Liquid crystal composition, optical film, display device, and compound

Abstract

The present invention addresses the problem of providing: a liquid crystal composition with which it is possible to produce a liquid crystal cured layer having excellent light resistance while maintaining excellent adhesion to an adjacent layer; an optical film; a display device; and a compound. The liquid crystal composition according to the present invention contains a compound represented by formula (1) and a liquid crystal compound. In formula (1), l represents an integer of at least 1, m represents an integer of 0-4, and n represents an integer of at least 2. P represents a polymerizable group, and a plurality of Ps may be the same as or different from each other. L1 represents a single bond or an (n+m)-valent linking group. L2 represents an (l+1)-valent linking group, and a plurality of L2s may be the same as or different from each other. Here, the total number of aromatic rings contained in L1 and L2 is at most 2.

Description

Liquid crystal compositions, optical films, display devices, and compounds

[0001] This invention relates to liquid crystal compositions, optical films, display devices, and compounds.

[0002] In liquid crystal display devices (LCDs) and organic electroluminescent display devices (OLEDs), films with birefringence, consisting of a liquid crystal cured layer (optical anisotropy layer) formed by applying an orientation treatment to a liquid crystal compound and then curing it with ultraviolet light to fix its orientation, have been put into practical use to prevent light reflection.

[0003] As a composition for forming such a liquid crystal cured layer, for example, Patent Document 1 describes "a composition for forming a liquid crystal cured film comprising at least two polymerizable liquid crystal compounds, a solvent, a polymerization initiator, a tertiary amine compound, and a compound containing three or more thiol groups" (see, for example, [Claim 1]).

[0004] Japanese Patent Publication No. 2015-143787

[0005] The present inventors investigated the composition described in Patent Document 1 and found that the formed liquid crystal cured layer had excellent adhesion to adjacent layers (for example, other liquid crystal cured layers or polarizers), but it was found to have poor light resistance.

[0006] Therefore, the object of the present invention is to provide a liquid crystal composition, optical film, display device, and compound that can produce a liquid crystal cured layer that maintains excellent adhesion to adjacent layers while also having excellent light resistance.

[0007] As a result of diligent research to achieve the above objectives, the inventors discovered that by using a liquid crystal composition containing a predetermined compound having a thioether group, it is possible to produce a liquid crystal cured layer that maintains excellent adhesion to adjacent layers while also exhibiting excellent light resistance, thus completing the present invention. In other words, the inventors found that the above objectives can be solved by the following configuration.

[0008] [1] A liquid crystal composition comprising a compound represented by Formula (1) described below and a liquid crystal compound. [2] The liquid crystal composition according to [1], wherein P in Formula (1) described below is a radically polymerizable group or a cationically polymerizable group. [3] The liquid crystal composition according to [1] or [2], wherein P in Formula (1) described below is a radically polymerizable group. [4] The liquid crystal composition according to any one of [1] to [3], wherein m in Formula (1) described below is 0. [5] The liquid crystal composition according to [4], wherein n in Formula (1) described below is an integer of 2 to 4. [6] L in Formula (1) described below １ represents a single bond, an alkylene group which may have a substituent, or a linking group represented by Formula (L1-1) described below, the liquid crystal composition according to any one of [1] to [5], provided that one or more -CH ２ - constituting the alkylene group may be substituted with -O-, -CO- or -NH-. [7] L in Formula (1) described below １ is an alkylene group, or is represented by Formula (L1-1) described below, and X in Formula (L1-1) described below is a carbon atom, (**-) ３ CR, or (**-) ３ C-L ４ -C(-**) ３ which represents, the liquid crystal composition according to [6], wherein L represents said linking group. [8] L in Formula (1) described below ２ represents an alkylene group which may have a substituent, the liquid crystal composition according to any one of [1] to [7], provided that one or more -CH ２One or more of the -s may be substituted with -O-, -CO-, or -NH-. [9] A liquid crystal composition according to any one of [1] to [8], wherein the molecular weight of the compound represented by formula (1) described later is 300 to 1500.

[10] A liquid crystal composition according to any one of [1] to [9], wherein the content of the compound represented by formula (1) described later is 0.1 to 10 parts by mass per 100 parts by mass of the liquid crystal compound.

[11] An optical film having a liquid crystal cured layer in which the orientation state of the liquid crystal composition according to any one of [1] to

[10] is fixed.

[12] A display device having the optical film according to

[11] .

[13] A compound represented by formula (1) described later.

[14] A compound according to

[13] , wherein m in formula (1) described later is 0.

[15] A compound according to

[14] , wherein n in formula (1) described later is 2 to 4.

[16] L in formula (1) described later １ The compound according to any of

[13] to

[15] , which represents a single bond, an alkylene group which may have substituents, or a linking group represented by formula (L1-1) described later. However, the -CH constituting the alkylene group ２ One or more of the -s may be replaced by -O-, -CO-, or -NH-.

[17] L in formula (1) described later １ However, it is represented by an alkylene group, or by formula (L1-1) described later, and X in formula (L1-1) described later is a carbon atom, (**-) ３ CR, or (**-) ３ C-L ４ -C (-**) ３ A compound described in

[16] that represents a linking group.

[18] L in formula (1) described later. ２ The compound according to any one of

[13] to

[17] , which represents an alkylene group that may have substituents. ２ One or more of the hyphens may be replaced by -O-, -CO-, or -NH-.

[0009] According to the present invention, it is possible to provide a liquid crystal composition, optical film, display device, and compound that can produce a liquid crystal cured layer that maintains excellent adhesion to adjacent layers while also having excellent light resistance.

[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 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. In this specification, "(meth)acrylic" is a notation that represents "acrylic" or "methacrylic," and "(meth)acryloyl" is a notation that represents "acryloyl" or "methacryloyl." Furthermore, the bonding direction of the divalent group (e.g., -O-CO-) as expressed herein is not particularly limited, for example, "L １ -L ２ -L ３ In the combination of "L ２ If L is -O-CO-, １ The position where it is joined to the side is *1, L ３ If we denote the position where it is joined to the side as *2, then L ２ *1-O-CO-*2 may also be *1-CO-O-*2.

[0011] In this specification, Re(λ) and Rth(λ) represent the in-plane retardation and thickness-direction retardation at wavelength λ, respectively. Unless otherwise specified, wavelength λ is assumed to be 550 nm. Furthermore, in this specification, Re(λ) and Rth(λ) are values ​​measured at wavelength λ using an AxoScan OPMF-1 (manufactured by OptoScience Co., Ltd.). 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 in the slow-speed axis direction (°): Re(λ) = R0(λ) Rth(λ) = ((nx + ny) / 2 - nz) × d Note that R0(λ) is displayed as a value calculated by the AxoScan OPMF-1, but it means Re(λ).

[0012] 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); alkyl groups (preferably C1 to C48, more preferably C1 to C24, particularly preferably C1 to C8 alkyl groups, for example, linear alkyl groups having C1 to C6 (e.g., methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group), branched alkyl groups having C3 to C6 (e.g., isopropyl group, isobutyl group, tert-butyl group, sec-butyl group, neopentyl group, isohexyl group, 3-methylpentyl group), and cyclic alkyl groups having C3 to C12 (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);Hydroxyalkyl groups (preferably hydroxyalkyl groups having 1 to 12 carbon atoms, for example, hydroxymethyl groups); hydroxyalkyleneoxy groups (preferably hydroxyalkyleneoxy groups having 2 to 10 carbon atoms, for example, hydroxyethyleneoxy groups); alkoxycarbonyloxy groups (preferably alkoxycarbonyloxy groups having 2 to 48 carbon atoms, more preferably 2 to 24 carbon atoms, for example, ethoxycarbonyloxy groups, t-butoxycarbonyloxy groups, cycloalkyloxycarbonyloxy groups (for example, cyclohexyloxycarbonyloxy groups)); aryloxycarbonyloxy groups (preferably aryloxycarbonyloxy groups having 7 to 32 carbon atoms, more preferably 7 to 24 carbon atoms, for example, phenoxycarbonyloxy 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);Alkylsulfonyl groups (preferably alkylsulfonyl groups having 1 to 48 carbon atoms, more preferably 1 to 24 carbon atoms, for example methylsulfonyl group, ethylsulfonyl group, propylsulfonyl group, butylsulfonyl group, isopropylsulfonyl group, 2-ethylhexylsulfonyl group, hexadecylsulfonyl group, octylsulfonyl group, cyclohexylsulfonyl group); arylsulfonyl groups (preferably arylsulfonyl groups having 6 to 48 carbon atoms, more preferably 6 to 24 carbon atoms, for example phenylsulfonyl group, 1-naphthylsulfonyl group); sulfamoyl groups (preferably sulfamoyl groups having 32 or fewer carbon atoms, more preferably 24 or fewer carbon atoms, for example sulfamoyl group, N,N-dipropylsulfamoyl group, N-ethyl-N-dodecylsulfamoyl group, N-ethyl-N-phenylsulfamoyl group, N-cyclohexylsulfamoyl group, N-(2-ethylhexyl)sulfamoyl group); Phosphonyl group (preferably a phosphonyl group having 1 to 32 carbon atoms, more preferably a phosphonyl group having 1 to 24 carbon atoms, for example, a phenoxyphosphonyl group, an octyloxyphosphonyl group, or a phenylphosphonyl group); phosphinoylamino group (preferably a phosphinoylamino group having 1 to 32 carbon atoms, more preferably a phosphinoylamino group having 1 to 24 carbon atoms, for example, a diethoxyphosphinoylamino group or a dioctyloxyphosphinoylamino group); epoxy group; -NHCOCH; ３ ;-SO ２ NHC ２ H ４ OCH ３ ;-NHSO ２ CH ３ Examples include ;, and two or more of these may be combined. These substituents may be further substituted by other substituents. If there are two or more substituents, they may be the same or different. Also, if possible, they may be bonded to each other to form a ring.

[0013] [Liquid Crystal Composition] The liquid crystal composition of the present invention is a liquid crystal composition containing a compound represented by formula (1) described later (hereinafter also referred to as "specific compound") and a liquid crystal compound.

[0014] As described above, in the present invention, by using a liquid crystal composition containing a specific compound, a liquid crystal cured layer can be produced that maintains excellent adhesion to adjacent layers while also exhibiting excellent light resistance. Although the details of this reason are not yet clear, the inventors speculate that it is due to the following reasons. First, it is thought that the toughness of the liquid crystal cured layer is improved because the specific compound has a thioether group (sulfide bond), thus maintaining good adhesion. Furthermore, it is thought that the fact that m in formula (1), described later, is an integer from 0 to 4 and n is an integer of 2 or more makes it difficult for nucleophiles that can promote the decomposition of liquid crystal compounds, derived from the specific compound, to be generated, thus improving light resistance. The components of the liquid crystal composition of the present invention will be described in detail below.

[0015] [Specific Compound] The specific compound contained in the liquid crystal composition of the present invention is a compound represented by the following formula (1). Note that, from the viewpoint of distinguishing it from the liquid crystal compounds described later, the specific compound is a compound that does not exhibit liquid crystal properties.

[0016] In the above formula (1), l represents an integer of 1 or more, preferably an integer between 1 and 3, more preferably 1 or 2, and even more preferably 1. Also, m represents an integer between 0 and 4, preferably an integer between 0 and 2, more preferably 0 or 1, and even more preferably 0. Also, n represents an integer of 2 or more, preferably an integer between 2 and 8, more preferably an integer between 2 and 6, and even more preferably an integer between 2 and 4.

[0017] In the present invention, it is preferable that m is 0, and more preferably that m is 0 and n is an integer between 2 and 4, because the light resistance of the resulting liquid crystal cured layer is better.

[0018] In formula (1) above, P represents a polymerizable group, and multiple Ps may be the same or different. For better adhesion between the cured liquid crystal layer and adjacent layers, the polymerizable group is preferably a radical polymerizable group or a cationic polymerizable group, with a radical polymerizable group being more preferred. Known radical polymerizable groups can be used as radical polymerizable groups, such as vinyl groups, (meth)acryloyloxy groups, and (meth)acrylamide groups. Known cationic polymerizable groups can be used as cationic polymerizable groups, such as alicyclic ether groups, cyclic acetal groups, cyclic lactone groups, cyclic thioether groups, spiroorthoester groups, and vinyloxy groups.

[0019] In the above formula (1), L １ This represents a single bond or a (n+m) valence linking group. Also, L ２ represents a (l+1) valence linking group, and multiple L ２ These may be the same or different. However, L １ and L ２ The total number of aromatic rings contained in the liquid crystal is two or less, preferably one or less, and more preferably zero. It is presumed that the toughness of the liquid crystal hardened film will improve as the total number of aromatic rings decreases. Examples of aromatic rings include aromatic hydrocarbon rings such as benzene rings, naphthalene rings, anthracene rings, and phenanthroline rings; and aromatic heterocycles such as furan rings, pyrrole rings, thiophene rings, pyridine rings, thiazole rings, and benzothiazole rings. Note that condensed rings such as naphthalene rings are counted as one, just like monocyclic rings such as benzene rings.

[0020] In the present invention, L in formula (1) above １ However, it is preferable to represent a single bond, an alkylene group which may have substituents, or a linking group represented by formula (L1-1) described later. However, the -CH that constitutes the alkylene group ２ One or more of the hyphens may be replaced by -O-, -CO-, or -NH-.

[0021] Here, L １Regarding the "alkylene group which may have substituents" in one aspect, examples of alkylene groups include alkylene groups having 1 to 20 carbon atoms, specifically linear alkylene groups such as methylene, ethylene, propylene, butylene, pentylene, hexylene, and heptylene groups; and cyclic alkylene groups such as cyclohexylene and cyclopentylene groups; among these, linear alkylene groups having 1 to 20 carbon atoms are preferred. Furthermore, examples of substituents that the alkylene group may have include the substituents listed in substituent group A above, among which alkyl groups, alkoxy groups, and hydroxyalkyl groups are preferred.

[0022] In the present invention, L １ One embodiment of the "alkylene group which may have substituents" is a linear alkylene group having 1 to 4 carbon atoms which may have substituents, or -CH ２ A C2 to C20 alkylene group in which one or more negative atoms are substituted with -O- is preferred.

[0023] X-(L) ３ -*)p (L1-1)

[0024] In the above formula (L1-1), p represents an integer from 2 to 6, preferably an integer from 3 to 6, and more preferably 3 or 4. Also, * represents the bonding position with S or SH in (1) above, that is, L in formula (1) above. １ and L ２ The -S- (sulfide bond) that exists between them, or L in formula (1) above. １ This indicates the bonding position with the -SH (thiol group) that is directly bonded to it.

[0025] In the above formula (L1-1), L ３ represents a single bond or an alkylene group which may have substituents. However, the -CH that constitutes the alkylene group ２ One or more of the -s may be replaced by -O-, -CO-, or -NH-. Multiple L ３ These may be the same or different. Here, L ３ One aspect of the "alkylene group which may have substituents" is the L in formula (1) above.１ Examples include those similar to those described as one embodiment. In particular, linear alkylene groups having 1 to 4 carbon atoms, which may have substituents, or -CH ２ A C4 to C10 alkylene group in which one or more of the negatives are substituted with -O- and -CO- (for example, an alkylene group -O-CO-alkylene group) is preferred.

[0026] In the above formula (L1-1), X is a carbon atom, (**-) ３ CR, (**-) ３ C-L ４ -C (-**) ３ , or represents a p-valent ring group. However, if X is a carbon atom, p represents 4, and X is (**-) ３ If it is CR, then p represents 3 and X is (**-) ３ C-L ４ -C (-**) ３ When representing this, p represents 6. Here, ** represents L ３ R represents the bonding position with, R represents a substituent, and L represents a substituent. ４ represents a single bond or an alkylene group which may have substituents. However, the -CH that constitutes the alkylene group ２ One or more of the -s may be substituted with -O-, -CO-, or -NH-. Furthermore, examples of substituents represented by R include those listed in substituent group A above, with alkyl groups and alkoxy groups being preferred. Also, L ４ One aspect of the "alkylene group which may have substituents" represented is the L in formula (1) above. １ Examples include those similar to those described as one embodiment. In particular, linear alkylene groups having 1 to 4 carbon atoms, which may have substituents, or -CH ２A C2-C20 alkylene group in which one or more negative atoms are substituted with -O- is preferred. Examples of p-valent ring groups include aromatic hydrocarbon rings such as benzene rings, naphthalene rings, anthracene rings, phenanthroline rings, and biphenyl structures; aromatic heterocycles such as furan rings, pyrrole rings, thiophene rings, pyridine rings, imidazole rings, thiazole rings, and benzothiazole rings; cycloalkane rings such as cyclohexane rings, cyclopeptane rings, cyclooctane rings, cyclododecane rings, and cyclodocosane rings; and nitrogen-containing heterocycles such as isocyanurate rings and glycoluryl rings.

[0027] In the present invention, L in formula (1) above is used because it improves the adhesion between the fabricated liquid crystal cured layer and the adjacent layer. １ However, an alkylene group which may have substituents, or represented by the above formula (L1-1), wherein X in the above formula (L1-1) is a carbon atom, (**-) ３ CR, or (**-) ３ C-L ４ -C (-**) ３ It is preferable to represent the linking group. However, the -CH that constitutes the alkylene group is preferable. ２ One or more of the hyphens may be replaced by -O-, -CO-, or -NH-.

[0028] In the above formula (1), L ２ It is preferable that this represents an alkylene group which may have substituents, because it results in better adhesion between the fabricated liquid crystal cured layer and the adjacent layer. However, the alkylene group may consist of -CH ２ One or more of the -s may be substituted with -O-, -CO-, or -NH-. Here, L ２ A preferred embodiment of the "alkylene group which may have substituents" is the L in formula (1) above. １ Examples similar to those described as one aspect include -CH ２ A C4 to C10 alkylene group in which one or more of the negatives are substituted with -O- and -CO- (for example, an alkylene group -O-CO-alkylene group) is preferred.

[0029] In the present invention, the molecular weight of the specific compound is preferably 200 to 2000, more preferably 300 to 1500, and even more preferably 300 to 1300, for the reason that the adhesion of the produced liquid crystal cured layer to the adjacent layer is better.

[0030] Specific examples of designated compounds include, for instance, the compounds represented by the following formulas A-1 to A-15. In the following text, the compounds represented by the following formulas A-1 to A-15 will also be abbreviated as designated compounds A-1 to A-15.

[0031] In the present invention, for the reason that the adhesion of the produced liquid crystal cured layer to adjacent layers is better, the content of the specific compound is preferably 0.1 to 10 parts by mass, more preferably more than 0.5 parts by mass and 10 parts by mass or less, and even more preferably more than 2 parts by mass and 6 parts by mass or less, based on 100 parts by mass of the liquid crystal compound described later (if multiple liquid crystal compounds are included, this refers to the total of 100 parts by mass of the multiple liquid crystal compounds; the same applies hereinafter).

[0032] [Liquid Crystal Compounds] The liquid crystal compounds contained in the liquid crystal composition of the present invention are not particularly limited. Furthermore, the type of liquid crystal compound is not particularly limited, but generally, liquid crystal compounds can be classified into rod-shaped and disc-shaped types based on their shape. Each of these further has low molecular weight and high molecular weight types. High molecular weight generally refers to compounds with a degree of polymerization of 100 or more (Polymer Physics and Phase Transition Dynamics, by Masao Doi, p. 2, Iwanami Shoten, 1992).

[0033] In this invention, any liquid crystal compound can be used, but it is preferable to use a rod-shaped liquid crystal compound or a disc-shaped liquid crystal compound (discotic liquid crystal compound). Two or more rod-shaped liquid crystal compounds, two or more disc-shaped liquid crystal compounds, or a mixture of rod-shaped and disc-shaped liquid crystal compounds may also be used.

[0034] As the rod-shaped liquid crystal compound, for example, the one described in claim 1 of Japanese Patent Publication No. 11-513019 or paragraphs

[0026] to

[0098] of Japanese Patent Application Publication No. 2005-289980 is preferred, and as the disc-shaped liquid crystal compound, for example, the one described in paragraphs

[0020] to

[0067] of Japanese Patent Application Publication No. 2007-108732 or paragraphs

[0013] to

[0108] of Japanese Patent Application Publication No. 2010-244038 is preferred.

[0035] In the present invention, the liquid crystal compound is preferably a liquid crystal compound having a polymerizable group (i.e., a polymerizable liquid crystal compound). Here, examples of polymerizable groups include those described in P in formula (1) above, and among these, radical polymerizable groups are preferred, and (meth)acryloyloxy groups are more preferred. The polymerizable liquid crystal compound is preferably at least one polymerizable liquid crystal compound selected from the group consisting of polymerizable rod-shaped liquid crystal compounds and polymerizable disc-shaped liquid crystal compounds. The orientation of the liquid crystal compound can be fixed by polymerizing the polymerizable liquid crystal compound. After the liquid crystal compound has been fixed by polymerization, it is no longer necessary for it to exhibit liquid crystal properties.

[0036] Furthermore, in the present invention, for the reason that the effects of the present invention, particularly the effect of improved light resistance, become apparent, a liquid crystal compound with reverse wavelength dispersion may be used. Hereinafter, in this specification, a liquid crystal compound with reverse wavelength dispersion refers to a liquid crystal compound in which, when the in-plane retardation (Re) value of a phase difference film made using the same is measured at a specific wavelength (visible light range), the Re value becomes equivalent or higher as the measured wavelength increases.

[0037] The inverse wavelength dispersive liquid crystal compound is not particularly limited as long as it can form an inverse wavelength dispersive film. Examples include the compound represented by general formula (I) described in Japanese Patent Application Publication No. 2008-297210 (particularly the compound described in paragraphs

[0034] to

[0039] ), the compound represented by general formula (1) described in Japanese Patent Application Publication No. 2010-084032 (particularly the compound described in paragraphs

[0067] to

[0073] ), and the compound represented by general formula (1) described in Japanese Patent Application Publication No. 2016-081035 (particularly the compound described in paragraphs

[0043] to

[0055] ). Furthermore, examples include the compounds described in paragraphs

[0027] to

[0100] of Japanese Patent Publication No. 2011-006360, paragraphs

[0028] to

[0125] of Japanese Patent Publication No. 2011-006361, paragraphs

[0034] to

[0298] of Japanese Patent Publication No. 2012-207765, paragraphs

[0016] to

[0345] of Japanese Patent Publication No. 2012-077055, paragraphs

[0017] to

[0072] of WO12 / 141245, paragraphs

[0021] to

[0088] of WO12 / 147904, and paragraphs

[0028] to

[0115] of WO14 / 147904.

[0038] In the present invention, the liquid crystal compound may be used alone or in combination of two or more types. The content of the liquid crystal compound is preferably 10 to 99% by mass, and more preferably 50 to 95% by mass, based on the total solid content (100% by mass) of the liquid crystal composition.

[0039] [Surfactants] The liquid crystal composition of the present invention preferably contains a surfactant from the viewpoint of keeping the surface of the produced liquid crystal cured layer smooth and facilitating orientation control. As such a surfactant, a fluorine-based or silicon-based surfactant is preferred because it has a high leveling effect with respect to the amount added. Specifically, as surfactants, for example, are the compounds described in paragraphs

[0079] to

[0102] of JP 2007-069471 A, the compounds represented by general formula (I) described in JP 2013-047204 A (particularly the compounds described in paragraphs

[0020] to

[0032] ), the compounds represented by general formula (I) described in JP 2012-211306 A (particularly the compounds described in paragraphs

[0022] to

[0029] ), and JP 2002-1291 A Examples include liquid crystal alignment promoters represented by general formula (I) as described in Japanese Patent Publication No. 62 (particularly the compounds described in paragraphs

[0076] to

[0078] and

[0082] to

[0084] ), 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] ), and compounds described in International Publication No. 2024 / 176900 (particularly the compound described in paragraph

[0163] ). The descriptions in these publications are incorporated herein by reference. Furthermore, surfactants may also function as alignment control agents as described later.

[0040] [Solvent] The liquid crystal composition of the present invention preferably contains a solvent. Examples of solvents include ketones [e.g., acetone, 2-butanone, methyl ethyl ketone (MEK), methyl isobutyl ketone, cyclohexanone, cyclopentanone (CPO), etc.], ethers [e.g., dioxane, tetrahydrofuran (THF), propylene glycol monomethyl ether acetate (PGMEA), etc.], aliphatic hydrocarbons [e.g., hexane, etc.], alicyclic hydrocarbons [e.g., cyclohexane, etc.], aromatic hydrocarbons [e.g., toluene, xylene, trimethylbenzene, etc.], and halogenated carbons [e.g., di Examples of solvents include chloromethane, dichloroethane, dichlorobenzene, chlorotoluene, etc., esters (e.g., methyl acetate, ethyl acetate, butyl acetate, etc.), water, alcohols (e.g., methanol (MeOH), ethanol, isopropyl alcohol (IPA), butanol, cyclohexanol, etc.), cellosolves (e.g., methyl cellosolve, ethyl cellosolve, etc.), cellosolve acetates, sulfoxides (e.g., dimethyl sulfoxide, etc.), and amides (e.g., dimethylformamide, dimethylacetamide, etc.). These solvents may be used individually or in combination of two or more.

[0041] [Polymerization Initiator] The liquid crystal composition of the present invention preferably contains a polymerization initiator. The polymerization initiator 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. Oxime-type polymerization initiators are also preferred. Specific examples include the initiators described in paragraphs

[0049] to

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

[0042] [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.

[0043] 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. As for low molecular weight orientation control agents, for example, refer to paragraphs

[0009] to

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

[0111] to

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

[0021] to

[0029] of Japanese Patent Application Publication No. 2012-211306, and this content is incorporated herein by reference. As for high molecular weight orientation control agents, for example, refer to paragraphs

[0021] to

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

[0121] to

[0167] of Japanese Patent Application Publication No. 2006-106662, and this content is incorporated herein by reference.

[0044] Furthermore, examples of orientation-controlling agents that form or promote homeotropic orientation include boronic acid compounds and onium salt compounds. Specifically, reference can be made to the 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.

[0045] [Other Components] The liquid crystal composition of the present invention may contain other components besides those described above. Examples of other components include plasticizers and crosslinking agents.

[0046] [Optical Film] The optical film of the present invention is an optical film having a liquid crystal cured layer in which the orientation state of the liquid crystal composition of the present invention described above is fixed. The optical film of the present invention may also have a plurality of (preferably two or three) liquid crystal cured layers. When the optical film has a plurality of liquid crystal cured layers, it is preferable that the plurality of liquid crystal cured layers are adjacent to each other or laminated via a known adhesive layer, and it is more preferable that the plurality of liquid crystal cured layers are adjacent to each other (directly laminated) from the viewpoint of good adhesion.

[0047] [Liquid Crystal Cured Layer] As a method for forming the liquid crystal cured layer, for example, a method in which the liquid crystal composition of the present invention described above is used to achieve a desired orientation state, and then fixed by polymerization is used. Here, the conditions for achieving the desired orientation state are not particularly limited, but it is preferable to perform a heat treatment, and it is more preferable to perform a cooling treatment after the heat treatment. The heating temperature in the heat treatment is preferably 10 to 250°C, more preferably 50 to 200°C, and even more preferably 70 to 150°C, from the viewpoint of suitability for manufacturing. The heating time in the heat treatment is preferably 1 to 300 seconds, and more preferably 1 to 60 seconds. The temperature in the cooling treatment after the heat treatment is not particularly limited as long as it is lower than the heating temperature in the heat treatment, but it is preferably room temperature (23°C) to 80°C. The conditions for polymerization are not particularly limited, but it is preferable to use ultraviolet light in polymerization by light irradiation. 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 ２ More preferably, 50 to 1000 mJ / cm ２ This is particularly preferable. Furthermore, the polymerization reaction may be carried out under heating conditions to accelerate it.

[0048] The orientation state of the liquid crystal compound in the liquid crystal cured layer may be any of the following: horizontal orientation, vertical orientation, tilted orientation, or torsional orientation.

[0049] In the present invention, the liquid crystal curing layer is preferably an optically anisotropic layer, more preferably a positive A plate or a positive C plate, and even more preferably a positive A plate.

[0050] Here, a positive A plate and a positive C plate are defined as follows: When the refractive index in the slow axis direction within the film plane (the direction in which the refractive index is maximum within the plane) is nx, the refractive index in the direction perpendicular to the slow axis within the plane is ny, and the refractive index in the thickness direction is nz, a positive A plate satisfies the relationship in equation (A1), and a positive C plate satisfies the relationship in equation (C1). Note that a positive A plate has a positive Rth value, and a positive C plate has a negative Rth value. Equation (A1) nx > ny ≈ nz Equation (C1) nz > nx ≈ ny Note that the above "≈" includes not only cases where the two are completely identical, but also cases where the two are substantially identical. Regarding this "substantially identical" condition, for positive A plates, for example, cases where (ny - nz) × d (where d is the film thickness) is -10 to 10 nm, preferably -5 to 5 nm, are included in "ny ≈ nz", and cases where (nx - nz) × d is -10 to 10 nm, preferably -5 to 5 nm, are also included in "nx ≈ nz". Furthermore, for positive C plates, for example, cases where (nx - ny) × d (where d is the film thickness) is 0 to 10 nm, preferably 0 to 5 nm, are also included in "nx ≈ ny".

[0051] The thickness of the liquid crystal curing layer is not particularly limited, but is preferably 0.1 to 10 μm, and more preferably 0.5 to 5 μm.

[0052] [Substrate] The optical film of the present invention may have a substrate for supporting the liquid crystal curing layer. Such a substrate is preferably transparent. In this invention, "transparent" means that the transmittance of visible light is 60% or more, preferably 80% or more, and more preferably 90% or more.

[0053] Examples of the above-mentioned substrates 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; and polymers obtained by mixing these polymers.

[0054] The thickness of the above-mentioned substrate is not particularly limited, but is preferably 1 to 200 μm, and more preferably 2 to 100 μm. Furthermore, the above-mentioned substrate may be a liquid crystal curing layer other than the liquid crystal curing layer described above (especially an optically anisotropic layer).

[0055] [Alignment layer] The liquid crystal cured layer and any other liquid crystal cured layer in the optical film of the present invention may be formed on the surface of an alignment layer (in particular, a photo-alignment layer described later).

[0056] The alignment film can be any film that has the function of aligning the liquid crystal compounds contained in the composition. The alignment film is generally composed mainly of a polymer. Numerous polymer materials for alignment films are described in various publications, and many commercially available products are available. As polymer materials for alignment films, polyvinyl alcohol, polyimide, or derivatives thereof are preferred, and modified or unmodified polyvinyl alcohol is more preferred. Examples of alignment films that an optical film may have include the alignment film described on pages 43, line 24 to 49, line 8 of International Publication No. 01 / 88574; the alignment film made of modified polyvinyl alcohol described in paragraphs

[0071] to

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

[0057] It is preferable to use a photo-alignment film as the alignment film because it prevents deterioration of the surface by preventing objects from coming into contact with the surface of the alignment film during its formation. The photo-alignment film is not particularly limited, but it can be an alignment film formed from polymer materials such as polyamide compounds and polyimide compounds as described in paragraphs

[0024] to

[0043] of International Publication No. 2005 / 096041; a liquid crystal alignment film formed from a liquid crystal alignment agent having photo-aligning groups as described in Japanese Patent Application Publication No. 2012-155308; or a product such as LPP-JP265CP from Rolic Technologies.

[0058] The thickness of the orientation film is not particularly limited, but is preferably 0.01 to 10 μm, more preferably 0.01 to 1 μm, and even more preferably 0.01 to 0.5 μm.

[0059] [Polarizing plate] The optical film of the present invention described above can also be used as a polarizing plate in combination with a polarizer.

[0060] [Polarizer] The polarizer in a polarizing plate is not particularly limited as long as it is a material that has the function of converting light into a specific linear polarization, and conventionally known absorptive polarizers and reflective polarizers can be used. Absorbent polarizers include iodine-based polarizers, dye-based polarizers using dichroic dyes, and polyene-based polarizers. Iodine-based polarizers and dye-based polarizers include coated polarizers and stretched polarizers, both of which can be applied, but polarizers made by adsorbing iodine or a dichroic dye onto polyvinyl alcohol and stretching it are preferred. Reflective polarizers include polarizers made by laminating thin films with different birefringences, wire grid type polarizers, and polarizers combining a cholesteric liquid crystal with a selective reflection range and a quarter-wave plate. The thickness of the polarizer is not particularly limited, but is preferably 5 to 40 μm, more preferably 5 to 30 μm, and even more preferably 5 to 20 μm.

[0061] [Method for Manufacturing Polarizing Plates] The method for manufacturing polarizing plates is not particularly limited, and known methods can be used. For example, a polarizing plate can be manufactured by preparing a polarizer and an optical film separately, and then bonding them together in a predetermined direction via an adhesive layer. The adhesive layer used to bond the polarizer and the optical film is not particularly limited, and known adhesive layers and tack layers can be used.

[0062] [Display Device] The image display device of the present invention is a display device having the optical film described above.

[0063] [Display Element] The display element used in the display device of the present invention is not particularly limited, and examples include liquid crystal cells, organic electroluminescent (hereinafter abbreviated as "EL") display panels, and plasma display panels. Of these, liquid crystal cells or organic EL display panels are preferred. That is, the display device of the present invention is preferably a liquid crystal display device using a liquid crystal cell as the display element, or an organic EL display device using an organic EL display panel as the display element.

[0064] <Liquid Crystal Cells> Liquid crystal cells used in liquid crystal display devices are preferably in VA (Vertical Alignment) mode, OCB (Optical Compensated Bend) mode, FFS or IPS (In-Plane-Switching) mode, or TN (Twisted Nematic) mode, but are not limited to these.

[0065] <Organic EL Display Panel> The organic EL display panel used as an image display element in the present invention is a display panel constructed using an organic EL element in which an organic light-emitting layer (organic electroluminescent layer) is sandwiched between electrodes (between the cathode and the anode). The configuration of the organic EL display panel is not particularly limited, and known configurations can be adopted.

[0066] [Compound] The compound of the present invention is a compound represented by the above formula (1) (i.e., the specified compound described above), and the preferred embodiment thereof is the same.

[0067] The present invention will be described in more detail below based on 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 examples shown below.

[0068] [Synthesis Example 1] [Synthesis of Specific Compound A-1] Specific compound A-1 was synthesized according to the scheme shown below.

[0069] Specifically, 10 ml of dimethylacetamide (DMAc), 4.0 g of 4-hydroxyethyl acrylate, and 3.0 g of pentaerythritol tetrakis (mercaptoacetate) were placed in a 100 mL three-necked flask equipped with a calcium chloride tube, thermometer, dropping funnel, and stirrer, and the mixture was cooled on ice. Then, 48.1 μL of triethylamine (TEA) was added, and the mixture was heated to room temperature and stirred for 1 hour. After cooling on ice again, 3.0 g of acrylate chloride was added, and the mixture was heated to room temperature and stirred for 1 hour. The resulting solution was transferred to a separatory funnel, 50 mL of ethyl acetate was added, and after separation with saturated sodium bicarbonate aqueous solution, the mixture was washed with saturated brine and the organic layer was removed. Magnesium sulfate was added to the organic layer and dried, and the solvent was removed by distillation. The obtained crude product was purified by silica gel column chromatography to obtain 7.2 g of the target compound A-1 (molecular weight: 1225). １ The results of the H-NMR (Nuclear Magnetic Resonance) analysis are shown below. １ H-NMR (CDCl ３ ): δ = 1.75 (s, 16H), 2.65 (t, 8H), 2.89 (t, 8H), 3.28 (s, 8H), 4.14-4.22 (m, 24H), 5.84 (d, 4H), 6.13 (dd, 4H), 6.39 (d, 4H)

[0070] [Synthesis Example 2] [Synthesis of Specific Compound A-8] Specific compound A-8 was synthesized according to the scheme shown below.

[0071] Specifically, 10 mL of dimethylacetamide (DMAc) and 2.5 g of 4,4'-dithiodiphenol were placed in a 100 mL three-neck flask equipped with a calcium chloride tube, a thermometer, a dropping funnel and a stirrer, and cooled with ice. Thereafter, 2.3 g of acrylic acid chloride was added, and the mixture was warmed to room temperature and stirred for 1 hour. The resulting solution was transferred to a separatory funnel, 50 mL of ethyl acetate was added, after liquid separation with a saturated aqueous sodium hydrogen carbonate solution, the organic layer was taken out and washed with saturated brine. Magnesium sulfate was added to the organic layer for drying, and then the solvent was distilled off. The obtained crude product was purified by silica gel column chromatography to obtain 3.2 g of the target specific compound A-8 (molecular weight: 358). Of the obtained specific compound A-8 １ The results of ¹H-NMR analysis are shown below. １ ¹H-NMR (CDCl ３ ₃): δ = 5.90 (d, 2H), 6.16 (dd, 2H), 6.46 (d, 2H), 7.08 (d, 4H), 7.47 (d, 4H)

[0072] [Other Synthesis Examples] Specific compounds A-2 to A-6 used in Examples 4 to 8 described below were synthesized according to the method described in Synthesis Example 1 above.

[0073] [Example 1] [Formation of Positive C Plate (1A)] A composition for forming a vertically aligned liquid crystal layer (1A) containing a rod-like liquid crystal compound having the following composition was coated on a cellulose acylate film (TG40 manufactured by FUJIFILM Corporation, thickness 40 µm) using a wire bar coater to form a composition layer. Next, the film on which the composition layer was formed was heated with warm air at 60°C for 1 minute, and while purging with nitrogen to obtain an atmosphere with an oxygen concentration of 100 volume ppm or less, irradiation was performed using a 365 nm UV (ultraviolet)-LED (light-emitting diode) at an irradiation dose of 100 mJ / cm ２The film was irradiated with ultraviolet light. Subsequently, the resulting coating was annealed with hot air at 130°C for 1 minute to form a 40.7 μm thick positive C plate (1A) on a cellulose acylate film, with a 0.7 μm thick vertically oriented liquid crystal layer (1A) formed on the film. The in-plane retardation Re of the positive C plate (1A) at a wavelength of 550 nm was 0 nm, and the retardation Rth in the thickness direction at a wavelength of 550 nm was -85 nm. The average inclination angle of the rod-shaped liquid crystal compound in the direction of the long axis with respect to the film surface was 90°, confirming that it was oriented perpendicular to the film surface.

[0074] -------------------------------------------------- Composition for forming a vertically aligned liquid crystal layer (1A) -------------------------------------------------- ・The following rod-shaped liquid crystal compound (A) 100 parts by mass ・Polymerizable monomer (A-400, manufactured by Shin Nakamura Chemical Industry Co., Ltd.) 4.2 parts by mass ・The following polymerization initiator S-1 (oxime type) 5.1 parts by mass ・The following photoacid generator D-1 3.0 parts by mass ・The following polymer M-1 4.0 parts by mass ・The following orientation control agent C-1 1.9 parts by mass ・The following photo-oriented polymer PA-1 0.8 parts by mass ・Diisopropylethylamine 0.2 parts by mass ・Methyl ethyl ketone 93.8 parts by mass ・Methyl isobutyl ketone 372.0 parts by mass --------------------------------------------------

[0075] Rod-shaped liquid crystal compound (A) [A mixture of the following liquid crystal compounds (RA): (RB): (RC) = 84:14:2 (mass ratio)]

[0076] Polymerization initiator S-1

[0077] Photoacid Generator D-1

[0078] Polymer M-1 [Weight-average molecular weight: 52,000; the numerical value indicated within each repeating unit represents the content (mass%) of that repeating unit relative to the total number of repeating units.]

[0079] Orientation control agent C-1

[0080] Photo-oriented polymer PA-1 [The numerical values ​​indicated within each repeating unit represent the content (mass%) of each repeating unit relative to the total number of repeating units. Weight-average molecular weight: 90,000. Me represents a methyl group.]

[0081] [Formation of Positive A Plate (1B)] On the vertically aligned liquid crystal layer (1A) side of the elongated positive C plate (1A), UV light (ultra-high pressure mercury lamp: UL750, manufactured by HOYA) passed through a wire grid polarizer is applied at 7.9 mJ / cm². ２ By irradiating with ultraviolet light (wavelength: 313 nm), a composition layer with orientation control capability was formed on the surface. Next, liquid crystal composition X-1 [composition for forming a horizontally aligned liquid crystal layer (1B)] containing a rod-shaped liquid crystal compound of the following composition was applied onto the vertically aligned liquid crystal layer (1A) using a Gieser coating machine, and after being heated to 120°C with hot air, it was cooled to 60°C to stabilize the orientation. After that, the first ultraviolet irradiation (80 mJ / cm²) was performed under a nitrogen atmosphere (oxygen concentration less than 100 ppm) using an ultra-high pressure mercury lamp while maintaining the film temperature at 60°C. ２ After the first irradiation, the film temperature was kept at 100°C and a second UV irradiation (300 mJ / cm²) was performed. ２ The orientation was fixed by ) and a positive A plate (1B) was formed. The thickness of the positive A plate (1B) was 2.8 μm, and the Re(550) at a wavelength of 550 nm was 141 nm. When the width direction of the film was 0° (longitudinal direction was 90°), the in-plane slow phase axis direction (orientation axis angle of the liquid crystal compound) was 45°.

[0082] ------------------------------------------------------------------- Liquid Crystal Composition X-1 [Composition for Forming Horizontally Aligned Liquid Crystal Layer (1B)] ------------------------------------------------------------------- ・The following rod-shaped liquid crystal compound (B) 21.2 parts by mass ・The following rod-shaped liquid crystal compound (C) 26.1 parts by mass ・The following rod-shaped liquid crystal compound (D) 29.0 parts by mass ・The following rod-shaped liquid crystal compound (E) 8.5 parts by mass ・The following rod-shaped liquid crystal compound (F) 15.3 parts by mass ・The above polymerization initiator S-1 (oxime type) 0.5 parts by mass ・The following leveling agent L-1 0.1 parts by mass ・Boron acid compound T-1 0.9 parts by mass ・Specific compound A-1 4.0 parts by mass ・Cyclopentanone 175.0 parts by mass ・Methyl ethyl ketone 50.0 parts by mass ・Ethyl laurate 10.0 parts by mass ------------------------------------------------------------------

[0083] Rod-shaped liquid crystal compound (B)

[0084] Rod-shaped liquid crystal compound (C)

[0085] Rod-shaped liquid crystal compound (D)

[0086] Rod-shaped liquid crystal compound (E)

[0087] Rod-shaped liquid crystal compound (F)

[0088] Leveling agent L-1 [Weight-average molecular weight: 28,500; the numerical value indicated within each repeating unit represents the content (mass %) of that repeating unit relative to the total number of repeating units.]

[0089] Boronic acid compound T-1

[0090] [Preparation of optical film (1)] Following the procedure described above, a long optical film (1) with a thickness of 43.5 μm was prepared by directly laminating a positive C plate (1A) and a positive A plate (1B).

[0091] [Preparation of Polyvinyl Alcohol (PVA) Adhesive] A PVA adhesive was prepared by dissolving 100 parts by mass of a PVA resin having an acetoacetyl group (average degree of polymerization: 1200, degree of saponification: 98.5 mol%, degree of acetoacetylation: 5 mol%) and 20 parts by mass of methylolmelamine in pure water at a temperature of 30°C, and adjusting the solid content concentration to 3.7% by mass as an aqueous solution.

[0092] [Preparation of the adhesive layer] An adhesive layer (acrylic adhesive) with a thickness of 20 μm was formed on the separator film by the same method as described in Example 1 of Japanese Patent Publication No. 2023-126297.

[0093] [Preparation of polarizer (P1)] The surface of a cellulose triacetate film TJ25 (manufactured by Fujifilm Corporation: 25 μm thick) support was subjected to alkaline saponification treatment. Specifically, the support was immersed in a 1.5 N sodium hydroxide aqueous solution at 55°C for 2 minutes, then washed in a water bath at room temperature, and further neutralized with 0.1 N sulfuric acid at 30°C. After neutralization, the support was washed in a water bath at room temperature and further dried with hot air at 100°C to obtain a polarizer protective film (1). A roll-shaped polyvinyl alcohol (PVA) film with a thickness of 60 μm was continuously stretched in the longitudinal direction in an iodine aqueous solution and dried to obtain a polarizer (1) with a thickness of 13 μm. The luminous efficiency corrected single transmittance of polarizer (1) was 43%. At this time, the absorption axis direction and the longitudinal direction of polarizer (1) coincided. The positive A plate (1B) surface of the long optical film (1) prepared above was bonded to one side of the polarizer (1) using the PVA-based adhesive, and the polarizer protective film (1) was bonded to the other side of the polarizer (1). Then, a laminate film made of a 50 μm thick weak adhesive PET (polyethylene terephthalate) film was bonded to the polarizer protective film (1) side. After that, the adhesive layer formed on the separator film was bonded to the optical film (1) side. An adhesive-coated polarizer plate (P1) was prepared by the above procedure. At this time, the laminate film, polarizer protective film (1), PVA-based adhesive, polarizer (1), PVA-based adhesive, positive A plate (1B), positive C plate (1A) (vertically aligned liquid crystal layer (1A), cellulose acylate film (1)), adhesive, and separator film were laminated in this order, and the angle between the absorption axis of the polarizer (1) and the in-plane slow axis of the positive A plate (1B) was 45°.

[0094] [Examples 2-9] Optical films and polarizing plates were prepared in the same manner as in Example 1, except that the specific compound A-1 and its content, which were incorporated in liquid crystal composition X-1 [Composition for forming a horizontally aligned liquid crystal layer (1B)], were changed to the compounds and their contents listed in the "Specific Compounds, etc." column of Table 1 below.

[0095] [Example 10] An optical film and a polarizing plate were prepared in the same manner as in Example 1, except that the liquid crystal composition X-10 shown below was used instead of liquid crystal composition X-1 [composition for forming a horizontally aligned liquid crystal layer (1B)]. -------------------------------------------------- Liquid crystal composition X-10 [Composition for forming a horizontally aligned liquid crystal layer (10B)] -------------------------------------------------- ・83 parts by mass of the liquid crystal compound (B1) below ・3 parts by mass of the liquid crystal compound (B2) below ・14 parts by mass of the liquid crystal compound (B3) below ・3 parts by mass of the polymerization initiator S-1 above ・4 parts by mass of the A-1 compound above ・0.1 parts by mass of the leveling agent L-1 above ・0.9 parts by mass of the boronic acid compound T-1 above ・175.0 parts by mass of cyclopentanone ・50.0 parts by mass of methyl ethyl ketone ・10.0 parts by mass of ethyl laurate -------------------------------------------------- The liquid crystal compounds (B1) to (B3) below can be synthesized by the method described in Japanese Patent Application Publication No. 2021-081651.

[0096] Liquid crystal compound (B1)

[0097] Liquid crystal compounds (B2)

[0098] Liquid crystal compounds (B3)

[0099] [Example 11] An optical film and a polarizing plate were prepared in the same manner as in Example 1, except that the liquid crystal composition X-11 shown below was used instead of liquid crystal composition X-1 [composition for forming a horizontally aligned liquid crystal layer (1B)]. -------------------------------------------------- Liquid crystal composition X-11 [Composition for forming a horizontally aligned liquid crystal layer (11B)] -------------------------------------------------- ・100 parts by mass of the liquid crystal compound (B4) below ・3 parts by mass of the polymerization initiator S-1 above ・4 parts by mass of the A-1 compound above ・0.1 parts by mass of the leveling agent L-1 above ・0.9 parts by mass of the boronic acid compound T-1 above ・95.0 parts by mass of toluene ・142.6 parts by mass of cyclopentanone -------------------------------------------------- The liquid crystal compound (B4) below can be synthesized by the method described in Japanese Patent Application Publication No. 2021-081651.

[0100] Liquid crystal compound (B4)

[0101] [Comparative Examples 1-3] Optical films and polarizing plates were prepared in the same manner as in Example 1, except that a liquid crystal composition was used in which specific compound A-1, which was incorporated in liquid crystal composition X-1 [Composition for forming a horizontally aligned liquid crystal layer (1B)], was replaced with a compound listed in the "Specific Compounds, etc." column of Table 1 below.

[0102] [Evaluation] (1) Adhesion Evaluation Each polarizing plate with adhesive layer prepared in the examples and comparative examples was cut into strips of 30 mm x 120 mm, and the separator film on the adhesive layer side was peeled off. After the exposed adhesive layer was bonded to glass, the laminate film on the opposite side was peeled off. Eleven cuts were made at 1 mm intervals from the surface of the polarizing plate to a depth that reached the adhesive bonded to the glass, and then eleven more cuts were made in the same manner in a perpendicular direction to form 100 squares. Adhesive tape (polyester adhesive tape No. 31B, manufactured by Nitto Denko Corporation) was applied to the squares, and the tape was peeled off at an angle of approximately 60°. The number of peeled squares was counted, and the results were evaluated according to the following criteria. The results are shown in Table 1 below. <Evaluation Criteria> A: Number of peeled-off squares is 20 or less B: Number of peeled-off squares is 21 to 40 C: Number of peeled-off squares is 41 to 50 D: Number of peeled-off squares is 51 or more

[0103] (2) Evaluation of lightfastness The glass substrates of the optical films prepared in the examples and comparative examples were set in a xenon irradiation machine (SX75 manufactured by Suga Test Instruments Co., Ltd.) so that the cured film on the positive A plate of each optical film was the irradiation surface, and light was irradiated for 200 hours in an environment of 60°C and 50% relative humidity. The residual retardation (residual Re) of the cured film after the lightfastness test was measured, and the lightfastness retention rate Y (%) was calculated from the initial Re (550 nm) before the test and the residual Re using the following formula, and the lightfastness was evaluated according to the following criteria. The results are shown in Table 1 below. Lightfastness retention rate (%) = (residual Re / initial Re) × 100 <Evaluation criteria> A: Lightfastness retention rate of 90% or more B: Lightfastness retention rate of 55% or more and less than 90% C: Lightfastness retention rate of less than 55%

[0104]

[0105] The structures of the specific compounds in Table 1 are shown below.

[0106] Specific compound A-1

[0107] Specific compound A-2

[0108] Specific compound A-3

[0109] Specific compound A-4

[0110] Specific compound A-5

[0111] Specific compound A-6

[0112] Specific compound A-8

[0113] Karens PE-1

[0114] PETA

[0115] B-1

[0116] As shown in Table 1, when a compound having a thiol group but no polymerizable group was incorporated, the light resistance of the resulting liquid crystal cured layer was found to be poor (Comparative Example 1). Furthermore, when a compound having a polymerizable group but no sulfide bond (thioether group) was incorporated, the adhesion between the resulting liquid crystal cured layer and the adjacent layer was found to be poor (Comparative Example 2). Also, L in formula (1) above １ and L ２ It was found that when a compound containing three or more aromatic rings was incorporated, the adhesion between the resulting liquid crystal cured layer and the adjacent layer was poor (Comparative Example 3).

[0117] In contrast, it was found that when a liquid crystal composition containing the specific compound represented by the above formula (1) is used, a cured liquid crystal layer having excellent adhesion to an adjacent layer and good light resistance can be produced (Examples 1 to 11). In particular, from the comparison of Examples 1 to 3, when the content of the specific compound is more than 0.5 parts by mass and 10 parts by mass or less based on 100 parts by mass of the liquid crystal compound, the adhesion to the adjacent layer becomes better, and it was found that when the content is more than 2 parts by mass and 6 parts by mass or less, the adhesion to the adjacent layer is further improved. Further, from the comparison between Example 1 and Example 4, it was found that when the molecular weight of the specific compound is 300 to 1500, the adhesion of the produced cured liquid crystal layer to the adjacent layer becomes better. Further, from the comparison between Example 1 and Example 6, it was found that when m in the above formula (1) is 0, the adhesion of the produced cured liquid crystal layer to the adjacent layer becomes better. Further, from the comparison between Example 1 and Example 9, L in the above formula (1) ２ is an alkylene group which may have a substituent (provided that one or more of -CH ２ - constituting the alkylene group may be substituted with -O-, -CO- or -NH-.), it was found that the adhesion of the produced cured liquid crystal layer to the adjacent layer becomes better.

Claims

1. A liquid crystal composition containing a compound represented by the following formula (1) and a liquid crystal compound. Here, in formula (1) above, l represents an integer of 1 or more. m represents an integer from 0 to 4. n represents an integer of 2 or more. P represents a polymerizable group, and multiple Ps may be the same or different. １ L represents a single bond or a (n+m) valence linking group. ２ represents a (l+1) valence linking group, and multiple L ２ These may be the same or different. However, L １ and L ２ The total number of aromatic rings contained in it is two or less.

2. The liquid crystal composition according to claim 1, wherein P in formula (1) is a radical polymerizable group or a cationic polymerizable group.

3. The liquid crystal composition according to claim 1, wherein P in formula (1) is a radical polymerizable group.

4. The liquid crystal composition according to claim 1, wherein m in formula (1) is 0.

5. The liquid crystal composition according to claim 4, wherein n in formula (1) is an integer from 2 to 4.

6. L in the above formula (1) １ represents a single bond, an optionally substituted alkylene group, or a linking group represented by the following formula (L1-1), the liquid crystal composition according to claim 1, provided that one or more -CH ２ - constituting the alkylene group may be substituted with -O-, -CO- or -NH-. X-(L ３ -*)p (L1-1) wherein, in the above formula (L1-1), p represents an integer of 2 to 6. * represents a bonding position to S or SH in the above formula (1). L ３ represents a single bond or an optionally substituted alkylene group, provided that one or more -CH ２ - constituting the alkylene group may be substituted with -O-, -CO- or -NH-. A plurality of L ３ may each be the same or different. X represents a carbon atom, (**-) ３ CR, (**-) ３ C-L ４ -C(-**) ３ , or a p-valent cyclic group, provided that when X is a carbon atom, p represents 4; when X is (**-) ３ CR, p represents 3; when X represents (**-) ３ C-L ４ -C(-**) ３ , p represents 6. ** represents a bonding position to L ３ , R represents a substituent, L ４ represents a single bond or an optionally substituted alkylene group, provided that one or more -CH ２ - constituting the alkylene group may be substituted with -O-, -CO- or -NH-.

7. L in formula (1) above １ However, the alkylene group is represented by the formula (L1-1), and X in the formula (L1-1) is a carbon atom, (**-) ３ CR, or (**-) ３ C-L ４ -C (-**) ３ The liquid crystal composition according to claim 6, which represents a linking group.

8. L in formula (1) above ２ The liquid crystal composition according to claim 1, wherein the alkylene group may have substituents. ２ One or more of the hyphens may be replaced by -O-, -CO-, or -NH-.

9. The liquid crystal composition according to claim 1, wherein the molecular weight of the compound represented by formula (1) is 300 to 1500.

10. The liquid crystal composition according to claim 1, wherein the content of the compound represented by formula (1) is 0.1 to 10 parts by mass per 100 parts by mass of the liquid crystal compound.

11. An optical film having a liquid crystal cured layer in which the orientation state of the liquid crystal composition according to any one of claims 1 to 10 is fixed.

12. A display device having the optical film described in claim 11.

13. A compound represented by the following formula (1). Here, in formula (1) above, l represents an integer of 1 or more. m represents an integer from 0 to 4. n represents an integer of 2 or more. P represents a polymerizable group, and multiple Ps may be the same or different. １ L represents a single bond or a (n+m) valence linking group. ２ represents a (l+1) valence linking group, and multiple L ２ These may be the same or different. However, L １ and L ２ The total number of aromatic rings contained in it is two or less.

14. The compound according to claim 13, wherein m in formula (1) is 0.

15. The compound according to claim 14, wherein n in formula (1) is 2 to 4.

16. L in formula (1) above １ The compound according to claim 13, wherein the alkylene group may have a single bond, a substituent, or a linking group represented by the following formula (L1-1). ２ One or more of the hyphens may be substituted with -O-, -CO-, or -NH-. X-(L ３ -*)p (L1-1) Here, in the above formula (L1-1), p represents an integer from 2 to 6. * represents the bonding position with S or SH in the above formula (1). L ３ represents a single bond or an alkylene group which may have substituents. However, the -CH constituting the alkylene group is not ２ One or more of the -s may be replaced by -O-, -CO-, or -NH-. Multiple L ３ These may be the same or different. X is a carbon atom, (**-) ３ CR, (**-) ３ C-L ４ -C (-**) ３ , or represents a p-valent ring group. However, if X is a carbon atom, p represents 4, and X is (**-) ３ If it is CR, then p represents 3, and X(**-) ３ C-L ４ -C (-**) ３ When representing this, p represents 6. ** represents L ３ R represents the bonding position with, R represents a substituent, and L represents a substituent. ４ represents a single bond or an alkylene group which may have substituents. However, the -CH constituting the alkylene group is not ２ One or more of the hyphens may be replaced by -O-, -CO-, or -NH-.

17. L in equation (1) above １ However, the alkylene group is represented by the formula (L1-1), and X in the formula (L1-1) is a carbon atom, (**-) ３ CR, or (**-) ３ C-L ４ -C (-**) ３ The compound according to claim 16, which represents a linking group.

18. L in equation (1) above ２ The compound according to claim 13, wherein the alkylene group may have substituents. ２ One or more of the hyphens may be replaced by -O-, -CO-, or -NH-.

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