Liquid crystal composition, benzoquinone derivative, liquid crystal cured layer, optical film, polarizing plate, and image display device

Abstract

The present invention addresses the problem of providing a liquid crystal composition, a benzoquinone derivative, a liquid crystal cured layer, an optical film, a polarizing plate, and an image display device with which it is possible to produce a liquid crystal cured layer having good alignment properties and light resistance. This liquid crystal composition contains a compound represented by formula (A) and a liquid crystal compound.

Description

TECHNICAL FIELD

[0001] The present application relates to a liquid crystal composition, a benzoquinone derivative, a liquid crystal cured layer, an optical film, a polarizing plate, and an image display device. BACKGROUND

[0002] In order to eliminate image coloring and expand the viewing angle, optical films such as optical compensation sheets or phase difference films are used in various image display devices.

[0003] A stretched birefringent film is used as the optical film, but in recent years, an optical film having an optically anisotropic layer composed of a liquid crystal compound has been proposed instead of the stretched birefringent film.

[0004] As such an optical film, an optical film formed using a liquid crystal composition containing a compound represented by a prescribed formula and a liquid crystal compound is known (for example, see Patent Document 1).

[0005] PRIOR ART DOCUMENTS PATENT DOCUMENTS Patent Document 1: Japanese Patent Application Publication No. 2011-207765 SUMMARY

[0006] PROBLEMS TO BE SOLVED BY THE INVENTION As a result of the present inventors' study on the liquid crystal composition described in Patent Document 1, it was found that the alignment property (hereinafter, simply referred to as "alignment property") of the liquid crystal compound in a liquid crystal cured layer formed using the liquid crystal composition becomes good, but it was confirmed that there is room for improvement in the light resistance.

[0007] Therefore, an object of the present application is to provide a liquid crystal composition, a benzoquinone derivative, a liquid crystal cured layer, an optical film, a polarizing plate, and an image display device, which enable the production of a liquid crystal cured layer having both good alignment property and light resistance.

[0008] MEANS FOR SOLVING THE PROBLEMS As a result of the present inventors' intensive study in order to solve the above problems, it was found that a liquid crystal cured layer having both good alignment property and light resistance can be produced if a liquid crystal composition containing a compound represented by Formula (A) and a liquid crystal compound is used, and thus the present application was completed.

[0009] That is, the present inventors found that the above problems can be solved by the following structure.

[0010] [1] A liquid crystal composition containing a compound represented by the following Formula (A) and a liquid crystal compound.

[0011] [2] The liquid crystal composition according to [1], wherein the liquid crystal compound is a compound represented by the following Formula (B).

[0012] [3] The liquid crystal composition according to [1] or [2], wherein the content of the compound represented by the following formula (A) is 18% by mass or less, relative to the total mass of the compound represented by the following formula (A) and the liquid crystal compound.

[0013] [4] The liquid crystal composition according to any one of [1] to [3], wherein Ar in the following formula (A) 1 is an aromatic ring represented by the following formula (BQ-1) or (BQ-2).

[0014] [5] The liquid crystal composition according to any one of [2] to [4], wherein Ar in the following formula (A) 1 is the same structure as Ar in the following formula (B) 2

[0015] [6] A benzoquinone derivative represented by the following formula (A).

[0016] [7] A liquid crystal cured layer formed by fixing the alignment state of the liquid crystal composition according to any one of [1] to [5].

[0017] [8] An optical film having the liquid crystal cured layer according to [7].

[0018] [9] A polarizing plate having the optical film according to [8] and a polarizer.

[0019]

[10] An image display device having the optical film according to [8].

[0020] Effects of Invention According to the present application, it is possible to provide a liquid crystal composition, a benzoquinone derivative, a liquid crystal cured layer, an optical film, a polarizing plate, and an image display device, which can produce a liquid crystal cured layer having both good alignment properties and light resistance. BRIEF DESCRIPTION OF DRAWINGS

[0021] Figure 1 is a schematic cross-sectional view showing an example of an optical film. DETAILED DESCRIPTION

[0022] Hereinafter, the present application will be described in detail.

[0023] The following description of the components is sometimes completed based on the representative embodiment of the present application, but the present application is not limited to this embodiment.

[0024] In addition, in the present specification, a numerical range represented by "to" indicates a range including the numerical values recited before and after "to" as lower limit values and upper limit values.

[0025] ​Furthermore, in this specification, the upper or lower limit value of a numerical range recorded in a certain numerical range can be replaced with the upper or lower limit value of other numerical ranges recorded in a certain period. Also, the upper or lower limit value of a numerical range recorded in this specification can be replaced with the value shown in the embodiment.

[0026] Furthermore, in this specification, each component may be used alone as one of its own substances, or two or more substances may be used together. Where two or more substances are used simultaneously for each component, the content of that component, unless otherwise stated, refers to the total content of the substances used simultaneously.

[0027] Furthermore, in this specification, "(meth)acrylate" is the expression for "acrylate" or "methacrylate", "(meth)acrylate group" is the expression for "acrylate group" or "methacrylate group", and "(meth)acryloyl group" is the expression for "acryloyl group" or "methacryloyl group".

[0028] Furthermore, the bonding direction of the divalent groups (e.g., -O-CO-) described in this specification is not particularly limited; for example, in "L 1 -L 2 -L 3 In the bonding of ", in L 2 In the case of -O-CO-, if the bond is placed on L 1 The side position is set as 1. Bonded to L 3 The side position is set as 2, then L 2 It can be 1-O-CO- 2, can also be 1-CO-O- 2.

[0029] Furthermore, in this specification, Re(λ) and Rth(λ) represent the in-plane retardation and the thickness-direction retardation at wavelength λ, respectively. Unless otherwise specified, wavelength λ is set to 550 nm.

[0030] In this invention, Re(λ) and Rth(λ) are values ​​obtained by measurement at wavelength λ using an AxoScan (manufactured by Axometrics). The following values ​​are calculated by inputting the average refractive index ((nx+ny+nz) / 3) and film thickness (d(μm)) into the AxoScan: Slow axis direction (°); Re(λ) = R0(λ); and Rth(λ) = ((nx+ny) / 2-nz) x d.

[0031] In addition, R0(λ) is shown as a value calculated by AxoScan, but refers to Re(λ).

[0032] Also, in the present specification, as a substituent (1 valent substituent), for example, a substituent described in Substituent Group A described below can be mentioned.

[0033] In addition, in the present specification, "may have a substituent" includes not only a form having no substituent, but also a form having one or more substituents.

[0034] <Substituent Group A> As a substituent, for example, the following can be mentioned a halogen atom (for example, a fluorine atom, a chlorine atom, a bromine atom, preferably a chlorine atom, a fluorine atom, more preferably a fluorine atom); an alkyl group (preferably a linear, branched or cyclic alkyl group having 1 to 48 carbon atoms, more preferably a linear, branched or cyclic alkyl group having 1 to 24 carbon atoms, particularly preferably a linear, branched or cyclic alkyl group having 1 to 8 carbon atoms, for example, a linear alkyl group having 1 to 6 carbon atoms (for example, a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an n-pentyl group, an n-hexyl group), a branched alkyl group having 3 to 6 carbon atoms (for example, an isopropyl group, an isobutyl group, a tert-butyl group, a sec-butyl group, a neopentyl group, an isohexyl group, a 3-methylpentyl group), a cyclic alkyl group having 3 to 12 carbon atoms (for example, a cyclopropyl group, a cyclopentyl group, a cyclohexyl group, a 1-norbornyl group, a 1-adamantyl group)); an alkenyl group (preferably an alkenyl group having 2 to 48 carbon atoms, more preferably an alkenyl group having 2 to 18 carbon atoms, for example, a vinyl group, an allyl group, a 1-butenyl group, a 2-butenyl group); an alkynyl group (preferably an alkynyl group having 2 to 6 carbon atoms, more preferably an alkynyl group having 2 to 4 carbon atoms, for example, an ethynyl group, a 1-propynyl group, a propargyl group, a 1-butynyl group, a 2-butynyl group); an aryl group (preferably an aryl group having 6 to 48 carbon atoms, more preferably an aryl group having 6 to 24 carbon atoms, for example, a phenyl group, an oligoaryl group (a naphthyl group, an anthryl group), a phenanthryl group, a fluorenyl group, a pyrenyl group, a triphenylenyl group, a biphenyl group); a heteroaryl group (preferably a heteroaryl group having 1 to 32 carbon atoms, more preferably a heteroaryl group having 1 to 18 carbon atoms, for example, a 2-thienyl group, a 4-pyridyl group, a 2-furyl group, a 2-pyrimidyl group, a 1-pyridyl group, a 2-benzothiazolyl group, a 1-imidazolyl group, a 1-pyrazolyl group, a benzotriazol-1-yl group); Aryloxy (preferably aryloxy having 6 to 48 carbon atoms, more preferably 6 to 24 carbon atoms, for example, phenoxy, 1-naphthoxy); Silyl group (preferably silyl group having 3 to 38 carbon atoms, more preferably 3 to 18 carbon atoms, for example, trimethylsilyl group, triethylsilyl group, tributylsilyl group, t-butyldimethylsilyl group, t-hexyldimethylsilyl group); Hydroxy; cyano; nitro; morpholinyl; Alkoxy (preferably alkoxy having 1 to 48 carbon atoms, more preferably 1 to 24 carbon atoms, for example, methoxy, ethoxy, 1-butyloxy, 2-butyloxy, isopropoxy, t-butyloxy, dodecyloxy, cycloalkyloxy (for example, cyclopentyloxy, cyclohexyloxy)); Aryloxy (preferably aryloxy having 6 to 48 carbon atoms, more preferably 6 to 24 carbon atoms, for example, phenoxy, 1-naphthoxy); Alkenyloxy (preferably alkenyloxy having 2 to 6 carbon atoms, for example, ethenyloxy, 1-propenyloxy, 2-n-propenyloxy (allyloxy), 1-n-butenyloxy, isoprenyloxy); Heterocyclic oxy group (preferably heterocyclic oxy group having 1 to 32 carbon atoms, more preferably 1 to 18 carbon atoms, for example, 1-phenyltetrazol-5-yloxy, 2-tetrahydropyranyloxy); Silyloxy (preferably silyloxy having 1 to 32 carbon atoms, more preferably 1 to 18 carbon atoms, for example, trimethylsilyloxy, t-butyldimethylsilyloxy, diphenylmethylsilyloxy); Acyloxy (preferably acyloxy having 2 to 48 carbon atoms, more preferably 2 to 24 carbon atoms, for example, acetyloxy, pivaloyloxy, benzoyloxy, dodecanoyloxy, propenoyloxy, methacryloyloxy); Hydroxyalkyleneoxy (preferably hydroxyalkyleneoxy having 2 to 10 carbon atoms, for example, hydroxyethyleneoxy); Alkoxycarbonyloxy (preferably alkoxycarbonyloxy having 2 to 48 carbon atoms, more preferably 2 to 24 carbon atoms, for example, ethoxycarbonyloxy, t-butyloxycarbonyloxy, cycloalkoxycarbonyloxy (for example, cyclohexyloxycarbonyloxy)); Aryloxycarbonyloxy (preferably aryloxycarbonyloxy having 7 to 32 carbon atoms, more preferably 7 to 24 carbon atoms, for example, phenoxycarbonyloxy); Carbamoyloxy (preferably carbamoyloxy having 1 to 48 carbon atoms, more preferably 1 to 24 carbon atoms, for example, N,N-dimethylcarbamoyloxy, N-butylcarbamoyloxy, N-phenylcarbamoyloxy, N-ethyl-N-phenylcarbamoyloxy); Sulfamoyloxy (preferably sulfamoyloxy having 1 to 32 carbon atoms, more preferably 1 to 24 carbon atoms, for example, N,N-diethylsulfamoyloxy, N-propylsulfamoyloxy); Alkylsulfonyloxy (preferably alkylsulfonyloxy having 1 to 38 carbon atoms, more preferably 1 to 24 carbon atoms, for example, methylsulfonyloxy, hexadecylsulfonyloxy, cyclohexylsulfonyloxy); Arylsulfonyloxy (preferably arylsulfonyloxy having 6 to 32 carbon atoms, more preferably 6 to 24 carbon atoms, for example, phenylsulfonyloxy); Acyl (preferably acyl having 1 to 48 carbon atoms, more preferably 1 to 24 carbon atoms, for example, formyl, acetyl, propenoyl, methacryloyl, pivaloyl, benzoyl, tetradecanoyl, cyclohexanoyl); Alkoxycarbonyl (preferably alkoxycarbonyl having 2 to 48 carbon atoms, more preferably 2 to 24 carbon atoms, for example, methoxycarbonyl, ethoxycarbonyl, octadecyloxycarbonyl, cyclohexyloxycarbonyl, 2,6-di-tert-butyl-4-methylcyclohexyloxycarbonyl); Aryloxycarbonyl (preferably aryloxycarbonyl having 7 to 32 carbon atoms, more preferably 7 to 24 carbon atoms, for example, phenoxycarbonyl); Carbamoyl (preferably carbamoyl having 1 to 48 carbon atoms, more preferably 1 to 24 carbon atoms, for example, carbamoyl, N,N-diethylcarbamoyl, N-ethyl-N-octylcarbamoyl, N,N-dibutylcarbamoyl, N-propylcarbamoyl, N-phenylcarbamoyl, N-methyl N-phenylcarbamoyl, N,N-dicyclohexylcarbamoyl); Amino (preferably amino having 32 or less carbon atoms, more preferably 24 or less carbon atoms, for example, amino, methylamino, N,N-dibutylamino, tetradecylamino, 2-ethylhexylamino, cyclohexylamino); Anilino (preferably anilino having 6 to 32 carbon atoms, more preferably 6 to 24 carbon atoms, for example, anilino, N-methylanilino); Heterocyclic amino (preferably heterocyclic amino having 1 to 32 carbon atoms, more preferably 1 to 18 carbon atoms, for example, 4-pyridylamino); Carboxamido (preferably carboxamido having 2 to 48 carbon atoms, more preferably 2 to 24 carbon atoms, for example, acetamido, benzamido, tetradecanamido, pivaloylamido, cyclohexanamido). ureido group (preferably ureido group having 1 to 32 carbon atoms, more preferably ureido group having 1 to 24 carbon atoms, for example, ureido group, N,N-dimethylureido group, N-phenylureido group); imido group (preferably imido group having 36 or less carbon atoms, more preferably imido group having 24 or less carbon atoms, for example, N-succinimidyl group, N-phthalimidyl group); alkoxycarbonylamino group (preferably alkoxycarbonylamino group having 2 to 48 carbon atoms, more preferably alkoxycarbonylamino group having 2 to 24 carbon atoms, for example, methoxycarbonylamino group, ethoxycarbonylamino group, t-butoxycarbonylamino group, octadecyloxycarbonylamino group, cyclohexyloxycarbonylamino group); aryloxy carbonylamino group (preferably aryloxy carbonylamino group having 7 to 32 carbon atoms, more preferably aryloxy carbonylamino group having 7 to 24 carbon atoms, for example, phenyloxy carbonylamino group); sulfonamido group (preferably sulfonamido group having 1 to 48 carbon atoms, more preferably sulfonamido group having 1 to 24 carbon atoms, for example, methanesulfonamido group, butanesulfonamido group, benzenesulfonamido group, hexadecanesulfonamido group, cyclohexanesulfonamido group); sulfamoylamino group (preferably sulfamoylamino group having 1 to 48 carbon atoms, more preferably sulfamoylamino group having 1 to 24 carbon atoms, for example, N,N-dipropylsulfamoylamino group, N-ethyl-N-dodecylsulfamoylamino group); azo group (preferably azo group having 1 to 32 carbon atoms, more preferably azo group having 1 to 24 carbon atoms, for example, phenylazo group, 3-pyrazolylazo group); alkylthio group (preferably alkylthio group having 1 to 48 carbon atoms, more preferably alkylthio group having 1 to 24 carbon atoms, for example, methylthio group, ethylthio group, octylthio group, cyclohexylthio group); arylthio group (preferably arylthio group having 6 to 48 carbon atoms, more preferably arylthio group having 6 to 24 carbon atoms, for example, phenylthio group); heterocyclic thio group (preferably heterocyclic thio group having 1 to 32 carbon atoms, more preferably heterocyclic thio group having 1 to 18 carbon atoms, for example, 2-benzothiazolylthio group, 2-pyridylthio group, 1-phenyltetrazolylthio group); alkylsulfinyl group (preferably alkylsulfinyl group having 1 to 32 carbon atoms, more preferably alkylsulfinyl group having 1 to 24 carbon atoms, for example, dodecylsulfinyl group); aryl sulfinyl group (preferably aryl sulfinyl group having 6 to 32 carbon atoms, more preferably aryl sulfinyl group having 6 to 24 carbon atoms, for example, phenyl sulfinyl group); alkylsulfonyl group (preferably alkylsulfonyl group having 1 to 48 carbon atoms, more preferably alkylsulfonyl group having 1 to 24 carbon atoms, for example, methylsulfonyl group, ethylsulfonyl group, propylsulfonyl group, butylsulfonyl group, isopropylsulfonyl group, 2-ethylhexylsulfonyl group, hexadecylsulfonyl group, octylsulfonyl group, cyclohexylsulfonyl group); Arylsulfonyl group (preferably arylsulfonyl group having 6 to 48 carbon atoms, more preferably arylsulfonyl group having 6 to 24 carbon atoms, for example, phenylsulfonyl group, 1-naphthylsulfonyl group); Sulfamoyl group (preferably sulfamoyl group having 32 or less carbon atoms, more preferably sulfamoyl group having 24 or less carbon atoms, for example, sulfamoyl group, N,N-dipropylsulfamoyl group, N-ethyl-N-dodecylsulfamoyl group, N-ethyl-N-phenylsulfamoyl group, N-cyclohexylsulfamoyl group, N-(2-ethylhexyl)sulfamoyl group); Phosphono group (preferably phosphono group having 1 to 32 carbon atoms, more preferably phosphono group having 1 to 24 carbon atoms, for example, phenyloxyphosphono group, octyloxyphosphono group, phenylphosphono group); Phosphinylamino group (preferably phosphinylamino group having 1 to 32 carbon atoms, more preferably phosphinylamino group having 1 to 24 carbon atoms, for example, ethyloxyphosphinylamino group, dioctyloxyphosphinylamino group); Epoxy group; -NHCOCH3; -SO2NHC2H4OCH3; -NHSO2CH3; These substituents can be combined two or more.

[0035] These substituents can be further substituted with these substituents. Also, in the case of having two or more substituents, they can be the same or different. Also, in the case where possible, they can be bonded to each other to form a ring.

[0036] [LIQUID CRYSTAL COMPOSITION] The liquid crystal composition of the present application is a liquid crystal composition containing a compound represented by the following formula (A) (hereinafter, also referred to simply as "specific compound A") and a liquid crystal compound.

[0037] In the present application, as described above, if a liquid crystal composition containing the specific compound A and the liquid crystal compound is used, a liquid crystal cured layer having both good orientation and good light resistance can be produced.

[0038] Although the details thereof are not clear, the present inventors and others have conjectured as follows.

[0039] That is, it is considered that since the specific compound A has a specific aromatic ring, the compatibility with the liquid crystal compound becomes good, and the excellent orientation of the liquid crystal compound can be maintained. Also, it is considered that since the specific compound A is a quinone compound, it is affected by ultraviolet rays earlier than the liquid crystal compound, and also functions as an ultraviolet ray absorber, and thus the light resistance of the produced liquid crystal cured layer becomes good.

[0040] Hereinafter, the specific compound A and the liquid crystal compound contained in the liquid crystal composition of the present application will be described in detail.

[0041] [Specific Compound A] A specific compound A is a compound represented by the following formula (A).

[0042] [Chemical Formula 1] In the above formula (A), Ar 1 represents any one aromatic ring selected from the group consisting of groups represented by the following formulas (BQ-1) to (BQ-5). In addition, in the following formulas (BQ-1) to (BQ-5), represents a bonding position to the oxygen atom in the above formula (A).

[0043] [Chemical Formula 2] In the above formula (BQ-1), Q 1 represents N or CH, Q 2 represents -S-, -O-, or -N(R 6 )-, R 6 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and Y 1 represents an aromatic hydrocarbon group having 6 to 12 carbon atoms which can have a substituent, an aromatic heterocyclic group having 3 to 12 carbon atoms which can have a substituent, or an alicyclic hydrocarbon group having 6 to 20 carbon atoms which can have a substituent, one or more -CH2- constituting the alicyclic hydrocarbon group can be substituted with -O-, -S-, or -NH-.

[0044] Among the alkyl groups having 1 to 6 carbon atoms represented as a mode of R 6 , specifically, 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, a t-butyl group, an n-pentyl group, an n-hexyl group, and the like can be mentioned.

[0045] The aromatic hydrocarbon group having 6 to 12 carbon atoms represented as a mode of Y 1 , for example, an aryl group such as a phenyl group, a 2,6-diethylphenyl group, a naphthyl group, and the like can be mentioned.

[0046] The aromatic heterocyclic group having 3 to 12 carbon atoms represented as a mode of Y 1 , for example, a heteroaryl group such as a thienyl group, a thiazolyl group, a furanyl group, a pyridyl group, and the like, and a group obtained by removing one hydrogen atom from any one of an indole ring, a benzofuran ring, a benzothiophene ring, a benzimidazole ring, a benzothiazole ring, and a benzoxazole ring can be mentioned. Among the aromatic heterocyclic groups having 3 to 12 carbon atoms represented as Y 1 , a group obtained by removing one hydrogen atom from a benzofuran ring or a benzothiazole ring is preferable.

[0047] The alicyclic hydrocarbon group having 6 to 20 carbon atoms represented as a mode of Y 1As the alicyclic hydrocarbon group having 6 to 20 carbon atoms, for example, cyclohexyl, cyclopentyl, norbornyl, adamantyl, and the like can be given.

[0048] As Y 1 As the substituent which can be present, the substituents described in the above-mentioned Substituent Group A can be given, and among them, an alkyl group, an alkoxy group, an alkoxycarbonyl group, an alkylcarbonyloxy group, a nitro group, a cyano group, or a halogen atom is preferable.

[0049] In the above-mentioned formulae (BQ-1) to (BQ-5), Z 1 , Z 2 , and Z 3 each independently represent 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, a monovalent aromatic hydrocarbon group having 6 to 20 carbon atoms, a monovalent aromatic heterocyclic group having 6 to 20 carbon atoms, a halogen atom, a cyano group, a nitro group, -OR 7 , -NR 8 R 9 , -SR 10 , -COOR 11 , or -COR 12 , R 7 to R 12 each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, Z 1 and Z 2 may be bonded to each other to form an aromatic ring.

[0050] As the monovalent aliphatic hydrocarbon group having 1 to 20 carbon atoms, an alkyl group having 1 to 15 carbon atoms is preferable, and an alkyl group having 1 to 8 carbon atoms is more preferable, and specifically, a methyl group, an ethyl group, an isopropyl group, a tert-pentyl group (1,1-dimethylpropyl group), a tert-butyl group, a 1,1-dimethyl-3,3-dimethyl-butyl group are further preferable, and a methyl group, an ethyl group, a tert-butyl group are particularly preferable.

[0051] As the monovalent alicyclic hydrocarbon group having 3 to 20 carbon atoms, for example, a monocyclic saturated hydrocarbon group such as a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, a cyclodecyl group, a methylcyclohexyl group, an ethylcyclohexyl group, and the like; a monocyclic unsaturated hydrocarbon group such as a cyclobutenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a cyclooctenyl group, a cyclodecenyl group, a cyclopentadienyl group, a cyclohexadienyl group, a cyclooctadienyl group, a cyclodecadienyl group, and the like; a bicyclo[2.2.1]heptyl group, a bicyclo[2.2.2]octyl group, a tricyclo[5.2.1.0 2,6 ]decyl group, a tricyclo[3.3.1.1 3,7 ]decyl group, a tetracyclo[6.2.1.1 3,6 .0 2,7 ]dodecyl group, an adamantyl group, and the like; and the like can be given.

[0052] The aromatic hydrocarbon group with a carbon number of 6 to 20 is a monovalent aromatic hydrocarbon group. Specifically, examples include phenyl, 2,6-diethylphenyl, naphthyl, biphenyl, etc., and preferably an aryl group with a carbon number of 6 to 12 (especially phenyl).

[0053] As a monovalent aromatic heterocyclic group with 6 to 20 carbon atoms, examples include 4-pyridyl, 2-furanyl, 2-thienyl, 2-pyrimidinyl, 2-benzothiazolyl, etc.

[0054] Examples of halogen atoms include fluorine, chlorine, bromine, and iodine atoms, with fluorine, chlorine, and bromine atoms being preferred.

[0055] On the other hand, as R 7 ~R 10 The alkyl group represented by carbon atoms is 1 to 6. Specifically, examples include methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, and n-hexyl.

[0056] As mentioned above, Z 1 and Z 2 They can bond with each other to form aromatic rings, for example, as Z in the above formula (BQ-1). 1 and Z 2 The structure in which groups bond together to form an aromatic ring can be exemplified by groups represented by the following formula (BQ-1a). Furthermore, in the following formula (BQ-1a), This indicates the bonding position with the oxygen atom in formula (A) above.

[0057] [Chemical Formula 3] Here, in the above equation (BQ-1a), Q 1 Q 2 and Y 1 Examples of the same groups as those described in the above formula (BQ-1) can be cited.

[0058] Furthermore, in the above equations (BQ-2) and (BQ-3), A 3 and A 4 Each can be independently represented by a selection from -O-, -N(R) 13 The groups in the group consisting of -, -S- and -CO-, R 13 It represents a hydrogen atom or a substituent.

[0059] As R 13 The substituents represented in one manner may be those described in the substituent group A above, wherein preferably alkyl, alkoxy, alkoxycarbonyl, alkylcarbonyloxy or halogen atoms.

[0060] Further, in the above formula (BQ-2), X represents a non-metal atom of Group 14 to 16. Among them, the non-metal atom can be bonded with a hydrogen atom or a substituent.

[0061] Further, as the non-metal atom of Group 14 to 16 represented by X, for example, an oxygen atom, a sulfur atom, a nitrogen atom bonded with a hydrogen atom or a substituent [=N-R N1 , R N1 represents a hydrogen atom or a substituent.], a carbon atom bonded with a hydrogen atom or a substituent [=C-R C1 , R C1 represents a hydrogen atom or a substituent.], etc. can be mentioned.

[0062] As the substituent, the substituents described in the above substituent group A can be mentioned, and among them, 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, an alkylcarbonyl group, a sulfo group, a hydroxy group, etc. are preferable.

[0063] Further, in the above formula (BQ-3), D 7 and D 8 each independently represent 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 by combination of two or more of them, and R 1 to R 5 each independently represent a hydrogen atom, a fluorine atom or an alkyl group having 1 to 12 carbon atoms.

[0064] Here, as the divalent linking group, specifically, for example, -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 R2 -O-CO-CR 1 R 2 -、-CR 1 R 2 -CO-O-CR 1 R 2 -、-NR 5 -CR 1 R 2 -and-CO-NR 5 - etc. R 1 R 2 and R 5 Each can be an alkyl group, representing a hydrogen atom, a fluorine atom, or a carbon atom numbering 1 to 12, respectively.

[0065] Among these, the preferred choice is any one of -CO-, -O-, and -CO-O-.

[0066] Furthermore, in the above formula (BQ-3), SP 3 and SP 4 Each of these groups independently represents a single bond or a divalent aliphatic hydrocarbon group having 1 to 20 carbon atoms. One or more of the -CH2- groups constituting the aliphatic hydrocarbon group may be substituted with -O-, -S-, -NH-, -N(Q)-, or -CO-. Q represents a substituent. Examples of substituents represented by Q are those described in substituent group A above, preferably alkyl, alkoxy, alkoxycarbonyl, alkylcarbonyloxy, or halogen atoms.

[0067] Here, examples of divalent aliphatic hydrocarbon groups include, for example, straight-chain or branched alkylene groups with 1 to 20 carbon atoms, straight-chain or branched alkenylene groups with 1 to 20 carbon atoms, and straight-chain or branched alkyne groups with 1 to 20 carbon atoms.

[0068] As a straight-chain or branched alkylene group having 1 to 20 carbon atoms, an alkylene group having 1 to 12 carbon atoms is preferred, and an alkylene group having 1 to 10 carbon atoms is more preferred. Examples of preferred alkylene groups include methylene, ethylene, propylene, butylene, pentylene, and hexylene.

[0069] As a straight-chain or branched alkenyl group with 1 to 20 carbon atoms, an alkenyl group with 2 to 10 carbon atoms is preferred, and an alkenyl group with 2 to 4 carbon atoms is more preferred, for example, vinylidene.

[0070] As a straight-chain or branched ynyl group with 1 to 20 carbon atoms, an ynyl group with 2 to 10 carbon atoms is preferred, and an ynyl group with 2 to 4 carbon atoms is more preferred, for example, an ethynyl group.

[0071] Furthermore, in the above formula (BQ-3), L 3 and L 4each independently represents a monovalent organic group.

[0072] Here, as the monovalent organic group, for example, the substituents described in the above-mentioned substituent group A can be cited, of which, an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, a cyano group, and a carboxyl group, etc. can be preferably cited.

[0073] The alkyl group can be linear, branched, or cyclic, but is preferably linear. The number of carbon atoms of the alkyl group is preferably from 1 to 30, more preferably from 1 to 20, and further preferably from 1 to 10.

[0074] Further, the aryl group can be monocyclic or polycyclic, but is preferably monocyclic. The number of carbon atoms of the aryl group is preferably from 6 to 25, and more preferably from 6 to 10.

[0075] Further, the heteroaryl group can be monocyclic or polycyclic. The number of heteroatoms constituting the heteroaryl group is preferably from 1 to 3. The heteroatoms constituting the heteroaryl group are preferably a nitrogen atom, a sulfur atom, and an oxygen atom. The number of carbon atoms of the heteroaryl group is preferably from 6 to 18, and more preferably from 6 to 12.

[0076] Further, the alkyl group, the aryl group, and the heteroaryl group can be unsubstituted or can have a substituent. As the substituent, the substituents described in the above-mentioned substituent group A can be cited, of which, an alkyl group, an alkoxy group, an alkoxycarbonyl group, an alkylcarbonyloxy group, or a halogen atom is preferable.

[0077] Further, in the above-mentioned formula (BQ-3), at least one of L 3 and L 4 may be a polymerizable group.

[0078] Here, the polymerizable group is not particularly limited, but is preferably a radical polymerizable or cationic polymerizable polymerizable group.

[0079] As the radical polymerizable group, a publicly known radical polymerizable group can be used, and as a preferable radical polymerizable group, an acryloyloxy group or a methacryloyloxy group can be cited. It is known that in this case, the polymerization speed of the acryloyloxy group is fast, and from the viewpoint of improving productivity, the acryloyloxy group is preferable, and the methacryloyloxy group can also be used as a polymerizable group.

[0080] As the cationic polymerizable group, a publicly known cationic polymerizable group can be used, and specifically, an alicyclic ether group, a cyclic acetal group, a cyclic lactone group, a cyclic sulfide group, a spiro ortho ester group, and a vinyloxy group, etc. can be cited. 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.

[0081] As examples of particularly preferable polymerizable groups, polymerizable groups represented by any one of the following formulas (P-1) to (P-20) can be cited.

[0082] [Chemical Formula 4] In the formulae (BQ-4) to (BQ-5), 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.

[0083] In the formulae (BQ-4) to (BQ-5), Ay represents a hydrogen atom, an alkyl group having 1 to 12 carbon atoms which can have a substituent, or 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.

[0084] The aromatic ring in Ax and Ay can have a substituent, or Ax and Ay can be bonded to form a ring.

[0085] Q represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms which can have a substituent. 3

[0086] As Ax and Ay, the groups described in

[0039] to

[0095] of International Publication No. 2014 / 010325 can be mentioned.

[0087] As 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, an n-butyl group, an isobutyl group, a sec-butyl group, a t-butyl group, an n-pentyl group, an n-hexyl group, or the like can be mentioned as the alkyl group having 1 to 6 carbon atoms represented by Q, and as the substituent, the substituents described in the above-mentioned substituent group A can be mentioned, of which an alkyl group, an alkoxy group, an alkoxycarbonyl group, an alkylcarbonyloxy group, or a halogen atom is preferred.

[0088] In the present application, Ar 1 is preferably an aromatic ring represented by the above-mentioned formula (BQ-1) or (BQ-2).

[0089] As the specific compound A, the specific compounds (A-1) to (A-12) represented by the following formulae are preferably mentioned.

[0090] [Chemical Formula 5] [LIQUID CRYSTAL COMPOUND] The liquid crystal compound contained in the liquid crystal composition of the present application is not particularly limited, and a conventionally known liquid crystal compound can be used.​

[0091] Generally, liquid crystal compounds can be classified into a rod type and a disc type according to their shape. Further, there are low molecular and high molecular types, respectively. The high molecular generally refers to a high molecule having a polymerization degree of 100 or more (High Molecular Physics · Phase Transition Dynamics, Masao Doi, p. 2, Gakushu-no-Tomo, 1992).

[0092] In the present application, any liquid crystal compound can be used, but a rod-like liquid crystal compound or a disc-like 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 disc-like liquid crystal compounds, or a mixture of a rod-like liquid crystal compound and a disc-like liquid crystal compound can also be used.

[0093] As the rod-like liquid crystal compound, for example, a compound described in Technical Solution 1 of Japanese Patent Application Laid-Open No. 11-513019 or

[0026] to

[0098] of Japanese Patent Application Laid-Open No. 2005-289980 can be preferably used, and as the disc-like liquid crystal compound, for example, a compound described in

[0020] to

[0067] of Japanese Patent Application Laid-Open No. 2007-108732 or

[0013] to

[0108] of Japanese Patent Application Laid-Open No. 2010-244038 can be preferably used, but is not limited to these.

[0094] In the present application, the above liquid crystal compound preferably has a polymerizable group, and more preferably has two or more polymerizable groups, from the viewpoint of improving the durability of the liquid crystal cured layer.

[0095] Here, as the polymerizable group, a polymerizable group represented by any one of the above formulae (P-1) to (P-20) is preferably selected.

[0096] Further, in the present application, the above liquid crystal compound is preferably a compound represented by the following formula (B), from the viewpoint of the alignment property of the liquid crystal cured layer becoming better.

[0097] L 1 -SP 1 -D 5 - (A 1 ) a1 -D 3 - (G 1 ) g1 -D 1 -Ar 2 -D 2 - (G 2 ) g2 -D 4 - (A 2 ) a2 -D 6 -SP 2 -L2 (B) In the above formula (B), a1, a2, g1, and g2 each independently represent 0 or 1. Of these, at least one of a1 and g1 represents 1, and at least one of a2 and g2 represents 1.

[0098] and D 1 , D 2 , D 3 , D 4 , D 5 , and D 6 each independently represent 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 a combination of two or more thereof, R 1 ~ R 5 each independently represent a hydrogen atom, a fluorine atom, or an alkyl group having 1 to 12 carbon atoms.

[0099] and G 1 and G 2 each independently represent an aromatic ring having 6 to 20 carbon atoms which can have a substituent or a divalent alicyclic hydrocarbon group having 5 to 20 carbon atoms which can have a substituent, and one or more -CH2- groups in the alicyclic hydrocarbon group can be substituted with -O-, -S-, or -NH-.

[0100] and A 1 and A 2 each independently represent an aromatic ring having 6 to 20 carbon atoms which can have a substituent or a divalent alicyclic hydrocarbon group having 5 to 20 carbon atoms which can have a substituent, and one or more -CH2- groups in the alicyclic hydrocarbon group can be substituted with -O-, -S-, or -NH-.

[0101] and SP 1 and SP 2 each independently represent a single bond or a divalent aliphatic hydrocarbon group having 1 to 20 carbon atoms, wherein one or more -CH2- groups in the aliphatic hydrocarbon group can be substituted with -O-, -S-, -NH-, -N(Q)-, or -CO-. Q represents a substituent.

[0102] and 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. Of these, Ar 2In the case of an aromatic ring represented by the following formula (Ar-3), L 1 and L 2 and L in the following formula (Ar-3) 3 and L 4 At least one of them represents a polymerizable group.

[0103] Furthermore, Ar 2 It represents any aromatic ring selected from the group consisting of groups represented by the formulas (Ar-1) to (Ar-7) described later.

[0104] In the above formula (B), considering that the liquid crystal composition of the present invention can easily display a smectic liquid crystal state, a1, a2, g1 and g2 are preferably all 1.

[0105] Furthermore, considering that the durability of the liquid crystal curing layer is improved, it is preferable that a1 and a2 are both 0 and g1 and g2 are both 1.

[0106] In the above formula (B), as D 1 D 2 D 3 D 4 D 5 and D 6 The divalent linking group represented in one manner, for example, can be exemplified by Ar in the above formula (A). 1 The D in the above formula (BQ-3) is represented in one way. 7 and D 8 The same group as the group described in the text.

[0107] In the above formula (B), as G 1 and G 2 The aromatic ring with 6 to 20 carbon atoms represented in one manner can include, for example, aromatic hydrocarbon rings such as benzene ring, naphthalene ring, anthracene ring, and 1,10-phenanthroline ring; and aromatic heterocycles such as furan ring, pyrrole ring, thiophene ring, pyridine ring, thiazole ring, and benzothiazole ring. Among these, a benzene ring (e.g., 1,4-phenyl ring) is preferred.

[0108] In the above formula (B), as G 1 and G 2 The alicyclic hydrocarbon group with 5 to 20 carbon atoms, represented by one of the methods, is preferably a 5-membered or 6-membered ring. Furthermore, the alicyclic hydrocarbon group can be saturated or unsaturated, but a saturated alicyclic hydrocarbon group is preferred. As G... 1 and G 2 The divalent alicyclic hydrocarbon group represented can be referred to, for example, the description in paragraph

[0078] of Japanese Patent Application Publication No. 2012-21068, the contents of which are incorporated herein by reference.

[0109] In the present application, from the reason that the durability of the liquid crystal cured layer produced becomes more excellent, G 1 and G 2 is preferably a cycloalkane ring.

[0110] As the cycloalkane ring, specifically, for example, a cyclohexane ring, a cycloheptane ring, a cyclooctane ring, a cyclododecane ring, a cyclodocosane ring, or the like can be mentioned.

[0111] Among these, a cyclohexane ring is preferred, a 1,4-cyclohexylene group is more preferred, and a trans-1,4-cyclohexylene group is further preferred.

[0112] In the above formula (B), as for G 1 and G 2 , as the substituents that the aromatic ring having 6 to 20 carbon atoms or the divalent alicyclic hydrocarbon group having 5 to 20 carbon atoms can have, the substituents described in the above-mentioned substituent group A can be mentioned, of which an alkyl group, an alkoxy group, an alkoxycarbonyl group, an alkylcarbonyloxy group, or a halogen atom is preferred.

[0113] In the above formula (B), as the aromatic ring having 6 or more to 20 carbon atoms represented as one mode of A 1 and A 2 , the same groups as the aromatic rings explained in G 1 and G 2 in the above formula (B) can be mentioned.

[0114] In the above formula (B), as the divalent alicyclic hydrocarbon group having 5 to 20 carbon atoms represented as one mode of A 1 and A 2 , the same groups as the alicyclic hydrocarbon groups explained in G 1 and G 2 in the above formula (B) can be mentioned.

[0115] In addition, as the substituents that A 1 and A 2 can have, the same groups as the substituents that G 1 and G 2 in the above formula (B) can have can be mentioned.

[0116] In the above formula (B), as the divalent aliphatic hydrocarbon group having 1 to 20 carbon atoms represented as one mode of SP 1 and SP 2 , for example, a linear or branched alkylene group having 1 to 20 carbon atoms, a linear or branched alkenylene group having 1 to 20 carbon atoms, a linear or branched alkynylene group having 1 to 20 carbon atoms, or the like can be mentioned.

[0117] As the linear or branched alkylene group having 1 to 20 carbon atoms, an alkylene group having 1 to 12 carbon atoms is preferable, and an alkylene group having 1 to 10 carbon atoms is more preferable, for example, methylene, ethylene, propylene, butylene, pentylene, hexylene, and the like are preferably selected.

[0118] As the linear or branched alkenylene group having 1 to 20 carbon atoms, an alkenylene group having 2 to 10 carbon atoms is preferable, and an alkenylene group having 2 to 4 carbon atoms is more preferable, for example, vinylene and the like are preferably selected.

[0119] As the linear or branched alkynylene group having 1 to 20 carbon atoms, an alkynylene group having 2 to 10 carbon atoms is preferable, and an alkynylene group having 2 to 4 carbon atoms is more preferable, for example, ethynylene and the like are preferably selected.

[0120] Further, as described above, one or more of -CH2- constituting the aliphatic hydrocarbon group can be substituted with -0-, -S-, -NH-, -N(Q)-, or -CO-, and as the substituent represented by Q, the substituents described in the above-mentioned Substituent Group A can be cited, of which, alkyl group, alkoxy group, alkoxycarbonyl group, alkylcarbonyloxy group, or halogen atom is preferable.

[0121] In the above-mentioned formula (B), as the monovalent organic group represented by L 1 and L 2 , the same groups as those described in L 1 and L 3 in the above-mentioned formula (BQ-3) represented by one of the modes of Ar 4 in the above-mentioned formula (A) can be cited.

[0122] Further, as the polymerizable group represented by at least one of L 1 and L 2 , the polymerizable groups represented by any one of the above-mentioned formulae (P-1) to (P-20) are preferably selected.

[0123] In the above-mentioned formula (B), as described above, Ar 2 represents any one aromatic ring selected from the group consisting of the groups represented by the following formulae (Ar-1) to (Ar-7). Further, in the following formulae (Ar-1) to (Ar-7), represents the bonding position to D 1 or D 2 in the above-mentioned formula (B).

[0124] [Chemical Formula 6] Here, each symbol in the above-mentioned formulae (Ar-1) to (Ar-7) respectively corresponds to Ar 1Each symbol in the above formulae (BQ-1) to (BQ-5) represented is the same.

[0125] As the above liquid crystal compound, for example, a compound represented by general formula (1) (particularly, the compounds described in

[0067] to

[0073] in Japanese Patent Application Publication No. 2010-084032), a compound represented by general formula (II) (particularly, the compounds described in

[0036] to

[0043] in Japanese Patent Application Publication No. 2016-053709), and a compound represented by general formula (1) (particularly, the compounds described in

[0043] to

[0055] in Japanese Patent Application Publication No. 2016-081035) described in Japanese Patent Application Publication No. 2010-084032,

[0025] to

[0056] in International Publication No. 2021 / 060427 can be mentioned.

[0126] Among these, as the liquid crystal compound, a liquid crystal compound (B-1) to (B-14) represented by the following formula is preferably selected.

[0127] [Chemical Formula 7] In the present application, from the reason why the alignment property of the liquid crystal cured layer becomes better, the content of the compound represented by the above formula (A) is preferably 18% by mass or less, more preferably 5 to 18% by mass, with respect to the total mass of the compound represented by the above formula (A) and the above liquid crystal compound (particularly, the compound represented by the above formula (B)).

[0128] In the present application, from the reason why the alignment property of the liquid crystal cured layer becomes better, with respect to the structure of the compound represented by the above formula (A) (specific compound A) and the compound represented by the above formula (B) (liquid crystal compound), it is preferable that Ar 1 in the above formula (A) is the same structure as Ar 2 in the above formula (B).

[0129] [Other polymerizable compound] From the viewpoint of the alignment temperature and the solubility, the liquid crystal composition of the present application preferably contains, in addition to the above specific compound A and the liquid crystal compound, an other polymerizable compound having one or more polymerizable groups.

[0130] Here, the polymerizable group possessed by the other polymerizable compound is not particularly limited, and a polymerizable group represented by any one of the above formulae (P-1) to (P-20) is preferably selected.

[0131] As the other polymerizable compound, from the viewpoint of further improving the durability of the formed liquid crystal cured layer, an other polymerizable compound having 2 to 4 polymerizable groups is preferred, and an other polymerizable compound having 2 polymerizable groups is more preferred.

[0132] As such an other polymerizable compound, the compounds represented by formulae (M1), (M2), and (M3) described in

[0030] to

[0033] of Japanese Patent Application Publication No. 2014-077068 can be given, and more specifically, the specific examples described in

[0046] to

[0055] of Japanese Patent Application Publication No. 2014-077068 can be given.

[0133] 〔Polymerization initiator〕 The liquid crystal composition of the present application preferably contains a polymerization initiator.

[0134] The polymerization initiator used is preferably a photopolymerization initiator capable of initiating a polymerization reaction by ultraviolet irradiation.

[0135] As the photopolymerization initiator, for example, α-ketone compounds (described in the specification of U.S. Patent No. 2367661, U.S. Patent No. 2367670), pinacol ethers (described in the specification of U.S. Patent No. 2448828), α-hydrocarbon-substituted aromatic pinacol compounds (described in the specification of U.S. Patent No. 2722512), polynuclear quinone compounds (described in the specification of U.S. Patent No. 3046127, U.S. Patent No. 2951758), combinations of triarylimidazole dimers and p-aminophenyl ketones (described in the specification of U.S. Patent No. 3549367), acridine and phenoxazine compounds (described in Japanese Patent Application Publication No. Sho 60-105667, the specification of U.S. Patent No. 4239850), and oxadiazole compounds (described in the specification of U.S. Patent No. 4212970), acylphosphine oxide compounds (described in Japanese Patent Application Publication No. Sho 63-40799, Japanese Patent Application Publication No. Hei 5-29234, Japanese Patent Application Publication No. Hei 10-95788, Japanese Patent Application Publication No. Hei 10-29997), and the like can be given.

[0136] Further, in the present application, the polymerization initiator is also preferably an oxime-type polymerization initiator, and as specific examples thereof, the initiators described in

[0049] to

[0052] of International Publication No. 2017 / 170443 can be given.

[0137] 〔Solvent〕 From the viewpoint of the workability and the like in forming the liquid crystal cured layer, the liquid crystal composition of the present application preferably contains a solvent.

[0138] As the solvent, specifically, for example, ketones (for example, acetone, 2-butanone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, cyclopentanone, and the like), ethers (for example, dioxane, tetrahydrofuran, and the like), aliphatic hydrocarbons (for example, hexane, and the like), alicyclic hydrocarbons (for example, cyclohexane, and the like), aromatic hydrocarbons (for example, toluene, xylene, mesitylene, and the like), halogenated carbons (for example, dichloromethane, dichloroethane, dichlorobenzene, chlorotoluene, and the like), esters (for example, methyl acetate, ethyl acetate, butyl acetate, and the like), water, alcohols (for example, ethanol, isopropanol, butanol, cyclohexanol, and the like), cellosolves (for example, methyl cellosolve, ethyl cellosolve, and the like), cellosolve acetates, sulfoxides (for example, dimethyl sulfoxide, and the like), amides (for example, dimethylformamide, dimethylacetamide, and the like), and the like can be cited, and one of them can be used alone, or two or more of them can be used simultaneously.

[0139] [Leveling agent] From the viewpoint of easy orientation control, the liquid crystal composition of the present application preferably contains a leveling agent.

[0140] As such a leveling agent, from the reason that the leveling effect is high with respect to the added amount, a fluorine-based leveling agent or a silicon-based leveling agent is preferred, and from the viewpoint that bleeding (blushing, bleeding) is less likely to occur, a fluorine-based leveling agent is more preferred.

[0141] As the leveling agent, specifically, for example, the compounds described in

[0079] to

[0102] of Japanese Patent Application Publication No. 2007-069471, the compounds represented by General Formula (I) described in Japanese Patent Application Publication No. 2013-047204 (in particular, the compounds described in

[0020] to

[0032] ), the compounds represented by General Formula (I) described in Japanese Patent Application Publication No. 2012-211306 (in particular, the compounds described in

[0022] to

[0029] ), the liquid crystal alignment promoters represented by General Formula (I) described in Japanese Patent Application Publication No. 2002-129162 (in particular, the compounds described in

[0076] to

[0078] and

[0082] to

[0084] ), the compounds represented by General Formulae (I), (II), and (III) described in Japanese Patent Application Publication No. 2005-099248 (in particular, the compounds described in

[0092] to

[0096] ), and the like can be cited. In addition, the function as the alignment control agent described later can be combined.

[0142] [Alignment control agent] As needed, the liquid crystal composition of the present application can contain an alignment control agent.

[0143] By the use of the alignment control agent, in addition to uniform alignment, various alignment states such as vertical alignment, oblique alignment, mixed alignment, cholesteric alignment, and the like can be formed, and a specific alignment state can be controlled more uniformly and more precisely and realized.

[0144] As the alignment control agent that promotes uniform alignment, for example, a low-molecular alignment control agent or a high-molecular alignment control agent can be used.

[0145] As the low-molecular alignment control agent, for example, the description of

[0009] to

[0083] of Japanese Patent Application Publication No. 2002-20363,

[0111] to

[0120] of Japanese Patent Application Publication No. 2006-106662, and

[0021] to

[0029] of Japanese Patent Application Publication No. 2012-211306 can be referred to, and the contents are incorporated into the present specification.

[0146] Further, as the high-molecular alignment control agent, for example, the description of

[0021] to

[0057] of Japanese Patent Application Publication No. 2004-198511 and

[0121] to

[0167] of Japanese Patent Application Publication No. 2006-106662 can be referred to, and the contents are incorporated into the present specification.

[0147] Further, as the alignment control agent that forms or promotes vertical alignment, for example, boronic acid compounds, onium salt compounds can be given, and specifically, the compounds described in

[0023] to

[0032] of Japanese Patent Application Publication No. 2008-225281,

[0052] to

[0058] of Japanese Patent Application Publication No. 2012-208397,

[0024] to

[0055] of Japanese Patent Application Publication No. 2008-026730,

[0043] to

[0055] of Japanese Patent Application Publication No. 2016-193869, and the like can be referred to, and the contents are incorporated into the present specification.

[0148] On the other hand, as for cholesteric alignment, it can be realized by adding a chiral reagent to the polymerizable liquid crystal composition of the present application, and the direction of rotation of the cholesteric alignment can be controlled according to the chiral direction.

[0149] In addition, the pitch of the cholesteric alignment can be controlled according to the alignment restriction force of the chiral reagent.

[0150] The content of the alignment control agent, when contained, is preferably 0.01 to 10% by mass, and more preferably 0.05 to 5% by mass, with respect to the total solid content mass in the composition. If the content is within this range, a cured product that realizes the desired alignment state and has no separation, phase separation, alignment defects, and the like, and is uniform and highly transparent can be obtained.

[0151] [Other Components] The liquid crystal composition of the present application can also contain components other than the above-mentioned components, and examples thereof include surfactants, tilt angle control agents, alignment aids, plasticizers, crosslinking agents, and the like.

[0152] [benzoquinone derivative] The benzoquinone derivative of the present application is a compound represented by the above-mentioned formula (A) (specific compound A).

[0153] [liquid crystal cured layer] The liquid crystal cured layer of the present application is a liquid crystal cured layer in which the alignment state of the above-mentioned liquid crystal composition of the present application is fixed.

[0154] As a method for forming the liquid crystal cured layer, for example, a method in which the above-mentioned liquid crystal composition of the present application is made to have a desired alignment state and then fixed by polymerization, or the like, can be mentioned.

[0155] Here, the polymerization conditions are not particularly limited, and in the polymerization using light irradiation, ultraviolet rays are preferably used. The irradiation amount is preferably 10 mJ / cm 2 ~ 50 J / cm 2 , more preferably 20 mJ / cm 2 ~ 5 J / cm 2 , further preferably 30 mJ / cm 2 ~ 3 J / cm 2 , particularly preferably 50 mJ / cm 2 ~ 1000 mJ / cm 2 . Furthermore, the polymerization can be performed under heating conditions in order to promote the polymerization reaction.

[0156] In addition, the liquid crystal cured layer can be formed on any of the supports or alignment films in the optical films described later or on the polarizer in the polarizing plate described later.

[0157] As the alignment state of the liquid crystal compound in the liquid crystal cured layer of the present application, any of the horizontal alignment, vertical alignment, oblique alignment, and twisted alignment can be mentioned, and it is preferably fixed in a state in which it is horizontally aligned with respect to the main surface of the liquid crystal cured layer.

[0158] In addition, in the present specification, the "horizontal alignment" means that the main surface of the liquid crystal cured layer (or, in the case where the liquid crystal cured layer is formed on a member such as a support and an alignment film, the surface of the member) is parallel to the long axis direction of the liquid crystal compound. In addition, it is not required to be strictly parallel, and in the present specification, it means an alignment in which the angle formed between the long axis direction of the liquid crystal compound and the main surface of the liquid crystal cured layer is less than 10°.

[0159] In the liquid crystal cured layer, the angle formed between the long axis direction of the liquid crystal compound and the main surface of the liquid crystal cured layer is preferably 0 to 5°, more preferably 0 to 3°, and further preferably 0 to 2°.

[0160] The liquid crystal cured layer of the present application is preferably an optically anisotropic layer, more preferably a positive A plate or a positive C plate, further preferably a positive A plate.

[0161] Among them, the positive A plate and the positive C plate are defined as follows.

[0162] When the refractive index of the slow axis direction in the film surface (the direction of the largest refractive index in the surface) is set as nx, the refractive index of the direction orthogonal to the slow axis in the surface is set as ny, and the refractive index in the thickness direction is set as nz, the positive A plate satisfies the relationship of formula (A1), and the positive C plate satisfies the relationship of formula (C1). In addition, the positive A plate indicates that Rth is a positive value, and the positive C plate indicates that Rth is a negative value.

[0163] Formula (A1) nx > ny ≈ nz Formula (C1) nz > nx ≈ ny In addition, the above "≈" includes not only the case where both are completely the same, but also the case where both are substantially the same.

[0164] Regarding the "substantially the same", in the positive A plate, for example, the case where (ny - nz) x d (where d is the thickness of the film) is -10 to 10 nm, preferably -5 to 5 nm, is also included in "ny ≈ nz", and the case where (nx - nz) x d is -10 to 10 nm, preferably -5 to 5 nm, is also included in "nx ≈ nz". Also, in the positive C plate, for example, the case where (nx - ny) x d (where d is the thickness of the film) is 0 to 10 nm, preferably 0 to 5 nm, is also included in "nx ≈ ny".

[0165] In the case where the liquid crystal cured layer of the present application is a positive A plate, Re(550) is preferably 100 to 180 nm, more preferably 120 to 160 nm, further preferably 130 to 150 nm, and particularly preferably 130 to 145 nm, from the viewpoint of functioning as a λ / 4 plate.

[0166] Among them, the "λ / 4 plate" refers to a plate having a λ / 4 function, specifically, a plate having a function of converting linearly polarized light of a certain specific wavelength into circularly polarized light (or converting circularly polarized light into linearly polarized light).

[0167] In the case where the liquid crystal composition of the present application described above contains a dichroic substance, the liquid crystal cured layer of the present application can be used as a polarizer (absorbing anisotropic film).

[0168] [Optical film] The optical film of the present application is an optical film having the liquid crystal cured layer of the present application.

[0169] Reference Figure 1 The structure of the optical film will be described. Figure 1 is a schematic cross-sectional view showing an example of the optical film.

[0170] In addition, Figure 1 The thickness relationship and positional relationship of each layer, etc. are not necessarily consistent with the actual situation as the drawing is a schematic view, Figure 1 The support and the orientation film shown in the above embodiment are arbitrary components.

[0171] Figure 1 The optical film 10 shown in the above embodiment has, in order, a support 16, an orientation film 14, and a cured product of the liquid crystal composition of the present application, i.e., a liquid crystal cured layer 12.

[0172] Further, the liquid crystal cured layer 12 can be a laminate of two or more different liquid crystal cured layers. For example, in the case where the polarizing plate of the present application described later is used as a circular polarizing plate or the optical film of the present application is used as an optical compensation film for a liquid crystal display device of an IPS (In-Plane-Switching) mode or an FFS (Fringe-Field-Switching) mode, a laminate of a positive A plate and a positive C plate is preferable.

[0173] Further, the liquid crystal cured layer can be peeled off from the support and used alone as an optical film.

[0174] Hereinafter, various components used in the optical film will be described in detail.

[0175] 〔Liquid crystal cured layer〕 The liquid crystal cured layer possessed by the optical film of the present application is the liquid crystal cured layer of the present application described above.

[0176] In the optical film, the thickness of the liquid crystal cured layer is not particularly limited, and is preferably 0.1 to 10 μm, and more preferably 0.5 to 5 μm.

[0177] 〔Support〕 As described above, the optical film can have a support as a base material for forming the liquid crystal cured layer.

[0178] Such a support is preferably transparent. Specifically, the light transmittance is preferably 80% or more.

[0179] As such a support, for example, a glass substrate and a polymer film can be given. As a material of the polymer film, a cellulose-based polymer; an acrylic-based polymer having an acrylate polymer such as polymethyl methacrylate and a polymer containing a lactone ring; a thermoplastic norbornene-based polymer; a polycarbonate-based polymer; a polyester-based polymer such as polyethylene terephthalate and polyethylene naphthalate; a styrene-based polymer such as polystyrene and acrylonitrile-styrene copolymer (AS resin); a polyolefin-based polymer such as polyethylene, polypropylene, and ethylene-propylene copolymer; a vinyl chloride-based polymer; an amide-based polymer such as nylon and aromatic polyamide; an imide-based polymer; a sulfone-based polymer; a polyether sulfone-based polymer; a polyether ether ketone-based polymer; a polyphenylene sulfide-based polymer; a vinylidene chloride-based polymer; a vinyl alcohol-based polymer; a vinyl butyral-based polymer; an aryl ester-based polymer; a polyformaldehyde-based polymer; an epoxy-based polymer; and a polymer obtained by mixing these polymers can be given.

[0180] Also, a polarizer described later can be used as such a support.

[0181] The thickness of the above support is not particularly limited, but is preferably 5 to 60 μm, and more preferably 5 to 40 μm.

[0182] [Alignment film] In the optical film, the liquid crystal cured layer is preferably formed on the surface of an alignment film (particularly, a photo-alignment film described later). In the case where the optical film has the above-described arbitrary support, the alignment film can be interposed between the support and the liquid crystal cured layer. Also, the above-described support can be used as the alignment film.

[0183] The alignment film can be any film as long as it has a function of horizontally aligning the polymerizable liquid crystal compound contained in the composition.

[0184] The alignment film generally uses a polymer as a main component. As a polymer material for the alignment film, many are described in many documents, and many commercial products are available.

[0185] As the polymer material for the alignment film, polyvinyl alcohol, polyimide, or any derivative thereof is preferable, and modified or unmodified polyvinyl alcohol is more preferable.

[0186] As the alignment film that the optical film can have, for example, the alignment film described in International Publication No. 01 / 88574, page 43, line 24 to page 49, line 8; the alignment film composed of modified polyvinyl alcohol described in Japanese Patent No. 3907735,

[0071] to

[0095] , and the liquid crystal alignment film formed by a liquid crystal alignment agent described in Japanese Patent Application Publication No. 2012-155308 can be given.

[0187] The object is not in contact with the surface of the alignment film when the alignment film is formed, and thus the surface state can be prevented from deteriorating, and thus it is preferable to use a photoalignment film as the alignment film.

[0188] There is no particular limitation on the photoalignment film, but an alignment film formed of a polymer such as a polyamide compound and a polyimide compound described in

[0024] to

[0043] of International Publication No. 2005 / 096041; a liquid crystal alignment film formed of a liquid crystal aligning agent having a photoalignment group described in Japanese Patent Application Publication No. 2012-155308; and LPP-JP265CP manufactured by Rolic Technologies Co., Ltd., and the like can be used.

[0189] The thickness of the alignment film is not particularly limited, but from the viewpoint of forming a liquid crystal cured layer having a uniform film thickness while mitigating surface irregularities that can exist on the support, it is preferably 0.01 to 10 μm, more preferably 0.01 to 1 μm, and further preferably 0.01 to 0.5 μm.

[0190] [Other liquid crystal cured layer] In the optical film, the liquid crystal cured layer is preferably formed on the surface of the other liquid crystal cured layer.

[0191] Here, as the other liquid crystal cured layer, for example, a liquid crystal cured layer in which the alignment state of a composition obtained by removing a specific compound A from the above-described liquid crystal composition of the present application is fixed can be given. Specifically, a liquid crystal cured layer in which the alignment state of a composition containing the above-described liquid crystal compound, a polymerization initiator, a leveling agent, a solvent, and the like is fixed can be given.

[0192] [UV absorber] In consideration of the influence of external light (particularly, ultraviolet rays), the optical film preferably contains a UV absorber.

[0193] The UV absorber can be contained in the liquid crystal cured layer, or can be contained in a member other than the liquid crystal cured layer that constitutes the optical film. As the member other than the liquid crystal cured layer, for example, a support can be preferably given.

[0194] As the UV absorber, any of the conventionally known UV absorbers that can exhibit UV absorbability can be used. Among such UV absorbers, from the viewpoint of high UV absorbability and obtaining UV absorbency (UV cutoff ability) used in an image display device, a benzotriazole-based or a hydroxyphenyl triazine-based UV absorber is preferable.

[0195] Further, in order to expand the absorption range of ultraviolet rays, it is also preferable to be able to use two or more kinds of UV absorbers having different maximum absorption wavelengths in combination.

[0196] As the ultraviolet absorber, for example, a compound described in

[0258] to

[0259] of Japanese Patent Application Laid-Open No. 2012-18395 and a compound described in

[0055] to

[0105] of Japanese Patent Application Laid-Open No. 2007-72163, and the like can be given.

[0197] Further, as a commercial product, Tinuvin 400, Tinuvin 405, Tinuvin 460, Tinuvin 477, Tinuvin 479, and Tinuvin 1577 (all manufactured by BASF Corporation), and the like can be used.

[0198] [Polarizing plate] The polarizing plate of the present application has the optical film of the present application described above and a polarizer.

[0199] Further, in the case where the liquid crystal cured layer of the present application described above is a λ / 4 plate (positive A plate), the polarizing plate of the present application can be used as a circularly polarizing plate.

[0200] Further, in the case where the liquid crystal cured layer of the present application described above is a λ / 4 plate (positive A plate), the angle that the slow axis of the λ / 4 plate makes with the absorption axis of the polarizer described later is preferably 30 to 60°, more preferably 40 to 50°, further preferably 42 to 48°, and particularly preferably 45°.

[0201] Here, the "slow axis" of the λ / 4 plate indicates the direction in which the refractive index in the plane of the λ / 4 plate becomes the largest, and the "absorption axis" of the polarizer indicates the direction in which the absorbance is the highest.

[0202] Further, the polarizing plate of the present application can also be used as an optical compensation film for a liquid crystal display device of an IPS mode or an FFS mode.

[0203] In the case where the polarizing plate of the present application is used as an optical compensation film for a liquid crystal display device of an IPS mode or an FFS mode, the liquid crystal cured layer of the present application described above can be used as a plate of at least one of a laminate of a positive A plate and a positive C plate, and preferably a positive A plate. In this case, it is preferable that the angle that the slow axis of the positive A plate makes with the absorption axis of the polarizer described later be orthogonal or parallel, and specifically, more preferably, the angle that the slow axis of the positive A plate makes with the absorption axis of the polarizer described later be 0 to 5° or 85 to 95°.

[0204] Further, in the case where the polarizing plate of the present application has a polarizer, a positive C plate, and a positive A plate laminated in this order, it is further preferable that the angle that the slow axis of the positive A plate makes with the absorption axis of the polarizer be parallel.

[0205] Likewise, in the case where the polarizing plate of the present application has a polarizer, a positive A plate, and a positive C plate laminated in this order, it is further preferable that the angle that the slow axis of the positive A plate makes with the absorption axis of the polarizer be orthogonal. Likewise, in the case where the polarizing plate of the present application has a polarizer, a positive A plate, and a positive C plate laminated in this order, it is further preferable that the angle that the slow axis of the positive A plate makes with the absorption axis of the polarizer be orthogonal.

[0206] In the case where the polarizing plate of the present application is used in the liquid crystal display device described later, it is preferable that the angle formed by the slow axis of the liquid crystal cured layer and the absorption axis of the polarizer described later be parallel or orthogonal.

[0207] In addition, in the present specification, "parallel" means not requiring strict parallelism and an angle formed by one and the other being less than 10°. Also, in the present specification, "orthogonal" means not requiring strict orthogonality and an angle formed by one and the other being more than 80° and less than 100°.

[0208] 〔Polarizer〕 As for the polarizer possessed by the polarizing plate of the present application, as long as it is a member having a function of converting light into a specific linearly polarized light, it is not particularly limited and can utilize the absorption type polarizer and the reflection type polarizer which have been known heretofore.

[0209] As the absorption type polarizer, an iodine type polarizer, a dye type polarizer utilizing a dichroic dye, a polyene type polarizer and the like can be used. The iodine type polarizer and the dye type polarizer have a coating type polarizer and a stretched type polarizer, and although both can be applied, a polarizer produced by adsorbing iodine or a dichroic dye to polyvinyl alcohol and stretching it is preferable.

[0210] Also, as a method of obtaining a polarizer by performing stretching and dyeing in a state where a laminated film having a polyvinyl alcohol layer formed on a substrate is implemented, Japanese Patent No. 5048120, Japanese Patent No. 5143918, Japanese Patent No. 4691205, Japanese Patent No. 4751481, Japanese Patent No. 4751486 can be cited, and it is also preferable to utilize the known technology related to these polarizers.

[0211] As the reflection type polarizer, a polarizer obtained by laminating films different in birefringence, a wire grid type polarizer, a polarizer obtained by combining a cholesteric liquid crystal having a selective reflection region and a 1 / 4 wave plate, and the like can be used.

[0212] Among them, from the aspect that adhesion is more excellent, a polarizer containing a polyvinyl alcohol-based resin (a polymer containing -CH2-CHOH- as a repeating unit. In particular, at least one selected from the group consisting of polyvinyl alcohol and ethylene-vinyl alcohol copolymer) is preferable.

[0213] In the present application, the thickness of the polarizer is not particularly limited, but it is preferably 3 μm to 60 μm, more preferably 5 μm to 30 μm, and further preferably 5 μm to 15 μm.

[0214] 〔Adhesive layer〕 The polarizing plate of the present application can be provided with an adhesive layer between the liquid crystal cured layer in the optical film of the present application and the polarizer.

[0215] As the adhesive layer for laminating the liquid crystal cured layer and the polarizer, for example, a substance having a ratio of storage elastic modulus G' to loss elastic modulus G" (tan δ = G" / G') measured by a dynamic viscoelasticity measuring device of 0.001 to 1.5, so-called adhesive and easily-creepable substance, and the like are included. As the adhesive which can be used in the present application, for example, a polyvinyl alcohol-based adhesive can be given, but is not limited thereto.

[0216] [Image display device] The image display device of the present application is an image display device having the optical film of the present application or the polarizing plate of the present application.

[0217] The display element used in the image display device is not particularly limited, and for example, a liquid crystal cell, an organic electroluminescence (hereinafter, abbreviated as "EL") display panel, a plasma display panel, and the like can be given. Among these, a liquid crystal cell and an organic EL display panel are preferred, and a liquid crystal cell is more preferred.

[0218] That is, as the image display device, a liquid crystal display device using a liquid crystal cell as the display element or an organic EL display device using an organic EL display panel as the display element is preferred, and a liquid crystal display device is more preferred.

[0219] [Image display device] The liquid crystal display device as an example of the image display device is a liquid crystal display device having the above-mentioned polarizing plate and liquid crystal cell.

[0220] Further, among the polarizing plates provided on both sides of the liquid crystal cell, the above-mentioned polarizing plate is preferably used as the front-side polarizing plate, and the above-mentioned polarizing plate is more preferably used as the front-side and rear-side polarizing plates.

[0221] Hereinafter, the liquid crystal cell constituting the liquid crystal display device will be described in detail.

[0222] < Liquid crystal cell > The liquid crystal cell used in the liquid crystal display device is preferably a VA (Vertical Alignment) mode, an OCB (Optically Compensated Bend) mode, an IPS (In-Plane-Switching) mode, an FFS (Fringe-Field-Switching) mode, or a TN (Twisted Nematic) mode, but is not limited thereto.

[0223] In a TN mode liquid crystal cell, rod-like liquid crystal molecules are oriented substantially horizontally in the absence of an applied voltage, and are twisted and oriented by 60 to 120°. The TN mode liquid crystal cell is most commonly used as a color TFT liquid crystal display device, and is described in many documents.

[0224] In a VA mode liquid crystal cell, rod-like liquid crystal molecules are oriented substantially vertically in the absence of an applied voltage. In the VA mode liquid crystal cell, in addition to a narrow sense VA mode liquid crystal cell (described in Japanese Patent Laid-Open No. 2-176625) which includes (1) a liquid crystal cell in which rod-like liquid crystal molecules are oriented substantially vertically in the absence of an applied voltage, and are oriented substantially horizontally in the presence of an applied voltage, a liquid crystal cell of (2) a MVA mode (described in SID 97, Digest of tech. Papers 28 (1997) 845) in which the VA mode is multi-domainized in order to widen the viewing angle, (3) a liquid crystal cell of an n-ASM mode (described in Proceedings of the Japan Liquid Crystal Discussion Meeting 58-59 (1998)) in which rod-like liquid crystal molecules are oriented substantially vertically in the absence of an applied voltage, and are twisted and oriented in a multi-domain manner in the presence of an applied voltage, and (4) a liquid crystal cell of a SURVIVAL mode (published in LCD International 98) are included. Further, the VA mode liquid crystal cell can be any one of a PVA (Patterned Vertical Alignment) type, an optical alignment type, and a PSA (Polymer-Sustained Alignment) type. Details of these modes are described in detail in Japanese Patent Laid-Open No. 2006-215326 and Japanese Patent Kokai No. 2008-538819.

[0225] In an IPS mode liquid crystal cell, rod-like liquid crystal molecules are oriented substantially parallel with respect to a substrate, and the liquid crystal molecules are planarly responsive by applying an electric field parallel with the substrate plane. In the IPS mode, black display is obtained in the absence of an applied electric field, and the absorption axes of the upper and lower pair of polarizing plates are orthogonal to each other. In Japanese Patent Laid-Open No. 10-54982, Japanese Patent Laid-Open No. 11-202323, Japanese Patent Laid-Open No. 9-292522, Japanese Patent Laid-Open No. 11-133408, Japanese Patent Laid-Open No. 11-305217, Japanese Patent Laid-Open No. 10-307291, and the like, a method of using an optical compensation sheet to reduce light leakage in the black display in the oblique direction and to improve the viewing angle is disclosed.

[0226] [Organic EL Display Device] As an example of the image display device, for example, there can be mentioned a mode in which a polarizer, a λ / 4 plate (positive A plate) composed of the liquid crystal cured layer described above, and an organic EL display panel are provided in this order from the visual recognition side.

[0227] Further, the organic EL display panel is a display panel composed of an organic EL element in which an organic light emitting layer (organic electroluminescent layer) is interposed between electrodes (cathode and anode). The structure of the organic EL display panel is not particularly limited, and a publicly known structure can be adopted.

[0228] Example Hereinafter, the present application will be further explained in detail according to examples. The materials, amounts, proportions, contents of treatment, steps of treatment, and the like shown in the following examples can be appropriately changed as long as the purpose of the present application is not deviated. Therefore, the scope of the present application should not be interpreted limitatively by the examples shown below.

[0229] [Synthesis of specific compound (A-1)] According to the synthesis method described in Japanese Patent Application Publication No. 2012-97078, specific compound (A-1) was synthesized by the following scheme.

[0230] [Chemical Formula 8] Specifically, 8 g of compound (A-1-3), 4.6 g of Lawesson's reagent, and 60 g of toluene were added to a 200 mL three-necked flask, heated to 80°C, and reacted for 12 hours.

[0231] After cooling to room temperature, a crude product containing compound (A-1-2) was obtained.

[0232] Then, the crude product containing compound (A-1-2), 5.9 g of NaOH, and 125 g of water were mixed and cooled under ice cooling. Then, an aqueous solution containing 22 g of potassium ferrocyanide was added under ice cooling, and reacted. After reacting at 60°C for 12 hours, the precipitated solid was suction filtered. The filtered solid was washed with water and heptane, and crystallized with toluene, thereby obtaining a yellow solid (A-1-1).

[0233] Next, to a 100 mL three-necked flask, aluminum chloride 2.45 g, toluene 25 mL were added, and stirring was performed under nitrogen. To this, yellow solid (A-1-1) 2.5 g was added, and after stirring for 3 hours at room temperature, further stirring was performed for 5 hours at 60°C. Then, after natural cooling to room temperature, 1N hydrochloric acid was added and stirred for 30 minutes. The precipitated solid (a mixture of (A-1) and (A-1-O)) was suction-filtered, suspended with 1N hydrochloric acid, and further washed with pure water 25 mL. The obtained solid was oxidized by a general method (Tetrahedron letters 46.26 (2005): 4449-4451.) using silver oxide, and 1.1 g of the specific compound (A-1) was obtained.

[0234] The following shows the results of mass spectrometry (MS) of the obtained specific compound (A-1).

[0235] m / z: 309.05 (100.0%), 310.05 (19.4%), 311.04 (4.5%), 311.05 (2.4%), 312.05 (1.0%) [Synthesis of other specific compounds] As for the specific compounds other than the specific compound (A-1), too, the starting phenol was oxidized in the same manner as described above to synthesize.

[0236] [Example 1] A liquid crystal composition 1 of the following composition was prepared.

[0237] --------------------------------- Liquid crystal composition 1 --------------------------------- • The following liquid crystal compound (B-1) 222.5 parts by mass • The following specific compound (A-1) 47.0 parts by mass • The following polymerizable compound (D-1) 3.0 parts by mass • The following polymerization initiator S1 1.5 parts by mass • The following leveling agent P1 0.1 parts by mass • Cyclopentanone 92.5 parts by mass • Methyl ethyl ketone 64.2 parts by mass --------------------------------- Liquid crystal compound (B-1) [Chemical Formula 9] Specific compound (A-1) [Chemical Formula 10] Polymerizable compound (D-1) [Chemical Formula 11] Polymerization initiator S1 [Chemical Formula 12] Leveling agent P1 (a, b, c in the following respectively represent the content ratio (mass%) of each repeating unit with respect to all repeating units, and a = 44.8, b = 50.3, c = 4.9 are indicated.) [Chemical Formula 13] [Example 2] A liquid crystal composition 2 of the following composition was prepared.

[0238] --------------------------------- Liquid crystal composition 2 --------------------------------- • The following liquid crystal compound (B-2) 222.5 parts by mass • The following specific compound (A-2) 47.0 parts by mass • The above polymerizable compound (D-1) 3.0 parts by mass • The above polymerization initiator S1 1.5 parts by mass • The above leveling agent P1 0.1 parts by mass • Cyclopentanone 92.5 parts by mass • Methyl ethyl ketone 64.2 parts by mass --------------------------------- Liquid crystal compound (B-2) [Chemical Formula 14] Specific compound (A-2) [Chemical Formula 15] [Example 3] A liquid crystal composition 3 of the following composition was prepared.

[0239] --------------------------------- Liquid crystal composition 3 --------------------------------- • The following liquid crystal compound (B-3) 222.5 parts by mass • The following specific compound (A-3) 47.0 parts by mass • The above polymeric compound (D-1) 3.0 parts by mass • The above polymerization initiator S1 1.5 parts by mass • The above leveling agent P1 0.1 parts by mass • Cyclopentanone 92.5 parts by mass • Methyl ethyl ketone 64.2 parts by mass --------------------------------- Liquid crystal compound (B-3) [Chemical Formula 16] Specific compound (A-3) [Chemical Formula 17] [Example 4] A liquid crystal composition 4 of the following composition was prepared.

[0240] --------------------------------- Liquid crystal composition 4 --------------------------------- • The above liquid crystal compound (B-1) 222.5 parts by mass • The above specific compound (A-1) 55.6 parts by mass • The above polymeric compound (D-1) 3.0 parts by mass • The above polymerization initiator S1 1.5 parts by mass • The above leveling agent P1 0.1 parts by mass • Cyclopentanone 92.5 parts by mass • Methyl ethyl ketone 64.2 parts by mass --------------------------------- [Example 5] A liquid crystal composition 5 of the following composition was prepared.

[0241] --------------------------------- Liquid crystal composition 5 --------------------------------- • The above liquid crystal compound (B-2) 222.5 parts by mass • The above specific compound (A-1) 47.0 parts by mass • The above polymerizable compound (D-1) 3.0 parts by mass • The above polymerization initiator S1 1.5 parts by mass • The above leveling agent P1 0.1 parts by mass • Cyclopentanone 92.5 parts by mass • Methyl ethyl ketone 64.2 parts by mass --------------------------------- [Example 6] A liquid crystal composition 6 of the following composition was prepared.

[0242] --------------------------------- Liquid crystal composition 6 --------------------------------- • The above liquid crystal compound (B-1) 222.5 parts by mass • The above specific compound (A-2) 47.0 parts by mass • The above polymerizable compound (D-1) 3.0 parts by mass • The above polymerization initiator S1 1.5 parts by mass • The above leveling agent P1 0.1 parts by mass • Cyclopentanone 92.5 parts by mass • Methyl ethyl ketone 64.2 parts by mass --------------------------------- [Example 7] A liquid crystal composition 7 of the following composition was prepared.

[0243] --------------------------------- Liquid crystal composition 7 --------------------------------- • The above liquid crystal compound (B-5) 222.5 parts by mass • the specific compound (A-5) described below 47.0 parts by mass • the above-described polymerizable compound (D-1) 3.0 parts by mass • the above-described polymerization initiator S1 1.5 parts by mass • the above-described leveling agent P1 0.1 parts by mass • cyclopentanone 92.5 parts by mass • methyl ethyl ketone 64.2 parts by mass --------------------------------- Liquid crystal compound (B-5) [Chemical Formula 18] Specific compound (A-5) [Chemical Formula 19] [Example 8] A liquid crystal composition 8 was prepared with the following composition.

[0244] --------------------------------- Liquid crystal composition 8 --------------------------------- • the liquid crystal compound (B-6) described below 222.5 parts by mass • the specific compound (A-6) described below 47.0 parts by mass • the above-described polymerizable compound (D-1) 3.0 parts by mass • the above-described polymerization initiator S1 1.5 parts by mass • the above-described leveling agent P1 0.1 parts by mass • cyclopentanone 92.5 parts by mass • methyl ethyl ketone 64.2 parts by mass --------------------------------- Liquid crystal compound (B-6) [Chemical Formula 20] Specific compound (A-6) [Chemical Formula 21] [Example 9] A liquid crystal composition 9 was prepared with the following composition.

[0245] --------------------------------- Liquid crystal composition 9 --------------------------------- • The following liquid crystal compound (B-7) 222.5 parts by mass • The following specific compound (A-7) 47.0 parts by mass • The above polymeric compound (D-1) 3.0 parts by mass • The above polymerization initiator S1 1.5 parts by mass • The above leveling agent P1 0.1 parts by mass • Cyclopentanone 92.5 parts by mass • Methyl ethyl ketone 64.2 parts by mass --------------------------------- Liquid crystal compound (B-7) [Chemical Formula 22] Specific compound (A-7) [Chemical Formula 23] [Example 10] A liquid crystal composition 10 of the following composition was prepared.

[0246] --------------------------------- Liquid crystal composition 10 --------------------------------- • The following liquid crystal compound (B-8) 222.5 parts by mass • The following specific compound (A-8) 47.0 parts by mass • The above polymeric compound (D-1) 3.0 parts by mass • The above polymerization initiator S1 1.5 parts by mass • The above leveling agent P1 0.1 parts by mass • Cyclopentanone 92.5 parts by mass • Methyl ethyl ketone 64.2 parts by mass --------------------------------- Liquid crystal compound (B-8) [Chemical Formula 24] Specific compound (A-8) [Chemical Formula 25] [Example 11] A liquid crystal composition 11 was prepared with the following composition.

[0247] --------------------------------- Liquid crystal composition 11 --------------------------------- • The following liquid crystal compound (B-9) 222.5 parts by mass • The following specific compound (A-9) 47.0 parts by mass • The above polymeric compound (D-1) 3.0 parts by mass • The above polymerization initiator S1 1.5 parts by mass • The above leveling agent P1 0.1 parts by mass • Cyclopentanone 92.5 parts by mass • Methyl ethyl ketone 64.2 parts by mass --------------------------------- Liquid crystal compound (B-9) [Chemical Formula 26] Specific compound (A-9) [Chemical Formula 27] [Comparative Example 1] A liquid crystal composition C1 was prepared with the following composition.

[0248] --------------------------------- Liquid crystal composition C1 --------------------------------- • The above liquid crystal compound (B-1) 269.5 parts by mass • The above polymeric compound (D-1) 3.0 parts by mass • The above polymerization initiator S1 1.5 parts by mass • The above leveling agent P1 0.1 parts by mass • Cyclopentanone 92.5 parts by mass • Methyl ethyl ketone 64.2 parts by mass --------------------------------- [Comparative Example 2] A liquid crystal composition C2 of the following composition was prepared.

[0249] --------------------------------- Liquid crystal composition C2 --------------------------------- • The above liquid crystal compound (B-1) 222.5 parts by mass • ADEKA STAB LA-29 47.0 parts by mass • The above polymerizable compound (D-1) 3.0 parts by mass • The above polymerization initiator S1 1.5 parts by mass • The above leveling agent P1 0.1 parts by mass • Cyclopentanone 92.5 parts by mass • Methyl ethyl ketone 64.2 parts by mass --------------------------------- [Production of optical film] The liquid crystal composition 1 prepared in Example 1 was coated on a glass substrate with a rubbed polyimide alignment film (SE-150 manufactured by Nissan Chemical Corporation) by a spin coating method. The coated film was subjected to an alignment treatment at 200°C to form a liquid crystal layer. Then, the cooling to 135°C and orientation fixation based on ultraviolet irradiation of 1000 mJ / cm 2 formed a liquid crystal cured layer (optical anisotropic layer), thereby producing an optical film 1 for wavelength dispersion measurement.

[0250] The phase difference of the optical film 1 was measured, and it was confirmed that Re(450) / Re(550) = 0.88.

[0251] In the same manner, a liquid crystal cured layer was formed for the liquid crystal compositions prepared in Examples 2 to 11 and Comparative Examples 1 and 2, thereby producing optical films.

[0252] [Light resistance evaluation] The optical films produced were exposed to light for 100 hours using a super xenon weather meter SX75.

[0253] At this time, a protective film 1 was interposed between the optical film and the super xenon weather meter SX75, and was arranged so that light was incident from the liquid crystal cured layer.

[0254] The change in color tone of the film was determined by comparing the exposed sample with the same sample that was not exposed, and was evaluated according to the following criteria. The results are shown in Table 1 below.

[0255] <Change in color tone> A: Δb for a sample that was not exposed to the xenon weather meter ≤ 2.0 B: 2.0 < Δb for a sample that was not exposed to the xenon weather meter ≤ 4.0 C: 4.0 < Δb for a sample that was not exposed to the xenon weather meter [Orientation evaluation] Regarding the determination of orientation, an LED (Light Emitting Diode) light source, a lower polarizing plate, a liquid crystal cured layer (an optical film made from each liquid crystal composition), and an upper polarizing plate were sequentially arranged on a table so that each face became horizontal. At this time, the test sample and the upper polarizing plate were set to be rotatable. The brightness of light emitted from the light source and transmitted sequentially through the lower polarizing plate, the test sample, and the upper polarizing plate was determined from the vertical direction using a brightness meter (BM-5A (manufactured by TOPCON CORPORATION)).

[0256] At the time of determination, first, the upper polarizing plate was rotated to align at the position where the brightness was the darkest (a state of orthogonal Nicols) in the absence of the test sample. The test sample peeled from the protective film was inserted between the polarizing plates, and the test sample was rotated under orthogonal Nicols, and the brightness that became the smallest was determined. Next, the two polarizing plates of the upper polarizing plate and the lower polarizing plate were arranged in a parallel Nicols configuration, the test sample was rotated, and the brightness that became the largest was determined.

[0257] In order to remove the influence of brightness leakage caused by the upper polarizing plate and the lower polarizing plate, the value obtained by the following equation was evaluated according to the following evaluation criteria. The results are shown in Table 1 below.

[0258] Orientation = 1 / ((minimum brightness under orthogonal Nicols when the test sample was set) / (maximum brightness under parallel Nicols when the test sample was set) - (minimum brightness under orthogonal Nicols in the absence of the test sample) / (maximum brightness under parallel Nicols in the absence of the test sample)) <Evaluation criteria> A: The above orientation was 200,000 or more B: The above orientation was 100,000 or more and less than 200,000 C: The above orientation was less than 100,000 [Table 1]

[0259] From the results shown in Table 1 above, it is known that, in the case where the specific compound A is not incorporated, the light resistance is poor (Comparative Example 1).

[0260] Further, it is known that, in the case where a compound not corresponding to the compound represented by the above formula (A) is incorporated, the light resistance is improved, but the alignment property is poor (Comparative Example 2).

[0261] In contrast, it is known that, if a liquid crystal composition containing the specific compound A and a liquid crystal compound is used, a liquid crystal cured layer having both good alignment property and good light resistance can be produced (Examples 1 to 11).

[0262] In particular, from the comparison between Example 1 and Example 4, it is known that, if the content of the specific compound A is 18 mass% or less with respect to the total mass of the specific compound and the liquid crystal compound, the alignment property becomes even better.

[0263] Further, from the comparison between Example 1 and Example 5 and the comparison between Example 2 and Example 6, it is known that, with respect to the structures of the compound represented by the above formula (A) (specific compound A) and the compound represented by the above formula (B) (liquid crystal compound), if Ar 1 in the above formula (A) and Ar 2 in the above formula (B) are the same structure, the alignment property becomes even better.

[0264] Explanation of symbols 10 - optical film, 12 - liquid crystal cured layer, 14 - alignment film, 16 - support.

Claims

1. A liquid crystal composition comprising a compound represented by the following formula (A) and a liquid crystal compound, Here, in equation (A), Ar 1 It represents any aromatic ring selected from the group consisting of groups represented by the following formulas (BQ-1) to (BQ-5). Here, in equations (BQ-1) to (BQ-5), Indicates the bonding position with the oxygen atom. Q 1 Indicates N or CH, Q 2 Indicates -S-, -O-, or -N(R) 6 )-,R 6 Indicates an alkyl group having 1 to 6 hydrogen atoms or carbon atoms. Y 1 This indicates an aromatic hydrocarbon group with 6 to 12 carbon atoms that may have substituents, an aromatic heterocyclic group with 3 to 12 carbon atoms that may have substituents, or an alicyclic hydrocarbon group with 6 to 20 carbon atoms that may have substituents, wherein one or more of the -CH2- groups constituting the alicyclic hydrocarbon group may be substituted with -O-, -S-, or -NH-. Z 1 Z 2 and Z 3 Each of the following can be independently represented: a hydrogen atom, a monovalent aliphatic hydrocarbon group with 1-20 carbon atoms, a monovalent alicyclic hydrocarbon group with 3-20 carbon atoms, a monovalent aromatic hydrocarbon group with 6-20 carbon atoms, a monovalent aromatic heterocyclic group with 6-20 carbon atoms, a halogen atom, a cyano group, a nitro group, or -OR. 7 -NR 8 R 9 -SR 10 -COOR 11 or -COR 12 R 7 ~R 12 Z represents, independently, either a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. 1 and Z 2 They can bond with each other to form aromatic rings. A 3 and A 4 Each can be independently represented by a selection from -O-, -N(R) 13 The groups in the group consisting of -, -S- and -CO-, R 13 Represents a hydrogen atom or a substituent. X represents a nonmetallic atom from groups 14 to 16, where, The non-metallic atoms may be bonded with hydrogen atoms or substituents. D 7 and D 8 Each can independently represent a single bond or -CO-, -O-, -S-, -C(=S)-, -CR 1 R 2 -、-CR 3 =CR 4 -、-NR 5 -or a divalent linker formed by two or more of them, R 1 ~R 5 Each of the following can be independently represented by a hydrogen atom, a fluorine atom, or an alkyl group having 1 to 12 carbon atoms. SP 3 and SP 4 Each of the above independently represents a single bond or a divalent aliphatic hydrocarbon group having 1 to 20 carbon atoms, wherein one or more of the -CH2- groups constituting the aliphatic hydrocarbon group can be substituted by -O-, -S-, -NH-, -N(Q)-, or -CO-, where Q represents a substituent. L 3 and L 4 Each of the above can independently represent a monovalent organic group. Ax represents an organic group having 2 to 30 carbon atoms in at least one aromatic ring selected from the group consisting of aromatic hydrocarbon rings and aromatic heterocycles. Ay represents a hydrogen atom, an alkyl group having 1 to 12 carbon atoms that may have substituents, or an organic group having 2 to 30 carbon atoms that has at least one aromatic ring selected from the group consisting of aromatic hydrocarbon rings and aromatic heterocycles. The aromatic rings in Ax and Ay can have substituents, and Ax and Ay can also bond to form a ring. Q 3 It represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms that may have substituents.

2. The liquid crystal composition according to claim 1, wherein, The liquid crystal compound is a compound represented by the following formula (B). L 1 -SP 1 -D 5 -(A 1 ) a1 -D 3 -(G 1 ) g1 -D 1 -Ar 2 -D 2 -(G 2 ) g2 -D 4 -(A 2 ) a2 -D 6 -SP 2 -L 2 (B) Here, in equation (B), a1, a2, g1, and g2 each independently represent 0 or 1, wherein at least one of a1 and g1 represents 1, and at least one of a2 and g2 represents 1. D 1 D 2 D 3 D 4 D 5 and D 6 Each can independently represent a single bond or -CO-, -O-, -S-, -C(=S)-, -CR 1 R 2 -、-CR 3 =CR 4 -、-NR 5 -or a divalent linker formed by two or more of them, R 1 ~R 5 Each of the following can be independently represented by a hydrogen atom, a fluorine atom, or an alkyl group having 1 to 12 carbon atoms. G 1 and G 2 Each of these groups independently represents an aromatic ring with 6 to 20 carbon atoms that may have substituents, or a divalent alicyclic hydrocarbon group with 5 to 20 carbon atoms that may have substituents, wherein one or more of the -CH2- groups constituting the alicyclic hydrocarbon group can be substituted with -O-, -S-, or -NH-. A 1 and A 2 Each of these groups independently represents an aromatic ring with 6 to 20 carbon atoms that may have substituents, or a divalent alicyclic hydrocarbon group with 5 to 20 carbon atoms that may have substituents, wherein one or more of the -CH2- groups constituting the alicyclic hydrocarbon group can be substituted with -O-, -S-, or -NH-. SP 1 and SP 2 Each of the above independently represents a single bond or a divalent aliphatic hydrocarbon group having 1 to 20 carbon atoms, wherein one or more of the -CH2- groups constituting the aliphatic hydrocarbon group can be substituted by -O-, -S-, -NH-, -N(Q)-, or -CO-, where Q represents a substituent. L 1 and L 2 Each of the L groups independently represents a monovalent organic group. 1 and L 2 At least one of them represents a polymerizable group, wherein, in Ar 2 In the case of an aromatic ring represented by the following formula (Ar-3), L 1 and L 2 and L in the following formula (Ar-3) 3 and L 4 At least one of them represents a polymerizable group. Ar 2 It represents any aromatic ring selected from the group consisting of groups represented by the following formulas (Ar-1) to (Ar-7). Here, in equations (Ar-1) to (Ar-7), Indicates with D 1 Or D 2 The bonding position, Q 1 Indicates N or CH, Q 2 Indicates -S-, -O-, or -N(R) 6 )-,R 6 Indicates an alkyl group having 1 to 6 hydrogen atoms or carbon atoms. Y 1 This indicates an aromatic hydrocarbon group with 6 to 12 carbon atoms that may have substituents, an aromatic heterocyclic group with 3 to 12 carbon atoms that may have substituents, or an alicyclic hydrocarbon group with 6 to 20 carbon atoms that may have substituents, wherein one or more of the -CH2- groups constituting the alicyclic hydrocarbon group may be substituted with -O-, -S-, or -NH-. Z 1 Z 2 and Z 3 Each of the following can be independently represented: a hydrogen atom, a monovalent aliphatic hydrocarbon group with 1-20 carbon atoms, a monovalent alicyclic hydrocarbon group with 3-20 carbon atoms, a monovalent aromatic hydrocarbon group with 6-20 carbon atoms, a monovalent aromatic heterocyclic group with 6-20 carbon atoms, a halogen atom, a cyano group, a nitro group, or -OR. 7 -NR 8 R 9 -SR 10 -COOR 11 or -COR 12 R 7 ~R 12 Z represents, independently, either a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. 1 and Z 2 They can bond with each other to form aromatic rings. A 3 and A 4 Each can be independently represented by a selection from -O-, -N(R) 13 The groups in the group consisting of -, -S- and -CO-, R 13 Represents a hydrogen atom or a substituent. X represents a nonmetallic atom from groups 14 to 16, wherein the nonmetallic atom may be bonded with hydrogen atoms or substituents. D 7 and D 8 Each can independently represent a single bond or -CO-, -O-, -S-, -C(=S)-, -CR 1 R 2 -、-CR 3 =CR 4 -、-NR 5 -or a divalent linker formed by two or more of them, R 1 ~R 5 Each of the following can be independently represented by a hydrogen atom, a fluorine atom, or an alkyl group having 1 to 12 carbon atoms. SP 3 and SP 4 Each of the above independently represents a single bond or a divalent aliphatic hydrocarbon group having 1 to 20 carbon atoms, wherein one or more of the -CH2- groups constituting the aliphatic hydrocarbon group can be substituted by -O-, -S-, -NH-, -N(Q)-, or -CO-, where Q represents a substituent. L 3 and L 4 Each of the L groups independently represents a monovalent organic group. 3 and L 4 and L in equation (B) 1 and L 2 At least one of them represents a polymerizable group. Ax represents an organic group having 2 to 30 carbon atoms in at least one aromatic ring selected from the group consisting of aromatic hydrocarbon rings and aromatic heterocycles. Ay represents a hydrogen atom, an alkyl group having 1 to 12 carbon atoms that may have substituents, or an organic group having 2 to 30 carbon atoms that has at least one aromatic ring selected from the group consisting of aromatic hydrocarbon rings and aromatic heterocycles. The aromatic rings in Ax and Ay can have substituents, and Ax and Ay can also bond to form a ring. Q 3 It represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms that may have substituents.

3. The liquid crystal composition according to claim 2, wherein, The content of the compound represented by formula (A) is 18% by mass or less relative to the total mass of the compound represented by formula (A) and the liquid crystal compound.

4. The liquid crystal composition according to any one of claims 1 to 3, wherein, Ar in formula (A) 1 It is an aromatic ring represented by the formula (BQ-1) or (BQ-2).

5. The liquid crystal composition according to claim 2 or 3, wherein, Ar in formula (A) 1 Ar in equation (B) 2 They have the same structure.

6. A benzoquinone derivative, represented by the following formula (A), Here, in equation (A), Ar 1 It represents any aromatic ring selected from the group consisting of groups represented by the following formulas (BQ-1) to (BQ-5). Here, in equations (BQ-1) to (BQ-5), Indicates the bonding position with the oxygen atom. Q 1 Indicates N or CH, Q 2 Indicates -S-, -O-, or -N(R) 6 )-,R 6 Indicates an alkyl group having 1 to 6 hydrogen atoms or carbon atoms. Y 1 This indicates an aromatic hydrocarbon group with 6 to 12 carbon atoms that may have substituents, an aromatic heterocyclic group with 3 to 12 carbon atoms that may have substituents, or an alicyclic hydrocarbon group with 6 to 20 carbon atoms that may have substituents, wherein one or more of the -CH2- groups constituting the alicyclic hydrocarbon group may be substituted with -O-, -S-, or -NH-. Z 1 Z 2 and Z 3 Each of the following can be independently represented: a hydrogen atom, a monovalent aliphatic hydrocarbon group with 1-20 carbon atoms, a monovalent alicyclic hydrocarbon group with 3-20 carbon atoms, a monovalent aromatic hydrocarbon group with 6-20 carbon atoms, a monovalent aromatic heterocyclic group with 6-20 carbon atoms, a halogen atom, a cyano group, a nitro group, or -OR. 7 -NR 8 R 9 -SR 10 -COOR 11 or -COR 12 R 7 ~R 12 Z represents, independently, either a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. 1 and Z 2 They can bond with each other to form aromatic rings. A 3 and A 4 Each can be independently represented by a selection from -O-, -N(R) 13 The groups in the group consisting of -, -S- and -CO-, R 13 Represents a hydrogen atom or a substituent. X represents a nonmetallic atom from groups 14 to 16, where, The non-metallic atoms may be bonded with hydrogen atoms or substituents. D 7 and D 8 Each can independently represent a single bond or -CO-, -O-, -S-, -C(=S)-, -CR 1 R 2 -、-CR 3 =CR 4 -、-NR 5 -or a divalent linker formed by two or more of them, R 1 ~R 5 Each of the following can be independently represented by a hydrogen atom, a fluorine atom, or an alkyl group having 1 to 12 carbon atoms. SP 3 and SP 4 Each of the above independently represents a single bond or a divalent aliphatic hydrocarbon group having 1 to 20 carbon atoms, wherein one or more of the -CH2- groups constituting the aliphatic hydrocarbon group can be substituted by -O-, -S-, -NH-, -N(Q)-, or -CO-, where Q represents a substituent. L 3 and L 4 Each of the above can independently represent a monovalent organic group. Ax represents an organic group having 2 to 30 carbon atoms in at least one aromatic ring selected from the group consisting of aromatic hydrocarbon rings and aromatic heterocycles. Ay represents a hydrogen atom, an alkyl group having 1 to 12 carbon atoms that may have substituents, or an organic group having 2 to 30 carbon atoms that has at least one aromatic ring selected from the group consisting of aromatic hydrocarbon rings and aromatic heterocycles. The aromatic rings in Ax and Ay can have substituents, and Ax and Ay can also bond to form a ring. Q 3 It represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms that may have substituents.

7. A liquid crystal curing layer formed by immobilizing the orientation state of the liquid crystal composition according to any one of claims 1 to 3.

8. An optical film having the liquid crystal curing layer of claim 7.

9. A polarizer having the optical film and polarizer of claim 8.

10. An image display device having the optical film of claim 8.

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