Liquid crystal composition, liquid crystal compound, light absorption anisotropic film, laminate, and display device

Abstract

The present invention addresses the problem of providing a liquid crystal composition capable of producing a light absorption anisotropic film in which a reduction in orientation due to curing is suppressed; a liquid crystal compound; a light absorption anisotropic film; a laminate; and a display device. This liquid crystal composition contains a dichroic substance and a liquid crystal compound having a polymerizable group. The polymerizable group is a ring-opening polymerizable group.

Description

Liquid crystal composition, liquid crystal compound, optically absorptive anisotropic film, laminate and display device

[0001] The present invention relates to a liquid crystal composition, a liquid crystal compound, an optically absorptive anisotropic film, a laminate, and a display device.

[0002] Conventionally, when light attenuation, polarization, scattering, or light blocking functions for irradiated light, including laser light or natural light, were required, devices operating on different principles for each function were used. Therefore, products corresponding to the above functions were also manufactured using different manufacturing processes for each function. For example, in liquid crystal displays (LCDs), linear polarizers and circular polarizers are used to control the optical rotation and birefringence of the display. Also, in organic light-emitting diodes (OLEDs), circular polarizers are used to prevent reflection of external light.

[0003] Conventionally, iodine has been widely used as a dichroic material in these polarizing plates (polarizing elements), but polarizing elements that use an organic dye as a dichroic material instead of iodine have also been studied. For example, Patent Document 1 describes a polarizing film that includes "a polymer formed from a polymerizable liquid crystal compound, and, when dispersed in the polymer and the light absorption is measured, at least one dichroic dye (1) having an absorption maximum in a wavelength range of 380 to 550 nm and at least two dichroic dyes (2) having an absorption maximum in a wavelength range of 550 to 700 nm" ([Claim 1]).

[0004] JP 2013-210624 A

[0005] The present inventors have studied the polarizing film (optically absorptive anisotropic film) described in Patent Document 1 and have found that, depending on the type of polymerizable liquid crystal compound, the degree of orientation decreases upon polymerization (curing).

[0006] Therefore, an object of the present invention is to provide a liquid crystal composition, a liquid crystal compound, an optically absorptive anisotropic film, a laminate, and a display device that can be used to prepare an optically absorptive anisotropic film in which the decrease in the degree of orientation due to curing is suppressed.

[0007] As a result of intensive research into the above-mentioned problems, the present inventors have found that an optically absorptive anisotropic film in which the decrease in the degree of orientation due to curing is suppressed can be produced by using a liquid crystal composition containing a dichroic substance and a liquid crystal compound having a ring-opening polymerizable group, and have completed the present invention. That is, the present inventors have found that the above-mentioned problems can be solved by the following configuration.

[0008] [1] A liquid crystal composition comprising a liquid crystal compound having a polymerizable group and a dichroic substance, wherein the polymerizable group is a ring-opening polymerizable group. [2] The liquid crystal composition according to [1], wherein the ring-opening polymerizable group is a radical ring-opening polymerizable group. [3] The liquid crystal composition according to [2], wherein the radical ring-opening polymerizable group is a group represented by formula (1) described later. [4] The liquid crystal composition according to [3], wherein the group represented by formula (1) described later is a group represented by any one of formulas (CP-1) to (CP-3) described later. [5] The liquid crystal composition according to any one of [1] to [4], wherein the liquid crystal compound is a compound represented by formula (2) described later or a polymer thereof. [6] The liquid crystal composition according to [5], wherein the compound represented by formula (2) described later exhibits nematic liquid crystallinity. [7] A liquid crystal compound which is a compound represented by formula (2) described later or a polymer thereof. [8] An optically absorptive anisotropic film obtained by fixing the alignment state of the liquid crystal composition according to any one of [1] to [6]. [9] A laminate comprising the optically absorptive anisotropic film according to [8] and a λ / 4 plate.

[10] A display device comprising the optically absorptive anisotropic film according to [8] and a display element.

[0009] As will be described below, the present invention can provide a liquid crystal composition, a liquid crystal compound, an optically absorptive anisotropic film, a laminate, and a display device that can produce an optically absorptive anisotropic film in which the decrease in the degree of orientation due to curing is suppressed.

[0010] The present invention will be described in detail below. The following description of the constituent elements may be based on a representative embodiment of the present invention, but the present invention is not limited to such an embodiment. In this specification, a numerical range expressed using "to" means a range that includes the numerical values ​​before and after "to" as the upper and lower limits. In this specification, the upper or lower limit of a numerical range described in a stepwise manner may be replaced with the upper or lower limit of another stepwise manner. In this specification, the upper or lower limit of a numerical range described in a stepwise manner may be replaced with a value shown in the Examples. In this specification, each component may be a single substance corresponding to the component, or two or more substances may be used in combination. When two or more substances are used in combination for each component, the content of that component refers to the total content of the substances used in combination, unless otherwise specified. Furthermore, in this specification, "(meth)acrylate" is a notation representing "acrylate" or "methacrylate", "(meth)acrylic" is a notation representing "acrylic" or "methacrylic", "(meth)acryloyl" is a notation representing "acryloyl" or "methacryloyl", and "(meth)acrylic acid" is a notation representing "acrylic acid" or "methacrylic acid".

[0011] In this specification, examples of the substituent (monovalent substituent) include the substituents described below in Substituent Group A. In this specification, the phrase "optionally having a substituent" includes not only an embodiment in which no substituent is present, but also an embodiment in which one or more substituents are present. <Substituent Group A> Examples of the substituent include halogen atoms (for example, fluorine atoms, chlorine atoms, and bromine atoms, preferably chlorine atoms and fluorine atoms, and more preferably fluorine atoms); alkyl groups (preferably alkyl groups having 1 to 48 carbon atoms, more preferably 1 to 24 carbon atoms, and particularly preferably 1 to 8 carbon atoms, such as linear alkyl groups having 1 to 6 carbon atoms (for example, methyl groups, ethyl groups, n-propyl groups, n-butyl groups, n-pentyl groups, and n-hexyl groups), branched alkyl groups having 3 to 6 carbon atoms (for example, isopropyl groups, isobutyl groups, tert-butyl groups, sec-butyl groups, neopentyl groups, isohexyl groups, and 3-methylpentyl groups), and cyclic alkyl groups having 3 to 12 carbon atoms (for example, cyclopropyl groups, cyclopentyl groups, cyclohexyl groups, 1-norbornyl groups, and 1-adamantyl groups)); alkenyl groups (preferably alkenyl groups having 2 to 48 carbon atoms, more preferably 2 to 18 carbon atoms, such as vinyl groups, allyl groups, 1-butenyl groups, and 2-butenyl groups); alkynyl groups (preferably alkynyl groups having 2 to 6 carbon atoms, more preferably 2 to 4 carbon atoms, such as ethynyl groups, 1-propynyl groups, propargyl groups, 1-butynyl groups, and 2-butynyl groups); aryl groups (preferably aryl groups having 6 to 48 carbon atoms, more preferably 6 to 24 carbon atoms, such as phenyl groups, oligoaryl groups (naphthyl groups, anthryl groups), phenanthrenyl groups, fluorenyl groups, pyrenyl groups, triphenylenyl groups, and biphenyl groups); Heteroaryl groups (preferably heterocyclic groups having 1 to 32 carbon atoms, more preferably 1 to 18 carbon atoms, such as a 2-thienyl group, a 4-pyridyl group, a 2-furyl group, a 2-pyrimidinyl group, a 1-pyridyl group, a 2-benzothiazolyl group, a 1-imidazolyl group, a 1-pyrazolyl group, or a benzotriazol-1-yl group);arylalkyl groups (preferably arylalkyl groups having 7 to 15 carbon atoms, for example, benzyl group, phenethyl group, methylbenzyl group, phenylpropyl group, 1-methylphenylethyl group, phenylbutyl group, 2-methylphenylpropyl group, tetrahydronaphthyl group, naphthylmethyl group, naphthylethyl group, indenyl group, fluorenyl group, anthracenylmethyl group (anthrylmethyl group), phenanthrenylmethyl group (phenanthrylmethyl group)); silyl groups (preferably silyl groups having 3 to 38 carbon atoms, more preferably 3 to 18 carbon atoms, for example, trimethylsilyl group, triethylsilyl group, tributylsilyl group, t-butyldimethylsilyl group, t-hexyldimethylsilyl group); hydroxy groups; cyano groups; nitro groups; morpholino groups; Alkoxy groups (preferably alkoxy groups having 1 to 48 carbon atoms, more preferably 1 to 24 carbon atoms, for example, methoxy, ethoxy, 1-butoxy, 2-butoxy, isopropoxy, t-butoxy, dodecyloxy, and cycloalkyloxy groups (for example, cyclopentyloxy and cyclohexyloxy)); aryloxy groups (preferably aryloxy groups having 6 to 48 carbon atoms, more preferably 6 to 24 carbon atoms, for example, phenoxy and 1-naphthoxy); alkenyloxy groups (preferably alkenyloxy groups having 2 to 6 carbon atoms, for example, vinyloxy, 1-propenyloxy, 2-n-propenyloxy (allyloxy), 1-n-butenyloxy, and prenyloxy); heterocyclic oxy groups (preferably heterocyclic oxy groups having 1 to 32 carbon atoms, more preferably 1 to 18 carbon atoms, such as a 1-phenyltetrazole-5-oxy group or a 2-tetrahydropyranyloxy group); silyloxy groups (preferably silyloxy groups having 1 to 32 carbon atoms, more preferably 1 to 18 carbon atoms, such as a trimethylsilyloxy group, a t-butyldimethylsilyloxy group or a diphenylmethylsilyloxy group); acyloxy groups (preferably acyloxy groups having 2 to 48 carbon atoms, more preferably 2 to 24 carbon atoms, such as an acetoxy group, a pivaloyloxy group, a benzoyloxy group, a dodecanoyloxy group, an acryloyloxy group or a methacryloyloxy group);hydroxyalkyleneoxy groups (preferably hydroxyalkyleneoxy groups having 2 to 10 carbon atoms, for example, a hydroxyethyleneoxy group); alkoxycarbonyloxy groups (preferably alkoxycarbonyloxy groups having 2 to 48 carbon atoms, more preferably 2 to 24 carbon atoms, for example, an ethoxycarbonyloxy group, a t-butoxycarbonyloxy group, or a cycloalkyloxycarbonyloxy group (for example, a cyclohexyloxycarbonyloxy group)); aryloxycarbonyloxy groups (preferably aryloxycarbonyloxy groups having 7 to 32 carbon atoms, more preferably 7 to 24 carbon atoms, for example, a phenoxycarbonyloxy group); carbamoyloxy groups (preferably carbamoyloxy groups having 1 to 48 carbon atoms, more preferably 1 to 24 carbon atoms, for example, an N,N-dimethylcarbamoyloxy group, an N-butylcarbamoyloxy group, an N-phenylcarbamoyloxy group, or an N-ethyl-N-phenylcarbamoyloxy group); sulfamoyloxy groups (preferably sulfamoyloxy groups having 1 to 32 carbon atoms, more preferably 1 to 24 carbon atoms, such as an N,N-diethylsulfamoyloxy group or an N-propylsulfamoyloxy group); alkylsulfonyloxy groups (preferably alkylsulfonyloxy groups having 1 to 38 carbon atoms, more preferably 1 to 24 carbon atoms, such as a methylsulfonyloxy group, a hexadecylsulfonyloxy group or a cyclohexylsulfonyloxy group); arylsulfonyloxy groups (preferably arylsulfonyloxy groups having 6 to 32 carbon atoms, more preferably 6 to 24 carbon atoms, such as a phenylsulfonyloxy group); acyl groups (preferably acyl groups having 1 to 48 carbon atoms, more preferably 1 to 24 carbon atoms, such as a formyl group, an acetyl group, an acryloyl group, a methacryloyl group, a pivaloyl group, a benzoyl group, a tetradecanoyl group or a cyclohexanoyl group); an alkoxycarbonyl group (preferably an alkoxycarbonyl group having 2 to 48 carbon atoms, more preferably 2 to 24 carbon atoms, for example, a methoxycarbonyl group, an ethoxycarbonyl group, an octadecyloxycarbonyl group, a cyclohexyloxycarbonyl group, or a 2,6-di-tert-butyl-4-methylcyclohexyloxycarbonyl group);an aryloxycarbonyl group (preferably an aryloxycarbonyl group having 7 to 32 carbon atoms, more preferably 7 to 24 carbon atoms, such as a phenoxycarbonyl group); a carbamoyl group (preferably a carbamoyl group having 1 to 48 carbon atoms, more preferably 1 to 24 carbon atoms, such as a carbamoyl group, N,N-diethylcarbamoyl group, N-ethyl-N-octylcarbamoyl group, N,N-dibutylcarbamoyl group, N-propylcarbamoyl group, N-phenylcarbamoyl group, N-methyl-N-phenylcarbamoyl group, or N,N-dicyclohexylcarbamoyl group); an amino group (preferably an amino group having 32 or less carbon atoms, more preferably 24 or less carbon atoms, such as an amino group, methylamino group, N,N-dimethylamino group, N,N-dibutylamino group, tetradecylamino group, 2-ethylhexylamino group, or cyclohexylamino group); anilino group (preferably an anilino group having 6 to 32 carbon atoms, more preferably 6 to 24 carbon atoms, for example, an anilino group, an N-methylanilino group); heterocyclic amino group (preferably a heterocyclic amino group having 1 to 32 carbon atoms, more preferably 1 to 18 carbon atoms, for example, a 4-pyridylamino group); carbonamido group (preferably a carbonamido group having 2 to 48 carbon atoms, more preferably 2 to 24 carbon atoms, for example, an acetamido group, a benzamido group, a tetradecanamido group, a pivaloylamido group, a cyclohexanamido group); ureido group (preferably a ureido group having 1 to 32 carbon atoms, more preferably 1 to 24 carbon atoms, for example, a ureido group, an N,N-dimethylureido group, an N-phenylureido group); imido group (preferably an imido group having 36 or less carbon atoms, more preferably 24 or less carbon atoms, for example, an N-succinimido group, an N-phthalimido group); an alkoxycarbonylamino group (preferably an alkoxycarbonylamino group having 2 to 48 carbon atoms, more preferably 2 to 24 carbon atoms, for example, a methoxycarbonylamino group, an ethoxycarbonylamino group, a t-butoxycarbonylamino group, an octadecyloxycarbonylamino group, or a cyclohexyloxycarbonylamino group); an aryloxycarbonylamino group (preferably an aryloxycarbonylamino group having 7 to 32 carbon atoms, more preferably 7 to 24 carbon atoms, for example, a phenoxycarbonylamino group);sulfonamido groups (preferably sulfonamido groups having 1 to 48 carbon atoms, more preferably 1 to 24 carbon atoms, for example, methanesulfonamido groups, butanesulfonamido groups, benzenesulfonamido groups, hexadecanesulfonamido groups, and cyclohexanesulfonamido groups); sulfamoylamino groups (preferably sulfamoylamino groups having 1 to 48 carbon atoms, more preferably 1 to 24 carbon atoms, for example, N,N-dipropylsulfamoylamino groups, and N-ethyl-N-dodecylsulfamoylamino groups); azo groups (preferably azo groups having 1 to 32 carbon atoms, more preferably 1 to 24 carbon atoms, for example, phenylazo groups and 3-pyrazolylazo groups); alkylthio groups (preferably alkylthio groups having 1 to 48 carbon atoms, more preferably 1 to 24 carbon atoms, for example, methylthio groups, ethylthio groups, octylthio groups, and cyclohexylthio groups); an arylthio group (preferably an arylthio group having 6 to 48 carbon atoms, more preferably an arylthio group having 6 to 24 carbon atoms, for example, a phenylthio group); a heterocyclic thio group (preferably a heterocyclic thio group having 1 to 32 carbon atoms, more preferably a heterocyclic thio group having 1 to 18 carbon atoms, for example, a 2-benzothiazolylthio group, a 2-pyridylthio group, or a 1-phenyltetrazolylthio group); an alkylsulfinyl group (preferably an alkylsulfinyl group having 1 to 32 carbon atoms, more preferably an alkylsulfinyl group having 1 to 24 carbon atoms, for example, a dodecanesulfinyl group); an arylsulfinyl group (preferably an arylsulfinyl group having 6 to 32 carbon atoms, more preferably an arylsulfinyl group having 6 to 24 carbon atoms, for example, a phenylsulfinyl group); alkylsulfonyl groups (preferably alkylsulfonyl groups having 1 to 48 carbon atoms, more preferably 1 to 24 carbon atoms, for example, methylsulfonyl, ethylsulfonyl, propylsulfonyl, butylsulfonyl, isopropylsulfonyl, 2-ethylhexylsulfonyl, hexadecylsulfonyl, octylsulfonyl, and cyclohexylsulfonyl groups); arylsulfonyl groups (preferably arylsulfonyl groups having 6 to 48 carbon atoms, more preferably 6 to 24 carbon atoms, for example, phenylsulfonyl, and 1-naphthylsulfonyl groups);sulfamoyl groups (preferably sulfamoyl groups having 32 or less carbon atoms, more preferably 24 or less carbon atoms, for example, a sulfamoyl group, an N,N-dipropylsulfamoyl group, an N-ethyl-N-dodecylsulfamoyl group, an N-ethyl-N-phenylsulfamoyl group, an N-cyclohexylsulfamoyl group, or an N-(2-ethylhexyl)sulfamoyl group); phosphonyl groups (preferably phosphonyl groups having 1 to 32 carbon atoms, more preferably 1 to 24 carbon atoms, for example, a phenoxyphosphonyl group, an octyloxyphosphonyl group, or a phenylphosphonyl group); phosphinoylamino groups (preferably phosphinoylamino groups having 1 to 32 carbon atoms, more preferably 1 to 24 carbon atoms, for example, a diethoxyphosphinoylamino group, or a dioctyloxyphosphinoylamino group); epoxy groups; —NHCOCH; ３ ;-SO ２ NHC ２ H ４ OCH ３ ;-NHSO ２ CH ３ and the like, and two or more of these may be combined. These substituents may be further substituted with other substituents. When two or more substituents are present, they may be the same or different. If possible, they may be bonded to each other to form a ring.

[0012] [Liquid Crystal Composition] The liquid crystal composition of the present invention is a liquid crystal composition containing a liquid crystal compound having a ring-opening polymerizable group and a dichroic substance. As described above, by using the liquid crystal composition of the present invention, an optically absorbing anisotropic film in which the decrease in the degree of alignment due to curing is suppressed can be produced. The reason for this effect is not clear in detail, but the inventors speculate as follows. That is, it is believed that the incorporation of a liquid crystal compound having a ring-opening polymerizable group suppresses the curing shrinkage that may occur when the alignment state of the liquid crystal composition of the present invention is fixed, thereby suppressing the decrease in the degree of alignment due to curing.

[0013] The liquid crystal compound and dichroic substance contained in the liquid crystal composition of the present invention, as well as any optional components, will be described in detail below.

[0014] Liquid Crystal Compound Having a Ring-Opening Polymerizable Group The liquid crystal composition of the present invention contains a liquid crystal compound having a ring-opening polymerizable group. Here, the term "ring-opening polymerizable group" refers to a polymerizable group capable of ring-opening polymerization. Ring-opening polymerization refers to a polymerization process that produces a linear polymer by ring-opening a cyclic compound. While conventional vinyl polymers are limited to polyethylene main chains, ring-opening polymerization allows the introduction of functional groups such as ethers, ketones, esters, amides, and carbonates into the polymer main chain, thereby imparting functionality not found in vinyl polymers. While cationic ring-opening polymerization of epoxy and oxetane is well known as a ring-opening polymerization technique, numerous reports have recently been published on radical ring-opening polymerizable monomers, which are less susceptible to residual catalysts, and these reports are incorporated herein by reference (Macromolecules 1990, 23, 1-5; Macromolecules 1993, 26, 1818-1824; Macromolecules 1996, 29, 6983-6989).

[0015] In the present invention, the ring-opening polymerizable group is preferably a polymerizable group capable of radical ring-opening polymerization (radical ring-opening polymerizable group) because it has versatility as a radical polymerization.

[0016] In the present invention, the radical ring-opening polymerizable group is preferably a group represented by the following formula (1) because it has excellent liquid crystal properties.

[0017] In the above formula (1), * represents a bonding position, i.e., a bonding position with the group represented by the above formula (1) in the liquid crystal compound. R1 represents a single bond or a divalent linking group, and R2 represents a hydrogen atom or a substituent. However, at least one of R1 and R2 represents a ring structure, or they are linked to each other to form a ring structure. R3 and R4 each independently represent a hydrogen atom or a substituent. Note that examples of the substituent represented by one embodiment of R2, R3, and R4 include the substituents described in the above-mentioned substituent group A, and among them, an alkyl group is preferred.

[0018] Examples of the divalent linking group represented by one embodiment of R1 include a divalent hydrocarbon group which may have a substituent, a divalent heterocyclic group which may have a substituent, -O-, -S-, -N(Q)-, -CO-, or a combination thereof. Q represents a hydrogen atom or a substituent. Examples of the divalent hydrocarbon group include divalent aliphatic hydrocarbon groups such as alkylene groups having 1 to 10 carbon atoms, alkenylene groups having 1 to 10 carbon atoms, and alkynylene groups having 1 to 10 carbon atoms, and divalent aromatic hydrocarbon groups such as arylene groups. Examples of the divalent heterocyclic group include divalent aromatic heterocyclic groups, and specific examples thereof include a pyridylene group (pyridine-diyl group), a pyridazine-diyl group, an imidazole-diyl group, a thienylene group (thiophene-diyl group), and a quinolylene group (quinoline-diyl group).

[0049] Note that examples of the substituent that the divalent hydrocarbon group and divalent heterocyclic group may have, as well as the substituent represented by one embodiment of Q, include the substituents described in the above-mentioned Substituent Group A, and among these, an alkyl group is preferable.

[0019] In the present invention, at least one of R1 and R2 in the above formula (1) represents a ring structure, or they are linked to each other to form a ring structure. Here, the atoms constituting the ring in the ring structure are not particularly limited, but are preferably carbon atoms or hetero atoms, more preferably any of carbon atoms, oxygen atoms, sulfur atoms, and nitrogen atoms, and even more preferably any of carbon atoms, oxygen atoms, and sulfur atoms. In addition, the ring structure is preferably an alicyclic structure in which some of the carbon atoms constituting the ring may be substituted with hetero atoms (particularly oxygen atoms or sulfur atoms).

[0020] Specific examples of the ring structure represented by at least one of R1 and R2 include ring structures represented by the following formulae.

[0021] Specific examples of the ring structure formed by R1 and R2 being linked to each other include ring structures represented by the following formulae.

[0022] In the present invention, for reasons of excellent liquid crystal properties, the group represented by the above formula (1) is preferably a group represented by any one of the following formulae (CP-1) to (CP-3), more preferably a group represented by the following formula (CP-1) or (CP-2), and even more preferably a group represented by the following formula (CP-1).

[0023] In the above formulas (CP-1) to (CP-3), * represents a bonding position, i.e., a bonding position in the liquid crystal compound with a group represented by any one of the above formulas (CP-1) to (CP-3). R1 ​​represents a single bond or a divalent linking group. Examples of the divalent linking group include those described as one embodiment of R1 in the above formula (1). Among these, a divalent hydrocarbon group which may have a substituent is preferred, a divalent aromatic hydrocarbon group which may have a substituent is more preferred, and a 1,4-phenylene group which may have a substituent is even more preferred. Rp1 represents a substituent. Examples of the substituent include the substituents described in the above-mentioned substituent group A, and among these, an alkyl group is preferred. Rp2 to Rp8 each independently represent a hydrogen atom or a substituent. Examples of the substituent include the substituents described in the above-mentioned substituent group A, and among these, an alkyl group is preferred. Rp2 to Rp8 each independently represent a hydrogen atom or a substituent. Examples of the substituent include the substituents described in the above-mentioned substituent group A, and among these, an alkyl group is preferred. Rp2 to Rp8 each independently represent a hydrogen atom or a methyl group, and a hydrogen atom is more preferred. D1 to D6 each independently represent -CR １ R ２ represents -, -C(=O)-, -O-, or -S-. １ and R ２ each independently represents a hydrogen atom or a substituent. Examples of the substituent include the substituents described in the above-mentioned substituent group A, and among them, an alkyl group is preferable. D1 and D6 each independently represent a —CH ２ - or -O- is preferred. D3 and D4 are -CH ２ -, -O-, or -C(=O)- is preferred, and -CH ２ D2 (limited to D2 adjacent to D3) and D5 are each preferably -CH ２-, -O-, or -S- is preferred, and -S- is more preferred. m1 represents 1 or 2, and when m1 represents 2, multiple D1s may be the same or different. r1 represents an integer of 0 to 3, and when r1 represents 2 or 3, multiple Rp1s may be the same or different, and multiple Rp1s may be linked to each other to form a ring structure. r1 is preferably an integer of 0 to 2, and more preferably 0 or 1. m2 represents an integer of 0 to 5, and when m2 represents an integer of 2 to 5, multiple D2s may be the same or different. m2 is preferably an integer of 0 to 4, and more preferably an integer of 1 to 3. m3 represents 1 or 2, and when m3 represents 2, multiple D6s may be the same or different.

[0024] Examples of the group represented by formula (CP-1) include groups represented by the following formulas: In the following formulas, * represents the bonding position.

[0025] Examples of the group represented by formula (CP-2) include groups represented by the following formulas: In the following formulas, * represents the bonding position.

[0026] Examples of the group represented by formula (CP-3) include groups represented by the following formulas: In the following formulas, * represents the bonding position.

[0027] As the liquid crystal compound having the ring-opening polymerizable group as described above, either a polymer liquid crystal compound or a low molecular weight liquid crystal compound can be used, and a combination of a polymer liquid crystal compound and a low molecular weight liquid crystal compound may be used. Here, "polymer liquid crystal compound" refers to a liquid crystal compound having a repeating unit in its chemical structure. Furthermore, "low molecular weight liquid crystal compound" refers to a liquid crystal compound having no repeating unit in its chemical structure.

[0028] In the present invention, the liquid crystal compound having a ring-opening polymerizable group is preferably a compound represented by the following formula (2) (low molecular weight liquid crystal compound) or a polymer thereof (polymer liquid crystal compound) because of its excellent liquid crystal properties:

[0029] In the above formula (2), P1 and P2 each independently represent a hydrogen atom, a halogen atom, a cyano group, a nitro group, or a polymerizable group. However, at least one of P1 and P2 represents a group represented by any of the above formulas (CP-1) to (CP-3). SP1 and SP2 each independently represent a single bond or a spacer group. Z1 and Z2 each independently represent a single bond, -O-, -COO-, -OCO-, -S-, -COS-, -SCO-, -NHCO-, -CONH-, -NHCONH-, -OCONH-, or -NHCOO-. A1 and A2 represent a ring structure which may have a substituent. L1 and L2 represent a single bond or a divalent linking group. G represents a divalent linking group. n1 and n2 each independently represent an integer of 0 to 6. Here, n1 + n2 represents an integer of 2 to 12. When n1 is an integer of 2 to 6, multiple Z1s may be the same or different, multiple A1s may be the same or different, and multiple L1s may be the same or different. When n2 is an integer of 2 to 6, multiple Z2s may be the same or different, multiple A2s may be the same or different, and multiple L2s may be the same or different. r1 and r2 each independently represent an integer of 1 to 3. When r1 represents 2 or 3, multiple P1s may be the same or different, and when r2 represents 2 or 3, multiple P2s may be the same or different.

[0030] Examples of the polymerizable group represented by one aspect of P1 and P2 in the above formula (2) include groups represented by any of the above formulae (CP-1) to (CP-3), as well as groups represented by the following formulae (P-1) to (P-30). As described above, at least one of P1 and P2 represents a group represented by any of the above formulae (CP-1) to (CP-3), and it is preferable that both P1 and P2 are polymerizable groups, it is more preferable that both P1 and P2 are groups represented by the above formula (CP-1) or (CP-2), and it is even more preferable that both P1 and P2 are groups represented by the above formula (CP-1).

[0031] In the above formulas (P-1) to (P-30), * represents a bonding position. Ｐ represents a hydrogen atom, a halogen atom, a linear, branched or cyclic alkylene group having 1 to 10 carbon atoms, a halogenated alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an alkenyl group having 1 to 20 carbon atoms, an alkynyl group having 1 to 20 carbon atoms, an aryl group having 1 to 20 carbon atoms, a heterocyclic group (which may also be called a heterocyclic group), a cyano group, a hydroxy group, a nitro group, a carboxy group, an aryloxy group, a silyloxy group, a heterocyclic oxy group, an acyloxy group, a carbamoyloxy group, an alkoxycarbonyloxy group, an aryloxycarbonyloxy group, an amino group (including an anilino group), an ammonio group, an acylamino group, an aminocarbonylamino group, Alkoxycarbonylamino group, aryloxycarbonylamino group, sulfamoylamino group, alkyl or arylsulfonylamino group, mercapto group, alkylthio group, arylthio group, heterocyclic thio group, sulfamoyl group, sulfo group, alkyl or arylsulfinyl group, alkyl or arylsulfonyl group, acyl group, aryloxycarbonyl group, alkoxycarbonyl group, carbamoyl group, aryl or heterocyclic azo group, imido group, phosphino group, phosphinyl group, phosphinyloxy group, phosphinylamino group, phosphono group, silyl group, hydrazino group, ureido group, boronic acid group (-B(OH) ２ ), phosphato group (—OPO(OH) ２ ), or a sulfato group (—OSO３ H), and a plurality of R Ｐ may be the same or different.

[0032] The valence of the spacer group represented by one embodiment of SP1 and SP2 in the above formula (2) is r1+1 and r2+1, respectively, as described below, and both are preferably divalent or trivalent, more preferably divalent. Examples of the divalent spacer group include a linear alkylene group having 1 to 12 carbon atoms; a branched alkylene group having 3 to 12 carbon atoms; and -CH ２ Examples of the trivalent spacer group include a divalent linking group in which one or more - groups have been substituted with -O-, -S-, -N(Q)-, or -CO-. Q represents a hydrogen atom or a substituent. Examples of the substituent include the substituents described in the above-mentioned substituent group A, and among these, an alkyl group is preferred. Examples of the trivalent spacer group include the -CH group at the terminal (the side bonding to P1 and P2) in the above-mentioned examples of the divalent spacer group. ２ a group obtained by removing one hydrogen atom from -; -C(Q)(R-)(R-) [R: an alkylene group having 1 to 12 carbon atoms or -CH constituting an alkylene group having 1 to 12 carbon atoms] ２ represents a divalent linking group in which one or more - are substituted with -O-, -S-, -N(Q)-, or -CO-. Q: represents a hydrogen atom or a substituent, and examples of the substituent include the substituents described in the above-mentioned Substituent Group A. ]; and the like. Furthermore, examples of the tetravalent spacer group include, for example, the -CH at the terminal (the side bonding to P1 and P2) in the above-mentioned examples of the divalent spacer group. ２ a group obtained by removing two hydrogen atoms from -; -C(R-)(R-)(R-) (R: an alkylene group having 1 to 12 carbon atoms or -CH constituting an alkylene group having 1 to 12 carbon atoms); ２ represents a divalent linking group in which one or more -'s are replaced by -O-, -S-, -N(Q)- or -CO-. Q represents a hydrogen atom or a substituent, and examples of the substituent include the substituents described in the above-mentioned substituent group A.]; and the like.

[0033] Z1 and Z2 in the above formula (2) each independently represent a single bond, —O—, —C(═O)O—, —OC(═O)—, —S—, —C(═O)S—, —SC(═O)—, —NHC(═O)—, —C(═O)NH—, —NHC(═O)NH—, —OC(═O)NH—, or —NHC(═O)O—, and among these, a single bond, —O—, —C(═O)O—, or —OC(═O)— is preferred.

[0034] A1 and A2 in the above formula (2) represent a ring structure which may have a substituent. Examples of the ring structure include an aromatic hydrocarbon ring, an aromatic heterocycle, and a divalent alicyclic hydrocarbon group. Examples of the aromatic hydrocarbon ring include an aromatic hydrocarbon ring having 6 to 20 carbon atoms, specifically a benzene ring, a naphthalene ring, an anthracene ring, and a phenanthroline ring. Of these, a benzene ring (e.g., a 1,4-phenyl group) is preferred. Examples of the aromatic heterocycle include an aromatic heterocycle having 5 to 20 carbon atoms, specifically a furan ring, a pyrrole ring, a thiophene ring, a pyridine ring, a thiazole ring, and a benzothiazole ring. The divalent alicyclic hydrocarbon group is preferably a 5- or 6-membered ring. The divalent alicyclic hydrocarbon group may be saturated or unsaturated, but a divalent saturated alicyclic hydrocarbon group is preferred. The —CH group constituting the divalent alicyclic hydrocarbon group is preferably a 5- or 6-membered ring. ２ One or more of the - may be substituted with -O-, -S-, or -NH-. Examples of such divalent alicyclic hydrocarbon groups include divalent alicyclic hydrocarbon groups having 5 to 12 carbon atoms, and specific examples include monocyclic hydrocarbon groups and bridged cyclic hydrocarbon groups, and more specific examples include those represented by the following formulae (g-1) to (g-10). Note that examples of the substituent that the ring structure may have include the substituents described in the above-mentioned substituent group A, and among them, an alkyl group is preferred.

[0035] In the formula (2), L1 and L2 represent a single bond or a divalent linking group. Examples of the divalent linking group represented by one embodiment of L1 and L2 include —O—, —C(═O)O—, —OC(═O)—, —S—, —C(═O)S—, —SC(═O)—, —C≡C—, —C═C—, —N═N—, —NHC(═O)—, and —C(═O)NH—.

[0036] In the above formula (2), G represents a divalent linking group. Examples of the divalent linking group represented by G include a divalent hydrocarbon group which may have a substituent, a divalent heterocyclic group which may have a substituent, -O-, -S-, -N(Q)-, -CO-, or a combination thereof. Q represents a hydrogen atom or a substituent. Examples of the divalent hydrocarbon group include divalent aliphatic hydrocarbon groups such as alkylene groups having 1 to 10 carbon atoms, alkenylene groups having 1 to 10 carbon atoms, and alkynylene groups having 1 to 10 carbon atoms, and divalent aromatic hydrocarbon groups such as arylene groups. Examples of the divalent heterocyclic group include divalent aromatic heterocyclic groups, and specific examples thereof include a pyridylene group (pyridine-diyl group), a pyridazine-diyl group, an imidazole-diyl group, a thienylene group (thiophene-diyl group), and a quinolylene group (quinoline-diyl group).

[0049] Note that examples of the substituent that the divalent hydrocarbon group and divalent heterocyclic group may have, as well as the substituent represented by one embodiment of Q, include the substituents described in the above-mentioned Substituent Group A, and among these, an alkyl group is preferable.

[0037] The divalent linking group represented by G includes a linear alkylene group having 1 to 12 carbon atoms; a branched alkylene group having 3 to 12 carbon atoms; and —CH ２ Preferred examples of the divalent linking group include a divalent linking group in which one or more -'s are replaced by -O-, -S-, -N(Q)-, or -CO-. When n1 and n2 in the above formula (2) are both 1, the divalent linking group represented by G preferably contains a divalent aromatic hydrocarbon group such as an arylene group.

[0038] In the above formula (2), n1 and n2 each independently represent an integer of 0 to 6. However, n1 + n2 represents an integer of 2 to 12. Here, n1 and n2 each independently represent an integer of 1 to 3.

[0039] In the above formula (2), r1 and r2 each independently represent an integer of 1 to 3, preferably 1 or 2, and more preferably 1.

[0040] Specific examples of the liquid crystal compound having a ring-opening polymerizable group described above include compounds represented by the following formulas.

[0041] In the present invention, it is preferable that the liquid crystal compound having a ring-opening polymerizable group, in particular the compound represented by the above formula (2) (low molecular weight liquid crystal compound) or its polymer (polymer liquid crystal compound) exhibit nematic liquid crystallinity, because it is excellent for forming a uniform film.

[0042] In the present invention, the content of the liquid crystal compound having a ring-opening polymerizable group is preferably 3 to 50% by mass, more preferably 4 to 30% by mass, and even more preferably 5 to 20% by mass, based on the total mass of the solid content of the liquid crystal composition, because this can further suppress a decrease in the degree of alignment due to curing. Here, in this specification, the "solid content of the liquid crystal composition" refers to components excluding the solvent, and specific examples of the solid content include the liquid crystal compound, the dichroic substance, the polymerization initiator, and the surfactant.

[0043] [Dichroic Substance] The liquid crystal composition of the present invention contains a dichroic substance. Here, the dichroic substance means a dye whose absorbance varies depending on the direction. The dichroic substance may or may not exhibit liquid crystallinity.

[0044] The dichroic substance is not particularly limited, and examples thereof include visible light absorbing substances (dichroic dyes), luminescent substances (fluorescent substances, phosphorescent substances), ultraviolet absorbing substances, infrared absorbing substances, nonlinear optical substances, carbon nanotubes, and inorganic substances (e.g., quantum rods), and any conventionally known dichroic substance (dichroic dye) can be used. Specifically, for example, paragraphs

[0067] to

[0071] of JP 2013-228706 A, paragraphs

[0008] to

[0026] of JP 2013-227532 A, paragraphs

[0008] to

[0015] of JP 2013-209367 A, paragraphs

[0045] to

[0058] of JP 2013-14883 A, paragraphs

[0012] to

[0029] of JP 2013-109090 A, paragraphs

[0009] to

[0017] of JP 2013-101328 A, Paragraphs

[0051] to

[0065] of JP 2013-37353 A, paragraphs

[0049] to

[0073] of JP 2012-63387 A, paragraphs

[0016] to

[0018] of JP 11-305036 A, paragraphs

[0009] to

[0011] of JP 2001-133630 A, paragraphs

[0030] to

[0169] of JP 2011-215337 A, paragraphs

[0021] to

[0075] of JP 2010-106242 A, paragraphs

[0016] to

[0018] of JP 2010-215846 A

[0011] to

[0025] paragraphs,

[0017] to

[0069] paragraphs of JP 2011-048311 A,

[0013] to

[0133] paragraphs of JP 2011-213610 A,

[0074] to

[0246] paragraphs of JP 2011-237513 A,

[0005] to

[0051] paragraphs of JP 2016-006502 A,

[0014] to

[0032] paragraphs of JP 2018-053167 A, and

[0014] to

[0033] paragraphs of JP 2020-11716 A paragraphs

[0005] to

[0041] of International Publication No. 2016 / 060173, paragraphs

[0008] to

[0062] of International Publication No. 2016 / 136561, paragraphs

[0014] to

[0033] of International Publication No. 2017 / 154835, paragraphs

[0014] to

[0033] of International Publication No. 2017 / 154695, paragraphs

[0013] to

[0037] of International Publication No. 2017 / 195833, paragraphs

[0014] to

[0034] of International Publication No. 2018 / 164252,Examples include those described in paragraphs

[0021] to

[0030] of International Publication No. 2018 / 186503, paragraphs

[0043] to

[0063] of International Publication No. 2019 / 189345, paragraphs

[0043] to

[0085] of International Publication No. 2019 / 225468, paragraphs

[0050] to

[0074] of International Publication No. 2020 / 004106, and paragraphs

[0015] to

[0038] of International Publication No. 2021 / 044843.

[0045] As the dichroic substance, a dichroic azo dye compound is preferred. A dichroic azo dye compound refers to an azo dye compound whose absorbance varies depending on the direction. A dichroic azo dye compound may or may not exhibit liquid crystallinity. When a dichroic azo dye compound exhibits liquid crystallinity, it may exhibit either nematic or smectic properties. The temperature range in which the liquid crystal phase is exhibited is preferably room temperature (approximately 20 to 28°C) to 300°C, and more preferably 50 to 200°C from the viewpoints of handleability and manufacturing suitability.

[0046] In the present invention, from the viewpoint of adjusting color hue, it is preferable to use at least one dye compound (first dichroic azo dye compound) having a maximum absorption wavelength in the wavelength range of 560 to 700 nm, and at least one dye compound (second dichroic azo dye compound) having a maximum absorption wavelength in the wavelength range of 455 nm or more and less than 560 nm.

[0047] In the present invention, three or more kinds of dichroic azo dye compounds may be used in combination. For example, from the viewpoint of making the light absorption anisotropic film closer to black, it is preferable to use a first dichroic azo dye compound, a second dichroic azo dye compound, and at least one dye compound (third dichroic azo dye compound) having a maximum absorption wavelength in the wavelength range of 380 nm or more and less than 455 nm in combination.

[0048] In the present invention, the dichroic azo dye compound preferably has a crosslinkable group, such as a (meth)acryloyl group, an epoxy group, an oxetanyl group, or a styryl group, with a (meth)acryloyl group being preferred.

[0049] The content of the dichroic substance is not particularly limited, but is preferably 3% by mass or more, more preferably 8% by mass or more, even more preferably 10% by mass or more, and particularly preferably 10 to 30% by mass, relative to the total mass of the optically absorptive anisotropic film, because the degree of orientation of the optically absorptive anisotropic film to be formed is high. When multiple dichroic substances are used in combination, the total amount of the multiple dichroic substances is preferably within the above-mentioned range. Furthermore, the content of the dichroic substance is preferably 10 to 400 mg / cm, because the degree of orientation of the optically absorptive anisotropic film to be formed is high. ３ is preferably 30 to 200 mg / cm ３ More preferably, it is 40 to 150 mg / cm ３ When a plurality of dichroic substances are used in combination, the total amount of the dichroic substances is preferably in the above-mentioned range. ３ The dichroic substance content can be obtained by measuring a solution in which an optically absorptive anisotropic film is dissolved, or an extract obtained by immersing an optically absorptive film in a solvent, using high-performance liquid chromatography (HPLC), but is not limited to the above method. Quantification can be performed using the dichroic substance contained in the optically absorptive anisotropic film as a standard sample. One example of a method for calculating the content of the dichroic substance is to calculate the volume by multiplying the thickness of the optically absorptive anisotropic film obtained from a microscopic image of the cross section of the optically absorptive film by the area of ​​the optically absorptive film used to measure the amount of dye, and then dividing the volume by the amount of dye measured by HPLC to calculate the dye content.

[0050] [Other Liquid Crystal Compounds] The liquid crystal composition of the present invention may contain other liquid crystal compounds in addition to the liquid crystal compound having the ring-opening polymerizable group described above.

[0051] As the other liquid crystal compound, either a polymer liquid crystal compound or a low molecular weight liquid crystal compound can be used, with the polymer liquid crystal compound being preferred due to its ability to increase the degree of orientation. Furthermore, as the liquid crystal compound, a polymer liquid crystal compound and a low molecular weight liquid crystal compound may be used in combination. Here, "polymer liquid crystal compound" refers to a liquid crystal compound having a repeating unit in its chemical structure. Furthermore, "low molecular weight liquid crystal compound" refers to a liquid crystal compound having no repeating unit in its chemical structure. Examples of polymer liquid crystal compounds include the thermotropic liquid crystal polymers described in JP 2011-237513 A and the polymer liquid crystal compounds described in paragraphs

[0012] to

[0042] of WO 2018 / 199096 A. Examples of low molecular weight liquid crystal compounds include the liquid crystal compounds described in paragraphs

[0072] to

[0088] of JP 2013-228706 A, with liquid crystal compounds exhibiting smectic properties being preferred. Examples of such liquid crystal compounds include those described in paragraphs

[0019] to

[0140] of WO 2022 / 014340, the disclosures of which are incorporated herein by reference.

[0052] The content of the other liquid crystal compound is preferably 50 to 99 mass %, more preferably 65 to 95 mass %, and even more preferably 75 to 90 mass %, relative to the total mass of the solid content of the liquid crystal composition, because the degree of orientation of the produced optically absorptive anisotropic film is higher and the heat resistance is also improved.

[0053] [Other Components] The liquid crystal composition of the present invention may contain components other than the above-described liquid crystal compound and dichroic substance (hereinafter also referred to as "other components"). Examples of the other components include an alignment agent, a polymerization initiator, an interfacial modifier, and a solvent.

[0054] <Alignment Agent> The liquid crystal composition of the present invention may contain an alignment agent. Examples of the alignment agent include a boronic acid compound and an onium salt. The boronic acid compound functions as a horizontal alignment agent or a vertical alignment agent. The onium salt functions as a vertical alignment agent. The alignment agent may be used alone or in combination of two or more types.

[0055] The boronic acid compound is preferably a compound represented by formula (30).

[0056] Formula (30)

[0057] In formula (30), R １ and R ２ R each independently represents a hydrogen atom, a substituted or unsubstituted aliphatic hydrocarbon group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group. ３ represents a substituent containing a (meth)acrylic group. Specific examples of the boronic acid compound include the boronic acid compounds represented by general formula (I) described in paragraphs 0023 to 0032 of JP-A 2008-225281. Preferred boronic acid compounds include the compounds exemplified below.

[0058]

[0059] Specific examples of the onium salt include the onium salts described in paragraphs 0052 to 0058 of JP-A No. 2012-208397, the onium salts described in paragraphs 0024 to 0055 of JP-A No. 2008-026730, and the onium salts described in JP-A No. 2002-37777.

[0060] When the liquid crystal composition of the present invention contains an aligning agent, the content of the aligning agent is preferably 0.01 to 30% by mass, more preferably 0.1 to 10% by mass, based on the total mass of the solid content of the liquid crystal composition.

[0061] <Polymerization initiator> The liquid crystal composition of the present invention may contain a polymerization initiator. There are no particular limitations on the polymerization initiator, but it is preferably a photosensitive compound, i.e., a photopolymerization initiator. As the photopolymerization initiator, various compounds can be used without particular limitations. Examples of photopolymerization initiators include α-carbonyl compounds (U.S. Pat. Nos. 2,367,661 and 2,367,670), acyloin ethers (U.S. Pat. No. 2,448,828), α-hydrocarbon-substituted aromatic acyloin compounds (U.S. Pat. No. 2,722,512), polynuclear quinone compounds (U.S. Pat. Nos. 3,046,127 and 2,951,758), and combinations of triarylimidazole dimers and p-aminophenyl ketones (U.S. Pat. No. 3,549,367). Examples of such photopolymerization initiators include acridine and phenazine compounds (JP 60-105667 A and U.S. Pat. No. 4,239,850 A), oxadiazole compounds (U.S. Pat. No. 4,212,970 A), o-acyloxime compounds (JP 2016-27384 A

[0065] ), and acylphosphine oxide compounds (JP 63-40799 A, JP 5-29234 B, JP 10-95788 A, and JP 10-29997 A). Commercially available photopolymerization initiators can also be used, including IRGACURE 184, IRGACURE 907, IRGACURE 369, IRGACURE 651, IRGACURE 819, IRGACURE OXE-01, and IRGACURE OXE-02 manufactured by BASF. The polymerization initiator may be used alone or in combination of two or more kinds.

[0062] When the liquid crystal composition of the present invention contains a polymerization initiator, the content of the polymerization initiator is preferably 0.01 to 30% by mass, more preferably 0.1 to 15% by mass, based on the total mass of the solid content of the liquid crystal composition.

[0063] <Interfacial Modifier> The liquid crystal composition of the present invention may contain an interfacial modifier. There are no particular limitations on the interfacial modifier, and polymer-based interfacial modifiers and low-molecular-weight interfacial modifiers can be used, including compounds described in paragraphs

[0253] to

[0293] of JP-A No. 2011-237513. Silicon-based polymers can also be used as interfacial modifiers. Fluorine (meth)acrylate-based polymers described in paragraphs

[0018] to

[0043] of JP-A No. 2007-272185 can also be used as interfacial modifiers. Examples of the interface improver include compounds described in paragraphs

[0079] to

[0102] of JP-A-2007-069471, polymerizable liquid crystal compounds represented by formula (4) described in JP-A-2013-047204 (particularly compounds described in paragraphs

[0020] to

[0032] ), polymerizable liquid crystal compounds represented by formula (4) described in JP-A-2012-211306 (particularly compounds described in paragraphs

[0022] to

[0029] ), and liquid crystal alignment promoters represented by formula (4) described in JP-A-2002-129162 (particularly compounds described in paragraphs

[0032] to

[0032] ). The compounds described in paragraphs

[0076] to

[0078] and

[0082] to

[0084] of the present invention, the compounds represented by formulas (4), (II) and (III) described in JP-A-2005-099248 (particularly the compounds described in paragraphs

[0092] to

[0096] ), the compounds described in paragraphs

[0013] to

[0059] of Japanese Patent No. 4,385,997, the compounds described in paragraphs

[0018] to

[0044] of Japanese Patent No. 5,034,200, and the compounds described in paragraphs

[0019] to

[0038] of Japanese Patent No. 4,895,088 can also be used. The interfacial modifiers may be used alone or in combination of two or more.

[0064] When the liquid crystal composition of the present invention contains an interfacial modifier, the content of the interfacial modifier is preferably 0.005 to 15% by mass, more preferably 0.01 to 5% by mass, and even more preferably 0.015 to 3% by mass, based on the total mass of the solid content of the liquid crystal composition. When multiple interfacial modifiers are used in combination, the total amount of the multiple interfacial modifiers is preferably in the above-mentioned range.

[0065] <Solvent> The liquid crystal composition of the present invention preferably contains a solvent from the viewpoint of workability, etc. Examples of the solvent include ketones (e.g., acetone, 2-butanone, methyl isobutyl ketone, cyclopentanone, and cyclohexanone), ethers (e.g., dioxane, tetrahydrofuran, tetrahydropyran, dioxolane, tetrahydrofurfuryl alcohol, and cyclopentyl methyl ether), aliphatic hydrocarbons (e.g., hexane), alicyclic hydrocarbons (e.g., cyclohexane), aromatic hydrocarbons (e.g., benzene, toluene, xylene, and trimethylbenzene), halogenated carbons (e.g., dichloromethane, trichloromethane (chloroform), dichloroethane, dichlorobenzene, and chloroform), and the like. Examples of suitable solvents include organic solvents such as toluene, esters (e.g., methyl acetate, ethyl acetate, butyl acetate, diethyl carbonate), alcohols (e.g., ethanol, isopropanol, butanol, cyclohexanol), cellosolves (e.g., methyl cellosolve, ethyl cellosolve, 1,2-dimethoxyethane), cellosolve acetates, sulfoxides (e.g., dimethyl sulfoxide), amides (e.g., dimethylformamide, dimethylacetamide, N-methylpyrrolidone, N-ethylpyrrolidone, 1,3-dimethyl-2-imidazolidinone), and heterocyclic compounds (e.g., pyridine), as well as water. These solvents may be used alone or in combination of two or more. Among these solvents, organic solvents are preferred because they provide better effects of the present invention, and halogenated carbons or ketones are more preferred.

[0066] When the liquid crystal composition of the present invention contains a solvent, the content of the solvent is preferably from 70 to 99% by mass, more preferably from 83 to 97% by mass, and even more preferably from 85 to 95% by mass, based on the total mass of the liquid crystal composition.

[0067] [Liquid Crystal Compound] The liquid crystal compound of the present invention is a compound represented by the above formula (2) or a polymer thereof, in which at least one of P1 and P2 in the above formula (2) represents a group represented by the above formula (CP-1) or (CP-2).

[0068] [Light-absorbing anisotropic film] The light-absorbing anisotropic film of the present invention is an light-absorbing anisotropic film obtained by fixing the alignment state of the liquid crystal composition of the present invention described above. The alignment state of the liquid crystal composition (particularly the liquid crystal compound) may be any of horizontal alignment, vertical alignment, tilt alignment, and twist alignment.

[0069] Although the method for producing the optically absorptive anisotropic film of the present invention is not particularly limited, a method (hereinafter also referred to as "the present production method") that includes, in this order, a step of forming a coating film by applying the above-mentioned liquid crystal composition on an alignment film (hereinafter also referred to as "coating film formation step") and a step of orienting the liquid crystal component contained in the coating film (hereinafter also referred to as "orientation step") is preferred because it results in a higher degree of orientation of the produced optically absorptive anisotropic film. The liquid crystal component refers to a component that includes not only the above-mentioned liquid crystal compound but also a dichroic substance having liquid crystal properties. Each step will be described below.

[0070] [Coating Film Forming Step] The coating film forming step is a step of forming a coating film by applying the above-described liquid crystal composition onto an alignment film. By using a liquid crystal composition containing the above-described solvent or by using a liquid crystal composition that has been converted into a molten liquid or the like by heating or the like, it becomes easy to apply the liquid crystal composition onto the alignment film. Examples of methods for applying the liquid crystal composition include known methods such as roll coating, gravure printing, spin coating, wire bar coating, extrusion coating, direct gravure coating, reverse gravure coating, die coating, spraying, and inkjet printing.

[0071] <Alignment Film> The alignment film can be formed by means of rubbing an organic compound (preferably a polymer) onto the film surface, oblique vapor deposition of an inorganic compound, formation of a layer having microgrooves, or accumulation of an organic compound (e.g., ω-tricosanoic acid, dioctadecylmethylammonium chloride, methyl stearate, etc.) by the Langmuir-Blodgett method (LB film). Furthermore, alignment films that exhibit alignment function upon application of an electric field, a magnetic field, or light irradiation are also known. Among these, in the present invention, alignment films formed by rubbing are preferred in terms of ease of control of the pretilt angle of the alignment film, and photo-alignment films formed by light irradiation are also preferred in terms of uniformity of alignment.

[0072] (Rubbing Treatment Alignment Film) Polymer materials used for the alignment film formed by rubbing treatment are described in many literatures, and many commercially available products are available. In the present invention, polyvinyl alcohol or polyimide, and derivatives thereof are preferably used. For details of the alignment film, see WO 2001 / 88574 A1, page 43, line 24 to page 49, line 8. The thickness of the alignment film is preferably 0.01 to 10 μm, and more preferably 0.01 to 1 μm.

[0073] (Photo-alignment film) Photo-alignment materials used for alignment films formed by light irradiation are described in many documents, etc. In the present invention, for example, azo compounds described in JP-A Nos. 2006-285197, 2007-76839, 2007-138138, 2007-94071, 2007-121721, 2007-140465, 2007-156439, 2007-133184, 2009-109831, Japanese Patent Nos. 3883848 and 4151746, and compounds described in JP-A No. 2002-229039 are used. Preferred examples include aromatic ester compounds of the above, maleimide and / or alkenyl-substituted nadimide compounds having a photo-alignable unit described in JP-A Nos. 2002-265541 and 2002-317013, photo-crosslinkable silane derivatives described in Japanese Patent Nos. 4205195 and 4205198, and photo-crosslinkable polyimides, polyamides, or esters described in Japanese Patent Publication Nos. 2003-520878, 2004-529220, or Japanese Patent No. 4162850. Azo compounds, photo-crosslinkable polyimides, polyamides, or esters are more preferred.

[0074] A photo-alignment film formed from the above materials is irradiated with linearly polarized or non-polarized light to produce a photo-alignment film. In this specification, "linearly polarized light irradiation" and "non-polarized light irradiation" refer to operations for causing a photoreaction in the photo-alignment material. The wavelength of the light used varies depending on the photo-alignment material used, and is not particularly limited as long as it is the wavelength necessary for the photoreaction. The peak wavelength of the light used for photoirradiation is preferably 200 nm to 700 nm, and ultraviolet light with a peak wavelength of 400 nm or less is more preferred.

[0075] Examples of light sources used for light irradiation include commonly used light sources, such as lamps such as tungsten lamps, halogen lamps, xenon lamps, xenon flash lamps, mercury lamps, mercury xenon lamps, and carbon arc lamps, various lasers [e.g., semiconductor lasers, helium-neon lasers, argon ion lasers, helium-cadmium lasers, and YAG (yttrium aluminum garnet) lasers], light-emitting diodes, and cathode ray tubes.

[0076] As a means for obtaining linearly polarized light, a method using a polarizer (e.g., an iodine polarizer, a dichroic material polarizer, and a wire grid polarizer), a method using a prism element (e.g., a Glan-Thompson prism) or a reflective polarizer utilizing the Brewster angle, or a method using light emitted from a polarized laser light source can be employed. Alternatively, a filter or a wavelength conversion element may be used to selectively irradiate only light of a required wavelength.

[0077] In the case of linearly polarized light, the light is irradiated from the top or back surface of the alignment film perpendicularly or obliquely to the surface of the alignment film. The incident angle of the light varies depending on the photo-alignment material, but is preferably 0 to 90° (perpendicular), and more preferably 40 to 90°. In the case of non-polarized light, the alignment film is irradiated with non-polarized light obliquely. The incident angle is preferably 10 to 80°, more preferably 20 to 60°, and even more preferably 30 to 50°. The irradiation time is preferably 1 to 60 minutes, and more preferably 1 to 10 minutes.

[0078] When patterning is required, a method of irradiating light using a photomask the number of times required to form a pattern, or a method of writing a pattern by laser light scanning can be used.

[0079] [Orientation Step] The orientation step is a step of orienting the dichroic material contained in the coating film. This results in the optically absorptive anisotropic film of the present invention. It is believed that in the orientation step, the dichroic material is oriented along the liquid crystal compound oriented by the orientation film. The orientation step may include a drying treatment. Components such as the solvent can be removed from the coating film by the drying treatment. The drying treatment may be performed by leaving the coating film at room temperature for a predetermined time (e.g., natural drying), or by heating and / or blowing air. Here, the dichroic material contained in the liquid crystal composition may be aligned by the above-described coating film formation step or drying treatment. For example, in an embodiment in which the liquid crystal composition is prepared as a coating liquid containing a solvent, the coating film may be dried to remove the solvent from the coating film, thereby aligning the dichroic material contained in the coating film, thereby obtaining the optically absorptive anisotropic film of the present invention.

[0080] The orientation step preferably includes a heat treatment. This further aligns the dichroic material contained in the coating film, resulting in a higher degree of orientation in the resulting optically absorptive anisotropic film. From the standpoint of manufacturability, the heat treatment is preferably performed at a temperature of 10 to 250°C, more preferably 25 to 190°C. The heating time is preferably 1 to 300 seconds, more preferably 1 to 60 seconds.

[0081] The orientation step may include a cooling treatment carried out after the heating treatment. The cooling treatment is a treatment in which the coated film after heating is cooled to about room temperature (20 to 25°C). This further fixes the orientation of the dichroic material contained in the coated film, and the degree of orientation of the resulting optically absorptive anisotropic film is increased. The cooling method is not particularly limited and can be carried out by a known method. The optically absorptive anisotropic film of the present invention can be obtained by the above steps.

[0082] [Other Steps] The present manufacturing method may include a step of curing the optically absorptive anisotropic film after the alignment step (hereinafter also referred to as a "curing step"). The curing step is performed, for example, by heating and / or light irradiation (exposure). Among these, the curing step is preferably performed by light irradiation. Various light sources such as infrared light, visible light, or ultraviolet light can be used as the light source for curing, but ultraviolet light is preferred. Furthermore, ultraviolet light may be irradiated while heating during curing, or ultraviolet light may be irradiated through a filter that transmits only specific wavelengths. Furthermore, exposure may be performed in a nitrogen atmosphere. When the curing of the optically absorptive anisotropic film proceeds by radical polymerization, exposure in a nitrogen atmosphere is preferred because inhibition of polymerization by oxygen is reduced.

[0083] The thickness of the optically absorptive anisotropic film of the present invention is not particularly limited, but is preferably 0.3 to 10 μm, more preferably 0.5 to 9 μm, for the reason that the effect of the present invention is more excellent.

[0084] The liquid crystal compound and dichroic substance contained in the optically absorptive anisotropic film of the present invention have a fixed alignment state. One embodiment of the optically absorptive anisotropic film of the present invention is one in which the angle θ between the transmittance central axis of the optically absorptive anisotropic film and the normal direction to the surface of the optically absorptive anisotropic film (hereinafter also referred to as "transmittance central axis angle θ") is more than 45° and 90° or less, more preferably 75° or more and 90° or less, and even more preferably 80° or more and 90° or less. A laminate comprising an optically absorptive anisotropic film (polarizer) having a transmittance central axis angle θ of more than 45° and 90° or less and a λ / 4 plate (described later) is suitably used as a circular polarizer.

[0085] Another embodiment of the optically absorptive anisotropic film of the present invention is one in which the transmittance central axis angle θ is 0° or more and 45° or less, more preferably 0° or more and 35° or less, and even more preferably 0° or more and less than 35°. A laminate comprising an optically absorptive anisotropic film in which the transmittance central axis angle θ is 0° or more and 45° or less, and a polarizer having an in-plane absorption axis, is suitably used as a viewing angle control film.

[0086] Here, the term "transmittance central axis" refers to the direction that exhibits the highest transmittance when the transmittance is measured by changing the tilt angle (polar angle) and tilt direction (azimuth angle) relative to the normal direction of the optically absorptive anisotropic film surface. Specifically, an AxoScan OPMF-1 (manufactured by OptoScience) is used to measure the Mueller matrix at a wavelength of 550 nm. More specifically, during measurement, the azimuth angle at which the transmittance central axis is tilted is first found, and then, within a plane containing the normal direction of the optically absorptive anisotropic film along that azimuth angle (a plane containing the transmittance central axis and perpendicular to the film surface), the polar angle, which is the angle relative to the normal direction of the optically absorptive anisotropic film surface, is changed in 1° increments from -70 to 70°, and the Mueller matrix at a wavelength of 550 nm is measured, and the transmittance of the optically absorptive anisotropic film is derived. As a result, the direction with the highest transmittance is designated as the transmittance central axis. The transmittance central axis means the direction of the absorption axis (the direction of the long axis of the molecule) of the dichroic material contained in the optically absorptive anisotropic film.

[0087] The transmittance central axis angle θ can be set to a desired value by, for example, adjusting the type and content of the alignment agent.

[0088] [Laminate] The laminate of the present invention is a laminate having the optically absorptive anisotropic film of the present invention described above. The optically absorptive anisotropic film may be disposed on a substrate. When the laminate of the present invention has a substrate, an alignment film may be disposed between the substrate and the optically absorptive anisotropic film. Hereinafter, each member constituting the laminate of the present invention will be described.

[0089] [Substrate] The substrate is preferably a transparent support. The transparent support refers to a support having a visible light transmittance of 60% or more, preferably 80% or more, and more preferably 90% or more. The transparent support may be any known transparent resin film, transparent resin plate, transparent resin sheet, etc., and is not particularly limited. The transparent resin film may be a cellulose acylate film (e.g., cellulose triacetate film (refractive index 1.48), cellulose diacetate film, cellulose acetate butyrate film, cellulose acetate propionate film), polyethylene terephthalate film, polyethersulfone film, polyacrylic resin film, polyurethane resin film, polyester film, polycarbonate film, polysulfone film, polyether film, polymethylpentene film, polyether ketone film, (meth)acrylonitrile film, etc.

[0090] Among these, a cellulose acylate film is preferred, and a cellulose triacetate film is more preferred, because it has high transparency, little optical birefringence, and is easy to manufacture, and is generally used as a protective film for a polarizing plate. The thickness of the substrate is usually 20 to 100 μm. In the present invention, it is particularly preferred that the substrate is a cellulose ester film, and that the film thickness is 20 to 70 μm.

[0091] [Light-Absorption Anisotropic Film] The light-absorption anisotropic film of the present invention is as described above, and therefore, its description will be omitted.

[0092] [Alignment Film] The alignment film (alignment layer) is as described above, and therefore a description thereof will be omitted.

[0093] [λ / 4 Plate] One preferred embodiment of the laminate of the present invention includes an optically absorptive anisotropic film (particularly, an optically absorptive anisotropic film having a transmittance central axis angle θ of more than 45° and not more than 90°) and a λ / 4 plate. Such a laminate (optical film) is suitable for use as a circularly polarizing plate.

[0094] A λ / 4 plate is a plate having a λ / 4 function, specifically, a plate having the function of converting linearly polarized light of a specific wavelength into circularly polarized light (or circularly polarized light into linearly polarized light). For example, specific examples of a λ / 4 plate having a single-layer structure include a stretched polymer film and a retardation film having a light-absorbing anisotropic film with λ / 4 function provided on a support, and specific examples of a λ / 4 plate having a multi-layer structure include a broadband λ / 4 plate formed by laminating a λ / 4 plate and a λ / 2 plate. The λ / 4 plate and the light-absorbing anisotropic film may be provided in contact with each other, or another layer may be provided between the λ / 4 plate and the light-absorbing anisotropic film. Examples of such layers include an adhesive layer or bonding layer for ensuring adhesion, and a barrier layer.

[0095] [Polarizer] Another preferred embodiment of the laminate of the present invention includes an optically absorptive anisotropic film (particularly an optically absorptive anisotropic film having a transmittance central axis angle θ of 0° or more and 45° or less) and a polarizer having an in-plane absorption axis. Such a laminate (optical film) is preferably used as a viewing angle control film used to control the viewing angle. The polarizer is preferably disposed on the side of the optically absorptive anisotropic film opposite the substrate. The polarizer may be disposed so as to be in contact with the surface of the optically absorptive anisotropic film, or may be disposed on the surface of the optically absorptive anisotropic film via another layer (for example, a known adhesive layer or pressure-sensitive adhesive layer).

[0096] The polarizer is not particularly limited as long as it has an absorption axis in its plane and functions to convert light into specific linearly polarized light, and conventionally known polarizers can be used. Examples of polarizers that can be used 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 are applicable. Preferred polarizers are those in which a dichroic organic dye is oriented by utilizing the orientation of a liquid crystal compound. Preferred stretched polarizers are those produced by adsorbing iodine or a dichroic dye to polyvinyl alcohol and stretching the resulting mixture. Examples of suitable polarizers include the optically absorptive anisotropic film described in JP 2010-152351 A and containing a horizontally aligned dichroic dye compound (a direction intersecting the thickness direction of the optically absorptive anisotropic film) without a liquid crystal compound, and the optically absorptive anisotropic film described in WO 2017 / 154907 A and containing a liquid crystal compound and a horizontally aligned dichroic dye compound.

[0097] [Barrier Layer] The laminate of the present invention preferably has a barrier layer together with the optically absorptive anisotropic film. Here, the barrier layer is also called a gas barrier layer (oxygen barrier layer), and has the function of protecting the polarizing element of the present invention from gases such as oxygen in the atmosphere, moisture, or compounds contained in adjacent layers. The laminate of the present invention preferably has a barrier layer having an oxygen permeability coefficient of 200 cc / m or more in the layer adjacent to the optically absorptive anisotropic film, for the reason that durability is further improved. ２ It is preferable that the barrier layer has an oxygen permeability of 50 cc / m or less. ２ It is more preferable that the optically absorptive anisotropic film has a barrier layer having an oxygen permeability coefficient of 200 cc / m or less other than the barrier layer. ２ If there is a layer where the permeability is 1 / 4 day atm or less, a barrier layer does not need to be provided. Here, the oxygen permeability coefficient is an index representing the amount of oxygen passing through a membrane per unit time and unit area, and in the present invention, a value measured with an oxygen concentration device (for example, Model 3600 manufactured by Hack Ultra Analytical) in an environment of 25°C and 50% relative humidity (RH) is used.

[0098] The organic compounds contained in the barrier layer have a high oxygen blocking function, and examples of such compounds include polymerizable compounds with high hydrogen bonding properties and compounds with many polymerizable groups per molecular weight. Examples of compounds with many polymerizable groups per molecular weight include pentaerythritol tetra(meth)acrylate and dipentaerythritol hexa(meth)acrylate.

[0099] Examples of polymerizable compounds with high hydrogen bonding properties include epoxy compounds, and specifically, compounds represented by the following formula are included. Among these, 3',4'-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate represented by CEL2021P below is preferred.

[0100]

[0101] From the viewpoint of preventing diffusion of the dichroic dye in the light absorption anisotropic film during durability testing, it is also preferable to use, as the barrier layer, a polymer having a hydrophilic group described in paragraph

[0056] of WO 2019-22121 or a water-soluble polymer described in paragraphs

[0117] to

[0133] of JP 2017-083843 A. In addition, reference can be made to the descriptions in paragraphs

[0014] to

[0054] of JP 2014-159124 A, paragraphs

[0042] to

[0075] of JP 2017-121721 A, paragraphs

[0045] to

[0054] of JP 2017-115076 A, paragraphs

[0010] to

[0061] of JP 2012-213938 A, and paragraphs

[0021] to

[0031] of JP 2005-169994 A.

[0102] [Adhesive Layer] The laminate of the present invention may or may not have an adhesive layer. Examples of adhesives constituting the adhesive layer include pressure-sensitive adhesives and adhesives. Examples of adhesives include rubber-based adhesives, acrylic-based adhesives, silicone-based adhesives, urethane-based adhesives, vinyl alkyl ether-based adhesives, polyvinyl alcohol-based adhesives, polyvinylpyrrolidone-based adhesives, polyacrylamide-based adhesives, and cellulose-based adhesives, with acrylic-based adhesives (pressure-sensitive adhesives) being preferred. Examples of adhesives include polyvinyl alcohol adhesives (water-based glues), solvent-based adhesives, emulsion-based adhesives, solventless adhesives, active energy ray-curable adhesives, and heat-curable adhesives. Examples of active energy ray-curable adhesives include electron beam-curable adhesives, ultraviolet-curable adhesives, and visible light-curable adhesives, with ultraviolet-curable adhesives being preferred.

[0103] The thickness of the pressure-sensitive adhesive layer is not particularly limited, but from the viewpoint of thinning, it is preferably 25 μm or less, more preferably 15 μm or less, and even more preferably 5 μm or less. The lower limit is not particularly limited, and it is often 0.1 μm or more.

[0104] From the viewpoint of simplification and thinning, it is also preferable to provide the pressure-sensitive adhesive layer with the function of improving the durability of the barrier layer, thereby eliminating the barrier layer and configuring the optically absorptive anisotropic film and the pressure-sensitive adhesive layer adjacent to each other. For example, a configuration in which an alignment layer / optically absorptive anisotropic film / pressure-sensitive adhesive layer / retardation layer are arranged adjacent to each other can be mentioned. In this case, the pressure-sensitive adhesive layer is preferably, for example, an adhesive containing polyvinyl alcohol as a main component, a UV (ultraviolet) adhesive with low oxygen permeability, or a pressure-sensitive adhesive having a hydrophilic group-containing polymer, from the viewpoint of preventing the diffusion of the dichroic substance in the optically absorptive anisotropic film during durability.

[0105] [Display Device] The display device of the present invention comprises the optically absorptive anisotropic film of the present invention (preferably the laminate of the present invention) and a display element. The optically absorptive anisotropic film and the display element may be laminated via a known adhesive layer or pressure-sensitive adhesive layer. The display element used in the display device of the present invention is not particularly limited, and examples thereof include liquid crystal cells, organic electroluminescence (hereinafter abbreviated as "EL") display panels, and plasma display panels. Of these, a liquid crystal cell or an organic EL display panel is 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. Some image display devices are thin and can be molded into a curved surface. The optically absorptive anisotropic film used in the present invention is thin and easily bendable, making it suitable for use in image display devices with curved display surfaces. Some image display devices have a pixel density of over 250 ppi, enabling high-resolution display. The optically absorptive anisotropic film used in the present invention can be suitably applied to such high-definition image display devices without causing moire.

[0106] [Liquid Crystal Display Device] A preferred example of a liquid crystal display device according to the present invention is one having the above-described viewing angle control film and a liquid crystal cell. A specific configuration includes a configuration in which the viewing angle control film is disposed on a front-side polarizing plate or a rear-side polarizing plate. These configurations enable viewing angle control in which light is blocked in the vertical or horizontal directions. Furthermore, viewing angle control films may be disposed on both the front-side polarizing plate and the rear-side polarizing plate. This configuration enables viewing angle control in which light is blocked in all directions and light is transmitted only in the front direction. Furthermore, multiple viewing angle control films may be laminated via retardation layers. Controlling the retardation value and optical axis direction allows for control of transmission and light-blocking performance. For example, arranging a polarizer, a viewing angle control film, a λ / 2 wavelength plate (with an axis angle shifted by 45° relative to the orientation direction of the polarizer), and a viewing angle control film enables viewing angle control in which light is blocked in all directions and light is transmitted only in the front direction. As the retardation layer, a positive A plate, a negative A plate, a positive C plate, a negative C plate, a B plate, an O plate, etc. can be used. From the viewpoint of thinning the viewing angle control system, the thickness of the retardation layer is preferably as thin as possible as long as it does not impair optical properties, mechanical properties, and manufacturability, and specifically, is preferably 1 to 150 μm, more preferably 1 to 70 μm, and even more preferably 1 to 30 μm. The liquid crystal cell constituting the liquid crystal display device will be described in detail below.

[0107] <Liquid Crystal Cell> The liquid crystal cell used in the liquid crystal display device is preferably, but not limited to, a VA (Vertical Alignment) mode, an OCB (Opticaly Compensated Bend) mode, an IPS (In-Plane-Switching) mode, or a TN (Twisted Nematic) mode. In a TN mode liquid crystal cell, when no voltage is applied, rod-shaped liquid crystal molecules are aligned substantially horizontally and further twisted at an angle of 60 to 120 degrees. TN mode liquid crystal cells are most commonly used in color TFT liquid crystal display devices and are described in many literatures. In a VA mode liquid crystal cell, rod-shaped liquid crystal molecules are aligned substantially vertically when no voltage is applied. VA mode liquid crystal cells include (1) narrowly defined VA mode liquid crystal cells in which rod-shaped liquid crystal molecules are aligned substantially vertically when no voltage is applied and substantially horizontally when a voltage is applied (described in JP-A-2-176625), (2) multi-domain VA mode liquid crystal cells (described in SID97, Digest of Tech. Papers (Proceedings) 28 (1997) 845) in order to widen the viewing angle (MVA mode liquid crystal cells), (3) n-ASM mode liquid crystal cells in which rod-shaped liquid crystal molecules are aligned substantially vertically when no voltage is applied and substantially horizontally when a voltage is applied (described in Proceedings of the Japan Liquid Crystal Symposium 58-59 (1998)), and (4) SURVIVAL mode liquid crystal cells (announced at LCD International 98). The liquid crystal display may be of any of a PVA (Patterned Vertical Alignment) type, an optical alignment type, and a PSA (Polymer-Sustained Alignment) type. Details of these modes are described in detail in Japanese Patent Laid-Open No. 2006-215326 and Japanese Patent Laid-Open No. 2008-538819.

[0108] In an IPS mode liquid crystal cell, the liquid crystal compound is oriented substantially parallel to the substrate, and when an electric field parallel to the substrate surface is applied, the liquid crystal molecules respond in a planar manner. That is, when no electric field is applied, the liquid crystal compound is oriented in-plane. In an IPS mode, when no electric field is applied, a black display is achieved, and the absorption axes of a pair of upper and lower polarizing plates are perpendicular to each other. Methods of using an optical compensation sheet to reduce light leakage during black display in an oblique direction and improve the viewing angle are disclosed in JP-A Nos. 10-54982, 11-202323, 9-292522, 11-133408, 11-305217, and 10-307291.

[0109] [Organic EL Display Device] An organic EL display device, which is an example of the display device of the present invention, preferably has, from the viewing side, the above-mentioned circular polarizer and an organic EL display panel. In this case, the substrate, the light absorption anisotropic film, and the λ / 4 plate are arranged in this order from the viewing side. The organic EL display panel is a display panel configured using an organic EL element in which an organic light-emitting layer (organic electroluminescence layer) is sandwiched between electrodes (between a cathode and an anode). The configuration of the organic EL display panel is not particularly limited, and a known configuration may be used.

[0110] [Reflective Linear Polarizer] The display device of the present invention may include a reflective linear polarizer. The reflective linear polarizer has the effect of reflecting a portion of the light emitted from the image display panel and causing the light to travel back and forth within the optical system. From the viewpoint of suppressing stray light and ghosting, the reflective linear polarizer preferably has a high degree of polarization. As the reflective linear polarizer, a film obtained by stretching a dielectric multilayer film, such as that described in JP 2011-053705 A, and a wire grid polarizer, etc., can be used. As commercially available products, reflective polarizers (product names APF, IQPE) manufactured by 3M and wire grid polarizers (product name WGF) manufactured by Asahi Kasei Corporation can be suitably used.

[0111] [Virtual reality display device] A first aspect of the virtual reality display device, which is an example of the display device of the present invention, is a virtual reality display device having, in this order, an image display panel, a first absorptive linear polarizer (optically absorptive anisotropic film), a first retardation layer, a second retardation layer, a reflective linear polarizer, a third retardation layer, a half mirror, and a second absorptive linear polarizer (optically absorptive anisotropic film). A second aspect is a virtual reality display device having, in this order, an image display panel, a first absorptive linear polarizer, a first retardation layer, a half mirror, a reflective circular polarizer, a second retardation layer, and a second absorptive linear polarizer. A third aspect is a virtual reality display device having, in this order, an image display panel, a first absorptive linear polarizer, a first retardation layer, a half mirror, a second retardation layer, a reflective linear polarizer, and a second absorptive linear polarizer. Furthermore, it is also preferable that a fourth retardation layer be provided on the viewing side of the second absorptive linear polarizer.

[0112] The present invention will be described in more detail below with reference to examples. The materials, amounts used, ratios, treatment details, and treatment procedures shown in the following examples can be changed as appropriate without departing from the spirit of the present invention. Therefore, the scope of the present invention should not be construed as being limited by the examples shown below.

[0113] [Synthesis of Liquid Crystal Compound L1] Liquid crystal compound L1 having a ring-opening polymerizable group was synthesized according to the following synthesis scheme: A specific synthesis method is shown below.

[0114] [Synthesis of Compound L1-2] 75 ml of dimethylacetamide was added to compound L1-1 (8.1 g), potassium carbonate (6.9 g), and 1-bromo-4-chlorobutane (8.6 g) in the above scheme, and the mixture was heated and stirred at 70°C. After completion of the reaction, ethyl acetate and water were added, and the organic layer was extracted and concentrated. The extract was separated and purified by silica gel column chromatography to obtain compound L1-2 (7.3 g).

[0115] Synthesis of Compound L1-3: To a suspension of methyltriphenylphosphonium bromide (17.2 g) in anhydrous tetrahydrofuran (anhydrous THF) (10 mL) was added a solution of potassium t-butoxide in THF (1 mol / L, 48 ml) in an ice-water bath under an argon atmosphere. The resulting suspension was stirred at 0°C for 30 minutes, and a solution of compound L1-2 (6.1 g) in THF (5 mL) was added. The reaction mixture was stirred for 1 hour, and after completion of the reaction was confirmed by thin-layer chromatography (TLC), brine was added to quench the reaction. The mixture was extracted with ethyl acetate, dried over MgSO4, filtered, and concentrated to dryness. The residue was purified by silica gel chromatography to give compound L1-3 (3.2 g).

[0116] [Synthesis of Compound L1] Compound L1-4 (10 g) was synthesized according to the literature (JP 2008-101187 A). Next, 20 ml of dimethylacetamide was added to the obtained compound L1-4 (1.5 g), potassium carbonate (1.5 g), potassium iodide (0.5 g), BHT (0.1 g), and compound L1-3 (2.6 g), and the mixture was heated and stirred at 80°C. After the reaction was completed, ethyl acetate and water were added to extract the organic layer, and after concentrating, methanol was added and the precipitated crystals were filtered off. The obtained white crystals were separated and purified by silica gel column chromatography to obtain liquid crystal compound L1 (1.3 g) having a ring-opening polymerizable group. Furthermore, liquid crystal compound L1 exhibited a nematic liquid crystal phase at 143°C to 193°C. Furthermore, the liquid crystal compound L1 １ The results of H-NMR (Nuclear Magnetic Resonance) analysis are shown below. １ H-NMR (CDCl ３ ) δ8.10-8.20 (m, 4H), 7.60-7.50 (m, 4H), 7.21-7.04 (m, 3H), 7.02-6.96 (m, 4H), 6.93-6.88 (m, 4H), 5.21 (s, 2H), 4.86 (s, 2H), 4 .18-4.12 (m, 4H), 4.10-4.05 (m, 4H), 2.25 (s, 3H), 2.10-1.95 (m, 8H), 1.68-1.58 (m, 2H), 0.87-0.78 (m, 4H), 0.62-0.55 (m, 4H).

[0117] Example 1 Preparation of Alignment Film A glass substrate (Central Glass Co., Ltd., soda lime glass, size 300 mm x 300 mm, thickness 1.1 mm) was washed with an alkaline detergent, and then pure water was poured over the glass substrate, followed by drying. The following alignment film-forming composition 1 was then applied to the dried glass substrate using a #12 bar, and the applied alignment film-forming composition 1 was dried at 110°C for 2 minutes to form a coating film on the glass substrate. The resulting coating film was subjected to a rubbing treatment (roller rotation speed: 1000 rotations / spacer thickness 2.9 mm, stage speed 1.8 m / min) once to prepare alignment film 1 on the glass substrate.

[0118] --------------------------------------------------- Composition of composition 1 for forming alignment film --------------------------------------------------- Modified vinyl alcohol (see formula (PVA-1) below) 2.00 parts by mass Water 74.08 parts by mass Methanol 23.86 parts by mass Photopolymerization initiator (IRGACURE 2959, manufactured by BASF) 0.06 parts by mass

[0119] Modified polyvinyl alcohol PVA-1

[0120] [Preparation of Optically Absorbent Anisotropic Film] A 30 mm x 30 mm piece was cut out from the obtained alignment film 1, and the following liquid crystal composition 1 was spin-coated at 1000 rpm to form a coating film. The coating film was then dried at room temperature for 30 seconds, and then heated at 100°C for 30 seconds. Then, the coating film was heated at an illuminance of 30 mW / cm. ２ The irradiation was performed for 20 seconds under the irradiation conditions of 1. Thus, an optically absorptive anisotropic film 1 was formed on the alignment film 1.

[0121] ------------------------------------------------ Composition of liquid crystal composition 1------------------------------------------------ Liquid crystal compound 1 (another liquid crystal compound) below: 90 parts by mass Liquid crystal compound L1 (synthesized above) below: 10 parts by mass Dichroic material Y1 below: 6 parts by mass Polymerization initiator I1 (IRGACUREOXE-02, manufactured by BASF) 3 parts by mass Surfactant A1 below: 0.5 parts by mass Chloroform 1,900 parts by mass------------------------------------------------

[0122] liquid crystal compound 1

[0123] Liquid crystal compound L1

[0124] Dichroic substance Y1

[0125] Surfactant A1

[0126] Comparative Example 1 An optically absorbing anisotropic film H1 was prepared on an alignment film 1 in the same manner as in Example 1, except that a liquid crystal composition containing 100 parts by mass of liquid crystal compound 1 was used without containing liquid crystal compound L1.

[0127] Example 2 An optically absorptive anisotropic film 2 was prepared on an alignment film 1 in the same manner as in Example 1, except that a liquid crystal composition was used in which liquid crystal compound 1 was replaced with liquid crystal compound 2 below.

[0128] liquid crystal compound 2

[0129] Comparative Example 2 An optically absorptive anisotropic film H2 was prepared on the alignment film 1 in the same manner as in Example 2, except that the liquid crystal compound L1 was not blended and 100 parts by mass of the liquid crystal compound 2 was blended.

[0130] [Evaluation] <Degree of Orientation> With a linear polarizer inserted on the light source side of an optical microscope (Nikon Corporation, product name "ECLIPSE E600 POL"), a coating film (before curing) of each composition used and each prepared optically absorptive anisotropic film (after curing) (hereinafter collectively referred to as "sample") were set on the sample stage. Using a multichannel spectrometer (Ocean Optics, product name "QE65000"), the absorbance in the wavelength range of 380 nm to 780 nm was measured at 1 nm intervals for the samples before and after curing, and the degree of orientation in the wavelength range of 400 nm to 500 nm was calculated using the following formula. Next, the degrees of orientation of the samples before and after curing were compared, and the rate of decrease in the degree of orientation due to curing was calculated and evaluated according to the following criteria. The results are shown in Table 1 below. Degree of orientation: S = ((Az0 / Ay0) - 1) / ((Az0 / Ay0) + 2) Az0: absorbance of polarized light in the absorption axis direction of the optically absorptive anisotropic film Ay0: absorbance of polarized light in the transmission axis direction of the optically absorptive anisotropic film <Criteria> A: Decrease in degree of orientation due to curing is less than 4% B: Decrease in degree of orientation due to curing is 4% or more but less than 7% C: Decrease in degree of orientation due to curing is 7% or more

[0131]

[0132] From the results shown in Table 1 above, a comparison between Comparative Example 1 and Example 1, and a comparison between Comparative Example 2 and Example 2, it was found that by using a liquid crystal composition containing a liquid crystal compound having a ring-opening polymerizable group, the decrease in the degree of orientation due to curing can be suppressed compared to when a liquid crystal composition not containing a liquid crystal compound having a ring-opening polymerizable group is used.

Claims

1. A liquid crystal composition comprising a liquid crystal compound having a polymerizable group and a dichroic substance, wherein the polymerizable group is a ring-opening polymerizable group.

2. The liquid crystal composition according to claim 1, wherein the ring-opening polymerizable group is a radical ring-opening polymerizable group.

3. The liquid crystal composition according to claim 2, wherein the radical ring-opening polymerizable group is a group represented by the following formula (1): In the formula (1), * represents a bonding position. R1 represents a single bond or a divalent linking group, and R2 represents a hydrogen atom or a substituent. However, at least one of R1 and R2 represents a ring structure, or they are linked to each other to form a ring structure. R3 and R4 each independently represent a hydrogen atom or a substituent.

4. The liquid crystal composition according to claim 3, wherein the group represented by formula (1) is a group represented by any one of the following formulae (CP-1) to (CP-3): In the formulae (CP-1) to (CP-3), * represents a bonding position. R1 represents a single bond or a divalent linking group. Rp1 represents a substituent. Rp2 to Rp8 each independently represent a hydrogen atom or a substituent. D1 to D6 each independently represent -CR １ R ２ represents -, -C(=O)-, -O-, or -S-. １ and R ２ each independently represents a hydrogen atom or a substituent. m1 represents 1 or 2, and when m1 represents 2, multiple D1s may be the same or different. r1 represents an integer of 0 to 3, and when r1 represents 2 or 3, multiple Rp1s may be the same or different, and multiple Rp1s may be linked to each other to form a ring structure. m2 represents an integer of 0 to 5, and when m2 represents an integer of 2 to 5, multiple D2s may be the same or different. m3 represents 1 or 2, and when m3 represents 2, multiple D6s may be the same or different.

5. The liquid crystal composition according to claim 4, wherein the liquid crystal compound is a compound represented by the following formula (2) or a polymer thereof: In the formula (2), P1 and P2 each independently represent a hydrogen atom, a halogen atom, a cyano group, a nitro group, or a polymerizable group. However, at least one of P1 and P2 represents a group represented by any of the formulae (CP-1) to (CP-3). SP1 and SP2 each independently represent a single bond or a spacer group. Z1 and Z2 each independently represent a single bond, -O-, -COO-, -OCO-, -S-, -COS-, -SCO-, -NHCO-, -CONH-, -NHCONH-, -OCONH-, or -NHCOO-. A1 and A2 represent a ring structure which may have a substituent. L1 and L2 represent a single bond or a divalent linking group. n1 and n2 each independently represent an integer of 0 to 6. However, n1 + n2 represents an integer of 2 to 12. When n1 is an integer of 2 to 6, multiple Z1s may be the same or different, multiple A1s may be the same or different, and multiple L1s may be the same or different. When n2 is an integer of 2 to 6, multiple Z2s may be the same or different, multiple A2s may be the same or different, and multiple L2s may be the same or different. r1 and r2 each independently represent an integer of 1 to 3. When r1 represents 2 or 3, multiple P1s may be the same or different, and when r2 represents 2 or 3, multiple P2s may be the same or different.

6. The liquid crystal composition according to claim 5, wherein the compound represented by formula (2) exhibits nematic liquid crystallinity.

7. A liquid crystal compound which is a compound represented by the following formula (2) or a polymer thereof: In the formula (2), P1 and P2 each independently represent a hydrogen atom, a halogen atom, a cyano group, a nitro group, or a polymerizable group. However, at least one of P1 and P2 represents a group represented by the following formula (CP-1) or (CP-2). SP1 and SP2 each independently represent a single bond or a spacer group. Z1 and Z2 each independently represent a single bond, -O-, -COO-, -OCO-, -S-, -COS-, -SCO-, -NHCO-, -CONH-, -NHCONH-, -OCONH-, or -NHCOO-. A1 and A2 represent a ring structure which may have a substituent. L1 and L2 represent a single bond or a divalent linking group. G represents a divalent linking group. n1 and n2 each independently represent an integer of 0 to 6. Here, n1 + n2 represents an integer of 2 to 12. When n1 is an integer of 2 to 6, multiple Z1s may be the same or different, multiple A1s may be the same or different, and multiple L1s may be the same or different. When n2 is an integer of 2 to 6, multiple Z2s may be the same or different, multiple A2s may be the same or different, and multiple L2s may be the same or different. r1 and r2 each independently represent an integer of 1 to 3. When r1 represents 2 or 3, the multiple P1s may be the same or different from each other, and when r2 represents 2 or 3, the multiple P2s may be the same or different from each other. In the formulas (CP-1) and (CP-2), * represents a bonding position. R1 represents a single bond or a divalent linking group. Rp1 represents a substituent. Rp2 to Rp5 each independently represent a hydrogen atom or a substituent. D1 to D5 each independently represent -CR １ R ２ represents -, -C(=O)-, -O-, or -S-. １ and R ２ each independently represents a hydrogen atom or a substituent. m1 represents 1 or 2, and when m1 represents 2, multiple D1s may be the same or different. r1 represents an integer of 0 to 3, and when r1 represents 2 or 3, multiple Rp1s may be the same or different, and multiple Rp1s may be linked together to form a ring structure. m2 represents an integer of 0 to 5, and when m2 represents an integer of 2 to 5, multiple D2s may be the same or different.

8. An optically absorptive anisotropic film obtained by fixing the alignment state of the liquid crystal composition according to any one of claims 1 to 6.

9. A laminate comprising the optically absorptive anisotropic film according to claim 8 and a λ / 4 plate.

10. A display device comprising the optically absorptive anisotropic film according to claim 8 and a display element.

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