WO2021060426A1

WO2021060426A1 - Polymerizable liquid-crystal composition, optically anisotropic film, optical film, polarizing plate, and image display device

Info

Publication number: WO2021060426A1
Application number: PCT/JP2020/036157
Authority: WO
Inventors: 有次吉田; 亮司後藤; 渡辺　徹; 慶太高橋
Original assignee: 富士フイルム株式会社
Priority date: 2019-09-27
Filing date: 2020-09-25
Publication date: 2021-04-01
Also published as: JP7371110B2; JPWO2021060426A1; KR20220050169A

Abstract

The present invention addresses the problem of providing: a polymerizable liquid-crystal composition which has reverse-wavelength dispersion characteristics and is for use in forming optically anisotropic films with excellent amine resistance; an optically anisotropic film; an optical film; a polarizing plate; and an image display device. This polymerizable liquid-crystal composition comprises a compound represented by formula (I-1) and a polymerizable smectic liquid-crystal compound.

Description

Polymerizable liquid crystal composition, optically anisotropic film, optical film, polarizing plate and image display device

The present invention relates to a polymerizable liquid crystal composition, an optically anisotropic film, an optical film, a polarizing plate, and an image display device.

A polymerizable liquid crystal compound exhibiting reverse wavelength dispersibility has features such as being able to accurately convert light wavelengths over a wide wavelength range and being able to thin a retardation film due to its high refractive index. Because it has, it is being actively researched.
Further, as a polymerizable liquid crystal compound exhibiting inverse wavelength dispersibility, a T-type molecular design guideline is generally taken, the wavelength of the major axis of the molecule is shortened, and the wavelength of the minor axis located at the center of the molecule is the longer wavelength. Is required to be.
Then, from the viewpoint of lengthening the wavelength of the short axis located at the center of the molecule, a hydrophilic nitrogen atom, oxygen atom, and sulfur atom are formed on the short axis skeleton (hereinafter, also referred to as “reverse wavelength dispersion expression part”). Is known to be introduced (see, for example, Patent Documents 1 to 3).

Japanese Unexamined Patent Publication No. 2010-031223 International Publication No. 2014/010325 Japanese Unexamined Patent Publication No. 2016-081035

Regarding Patent Documents 1 to 3, the present inventors have a durability that the birefringence of the formed optically anisotropic film is changed by ammonia, which is a basic nucleophile (hereinafter, "amine resistance"). It is also abbreviated.) It was confirmed that there was a problem.
Then, the present inventors can obtain amine resistance by using a strong bond (for example, an ether bond) for connecting the short-axis skeleton (reverse wavelength dispersion expressing part) located at the center of the molecule and the semi-major axis of the molecule. Although it is improved, it is clarified that the liquid crystal property is not exhibited and the reverse wavelength dispersibility is lost.

Therefore, the present invention presents a polymerizable liquid crystal composition, an optically anisotropic film, an optical film, a polarizing plate, and an image display device used for forming an optically anisotropic film having anti-wavelength dispersibility and excellent amine resistance. The challenge is to provide.

As a result of diligent studies to achieve the above problems, the present inventors have obtained a polymerizable liquid crystal composition containing a polymerizable smectic liquid crystal compound together with a compound represented by the formula (I-1) described later. The present invention has been completed by finding that the formed optically anisotropic film exhibits reverse wavelength dispersibility and good amine resistance.
That is, it was found that the above-mentioned problems can be achieved by the following configuration.

[1] A polymerizable liquid crystal composition containing a compound represented by the formula (I-1) described later and a polymerizable smectic liquid crystal compound.
^{[2] The polymerizable liquid crystal composition according to [1], wherein Ar 1} and Ar ² in the formula (I-1) described later represent an aromatic ring having a maximum absorption wavelength at 300 to 400 nm.
^{[3] Ar 1} and Ar ² in the formula (I-1) described later are any aromatics selected from the group consisting of the groups represented by the formulas (Ar-1) to (Ar-7) described later. The polymerizable liquid crystal composition according to [1] or [2], which represents a ring.
[4] The polymerizable liquid crystal composition according to any one of [1] to [3], wherein ^{X 1} and X ² in the formula (I-1) described later represent a linking group represented by —O—. ..
[5] P in the formula (I-3) described later represents any polymerizable group selected from the group consisting of the groups represented by the formulas (P-1) to (P-20) described later. , [1] to [4].
[6] The content of the polymerizable smectic liquid crystal compound is 15 to 75% by mass with respect to the total mass of the polymerizable smectic liquid crystal compound and the compound represented by the formula (I-1) described later, [1] to. The polymerizable liquid crystal composition according to any one of [5].

[7] An optically anisotropic film obtained by polymerizing the polymerizable liquid crystal composition according to any one of [1] to [6].
[8] The optically anisotropic film according to [7], which satisfies the following formula (III).
0.50 <Re (450) / Re (550) <1.00 ... (III)
Here, in the formula (III), Re (450) represents the in-plane retardation of the optically anisotropic film at a wavelength of 450 nm, and Re (550) represents the in-plane retardation of the optically anisotropic film at a wavelength of 550 nm. Represents.
[9] An optical film having the optically anisotropic film according to [7] or [8].
[10] A polarizing plate having the optical film according to [9] and a polarizer.
[11] An image display device having the optical film according to [9] or the polarizing plate according to [10].

According to the present invention, a polymerizable liquid crystal composition, an optically anisotropic film, an optical film, a polarizing plate and an image display device used for forming an optically anisotropic film having anti-wavelength dispersibility and excellent amine resistance. 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 based on a typical embodiment of the present invention, but the present invention is not limited to such an embodiment.
In the present specification, the numerical range represented by using "-" means a range including the numerical values before and after "-" as the lower limit value and the upper limit value.
Further, in the present specification, as each component, a substance corresponding to each component may be used alone or in combination of two or more. Here, when two or more kinds of substances are used in combination for each component, the content of the component means the total content of the substances used in combination unless otherwise specified.
Further, in the present specification, the bonding direction of the divalent group (for example, -CO-NR-) described is not particularly limited unless the bonding position is specified, and for example, the formula (for example) described later will be used. ^{When X 1} in I-1) is -CO-NR-, assuming that the ^{position bonded to the L 1} side is * 1 and the position bonded to the Ar ¹ side is * 2, X ¹ is It may be * 1-CO-NR- * 2 or * 1-NR-CO- * 2.

[Polymerizable liquid crystal composition]
The polymerizable liquid crystal composition of the present invention contains a compound represented by the formula (I-1) described later (hereinafter, also abbreviated as "specific compound") and a polymerizable smectic liquid crystal compound. It is a thing.

In the present invention, as described above, by using a polymerizable liquid crystal composition containing a polymerizable smectic liquid crystal compound together with a specific compound, inverse wavelength dispersibility is exhibited in the formed optically anisotropic film, and amine resistance is exhibited. Will also be good.
This is not clear in detail, but the present inventors speculate as follows.
That is, the specific compound is ester-bonded as a linking group (X ¹ and X ² ^{) to be bonded to an aromatic ring (Ar 1} and Ar ² ) having a maximum absorption wavelength at 280 to 420 nm in the formula (I-1) described later. It is considered that the amine resistance was improved because it has a strong bond that does not contain.
Further, when the specific compound and the polymerizable smectic liquid crystal compound are mixed, the structure represented by the formula (I-3) described later contained in the molecular major axis of the specific compound and the mesogen skeleton of the polymerizable smectic liquid crystal compound It is considered that the interaction between the compounds causes liquid crystallinity to be exhibited as a mixture and reverse wavelength dispersibility due to the structure of the specific compound.
Hereinafter, each component of the polymerizable liquid crystal composition of the present invention will be described in detail.

[Specific compound]
The specific compound contained in the polymerizable liquid crystal composition of the present invention is a compound represented by the following formula (I-1).

In the above formula (I-1), Ar ¹ and Ar ² each independently represent an aromatic ring having a maximum absorption wavelength of 280 to 420 nm.
Further, in the above formula (I-1), D ¹ is a single bond, or -CO-, -O-, -S-, -C (= S)-, -CR ¹ ^{R 2-} , -CR ³ ^{^{= CR 4 -, - NR 5}} -, or a divalent linking group formed from these two or more ^thereof, R 1 ~ ^{R 5} are each independently a hydrogen atom, a fluorine atom or a carbon atoms Represents 1 to 4 alkyl groups.
Further, in the above formula (I-1), p represents 0 or 1.
Further, in the above formula (I-1), X ¹ and X ² independently represent -O-, -S-, -CO-, -CO-NR ^6- , or a single bond, and R ⁶ Independently represent a hydrogen atom, a fluorine atom, or an alkyl group having 1 to 4 carbon atoms.

In the above formula (I-1), p represents 0 or 1 as described above, but it is 0, that is, D ¹ and Ar ^{2 in} the above formula (I-1) do not exist. Is preferable.

In the above formula (I-1) ^{, examples of the divalent linking group represented by one aspect of D 1} include -CO-, -O-, -CO-O-, -C (= S) O-,-. ^{^{^{^{CR 1 R 2 -, - CR}}}} 1 R 2 -CR 1 R 2 -, - O-CR 1 R 2 -, - CR 1 R 2 -O-CR 1 R 2 -, - CO-O-CR 1 R 2 ^{^{^{^{-, - O-CO-CR}}}} 1 R 2 -, - CR 1 R 2 -O-CO-CR 1 R 2 -, - CR 1 R 2 -CO-O-CR 1 R 2 -, - NR 5 -CR ¹ R ^2- , -CO-NR ^5- , and the like can be mentioned. R ¹ , R ² and R ⁵ independently represent a hydrogen atom, a fluorine atom, or an alkyl group having 1 to 4 carbon atoms.
Of these, any of -CO-, -O-, and -CO-O- is preferable.

In the above formula (I-1), X ¹ and X ² are preferably —O— or —S— because the amine resistance of the optically anisotropic film to be formed becomes better, and —O. -Is more preferable.

In the above formula (I-1), Ar ¹ and Ar ² represent an aromatic ring having a maximum absorption wavelength at 280 to 420 nm as described above, but the optical anisotropic film formed has better light resistance. For this reason, it is preferable to represent an aromatic ring having a maximum absorption wavelength of 300 to 400 nm.
Here, the maximum absorption wavelength refers to the maximum absorption wavelength in the absorption spectrum measured by the following method using a compound in which ^{the linking group (X 1} and X ^{2) with the aromatic ring is replaced with a methyl group.}
<Measurement method>
The compound is dissolved in chloroform to prepare a solution having a concentration of 1% by mass.
Next, the prepared solution is placed in a quartz cell (10 mm long square cell), and the absorbance in the wavelength range of 200 to 800 nm of the solution is measured using an ultraviolet visible infrared spectrophotometer U-3100PC (Shimadzu Seisakusho). ..
Next, the maximum absorption wavelength is obtained in the obtained absorption spectrum.

In the above formula (I-1), Ar ¹ and Ar ² have the following formulas (Ar-1) to (Ar-7) because the inverse wavelength dispersibility is likely to be exhibited in the formed optically anisotropic film. It is preferable to represent any aromatic ring selected from the group consisting of the groups represented by. In the following formulas (Ar-1) to (Ar-7), * represents the bonding position with X ¹ or D ¹ ^{for Ar 1} , and the bonding position with D ¹ or X ² ^{for Ar 2.} However, when p is 0, it represents the bonding position with ^{X 1} or X ^2.

In the above formula (Ar-1), Q ¹ represents N or CH, Q ² represents -S-, -O-, or -N (R ⁷ )-, and R ⁷ is a hydrogen atom or Representing an alkyl group having 1 to 6 carbon atoms, Y ¹ represents an aromatic hydrocarbon group having 6 to 12 carbon atoms or an aromatic heterocyclic group having 3 to 12 carbon atoms, which may have a substituent. Represent.
Specific examples of the alkyl group having 1 to 6 carbon atoms indicated by R ⁷ include 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. Examples include a group, an n-pentyl group, and an n-hexyl group.
Examples of the aromatic hydrocarbon group having 6 to 12 carbon atoms indicated by Y ¹ include an aryl group 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 indicated by Y ¹ include heteroaryl groups such as a thienyl group, a thiazolyl group, a frill group and a pyridyl group.
Examples of the substituent that Y ¹ may have include an alkyl group, an alkoxy group, an alkylcarbonyl group, an alkoxycarbonyl group, an alkylcarbonyloxy group, an alkylamino group, a dialkylamino group, an alkylamide group and an alkenyl. Examples thereof include a group, an alkynyl group, a halogen atom, a cyano group, a nitro group, an alkylthiol group, and an N-alkylcarbamate group. Among them, an alkyl group, an alkoxy group, an alkoxycarbonyl group, an alkylcarbonyloxy group, or a halogen. Atomic is preferred.
The alkyl group is preferably a linear, branched or cyclic alkyl group having 1 to 18 carbon atoms, and an alkyl group having 1 to 8 carbon atoms (for example, methyl group, ethyl group, propyl group, isopropyl group, n). -Butyl group, isobutyl group, sec-butyl group, t-butyl group, cyclohexyl group, etc.) are more preferable, alkyl groups having 1 to 4 carbon atoms are more preferable, and methyl groups or ethyl groups are particularly preferable.
As the alkoxy group, an alkoxy group having 1 to 18 carbon atoms is preferable, an alkoxy group having 1 to 8 carbon atoms (for example, a methoxy group, an ethoxy group, an n-butoxy group, a methoxyethoxy group, etc.) is more preferable, and an alkoxy group having 1 carbon number is preferable. Alkoxy groups of ~ 4 are more preferable, and methoxy groups or ethoxy groups are particularly preferable.
Examples of the alkoxycarbonyl group include a group in which an oxycarbonyl group (—O—CO— group) is bonded to the alkyl group exemplified above, and among them, a methoxycarbonyl group, an ethoxycarbonyl group, an n-propoxycarbonyl group or an isopropoxy. A carbonyl group is preferred, and a methoxycarbonyl group is more preferred.
Examples of the alkylcarbonyloxy group include a group in which a carbonyloxy group (-CO-O- group) is bonded to the alkyl group exemplified above, and among them, a methylcarbonyloxy group, an ethylcarbonyloxy group, and an n-propylcarbonyloxy group. A group or an isopropylcarbonyloxy group is preferable, and a methylcarbonyloxy group is more preferable.
Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom, and among them, a fluorine atom or a chlorine atom is preferable.

Further, in the above formulas (Ar-1) to (Ar-7), Z ¹ , Z ² and Z ³ are independently hydrogen atoms, monovalent aliphatic hydrocarbon groups having 1 to 20 carbon atoms, and carbon. A monovalent alicyclic hydrocarbon group of number 3 to 20, a monovalent aromatic hydrocarbon group of 6 to 20 carbons, a halogen atom, a cyano group, a nitro group, -OR ⁸ , -NR ⁹ R ¹⁰ , or , -SR ¹¹ and R ⁸ to R ¹¹ independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and Z ¹ and Z ² may be bonded to each other to form an aromatic ring. Good.
As the monovalent aliphatic hydrocarbon group having 1 to 20 carbon atoms, an alkyl group having 1 to 15 carbon atoms is preferable, an alkyl group having 1 to 8 carbon atoms is more preferable, and specifically, a methyl group and an 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, and methyl group, ethyl group, tert-butyl group. Groups are particularly preferred.
Examples of the monovalent alicyclic hydrocarbon group having 3 to 20 carbon atoms include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, a cyclodecyl group, a methylcyclohexyl group and an ethylcyclohexyl. Monocyclic saturated hydrocarbon groups such as groups; cyclobutenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, cyclooctenyl group, cyclodecenyl group, cyclopentadienyl group, cyclohexadienyl group, cyclooctadienyl group, cyclodeca Monocyclic unsaturated hydrocarbon groups such as diene; bicyclo [2.2.1] heptyl group, bicyclo [2.2.2] octyl group, tricyclo [5.2.1.0 ^2,6 ] decyl group, Tricyclo [3.3.1.1 ^3,7 ] decyl group, tetracyclo [6.2.1.1 ^3,6 . 0 ^2,7 ] Polycyclic saturated hydrocarbon groups such as dodecyl group and adamantyl group; and the like.
Specific examples of the monovalent aromatic hydrocarbon group having 6 to 20 carbon atoms include a phenyl group, a 2,6-diethylphenyl group, a naphthyl group, a biphenyl group and the like, and have 6 to 12 carbon atoms. Aryl groups (particularly phenyl groups) are preferred.
Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, an iodine atom and the like, and among them, a fluorine atom, a chlorine atom and a bromine atom are preferable.
On the other hand, ^{as the alkyl group having 1 to 6 carbon atoms indicated by R 8} to R ¹¹ , specifically, for example, a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an isobutyl group and a sec-butyl group. Examples include groups, tert-butyl groups, n-pentyl groups, n-hexyl groups and the like.

Further, in the above formulas (Ar-2) and (Ar-3), A ¹ and A ² are independently derived from -O-, -N (R ¹² )-, -S-, and -CO-, respectively. Represents a group selected from the group, where R ¹² represents a hydrogen atom or a substituent.
Examples of the substituent represented by R ¹² ^{include the same substituents that Y 1} in the above formula (Ar-1) may have.

Further, in the above formula (Ar-2), X represents a non-metal atom of Groups 14 to 16 to which a hydrogen atom or a substituent may be bonded.
Further, as the non-metal atom of Group 14 to 16 indicated by X, for example, an oxygen atom, a sulfur atom, a hydrogen atom or a nitrogen atom to which a substituent is bonded [= N- ^RN1 , ^RN1 is a hydrogen atom or a substituent. Represents. ], A carbon atom to which a hydrogen atom or a substituent is bonded [= C- ( ^RC1 ) ₂ , ^RC1 represents a hydrogen atom or a substituent. ] Can be mentioned.
Specific examples of the substituent include an alkyl group, an alkoxy group, an alkyl substituted alkoxy group, a cyclic alkyl group, an aryl group (for example, a phenyl group, a naphthyl group, etc.), a cyano group, an amino group, a nitro group, and an alkyl group. Examples thereof include a carbonyl group, a sulfo group and a hydroxyl group.

Further, in the above formula (Ar-3), D ⁴ and D ⁵ are independently single-bonded or -CO-, -O-, -S-, -C (= S)-, and -CR ^{1 respectively.} ^{^{^{R 2 -, - CR 3 =}}} CR 4 -, - NR 5 -, or a divalent linking group formed from these two or more ^thereof, R 1 ~ ^{R 5} are each independently a hydrogen atom, It represents a fluorine atom or an alkyl group having 1 to 4 carbon atoms.
Here, examples of the divalent linking group include those similar to those described in ^{D 1} in the above formula (I-1).

Further, in the above formula (Ar-3), SP ¹ and SP ² are independently single-bonded, linear or branched alkylene groups having 1 to 12 carbon atoms, or directly having 1 to 12 carbon atoms. _{Divalent in which one or more of -CH 2-} constituting the chain or branched alkylene group is substituted with -O-, -S-, -NH-, -N (Q)-, or -CO-. Represents the linking group of, and Q represents the substituent. Examples of the substituent include the same substituents that Y ¹ in the above formula (Ar-1) may have.
Here, examples of the linear or branched alkylene group having 1 to 12 carbon atoms include a methylene group, an ethylene group, a propylene group, a butylene group, a pentylene group, a hexylene group, a methylhexylene group and a heptylene group. Is preferably mentioned.

Further, in the above formula (Ar-3), L ³ and L ⁴ each independently represent a monovalent organic group.
Examples of the monovalent organic group include an alkyl group, an aryl group, and a heteroaryl group. The alkyl group may be linear, branched or cyclic, but linear is preferred. The number of carbon atoms of the alkyl group is preferably 1 to 30, more preferably 1 to 20, and even more preferably 1 to 10. The aryl group may be monocyclic or polycyclic, but monocyclic is preferable. The aryl group preferably has 6 to 25 carbon atoms, more preferably 6 to 10 carbon atoms. Further, 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. The heteroaryl group preferably has 6 to 18 carbon atoms, more preferably 6 to 12 carbon atoms. Further, the alkyl group, the aryl group and the heteroaryl group may be unsubstituted or have a substituent. Examples of the substituent include the same substituents that Y ¹ in the above formula (Ar-1) may have.

Further, in the above formulas (Ar-4) to (Ar-7), Ax has at least one aromatic ring selected from the group consisting of an aromatic hydrocarbon ring and an aromatic heterocycle, and has 2 to 30 carbon atoms. Represents an organic group.
Further, in the above formulas (Ar-4) to (Ar-7), Ay is a hydrogen atom, an alkyl group having 1 to 12 carbon atoms which may have a substituent, or an aromatic hydrocarbon ring and aromatic. Represents an organic group having 2 to 30 carbon atoms and having at least one aromatic ring selected from the group consisting of group heterocycles.
Here, the aromatic ring in Ax and Ay may have a substituent, or Ax and Ay may be bonded to form a ring.
Further, 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 [0995] of Patent Document 2 (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 can be mentioned, and examples of the substituent include the same substituents that Y ¹ in the above formula (Ar-1) may have. Can be mentioned.

On the other hand, in the above formula (I-1), L ¹ and L ² independently represent an alkylene group represented by the following formula (I-2). In the following formula (I-2), * represents the bonding position with Mes ¹ or X ¹ ^{for L 1} , and represents the bonding position with Mes ² or X ² ^{for L 2} .

In the above formula (I-2), m represents an integer of 1 or more, preferably an integer of 2 to 20, more preferably an integer of 2 to 15, and an integer of 2 to 10. Is particularly preferable.

The hydrogen atom contained in the alkylene group represented by the above formula (I-2) is a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfuranyl group, a cyano group, a nitro group, an isocyano group, and the like. It may be substituted with a thioisocyano group or an alkyl group having 1 to 20 carbon atoms.
Specific examples of the alkyl group having 1 to 20 carbon atoms include a methyl group, an ethyl group, an isopropyl group, an n-propyl group, an n-butyl group, a t-butyl group, an amyl group, and a 2-ethylhexyl group. Examples thereof include a nonyl group, a decanyl group, a lauryl group, a cetyl group, a stearyl group, and a cyclohexyl group.

Further, one of _{-CH 2-} , which constitutes the alkylene group represented by the above formula (I-2) and is not directly bonded to ^{X 1} or X ^{2 in the above formula (I-1).} Or two or more non-adjacent -CH _2- are -O-, -S-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O- It may be substituted with CO-O-, -CO-NH-, -NH-CO-, or -C≡C-.

On the other hand, in the above formula (I-1), Mes ¹ and Mes ² independently represent the polymerizable group-containing group represented by the following formula (I-3). In the following formulas (I-3), * represents a bonding position with ^{L 1} for Mes ^1, represents a bonding position to ^{L 2} for Mes ^2.

In the above formula (I-3), M is a 1,4-phenylene group, a 1,4-cyclohexylene group, a pyridine-2,5-diyl group, a pyrimidine-2,5-diyl group, a naphthalene-2,6. -Represents a diyl group, naphthalene-1,4-diyl group, tetrahydronaphthalene-2,6-diyl group, decahydronaphthalene-2,6-diyl group, or 1,3-dioxane-2,5-diyl group. ..
However, the hydrogen atom contained in these groups is a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfuranyl group, a cyano group, a nitro group, an isocyano group, a thioisocyano group, or 1 to 20 carbon atoms. It may be substituted with an alkyl group of.

Further, in the above formula (I-3), D ² and D ³ are independently of -O-, -S-, -OCH _2- , -CH ₂ CH _2- , -CO-, -COO-, respectively. -CO-S-, -OCO-O-, -CO-NH-, -SCH _2- , -CF ₂ O-, -CF ₂ S-, -CH = CH-COO-, -CH = CH-OCO- _{_{_{, -COO-CH 2 CH 2 -}}} , - OCO-CH 2 CH 2 -, - COO-CH 2 -, - OCO-CH 2 -, - CH = CH -, - N = N -, - CH = N- , -CH = NN = CH-, -CF = CF-, -C≡C-, or a single bond.

Further, in the above formula (I-3), SP is 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. _{One or more of -CH 2-} constituting the above represents a divalent linking group substituted with -O-, -S-, -NH-, -N (Q)-, or -CO-, where Q is , Represents a substituent. Examples of the substituent include the same substituents that Y ¹ in the above formula (Ar-1) may have.
Here, examples of the linear or branched alkylene group having 1 to 12 carbon atoms include a methylene group, an ethylene group, a propylene group, a butylene group, a pentylene group, a hexylene group, a methylhexylene group and a heptylene group. Is preferably mentioned.

Further, in the above formula (I-3), P represents a polymerizable group.
As the polymerizable group, a polymerizable group capable of radical polymerization or cationic polymerization is preferable.
As the radically polymerizable group, a known radically polymerizable group can be used, and suitable examples thereof include an acryloyloxy group and a methacryloyloxy group. In this case, it is known that the acryloyloxy group is generally faster in terms of polymerization rate, and the acryloyloxy group is preferable from the viewpoint of improving productivity, but the methacryloyloxy group can also be used as the polymerizable group in the same manner.
As the cationically polymerizable group, a known cationically polymerizable group can be used, and specifically, an alicyclic ether group, a cyclic acetal group, a cyclic lactone group, a cyclic thioether group, a spiroorthoester group, and vinyloxy. The group can be mentioned. Of 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 preferable polymerizable groups include any polymerizable group selected from the group consisting of the groups represented by the following formulas (P-1) to (P-20). Of these, an acryloyloxy group or a methacryloyloxy group is more preferable. In the following formulas (P-1) to (P-20), * represents the bonding position with the SP.

Further, in the above formula (I-3), n represents an integer of 2 or more, preferably an integer of 2 to 5, more preferably an integer of 2 to 4, and 2 or 3. Is more preferable.
The plurality of Ms may be the same or different, the plurality of D ^2s may be the same or different, and the plurality of D ^3s may be the same or different. The plurality of SPs may be the same or different.

Specific examples of the specific compound include compounds represented by the following formulas (1) to (22), and specifically, K (specifically, K (1) to (22) in the following formulas (1) to (22). Examples of the side chain structure) include compounds having the side chain structures shown in Tables 1 and 2 below.
In Tables 1 and 2 below, "*" shown in the side chain structure of K represents the bonding position with the aromatic ring.
Further, in the side chain structures represented by 1-9 in Table 1 below and 2-9 in Table 2 below, the groups adjacent to the acryloyloxy group and the methacryloyl group are propylene groups (methyl groups are ethylene groups, respectively). It represents a substituted group) and represents a mixture of positional isomers with different methyl group positions.

[Polymerizable smectic liquid crystal compound]
The polymerizable smectic liquid crystal compound contained in the polymerizable liquid crystal composition of the present invention is a compound having a polymerizable group and exhibiting a liquid crystal state of the smectic phase.
Here, as the polymerizable group, the same group as described in P in the above-mentioned formula (I-3) can be mentioned. Among them, any polymerizable group selected from the group consisting of the groups represented by the above-mentioned formulas (P-1) to (P-20) is preferable, and it is an acryloyloxy group or a methacryloyloxy group. Is more preferable.
Further, the liquid crystal state exhibited by the polymerizable smectic liquid crystal compound is preferably a higher-order smectic phase. The higher-order smectic phase referred to here is smectic A phase, smectic B phase, smectic D phase, smectic E phase, smectic F phase, smectic G phase, smectic H phase, smectic I phase, smectic J phase, smectic K phase. And the smectic L phase, among which the smectic A phase, the smectic B phase, the smectic F phase, the smectic I phase, the slanted smectic F phase and the slanted smectic I phase are preferable, and the smectic A phase and the smectic B phase are more preferable.
As such a polymerizable smectic liquid crystal compound, various literatures (C. Destrade et al., Mol. Crysr. Liq. Cryst., Vol. 71, page 111 (1981); edited by the Japanese Society of Chemistry, Quarterly Chemistry Review, No. 22, Chemistry of liquid crystal, Chapter 5, Chapter 10, Section 2 (1994); B. Kohne et al., Angew. Chem. Soc. Chem. Comm., Page 1794 (1985); J. Zhang et. Al., J. Am. Chem. Soc., Vol. 116, page 2655 (1994)).

In the present invention, the polymerizable smectic liquid crystal compound may be a polymerizable liquid crystal compound exhibiting reverse wavelength dispersibility, but is preferably a polymerizable liquid crystal compound exhibiting forward wavelength dispersibility.
Here, in the present specification, the "polymerizable liquid crystal compound exhibiting inverse wavelength dispersibility" is an in-plane retardation (Re) value at a specific wavelength (visible light range) of a retardation film produced using the same. When the measurement is performed, the Re value becomes equal or higher as the measurement wavelength becomes larger.
On the other hand, the "polymerizable liquid crystal compound exhibiting forward wavelength dispersibility" is when the in-plane retardation (Re) value at a specific wavelength (visible light range) of a retardation film produced using the compound is measured. , The Re value decreases as the measurement wavelength increases.

In the present invention, the content of the polymerizable smectic liquid crystal compound is determined because the interaction between the side chain of the molecular major axis of the specific compound and the mesogen skeleton of the polymerizable smectic liquid crystal facilitates the development of liquid crystallinity as a mixture. It is preferably 15 to 75% by mass, more preferably 30 to 60% by mass, based on the total mass of the polymerizable smectic liquid crystal compound and the above-mentioned specific compound.

[Other polymerizable compounds]
The polymerizable liquid crystal composition of the present invention may contain other polymerizable compounds having one or more polymerizable groups, in addition to the above-mentioned polymerizable smectic liquid crystal compound.
Here, the polymerizable group of the other polymerizable compound is not particularly limited, and examples thereof include an acryloyl group, a methacryloyl group, a vinyl group, a styryl group, and an allyl group. Among them, it is preferable to have an acryloyl group and a methacryloyl group.

The other polymerizable compound is preferably another polymerizable compound having 1 to 4 polymerizable groups because the durability of the optically anisotropic film to be formed is improved, and the polymerizable group is used. More preferably, it is another polymerizable compound having two.

The other polymerizable compound is preferably a non-liquid crystal polymerizable compound, and specific examples thereof include the compounds described in paragraphs [0073] to [0074] of JP-A-2016-053709. Be done.

When such another polymerizable compound is contained, the content is preferably less than 50% by mass, more preferably 40% by mass or less, based on the mass of the above-mentioned polymerizable liquid crystal compound. It is more preferably 2 to 30% by mass.

[Polymerization initiator]
The polymerizable liquid crystal composition of the present invention preferably contains a polymerization initiator.
The polymerization initiator used is preferably a photopolymerization initiator capable of initiating a polymerization reaction by irradiation with ultraviolet rays.
Examples of the photopolymerization initiator include α-carbonyl compounds (described in US Pat. No. 2,376,661 and US Pat. No. 2,376,670), acidoin ethers (described in US Pat. No. 2,448,828), and α-hydrogen-substituted fragrances. Group acidoine compounds (described in US Pat. No. 2722512), polynuclear quinone compounds (described in US Pat. Nos. 3,043127 and 2951758), combinations of triarylimidazole dimers and p-aminophenyl ketone (US patents). 3549367 (described in US Pat. No. 3,549,67), aclysine and phenazine compounds (Japanese Patent Laid-Open No. 60-105667, US Pat. No. 4,239,850), oxadiazole compounds (described in US Pat. No. 4,212,970), acylphosphine. Examples thereof include oxide compounds (described in Japanese Patent Application Laid-Open No. 63-40799, Japanese Patent Application Laid-Open No. 5-29234, Japanese Patent Application Laid-Open No. 10-95788, Japanese Patent Application Laid-Open No. 10-29997) and the like.
Further, in the present invention, the polymerization initiator is preferably an oxime type polymerization initiator, and specific examples thereof are described in paragraphs [0049] to [0052] of International Publication No. 2017/170443. Agents are mentioned.

〔solvent〕
The polymerizable liquid crystal 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 a ketone solvent (for example, acetone, 2-butanone, methylisobutylketone, cyclohexanone, cyclopentanone, etc.), an ether solvent (for example, dioxane, tetrahydrofuran, etc.), and a cyclic amide solvent. Solvents (eg, N-methylpyrrolidone, N-ethylpyrrolidone, N, N'-dimethylimidazolidinone, etc.), aliphatic hydrocarbon solvents (eg, hexane, etc.), alicyclic hydrocarbon solvents (eg, cyclohexane) Aromatic hydrocarbon solvents (eg toluene, xylene, trimethylbenzene, etc.), carbon halide solvents (eg dichloromethane, dichloroethane, dichlorobenzene, chlorotoluene, etc.), ester solvents (eg methyl acetate, etc.) Ethyl acetate, butyl acetate, etc.), water, alcohol solvents (eg ethanol, isopropanol, butanol, cyclohexanol, etc.), cellosolve solvents (eg, methyl cellosolve, ethyl cellosolve, etc.), cellosolve acetate solvents, sulfoxide solvents (eg, methyl cellosolve, ethyl cellosolve, etc.) For example, dimethylsulfoxide, etc.), chain amide-based solvents (for example, dimethylformamide, dimethylacetamide, etc.) and the like can be mentioned, and these may be used alone or in combination of two or more.

In the present invention, at least one of the above-mentioned solvents selected from the group consisting of a ketone solvent, an ether solvent and a cyclic amide solvent for the reason that the effect of the present invention for suppressing an increase in filtration pressure becomes apparent. It is preferably a seed solvent.

[Leveling agent]
The polymerizable liquid crystal composition of the present invention preferably contains a leveling agent from the viewpoint of keeping the surface of the optically anisotropic film smooth and facilitating orientation control.
Such a leveling agent is preferably a fluorine-based leveling agent or a silicon-based leveling agent because it has a high leveling effect on the amount of addition, and a fluorine-based leveling agent from the viewpoint of less likely to cause crying (bloom, bleed). Is more preferable.
Specific examples of the leveling agent include the compounds described in paragraphs [0079] to [0102] of JP-A-2007-069471, and the general formulas described in JP-A-2013-047204. The compound represented by I) (particularly the compound described in paragraphs [0020] to [0032]) and the compound represented by the general formula (I) described in JP2012-211306 (particularly [0022]). -The compound described in paragraph [0029], the liquid crystal orientation promoter represented by the general formula (I) described in JP-A-2002-129162 (particularly [0076] to [0078] and [0082]- Compounds described in paragraph [0084], compounds represented by general formulas (I), (II) and (III) described in JP-A-2005-09248 (particularly paragraphs [0092] to [0996]). The compounds described in (1) and the like. In addition, it may also have a function as an orientation control agent described later.

[Orientation control agent]
The polymerizable liquid crystal composition of the present invention may contain an orientation control agent, if necessary.
The orientation control agent can form various orientation states such as homeotropic orientation (vertical orientation), tilt orientation, hybrid orientation, and cholesteric orientation in addition to homogenius orientation, and can make a specific orientation state more uniform and more uniform. It can be realized by precise control.

As the orientation control agent that promotes homogenous orientation, for example, a low-molecular-weight orientation control agent or a high-molecular-weight orientation control agent can be used.
Examples of the low-molecular-weight orientation control agent include paragraphs [0009] to [0083] of JP-A-2002-20363, paragraphs [0111]-[0120] of JP-A-2006-106662, and JP-A-2012. -The description in paragraphs [0021] to [0029] of Japanese Patent Application Laid-Open No. 211306 can be referred to, and this content is incorporated in the present specification.
Further, as the polymer orientation control agent, for example, paragraphs [0021] to [0057] of JP-A-2004-198511 and paragraphs [0121] to [0167] of JP-A-2006-106662 are referred to. And this content is incorporated herein by reference.

Examples of the orientation control agent for forming or promoting homeotropic orientation include boronic acid compounds and onium salt compounds. Specifically, paragraphs [0023] to [0032] of JP-A-2008-225281. , Paragraphs [0052] to [0058] of JP2012-208397A, paragraphs [0024] to [0055] of JP2008-026730, and [0043] to [0055] of JP2016-193869. The compounds described in paragraphs and the like can be taken into account, the contents of which are incorporated herein by reference.

On the other hand, the cholesteric orientation can be realized by adding a chiral agent to the polymerizable liquid crystal composition of the present invention, and the turning direction of the cholesteric orientation can be controlled by the direction of the chirality. The pitch of cholesteric orientation can be controlled according to the orientation regulating force of the chiral agent.

When the orientation control agent is contained, the content is preferably 0.01 to 10% by mass and preferably 0.05 to 5% by mass with respect to the total solid content mass in the polymerizable liquid crystal composition. More preferred. When the content is in this range, it is possible to obtain a uniform and highly transparent optically anisotropic film without precipitation, phase separation, orientation defects, etc., while achieving the desired orientation state.
These orientation control agents can further impart a polymerizable functional group, particularly a polymerizable functional group that can be polymerized with the polymerizable liquid crystal compound constituting the polymerizable liquid crystal composition of the present invention.

[Other ingredients]
The polymerizable liquid crystal composition of the present invention may contain a component other than the above-mentioned components, for example, a liquid crystal compound other than the above-mentioned polymerizable smectic liquid crystal compound, a surfactant, a tilt angle control agent, an orientation aid, and the like. Examples thereof include a plasticizer and a cross-linking agent.

[Optically anisotropic film]
The optically anisotropic film of the present invention is an optically anisotropic film obtained by polymerizing the above-mentioned polymerizable liquid crystal composition of the present invention.
Examples of the method for forming the optically anisotropic film include a method of using the above-mentioned polymerizable liquid crystal composition of the present invention to achieve a desired orientation state and then immobilizing the film by polymerization. In particular, in the present invention, it is preferable to form an optically anisotropic film after the above-mentioned polymerizable liquid crystal composition of the present invention is prepared and then stored.
Here, the polymerization conditions are not particularly limited, but it is preferable to use ultraviolet rays in the polymerization by light irradiation. The irradiation amount is ^{preferably 10 mJ / cm 2} to 50 J / cm ² , more preferably 20 mJ / cm ² to 5 J / cm ² , and even more preferably 30 mJ / cm ² to 3 J / cm ^2. , 50 to 1000 mJ / cm ² is particularly preferable. Further, in order to promote the polymerization reaction, it may be carried out under heating conditions.
In the present invention, the optically anisotropic film can be formed on an arbitrary support in the optical film of the present invention described later or on a polarizer in the polarizing plate of the present invention described later.

The optically anisotropic film of the present invention preferably satisfies the following formula (III).
0.50 <Re (450) / Re (550) <1.00 ... (III)
Here, in the above formula (III), Re (450) represents the in-plane lettering of the optically anisotropic film at a wavelength of 450 nm, and Re (550) represents the in-plane letter of the optically anisotropic film at a wavelength of 550 nm. Represents the optics. If the measurement wavelength of the retardation is not specified in the present specification, the measurement wavelength is 550 nm.
The values of in-plane retardation and retardation in the thickness direction refer to values measured using light of a measurement wavelength using AxoScan OPMF-1 (manufactured by Optoscience).
Specifically, by inputting the average refractive index ((Nx + Ny + Nz) / 3) and the film thickness (d (μm)) in AxoScan OPMF-1.
Slow phase axial direction (°)
Re (λ) = R0 (λ)
Rth (λ) = ((nx + ny) /2-nz) × d
Is calculated.
Although R0 (λ) is displayed as a numerical value calculated by AxoScan OPMF-1, it means Re (λ).

The optically anisotropic membrane 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 (the direction in which the refractive index in the plane is maximized) is nx, the refractive index in the direction orthogonal to the slow phase axis in the plane in the plane is ny, and the refraction in the thickness direction. When the rate is nz, the positive A plate satisfies the relation of the formula (A1), and the positive C plate satisfies the relation 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.
Equation (A1) nx> ny≈nz
Equation (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 example, in the positive A plate, (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 when (nx-nz) xd is -10 to 10 nm, preferably -5 to 5 nm, it is also included in "nx≈nz". Further, in the positive C plate, for example, when (nx−ny) × d (where d is the thickness of the film) is 0 to 10 nm, preferably 0 to 5 nm, it is also included in “nx≈ny”.

When the optically anisotropic film of the present invention is a positive A plate, Re (550) is preferably 100 to 180 nm, more preferably 120 to 160 nm, from the viewpoint of functioning as a λ / 4 plate. It is more preferably 130 to 150 nm, and particularly preferably 130 to 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 converting circularly polarized light into linearly polarized light). It is a plate having.

[Optical film]
The optical film of the present invention is an optical film having the optically anisotropic film of the present invention.
1A, 1B and 1C (hereinafter, these drawings are abbreviated as "FIG. 1" when no particular distinction is required) are schematic cross-sectional views showing an example of the optical film of the present invention, respectively.
Note that FIG. 1 is a schematic view, and the thickness relationship and positional relationship of each layer do not always match the actual ones, and the support, alignment film, and hard coat layer shown in FIG. 1 all have an arbitrary configuration. It is a member.
The optical film 10 shown in FIG. 1 has a support 16, an alignment film 14, and an optically anisotropic film 12 in this order.
Further, as shown in FIG. 1B, the optical film 10 may have a hard coat layer 18 on the side opposite to the side where the alignment film 14 of the support 16 is provided, and as shown in FIG. 1C, the optical film 10 may have a hard coat layer 18. The hard coat layer 18 may be provided on the side of the optically anisotropic film 12 opposite to the side on which 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 of the optical film of the present invention is the above-mentioned optically anisotropic film of the present invention.
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, 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 an optically anisotropic film.
Such a support is preferably transparent, and specifically, the light transmittance is preferably 80% or more.

Examples of such a support include a glass substrate and a polymer film, and examples of the polymer film material include a cellulose-based polymer; an acrylic-based polymer having an acrylic acid ester polymer such as polymethylmethacrylate and a lactone ring-containing polymer. Polymers; Thermoplastic norbornene-based polymers; Polycarbonate-based polymers; Polyester-based polymers such as polyethylene terephthalate and polyethylene naphthalate; Stylized polymers such as polystyrene and acrylonitrile-styrene copolymer (AS resin); Polyethylene, polypropylene, ethylene and propylene Polyolefin-based polymers such as polymers; Vinyl chloride-based polymers; Amid-based polymers such as nylon and aromatic polyamides; Imid-based polymers; Examples thereof include vinylidene chloride-based polymers; vinyl alcohol-based polymers; vinyl butyral-based polymers; allylate-based polymers; polyoxymethylene-based polymers; epoxy-based polymers; or polymers in which these polymers are mixed.
Further, the polarizer described later may also serve as such a support.

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

[Alignment film]
When the optical film of the present invention has any of the above-mentioned supports, it is preferable that the optical film has an alignment film between the support and the optically anisotropic film. The support described above may also serve as an alignment film.

The alignment film generally contains a polymer as a main component. The polymer material for an alignment film has been described in a large number of documents, and a large number of commercially available products are available.
The polymer material used in the present invention is preferably polyvinyl alcohol or polyimide, or a derivative thereof. Particularly modified or unmodified polyvinyl alcohol is preferable.
Regarding the alignment film that can be used in the present invention, for example, the alignment film described in International Publication No. 01/88574, p. 43, p. 24 to p. 49, p. 8; ], And the like; a liquid crystal alignment film formed by the liquid crystal alignment agent described in Japanese Patent Application Laid-Open No. 2012-155308; and the like.

In the present invention, it is also preferable to use a photoalignment film as the alignment film because it is possible to prevent surface deterioration by not contacting the surface of the alignment film when forming the alignment film.
The photoalignment film is not particularly limited, but is a polymer material such as a polyamide compound or a polyimide compound described in paragraphs [0024] to [0043] of International Publication No. 2005/096041; A liquid crystal alignment film formed by a liquid crystal alignment agent having a photo-oriented group; a trade name LPP-JP265CP manufactured by Polyimide, Inc. can be used.

Further, in the present invention, the thickness of the alignment film is not particularly limited, but from the viewpoint of alleviating the surface irregularities that may exist on the support and forming an optically anisotropic film having a uniform film thickness, 0. It is preferably 01 to 10 μm, more preferably 0.01 to 1 μm, and even 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 hard coat layer may be provided on the side opposite to the side where the alignment film of the support is provided (see FIG. 1B), and the side where the alignment film of the optically 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 JP2009-98658A can be used.

[Other optically anisotropic membranes]
The optical film of the present invention may have another optically anisotropic film in addition to the optically anisotropic film of the present invention.
That is, the optical film of the present invention may have a laminated structure of the optically anisotropic film of the present invention and another optically anisotropic film.
Such other optically anisotropic films are optically anisotropic films obtained by using the above-mentioned polymerizable smectic liquid crystal compound or other polymerizable compound (particularly, liquid crystal compound) without blending the above-mentioned specific compound. If so, it is not particularly limited.
Here, in general, liquid crystal compounds can be classified into rod-shaped type and disk-shaped type according to their shapes. Furthermore, there are low molecular weight and high molecular weight types, respectively. A polymer generally refers to a polymer having a degree of polymerization of 100 or more (Polymer Physics / Phase Transition Dynamics, Masao Doi, p. 2, Iwanami Shoten, 1992). In the present invention, any liquid crystal compound can be used, but it is preferable to use a rod-shaped liquid crystal compound or a discotic liquid crystal compound (disk-shaped liquid crystal compound). Two or more kinds of rod-shaped liquid crystal compounds, two or more kinds of disk-shaped liquid crystal compounds, or a mixture of a rod-shaped liquid crystal compound and a disk-shaped liquid crystal compound may be used. For the immobilization of the above-mentioned liquid crystal compound, it is more preferable to form a rod-shaped liquid crystal compound or a disk-shaped liquid crystal compound having a polymerizable group, and the liquid crystal compound may have two or more polymerizable groups in one molecule. More preferred. When the liquid crystal compound is a mixture of two or more kinds, it is preferable that at least one kind of 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-A-11-513019 and paragraphs [0026] to [0098] of JP-A-2005-289980 can be preferably used, and discotics can be used. As the liquid crystal compound, for example, those described in paragraphs [0020] to [0067] of JP2007-108732 and paragraphs [0013] to [0108] of JP2010-244038 can be preferably used. However, it is not limited to these.

[UV absorber]
The optical film of the present invention preferably contains an ultraviolet (UV) absorber in consideration of the influence of external light (particularly ultraviolet rays).
The ultraviolet absorber may be contained in the optically anisotropic film of the present invention, or may be contained in a member other than the optically anisotropic film constituting the optical film of the present invention. As the member other than the optically anisotropic film, for example, a support is preferably mentioned.
As the ultraviolet absorber, any conventionally known one capable of exhibiting ultraviolet absorption can be used. Among such ultraviolet absorbers, a benzotriazole-based or hydroxyphenyltriazine-based ultraviolet absorber may be used from the viewpoint of obtaining the ultraviolet absorbing ability (ultraviolet blocking ability) used in an image display device because of its high ultraviolet absorbing ability. preferable.
Further, in order to widen the absorption range of ultraviolet rays, two or more kinds of ultraviolet absorbers having different maximum absorption wavelengths can be used in combination.
Specific examples of the ultraviolet absorber include compounds described in paragraphs [0258] to [0259] of JP2012-18395, paragraphs [0055] to [0105] of JP2007-72163. Examples thereof include the compounds described in.
Further, as commercially available products, Tinuvin400, Tinuvin405, Tinuvin460, Tinuvin477, Tinuvin479, Tinuvin1577 (all manufactured by BASF) and the like can be used.

[Polarizer]
The polarizing plate of the present invention has the above-mentioned optical film of the present invention and a polarizer.
Further, the polarizing plate of the present invention can be used as a circular polarizing plate when the above-mentioned optically anisotropic film of the present invention is a λ / 4 plate (positive A plate).
Further, when the optically anisotropic film of the present invention described above is a λ / 4 plate (positive A plate), the polarizing plate of the present invention has a slow phase axis of the λ / 4 plate and an absorption axis of a polarizer described later. The angle formed by the light is preferably 30 to 60 °, more preferably 40 to 50 °, further preferably 42 to 48 °, and particularly preferably 45 °.
Here, the "slow phase axis" of the λ / 4 plate means the direction in which the refractive index becomes maximum in the plane of the λ / 4 plate, and the "absorption axis" of the polarizer means the direction in which the absorbance is highest. To do.

[Polarizer]
The polarizer of the polarizing plate of the present invention is not particularly limited as long as it is a member having a function of converting light into specific linearly polarized light, and conventionally known absorption type polarizers and reflection type polarizers can be used. ..
As the absorption type polarizer, an iodine-based polarizer, a dye-based polarizer using a dichroic dye, a polyene-based polarizer, and the like are used. Iodine-based polarized light and dye-based polarized light include coated and stretched polarized light, and both can be applied. However, polarized light produced by adsorbing iodine or a dichroic dye on polyvinyl alcohol and stretching it. Children are preferred.
Further, as a method for obtaining a polarizer by stretching and dyeing a laminated film having a polyvinyl alcohol layer formed on a substrate, Japanese Patent No. 5048120, Japanese Patent No. 5143918, Japanese Patent No. 46910205, and Japanese Patent No. Japanese Patent No. 4751481 and Japanese Patent No. 4751486 can be mentioned, and known techniques relating to these polarizers can also be preferably used.
As the reflective polarizer, a polarizer in which thin films having different birefringences are laminated, a wire grid type polarizer, a polarizer in which a cholesteric liquid crystal having a selective reflection region and a 1/4 wave plate are combined, and the like are used.
Among them, in terms of adhesion more excellent, polyvinyl alcohol-based resin (polymer containing as a repeating unit -CH ₂ -CHOH-, in particular, polyvinyl alcohol and ethylene - at least one selected from the group consisting of vinyl alcohol copolymer It is preferable that the polymer contains one).

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 even more preferably 5 μm to 15 μm.

[Adhesive layer]
In the polarizing plate of the present invention, an adhesive layer may be arranged between the optically anisotropic film in the optical film of the present invention and the polarizer.
The pressure-sensitive adhesive layer used for laminating the optically anisotropic film and the polarizer includes, for example, the ratio of the storage elastic modulus G'measured by a dynamic viscoelasticity measuring device to the loss elastic modulus G'(tan δ =). G "/ G') represents a substance having a value of 0.001 to 1.5, and includes so-called adhesives, substances that easily creep, and the like. Examples of the pressure-sensitive adhesive that can be used in the present invention include, but are not limited to, a polyvinyl alcohol-based pressure-sensitive 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, and a plasma display panel.
Of 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 the liquid crystal display device is preferable. More preferred.

[Liquid crystal display device]
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-mentioned 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, it is preferable to use the polarizing plate of the present invention as the polarizing plate on the front side, and the polarizing plate of the present invention as the polarizing plate on the front side and the rear side. Is more preferable to use.
The liquid crystal cells constituting the liquid crystal display device will be described in detail below.

<LCD cell>
The liquid crystal cell used in the liquid crystal display device is a VA (Vertical Element) mode, an OCB (Optically Compensated Bend) mode, an IPS (In-Plane-Switching) mode, an FFS (Fringe-Field-Switching) mode, or a TN (Twisted) mode. The Nematic mode is preferred, but is not limited to these.
In the liquid crystal cell in the TN mode, the rod-shaped liquid crystal molecules are substantially horizontally oriented when no voltage is applied, and are further twisted to 60 to 120 °. The TN mode liquid crystal cell is most often used as a color TFT liquid crystal display device, and has been described in many documents.
In the VA mode liquid crystal cell, the rod-shaped liquid crystal molecules are substantially vertically oriented when no voltage is applied. In the VA mode liquid crystal cell, (1) a VA mode liquid crystal cell in a narrow sense in which rod-shaped liquid crystal molecules are oriented substantially vertically when no voltage is applied and substantially horizontally when a voltage is applied (Japanese Patent Laid-Open No. 2-). In addition to (described in Japanese Patent Application Laid-Open No. 176625), (2) a liquid crystal cell (SID97, Digital of technique. Papers (Proceedings) 28 (1997) 845 in which the VA mode is multi-domainized for expanding the viewing angle). ), (3) Liquid crystal cells in a mode (n-ASM mode) in which rod-shaped liquid crystal molecules are substantially vertically oriented when no voltage is applied and twisted and multi-domain oriented when a voltage is applied. (1998)) and (4) SURVIVAL mode liquid crystal cells (announced at LCD International 98) are included. Further, it may be any of PVA (Patternized Vertical Alignment) type, optical alignment type (Optical Alignment), and PSA (Polymer-Sustained Alignment). Details of these modes are described in Japanese Patent Application Laid-Open No. 2006-215326 and Japanese Patent Application Laid-Open No. 2008-538819.
In the liquid crystal cell in the IPS mode, the rod-shaped liquid crystal molecules are oriented substantially parallel to the substrate, and the liquid crystal molecules respond in a plane by applying an electric field parallel to the substrate surface. In the IPS mode, the display is black when no electric field is applied, and the absorption axes of the pair of upper and lower polarizing plates are orthogonal to each other. Methods for reducing leakage light when displaying black in an oblique direction and improving the viewing angle by using an optical compensation sheet are described in JP-A-10-54982, JP-A-11-202323, and JP-A-9-292522. It is disclosed in JP-A-11-133408, JP-A-11-305217, JP-A-10-307291, and the like.

[Organic EL display device]
Examples of the organic EL display device which is an example of the image display device of the present invention include, from the visual side, a polarizer, a λ / 4 plate (positive A plate) made of the optically anisotropic film of the present invention, and an organic EL. A mode in which the display panel and the display panel are provided in this order is preferably mentioned.
Further, the organic EL display panel is a display panel configured by using an organic EL element formed by sandwiching an organic light emitting layer (organic electroluminescence layer) 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.

The present invention will be described in more detail below based on examples. The materials, amounts used, ratios, treatment contents, treatment procedures, etc. shown in the following examples can be appropriately changed as long as they do not deviate from the gist of the present invention. Therefore, the scope of the present invention should not be construed as limiting by the examples shown below.

[Synthesis of specific compound (Ig)]

As shown in the above scheme, 60.0 g of compound (Ia: 4-hydroxybutyl acrylate), 49.3 g of triethylamine, and 0.9 g of BHT (dibutylhydroxytoluene), 120.1 mL of DMAc (dimethylacetamide), and , Toluene was mixed with 114.1 mL. Then, the temperature was cooled to 0 ° C., and 50.6 g of mesylate chloride was slowly added dropwise. After completion of the dropping, the mixture was stirred at an internal temperature of 0 ° C. for 1 hour. Then, the temperature was returned to room temperature (23 ° C.), the liquid was separated with dilute hydrochloric acid, and the second liquid separation was carried out with brine to obtain compound (Ib).
Toluene solution of the compound (Ib) obtained above, 91.40 g of 1,1'-bisimouth hexyl-4,4'-dicarboxylic acid, 72.73 g of triethylamine, and 0.8 g of dibutylhydroxytoluene were added. , DMAc 274.2 mL, and toluene 69.7 mL. Then, it was heated to an internal temperature of 90 ° C. and reacted for 5 hours. Then, the temperature was returned to room temperature, dilute hydrochloric acid was added, and the mixture was heated to 42 ° C. to separate the liquids. Then, 0.5 g of TEMPO (2,2,6,6-tetramethylpiperidin1-oxyl) and 164.5 mL of toluene were added, and then the liquid was divided twice with an aqueous sodium hydrogen carbonate solution. The obtained solution was concentrated with an evaporator, the toluene concentration was adjusted to 50%, and 25.7 g of N, N-dimethylformamide (DMF) was added to obtain compound (Ic).
235.0 g of a toluene solution of the compound (Ic) obtained above and 0.2 g of dibutylhydroxytoluene were mixed with 41.9 mL of toluene. Then, the mixture was cooled to an internal temperature of 0 ° C., and 21.0 g of thionyl chloride was slowly added dropwise. After completion of the dropping, the temperature was returned to room temperature and the mixture was stirred for 30 minutes. Then, it was allowed to stand to remove the emulsion that settled on the bottom of the reaction vessel. Then, the mixture was cooled to an internal temperature of 0 ° C., and a mixed solution of 26.5 g of trans-4-hydroxycyclohexanecarboxylic acid and 56.0 mL of DMAc was slowly added dropwise. After completion of the dropping, the temperature was returned to room temperature and the mixture was stirred for 5 hours. Then, 300 ml of a 5% aqueous sodium hydrogen carbonate solution and 300 mL of hexane were added, and the precipitated solid was taken out by filtration. The obtained solid was mixed with 300 mL of ethyl acetate, heated to 60 ° C. and stirred for 1 hour, and then the solid was removed by filtration to obtain compound (Id).
10 g of the compound (Id) obtained above was weighed, 3.7 g of DMF and 0.02 g of dibutylhydroxytoluene were added, and the mixture was mixed with 50.0 mL of toluene. Then, the mixture is cooled to an internal temperature of 0 ° C., and 2.8 g of thionyl chloride is slowly added dropwise. After completion of the dropping, the temperature is returned to room temperature and the mixture is stirred for 30 minutes. Then, the mixture was cooled to an internal temperature of 0 ° C., and a mixed solution of 5.8 g of 7-bromo-1-heptanol and 10.0 mL of DMAc was slowly added dropwise. After completion of the dropping, the temperature was returned to room temperature and the mixture was stirred for 5 hours. Then, 120 ml of water and 120 mL of hexane were added, and the precipitated solid was taken out by filtration. The obtained solid was purified by column chromatography to obtain compound (Ie).
1.7 g of the compound (Ie) obtained above is weighed, 0.24 g of the compound (If), 0.34 g of potassium carbonate, and 0.01 g of dibutylhydroxytoluene are added, and 1.0 mL of THF and DMAc1 are added. .Mixed to 4 mL. The mixture was heated to an internal temperature of 60 ° C. and stirred for 2 hours. Then, the temperature was returned to room temperature, 35 mL of water was added, and the precipitated solid was taken out by filtration. The obtained solid was purified by column chromatography to obtain 1.05 g (yield 76%) of compound (Ig).
^{The 1} H-NMR (Nuclear Magnetic Resonance) data of the obtained compound (Ig) is shown below.
^{1 1} HNMR (CDCl ₃ ) δ (ppm) = 0.91 (m, 8H), 1.20-1.29 (m, 12H), 1.43 (m, 8H), 1.61 (m, 12H) , 1.75 (m, 16H), 2.20 (m, 6H), 2.75 (m, 12H), 3.88-4.16 (30H), 5.83 (d, 2H), 6. 12 (q, 2H), 6.41 (d, 2H), 6.94 (s, 2H)

[Synthesis of specific compound (II-g)]
The compound (II-f) represented by the following formula (II-f) was synthesized by the method described in paragraphs [0252] to [0254] of JP-A-2011-162678.
After that, the specific compound represented by the following formula (II-g) is used in the same manner as the specific compound (Ig) except that the compound (II-f) is used instead of the compound (If). (II-g) was synthesized.

^{The 1} H-NMR data of the obtained specific compound (II-g) is shown below.
^{1 1} H-NMR (CDCl ₃ ) δ (ppm) = 0.91 (m, 8H), 1.20-1.29 (m, 12H), 1.43 (m, 8H), 1.61 (m, 12H), 1.75 (m, 16H), 2.20 (m, 6H), 2.43 (s, 3H), 2.75 (m, 12H), 3.88-4.16 (30H), 5.83 (d, 2H), 6.12 (q, 2H), 6.41 (d, 2H), 7.01 (s, 2H), 7.13 (s, 1H), 7.25 (s) , 2H), 7.81 (d, 1H)

[Synthesis of reverse wavelength dispersible liquid crystal compound (II-a)]
A reverse wavelength dispersive liquid crystal compound (II-a) represented by the following formula (II-a) was synthesized according to the method described in paragraph [0122] (Example 4) of JP-A-2016-081035. In the following formula (II-a), the group adjacent to the acryloyloxy group represents a propylene group (a group in which a methyl group is replaced with an ethylene group), and represents a mixture of positional isomers having different methyl group positions.

[Example 1]
[Manufacturing of optical film]
A polymerizable liquid crystal composition having the following composition was prepared and applied to a glass substrate with a rubbing-treated polyimide alignment film (SE-150 manufactured by Nissan Chemical Industries, Ltd.) by spin coating.
The coating film was oriented at the temperatures shown in Table 5 below to form a liquid crystal layer.
Then, the film was cooled to the exposure temperature shown in Table 5 below ^{, and the orientation was fixed by irradiation with ultraviolet rays of 1000 mJ / cm 2} , to form an optically anisotropic film, and an optical film was prepared.

―――――――――――――――――――――――――――――――――
Optically anisotropic layer film coating liquid ――――――――――――――――――――――――――――――――――
-Specific compound (Ig) 50 parts by mass-The following polymerizable smectic liquid crystal compound (Sm-1) 50 parts by mass-Photopolymerization initiator (Irgacure 819, manufactured by BASF) 2 parts by mass-The following fluorine-containing compound A 1 mass Part ・ Chloroform 521 parts by mass ――――――――――――――――――――――――――――――――――

Polymerizable smectic liquid crystal compound (Sm-1)

Fluorine-containing compound A

[Example 2]
An optical film was produced in the same manner as in Example 1 except that the specific compound was changed to the compound shown in Table 3 below.

[Comparative Example 1]
An optical film was produced in the same manner as in Example 1 except that the following polymerizable nematic liquid crystal compound (Ne-1) was blended in place of the polymerizable smectic liquid crystal compound (Sm-1).

Polymerizable nematic liquid crystal compound (Ne-1)

[Comparative Example 2]
The optical film was prepared in the same manner as in Example 1 except that the inverse wavelength dispersible liquid crystal compound (II-a) was blended in place of the specific compound and the polymerizable smectic liquid crystal compound (Sm-1) was not blended. Made.

[Comparative Example 3]
An optical film was produced in the same manner as in Example 1 except that the polymerizable smectic liquid crystal compound (Sm-1) was not blended.

<Letteration>
With respect to the produced optical film, a retardation value (Re (450)) having a wavelength of 450 nm and a retardation value (Re (550)) having a wavelength of 550 nm were obtained using Axo Scan (OPMF-1, manufactured by Optoscience). The measurement was performed, and Re (450) / Re (550) was calculated. These results are shown in Table 5 below.

<Moist heat durability>
As the test conditions for moist heat durability, a test was conducted in which the mixture was left to stand for 500 hours in an environment of 85 ° C. and 85% relative humidity.
The Re (550) of the optical film before the test and the Re (550) of the optical film after the test were measured, and the wet heat durability was evaluated according to the following criteria. The results are shown in Table 3 below.
A: The amount of change in Re (550) after the test with respect to Re (550) before the test is less than 10% of Re (550) before the test. B: Re (550) after the test with respect to Re (550) before the test. The amount of change is 10% or more and less than 30% of Re (550) before the test C: The amount of change of Re (550) after the test with respect to Re (550) before the test is 30% or more of Re (550) before the test.

<Amine resistance>
Test conditions for amine _resistance, placed 2 mol% solution of NH 3 / MeOH in a vial, place the optical film to the outlet portion, was tested to stand for 10 hours.
The Re (550) of the optical film before the test and the Re (550) of the optical film after the test were measured, and the amine resistance was evaluated according to the following criteria. The results are shown in Table 3 below.
A: The amount of change in Re (550) after the test with respect to Re (550) before the test is less than 10% of Re (550) before the test. B: Re (550) after the test with respect to Re (550) before the test. The amount of change is 10% or more and less than 30% of Re (550) before the test C: The amount of change of Re (550) after the test with respect to Re (550) before the test is 30% or more of Re (550) before the test.

<Light resistance>
For the produced optical film, set the glass substrate on a xenon irradiator (SX75 manufactured by Suga Test Instruments Co., Ltd.) so that the coating film of the polymerizable liquid crystal composition serves as the irradiation surface, and use a # 275 filter for 200 hours. An irradiation test was conducted.
The Re (550) of the optical film before the test and the Re (550) of the optical film after the test were measured, and the light resistance was evaluated according to the following criteria. The results are shown in Table 3 below.
A: The amount of change in Re (550) after the test with respect to Re (550) before the test is less than 5% of Re (550) before the test. B: Re (550) after the test with respect to Re (550) before the test. The amount of change is 5% or more and less than 15% of Re (550) before the test C: The amount of change of Re (550) after the test with respect to Re (550) before the test is 15% or more of Re (550) before the test.

From the results shown in Table 3 above, it was found that when the polymerizable nematic liquid crystal compound was blended with the specific compound, the amine resistance of the formed optically anisotropic film was inferior (Comparative Example 1).
Further, it was found that when the inverse wavelength dispersible liquid crystal compound (II-a) was blended in place of the specific compound and the polymerizable smectic liquid crystal compound was not blended, the amine resistance of the formed optically anisotropic film was inferior. (Comparative example 2).
Further, it was found that when the specific compound was blended and neither the polymerizable smectic liquid crystal compound nor the polymerizable nematic liquid crystal compound was blended, the inverse wavelength dispersibility was not exhibited in the formed optically anisotropic film (comparison). Example 3).
On the other hand, it was found that when the polymerizable smectic liquid crystal compound was blended with the specific compound, the formed optically anisotropic film exhibited reverse wavelength dispersibility and the amine resistance was also good (Example 1 and). 2).

10 Optical film 12 Optical anisotropic film 14 Alignment film 16 Support 18 Hard coat layer

Claims

A polymerizable liquid crystal composition containing a compound represented by the following formula (I-1) and a polymerizable smectic liquid crystal compound.

Here, in the above formula (I-1),
Ar 1 and Ar 2 each independently represent an aromatic ring having a maximum absorption wavelength of 280 to 420 nm.
D 1 represents a single bond, or, -CO -, - O -, - S -, - C (= S) -, - CR 1 R 2 -, - CR 3 = CR 4 -, - NR 5 -, or , Representing a divalent linking group consisting of a combination of two or more of these, and R 1 to R 5 independently represent a hydrogen atom, a fluorine atom, or an alkyl group having 1 to 4 carbon atoms.
p represents 0 or 1.
X 1 and X 2 independently represent -O-, -S-, -CO-, -CO-NR 6- , or a single bond, and R 6 independently represents a hydrogen atom and a fluorine atom, respectively. , Or an alkyl group having 1 to 4 carbon atoms.
L 1 and L 2 independently represent an alkylene group represented by the following formula (I-2).
Mes 1 and Mes 2 independently represent a polymerizable group-containing group represented by the following formula (I-3).

Here, in the above formula (I-2),
*, For L 1 represents a bonding position to Mes 1 or X 1, represents a bonding position to Mes 2 or X 2 for L 2.
m represents an integer of 1 or more.
However, the hydrogen atom contained in the alkylene group is a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfuranyl group, a cyano group, a nitro group, an isocyano group, a thioisocyano group, or 1 to 20 carbon atoms. It may be substituted with an alkyl group of.
Further, of -CH 2- that constitutes the alkylene group and is not directly bonded to X 1 or X 2 , one or two or more -CH 2- that are not adjacent to each other are -O-, -S-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, or It may be replaced with -C≡C-.

Here, in the above formula (I-3),
* Represents a bonding position with L 1 for Mes 1, represents a bonding position to L 2 for Mes 2.
M is a 1,4-phenylene group, a 1,4-cyclohexylene group, a pyridine-2,5-diyl group, a pyrimidine-2,5-diyl group, a naphthalene-2,6-diyl group, a naphthalene-1,4. It represents a diyl group, a tetrahydronaphthalene-2,6-diyl group, a decahydronaphthalene-2,6-diyl group, or a 1,3-dioxane-2,5-diyl group. However, the hydrogen atom contained in these groups is a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfuranyl group, a cyano group, a nitro group, an isocyano group, a thioisocyano group, or 1 to 20 carbon atoms. It may be substituted with an alkyl group of.
D 2 and D 3 are independently -O-, -S-, -OCH 2- , -CH 2 CH 2- , -CO-, -COO-, -CO-S-, -OCO-O-, respectively. , -CO-NH-, -SCH 2- , -CF 2 O-, -CF 2 S-, -CH = CH-COO-, -CH = CH-OCO-, -COO-CH 2 CH 2 -,- OCO-CH 2 CH 2- , -COO-CH 2- , -OCO-CH 2- , -CH = CH-, -N = N-, -CH = N-, -CH = NN = CH-, Represents -CF = CF-, -C≡C-, or a single bond.
The SP is one or more of —CH 2- that constitutes 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. Represents a divalent linking group substituted with -O-, -S-, -NH-, -N (Q)-, or -CO-, and Q represents a substituent.
P represents a polymerizable group.
n represents an integer of 2 or more, the plurality of M, each may be the same or different and a plurality of D 2, respectively may be the same or different and a plurality of D 3 is , Each may be the same or different, and the plurality of SPs may be the same or different.
The polymerizable liquid crystal composition according to claim 1, wherein Ar 1 and Ar 2 in the formula (I-1) represent an aromatic ring having a maximum absorption wavelength at 300 to 400 nm.
Claimed that Ar 1 and Ar 2 in the formula (I-1) represent any aromatic ring selected from the group consisting of groups represented by the following formulas (Ar-1) to (Ar-7). Item 2. The polymerizable liquid crystal composition according to Item 1 or 2.

Here, in the above formulas (Ar-1) to (Ar-7),
* Represents a bonding position with X 1 or D 1 for Ar 1, for Ar 2 represents a bonding position to D 1 or X 2.
Q 1 represents an N or CH.
Q 2 is, -S -, - O-, or, -N (R 7) - represents, R 7 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 or an aromatic heterocyclic group having 3 to 12 carbon atoms, which may have a substituent.
Z 1 , Z 2 and Z 3 independently have 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, and a carbon number of carbons. 6 to 20 monovalent aromatic hydrocarbon groups, halogen atoms, cyano groups, nitro groups, -OR 8 , -NR 9 R 10 , or -SR 11 are represented, and R 8 to R 11 are independent of each other. , A hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and Z 1 and Z 2 may be bonded to each other to form an aromatic ring.
A 1 and A 2 each independently represent a group selected from the group consisting of -O-, -N (R 12 )-, -S-, and -CO-, where R 12 is a hydrogen atom or Represents a substituent.
X represents a non-metal atom of groups 14-16 to which a hydrogen atom or a substituent may be bonded.
D 4 and D 5 are each independently a single bond, or, -CO -, - O -, - S -, - C (= S) -, - CR 1 R 2 -, - CR 3 = CR 4 - , -NR 5- , or a divalent linking group consisting of a combination of two or more of these, and R 1 to R 5 each independently have a hydrogen atom, a fluorine atom, or a carbon number of 1 to 4. Represents an alkyl group.
SP 1 and SP 2 independently constitute 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. One or more of -CH 2- represents a divalent linking group substituted with -O-, -S-, -NH-, -N (Q)-, or -CO-, where Q is a substituent. Represents.
L 3 and L 4 each independently represent a monovalent organic group.
Ax represents 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 heterocycle.
Ay has a hydrogen atom, an alkyl group having 1 to 12 carbon atoms which may have a substituent, or at least one aromatic ring selected from the group consisting of an aromatic hydrocarbon ring and an aromatic heterocycle. , Represents an organic group having 2 to 30 carbon atoms.
The aromatic ring in Ax and Ay may have a substituent, or Ax and Ay may be bonded to form a ring.
Q 3 are a hydrogen atom or an alkyl group having 1 to 6 carbon atoms which may have a substituent.
The polymerizable liquid crystal composition according to any one of claims 1 to 3, wherein X 1 and X 2 in the formula (I-1) represent a linking group represented by —O—.
Claims 1 to 1, wherein P in the formula (I-3) represents any polymerizable group selected from the group consisting of groups represented by the following formulas (P-1) to (P-20). 4. The polymerizable liquid crystal composition according to any one of 4.

Here, in the above formulas (P-1) to (P-20), * represents a bonding position with SP.
The content of the polymerizable smectic liquid crystal compound is 15 to 75% by mass with respect to the total mass of the polymerizable smectic liquid crystal compound and the compound represented by the formula (I-1), according to claims 1 to 5. The polymerizable liquid crystal composition according to any one of the following items.
An optically anisotropic film obtained by polymerizing the polymerizable liquid crystal composition according to any one of claims 1 to 6.
The optically anisotropic film according to claim 7, which satisfies the following formula (III).
0.50 <Re (450) / Re (550) <1.00 ... (III)
Here, in the formula (III), Re (450) represents the in-plane retardation of the optically anisotropic film at a wavelength of 450 nm, and Re (550) represents the in-plane retardation of the optically anisotropic film at a wavelength of 550 nm. Represents a letteration.
An optical film having the optically anisotropic film according to claim 7 or 8.
A polarizing plate having the optical film according to claim 9 and a polarizer.
An image display device having the optical film according to claim 9 or the polarizing plate according to claim 10.