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 allowing to produce a liquid crystal cured layer having good orientation and light stability characteristics. Also provided are a benzoquinone derivative, a liquid crystal cured layer, an optical film, a polarizing plate, and an image display device. The liquid crystal composition according to the present invention contains a compound represented by formula (A) and a liquid crystal compound.

Description

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

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

[0002] Optical films such as optical compensation sheets and retardation films are used in various image display devices to eliminate image coloration or widen the viewing angle. Stretched birefringent films have been used as optical films, but in recent years, it has been proposed to use optical films having an optically anisotropic layer made of a liquid crystal compound instead of stretched birefringent films.

[0003] As such an optical film, an optical film formed using a liquid crystal composition containing a compound represented by a predetermined formula and a liquid crystal compound is known (see, for example, Patent Document 1).

[0004] JP 2011-207765 A

[0005] The present inventors have studied the liquid crystal composition described in Patent Document 1 and found that the orientation of the liquid crystal compound in a cured liquid crystal layer formed using the composition (hereinafter simply referred to as "orientation") is good, but that there is room for improvement in terms of light resistance.

[0006] Therefore, an object of the present invention 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 can be used to prepare a liquid crystal cured layer having both good alignment properties and light resistance.

[0007] As a result of intensive research to achieve the above object, the present inventors have found that a liquid crystal cured layer having good alignment properties and good light resistance can be prepared by using a liquid crystal composition containing a compound represented by formula (A) and a liquid crystal compound, and have completed the present invention. That is, the present inventors have found that the above object can be achieved by the following configuration.

[0008] [1] A liquid crystal composition containing a compound represented by formula (A) described later and a liquid crystal compound. [2] The liquid crystal composition according to [1], wherein the liquid crystal compound is a compound represented by formula (B) described later. [3] The liquid crystal composition according to [1] or [2], wherein the content of the compound represented by formula (A) described later is 18 mass % or less with respect to the total mass of the compound represented by formula (A) described later and the liquid crystal compound. [4] The liquid crystal composition according to [1] or [2], wherein Ar in formula (A) described later １ is an aromatic ring represented by formula (BQ-1) or (BQ-2) described later. [5] The liquid crystal composition according to any one of [1] to [3], １ and Ar in formula (B) described later. ２ and have the same structure. [6] A benzoquinone derivative represented by formula (A) described later. [7] A liquid crystal cured layer obtained by fixing the alignment state of the liquid crystal composition according to any one of [1] to [5]. [8] An optical film having the liquid crystal cured layer according to [7]. [9] A polarizing plate having the optical film according to [8] and a polarizer.

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

[0009] According to the present invention, 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 be used to prepare a liquid crystal cured layer having both good alignment properties and light resistance.

[0010] FIG. 1 is a schematic cross-sectional view showing an example of an optical film.

[0011] The present invention will be described in detail below. The following description of the constituent elements may be based on a representative embodiment of the present invention, but the present invention is not limited to such an embodiment. In this specification, a numerical range expressed using "to" means a range that includes the numerical values ​​before and after "to" as the upper and lower limits. In this specification, the upper or lower limit of a numerical range described in a stepwise manner may be replaced with the upper or lower limit of another stepwise manner. In this specification, the upper or lower limit of a numerical range described in a stepwise manner may be replaced with a value shown in the Examples. In this specification, each component may be a single substance corresponding to the component, or two or more substances may be used in combination. When two or more substances are used in combination for each component, the content of that component refers to the total content of the substances used in combination, unless otherwise specified. In addition, in this specification, "(meth)acrylate" is a notation representing "acrylate" or "methacrylate", "(meth)acrylic" is a notation representing "acrylic" or "methacrylic", and "(meth)acryloyl" is a notation representing "acryloyl" or "methacryloyl". In addition, the bonding direction of the divalent group (e.g., -O-CO-) represented in this specification is not particularly limited, and for example, "L １ -L ２ -L ３ In the bond ２ When is —O—CO—, L １ The position where it is bonded to the side is *1, L ３ If the position bonded to the side is *2, then L ２ may be *1-O-CO-*2 or *1-CO-O-*2.

[0012] In this specification, Re(λ) and Rth(λ) represent the in-plane retardation and the thickness direction retardation, respectively, at a wavelength λ. Unless otherwise specified, the wavelength λ is 550 nm. In the present invention, Re(λ) and Rth(λ) are values ​​measured at a wavelength λ using an AxoScan (manufactured by Axometrics). By inputting the average refractive index ((nx+ny+nz) / 3) and film thickness (d (μm)) into AxoScan, the following slow axis direction (°) is calculated: Re(λ) = R0(λ) Rth(λ) = ((nx+ny) / 2-nz)×d. Note that R0(λ) is displayed as a numerical value calculated by AxoScan, but it means Re(λ).

[0013] In this specification, examples of the substituent (monovalent substituent) include the substituents described below in Substituent Group A. In this specification, the phrase "optionally having a substituent" includes not only an embodiment in which no substituent is present, but also an embodiment in which one or more substituents are present. <Substituent Group A> Examples of the substituent include halogen atoms (for example, fluorine atoms, chlorine atoms, and bromine atoms, preferably chlorine atoms and fluorine atoms, and more preferably fluorine atoms); alkyl groups (preferably linear, branched, or cyclic alkyl groups having 1 to 48 carbon atoms, more preferably 1 to 24 carbon atoms, and particularly preferably 1 to 8 carbon atoms, such as linear alkyl groups having 1 to 6 carbon atoms (for example, methyl, ethyl, n-propyl, n-butyl, n-pentyl, and n-hexyl), branched alkyl groups having 3 to 6 carbon atoms (for example, isopropyl, isobutyl, tert-butyl, sec-butyl, neopentyl, isohexyl, and 3-methylpentyl), and cyclic alkyl groups having 3 to 12 carbon atoms (for example, cyclopropyl, cyclopentyl, cyclohexyl, 1-norbornyl, and 1-adamantyl)); alkenyl groups (preferably alkenyl groups having 2 to 48 carbon atoms, more preferably 2 to 18 carbon atoms, such as vinyl groups, allyl groups, 1-butenyl groups, and 2-butenyl groups); alkynyl groups (preferably alkynyl groups having 2 to 6 carbon atoms, more preferably 2 to 4 carbon atoms, such as ethynyl groups, 1-propynyl groups, propargyl groups, 1-butynyl groups, and 2-butynyl groups); aryl groups (preferably aryl groups having 6 to 48 carbon atoms, more preferably 6 to 24 carbon atoms, such as phenyl groups, oligoaryl groups (naphthyl groups, anthryl groups), phenanthrenyl groups, fluorenyl groups, pyrenyl groups, triphenylenyl groups, and biphenyl groups); Heteroaryl groups (preferably heterocyclic groups having 1 to 32 carbon atoms, more preferably 1 to 18 carbon atoms, such as a 2-thienyl group, a 4-pyridyl group, a 2-furyl group, a 2-pyrimidinyl group, a 1-pyridyl group, a 2-benzothiazolyl group, a 1-imidazolyl group, a 1-pyrazolyl group, or a benzotriazol-1-yl group);arylalkyl groups (preferably arylalkyl groups having 7 to 15 carbon atoms, for example, benzyl group, phenethyl group, methylbenzyl group, phenylpropyl group, 1-methylphenylethyl group, phenylbutyl group, 2-methylphenylpropyl group, tetrahydronaphthyl group, naphthylmethyl group, naphthylethyl group, indenyl group, fluorenyl group, anthracenylmethyl group (anthrylmethyl group), phenanthrenylmethyl group (phenanthrylmethyl group)); silyl groups (preferably silyl groups 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 groups; cyano groups; nitro groups; morpholino groups; Alkoxy groups (preferably alkoxy groups having 1 to 48 carbon atoms, more preferably 1 to 24 carbon atoms, for example, methoxy, ethoxy, 1-butoxy, 2-butoxy, isopropoxy, t-butoxy, dodecyloxy, and cycloalkyloxy groups (for example, cyclopentyloxy and cyclohexyloxy)); aryloxy groups (preferably aryloxy groups having 6 to 48 carbon atoms, more preferably 6 to 24 carbon atoms, for example, phenoxy and 1-naphthoxy); alkenyloxy groups (preferably alkenyloxy groups having 2 to 6 carbon atoms, for example, vinyloxy, 1-propenyloxy, 2-n-propenyloxy (allyloxy), 1-n-butenyloxy, and prenyloxy); heterocyclic oxy groups (preferably heterocyclic oxy groups having 1 to 32 carbon atoms, more preferably 1 to 18 carbon atoms, such as a 1-phenyltetrazole-5-oxy group or a 2-tetrahydropyranyloxy group); silyloxy groups (preferably silyloxy groups having 1 to 32 carbon atoms, more preferably 1 to 18 carbon atoms, such as a trimethylsilyloxy group, a t-butyldimethylsilyloxy group or a diphenylmethylsilyloxy group); acyloxy groups (preferably acyloxy groups having 2 to 48 carbon atoms, more preferably 2 to 24 carbon atoms, such as an acetoxy group, a pivaloyloxy group, a benzoyloxy group, a dodecanoyloxy group, an acryloyloxy group or a methacryloyloxy group);hydroxyalkyleneoxy groups (preferably hydroxyalkyleneoxy groups having 2 to 10 carbon atoms, for example, a hydroxyethyleneoxy group); alkoxycarbonyloxy groups (preferably alkoxycarbonyloxy groups having 2 to 48 carbon atoms, more preferably 2 to 24 carbon atoms, for example, an ethoxycarbonyloxy group, a t-butoxycarbonyloxy group, or a cycloalkyloxycarbonyloxy group (for example, a cyclohexyloxycarbonyloxy group)); aryloxycarbonyloxy groups (preferably aryloxycarbonyloxy groups having 7 to 32 carbon atoms, more preferably 7 to 24 carbon atoms, for example, a phenoxycarbonyloxy group); carbamoyloxy groups (preferably carbamoyloxy groups having 1 to 48 carbon atoms, more preferably 1 to 24 carbon atoms, for example, an N,N-dimethylcarbamoyloxy group, an N-butylcarbamoyloxy group, an N-phenylcarbamoyloxy group, or an N-ethyl-N-phenylcarbamoyloxy group); sulfamoyloxy groups (preferably sulfamoyloxy groups having 1 to 32 carbon atoms, more preferably 1 to 24 carbon atoms, such as an N,N-diethylsulfamoyloxy group or an N-propylsulfamoyloxy group); alkylsulfonyloxy groups (preferably alkylsulfonyloxy groups having 1 to 38 carbon atoms, more preferably 1 to 24 carbon atoms, such as a methylsulfonyloxy group, a hexadecylsulfonyloxy group or a cyclohexylsulfonyloxy group); arylsulfonyloxy groups (preferably arylsulfonyloxy groups having 6 to 32 carbon atoms, more preferably 6 to 24 carbon atoms, such as a phenylsulfonyloxy group); acyl groups (preferably acyl groups having 1 to 48 carbon atoms, more preferably 1 to 24 carbon atoms, such as a formyl group, an acetyl group, an acryloyl group, a methacryloyl group, a pivaloyl group, a benzoyl group, a tetradecanoyl group or a cyclohexanoyl group); an alkoxycarbonyl group (preferably an alkoxycarbonyl group having 2 to 48 carbon atoms, more preferably 2 to 24 carbon atoms, for example, a methoxycarbonyl group, an ethoxycarbonyl group, an octadecyloxycarbonyl group, a cyclohexyloxycarbonyl group, or a 2,6-di-tert-butyl-4-methylcyclohexyloxycarbonyl group);an aryloxycarbonyl group (preferably an aryloxycarbonyl group having 7 to 32 carbon atoms, more preferably an aryloxycarbonyl group having 7 to 24 carbon atoms, for example, a phenoxycarbonyl group); a carbamoyl group (preferably a carbamoyl group having 1 to 48 carbon atoms, more preferably a carbamoyl group having 1 to 24 carbon atoms, for example, a carbamoyl group, N,N-diethylcarbamoyl group, N-ethyl-N-octylcarbamoyl group, N,N-dibutylcarbamoyl group, N-propylcarbamoyl group, N-phenylcarbamoyl group, N-methyl-N-phenylcarbamoyl group, or N,N-dicyclohexylcarbamoyl group); an amino group (preferably an amino group having 32 or less carbon atoms, more preferably an amino group having 24 or less carbon atoms, for example, an amino group, a methylamino group, an N,N-dibutylamino group, a tetradecylamino group, a 2-ethylhexylamino group, or a cyclohexylamino group); anilino group (preferably an anilino group having 6 to 32 carbon atoms, more preferably 6 to 24 carbon atoms, for example, an anilino group, an N-methylanilino group); heterocyclic amino group (preferably a heterocyclic amino group having 1 to 32 carbon atoms, more preferably 1 to 18 carbon atoms, for example, a 4-pyridylamino group); carbonamido group (preferably a carbonamido group having 2 to 48 carbon atoms, more preferably 2 to 24 carbon atoms, for example, an acetamido group, a benzamido group, a tetradecanamido group, a pivaloylamido group, a cyclohexanamido group); ureido group (preferably a ureido group having 1 to 32 carbon atoms, more preferably 1 to 24 carbon atoms, for example, a ureido group, an N,N-dimethylureido group, an N-phenylureido group); imido group (preferably an imido group having 36 or less carbon atoms, more preferably 24 or less carbon atoms, for example, an N-succinimido group, an N-phthalimido group); an alkoxycarbonylamino group (preferably an alkoxycarbonylamino group having 2 to 48 carbon atoms, more preferably 2 to 24 carbon atoms, for example, a methoxycarbonylamino group, an ethoxycarbonylamino group, a t-butoxycarbonylamino group, an octadecyloxycarbonylamino group, or a cyclohexyloxycarbonylamino group); an aryloxycarbonylamino group (preferably an aryloxycarbonylamino group having 7 to 32 carbon atoms, more preferably 7 to 24 carbon atoms, for example, a phenoxycarbonylamino group);sulfonamido groups (preferably sulfonamido groups having 1 to 48 carbon atoms, more preferably 1 to 24 carbon atoms, for example, methanesulfonamido groups, butanesulfonamido groups, benzenesulfonamido groups, hexadecanesulfonamido groups, and cyclohexanesulfonamido groups); sulfamoylamino groups (preferably sulfamoylamino groups having 1 to 48 carbon atoms, more preferably 1 to 24 carbon atoms, for example, N,N-dipropylsulfamoylamino groups, and N-ethyl-N-dodecylsulfamoylamino groups); azo groups (preferably azo groups having 1 to 32 carbon atoms, more preferably 1 to 24 carbon atoms, for example, phenylazo groups and 3-pyrazolylazo groups); alkylthio groups (preferably alkylthio groups having 1 to 48 carbon atoms, more preferably 1 to 24 carbon atoms, for example, methylthio groups, ethylthio groups, octylthio groups, and cyclohexylthio groups); an arylthio group (preferably an arylthio group having 6 to 48 carbon atoms, more preferably an arylthio group having 6 to 24 carbon atoms, for example, a phenylthio group); a heterocyclic thio group (preferably a heterocyclic thio group having 1 to 32 carbon atoms, more preferably a heterocyclic thio group having 1 to 18 carbon atoms, for example, a 2-benzothiazolylthio group, a 2-pyridylthio group, or a 1-phenyltetrazolylthio group); an alkylsulfinyl group (preferably an alkylsulfinyl group having 1 to 32 carbon atoms, more preferably an alkylsulfinyl group having 1 to 24 carbon atoms, for example, a dodecanesulfinyl group); an arylsulfinyl group (preferably an arylsulfinyl group having 6 to 32 carbon atoms, more preferably an arylsulfinyl group having 6 to 24 carbon atoms, for example, a phenylsulfinyl group); alkylsulfonyl groups (preferably alkylsulfonyl groups having 1 to 48 carbon atoms, more preferably 1 to 24 carbon atoms, for example, methylsulfonyl, ethylsulfonyl, propylsulfonyl, butylsulfonyl, isopropylsulfonyl, 2-ethylhexylsulfonyl, hexadecylsulfonyl, octylsulfonyl, and cyclohexylsulfonyl groups); arylsulfonyl groups (preferably arylsulfonyl groups having 6 to 48 carbon atoms, more preferably 6 to 24 carbon atoms, for example, phenylsulfonyl, and 1-naphthylsulfonyl groups);sulfamoyl groups (preferably sulfamoyl groups having 32 or less carbon atoms, more preferably 24 or less carbon atoms, for example, a sulfamoyl group, an N,N-dipropylsulfamoyl group, an N-ethyl-N-dodecylsulfamoyl group, an N-ethyl-N-phenylsulfamoyl group, an N-cyclohexylsulfamoyl group, or an N-(2-ethylhexyl)sulfamoyl group); phosphonyl groups (preferably phosphonyl groups having 1 to 32 carbon atoms, more preferably 1 to 24 carbon atoms, for example, a phenoxyphosphonyl group, an octyloxyphosphonyl group, or a phenylphosphonyl group); phosphinoylamino groups (preferably phosphinoylamino groups having 1 to 32 carbon atoms, more preferably 1 to 24 carbon atoms, for example, a diethoxyphosphinoylamino group, or a dioctyloxyphosphinoylamino group); epoxy groups; —NHCOCH; ３ ;-SO ２ NHC ２ H ４ OCH ３ ;-NHSO ２ CH ３ and the like, and two or more of these may be combined. These substituents may be further substituted with other substituents. When two or more substituents are present, they may be the same or different. If possible, they may be bonded to each other to form a ring.

[0014] [Liquid Crystal Composition] The liquid crystal composition of the present invention is a liquid crystal composition containing a compound represented by formula (A) described below (hereinafter also abbreviated as "specific compound A") and a liquid crystal compound.

[0015] In the present invention, as described above, by using a liquid crystal composition containing the specific compound A and a liquid crystal compound, a cured liquid crystal layer having both good alignment and light resistance can be prepared. Although the details of this are not clear, the inventors speculate as follows. Specifically, it is believed that the specific compound A has a specific aromatic ring, which improves compatibility with the liquid crystal compound and allows the liquid crystal compound to maintain excellent alignment. Furthermore, since the specific compound A is a quinone compound, it is affected by ultraviolet light more quickly than the liquid crystal compound and can also function as an ultraviolet absorber, which is believed to improve the light resistance of the prepared cured liquid crystal layer. The specific compound A and the liquid crystal compound contained in the liquid crystal composition of the present invention are described in detail below.

[0016] [Specific Compound A] Specific compound A is a compound represented by the following formula (A).

[0017] In the above formula (A), Ar １ represents any aromatic ring selected from the group consisting of groups represented by the following formulas (BQ-1) to (BQ-5): In the following formulas (BQ-1) to (BQ-5), * represents the bonding position with the oxygen atom in the above formula (A).

[0018] In the above formula (BQ-1), Q １ represents N or CH, and Q ２ is -S-, -O-, or -N(R ６ )-, R ６ represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms; Y １ represents an aromatic hydrocarbon group having 6 to 12 carbon atoms which may have a substituent, an aromatic heterocyclic group having 3 to 12 carbon atoms which may have a substituent, or an alicyclic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent, and -CH ２ One or more of - may be replaced by -O-, -S- or -NH-. ６Specific examples of the alkyl group having 1 to 6 carbon atoms represented by one embodiment of the formula (1) include a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, and an n-hexyl group. １ Examples of the aromatic hydrocarbon group having 6 to 12 carbon atoms represented by one embodiment of the formula (I) include aryl groups such as a phenyl group, a 2,6-diethylphenyl group, and a naphthyl group. １ Examples of the aromatic heterocyclic group having 3 to 12 carbon atoms represented by one embodiment of the formula (1) include heteroaryl groups such as a thienyl group, a thiazolyl group, a furyl group, and a pyridyl group, as well as groups formed by removing one hydrogen atom from an indole ring, a benzofuran ring, a benzothiophene ring, a benzimidazole ring, a benzothiazole ring, and a benzoxazole ring. １ The aromatic heterocyclic group having 3 to 12 carbon atoms represented by Y is preferably a group obtained by removing one hydrogen atom from a benzofuran ring or a benzothiazole ring. １ Examples of the alicyclic hydrocarbon group having 6 to 20 carbon atoms represented by one embodiment of the formula (1) include a cyclohexylene group, a cyclopentylene group, a norbornylene group, and an adamantylene group. １ Examples of the substituent that may be possessed by the group include the substituents described in the above-mentioned substituent group A, 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.

[0019] In addition, in the above formulas (BQ-1) to (BQ-5), Z １ , Z ２ and Z ３ each independently represents 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 １２represents R ７ ~R １２ each independently represents 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. As the monovalent aliphatic hydrocarbon group having 1 to 20 carbon atoms, an alkyl group having 1 to 15 carbon atoms is preferred, an alkyl group having 1 to 8 carbon atoms is more preferred, specifically, a methyl group, an ethyl group, an isopropyl group, a tert-pentyl group (1,1-dimethylpropyl group), a tert-butyl group, or a 1,1-dimethyl-3,3-dimethyl-butyl group is further preferred, and a methyl group, an ethyl group, or a tert-butyl group is particularly preferred. Examples of the monovalent alicyclic hydrocarbon group having 3 to 20 carbon atoms include monocyclic saturated hydrocarbon groups such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclodecyl, methylcyclohexyl, and ethylcyclohexyl groups; monocyclic unsaturated hydrocarbon groups such as cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, cyclooctenyl, cyclodecenyl, cyclopentadienyl, cyclohexadienyl, cyclooctadienyl, and cyclodecadiene; bicyclo[2.2.1]heptyl, bicyclo[2.2.2]octyl, and tricyclo[5.2.1.0]diene; ２，６ ]decyl group, tricyclo[3.3.1.1 ３，７ ]decyl group, tetracyclo[6.2.1.1 ３，６ .0 ２，７ ] dodecyl group, adamantyl group, and other polycyclic saturated hydrocarbon groups. Specific examples of the monovalent aromatic hydrocarbon group having 6 to 20 carbon atoms include a phenyl group, a 2,6-diethylphenyl group, a naphthyl group, and a biphenyl group, with an aryl group having 6 to 12 carbon atoms (particularly a phenyl group) being preferred. Specific examples of the monovalent aromatic heterocyclic group having 6 to 20 carbon atoms include a 4-pyridyl group, a 2-furyl group, a 2-thienyl group, a 2-pyrimidinyl group, and a 2-benzothiazolyl group. Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom, with a fluorine atom, a chlorine atom, and a bromine atom being preferred. On the other hand, R ７~R １０ Specific examples of the alkyl group having 1 to 6 carbon atoms include a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, and an n-hexyl group.

[0020] Z １ and Z ２ As described above, may be bonded to each other to form an aromatic ring, and for example, Z １ and Z ２ Examples of the structure in which these bond to each other to form an aromatic ring include a group represented by the following formula (BQ-1a): In the following formula (BQ-1a), * represents the bonding position with the oxygen atom in the above formula (A). Here, in the above formula (BQ-1a), Q １ , Q ２ and Y １ The examples of the formula (BQ-1) include those similar to those explained above.

[0021] In addition, in the above formulas (BQ-2) and (BQ-3), A ３ and A ４ are each independently —O—, —N(R １３ represents a group selected from the group consisting of —, —S—, and —CO—; R １３ represents a hydrogen atom or a substituent. １３ Examples of the substituent represented by one embodiment of the formula (I) include the substituents described in the above-mentioned Substituent Group A, and among them, an alkyl group, an alkoxy group, an alkoxycarbonyl group, an alkylcarbonyloxy group, or a halogen atom is preferable.

[0022] In the formula (BQ-2), X represents a nonmetallic atom of Groups 14 to 16. However, the nonmetallic atom may have a hydrogen atom or a substituent bonded thereto. Examples of the nonmetallic atom of Groups 14 to 16 represented by X include an oxygen atom, a sulfur atom, a hydrogen atom, or a nitrogen atom bonded to a substituent [═N-R Ｎ１ , R Ｎ１ represents a hydrogen atom or a substituent.], a carbon atom to which a hydrogen atom or a substituent is bonded [═C—(R Ｃ１ )２ , R Ｃ１ represents a hydrogen atom or a substituent.] Examples of the substituent include the substituents described in the above-mentioned substituent group A, and among them, preferred examples include an alkyl group, an alkoxy group, an alkyl-substituted alkoxy group, a cyclic alkyl group, an aryl group (for example, a phenyl group, a naphthyl group, etc.), a cyano group, an amino group, a nitro group, an alkylcarbonyl group, a sulfo group, and a hydroxyl group.

[0023] In addition, in the above formula (BQ-3), D ７ and D ８ each independently represents a single bond, or —CO—, —O—, —S—, —C(═S)—, or —CR １ R ２ -, -CR ３ =CR ４ -, -NR ５ -, or a divalent linking group formed by a combination of two or more thereof, R １ ~R ５ each independently represents a hydrogen atom, a fluorine atom, or an alkyl group having 1 to 12 carbon atoms. Specific examples of the divalent linking group include -CO-, -O-, -CO-O-, -C(=S)O-, and -CR １ R ２ -, -CR １ R ２ -CR １ R ２ -, -O-CR １ R ２ -, -CR １ R ２ -O-CR １ R ２ -, -CO-O-CR １ R ２ -, -O-CO-CR １ R ２ -, -CR １ R ２ -O-CO-CR １ R ２ -, -CR １ R ２ -CO-O-CR １ R ２ -, -NR ５ -CR １ R ２ - and -CO-NR５ -, etc. １ , R ２ and R ５ each independently represents a hydrogen atom, a fluorine atom, or an alkyl group having 1 to 12 carbon atoms. Among these, any of —CO—, —O—, and —CO—O— is preferred.

[0024] In addition, in the above formula (BQ-3), SP ３ and SP ４ each independently represents a single bond or a divalent aliphatic hydrocarbon group having 1 to 20 carbon atoms, provided that —CH ２ One or more of the - may be substituted with -O-, -S-, -NH-, -N(Q)-, or -CO-. Q represents a substituent. Examples of the substituent represented by Q include the substituents described in the above-mentioned substituent group A, and among these, an alkyl group, an alkoxy group, an alkoxycarbonyl group, an alkylcarbonyloxy group, or a halogen atom is preferred. Here, examples of the divalent aliphatic hydrocarbon group include a linear or branched alkylene group having 1 to 20 carbon atoms, a linear or branched alkenylene group having 1 to 20 carbon atoms, and a linear or branched alkynylene group having 1 to 20 carbon atoms. As the linear 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. Suitable examples include a methylene group, an ethylene group, a propylene group, a butylene group, a pentylene group, and a hexylene group. The linear or branched alkenylene group having 1 to 20 carbon atoms is preferably an alkenylene group having 2 to 10 carbon atoms, more preferably an alkenylene group having 2 to 4 carbon atoms, and suitable examples thereof include an ethenylene group. The linear or branched alkynylene group having 1 to 20 carbon atoms is preferably an alkynylene group having 2 to 10 carbon atoms, more preferably an alkynylene group having 2 to 4 carbon atoms, and suitable examples thereof include an ethynylene group.

[0025] In addition, in the above formula (BQ-3), L ３ and L ４Each independently represents a monovalent organic group. Examples of the monovalent organic group include the substituents described in the above-mentioned Substituent Group A, and among these, preferred are alkyl groups, aryl groups, heteroaryl groups, alkoxy groups, cyano groups, and carboxy groups. The alkyl group may be linear, branched, or cyclic, but linear groups are preferred. The alkyl group preferably has 1 to 30 carbon atoms, more preferably 1 to 20, and even more preferably 1 to 10. The aryl group may be monocyclic or polycyclic, but monocyclic groups are preferred. The aryl group preferably has 6 to 25 carbon atoms, more preferably 6 to 10. The heteroaryl group may be monocyclic or polycyclic. The number of heteroatoms constituting the heteroaryl group is preferably 1 to 3. The heteroatoms constituting the heteroaryl group are preferably nitrogen atoms, sulfur atoms, or oxygen atoms. The heteroaryl group preferably has 6 to 18 carbon atoms, more preferably 6 to 12. The alkyl group, aryl group, and heteroaryl group may be unsubstituted or may have a substituent. Examples of the substituent include the substituents described in the above-mentioned substituent group A, and among them, an alkyl group, an alkoxy group, an alkoxycarbonyl group, an alkylcarbonyloxy group, or a halogen atom is preferred.

[0026] In addition, in the above formula (BQ-3), L ３ and L ４At least one of the groups may be a polymerizable group. The polymerizable group is not particularly limited, but is preferably a polymerizable group capable of radical polymerization or cation polymerization. The radical polymerizable group may be a known radical polymerizable group, and preferred examples include an acryloyloxy group or a methacryloyloxy group. In this case, the polymerization rate of an acryloyloxy group is generally known to be fast, and an acryloyloxy group is preferred from the viewpoint of improving productivity, but a methacryloyloxy group can also be used as the polymerizable group. The cationic polymerizable group may be a known cationic polymerizable group, and specific examples include an alicyclic ether group, a cyclic acetal group, a cyclic lactone group, a cyclic thioether group, a spiro orthoester group, and a vinyloxy group. Among these, an alicyclic ether group or a vinyloxy group is preferred, and an epoxy group, an oxetanyl group, or a vinyloxy group is particularly preferred. Particularly preferred examples of the polymerizable group include polymerizable groups represented by any of the following formulas (P-1) to (P-20):

[0027]

[0028] In the above formulas (BQ-4) to (BQ-5), Ax represents an organic group having 2 to 30 carbon atoms and having at least one aromatic ring selected from the group consisting of aromatic hydrocarbon rings and aromatic heterocycles. In the above formulas (BQ-4) to (BQ-5), Ay represents a hydrogen atom, an alkyl group having 1 to 12 carbon atoms which may have a substituent, or an organic group having 2 to 30 carbon atoms and having at least one aromatic ring selected from the group consisting of aromatic hydrocarbon rings and aromatic heterocycles. Here, the aromatic rings in Ax and Ay may have a substituent, and Ax and Ay may be bonded to form a ring. In addition, Q ３ represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms which may have a substituent. Examples of Ax and Ay include those described in paragraphs

[0039] to

[0095] of WO 2014 / 010325. ３Specific examples of the alkyl group having 1 to 6 carbon atoms represented by include a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, and an n-hexyl group. Examples of the substituent include the substituents described in the above-mentioned substituent group A. Among these, an alkyl group, an alkoxy group, an alkoxycarbonyl group, an alkylcarbonyloxy group, or a halogen atom is preferred.

[0029] In the present invention, from the viewpoint of achieving desired optical properties, Ar in the above formula (A) １ is preferably an aromatic ring represented by the above formula (BQ-1) or (BQ-2).

[0030] Suitable examples of the specific compound A include specific compounds (A-1) to (A-12) represented by the following formulae:

[0031] [Liquid Crystal Compound] The liquid crystal compound contained in the liquid crystal composition of the present invention is not particularly limited, and conventionally known liquid crystal compounds can be used. Generally, liquid crystal compounds can be classified into rod-shaped and discotic types based on their shape. Each type can further be divided into low-molecular-weight and high-molecular-weight types. High-molecular-weight compounds generally refer to compounds with a degree of polymerization of 100 or more (see "Polymer Physics: Phase Transition Dynamics," by Masao Doi, p. 2, Iwanami Shoten, 1992). While any liquid crystal compound can be used in the present invention, rod-shaped or discotic liquid crystal compounds (discotic liquid crystal compounds) are preferred. Two or more rod-shaped liquid crystal compounds, two or more discotic liquid crystal compounds, or a mixture of a rod-shaped liquid crystal compound and a discotic liquid crystal compound may also be used. As the rod-shaped liquid crystal compound, for example, those described in claim 1 of JP-A-11-513019 and paragraphs

[0026] to

[0098] of JP-A-2005-289980 can be preferably used, and as the discotic liquid crystal compound, for example, those described in paragraphs

[0020] to

[0067] of JP-A-2007-108732 and paragraphs

[0013] to

[0108] of JP-A-2010-244038 can be preferably used, but are not limited to these.

[0032] In the present invention, the liquid crystal compound preferably has a polymerizable group, more preferably has two or more polymerizable groups, for the reason that the durability of the cured liquid crystal layer is improved. Here, the polymerizable group is preferably a polymerizable group represented by any one of the above formulas (P-1) to (P-20).

[0033] In the present invention, the liquid crystal compound is preferably a compound represented by the following formula (B) because the alignment of the cured liquid crystal layer is improved. 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)

[0034] In the above formula (B), a1, a2, g1, and g2 each independently represent 0 or 1. However, at least one of a1 and g1 represents 1, and at least one of a2 and g2 represents 1. １ , D ２ , D ３ , D ４ , D ５ and D ６ each independently represents a single bond, or —CO—, —O—, —S—, —C(═S)—, or —CR １ R ２ -, -CR ３ =CR ４ -, -NR ５ -, or a divalent linking group formed by a combination of two or more thereof, R １ ~R ５ each independently represents a hydrogen atom, a fluorine atom, or an alkyl group having 1 to 12 carbon atoms.１ and G ２ each independently represents an aromatic ring having 6 to 20 carbon atoms which may have a substituent, or a divalent alicyclic hydrocarbon group having 5 to 20 carbon atoms which may have a substituent, and -CH ２ One or more of - may be substituted with -O-, -S- or -NH-. １ and A ２ each independently represents an aromatic ring having 6 to 20 carbon atoms which may have a substituent, or a divalent alicyclic hydrocarbon group having 5 to 20 carbon atoms which may have a substituent, and -CH ２ One or more of - may be substituted with -O-, -S- or -NH-. １ and SP ２ each independently represents a single bond or a divalent aliphatic hydrocarbon group having 1 to 20 carbon atoms, provided that —CH ２ One or more of - may be substituted with -O-, -S-, -NH-, -N(Q)- or -CO-. Q represents a substituent. １ and L ２ each independently represents a monovalent organic group; １ and L ２ At least one of Ar represents a polymerizable group. ２ is 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 Ar represents a polymerizable group. ２ represents any aromatic ring selected from the group consisting of groups represented by formulas (Ar-1) to (Ar-7) described below.

[0035] In the above formula (B), a1, a2, g1, and g2 are preferably all 1 because the liquid crystal composition of the present invention is more likely to exhibit a smectic liquid crystal state. In addition, it is preferable that a1 and a2 are all 0 and g1 and g2 are all 1 because the durability of the produced cured liquid crystal layer is improved.

[0036] In the above formula (B), D １ , D ２ , D ３ , D ４ , D ５ and D ６ Examples of the divalent linking group represented by one embodiment of the formula (A) include Ar １ D in the above formula (BQ-3) ７ and D ８ Examples of the above-described examples are the same as those described above.

[0037] In the above formula (B), G １ and G ２ Examples of the aromatic ring having 6 to 20 carbon atoms represented by one embodiment of the formula (1) include aromatic hydrocarbon rings such as a benzene ring, a naphthalene ring, an anthracene ring, and a phenanthroline ring; and aromatic heterocycles such as a furan ring, a pyrrole ring, a thiophene ring, a pyridine ring, a thiazole ring, and a benzothiazole ring. Of these, a benzene ring (for example, a 1,4-phenyl group) is preferred.

[0038] In the above formula (B), G １ and G ２ The divalent alicyclic hydrocarbon group having 5 to 20 carbon atoms represented by one embodiment of the formula (1) is preferably a 5-membered or 6-membered ring. The alicyclic hydrocarbon group may be saturated or unsaturated, but is preferably a saturated alicyclic hydrocarbon group. １ and G ２ For the divalent alicyclic hydrocarbon group represented by the formula (I), reference can be made to, for example, paragraph

[0078] of JP-A-2012-21068, the contents of which are incorporated herein by reference.

[0039] In the present invention, the durability of the produced cured liquid crystal layer is improved, so that G in the above formula (B) １ and G ２is preferably a cycloalkane ring. Specific examples of the cycloalkane ring include a cyclohexane ring, a cycloheptane ring, a cyclooctane ring, a cyclododecane ring, and a cyclodocosane ring. Of these, a cyclohexane ring is preferred, a 1,4-cyclohexylene group is more preferred, and a trans-1,4-cyclohexylene group is even more preferred.

[0040] In addition, in the above formula (B), G １ and G ２ With regard to the above, examples of the substituent that the aromatic ring having 6 to 20 carbon atoms or the divalent alicyclic hydrocarbon group having 5 to 20 carbon atoms may have include the substituents described in the above-mentioned substituent group A, and among them, an alkyl group, an alkoxy group, an alkoxycarbonyl group, an alkylcarbonyloxy group, or a halogen atom is preferable.

[0041] In the above formula (B), A １ and A ２ The aromatic ring having 6 to 20 carbon atoms in one embodiment of the formula (B) is G １ and G ２ In addition, in the above formula (B), A １ and A ２ The divalent alicyclic hydrocarbon group having 5 to 20 carbon atoms represented by one embodiment of the formula (B) is G １ and G ２ The same as those explained in A １ and A ２ With respect to the above, examples of the substituent that the aromatic ring having 6 to 20 carbon atoms or the divalent alicyclic hydrocarbon group having 5 to 20 carbon atoms may have include G １ and G ２ Examples of the substituents include the same as those that may be possessed by the group.

[0042] In the above formula (B), SP １ and SP ２Examples of the divalent aliphatic hydrocarbon group having 1 to 20 carbon atoms represented by one embodiment of the formula (1) include a linear or branched alkylene group having 1 to 20 carbon atoms, a linear or branched alkenylene group having 1 to 20 carbon atoms, and a linear or branched alkynylene group having 1 to 20 carbon atoms. As the linear 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, and suitable examples include a methylene group, an ethylene group, a propylene group, a butylene group, a pentylene group, and a hexylene group. As the linear or branched alkenylene group having 1 to 20 carbon atoms, an alkenylene group having 2 to 10 carbon atoms is preferred, and an alkenylene group having 2 to 4 carbon atoms is more preferred, and suitable examples include an ethenylene group. As the linear or branched alkynylene group having 1 to 20 carbon atoms, an alkynylene group having 2 to 10 carbon atoms is preferred, an alkynylene group having 2 to 4 carbon atoms is more preferred, and a suitable example is an ethynylene group. As described above, -CH ２ One or more of - may be substituted with -O-, -S-, -NH-, -N(Q)-, or -CO-. Examples of the substituent represented by Q include the substituents described in the above-mentioned substituent group A. Among them, an alkyl group, an alkoxy group, an alkoxycarbonyl group, an alkylcarbonyloxy group, or a halogen atom is preferable.

[0043] In the above formula (B), L １ and L ２ The monovalent organic group represented by is Ar in the above formula (A). １ In one embodiment, L in the formula (BQ-3) ３ and L ４ In addition, the same as those explained in the above. １ and L ２ The polymerizable group represented by at least one of the formulae (P-1) to (P-20) is preferably a polymerizable group represented by any one of the formulae (P-1) to (P-20) above.

[0044] In the above formula (B), Ar ２As described above, represents any aromatic ring selected from the group consisting of groups represented by the following formulae (Ar-1) to (Ar-7). In the following formulae (Ar-1) to (Ar-7), * represents D in the above formula (B). １ or D ２ represents the bonding position with

[0045] Here, each symbol in the above formulas (Ar-1) to (Ar-7) represents Ar in the above formula (A). １ is the same as each symbol in the above formulas (BQ-1) to (BQ-5).

[0046] Examples of the liquid crystal compound include compounds represented by the general formula (1) described in JP-A-2010-084032 (particularly, compounds described in paragraphs

[0067] to

[0073] ), compounds represented by the general formula (II) described in JP-A-2016-053709 (particularly, compounds described in paragraphs

[0036] to

[0043] ), and compounds represented by the general formula (1) described in JP-A-2016-081035 (particularly, compounds described in paragraphs

[0043] to

[0055] ), and compounds described in paragraphs

[0025] to

[0056] of WO 2021 / 060427.

[0047] Of these, the liquid crystal compounds preferably include liquid crystal compounds (B-1) to (B-14) represented by the following formulas:

[0048] In the present invention, for the reason that the alignment property of the cured liquid crystal layer becomes better, the content of the compound represented by the formula (A) is preferably 18% by mass or less, and more preferably 5 to 18% by mass, based on the total mass of the compound represented by the formula (A) and the liquid crystal compound (particularly, the compound represented by the formula (B)).

[0049] In the present invention, in order to improve the alignment of the cured liquid crystal layer, the compound represented by the formula (A) (specific compound A) and the compound represented by the formula (B) (liquid crystal compound) are preferably formed by the following formula (A): Ar １ and Ar in the above formula (B) ２It is preferable that the structures are the same.

[0050] [Other Polymerizable Compounds] From the viewpoints of alignment temperature and solubility, the liquid crystal composition of the present invention preferably contains, in addition to the above-described specific compound A and the liquid crystal compound, another polymerizable compound having one or more polymerizable groups. Here, the polymerizable group possessed by the other polymerizable compound is not particularly limited, and preferred examples thereof include the polymerizable groups represented by any of the above-described formulas (P-1) to (P-20).

[0051] The other polymerizable compound is preferably an other polymerizable compound having 2 to 4 polymerizable groups, more preferably an other polymerizable compound having 2 polymerizable groups, for the reason that the durability of the formed liquid crystal cured layer is further improved.

[0052] Examples of such other polymerizable compounds include compounds represented by formulae (M1), (M2), and (M3) described in paragraphs

[0030] to

[0033] of JP2014-077068A, and more specifically, specific examples described in paragraphs

[0046] to

[0055] of the same publication.

[0053] [Polymerization Initiator] The liquid crystal composition of the present invention preferably contains a polymerization initiator. The polymerization initiator used is preferably a photopolymerization initiator capable of initiating a polymerization reaction by ultraviolet irradiation. Examples of the photopolymerization initiator include α-carbonyl compounds (described in U.S. Pat. Nos. 2,367,661 and 2,367,670), acyloin ethers (described in U.S. Pat. No. 2,448,828), α-hydrocarbon-substituted aromatic acyloin compounds (described in U.S. Pat. No. 2,722,512), polynuclear quinone compounds (described in U.S. Pat. Nos. 3,046,127 and 2,951,758), and mixtures of triarylimidazole dimers and p-aminophenyl ketones. (described in U.S. Pat. No. 3,549,367), acridine and phenazine compounds (described in JP-A-60-105667 and U.S. Pat. No. 4,239,850), oxadiazole compounds (described in U.S. Pat. No. 4,212,970), acylphosphine oxide compounds (described in JP-B-63-40799, JP-B-5-29234, JP-A-10-95788, and JP-A-10-29997), etc. In the present invention, the polymerization initiator is preferably an oxime-type polymerization initiator, and specific examples thereof include the initiators described in paragraphs

[0049] to

[0052] of WO 2017 / 170443.

[0054] [Solvent] The liquid crystal composition of the present invention preferably contains a solvent from the viewpoint of workability in forming a cured liquid crystal layer. Specific examples of the solvent include ketones (e.g., acetone, 2-butanone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, cyclopentanone, etc.), ethers (e.g., dioxane, tetrahydrofuran, etc.), aliphatic hydrocarbons (e.g., hexane, etc.), alicyclic hydrocarbons (e.g., cyclohexane, etc.), aromatic hydrocarbons (e.g., toluene, xylene, trimethylbenzene, etc.), halogenated carbons (e.g., dichloromethane, dichloroethane, dichlorobenzene, chlorotoluene, etc.), esters (e.g., methyl acetate, ethyl acetate, butyl acetate, etc.), water, alcohols (e.g., ethanol, isopropanol, butanol, cyclohexanol, etc.), cellosolves (e.g., methyl cellosolve, ethyl cellosolve, etc.), cellosolve acetates, sulfoxides (e.g., dimethyl sulfoxide, etc.), amides (e.g., dimethylformamide, dimethylacetamide, etc.), and the like. These may be used alone or in combination of two or more.

[0055] [Leveling Agent] The liquid crystal composition of the present invention preferably contains a leveling agent from the viewpoint of facilitating alignment control. Such a leveling agent is preferably a fluorine-based leveling agent or a silicon-based leveling agent because of its high leveling effect relative to the amount added, and more preferably a fluorine-based leveling agent from the viewpoint of being less likely to cause bleeding (bloom, bleed). Specific examples of the leveling agent include compounds described in paragraphs

[0079] to

[0102] of JP-A No. 2007-069471, compounds represented by general formula (I) described in JP-A No. 2013-047204 (particularly compounds described in paragraphs

[0020] to

[0032] ), and compounds represented by general formula (I) described in JP-A No. 2012-211306 (particularly compounds

[0022] to

[0029] ). Examples of the compound include the compounds described in paragraphs

[0076] to

[0078] and

[0082] to

[0084] ), liquid crystal alignment promoters represented by general formula (I) described in JP-A-2002-129162 (particularly the compounds described in paragraphs

[0076] to

[0078] and

[0082] to

[0084] ), and compounds represented by general formulas (I), (II), and (III) described in JP-A-2005-099248 (particularly the compounds described in paragraphs

[0092] to

[0096] ). The compound may also function as an alignment control agent, which will be described later.

[0056] [Alignment Control Agent] The liquid crystal composition of the present invention may contain an alignment control agent, if necessary. The alignment control agent can form various alignment states such as homogeneous alignment, homeotropic alignment (vertical alignment), tilted alignment, hybrid alignment, and cholesteric alignment, and can also realize a specific alignment state by controlling it more uniformly and more precisely.

[0057] As the alignment control agent that promotes homogeneous alignment, for example, a low molecular weight alignment control agent or a high molecular weight alignment control agent can be used. For low molecular weight alignment control agents, for example, the descriptions in paragraphs

[0009] to

[0083] of JP 2002-20363 A, paragraphs

[0111] to

[0120] of JP 2006-106662 A, and paragraphs

[0021] to

[0029] of JP 2012-211306 A can be referred to, the contents of which are incorporated herein by reference. Furthermore, for polymer orientation control agents, reference can be made to, for example, paragraphs

[0021] to

[0057] of JP-A No. 2004-198511 and paragraphs

[0121] to

[0167] of JP-A No. 2006-106662, the contents of which are incorporated herein by reference.

[0058] Examples of alignment control agents that form or promote homeotropic alignment include boronic acid compounds and onium salt compounds. Specific examples of such compounds include those described in JP-A-2008-225281, paragraphs

[0023] to

[0032] , JP-A-2012-208397, paragraphs

[0052] to

[0058] , JP-A-2008-026730, paragraphs

[0024] to

[0055] , and JP-A-2016-193869, paragraphs

[0043] to

[0055] , and the like, the contents of which are incorporated herein by reference.

[0059] On the other hand, cholesteric alignment can be achieved by adding a chiral agent to the polymerizable liquid crystal composition of the present invention, and the rotation direction of the cholesteric alignment can be controlled by the direction of the chirality. The pitch of the cholesteric alignment can be controlled depending on the alignment control force of the chiral agent.

[0060] When an alignment control agent is contained, its content is preferably 0.01 to 10 mass %, more preferably 0.05 to 5 mass %, based on the total mass of solids in the composition. When the content is within this range, a desired alignment state can be achieved, and a uniform, highly transparent cured product can be obtained without precipitation, phase separation, alignment defects, etc.

[0061] [Other Components] The liquid crystal composition of the present invention may contain components other than the above-mentioned components, such as a surfactant, a tilt angle control agent, an alignment aid, a plasticizer, and a crosslinking agent.

[0062] [Benzoquinone Derivative] The benzoquinone derivative of the present invention is a compound represented by the above formula (A) (specific compound A).

[0063] [Liquid Crystal Cured Layer] The liquid crystal cured layer of the present invention is a liquid crystal cured layer obtained by fixing the alignment state of the liquid crystal composition of the present invention described above. Examples of methods for forming the liquid crystal cured layer include a method in which the liquid crystal composition of the present invention described above is used to achieve a desired alignment state, and then the liquid crystal composition is fixed by polymerization. While the polymerization conditions are not particularly limited, it is preferable to use ultraviolet light for polymerization by light irradiation. The irradiation dose is 10 mJ / cm. ２ ~50 J / cm ２ is preferred, and 20 mJ / cm ２ ~5 J / cm ２ More preferably, 30 mJ / cm ２ ~3 J / cm ２ is more preferably 50 mJ / cm ２ ~1000mJ / cm ２ is particularly preferred. In order to promote the polymerization reaction, the polymerization may be carried out under heating conditions. The liquid crystal cured layer can be formed on any support or alignment film in an optical film described later, or on a polarizer in a polarizing plate described later.

[0064] The orientation state of the liquid crystal compound in the cured liquid crystal layer of the present invention may be any of horizontal, vertical, tilted, and twisted orientations, and is preferably fixed in a state of horizontal orientation relative to the main surface of the cured liquid crystal layer. In this specification, "horizontal orientation" refers to a state in which the major axis direction of the liquid crystal compound is parallel to the main surface of the cured liquid crystal layer (or, when the cured liquid crystal layer is formed on a member such as a support or an alignment film, the surface of the member). Strict parallelism is not required, and in this specification, it refers to an orientation in which the angle between the major axis direction of the liquid crystal compound and the main surface of the cured liquid crystal layer is less than 10°. In the cured liquid crystal layer, the angle between the major axis direction of the liquid crystal compound and the main surface of the cured liquid crystal layer is preferably 0 to 5°, more preferably 0 to 3°, and even more preferably 0 to 2°.

[0065] The liquid crystal cured layer of the present invention is preferably an optically anisotropic layer, more preferably a positive A plate or a positive C plate, and even more preferably a positive A plate.

[0066] Here, a positive A plate (positive A plate) and a positive C plate (positive C plate) are defined as follows. When the refractive index in the in-plane slow axis direction of the film (the direction in which the in-plane refractive index is maximum) is nx, the refractive index in the in-plane direction perpendicular to the in-plane slow axis is ny, and the refractive index in the thickness direction is nz, a positive A plate satisfies the relationship of formula (A1), and a positive C plate satisfies the relationship of formula (C1). Note that a positive A plate has a positive Rth, and a positive C plate has a negative Rth. Formula (A1) nx>ny≒nz Formula (C1) nz>nx≒ny Note that the above "≒" encompasses not only the case where both are completely identical, but also the case where both are substantially identical. Regarding "substantially the same," for a positive A plate, "ny ≒ nz" includes, for example, a case where (ny - nz) x d (where d is the film thickness) is -10 to 10 nm, preferably -5 to 5 nm, and "nx ≒ nz" includes, for example, a case where (nx - nz) x d (where d is the film thickness) is -10 to 10 nm, preferably -5 to 5 nm. Also, for a positive C plate, "nx ≒ ny" includes, for example, a case where (nx - ny) x d (where d is the film thickness) is 0 to 10 nm, preferably 0 to 5 nm.

[0067] When the liquid crystal cured layer of the present invention is a positive A plate, from the viewpoint of functioning as a λ / 4 plate, Re(550) is preferably 100 to 180 nm, more preferably 120 to 160 nm, even more preferably 130 to 150 nm, and particularly preferably 130 to 145 nm. Here, the "λ / 4 plate" is a plate having a λ / 4 function, specifically, a plate having a function of converting linearly polarized light of a certain wavelength into circularly polarized light (or circularly polarized light into linearly polarized light).

[0068] When the liquid crystal composition of the present invention contains a dichroic material, the liquid crystal cured layer of the present invention can be used as a polarizer (light absorption anisotropic film).

[0069] [Optical Film] The optical film of the present invention is an optical film having the liquid crystal cured layer of the present invention. The structure of the optical film will be described with reference to FIG. 1. FIG. 1 is a schematic cross-sectional view showing an example of an optical film. Note that FIG. 1 is a schematic view, and the thickness relationships and positional relationships of the layers do not necessarily correspond to the actual ones, and the support and alignment film shown in FIG. 1 are both optional components.

[0070] The optical film 10 shown in FIG. 1 includes, in this order, a support 16, an alignment film 14, and a cured liquid crystal layer 12 formed from the cured liquid crystal composition of the present invention. The cured liquid crystal layer 12 may also be a laminate of two or more different cured liquid crystal layers. For example, when the polarizing plate of the present invention (described later) is used as a circular polarizing plate, or when the optical film of the present invention is used as an optical compensation film for an IPS (In-Plane-Switching) or FFS (Fringe-Field-Switching) liquid crystal display device, a laminate of a positive A plate and a positive C plate is preferred. The cured liquid crystal layer may also be peeled from the support and used alone as an optical film. Various components used in the optical film are described in detail below.

[0071] [Liquid Crystal Cured Layer] The liquid crystal cured layer of the optical film of the present invention is the liquid crystal cured layer of the present invention described above. In the optical film, the thickness of the liquid crystal cured layer is not particularly limited, but is preferably 0.1 to 10 μm, more preferably 0.5 to 5 μm.

[0072] [Support] As described above, the optical film may have a support as a substrate for forming the liquid crystal cured layer. Such a support is preferably transparent. Specifically, it is preferable that the light transmittance is 80% or more.

[0073] Examples of such a support include glass substrates and polymer films. Examples of materials for the polymer film include cellulose-based polymers; acrylic polymers having acrylic acid ester polymers such as polymethyl methacrylate and lactone ring-containing polymers; thermoplastic norbornene-based polymers; polycarbonate-based polymers; polyester-based polymers such as polyethylene terephthalate and polyethylene naphthalate; styrene-based polymers such as polystyrene and acrylonitrile-styrene copolymers (AS resins); polyolefin-based polymers such as polyethylene, polypropylene, and ethylene-propylene copolymers; vinyl chloride-based polymers; amide-based polymers such as nylon and aromatic polyamide; imide-based polymers; sulfone-based polymers; polyethersulfone-based polymers; polyetheretherketone-based polymers; polyphenylene sulfide-based polymers; vinylidene chloride-based polymers; vinyl alcohol-based polymers; vinyl butyral-based polymers; arylate-based polymers; polyoxymethylene-based polymers; epoxy-based polymers; and polymers obtained by mixing these polymers. In addition, the polarizer described below may also serve as such a support.

[0074] The thickness of the support is not particularly limited, but is preferably 5 to 60 μm, and more preferably 5 to 40 μm.

[0075] [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). When the optical film has any of the above-mentioned supports, the alignment film may be sandwiched between the support and the liquid crystal cured layer. In addition, the above-mentioned support may also serve as the alignment film.

[0076] The alignment film may be any film capable of horizontally aligning the polymerizable liquid crystal compound contained in the composition. Alignment films generally contain a polymer as the main component. Polymer materials for alignment films are described in numerous literature, and many commercially available products are available. Preferred polymer materials for alignment films are polyvinyl alcohol, polyimide, or derivatives thereof, with modified or unmodified polyvinyl alcohol being more preferred. Examples of alignment films that may be included in the optical film include the alignment film described in WO 01 / 88574, page 43, line 24 to page 49, line 8; the alignment film made of modified polyvinyl alcohol described in paragraphs

[0071] to

[0095] of Japanese Patent No. 3907735; and the liquid crystal alignment film formed from the liquid crystal aligning agent described in JP 2012-155308 A.

[0077] It is preferable to use a photo-alignment film as the alignment film, since the surface of the alignment film is not in contact with any object during the formation of the alignment film, and it is possible to prevent deterioration of the surface condition. The photo-alignment film is not particularly limited, but it can be an alignment film formed from a polymer material such as a polyamide compound and a polyimide compound described in paragraphs

[0024] to

[0043] of International Publication No. 2005 / 096041; a liquid crystal alignment film formed from a liquid crystal alignment agent having a photo-alignment group described in Japanese Patent Laid-Open No. 2012-155308; and a product name LPP-JP265CP manufactured by Rolic Technologies, Inc., or the like.

[0078] The thickness of the alignment film is not particularly limited, but from the viewpoint of reducing surface irregularities that may be present on the support and forming a liquid crystal cured layer with a uniform film thickness, the thickness is preferably 0.01 to 10 μm, more preferably 0.01 to 1 μm, and even more preferably 0.01 to 0.5 μm.

[0079] [Another liquid crystal cured layer] In the optical film, the liquid crystal cured layer is preferably formed on the surface of another liquid crystal cured layer. Here, the other liquid crystal cured layer may be, for example, a liquid crystal cured layer obtained by fixing the alignment state of a composition obtained by removing the specific compound A from the liquid crystal composition of the present invention described above. Specifically, it may be a liquid crystal cured layer obtained by fixing the alignment state of a composition containing the above-mentioned liquid crystal compound, a polymerization initiator, a leveling agent, a solvent, etc.

[0080] [Ultraviolet Absorber] In consideration of the influence of external light (especially ultraviolet light), the optical film preferably contains an ultraviolet (UV) absorber. The ultraviolet absorber may be contained in the cured liquid crystal layer, or may be contained in a member other than the cured liquid crystal layer constituting the optical film. A suitable example of the member other than the cured liquid crystal layer is a support. As the ultraviolet absorber, any conventionally known material capable of exhibiting ultraviolet absorption properties can be used. Among such ultraviolet absorbers, benzotriazole-based or hydroxyphenyltriazine-based ultraviolet absorbers are preferred from the viewpoint of high ultraviolet absorption and obtaining ultraviolet absorption ability (ultraviolet blocking ability) used in image display devices. Furthermore, in order to widen the ultraviolet absorption width, it is also preferable to use two or more ultraviolet absorbers with different maximum absorption wavelengths in combination.

[0081] Examples of ultraviolet absorbers include the compounds described in paragraphs

[0258] to

[0259] of JP 2012-18395 A and the compounds described in paragraphs

[0055] to

[0105] of JP 2007-72163 A. Commercially available products that can be used include Tinuvin 400, Tinuvin 405, Tinuvin 460, Tinuvin 477, Tinuvin 479, and Tinuvin 1577 (all manufactured by BASF).

[0082] [Polarizing Plate] The polarizing plate of the present invention comprises the optical film of the present invention described above and a polarizer. Furthermore, when the liquid crystal cured layer of the present invention described above is a λ / 4 plate (positive A plate), the polarizing plate of the present invention can be used as a circular polarizing plate. Furthermore, when the liquid crystal cured layer of the present invention described above is a λ / 4 plate (positive A plate), the angle between the slow axis of the λ / 4 plate and the absorption axis of the polarizer described below is preferably 30 to 60°, more preferably 40 to 50°, even more preferably 42 to 48°, and particularly preferably 45°. Here, the "slow axis" of the λ / 4 plate refers to the direction in which the refractive index is maximized in the plane of the λ / 4 plate, and the "absorption axis" of the polarizer refers to the direction in which the absorbance is highest. Furthermore, the polarizing plate of the present invention can also be used as an optical compensation film for an IPS-type or FFS-type liquid crystal display device. When the polarizing plate of the present invention is used as an optical compensation film for an IPS-type or FFS-type liquid crystal display device, the above-mentioned liquid crystal cured layer of the present invention can be at least one plate of a laminate of a positive A plate and a positive C plate, and is preferably a positive A plate. In this case, it is preferable that the angle between the slow axis of the positive A plate and the absorption axis of the polarizer described below is perpendicular or parallel. Specifically, it is more preferable that the angle between the slow axis of the positive A plate and the absorption axis of the polarizer described below is 0 to 5° or 85 to 95°. Furthermore, when the polarizing plate of the present invention is formed by laminating a polarizer, a positive C plate, and a positive A plate in this order, it is more preferable that the angle between the slow axis of the positive A plate and the absorption axis of the polarizer is parallel. Similarly, when the polarizing plate of the present invention is formed by laminating a polarizer, a positive A plate, and a positive C plate in this order, it is more preferable that the angle between the slow axis of the positive A plate and the absorption axis of the polarizer is perpendicular. When the polarizing plate of the present invention is used in a liquid crystal display device described later, the angle between the slow axis of the cured liquid crystal layer and the absorption axis of the polarizer described later is preferably parallel or perpendicular. In this specification, "parallel" does not require strict parallelism, but means that the angle between one axis and the other is less than 10°.Furthermore, in this specification, "orthogonal" does not require that they be strictly orthogonal, but rather means that the angle between one side and the other is greater than 80° and less than 100°.

[0083] [Polarizer] The polarizer of the polarizing plate of the present invention is not particularly limited as long as it has the function of converting light into specific linearly polarized light, and conventionally known absorptive polarizers and reflective polarizers can be used. Examples of absorptive polarizers include iodine-based polarizers, dye-based polarizers using dichroic dyes, and polyene-based polarizers. Iodine-based polarizers and dye-based polarizers include coated polarizers and stretched polarizers, and either type can be used. However, polarizers produced by adsorbing iodine or a dichroic dye onto polyvinyl alcohol and stretching the resulting film are preferred. Furthermore, methods for obtaining polarizers by stretching and dyeing a laminated film having a polyvinyl alcohol layer formed on a substrate are described in Japanese Patent Nos. 5,048,120, 5,143,918, 4,691,205, 4,751,481, and 4,751,486. These known techniques related to polarizers can also be preferably used. As the reflective polarizer, a polarizer in which thin films with different birefringence are laminated, a wire grid polarizer, a polarizer in which a cholesteric liquid crystal having a selective reflection region is combined with a quarter-wave plate, etc. are used. Among them, a polyvinyl alcohol-based resin (-CH ２ A polymer containing —CHOH— as a repeating unit, particularly at least one selected from the group consisting of polyvinyl alcohol and an ethylene-vinyl alcohol copolymer, is preferred.

[0084] In the present invention, the thickness of the polarizer is not particularly limited, but is preferably 3 μm to 60 μm, more preferably 5 μm to 30 μm, and even more preferably 5 μm to 15 μm.

[0085] [Adhesive Layer] The polarizing plate of the present invention may have an adhesive layer disposed between the liquid crystal cured layer in the optical film of the present invention and the polarizer. The adhesive layer used for laminating the liquid crystal cured layer and the polarizer refers to, for example, a substance having a ratio of storage modulus G' to loss modulus G" (tan δ = G" / G') measured with a dynamic viscoelasticity measuring device of 0.001 to 1.5, and includes so-called adhesives and substances that tend to creep. Adhesives that can be used in the present invention include, but are not limited to, polyvinyl alcohol-based adhesives.

[0086] [Image Display Device] The image display device of the present invention is an image display device having the optical film of the present invention or the polarizing plate of the present invention. The display element used in the image display device is not particularly limited, and examples thereof include a liquid crystal cell, an organic electroluminescence (hereinafter abbreviated as "EL (Electro Luminescence)") display panel, and a plasma display panel. Of these, a liquid crystal cell and an organic EL display panel are preferred, and a liquid crystal cell is more preferred. 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.

[0087] [Liquid Crystal Display Device] A liquid crystal display device, which is an example of an image display device, is a liquid crystal display device having the above-described polarizing plate and a liquid crystal cell. Of the polarizing plates provided on both sides of the liquid crystal cell, it is preferable to use the above-described polarizing plate as the front-side polarizing plate, and it is more preferable to use the above-described polarizing plate as the front-side and rear-side polarizing plates. The liquid crystal cell constituting the liquid crystal display device will be described in detail below.

[0088] <Liquid Crystal Cell> The liquid crystal cell used in the liquid crystal display device is preferably, but not limited to, 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. In a TN mode liquid crystal cell, when no voltage is applied, the rod-shaped liquid crystal molecules are aligned substantially horizontally and further twisted at an angle of 60 to 120 degrees. TN mode liquid crystal cells are most commonly used in color TFT liquid crystal displays and are described in numerous literature. In a VA mode liquid crystal cell, the rod-shaped liquid crystal molecules are aligned substantially vertically when no voltage is applied. VA mode liquid crystal cells include (1) narrowly defined VA mode liquid crystal cells in which rod-shaped liquid crystal molecules are aligned substantially vertically when no voltage is applied and substantially horizontally when a voltage is applied (described in Japanese Patent Application Laid-Open No. 2-176625), (2) multi-domain VA mode liquid crystal cells (described in SID97, Digest of tech. Papers (Proceedings) 28 (1997) 845) in order to widen the viewing angle (MVA mode liquid crystal cells), (3) n-ASM mode liquid crystal cells in which rod-shaped liquid crystal molecules are aligned substantially vertically when no voltage is applied and substantially horizontally when a voltage is applied (described in Proceedings of the Japan Liquid Crystal Symposium 58-59 (1998)), and (4) SURVIVAL mode liquid crystal cells (announced at LCD International 98). Furthermore, VA-mode liquid crystal cells may be any of PVA (Patterned Vertical Alignment) type, optical alignment type, and PSA (Polymer-Sustained Alignment) type. Details of these modes are described in Japanese Patent Application Laid-Open No. 2006-215326 and Japanese Patent Application Laid-Open No. 2008-538819. In IPS-mode liquid crystal cells, rod-shaped liquid crystal molecules are aligned substantially parallel to the substrates, and the liquid crystal molecules respond in a planar manner when an electric field parallel to the substrate surface is applied. In IPS-mode cells, black is displayed when no electric field is applied, and the absorption axes of a pair of upper and lower polarizing plates are perpendicular to each other.Methods of using an optical compensation sheet to reduce light leakage in oblique directions during black display and improve the viewing angle are disclosed in JP-A Nos. 10-54982, 11-202323, 9-292522, 11-133408, 11-305217, and 10-307291.

[0089] [Organic EL Display Device] An example of an organic EL display device, which is an example of an image display device, includes, from the viewing side, a polarizer, a λ / 4 plate (positive A plate) made of the above-mentioned liquid crystal cured layer, and an organic EL display panel, in this order. The organic EL display panel is a display panel configured using organic EL elements in which an organic light-emitting layer (organic electroluminescence layer) is sandwiched between electrodes (between a cathode and an anode). The configuration of the organic EL display panel is not particularly limited, and a known configuration may be adopted.

[0090] The present invention will be described in more detail below with reference to examples. The materials, amounts used, ratios, treatment contents, treatment procedures, etc. shown in the following examples can be changed as appropriate without departing from the spirit of the present invention. Therefore, the scope of the present invention should not be construed as being limited by the examples shown below.

[0091] [Synthesis of Specific Compound (A-1)] Specific compound (A-1) was synthesized according to the synthesis method described in JP-A-2012-97078 and the following scheme.

[0092] Specifically, 8 g of compound (A-1-3), 4.6 g of Lawesson's reagent, and 60 g of toluene were placed in a 200 mL three-neck flask, heated to 80°C, and reacted for 12 hours. After cooling to room temperature, a crude containing compound (A-1-2) was obtained. Subsequently, the crude containing compound (A-1-2), 5.9 g of NaOH, and 125 g of water were mixed and cooled under ice-cooling. An aqueous solution containing 22 g of potassium ferricyanate was then added under ice-cooling, and the reaction was continued. After reacting for 12 hours at 60°C, the precipitated solid was filtered by suction. The filtered solid was washed with water and heptane and crystallized with toluene to obtain a yellow solid (A-1-1). Next, 2.45 g of aluminum chloride and 25 mL of toluene were added to a 100 mL three-neck flask and stirred under nitrogen. 2.5 g of the yellow solid (A-1-1) was added to the mixture, stirred at room temperature for 3 hours, and then further stirred at 60°C for 5 hours. After that, the mixture was allowed to cool to room temperature, 1N hydrochloric acid was added, and the mixture was stirred for 30 minutes. The precipitated solid [a mixture of (A-1) and (A-1-O)] was filtered by suction, washed by suspending it in 1N hydrochloric acid, and then washed with 25 mL of pure water. The obtained solid was oxidized using silver oxide by a general method (Tetrahedron Letters 46.26 (2005): 4449-4451.), to obtain 1.1 g of specific compound (A-1). The results of mass spectrometry (MS) of the obtained specific compound (A-1) are shown below. m / z: 309.05 (100.0%), 310.05 (19.4%), 311.04 (4.5%), 311.05 (2.4%), 312.05 (1.0%)

[0093] [Synthesis of Other Specific Compounds] Specific compounds other than the specific compound (A-1) were also synthesized by oxidizing the phenol compound as the raw material in the same manner as above.

[0094] Example 1 Liquid crystal composition 1 was prepared having the following composition: Liquid crystal composition 1 222.5 parts by mass of liquid crystal compound (B-1) below 47.0 parts by mass of specific compound (A-1) below 3.0 parts by mass of polymerizable compound (D-1) below 1.5 parts by mass of polymerization initiator S1 below 0.1 parts by mass of leveling agent P1 below Cyclopentanone 92.5 parts by mass Methyl ethyl ketone 64.2 parts by mass

[0095] Liquid crystal compound (B-1)

[0096] Specific compound (A-1)

[0097] Polymerizable compound (D-1)

[0098] Polymerization initiator S1

[0099] Leveling agent P1 (in the following, a, b, and c represent the content (mass %) of each repeating unit relative to the total repeating units, with a = 44.8, b = 50.3, and c = 4.9.)

[0100] Example 2 Liquid crystal composition 2 was prepared having the following composition: Liquid crystal composition 2 222.5 parts by mass of the following liquid crystal compound (B-2) 47.0 parts by mass of the following specific compound (A-2) 3.0 parts by mass of the above polymerizable compound (D-1) 1.5 parts by mass of the above polymerization initiator S1 0.1 parts by mass of the above leveling agent P1 Cyclopentanone 92.5 parts by mass Methyl ethyl ketone 64.2 parts by mass

[0101] Liquid crystal compound (B-2)

[0102] Specific compound (A-2)

[0103] Example 3 Liquid crystal composition 3 was prepared having the following composition. ---------------- Liquid crystal composition 3 ---------------- - 222.5 parts by mass of the following liquid crystal compound (B-3) - 47.0 parts by mass of the following specific compound (A-3) - 3.0 parts by mass of the above polymerizable compound (D-1) - 1.5 parts by mass of the above polymerization initiator S1 - 0.1 parts by mass of the above leveling agent P1 - 92.5 parts by mass of cyclopentanone - 64.2 parts by mass of methyl ethyl ketone.

[0104] Liquid crystal compound (B-3)

[0105] Specific compound (A-3)

[0106] Example 4 Liquid crystal composition 4 was prepared having the following composition: Liquid crystal composition 4 - 222.5 parts by mass of the above liquid crystal compound (B-1) - 55.6 parts by mass of the above specific compound (A-1) - 3.0 parts by mass of the above polymerizable compound (D-1) - 1.5 parts by mass of the above polymerization initiator S1 - 0.1 parts by mass of the above leveling agent P1 - 92.5 parts by mass of cyclopentanone - 64.2 parts by mass of methyl ethyl ketone.

[0107] Example 5 Liquid crystal composition 5 was prepared having the following composition: Liquid crystal composition 5 - 222.5 parts by mass of the liquid crystal compound (B-2) - 47.0 parts by mass of the specific compound (A-1) - 3.0 parts by mass of the polymerizable compound (D-1) - 1.5 parts by mass of the polymerization initiator S1 - 0.1 parts by mass of the leveling agent P1 - 92.5 parts by mass of cyclopentanone - 64.2 parts by mass of methyl ethyl ketone.

[0108] Example 6 Liquid crystal composition 6 was prepared having the following composition: Liquid crystal composition 6 - 222.5 parts by mass of the liquid crystal compound (B-1) - 47.0 parts by mass of the specific compound (A-2) - 3.0 parts by mass of the polymerizable compound (D-1) - 1.5 parts by mass of the polymerization initiator S1 - 0.1 parts by mass of the leveling agent P1 - 92.5 parts by mass of cyclopentanone - 64.2 parts by mass of methyl ethyl ketone.

[0109] Example 7 Liquid crystal composition 7 was prepared having the following composition. ---------------- Liquid crystal composition 7 ---------------- 222.5 parts by mass of the following liquid crystal compound (B-5) 47.0 parts by mass of the following specific compound (A-5) 3.0 parts by mass of the above polymerizable compound (D-1) 1.5 parts by mass of the above polymerization initiator S1 0.1 parts by mass of the above leveling agent P1 Cyclopentanone 92.5 parts by mass Methyl ethyl ketone 64.2 parts by mass

[0110] Liquid crystal compound (B-5)

[0111] Specific compound (A-5)

[0112] Example 8 Liquid crystal composition 8 was prepared having the following composition. ---------------- Liquid crystal composition 8 ------------------ 222.5 parts by mass of the following liquid crystal compound (B-6) -- 47.0 parts by mass of the following specific compound (A-6) -- 3.0 parts by mass of the above polymerizable compound (D-1) -- 1.5 parts by mass of the above polymerization initiator S1 -- 0.1 parts by mass of the above leveling agent P1 -- 92.5 parts by mass of cyclopentanone -- 64.2 parts by mass of methyl ethyl ketone.

[0113] Liquid crystal compound (B-6)

[0114] Specific compound (A-6)

[0115] Example 9 Liquid crystal composition 9 was prepared having the following composition: Liquid crystal composition 9 - 222.5 parts by mass of the following liquid crystal compound (B-7) - 47.0 parts by mass of the following specific compound (A-7) - 3.0 parts by mass of the above polymerizable compound (D-1) - 1.5 parts by mass of the above polymerization initiator S1 - 0.1 parts by mass of the above leveling agent P1 - 92.5 parts by mass of cyclopentanone - 64.2 parts by mass of methyl ethyl ketone.

[0116] Liquid crystal compound (B-7)

[0117] Specific compound (A-7)

[0118] Example 10 A liquid crystal composition 10 was prepared having the following composition. -------------------------------- Liquid Crystal Composition 10-------------------------------- 222.5 parts by mass of the following liquid crystal compound (B-8) 47.0 parts by mass of the following specific compound (A-8) 3.0 parts by mass of the above polymerizable compound (D-1) 1.5 parts by mass of the above polymerization initiator S1 0.1 parts by mass of the above leveling agent P1 Cyclopentanone 92.5 parts by mass Methyl ethyl ketone 64.2 parts by mass

[0119] Liquid crystal compound (B-8)

[0120] Specific compound (A-8)

[0121] Example 11 Liquid crystal composition 11 was prepared having the following composition. ---------------- Liquid crystal composition 11 ---------------- - 222.5 parts by mass of the following liquid crystal compound (B-9) - 47.0 parts by mass of the following specific compound (A-9) - 3.0 parts by mass of the above polymerizable compound (D-1) - 1.5 parts by mass of the above polymerization initiator S1 - 0.1 parts by mass of the above leveling agent P1 - 92.5 parts by mass of cyclopentanone - 64.2 parts by mass of methyl ethyl ketone.

[0122] Liquid crystal compound (B-9)

[0123] Specific compound (A-9)

[0124] Comparative Example 1 A liquid crystal composition C1 was prepared having the following composition: Liquid Crystal Composition C1 269.5 parts by mass of the above liquid crystal compound (B-1) 3.0 parts by mass of the above polymerizable compound (D-1) 1.5 parts by mass of the above polymerization initiator S1 0.1 parts by mass of the above leveling agent P1 92.5 parts by mass of cyclopentanone 64.2 parts by mass of methyl ethyl ketone

[0125] Comparative Example 2 Liquid crystal composition C2 was prepared having the following composition: Liquid crystal composition C2 - 222.5 parts by mass of the above liquid crystal compound (B-1) - 47.0 parts by mass of ADK STAB LA-29 - 3.0 parts by mass of the above polymerizable compound (D-1) - 1.5 parts by mass of the above polymerization initiator S1 - 0.1 parts by mass of the above leveling agent P1 - 92.5 parts by mass of cyclopentanone - 64.2 parts by mass of methyl ethyl ketone.

[0126] [Preparation of Optical Film] Liquid crystal composition 1 prepared in Example 1 was applied by spin coating to a glass substrate with a rubbed polyimide alignment film (SE-150 manufactured by Nissan Chemical Industries, Ltd.). The coating film was subjected to an alignment treatment at 200°C to form a liquid crystal layer. Thereafter, the film was cooled to 135°C and irradiated with 1000 mJ / cm. ２ The alignment was fixed by ultraviolet irradiation to form a liquid crystal cured layer (optically anisotropic layer), and optical film 1 for wavelength dispersion measurement was produced. The retardation of optical film 1 was measured, and it was confirmed that Re(450) / Re(550)=0.88. In a similar manner, liquid crystal cured layers were formed for the liquid crystal compositions prepared in Examples 2 to 11 and Comparative Examples 1 and 2, and optical films were produced.

[0127] [Lightfastness Evaluation] The prepared optical film was exposed to light for 100 hours using a Super Xenon Weather Meter SX75. During this time, a protective film 1 was sandwiched between the optical film and the Super Xenon Weather Meter SX75, and the light was arranged so that it was incident from the liquid crystal cured layer. The exposed sample was compared with a similar unexposed sample to measure the color change of the film and evaluate it according to the following criteria. The results are shown in Table 1 below. <Color Change> A: Δb*≦2.0 compared to the sample not exposed to the xenon weather meter B: 2.0<Δb*≦4.0 compared to the sample not exposed to the xenon weather meter C: 4.0<Δb* compared to the sample not exposed to the xenon weather meter

[0128] [Alignment Evaluation] The alignment was measured by placing an LED (Light Emitting Diode) light source, a lower polarizing plate, a cured liquid crystal layer (an optical film made from each liquid crystal composition), and an upper polarizing plate on a table, from bottom to top, so that each surface was horizontal. At this time, the sample and the upper polarizing plate were rotatable. The luminance of light emitted from the light source and transmitted through the lower polarizing plate, the sample, and the upper polarizing plate in this order was measured from the vertical direction using a luminance meter (BM-5A (manufactured by TOPCON)). The measurement was first performed by rotating the upper polarizing plate in the absence of a sample to the position where the luminance was lowest (crossed Nicols state). The sample peeled from the protective film was inserted between the polarizing plates, and the sample was rotated under crossed Nicols to measure the minimum luminance. Next, the two polarizing plates, the upper polarizing plate and the lower polarizing plate, were arranged in parallel Nicols, and the sample was rotated to measure the maximum luminance. In order to eliminate the contribution of luminance leakage due to the upper and lower polarizing plates, the value calculated by the following formula was evaluated according to the following evaluation criteria. The results are shown in Table 1 below. Orientation=1 / ((minimum luminance under crossed Nicols with a sample placed) / (maximum luminance under parallel Nicols with a sample placed)-(minimum luminance under crossed Nicols without a sample) / (maximum luminance under parallel Nicols without a sample)) <Evaluation criteria> A: The orientation is 200,000 or more B: The orientation is 100,000 or more and less than 200,000 C: The orientation is less than 100,000

[0129]

[0130] The results shown in Table 1 above indicate that the absence of specific compound A resulted in poor lightfastness (Comparative Example 1). Furthermore, the addition of a compound other than the compound represented by formula (A) improved lightfastness, but resulted in poor alignment (Comparative Example 2). In contrast, it was found that the use of a liquid crystal composition containing specific compound A and a liquid crystal compound allowed the preparation of a cured liquid crystal layer with both good alignment and lightfastness (Examples 1 to 11). In particular, a comparison between Example 1 and Example 4 indicated that the alignment was better when the content of specific compound A was 18% by mass or less relative to the total mass of the specific compound and the liquid crystal compound. Furthermore, a comparison between Example 1 and Example 5, and a comparison between Example 2 and Example 6 indicated that, with regard to the structures of the compound represented by formula (A) (specific compound A) and the compound represented by formula (B) (liquid crystal compound), the Ar １ and Ar in the above formula (B) ２ It was found that when the structure of the film is the same as that of the film, the orientation becomes better.

[0131] 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: 【Chemistry 1】 Here, in the formula (A), Ar １ represents any aromatic ring selected from the group consisting of groups represented by the following formulas (BQ-1) to (BQ-5). 【Chemistry 2】 Here, in the formulas (BQ-1) to (BQ-5), * indicates the bonding position with the oxygen atom. Q １ represents N or CH. Q ２ is -S-, -O-, or -N(R ６ )-, R ６ represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. Y １ represents an aromatic hydrocarbon group having 6 to 12 carbon atoms which may have a substituent, an aromatic heterocyclic group having 3 to 12 carbon atoms which may have a substituent, or an alicyclic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent, and -CH ２ One or more of - may be substituted with -O-, -S- or -NH-. Z １ , Z ２ and Z ３ each independently represents 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 represents R ７ ~R １２ each independently represents 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. A ３ and A ４ are each independently —O—, —N(R １３ represents a group selected from the group consisting of —, —S—, and —CO—; R １３ represents a hydrogen atom or a substituent. X represents a nonmetallic atom of Groups 14 to 16. However, the nonmetallic atom may be bonded to a hydrogen atom or a substituent. D ７ and D ８ each independently represents a single bond, or —CO—, —O—, —S—, —C(═S)—, or —CR １ R ２ -, -CR ３ =CR ４ -, -NR ５ -, or a divalent linking group formed by a combination of two or more thereof, R １ ~R ５ each independently represents a hydrogen atom, a fluorine atom, or an alkyl group having 1 to 12 carbon atoms. SP ３ and SP ４ each independently represents a single bond or a divalent aliphatic hydrocarbon group having 1 to 20 carbon atoms, provided that the —CH ２ One or more of - may be substituted with -O-, -S-, -NH-, -N(Q)- or -CO-. Q represents a substituent. L ３ and L ４ each independently represents a monovalent organic group. Ax represents an organic group having 2 to 30 carbon atoms and having at least one aromatic ring selected from the group consisting of aromatic hydrocarbon rings and aromatic heterocycles. Ay represents a hydrogen atom, an alkyl group having 1 to 12 carbon atoms which may have a substituent, or an organic group having 2 to 30 carbon atoms and having at least one aromatic ring selected from the group consisting of an aromatic hydrocarbon ring and an aromatic heterocycle. The aromatic rings in Ax and Ay may have a substituent, and Ax and Ay may be bonded to form a ring. Q ３ represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms which may have a substituent.

2. 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 the formula (B), a1, a2, g1, and g2 each independently represent 0 or 1, provided that 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 independently represents a single bond, or —CO—, —O—, —S—, —C(═S)—, or —CR １ R ２ -, -CR ３ =CR ４ -, -NR ５ -, or a divalent linking group formed by a combination of two or more thereof, R １ ~R ５ each independently represents a hydrogen atom, a fluorine atom, or an alkyl group having 1 to 12 carbon atoms. G １ and G ２ each independently represents an aromatic ring having 6 to 20 carbon atoms which may have a substituent, or a divalent alicyclic hydrocarbon group having 5 to 20 carbon atoms which may have a substituent, and —CH ２ One or more of - may be substituted with -O-, -S- or -NH-. A １ and A ２ each independently represents an aromatic ring having 6 to 20 carbon atoms which may have a substituent, or a divalent alicyclic hydrocarbon group having 5 to 20 carbon atoms which may have a substituent, and —CH ２ One or more of - may be substituted with -O-, -S- or -NH-. SP １ and SP ２ each independently represents a single bond or a divalent aliphatic hydrocarbon group having 1 to 20 carbon atoms, provided that the —CH ２ One or more of - may be substituted with -O-, -S-, -NH-, -N(Q)- or -CO-. Q represents a substituent. L １ and L ２ each independently represents a monovalent organic group; １ and L ２ At least one of Ar represents a polymerizable group. ２ is 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 the groups represents a polymerizable group. Ar ２ represents any aromatic ring selected from the group consisting of groups represented by the following formulae (Ar-1) to (Ar-7). 【Transformation 3】 Here, in the formulas (Ar-1) to (Ar-7), * is D １ or D ２ represents the bonding position with Q １ represents N or CH. Q ２ is -S-, -O-, or -N(R ６ )-, R ６ represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. Y １ represents an aromatic hydrocarbon group having 6 to 12 carbon atoms which may have a substituent, an aromatic heterocyclic group having 3 to 12 carbon atoms which may have a substituent, or an alicyclic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent, and -CH ２ One or more of - may be substituted with -O-, -S- or -NH-. Z １ , Z ２ and Z ３ each independently represents 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 represents R ７ ~R １２ each independently represents 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. A ３ and A ４ are each independently —O—, —N(R １３ represents a group selected from the group consisting of —, —S—, and —CO—; R １３ represents a hydrogen atom or a substituent. X represents a nonmetallic atom of Groups 14 to 16. However, the nonmetallic atom may be bonded to a hydrogen atom or a substituent. D ７ and D ８ each independently represents a single bond, or —CO—, —O—, —S—, —C(═S)—, or —CR １ R ２ -, -CR ３ =CR ４ -, -NR ５ -, or a divalent linking group formed by a combination of two or more thereof, R １ ~R ５ each independently represents a hydrogen atom, a fluorine atom, or an alkyl group having 1 to 12 carbon atoms. SP ３ and SP ４ each independently represents a single bond or a divalent aliphatic hydrocarbon group having 1 to 20 carbon atoms, provided that the —CH ２ One or more of - may be substituted with -O-, -S-, -NH-, -N(Q)- or -CO-. Q represents a substituent. L ３ and L ４ each independently represents a monovalent organic group; ３ and L ４ and L in the formula (B). １ and L ２ At least one of the groups represents a polymerizable group. Ax represents an organic group having 2 to 30 carbon atoms and having at least one aromatic ring selected from the group consisting of aromatic hydrocarbon rings and aromatic heterocycles. Ay represents a hydrogen atom, an alkyl group having 1 to 12 carbon atoms which may have a substituent, or an organic group having 2 to 30 carbon atoms and having at least one aromatic ring selected from the group consisting of an aromatic hydrocarbon ring and an aromatic heterocycle. The aromatic rings in Ax and Ay may have a substituent, and Ax and Ay may be bonded to form a ring. Q ３ represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms which may have a substituent.

3. 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 based on the total mass of the compound represented by formula (A) and the liquid crystal compound.

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

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

6. A benzoquinone derivative represented by the following formula (A): 【Chemistry 4】 Here, in the formula (A), Ar １ represents any aromatic ring selected from the group consisting of groups represented by the following formulas (BQ-1) to (BQ-5). 【Transformation 5】 Here, in the formulas (BQ-1) to (BQ-5), * indicates the bonding position with the oxygen atom. Q １ represents N or CH. Q ２ is -S-, -O-, or -N(R ６ )-, R ６ represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. Y １ represents an aromatic hydrocarbon group having 6 to 12 carbon atoms which may have a substituent, an aromatic heterocyclic group having 3 to 12 carbon atoms which may have a substituent, or an alicyclic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent, and -CH ２ One or more of - may be substituted with -O-, -S- or -NH-. Z １ , Z ２ and Z ３ each independently represents 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 represents R ７ ~R １２ each independently represents 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. A ３ and A ４ are each independently —O—, —N(R １３ represents a group selected from the group consisting of —, —S—, and —CO—; R １３ represents a hydrogen atom or a substituent. X represents a nonmetallic atom of Groups 14 to 16. However, the nonmetallic atom may be bonded to a hydrogen atom or a substituent. D ７ and D ８ each independently represents a single bond, or —CO—, —O—, —S—, —C(═S)—, or —CR １ R ２ -, -CR ３ =CR ４ -, -NR ５ -, or a divalent linking group formed by a combination of two or more thereof, R １ ~R ５ each independently represents a hydrogen atom, a fluorine atom, or an alkyl group having 1 to 12 carbon atoms. SP ３ and SP ４ each independently represents a single bond or a divalent aliphatic hydrocarbon group having 1 to 20 carbon atoms, provided that the —CH ２ One or more of - may be substituted with -O-, -S-, -NH-, -N(Q)- or -CO-. Q represents a substituent. L ３ and L ４ each independently represents a monovalent organic group. Ax represents an organic group having 2 to 30 carbon atoms and having at least one aromatic ring selected from the group consisting of aromatic hydrocarbon rings and aromatic heterocycles. Ay represents a hydrogen atom, an alkyl group having 1 to 12 carbon atoms which may have a substituent, or an organic group having 2 to 30 carbon atoms and having at least one aromatic ring selected from the group consisting of an aromatic hydrocarbon ring and an aromatic heterocycle. The aromatic rings in Ax and Ay may have a substituent, and Ax and Ay may be bonded to form a ring. Q ３ represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms which may have a substituent.

7. The benzoquinone derivative according to claim 6, wherein Ar 1 represents any aromatic ring selected from the group consisting of groups represented by the above formulae (BQ-2) to (BQ-5).

8. A liquid crystal cured layer obtained by fixing the alignment state of the liquid crystal composition according to any one of claims 1 to 3.

9. An optical film comprising the liquid crystal cured layer according to claim 8 .

10. A polarizing plate comprising the optical film according to claim 9 and a polarizer.

11. An image display device comprising the optical film according to claim 9 .