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

Abstract

The present invention addresses the problem of providing a liquid crystal composition, a liquid crystal compound, a liquid crystal cured layer, an optical film, a polarizing plate, and an image display device in which the precipitation of the liquid crystal compound is suppressed. This liquid crystal composition contains a first liquid crystal compound represented by formula (1) and a second liquid crystal compound represented by formula (2), and both the first liquid crystal compound and the second liquid crystal compound have a maximum absorption wavelength in the wavelength range of 280-420 nm. .

Description

Technical Field

[0001] This invention relates to a liquid crystal composition, a liquid crystal compound, a liquid crystal cured layer, an optical film, a polarizer, and an image display device. Background Technology

[0002] To eliminate image tinting and expand the viewing angle, optical films such as optical compensation sheets or phase retardation films are used in various image display devices.

[0003] Stretched birefringent films have been used as optical films, but in recent years, it has been proposed to replace stretched birefringent films with optical anisotropic films having optical layers composed of liquid crystal compounds.

[0004] As such optical films, optical films made by polymerizing compounds containing groups represented by a given formula and polymerizable groups are known (for example, see Patent Document 1).

[0005] Existing technical documents Patent documents Patent Document 1: Japanese Patent Application Publication No. 2010-031223 Summary of the Invention

[0006] The technical problem to be solved by the invention The inventors have conducted research on liquid crystal compositions containing the compounds described in Patent Document 1 and have determined that there is room for improvement in the segregation properties of the liquid crystal compounds.

[0007] Therefore, the objective of this invention is to provide a liquid crystal composition, a liquid crystal compound, a liquid crystal curing layer, an optical film, a polarizer, and an image display device in which the precipitation of liquid crystal compounds is suppressed.

[0008] means for solving technical problems As a result of in-depth research conducted by the inventors to solve the above-mentioned problems, they discovered that if a liquid crystal composition containing a specified liquid crystal compound having polymerizable groups at both ends and a liquid crystal compound that differs in structure only at one end from the specified liquid crystal compound is used, the precipitation property of the liquid crystal compound is suppressed, thereby completing the present invention.

[0009] That is, the inventors have discovered that the above-mentioned problems can be solved by the following configuration.

[0010] [1] A liquid crystal composition comprising a first liquid crystal compound represented by formula (1) described below and a second liquid crystal compound represented by formula (2) described below. Both the first and second liquid crystal compounds have extremely high absorption wavelengths in the range of 280–420 nm.

[0011] [2] According to the liquid crystal composition of [1], wherein, In equations (1) and (2) described later, M represents the divalent mesocrystalline framework represented by equation (5) described later.

[0012] [3] The liquid crystal composition according to [1] or [2], wherein, The content of the second liquid crystal compound is 0.01 to 20% of the total mass of the first and second liquid crystal compounds.

[0013] [4] A liquid crystal compound, which is represented by formula (2) described below.

[0014] [5] A liquid crystal curing layer, which fixes the orientation state of the liquid crystal composition described in any one of [1] to [3].

[0015] [6] An optical film having the liquid crystal curing layer described in [5].

[0016] [7] A polarizer having the optical film and polarizer described in [6].

[0017] [8] An image display device having the optical film described in [6] or the polarizer described in [7].

[0018] Invention Effects According to the present invention, a liquid crystal composition, a liquid crystal compound, a liquid crystal cured layer, an optical film, a polarizer, and an image display device are provided in which the precipitation of liquid crystal compounds is suppressed. Attached Figure Description

[0019] Figure 1 This is a schematic cross-sectional view showing an example of an optical film. Detailed Implementation

[0020] The present invention will now be described in detail.

[0021] The following description of the constituent elements is sometimes based on representative embodiments of the present invention, but the present invention is not limited to such embodiments.

[0022] In addition, in this specification, the numerical range indicated by “~” represents the range including the values ​​recorded before and after “~” as the lower and upper limits.

[0023] Furthermore, in this specification, the upper or lower limit of a numerical range recorded in a certain numerical range can be replaced with the upper or lower limit of other numerical ranges recorded in a certain period. Also, the upper or lower limit of a numerical range recorded in this specification can be replaced with the values ​​shown in the embodiments.

[0024] Furthermore, in this specification, each component may be used individually with one corresponding substance, or two or more substances may be used simultaneously. In cases where two or more substances are used simultaneously for each component, the content of that component, unless otherwise stated, refers to the total content of the substances used simultaneously.

[0025] Furthermore, in this specification, "(meth)acrylate" is the expression for "acrylate" or "methacrylate", "(meth)acrylate group" is the expression for "acrylate group" or "methacrylate group", and "(meth)acryloyl group" is the expression for "acryloyl group" or "methacryloyl group".

[0026] Furthermore, the bonding direction of divalent groups (e.g., -O-CO-) described in this specification is not particularly limited, for example, in "L 1 -L 2 -L 3 In the bonding of "L" 2 In the case of -O-CO-, if the bond to L 1 The side position is set as 1. Bond to L 3 The side position is set as 2, then L 2 It can be 1-O-CO- 2, or it could be 1-CO-O- 2.

[0027] Furthermore, in this specification, Re(λ) and Rth(λ) represent the in-plane retardation and the retardation in the thickness direction at wavelength λ, respectively. Unless otherwise specified, wavelength λ is set to 550 nm.

[0028] In this invention, Re(λ) and Rth(λ) are values ​​measured at wavelength λ using an AxoScan (manufactured by Axometrics). The following values ​​are calculated by inputting the average refractive index ((nx+ny+nz) / 3) and film thickness (d(μm)) into the AxoScan.

[0029] Slow axis direction (°) Re(λ) = R0(λ) Rth(λ)=((nx+ny) / 2-nz)×d Additionally, R0(λ) is displayed as a value calculated by AxoScan, but refers to Re(λ).

[0030] Furthermore, in this specification, as a substituent (a monovalent substituent), examples of substituents described in substituent group A below can be cited.

[0031] Furthermore, in this specification, "may have substituents" includes not only the form without substituents, but also the form with one or more substituents.

[0032] <Substituent group A> As substituents, examples include the following, and more than two of them can be combined: Halogen atom (e.g., fluorine atom, chlorine atom, bromine atom, preferably chlorine atom, fluorine atom, more preferably fluorine atom); Alkyl groups (preferably straight-chain, branched, or cyclic alkyl groups having 1 to 48 carbon atoms, more preferably 1 to 24 carbon atoms, and especially preferably 1 to 8 carbon atoms, for example, straight-chain alkyl groups having 1 to 6 carbon atoms (e.g., methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl), branched alkyl groups having 3 to 6 carbon atoms (e.g., isopropyl, isobutyl, tert-butyl, sec-butyl, neopentyl, isohexyl, 3-methylpentyl), and cyclic alkyl groups having 3 to 12 carbon atoms (e.g., cyclopropyl, cyclopentyl, cyclohexyl, 1-norbornyl, 1-adamantyl)). Alkenyl (preferably alkenyl with 2 to 48 carbon atoms, more preferably alkenyl with 2 to 18 carbon atoms, for example, vinyl, allyl, 1-butenyl, 2-butenyl); Alkynyl (preferably an alkynyl group with 2 to 6 carbon atoms, more preferably an alkynyl group with 2 to 4 carbon atoms, for example, ethynyl, 1-propynyl, propynyl, 1-butynyl, 2-butynyl); Aryl (preferably aryl with 6 to 48 carbon atoms, more preferably aryl with 6 to 24 carbon atoms, for example, phenyl, oligoaryl (naphthyl, anthracene), phenanthrene, fluorene, pyrene, triphenylene, biphenyl); Heteroaryl groups (preferably heterocyclic groups with 1 to 32 carbon atoms, more preferably heterocyclic groups with 1 to 18 carbon atoms, for example, 2-thienyl, 4-pyridyl, 2-furanyl, 2-pyrimidinyl, 1-pyridyl, 2-benzothiazolyl, 1-imidazolyl, 1-pyrazolyl, benzotriazol-1-yl); Aryl group (preferably an aryl group having 7 to 15 carbon atoms, for example, benzyl, phenethyl, methylbenzyl, phenylpropyl, 1-methylphenylethyl, phenylbutyl, 2-methylphenylpropyl, tetrahydronaphthyl, naphthylmethyl, naphthylethyl, indene, fluorenyl, anthrylmethyl, phenanthrylmethyl)); Silyl group (preferably silyl group with 3 to 38 carbon atoms, more preferably silyl group with 3 to 18 carbon atoms, for example, trimethylsilyl, triethylsilyl, tributylsilyl, tert-butyldimethylsilyl, tert-hexyldimethylsilyl); Hydroxyl; cyano; nitro; morpholino; Alkoxy groups (preferably alkoxy groups with 1 to 48 carbon atoms, more preferably alkoxy groups with 1 to 24 carbon atoms, such as methoxy, ethoxy, 1-butoxy, 2-butoxy, isopropoxy, tert-butoxy, dodecyloxy, cycloalkoxy (e.g., cyclopentoxy, cyclohexyloxy)). Aryloxy group (preferably an aryloxy group with 6 to 48 carbon atoms, more preferably an aryloxy group with 6 to 24 carbon atoms, for example, phenoxy group, 1-naphthoxy group); Alkenyloxy group (preferably an alkenyloxy group having 2 to 6 carbon atoms, for example, ethyleneoxy, 1-propenoxy, 2-n-propenoxy (allyloxy), 1-n-butenoxy, isopreneoxy). Heterocyclic groups (preferably heterocyclic groups with 1 to 32 carbon atoms, more preferably heterocyclic groups with 1 to 18 carbon atoms, for example, 1-phenyltetrazole-5-oxy, 2-tetrahydropyranoxy); Silyoxy group (preferably siloxy group with 1 to 32 carbon atoms, more preferably siloxy group with 1 to 18 carbon atoms, for example, trimethylsiloxy group, tert-butyldimethylsiloxy group, diphenylmethylsiloxy group). Acyloxy group (preferably an acyloxy group with 2 to 48 carbon atoms, more preferably an acyloxy group with 2 to 24 carbon atoms, for example, acetoxy, neopentyloxy, benzoyloxy, dodecyloxy, acryloyloxy, methacryloyloxy). Hydroxyalkoxide (preferably a hydroxyalkoxide with 2 to 10 carbon atoms, for example, hydroxyethoxy); Alkoxycarbonyloxy (preferably alkoxycarbonyloxy with 2 to 48 carbon atoms, more preferably alkoxycarbonyloxy with 2 to 24 carbon atoms, for example, ethoxycarbonyloxy, tert-butoxycarbonyloxy, cycloalkoxycarbonyloxy (for example, cyclohexyloxycarbonyloxy)); Aryloxycarbonyloxy (preferably aryloxycarbonyloxy with 7 to 32 carbon atoms, more preferably aryloxycarbonyloxy with 7 to 24 carbon atoms, for example, phenoxycarbonyloxy); Carbamoyloxy (preferably carbamoyloxy with 1 to 48 carbon atoms, more preferably with 1 to 24 carbon atoms, for example, N,N-dimethylcarbamoyloxy, N-butylcarbamoyloxy, N-phenylcarbamoyloxy, N-ethyl-N-phenylcarbamoyloxy). Aminosulfonyloxy (preferably an aminosulfonyloxy with 1 to 32 carbon atoms, more preferably an aminosulfonyloxy with 1 to 24 carbon atoms, for example, N,N-diethylaminosulfonyloxy, N-propylaminosulfonyloxy). Alkylsulfonyloxy (preferably alkylsulfonyloxy with 1 to 38 carbon atoms, more preferably alkylsulfonyloxy with 1 to 24 carbon atoms, for example, methylsulfonyloxy, hexadecylsulfonyloxy, cyclohexylsulfonyloxy); Arylsulfonyloxy group (preferably arylsulfonyloxy group with 6 to 32 carbon atoms, more preferably arylsulfonyloxy group with 6 to 24 carbon atoms, for example, phenylsulfonyloxy group); Acyl group (preferably an acyl group with 1 to 48 carbon atoms, more preferably an acyl group with 1 to 24 carbon atoms, for example, formyl, acetyl, acryloyl, methacryloyl, neopentyl, benzoyl, tetradecanoyl, cyclohexyl); Alkoxycarbonyl (preferably an alkoxycarbonyl with 2 to 48 carbon atoms, more preferably an alkoxycarbonyl with 2 to 24 carbon atoms, for example, methoxycarbonyl, ethoxycarbonyl, octadecyloxycarbonyl, cyclohexyloxycarbonyl, 2,6-di-tert-butyl-4-methylcyclohexyloxycarbonyl); Aryloxycarbonyl (preferably an aryloxycarbonyl with 7 to 32 carbon atoms, more preferably an aryloxycarbonyl with 7 to 24 carbon atoms, for example, phenoxycarbonyl); Carbamoyl group (preferably a carbamoyl group with 1 to 48 carbon atoms, more preferably a carbamoyl group with 1 to 24 carbon atoms, for example, 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, N,N-dicyclohexylcarbamoyl group); Amino group (preferably an amino group with 32 or fewer carbon atoms, more preferably an amino group with 24 or fewer carbon atoms, for example, amino, methylamino, N,N-dimethylamino, N,N-dibutylamino, tetradecylamino, 2-ethylhexylamino, cyclohexylamino); Aniline (preferably aniline with 6 to 32 carbon atoms, more preferably 6 to 24 carbon atoms, for example, aniline or N-methylaniline); Heterocyclic amino group (preferably a heterocyclic amino group with 1 to 32 carbon atoms, more preferably 1 to 18 carbon atoms, for example, 4-pyridylamino group); Carboxylamide group (preferably a carboxylamide group with 2 to 48 carbon atoms, more preferably 2 to 24 carbon atoms, for example, acetamide group, benzamide group, tetradecanoamide group, neopentanoylamide group, cyclohexaneamide group); Urea group (preferably a urea group with 1 to 32 carbon atoms, more preferably a urea group with 1 to 24 carbon atoms, for example, urea group, N,N-dimethylurea group, N-phenylurea group); Imide group (preferably an imide group with 36 or fewer carbon atoms, more preferably an imide group with 24 or fewer carbon atoms, for example, N-succinimide group, N-phthalimide group); Alkoxycarbonylamino (preferably alkoxycarbonylamino with 2 to 48 carbon atoms, more preferably alkoxycarbonylamino with 2 to 24 carbon atoms, for example, methoxycarbonylamino, ethoxycarbonylamino, tert-butoxycarbonylamino, octadecyloxycarbonylamino, cyclohexyloxycarbonylamino). Aryloxycarbonylamino (preferably aryloxycarbonylamino with 7 to 32 carbon atoms, more preferably aryloxycarbonylamino with 7 to 24 carbon atoms, for example, phenoxycarbonylamino); Sulfonamide group (preferably a sulfonamide group with 1 to 48 carbon atoms, more preferably a sulfonamide group with 1 to 24 carbon atoms, for example, methanesulfonamide group, butanesulfonamide group, benzenesulfonamide group, hexadecanesulfonamide group, cyclohexanesulfonamide group); Aminosulfonylamino (preferably an aminosulfonylamino with 1 to 48 carbon atoms, more preferably an aminosulfonylamino with 1 to 24 carbon atoms, for example, N,N-dipropylaminosulfonylamino, N-ethyl-N-dodecylaminosulfonylamino). Azo group (preferably an azo group with 1 to 32 carbon atoms, more preferably an azo group with 1 to 24 carbon atoms, for example, phenyl azo group, 3-pyrazolyl azo group); Alkylthio (preferably alkylthio with 1 to 48 carbon atoms, more preferably alkylthio with 1 to 24 carbon atoms, for example, methylthio, ethylthio, octylthio, cyclohexylthio); Arylthio (preferably arylthio with 6 to 48 carbon atoms, more preferably arylthio with 6 to 24 carbon atoms, for example, phenylthio); Heterocyclic thio groups (preferably heterocyclic thio groups with 1 to 32 carbon atoms, more preferably heterocyclic thio groups with 1 to 18 carbon atoms, for example, 2-benzothiazolyl thio group, 2-pyridyl thio group, 1-phenyltetrazole thio group); Alkyl sulfinyl group (preferably an alkyl sulfinyl group with 1 to 32 carbon atoms, more preferably an alkyl sulfinyl group with 1 to 24 carbon atoms, for example, dodecane sulfinyl group); Arylsulfinyl group (preferably arylsulfinyl group with 6 to 32 carbon atoms, more preferably arylsulfinyl group with 6 to 24 carbon atoms, for example, phenylsulfinyl group); Alkyl sulfonyl group (preferably an alkyl sulfonyl group with 1 to 48 carbon atoms, more preferably an alkyl sulfonyl group with 1 to 24 carbon atoms, for example, methyl sulfonyl, ethyl sulfonyl, propyl sulfonyl, butyl sulfonyl, isopropyl sulfonyl, 2-ethylhexyl sulfonyl, hexadecyl sulfonyl, octyl sulfonyl, cyclohexyl sulfonyl). Arylsulfonyl group (preferably arylsulfonyl group with 6 to 48 carbon atoms, more preferably arylsulfonyl group with 6 to 24 carbon atoms, for example, phenylsulfonyl group, 1-naphthylsulfonyl group); Aminosulfonyl group (preferably an aminosulfonyl group with 32 or fewer carbon atoms, more preferably an aminosulfonyl group with 24 or fewer carbon atoms, for example, aminosulfonyl group, N,N-dipropylaminosulfonyl group, N-ethyl-N-dodecylaminosulfonyl group, N-ethyl-N-phenylaminosulfonyl group, N-cyclohexylaminosulfonyl group, N-(2-ethylhexyl)aminosulfonyl group); Phosphonoyl group (preferably a phosphonoyl group with 1 to 32 carbon atoms, more preferably a phosphonoyl group with 1 to 24 carbon atoms, for example, phenoxyphosphonoyl group, octoxyphosphonoyl group, phenylphosphonoyl group); Oxyphosphinoamino (preferably oxyphosphinoamino with 1 to 32 carbon atoms, more preferably oxyphosphinoamino with 1 to 24 carbon atoms, for example, ethoxyphosphinoamino, dioctyloxyphosphinoamino). Epoxy groups; -NHCOCH3; -SO2NHC2H4OCH3; -NHSO2CH3, etc.

[0033] These substituents can be further replaced by these substituents. Furthermore, in the case of two or more substituents, they can be the same or different. And, where possible, they can bond together to form a ring.

[0034] [Liquid Crystal Composition] The liquid crystal composition of the present invention is a liquid crystal composition containing a first liquid crystal compound represented by formula (1) described later and a second liquid crystal compound represented by formula (2) described later.

[0035] Furthermore, the liquid crystal composition of the present invention is a liquid crystal compound in which both the first liquid crystal compound and the second liquid crystal compound have a large absorption wavelength in the wavelength range of 280 to 420 nm.

[0036] Here, the "maximum absorption wavelength" of the liquid crystal compound can be measured using a UV-Vis spectrophotometer (e.g., UV-1800 (manufactured by SHIMADZU CORPORATION)) in the wavelength range of 200–800 nm, and calculated based on the obtained absorption spectrum.

[0037] Furthermore, in calculating the "maximum absorption wavelength" of each component in the mixture, a high-speed liquid chromatography (HPLC) apparatus equipped with a photodiode array detector (e.g., the Prominence series (manufactured by SHIMADZU CORPORATION)) can be used to detect the UV-Vis absorption spectrum of each separated peak, and the wavelength can be calculated based on the maximum value of that spectrum. Additionally, the solvent used is not particularly limited as long as it is a common eluent for HPLC apparatus, and can contain additives such as weak acids or weak bases as buffers. Moreover, methanol, acetonitrile, tetrahydrofuran, and water are preferred as eluents; acetic acid and phosphoric acid are preferred as buffering acids; and triethylamine is preferred as a weak base.

[0038] In this invention, as described above, if a liquid crystal composition containing a specified liquid crystal compound having polymerizable groups at both ends and a liquid crystal compound that is structurally different from the first liquid crystal compound and the second liquid crystal compound is used, the precipitation property of the liquid crystal compound is suppressed.

[0039] Although the detailed mechanism is unclear, the inventors speculate as follows.

[0040] That is, it is speculated that this is because the structure of the second liquid crystal compound, except for T (hydroxyl group, etc.) in formula (2) described later, is the same as that of the first liquid crystal compound, and therefore the crystallization of the first liquid crystal compound can be suppressed without hindering the orientation of the first liquid crystal compound.

[0041] The first liquid crystal compound and the second liquid crystal compound contained in the liquid crystal composition of the present invention will be described in detail below.

[0042] [First liquid crystal compound] The first liquid crystal compound is the liquid crystal compound represented by the following formula (1).

[0043] [Chemical Formula 1] In the above formula (1), L 1 and L 2 Each can be used to represent a polymeric group independently.

[0044] Here, polymerizable groups are not particularly limited, but polymerizable groups capable of free radical polymerization or cationic polymerization are preferred.

[0045] As a free radical polymerizable group, known free radical polymerizable groups can be used. Preferred free radical polymerizable groups include acryloyloxy and methacryloyloxy. In this case, it is known that acryloyloxy generally has a faster polymerization rate, and from the viewpoint of improving productivity, acryloyloxy is preferred. However, methacryloyloxy can also be used as a polymerizable group.

[0046] As the cationic polymerizable group, known cationic polymerizable groups can be used. Specifically, examples include alicyclic ether groups, cyclic acetal groups, cyclic lactone groups, cyclic thioether groups, spirocyclic orthoester groups, and ethyleneoxy groups. Among these, alicyclic ether groups or ethyleneoxy groups are preferred, and epoxy groups, oxetyl groups, or ethyleneoxy groups are particularly preferred.

[0047] Examples of particularly preferred polymerizable groups include polymerizable groups represented by any one of the following formulas (P-1) to (P-20).

[0048] [Chemical Formula 2] In the above formula (1), SP 1 and SP 2 Each group independently represents a single bond or a divalent aliphatic hydrocarbon group with 1 to 20 carbon atoms. One or more of the -CH2- groups constituting the aliphatic hydrocarbon group can be substituted by -O-, -S-, -NH-, -N(Q)-, or -CO-. Q represents a substituent.

[0049] Here, examples of divalent aliphatic hydrocarbon groups with 1 to 20 carbon atoms include linear or branched alkylene groups with 1 to 20 carbon atoms, alkenyl groups with 1 to 20 carbon atoms, and alkyne groups with 1 to 20 carbon atoms.

[0050] As a straight-chain or branched alkylene group having 1 to 20 carbon atoms, an alkylene group having 1 to 12 carbon atoms is preferred, and an alkylene group having 1 to 10 carbon atoms is more preferred. Examples of preferred alkylene groups include methylene, ethylene, propylene, butylene, pentylene, and hexylene.

[0051] As a straight-chain or branched alkenyl group with 1 to 20 carbon atoms, an alkenyl group with 2 to 10 carbon atoms is preferred, and an alkenyl group with 2 to 4 carbon atoms is more preferred, for example, vinylidene.

[0052] As a straight-chain or branched ynyl group with 1 to 20 carbon atoms, an ynyl group with 2 to 10 carbon atoms is preferred, and an ynyl group with 2 to 4 carbon atoms is more preferred, for example, an ethynyl group.

[0053] Furthermore, as described above, one or more of the -CH2- constituting the aliphatic hydrocarbon group can be replaced by -O-, -S-, -NH-, -N(Q)- or -CO-. As the substituent represented by Q, the substituents described in the substituent group A above can be cited, wherein alkyl, alkoxy, alkoxycarbonyl, alkylcarbonyloxy or halogen atom are preferred.

[0054] In the above formula (1), M represents a divalent mesocrystalline framework having more than 3 rings, which may have substituents, aromatic rings or aliphatic rings.

[0055] Here, aromatic rings can be exemplified by, for example, aromatic rings with 6 to 20 carbon atoms. Specifically, aromatic hydrocarbon rings such as benzene rings, naphthalene rings, anthracene rings, and phenanthroline rings can be exemplified; aromatic heterocycles such as furan rings, pyrrole rings, thiophene rings, pyridine rings, thiazole rings, and benzothiazole rings can be exemplified. Among these, benzene rings (e.g., 1,4-phenyl rings) are preferred.

[0056] Furthermore, aliphatic rings can be exemplified by cycloalkane rings, specifically cyclohexane rings, cyclopentane rings, cyclooctane rings, cyclododecane rings, and cyclodocosahexane rings. Among these, cyclohexane rings are preferred, 1,4-cyclohexene rings are more preferred, and trans-1,4-cyclohexene rings are even more preferred.

[0057] Substituents that can be present in the aromatic or aliphatic ring include those described in substituent group A above, wherein alkyl, alkoxy, alkoxycarbonyl, alkylcarbonyloxy, or halogen atoms are preferred.

[0058] In formula (1) above, the number of aromatic rings or aliphatic rings in M ​​is not particularly limited as long as the total number of rings is 3 or more, but is preferably 3 to 10 rings, more preferably 3 to 7 rings, and even more preferably 3 to 5 rings.

[0059] In this invention, for the sake of easily exhibiting liquid crystal properties and also easily imparting optical properties, M in the above formula (1) preferably represents the divalent mesocrystalline framework represented by the following formula (5). Furthermore, in the following formula (5), Indicates SP 1 or SP 2 The bonding positions.

[0060] [Chemical Formula 3] In the above formula (5), B 1 and B 2 Each can independently represent an aromatic ring with 6 to 20 carbon atoms that may have substituents or a divalent alicyclic hydrocarbon group with 5 to 20 carbon atoms that may have substituents, wherein one or more of the -CH2- constituting the alicyclic hydrocarbon group can be substituted by -O-, -S- or -NH-.

[0061] As B 1 and B 2 The aromatic ring represented by one of the methods has 6 to 20 carbon atoms, and examples include aromatic hydrocarbon rings such as benzene rings, naphthalene rings, anthracene rings, and phenanthroline rings; and aromatic heterocycles such as furan rings, pyrrole rings, thiophene rings, pyridine rings, thiazole rings, and benzothiazole rings. Among these, benzene rings (e.g., 1,4-phenyl rings) are preferred.

[0062] As B 1 and B 2 The alicyclic hydrocarbon group with 5 to 20 carbon atoms, represented by one of the methods, is preferably a 5-membered or 6-membered ring. Furthermore, the alicyclic hydrocarbon group can be saturated or unsaturated, but a saturated alicyclic hydrocarbon group is preferred. As G 1 and G 2 The divalent alicyclic hydrocarbon group represented can be referred to, for example, in paragraph

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

[0063] Furthermore, as an alicyclic hydrocarbon group, a cycloalkane ring is preferred.

[0064] Examples of cycloalkane rings include cyclohexane, cyclopentane, cyclooctane, cyclododecane, and cyclododecane.

[0065] Among these, cyclohexane ring is preferred, 1,4-cyclohexene ring is more preferred, and trans-1,4-cyclohexene ring is even more preferred.

[0066] Furthermore, in the above equation (5), regarding B 1 and B 2 The substituents that can be present as aromatic rings with 6 to 20 carbon atoms or divalent alicyclic hydrocarbon groups with 5 to 20 carbon atoms are examples of substituents described in substituent group A above, wherein alkyl, alkoxy, alkoxycarbonyl, alkylcarbonyloxy or halogen atoms are preferred.

[0067] In the above formula (5), D 1 D 2 D 3 and D 4 Each can independently represent a single bond or -CO-, -O-, -S-, -C(=S)-, -CR 1 R 2 -、-CR 3 =CR 4 -、-NR 5 - or a divalent linker consisting of two or more of them, R 1 ~R 5 Each can be an alkyl group, representing a hydrogen atom, a fluorine atom, or a carbon atom numbering 1 to 12, respectively.

[0068] Here, as divalent linking groups, examples 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-NR 5 - etc. Additionally, R 1 R2 and R 5 Each can be an alkyl group, representing a hydrogen atom, a fluorine atom, or a carbon atom numbering 1 to 12, respectively.

[0069] Among these, the preferred choice is any one of -CO-, -O-, and -CO-O-.

[0070] In the above formula (5), m1 and m2 independently represent integers from 1 to 3. When m1 represents 2 or 3, multiple B 1 and D 1 The terms can be the same or different. When m2 represents 2 or 3, multiple B's... 2 and D 2 They can be the same or different.

[0071] Here, m1 and m2 are both preferably 1 or 2, and more preferably 2.

[0072] In formula (5) above, Ar represents any aromatic ring selected from the group consisting of the groups represented by formulas (Ar-1) to (Ar-7) below. Furthermore, in formulas (Ar-1) to (Ar-7) below, This represents D in equation (5) above. 1 Or D 2 The bonding positions.

[0073] [Chemical Formula 4] In the above equation (Ar-1), Q 1 Represents N or CH, Q 2 Indicates -S-, -O-, or -N(R) 6 )-,R 6 Y represents an alkyl group having 1 to 6 hydrogen atoms or carbon atoms. 1 It indicates an aromatic hydrocarbon group with 6 to 12 carbon atoms that may have substituents, an aromatic heterocyclic group with 3 to 12 carbon atoms that may have substituents, or an alicyclic hydrocarbon group with 6 to 20 carbon atoms that may have substituents, wherein one or more of the -CH2- constituting the alicyclic hydrocarbon group can be replaced by -O-, -S- or -NH-.

[0074] Here, as R 6 The alkyl group having 1 to 6 carbon atoms is represented by a certain method. Specifically, examples include methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, and n-hexyl.

[0075] As Y 1 The aromatic hydrocarbon group with 6 to 12 carbon atoms can be represented in one way, for example, aryl groups such as phenyl, 2,6-diethylphenyl, and naphthyl.

[0076] As Y 1 The aromatic heterocyclic group with 3 to 12 carbon atoms represented in one manner includes, for example, heteroaryl groups such as thienyl, thiazolyl, furanyl, and pyridyl, as well as groups formed by removing one hydrogen atom from any one of the indole ring, benzofuran ring, benzothiophene ring, benzimidazole ring, benzothiazole ring, and benzoxazole ring. Among these, Y... 1 The aromatic heterocyclic group represented by carbon atoms with 3 to 12 is preferably a group formed by removing one hydrogen atom from a benzofuran ring or a benzothiazole ring.

[0077] As Y 1 The alicyclic hydrocarbon group with 6 to 20 carbon atoms can be represented in one way, for example, cyclohexylene, cyclopentylene, norbornylene, adamantylene, etc.

[0078] And, as Y 1 The substituents that may be present include those described in substituent group A above, wherein preferably alkyl, alkoxy, alkoxycarbonyl, alkylcarbonyloxy, nitro, cyano or halogen atoms.

[0079] Furthermore, in the above equations (Ar-1) to (Ar-7), Z 1 Z 2 and Z 3 Each of the following can be independently represented: a hydrogen atom, a monovalent aliphatic hydrocarbon group with 1-20 carbon atoms, a monovalent alicyclic hydrocarbon group with 3-20 carbon atoms, a monovalent aromatic hydrocarbon group with 6-20 carbon atoms, a monovalent aromatic heterocyclic group with 6-20 carbon atoms, a halogen atom, a cyano group, a nitro group, or -OR. 7 -NR 8 R 9 -SR 10 -COOR 11 or -COR 12 R 7 ~R 12 Z represents, independently, either a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. 1 and Z 2 They can bond with each other to form aromatic rings.

[0080] As a 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, and specifically, methyl, ethyl, isopropyl, tert-amyl (1,1-dimethylpropyl), tert-butyl, 1,1-dimethyl-3,3-dimethyl-butyl is even more preferred, and methyl, ethyl, and tert-butyl are particularly preferred.

[0081] Examples of monocyclic alicyclic hydrocarbon groups with 3 to 20 carbon atoms include monocyclic saturated hydrocarbon groups such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclodecyl, methylcyclohexyl, and ethylcyclohexyl; monocyclic unsaturated hydrocarbon groups such as cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, cyclooctenyl, cyclodecenyl, cyclopentadienyl, cyclohexadienyl, cyclooctadienyl, and cyclodecadienyl; and bicyclic [2.2.1]heptyl, bicyclic [2.2.2]octyl, and tricyclic [5.2.1.0]heptyl. 2,6 ] decyl, tricyclic [3.3.1.1] 3,7 ] decyl, tetracyclic [6.2.1.1 3,6 .0 2,7 Dodecyl, adamantyl, and other polycyclic saturated hydrocarbon groups, etc.

[0082] As a monovalent aromatic hydrocarbon group with 6 to 20 carbon atoms, examples include phenyl, 2,6-diethylphenyl, naphthyl, biphenyl, etc., with aryl groups having 6 to 12 carbon atoms (especially phenyl) being preferred.

[0083] As a monovalent aromatic heterocyclic group with 6 to 20 carbon atoms, examples include 4-pyridyl, 2-furanyl, 2-thienyl, 2-pyrimidinyl, and 2-benzothiazolyl.

[0084] Examples of halogen atoms include fluorine, chlorine, bromine, and iodine atoms, with fluorine, chlorine, and bromine atoms being preferred.

[0085] On the other hand, as R 7 ~R 10 The alkyl groups having 1 to 6 carbon atoms shown include, for example, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, and n-hexyl.

[0086] As mentioned above, Z 1 and Z 2 They can bond with each other to form aromatic rings, for example, as Z in the above formula (Ar-1). 1 and Z 2 The structure in which groups bond together to form an aromatic ring can be exemplified by groups represented by the following formula (Ar-1a). Furthermore, in the following formula (Ar-1a), This indicates that D in equation (A) above... 11 or X 1 The bonding positions.

[0087] [Chemical Formula 5] Here, in the above equation (Ar-1a), Q 1 Q2 and Y 1 Groups that are the same as those described in the above formula (Ar-1) can be cited.

[0088] Furthermore, in the above equations (Ar-2) and (Ar-3), A 3 and A 4 Represent the selection independently of -O- and -N(R) 13 The group consisting of -, -S- and -CO-, R 13 It represents a hydrogen atom or a substituent.

[0089] As R 13 The substituents represented in one manner can be exemplified by those described in the substituent group A above, wherein preferably alkyl, alkoxy, alkoxycarbonyl, alkylcarbonyloxy or halogen atoms.

[0090] Furthermore, in the above formula (Ar-2), X represents a nonmetallic atom from groups 14 to 16. These nonmetallic atoms may be bonded with hydrogen atoms or substituents.

[0091] Furthermore, examples of nonmetallic atoms in groups 14-16 represented by X include oxygen atoms, sulfur atoms, and nitrogen atoms bonded with hydrogen atoms or substituents [=NR]. N1 R N1 Represents a hydrogen atom or substituent. A carbon atom bonded with a hydrogen atom or substituent [=C-(R] C1 )2,R C1 This represents a hydrogen atom or a substituent.

[0092] Examples of substituents can be found in substituent group A above, among which alkyl, alkoxy, alkyl-substituted alkoxy, cyclic alkyl, aryl (e.g., phenyl, naphthyl, etc.), cyano, amino, nitro, alkyl carbonyl, sulfonyl, hydroxyl, etc. are preferred.

[0093] Furthermore, in the above equation (Ar-3), D 7 and D 8 Each can independently represent a single bond or -CO-, -O-, -S-, -C(=S)-, -CR 1 R 2 -、-CR 3 =CR 4 -、-NR 5 - or a divalent linker consisting of two or more of them, R 1 ~R 5 Each can be an alkyl group, representing a hydrogen atom, a fluorine atom, or a carbon atom numbering 1 to 12, respectively.

[0094] Here, as a divalent linking group, examples can be given of D in the above formula (5). 1 and D 2 The linking group is the same as the linking group described in the document.

[0095] Furthermore, in the above formula (Ar-3), SP 3 and SP 4 Each of these groups independently represents a single bond or a divalent aliphatic hydrocarbon group having 1 to 20 carbon atoms. One or more of the -CH2- groups constituting the aliphatic hydrocarbon group may be substituted with -O-, -S-, -NH-, -N(Q)-, or -CO-. Q represents a substituent. Examples of substituents represented by Q can be those described in substituent group A above, preferably alkyl, alkoxy, alkoxycarbonyl, alkylcarbonyloxy, or halogen atoms.

[0096] Here, as a divalent aliphatic hydrocarbon group, examples can be given that SP in the above formula (1) is... 1 and SP 2 The aliphatic hydrocarbon groups described herein are the same as those in the aliphatic hydrocarbon groups.

[0097] Furthermore, in the above equation (Ar-3), L 3 and L 4 Each of these represents a monovalent organic group independently.

[0098] Here, examples of monovalent organic groups include substituents described in substituent group A above, polymeric groups, etc., among which alkyl, aryl, heteroaryl, alkoxy, cyano, carboxyl and polymeric groups are preferred.

[0099] The alkyl group can be straight-chain, branched, or cyclic, but is preferably straight-chain. The alkyl group preferably has 1 to 30 carbon atoms, more preferably 1 to 20, and even more preferably 1 to 10.

[0100] Furthermore, the aryl group can be monocyclic or polycyclic, but monocyclic is preferred. The number of carbon atoms in the aryl group is preferably 6 to 25, more preferably 6 to 10.

[0101] Furthermore, the heteroaryl group can 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, sulfur, or oxygen atoms. The number of carbon atoms in the heteroaryl group is preferably 6 to 18, more preferably 6 to 12.

[0102] Furthermore, the alkyl, aryl, and heteroaryl groups may be unsubstituted or have substituents. Examples of substituents include those described in substituent group A above, with alkyl, alkoxy, alkoxycarbonyl, alkylcarbonyloxy, or halogen atoms being preferred.

[0103] Furthermore, as a polymerizable group, any one of the polymerizable groups represented by the above formulas (P-1) to (P-20) can be preferably cited.

[0104] In the above formulas (Ar-4) to (Ar-7), Ax represents an organic group having 2 to 30 carbon atoms in at least one aromatic ring selected from the group consisting of aromatic hydrocarbon rings and aromatic heterocycles.

[0105] Furthermore, in the above formulas (Ar-4) to (Ar-7), Ay represents a hydrogen atom, an alkyl group having 1 to 12 carbon atoms that may have substituents, or an organic group having 2 to 30 carbon atoms of at least one aromatic ring selected from the group consisting of aromatic hydrocarbon rings and aromatic heterocycles.

[0106] Here, the aromatic rings in Ax and Ay can have substituents, and Ax and Ay can also bond together to form a ring.

[0107] And Q 3 It represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms that may have substituents.

[0108] As for Ax and Ay, examples can be found in paragraphs

[0039] to

[0095] of International Publication No. 2014 / 010325.

[0109] And, as Q 3 The alkyl group representing 1 to 6 carbon atoms can specifically include, for example, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, and n-hexyl. As a substituent, the substituents described in the substituent group A above can be included, wherein alkyl, alkoxy, alkoxycarbonyl, alkylcarbonyloxy, or halogen atoms are preferred.

[0110] Examples of first liquid crystal compounds include compounds represented by general formula (1) as described in Japanese Patent Application Publication No. 2010-084032 (especially compounds described in paragraphs

[0067] to

[0073] ), compounds represented by general formula (II) as described in Japanese Patent Application Publication No. 2016-053709 (especially compounds described in paragraphs

[0036] to

[0043] ), compounds represented by general formula (1) as described in Japanese Patent Application Publication No. 2016-081035 (especially compounds described in paragraphs

[0043] to

[0055] ), and compounds described in paragraphs

[0025] to

[0056] of International Publication No. 2021 / 060427.

[0111] [Second liquid crystal compound] The second liquid crystal compound is the liquid crystal compound represented by the following formula (2).

[0112] [Chemical Formula 6] In the above formula (2), M and SP 1 SP 2 and L 1 The meanings are the same as those explained in equation (1) above.

[0113] Furthermore, in the first and second liquid crystal compounds contained in the liquid crystal composition of the present invention, M and SP in the above formulas (1) and (2) are... 1 SP 2 and L 1 This indicates that the groups are the same as each other. That is, for example, if L in the above formula (1) 1 If it is an acryloxy group, then L in the above formula (2) 1 It also represents acryloyloxy, if SP in the above formula (1) 1 If it is propylidene, then SP in the above formula (2) 1 It also refers to propylidene.

[0114] On the other hand, in formula (2) above, T represents a hydroxyl group, a halogen atom, an alkyl carbonyl group having 1 to 6 carbon atoms, or a substituent represented by formula (3) or (4) below. Furthermore, in formulas (3) and (4) below, Indicates SP 2 The bonding positions.

[0115] [Chemical Formula 7] In equations (3) and (4) above, X - It indicates a counter-anion.

[0116] Here, counteracting anions can be exemplified by, for example, alkylborate anions, arylborate anions, perchlorate ions, and halide anions, among which halide anions (especially F) are preferred. - and Cl - ).

[0117] In equations (3) and (4) above, R T1 ~R T3 Each alkyl group, having 1 to 6 carbon atoms, is represented independently. R T4 and R T5 Each can be independently represented by an alkyl group having 1 to 6 hydrogen atoms or carbon atoms.

[0118] Here, the alkyl groups mentioned above can be specifically exemplified by, for example, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, and n-hexyl.

[0119] Furthermore, one or more of the -CH2- groups constituting the aforementioned alkyl group can be replaced by -O-, -S-, -NH-, -N(Q)-, or -CO-. Q represents a substituent. Additionally, examples of substituents described in substituent group A above can be cited as substituents, with alkyl, alkoxy, alkoxycarbonyl, alkylcarbonyloxy, or halogen atoms being preferred.

[0120] Furthermore, regarding R T1 ~R T3 R T1 ~R T3 Two or three of them can bond together to form a ring. In the above formulas (3) and (4), A represents a 5- or 6-membered nitrogen-containing aromatic ring that may have substituents.

[0121] Here, a 5-membered nitrogen-containing aromatic ring can specifically be exemplified by pyrazole rings, imidazole rings, triazole rings, tetraazole rings, thiazole rings, etc.

[0122] Furthermore, examples of 6-membered nitrogen-containing aromatic rings include pyridine rings, pyridazine rings, pyrimidine rings, and pyrazine rings.

[0123] Furthermore, the substituents that can be present in the 5- or 6-membered nitrogen-containing aromatic ring include those described in the substituent group A above, wherein alkyl, alkoxy, alkoxycarbonyl, alkylcarbonyloxy, amino, or halogen atoms are preferred.

[0124] As a second liquid crystal compound, for example, specific compounds (2-1) to (2-11) represented by the following formulas can be preferred.

[0125] [Chemical Formula 8] In this invention, from the viewpoint of balancing the suppression of liquid crystal compound exudation and the stretching properties (degree of crosslinking) of the liquid crystal cured layer, the content of the second liquid crystal compound is preferably 0.01 to 20% by mass relative to the total mass of the first liquid crystal compound and the second liquid crystal compound, more preferably 0.05 to 15% by mass, and even more preferably 0.1 to 10% by mass.

[0126] [Other polymeric compounds] From the viewpoint of orientation temperature and solubility, the liquid crystal composition of the present invention preferably contains, in addition to the first liquid crystal compound and the second liquid crystal compound described above, other polymeric compounds having one or more polymeric groups.

[0127] Here, the polymeric groups of other polymeric compounds are not particularly limited, and the polymeric groups represented by any one of the above formulas (P-1) to (P-20) can be preferred.

[0128] As for other polymeric compounds, in order to further improve the durability of the formed liquid crystal cured layer, other polymeric compounds having 2 to 4 polymeric groups are preferred, and other polymeric compounds having 2 polymeric groups are more preferred.

[0129] As other polymeric compounds, examples can be given of compounds represented by formulas (M1), (M2), and (M3) as described in paragraphs

[0030] to

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

[0046] to

[0055] of the same publication.

[0130] [Polymerization initiator] The liquid crystal composition of the present invention preferably contains a polymerization initiator.

[0131] The preferred polymerization initiator is a photopolymerization initiator that can initiate a polymerization reaction by ultraviolet irradiation.

[0132] Examples of photopolymerization initiators include α-carbonyl compounds (described in U.S. Patent Nos. 2,367,661 and 2,367,670), azobin ethers (described in U.S. Patent No. 2,448,828), α-hydrocarbon-substituted aromatic azobin compounds (described in U.S. Patent No. 2,722,512), polynuclear quinone compounds (described in U.S. Patent Nos. 3,046,127 and 2,951,758), triarylimidazolium dimers, and p-aminophenyl ketones. Combinations (described in U.S. Patent No. 3,549,367), acridine and phenazine compounds (described in Japanese Patent Application Publication No. 60-105,667 and U.S. Patent No. 4,239,850), oxadiazole compounds (described in U.S. Patent No. 4,212,970), acylphosphine oxide compounds (described in Japanese Patent Application Publication No. 63-40,799, Japanese Patent Application Publication No. 5-29,234, Japanese Patent Application Publication No. 10-95,788 and Japanese Patent Application Publication No. 10-29,997), etc.

[0133] Furthermore, in this invention, it is preferred that the polymerization initiator be an oxime-type polymerization initiator. As a specific example, the initiator described in paragraphs

[0049] to

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

[0134] [Solvent] From the viewpoint of operability in forming a liquid crystal curing layer, the liquid crystal composition of the present invention preferably contains a solvent.

[0135] As solvents, examples 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.), cellosols (e.g., methyl cellosol, ethyl cellosol, etc.), cellosol acetates, sulfoxides (e.g., dimethyl sulfoxide, etc.), and amides (e.g., dimethylformamide, dimethylacetamide, etc.). One of these solvents can be used alone, or two or more can be used simultaneously.

[0136] [Leveling agent] From the viewpoint of easy orientation control, the liquid crystal composition of the present invention preferably contains a leveling agent.

[0137] As such leveling agents, fluorinated or silicone leveling agents are preferred because of their high leveling effect relative to the amount added. From the viewpoint that they are less likely to cause exudation (frost, leakage), fluorinated leveling agents are more preferred.

[0138] As leveling agents, specifically, examples include compounds described in paragraphs

[0079] to

[0102] of Japanese Patent Application Publication No. 2007-069471, compounds represented by general formula (I) described in Japanese Patent Application Publication No. 2013-047204 (especially compounds described in paragraphs

[0020] to

[0032] ), and compounds represented by general formula (I) described in Japanese Patent Application Publication No. 2012-211306 (especially compounds represented by paragraphs

[0022] to

[0032] ). The compounds described in paragraph 029), liquid crystal alignment promoters represented by general formula (I) as described in Japanese Patent Application Publication No. 2002-129162 (especially the compounds described in paragraphs

[0076] to

[0078] and

[0082] to

[0084] ), and compounds represented by general formulas (I), (II) and (III) as described in Japanese Patent Application Publication No. 2005-099248 (especially the compounds described in paragraphs

[0092] to

[0096] ), etc. Additionally, they may also function as alignment control agents as described later.

[0139] [Orientation control agent] The liquid crystal composition of the present invention may contain an orientation control agent as needed.

[0140] Orientation control agents can be used to form various orientation states, including vertical orientation, tilted orientation, mixed orientation, and cholesteric orientation, in addition to uniform orientation. Furthermore, specific orientation states can be controlled and achieved more uniformly and precisely.

[0141] As orientation control agents that promote uniform orientation, low-molecular-weight or high-molecular-weight orientation control agents can be used, for example.

[0142] As a low-molecular-weight orientation control agent, reference can be made to paragraphs

[0009] to

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

[0111] to

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

[0021] to

[0029] of Japanese Patent Application Publication No. 2012-211306, the contents of which are incorporated herein by reference.

[0143] Furthermore, as an orientation control agent for polymers, reference can be made to paragraphs

[0021] to

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

[0121] to

[0167] of Japanese Patent Application Publication No. 2006-106662, the contents of which are incorporated into the specification of this application.

[0144] Furthermore, as orientation control agents that form or promote vertical orientation, examples include boric acid compounds and onium salt compounds. Specifically, reference can be made to the compounds described in Japanese Patent Application Publication No. 2008-225281, paragraphs

[0023] to

[0032] , Japanese Patent Application Publication No. 2012-208397, paragraphs

[0052] to

[0058] , Japanese Patent Application Publication No. 2008-026730, paragraphs

[0024] to

[0055] , and Japanese Patent Application Publication No. 2016-193869, paragraphs

[0043] to

[0055] , which are incorporated into the specification of this application.

[0145] On the other hand, regarding the cholesteric phase orientation, it can be achieved by adding a chiral reagent to the liquid crystal composition of the present invention, and the cycloid direction of the cholesteric phase orientation can be controlled according to its chiral direction.

[0146] In addition, the pitch of the cholesteric phase orientation can be controlled based on the orientation constraint force of the chiral reagent.

[0147] The content of the orientation control agent is preferably 0.01 to 10% by mass relative to the total solid content in the composition, more preferably 0.05 to 5% by mass. If the content is within this range, the desired orientation state is achieved, and there is no precipitation or phase separation, orientation defects, etc., resulting in a uniform and highly transparent cured product.

[0148] [Other ingredients] The liquid crystal composition of the present invention may also contain components other than those described above, such as surfactants, tilt angle control agents, orientation aids, plasticizers, and crosslinking agents.

[0149] [Liquid Crystal Compounds] The liquid crystal compound of the present invention is the compound represented by the above formula (2), and M in formula (2) represents the compound with a divalent mesocrystalline framework represented by the above formula (5).

[0150] [Liquid Crystal Curing Layer] The liquid crystal curing layer of the present invention is a liquid crystal curing layer formed by fixing the orientation state of the liquid crystal composition of the present invention as described above.

[0151] Examples of methods for forming a liquid crystal curable layer include, for instance, forming a desired orientation state using the liquid crystal composition of the present invention described above, followed by immobilization through polymerization.

[0152] The polymerization conditions are not particularly limited, but in light-based polymerization, ultraviolet light is preferred. The preferred irradiation dose is 10 mJ / cm². 2 ~50J / cm 2 More preferably 20 mJ / cm 2 ~5J / cm 2 Further optimization of 30mJ / cm 2 ~3J / cm 2 50mJ / cm is particularly preferred. 2 ~1000mJ / cm 2 Furthermore, to promote the polymerization reaction, it can be carried out under heating conditions.

[0153] In addition, the liquid crystal curing layer can be formed on any support or alignment film in the optical film described later, or on the polarizer in the polarizer described later.

[0154] The orientation state of the liquid crystal compound in the liquid crystal curing layer of the present invention can be any of the following states: horizontal orientation, vertical orientation, tilted orientation, and twisted orientation. It is preferred that it is fixed in a state of horizontal orientation relative to the main surface of the liquid crystal curing layer.

[0155] In this specification, "horizontal alignment" means that the main surface of the liquid crystal curing layer (or, in the case where the liquid crystal curing layer is formed on a support or alignment film, the surface of that component) is parallel to the long axis of the liquid crystal compound. However, strict parallelism is not required; in this specification, it refers to an alignment where the angle between the long axis of the liquid crystal compound and the main surface of the liquid crystal curing layer is less than 10°.

[0156] In the liquid crystal curing layer, the angle between the long axis of the liquid crystal compound and the main surface of the liquid crystal curing layer is preferably 0 to 5°, more preferably 0 to 3°, and even more preferably 0 to 2°.

[0157] The liquid crystal curing 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.

[0158] Here, the positive A plate and the positive C plate are defined as follows.

[0159] When the refractive index along the slow axis (the direction with the highest refractive index in the plane) is set as nx, the refractive index along the direction orthogonal to the slow axis in the plane is set as ny, and the refractive index along the thickness direction is set as nz, the positive A plate satisfies equation (A1), and the positive C plate satisfies equation (C1). Furthermore, the Rth of the positive A plate shows a positive value, while the Rth of the positive C plate shows a negative value.

[0160] Equation (A1) nx>ny≈nz Equation (C1) nz>nx≈ny Furthermore, the above "≈" includes not only cases where the two are exactly the same, but also cases where the two are substantially the same.

[0161] Regarding the phrase "substantially identical," in the positive A-plate, for example, the case where (ny-nz)×d (where d is the film thickness) is -10 to 10 nm, preferably -5 to 5 nm, is also included in "ny≈nz," and the case where (nx-nz)×d is -10 to 10 nm, preferably -5 to 5 nm, is also included in "nx≈nz." Furthermore, in the positive C-plate, for example, the case where (nx-ny)×d (where d is the film thickness) is 0 to 10 nm, preferably 0 to 5 nm, is also included in "nx≈ny."

[0162] When the liquid crystal curing 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 especially preferably 130 to 145 nm.

[0163] Here, "λ / 4 plate" refers to a plate with λ / 4 function, specifically a plate that has the function of converting linearly polarized light of a specific wavelength into circularly polarized light (or converting circularly polarized light into linearly polarized light).

[0164] In the case where the liquid crystal composition of the present invention contains a dichroic substance, the liquid crystal cured layer of the present invention can be used as a polarizer (light-absorbing anisotropic film).

[0165] [Optical film] The optical film of the present invention is an optical film having the liquid crystal curing layer of the present invention.

[0166] refer to Figure 1 The structure of the optical film is explained. Figure 1 This is a schematic cross-sectional view showing an example of an optical film.

[0167] in addition, Figure 1 This is a schematic diagram; the thickness and positional relationships of the layers may not necessarily match the actual situation. Figure 1 The support and orientation film shown are arbitrary components.

[0168] Figure 1 The optical film 10 shown has a support 16, an alignment film 14 and a liquid crystal curing layer 12, which is a cured liquid crystal composition of the present invention.

[0169] Furthermore, the liquid crystal curing layer 12 can be a stack of two or more different liquid crystal curing layers. For example, when the polarizer of the present invention described later is used as a circular polarizer, or when the optical film of the present invention is used as an optical compensation film for a liquid crystal display device of IPS (In-Plane-Switching) or FFS (Fringe-Field-Switching) mode, a stack of positive A plate and positive C plate is preferred.

[0170] Furthermore, the liquid crystal curing layer can also be peeled off from the support and used separately as an optical film.

[0171] The following is a detailed description of the various components used in optical films.

[0172] [Liquid Crystal Curing Layer] The liquid crystal curing layer of the optical film of the present invention is the liquid crystal curing layer of the present invention described above.

[0173] In optical films, the thickness of the liquid crystal curing layer is not particularly limited, but it is preferably 0.1 to 10 μm, more preferably 0.5 to 5 μm.

[0174] [Support] As described above, the optical film may have a support as a substrate for forming the liquid crystal curing layer.

[0175] This support is preferably transparent. Specifically, the light transmittance is preferably 80% or higher.

[0176] Examples of such supports include glass substrates and polymer films. Examples of polymer film materials include cellulose-based polymers; acrylic polymers such as polymethyl methacrylate and polymers containing lactone rings; 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 polyamides; 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; aromatic ester-based polymers; polyoxymethylene-based polymers; epoxy-based polymers; and polymers composed of mixtures of these polymers.

[0177] Furthermore, the deflector described later can also serve as this support.

[0178] The thickness of the aforementioned support is not particularly limited, but is preferably 5 to 60 μm, more preferably 5 to 40 μm.

[0179] [Orientation film] In optical films, the liquid crystal curing layer is preferably formed on the surface of the alignment film (especially the photoalignment film described later). When the optical film has any of the aforementioned supports, the alignment film can be sandwiched between the support and the liquid crystal curing layer. Furthermore, the aforementioned support can also serve as the alignment film.

[0180] The alignment film can be any film as long as it has the function of horizontally aligning the liquid crystal compound contained in the composition.

[0181] Alignment films typically use polymers as the main component. Polymer materials for alignment films are documented in numerous publications, and several commercially available products are readily available.

[0182] Polyvinyl alcohol, polyimide, or any derivative thereof are preferred as polymer materials for orientation films, with modified or unmodified polyvinyl alcohol being more preferred.

[0183] As an optical film, an alignment film can be described, for example, the alignment film described on page 43, line 24 to page 49, line 8 of International Publication No. 01 / 88574; 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 of a liquid crystal alignment agent described in Japanese Patent Application Publication No. 2012-155308.

[0184] Optical alignment film is preferred as the alignment film because the object does not come into contact with the surface of the alignment film during the formation of the alignment film, which can prevent the surface condition from deteriorating.

[0185] As a photoalignment film, it is not particularly limited and can include alignment films formed from polymer materials such as polyamide compounds and polyimide compounds as described in paragraphs

[0024] to

[0043] of International Publication No. 2005 / 096041; liquid crystal alignment films formed from liquid crystal alignment agents having photoalignment groups as described in Japanese Patent Application Publication No. 2012-155308; and products manufactured by Rolic Technologies under the trade name LPP-JP265CP.

[0186] The thickness of the alignment film is not particularly limited, but from the viewpoint of forming a liquid crystal curing layer with uniform film thickness by mitigating the surface irregularities that may exist in the support, it is preferred to be 0.01 to 10 μm, more preferably 0.01 to 1 μm, and even more preferably 0.01 to 0.5 μm.

[0187] [Other liquid crystal curing layers] In optical films, the liquid crystal curing layer is preferably formed on the surface of other liquid crystal curing layers.

[0188] Here, as other liquid crystal curable layers, examples include liquid crystal curable layers formed by fixing the orientation state of a composition after removing a specific compound A from the liquid crystal composition of the present invention described above. Specifically, examples include liquid crystal curable layers formed by fixing the orientation state of a composition containing the liquid crystal compound, polymerization initiator, leveling agent, and solvent described above.

[0189] [Ultraviolet absorber] Considering the influence of external light (especially ultraviolet light), the optical film preferably contains an ultraviolet (UV) absorber.

[0190] The ultraviolet absorber can be contained in the liquid crystal curing layer or in components other than the liquid crystal curing layer that constitute the optical film. A support is a preferred example of a component other than the liquid crystal curing layer.

[0191] As a UV absorber, any conventionally known UV absorber capable of exhibiting UV absorption properties can be used. Among such UV absorbers, benzotriazole-based or hydroxyphenyltriazine-based UV absorbers are preferred from the viewpoint of high UV absorption and obtaining UV absorption capacity (UV cutoff capacity) for use in image display devices.

[0192] Furthermore, in order to broaden the absorption range of ultraviolet light, it is preferable to use two or more ultraviolet absorbers with different maximum absorption wavelengths simultaneously.

[0193] Examples of ultraviolet absorbers include compounds described in paragraphs

[0258] to

[0259] of Japanese Patent Application Publication No. 2012-18395 and compounds described in paragraphs

[0055] to

[0105] of Japanese Patent Application Publication No. 2007-72163.

[0194] Furthermore, as a commercially available product, it can be used with Tinuvin 400, Tinuvin 405, Tinuvin 460, Tinuvin 477, Tinuvin 479 and Tinuvin 1577 (all manufactured by BASF).

[0195] [Polarizing filter] The polarizer of the present invention has the optical film and polarizer described above.

[0196] Furthermore, when the liquid crystal curing layer of the present invention is a λ / 4 plate (positive A plate), the polarizer of the present invention can be used as a circular polarizer.

[0197] Furthermore, in the polarizer of the present invention, when the liquid crystal curing 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 later is preferably 30 to 60°, more preferably 40 to 50°, even more preferably 42 to 48°, and particularly preferably 45°.

[0198] Here, the "slow axis" of the λ / 4 plate refers to the direction in which the refractive index is at its maximum within the plane of the λ / 4 plate, and the "absorption axis" of the polarizer refers to the direction in which the absorbance is at its highest.

[0199] Furthermore, the polarizer of the present invention can also be used as an optical compensation film for liquid crystal display devices of IPS or FFS types.

[0200] When the polarizer of the present invention is used as an optical compensation film in an IPS or FFS type liquid crystal display device, the liquid crystal curing layer of the present invention can be used as at least one of the plates in a laminate of a positive A plate and a positive C plate, preferably the 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 later is orthogonal or parallel; more 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 later is 0 to 5° or 85 to 95°.

[0201] Furthermore, when the polarizer, positive C plate and positive A plate are stacked sequentially in the polarizer of the present invention, it is even more preferable that the angle between the slow axis of the positive A plate and the absorption axis of the polarizer is parallel.

[0202] Similarly, when the polarizer, positive A plate and positive C plate are stacked sequentially in the polarizer of the present invention, it is even more preferable that the angle between the slow axis of the positive A plate and the absorption axis of the polarizer is orthogonal.

[0203] When the polarizer of the present invention is used in the liquid crystal display device described later, it is preferable that the angle between the slow axis of the liquid crystal curing layer and the absorption axis of the polarizer described later is parallel or orthogonal.

[0204] Furthermore, in this specification, "parallel" means that the angle between one and another is less than 10°, and strict parallelism is not required. Also, in this specification, "orthogonal" means that the angle between one and another is greater than 80° but less than 100°, and strict orthogonality is not required.

[0205] [Polarizer] The polarizer of the polarizer of the present invention is not particularly limited as long as it is a component that has the function of converting light into specific linearly polarized light, and conventionally known absorption polarizers and reflection polarizers can be used.

[0206] As an absorption-type polarizer, iodine-based polarizers, dye-based polarizers utilizing dichroic dyes, and polyene-based polarizers can be used. Iodine-based polarizers and dye-based polarizers include coated polarizers and stretched polarizers, both of which are applicable, but polarizers made by adsorbing iodine or dichroic dyes onto polyvinyl alcohol and then stretching it are preferred.

[0207] Furthermore, as a method for obtaining a polarizer by stretching and dyeing a laminated film in which a polyvinyl alcohol layer is formed on a substrate, examples include Japanese Patent No. 5048120, Japanese Patent No. 5143918, Japanese Patent No. 4691205, Japanese Patent No. 4751481, and Japanese Patent No. 4751486, and these known technologies related to polarizers can be preferably utilized.

[0208] As a reflective polarizer, polarizers can be made by stacking different birefringent thin films, wire grid polarizers, polarizers that combine cholesteric liquid crystal with a selective reflection region with a 1 / 4 wavelength plate, etc.

[0209] From the viewpoint of superior adhesion, a polarizer comprising a polyvinyl alcohol-based resin (a polymer containing -CH2-CHOH- as repeating units, particularly selected from at least one of the groups consisting of polyvinyl alcohol and ethylene-vinyl alcohol copolymers) is preferred.

[0210] In this invention, the thickness of the polarizer is not particularly limited, but is preferably 3μm to 60μm, more preferably 5μm to 30μm, and even more preferably 5μm to 15μm.

[0211] [Adhesive layer] The polarizer of the present invention may have an adhesive layer disposed between the liquid crystal curing layer and the polarizer in the optical film of the present invention.

[0212] As an adhesive layer used for laminating the liquid crystal curing layer and the polarizer, it may be a so-called adhesive or a material prone to creep, for example, containing a substance that represents a ratio (tanδ=G” / G’) of 0.001 to 1.5 of the storage modulus G’ measured by a dynamic viscoelasticity measuring device. Examples of adhesives that can be used in this invention include polyvinyl alcohol-based adhesives, but are not limited thereto.

[0213] [Image display device] The image display device of the present invention is an image display device having the optical film or polarizer of the present invention.

[0214] The display element used in the image display device is not particularly limited, and examples include liquid crystal cells, organic electroluminescent (hereinafter referred to as "EL (Electro Luminescence)") display panels, and plasma display panels. Among these, liquid crystal cells and organic EL display panels are preferred, and liquid crystal cells are more preferred.

[0215] That is, as an image display device, a liquid crystal display device that uses liquid crystal cells as display elements or an organic EL display device that uses organic EL display panels as display elements is preferred, and a liquid crystal display device is even more preferred.

[0216] [Liquid Crystal Display Device] As an example of an image display device, a liquid crystal display device is a liquid crystal display device having the aforementioned polarizer and liquid crystal unit.

[0217] Furthermore, it is preferable to use the aforementioned polarizer as the front polarizer among the polarizers disposed on both sides of the liquid crystal cell, and more preferably to use the aforementioned polarizer as both the front and rear polarizers.

[0218] The liquid crystal unit that constitutes a liquid crystal display device will be described in detail below.

[0219] <Liquid Crystal Unit> The liquid crystal cells used in the liquid crystal display device are preferably in VA (Vertical Alignment) mode, OCB (Optically Compensated Bend) mode, IPS (In-Plane-Switching) mode, FFS (Fringe-Field-Switching) mode or TN (Twisted Nematic) mode, but are not limited to these.

[0220] In TN mode liquid crystal cells, the rod-shaped liquid crystal molecules are substantially horizontally oriented when no voltage is applied, and their twisted orientation is 60–120°. TN mode liquid crystal cells are most commonly used in color TFT liquid crystal display devices and are documented in numerous publications.

[0221] In a VA-mode liquid crystal cell, the rod-shaped liquid crystal molecules are substantially vertically oriented when no voltage is applied. In a VA-mode liquid crystal cell, in addition to (1) a narrow VA-mode liquid crystal cell in which the rod-shaped liquid crystal molecules are substantially vertically oriented when no voltage is applied and substantially horizontally oriented when a voltage is applied (described in Japanese Patent Application Publication No. 2-176625), there are also (2) a liquid crystal cell in which the VA mode is multi-domainized (MVA mode) in order to expand the viewing angle (described in SID97, Digest of tech. Papers (preprint) 28 (1997) 845), (3) a liquid crystal cell in which the rod-shaped liquid crystal molecules are substantially vertically oriented when no voltage is applied and twisted into multi-domain orientation when a voltage is applied (n-ASM mode) (described in preprints 58-59 (1998) of the Japan Liquid Crystal Conference), and (4) a SURVIVAL mode liquid crystal cell (published in LCD International 98). Furthermore, the liquid crystal cell in VA mode can be any of PVA (Patterned Vertical Alignment), Optical Alignment, or PSA (Polymer-Sustained Alignment). Detailed information about these modes can be found in Japanese Patent Application Publication Nos. 2006-215326 and 2008-538819.

[0222] In IPS-mode liquid crystal cells, rod-shaped liquid crystal molecules are substantially parallel to the substrate, and by applying an electric field parallel to the substrate surface, the liquid crystal molecules respond planarly. In IPS mode, black is displayed when no electric field is applied, and the absorption axes of the upper and lower polarizers are orthogonal. Methods for reducing light leakage and improving viewing angles when displaying black in the tilt direction using optical compensation sheets are disclosed in Japanese Patent Application Publications Nos. 10-54982, 11-202323, 9-292522, 11-133408, 11-305217, and 10-307291.

[0223] [Organic EL display device] Regarding an organic EL display device as an example of an image display device, one example is a device that, from the visual recognition side, has a polarizer, a λ / 4 plate (positive A plate) composed of the aforementioned liquid crystal curing layer, and an organic EL display panel in sequence.

[0224] Furthermore, organic EL display panels are display panels made of organic EL elements formed by sandwiching an organic light-emitting layer (organic electroluminescent layer) between electrodes (between the cathode and the anode). The structure of organic EL display panels is not particularly limited and can adopt known structures.

[0225] Example The present invention will now be described in further detail with reference to embodiments. Regarding the materials, amounts, proportions, processing contents, and processing steps shown in the following embodiments, appropriate modifications can be made without departing from the spirit of the invention. Therefore, the scope of the present invention should not be interpreted as limited by the embodiments shown below.

[0226] [Synthesis example] Synthesis of intermediate (AH) The intermediate (AH) represented by the following formula (AH) was synthesized according to the synthetic method of compound I-1-e described in International Publication No. 2019 / 111853.

[0227] [Chemical Formula 9] [Synthesis of intermediate (B-1)] The intermediate (B-1) represented by the following formula (B-1) was synthesized according to the following scheme.

[0228] [Chemical Formula 10] Specifically, 7.88 g (40.6 mmol) of monotetrahydropyranyl-protected hydroquinone synthesized by the method described in Japanese Patent Application Publication No. 2010-031223, 10.0 g (36.9 mmol) of 6-bromohexanebenzyl ether synthesized by the method described in Chemistry Letters (2000), (12), 1352-1355, and 7.65 g (55.4 mmol) of potassium carbonate were dissolved or dispersed in 200 mL of dimethylacetamide.

[0229] Next, the mixture was stirred at 100°C under nitrogen atmosphere. After cooling to room temperature, pure water and methyl isobutyl ketone were added. The recovered organic layer was washed with sodium hydroxide solution and pure water, then dehydrated, filtered, and concentrated under reduced pressure. Methanol was added to the residue, and the resulting precipitate was filtered and then dried under vacuum to obtain 12.5 g (32.5 mmol, 88%) of intermediate (B-1).

[0230] [Synthesis of intermediate (B-2)] The intermediate (B-2) represented by the following formula (B-2) was synthesized according to the following scheme.

[0231] [Chemical Formula 11] Specifically, 12.0 g (31.2 mmol) of intermediate (B-1) was dissolved in 200 mL of tetrahydrofuran (hereinafter referred to as "THF"), and 50 mL of 2N hydrochloric acid water was added. The mixture was stirred under nitrogen atmosphere at 60 °C. 200 mL of saturated brine was added to the reaction solution, and the mixture was stirred further. The separated organic layer was recovered. The recovered organic layer was dehydrated, filtered, and then concentrated under reduced pressure. Hexane was added to the organic layer, and the mixture was stirred under ice-cold conditions. The precipitated powder was filtered and then dried under vacuum to obtain 7.5 g (25.0 mmol, 80%) of intermediate (B-2).

[0232] [Synthesis of intermediate (B-3)] The intermediate (B-3) represented by the following formula (B-3) was synthesized according to the following scheme.

[0233] [Chemical Formula 12] Specifically, 7.0 g (23.3 mmol) of intermediate (B-2) was dissolved in 100 mL of THF. After stirring at 0 °C under ice-cold conditions, 14.6 g (69.8 mmol) of cyclohexanedicarboxylic acid powder was added. Triethylamine (46.6 mmol) was then added, and the mixture was stirred at 0 °C for 2 hours. After the reaction, 50 mL of water was added, and the mixture was stirred for 1 hour. Then, 200 mL of methanol was added dropwise, and the precipitate was filtered off. Recrystallization of the crude product from THF-methanol yielded 5.2 g (11.4 mmol, 49%) of intermediate (B-3).

[0234] Synthesis of intermediate (BH) The intermediate (BH) represented by the following formula (BH) was synthesized according to the following scheme.

[0235] [Chemical Formula 13] Specifically, 5.0 g (11.0 mmol) of intermediate (B-3) was dissolved in 50 mL of THF, and 0.5 g of 10% palladium on carbon was added. The mixture was stirred for 3 hours under hydrogen atmosphere. The reaction solution was filtered through diatomaceous earth, methanol was added, and the precipitate was filtered off. 3.81 g (10.5 mmol, 95%) of intermediate (BH) was obtained.

[0236] [Example 1] [Preparation of Liquid Crystal Composition 1] A liquid crystal composition 1 containing liquid crystal compounds (1-A), (1-B) and (1-C) represented by the following formulas was prepared according to the following scheme.

[0237] [Chemical Formula 14] Specifically, 9.0 g (23.7 mmol) of intermediate (A) represented by formula (A), 1.0 g (3.1 mmol) of intermediate (AH) represented by formula (AH), 40 mL of toluene, 15 mL of N,N-dimethylacetamide (DMAc), and 150 mg of 2,6-di-tert-butyl-4-methylphenol were mixed at room temperature, and the internal temperature was cooled to 5 °C. 2.9 mL (40.2 mmol) of thionyl chloride (SOCl2) was added dropwise to the mixture to prevent the internal temperature from rising above 10 °C. After stirring at 5 °C for 1 hour, 3.0 g (12.1 mmol) of tetrahydrofuran (THF) solution (50 mL) was added to the core (1-1) represented by formula (1-1). After adding 11.6 mL (66.4 mmol) of N,N-diisopropylethylamine (DIPEA), the mixture was stirred at room temperature for 2 hours. After stirring, 40 ml of 1N hydrochloric acid solution and 40 ml of ethyl acetate were added to stop the reaction, and the mixture was separated. After washing the organic layer with 10% saline solution, 60 mL of isopropanol and 40 mL of methanol were added dropwise, and the mixture was cooled to 5°C and the precipitated crystals were filtered off.

[0238] Analysis of the products by liquid chromatography-mass spectrometry (LC-MS) confirmed that the liquid crystal compounds (1-A) / (1-B) / (1-C) contained 85 / 7 / 8 by mass. Furthermore, based on the mass spectrometry (MS) spectra of each component, the molecular weights of the liquid crystal compounds (1-A) / (1-B) / (1-C) were confirmed to be 972.39 / 918.38 / 936.35 (M+). Additionally, based on the ultraviolet (UV) spectra of each component, it was confirmed that the liquid crystal compounds (1-A) / (1-B) / (1-C) all exhibited a maximum absorption wavelength at 355 nm.

[0239] [Example 2] [Preparation of Liquid Crystal Composition 2] A liquid crystal composition 2 containing liquid crystal compounds (1-A) and (2) represented by the following formulas was prepared according to the following scheme.

[0240] [Chemical Formula 15] Specifically, 10 g (10.3 mmol) of compound (1-A), represented by the above formula (1-A) and synthesized by the method described in International Publication No. 2019 / 017445, was dissolved in 100 mL of THF, 0.13 g (1.0 mmol) of dimethylaminopyridine (DMAP) and 1.0 mL of 1N hydrochloric acid were added, and the mixture was stirred at room temperature for 2 hours. After stirring, 100 mL of methanol was added, and the precipitated crystals were filtered off.

[0241] LC-MS analysis of the products confirmed that the liquid crystal compound (1-A) / compound (2) comprised a mass ratio of 99 / 1. Furthermore, based on the MS spectrum, the molecular weight of the cationic component of liquid crystal compound (2) was confirmed to be 1095.48. Additionally, based on the UV spectra of each component, liquid crystal compound (2) was confirmed to have a maximum absorption wavelength at 355 nm.

[0242] [Example 3] [Preparation of liquid crystal composition 3] A liquid crystal composition 3 containing liquid crystal compounds (3-A), (3-B) and (3-C) represented by the following formulas was prepared according to the following scheme.

[0243] [Chemical Formula 16] Specifically, intermediate (B) represented by formula (B) above is used instead of intermediate (A), intermediate (BH) represented by formula (BH) above is used instead of intermediate (AH), and core (2-1) represented by formula (2-1) above is used instead of core (1-1). Otherwise, liquid crystal composition 3 is prepared by the same method as liquid crystal composition 1.

[0244] LC-MS analysis of the products confirmed that the liquid crystal compounds (3-A) / (3-B) / (3-C) comprised 83 / 8 / 9 by mass. Furthermore, based on the MS spectra of each component, the molecular weights of the liquid crystal compounds (3-A) / (3-B) / (3-C) were determined to be 1128.41 / 1074.40 / 1092.37 (M+). Additionally, based on the UV spectra of each component, it was confirmed that the liquid crystal compounds (3-A) / (3-B) / (3-C) all exhibited a maximum absorption wavelength at 355 nm.

[0245] Liquid crystal composition 3 was purified by column chromatography, and liquid crystal compounds (3-B) and (3-C) were separated. The MS spectra of liquid crystal compound (3-B) were 1074.40 (100.0%) and 1075.40 (66.6%), and the MS spectra of liquid crystal compound (3-C) were 1092.37 (100.0%) and 1093.37 (66.6%).

[0246] Synthesis of liquid crystal compound (3-A) Intermediate (B) 1.2 g (26.8 mmol), toluene 40 mL, N,N-dimethylacetamide (DMAc) 15 mL, and 2,6-di-tert-butyl-4-methylphenol 150 mg were mixed at room temperature, and the internal temperature was cooled to 5 °C. Thionyl chloride (SOCl2) 2.9 mL (40.2 mmol) was added dropwise to the mixture to prevent the internal temperature from rising above 10 °C. After stirring at 5 °C for 1 hour, 4.0 g (12.2 mmol) of tetrahydrofuran (THF) solution (50 mL) was added to the core (2-1). N,N-diisopropylethylamine (DIPEA) 11.6 mL (66.4 mmol) was added dropwise, and the mixture was stirred at room temperature for 2 hours. After stirring, the reaction was stopped by adding 40 mL of 1N hydrochloric acid and 40 mL of ethyl acetate, and the mixture was separated. After washing the organic layer with 10% saline solution, 60 mL of isopropanol and 40 mL of methanol were added dropwise, then the mixture was cooled to 5°C and the precipitated crystals were filtered off. The crude product was purified by column chromatography to obtain 5.0 g (4.4 mmol, 36%) of liquid crystal compound (3-A).

[0247] [Example 4] [Preparation of liquid crystal composition 4] A liquid crystal composition 4 containing liquid crystal compounds (3-A) and (4) represented by the following formulas was prepared according to the following scheme.

[0248] [Chemical Formula 17] Specifically, instead of compound (1-A), compound (3-A) represented by the above formula (3-A) was used, and liquid crystal composition 4 was prepared by the same method as liquid crystal composition 2.

[0249] LC-MS analysis of the products confirmed that the liquid crystal compound (3-A) / (4) contained 99 / 1 by mass. Furthermore, based on the MS spectrum, the molecular weight of the cationic component of compound (4) was confirmed to be 1251.50. Furthermore, based on the UV spectra of each component, compound (4) was confirmed to have a maximum absorption wavelength at 355 nm.

[0250] [Example 5] [Preparation of liquid crystal composition 5] A liquid crystal composition 5 containing liquid crystal compounds (5-A), (5-B) and (5-C) represented by the following formulas was prepared according to the following scheme.

[0251] [Chemical Formula 18] Specifically, intermediate (B) was used instead of intermediate (A), intermediate (BH) was used instead of intermediate (AH), and the core (3-1) represented by the above formula (3-1) was used instead of core (1-1). Otherwise, liquid crystal composition 5 was prepared by the same method as liquid crystal composition 1.

[0252] LC-MS analysis of the products confirmed the presence of liquid crystal compounds (5-A) / (5-B) / (5-C) in a mass ratio of 82 / 9 / 9. Furthermore, based on the MS spectra of each component, the molecular weights of liquid crystal compounds (5-A) / (5-B) / (5-C) were determined to be 1111.44 / 1057.43 / 1075.39 (M+). Additionally, UV spectra of each component confirmed that liquid crystal compounds (5-A) / (5-B) / (5-C) all exhibited a maximum absorption wavelength at 349 nm.

[0253] Liquid crystal composition 5 was purified by column chromatography, and liquid crystal compounds (5-B) and (5-C) were separated. The MS spectra of liquid crystal compound (5-B) were 1057.43 (100.0%) and 1058.43 (67.4%), and the MS spectra of liquid crystal compound (5-C) were 1075.39 (100.0%) and 1076.40 (66.1%).

[0254] Synthesis of liquid crystal compound (5-A) The core (2-1) was replaced with the core (3-1), and the liquid crystal compound (5-A) was synthesized by the same method as the liquid crystal compound (3-A).

[0255] [Example 6] [Preparation of liquid crystal composition 6] A liquid crystal composition 6 containing liquid crystal compounds (5-A) and (6) represented by the following formulas was prepared according to the following scheme.

[0256] [Chemical Formula 19] Specifically, instead of compound (1-A), liquid crystal compound (5-A) represented by the above formula (5-A) was used, and liquid crystal composition 6 was prepared by the same method as liquid crystal composition 2.

[0257] LC-MS analysis of the products confirmed that the liquid crystal compounds (5-A) / (6) comprised 99 / 1 by mass. Furthermore, based on the MS spectrum, the molecular weight of the cationic component of compound (6) was confirmed to be 1234.53. Additionally, based on the UV spectra of each component, compound (6) was confirmed to have a maximum absorption wavelength of 349 nm.

[0258] [Compare Examples 1 and 2] As comparative examples 1 and 2, the above-mentioned liquid crystal compound (3-A) and liquid crystal compound (5-A) were used respectively.

[0259] [evaluate] [Stretchability] A coating liquid (liquid crystal composition) having the following composition was prepared and coated onto 75 μm thick PET manufactured by FUJIFILM Corporation using a rod coating method. The coating was then oriented at 140°C to form a liquid crystal layer. The mixture was then cooled to 60°C and subjected to a process based on 300 mJ / cm². 2 An optical film for tensile evaluation was obtained by fixing the orientation of the film under ultraviolet light to form a liquid crystal cured layer. Furthermore, the wavelength dispersion of the obtained optical film was measured using an AxoScan (manufactured by Axometrics Corporation), confirming that all films exhibited anti-wavelength dispersion.

[0260] ――――――――――――――――――――――――――――― Coating liquid ――――――――――――――――――――――――――――― • Liquid crystal compound (the compound or composition listed in Table 1 below) 15.00 parts by weight • Photopolymerization initiator (IRGACURE 819, manufactured by BASF) 0.45 parts by weight • 0.12 parts by weight of the following fluorinated compound A Chloroform 35.00 parts by weight ――――――――――――――――――――――――――――― Fluorine compound A [Chemical Formula 20] The obtained optical film was cut into 1cm × 5cm samples. The samples were gripped at the top and bottom 1cm using clamps, and a tensile test was performed at 300mm / s in a 150°C environment using a heated Tensilon (RTF-1310 and TKC thermostatic testing apparatus manufactured by A&D Company, Limited). The state of the liquid crystal cured layer in the samples was observed, and the elongation at break of the liquid crystal cured layer was determined according to the following formula. In the following formula, "distance between punctuation marks at fracture" refers to the distance between punctuation marks in the liquid crystal layer of the sample at the point of fracture.

[0261] Formula: Elongation at break (%) = {(Distance between markers at break - Distance between markers before test) / (Distance between markers before test)} × 100 <Standard> A: Elongation at break is 30% or more B: Elongation at break is 10% or more but less than 30%. C: Elongation at break is less than 10%. [Extraction] 20 μL of the coating solution prepared above was dropped onto a glass plate and placed at 25°C for 1 hour. The degree of precipitation of the solid film was then visually observed. Specifically, the area of ​​the turbid portion (whitened portion) was estimated relative to the area of ​​the solid film, and the precipitation was judged according to the following criteria with an index of 1 to 3. The results are shown in Table 1 below.

[0262] <Standard> Extraction 1: Whitening of 75% or more but less than 100% Extraction 2: Whitening of 25% or more but less than 75% Extraction property 3: less than 25% whitening [Table 1]

[0263] According to the results shown in Table 1 above, in the absence of the second liquid crystal compound, the liquid crystal composition becomes one in which the exudation cannot be suppressed, and the tensile properties of the liquid crystal cured layer produced are also poor (Comparative Examples 1-2).

[0264] In contrast, it can be seen that the precipitation of the liquid crystal composition containing the first liquid crystal compound and the second liquid crystal compound is suppressed, and the tensile properties of the prepared liquid crystal cured layer are also improved (Examples 1-6).

[0265] Symbol Explanation 10-Optical film, 12-Liquid crystal curing layer, 14-Orientation film, 16-Support.

Claims

1. A liquid crystal composition comprising a first liquid crystal compound represented by formula (1) and a second liquid crystal compound represented by formula (2). Both the first liquid crystal compound and the second liquid crystal compound have extremely high absorption wavelengths in the wavelength range of 280–420 nm. [Chemical Formula 1] in, In equations (1) and (2), M represents a divalent mesocrystalline framework having three or more rings, including aromatic or aliphatic rings that may have substituents. In formulas (1) and (2), M represents the same group. SP 1 The term represents a single bond or a divalent aliphatic hydrocarbon group with 1 to 20 carbon atoms, wherein one or more of the -CH2- atoms constituting the aliphatic hydrocarbon group can be substituted by -O-, -S-, -NH-, -N(Q)- or -CO-, where Q represents a substituent, and SP in formulas (1) and (2) represents a single bond or a divalent aliphatic hydrocarbon group with 1 to 20 carbon atoms. 1 Indicates groups that are the same as each other. SP 2 The term represents a single bond or a divalent aliphatic hydrocarbon group with 1 to 20 carbon atoms, wherein one or more of the -CH2- atoms constituting the aliphatic hydrocarbon group can be substituted by -O-, -S-, -NH-, -N(Q)- or -CO-, where Q represents a substituent, and SP in formulas (1) and (2) represents a single bond or a divalent aliphatic hydrocarbon group with 1 to 20 carbon atoms. 2 Indicates groups that are the same as each other. L 1 The L in formulas (1) and (2) represents a polymerizable group. 1 Indicates groups that are the same as each other. L 2 Indicates a polymerizable group. T represents a hydroxyl group, a halogen atom, an alkyl carbonyl group having 1 to 6 carbon atoms, or a substituent represented by formula (3) or (4) below. [Chemical Formula 2] In equations (3) and (4), Indicates SP 2 The bonding position, X - Indicates resistance to anions, R T1 ~R T3 Each alkyl group independently represents an alkyl group having 1 to 6 carbon atoms, wherein one or more of the -CH2- groups constituting the alkyl group can be substituted with -O-, -S-, -NH-, -N(Q)-, or -CO-, where Q represents a substituent, and regarding R... T1 ~R T3 R T1 ~R T3 Two or three of them can bond together to form a ring. R T4 and R T5 Each of the following independently represents an alkyl group having 1 to 6 hydrogen atoms or carbon atoms, wherein one or more of the -CH2- groups constituting the alkyl group can be substituted with -O-, -S-, -NH-, -N(Q)-, or -CO-, where Q represents a substituent. A represents a 5- or 6-membered nitrogen-containing aromatic ring that may have substituents.

2. The liquid crystal composition according to claim 1, wherein, In equations (1) and (2), M represents the divalent mesocrystalline framework represented by equation (5) below. [Chemical Formula 3] In equation (5), Indicates SP 1 or SP 2 The bonding position, B 1 and B 2 Each of these groups independently represents an aromatic ring with 6 to 20 carbon atoms that may have substituents, or a divalent alicyclic hydrocarbon group with 5 to 20 carbon atoms that may have substituents, wherein one or more of the -CH2- groups constituting the alicyclic hydrocarbon group can be substituted with -O-, -S-, or -NH-. D 1 D 2 D 3 and D 4 Each can independently represent a single bond or -CO-, -O-, -S-, -C(=S)-, -CR 1 R 2 -、-CR 3 =CR 4 -、-NR 5 - or a divalent linker consisting of two or more of them, R 1 ~R 5 Each of the following can be independently represented by a hydrogen atom, a fluorine atom, or an alkyl group having 1 to 12 carbon atoms. m1 and m2 independently represent integers from 1 to 3. When m1 represents 2 or 3, multiple B 1 and D 1 The terms can be the same or different. When m2 represents 2 or 3, multiple B's... 2 and D 2 They can be the same or different. Ar represents any aromatic ring selected from the group consisting of the groups represented by the following formulas (Ar-1) to (Ar-7). [Chemical Formula 4] Among them, in the formulas (Ar-1) to (Ar-7), Indicates D 1 Or D 2 The bonding position, Q 1 Indicates N or CH, Q 2 Indicates -S-, -O-, or -N(R) 6 )-,R 6 Indicates an alkyl group having 1 to 6 hydrogen atoms or carbon atoms. Y 1 This indicates an aromatic hydrocarbon group with 6 to 12 carbon atoms that may have substituents, an aromatic heterocyclic group with 3 to 12 carbon atoms that may have substituents, or an alicyclic hydrocarbon group with 6 to 20 carbon atoms that may have substituents, wherein one or more of the -CH2- groups constituting the alicyclic hydrocarbon group may be substituted with -O-, -S-, or -NH-. Z 1 Z 2 and Z 3 Each of the following can be independently represented: a hydrogen atom, a monovalent aliphatic hydrocarbon group with 1-20 carbon atoms, a monovalent alicyclic hydrocarbon group with 3-20 carbon atoms, a monovalent aromatic hydrocarbon group with 6-20 carbon atoms, a monovalent aromatic heterocyclic group with 6-20 carbon atoms, a halogen atom, a cyano group, a nitro group, or -OR. 7 -NR 8 R 9 -SR 10 -COOR 11 or -COR 12 R 7 ~R 12 Z represents, independently, either a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. 1 and Z 2 They can bond with each other to form aromatic rings. A 3 and A 4 Represent the selection independently of -O- and -N(R) 13 The group consisting of -, -S- and -CO-, R 13 Represents a hydrogen atom or a substituent. X represents a nonmetallic atom from groups 14 to 16, wherein the nonmetallic atom may be bonded with hydrogen atoms or substituents. D 7 and D 8 Each can independently represent a single bond or -CO-, -O-, -S-, -C(=S)-, -CR 1 R 2 -、-CR 3 =CR 4 -、-NR 5 - or a divalent linker consisting of two or more of them, R 1 ~R 5 Each of the following can be independently represented by a hydrogen atom, a fluorine atom, or an alkyl group having 1 to 12 carbon atoms. SP 3 and SP 4 Each of the above independently represents a single bond or a divalent aliphatic hydrocarbon group having 1 to 20 carbon atoms, wherein one or more of the -CH2- groups constituting the aliphatic hydrocarbon group can be substituted by -O-, -S-, -NH-, -N(Q)-, or -CO-, where Q represents a substituent. L 3 and L 4 Each of the above can independently represent a monovalent organic group. Ax represents an organic group having 2 to 30 carbon atoms in at least one aromatic ring selected from the group consisting of aromatic hydrocarbon rings and aromatic heterocycles. Ay represents a hydrogen atom, an alkyl group having 1 to 12 carbon atoms that may have substituents, or an organic group having 2 to 30 carbon atoms in at least one aromatic ring selected from the group consisting of aromatic hydrocarbon rings and aromatic heterocycles. The aromatic rings in Ax and Ay can have substituents, and Ax and Ay can also bond together to form a ring. Q 3 It represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms that may have substituents.

3. The liquid crystal composition according to claim 1, wherein, The content of the second liquid crystal compound is 0.01 to 20% of the total mass of the first liquid crystal compound and the second liquid crystal compound.

4. A liquid crystal compound, represented by the following formula (2), [Chemical Formula 5] in, In the above formula (2), M represents the divalent mesocrystalline framework represented by the following equation (5), SP 1 This refers to a single bond or a divalent aliphatic hydrocarbon group with 1 to 20 carbon atoms, wherein one or more of the -CH2- groups constituting the aliphatic hydrocarbon group can be substituted by -O-, -S-, -NH-, -N(Q)-, or -CO-, where Q represents a substituent. SP 2 This refers to a single bond or a divalent aliphatic hydrocarbon group with 1 to 20 carbon atoms, wherein one or more of the -CH2- groups constituting the aliphatic hydrocarbon group can be substituted by -O-, -S-, -NH-, -N(Q)-, or -CO-, where Q represents a substituent. L 1 Indicates a polymerizable group. T represents a hydroxyl group, a halogen atom, an alkyl carbonyl group having 1 to 6 carbon atoms, or a substituent represented by formula (3) or (4) below. [Chemical Formula 6] In equation (5), Indicates SP 1 or SP 2 The bonding position, B 1 and B 2 Each of these groups independently represents an aromatic ring with 6 to 20 carbon atoms that may have substituents, or a divalent alicyclic hydrocarbon group with 5 to 20 carbon atoms that may have substituents, wherein one or more of the -CH2- groups constituting the alicyclic hydrocarbon group can be substituted with -O-, -S-, or -NH-. D 1 D 2 D 3 and D 4 Each can independently represent a single bond or -CO-, -O-, -S-, -C(=S)-, -CR 1 R 2 -、-CR 3 =CR 4 -、-NR 5 - or a divalent linker consisting of two or more of them, R 1 ~R 5 Each of the following can be independently represented by a hydrogen atom, a fluorine atom, or an alkyl group having 1 to 12 carbon atoms. m1 and m2 independently represent integers from 1 to 3. When m1 represents 2 or 3, multiple B 1 and D 1 The terms can be the same or different. When m2 represents 2 or 3, multiple B's... 2 and D 2 They can be the same or different. Ar represents any aromatic ring selected from the group consisting of the groups represented by the following formulas (Ar-1) to (Ar-7). [Chemical Formula 7] Among them, in the formulas (Ar-1) to (Ar-7), Indicates D 1 Or D 2 The bonding position, Q 1 Indicates N or CH, Q 2 Indicates -S-, -O-, or -N(R) 6 )-,R 6 Indicates an alkyl group having 1 to 6 hydrogen atoms or carbon atoms. Y 1 This indicates an aromatic hydrocarbon group with 6 to 12 carbon atoms that may have substituents, an aromatic heterocyclic group with 3 to 12 carbon atoms that may have substituents, or an alicyclic hydrocarbon group with 6 to 20 carbon atoms that may have substituents, wherein one or more of the -CH2- groups constituting the alicyclic hydrocarbon group may be substituted with -O-, -S-, or -NH-. Z 1 Z 2 and Z 3 Each of the following can be independently represented: a hydrogen atom, a monovalent aliphatic hydrocarbon group with 1-20 carbon atoms, a monovalent alicyclic hydrocarbon group with 3-20 carbon atoms, a monovalent aromatic hydrocarbon group with 6-20 carbon atoms, a monovalent aromatic heterocyclic group with 6-20 carbon atoms, a halogen atom, a cyano group, a nitro group, or -OR. 7 -NR 8 R 9 -SR 10 -COOR 11 or -COR 12 R 7 ~R 12 Z represents, independently, either a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. 1 and Z 2 They can bond with each other to form aromatic rings. A 3 and A 4 Represent the selection independently of -O- and -N(R) 13 The group consisting of -, -S- and -CO-, R 13 Represents a hydrogen atom or a substituent. X represents a nonmetallic atom from groups 14 to 16, wherein the nonmetallic atom may be bonded with hydrogen atoms or substituents. D 7 and D 8 Each can independently represent a single bond or -CO-, -O-, -S-, -C(=S)-, -CR 1 R 2 -、-CR 3 =CR 4 -、-NR 5 - or a divalent linker consisting of two or more of them, R 1 ~R 5 Each of the following can be independently represented by a hydrogen atom, a fluorine atom, or an alkyl group having 1 to 12 carbon atoms. SP 3 and SP 4 Each of the above independently represents a single bond or a divalent aliphatic hydrocarbon group having 1 to 20 carbon atoms, wherein one or more of the -CH2- groups constituting the aliphatic hydrocarbon group can be substituted by -O-, -S-, -NH-, -N(Q)-, or -CO-, where Q represents a substituent. L 3 and L 4 Each of the L groups independently represents a monovalent organic group. 3 and L 4 and L in equation (B) 1 and L 2 At least one of them represents a polymerizable group. Ax represents an organic group having 2 to 30 carbon atoms in at least one aromatic ring selected from the group consisting of aromatic hydrocarbon rings and aromatic heterocycles. Ay represents a hydrogen atom, an alkyl group having 1 to 12 carbon atoms that may have substituents, or an organic group having 2 to 30 carbon atoms in at least one aromatic ring selected from the group consisting of aromatic hydrocarbon rings and aromatic heterocycles. The aromatic rings in Ax and Ay can have substituents, and Ax and Ay can also bond together to form a ring. Q 3 Represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms that may have substituents. [Chemical Formula 8] In equations (3) and (4), Indicates SP 2 The bonding position, X - Indicates resistance to anions, R T1 ~R T3 Each alkyl group independently represents an alkyl group having 1 to 6 carbon atoms, wherein one or more of the -CH2- groups constituting the alkyl group can be substituted with -O-, -S-, -NH-, -N(Q)-, or -CO-, where Q represents a substituent, and regarding R... T1 ~R T3 R T1 ~R T3 Two or three of them can bond together to form a ring. R T4 and R T5 Each of the following independently represents an alkyl group having 1 to 6 hydrogen atoms or carbon atoms, wherein one or more of the -CH2- groups constituting the alkyl group can be substituted with -O-, -S-, -NH-, -N(Q)-, or -CO-, where Q represents a substituent. A represents a 5- or 6-membered nitrogen-containing aromatic ring that may have substituents.

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

6. An optical film having the liquid crystal curing layer of claim 5.

7. A polarizer having the optical film and polarizer as described in claim 6.

8. An image display device having the optical film of claim 6.

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