Resin composition for thermosetting optical alignment film

Abstract

[Problem] To provide a composition capable of obtaining, through a brief low-temperature firing, an alignment material having excellent alignment properties and adhesiveness without using a crosslinking agent including an N-methylol group, an N-alkoxymethyl group, or the like. [Solution] A cured film-forming composition of the present invention contains (A) a compound represented by formula (a), (B) a polymer having an epoxy group, (C) a thermal acid generator, and (D) a compound having a nucleophilic group and a radically polymerizable group including a C=C double bond.

Description

Resin composition for thermosetting photo-alignment film

[0001] The present invention relates to a thermosetting resin composition for a photoalignment film (also referred to as a cured film-forming composition), an alignment material, and a retardation material.

[0002] In a 3D display using circularly polarized glasses, a retardation agent is usually placed on a display element that forms an image, such as a liquid crystal panel. The retardation material used for this purpose has a patterned configuration in which two types of retardation regions with different retardation properties are regularly arranged in multiple numbers. In the following description, such a patterned retardation material in which multiple retardation regions with different retardation properties are arranged is referred to as a patterned retardation material.

[0003] A patterned retardation material can be produced by optically patterning a retardation material made of polymerizable liquid crystal, as disclosed in, for example, Patent Document 1. Optical patterning of a retardation material made of polymerizable liquid crystal utilizes photo-alignment technology known for forming alignment materials for liquid crystal panels. That is, a coating film made of a photo-alignable material is provided on a substrate, and two types of polarized light with different polarization directions are irradiated onto the coating. A photo-alignment film is then obtained as an alignment material in which two types of liquid crystal alignment regions with different liquid crystal alignment control directions are formed. A solution-like retardation material containing polymerizable liquid crystal is applied onto this photo-alignment film to achieve alignment of the polymerizable liquid crystal. The aligned polymerizable liquid crystal is then cured to form a patterned retardation material.

[0004] The anti-reflection film of an organic EL display is composed of a linear polarizer and a quarter-wave retardation plate. External light directed toward the panel surface of the image display panel is converted into linearly polarized light by the linear polarizer, and then converted into circularly polarized light by the subsequent quarter-wave retardation plate. This circularly polarized external light is reflected by the surface of the image display panel, but the direction of rotation of the polarization plane is reversed during this reflection. As a result, this reflected light is converted by the quarter-wave retardation plate into linearly polarized light in the direction that is blocked by the linear polarizer, in the opposite direction to when it arrived, and is then blocked by the subsequent linear polarizer, resulting in significant suppression of external emission.

[0005] Regarding this quarter-wave retardation plate, Patent Document 2 proposes a method of constructing an optical film with reverse dispersion characteristics by combining a half-wave plate and a quarter-wave plate to construct a quarter-wave retardation plate. In this method, an optical film with reverse dispersion characteristics can be constructed using a liquid crystal material with positive dispersion characteristics in a wide wavelength band used for displaying color images.

[0006] In recent years, liquid crystal materials applicable to this retardation plate (retardation layer) have been proposed that have reverse dispersion characteristics (Patent Documents 3 and 4). By using such liquid crystal materials with reverse dispersion characteristics, instead of a conventional quarter-wave retardation plate formed of two retardation layers by combining a half-wave plate and a quarter-wave plate, it is possible to ensure reverse dispersion characteristics by forming the retardation layer from a single layer, thereby realizing an optical film that can ensure a desired retardation over a wide wavelength band with a simple configuration.

[0007] An alignment layer is used to align liquid crystals. Known methods for forming alignment layers include rubbing and photo-alignment. Photo-alignment is advantageous in that it does not generate static electricity or dust, which are problems with rubbing, and allows for quantitative control of the alignment process.

[0008] Acrylic resins and polyimide resins having photodimerization moieties such as cinnamoyl groups and chalcone groups in their side chains are known as photoalignment materials that can be used in forming alignment materials using photoalignment methods. These resins have been reported to exhibit the ability to control the alignment of liquid crystals (hereinafter referred to as liquid crystal alignment property (liquid crystal alignment ability)) when irradiated with polarized UV light (see Patent Documents 5 to 7).

[0009] Furthermore, there are also examples in which a thermal crosslinking system is introduced into a photoalignment agent using a cinnamoyl moiety in order to improve alignment sensitivity and impart solvent resistance (see Patent Documents 8 and 9).

[0010] Incidentally, Patent Document 10 describes a thermosetting liquid crystal alignment material using a resin composition containing a compound having an N-methylol group or an N-alkoxymethyl group as a highly sensitive photoalignment agent.

[0011] However, compounds containing N-methylol groups are obtained by forming N-methylol groups through the reaction of amino groups with formaldehyde, and therefore, in principle, often contain trace amounts of formaldehyde. As of April 2023, formaldehyde is designated as a deleterious substance under the Poisonous and Deleterious Substances Control Act and is highly toxic to living organisms. It has also been shown by the International Agency for Research on Cancer to be carcinogenic. Furthermore, formaldehyde is released into the air from compounds used in building materials and furniture, causing sick building syndrome, which has become a problem. Therefore, when using compounds containing at least one of an N-methylol group and an N-alkoxymethyl group in products, it is necessary to reduce the formaldehyde concentration in the composition and, particularly in the case of molded products and paints, to ensure the safety of manufacturers and consumers who use the products.

[0012] Japanese Patent Application Laid-Open No. 2005-49865 Japanese Patent Application Laid-Open No. 10-68816 U.S. Patent No. 8,119,026 Specification Japanese Patent Application Laid-Open No. 2009-179563 Japanese Patent No. 3,611,342 Japanese Patent Application Laid-Open No. 2009-058584 Japanese Patent Publication No. 2001-517719 International Publication No. 2011 / 126022 International Publication No. 2014 / 010688 International Publication No. 2010 / 150748

[0013] When a thermal crosslinking system is introduced into a cured film, there is a concern about the generation of formaldehyde in cured film formation systems using crosslinking agents containing N-methylol groups, N-alkoxymethyl groups, etc. Therefore, there is a demand for a composition that can be used to obtain an alignment material with excellent alignment properties and adhesion by baking at a low temperature and for a short time using a thermal crosslinking system that does not involve the risk of generating formaldehyde.

[0014] The present invention has been made based on the above findings and investigations, and an object of the present invention is to provide a cured film-forming composition that does not generate formaldehyde.

[0015] As a result of extensive research to achieve the above-mentioned objective, the inventors have discovered that by using a composition to which a polymer having an epoxy group and a thermal acid generator are added as a photo-alignment component, an alignment material with excellent alignment properties and adhesion can be obtained by baking at a low temperature for a short time without the risk of generating formaldehyde, and have completed the present invention, which has the following gist.

[0016] That is, the present invention includes the following: [1] A cured film-forming composition comprising: (A) a compound represented by the following formula (a), (B) a polymer having an epoxy group, (C) a thermal acid generator, and (D) a compound having a radically polymerizable group containing a C═C double bond and a nucleophilic group: [In the formula, A １ and A ２ each independently represents a hydrogen atom, a methyl group, or a cyano group. １ represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 6 carbon atoms, a haloalkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a haloalkoxy group having 1 to 6 carbon atoms, an alkylamino group having 1 to 6 carbon atoms, a di(alkyl)amino group having 1 to 6 carbon atoms, an OH group, or an NH ２ a group, a carboxy group, a trialkoxysilyl group, a cyano group, a nitro group, or a group represented by the following formula (c-1): (In formula (c-1), the dashed line represents Q ２ represents a bond with １０１ is an alkylene group having 1 to 30 carbon atoms, and one or more hydrogen atoms of this alkylene group may be replaced by a fluorine atom or an organic group. １０１ -CH in ２ CH ２ - may be replaced by -CH=CH-, and further, when any of the following groups are not adjacent to each other, the alkylene group may be interrupted by a group selected from the group consisting of -O-, -NHCO-, -CONH-, -COO-, -OCO-, -NH-, -NHCONH- and -CO-, and M １ represents a hydrogen atom or a methyl group; ２represents a single bond or an alkylene group having 1 to 20 carbon atoms, which may be branched or linear; Q ３ represents a single bond, —O—, —NHCO—, —CONH—, —COO—, —OCO—, —NH—, —NHCONH—, or —CO—, with the proviso that Q ２ If is a single bond, Q ３ is also a single bond, and Q ４ represents a divalent aromatic group, a divalent alicyclic group, a divalent heterocyclic group, or a divalent fused ring group; Q ５ represents a single bond, an oxygen atom, —COO—, or —OCO—; q1 is an integer of 0 to 3; q2 is 0 or 1; and Q ６ represents a single bond, an oxygen atom or a sulfur atom; ７ represents a single bond, an alkylene group having 1 to 20 carbon atoms, a divalent aromatic ring group, or a divalent aliphatic ring group. Here, the alkylene group having 1 to 20 carbon atoms may be branched or linear, and Q ６ When Q is a single bond, ７ is a single bond, and Q ８ is an OH group, NH ２ Q represents a hydroxyphenoxy group, a carboxyphenoxy group, an aminophenoxy group, an aminocarbonylphenoxy group, a phenylamino group, a hydroxyphenylamino group, a carboxyphenylamino group, an aminophenylamino group, a hydroxyalkylamino group, a bis(hydroxyalkyl)amino group, an alkoxysilyl group, a cyanophenylamino group, an alkoxy group having 1 to 12 carbon atoms, a haloalkoxy group having 1 to 12 carbon atoms, a cycloalkoxy group having 3 to 12 carbon atoms, a phenoxy group, or a biphenyloxy group, ２ , Q ３ , Q ６ and Q ７ are both single bonds, q1 is 0, and Q ８ When Q is an OH group, １represents a group other than a hydrogen atom as defined above.] [2] The cured film-forming composition according to the above [1], wherein q2 is 0. [3] The cured film-forming composition according to the above [1], wherein the polymer having an epoxy group, component (B), is a homopolymer of a polymerizable unsaturated compound having an epoxy group or a copolymer of a polymerizable unsaturated compound having an epoxy group and another polymerizable unsaturated compound. [4] The cured film-forming composition according to the above [1], wherein the thermal acid generator, component (C), is a sulfonium salt. [5] The cured film-forming composition according to the above [1], wherein the nucleophilic group of the compound, component (D), is selected from the group consisting of a carboxy group, an epoxy group, an oxetanyl group, a hydroxy group, an amino group, a vinyl ether group, and an isocyanate group. [6] An alignment material obtained using the cured film-forming composition according to any one of the above [1] to [5]. [7] A retardation material formed using a cured film obtained from the cured film-forming composition according to any one of the above [1] to [5]. [8] A compound represented by the following formula (a): In the formula, A １ and A ２ each independently represents a hydrogen atom, a methyl group, or a cyano group. １ represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 6 carbon atoms, a haloalkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a haloalkoxy group having 1 to 6 carbon atoms, an alkylamino group having 1 to 6 carbon atoms, a di(alkyl)amino group having 1 to 6 carbon atoms, an OH group, or an NH ２ a group, a carboxy group, a trialkoxysilyl group, a cyano group, a nitro group, or a group represented by the following formula (c-1): (In formula (c-1), the dashed line represents Q ２ represents a bond with １０１ is an alkylene group having 1 to 30 carbon atoms, and one or more hydrogen atoms of this alkylene group may be replaced by a fluorine atom or an organic group. １０１ -CH in ２ CH ２- may be replaced by -CH=CH-, and further, when any of the following groups are not adjacent to each other, the alkylene group may be interrupted by a group selected from the group consisting of -O-, -NHCO-, -CONH-, -COO-, -OCO-, -NH-, -NHCONH- and -CO-, and M １ represents a hydrogen atom or a methyl group; ２ represents a single bond or an alkylene group having 1 to 20 carbon atoms, which may be branched or linear; Q ３ represents a single bond, —O—, —NHCO—, —CONH—, —COO—, —OCO—, —NH—, —NHCONH—, or —CO—, with the proviso that Q ２ If is a single bond, Q ３ is also a single bond, and Q ４ represents a divalent aromatic group, a divalent alicyclic group, a divalent heterocyclic group, or a divalent fused ring group; Q ５ represents a single bond, an oxygen atom, —COO—, or —OCO—; q1 is an integer of 0 to 3; q2 is 0 or 1; and Q ６ represents an oxygen atom or a sulfur atom; ７ represents an alkylene group having 1 to 20 carbon atoms, which may be branched or linear; Q ８ represents an alkoxy group having 1 to 12 carbon atoms; ２ , Q ３ , Q ６ and Q ７ are both single bonds, q1 is 0, and Q ８ When Q is an OH group, １ represents a group other than a hydrogen atom as defined above. [9] A compound represented by the following formula:

[0017] According to the present invention, it is possible to obtain an alignment material having excellent alignment and adhesion by firing at a low temperature for a short time without using a crosslinking agent containing an N-methylol group or an N-alkoxymethyl group, which may generate formaldehyde.

[0018] The present invention will be described in detail below. Note that the following explanation of the constituent elements is an example for explaining the present invention, and the present invention is not limited to these contents.

[0019] <Cured Film-Forming Composition> The cured film-forming composition of the present invention is a cured film-forming composition comprising (A) a compound represented by the above formula (a) (a compound having a photoalignable group), (B) a polymer having an epoxy group, (C) a thermal acid generator, and (D) a compound having a radical polymerizable group containing a C=C double bond and a nucleophilic group. Each component will be described in detail below.

[0020] [Component (A)] The component (A) in the cured film-forming composition of the present invention is a compound represented by the above formula (a) and can be considered a low-molecular-weight compound having a photoalignable group and a thermally crosslinkable group. That is, the component (A) is a component that imparts photoalignment to the cured film obtained from the cured film-forming composition of the present invention. Herein, the component (A) is also referred to as a photoalignment component. Herein, the photoalignable group refers to a functional group that undergoes photodimerization or photoisomerization (e.g., a photodimerization moiety such as a cinnamoyl group, a chalcone group, a coumarin group, or an anthracene group, and a photoisomerization moiety such as an azobenzene structure or a stilbene structure). The thermally crosslinkable group may be, for example, a group selected from the group consisting of a hydroxy group, a carboxy group, an amide group, an amino group, and an alkoxysilyl group. The thermally crosslinkable group may be protected by a protecting group. For example, it is preferably deprotected by an acid generated from the thermal acid generator (component (C)) described below during baking of the cured film-forming composition.

[0021] The compound serving as component (A) is Q １ is a halogen atom, an alkyl group having 1 to 6 carbon atoms, a haloalkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a haloalkoxy group having 1 to 6 carbon atoms, a di(alkyl group having 1 to 6 carbon atoms)amino group, or OH; and Q ２ and Q ３ is a single bond, q1 is 0, q2 is 0, and Q ６ and Q ７ is a single bond, and Q ８Compound (a-1) in which is OH is preferred.

[0022] Examples of such compounds (a-1) include ferulic acid, 4-methoxycinnamic acid, 4-propoxycinnamic acid, 4-cyclohexylcinnamic acid, and 4-(N,N-dimethylamino)cinnamic acid.

[0023] The compound serving as component (A) is Q １ is a halogen atom, an alkyl group having 1 to 6 carbon atoms, a haloalkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a haloalkoxy group having 1 to 6 carbon atoms, or OH; Q ２ and Q ３ is a single bond, q1 is 0, q2 is 0, and Q ６ and Q ７ is a single bond, and Q ８ NH ２ Compound (a-2) which is a group is preferred.

[0024] Examples of such compounds (a-2) include 4-methylcinnamic acid amide, 4-ethylcinnamic acid amide, 4-methoxycinnamic acid amide, and 4-ethoxycinnamic acid amide.

[0025] The compound serving as component (A) is Q １ is an OH group, and Q ２ is a single bond or an alkylene group having 1 to 20 carbon atoms, and Q ３ is a single bond, —O—, —COO— or —OCO—, q1 is 0, q2 is 0, and Q ６ and Q ７ is a single bond, and Q ８ Also preferred is a compound (a-3) in which is an alkoxy group having 1 to 12 carbon atoms, a haloalkoxy group having 1 to 12 carbon atoms, a phenoxy group or a biphenyloxy group.

[0026] Specific examples of the compound (a-3) include 4-(8-hydroxyoctyloxy)cinnamic acid methyl ester, 4-(6-hydroxyhexyloxy)cinnamic acid methyl ester, 4-(4-hydroxybutyloxy)cinnamic acid methyl ester, 4-(3-hydroxypropyloxy)cinnamic acid methyl ester, 4-(2-hydroxyethyloxy)cinnamic acid methyl ester, 4-hydroxymethyloxycinnamic acid methyl ester, 4-hydroxycinnamic acid methyl ester, 4-(8-hydroxyoctyloxy)cinnamic acid ethyl ester, 4-(6-hydroxyhexyloxy)cinnamic acid ethyl ester, 4-(4-hydroxybutyloxy)cinnamic acid ethyl ester, 4-(3-hydroxypropyloxy)cinnamic acid ethyl ester, 4-(2-hydroxyethyloxy)cinnamic acid ethyl ester, 4-hydroxymethyloxycinnamic acid ethyl ester, 4-hydroxycinnamic acid ethyl ester, 4-( Examples of the cinnamic acid phenyl ester include 4-(8-hydroxyoctyloxy)cinnamic acid phenyl ester, 4-(6-hydroxyhexyloxy)cinnamic acid phenyl ester, 4-(4-hydroxybutyloxy)cinnamic acid phenyl ester, 4-(3-hydroxypropyloxy)cinnamic acid phenyl ester, 4-(2-hydroxyethyloxy)cinnamic acid phenyl ester, 4-hydroxymethyloxycinnamic acid phenyl ester, 4-hydroxycinnamic acid phenyl ester, 4-(8-hydroxyoctyloxy)cinnamic acid biphenyl ester, 4-(6-hydroxyhexyloxy)cinnamic acid biphenyl ester, 4-(4-hydroxybutyloxy)cinnamic acid biphenyl ester, 4-(3-hydroxypropyloxy)cinnamic acid biphenyl ester, 4-(2-hydroxyethyloxy)cinnamic acid biphenyl ester, 4-hydroxymethyloxycinnamic acid biphenyl ester, and 4-hydroxycinnamic acid biphenyl ester.

[0027] The compound serving as component (A) is Q １ NH ２ group, and Q ２ is a single bond or an alkylene group having 1 to 20 carbon atoms, and Q ３ is a single bond, —O—, —COO— or —OCO—, q1 is 0, q2 is 0, and Q６ and Q ７ is a single bond, and Q ８ Also preferred is a compound (a-4) in which is an alkoxy group having 1 to 12 carbon atoms, a haloalkoxy group having 1 to 12 carbon atoms, a phenoxy group or a biphenyloxy group.

[0028] Specific examples of the compound (a-4) include 4-aminocinnamic acid methyl ester, 4-aminocinnamic acid ethyl ester, and the like.

[0029] The compound serving as component (A) is Q １ is a trialkoxysilyl group, and Q ２ is an alkylene group having 1 to 20 carbon atoms, and Q ３ is —O—, —COO—, or —OCO—, q1 is 0, q2 is 0, and Q ６ and Q ７ is a single bond, and Q ８ is also preferred a compound (a-5) in which is an alkoxy group having 1 to 12 carbon atoms, a haloalkoxy group having 1 to 12 carbon atoms, a phenoxy group, or a biphenyloxy group. The "alkoxy (group)" in the (tri)alkoxysilyl group can be an alkoxy (group) having 1 to 12 carbon atoms.

[0030] Specific examples of compound (a-5) include 4-(3-trimethoxysilylpropyloxy)cinnamic acid methyl ester, 4-(3-triethoxysilylpropyloxy)cinnamic acid methyl ester, 4-(3-trimethoxysilylpropyloxy)cinnamic acid ethyl ester, 4-(3-triethoxysilylpropyloxy)cinnamic acid ethyl ester, 4-(3-trimethoxysilylhexyloxy)cinnamic acid methyl ester, 4-(3-triethoxysilylhexyloxy)cinnamic acid methyl ester, 4-(3-trimethoxysilylhexyloxy)cinnamic acid ethyl ester, and 4-(3-triethoxysilylhexyloxy)cinnamic acid ethyl ester.

[0031] The compound serving as component (A) is Q １is a hydrogen atom, a halogen atom, an alkyl group having 1 to 6 carbon atoms, a haloalkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a haloalkoxy group having 1 to 6 carbon atoms, or OH; ２ and Q ３ is a single bond, q1 is 0, q2 is 0, and Q ６ is a single bond or an oxygen atom, and Q ７ is an alkylene group having 1 to 20 carbon atoms, and Q ８ Compound (a-6) in which is OH is preferred.

[0032] Examples of such compounds (a-6) include cinnamic acid 8-hydroxyoctyl ester, cinnamic acid 6-hydroxyhexyl ester, cinnamic acid 4-hydroxybutyl ester, cinnamic acid 3-hydroxypropyl ester, cinnamic acid 2-hydroxyethyl ester, and cinnamic acid hydroxymethyl ester.

[0033] The low molecular weight compound of component (A) is a compound represented by the formula (a) above, １ is a group represented by formula (c-1), and Q ２ is a single bond or an alkylene group having 1 to 20 carbon atoms, q1 is 0, q2 is 0, and Q ６ is a single bond, and Q ７ is a single bond, and Q ８ is an OH group, NH ２ Also preferred is compound (a-7), which is a group, a hydroxyphenoxy group, a carboxyphenoxy group, an aminophenoxy group, an aminocarbonylphenoxy group, a phenylamino group, a hydroxyphenylamino group, a carboxyphenylamino group, an aminophenylamino group, a hydroxyalkylamino group, a bis(hydroxyalkyl)amino group, a cyanophenylamino group, an alkoxy group having 1 to 12 carbon atoms, or a haloalkoxy group having 1 to 12 carbon atoms.

[0034] Specific examples of compound (a-7) which is component (A) include 4-(6-methacryloxyhexyl-1-oxy)cinnamic acid, 4-(6-acryloxyhexyl-1-oxy)cinnamic acid, 4-(3-methacryloxypropyl-1-oxy)cinnamic acid, 4-(4-(3-methacryloxypropyl-1-oxy)acryloxy)benzoic acid, 4-(4-(6-methacryloxyhexyl-1-oxy)benzoyloxy)cinnamic acid, 4-(6-methacryloxyhexyl-1-oxy)cinnamamide, 4-(6-methacryloxyhexyl-1-oxy)-N-(4-cyanophenyl)cinnamamide, and 4-(6-methacryloxyhexyl-1-oxy)-N-bishydroxyethylcinnamamide.

[0035] The low molecular weight compound of component (A) is a compound represented by the formula (a) above, １ is a halogen atom, an alkyl group having 1 to 6 carbon atoms, a haloalkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a haloalkoxy group having 1 to 6 carbon atoms, or an OH group; Q ２ is a single bond or an alkylene group having 1 to 20 carbon atoms; ３ is a single bond or —O—, q1 is 0, q2 is 0, and Q ６ is an oxygen atom, and Q ７ is an alkylene group having 1 to 20 carbon atoms, and Q ８ Also preferred is a compound (a-8) in which is an alkoxy group having 1 to 12 carbon atoms, a haloalkoxy group having 1 to 12 carbon atoms, a phenoxy group, or a biphenyloxy group.

[0036] Specific examples of the compound (a-8) that is the component (A) include compounds represented by the following formula:

[0037] The low molecular weight compound of component (A) is a compound represented by the formula (a) above, １ is a group represented by formula (c-1), and Q ２ is a single bond or an alkylene group having 1 to 20 carbon atoms, Q3 is —O—, q1 is 0, q2 is 0, and Q ６is an oxygen atom, and Q ７ is an alkylene group having 1 to 20 carbon atoms, and Q ８ Also preferred is a compound (a-9) in which is an alkoxy group having 1 to 12 carbon atoms, a haloalkoxy group having 1 to 12 carbon atoms, a phenoxy group, or a biphenyloxy group.

[0038] Specific examples of the compound (a-9) that is the component (A) include compounds represented by the following formula:

[0039] Among the compounds exemplified above, novel compounds can be produced from known raw materials according to the methods described in the examples.

[0040] The low-molecular-weight photoalignment component (A) may be, but is not limited to, the above specific examples. Component (A) may also be a mixture of one or more compounds.

[0041] [Component (B)] The cured film-forming composition of the present invention contains a polymer having an epoxy group as component (B). When component (B) is cured by a crosslinking reaction, the alignment material obtained from the composition of the present invention exhibits alignment properties and solvent resistance.

[0042] The polymer having an epoxy group can be, for example, a homopolymer of a polymerizable unsaturated compound having an epoxy group, or a copolymer of a polymerizable unsaturated compound having an epoxy group and another polymerizable unsaturated compound.

[0043] Specific examples of the polymerizable unsaturated compound having an epoxy group include glycidyl acrylate, glycidyl methacrylate, α-ethyl glycidyl acrylate, α-n-propyl glycidyl acrylate, α-n-butyl glycidyl acrylate, 3,4-epoxybutyl acrylate, 3,4-epoxybutyl methacrylate, 6,7-epoxyheptyl acrylate, 6,7-epoxyheptyl methacrylate, 3,4-epoxycyclohexylmethyl acrylate, 3,4-epoxycyclohexylmethyl methacrylate, 6,7-epoxyheptyl α-ethyl acrylate, o-vinylbenzyl glycidyl ether, m-vinylbenzyl glycidyl ether, p-vinylbenzyl glycidyl ether, 4-hydroxybutyl methacrylate glycidyl ether, allyl glycidyl ether, 3-ethenyl-7-oxabicyclo[4.1.0]heptane, and 1,7-octadiene monoepoxide. Among these, 3,4-epoxycyclohexylmethyl acrylate and 3,4-epoxycyclohexylmethyl methacrylate are particularly preferred in terms of availability and the properties of the cured film obtained.

[0044] Examples of other polymerizable unsaturated compounds include (meth)acrylic acid alkyl esters, (meth)acrylic acid cyclic alkyl esters, methacrylic acid aryl esters, acrylic acid aryl esters, unsaturated dicarboxylic acid diesters, bicyclounsaturated compounds, maleimide compounds, unsaturated aromatic compounds, conjugated diene compounds, unsaturated monocarboxylic acids, unsaturated dicarboxylic acids, unsaturated dicarboxylic acid anhydrides, and other polymerizable unsaturated compounds. Throughout this specification, (meth)acrylic means both acrylic and methacrylic.

[0045] Specific examples of these include alkyl methacrylates such as hydroxymethyl methacrylate, 2-hydroxyethyl methacrylate, 3-hydroxypropyl methacrylate, 4-hydroxybutyl methacrylate, diethylene glycol monomethacrylate, 2,3-dihydroxypropyl methacrylate, 2-methacryloxyethyl glycoside, 4-hydroxyphenyl methacrylate, methyl methacrylate, ethyl methacrylate, n-butyl methacrylate, sec-butyl methacrylate, 2-ethylhexyl methacrylate, isodecyl methacrylate, n-lauryl methacrylate, tridecyl methacrylate, and n-stearyl methacrylate; alkyl acrylates such as methyl acrylate and isopropyl acrylate; and cyclic alkyl methacrylates such as cyclohexyl methacrylate, 2-methylcyclohexyl methacrylate, tricyclo[5.2.1.0]methacrylate. ２，６ ] decan-8-yl methacrylate, tricyclo[5.2.1.0 ２，６ ] decan-8-yloxyethyl methacrylate, isobornyl methacrylate, cholestanyl methacrylate, etc.; acrylic acid cyclic alkyl esters such as cyclohexyl acrylate, 2-methylcyclohexyl acrylate, tricyclo[5.2.1.0 ２，６ ] decan-8-yl acrylate, tricyclo[5.2.1.0 ２，６]decan-8-yloxyethyl acrylate, isobornyl acrylate, cholestanyl acrylate, etc.; methacrylic acid aryl esters such as phenyl methacrylate, benzyl methacrylate, etc.; acrylic acid aryl esters such as phenyl acrylate, benzyl acrylate, etc.; unsaturated dicarboxylic acid diesters such as diethyl maleate, diethyl fumarate, diethyl itaconate, etc.; bicyclo unsaturated compounds such as bicyclo[2.2.1]hept-2-ene, 5-methylbicyclo[2.2.1]hept-2-ene, etc. , 5-ethylbicyclo[2.2.1]hept-2-ene, 5-methoxybicyclo[2.2.1]hept-2-ene, 5-ethoxybicyclo[2.2.1]hept-2-ene, 5,6-dimethoxybicyclo[2.2.1]hept-2-ene, 5,6-diethoxybicyclo[2.2.1]hept-2-ene, 5-(2'-hydroxyethyl)bicyclo[2.2.1]hept-2-ene, 5,6-dihydroxybicyclo[2.2.1]hept-2-ene, 5,6-di(hydroxymethyl)bicyclo[2.2.1]hept-2-ene, 5,6-di(2'-hydroxy 5-hydroxy-5-methylbicyclo[2.2.1]hept-2-ene, 5-hydroxy-5-ethylbicyclo[2.2.1]hept-2-ene, 5-hydroxy-5-ethylbicyclo[2.2.1]hept-2-ene, 5-hydroxymethyl-5-methylbicyclo[2.2.1]hept-2-ene, etc.; maleimide compounds such as phenylmaleimide, cyclohexylmaleimide, benzylmaleimide, N-succinimidyl-3-maleimidobenzoate, N-succinimidyl-4-maleimidobutyrate, and N-succinimidyl-6-maleimidocaproate. ester, N-succinimidyl-3-maleimidopropionate, N-(9-acridinyl)maleimide, etc.; unsaturated aromatic compounds, for example, styrene, α-methylstyrene, m-methylstyrene, p-methylstyrene, vinyltoluene, p-methoxystyrene, etc.; conjugated diene compounds, for example, 1,3-butadiene, isoprene, 2,3-dimethyl-1,3-butadiene, etc.; unsaturated monocarboxylic acids, for example, acrylic acid, methacrylic acid, crotonic acid, etc.; unsaturated dicarboxylic acids, for example, maleic acid, fumaric acid, citraconic acid, mesaconic acid, itaconic acid, etc.;Examples of unsaturated dicarboxylic acid anhydrides include the anhydrides of the above-mentioned unsaturated dicarboxylic acids; examples of polymerizable unsaturated compounds other than those mentioned above include acrylonitrile, methacrylonitrile, vinyl chloride, vinylidene chloride, acrylamide, methacrylamide, vinyl acetate, etc.;

[0046] The copolymerization ratio of the polymerizable unsaturated compound having an epoxy group in the copolymer having an epoxy group is preferably 30% by mass or more, more preferably 50% by mass or more.

[0047] The synthesis of the (co)polymer having an epoxy group can be carried out by a known radical polymerization method, preferably in a solvent in the presence of a suitable polymerization initiator.

[0048] The weight average molecular weight (polystyrene equivalent) of the epoxy group-containing polymer, component (B), is 1,000 to 500,000, preferably 2,000 to 200,000, more preferably 3,000 to 150,000, and even more preferably 3,000 to 80,000.

[0049] As the polymer having an epoxy group, a commercially available product may be used. Examples of such commercially available products include EHPE3150 and EHPE3150CE (manufactured by Daicel Chemical Industries, Ltd.), UG-4010, UG-4035, UG-4040, and UG-4070 (manufactured by Toagosei Co., Ltd., ALUFON series), ECN-1299 (manufactured by Asahi Kasei Corporation), DEN431 and DEN438 (manufactured by The Dow Chemical Company), jER-152 (manufactured by Mitsubishi Chemical Corporation), Epicron N-660, N-665, N-670, N-673, N-695, N-740, N-770, and N-775 (manufactured by DIC Corporation), and EOCN-1020, EOCN-102S, and EOCN-104S (manufactured by Nippon Kayaku Co., Ltd.).

[0050] These polymers may be used alone or in combination of two or more.

[0051] The content of the polymer having an epoxy group as component (B) in the cured film-forming composition of the present invention is preferably 200 parts by mass to 1500 parts by mass, and more preferably 400 parts by mass to 1300 parts by mass, based on 100 parts by mass of the photoalignment component as component (A).

[0052] [Component (C)] The cured film-forming composition of the present invention further contains a thermal acid generator as component (C) in addition to the above-mentioned components (A) and (B). Component (C) is effective in accelerating the thermal curing reaction in the formation of a cured film using the cured film-forming composition that forms a cured film on the surface of the optical film of the present invention.

[0053] There are no particular limitations on the component (C), as long as it is a compound that undergoes thermal decomposition during pre-baking or post-baking to generate an acid, that is, a compound that undergoes thermal decomposition at a temperature of 60°C to 150°C to generate an acid.

[0054] Examples of the thermal acid generator include bis(tosyloxy)ethane, bis(tosyloxy)propane, bis(tosyloxy)butane, p-nitrobenzyl tosylate, o-nitrobenzyl tosylate, 1,2,3-phenylene tris(methylsulfonate), p-toluenesulfonic acid pyridinium salt, p-toluenesulfonic acid morphonium salt, p-toluenesulfonic acid ethyl ester, p-toluenesulfonic acid propyl ester, p-toluenesulfonic acid butyl ester, p-toluenesulfonic acid isobutyl ester, p-toluenesulfonic acid methyl ester, p-toluenesulfonic acid phenethyl ester, cyanomethyl p-toluenesulfonate, 2,2,2-trifluoroethyl p-toluenesulfonate, 2-hydroxybutyl p-tosylate, N-ethyl-4-toluenesulfonamide, and compounds represented by the following formulae [TAG-1] to [TAG-41], as well as onium salts such as iodonium salts, sulfonium salts, phosphonium salts, and selenium salts.

[0055]

[0056]

[0057]

[0058]

[0059]

[0060]

[0061]

[0062] Examples of the iodonium in the iodonium salt include diaryliodoniums such as diphenyliodonium, 4,4'-dichlorodiphenyliodonium, 4,4'-dimethoxydiphenyliodonium, 4,4'-di-tert-butyldiphenyliodonium, 4-methylphenyl(4-(2-methylpropyl)phenyl)iodonium, 3,3'-dinitrophenyliodonium, 4-(1-ethoxycarbonylethoxy)phenyl(2,4,6-trimethylphenyl)iodonium, and 4-methoxyphenyl(phenyl)iodonium. Examples of the iodonium salt include diaryliodonium salts having the above-mentioned iodonium as the cation moiety and chloride, bromide, mesylate, tosylate, trifluoromethanesulfonate, tetrafluoroborate, tetrakis(pentafluorophenyl)borate, hexafluorophosphate, hexafluoroarsenate, hexafluoroantimonate, or the like as the anion moiety.

[0063] Examples of the sulfonium in the sulfonium salt include arylsulfonium such as triphenylsulfonium, diphenyl(4-tert-butylphenyl)sulfonium, tris(4-tert-butylphenyl)sulfonium, diphenyl(4-methoxyphenyl)sulfonium, tris(4-methylphenyl)sulfonium, tris(4-methoxyphenyl)sulfonium, tris(4-ethoxyphenyl)sulfonium, diphenyl(4-(phenylthio)phenyl)sulfonium, tris(4-(phenylthio)phenyl)sulfonium, benzyl(4-acetoxyphenyl)(methyl)sulfonium, 2-methylbenzyl(4-acetoxyphenyl)(methyl)sulfonium, and 4-methylbenzyl(4-hydroxyphenyl)(methyl)sulfonium. Examples of sulfonium salts include arylsulfonium salts in which the above-mentioned sulfonium is used as the cation moiety and chloride, bromide, trifluoromethanesulfonate, tetrafluoroborate, hexafluorophosphate, hexafluoroarsenate, tetrakis(pentafluorophenyl)borate, hexafluoroantimonate, or the like is used as the anion moiety.

[0064] Examples of the phosphonium in the phosphonium salt include arylphosphonium such as tetraphenylphosphonium, ethyltriphenylphosphonium, tetra(p-methoxyphenyl)phosphonium, ethyltri(p-methoxyphenyl)phosphonium, benzyltriphenylphosphonium, etc. Examples of the phosphonium salt include arylphosphonium salts having the above phosphonium as the cation moiety and chloride, bromide, tetrafluoroborate, hexafluorophosphate, hexafluoroantimonate, or the like as the anion moiety.

[0065] The selenium salts include triarylselenium salts such as triphenylselenium hexafluorophosphate.

[0066] The component (C) is commercially available, and examples thereof include TA-100, TA-100FG, IK-1, and IK-1FG (all manufactured by San-Apro Ltd.), San-Aid (registered trademark) SI-B2A, San-Aid (registered trademark) SI-B7, San-Aid (registered trademark) SI-B3A, San-Aid (registered trademark) SI-B3, San-Aid (registered trademark) SI-B5, San-Aid (registered trademark) SI-B4, San-Aid (registered trademark) SI-150, San-Aid (registered trademark) SI-110, San-Aid (registered trademark) SI-60, San-Aid (registered trademark) SI-80, and San-Aid (registered trademark) SI-100 (all manufactured by Sanshin Chemical Industry Co., Ltd.).

[0067] The content of component (C) in the cured film-forming composition of the present invention is 1 part by mass to 150 parts by mass, preferably 3 parts by mass to 120 parts by mass, more preferably 5 parts by mass to 100 parts by mass, and even more preferably 10 parts by mass to 80 parts by mass, per 100 parts by mass of the photoalignment component (A). By ensuring that the content of component (C) is 1 part by mass or more, sufficient thermosetting properties and solvent resistance can be imparted, and high sensitivity to light exposure can also be imparted. Furthermore, by ensuring that the content is 150 parts by mass or less, the storage stability of the cured film-forming composition can be improved.

[0068] [Component (D)] In addition to the above-described components (A), (B), and (C), the cured film-forming composition of the present invention further contains, as component (D), a compound having a radical polymerizable group containing a C═C double bond and a nucleophilic group. This component (D) functions as an adhesion promoter between the alignment film and the liquid crystal layer. That is, the component (D) bonds to component (B) via the nucleophilic group and bonds to the polymerizable liquid crystal via the radical polymerizable group containing a C═C double bond, thereby promoting adhesion between the alignment film and the liquid crystal layer.

[0069] Examples of the nucleophilic group of the compound that is component (D) include a carboxy group, an epoxy group, an oxetanyl group, a hydroxy group, an amino group, a vinyl ether group, and an isocyanate group. Of these, the carboxy group and the epoxy group are preferred.

[0070] Examples of the compound having a radically polymerizable group containing a C═C double bond and a carboxy group include acrylic acid, methacrylic acid, crotonic acid, mono-(2-(acryloyloxy)ethyl)phthalate, mono-(2-(methacryloyloxy)ethyl)phthalate, mono-(2-(acryloyloxy)ethyl)hexahydrophthalate, mono-(2-(methacryloyloxy)ethyl)hexahydrophthalate, mono-(2-(acryloyloxy)ethyl)succinate, mono-(2-(methacryloyloxy)ethyl)succinate, N-(carboxyphenyl)maleimide, N-(carboxyphenyl)methacrylamide, N-(carboxyphenyl)acrylamide, and ω-carboxy-polycaprolactone mono(meth)acrylate. As these monomers, for example, commercially available products such as "Light Ester HO-MS," "Light Acrylate HOA-MS(N)," "Light Acrylate HOA-HH(N)," and "Light Acrylate HOA-MPL(N)" (all of which are product names of Kyoeisha Chemical Co., Ltd.), Aronix M-5300 and Aronix M-5400 (all of which are product names of Toagosei Co., Ltd.), A-SA, and SA (all of which are product names of Shin-Nakamura Chemical Co., Ltd.) can be used.

[0071] Examples of compounds having a radical polymerizable group containing a C═C double bond and an epoxy group include glycidyl methacrylate, glycidyl acrylate, 4-hydroxybutyl methacrylate glycidyl ether, 4-hydroxybutyl acrylate glycidyl ether, allyl glycidyl ether, o-vinylbenzyl glycidyl ether, m-vinylbenzyl glycidyl ether, p-vinylbenzyl glycidyl ether, 3-ethenyl-7-oxabicyclo[4.1.0]heptane, 1,2-epoxy-5-hexene, 1,7-octadiene monoepoxide, 3,4 3,4-epoxycyclohexylmethyl methacrylate, 3,4-epoxycyclohexylmethyl acrylate, α-ethyl glycidyl acrylate, α-n-propyl glycidyl acrylate, α-n-butyl glycidyl acrylate, 3,4-epoxybutyl acrylate, 3,4-epoxybutyl methacrylate, 6,7-epoxyheptyl acrylate, 6,7-epoxyheptyl methacrylate, 3,4-epoxycyclohexylmethyl acrylate, 3,4-epoxycyclohexylmethyl methacrylate, and α-ethyl 6,7-epoxyheptyl acrylate. As these monomers, for example, commercially available products such as CYCLOMER M-100 (manufactured by Daicel Corporation, trade name) and 4HBAGE (manufactured by Shinryo Corporation, trade name) can be used.

[0072] Furthermore, as the component (D), a compound having a spacer between the group selected from the epoxy group and the carboxy group and the radical polymerizable group can also be selected.

[0073] Preferred examples of the compound having a radical polymerizable group containing a C═C double bond, a spacer, and a carboxy group include the compounds represented by the following formulas (SC-1) and (SC-2). In formulas (SC-1) and (SC-2), X ４ represents a polymerizable group. ４ Specific examples of the polymerizable group represented by L include an acryloyl group, a methacryloyl group, a styrene group, a maleimide group, an acrylamide group, and a methacrylamide group. １ represents a single bond, an ether bond, an ester bond, an amide bond, a urea bond, or a urethane bond.１ and Q ３ Each independently represents an alkylene group having 2 to 10 carbon atoms. ２ represents a divalent group having a structure derived from a dicarboxylic acid anhydride, and n represents a natural number of 1 to 10.

[0074] Preferred examples of such compounds having a radical polymerizable group containing a C═C double bond, a spacer, and a carboxy group include mono-(2-(acryloyloxy)ethyl)phthalate, mono-(2-(methacryloyloxy)ethyl)phthalate, mono-(2-(acryloyloxy)ethyl)hexahydrophthalate, mono-(2-(methacryloyloxy)ethyl)hexahydrophthalate, mono-(2-(acryloyloxy)ethyl)succinate, mono-(2-(methacryloyloxy)ethyl)succinate, and ω-carboxy-polycaprolactone mono(meth)acrylate. Polyfunctional acrylates having a carboxy group are also preferred. Examples of commercially available products that can be used include those commercially available as "Light Ester HO-MS," "Light Acrylate HOA-MS(N)," "Light Acrylate HOA-HH(N)," and "Light Acrylate HOA-MPL(N)" (all of which are product names manufactured by Kyoeisha Chemical Co., Ltd.), Aronix M-5300, and Aronix M-5400 (all of which are product names manufactured by Toagosei Co., Ltd.).

[0075] Examples of the compound having a radical polymerizable group containing a C═C double bond, a spacer, and an epoxy group include the compound represented by the following formula (SE-1). In formula (SE-1), X ４ represents a polymerizable group. ４ Specific examples of the polymerizable group represented by L include an acryloyl group, a methacryloyl group, a styrene group, a maleimide group, an acrylamide group, and a methacrylamide group. １ represents a single bond, an ether bond, an ester bond, an amide bond, a urea bond, or a urethane bond. １ represents an alkylene group having 2 to 10 carbon atoms.

[0076] Examples of such a monomer having a radical polymerizable group containing a C═C double bond, a spacer, and an epoxy group include 4-hydroxybutyl methacrylate glycidyl ether, o-vinylbenzyl glycidyl ether, m-vinylbenzyl glycidyl ether, and p-vinylbenzyl glycidyl ether.

[0077] As the monomer having a radical polymerizable group containing a C═C double bond and a carboxy group, a polyfunctional acrylate having a carboxy group represented by the following (SC-3) is also preferred. In formula (SC-3), X ４ represents a polymerizable group, and specific examples of the polymerizable group include an acryloyl group, a methacryloyl group, a styrene group, a maleimide group, an acrylamide group, and a methacrylamide group. １ represents a single bond, an ether bond, an ester bond, an amide bond, a urea bond, or a urethane bond. ４ represents an (m+1)-valent organic group, and m represents a natural number of 2 to 10.

[0078] As such compounds, commercially available products such as Aronix M-510 and M-520 (trade names, manufactured by Toagosei Co., Ltd.) can be used.

[0079] Examples of the compound having a radical polymerizable group containing a C═C double bond and a hydroxy group include 2-hydroxyethyl acrylate, 2-hydroxyethyl methacrylate, 2-hydroxypropyl acrylate, 2-hydroxypropyl methacrylate, 4-hydroxybutyl acrylate, 4-hydroxybutyl methacrylate, 6-hydroxyhexyl acrylate, 6-hydroxyhexyl methacrylate, 8-hydroxyoctyl acrylate, 8-hydroxyoctyl methacrylate, 10-hydroxydecyl acrylate, 10-hydroxydecyl methacrylate, 12-hydroxydodecyl acrylate, and 12-hydroxydodecyl methacrylate. acrylate, 2,3-dihydroxypropyl acrylate, 2,3-dihydroxypropyl methacrylate, diethylene glycol monoacrylate, diethylene glycol monomethacrylate, caprolactone 2-(acryloyloxy)ethyl ester, caprolactone 2-(methacryloyloxy)ethyl ester, poly(ethylene glycol) ethyl ether acrylate, poly(ethylene glycol) ethyl ether methacrylate, 5-acryloyloxy-6-hydroxynorbornene-2-carboxylic-6-lactone, 5-methacryloyloxy-6-hydroxynorbornene-2-carboxylic-6-lactone, and the like.

[0080] Preferred examples of the compound having an oxetanyl group and a radically polymerizable group containing a C═C double bond include (3-ethyl-3-oxetanyl)methyl methacrylate and (3-ethyl-3-oxetanyl)methyl acrylate. Commercially available compounds include, for example, Eternacol (registered trademark) OXMA (manufactured by UBE Co., Ltd.).

[0081] Preferred compounds having a radically polymerizable group containing a C═C double bond and an isocyanate group include 2-(acryloyloxy)ethyl isocyanate and 2-(methacryloyloxy)ethyl isocyanate. Also preferred are polyfunctional acrylates having an isocyanate group, such as 1,1-(bisacryloyloxymethyl)ethyl isocyanate. Commercially available compounds that can be used include those commercially available as Karenz (registered trademark) AOI (manufactured by Resonac Co., Ltd.), Karenz (registered trademark) MOI (manufactured by Resonac Co., Ltd.), and Karenz (registered trademark) BEI (manufactured by Resonac Co., Ltd.).

[0082] Preferred examples of the compound having a radically polymerizable group containing a C═C double bond and a vinyl ether group include 2-(2-vinyloxyethoxy)ethyl acrylate and 2-(2-vinyloxyethoxy)ethyl methacrylate. Commercially available compounds that can be used include those sold under the trademark VEEA (manufactured by Nippon Shokubai Co., Ltd.) and VEEM (manufactured by Nippon Shokubai Co., Ltd.).

[0083] Examples of the compound having an amino group and a radically polymerizable group containing a C═C double bond include aminoalkyl (meth)acrylates such as aminomethyl (meth)acrylate, aminoethyl (meth)acrylate, aminopropyl (meth)acrylate, and aminoisopropyl (meth)acrylate.

[0084] The content of the component (D) in the cured film-forming composition according to an embodiment of the present invention is preferably 30 parts by mass to 300 parts by mass, and more preferably 50 parts by mass to 250 parts by mass, relative to the component (A), the compound represented by formula (a) (low molecular weight compound).

[0085] In the cured film-forming composition of the present embodiment, the component (D) may be a mixture of multiple types of compounds of the component (D).

[0086] [Other Additives] The cured film-forming composition of the present invention may contain other additives as long as the effects of the present invention are not impaired. Examples of other additives include a sensitizer. The sensitizer is effective in accelerating the photoreaction when forming a cured film on the surface of the optical film of the present invention.

[0087] Examples of the sensitizer include derivatives of benzophenone, anthracene, anthraquinone, thioxanthone, etc., and nitrophenyl compounds, etc. Among these, N,N-diethylaminobenzophenone, which is a benzophenone derivative, and 2-nitrofluorene, 2-nitrofluorenone, 5-nitroacenaphthene, 4-nitrobiphenyl, 4-nitrocinnamic acid, 4-nitrostilbene, 4-nitrobenzophenone, and 5-nitroindole, which are nitrophenyl compounds, are particularly preferred.

[0088] The sensitizer is not particularly limited to those mentioned above, and these compounds can be used alone or in combination of two or more kinds.

[0089] In an embodiment of the present invention, the proportion of the sensitizer used is preferably 0.1 to 20 parts by mass, and more preferably 0.2 to 10 parts by mass, per 100 parts by mass of component (A). If this proportion is too small, the effect as a sensitizer may not be fully obtained, whereas if it is too large, the transmittance of the formed cured film may decrease or the coating film may become rough.

[0090] The cured film-forming composition according to an embodiment of the present invention may contain other additives such as a silane coupling agent, a surfactant, a rheology modifier, a pigment, a dye, a storage stabilizer, an antifoaming agent, and an antioxidant, as long as the effects of the present invention are not impaired.

[0091] [Solvent] The cured film-forming composition according to an embodiment of the present invention can be used in the form of a solution (varnish) dissolved in a solvent (also referred to as "solvent"). The solvent used in this case dissolves the components (A), (B), (C), and (D) and, if desired, other additives, and the type and structure of the solvent are not particularly limited as long as the solvent has such dissolving ability.

[0092] Specific examples of the solvent include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, methyl cellosolve acetate, ethyl cellosolve acetate, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, propylene glycol, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, propylene glycol propyl ether, propylene glycol propyl ether acetate, cyclopentyl methyl ether, toluene, xylene, methyl ethyl ketone, cyclopentanone, cyclohexanone, 2-butanone, and 3-methyl-2-pentanone. , 2-pentanone, 2-heptanone, γ-butyrolactone, ethyl 2-hydroxypropionate, ethyl 2-hydroxy-2-methylpropionate, ethyl ethoxyacetate, ethyl hydroxyacetate, methyl 2-hydroxy-3-methylbutanoate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, methyl pyruvate, ethyl pyruvate, ethyl acetate, butyl acetate, ethyl lactate, butyl lactate, n-propyl acetate, isopropyl acetate, isopropanol, N,N-dimethylformamide, N,N-dimethylacetamide, and N-methyl-2-pyrrolidone. These solvents can be used alone or in combination of two or more.

[0093] The solvent is also commercially available. Examples of commercially available mixed solvents include Neoethanol (registered trademark) PM, Neoethanol (registered trademark) MIP, Neoethanol (registered trademark) IPM, Neoethanol (registered trademark) IPE, Neoethanol (registered trademark) PHI, Neoethanol (registered trademark) MHI, Neoethanol (registered trademark) PIP, Neoethanol (registered trademark) HIMTE, Neoethanol (registered trademark) PHM, Neoethanol (registered trademark) IPME, and Neoethanol (registered trademark) P-7 (all manufactured by Taishin Chemical Co., Ltd.).

[0094] Of these solvents, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, methyl ethyl ketone, cyclohexanone, 2-heptanone, propylene glycol propyl ether, propylene glycol propyl ether acetate, ethyl acetate, ethyl lactate, butyl lactate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, ethyl 3-ethoxypropionate, methyl 3-ethoxypropionate, and Neoethanol (registered trademark) IPM are more preferred due to their excellent film-forming properties and high safety.

[0095] <Preparation of Cured Film-Forming Composition> As described above, the cured film-forming composition of the present invention comprises a component (A) that is a photoalignment component represented by the above formula (a), a component (B) that is a polymer having an epoxy group, a component (C) that is a thermal acid generator, and a component (D) that is a compound having a radical polymerizable group containing a C═C double bond and a nucleophilic group, and in one embodiment, further comprises a solvent, so that the above-mentioned components are dissolved. The cured film-forming composition of the present invention may contain other additives as long as the effects of the present invention are not impaired.

[0096] Preferred examples of the cured film-forming composition of the present invention are as follows: [1]: A cured film-forming composition containing the component (A), 400 parts by mass to 1,300 parts by mass of the component (B) based on 100 parts by mass of the component (A), 10 parts by mass to 80 parts by mass of the component (C) based on 100 parts by mass of the component (A), and 50 parts by mass to 250 parts by mass of the component (D) based on 100 parts by mass of the component (A).

[0097] The blending ratios, preparation method, etc., when the cured film-forming composition of the present invention is used as a solution (in the form of a so-called varnish) are described in detail below. The solid content of the cured film-forming composition of the present invention is not particularly limited as long as each component is uniformly dissolved in the solvent, but is 1 to 80% by mass, preferably 2 to 60% by mass, and more preferably 3 to 40% by mass. Here, the solid content refers to all components of the cured film-forming composition excluding the solvent.

[0098] The method for preparing the cured film-forming composition of the present invention is not particularly limited. Examples of the preparation method include a method in which components (A), (C), and (D) are mixed in a predetermined ratio with a solution of component (B) dissolved in a solvent to obtain a homogeneous solution, or a method in which other additives are further added as necessary at an appropriate stage of this preparation method and mixed. In this case, component (C) may be added later, for example, immediately before use of the composition, in order to improve the storage stability of the composition.

[0099] In preparing the cured film-forming composition of the present invention, as described above, the solution of component (B) obtained by polymerization in a solvent can be used as is. In this case, for example, the component (A), the component (C), and the component (D) can be added to the solution of component (B) obtained by (co)polymerizing the above-mentioned polymerizable unsaturated compound having an epoxy group and, if desired, other polymerizable unsaturated compounds to obtain a uniform solution of the cured film-forming composition. In this case, additional solvent may be added for the purpose of adjusting the concentration. In this case, the solvent used in the production process of component (B) and the solvent used to adjust the concentration of the cured film-forming composition may be the same or different.

[0100] The prepared solution of the cured film-forming composition is preferably filtered using a filter having a pore size of about 0.2 μm before use in forming the cured film.

[0101] <Cured Film, Alignment Material, and Retardation Material> The cured film of the present invention can be formed by applying the above-mentioned cured film-forming composition (a solution thereof) onto a substrate (e.g., a silicon / silicon dioxide-coated substrate, a silicon nitride substrate, a substrate coated with a metal such as aluminum, molybdenum, or chromium, a glass substrate, a quartz substrate, an ITO substrate, etc.) or a film (e.g., a resin film such as a triacetyl cellulose (TAC) film, a cycloolefin polymer film, a polyethylene terephthalate film, or an acrylic film) by bar coating, spin coating, flow coating, roll coating, slit coating, spin coating followed by slit coating, inkjet coating, printing, or the like to form a coating film, and then heating and drying the resulting coating on a hot plate, in an oven, or the like.

[0102] The heating and drying conditions are such that, when a cured film is used as a liquid crystal alignment film as described below, the curing reaction proceeds to such an extent that the components of the liquid crystal alignment film are not eluted into the polymerizable liquid crystal solution to be applied thereon, and for example, a heating temperature and heating time appropriately selected from the ranges of 50°C to 150°C and 0.4 to 60 minutes are employed. The heating temperature and heating time are preferably 60°C to 130°C and 0.5 to 10 minutes.

[0103] The thickness of the cured film of the present invention is, for example, 0.05 μm to 5 μm, and can be appropriately selected taking into consideration the step and optical and electrical properties of the film used as the substrate or base material.

[0104] The cured film of the present invention thus produced can be irradiated with polarized UV light to function as a liquid crystal alignment film, i.e., as a component for aligning compounds having liquid crystallinity, including polymerizable liquid crystals, on a substrate, and thus the cured film can be used as an alignment material. This alignment material is also within the scope of the present invention.

[0105] The polarized UV irradiation method generally uses ultraviolet to visible light with a wavelength of 150 nm to 450 nm, and is carried out by irradiating linearly polarized light from a vertical or oblique direction at room temperature or in a heated state.

[0106] In the alignment material of the present invention, the cured film that becomes the liquid crystal alignment film has solvent resistance and heat resistance, so that a retardation material made of a polymerizable liquid crystal solution is applied onto this alignment material, and then heated to the phase transition temperature of the liquid crystal to turn the retardation material into a liquid crystal state, which can be aligned on the alignment material. Then, by curing the retardation material in the desired alignment state as it is, a retardation material having a layer with optical anisotropy can be formed.

[0107] As the retardation material, for example, the liquid crystal monomer having polymerizable group and the composition containing it are used.And, in the present invention, when the substrate on which the alignment material is formed is a film, the retardation material of the present invention is useful as a retardation film.The retardation material that forms such a retardation material is in a liquid crystal state, and on the alignment material, there are some that take the alignment state such as horizontal alignment, cholesteric alignment, vertical alignment, hybrid alignment, etc., and can be used according to the retardation properties that are required.

[0108] Furthermore, when manufacturing a patterned retardation material for use in a 3D display, the cured film on the surface of the alignment material of the present invention is exposed to polarized UV light through a line-and-space pattern mask at an angle of, for example, +45 degrees from a predetermined reference, and then the mask is removed and exposed to polarized UV light at a lower exposure dose at an angle of -45 degrees. This converts the cured film on the film surface into a liquid crystal alignment film in which two types of liquid crystal alignment domains with different liquid crystal alignment control directions are formed, and the optical film can be used as an alignment material. A retardation material made of a polymerizable liquid crystal solution is then applied to the alignment material, and the retardation material is then placed in a liquid crystal state by heating to the liquid crystal phase transition temperature. The polymerizable liquid crystal in the liquid crystal state is oriented on the alignment material in which the two types of liquid crystal alignment domains are formed, forming alignment states corresponding to each liquid crystal alignment domain. The retardation material in this alignment state is then cured as is, and the above-mentioned alignment state is fixed, resulting in a patterned retardation material in which two types of retardation domains with different retardation characteristics are regularly arranged.

[0109] The cured film of the present invention can also be used as a liquid crystal alignment film for a liquid crystal display element. For example, a liquid crystal display element in which the liquid crystal is aligned can be produced by using substrates on which the cured film of the present embodiment formed as described above is formed and laminating the substrates with the alignment materials facing each other via a spacer, and then injecting liquid crystal between the substrates. Therefore, the cured film of the present invention can be suitably used for producing various retardation materials (retardation films), liquid crystal display elements, etc.

[0110] EXAMPLES The present invention will be specifically described below with reference to examples of the present invention, but the present invention should not be construed as being limited to these examples.

[0111] [Abbreviations Used in Examples] The meanings of the abbreviations used in the following examples are as follows: <Polymerization initiator> MAIB: 2,2'-azobis(isobutyrate) dimethyl

[0112] <Component A> CIN1:

[0113] CIN2:

[0114] <Component D> M100: Cyclomer M-100 (manufactured by Daicel Corporation, 3,4-epoxycyclohexylmethyl methacrylate) 4HBAGE: 4-hydroxybutyl acrylate glycidyl ether (manufactured by Shinryo Corporation) M5300: Aronix M-5300 (manufactured by Toagosei Co., Ltd., ω-carboxy-polycaprolactone monoacrylate) 4HBA: 4-hydroxybutyl acrylate (manufactured by Shinryo Corporation) BEI: Karenz (registered trademark) BEI (manufactured by Resonac Corporation, 1,1-(bisacryloyloxymethyl)ethyl isocyanate) OXMA: Eternacol (registered trademark) OXMA (manufactured by UBE Corporation, (3-ethyl-3-oxetanyl)methyl methacrylate)

[0115] <Component C> B2A: San-Aid (registered trademark) SI-B2A (manufactured by Sanshin Chemical Industry Co., Ltd.) (thermal acid generator)

[0116] B7: San-Aid (registered trademark) SI-B7 (manufactured by Sanshin Chemical Industry Co., Ltd.) (thermal acid generator)

[0117] <Solvents> PMA: Propylene glycol monomethyl ether acetate BA: Butyl acetate EA: Ethyl acetate AcOEt: Ethyl acetate THF: Tetrahydrofuran

[0118] <Measurement of Weight Average Molecular Weight> Apparatus: GPC apparatus (HLC-8320) manufactured by Tosoh Corporation Column: TSKgel (registered trademark) α-4000 and TSKgel (registered trademark) α-3000 manufactured by Tosoh Corporation Column oven: 40°C Flow rate: 1 mL / min Eluent: N,N-dimethylformamide Standard sample: polystyrene

[0119] < １ H-NMR Measurement> Apparatus: Fourier transform superconducting nuclear magnetic resonance spectrometer (FT-NMR) "AVANCE III" (manufactured by BRUKER) 500 MHz. Solvent: deuterated dimethyl sulfoxide (DMSO-d ６ ). Standard substance: tetramethylsilane (TMS).

[0120] <Synthesis of Component A> <Synthesis Example 1 (Synthesis of CIN2)>

[0121] CIN1 (10.0 g, 30 mmol) and THF (120 g) were placed in a 500 mL four-neck flask, and after replacing the atmosphere with nitrogen, the flask was cooled to 0°C and chloromethyl ethyl ether (3.3 g, 34.5 mmol) was added dropwise. ３ N, 3.7 g, 36.0 mmol) was slowly added dropwise, and after confirming that the heat generation had subsided, the mixture was stirred at room temperature. After the reaction was completed, AcOEt (150 g) and ion-exchanged water (150 g) were added to the reaction solution, and the organic phase was extracted. The obtained organic phase was washed twice with ion-exchanged water (150 g) and concentrated to obtain 11.6 g of CIN2 (yellow liquid, 99% yield).

[0122] １ H-NMR (500MHz) in DMSO-d ６ ​: δ (ppm) = 7.64-7.68 (m, 3H), 6.95-6.96 (d, 2H), 6.46-6.50 (d, 1H), 6.01 (s, 1H), 5.65 (s, 1H), 5.34 (s, 2H), 4.08-4.10 (t, 2H), 3 99-4.01 (t, 2H), 3.64-3.69 (t, 2H), 1.87 (s, 3H), 1.70-1.73 (m, 2H), 1.62-1.65 (m, 2H), 1.35-1.44 (m, 4H), 1.13-1.16 (t, 3H).

[0123] <Synthesis of Component B> <Synthesis Example 2> M100 (37.6 g, 191.6 mmol) and MAIB (0.441 g, 1.92 mmol) as a polymerization catalyst were dissolved in a PMA / BA=5 / 5 (mass ratio) mixed solvent (57.1 g), and this solution was then added dropwise over 60 minutes to a flask containing a PMA / BA=5 / 5 (mass ratio) mixed solvent (95.1 g) maintained at 80°C. After completion of the addition, the mixture was allowed to react overnight at 80°C, yielding an acrylic polymer solution (PB-1) (solids concentration 20% by mass). The weight average molecular weight Mw of the resulting acrylic polymer was 52,460.

[0124] Preparation Example 1 CIN1 (10 parts by mass) was mixed as the component (A), PB-1 (70 parts by mass) obtained in Synthesis Example 2 as the component (B), and M100 (20 parts by mass) as the component (D), to which PMA and BA were added so that the solvent composition was PMA:BA = 20:80 (mass ratio), and the mixture was stirred for 2 hours. Dissolution was confirmed visually, and a solution was obtained. The resulting solution was then filtered through a filter with a pore size of 0.2 μm, thereby preparing composition (A-1) with a solids concentration of 8.0 mass%.

[0125] Preparation Examples 2 to 12 (A-2) to (A-11) and (B-1) were prepared in the same manner as in Preparation Example 1, except that the types and amounts of each component shown in Table 1 below were used.

[0126]

[0127] Preparation of Thermal Acid Generator Solution Preparation Example 13 1.0 g of B2A (component (C)) and 19.0 g of BA (solvent) were added and stirred for 1 hour. Dissolution was confirmed visually. The solution was filtered through a filter with a pore size of 0.2 μm to prepare a thermal acid generator solution (C-1).

[0128] Preparation Example 14: 1.0 g of B7 (component (C)) and 19.0 g of BA (solvent) were added and stirred for 1 hour. Dissolution was confirmed visually. The solution was filtered through a filter with a pore size of 0.2 μm to prepare a thermal acid generator solution (C-2).

[0129] <Preparation of cured film-forming composition and liquid crystal aligning agent> <Example 1-1> C-1 (0.08 g) obtained in Preparation Example 13 and EA (0.54 g) as a dilution solvent were added to A-1 (2.00 g) obtained in Preparation Example 1, and the mixture was stirred for 1 minute to obtain a cured film-forming composition (AL-1). (AL-1) was used as it was as a liquid crystal aligning agent.

[0130] Examples 1-2 to 1-12, Comparative Example 1-1 Cured film-forming compositions (AL-2) to (AL-12) and (BL-1) were prepared in the same manner as in Example 1-1, except that the types and amounts of each component were used as shown in Table 2. (AL-2) to (AL-12) and (BL-1) were used as liquid crystal aligning agents as they were.

[0131]

[0132] <Preparation of polymerizable liquid crystal solution for horizontal alignment> Paliocolor (registered trademark) LC-242 (manufactured by BASF Japan Ltd.) (19.3 g), which is a polymerizable liquid crystal for horizontal alignment, Omnirad (registered trademark) 907 (manufactured by IGM Resins B.V.) (0.6 g) as a photoradical initiator, and BYK (registered trademark)-361N (manufactured by BYK Japan KK) (0.1 g) as a leveling agent were added, and CPN (80 g) was further added as a solvent, followed by stirring for 2 hours and visually confirming that the mixture had dissolved, thereby obtaining a 20 mass % polymerizable liquid crystal solution (LC-1).

[0133] <Formation of Liquid Crystal Alignment Film and Preparation of Retardation Film> <Example 2-1> The liquid crystal alignment agent (AL-1) obtained in Example 1-1 was applied to a TAC film substrate using a bar coater to a wet film thickness of 4 μm. The film was dried by heating at 120° C. for 2 minutes in a hot air circulation oven to form a cured film on the film. Next, linearly polarized light with a wavelength of 313 nm was applied to the surface of this cured film at 20 mJ / cm ２ The liquid crystal alignment film was then vertically irradiated with an exposure dose of 500 mJ / cm. The polymerizable liquid crystal solution LC-1 for horizontal alignment was applied to the liquid crystal alignment film to a wet film thickness of 8 μm using a bar coater. The film was then dried by heating in an oven at 100°C for 2 minutes, and then irradiated with unpolarized light of 365 nm wavelength at 500 mJ / cm under a nitrogen atmosphere. ２ The polymerizable liquid crystal was cured by vertical irradiation with an exposure amount of 10 ...

[0134] Examples 2-2 to 2-12, Comparative Example 2-1 Using (AL-2) to (AL-12) and (BL-1) as liquid crystal aligning agents, retardation films were prepared in the same manner as in Example 2-1.

[0135] The retardation films prepared above were evaluated by the following methods. The evaluation results are shown in Table 3.

[0136] [Evaluation of Orientation] The prepared retardation film on the substrate was sandwiched between a pair of polarizing plates, and the state of expression of retardation properties under crossed Nicols was visually observed. When the retardation film exhibits retardation, light is transmitted evenly when rotated 45°, with the angle at which light does not transmit being 0°. When there are defects due to disordered alignment of the liquid crystal, light transmission defects occur. The results were recorded in the "Orientation" column as "excellent" when retardation is exhibited without defects, "good" when retardation is exhibited but with defects, and "poor" when no retardation is exhibited.

[0137] [Evaluation of Adhesion] Cross-cuts (1 mm x 1 mm x 100 squares) were made on the surface of the prepared retardation film (the surface on which the polymerizable liquid crystal layer was formed) using a cutter knife, and then cellophane tape (Cellotape (registered trademark), manufactured by Nichiban Co., Ltd., 24 mm wide) was attached. Next, when the cellophane tape was peeled off, the number of squares where the polymerized polymerizable liquid crystal layer remained on the underlying cured film and the underlying film substrate without peeling was counted. The results were recorded in the "Adhesion" column as "excellent" when all the layer remained, "good" when only some of the layer peeled off, and "poor" when all the layer peeled off.

[0138]

[0139] As is clear from the results in Table 3, all of the retardation films obtained from the cured film-forming compositions containing the component (A), component (B), component (D), and component (C) according to the present invention had good liquid crystal alignment properties and also good adhesion. In contrast, the cured film-forming compositions not containing the component (A), component (B), component (D), or component (C) according to the present invention did not provide sufficient liquid crystal alignment properties or adhesion.

[0140] The film having the cured film formed thereon according to the present invention is very useful as a liquid crystal alignment material for liquid crystal display elements or as an alignment material for forming optically anisotropic films provided inside or outside liquid crystal display elements, and is particularly suitable as a material for forming patterned retardation materials for 3D displays.Furthermore, it is also suitable as a material for forming cured films such as protective films, planarizing films, and insulating films in various displays such as thin film transistor (TFT) liquid crystal display elements and organic EL elements, and is particularly suitable as a material for forming interlayer insulating films in TFT liquid crystal elements, protective films in color filters, or insulating films in organic EL elements.

Claims

1. A cured film-forming composition comprising: (A) a compound represented by the following formula (a); (B) a polymer having an epoxy group; (C) a thermal acid generator; and (D) a compound having a radically polymerizable group containing a C═C double bond and a nucleophilic group. [In the formula, A １ and A ２ each independently represents a hydrogen atom, a methyl group, or a cyano group. １ represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 6 carbon atoms, a haloalkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a haloalkoxy group having 1 to 6 carbon atoms, an alkylamino group having 1 to 6 carbon atoms, a di(alkyl)amino group having 1 to 6 carbon atoms, an OH group, or an NH ２ a group, a carboxy group, a trialkoxysilyl group, a cyano group, a nitro group, or a group represented by the following formula (c-1): (In formula (c-1), the dashed line represents Q ２ represents a bond with １０１ is an alkylene group having 1 to 30 carbon atoms, and one or more hydrogen atoms of this alkylene group may be replaced by a fluorine atom or an organic group. １０１ -CH in ２ CH ２ - may be replaced by -CH=CH-, and further, when any of the following groups are not adjacent to each other, the alkylene group may be interrupted by a group selected from the group consisting of -O-, -NHCO-, -CONH-, -COO-, -OCO-, -NH-, -NHCONH- and -CO-, and M １ represents a hydrogen atom or a methyl group; ２ represents a single bond or an alkylene group having 1 to 20 carbon atoms, which may be branched or linear; Q ３ represents a single bond, —O—, —NHCO—, —CONH—, —COO—, —OCO—, —NH—, —NHCONH—, or —CO—, with the proviso that Q ２ If is a single bond, Q ３ is also a single bond, and Q ４ represents a divalent aromatic group, a divalent alicyclic group, a divalent heterocyclic group, or a divalent fused ring group; Q ５ represents a single bond, an oxygen atom, —COO—, or —OCO—; q1 is an integer of 0 to 3; q2 is 0 or 1; and Q ６ represents a single bond, an oxygen atom or a sulfur atom; ７ represents a single bond, an alkylene group having 1 to 20 carbon atoms, a divalent aromatic ring group, or a divalent aliphatic ring group. Here, the alkylene group having 1 to 20 carbon atoms may be branched or linear, and Q ６ When Q is a single bond, ７ is a single bond, and Q ８ is an OH group, NH ２ Q represents a hydroxyphenoxy group, a carboxyphenoxy group, an aminophenoxy group, an aminocarbonylphenoxy group, a phenylamino group, a hydroxyphenylamino group, a carboxyphenylamino group, an aminophenylamino group, a hydroxyalkylamino group, a bis(hydroxyalkyl)amino group, an alkoxysilyl group, a cyanophenylamino group, an alkoxy group having 1 to 12 carbon atoms, a haloalkoxy group having 1 to 12 carbon atoms, a cycloalkoxy group having 3 to 12 carbon atoms, a phenoxy group, or a biphenyloxy group, ２ , Q ３ , Q ６ and Q ７ are both single bonds, q1 is 0, and Q ８ is an OH group, Q １ represents a group other than a hydrogen atom as defined above.

2. The cured film-forming composition according to claim 1, wherein q2 is 0.

3. The cured film-forming composition according to claim 1, wherein the polymer having an epoxy group of component (B) is a homopolymer of a polymerizable unsaturated compound having an epoxy group or a copolymer of a polymerizable unsaturated compound having an epoxy group and another polymerizable unsaturated compound.

4. The cured film-forming composition according to claim 1, wherein the thermal acid generator (C) is a sulfonium salt.

5. The cured film-forming composition according to claim 1, wherein the nucleophilic group of the compound serving as component (D) is selected from the group consisting of a carboxy group, an epoxy group, an oxetanyl group, a hydroxy group, an amino group, a vinyl ether group, and an isocyanate group.

6. An alignment material obtained by using the cured film-forming composition according to any one of claims 1 to 5.

7. A retardation material formed using a cured film obtained from the cured film-forming composition according to any one of claims 1 to 5.

8. A compound represented by the following formula (a): [In the formula, A １ and A ２ each independently represents a hydrogen atom, a methyl group, or a cyano group. １ represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 6 carbon atoms, a haloalkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a haloalkoxy group having 1 to 6 carbon atoms, an alkylamino group having 1 to 6 carbon atoms, a di(alkyl)amino group having 1 to 6 carbon atoms, an OH group, or an NH ２ a group, a carboxy group, a trialkoxysilyl group, a cyano group, a nitro group, or a group represented by the following formula (c-1): (In formula (c-1), the dashed line represents Q ２ represents a bond with １０１ is an alkylene group having 1 to 30 carbon atoms, and one or more hydrogen atoms of this alkylene group may be replaced by a fluorine atom or an organic group. １０１ -CH in ２ CH ２ - may be replaced by -CH=CH-, and further, when any of the following groups are not adjacent to each other, the alkylene group may be interrupted by a group selected from the group consisting of -O-, -NHCO-, -CONH-, -COO-, -OCO-, -NH-, -NHCONH- and -CO-, and M １ represents a hydrogen atom or a methyl group; ２ represents a single bond or an alkylene group having 1 to 20 carbon atoms, which may be branched or linear; Q ３ represents a single bond, —O—, —NHCO—, —CONH—, —COO—, —OCO—, —NH—, —NHCONH—, or —CO—, with the proviso that Q ２ If is a single bond, Q ３ is also a single bond, and Q ４ represents a divalent aromatic group, a divalent alicyclic group, a divalent heterocyclic group, or a divalent fused ring group; Q ５ represents a single bond, an oxygen atom, —COO—, or —OCO—; q1 is an integer of 0 to 3; q2 is 0 or 1; and Q ６ represents an oxygen atom or a sulfur atom; ７ represents an alkylene group having 1 to 20 carbon atoms, which may be branched or linear; Q ８ represents an alkoxy group having 1 to 12 carbon atoms; ２ , Q ３ , Q ６ and Q ７ are both single bonds, q1 is 0, and Q ８ is an OH group, Q １ represents a group other than a hydrogen atom as defined above.

9. A compound represented by the following formula:

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