-2.7 (m, 12H), 2.9 (t, 4H), 4.1-4.3 (m, 8H), 5.2 (m, 2H), 5 .8 (dd, 2H), 6.1 (dd, 2H), 6.4 (dd, 2H), 7.0 (d, 4H), 7.2 (d, 4H), 7.4 (s, 2H)

Example 7
<Synthesis of Compound (I-7c)>

As shown in the above scheme, 2.0 g (6.57 mmol) of compound (Ic) and 0.78 g (3.29 mmol) of compound (I-7b) were stirred in DMAc (20 mL) at room temperature under a nitrogen atmosphere. Then, 1.2 g (8.21 mmol) of K ₂ CO ₃ was added thereto. After stirring at 70 ° C. for 3 hours, ethyl acetate (60 mL) and 1N aqueous hydrochloric acid (50 mL) were added at room temperature. The aqueous layer was removed, and the organic layer was washed with 1N hydrochloric acid and brine in this order. The organic layer was dried over sodium sulfate and the desiccant was filtered, and then the solvent was distilled off under reduced pressure. After the obtained crude product was purified by silica gel column chromatography, acetonitrile was added and the precipitated solid was filtered to obtain 0.63 g (0.628 mmol) of Compound (I-7c) (yield 30%). ).

<Synthesis of Compound (I-7-1)>

As shown in the above scheme, the same method as compound (I-2-1) except that compound (I-2c) was changed to compound (I-7c) in the synthesis method of compound (I-2-1) Thus, compound (I-7-1) was synthesized.
¹ H-NMR of the obtained compound (I-7-1) is shown below.
¹ H-NMR (solvent: CDCl ₃ ) δ (ppm): 1.3 (m, 6H), 1.4 (s, 18H), 1.7-1.8 (m, 8H), 2.4 ( m, 8H), 2.6-2.7 (m, 12H), 2.9 (t, 4H), 4.1-4.3 (m, 8H), 4.5 (m, 4H), 5 .2 (m, 2H), 5.8 (dd, 2H), 6.1 (dd, 2H), 6.4 (dd, 2H), 7.0 (d, 4H), 7.2 (d, 4H), 7.3 (s, 2H)

Example 8
<Synthesis of Compound (I-8b)>

  As shown in the above scheme, compound (I-2b) was synthesized in the same manner as compound (I-2b) except that compound (I-2a) was changed to compound (I-8a) in the synthesis method of compound (I-2b). I-8b) was synthesized.

<Synthesis of Compound (I-8c)>

  As shown in the above scheme, compound (I-2c) was synthesized in the same manner as compound (I-2c) except that compound (I-2b) was changed to compound (I-8b) in the synthesis method of compound (I-2c). I-8c) was synthesized (yield 73%).

<Synthesis of Compound (I-8-5)>

As shown in the above scheme, the same method as compound (I-2-5) except that compound (I-2c) was changed to compound (I-8c) in the synthesis method of compound (I-2-5) Thus, compound (I-8-5) was synthesized (yield 68%).
¹ H-NMR of the obtained compound (I-8-5) is shown below.
¹ H-NMR (solvent: CDCl ₃ ) δ (ppm): 1.3 (s, 18H), 1.4 (m, 3H), 1.6-1.8 (m, 16H), 2.2- 2.4 (m, 10H), 2.6 (m, 2H), 3.2-3.6 (m, 3H), 4.1-4.3 (m, 11H), 4.5 (m, 1H), 5.8 (dd, 2H), 6.1 (dd, 2H), 6.4 (dd, 2H), 7.3 (s, 2H)

Example 9
<Synthesis of Compound (I-8-10)>

As shown in the above scheme, the same method as compound (I-2-10) except that compound (I-2c) was changed to compound (I-8c) in the synthesis method of compound (I-2-10) Thus, compound (I-8-10) was synthesized (yield 59%).
¹ H-NMR of the obtained compound (I-8-10) is shown below.
¹ H-NMR (solvent: CDCl ₃ ) δ (ppm): 1.3 (s, 18H), 1.4 (m, 3H), 1.8-2.0 (m, 8H), 3.2 3.6 (m, 3H), 4.1 (m, 2H), 4.2 (m, 5H), 4.4 (t, 4H), 4.5 (m, 1H), 5.8 (dd , 2H), 6.1 (dd, 2H), 6.4 (dd, 2H), 7.3 (s, 2H)

Example 10
<Synthesis of Compound (I-1-1b)>

  As shown in the above scheme, 3.01 g (5.97 mmol) of compound (I-1-1a), 15 mL of ethyl acetate, 4.5 mL of N, N-dimethylacetamide, and 2,6-di-t-butyl- 4-methylphenol 65mg was mixed at room temperature, and internal temperature was cooled to 5 degreeC. To the mixture, 0.52 ml (7.17 mmol) of thionyl chloride was added dropwise so that the internal temperature did not rise above 10 ° C. After stirring at 5 ° C. for 1 hour, a THF solution (8 ml) of 2.0 g (6.57 mmol) of compound (Ic) was added dropwise. After dropwise addition of 2.6 ml (14.9 mmol) of N, N-diisopropylethylamine so that the internal temperature did not exceed -5 ° C, the mixture was stirred at -5 ° C or lower for 30 minutes. After stirring, 10 ml of 1N hydrochloric acid and 10 ml of ethyl acetate were added to stop the reaction, and liquid separation was performed. The organic layer was washed with 10% brine, dried over magnesium sulfate, and the solvent was distilled off under reduced pressure. As a result of measuring the ratio of (I-1-1b) :( I-1-1c) of the obtained crude product by high performance liquid chromatography, (I-1-1b) :( I-1-1c) = 97 : 3. The resulting crude product was purified by silica gel column chromatography to obtain 2.83 g (3.58 mmol) of compound (I-1-1b) (yield 65%).

<Synthesis of Compound (II-1-1)>

Next, as shown in the above scheme, 1.0 g (1.26 mmol) of the compound (I-1-1b) was stirred in ethyl acetate (15 mL) and DMAc (7 mL) at 0 ° C., and the compound (I -1b) 0.12 g (0.57 mmol) was added. After 0.25 ml (1.47 mmol) of DIPEA was added dropwise, 3.5 mg of DMAP was added. After stirring at room temperature for 2 hours, ethyl acetate (20 mL) and 1N aqueous hydrochloric acid (50 mL) were added at 0 ° C. The aqueous layer was removed and the organic layer was washed with brine. The organic layer was dried over sodium sulfate and the desiccant was filtered, and then the solvent was distilled off under reduced pressure. A crude product was obtained by adding methanol and filtering the precipitated solid. The resulting crude product was purified by column chromatography to obtain 0.3 g of compound (II-1-1) (yield 30%).
¹ H-NMR of the obtained compound (II-1-1) is shown below.
¹ H-NMR (solvent: CDCl ₃ ) δ (ppm): 1.3 (m, 6H), 1.4 (s, 18H), 1.7-1.8 (m, 12H), 2.4 ( m, 14H), 2.6-2.7 (m, 12H), 2.9 (t, 4H), 4.1-4.3 (m, 8H), 5.2 (m, 2H), 5 .8 (dd, 2H), 6.1 (dd, 2H), 6.4 (dd, 2H), 7.0 (d, 4H), 7.2 (d, 4H), 7.4 (s, 2H)

Example 11
<Synthesis of Compound (I-9c)>

  As shown in the above scheme, compound (I-9c) was prepared in the same manner as compound (I-1c) except that compound (I-1b) in the synthesis of compound (I-1c) was changed to compound (I-9b). Synthesized (yield 65%).

<Synthesis of Compound (VII-9-6)>

In the above scheme, compound (I-1-6a) was synthesized by the method described in paragraphs [0091] to [0092] of JP-A-2018-25770.
Next, as shown in the above scheme, compound (I-1-1a) in the synthesis of compound (I-1-1) is changed to compound (I-1-6a), and compound (I-1c) is converted to compound (I-1c). Compound (VII-9-6) was synthesized in the same manner as Compound (I-1-1) except that it was changed to (I-9c) (yield 65%).

[Comparative Example 1]
<Synthesis of Compound (VII-1-1)>
Compound (XIII-1-1) was obtained in the same manner as in Example 1 except that p-benzoquinone which was compound (Ia) was used as a starting material and the following scheme was followed.

[Comparative Example 2]
Compound (XIII-1-2) was obtained in the same manner as in Example 1 except that the following scheme was followed.

<Compatibility>
The synthesis suitability of the polymerizable compounds synthesized in Examples 1 to 11 and Comparative Examples 1 and 2 was evaluated according to the following criteria. The results are shown in Table 10 and Table 11 below.
A: Phenol intermediate [refers to any compound of compound (Ic) and compound (If). The same applies to the following paragraphs. ] Is 50% or more in any step, and column purification is unnecessary.
B: The yield from the phenol intermediate is 50% or more in any step, but column purification is required.
C: The yield from the phenol intermediate is less than 50% in any step.

<Phase transition temperature>
Using a polarizing microscope, the phase transition temperatures of the polymerizable compounds synthesized in Examples 1 to 11 and Comparative Examples 1 and 2 were measured. The results are shown in Table 10 and Table 11 below. From the results shown in Table 10 and Table 11 below, it was confirmed that only the compound (I-6-1) had liquid crystallinity.

<Solubility>
The solubility measurement of the polymerizable compounds synthesized in Examples 1 to 11 and Comparative Examples 1 and 2 was performed by the method shown below. The results are shown in Table 10 and Table 11 below.
Specifically, 50 mg of the compound was weighed into a 1.5 mL sample bottle, and the solvent was added until the solid content became 40 wt% (75 mg).
The mixture was thoroughly shaken by hand at room temperature (23 ° C.), then visually observed to finish if it was clear, and the solubility was determined to be 40 wt%. If there was any undissolved residue, the solvent was added so that the solid content was 35 wt% (+18 mg). After thoroughly shaking by hand at room temperature (23 ° C.), the sample was visually observed and cleared if it was clear, and determined to be 35 wt%. If there was any undissolved residue, the solvent was added so that it might be 30 wt%. The same operation was repeated in increments of 5 wt% until it was 5 wt%. If there was any undissolved residue, it was determined that the solubility was less than 5 wt% (<5 wt%), and the process was completed. MEK (methyl ethyl ketone) and CPN (cyclopentanone) were used as solvents for solubility measurement.
A: Any solubility in MEK and CPN is 30% or more B: Any solubility in MEK and CPN is 15% or more and less than 30% C: Any solubility in MEK and CPN is 15% or more

[Examples 1 to 11 and Comparative Examples 1 and 2]
<Formation of photo-alignment film P-1>
According to Example 1 of JP 2001-141926 A, an example of JP 2012-155308 A is provided on one surface of a polarizer 1 having a thickness of 20 μm prepared by adsorbing iodine to a stretched polyvinyl alcohol film. The coating liquid 1 for photo-alignment prepared with reference to the description of 3 was applied using a second-numbered bar.
After coating, the solvent was removed by drying to form the photoisomerizable composition layer 1.
The resulting photoisomerized composition layer 1 was irradiated with polarized ultraviolet light (500 mJ / cm ² , using a 750 W ultra-high pressure mercury lamp) to form a photo-alignment film P-1.

<Production of optical film>
On the photo-alignment film P-1, a coating liquid for optically anisotropic film having the following composition was applied by spin coating to form a liquid crystal composition layer.
The formed liquid crystal composition layer was heated on a hot plate and then cooled to 60 ° C. to stabilize the alignment.
Thereafter, the orientation was fixed by ultraviolet irradiation while maintaining the temperature at 60 ° C. to form an optically anisotropic film, thereby producing an optical film.
―――――――――――――――――――――――――――――――――
Coating liquid for optically anisotropic film ―――――――――――――――――――――――――――――――――
-33.17 parts by mass of the following liquid crystal compound L-1 33.17 parts by mass of the following liquid crystal compound L-2-Polymerizable compound (compounds described in Table 10 and Table 11 below)
33.17 parts by mass-The following polymerization initiator S-1 (oxime type) 3.00 parts by mass-Leveling agent (the following compound T-1) 0.20 parts by mass-Chloroform 219.30 parts by mass--- ―――――――――――――――――――――――――――

[Comparative Example 3]
The same method as in Example 1 except that the polymerizable compound (I-1-1) was not used and the amounts of the liquid crystal compound L-1 and the liquid crystal compound L-2 were changed to 50.0 parts by mass, respectively. An optical film was prepared.

[Comparative Example 4]
An optical film was produced in the same manner as in Example 1, except that the following polymerizable compound (G-1) was used instead of the polymerizable compound (I-1-1).

  The optical films produced in the above-described Examples and Comparative Examples were immersed in warm water at 50 ° C. for 30 minutes or more, the softened polarizer 1 was removed, and the optical anisotropic film was isolated.

<Reverse wavelength dispersion>
For each optically anisotropic film, in-plane retardation at wavelengths of 450 nm and 550 nm was measured using Axo Scan (0 PMF-1, manufactured by Axometrics), and Re (450) / Re (550) was expressed by the following index. evaluated. The results are shown in Table 10 and Table 11 below. In addition, since the optically anisotropic film isolated from the optical film produced in Comparative Examples 1 and 2 was not oriented, it was not evaluated and is represented as “−” in Table 11 below.
A: Reversed wavelength dispersibility is better than when no polymerizable compound is added (Comparative Example 2) B: Equivalent to not adding a polymerizable compound (Comparative Example 2) C: No polymerizable compound is added (Comparative Example 2) ) Reverse wavelength dispersion is worse than when

<Durability>
About each optical film produced by the Example and comparative example which were mentioned above, the optically anisotropic film side was made into the glass side on the glass plate, and it bonded together through the adhesive.
Subsequently, the durability of the retardation value was evaluated with the following index using Axo Scan (0 PMF-1, manufactured by Axometrics). The results are shown in Table 10 and Table 11 below. In addition, since the optically anisotropic film isolated from the optical film produced in Comparative Examples 1 and 2 was not oriented, it was not evaluated and is represented as “−” in Table 11 below.
In addition, if the test condition is evaluated as “A” in a test that is allowed to stand for 120 hours in an environment of 100 ° C. and a relative humidity of 95%, it can be determined that the durability is good.
A: The amount of change in the value after the test with respect to the initial phase difference value is less than 10% of the initial value B: The amount of change in the value after the test with respect to the initial phase difference value is 10% or more and less than 20% of the initial value C : The amount of change in the value after the test relative to the initial phase difference value is 20% or more of the initial value

From the results shown in Table 10 and Table 11, even when the reverse wavelength dispersion expression part has two in the molecule, the aromatic ring constituting the reverse wavelength dispersion expression part has no steric hindrance group, It was found that the solubility was poor and the polymerizable composition was not oriented (Comparative Examples 1 and 2).
In contrast, a polymerizable compound having two reverse wavelength dispersion expressing parts in the molecule and the aromatic ring constituting the reverse wavelength dispersion expressing part having a steric hindrance group has excellent solubility (implementation). From comparison between Examples 1 to 11) and Examples 1 to 11 and Comparative Example 3, it was found that the durability of the optically anisotropic film was improved.
Further, from the comparison of Examples 1 to 11, it was found that Example 6 using a polymerizable compound having liquid crystallinity was excellent when synthetic suitability, solubility, reverse wavelength dispersibility and durability were comprehensively considered. .

DESCRIPTION OF SYMBOLS 10 Optical film 12 Optical anisotropic film 14 Orientation film 16 Support body 18 Hard-coat layer

Claims (13)

The polymeric compound represented by following formula (1).
Here, the formula ^(1), D ^1, D 2, ^{D 3} and ^{D 4} are independently a single bond, -O -, - CO-O -, - C (= S) O -, - ^{CR 1 R 2 -, - CR} 1 R 2 -CR 3 R 4 -, - O-CR 1 R 2 -, - CR 1 R 2 -O-CR 3 R 4 -, - CO-O-CR 1 R 2 ^{-, - O-CO-CR} 1 R 2 -, - CR 1 R 2 -O-CO-CR 3 R 4 -, - CR 1 R 2 -CO-O-CR 3 R 4 -, - NR 1 -CR ² R ³ — or —CO—NR ¹ — is represented. R ¹ , R ² , R ³ and R ⁴ each independently represent a hydrogen atom, a fluorine atom, or an alkyl group having 1 to 4 carbon atoms.
G ¹ represents ^AG or SP ^G.
A ¹ , A ² and ^AG each independently represent an aromatic ring having 6 or more carbon atoms or a cycloalkane ring having 6 or more carbon atoms, and one or more of —CH ₂ — constituting the cycloalkane ring. May be substituted with -O-, -S- or -NH-.
SP ¹ , SP ² and SP ^G are each independently a single bond, a linear or branched alkylene group having 1 to 20 carbon atoms, a linear or branched alkenylene group having 1 to 20 carbon atoms, carbon 1 to 20 linear or branched alkynylene groups or one or more of —CH ₂ — constituting the alkylene group, the alkenylene group or the alkynylene group is —O—, —S—, —NH It represents a divalent linking group substituted with-, -N (Q)-or -CO-, and Q represents a substituent.
L ¹ and L ² each independently represent a monovalent organic group, and at least one of L ¹ and L ² represents a polymerizable group. However, when at least one of Ar ¹ and Ar ² is an aromatic ring represented by the following formula (Ar-4), L ¹ and L ² and L ³ and L ^{4 in the following} formula (Ar-4) At least one of represents a polymerizable group.
m represents an integer of 0 to 2, and when m is 2, a plurality of G ¹ may be the same or different, and a plurality of D ¹ may be the same or different. Good.
l and n each independently represents 0 or an integer of 1 or more, and when l is an integer of 2 or more, a plurality of A ^{1 s} may be the same or different, and a plurality of D ³ are Each may be the same or different. When n is an integer of 2 or more, the plurality of D ⁴ may be the same or different, and the plurality of A ² may be the same or different.
Ar ¹ and Ar ² each independently represent any aromatic ring selected from the group consisting of groups represented by the following formulas (Ar-1) to (Ar-8).
Here, in the formulas (Ar-1) to (Ar-8), * 1 represents a bonding position with D ¹ or D ^3, and * 2 represents a bonding position with D ² or D ⁴ .
Q ¹ represents N or CH.
Q ² represents —S—, —O—, or —N (R ⁵ ) —, and R ⁵ represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.
Y ¹ represents an optionally substituted aromatic hydrocarbon group having 6 to 12 carbon atoms or an aromatic heterocyclic group having 3 to 12 carbon atoms.
Z ¹ represents a monovalent aliphatic hydrocarbon group having 3 to 20 carbon atoms, a monovalent aromatic hydrocarbon group having 6 to 20 carbon atoms, a halogen atom, —OR ⁶ , —NR ⁷ R ⁸ , or , -SR ⁹ , and R ^{6 to} R ⁹ each independently represent a monovalent aliphatic hydrocarbon group having 3 to 20 carbon atoms or a monovalent aromatic hydrocarbon group having 6 to 20 carbon atoms.
Z ² is a hydrogen atom, a monovalent aliphatic hydrocarbon group having 1 to 20 carbon atoms, a monovalent alicyclic hydrocarbon group having 3 to 20 carbon atoms, or a monovalent aromatic having 6 to 20 carbon atoms. Represents a hydrocarbon group, a halogen atom, a cyano group, a nitro group, —OR ¹⁰ , —NR ¹¹ R ¹² , or —SR ¹³ , wherein R ^{10 to} R ¹³ each independently represent a hydrogen atom or a carbon number of 1 to Represents an alkyl group of 6;
A ³ and A ⁴ each independently represent a group selected from the group consisting of —O—, —N (R ¹⁴ ) —, —S—, and —CO—, and R ¹⁴ represents hydrogen. Represents an atom or substituent.
X represents a hydrogen atom or a nonmetallic atom of Groups 14 to 16 to which a substituent may be bonded.
D ⁵ and D ⁶ are each independently a single bond, —O—CO—, —C (═S) O—, —CR ¹ R ² —, —CR ¹ R ² —CR ³ R ⁴ —, ^{-O-CR 1 R 2 -,} - CR 1 R 2 -O-CR 3 R 4 -, - CO-O-CR 1 R 2 -, - O-CO-CR 1 R 2 -, - CR 1 R 2 ^{-O-CO-CR 3 R 4} -, - CR 1 R 2 -CO-O-CR 3 R 4 -, - NR 1 -CR 2 R 3 -, or, -CO-NR ¹ - represents a. R ¹ , R ² , R ³ and R ⁴ each independently represent a hydrogen atom, a fluorine atom, or an alkyl group having 1 to 4 carbon atoms.
SP ³ and SP ⁴ each independently represent a single bond, a linear or branched alkylene group having 1 to 12 carbon atoms, or a linear or branched alkylene group having 1 to 12 carbon atoms. A divalent linking group in which at least one of —CH ₂ — constituting is substituted with —O—, —S—, —NH—, —N (Q) —, or —CO—; Represents a substituent.
L ³ and L ⁴ each independently represent a monovalent organic group, and at least one of L ³ and L ⁴ and L ¹ and L ^{2 in} the formula (1) represents a polymerizable group.
Ax represents an organic group having 2 to 30 carbon atoms having at least one aromatic ring selected from the group consisting of an aromatic hydrocarbon ring and an aromatic heterocyclic ring.
Ay represents a hydrogen atom, an optionally substituted alkyl group having 1 to 12 carbon atoms, or at least one aromatic ring selected from the group consisting of an aromatic hydrocarbon ring and an aromatic heterocyclic ring. And an organic group having 2 to 30 carbon atoms.
Further, the aromatic ring in Ax and Ay may have a substituent, and Ax and Ay may be bonded to form a ring.
Q ³ represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms which may have a substituent.   The polymerizable compound according to claim 1, wherein m in the formula (1) is 1. The polymerizable compound according to claim 1 or 2, wherein Z ¹ in the formulas (Ar-1) to (Ar-8) represents a monovalent aliphatic hydrocarbon group having 3 to 20 carbon atoms. The polymerizable compound according to claim 1, wherein Z ¹ in the formulas (Ar-1) to (Ar-8) represents a tert-butyl group.   The polymerizable compound according to any one of claims 1 to 4, which has liquid crystallinity. A method for producing a polymerizable compound for synthesizing the polymerizable compound according to claim 1,
A first esterification step of reacting a compound represented by the following formula (2) with a compound represented by the following formula (3) to produce a first phenol compound;
A second esterification step of reacting the first phenol reactant obtained in the first esterification step with a compound represented by the following formula (4) to obtain a polymerizable compound according to claim 1; The manufacturing method of the polymeric compound which has these.
In the formula (2), Ar represents any aromatic ring selected from the group consisting of groups represented by the following formulas (Ar-1) to (Ar-8).
Here, in the formulas (Ar-1) to (Ar-8), * 1 and * 2 each represent a bonding position with a hydroxyl group.
Q ¹ represents N or CH.
Q ² represents —S—, —O—, or —N (R ⁵ ) —, and R ⁵ represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.
Y ¹ represents an optionally substituted aromatic hydrocarbon group having 6 to 12 carbon atoms or an aromatic heterocyclic group having 3 to 12 carbon atoms.
Z ¹ represents a monovalent aliphatic hydrocarbon group having 3 to 20 carbon atoms, a monovalent aromatic hydrocarbon group having 6 to 20 carbon atoms, a halogen atom, —OR ⁶ , —NR ⁷ R ⁸ , or , -SR ⁹ , and R ^{6 to} R ⁹ each independently represent a monovalent aliphatic hydrocarbon group having 3 to 20 carbon atoms or a monovalent aromatic hydrocarbon group having 6 to 20 carbon atoms.
Z ² is a hydrogen atom, a monovalent aliphatic hydrocarbon group having 1 to 20 carbon atoms, a monovalent alicyclic hydrocarbon group having 3 to 20 carbon atoms, or a monovalent aromatic having 6 to 20 carbon atoms. Represents a hydrocarbon group, a halogen atom, a cyano group, a nitro group, —OR ¹⁰ , —NR ¹¹ R ¹² , or —SR ¹³ , wherein R ^{10 to} R ¹³ each independently represent a hydrogen atom or a carbon number of 1 to Represents an alkyl group of 6;
A ³ and A ⁴ each independently represent a group selected from the group consisting of —O—, —N (R ¹⁴ ) —, —S—, and —CO—, and R ¹⁴ represents hydrogen. Represents an atom or substituent.
X represents a hydrogen atom or a nonmetallic atom of Groups 14 to 16 to which a substituent may be bonded.
D ⁵ and D ⁶ are each independently a single bond, —O—CO—, —C (═S) O—, —CR ¹ R ² —, —CR ¹ R ² —CR ³ R ⁴ —, ^{-O-CR 1 R 2 -,} - CR 1 R 2 -O-CR 3 R 4 -, - CO-O-CR 1 R 2 -, - O-CO-CR 1 R 2 -, - CR 1 R 2 ^{-O-CO-CR 3 R 4} -, - CR 1 R 2 -CO-O-CR 3 R 4 -, - NR 1 -CR 2 R 3 -, or, -CO-NR ¹ - represents a. R ¹ , R ² , R ³ and R ⁴ each independently represent a hydrogen atom, a fluorine atom, or an alkyl group having 1 to 4 carbon atoms.
SP ³ and SP ⁴ each independently represent a single bond, a linear or branched alkylene group having 1 to 12 carbon atoms, or a linear or branched alkylene group having 1 to 12 carbon atoms. A divalent linking group in which at least one of —CH ₂ — constituting is substituted with —O—, —S—, —NH—, —N (Q) —, or —CO—; Represents a substituent.
L ³ and L ⁴ each independently represent a monovalent organic group, and at least one of L ³ and L ⁴ and L in the formula (2) represents a polymerizable group.
Ax represents an organic group having 2 to 30 carbon atoms having at least one aromatic ring selected from the group consisting of an aromatic hydrocarbon ring and an aromatic heterocyclic ring.
Ay represents a hydrogen atom, an optionally substituted alkyl group having 1 to 12 carbon atoms, or at least one aromatic ring selected from the group consisting of an aromatic hydrocarbon ring and an aromatic heterocyclic ring. And an organic group having 2 to 30 carbon atoms.
Further, the aromatic ring in Ax and Ay may have a substituent, and Ax and Ay may be bonded to form a ring.
Q ³ represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms which may have a substituent.
On the other hand, in the formulas (3) and (4), D and D ¹ are each independently a single bond, —O—, —CO—O—, —C (═S) O—, —CR ¹ R ^{2. -, - CR 1 R 2 -CR} 3 R 4 -, - O-CR 1 R 2 -, - CR 1 R 2 -O-CR 3 R 4 -, - CO-O-CR 1 R 2 -, - O ^{-CO-CR 1 R 2 -,} - CR 1 R 2 -O-CO-CR 3 R 4 -, - CR 1 R 2 -CO-O-CR 3 R 4 -, - NR 1 -CR 2 R 3 - Or represents —CO—NR ¹ —. R ¹ , R ² , R ³ and R ⁴ each independently represent a hydrogen atom, a fluorine atom, or an alkyl group having 1 to 4 carbon atoms.
G ¹ represents ^AG or SP ^G.
A and ^AG each independently represent an aromatic ring having 6 or more carbon atoms or a cycloalkane ring having 6 or more carbon atoms, and one or more of —CH ₂ — constituting the cycloalkane ring is —O—. , -S- or -NH- may be substituted.
SP and SP ^G are each independently a single bond, a linear or branched alkylene group having 1 to 20 carbon atoms, a linear or branched alkenylene group having 1 to 20 carbon atoms, or 1 to 20 carbon atoms. A linear or branched alkynylene group, or one or more of —CH ₂ — constituting the alkylene group, the alkenylene group or the alkynylene group is —O—, —S—, —NH—, —N (Q) represents a divalent linking group substituted with-or -CO-, and Q represents a substituent.
L represents a polymerizable group. However, when Ar in the formula (2) is an aromatic ring represented by the formula (Ar-4), at least one of L ³ and L ^{4 in} the formula (Ar-4) is polymerizable. When it is a group, L represents a monovalent organic group.
q represents an integer of 0 to 2, and when q is 2, a plurality of G ¹ may be the same or different, and a plurality of D ¹ may be the same or different. Good.
p represents 0 or an integer of 1 or more, and when p is an integer of 2 or more, a plurality of A may be the same or different, and a plurality of D may be the same or different. May be. A method for producing a polymerizable compound for synthesizing the polymerizable compound according to claim 1,
A first esterification step of reacting a compound represented by the following formula (2) with a compound represented by the following formula (4) to produce a second phenol compound;
A second esterification step of reacting the second phenol reactant obtained in the first esterification step with a compound represented by the following formula (3) to obtain a polymerizable compound according to claim 1; The manufacturing method of the polymeric compound which has these.
In the formula (2), Ar represents any aromatic ring selected from the group consisting of groups represented by the following formulas (Ar-1) to (Ar-8).
Here, in the formulas (Ar-1) to (Ar-8), * 1 and * 2 each represent a bonding position with a hydroxyl group.
Q ¹ represents N or CH.
Q ² represents —S—, —O—, or —N (R ⁵ ) —, and R ⁵ represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.
Y ¹ represents an optionally substituted aromatic hydrocarbon group having 6 to 12 carbon atoms or an aromatic heterocyclic group having 3 to 12 carbon atoms.
Z ¹ represents a monovalent aliphatic hydrocarbon group having 3 to 20 carbon atoms, a monovalent aromatic hydrocarbon group having 6 to 20 carbon atoms, a halogen atom, —OR ⁶ , —NR ⁷ R ⁸ , or , -SR ⁹ , and R ^{6 to} R ⁹ each independently represent a monovalent aliphatic hydrocarbon group having 3 to 20 carbon atoms or a monovalent aromatic hydrocarbon group having 6 to 20 carbon atoms.
Z ² is a hydrogen atom, a monovalent aliphatic hydrocarbon group having 1 to 20 carbon atoms, a monovalent alicyclic hydrocarbon group having 3 to 20 carbon atoms, or a monovalent aromatic having 6 to 20 carbon atoms. Represents a hydrocarbon group, a halogen atom, a cyano group, a nitro group, —OR ¹⁰ , —NR ¹¹ R ¹² , or —SR ¹³ , wherein R ^{10 to} R ¹³ each independently represent a hydrogen atom or a carbon number of 1 to Represents an alkyl group of 6;
A ³ and A ⁴ each independently represent a group selected from the group consisting of —O—, —N (R ¹⁴ ) —, —S—, and —CO—, and R ¹⁴ represents hydrogen. Represents an atom or substituent.
X represents a hydrogen atom or a nonmetallic atom of Groups 14 to 16 to which a substituent may be bonded.
D ⁵ and D ⁶ are each independently a single bond, —O—CO—, —C (═S) O—, —CR ¹ R ² —, —CR ¹ R ² —CR ³ R ⁴ —, ^{-O-CR 1 R 2 -,} - CR 1 R 2 -O-CR 3 R 4 -, - CO-O-CR 1 R 2 -, - O-CO-CR 1 R 2 -, - CR 1 R 2 ^{-O-CO-CR 3 R 4} -, - CR 1 R 2 -CO-O-CR 3 R 4 -, - NR 1 -CR 2 R 3 -, or, -CO-NR ¹ - represents a. R ¹ , R ² , R ³ and R ⁴ each independently represent a hydrogen atom, a fluorine atom, or an alkyl group having 1 to 4 carbon atoms.
SP ³ and SP ⁴ each independently represent a single bond, a linear or branched alkylene group having 1 to 12 carbon atoms, or a linear or branched alkylene group having 1 to 12 carbon atoms. A divalent linking group in which at least one of —CH ₂ — constituting is substituted with —O—, —S—, —NH—, —N (Q) —, or —CO—; Represents a substituent.
L ³ and L ⁴ each independently represent a monovalent organic group, and at least one of L ³ and L ⁴ and L in the formula (2) represents a polymerizable group.
Ax represents an organic group having 2 to 30 carbon atoms having at least one aromatic ring selected from the group consisting of an aromatic hydrocarbon ring and an aromatic heterocyclic ring.
Ay represents a hydrogen atom, an optionally substituted alkyl group having 1 to 12 carbon atoms, or at least one aromatic ring selected from the group consisting of an aromatic hydrocarbon ring and an aromatic heterocyclic ring. And an organic group having 2 to 30 carbon atoms.
Further, the aromatic ring in Ax and Ay may have a substituent, and Ax and Ay may be bonded to form a ring.
Q ³ represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms which may have a substituent.
On the other hand, in the formulas (3) and (4), D and D ¹ are each independently a single bond, —O—, —CO—O—, —C (═S) O—, —CR ¹ R ^{2. -, - CR 1 R 2 -CR} 3 R 4 -, - O-CR 1 R 2 -, - CR 1 R 2 -O-CR 3 R 4 -, - CO-O-CR 1 R 2 -, - O ^{-CO-CR 1 R 2 -,} - CR 1 R 2 -O-CO-CR 3 R 4 -, - CR 1 R 2 -CO-O-CR 3 R 4 -, - NR 1 -CR 2 R 3 - Or represents —CO—NR ¹ —. R ¹ , R ² , R ³ and R ⁴ each independently represent a hydrogen atom, a fluorine atom, or an alkyl group having 1 to 4 carbon atoms.
G ¹ represents ^AG or SP ^G.
A and ^AG each independently represent an aromatic ring having 6 or more carbon atoms or a cycloalkane ring having 6 or more carbon atoms, and one or more of —CH ₂ — constituting the cycloalkane ring is —O—. , -S- or -NH- may be substituted.
SP and SP ^G are each independently a single bond, a linear or branched alkylene group having 1 to 20 carbon atoms, a linear or branched alkenylene group having 1 to 20 carbon atoms, or 1 to 20 carbon atoms. A linear or branched alkynylene group, or one or more of —CH ₂ — constituting the alkylene group, the alkenylene group or the alkynylene group is —O—, —S—, —NH—, —N (Q) represents a divalent linking group substituted with-or -CO-, and Q represents a substituent.
L represents a polymerizable group. However, when Ar in the formula (2) is an aromatic ring represented by the formula (Ar-4), at least one of L ³ and L ^{4 in} the formula (Ar-4) is polymerizable. When it is a group, L represents a monovalent organic group.
q represents an integer of 0 to 2, and when q is 2, a plurality of G ¹ may be the same or different, and a plurality of D ¹ may be the same or different. Good.
p represents 0 or an integer of 1 or more, and when p is an integer of 2 or more, a plurality of A may be the same or different, and a plurality of D may be the same or different. May be.   The polymeric composition containing the polymeric compound of any one of Claims 1-5.   Furthermore, the polymeric composition of Claim 8 containing the polymeric compound which has two or more polymeric groups different from the said polymeric compound.   An optically anisotropic film obtained by curing the polymerizable composition according to claim 8 or 9.   An optical film having the optically anisotropic film according to claim 10.   A polarizing plate comprising the optical film according to claim 11 and a polarizer.   An image display device comprising the optical film according to claim 11 or the polarizing plate according to claim 12.