Compound, liquid crystal composition, liquid crystal cured layer, optical film, and image display device

Abstract

The present invention addresses the problem of providing: a compound having a high Δn and having excellent solubility in a solvent; a liquid crystal composition; a liquid crystal cured layer; an optical film; and an image display device. The compound of the present invention is represented by any of formulas (1)-(6), which are prescribed general formulas.

Description

Compounds, liquid crystal compositions, liquid crystal cured layers, optical films, and image display devices.

[0001] The present invention relates to compounds, liquid crystal compositions, liquid crystal cured layers, optical films, and image display devices.

[0002] Cholesteric liquid crystal phases using disc-shaped liquid crystal compounds exhibit large birefringence in the thickness direction and have different optical properties than cholesteric liquid crystal phases using rod-shaped liquid crystal compounds. In the case of cholesteric liquid crystal phases of rod-shaped liquid crystal compositions, the retardation value in the thickness direction is generally positive, whereas in the case of cholesteric liquid crystal phases of disc-shaped liquid crystal compositions, the retardation value in the thickness direction is generally negative. Thus, disc-shaped liquid crystal compositions are useful because they possess properties that cannot be achieved with rod-shaped liquid crystal compositions (for example, optical compensation using refractive index adjustment in the film thickness direction).

[0003] Examples of such disc-shaped liquid crystal compounds include compounds consisting of a rigid, planar core portion having π electrons (e.g., trisubstituted benzene, triphenylene, etc.) and terminal spacer portions that contribute to improving molecular mobility (e.g., alkylene) (see, for example, Patent Documents 1 and 2).

[0004] Japanese Patent Publication No. 2006-273781 Japanese Patent Publication No. 2007-246672

[0005] The present inventors investigated conventionally known disc-shaped liquid crystal compounds described in Patent Documents 1 and 2, and found that when attempting to increase the refractive index (Δn) of the disc-shaped liquid crystal compound from the viewpoint of broadening the reflection bandwidth of the resulting liquid crystal cured layer, the solubility in the solvent may be poor, indicating that there is room for improvement in achieving both Δn and solubility.

[0006] Therefore, the object of the present invention is to provide a compound having a high Δn and excellent solubility in solvents, a liquid crystal composition, a liquid crystal cured layer, an optical film, and an image display device.

[0007] As a result of diligent research into the above-mentioned problems, the inventors of the present invention have found that compounds represented by any of the following formulas (1) to (6) have a high Δn and excellent solubility in solvents, and have completed the present invention. That is, the inventors of the present invention have found that the above-mentioned problems can be solved by the following configuration.

[0008] [1] A compound represented by any of the formulas (1) to (6) described later. [2] The compound according to [1], wherein the compound represented by any of the formulas (1) to (6) described later has a fused aromatic hydrocarbon ring group or a fused aromatic heterocyclic group, the fused aromatic hydrocarbon ring group is a group obtained by removing two hydrogen atoms bonded to the ring from a fused aromatic hydrocarbon ring represented by any of the formulas (X51-1) to (X51-3) described later, and the fused aromatic heterocyclic group is a group obtained by removing two hydrogen atoms bonded to the ring from a fused aromatic heterocyclic ring represented by any of the formulas (X51-4) to (X51-20) described later. [3] X １１ , X ３１ and X ４１ However, the compound described in [1] or [2] represents a five-membered heterocyclic group represented by any of the following formulas (X11-2), (X11-5), (X11-7), (X11-9), (X11-12), and (X11-14). [4] The compound described in any of [1] to [3], which is represented by formula (1) described later. [5] X in formula (A1) described later. １１ However, the compound described in [4] represents a five-membered heterocyclic group represented by formula (X11-2) described later. [6] L in formula (A1) described later １１The compound according to [4] or [5], wherein the branched alkylene group is [7] The compound according to [2], wherein the fused aromatic hydrocarbon ring group is a group obtained by removing two hydrogen atoms bonded to the ring from a fused aromatic hydrocarbon ring represented by formula (X51-1) described later. [8] The compound according to [2], wherein the fused aromatic heterocyclic group is a group obtained by removing two hydrogen atoms bonded to the ring from a fused aromatic heterocyclic ring represented by any of the formulas (X51-4), (X51-5), (X51-10), (X51-11), (X51-16), and (X51-17) described later. [9] A liquid crystal composition containing any of the compounds according to [1] to [8].

[10] The liquid crystal composition according to [9] further containing a chiral agent.

[11] A liquid crystal cured layer obtained by fixing the orientation state of the liquid crystal composition according to [9] or

[10] .

[12] An optical film having the liquid crystal cured layer according to

[11] .

[13] An image display device having the optical film described in

[12] .

[0009] As shown below, the present invention provides compounds, liquid crystal compositions, liquid crystal cured layers, optical films, and image display devices that have a high Δn and excellent solubility in solvents.

[0010] The present invention will now be described in detail. The following descriptions of constituent elements may be based on representative embodiments of the present invention, but the present invention is not limited to such embodiments. In this specification, numerical ranges expressed using "~" mean ranges that include the numbers written before and after "~" as the lower and upper limits. In this specification, an upper or lower limit stated in a numerical range described in steps may be replaced with an upper or lower limit in another numerical range described in steps. In addition, an upper or lower limit stated in a numerical range described in this specification may be replaced with a value shown in the examples. In this specification, each component may be made using one substance alone or using two or more substances in combination. Here, when two or more substances are used in combination for each component, the content for that component refers to the total content of the substances used in combination, unless otherwise specified. Furthermore, in this specification, "(meth)acrylate" refers to "acrylate" or "methacrylate," "(meth)acrylic" refers to "acrylic" or "methacrylic," "(meth)acryloyl" refers to "acryloyl" or "methacryloyl," and "(meth)acrylic acid" refers to "acrylic acid" or "methacrylic acid." Also, in this specification, unless otherwise specified, the measurement wavelength is 550 nm.

[0011] In this specification, "late axis" refers to the direction in which the refractive index is maximum within the plane. Furthermore, when referring to the late axis of the liquid crystal curing layer, it refers to the late axis of the entire liquid crystal curing layer.

[0012] In this specification, "Re(λ)" and "Rth(λ)" represent the in-plane retardation and thickness-direction retardation at wavelength λ, respectively. Here, the values ​​for in-plane retardation and thickness-direction retardation are those measured using an AxoScan OPMF-1 (manufactured by OptoScience Co., Ltd.) with light at the measurement wavelength. Specifically, by inputting the average refractive index ((nx + ny + nz) / 3) and film thickness (d) into the AxoScan OPMF-1, the following can be calculated: Late axis direction (°) Re(λ) = R0(λ) Rth(λ) = ((nx + ny) / 2 - nz) × d Note that R0(λ) is displayed as a numerical value calculated by the AxoScan OPMF-1, but it means Re(λ).

[0013] In this specification, examples of substituents (monovalent substituents) include the substituents listed in substituent group A below. In this specification, "may have substituents" includes not only embodiments without substituents but also embodiments having one or more substituents. <Substituent Group A> Substituents include, for example, halogen atoms (e.g., fluorine atom, chlorine atom, bromine atom, preferably chlorine atom, fluorine atom, more preferably fluorine atom); alkyl groups (preferably C1 to C48, more preferably C1 to C24, particularly preferably C1 to C8 alkyl groups, for example, C1 to C6 linear alkyl groups (e.g., methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group), C3 to C6 branched alkyl groups (e.g., isopropyl group, isobutyl group, tert-butyl group, sec-butyl group, neopentyl group, isohexyl group, 3-methylpentyl group), C3 to C12 cyclic alkyl groups (e.g., cyclopropyl group, cyclopentyl group, cyclohexyl group, 1-norbornyl group, 1-adamantyl group)); Alkenyl groups (preferably 2 to 48 C12, more preferably 2 to 18 C12 alkenyl groups, for example vinyl groups, allyl groups, 1-butenyl groups, 2-butenyl groups); Alkynyl groups (preferably 2 to 6 C12 alkynyl groups, more preferably 2 to 4 C12 alkynyl groups, for example ethynyl groups, 1-propynyl groups, propargyl groups, 1-butynyl groups, 2-butynyl groups); Aryl groups (preferably 6 to 48 C12, more preferably 6 to 24 C12 aryl groups, for example phenyl groups, oligoaryl groups (naphthyl groups, anthryl groups), phenanthrenyl groups, fluorenyl groups, pyrenyl groups, triphenylenyl groups, biphenyl groups); Heteroaryl groups (preferably heterocyclic groups having 1 to 32 carbon atoms, more preferably 1 to 18 carbon atoms, for example, 2-thienyl group, 4-pyridyl group, 2-furyl group, 2-pyrimidinyl group, 1-pyridyl group, 2-benzothiazolyl group, 1-imidazolyl group, 1-pyrazolyl group, benzotriazole-1-yl group);Arylalkyl groups (preferably arylalkyl groups having 7 to 15 carbon atoms, for example, benzyl group, phenethyl group, methylbenzyl group, phenylpropyl group, 1-methylphenylethyl group, phenylbutyl group, 2-methylphenylpropyl group, tetrahydronaphthyl group, naphthylmethyl group, naphthylethyl group, indenyl group, fluorenyl group, anthracenylmethyl group (anthrylmethyl group), phenanthrylmethyl group (phenanthrylmethyl group)); silyl groups (preferably silyl groups having 3 to 38 carbon atoms, more preferably silyl groups having 3 to 18 carbon atoms, for example, trimethylsilyl group, triethylsilyl group, tributylsilyl group, t-butyldimethylsilyl group, t-hexyldimethylsilyl group); hydroxyl groups; cyano groups; nitro groups; morpholino groups; Alkoxy groups (preferably alkoxy groups having 1 to 48 carbon atoms, more preferably 1 to 24 carbon atoms, for example, methoxy group, ethoxy group, 1-butoxy group, 2-butoxy group, isopropoxy group, t-butoxy group, dodecyloxy group, cycloalkyloxy group (for example, cyclopentyloxy group, cyclohexyloxy group)); aryloxy groups (preferably aryloxy groups having 6 to 48 carbon atoms, more preferably 6 to 24 carbon atoms, for example, phenoxy group, 1-naphthoxy group); alkenyloxy groups (preferably alkenyloxy groups having 2 to 6 carbon atoms, for example, vinyloxy group, 1-propenyloxy group, 2-n-propenyloxy group (allyloxy group), 1-n-butenyloxy group, prenyloxy group); Heterocyclic oxy groups (preferably heterocyclic oxy groups having 1 to 32 carbon atoms, more preferably 1 to 18 carbon atoms, for example, 1-phenyltetrazole-5-oxy group, 2-tetrahydropyranyloxy group); silyloxy groups (preferably silyloxy groups having 1 to 32 carbon atoms, more preferably 1 to 18 carbon atoms, for example, trimethylsilyloxy group, t-butyldimethylsilyloxy group, diphenylmethylsilyloxy group); acyloxy groups (preferably acyloxy groups having 2 to 48 carbon atoms, more preferably 2 to 24 carbon atoms, for example, acetoxy group, pivaloyloxy group, benzoyloxy group, dodecanoyloxy group, acryloyloxy group, methacryloyloxy group);Hydroxyalkylene oxy groups (preferably hydroxyalkylene oxy groups having 2 to 10 carbon atoms, for example, hydroxyethylene oxy groups); alkylcarbonyl oxy groups (preferably alkylcarbonyl oxy groups having 2 to 10 carbon atoms, for example, ethylcarbonyl oxy groups); alkoxycarbonyl oxy groups (preferably alkoxycarbonyl oxy groups having 2 to 48 carbon atoms, more preferably 2 to 24 carbon atoms, for example, ethoxycarbonyl oxy groups, t-butoxycarbonyl oxy groups, cycloalkyloxycarbonyl oxy groups (for example, cyclohexyloxycarbonyl oxy groups)); aryloxycarbonyl oxy groups (preferably aryloxycarbonyl oxy groups having 7 to 32 carbon atoms, more preferably 7 to 24 carbon atoms, for example, phenoxycarbonyl oxy groups); Carbamoyloxy groups (preferably carbamoyloxy groups having 1 to 48 carbon atoms, more preferably 1 to 24 carbon atoms, for example, N,N-dimethylcarbamoyloxy group, N-butylcarbamoyloxy group, N-phenylcarbamoyloxy group, N-ethyl-N-phenylcarbamoyloxy group); sulfamoyloxy groups (preferably sulfamoyloxy groups having 1 to 32 carbon atoms, more preferably 1 to 24 carbon atoms, for example, N,N-diethylsulfamoyloxy group, N-propylsulfamoyloxy group); alkylsulfonyloxy groups (preferably alkylsulfonyloxy groups having 1 to 38 carbon atoms, more preferably 1 to 24 carbon atoms, for example, methylsulfonyloxy group, hexadecylsulfonyloxy group, cyclohexylsulfonyloxy group); arylsulfonyloxy groups (preferably arylsulfonyloxy groups having 6 to 32 carbon atoms, more preferably 6 to 24 carbon atoms, for example, phenylsulfonyloxy group); Acyl groups (preferably acyl groups having 1 to 48 carbon atoms, more preferably acyl groups having 1 to 24 carbon atoms, for example, formyl group, acetyl group, acryloyl group, methacryloyl group, pivaloyl group, benzoyl group, tetradecanoyl group, cyclohexanoyl group);Alkoxycarbonyl groups (preferably alkoxycarbonyl groups having 2 to 48 carbon atoms, more preferably 2 to 24 carbon atoms, for example, methoxycarbonyl group, ethoxycarbonyl group, octadecyloxycarbonyl group, cyclohexyloxycarbonyl group, 2,6-di-tert-butyl-4-methylcyclohexyloxycarbonyl group); aryloxycarbonyl groups (preferably aryloxycarbonyl groups having 7 to 32 carbon atoms, more preferably 7 to 24 carbon atoms, for example, phenoxycarbonyl group); Carbamoyl groups (preferably carbamoyl groups having 1 to 48 carbon atoms, more preferably 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-methylN-phenylcarbamoyl group, N,N-dicyclohexylcarbamoyl group); amino groups (preferably amino groups having 32 or fewer carbon atoms, more preferably 24 or fewer carbon atoms, for example, amino group, methylamino group, N,N-dimethylamino group, N,N-dibutylamino group, tetradecylamino group, 2-ethylhexylamino group, cyclohexylamino group); anilino groups (preferably anilino groups having 6 to 32 carbon atoms, more preferably 6 to 24 carbon atoms, for example, anilino group, N-methylanilino group); Heterocyclic amino groups (preferably heterocyclic amino groups having 1 to 32 carbon atoms, more preferably 1 to 18 carbon atoms, for example, 4-pyridylamino group); carbonamide groups (preferably carbonamide groups having 2 to 48 carbon atoms, more preferably 2 to 24 carbon atoms, for example, acetamide group, benzamide group, tetradecaneamide group, pivaloylamide group, cyclohexaneamide group); ureido groups (preferably carbonamide groups having 1 to 32 carbon atoms, more preferably carbonamide groups having 1 to 24 carbon atoms, for example, ureido group, N,N-dimethylureido group, N-phenylureido group); imide groups (preferably imide groups having 36 carbon atoms or less, more preferably carbon atoms of 24 carbon atoms or less, for example, N-succinimide group, N-phthalimide group);Alkoxycarbonylamino groups (preferably alkoxycarbonylamino groups having 2 to 48 carbon atoms, more preferably 2 to 24 carbon atoms, for example, methoxycarbonylamino group, ethoxycarbonylamino group, t-butoxycarbonylamino group, octadecyloxycarbonylamino group, cyclohexyloxycarbonylamino group); aryloxycarbonylamino groups (preferably aryloxycarbonylamino groups having 7 to 32 carbon atoms, more preferably 7 to 24 carbon atoms, for example, phenoxycarbonylamino group); sulfonamide groups (preferably sulfonamide groups having 1 to 48 carbon atoms, more preferably 1 to 24 carbon atoms, for example, methanesulfonamide group, butanesulfonamide group, benzenesulfonamide group, hexadecanesulfonamide group, cyclohexanesulfonamide group); Sulfamoylamino groups (preferably C1-C48, more preferably C1-C24 sulfamoylamino groups, for example, N,N-dipropylsulfamoylamino group, N-ethyl-N-dodecylsulfamoylamino group); Azo groups (preferably C1-C32, more preferably C1-C24 azo groups, for example, phenylazo group, 3-pyrazolylazo group); Alkylthio groups (preferably C1-C48, more preferably C1-C24 alkylthio groups, for example, methylthio group, ethylthio group, octylthio group, cyclohexylthio group); Arylthio groups (preferably C6-C48, more preferably C6-C24 arylthio groups, for example, phenylthio group); Heterocyclic thio groups (preferably C1-C32, more preferably C1-C18 heterocyclic thio groups, for example, 2-benzothiazolylthio group, 2-pyridylthio group, 1-phenyltetrazolylthio group); Alkyl sulfinyl group (preferably an alkyl sulfinyl group having 1 to 32 carbon atoms, more preferably an alkyl sulfinyl group having 1 to 24 carbon atoms, for example, dodecane sulfinyl group); aryl sulfinyl group (preferably an aryl sulfinyl group having 6 to 32 carbon atoms, more preferably an aryl sulfinyl group having 6 to 24 carbon atoms, for example, phenyl sulfinyl group);An alkylsulfonyl group (preferably an alkylsulfonyl group having 1 to 48 carbon atoms, more preferably 1 to 24 carbon atoms, such as methylsulfonyl group, ethylsulfonyl group, propylsulfonyl group, butylsulfonyl group, isopropylsulfonyl group, 2-ethylhexylsulfonyl group, hexadecylsulfonyl group, octylsulfonyl group, cyclohexylsulfonyl group); an arylsulfonyl group (preferably an arylsulfonyl group having 6 to 48 carbon atoms, more preferably 6 to 24 carbon atoms, such as phenylsulfonyl group, 1-naphthylsulfonyl group); a sulfamoyl group (preferably a sulfamoyl group having 32 or less carbon atoms, more preferably 24 or less carbon atoms, such as sulfamoyl group, N,N-dipropylsulfamoyl group, N-ethyl-N-dodecylsulfamoyl group, N-ethyl-N-phenylsulfamoyl group, N-cyclohexylsulfamoyl group, N-(2-ethylhexyl)sulfamoyl group); a phosphonyl group (preferably a phosphonyl group having 1 to 32 carbon atoms, more preferably 1 to 24 carbon atoms, such as phenoxyphosphonyl group, octyloxyphosphonyl group, phenylphosphonyl group); a phosphinoylamino group (preferably a phosphinoylamino group having 1 to 32 carbon atoms, more preferably 1 to 24 carbon atoms, such as diethoxyphosphinoylamino group, dioctyloxyphosphinoylamino group); an epoxy group; -NHCOCH; ３ ; -SO ２ NH C ２ H ４ OCH ３ ; -NHSO ２ CH ３ ; etc. may be mentioned, and two or more of these may be combined. These substituents may be further substituted by these substituents. Also, when having two or more substituents, they may be the same or different from each other. Also, when possible, they may be bonded to each other to form a ring.[[ID=_{15}]] [[ID=_{16}]]

[0014] [[ID=_{17}]] [Compound] The compound of the present invention is a compound represented by any of the following formulas (1) to (6) (hereinafter also abbreviated as "specific compound").[[ID=_{18}]] [[ID=_{19}]]

[0015] As described above, the compounds of the present invention have a high Δn and excellent solubility in solvents. The reason for this effect is not entirely clear, but the inventors speculate as follows: The specific compounds are thought to have a high Δn because the conjugated system in the core portion (particularly the ring structure such as the five-membered heterocyclic group linked by a single bond from the central ring structure, or the fused aromatic hydrocarbon ring group) has been expanded. Furthermore, the specific compounds are thought to have good solubility in solvents because they have introduced a predetermined terminal spacer portion (for example, a branched alkylene group) in relation to the core portion.

[0016] The compounds of the present invention will be described in detail below using their general formulas.

[0017] [Formula (1)] One of the compounds of the present invention is a compound represented by the following formula (1).

[0018] In the above formula (1), T １１ , T １２ and T １３ Each of these independently represents either a methine or a nitrogen atom, and T １１ , T １２ and T １３ Preferably, all of them represent methine. That is, R １１ ~R １３ The ring structure to which the atoms are bonded (hereinafter also referred to as the "central ring structure") is preferably a benzene ring.

[0019] In the above formula (1), R １１ , R １２ and R １３ Each of these independently represents either the following formula (A1) or a hydrogen atom. However, R １１ , R １２ and R １３ Preferably, at least two of them represent the following formula (A1), and all of them represent the following formula (A1).

[0020] In the above formula (A1), * represents the bond position, that is, the bond position with the central ring structure. For example, R １１ If the above formula (A1) is represented by the above formula (A1), then the * in the above formula (A1) is R １１This indicates the bonding position with the carbon atom to which it is bonded.

[0021] In the above formula (A1), X １１ This represents a five-membered heterocyclic group represented by any of the following formulas (X11-1) to (X11-14).

[0022] In the above equations (X11-1) to (X11-14), * represents the bond position. That is, of the two *s in each equation, one represents the bond position with the central ring structure, and the other represents Y １１ This represents the bonding position with Y. In particular, of the two asterisks in each formula, the asterisk on the left represents the bonding position with the central ring structure, and the asterisk on the right represents Y. １１ It is preferable to represent the bonding position with [the other element].

[0023] In this invention, X is used because Δn becomes higher. １１ However, it is preferable to represent a five-membered heterocyclic ring group represented by any of the above formulas (X11-2), (X11-5), (X11-7), (X11-9), (X11-12), and (X11-14), more preferably a five-membered heterocyclic ring group represented by the above formula (X11-2) or (X11-5), and even more preferably a five-membered heterocyclic ring group represented by the above formula (X11-2).

[0024] In the above formula (A1), Y １１ X represents a five-membered heterocyclic ring group, a fused aromatic hydrocarbon ring group, or a fused aromatic heterocyclic ring group represented by any of the above formulas (X11-1) to (X11-14), and preferably represents a fused aromatic hydrocarbon ring group or a fused aromatic heterocyclic ring group. However, X １１ However, when representing a five-membered heterocyclic ring group represented by the above formula (X11-1), Y １１ X represents a five-membered heterocyclic group represented by any of the above formulas (X11-1) to (X11-14). Also, X １１ However, when it represents a five-membered heterocyclic ring group represented by any of the above formulas (X11-3), (X11-4), (X11-8), (X11-10), (X11-12), and (X11-13), Y １１This represents a five-membered heterocyclic ring group or a fused aromatic hydrocarbon ring group represented by any of the above formulas (X11-1) to (X11-14).

[0025] Here, Y １１ One embodiment of the fused aromatic hydrocarbon ring group is, for example, a group obtained by removing two hydrogen atoms bonded to a fused aromatic hydrocarbon ring represented by any of the following formulas (X51-1) to (X51-3), and among these, the group obtained by removing two hydrogen atoms bonded to a fused aromatic hydrocarbon ring represented by the following formula (X51-1) is preferred. Also, Y １１ One embodiment of the fused ring aromatic heterocyclic group is, for example, a group obtained by removing two hydrogen atoms bonded to the ring from a fused ring aromatic heterocyclic group represented by any of the following formulas (X51-4) to (X51-20). Among these, a group obtained by removing two hydrogen atoms bonded to the ring from a fused ring aromatic heterocyclic group represented by any of the following formulas (X51-4), (X51-5), (X51-10), (X51-11), (X51-16), and (X51-17) is preferred.

[0026] In the present invention, Y in formula (A1) １１ It is preferable that the group is represented by any of the following formulas (X51-1-Y), (X51-1-Y-2), (X51-4-Y), (X51-5-Y), (X51-10-Y), (X51-11-Y), (X51-16-Y), (X51-17-Y), (X51-19-Y), (X11-2-Y), and (X11-7-Y), and more preferably the group is represented by any of the following formulas (X51-1-Y), (X51-4-Y), (X51-10-Y), and (X51-16-Y). In the following formulas, (X) is the same as X in formula (A1) above. １１ This represents the bonding position with, where (L) is L in the above formula (A1). １１ This indicates the connection point with [the other element].

[0027] In the above formula (A1), L １１This represents a linear or branched alkylene group, or a linear or branched alkenylene group. However, this refers to one or more non-adjacent -CH groups contained within the alkylene group or alkenylene group. ２ - is -O-, -COO-, -OCO-, -OCOO-, -CO-, -S-, -SO ２ -, -NR-, -NRSO ２ -, or -SO ２ It may be substituted with NR-. R represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. Also, one or more hydrogen atoms in the alkylene group or alkenylene group may be substituted with halogen atoms. Also, X １１ This represents a five-membered heterocyclic group represented by the above formula (X11-2), and Y １１ When L represents a fused aromatic hydrocarbon ring group, １１ represents a branched alkylene group or a branched alkenylene group.

[0028] Examples of linear or branched alkylene groups include linear alkylene groups having 1 to 15 carbon atoms or branched alkylene groups having 3 to 15 carbon atoms. Specifically, methylene groups, ethylene groups, propylene groups, butylene groups, pentylene groups, hexylene groups, methylhexylene groups, and heptylene groups are preferred. Examples of linear or branched alkenylene groups include linear alkenylene groups having 2 to 15 carbon atoms or branched alkenylene groups having 3 to 15 carbon atoms. Specifically, etenylene groups, propenylene groups, and butenylene groups are preferred. Of these, branched alkylene groups are preferred.

[0029] In the present invention, L in formula (A1) １１ The alkylene group is preferably a linear alkylene group having 1 to 15 carbon atoms or a branched alkylene group having 3 to 15 carbon atoms, and more preferably a branched alkylene group having 3 to 15 carbon atoms. However, the alkylene group may contain one or two or more non-adjacent -CH groups. ２ The dash may be replaced with -O-, -COO-, -OCO-, -OCOO-, -CO-, or -S-.

[0030] In the above formula (A1), Q １１ Q represents a polymerizable group, a hydrogen atom, a hydroxyl group, a carboxyl group, or a halogen atom, and at least one Q １１ It is preferable that represents a polymerizable group, and all Q １１ It is more preferable that represents a polymerizable group. Here, Q １１ As a polymerizable group in one aspect, a polymerizable group capable of radical polymerization or cationic polymerization is preferred. As a radical polymerizable group, known radical polymerizable groups can be used, and preferred examples include acryloyloxy groups and methacryloyloxy groups. In this case, the polymerization rate of acryloyloxy groups is generally known to be faster, and from the viewpoint of improving productivity, acryloyloxy groups are preferred, but methacryloyloxy groups can also be used as polymerizable groups in the same way. As a cationic polymerizable group, known cationic polymerizable groups can be used, and specifically, examples include alicyclic ether groups, cyclic acetal groups, cyclic lactone groups, cyclic thioether groups, spiroorthoester groups, and vinyloxy groups. Among these, alicyclic ether groups or vinyloxy groups are preferred, and epoxy groups, oxetanyl groups, or vinyloxy groups are particularly preferred.

[0031] In the present invention, Q in formula (A1) above １１ It is preferably a polymerizable group, and more preferably a (meth)acryloyloxy group.

[0032] Examples of compounds represented by the above formula (1) include, for example, compounds represented by the following formula.

[0033]

[0034]

[0035]

[0036]

[0037]

[0038]

[0039]

[0040]

[0041]

[0042]

[0043]

[0044]

[0045]

[0046] [Formula (2)] One of the compounds of the present invention is a compound represented by the following formula (2).

[0047] In the above formula (2), T ２１ , T ２２ and T ２３ Each of these independently represents either a methine or a nitrogen atom, and T ２１ , T ２２ and T ２３ Preferably, all of them represent methine. That is, R ２１ ~R ２３ The ring structure to which the atoms are bonded (central ring structure) is preferably a benzene ring.

[0048] In the above formula (2), R ２１ , R ２２ and R ２３ Each of these independently represents either the following formula (A2) or a hydrogen atom. However, R ２１ , R ２２ and R ２３ Preferably, at least two of them represent the following formula (A2), and all of them represent the following formula (A2).

[0049] In the above formula (A2), * represents the bonding position, that is, the bonding position with the central ring structure. For example, R ２１ If the above formula (A2) represents the above formula (A2), then the * in the above formula (A2) is R ２１ This indicates the bonding position with the carbon atom to which it is bonded.

[0050] In the above formula (A2), X ２１X represents a fused aromatic hydrocarbon ring group or a fused aromatic heterocyclic ring group, and preferably represents a fused aromatic heterocyclic ring group. ２１ One embodiment of a fused aromatic hydrocarbon ring group is, for example, a group obtained by removing two hydrogen atoms bonded to a fused aromatic hydrocarbon ring represented by any of the above formulas (X51-1) to (X51-3), and among these, the group obtained by removing two hydrogen atoms bonded to a fused aromatic hydrocarbon ring represented by the above formula (X51-1) is preferred. ２１ One embodiment of a fused ring aromatic heterocyclic group is, for example, a group obtained by removing two hydrogen atoms bonded to the ring from a fused ring aromatic heterocyclic group represented by any of the above formulas (X51-4) to (X51-20). Among these, a group obtained by removing two hydrogen atoms bonded to the ring from a fused ring aromatic heterocyclic group represented by any of the above formulas (X51-4), (X51-5), (X51-10), (X51-11), (X51-16), and (X51-17) is preferred.

[0051] In the present invention, X in formula (A2) above ２１ Preferably, the group is represented by any of the following formulas: (X51-4-X), (X51-5-X), (X51-10-X), (X51-11-X), (X51-16-X), and (X51-17-X). In the following formulas, (C) represents the bonding position with the central ring structure in formula (2) above, and (L) represents the Y in formula (A2) above. ２１ This indicates the connection point with [the other element].

[0052] In the above formula (A2), Y ２１ This represents a phenylene group which may have substituents, a monocyclic aromatic heterocyclic group, a fused aromatic hydrocarbon ring group, or a fused aromatic heterocyclic group.

[0053] Here, Y ２１Examples of phenylene groups that may have substituents in one aspect include 1,4-phenylene groups and 1,3-phenylene groups. Examples of substituents that the phenylene group may have include those listed in substituent group A above, among which alkyl groups and alkoxy groups are preferred. In the present invention, Y ２１ As a phenylene group which may have a substituent as one embodiment, it is preferable that it is an unsubstituted phenylene group.

[0054] Also, Y ２１ Examples of monocyclic aromatic heterocyclic groups include five-membered aromatic heterocyclic groups or six-membered aromatic heterocyclic groups. Examples of five-membered aromatic heterocyclic groups include five-membered aromatic heterocyclic groups represented by any of the above formulas (X11-1) to (X11-14). Examples of six-membered aromatic heterocyclic groups include groups obtained by removing two hydrogen atoms bonded to the ring from a pyridine ring, pyridazine ring, pyrimidine ring, pyrazine ring, and triazine ring.

[0055] Also, Y ２１ One embodiment of a fused aromatic hydrocarbon ring group is, for example, a group obtained by removing two hydrogen atoms bonded to a fused aromatic hydrocarbon ring represented by any of the above formulas (X51-1) to (X51-3), and among these, the group obtained by removing two hydrogen atoms bonded to a fused aromatic hydrocarbon ring represented by the above formula (X51-1) is preferred. Also, Y ２１ One embodiment of a fused ring aromatic heterocyclic group is, for example, a group obtained by removing two hydrogen atoms bonded to the ring from a fused ring aromatic heterocyclic group represented by any of the above formulas (X51-4) to (X51-20). Among these, a group obtained by removing two hydrogen atoms bonded to the ring from a fused ring aromatic heterocyclic group represented by any of the above formulas (X51-4), (X51-5), (X51-10), (X51-11), (X51-16), and (X51-17) is preferred.

[0056] In the present invention, Y in formula (A2) above ２１is preferably a 5-membered heterocyclic group represented by any of the above formulas (X11-1) to (X11-14), or a condensed aromatic heterocyclic group. In the above formulas (X11-1) to (X11-14), * represents the bonding position. That is, among the two * in each formula, one represents the bonding position with X ２１ and the other represents the bonding position with Z ２１ . In particular, among the two * in each formula, the left * preferably represents the bonding position with X ２１ and the right * preferably represents the bonding position with Z ２１ .

[0057] In the present invention, Y ２１ in the above formula (A2) is preferably a group represented by any of the following formulas (X11-2-Y), (X11-5-Y), (X11-7-Y), (X11-9-Y), (X11-12-Y) and (X11-14-Y). In the following formulas, (X) represents the bonding position with X ２１ in the above formula (A2), and (Z) represents the bonding position with Z ２１ in the above formula (A2).

[0058] In the above formula (A2), Z ２１ represents a phenylene group which may have a substituent, a monocyclic aromatic heterocyclic group, a condensed aromatic hydrocarbon ring group, or a condensed aromatic heterocyclic group. Specific examples of these Z ２１ are the same as those described for Y ２１ in the above formula (A2). Among them, Z ２１ is preferably a phenylene group which may have a substituent.

[0059] In the above formula (A2), L ２１ represents a linear or branched alkylene group, or a linear or branched alkenylene group. However, one or two or more non-adjacent -CH ２ -s contained in the alkylene group or alkenylene group are -O-, -COO-, -OCO-, -OCOO-, -CO-, -S-, -SO ２ -, -NR-, -NRSO ２ -, or -SO ２It may be substituted with NR-. R represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. In addition, one or more hydrogen atoms in the alkylene group or alkenylene group may be substituted with halogen atoms. Note that the linear or branched alkylene group or linear or branched alkenylene group is L in the above formula (A1). １１ The same examples as those explained in [previous section] can be cited.

[0060] In the present invention, L in formula (A2) above ２１ The alkylene group is preferably a linear alkylene group having 1 to 15 carbon atoms or a branched alkylene group having 3 to 15 carbon atoms, and more preferably a branched alkylene group having 3 to 15 carbon atoms. However, the alkylene group may contain one or two or more non-adjacent -CH groups. ２ The dash may be replaced with -O-, -COO-, -OCO-, -OCOO-, -CO-, or -S-.

[0061] In the above formula (A2), Q ２１ Q represents a polymerizable group, a hydrogen atom, a hydroxyl group, a carboxyl group, or a halogen atom. However, at least one Q is specified. ２１ This represents a polymerizable group, and all Q ７１ It is preferable that Q represents a polymerizable group. Here, Q ２１ One embodiment of the polymerizable group is Q in formula (A1) above. １１ Examples similar to those described above include Q in formula (A2) above. ２１ It is preferably a polymerizable group, and more preferably a (meth)acryloyloxy group.

[0062] Examples of compounds represented by the above formula (2) include, for example, compounds represented by the following formula.

[0063]

[0064]

[0065] [Formula (3)] One of the compounds of the present invention is a compound represented by the following formula (3).

[0066] In the above formula (3), T ３１ , T ３２ and T ３３ Each of these independently represents either a methine or a nitrogen atom, and T ３１ , T ３２ and T ３３ Preferably, all of them represent methine. That is, R ３１ ~R ３３ The ring structure to which the atoms are bonded (central ring structure) is preferably a benzene ring.

[0067] In the above formula (3), R ３１ , R ３２ and R ３３ Each of these independently represents either the following formula (A3) or a hydrogen atom. However, R ３１ , R ３２ and R ３３ Preferably, at least two of them represent the following formula (A3), and all of them represent the following formula (A3).

[0068] In the above formula (A3), * represents the bond position, that is, the bond position with the central ring structure. For example, R ３１ If the above formula (A3) is represented by the above formula (A3), then the * in the above formula (A3) is R ３１ This indicates the bonding position with the carbon atom to which it is bonded.

[0069] In the above formula (A3), X ３１ This represents a five-membered heterocyclic group represented by any of the above formulas (X11-1) to (X11-14). In the above formulas (X11-1) to (X11-14), * represents the bond position. That is, of the two *s in each formula, one represents the bond position to the central ring structure, and the other represents Y ３１ This represents the bonding position with Y. In particular, of the two asterisks in each formula, the asterisk on the left represents the bonding position with the central ring structure, and the asterisk on the right represents Y. ３１ It is preferable to represent the bonding position with [the other element].

[0070] In this invention, X is used because Δn becomes higher. ３１However, it is preferable to represent a five-membered heterocyclic ring group represented by any of the above formulas (X11-2), (X11-5), (X11-7), (X11-9), (X11-12), and (X11-14), and it is more preferable to represent a five-membered heterocyclic ring group represented by the above formula (X11-2) or (X11-5).

[0071] In the above formula (A3), Y ３１ represents a phenylene group which may have substituents. Here, the phenylene group and any substituents are, for example, Y in formula (A2) above. ２１ Examples similar to those described above include the following. In the present invention, Y in formula (A3) above ３１ It is preferable that this is an unsubstituted phenylene group.

[0072] In the above formula (A3), Z ３１ X represents a phenylene group which may have substituents, a monocyclic aromatic heterocyclic group, a fused aromatic hydrocarbon ring group, or a fused aromatic heterocyclic group, and preferably represents a fused aromatic hydrocarbon ring group or a fused aromatic heterocyclic group. ３１ However, when representing a five-membered heterocyclic group represented by any of the above (X11-1), (X11-2), (X11-8), and (X11-9), Z ３１ This represents a fused aromatic hydrocarbon ring group or a fused aromatic heterocyclic ring group.

[0073] Here, Z ３１ An example of a phenylene group which may have a substituent in one aspect is Y in formula (A2) above. ２１ The same things as those explained in [previous section] can be cited. Also, Z ３１ One embodiment of a monocyclic aromatic heterocyclic group is, for example, Y in formula (A2) above. ２１ The same things as those explained in [previous section] can be cited. Also, Z ３１One embodiment of a fused aromatic hydrocarbon ring group is, for example, a group obtained by removing two hydrogen atoms bonded to a fused aromatic hydrocarbon ring represented by any of the above formulas (X51-1) to (X51-3), and among these, the group obtained by removing two hydrogen atoms bonded to a fused aromatic hydrocarbon ring represented by the above formula (X51-1) is preferred. Also, Z ３１ One embodiment of a fused ring aromatic heterocyclic group is, for example, a group obtained by removing two hydrogen atoms bonded to the ring from a fused ring aromatic heterocyclic group represented by any of the above formulas (X51-4) to (X51-20). Among these, a group obtained by removing two hydrogen atoms bonded to the ring from a fused ring aromatic heterocyclic group represented by any of the above formulas (X51-4), (X51-5), (X51-10), (X51-11), (X51-16), and (X51-17) is preferred.

[0074] In the present invention, Z in formula (A3) above ３１ This refers to any of the following formulas (Z31-1), (Z31-2), (X11-2-Z), (X11-5-Z), (X11-7-Z), (X11-9-Z), (X11-12-Z), (X11-14-Z), (Z51-1-Z), (X51-4-Z), (X51-5-Z), (X51-10-Z), (X51-11-Z), (X51-16-Z), and (X51-17-Z). It is preferable that the group be represented by any of the following formulas, and more preferably that it be represented by any of the following formulas: (X11-2-Z), (X11-5-Z), (X11-7-Z), (X11-9-Z), (X11-12-Z), (X11-14-Z), (Z51-1-Z), (X51-4-Z), (X51-5-Z), (X51-10-Z), and (X51-11-Z). In the following formulas, (Y) is the same as Y in formula (A3) above. ３１ This represents the bonding position with, where (L) is L in the above formula (A3). ３１ This indicates the connection point with [the other element].

[0075] In the above formula (A3), L ３１This represents a linear or branched alkylene group, or a linear or branched alkenylene group. However, this refers to one or more non-adjacent -CH groups contained within the alkylene group or alkenylene group. ２ - is -O-, -COO-, -OCO-, -OCOO-, -CO-, -S-, -SO ２ -, -NR-, -NRSO ２ -, or -SO ２ It may be substituted with NR-. R represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. In addition, one or more hydrogen atoms in the alkylene group or alkenylene group may be substituted with halogen atoms. Note that the linear or branched alkylene group or linear or branched alkenylene group is L in the above formula (A1). １１ The same examples as those explained in [previous section] can be cited.

[0076] In the present invention, L in formula (A3) above ３１ The alkylene group is preferably a linear alkylene group having 1 to 15 carbon atoms or a branched alkylene group having 3 to 15 carbon atoms, and more preferably a branched alkylene group having 3 to 15 carbon atoms. However, the alkylene group may contain one or two or more non-adjacent -CH groups. ２ The dash may be replaced with -O-, -COO-, -OCO-, -OCOO-, -CO-, or -S-.

[0077] In the above formula (A3), Q ３１ Q represents a polymerizable group, a hydrogen atom, a hydroxyl group, a carboxyl group, or a halogen atom, and at least one Q ３１ It is preferable that represents a polymerizable group, and all Q ３１ It is more preferable that represents a polymerizable group. Here, Q ３１ One embodiment of the polymerizable group is Q in formula (A1) above. １１ Examples similar to those described above include the following. In the present invention, Q in formula (A3) above ３１ It is preferably a polymerizable group, and more preferably a (meth)acryloyloxy group.

[0078] Examples of compounds represented by the above formula (3) include, for example, compounds represented by the following formula.

[0079]

[0080]

[0081]

[0082] [Formula (4)] One of the compounds of the present invention is a compound represented by the following formula (4).

[0083] In the above formula (4), T ４１ , T ４２ and T ４３ Each of these independently represents either a methine or a nitrogen atom, and T ４１ , T ４２ and T ４３ Preferably, all of them represent methine. That is, R ４１ ~R ４３ The ring structure to which the atoms are bonded (central ring structure) is preferably a benzene ring.

[0084] In the above formula (4), R ４１ , R ４２ and R ４３ Each of these independently represents either the following formula (A4) or a hydrogen atom. However, R ４１ , R ４２ and R ４３ Preferably, at least two of them represent the following formula (A4), and all of them represent the following formula (A4).

[0085] In the above formula (A4), * represents the bond position, that is, the bond position with the central ring structure. For example, R ４１ If the above formula (A4) is represented, then the * in the above formula (A4) is R ４１ This indicates the bonding position with the carbon atom to which it is bonded.

[0086] In the above formula (A4), X ４１This represents a five-membered heterocyclic group represented by any of the above formulas (X11-1) to (X11-14). In the above formulas (X11-1) to (X11-14), * represents the bond position. That is, of the two *s in each formula, one represents the bond position to the central ring structure, and the other represents Y ４１ This represents the bonding position with Y. In particular, of the two asterisks in each formula, the asterisk on the left represents the bonding position with the central ring structure, and the asterisk on the right represents Y. ４１ It is preferable to represent the bonding position with [the other element].

[0087] In this invention, X is used because Δn becomes higher. ４１ However, it is preferable to represent a five-membered heterocyclic ring group represented by any of the above formulas (X11-2), (X11-5), (X11-7), (X11-9), (X11-12), and (X11-14), and it is more preferable to represent a five-membered heterocyclic ring group represented by the above formula (X11-2) or (X11-5).

[0088] In the above formula (A4), Y ４１ This represents a monocyclic aromatic heterocyclic group, a fused aromatic hydrocarbon ring group, or a fused aromatic heterocyclic group.

[0089] Here, Y ４１ One embodiment of a monocyclic aromatic heterocyclic group is, for example, Y in formula (A2) above. ２１ Examples similar to those explained in [previous section] can be given. Also, Y ４１ One embodiment of a fused aromatic hydrocarbon ring group is, for example, a group obtained by removing two hydrogen atoms bonded to a fused aromatic hydrocarbon ring represented by any of the above formulas (X51-1) to (X51-3), and among these, the group obtained by removing two hydrogen atoms bonded to a fused aromatic hydrocarbon ring represented by the above formula (X51-1) is preferred. Also, Y ４１One embodiment of a fused ring aromatic heterocyclic group is, for example, a group obtained by removing two hydrogen atoms bonded to the ring from a fused ring aromatic heterocyclic group represented by any of the above formulas (X51-4) to (X51-20), and among these, a group obtained by removing two hydrogen atoms bonded to the ring from a fused ring aromatic heterocyclic group represented by any of the above formulas (X51-4), (X51-5), (X51-10), (X51-11), (X51-16), and (X51-17) is preferred. In the present invention, Y in formula (A4) ４１ Preferably, the group is formed by removing two hydrogen atoms bonded to a ring from a fused aromatic hydrocarbon ring or a fused aromatic heteroring.

[0090] In the present invention, Y in formula (A4) above ４１ Preferably, the group is represented by any of the following formulas: (X51-1-Y), (X51-1-Y-3), (X51-4-Y), (X51-5-Y), (X51-10-Y), and (X51-11-Y). In the following formulas, (X) is the same as the X in formula (A1) above. ４１ This represents the bonding position with, where (Z) is Z in the above formula (A4). ４１ This indicates the connection point with [the other element].

[0091] In the above formula (A4), Z ４１ This represents a phenylene group which may have substituents, a monocyclic aromatic heterocyclic group, a fused aromatic hydrocarbon ring group, or a fused aromatic heterocyclic group.

[0092] Here, Z ４１ An example of a phenylene group which may have a substituent in one aspect is Y in formula (A2) above. ２１ The same things as those explained in [previous section] can be cited. Also, Z ４１ One embodiment of a monocyclic aromatic heterocyclic group is, for example, Y in formula (A2) above. ２１ The same things as those explained in [previous section] can be cited. Also, Z ４１One embodiment of a fused aromatic hydrocarbon ring group is, for example, a group obtained by removing two hydrogen atoms bonded to a fused aromatic hydrocarbon ring represented by any of the above formulas (X51-1) to (X51-3), and among these, the group obtained by removing two hydrogen atoms bonded to a fused aromatic hydrocarbon ring represented by the above formula (X51-1) is preferred. Also, Z ４１ One embodiment of a fused ring aromatic heterocyclic group is, for example, a group obtained by removing two hydrogen atoms bonded to the ring from a fused ring aromatic heterocyclic group represented by any of the above formulas (X51-4) to (X51-20). Among these, a group obtained by removing two hydrogen atoms bonded to the ring from a fused ring aromatic heterocyclic group represented by any of the above formulas (X51-4), (X51-5), (X51-10), (X51-11), (X51-16), and (X51-17) is preferred.

[0093] In the present invention, Z in formula (A4) above ４１ It is preferable that is a five-membered heterocyclic group represented by any of the above formulas (X11-1) to (X11-14). In the above formulas (X11-1) to (X11-14), * represents the bond position. That is, of the two * in each formula, one is Y ４１ This represents the bonding position with L. ４１ This indicates the bonding position with Y. In particular, of the two *s in each equation, the left * is Y ４１ This indicates the connection position with, and the asterisk on the right is L ４１ It is preferable to represent the bonding position with [the other element].

[0094] In the present invention, Z in formula (A4) above ４１ Preferably, the group is represented by any of the following formulas: (X11-1-Z), (X11-2-Z), (X11-5-Z), (X11-7-Z), (X11-9-Z), (X11-12-Z), and (X11-14-Z). In the following formulas, (Y) is the same as Y in formula (A4) above. ４１ This represents the bonding position with, where (L) is L in the above formula (A4). ４１ This indicates the connection point with [the other element].

[0095] In the above formula (A4), L ４１This represents a linear or branched alkylene group, or a linear or branched alkenylene group. However, this refers to one or more non-adjacent -CH groups contained within the alkylene group or alkenylene group. ２ - is -O-, -COO-, -OCO-, -OCOO-, -CO-, -S-, -SO ２ -, -NR-, -NRSO ２ -, or -SO ２ It may be substituted with NR-. R represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. In addition, one or more hydrogen atoms in the alkylene group or alkenylene group may be substituted with halogen atoms. Note that the linear or branched alkylene group or linear or branched alkenylene group is L in the above formula (A1). １１ The same examples as those explained in [previous section] can be cited.

[0096] In the present invention, L in formula (A4) above ４１ The alkylene group is preferably a linear alkylene group having 1 to 15 carbon atoms or a branched alkylene group having 3 to 15 carbon atoms, and more preferably a branched alkylene group having 3 to 15 carbon atoms. However, the alkylene group may contain one or two or more non-adjacent -CH groups. ２ The dash may be replaced with -O-, -COO-, -OCO-, -OCOO-, -CO-, or -S-.

[0097] In the above formula (A4), Q ４１ Q represents a polymerizable group, a hydrogen atom, a hydroxyl group, a carboxyl group, or a halogen atom, and at least one Q ４１ It is preferable that represents a polymerizable group, and all Q ４１ It is more preferable that represents a polymerizable group. Here, Q ４１ One embodiment of the polymerizable group is Q in formula (A1) above. １１ Examples similar to those described above include Q in formula (A4) above. ４１ It is preferably a polymerizable group, and more preferably a (meth)acryloyloxy group.

[0098] Examples of compounds represented by the above formula (4) include, for example, compounds represented by the following formula.

[0099]

[0100]

[0101]

[0102] [Formula (5)] One of the compounds of the present invention is a compound represented by the following formula (5).

[0103] In the above formula (5), T ５１ , T ５２ and T ５３ Each of these independently represents either a methine or a nitrogen atom, and T ５１ , T ５２ and T ５３ Preferably, all of them represent methine. That is, R ５１ ~R ５３ The ring structure to which the atoms are bonded (central ring structure) is preferably a benzene ring.

[0104] In the above formula (5), R ５１ , R ５２ and R ５３ Each of these independently represents the following formula (A5).

[0105] In the above formula (A5), * represents the bond position, that is, the bond position with the central ring structure. For example, R ５１ In the above formula (A5) represented by, * in the above formula (A5) is R ５１ This indicates the bonding position with the carbon atom to which it is bonded.

[0106] In the above formula (A5), X ５１ X represents a fused aromatic hydrocarbon ring group or a fused aromatic heterocyclic ring group, and preferably represents a fused aromatic heterocyclic ring group. ５１One embodiment of a fused aromatic hydrocarbon ring group is, for example, a group obtained by removing two hydrogen atoms bonded to a fused aromatic hydrocarbon ring represented by any of the above formulas (X51-1) to (X51-3), and among these, the group obtained by removing two hydrogen atoms bonded to a fused aromatic hydrocarbon ring represented by the above formula (X51-1) is preferred. ５１ One embodiment of a fused ring aromatic heterocyclic group is, for example, a group obtained by removing two hydrogen atoms bonded to the ring from a fused ring aromatic heterocyclic group represented by any of the above formulas (X51-4) to (X51-20). Among these, a group obtained by removing two hydrogen atoms bonded to the ring from a fused ring aromatic heterocyclic group represented by any of the above formulas (X51-4), (X51-5), (X51-10), (X51-11), (X51-16), and (X51-17) is preferred.

[0107] In the present invention, X in formula (A5) above ５１ It is preferable that the group is represented by any of the following formulas: (X51-4-X), (X51-5-X), (X51-10-X), (X51-11-X), (X51-16-X), and (X51-17-X). In the following formulas, (C) represents the bonding position with the central ring structure in formula (5) above, and (L) represents L in formula (A5) above. ５１ This indicates the connection point with [the other element].

[0108] In the above formula (A5), L ５１ This represents a linear or branched alkylene group, or a linear or branched alkenylene group. However, this refers to one or more non-adjacent -CH groups contained within the alkylene group or alkenylene group. ２ - is -O-, -COO-, -OCO-, -OCOO-, -CO-, -S-, -SO ２ -, -NR-, -NRSO ２ -, or -SO ２It may be substituted with NR-. R represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. In addition, one or more hydrogen atoms in the alkylene group or alkenylene group may be substituted with halogen atoms. Note that the linear or branched alkylene group or linear or branched alkenylene group is L in the above formula (A1). １１ The same examples as those explained in [previous section] can be cited.

[0109] In the present invention, L in formula (A5) above ５１ The alkylene group is preferably a linear alkylene group having 1 to 15 carbon atoms or a branched alkylene group having 3 to 15 carbon atoms, and more preferably a branched alkylene group having 3 to 15 carbon atoms. However, the alkylene group may contain one or two or more non-adjacent -CH groups. ２ The dash may be replaced with -O-, -COO-, -OCO-, -OCOO-, -CO-, or -S-.

[0110] In the above formula (A5), Q ５１ represents a polymerizable group. Here, Q ５１ The polymerizable group represented by is Q in formula (A1) above. １１ Examples similar to those described above include Q in formula (A5) above. ５１ It is more preferable that it be a (meth)acryloyloxy group.

[0111] Examples of compounds represented by the above formula (5) include, for example, compounds represented by the following formula.

[0112]

[0113]

[0114]

[0115]

[0116]

[0117]

[0118] [Formula (6)] One of the compounds of the present invention is a compound represented by the following formula (6).

[0119] In the above formula (6), T ６１ , T ６２ and T ６３ Each of these independently represents either a methine or a nitrogen atom, and T ６１ , T ６２ and T ６３ Preferably, all of them represent methine. That is, R ６１ ~R ６３ The ring structure to which the atoms are bonded (central ring structure) is preferably a benzene ring.

[0120] In the above formula (6), R ６１ , R ６２ and R ６３ Each of these independently represents the following formula (A6).

[0121] In the above formula (A6), * represents the bond position, that is, the bond position with the central ring structure. For example, R ６１ In the above formula (A6) represented by, * in the above formula (A6) is R ６１ This indicates the bonding position with the carbon atom to which it is bonded.

[0122] In the above formula (A6), X ６１ X represents a fused aromatic hydrocarbon ring group or a fused aromatic heterocyclic ring group, and preferably represents a fused aromatic heterocyclic ring group. ６１ One embodiment of a fused aromatic hydrocarbon ring group is, for example, a group obtained by removing two hydrogen atoms bonded to a fused aromatic hydrocarbon ring represented by any of the above formulas (X51-1) to (X51-3), and among these, the group obtained by removing two hydrogen atoms bonded to a fused aromatic hydrocarbon ring represented by the above formula (X51-1) is preferred. ６１One embodiment of a fused ring aromatic heterocyclic group is, for example, a group obtained by removing two hydrogen atoms bonded to the ring from a fused ring aromatic heterocyclic group represented by any of the above formulas (X51-4) to (X51-20). Among these, a group obtained by removing two hydrogen atoms bonded to the ring from a fused ring aromatic heterocyclic group represented by any of the above formulas (X51-4), (X51-5), (X51-10), (X51-11), (X51-16), and (X51-17) is preferred.

[0123] In the present invention, X in formula (A6) above ６１ Preferably, the group is represented by one of the following formulas: (X51-4-X), (X51-5-X), (X51-10-X), (X51-11-X), (X51-16-X), and (X51-17-X). In the following formulas, (C) represents the bonding position with the central ring structure in formula (6) above, and (Y) represents the Y in formula (A6) above. ６１ This indicates the connection point with [the other element].

[0124] In the above formula (A6), Y ６１ This represents a phenylene group which may have substituents, a monocyclic aromatic heterocyclic group, a fused aromatic hydrocarbon ring group, or a fused aromatic heterocyclic group.

[0125] Here, Y ６１ An example of a phenylene group which may have a substituent in one aspect is Y in formula (A2) above. ２１ Examples similar to those explained in [previous section] can be given. Also, Y ６１ One embodiment of a monocyclic aromatic heterocyclic group is, for example, Y in formula (A2) above. ２１ Examples similar to those explained in [previous section] can be given. Also, Y ６１ One embodiment of a fused aromatic hydrocarbon ring group is, for example, a group obtained by removing two hydrogen atoms bonded to a fused aromatic hydrocarbon ring represented by any of the above formulas (X51-1) to (X51-3), and among these, the group obtained by removing two hydrogen atoms bonded to a fused aromatic hydrocarbon ring represented by the above formula (X51-1) is preferred. Also, Y ６１One embodiment of a fused ring aromatic heterocyclic group is, for example, a group obtained by removing two hydrogen atoms bonded to the ring from a fused ring aromatic heterocyclic group represented by any of the above formulas (X51-4) to (X51-20). Among these, a group obtained by removing two hydrogen atoms bonded to the ring from a fused ring aromatic heterocyclic group represented by any of the above formulas (X51-4), (X51-5), (X51-10), (X51-11), (X51-16), and (X51-17) is preferred.

[0126] In the present invention, Y in formula (A6) above ６１ It is preferable that is a five-membered heterocyclic group represented by any of the above formulas (X11-1) to (X11-14), or a fused aromatic heterocyclic group. In the above formulas (X11-1) to (X11-14), * represents a bond position. That is, of the two * in each formula, one is X ６１ This represents the bonding position with L. ６１ This indicates the bonding position with X. In particular, of the two *s in each expression, the left * is X ６１ This indicates the connection position with, and the asterisk on the right is L ６１ It is preferable to represent the bonding position with [the other element].

[0127] In the present invention, Y in formula (A6) above ６１ Preferably, the group is represented by any of the following formulas: (X11-1-Y), (X11-2-Y), (X11-5-Y), (X11-7-Y), (X11-9-Y), (X11-12-Y), and (X11-14-Y). In the following formulas, (X) is the same as the X in formula (A6) above. ６１ This represents the bonding position with, where (L) is L in the above formula (A6). ６１ This indicates the connection point with [the other element].

[0128] In the above formula (A6), L ６１ This represents a linear or branched alkylene group, or a linear or branched alkenylene group. However, this refers to one or more non-adjacent -CH groups contained within the alkylene group or alkenylene group. ２ - is -O-, -COO-, -OCO-, -OCOO-, -CO-, -S-, -SO ２ -, -NR-, -NRSO２ -, or -SO ２ It may be substituted with NR-. R represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. In addition, one or more hydrogen atoms in the alkylene group or alkenylene group may be substituted with halogen atoms. Note that the linear or branched alkylene group or linear or branched alkenylene group is L in the above formula (A1). １１ The same examples as those explained in [previous section] can be cited.

[0129] In the present invention, L in formula (A6) above ６１ The alkylene group is preferably a linear alkylene group having 1 to 15 carbon atoms or a branched alkylene group having 3 to 15 carbon atoms, and more preferably a branched alkylene group having 3 to 15 carbon atoms. However, the alkylene group may contain one or two or more non-adjacent -CH groups. ２ The dash may be replaced with -O-, -COO-, -OCO-, -OCOO-, -CO-, or -S-.

[0130] In the above formula (A6), Q ６１ represents a polymerizable group. Here, Q ６１ The polymerizable group represented by is Q in formula (A1) above. １１ Examples similar to those described above include Q in formula (A6) above. ６１ It is more preferable that it be a (meth)acryloyloxy group.

[0131] Examples of compounds represented by the above formula (6) include, for example, compounds represented by the following formula.

[0132]

[0133]

[0134]

[0135]

[0136] [Liquid Crystal Composition] The liquid crystal composition of the present invention is a liquid crystal composition containing the compound of the present invention described above. Here, the content of the compound of the present invention in the liquid crystal composition of the present invention is preferably 10 to 99% by mass, and more preferably 20 to 95% by mass, based on the total solid content mass in the liquid crystal composition.

[0137] [Orientation Control Agent] The liquid crystal composition of the present invention may contain an orientation control agent as needed. The orientation control agent can form various orientation states such as homogeneous orientation, homeotropic orientation (vertical orientation), tilted orientation, hybrid orientation, and cholesteric orientation, and can also control and realize a specific orientation state more uniformly and precisely.

[0138] As orientation control agents that promote homogeneous orientation, for example, low molecular weight orientation control agents and high molecular weight orientation control agents can be used. For low molecular weight orientation control agents, for example, the descriptions in 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 can be referenced, and this content is incorporated herein by reference. Furthermore, as high molecular weight orientation control agents, for example, 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 can be referenced, and this content is incorporated herein by reference.

[0139] Furthermore, examples of orientation-controlling agents that form or promote homeotropic orientation include boronic acid compounds and onium salt compounds. Specifically, reference can be given to compounds described in paragraphs

[0023] to

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

[0052] to

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

[0024] to

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

[0043] to

[0055] of Japanese Patent Publication No. 2016-193869, and this information is incorporated herein by reference.

[0140] On the other hand, cholesteric orientation can be achieved by adding a chiral agent to the polymerizable liquid crystal composition of the present invention, and the direction of rotation of the cholesteric orientation can be controlled by the direction of its chirality. Furthermore, the pitch of the cholesteric orientation can be controlled according to the orientation-regulating force of the chiral agent. As such a chiral agent, an optically active compound represented by general formula (1) as defined in claim 1 of Japanese Patent Application Publication No. 2002-302487 can be considered, and this content is incorporated herein.

[0141] When the liquid crystal composition of the present invention contains an orientation control agent, the content of the orientation control agent is not particularly limited, but it is preferably 0.01 to 10% by mass, and more preferably 0.05 to 5% by mass, relative to the total solid content mass in the liquid crystal composition. When the content is within this range, a uniform and highly transparent cured product can be obtained without precipitation, phase separation, orientation defects, etc., while achieving the desired orientation state.

[0142] [Polymerization Initiator] The liquid crystal composition of the present invention preferably contains a polymerization initiator. The polymerization initiator used is preferably a photopolymerization initiator that can initiate the polymerization reaction by ultraviolet irradiation. Examples of photopolymerization initiators include α-carbonyl compounds, acyloin ethers, α-hydrocarbon-substituted aromatic acyloin compounds, polynuclear quinone compounds, combinations of triarylimidazole dimers and p-aminophenyl ketones, acridine and phenazine compounds and oxadiazole compounds, acylphosphine oxide compounds, and the like. In addition, in the present invention, it is also preferable that the polymerization initiator is an oxime-type polymerization initiator, and specific examples include the initiators described in paragraphs

[0049] to

[0052] of International Publication No. 2017 / 170443.

[0143] [Solvent] The liquid crystal composition of the present invention preferably contains a solvent from the viewpoint of ease of forming a liquid crystal cured layer. Examples of solvents include ketones (e.g., acetone, 2-butanone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, cyclopentanone, etc.), ethers (e.g., dioxane, tetrahydrofuran, etc.), aliphatic hydrocarbons (e.g., hexane, etc.), alicyclic hydrocarbons (e.g., cyclohexane, etc.), aromatic hydrocarbons (e.g., toluene, xylene, trimethylbenzene, etc.), halogenated carbons (e.g., dichloromethane, dichloroethane, dichlorobenzene, chlorotoluene, etc.), esters (e.g., methyl acetate, ethyl acetate, butyl acetate, etc.), water, alcohols (e.g., ethanol, isopropanol, butanol, cyclohexanol, etc.), cellosolves (e.g., methyl cellosolve, ethyl cellosolve, etc.), cellosolve acetates, sulfoxides (e.g., dimethyl sulfoxide, etc.), amides (e.g., dimethylformamide, dimethylacetamide, etc.), etc., and these may be used individually or in combination of two or more.

[0144] [Leveling Agent] The liquid crystal composition of the present invention preferably contains a leveling agent from the viewpoint of keeping the surface of the liquid crystal cured layer of the present invention, which will be described later, smooth and facilitating orientation control. As such a leveling agent, a fluorine-based leveling agent or a silicon-based leveling agent is preferred because it has a high leveling effect relative to the amount added. Specifically, as a leveling agent, for example, the compounds described in paragraphs

[0079] to

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

[0020] to

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

[0022] to

[0029] ) Examples include the compounds described in the paragraphs, liquid crystal alignment promoters represented by general formula (I) as described in Japanese Patent Application Publication No. 2002-129162 (particularly the compounds described in paragraphs

[0076] to

[0078] and

[0082] to

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

[0092] to

[0096] ). These may also have the function of an alignment control agent, as described later.

[0145] [Other Components] The liquid crystal composition of the present invention may contain components other than those described above, such as tilt angle control agents, plasticizers, and crosslinking agents.

[0146] [Liquid Crystal Cured Layer] The liquid crystal cured layer of the present invention is a liquid crystal cured layer obtained by fixing the orientation state of the liquid crystal composition of the present invention as described above. As a method for forming the liquid crystal cured layer, for example, a method in which the liquid crystal composition of the present invention as described above is used to achieve a desired orientation state and then fixed by polymerization is used. Here, the polymerization conditions are not particularly limited, but in polymerization by light irradiation, it is preferable to use ultraviolet light. The irradiation dose is 10 mJ / cm ２ ~50 J / cm ２ Preferably, 20 mJ / cm ２ ~5J / cm ２ More preferably, 30 mJ / cm ２ ~3J / cm ２More preferably, 50 to 1000 mJ / cm ２ This is particularly preferable. Furthermore, the polymerization reaction may be carried out under heating conditions to promote it. The liquid crystal cured layer can be formed on any support or alignment film in the optical film described later.

[0147] As described above, the orientation state of the liquid crystal compound in the liquid crystal cured layer of the present invention may be any of homogeneous orientation, homeotropic orientation (vertical orientation), skewed orientation, hybrid orientation, or cholesteric orientation. However, it is preferable that the liquid crystal cured layer is fixed in a cholesteric orientation state because it can be effectively used as a reflective layer (reflective polarizer).

[0148] [Optical Film] The optical film of the present invention is an optical film having the liquid crystal curing layer of the present invention. Various components used in the optical film of the present invention will be described in detail below.

[0149] [Optical Anisotropic Film] 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. In the optical film of the present invention, the thickness of the liquid crystal curing layer is not particularly limited, but it is preferably 0.1 to 10 μm, and more preferably 0.5 to 5 μm.

[0150] [Support] As described above, the optical film of the present invention may have a support as a substrate for supporting the liquid crystal cured layer. Such a support is preferably transparent, and more specifically, it is preferably light transmittance of 80% or more.

[0151] Examples of such supports include glass substrates and polymer films. Examples of polymer film materials include cellulose polymers; acrylic polymers having acrylic acid ester polymers such as polymethyl methacrylate and lactone ring-containing polymers; thermoplastic norbornene polymers; polycarbonate polymers; polyester polymers such as polyethylene terephthalate and polyethylene naphthalate; styrene polymers such as polystyrene and acrylonitrile-styrene copolymer (AS resin); polyolefin polymers such as polyethylene, polypropylene, and ethylene-propylene copolymer; vinyl chloride polymers; amide polymers such as nylon and aromatic polyamides; imide polymers; sulfone polymers; polyethersulfone polymers; polyetheretherketone polymers; polyphenylene sulfide polymers; vinylidene chloride polymers; vinyl alcohol polymers; vinyl butyral polymers; arylate polymers; polyoxymethylene polymers; epoxy polymers; or polymers which are mixtures of these polymers.

[0152] In the present invention, the thickness of the support is not particularly limited, but it is preferably 5 to 60 μm, and more preferably 5 to 30 μm.

[0153] [Alignment Film] When the optical film of the present invention has any of the above-described supports, it is preferable that an alignment film is provided between the support and the liquid crystal cured layer. In addition, the above-described support may also serve as the alignment film.

[0154] Alignment films generally consist mainly of polymers. Numerous polymer materials for alignment films are described in various publications, and many commercially available products are available. The polymer material used in the present invention is preferably polyvinyl alcohol or polyimide, or its derivatives. Modified or unmodified polyvinyl alcohol is particularly preferred. Examples of alignment films usable in the present invention include the alignment film described on pages 43, line 24 to 49, line 8 of International Publication No. 01 / 88574; the modified polyvinyl alcohol described in paragraphs

[0071] to

[0095] of Japanese Patent Publication No. 3907735; and the liquid crystal alignment film formed by the liquid crystal alignment agent described in Japanese Patent Application Publication No. 2012-155308.

[0155] In the present invention, it is preferable to use a photo-alignment film as the alignment film because it is possible to prevent deterioration of the surface by not contacting the surface of the alignment film during its formation. The photo-alignment film is not particularly limited, but polymer materials such as polyamide compounds and polyimide compounds described in paragraphs

[0024] to

[0043] of International Publication No. 2005 / 096041; liquid crystal alignment films formed by liquid crystal alignment agents having photo-aligning groups described in Japanese Patent Application Publication No. 2012-155308; and Rolic Technologies' trade name LPP-JP265CP can be used.

[0156] Furthermore, in the present invention, the thickness of the orientation film is not particularly limited, but from the viewpoint of mitigating surface irregularities that may exist on the support and forming a liquid crystal cured layer with a uniform film thickness, it is preferably 0.01 to 10 μm, more preferably 0.01 to 1 μm, and even more preferably 0.01 to 0.5 μm.

[0157] [Image Display Device] The image display device of the present invention is an image display device having the optical film of the present invention. The display element used in the image display device of the present invention is not particularly limited and examples include liquid crystal cells, organic electroluminescent (hereinafter abbreviated as "EL") display panels, plasma display panels, etc. Of these, liquid crystal cells and organic EL display panels are preferred. That is, the image display device of the present invention is preferably a liquid crystal display device using a liquid crystal cell as a display element, and preferably an organic EL display device using an organic EL display panel as a display element.

[0158] The present invention will be described in more detail below based on the following examples. The materials, amounts used, proportions, processing content, and processing procedures shown in the following examples can be modified as appropriate without departing from the spirit of the present invention. Therefore, the scope of the present invention should not be interpreted as being limited by the following examples.

[0159] [Example 1] [Synthesis of Compound (A-1-1)] Compound (A-1-1), represented by the following formula (A-1-1), was synthesized according to the following scheme.

[0160] <Synthesis of compound (A-1-1-b)> In a 200 mL three-necked flask, combine 3.00 g of 6-hydroxy-2-naphthaldehyde, 5.60 g of compound (A-1-1a), and potassium carbonate (K ２ CO ３ 3.61 g of ), 0.29 g of potassium iodide (KI), 0.38 g of dibutylhydroxytoluene, and 55 mL of dimethylformamide (DMF) were added and the mixture was stirred at 80°C for 2 hours. The reaction mixture was then cooled to room temperature and added to a mixture of 50 mL of water, 4 mL of concentrated hydrochloric acid, and 100 mL of ethyl acetate. After stirring, the aqueous layer was removed and the organic layer was washed twice with 30 mL of 10% saline solution. The organic layer was dried over anhydrous magnesium sulfate to remove the drying agent, and the solvent was removed by distillation. The resulting oily composition was purified by silica gel column chromatography to obtain 5.01 g of the pale yellow oily compound (A-1-1-b) represented by the above formula (A-1-1-b).

[0161] <Synthesis of compound (A-1-1-c)> In a 100 mL three-necked flask, add 4.50 g of compound (A-1-1-b), 11.3 mL of ethyl acetate (AcOEt), 0.53 g of sodium dihydrogen phosphate, 3.5 mL of water, and 83 mg of tetrabutylammonium bisulfate. Finally, add 30% hydrogen peroxide (H ２ O ２ ) 1.5 mL was added. Sodium chlorite (NaClO) was added to it. ２ A solution of 1.66 g dissolved in 4 mL of water was added dropwise. The reaction mixture was heated to 40°C and stirred at 40°C for 3 hours. The reaction mixture was then cooled to room temperature, 11 mL of ethyl acetate was added, and the organic layer was washed twice with 11 mL of 5% sodium bisulfite aqueous solution, and then once with 11 mL of 10% saline solution. The organic layer was dried over anhydrous magnesium sulfate to remove the drying agent, and the solvent was removed by distillation to obtain 4.46 g of the yellow oily compound (A-1-1-c) represented by the above formula (A-1-1-c).

[0162] <Synthesis of Compound (A-1-1)> Place 4.4 g of compound (A-1-1-c), 250 mg of dibutylhydroxytoluene, 180 μL of dimethylformamide (DMF), and 62 mL of dichloromethane (DCM) into a 200 mL three-necked flask, and add oxalyl chloride ((COCl) ２2.0 mL of ) was added dropwise. The mixture was stirred at room temperature for 1 hour, and the solvent and excess oxalyl chloride were removed by distillation. To the obtained acid chloride, 22 mL of N-methylpyrrolidone (NMP) and 0.66 g of hydrazide (H-1) were added, and the mixture was stirred at 50°C for 3 hours. Then, 6.6 g of p-toluenesulfonic acid chloride (TsCl) and 8.0 mL of ethyl diisopropylamine (DIPEA) were added, and the mixture was stirred at 50°C for a further 2 hours. Next, the reaction mixture cooled to room temperature was added dropwise to 300 mL of methanol, and the precipitated solid was filtered off. The obtained crude material was purified by silica gel column chromatography to obtain 1.2 g of the pale yellow solid compound (A-1-1). The MALDI-MS (matrix-assisted laser desorption / ionization-mass spectrometry) measurement results of the obtained compound (A-1-1) are shown below. m / z: 1086.38 (100.0%), 1087.38 (70.8%), 1088.39 (23.6%), 1089.39 (7.0%), 1088.38 (4.0%), 1090.39 (1.6%)

[0163] [Example 2] [Synthesis of Compound (A-1-2)] Compound (A-1-2), represented by the following formula (A-1-2), was synthesized in the same manner as compound (A-1-1). The MALDI-MS measurement results of the obtained compound (A-1-2) are shown below. m / z: 1296.61 (100.0%), 1297.62 (85.8%), 1298.62 (40.7%), 1299.62 (12.6%), 1300.63 (3.0%), 1297.61 (2.2%)

[0164] [Example 3] [Synthesis of Compound (A-1-3)] Compound (A-1-3), represented by the following formula (A-1-3), was synthesized in the same manner as compound (A-1-1). The MALDI-MS measurement results of the obtained compound (A-1-3) are shown below. m / z: 1086.38 (100.0%), 1087.38 (70.8%), 1088.39 (23.6%), 1089.39 (7.0%), 1088.38 (4.0%), 1090.39 (1.6%)

[0165] [Example 4] [Synthesis of Compound (A-1-4)] Compound (A-1-4), represented by the following formula (A-1-4), was synthesized in the same manner as compound (A-1-1). The MALDI-MS measurement results of the obtained compound (A-1-4) are shown below. m / z: 1380.60 (100.0%), 1381.60 (90.4%), 1382.61 (39.3%), 1383.61 (14.1%), 1382.60 (5.0%), 1384.61 (3.8%), 1381.61 (1.0%)

[0166] [Example 5] [Synthesis of compound (A-1-5)] Compound (A-1-5), represented by the following formula (A-1-5), is synthesized in the same manner as compound (A-1-1).

[0167] [Example 6] [Synthesis of Compound (A-1-6)] Compound (A-1-6), represented by the following formula (A-1-6), was synthesized according to the following scheme.

[0168] <Synthesis of compound (A-1-6-a)> In a 1 L three-necked flask, combine 50.0 g of 2-hydroxy-4-methoxybenzaldehyde, 54.9 g of ethyl bromoacetate, and potassium carbonate (K ２ CO ３ 90.8 g of ) and 500 mL of dimethylformamide (DMF) were added and reacted at 90°C for 2 hours. The reaction solution was then cooled to room temperature, 500 mL of water and 80 mL of concentrated hydrochloric acid were added, and the mixture was stirred at room temperature for 15 minutes. The precipitated solid was filtered off, and 39.1 g of the light brown solid compound (A-1-6) represented by the above formula (A-1-6-a) was obtained.

[0169] <Synthesis of compound (A-1-6-b)> In a 500 mL three-necked flask, combine 22.4 g of compound (A-1-6-a), 224 mL of dichloromethane (DCM), and 1 M BBr ３ 310 mL of dichloromethane solution was added, and the mixture was heated under reflux for 2 hours. The reaction mixture was then cooled to below 5°C, and 100 mL of water was added. The precipitated solid was filtered, washed with water, and dried under reduced pressure at 70°C to obtain 18.4 g of the brown solid compound (A-1-6-b) represented by the above formula (A-1-6-b).

[0170] <Synthesis of Compound (A-1-6-c)> In a 1 L three-necked flask, 14.0 g of compound (A-1-6-b), 98 mL of dimethylformamide, 98 mL of tetrahydrofuran (THF), and 10.7 g of imidazole were placed. A solution of 30.3 g of triisopropylsilyl chloride (TIPS-Cl) dissolved in 39 mL of tetrahydrofuran was added dropwise. The mixture was stirred at room temperature for 1 hour, then 10 mL of acetic acid (AcOH) and 10 mL of water were added, and the mixture was stirred for a further 30 minutes. Next, 150 mL of water, 150 mL of acetic acid, and 80 mL of hexane were added to the reaction mixture, and the aqueous layer was removed. The organic layer was washed twice with 10% saline solution, dried over anhydrous magnesium sulfate, the drying agent was removed, and then the solvent was removed by distillation. 200 mL of hexane was added to the resulting crude mixture, and the precipitated solid was filtered off. The solid was dried under reduced pressure at 60°C to obtain 15.1 g of the white solid compound (A-1-6-c) represented by the above formula (A-1-6-c).

[0171] <Synthesis of compound (A-1-6-d)> Place 14.0 g of compound (A-1-6-c), 0.7 mL of dimethylformamide (DMF), and 50 mL of dichloromethane (DCM) into a 500 mL three-necked flask, and add oxalyl chloride ((COCl) ２ 10.1 mL of ) was added dropwise. The mixture was stirred at room temperature for 1 hour, and the solvent was removed by distillation under reduced pressure. Next, 50 mL of N-methylpyrrolidone (NMP) and 2.6 g of compound (H-1) were added to the obtained acid chloride and the mixture was stirred at 40°C for 3 hours. Then, 6.0 g of p-toluenesulfonic acid chloride (TsCl) and 11 mL of ethyl diisopropylamine (DIPEA) were added and the mixture was stirred at 40°C for 2 hours. Next, the reaction mixture was added dropwise to 500 mL of methanol, and the precipitated solid was filtered off. The solid was dried overnight in a forced-air dryer at 40°C to obtain 18.0 g of compound (A-1-6-d), a light brown solid represented by the above formula (A-1-6-d).

[0172] <Synthesis of Compound (A-1-6-e)> 15.0 g of compound (A-1-6-d), 150 mL of dimethylformamide, and 110 mL of tetrabutylammonium fluoride (TBAF) (1 M THF solution) were placed in a 1 L three-necked flask and stirred at room temperature for 3 hours. The reaction mixture was then added dropwise to a mixed solution of 3 L of methanol and 300 mL of water, and the precipitated solid was filtered off. The solid was dried under reduced pressure at 60°C to obtain 7.8 g of compound (A-1-6-e), a yellow solid represented by the above formula (A-1-6-e).

[0173] <Synthesis of compound (A-1-6)> In a 100 mL three-necked flask, combine 0.78 g of compound (A-1-6-e), 1.53 g of compound (A-1-1-a), and potassium carbonate (K ２ CO ３ 0.95 g of ) , 38.2 mg of potassium iodide (KI), and 15.6 mL of dimethylformamide (DMF) were added and stirred at 100°C for 4 hours. The reaction mixture was then cooled to room temperature, 20 mL of water, 50 mL of ethyl acetate, and 1 mL of concentrated hydrochloric acid were added and stirred, and the aqueous layer was removed. The organic layer was washed twice with 10% saline solution, dried over anhydrous magnesium sulfate to remove the drying agent, and then the solvent was removed by distillation. The resulting crude product was purified by silica gel column chromatography to obtain 600 mg of the pale yellow solid compound (A-1-6). The MALDI-MS measurement results of the obtained compound (A-1-6) are shown below. m / z: 1056.32 (100.0%), 1057.32 (62.8%), 1058.32 (23.1%), 1059.33 (5.8%), 1057.31 (2.2%), 1060.33 (1.2%)

[0174] [Example 7] [Synthesis of Compound (A-1-7)] Compound (A-1-7), represented by the following formula (A-1-7), was synthesized in the same manner as compound (A-1-6). The MALDI-MS measurement results of the obtained compound (A-1-7) are shown below. m / z: 1188.40 (100.0%), 1189.40 (69.5%), 1190.40 (28.5%), 1191.41 (5.4%), 1191.40 (3.1%), 1189.39 (2.2%), 1192.41 (1.8%)

[0175] [Example 8] [Synthesis of compound (A-1-8)] Compound (A-1-8), represented by the following formula (A-1-8), was synthesized according to the following scheme.

[0176] <Synthesis of compound (A-1-8-a)> In a 300 mL three-necked flask, under a nitrogen stream, 25.0 g of 4-bromo-3-fluorobenzaldehyde, 18.0 g of 3-methoxyphenol, and potassium carbonate (K) ２ CO ３ 25.0 g of ) and 81 mL of dimethyl sulfoxide (DMSO) were added, and the mixture was stirred at 85°C for 8 hours. The reaction mixture was then cooled to room temperature, and 200 mL of water was added. The precipitated solid was filtered and washed with a methanol / water = 1 / 1 mixed solution. The solid was air-dried overnight at 40°C to obtain 35.2 g of the light brown solid compound (A-1-8-a) represented by the above formula (A-1-8-a).

[0177] <Synthesis of Compound (A-1-8-b)> 32.0 g of compound (A-1-8-a), 25.6 g of sodium acetate (NaOAc), and 1 L of dimethylacetamide (DMAc) were placed in a 2 L three-necked flask and degassed under a nitrogen flow for 30 minutes. 1.2 g of palladium / carbon (10%) was added, and the mixture was degassed under a nitrogen flow for another 30 minutes. The reaction mixture was stirred at 135°C for 2 hours, and the catalyst was removed by Celite filtration. 400 mL of water was added dropwise to the filtrate, and the mixture was stirred at a temperature below 10°C. The precipitated solid was filtered off and air-dried at 40°C to obtain 16.4 g of compound (A-1-8-b), a light brown solid represented by the above formula (A-1-8-b).

[0178] <Synthesis of Compound (A-1-8-c)> In a 200 mL three-necked flask, 8.00 g of compound (A-1-8-b) and 132 mL of dichloromethane (DCM) were placed under a nitrogen stream, and the internal temperature was cooled to -78°C. 50 mL of diisobutylaluminum hydride (DIBAL) (1 M toluene solution) was added dropwise. The reaction mixture was then stirred for 1 hour, 13.5 g of silica gel and 1.5 mL of water were added, and the mixture was heated to room temperature and stirred for 2 hours. Next, 100 mL of 10% tartaric acid aqueous solution was added and stirred, the aqueous layer and solids were removed, and the organic layer was concentrated to obtain 6.8 g of compound (A-1-8-c), a pale yellow solid represented by the above formula (A-1-8-c).

[0179] <Synthesis of compound (A-1-8-d)> In a 500 mL three-necked flask, combine 6.50 g of compound (A-1-8-c) and sodium dihydrogen phosphate (NaH) ２ PO ４ 17.2 g of ) was added, along with 115 mL of tetrahydrofuran (THF), 115 mL of t-butyl alcohol (t-BuOH), 24 mL of water, and 20.0 g of 2-methyl-2-butene. Sodium chlorite (NaClO) was added to the mixture. ２ 6.50 g was added and the mixture was stirred for 30 minutes. Approximately 100 mL of the solvent was removed by vacuum distillation, and 100 mL of water was added thereto. The precipitated solid was filtered off and air-dried overnight at 40°C to obtain 5.60 g of the pale yellow solid compound (A-1-8-d) represented by the above formula (A-1-8-d).

[0180] <Synthesis of Compound (A-1-8)> Compound (A-1-8) was synthesized using compound (A-1-8-d) in the same manner as compound (A-1-6). The MALDI-MS measurement results of the obtained compound (A-1-8) are shown below. m / z: 1416.60 (100.0%), 1417.60 (93.6%), 1418.61 (42.2%), 1419.61 (15.6%), 1418.60 (5.1%), 1420.61 (4.3%), 1419.60 (1.0%), 1417.61 (1.0%)

[0181] [Examples 9-16] Compounds (A-1-9) to (A-1-16) represented by the following formulas (A-1-9) to (A-1-16) were synthesized according to the synthesis examples and standard methods described above.

[0182] [Example 17] [Synthesis of Compound (A-2-1)] Compound (A-2-1), represented by the following formula (A-2-1), was synthesized according to the following scheme.

[0183] <Synthesis of compound (A-2-1-a)> Compound (A-2-1-a), represented by the above formula (A-2-1-a), was synthesized in the same manner as compound (A-5-1-a) described later.

[0184] <Synthesis of compound (A-2-1-b)> Compound (A-2-1-b), represented by the above formula (A-2-1-b), was synthesized in the same manner as compound (A-4-1-c) described later.

[0185] Compound (A-2-1) was synthesized using the same method as compound (A-1-1). The MALDI-MS measurement results for the obtained compound (A-2-1) are shown below. m / z: 1287.40 (100.0%), 1288.40 (79.1%), 1289.40 (36.0%), 1290.41 (10.3%), 1288.39 (3.3%), 1291.41 (2.5%), 1290.40 (1.1%)

[0186] [Example 18] [Synthesis of Compound (A-3-1)] Compound (A-3-1), represented by the following formula (A-3-1), is synthesized according to the following scheme.

[0187] <Synthesis of compound (A-3-1-a)> In a 500 mL three-necked flask, 5.00 g of p-formylbenzoic acid, 5.56 g of 2-amino-5-methoxyphenol, and 300 mL of toluene are placed under a nitrogen stream and heated under reflux for 3 hours. The precipitated solid is filtered off to obtain compound (A-3-1-a) represented by the above formula (A-3-1-a).

[0188] <Synthesis of compound (A-3-1-b)> 5.00 g of compound (A-3-1-a), 8.37 g of 2,3-dichloro-5,6-dicyano-p-benzoquinone, 150 mL of dichloromethane, and 50 mL of tetrahydrofuran are placed in a 300 mL three-necked flask and heated under a nitrogen stream for 5 hours under reflux. The reaction solvent is then concentrated under reduced pressure and purified by silica gel chromatography to obtain compound (A-3-1-b) represented by the above formula (A-3-1-b).

[0189] <Synthesis of compound (A-3-1-c)> Using compound (A-3-1-b), compound (A-3-1-c), represented by the above formula (A-3-1-c), is synthesized in the same manner as compound (A-1-6-d).

[0190] <Synthesis of compound (A-3-1-d)> Using compound (A-3-1-c), compound (A-3-1-d), represented by the above formula (A-3-1-d), is synthesized in the same manner as compound (A-1-6-b).

[0191] <Synthesis of Compound (A-3-1)> Compound (A-3-1) is synthesized using compound (A-3-1-d) in the same manner as compound (A-1-6).

[0192] [Examples 19-21] Compounds (A-3-2) to (A-3-4) represented by the following formulas (A-3-2) to (A-3-4) were synthesized according to the synthesis examples and standard methods described above.

[0193] [Example 22] [Synthesis of Compound (A-4-1)] Compound (A-4-1), represented by the following formula (A-4-1), was synthesized according to the following scheme.

[0194] <Synthesis of Compound (A-4-1-a)> 30.0 g of 1,3-butanediol, 56.6 g of imidazole (Im), and 300 mL of dichloromethane were placed in a 1 L three-necked flask and cooled to below 10°C. 50.2 g of triisopropylsilyl chloride (TIPSCl) was added dropwise, and the temperature was raised to 25°C. The mixture was stirred at 25°C for 2 hours, 150 mL of 10% saline solution was added to the reaction mixture, and after stirring, the aqueous layer was removed. The aqueous layer was extracted twice with 75 mL of dichloromethane, and the organic layer was concentrated under reduced pressure. 100 mL of hexane and 100 mL of water were added to the obtained oily composition, and after stirring, the aqueous layer was removed. The organic layer was dried over anhydrous magnesium sulfate, the drying agent was filtered off, and the solvent was removed by distillation to obtain 65.2 g of the colorless oily compound (A-4-1-a) represented by the above formula (A-4-1-a).

[0195] <Synthesis of Compound (A-4-1-b)> 10.0 g of compound (A-4-1-a), 50 mL of dichloromethane (DCM), and 4.81 g of pyridine (Py) were placed in a 200 mL three-necked flask and cooled to below 5°C. A solution of 6.99 g of phenyl chloroformate and 30 mL of dichloromethane was added dropwise. The mixture was stirred at 25°C for 2 hours, 20 mL of 1N hydrochloric acid and 20 mL of water were added, and after stirring, the aqueous layer was removed. The aqueous layer was re-extracted with 50 mL of dichloromethane, and the organic layers were washed together with 10% saline solution and dried over anhydrous magnesium sulfate. The drying agent was filtered off, and the mixture was concentrated under reduced pressure to obtain 14.6 g of the colorless oily compound (A-4-1-b) represented by the above formula (A-4-1-b).

[0196] <Synthesis of compound (A-4-1-c)> In a 200 mL three-necked flask, combine 14.6 g of compound (A-4-1-b), 50 mL of ethanol (EtOH), and hydrazine monohydrate (NH₄). ２ NH ２ -H ２4.91 mL of (79 wt%) O) was added and stirred at 80°C for 1 hour. The reaction mixture was cooled to room temperature, and 50 mL of water, 150 mL of ethyl acetate, and 50 mL of hexane were added and stirred. The aqueous layer was removed, and the organic layer was washed twice with water and once with 10% saline solution, and dried over anhydrous sodium sulfate. The drying agent was filtered off, and the organic layer was concentrated. The resulting crude product was purified by silica gel column chromatography to obtain 11.4 g of the colorless oily compound (A-4-1-c) represented by the above formula (A-4-1-c).

[0197] <Synthesis of compound (A-4-1-d)> Compound (A-4-1-d), represented by the above formula (A-4-1-d), was synthesized using compound (A-4-1-c) instead of compound (H-1) in the same manner as compound (A-1-6-d).

[0198] <Synthesis of Compound (A-4-1-e)> 8.26 g of compound (A-4-1-d), 92 mL of acetonitrile (MeCN), 1.8 mL of water, 6.9 mL of triethylamine, and 14.4 g of lithium bromide (LiBr) were placed in a 200 mL three-necked flask and stirred at 70°C for 1 hour. The mixture was filtered at 70°C to collect the solid, which was then washed with acetonitrile. The solid was dissolved in 200 mL of water, and 20 mL of 1 N hydrochloric acid was added and stirred. The precipitated solid was filtered, washed with water, and dried under reduced pressure at 70°C to obtain 5.10 g of the pale red compound (A-4-1-e) represented by the above formula (A-4-1-e).

[0199] <Synthesis of compound (A-4-1-f)> Compound (A-4-1-f), represented by the above formula (A-4-1-f), was synthesized in the same manner as compound (A-1-6-d).

[0200] <Synthesis of compound (A-4-1-g)> Compound (A-4-1-g), represented by the above formula (A-4-1-g), was synthesized in the same manner as compound (A-1-6-e).

[0201] <Synthesis of Compound (A-4-1)> 2.10 g of compound (A-4-1-g), 0.84 g of acrylate chloride, and 30 mL of tetrahydrofuran (THF) were placed in a 200 mL three-necked flask and cooled to below 5°C. 0.94 g of triethylamine (TEA) was added dropwise and the mixture was stirred at room temperature for 2 hours. 50 mL of water and 100 mL of ethyl acetate were added to the reaction mixture and stirred, after which the aqueous layer was removed. The organic layer was dried over anhydrous magnesium sulfate, the drying agent was filtered off, and the solvent was removed by distillation. The resulting crude product was purified by silica gel column chromatography to obtain 0.89 g of compound (A-4-1) as a pale yellow solid. The MALDI-MS measurement results of the obtained compound (A-4-1) are shown below. m / z: 1318.41 (100.0%), 1319.42 (78.0%), 1320.42 (33.2%), 1321.42 (11.1%), 1319.41 (4.4%), 1320.41 (3.5%), 1322.43 (2.3%)

[0202] [Examples 23-24] Compounds (A-4-2) to (A-4-3) represented by the following formulas (A-4-2) to (A-4-3) were synthesized according to the synthesis examples and standard methods described above.

[0203] [Example 25] Compound (A-5-1) represented by the following formula (A-5-1) is synthesized according to the following scheme.

[0204] <Synthesis of compound (A-5-1-a)> By replacing p-formylbenzoic acid with 1,3,5-triformylbenzene, compound (A-5-1-a) represented by the above formula (A-5-1-a) is synthesized in the same manner as compound (A-3-1-b).

[0205] <Synthesis of compound (A-5-1-b)> Compound (A-5-1-b), represented by the above formula (A-5-1-b), is synthesized in the same manner as compound (A-1-6-b).

[0206] <Synthesis of Compound (A-5-1)> Compound (A-5-1) is synthesized in the same manner as compound (A-1-6).

[0207] [Example 26] Compound (A-6-1) represented by the following formula (A-6-1) is synthesized according to the following scheme.

[0208] <Synthesis of compound (A-6-1-a)> Compound (A-6-1-a), represented by the above formula (A-6-1-a), is synthesized in the same manner as compound (A-5-1-a).

[0209] <Synthesis of Compound (A-6-1)> Compound (A-6-1) is synthesized in the same manner as compound (A-4-1).

[0210] [Example 27] Compound (A-6-2) represented by the following formula (A-6-2) was synthesized according to the synthesis examples and standard methods described above.

[0211] [Comparative Example 1] The following D-658 (hereinafter also referred to as "compound (C-1)") described in paragraph

[0137] of Japanese Patent Publication No. 2007-246672 is synthesized according to the method and standard procedures described in the said publication.

[0212] [Comparative Example 2] The following D-24 (hereinafter also referred to as "compound (C-2)") described in paragraph

[0071] of Japanese Patent Application Publication No. 2006-273781 is synthesized according to the method and standard procedures described in the said publication.

[0213] [Comparative Example 3] The following compound described in Japanese Patent Publication No. 2010-244038 (hereinafter also referred to as "compound (C-3)") was synthesized in the same manner as in Example 14 (synthesis of exemplary compound (13)) of the same publication.

[0214] [Evaluation] The compounds synthesized in Examples 1-4, 6-8, 17, and 22, as well as in Comparative Example 3, were evaluated as follows. The compounds synthesized in the other examples and comparative examples were also evaluated as follows. The results are shown in Tables 1 and 2 below.

[0215] (1) Δn <Preparation of coating solution> The following materials were mixed at room temperature to prepare the additive mother liquor. ------------------------------------------------------------------- Initiator (BASF IrgacureOXE01) 60 mg Orienting agent (V-1) 8 mg 2-Butanone 17.82 g -------------------------------------------------------------------

[0216] Orienting agent (V-1) [In the following formula, Me represents a methyl group]

[0217] The materials listed in the table below were mixed at room temperature to prepare the coating solution. ------------------------------------------------------------------- ・The above compound (C-3) 50 mg ・Each compound from Examples 1-27 and Comparative Examples 1-3 50 mg ・Additive mother liquor 930 mg -------------------------------------------------------------------

[0218] <Preparation of Cured Film> 100 μL of the prepared coating solution was spin-coated onto a glass substrate with an SD1 (DIC Corporation) alignment film at 1600 rpm for 10 seconds. The coated film was aged at 105°C for 1 minute and cured at 40°C at 10 mW / cm² under a nitrogen atmosphere. ２ The sample was exposed to light for 30 seconds to produce a cured film.

[0219] <Measurement> The retardation Re(λ) of the cured film in the slow axis orientation was measured using an AxoScan OPMF-1 (OptoScience Co., Ltd.). The measurement was performed at a measurement wavelength of 550 nm, polar angle 0°, azimuthal angle 0°, and in a 25°C 60% RH environment. The cured film was peeled off with tape, and the film thickness was measured using a non-contact three-dimensional surface roughness measuring instrument (VertScan, Ryoka Systems Co., Ltd.). Using the measured retardation (Re(550 nm)) and film thickness (d), the Δn of the composition was calculated from the following formula: Re(λ) = Δn × d × 1000 (nm) The Δn of each compound in Examples 1 to 27 and Comparative Examples 1 to 3 was determined by extrapolation from the Δn of the obtained composition and the Δn of compound (C-3) alone, and evaluated according to the following criteria. (Evaluation Criteria) A: 0.30 or higher B: 0.25 or higher and less than 0.30 C: 0.20 or higher and less than 0.25 D: Less than 0.20

[0220] (2) Solubility The compounds of Examples 1 to 27 and Comparative Examples 1 to 3 were weighed at 100 mg, and methyl ethyl ketone (MEK) was added to a total of 40% by mass. The compounds were then dissolved by heating at 70°C. If complete dissolution occurred, the MEK solubility was judged to be 40% by mass or more. If complete dissolution did not occur, MEK was added further, and the test was repeated at 70°C, diluting to 30% by mass, 20% by mass, 10% by mass, 5% by mass, and 1% by mass until the compound was completely dissolved. The concentration at which the compound was completely dissolved was defined as the MEK solubility and evaluated according to the following criteria: <Evaluation Criteria> A: 40% by mass or more B: 30% by mass or more and less than 40% by mass C: 20% by mass or more and less than 30% by mass D: Less than 20% by mass

[0221]

[0222]

[0223] From the results shown in Tables 1 and 2, it was found that compounds that do not correspond to any of the above formulas (1) to (6) have inferior refractive index (Δn) at a wavelength of 550 nm and solubility, or both (Comparative Examples 1 to 3). In contrast, compounds corresponding to any of the above formulas (1) to (6) have a high Δn and excellent solubility in solvents (Examples 1 to 27). In particular, from the comparison between Example 3 and Example 15, it was found that when the central ring structure is a benzene ring, the solubility in solvents is better. Also, from the comparison between Example 3 and Example 16, it was found that R in formula (1) １１ , R １２ and R １３ It was found that Δn becomes higher when all of the above equations (A1) are expressed.

Claims

A compound represented by any of the following formulas (1) to (6). Here, in equation (1) above, R １１ , R １２ and R １３ Each of these independently represents either the following formula (A1) or a hydrogen atom. However, R １１ , R １２ and R １３ Of these, at least two represent the following equation (A1). T １１ 、 T １２ and T １３ each independently represents a methine or a nitrogen atom. Here, in formula (A1), * indicates the joining position. X １１ This represents a five-membered heterocyclic group represented by any of the following formulas (X11-1) to (X11-14). Y １１ X represents a five-membered heterocyclic ring group, a fused aromatic hydrocarbon ring group, or a fused aromatic heterocyclic ring group represented by any of the following formulas (X11-1) to (X11-14). １１ However, when representing a five-membered heterocyclic ring group represented by the following formula (X11-1), Y １１ X represents a five-membered heterocyclic group represented by any of the following formulas (X11-1) to (X11-14). １１ However, if it represents a five-membered heterocyclic ring group represented by any of the following formulas (X11-3), (X11-4), (X11-8), (X11-10), (X11-12), and (X11-13), Y １１ This represents a five-membered heterocyclic ring group or a fused aromatic hydrocarbon ring group represented by any of the following formulas (X11-1) to (X11-14). L １１ -CH represents a linear or branched alkylene group, or a linear or branched alkenylene group. However, one or more non-adjacent -CH groups contained in the alkylene group or the alkenylene group. ２ - is -O-, -COO-, -OCO-, -OCOO-, -CO-, -S-, -SO ２ -, -NR-, -NRSO ２ -, or -SO ２ It may be substituted with NR-. R represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. In addition, one or more hydrogen atoms contained in the alkylene group or alkenylene group may be substituted with halogen atoms. Also, X １１ This represents a five-membered heterocyclic group represented by the following formula (X11-2), and Y １１ When L represents a fused aromatic hydrocarbon ring group, １１ represents a branched alkylene group or a branched alkenylene group. Q １１ represents a polymerizable group, a hydrogen atom, a hydroxyl group, a carboxyl group, or a halogen atom. Here, in the above formulas (X11-1) to (X11-14), * represents the bonding position. Here, in equation (2) above, R ２１ , R ２２ and R ２３ Each of these independently represents either the following formula (A2) or a hydrogen atom. However, R ２１ , R ２２ and R ２３ Of these, at least two represent the following equation (A2). T ２１ , T ２２ and T ２３ Each of these independently represents either a methine or a nitrogen atom. Here, in formula (A2), * indicates the joining position. X ２１ This represents a fused aromatic hydrocarbon ring group or a fused aromatic heterocyclic ring group. Y ２１ This represents a phenylene group which may have substituents, a monocyclic aromatic heterocyclic group, a fused aromatic hydrocarbon ring group, or a fused aromatic heterocyclic group. Z ２１ This represents a phenylene group which may have substituents, a monocyclic aromatic heterocyclic group, a fused aromatic hydrocarbon ring group, or a fused aromatic heterocyclic group. L ２１ -CH represents a linear or branched alkylene group, or a linear or branched alkenylene group. However, one or more non-adjacent -CH groups contained in the alkylene group or the alkenylene group. ２ - is -O-, -COO-, -OCO-, -OCOO-, -CO-, -S-, -SO ２ -, -NR-, -NRSO ２ -, or -SO ２ It may be substituted with NR-, where R represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. Furthermore, one or more hydrogen atoms contained in the alkylene group or alkenylene group may be substituted with halogen atoms. Q ２１ Q represents a polymerizable group, a hydrogen atom, a hydroxyl group, a carboxyl group, or a halogen atom. ２１ At least one of them represents a polymerizable group. Here, in equation (3) above, R ３１ , R ３２ and R ３３ Each of these independently represents either the following formula (A3) or a hydrogen atom. However, R ３１ , R ３２ and R ３３ Of these, at least two represent the following formula (A3). T ３１ , T ３２ and T ３３ Each of these independently represents either a methine or a nitrogen atom. Here, in formula (A3), * indicates the joining position. X ３１ This represents a five-membered heterocyclic group represented by any of the above formulas (X11-1) to (X11-14). Y ３１ This represents a phenylene group which may have substituents. Z ３１ X represents a phenylene group which may have substituents, a monocyclic aromatic heterocyclic group, a fused aromatic hydrocarbon ring group, or a fused aromatic heterocyclic group. ３１ However, when representing a five-membered heterocyclic group represented by any of the above (X11-1), (X11-2), (X11-8), and (X11-9), Z ３１ This represents a fused aromatic hydrocarbon ring group or a fused aromatic heterocyclic ring group. L ３１ -CH represents a linear or branched alkylene group, or a linear or branched alkenylene group. However, one or more non-adjacent -CH groups contained in the alkylene group or the alkenylene group. ２ - is -O-, -COO-, -OCO-, -OCOO-, -CO-, -S-, -SO ２ -, -NR-, -NRSO ２ -, or -SO ２ It may be substituted with NR-, where R represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. Furthermore, one or more hydrogen atoms contained in the alkylene group or alkenylene group may be substituted with halogen atoms. Q ３１ represents a polymerizable group, a hydrogen atom, a hydroxyl group, a carboxyl group, or a halogen atom. Here, in equation (4), R ４１ , R ４２ and R ４３ Each of these independently represents either the following formula (A4) or a hydrogen atom. However, R ４１ , R ４２ and R ４３ Of these, at least two represent the following formula (A4). T ４１ , T ４２ and T ４３ Each of these independently represents either a methine or a nitrogen atom. Here, in formula (A4), * indicates the joining position. X ４１ This represents a five-membered heterocyclic group represented by any of the above formulas (X11-1) to (X11-14). Y ４１ This represents a monocyclic aromatic heterocyclic group, a fused aromatic hydrocarbon ring group, or a fused aromatic heterocyclic group. Z ４１ This represents a phenylene group which may have substituents, a monocyclic aromatic heterocyclic group, a fused aromatic hydrocarbon ring group, or a fused aromatic heterocyclic group. L ４１ -CH represents a linear or branched alkylene group, or a linear or branched alkenylene group. However, one or more non-adjacent -CH groups contained in the alkylene group or the alkenylene group. ２ - is -O-, -COO-, -OCO-, -OCOO-, -CO-, -S-, -SO ２ -, -NR-, -NRSO ２ -, or -SO ２ It may be substituted with NR-, where R represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. Furthermore, one or more hydrogen atoms contained in the alkylene group or alkenylene group may be substituted with halogen atoms. Q ４１ represents a polymerizable group, a hydrogen atom, a hydroxyl group, a carboxyl group, or a halogen atom. Here, in equation (5) above, R ５１ , R ５２ and R ５３ Each of these independently represents the following formula (A5). T ５１ , T ５２ and T ５３ Each of these independently represents either a methine or a nitrogen atom. In the above formula (A5), * indicates the joining position. X ５１ This represents a fused aromatic hydrocarbon ring group or a fused aromatic heterocyclic ring group. L ５１ represents a linear or branched alkylene group or a linear or branched alkenylene group. However, one or two or more non-adjacent -CH ２ - in the alkylene group or the alkenylene group may be replaced by -O-, -COO-, -OCO-, -OCOO-, -CO-, -S-, -SO ２ -, -NR-, -NRSO ２ -, or -SO ２ NR-. R represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. Further, one or two or more hydrogen atoms contained in the alkylene group or the alkenylene group may be replaced by a halogen atom. Q ５１ This represents a polymerizable group. Here, in equation (6), R ６１ 、 R ６２ and R ６３ each independently represents the following formula (A6). T ６１ , T ６２ and T ６３ Each of these independently represents either a methine or a nitrogen atom. Here, in the above formula (A6), * indicates the joining position. X ６１ This represents a fused aromatic hydrocarbon ring group or a fused aromatic heterocyclic ring group. Y ６１ This represents a phenylene group which may have substituents, a monocyclic aromatic heterocyclic group, a fused aromatic hydrocarbon ring group, or a fused aromatic heterocyclic group. L ６１ -CH represents a linear or branched alkylene group, or a linear or branched alkenylene group. However, one or more non-adjacent -CH groups contained in the alkylene group or the alkenylene group. ２ - is -O-, -COO-, -OCO-, -OCOO-, -CO-, -S-, -SO ２ -, -NR-, -NRSO ２ -, or -SO ２ It may be substituted with NR-, where R represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. Furthermore, one or more hydrogen atoms contained in the alkylene group or alkenylene group may be substituted with halogen atoms. Q ６１ This represents a polymerizable group. 　 A compound represented by any of the above formulas (1) to (6) has a fused aromatic hydrocarbon ring group or a fused aromatic heterocyclic group, The aromatic hydrocarbon ring group of the fused ring is a group obtained by removing two hydrogen atoms bonded to the ring from an aromatic hydrocarbon ring of a fused ring represented by any of the following formulas (X51-1) to (X51-3), The compound according to claim 1, wherein the aromatic heterocyclic group of the fused ring is a group obtained by removing two hydrogen atoms bonded to the ring from an aromatic heterocyclic ring of a fused ring represented by any of the following formulas (X51-4) to (X51-20). X １１ , X ３１ and X ４１ The compound according to claim 1, wherein the compound represents a five-membered heterocyclic group represented by any of the formulas (X11-2), (X11-5), (X11-7), (X11-9), (X11-12), and (X11-14). 　 The compound according to claim 1, which is a compound represented by formula (1). 　 X in formula (A1) １１ The compound according to claim 4, wherein the compound represents a five-membered heterocyclic group represented by the formula (X11-2). 　 L in formula (A1) １１ The compound according to claim 4, wherein the group is a branched alkylene group. 　 The compound according to claim 2, wherein the aromatic hydrocarbon ring group of the fused ring is a group obtained by removing two hydrogen atoms bonded to the ring from the aromatic hydrocarbon ring of the fused ring represented by formula (X51-1). 　 The compound according to claim 2, wherein the aromatic heterocyclic group of the fused ring is a group obtained by removing two hydrogen atoms bonded to the ring from an aromatic heterocyclic ring of any of the formulas (X51-4), (X51-5), (X51-10), (X51-11), (X51-16), and (X51-17). 　 A liquid crystal composition containing the compound described in any one of claims 1 to 8. 　 Furthermore, the liquid crystal composition according to claim 9, further containing a chiral agent. 　 A liquid crystal cured layer having the orientation state of the liquid crystal composition described in claim 9 fixed. 　 An optical film having the liquid crystal curing layer described in claim 11. 　 An image display device having the optical film described in claim 12.

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