Liquid crystal composition, liquid crystal layer, optical laminate, image display device, method for producing optical laminate, and compound

Abstract

Provided is a liquid crystal composition that can suppress air-derived unevenness and that has excellent upper layer application property and liquid crystal alignment property after being formed into a layer. A liquid crystal composition according to the present invention comprises: a leveling agent that has a site that is cleaved by the action of at least one selected from the group consisting of acid, light, and heat; a photo-alignment compound; and a liquid crystal compound.

Description

Liquid crystal composition, liquid crystal layer, optical laminate, image display device, method for producing optical laminate, compound

[0001] The present invention relates to a liquid crystal composition, a liquid crystal layer, an optical laminate, an image display device, a method for producing an optical laminate, and a compound.

[0002] Optical films such as optical compensation sheets and retardation films are used in various image display devices in order to eliminate image coloration, widen the viewing angle, etc. Stretched birefringent films have been used as optical films, but in recent years, optically anisotropic layers formed using liquid crystal compounds have been proposed as replacements for stretched birefringent films.

[0003] When forming such an optically anisotropic layer, a liquid crystal layer (photo-alignment film) obtained by photo-alignment treatment may be used to align the liquid crystal compound. In the production of the liquid crystal layer, a method has been proposed in which the surface properties of the obtained liquid crystal layer are improved by using a perfluoroalkyl compound (so-called PFAS) (see Patent Document 1).

[0004] International Publication No. 2018 / 216812

[0005] However, because PFAS is persistent, it may accumulate in the environment or in living organisms, and the development of a substitute for PFAS is desired. The present inventors have investigated liquid crystal layers obtained using silicon compounds as a substitute for PFAS and have found that, depending on the solvent used, unevenness in the thickness of the liquid crystal layer caused by the drying wind during drying (hereinafter also referred to as "wind unevenness") occurs. In addition, the obtained liquid crystal layer also requires the alignment of the optically anisotropic layer formed on the liquid crystal layer (hereinafter also referred to as "liquid crystal alignment") and the coatability of the composition for the optically anisotropic layer formed on the liquid crystal layer (hereinafter also referred to as "upper layer coatability").

[0006] Therefore, an object of the present invention is to provide a liquid crystal composition, a liquid crystal layer, an optical laminate, an image display device, a method for manufacturing an optical laminate, and a compound that can suppress wind unevenness and have excellent liquid crystal alignment properties and upper layer coatability after being formed into a layer.

[0007] As a result of extensive research into achieving the above object, the present inventors have found that the above object can be achieved by the following configuration.

[0008] [1] A liquid crystal composition comprising: a leveling agent having a moiety that is cleaved by the action of at least one selected from the group consisting of acid, light, and heat; a photoalignment compound; and a liquid crystal compound. [2] The liquid crystal composition according to [1], wherein the leveling agent has a repeating unit A represented by formula (a1) described later and a repeating unit B represented by any one of formulas (b1) to (b3) described later. [3] The liquid crystal composition according to [1] or [2], wherein the content of the leveling agent is 0.01 to 5 parts by mass relative to 100 parts by mass of the liquid crystal compound. [4] L １is a group represented by any one of formulas (L1) to (L3) described later. [5] The liquid crystal composition according to any one of [1] to [4], wherein the leveling agent has a group represented by formula (1) described later. [6] The liquid crystal composition according to [2] or [4], wherein the content of the repeating unit A is 40% by mass or more and less than 100% by mass with respect to the total mass of all repeating units of the leveling agent. [7] The liquid crystal composition according to any one of [1] to [6], wherein the weight-average molecular weight of the leveling agent is 5,000 to 100,000. [8] The liquid crystal composition according to any one of [1] to [7], wherein the content of the photoalignment compound is 0.1 to 10 parts by mass with respect to 100 parts by mass of the liquid crystal compound. [9] The liquid crystal composition according to any one of [1] to [8], wherein the photo-alignment compound has a repeating unit X having a photo-alignment group and a repeating unit C having a crosslinkable group, the total content of the repeating unit X and the repeating unit C being 99 to 100% by mass with respect to the total mass of all repeating units of the photo-alignment compound, and the content of the repeating unit X being 40% by mass or more with respect to the total mass of all repeating units of the photo-alignment compound.

[10] The liquid crystal composition according to any one of [1] to [8], wherein the photo-alignment compound has a repeating unit A represented by formula (a1) described below, a repeating unit X having a photo-alignment group, and a repeating unit C having a crosslinkable group, the total content of the repeating unit A, the repeating unit X, and the repeating unit C being 99 to 100% by mass with respect to the total mass of all repeating units of the photo-alignment compound.

[11] The liquid crystal composition according to

[10] , wherein the content of the repeating unit A represented by formula (a1) is 10 to 60 mass % with respect to the total mass of all repeating units of the photoalignment compound.

[12] A liquid crystal layer formed using the liquid crystal composition according to any one of [1] to

[11] , and having alignment control ability.

[13] An optical laminate comprising the liquid crystal layer according to

[12] and an optically anisotropic layer disposed on the liquid crystal layer.

[14] An image display device comprising the optical laminate according to

[13] .

[15] A method for producing an optical laminate, comprising the steps of: subjecting a coating film obtained using the liquid crystal composition according to any one of [1] to

[11] to a photoalignment treatment to form a liquid crystal layer having alignment controllability; and applying a polymerizable liquid crystal composition containing a polymerizable liquid crystal compound onto the liquid crystal layer to form an optically anisotropic layer.

[16] A compound having a repeating unit A represented by formula (a1) described later and a repeating unit B represented by any one of formulas (b1) to (b3) described later.

[17] The compound according to

[16] , wherein the repeating unit A is a repeating unit represented by any one of formulas (a2) to (a4) described later.

[0009] According to the present invention, it is possible to provide a liquid crystal composition, a liquid crystal layer, an optical laminate, an image display device, a method for manufacturing an optical laminate, and a compound that can suppress wind unevenness and have excellent liquid crystal alignment properties and upper layer coatability after being formed into a layer.

[0010] The present invention will be described in detail below. The following description of the components may be based on representative embodiments of the present invention, but the present invention is not limited to such embodiments.

[0011] In this specification, a numerical range expressed using "to" means a range that includes the numerical values ​​written before and after "to" as the upper and lower limits. Furthermore, in this specification, in a numerical range described in stages, the upper or lower limit value described in a certain numerical range may be replaced with the upper or lower limit value of another numerical range described in stages. Furthermore, in a numerical range described in this specification, the upper or lower limit value described in a certain numerical range may be replaced with a value shown in the examples.

[0012] 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 the component refers to the total content of the substances used in combination, unless otherwise specified.

[0013] In this specification, the bonding direction of the divalent group (for example, —O—CO—) is not particularly limited. １ｚ -L ２ｚ -L ３ｚ In the bond ２ｚ When is —O—CO—, L １ｚ The position where it is bonded to the side is *1, L ３ｚ If the position bonded to the side is *2, then L ２ｚ may be *1-O-CO-*2 or *1-CO-O-*2.

[0014] [Liquid Crystal Composition] The liquid crystal composition of the present invention comprises a leveling agent (hereinafter also referred to as a "specific compound") having a moiety that is cleaved by the action of at least one selected from the group consisting of acid, light, and heat, a photoalignment compound, and a liquid crystal compound.

[0015] In the present invention, as described above, when the liquid crystal composition of the present invention is used, wind unevenness can be suppressed, and a liquid crystal layer having excellent liquid crystal alignment properties and upper layer coatability can be obtained after being formed as a layer. Although the details of this are not clear, the inventors speculate as follows. That is, it is speculated that the specific compound has leveling properties (especially when it has a repeating unit A represented by formula (a1)) and has a moiety that is cleaved by a predetermined action, thereby suppressing wind unevenness while also providing excellent upper layer coatability and liquid crystal alignment properties. Hereinafter, various components that the liquid crystal composition may contain will be described in detail.

[0016] [Specific Compound] The liquid crystal composition of the present invention contains a specific compound. The specific compound has a moiety that is cleaved by the action of at least one selected from the group consisting of acid, light, and heat, and preferably has a moiety that is cleaved by the action of at least one selected from the group consisting of acid and light. Furthermore, the specific compound preferably does not have a photoalignment group, and more preferably does not have either a photoalignment group or a fluorine atom. Furthermore, the specific compound is preferably a compound other than the photoalignment compound described below and the liquid crystal compound described below.

[0017] The moiety that is cleaved by the action of at least one selected from the group consisting of acid, light, and heat is not particularly limited as long as it is a moiety that is cleaved by the above action, but a cleavage group that decomposes to generate a polar group by the action of at least one selected from the group consisting of acid, light, and heat is preferred. The number of cleavage moieties possessed by the specific compound may be one or more, with 1 to 5 being preferred. Examples of the polar group include a hydroxyl group, a carbonyl group, a carboxyl group, an amino group, a nitro group, an ammonium group, and a cyano group, with a hydroxyl group or a carboxyl group being preferred. The term "cleavage group that generates a polar group" refers to a group that generates the above-mentioned polar group upon cleavage, and in the present invention, also includes a group that reacts with an oxygen molecule after radical cleavage to generate a polar group. Examples of the cleavage group that generates the above-mentioned polar group include a cleavage group represented by any of formulas (rk-1) to (rk-13).

[0018]

[0019] In formulas (rk-1) to (rk-13), *1 and *2 represent bonding positions, and R each independently represents a hydrogen atom or a monovalent organic group.

[0020] Examples of the monovalent organic group represented by one embodiment of R include a linear or cyclic alkyl group having 1 to 20 carbon atoms and an aryl group having 6 to 20 carbon atoms which may have a substituent.

[0021] The cleavable group represented by formula (rk-10) or formula (rk-11) may have an anion. The anion has little effect on the cleavage, so it is not particularly limited and may be either an inorganic anion or an organic anion. Examples of inorganic anions include halide ions such as chloride ion and bromide ion; and sulfonate anions. Examples of organic anions include carboxylate anions such as acetate anion; and organic sulfonate anions such as methanesulfonate anion and paratoluenesulfonate anion.

[0022] In the present invention, among the above-mentioned cleavage groups, the cleavage group represented by the above formula (rk-1) is preferred because it provides good quantum efficiency when cleaved using light, and the cleavage group represented by the above formula (rk-9) is preferred because it provides a good cleavage rate when cleaved using acid. Furthermore, an example of a moiety that is cleaved using heat is the moiety contained in Megafac DS21 (manufactured by DIC Corporation).

[0023] The specific compound preferably has a unidirectional group. The unidirectional group refers to a group that is unidirectionally distributed on the air interface side in the film when a film is formed on a substrate using a compound having the unidirectional group (a group that can cause the compound to be unidirectionally distributed on the air interface side). In other words, it refers to a group that has the function of making the content of the compound having the unidirectional group on the air interface side in the film formed by the above greater than the content of the compound having the unidirectional group on the substrate side in the film. For example, the unidirectional group may be a group that is highly hydrophobic and has the function of lowering the surface energy of the film surface on the air interface side compared to the surface energy of the film surface on the substrate interface side. Examples of the unidirectional group include a group having a fluorine atom and a group having a silicon atom, and a group having two or more silicon atoms is preferred, and a group having two or more groups represented by the formula (S) described below is more preferred.

[0024] <Repeating Unit A> The specific compound preferably has one or more repeating units A represented by formula (a1).

[0025]

[0026] In formula (a1), R １ and R ２ R each independently represents a hydrogen atom or an alkyl group. ３ represents a hydrogen atom or a substituent. X represents an (m+1)-valent linking group. L １represents an (n+1)-valent linking group having a site that is cleaved by the action of at least one selected from the group consisting of acid, light, and heat. n represents an integer of 1 to 4. m represents an integer of 1 to 5. Rh represents a substituent having two or more groups represented by formula (S) (hereinafter also referred to as "substituent SI"). However, L １ If there are multiple L １ When a plurality of Rh's are present, the Rh's may be the same or different. When a plurality of n's are present, the n's may be the same or different.

[0027] R １ and R ２ Examples of the alkyl group represented by one embodiment of R include linear alkyl groups having 1 to 18 carbon atoms, branched alkyl groups having 3 to 18 carbon atoms, and cyclic alkyl groups, and specific examples include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group (e.g., an n-butyl group, a sec-butyl group, an iso-butyl group, and a tert-butyl group), and a cyclohexyl group. １ and R ２ is preferably a hydrogen atom.

[0028] R ３ Examples of the substituent represented by one embodiment of R include a hydroxy group, an alkyl group, an alkenyl group, and an aryl group. ３ Examples of the substituents shown in one embodiment of the formula (I) include -L Ｒ -hydroxyl group, -L Ｒ -alkyl group, -L Ｒ -alkenyl group, and -L Ｒ -aryl groups are also included. Ｒ represents a divalent linking group. Ｒ Examples of the divalent linking group represented by the formula include —O—, —S—, —CO—, and —NR Ｎ -, -CH=CH-, -C≡C-, a divalent cyclic group, an alkylene group, and a divalent group combining these groups; ２ -COO-alkylene group-hydroxy group is preferred. Ｎ represents a hydrogen atom or an alkyl group having 1 to 12 carbon atoms. ３The alkyl group represented by one embodiment of R is preferably a linear alkyl group having 1 to 4 carbon atoms, and more preferably a methyl group or an ethyl group. ３ is preferably a hydrogen atom or a methyl group.

[0029] The (m+1) valent linking group represented by X is not particularly limited, but examples of divalent (i.e., m=1) linking groups include -CO-, -O-, -COO-, and -CONH-, and examples of trivalent to hexavalent (i.e., m=an integer of 2 to 5) linking groups include residues in which (m+1) hydrogen atoms bonded to carbon or nitrogen atoms constituting an aromatic ring have been removed (e.g., a benzene-1,2,3-triyl group). In addition, it is preferable that the (m+1) valent linking group does not have a site that is cleaved by the action of at least one selected from the group consisting of acid, light, and heat.

[0030] L １ The (n+1)-valent linking group represented by the formula (I) and having a moiety that is cleaved by the action of at least one selected from the group consisting of acid, light, and heat is preferably an (n+1)-valent hydrocarbon group having 1 to 24 carbon atoms that has a moiety that is cleaved by the action of at least one selected from the group consisting of acid, light, and heat and that may have a substituent, wherein some of the carbon atoms that constitute the hydrocarbon group may be substituted with heteroatoms, and more preferably an (n+1)-valent aliphatic hydrocarbon group having 1 to 10 carbon atoms that has a moiety that is cleaved by the action of at least one selected from the group consisting of acid, light, and heat and that may have an oxygen atom or a nitrogen atom.

[0031] In the present invention, L １ is preferably a group represented by any one of formulas (L1) to (L3).

[0032]

[0033] In formulas (L1) to (L3), *1 represents the bonding position with X, and *2 represents the bonding position with Rh. ｘ１ , L ｘ２ and L ｘ３R each independently represents an alkylene group having 1 to 20 carbon atoms which may have an —O— group, an aryl group having 6 to 18 carbon atoms which may have an —O— group, a combination of these, or a single bond. Ｌ１ and R Ｌ２ each independently represents a hydrogen atom or a substituent. Ｌ１ , L Ｌ２ and L Ｌ３ each independently represents a divalent linking group. Ｌ１ and m Ｌ２ Each independently represents 1 or 2. １ is a group represented by formula (L1), n ​​in formula (a1) is m Ｌ１ +m Ｌ２ Represents L １ is a group represented by formula (L2), n in formula (a1) represents 1. １ is a group represented by formula (L3), n in formula (a1) represents 2. Ｌ２ They may be the same or different. Ｌ１ They may be the same or different. Ｌ３ They may be the same or different.

[0034] L ｘ１ , L ｘ２ and L ｘ３ The alkylene group represented by one embodiment of is preferably an alkylene group having 1 to 20 carbon atoms which may have -O-, more preferably a linear alkylene group having 1 to 18 carbon atoms which may have -O-, a branched alkylene group having 3 to 18 carbon atoms which may have -O-, or a cyclic alkylene group having 3 to 20 carbon atoms which may have -O-, still more preferably a linear alkylene group having 1 to 18 carbon atoms which may have -O-, and particularly preferably a linear alkylene group having 1 to 8 carbon atoms which may have -O-. ｘ１ , L ｘ２ and L ｘ３ The aryl group represented by one embodiment of the formula (I) is preferably an aryl group having 6 to 12 carbon atoms. ｘ１ , L ｘ２ and L ｘ３As the combined group shown in one embodiment of (1), an alkylenearyl group is preferred, and an alkylenearyl group having 7 to 30 carbon atoms is more preferred.

[0035] R Ｌ１ and R Ｌ２ Examples of the substituent represented by one embodiment of R include a hydroxy group, an alkyl group, an alkenyl group, and an aryl group. Ｌ１ and R Ｌ２ The alkyl group represented by one embodiment of R is preferably a linear alkyl group having 1 to 4 carbon atoms, and more preferably a methyl group or an ethyl group. Ｌ１ and R Ｌ２ is preferably a hydrogen atom or an alkyl group.

[0036] L Ｌ１ , L Ｌ２ and L Ｌ３ Examples of the divalent linking group represented by the formula (I) include hydrocarbon groups having 1 to 20 carbon atoms, preferably alkylene groups having 1 to 20 carbon atoms, more preferably linear alkylene groups having 1 to 18 carbon atoms, branched alkylene groups having 3 to 18 carbon atoms, or cyclic alkylene groups having 3 to 20 carbon atoms, and even more preferably linear alkylene groups having 1 to 8 carbon atoms.

[0037] m Ｌ１ and m Ｌ２ It is preferable that m Ｌ１ and m Ｌ２ The sum of these is preferably an integer of 2 to 4, and more preferably 2 or 4.

[0038] The substituent SI represented by Rh is not particularly limited as long as it is a substituent having two or more groups represented by the following formula (S).

[0039]

[0040] In formula (S), * represents a bonding position. ４ , R ５ and R ６ each independently represents an alkyl group, an alkenyl group, an aryl group, or an alkylenearyl group, provided that, among the above substituents represented by Rh, R ４R may be the same or different. ５ R may be the same or different. ６ They may be the same or different.

[0041] R ４ , R ５ and R ６ Examples of the alkyl group represented by one embodiment of R include linear alkyl groups having 1 to 18 carbon atoms, branched alkyl groups having 3 to 18 carbon atoms, and cyclic alkyl groups. ４ , R ５ and R ６ Examples of the alkenyl group represented by one embodiment of R include alkenyl groups having 2 to 12 carbon atoms. ４ , R ５ and R ６ Examples of the aryl group represented by one embodiment of R include aryl groups having 6 to 12 carbon atoms. Specific examples include a phenyl group, an α-methylphenyl group, and a naphthyl group. ４ , R ５ and R ６ The alkylenearyl group represented by one embodiment of (1) above includes, for example, alkylenearyl groups having 7 to 30 carbon atoms.

[0042] The surface tension of the liquid crystal composition is reduced, and wind unevenness can be further suppressed when forming a liquid crystal layer. ４ , R ５ and R ６ As the alkyl group, an alkyl group is preferable, and a linear alkyl group having 1 to 18 carbon atoms is more preferable.

[0043] The number of groups represented by formula (S) that the substituent SI has is 2 or more, and is preferably 3 to 8, more preferably 3 to 6, and even more preferably 3 to 5, for the reasons that the surface tension of the liquid crystal composition is reduced and wind unevenness can be further suppressed during formation of a liquid crystal layer.

[0044] The substituent SI is preferably a group represented by formula (S1).

[0045]

[0046] In formula (S1), R ４ , R ５ and R６ R each independently represents an alkyl group, an alkenyl group, an aryl group, or an alkylenearyl group. Ｓ represents an alkyl group, and s represents 2 or 3. ４ R may be the same or different. ５ R may be the same or different. ６ They may be the same or different.

[0047] R in formula (S1) ４ , R ５ and R ６ are R in formula (S), respectively. ４ , R ５ and R ６ The same definition and preferred embodiments are also the same.

[0048] R Ｓ The alkyl group represented by is preferably an alkyl group having 1 to 18 carbon atoms, more preferably a linear alkyl group having 1 to 4 carbon atoms, and further preferably a methyl group or an ethyl group.

[0049] The repeating unit A is preferably a repeating unit represented by any one of formulas (a2) to (a4).

[0050]

[0051] In formulas (a2) to (a4), R １ and R ２ R each independently represents a hydrogen atom or an alkyl group. ３ represents a hydrogen atom or a substituent. ａ represents —COO— or —CONH—. ｘ１ , L ｘ２ and L ｘ３ R each independently represents an alkylene group having 1 to 20 carbon atoms which may have an —O— group, an aryl group having 6 to 18 carbon atoms which may have an —O— group, a combination of these, or a single bond. Ｌ１ and R Ｌ２ each independently represents a hydrogen atom or a substituent. Ｌ１ , L Ｌ２ and L Ｌ３each independently represents a divalent linking group. ａ represents a group represented by the above formula (S1). Ｌ１ and m Ｌ２ Each independently represents 1 or 2. Ｌ２ may be the same or different. Ｌ１ may be the same or different. Ｌ３ may be the same or different. ａ They may be the same or different.

[0052] R in formula (a2) to formula (a4) １ and R ２ are R in formula (a1), respectively. １ and R ２ The meanings and preferred embodiments are also the same. ３ is R in formula (a1). ３ The same definition and preferred embodiments are also the same.

[0053] L in formula (a2) to formula (a4) ｘ１ , L ｘ２ and L ｘ３ respectively represent L in formulas (L1) to (L3). ｘ１ , L ｘ２ and L ｘ３ The same definition and preferred embodiments are also the same.

[0054] R in formula (a2) to formula (a4) Ｌ１ and R Ｌ２ represents R in formulas (L1) to (L3), respectively. Ｌ１ and R Ｌ２ The same definition and preferred embodiments are also the same.

[0055] L in formula (a2) to formula (a4) Ｌ１ , L Ｌ２ and L Ｌ３ respectively represent L in formulas (L1) to (L3). Ｌ１ , L Ｌ２ and L Ｌ３ The same definition and preferred embodiments are also the same.

[0056] Rh ａThe group represented by formula (S1) represented by has the same meaning as the group represented by formula (S1) represented by Rh, and preferred embodiments are also the same.

[0057] m in formula (a2) to formula (a4) Ｌ１ and m Ｌ２ are m in formulas (L1) to (L3), respectively. Ｌ１ and m Ｌ２ The same definition and preferred embodiments are also the same.

[0058] The repeating unit A may be used alone or in combination of two or more types. The content of the repeating unit A is preferably 1 to 100% by mass, more preferably 30 to 100% by mass, based on the total mass of all repeating units of the specific compound, and even more preferably 40% by mass or more but less than 100% by mass, for the reason that wind unevenness is more improved.

[0059] <Repeating Unit B> The specific compound preferably has the repeating unit B, because this can further suppress aggregation in the resulting liquid crystal layer or improve compatibility with the liquid crystal compound. The specific compound may have, as the repeating unit B, a plurality of repeating units selected from the repeating unit represented by formula (b1), the repeating unit represented by formula (b2), and the repeating unit represented by formula (b3).

[0060]

[0061] In formulas (b1) to (b3), R ｂ１ , R ｂ２ , R ｂ３ and R ｂ４ each independently represents a hydrogen atom or an alkyl group. ｂ１ are each independently —O— or —NR Ｚｂ - represents. Ｚｂ represents a hydrogen atom or a substituent. ｂ２ represents a single bond or a divalent linking group. A represents an alkylene group. p represents a number of 2 or more. SP ｂ１ each independently represents a spacer group. ｂ１ represents a mesogenic group. ｂ１ each independently represents a terminal group, provided that each A may be the same or different.

[0062] R in formula (b1) to formula (b3) ｂ１ and R ｂ２ are R in formula (a1), respectively. １ and R ２ The meanings and preferred embodiments are also the same. ｂ３ is R in formula (a1). ３ The same definition and preferred embodiments are also the same.

[0063] R ｂ４ Examples of the alkyl group represented by one embodiment of (1) include linear alkyl groups having 1 to 18 carbon atoms, branched alkyl groups having 3 to 18 carbon atoms, and cyclic alkyl groups. A linear alkyl group having 1 to 4 carbon atoms is preferred, and a methyl group or an ethyl group is more preferred.

[0064] L ｂ１ One aspect of the invention is represented by -NR Ｚｂ -About R Ｚｂ The substituent represented by one embodiment of the formula (I) is preferably an alkyl group, more preferably a linear alkyl group having 1 to 4 carbon atoms, and even more preferably a methyl group or an ethyl group. ｂ１ As the group, —O— or —NH— is preferable, and —O— is more preferable.

[0065] L ｂ２ Examples of the divalent linking group represented by one embodiment of the formula (I) include divalent hydrocarbon groups having 1 to 20 carbon atoms, preferably alkylene groups having 1 to 20 carbon atoms, and more preferably linear alkylene groups having 1 to 18 carbon atoms, branched alkylene groups having 3 to 18 carbon atoms, or cyclic alkylene groups having 3 to 20 carbon atoms. ｂ２ is preferably a single bond or a linear alkylene group having 1 to 18 carbon atoms, and more preferably a single bond.

[0066] The number of carbon atoms in the alkylene group represented by A is preferably 1 to 4, and more preferably 2 or 3. For example, when A is an alkylene group having 1 carbon atom, -A-O- in formula (b1) is an oxymethylene group (-CH ２ When A is an alkylene group having 2 carbon atoms, -A-O- in formula (b1) represents an oxyethylene group (-CH ２ CH ２The alkylene group may be either linear or branched. -(A-O) ｐ The - may be an oxyalkylene group formed by linking an oxymethylene group and an oxypropylene group. The bonding order of each repeating unit may be either random or block.

[0067] The number represented by p is 2 or more, preferably a number from 2 to 1,000, and more preferably a number from 2 to 25.

[0068] SP ｂ１ The spacer group represented by the formula (I) is not particularly limited as long as it is a divalent linking group that does not have a ring structure. ｂ１ Examples of the spacer group represented by the formula (I) include divalent aliphatic hydrocarbon groups having 1 to 20 carbon atoms. As the divalent aliphatic hydrocarbon group having 1 to 20 carbon atoms, an alkylene group having 1 to 15 carbon atoms is preferred, and an alkylene group having 1 to 8 carbon atoms is more preferred. Specific examples include a methylene group, an ethylene group, a propylene group, a butylene group, a pentylene group, a hexylene group, a methylhexylene group, and a heptylene group. In addition, the spacer group may be a -CH group that constitutes a part of the divalent aliphatic hydrocarbon group. ２ -, one or two or more non-adjacent -CH ２ - is each independently -O-, -CO-, -S-, -NH-, -CH(Q)-, or -C(Q) ２ - or -N(Q)-. Each Q independently represents a substituent. The substituent represented by Q is preferably a hydroxyl group or an alkyl group. The alkyl group is preferably a linear alkyl group having 1 to 4 carbon atoms, more preferably a methyl group or an ethyl group.

[0069] M ｂ１The mesogenic group represented by is a group that represents the main skeleton of a liquid crystal molecule that contributes to the formation of liquid crystals. The liquid crystal molecules exhibit liquid crystallinity, which is an intermediate state (mesophase) between a crystalline state and an isotropic liquid state. For mesogenic groups, reference can be made to, for example, "Flussige Kristalle in Tablellen II" (VEB Deutsche Verlag fur Grundstoff Industrie, Leipzig, published in 1984), particularly the description on pages 7 to 16, and "Liquid Crystal Handbook" edited by the Liquid Crystal Handbook Editorial Committee (Maruzen, published in 2000), particularly the description in Chapter 3. The mesogenic group is preferably a group having at least one cyclic structure selected from the group consisting of aromatic hydrocarbon groups, heterocyclic groups, and alicyclic groups, more preferably a group having an aromatic hydrocarbon group (preferably 1 to 5 groups) or an alicyclic group (preferably 1 to 5 groups), and even more preferably a group having 2 to 4 aromatic hydrocarbon groups. The mesogenic group may have a substituent from the viewpoint of improving the degree of alignment of the cured liquid crystal layer. The substituent is preferably an alkyl group, an alkoxy group, an alkyl ester group, or an acetyl group, and more preferably a methyl group, a tert-butyl group, a methoxy group, or a methyl ester group.

[0070] M ｂ１ As the mesogenic group, a mesogenic group represented by formula (M1-A) is preferred from the viewpoint of further suppressing repelling during the formation of a liquid crystal cured layer.

[0071]

[0072] In formula (M1-A), * represents a bonding position. １１ and Ph １２ each independently represents a divalent aromatic ring group which may have a substituent. ｍ１ represents a single bond or a divalent linking group. ｍ represents an integer of 0 or 1 or more. １１ If there are multiple Ph １１ may be the same or different. ｍ１ If there are multiple L ｍ１ They may be the same or different.

[0073] Ph１１ and Ph １２ Examples of the divalent aromatic ring group represented by the formula (I) include a group in which two hydrogen atoms have been removed from an aromatic hydrocarbon ring, and a group in which two hydrogen atoms have been removed from an aromatic heterocycle. Examples of the aromatic hydrocarbon ring include a benzene ring, a naphthalene ring, an anthracene ring, and a phenanthroline ring. Examples of the aromatic heterocycle include a furan ring, a pyrrole ring, a thiophene ring, a pyridine ring, a thiazole ring, and a benzothiazole ring. Ph １１ and Ph １２ The divalent aromatic ring group represented by is preferably a group in which two hydrogen atoms have been removed from a benzene ring (for example, a 1,4-phenyl group). As a substituent that the divalent aromatic ring group may have, an alkyl ester group, an alkyl group, or an acetyl group is preferred, a methyl ester group or a linear alkyl group having 1 to 4 carbon atoms is more preferred, and a methyl group or an ethyl group is even more preferred.

[0074] L ｍ１ Examples of the divalent linking group in one embodiment include —CO—, —O—, —S—, —C(═S)—, —C(R ｍ１ ) (R ｍ２ ) -, -C(R ｍ３ ) = C(R ｍ４ ) -, -N(R ｍ５ )- and combinations thereof. ｍ１ ~R ｍ５ each independently represents a hydrogen atom, a fluorine atom, or an alkyl group having 1 to 12 carbon atoms.

[0075] n ｍ is preferably an integer of 1 to 10. ｍ is also preferably an integer of 0 to 10.

[0076] T ｂ１Examples of the terminal group represented by T include polymerizable groups such as a hydrogen atom, a halogen atom, a cyano group, a nitro group, a hydroxy group, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms, an alkoxycarbonyloxy group having 1 to 10 carbon atoms, an alkoxycarbonyl group having 1 to 10 carbon atoms, an acyloxy group having 1 to 10 carbon atoms, an acylamino group having 1 to 10 carbon atoms, an alkoxycarbonylamino group having 1 to 10 carbon atoms, a sulfonylamino group having 1 to 10 carbon atoms, a sulfamoyl group having 1 to 10 carbon atoms, a carbamoyl group having 1 to 10 carbon atoms, a sulfinyl group having 1 to 10 carbon atoms, a ureido group having 1 to 10 carbon atoms, a (meth)acryloyloxy group, and combinations thereof. ｂ１ is preferably a hydrogen atom or a polymerizable group, more preferably a hydrogen atom or a (meth)acryloyloxy group.

[0077] The repeating unit B may be used alone or in combination of two or more types. The total content of the repeating unit A and the repeating unit B is preferably 90 to 100 mass%, more preferably 99 to 100 mass%, and even more preferably 99.9 to 100 mass%, based on the total mass of all repeating units of the specific compound. Furthermore, it is preferable that the specific compound has only the repeating unit A and the repeating unit B as repeating units.

[0078] <Other Repeating Units> The specific compound may have other repeating units in addition to the repeating unit A and the repeating unit B. Examples of the other repeating units include repeating units derived from compounds such as maleimide compounds, maleic anhydride, styrene compounds, liquid crystal compounds, and vinyl compounds. The other repeating units may be used alone or in combination of two or more.

[0079] The specific compound preferably has a group represented by formula (1).

[0080]

[0081] In formula (1), * represents a bonding position. ７ , R ８ and R １２R each independently represents a hydrogen atom or a substituent. ９ , R １０ , R １１ , R １３ , R １４ and R １５ each independently represents an alkyl group, an alkenyl group, an aryl group, or an alkylenearyl group. x and y each independently represent an integer of 1 to 3. v and w each independently represent an integer of 1 to 4. When v represents 1, L ２ represents a single bond or a divalent linking group, and when v represents an integer of 2 to 4, L ２ represents a linking group with a valence of v+1. When w represents 1, L ３ represents a single bond or a divalent linking group, and when w represents an integer of 2 to 4, L ３ represents a w+1 valent linking group. ８ If there are multiple R ８ R may be the same or different. １２ If there are multiple R １２ R may be the same or different. ９ If there are multiple R ９ R may be the same or different. １０ If there are multiple R １０ R may be the same or different. １１ If there are multiple R １１ R may be the same or different. １３ If there are multiple R １３ R may be the same or different. １４ If there are multiple R １４ R may be the same or different. １５ If there are multiple R １５ They may be the same or different.

[0082] R ７ , R ８ and R １２ Examples of the substituent represented by one embodiment of R include a hydroxy group, an alkyl group, an alkenyl group, and an aryl group. ７ , R ８ and R１２ The alkyl group represented by one embodiment of R is preferably a linear alkyl group having 1 to 4 carbon atoms, and more preferably a methyl group or an ethyl group. ７ R is preferably a hydrogen atom or an alkyl group, more preferably a hydrogen atom. ８ and R １２ R is preferably a hydrogen atom or an alkyl group, more preferably an alkyl group, and further preferably a methyl group or an ethyl group. ８ and R １２ In formula (S1), R Ｓ The alkyl group represented by the formula: is also preferred.

[0083] L ２ and L ３ Examples of the divalent linking group represented by one embodiment of the formula (I) include hydrocarbon groups having 1 to 20 carbon atoms, preferably alkylene groups having 1 to 20 carbon atoms, more preferably linear alkylene groups having 1 to 18 carbon atoms, branched alkylene groups having 3 to 18 carbon atoms, or cyclic alkylene groups having 3 to 20 carbon atoms, and even more preferably linear alkylene groups having 1 to 8 carbon atoms. ２ and L ３ Examples of the w+1 valent linking group shown in one embodiment of (a) include, for example, a trivalent to pentavalent linking group (i.e., v or w = an integer of 2 to 4), a residue in which v+1 or w+1 hydrogen atoms bonded to carbon or nitrogen atoms constituting an aromatic ring have been removed (e.g., a benzene-1,2,3-triyl group), and a residue in which v+1 or w+1 hydrogen atoms have been removed from an aliphatic hydrocarbon. The aliphatic hydrocarbon is preferably an aliphatic hydrocarbon having 1 to 20 carbon atoms, more preferably an aliphatic hydrocarbon having 1 to 10 carbon atoms.

[0084] R ９ , R １０ , R １１ , R １３ , R １４ and R １５ are R in formula (S), respectively. ４ , R ５ and R ６ The same definition and preferred embodiments are also the same.

[0085] x and y are preferably 2 or 3. v and w are preferably 1 or 2.

[0086] Specific examples of the repeating unit A that the specific compound may have are shown below: In the following formula, Me represents a methyl group.

[0087]

[0088] Specific examples of the repeating unit B that the specific compound may have are shown below: In the following formula, p represents a number of 2 or more and has the same meaning as p in formula (b1) above.

[0089]

[0090] Specific examples of other repeating units that the specific compound may have are shown below.

[0091]

[0092] The weight-average molecular weight of the specific compound is preferably 2,000 to 1,000,000, and more preferably 5,000 to 100,000 because wind unevenness is improved. The weight-average molecular weight is a value measured by gel permeation chromatography (GPC). Solvent (eluent): tetrahydrofuran (THF) Apparatus name: EcoSEC HLC-8320GPC (manufactured by Tosoh Corporation) Column: Three columns were connected: TSKgel SuperHZM-H, TSKgel SuperHZ4000, and TSKgel SuperHZ200 (all manufactured by Tosoh Corporation) Column temperature: 40°C Sample concentration: 0.1% by mass Flow rate: 0.35 mL / min Calibration curve: A calibration curve using six samples of TSK standard polystyrene manufactured by Tosoh Corporation with Mw = 706,000 to 1013 (Mw / Mn = 1.03 to 1.06) was used.

[0093] The specific compound may be used alone or in combination of two or more. The content of the specific compound is preferably 0.001 to 10 parts by mass, more preferably 0.01 to 5 parts by mass, and even more preferably 0.1 to 3 parts by mass, relative to 100 parts by mass of the liquid crystal compound, for the reason that wind unevenness is further improved.

[0094] [Photo-alignment compound] The liquid crystal composition of the present invention contains a photo-alignment compound. The photo-alignment compound is a compound having a photo-alignment group. Furthermore, it is preferable that the photo-alignment compound does not have a fluorine atom. The photo-alignment group refers to a group having a photo-alignment function that induces rearrangement or an anisotropic chemical reaction when irradiated with anisotropic light (e.g., plane polarized light, etc.). A photo-alignment group that undergoes at least one of dimerization and isomerization under the action of light is preferred because it provides excellent alignment uniformity and good thermal and chemical stability.

[0095] Examples of photo-alignable groups that dimerize under the action of light include groups having a skeleton of at least one derivative selected from the group consisting of cinnamic acid derivatives, coumarin derivatives, chalcone derivatives, maleimide derivatives, and benzophenone derivatives. Examples of photo-alignable groups that isomerize under the action of light include groups having a skeleton of at least one compound selected from the group consisting of azobenzene compounds, stilbene compounds, spiropyran compounds, cinnamic acid compounds, and hydrazono-β-ketoester compounds.

[0096] The photoalignable group is preferably a group having a skeleton of at least one derivative selected from the group consisting of cinnamic acid derivatives, coumarin derivatives, chalcone derivatives, and maleimide derivatives, or a group having a skeleton of at least one compound selected from the group consisting of azobenzene compounds, stilbene compounds, and spiropyran compounds, and more preferably a group having a cinnamic acid derivative skeleton or a coumarin derivative skeleton.

[0097] The main chain structure of the repeating unit having a photo-alignment group can be, for example, a known structure.Among them, the main chain structure of the repeating unit X having a photo-alignment group is preferably a skeleton selected from the group consisting of (meth)acrylic, styrene, siloxane, cycloolefin, methylpentene, amide and aromatic ester, more preferably a skeleton selected from the group consisting of (meth)acrylic, siloxane and cycloolefin, and even more preferably a (meth)acrylic skeleton.

[0098] <Repeating Unit X> The photoalignment compound preferably has a repeating unit X having the above-described photoalignment group, more preferably has a repeating unit represented by formula (X1), and further preferably has a repeating unit represented by formula (X2).

[0099]

[0100] In formula (X1), R Ｘ１ and R Ｘ２ R each independently represents a hydrogen atom or an alkyl group. Ｘ３ represents a hydrogen atom or a substituent. Ｘ１ represents a single bond or a divalent linking group. Ｘ represents a photoalignable group.

[0101] R Ｘ１ and R Ｘ２ are R in formula (a1), respectively. １ and R ２ The same definition and preferred embodiments are also the same. Ｘ３ is R in formula (a1). ３ The same definition and preferred embodiments are also the same.

[0102] L Ｘ１ Examples of the divalent linking group in one embodiment of the formula (I) include —O—, —S—, —CO—, —NR ＮＸ -, -CH=CH-, -C≡C-, an arylene group, an alkylene group, and a divalent group formed by combining these groups. ＮＸ represents a hydrogen atom or a substituent. The substituent is preferably an alkyl group. Ｘ１ The alkylene group represented by one embodiment of is preferably an alkylene group having 1 to 20 carbon atoms, more preferably a linear alkylene group having 1 to 18 carbon atoms, a branched alkylene group having 3 to 18 carbon atoms, or a cyclic alkylene group having 3 to 20 carbon atoms, still more preferably a cyclic alkylene group having 3 to 20 carbon atoms, and particularly preferably a cyclic alkylene group having 3 to 10 carbon atoms and a 5- or 6-membered ring (a 5- or 6-membered cycloalkylene group having 3 to 10 carbon atoms). Ｘ１ Examples thereof include -COO- and -CONR ＮＸPreferred are --, --O--, an alkylene group, or a group formed by combining these.

[0103] T Ｘ１ The photo-alignment group represented by has the same meaning as the photo-alignment group contained in the above-mentioned photo-alignment compound, and the preferred embodiments are also the same.

[0104]

[0105] In formula (X2), R Ｘ４ represents a hydrogen atom or an alkyl group. Ｘ２ represents —COO— or —CONH—. Ｘ３ represents a cyclic alkylene group, —O—, —S—, —NQ—, —CO—, or a group formed by combining these. Ｘ５ , R Ｘ６ , R Ｘ７ , R Ｘ８ and R Ｘ９ each independently represents a hydrogen atom or a substituent.

[0106] R Ｘ４ The alkyl group represented by one embodiment of R is preferably a linear alkyl group having 1 to 4 carbon atoms, and more preferably a methyl group or an ethyl group. Ｘ４ is preferably a hydrogen atom or a methyl group.

[0107] L Ｘ２ As the group, —CONH— is preferred.

[0108] L Ｘ３ The cyclic alkylene group represented by one embodiment of is preferably a cyclic alkylene group having 3 to 20 carbon atoms, more preferably a cyclic alkylene group having 5 to 10 carbon atoms. The cyclic alkylene group may be either monocyclic or polycyclic, with monocyclic being preferred. The number of ring members in the cyclic alkylene group is preferably 3 to 12, more preferably 5 or 6. The cyclic alkylene group is preferably a cyclopentylene group or a cyclohexylene group. L Ｘ３ is preferably a cyclic alkylene group, -cyclic alkylene group -O-, or cyclic alkylene group -NH-.

[0109] R Ｘ５ , R Ｘ６ , RＸ７ , R Ｘ８ and R Ｘ９ Preferred examples of the substituent represented by one embodiment of the formula (I) include a halogen atom, a linear alkyl group having 1 to 20 carbon atoms, a branched or cyclic alkyl group having 3 to 20 carbon atoms, a linear halogenated alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, an aryloxy group having 6 to 20 carbon atoms, a hydroxy group, a cyano group, an amino group, and an —O—CO- hydrocarbon group (the hydrocarbon group is preferably an alkyl group having 1 to 20 carbon atoms).

[0110] Examples of halogen atoms include fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms.

[0111] As the linear alkyl group having 1 to 20 carbon atoms, an alkyl group having 1 to 6 carbon atoms is preferred, and examples thereof include a methyl group, an ethyl group, and an n-propyl group. As the branched alkyl group having 3 to 20 carbon atoms, an alkyl group having 3 to 6 carbon atoms is preferred, and examples thereof include an isopropyl group and a tert-butyl group. As the cyclic alkyl group, an alkyl group having 3 to 6 carbon atoms is preferred, and examples thereof include a cyclopropyl group, a cyclopentyl group, and a cyclohexyl group.

[0112] Examples of the linear halogenated alkyl group having 1 to 20 carbon atoms include a fluoroalkyl group having 1 to 4 carbon atoms.

[0113] The alkoxy group having 1 to 20 carbon atoms is preferably an alkoxy group having 1 to 18 carbon atoms, more preferably an alkoxy group having 3 to 18 carbon atoms, and even more preferably an alkoxy group having 6 to 18 carbon atoms. Examples of the alkoxy group having 1 to 20 carbon atoms include a methoxy group, an ethoxy group, an n-butoxy group, a methoxyethoxy group, an n-hexyloxy group, an n-octyloxy group, an n-decyloxy group, an n-dodecyloxy group, and an n-tetradecyloxy group.

[0114] As the aryl group having 6 to 20 carbon atoms, an aryl group having 6 to 12 carbon atoms is preferred, and examples thereof include a phenyl group, an α-methylphenyl group, and a naphthyl group.

[0115] As the aryloxy group having 6 to 20 carbon atoms, an aryloxy group having 6 to 12 carbon atoms is preferred, and examples thereof include a phenyloxy group and a 2-naphthyloxy group.

[0116] The amino group may be, for example, a primary amino group (—NH ２ ), secondary amino groups such as a methylamino group; and tertiary amino groups such as a dimethylamino group, a diethylamino group, a dibenzylamino group, and groups in which the nitrogen atom of a nitrogen-containing heterocyclic compound (e.g., pyrrolidine, piperidine, piperazine, etc.) serves as a bonding bond.

[0117] The photo-alignment compound easily interacts with the liquid crystal compound, resulting in good liquid crystal alignment. Ｘ５ , R Ｘ６ , R Ｘ７ , R Ｘ８ and R Ｘ９ Among them, at least R Ｘ７ represents the above-mentioned substituent (preferably an alkoxy group having 1 to 20 carbon atoms), and further, for the reasons that the linearity of the obtained photoalignment polymer is improved, interaction with the liquid crystal compound becomes easier, and the liquid crystal alignment property becomes better, R Ｘ５ , R Ｘ６ , R Ｘ８ and R Ｘ９ More preferably, both represent a hydrogen atom.

[0118] The repeating unit X may be used singly or in combination of two or more types. The content of the repeating unit X is preferably 10 to 90 mass %, more preferably 20 to 80 mass %, and even more preferably 40 to 80 mass %, based on the total mass of all repeating units of the photoalignment compound.

[0119] <Repeating Unit C> The photoalignment compound preferably has a repeating unit C having a crosslinkable group.

[0120] The photoalignment compound preferably has a repeating unit C having a crosslinkable group, because the improved solvent resistance suppresses alignment relaxation, resulting in better liquid crystal alignment. The type of crosslinkable group is not particularly limited, and known crosslinkable groups can be used. A cationically polymerizable group or a radically polymerizable group is preferred, because they provide good adhesion to an upper layer disposed on the liquid crystal layer.

[0121] Examples of the cationically polymerizable group include an epoxy group, an epoxycyclohexyl group, and an oxetanyl group.

[0122] Examples of the radically polymerizable group include an acryloyl group, a methacryloyl group, a vinyl group, a styryl group, and an allyl group.

[0123] The repeating unit C having a crosslinkable group is preferably a repeating unit represented by the following formula (C) because it provides better liquid crystal alignment properties.

[0124]

[0125] In formula (C), R Ｃ１ represents a hydrogen atom or a substituent. Ｃ１ represents a single bond or a divalent linking group. Ｃ２ is m Ｃ represents a +1-valent linking group. Z represents a crosslinkable group. m Ｃ represents an integer of 1 or more, provided that multiple Z's may be the same or different.

[0126] R Ｃ１ is R in formula (a1). ３ The meanings and preferred embodiments of the substituents are the same as those of the substituents represented by one embodiment of the formula (I) and (II).

[0127] L Ｃ１ Examples of the divalent linking group represented by one embodiment of the formula (I) include: Ｘ１ In order to obtain better liquid crystal alignment properties, examples of the divalent linking group include a linear alkylene group having 1 to 10 carbon atoms which may have a substituent, a branched or cyclic alkylene group having 3 to 10 carbon atoms, an arylene group having 6 to 12 carbon atoms which may have a substituent, -O-, -CO-, and -N(Q ＣA divalent linking group formed by combining at least two or more (preferably 2 to 8) groups selected from the group consisting of —CO—O— is preferred, and —CO—O— is more preferred. Ｃ represents a hydrogen atom or a substituent.

[0128] L Ｃ２ indicates m Ｃ As the +1-valent linking group, m Ｃ A monovalent hydrocarbon group in which some of the carbon atoms constituting the hydrocarbon group may be substituted with heteroatoms is preferred, an aliphatic hydrocarbon group having 1 to 10 carbon atoms which may contain an oxygen atom or a nitrogen atom is more preferred, and an aliphatic hydrocarbon group having 1 to 5 carbon atoms is even more preferred.

[0129] m Ｃ The number of carbon atoms contained in the +1-valent linking group is not particularly limited, and is preferably 1 to 24, more preferably 1 to 10, and even more preferably 1 to 5, for reasons of better liquid crystal alignment properties.

[0130] m Ｃ is preferably an integer of 1 to 5, more preferably an integer of 1 to 3, and even more preferably 1, because this improves the liquid crystal alignment property.

[0131] The crosslinkable group represented by Z has the same meaning as the crosslinkable group contained in the repeating unit C described above, and the preferred embodiments are also the same.

[0132] Specific examples of the repeating unit C include repeating units represented by any of the following formulae C-1 to C-10.

[0133]

[0134] The repeating unit C may be used alone or in combination of two or more types. The content of the repeating unit C is preferably 10 to 90 mass %, more preferably 20 to 80 mass %, and even more preferably 30 to 70 mass %, based on the total repeating units of the photoalignment compound, because this improves the liquid crystal alignment property.

[0135] <Repeating unit A> The photoalignment compound preferably has the above-mentioned repeating unit A. That is, it preferably has a repeating unit having a moiety that is cleaved by the action of at least one selected from the group consisting of acid, light, and heat. Examples of the repeating unit A include the repeating unit A that can be contained in the specific compound.

[0136] The repeating unit A may be used alone or in combination of two or more types. The content of the repeating unit A is preferably 10 to 90 mass% and more preferably 10 to 60 mass% relative to the total mass of all repeating units of the photoalignment compound. The content of the repeating unit A is also preferably 40 mass% or more relative to the total mass of all repeating units of the photoalignment compound. The upper limit is preferably 60 mass% or less.

[0137] The total content of repeating units X and C is preferably 99 to 100 mass%, more preferably 99.9 to 100 mass%, based on the total mass of all repeating units of the photoalignment compound. The total content of repeating units A, X and C is preferably 99 to 100 mass%, more preferably 99.9 to 100 mass%, based on the total mass of all repeating units of the photoalignment compound.

[0138] The photo-alignment compound has a repeating unit X having a photo-alignment group and a repeating unit C having a crosslinkable group, and the total content of the repeating unit X and the repeating unit C is preferably 99 to 100% by mass, based on the total mass of all repeating units of the photo-alignment compound, and the content of the repeating unit X is preferably 40% by mass or more, based on the total mass of all repeating units of the photo-alignment compound. In the above case, the photo-alignment compound preferably has only the repeating unit X and the repeating unit C as repeating units. Furthermore, the photo-alignment compound preferably has a repeating unit A represented by formula (a1), a repeating unit X having a photo-alignment group, and a repeating unit C having a crosslinkable group, and the total content of the repeating unit A, the repeating unit X, and the repeating unit C is preferably 99 to 100% by mass, based on the total mass of all repeating units of the photo-alignment compound. Furthermore, the content of the repeating unit A is more preferably 10 to 60% by mass, based on the total mass of all repeating units of the photo-alignment compound. In the above case, the photo-alignment compound preferably has only the repeating unit A, the repeating unit X, and the repeating unit C as repeating units.

[0139] The content of the photo-alignment compound is preferably 0.01 to 10.0 parts by mass, more preferably 0.1 to 10.0 parts by mass, and even more preferably 0.5 to 5.0 parts by mass, relative to 100 parts by mass of the liquid crystal compound, because this improves the liquid crystal alignment.

[0140] [Liquid Crystal Compound] The liquid crystal composition of the present invention contains a liquid crystal compound. The type of liquid crystal compound is not particularly limited. Generally, liquid crystal compounds can be classified into rod-shaped and discotic types based on their shape. Each type can further be divided into low-molecular-weight and high-molecular-weight types. The high-molecular-weight type generally refers to a compound with a degree of polymerization of 100 or more (Polymer Physics / Phase Transition Dynamics, Masao Doi, p. 2, Iwanami Shoten, 1992).

[0141] The liquid crystal compound is preferably a rod-shaped liquid crystal compound or a discotic liquid crystal compound (discotic liquid crystal compound). The liquid crystal compound may be a mixture of two or more rod-shaped liquid crystal compounds, two or more discotic liquid crystal compounds, or a mixture of a rod-shaped liquid crystal compound and a discotic liquid crystal compound.

[0142] The liquid crystal compound is preferably a polymerizable liquid crystal compound having a polymerizable group. The polymerizable liquid crystal compound is preferably at least one polymerizable liquid crystal compound selected from the group consisting of polymerizable rod-shaped liquid crystal compounds and polymerizable discotic liquid crystal compounds. Examples of the polymerizable group include a (meth)acryloyl group, an epoxy group, and a vinyl group. The orientation of the liquid crystal compound can be fixed by polymerizing the liquid crystal compound having the polymerizable group. It is not necessary for the liquid crystal compound to exhibit liquid crystallinity after being fixed by polymerization.

[0143] As the rod-shaped liquid crystal compound, those described in claim 1 of JP-A No. 11-513019 or paragraphs

[0026] to

[0098] of JP-A No. 2005-289980 are preferred. As the discotic liquid crystal compound, those described in paragraphs

[0020] to

[0067] of JP-A No. 2007-108732 or paragraphs

[0013] to

[0108] of JP-A No. 2010-244038 are preferred. Furthermore, as the liquid crystal compound, a liquid crystal compound with reverse wavelength dispersion may be used.

[0144] The liquid crystal compound may be used alone or in combination of two or more. The content of the liquid crystal compound is preferably 10 to 99% by mass, more preferably 50 to 95% by mass, based on the total solid content (100% by mass) of the liquid crystal composition.

[0145] [Solvent] From the viewpoint of workability and the like, the liquid crystal composition of the present invention preferably contains a solvent. The solvent may be either a single solvent or a mixed solvent. The solvent preferably contains solvent A having a boiling point of 100°C or less, and the content of solvent A is preferably 35% by mass or more relative to the total mass of the solvent. The content of solvent A is preferably 45% by mass or more relative to the total mass of the solvent. The upper limit may be 100% by mass or less, preferably 80% by mass or less, and more preferably 60% by mass or less. In this specification, "boiling point" refers to the normal boiling point. When a conventional liquid crystal composition contains a predetermined amount of solvent A as described above, the problem of wind unevenness is more likely to become apparent in the conventional liquid crystal composition, whereas the liquid crystal composition of the present invention can suppress wind unevenness even in the above case.

[0146] Examples of the solvent include ketones (e.g., acetone, 2-butanone, methyl ethyl ketone, methyl isobutyl ketone, cyclopentanone, and cyclohexanone), ethers (e.g., dioxane, tetrahydrofuran, tetrahydropyran, dioxolane, tetrahydrofurfuryl alcohol, propylene glycol monomethyl ether acetate, 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, dichlorobenzyl ether, and the like), and the like. Examples of suitable solvents include organic solvents such as benzene and chlorotoluene, esters (e.g., methyl acetate, ethyl acetate, ethyl propionate, butyl acetate, and diethyl carbonate), alcohols (e.g., methanol, ethanol, isopropanol, butanol, and cyclohexanol), cellosolves (e.g., methyl cellosolve, ethyl cellosolve, and 1,2-dimethoxyethane), cellosolve acetates, sulfoxides (e.g., dimethyl sulfoxide), amides (e.g., dimethylformamide, dimethylacetamide, N-methylpyrrolidone, N-ethylpyrrolidone, and 1,3-dimethyl-2-imidazolidinone), and heterocyclic compounds (e.g., pyridine), as well as water. These solvents may be used singly or in combination of two or more.

[0147] From the viewpoint of improving the alignment property and heat resistance of the cured liquid crystal layer formed using the liquid crystal composition, the solvent is preferably an organic solvent, and more preferably a ketone and / or an ester.

[0148] [Photoacid Generator] The liquid crystal composition of the present invention may contain a photoacid generator. The photoacid generator is not particularly limited, and is preferably a compound that is sensitive to actinic rays having a wavelength of 300 nm or more, preferably 300 to 450 nm, and generates an acid. Furthermore, even if a photoacid generator is not directly sensitive to actinic rays having a wavelength of 300 nm or more, it can be preferably used in combination with a sensitizer, as long as it is a compound that is sensitive to actinic rays having a wavelength of 300 nm or more and generates an acid when used in combination with a sensitizer.

[0149] Examples of photoacid generators include onium salt compounds, trichloromethyl-s-triazines, sulfonium salts, iodonium salts, quaternary ammonium salts, diazomethane compounds, imide sulfonate compounds, and oxime sulfonate compounds. Among these, onium salt compounds, imide sulfonate compounds, and oxime sulfonate compounds are preferred, and onium salt compounds and oxime sulfonate compounds are more preferred. The photoacid generators can be used alone or in combination of two or more.

[0150] [Polymerization Initiator] The liquid crystal composition of the present invention may contain a polymerization initiator. The polymerization initiator is preferably a photosensitive compound (i.e., a photopolymerization initiator). Examples of the photopolymerization initiator include α-carbonyl compounds, acyloin ethers, α-hydrocarbon-substituted aromatic acyloin compounds, polynuclear quinone compounds, combinations of triarylimidazole dimers and p-aminophenyl ketones, acridines, phenazine compounds, oxadiazole compounds, o-acyloxime compounds, acylphosphine oxide compounds, and oxime-type polymerization initiators. Commercially available photopolymerization initiators include Irgacure-184, Irgacure-907, Irgacure-369, Irgacure-651, Irgacure (Ominirad)-819, Irgacure-OXE-01, and Irgacure-OXE-02, all manufactured by BASF.

[0151] The polymerization initiator may be used alone or in combination of two or more. When the liquid crystal composition contains a polymerization initiator, the content of the polymerization initiator is preferably 0.01 to 30 mass %, more preferably 0.1 to 15 mass %, based on the total solid content (100 mass %) of the liquid crystal composition.

[0152] The liquid crystal composition may contain other components in addition to the above-mentioned various components, such as a polyfunctional monomer, an alignment aid such as a horizontal alignment agent or a vertical alignment agent, an adhesion improver, and a plasticizer.

[0153] [Liquid Crystal Layer] The liquid crystal layer of the present invention is not particularly limited as long as it is a layer formed using the liquid crystal composition of the present invention described above. The liquid crystal layer is formed by subjecting the liquid crystal composition to a curing treatment. Furthermore, the liquid crystal layer is preferably a layer whose surface has alignment control ability. Having alignment control ability means that the liquid crystal compound disposed on the liquid crystal layer has the function of aligning in a predetermined direction. A method for forming a liquid crystal layer whose surface has alignment control ability preferably includes, for example, a step (Step 1) of generating an acid from a photoacid generator in a coating film obtained using the liquid crystal composition, and then subjecting the coating film to a photoalignment treatment to form a liquid crystal layer having alignment control ability. When the liquid crystal composition contains a polymerizable liquid crystal compound, in Step 1, it is preferable to subject the coating film obtained using the liquid crystal composition to a curing treatment, followed by a treatment to generate an acid from the photoacid generator in the coating film (hereinafter simply referred to as "acid generation treatment"), and then subjecting the coating film to a photoalignment treatment to form a liquid crystal layer. The method for performing the curing treatment is described in detail below.

[0154] The method for forming a coating film of the liquid crystal composition is not particularly limited, and examples thereof include a method of applying the liquid crystal composition to a support and, if necessary, performing a drying treatment. The support will be described in detail later. An alignment layer may also be disposed on the support. The method for applying the liquid crystal composition is not particularly limited, and examples of the application method include spin coating, air knife coating, curtain coating, roller coating, wire bar coating, gravure coating, and die coating.

[0155] Next, the coating film of the liquid crystal composition is subjected to a curing treatment and an acid generating treatment. Examples of the curing treatment include a light irradiation treatment and a heat treatment. The conditions for the curing treatment are not particularly limited, but it is preferable to use ultraviolet light for polymerization by light irradiation. The irradiation dose is 10 mJ / cm. ２ ~50 J / cm ２ is preferred, and 20 mJ / cm ２ ~5 J / cm ２ More preferably, 30 mJ / cm ２ ~3 J / cm ２ is more preferably 50 to 1000 mJ / cm２ is particularly preferred. In order to promote the polymerization reaction, the polymerization may be carried out under heating conditions. The heating temperature is preferably 50 to 200°C, more preferably 60 to 150°C. The heating time is preferably 0.5 to 20 minutes, more preferably 1 to 5 minutes. The heating treatment and light irradiation treatment may be carried out multiple times. For example, the treatments may be carried out in the following order: heating treatment, light irradiation treatment, and heating treatment.

[0156] The treatment of generating acid from a photoacid generator in a coating film is a treatment of generating acid by irradiating light to which the photoacid generator contained in the liquid crystal composition is sensitive. By carrying out this treatment, if the specific compound has an acid-cleavable moiety, cleavage of the cleavage moiety progresses. If the photoalignment compound has an acid-cleavable moiety, cleavage of the cleavage moiety of the photoalignment compound also progresses. The light irradiation treatment carried out in the above treatment may be any treatment that sensitizes the photoacid generator, and examples thereof include a method of irradiating ultraviolet light. As a light source, a lamp that emits ultraviolet light, such as a high-pressure mercury lamp or a metal halide lamp, can be used. The irradiation dose is 10 mJ / cm. ２ ~50 J / cm ２ is preferred, and 20 mJ / cm ２ ~5 J / cm ２ More preferably, 30 mJ / cm ２ ~3 J / cm ２ is more preferably 50 to 1000 mJ / cm ２ is particularly preferred.

[0157] The curing treatment and the acid generating treatment may be carried out after the curing treatment, or may be carried out simultaneously. In particular, when the photoacid generator and the polymerization initiator in the liquid crystal composition are photosensitive to light of the same wavelength, it is preferable to carry out the curing treatment and the acid generating treatment simultaneously from the viewpoint of productivity.

[0158] The method of photo-alignment treatment to be performed on the coating film of the liquid crystal composition (including a cured film of the liquid crystal composition that has been cured) formed above is not particularly limited, and known methods can be used. Examples of the photo-alignment treatment include a method in which the coating film of the liquid crystal composition (including a cured film of the liquid crystal composition that has been cured) is irradiated with polarized light or non-polarized light from an oblique direction to the coating film surface.

[0159] In the photo-alignment treatment, the polarized light to be irradiated is not particularly limited, and examples thereof include linearly polarized light, circularly polarized light, and elliptically polarized light, with linearly polarized light being preferred. The "oblique direction" in which unpolarized light is irradiated is not particularly limited as long as it is a direction tilted at a polar angle θ (0<θ<90°) with respect to the normal direction of the coating film surface, and can be appropriately selected depending on the purpose, with θ being preferably 20 to 80°.

[0160] The wavelength of the polarized or unpolarized light is not particularly limited as long as it is light to which the photo-alignable group is photosensitive, and examples thereof include ultraviolet light, near ultraviolet light, and visible light, with near ultraviolet light of 250 to 450 nm being preferred. Examples of light sources for irradiating polarized or unpolarized light include xenon lamps, high-pressure mercury lamps, ultra-high-pressure mercury lamps, and metal halide lamps. The wavelength range of the irradiated ultraviolet or visible light obtained from such light sources can be limited by using an interference filter or color filter. Furthermore, linearly polarized light can be obtained by using a polarizing filter or polarizing prism on the light from these light sources.

[0161] In the above, an embodiment in which the curing treatment and acid generation treatment are performed before the photo-alignment treatment is described, but the present invention is not limited to this embodiment, and the curing treatment and acid generation treatment may be performed simultaneously during the photo-alignment treatment.

[0162] Although the method for forming a liquid crystal layer having a specific compound having an acid-cleavable moiety has been described in detail above, when forming a liquid crystal layer having a specific compound having a photocleavable or thermally cleavable moiety, the acid generation treatment described above may be omitted. When photocleaving the moiety having photocleavage, the irradiation dose in the photoalignment treatment described above is set to 50 to 1000 mJ / cm. ２When the thermally cleavable portion is thermally cleaved, the heating temperature is preferably set to 60 to 150° C. in the above-mentioned heat treatment.

[0163] The thickness of the liquid crystal layer is not particularly limited, but is preferably 0.1 to 10 μm, more preferably 0.5 to 5 μm, for the reason that the liquid crystal alignment property becomes better.

[0164] [Optical Laminate] The optical laminate of the present invention has the liquid crystal layer of the present invention and an optically anisotropic layer provided on the liquid crystal layer. Alternatively, as described above, it is preferable that the surface of the liquid crystal layer has alignment control ability. One suitable embodiment of the optical laminate of the present invention is an embodiment in which the optically anisotropic layer provided on the liquid crystal layer is formed using a polymerizable liquid crystal composition containing a polymerizable liquid crystal compound, and the liquid crystal layer and the optically anisotropic layer are laminated adjacent to each other. Furthermore, it is preferable that the optical laminate of the present invention has a support that supports the liquid crystal layer. Preferred embodiments of the optical laminate of the present invention will be described in detail below.

[0165] [Support] Examples of the support include glass substrates and polymer films. Materials for the polymer film include cellulose-based polymers; acrylic polymers having acrylic acid ester polymers such as polymethyl methacrylate and lactone ring-containing polymers; thermoplastic norbornene-based polymers; polycarbonate-based polymers; polyester-based polymers such as polyethylene terephthalate and polyethylene naphthalate; styrene-based polymers such as polystyrene and acrylonitrile-styrene copolymers; polyolefin-based polymers such as polyethylene, polypropylene and ethylene-propylene copolymers; vinyl chloride-based polymers; amide-based polymers such as nylon and aromatic polyamides; imide-based polymers; sulfone-based polymers; polyethersulfone-based polymers; polyetheretherketone-based polymers; polyphenylene sulfide-based polymers; vinylidene chloride-based polymers; vinyl alcohol-based polymers; vinyl butyral-based polymers; arylate-based polymers; polyoxymethylene-based polymers; epoxy-based polymers; and polymers obtained by mixing these polymers.

[0166] The thickness of the support is not particularly limited, but is preferably from 5 to 200 μm, more preferably from 10 to 100 μm, and even more preferably from 20 to 90 μm. The support is preferably peelable.

[0167] [Liquid Crystal Layer] The liquid crystal layer is the liquid crystal layer of the present invention described above.

[0168] [Optically Anisotropic Layer] The optically anisotropic layer is preferably formed using a polymerizable liquid crystal composition containing a polymerizable liquid crystal compound. Here, examples of the polymerizable liquid crystal composition for forming the optically anisotropic layer include a composition containing the polymerizable liquid crystal compound, a polymerization initiator, a solvent, and the like, which are described as optional components in the liquid crystal composition of the present invention.

[0169] The thickness of the optically anisotropic layer is not particularly limited, but is preferably from 0.1 to 10 μm, more preferably from 0.5 to 5 μm.

[0170] [Method for producing optical laminate] The method for producing the optical laminate of the present invention is a method for producing a preferred embodiment of the optical laminate of the present invention described above, and preferably includes the steps of generating an acid from a photoacid generator in a coating film obtained using the liquid crystal composition, and then subjecting the coating film to a photoalignment treatment to form a liquid crystal layer having alignment controllability (Step 1), and applying a polymerizable liquid crystal composition containing a polymerizable liquid crystal compound onto the liquid crystal layer to form an optically anisotropic layer (Step 2).

[0171] [Step 1] Step 1 is a step of generating an acid from a photoacid generator in a coating film obtained using the liquid crystal composition, and then subjecting the coating film to a photoalignment treatment to form a liquid crystal layer having alignment controllability. The procedure of Step 1 is as described above.

[0172] [Step 2] Step 2 is a step of forming an optically anisotropic layer by applying a polymerizable liquid crystal composition containing a polymerizable liquid crystal compound onto a liquid crystal layer. The method for applying the polymerizable liquid crystal composition is not particularly limited, and examples thereof include the application methods exemplified in Step 1.

[0173] A method for forming an optically anisotropic layer includes a method of subjecting a coating film of a polymerizable liquid crystal composition to a heat treatment and then subjecting it to a curing treatment. The heat treatment can align the polymerizable liquid crystal compound. Although the heat treatment and the curing treatment are performed separately in the above, a method in which the curing treatment is performed under heating conditions may also be used. Note that, depending on the type of polymerizable liquid crystal compound, if alignment is achieved without performing a heat treatment, the heat treatment may not be performed. After the coating film is heated, the coating film may be cooled as needed before the curing treatment described below.

[0174] The conditions for the heat treatment are not particularly limited as long as the temperature is such that the polymerizable liquid crystal compound is oriented. The heating temperature is usually preferably 50 to 200° C. The heating time is preferably 0.5 to 20 minutes, more preferably 1 to 5 minutes.

[0175] The curing method is not particularly limited, and examples thereof include light irradiation and heat treatment. Light irradiation is preferred. The light used in the light irradiation is preferably ultraviolet light. The conditions for light irradiation are not particularly limited, and the irradiation dose is preferably 10 mJ / cm. ２ ~50 J / cm ２ is preferred, and 20 mJ / cm ２ ~5 J / cm ２ More preferably, 30 mJ / cm ２ ~3 J / cm ２ It is more preferable that the polymerization reaction is carried out under heating conditions in order to accelerate the polymerization reaction. The heating treatment and curing treatment may be carried out multiple times.

[0176] [Image display device] The image display device of the present invention is an image display device having the optical laminate of the present invention. The display element used in the image display device of the present invention is not particularly limited, and examples thereof include a liquid crystal cell, an organic electroluminescence (hereinafter also referred to as "EL") display panel, and a plasma display panel. Of these, a liquid crystal cell or an organic EL display panel is preferred. That is, the image 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.

[0177] [Compound] The compound of the present invention is not particularly limited as long as it is the above-mentioned specific compound, but is preferably a compound having a repeating unit A represented by formula (a1) and a repeating unit B represented by any one of formulas (b1) to (b3). The repeating unit A and the repeating unit B have the same meanings as the repeating units A and B that the above-mentioned specific compound may have, and preferred embodiments are also the same. Furthermore, for preferred embodiments other than those mentioned above, reference can be made to the above-mentioned specific compound embodiments.

[0178] The features of the present invention will be explained in more detail below with reference to examples and comparative 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 specific examples shown below.

[0179] Example 1 Preparation of Liquid Crystal Layer A A polymerizable liquid crystal composition A having the following composition was prepared.

[0180] 4.5 parts by mass of the following photoacid generator A; 0.2 parts by mass of N,N-diisopropylethylamine; 238 parts by mass of methyl isobutyl ketone (boiling point 116°C); 214 parts by mass of ethyl propionate (boiling point 99°C); 24 parts by mass of methyl ethyl ketone (boiling point 80°C). ----------------------------------------------------------------------------------

[0181] Liquid crystal compound mixture A (containing 84 mass%, 14 mass%, and 2 mass% of liquid crystal compounds, respectively, from top to bottom)

[0182] Polymer A (The numerical values ​​in the following formula indicate the content (mass%) of each repeating unit relative to the total repeating units in the polymer. Weight average molecular weight: 60,000)

[0183] Photo-alignment compound 2-1 (The numerical values ​​in the formula below indicate the content (mass%) of each repeating unit relative to the total repeating units in the polymer. Hereinafter, Me represents a methyl group. Weight average molecular weight: 95,000) The synthesis method of photo-alignment compound 2-1 will be described later.

[0184] Specific Compound 1-1 (The numerical values ​​in the following formula indicate the content (mass %) of each repeating unit relative to all repeating units in the polymer. Weight average molecular weight: 35,000) The synthesis method of Specific Compound 1-1 will be described later.

[0185] Compound A

[0186] Photopolymerization initiator A

[0187] Photoacid generator A

[0188] The prepared polymerizable liquid crystal composition A was applied to a cellulose polymer film (TG40, manufactured by Fujifilm Corporation) as a substrate using a #3.0 wire bar, and heated at 80°C for 1 minute. The applied polymerizable liquid crystal composition A was then heated at 150 mJ / cm under conditions of an oxygen concentration of less than 100 ppm by volume. ２ Thereafter, the film was annealed at 115°C for 1 minute, and then irradiated with UV (ultraviolet) light (ultra-high pressure mercury lamp; UL750; manufactured by HOYA) at room temperature through a wire grid polarizer at 7.9 mJ / cm. ２ The liquid crystal layer A was irradiated with light (wavelength: 313 nm) to impart alignment control ability, thereby forming a liquid crystal layer A having a thickness of 0.7 μm. The liquid crystal layer A was a positive C plate. The retardation Rth(550) in the thickness direction of the liquid crystal layer A was −70 nm.

[0189] <Method for synthesizing specific compound 1-1> Monomer mB-57 represented by the following formula mB-57 was synthesized according to the following scheme: In the above scheme, TMS represents a trimethylsilyl group.

[0190]

[0191] (Synthesis of b) 100 g of 4-chlorobutyraldehyde dimethyl acetal (the compound represented by formula a in the above scheme), 118.1 g of 3-buten-1-ol, 1.52 g of (+)-10-camphorsulfonic acid, and 197 mL of hexane were weighed into a 2000 mL recovery flask equipped with a condenser, thermometer, and stirrer, and the mixture was stirred for 30 minutes at an external temperature of 75°C under a nitrogen atmosphere. The temperature was raised to 78°C, a Dean-Stark reaction vessel was attached, and 1075 mL of hexane was added dropwise over 3 to 4.5 hours using a dropping pump. Next, 70.9 g of 3-buten-1-ol was added, and the mixture was stirred for 30 minutes. 1075 mL of hexane was added dropwise over 3 to 4.5 hours using a dropping pump. The mixture was then stirred for 1 hour, the internal temperature was lowered to 50°C, and 2 mL of diisopropylethylamine was added. The mixture was separated and washed with hexane, acetonitrile, water, and triethylamine, and the obtained organic layer was concentrated to obtain 260.0 g of compound b (the compound represented by formula b in the above scheme) as a colorless, transparent liquid.

[0192] (Synthesis of c) 130 g of compound b, 1300 μL of Karstedt catalyst, and 1300 mL of toluene were weighed into a 2000 mL recovery flask equipped with a condenser, thermometer, and stirrer, and stirred for 30 minutes under a nitrogen atmosphere. The temperature was raised to 45°C, and 237.3 g of heptamethyltrisiloxane was added dropwise over 2 hours using a dropping pump. The mixture was cooled to 25°C and filtered through a Nutsche filter packed with activated carbon / Celite. The filtrate was concentrated to obtain 350.0 g of compound c (the compound represented by formula c in the above scheme) as a brown liquid.

[0193] Next, 330 g of compound c, 63.1 g of sodium methacrylate, 165 mg of BHT, 121.2 g of potassium iodide (KI), and 1650 mL of N,N-dimethylacetamide (DMAc) were weighed into a 3000 mL recovery flask equipped with a condenser, a thermometer, and a stirrer, and the mixture was stirred for 7 hours at 85° C. The mixture was separated and washed with heptane, ethyl acetate, and water, and the resulting organic phase was concentrated to obtain 350.0 g of monomer mB-57 as a colorless, transparent liquid.

[0194] (Polymerization Reaction) A flask equipped with a condenser, a thermometer, and a stirrer was charged with cyclopentanone (30 parts by mass) as a solvent, the repeating units and the respective monomers that constitute the repeating units and contents of Specific Compound 1-1 shown below, and 2,2'-azobis(isobutyronitrile) (0.1 parts by mass) as a polymerization initiator, and while flowing nitrogen into the flask at 15 mL / min, the mixture was stirred for 7 hours while maintaining a reflux state by heating in a water bath. After completion of the reaction, the mixture was allowed to cool to room temperature, and the resulting solution was poured into a large excess of methanol to precipitate Specific Compound 1-1. The recovered precipitate was filtered, washed with a large amount of methanol, and then vacuum-dried at 40°C for 6 hours to obtain Specific Compound 1-1.

[0195] <Method for synthesizing photoalignment compound 2-1> In a flask equipped with a cooling tube, a thermometer, and a stirrer, 1-methoxy-2-propanol (284.6 parts by mass) as a solvent, the following monomer mA-16 (28.0 parts by mass), the following monomer mB-57 (31.0 parts by mass), and the following monomer mC-4Cl (41.0 parts by mass) were weighed out, and the flask was heated to 70 ° C. in a water bath while flowing nitrogen into the flask at 15 mL / min, and a mixture of polymerization initiator 2,2'-azobis (isobutyric acid) dimethyl (1.74 parts by mass) and 1-methoxy-2-propanol (16.2 parts by mass) was added dropwise over 20 minutes, and the mixture was stirred while maintaining a reflux state for 9 hours.

[0196]

[0197] After the reaction was completed, the mixture was allowed to cool to room temperature, and the resulting solution was poured into a large excess of a mixed solution of methanol / water to precipitate photoalignment compound 2-1. The recovered precipitate was filtered, washed with a large amount of methanol / water, and then vacuum dried at 40°C for 12 hours to obtain the following photoalignment compound 2-1c having the repeating unit A-16, repeating unit B-57, and repeating unit C-4Cl.

[0198]

[0199] Subsequently, a flask equipped with a condenser, a thermometer, and a stirrer was charged with photoalignment compound 2-1c (90.0 parts by mass), 4-methoxyphenol (0.18 parts by mass), triethylamine (65.9 parts by mass), acetone (110 parts by mass), and dimethylacetamide (110 parts by mass), and stirred for 2 hours at 60 ° C. by heating in a water bath. After completion of the reaction, the mixture was allowed to cool to room temperature, and the resulting reaction solution was poured into a large excess of methanol / water (1 / 3) to precipitate a polymer. The recovered precipitate was filtered, washed with a large amount of methanol / water (1 / 3), and then dried by blowing air at 40 ° C. for 12 hours to obtain the following photoalignment compound 2-1.

[0200] [Formation of Optical Laminate] A polymerizable liquid crystal composition B having the following composition was prepared.

[0201] -------------------------------- Polymerizable liquid crystal composition B ---------------------------------- 45.36 parts by mass of liquid crystal compound B shown below 21.84 parts by mass of liquid crystal compound C shown below 20.00 parts by mass of liquid crystal compound D shown below 5.00 parts by mass of liquid crystal compound E shown below 7.80 parts by mass of mixture A of the above liquid crystal compounds 0.50 parts by mass of the above photopolymerization initiator A 0.09 parts by mass of leveling agent B shown below Cyclopentanone 180.73 parts by mass Methyl ethyl ketone 53.98 parts by mass ----------------------------------

[0202] Liquid crystal compound B (tBu represents a tertiary butyl group)

[0203] liquid crystal compound C

[0204] Liquid crystal compound D

[0205] Liquid crystal compound E (Me represents a methyl group)

[0206] Leveling agent B (in the formula below, the numerical values ​​shown for each repeating unit represent the content (% by mass) of each repeating unit relative to all repeating units, which are 50% by mass, 38% by mass, and 12% by mass from the left; weight average molecular weight: 20,000)

[0207] Polymerizable liquid crystal composition B was applied onto the previously formed liquid crystal layer A using a wire bar coater #7 to form a composition layer. The formed composition layer was heated to 120°C on a hot plate and then cooled to 60°C to stabilize the alignment. Thereafter, the film was irradiated with ultraviolet light (100 mJ / cm) for the first time in a nitrogen atmosphere (oxygen concentration less than 100 ppm by volume) using an ultra-high pressure mercury lamp while maintaining the film temperature at 60°C. ２), the film temperature was kept at 90°C and the second ultraviolet irradiation (200 mJ / cm ２ ) to fix the alignment, forming an optically anisotropic layer B with a thickness of 2.8 μm, and producing an optical laminate. The optically anisotropic layer B was a positive A plate. The optically anisotropic layer B had an in-plane retardation Re(550) of 141 nm at a wavelength of 550 nm, and the angle of the in-plane slow axis with respect to the width direction of the film was 45°. The above angle is expressed as a positive value in the counterclockwise direction, with the width direction of the film as the reference (0°) when the optically anisotropic layer B disposed on the liquid crystal layer A is observed from the optically anisotropic layer B side.

[0208] Examples 2 to 15, Comparative Examples 1 and 2 Polymerizable liquid crystal composition A was prepared in the same manner as in Example 1, and each optical laminate was obtained, except that the content or type of evaluation compound (specific compound or comparative compound) or photo-alignment compound in polymerizable liquid crystal composition A was changed as shown in Table 1 below. Furthermore, evaluation compounds other than specific compound 1-1 were synthesized with reference to the synthesis procedure for specific compound 1-1. Photo-alignment compounds other than photo-alignment compound 2-1 were synthesized with reference to the synthesis procedure for photo-alignment compound 2-1. The chemical structures of the evaluation compounds or photo-alignment compounds used in the examples and comparative examples are shown below. Evaluation compounds 1-1 and 1-3 to 1-10 are all specific compounds having a moiety that cleaves when exposed to acid, evaluation compound 1-2 is a specific compound having a moiety that cleaves when exposed to light, and evaluation compound 1-11 is a comparative compound.

[0209] [Evaluated Compounds]

[0210]

[0211]

[0212] [Photoalignment compound]

[0213] [Evaluation] [Evaluation of Wind Unevenness] Two polarizing plates were placed in a crossed Nicol configuration, and the prepared liquid crystal layer A was placed between them. The presence or absence of streaky unevenness was observed, and the suppression of wind unevenness was evaluated according to the following criteria: A: Unevenness was not visible. B: Unevenness was barely visible. C: Unevenness was visible.

[0214] [Evaluation of upper layer coatability] The surface area of ​​an A4 size sheet of the produced optical laminate was inspected, and defects that appeared as circular or oval holes were regarded as repellings, and the upper layer coatability was evaluated. A: 0 to 1 repellings were observed. B: 2 to 4 repellings were observed. C: 5 or more repellings were observed.

[0215] [Evaluation of liquid crystal alignment] Two polarizing plates were arranged in a crossed Nicol configuration, and the obtained optical laminate was placed between them, and the degree of light leakage and the surface state were observed with a polarizing microscope. A: No light leakage, no disturbance of the liquid crystal director, and stable surface state. B: No light leakage, only slight disturbance of the liquid crystal director, and stable surface state. C: Light leakage was observed, and the liquid crystal director was disturbed, resulting in an unstable surface state.

[0216] Furthermore, when the liquid crystal layer A prepared in the above-mentioned [Preparation of liquid crystal layer A] in each example was visually observed (the size of the liquid crystal layer A to be observed was A4 size), aggregates (e.g., aggregates derived from a specific compound) were observed in the liquid crystal layer A of Example 7, but no aggregates were observed in the liquid crystal layer A of Examples other than Example 7.

[0217] The evaluation results are shown in the table below. "Weight average molecular weight" indicates the weight average molecular weight of each evaluation compound or each photo-alignment compound, and the method for measuring the weight average molecular weight is as described above. The "content" of the "evaluation compound" or "photo-alignment compound" indicates the content (parts by mass) relative to 100 parts by mass of the liquid crystal compound in the polymerizable liquid crystal composition A.

[0218]

[0219] The results shown in Table 1 above indicate that liquid crystal compositions containing no specific compound are inferior in at least one of wind unevenness, liquid crystal alignment after formation into a layer, and upper layer coatability (Comparative Examples 1 and 2). On the other hand, liquid crystal compounds of the present invention are superior in all of wind unevenness, liquid crystal alignment after formation into a layer, and upper layer coatability (Examples 1 to 15). It was found that wind unevenness or aggregation (aggregation of the specific compound) can be more effectively suppressed when the content of repeating unit A is 40% by mass or more but less than 100% by mass relative to the total mass of all repeating units of the specific compound (e.g., comparison between Examples 1 to 6 and Examples 7 and 9). It was found that wind unevenness can be more effectively suppressed when the specific compound has a group represented by the above formula (1) (e.g., comparison between Examples 1 to 7 and Example 8). It was found that wind unevenness can be more effectively suppressed when the specific compound has a weight-average molecular weight of 5,000 to 100,000 (e.g., comparison between Examples 1 to 7 and Example 10). It was found that wind unevenness could be further suppressed when the content of the specific compound was 0.01 to 5 parts by mass relative to 100 parts by mass of the liquid crystal compound (e.g., comparison between Examples 1 to 7 and Example 11). It was also found that when the photo-alignment compound had a repeating unit X having a photo-alignment group and a repeating unit C having a crosslinkable group, the total content of the repeating unit X and the repeating unit C was 99 to 100% by mass relative to the total mass of all repeating units of the photo-alignment compound, and the content of the repeating unit X was 40% by mass or more relative to the total mass of all repeating units of the photo-alignment compound, the liquid crystal alignment property was more excellent (e.g., comparison between Examples 1, 12 and 13). It has been found that when a photo-alignment compound has a repeating unit A represented by formula (a1), a repeating unit X having a photo-alignment group, and a repeating unit C having a crosslinkable group, and the total content of repeating unit A, repeating unit X, and repeating unit C is 99 to 100 mass% relative to the total mass of all repeating units of the photo-alignment compound, and the content of repeating unit A represented by formula (a1) is 10 to 60 mass% relative to the total mass of all repeating units of the photo-alignment compound, the liquid crystal alignment property is better (e.g., comparison between Examples 1 and 12 and Example 14).It was found that when the content of the photoalignment compound was 0.1 to 10 parts by mass with respect to 100 parts by mass of the liquid crystal compound, the liquid crystal alignment property was better (eg, comparison between Examples 1 and 12 and Example 15).

Claims

1. A liquid crystal composition comprising: a leveling agent having a site that is cleaved by the action of at least one selected from the group consisting of acid, light, and heat; a photoalignment compound; and a liquid crystal compound.

2. The liquid crystal composition according to claim 1, wherein the leveling agent has a repeating unit A represented by formula (a1) and a repeating unit B represented by any one of formulas (b1) to (b3). In formula (a1), R １ and R ２ R each independently represents a hydrogen atom or an alkyl group. ３ represents a hydrogen atom or a substituent. X represents an (m+1)-valent linking group. L １ represents an (n+1)-valent linking group having a site that is cleaved by the action of at least one selected from the group consisting of acid, light, and heat. n represents an integer of 1 to 4. m represents an integer of 1 to 5. Rh represents a substituent having two or more groups represented by formula (S). In formula (S), * represents a bonding position. ４ , R ５ and R ６ each independently represents an alkyl group, an alkenyl group, an aryl group, or an alkylenearyl group. In formulas (b1) to (b3), R ｂ１ , R ｂ２ , R ｂ３ and R ｂ４ each independently represents a hydrogen atom or an alkyl group. ｂ１ are each independently —O— or —NR Ｚｂ - represents. Ｚｂ represents a hydrogen atom or a substituent. ｂ２ represents a single bond or a divalent linking group. A represents an alkylene group. p represents a number of 2 or more. SP ｂ１ each independently represents a spacer group. ｂ１ represents a mesogenic group. ｂ１ each independently represents a terminal group.

3. The liquid crystal composition according to claim 1, wherein the content of the leveling agent is 0.01 to 5 parts by mass relative to 100 parts by mass of the liquid crystal compound.

4. L １ The liquid crystal composition according to claim 2, wherein is a group represented by any one of formulas (L1) to (L3): In formulas (L1) to (L3), *1 represents the bonding position with X, and *2 represents the bonding position with Rh. ｘ１ , L ｘ２ and L ｘ３ R each independently represents an alkylene group having 1 to 20 carbon atoms which may have an —O— group, an aryl group having 6 to 18 carbon atoms which may have an —O— group, a combination of these, or a single bond. Ｌ１ and R Ｌ２ each independently represents a hydrogen atom or a substituent. Ｌ１ , L Ｌ２ and L Ｌ３ each independently represents a divalent linking group. Ｌ１ and m Ｌ２ Each independently represents 1 or 2. １ is a group represented by the formula (L1), n ​​in the formula (a1) is m Ｌ１ +m Ｌ２ Represents L １ is a group represented by the formula (L2), n in the formula (a1) represents 1. １ is a group represented by the formula (L3), n in the formula (a1) represents 2.

5. The liquid crystal composition according to claim 1, wherein the leveling agent has a group represented by formula (1). In formula (1), * represents a bonding position. ７ , R ８ and R １２ R each independently represents a hydrogen atom or a substituent. ９ , R １０ , R １１ , R １３ , R １４ and R １５ each independently represents an alkyl group, an alkenyl group, an aryl group, or an alkylenearyl group. x and y each independently represent an integer of 1 to 3. v and w each independently represent an integer of 1 to 4. When v represents 1, L ２ represents a single bond or a divalent linking group, and when v represents an integer of 2 to 4, L ２ represents a linking group with a valence of v+1. When w represents 1, L ３ represents a single bond or a divalent linking group, and when w represents an integer of 2 to 4, L ３ represents a (w+1)-valent linking group.

6. The liquid crystal composition according to claim 2, wherein the content of the repeating unit A is 40% by mass or more and less than 100% by mass with respect to the total mass of all repeating units of the leveling agent.

7. The liquid crystal composition according to claim 1, wherein the weight-average molecular weight of the leveling agent is 5,000 to 100,000.

8. The liquid crystal composition according to claim 1, wherein the content of the photoalignment compound is 0.1 to 10 parts by mass with respect to 100 parts by mass of the liquid crystal compound.

9. The liquid crystal composition according to claim 1, wherein the photo-alignment compound has a repeating unit X having a photo-alignment group and a repeating unit C having a crosslinkable group, the total content of the repeating unit X and the repeating unit C is 99 to 100% by mass relative to the total mass of all repeating units of the photo-alignment compound, and the content of the repeating unit X is 40% by mass or more relative to the total mass of all repeating units of the photo-alignment compound.

10. The liquid crystal composition according to claim 1, wherein the photo-alignment compound comprises a repeating unit A represented by formula (a1), a repeating unit X having a photo-alignment group, and a repeating unit C having a crosslinkable group, and the total content of the repeating unit A, the repeating unit X, and the repeating unit C is 99 to 100% by mass relative to the total mass of all repeating units of the photo-alignment compound. In formula (a1), R １ and R ２ R each independently represents a hydrogen atom or an alkyl group. ３ represents a hydrogen atom or a substituent. X represents an (m+1)-valent linking group. L １ represents an (n+1)-valent linking group having a site that is cleaved by the action of at least one selected from the group consisting of acid, light, and heat. n represents an integer of 1 to 4. m represents an integer of 1 to 5. Rh represents a substituent having two or more groups represented by formula (S). In formula (S), * represents a bonding position. ４ , R ５ and R ６ each independently represents an alkyl group, an alkenyl group, an aryl group, or an alkylenearyl group.

11. The liquid crystal composition according to claim 10, wherein the content of the repeating unit A represented by formula (a1) is 10 to 60% by mass relative to the total mass of all repeating units of the photoalignment compound.

12. A liquid crystal layer formed using the liquid crystal composition according to any one of claims 1 to 11, and having alignment control ability.

13. An optical laminate comprising the liquid crystal layer according to claim 12 and an optically anisotropic layer disposed on the liquid crystal layer.

14. An image display device comprising the optical laminate according to claim 13.

15. A method for producing an optical laminate, comprising the steps of: subjecting a coating film obtained using the liquid crystal composition according to any one of claims 1 to 11 to a photo-alignment treatment to form a liquid crystal layer having alignment controllability; and applying a polymerizable liquid crystal composition containing a polymerizable liquid crystal compound onto the liquid crystal layer to form an optically anisotropic layer.

16. A compound having a repeating unit A represented by formula (a1) and a repeating unit B represented by any one of formulas (b1) to (b3). In formula (a1), R １ and R ２ R each independently represents a hydrogen atom or an alkyl group. ３ represents a hydrogen atom or a substituent. X represents an (m+1)-valent linking group. L １ represents an (n+1)-valent linking group having a site that is cleaved by the action of at least one selected from the group consisting of acid, light, and heat. n represents an integer of 1 to 4. m represents an integer of 1 to 5. Rh represents a substituent having two or more groups represented by formula (S). In formula (S), * represents a bonding position. ４ , R ５ and R ６ each independently represents an alkyl group, an alkenyl group, an aryl group, or an alkylenearyl group. In formulas (b1) to (b3), R ｂ１ , R ｂ２ , R ｂ３ and R ｂ４ each independently represents a hydrogen atom or an alkyl group. ｂ１ are each independently —O— or —NR Ｚｂ - represents. Ｚｂ represents a hydrogen atom or a substituent. ｂ２ represents a single bond or a divalent linking group. A represents an alkylene group. p represents a number of 2 or more. SP ｂ１ each independently represents a spacer group. ｂ１ represents a mesogenic group. ｂ１ each independently represents a terminal group.

17. The compound according to claim 16, wherein the repeating unit A is a repeating unit represented by any one of formulas (a2) to (a4). In formulas (a2) to (a4), R １ and R ２ R each independently represents a hydrogen atom or an alkyl group. ３ represents a hydrogen atom or a substituent. ａ represents —COO— or —CONH—. ｘ１ , L ｘ２ and L ｘ３ R each independently represents an alkylene group having 1 to 20 carbon atoms which may have an —O— group, an aryl group having 6 to 18 carbon atoms which may have an —O— group, a combination of these, or a single bond. Ｌ１ and R Ｌ２ each independently represents a hydrogen atom or a substituent. Ｌ１ , L Ｌ２ and L Ｌ３ each independently represents a divalent linking group. ａ represents a group represented by formula (S1). Ｌ１ and m Ｌ２ each independently represents 1 or 2. In formula (S1), R ４ , R ５ and R ６ R each independently represents an alkyl group, an alkenyl group, an aryl group, or an alkylenearyl group. Ｓ represents an alkyl group; s represents 2 or 3;

Images