Cured film-forming composition, alignment material, and retardation material

Abstract

[Problem] To provide a cured film-forming composition that uses a film such as an acrylic film as the base material, has excellent solvent resistance, is capable of aligning a polymerizable liquid crystal with high sensitivity, and forms a cured film used for forming an alignment material with little cissing by low-temperature firing at less than 100° C. [Solution] A cured film-forming composition containing (A) a low-molecular compound having a photo-aligning group and a thermally crosslinkable group, (B) a polymer containing a monomer selected from N-hydroxymethyl(meth)acrylamide and N-alkoxymethyl(meth)acrylamide compounds as a monomer component, (C) a polymer having a hydroxy group (excluding those included in the definition of component (B)), (D) inorganic fine particles, and (E) a crosslinking catalyst.

Description

Cured film-forming composition, alignment material, and retardation material

[0001] The present invention relates to a cured film-forming composition for forming a cured film that aligns liquid crystal molecules, a cured film, an optical film, an alignment material, and a retardation material. In particular, the present invention relates to a patterned retardation material used in a 3D display using circularly polarized glasses, a retardation material used in a circular polarizer used as an anti-reflection film in an organic EL display, and a cured film-forming composition, a cured film, an optical film, an alignment material, and a retardation material useful for producing the retardation material.

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

[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 this optical film with reverse dispersion characteristics by combining a half-wave plate and a quarter-wave plate to form 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). With such liquid crystal materials with reverse dispersion characteristics, instead of forming a quarter-wave retardation plate using two retardation layers, each of which is a combination of a half-wave plate and a quarter-wave plate, the retardation layer can be formed from a single layer to ensure reverse dispersion characteristics, thereby enabling an optical film that can ensure a desired retardation over a wide wavelength band to be realized 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 also referred to as liquid crystal alignment ability) when irradiated with polarized UV light (see Patent Documents 5 to 7).

[0009] Furthermore, the alignment layer is required to have solvent resistance in addition to the ability to align liquid crystals. For example, the alignment layer may be exposed to heat or solvents during the manufacturing process of the retardation material. If an alignment layer lacking solvent resistance is exposed to a solvent, the ability to align liquid crystals may be significantly reduced.

[0010] Therefore, for example, Patent Document 8 proposes a liquid crystal aligning agent containing a polymer component having a structure capable of undergoing a crosslinking reaction by light and a structure that crosslinks by heat, in order to obtain stable liquid crystal alignment ability, and a liquid crystal aligning agent containing a polymer component having a structure that can undergo a crosslinking reaction by light and a compound having a structure that crosslinks by heat.

[0011] Furthermore, from the viewpoint of workability, it is required that the alignment layer can be formed by low-temperature firing at less than 100°C.

[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 Japanese Patent No. 4,207,430

[0013] When manufacturing retardation materials using photo-alignment technology, in recent years, in response to demands for reduced manufacturing costs, the production of optical materials using the so-called roll-to-roll method on inexpensive resin films such as acrylic film, TAC (triacetyl cellulose) film, and COP (cycloolefin polymer) film has become necessary. In particular, due to its excellent optical properties, reliability, and the advantage of being able to reduce manufacturing costs, there is a demand for the use of acrylic film as the resin film (substrate). However, with photo-alignment films formed from conventional materials such as those described above, the solvent resistance of the cured film formed by low-temperature baking at less than 100 ° C. is low, making it difficult to align polymerizable liquid crystals. In particular, when films such as acrylic film are used as substrates, the low solvent resistance of the alignment film causes areas that repel liquid crystals, so-called repelling, and there is a problem of alignment defects.

[0014] The present invention has been made based on the above findings and study results. That is, an object of the present invention is to provide a cured film-forming composition that can form a cured film used in the formation of an alignment material that has excellent solvent resistance, can align a polymerizable liquid crystal with high sensitivity, and has little repelling, by baking at a low temperature of less than 100°C, in an optical material that uses a film such as an acrylic film as a substrate.

[0015] Another object of the present invention is to provide an optical film having the above-mentioned cured film, and an alignment material and a retardation material formed using the cured film or the optical film.

[0016] Other objects and advantages of the present invention will become apparent from the following description.

[0017] A first aspect of the present invention relates to a cured film-forming composition containing: (A) a low molecular weight compound having a photoalignable group and a thermally crosslinkable group; (B) a polymer containing, as a monomer component, a monomer selected from N-hydroxymethyl(meth)acrylamide and N-alkoxymethyl(meth)acrylamide; (C) a polymer having a hydroxy group (excluding those included in the definition of component (B) above); (D) inorganic fine particles; and (E) a crosslinking catalyst.

[0018] In the first aspect of the present invention, the photoalignable group of component (A) is preferably a functional group having a structure that undergoes photodimerization or photoisomerization, and is preferably a cinnamoyl group or a group having an azobenzene structure.

[0019] A second aspect of the present invention relates to a cured film obtained from the cured film-forming composition of the first aspect of the present invention.

[0020] A third aspect of the present invention relates to an optical film having the cured film of the second aspect of the present invention.

[0021] A fourth aspect of the present invention relates to an alignment material formed using the cured film of the second aspect of the present invention.

[0022] A fifth aspect of the present invention relates to a retardation material formed using the cured film according to the second aspect of the present invention.

[0023] Throughout this specification, (meth)acrylic means both acrylic and methacrylic.

[0024] According to the present invention, it is possible to provide a cured film-forming composition that has excellent solvent resistance, can align polymerizable liquid crystals with high sensitivity, and can form a cured film that provides an alignment material with little liquid crystal repelling by baking at a low temperature of less than 100° C. Furthermore, according to the present invention, it is possible to provide an optical film having the cured film, and an alignment material and a retardation material that are formed using the cured film or the optical film.

[0025] As described above, there is a need for a cured film (alignment material) that has excellent solvent resistance, can align a polymerizable liquid crystal with high sensitivity, and causes little repelling of the liquid crystal. There is also a need for a cured film-forming composition that is suitable for forming a cured film (alignment material) with such properties.

[0026] The present inventors have conducted extensive research to meet the above-mentioned demands, and as a result have found that a cured film obtained from a cured film-forming composition having a specific composition has excellent solvent resistance, is capable of aligning polymerizable liquid crystals with high sensitivity, and can be used as an alignment material with little repelling of liquid crystals.

[0027] The cured film-forming composition of the present invention will be described in detail below, citing specific examples of components, etc. Then, the cured film and alignment material of the present invention using the cured film-forming composition of the present invention, as well as a retardation material and a liquid crystal display element, etc., formed using the alignment material will be described.

[0028] <Cured Film-Forming Composition> The cured film-forming composition of the present invention contains (A) a low molecular weight compound having a photoalignable group and a thermally crosslinkable group, (B) a polymer containing, as a monomer component, a monomer selected from N-hydroxymethyl(meth)acrylamide and N-alkoxymethyl(meth)acrylamide, (C) a polymer having a hydroxy group (excluding those included in the definition of component (B) above), (D) inorganic fine particles, and (E) a crosslinking catalyst. Furthermore, other additives may be added as long as they do not impair the effects of the present invention. Furthermore, the cured film-forming composition of the present invention contains a solvent and can be in the form of a so-called varnish. Details of each component are described below.

[0029] [Component (A)] The component (A) in the cured film-forming composition of the present invention is 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 properties to a cured film obtained from the cured film-forming composition of the present invention, and in this specification, the component (A) is also referred to as a photoalignment component.

[0030] <Low Molecular Weight Compound Having a Photo-Alignment Group and a Thermally Crosslinkable Group> The low molecular weight compound of the component (A) is a compound having a lower molecular weight than the polymer of the component (C) described below, which serves as the base for film formation in the cured film-forming composition of the present invention, and serves as a photo-alignment component in the cured film-forming composition.

[0031] In the cured film-forming composition of the present invention, the low-molecular-weight compound of component (A) is a compound having a photoalignment group, and further has a thermal crosslinkable group, preferably at least one group selected from the group consisting of a hydroxy group, a carboxy group, an amide group, an amino group, and an alkoxysilyl group. A portion of the photoalignment group may form a portion of the carboxy group or amide group listed as the thermal crosslinkable group. In the present invention, the photoalignment group generally refers to a functional group that exhibits the property of being aligned by light irradiation, typically a functional group at a structural site that undergoes photodimerization or photoisomerization. Other photoalignment groups include, for example, functional groups that undergo a photo-induced Fries rearrangement reaction (e.g., benzoic acid ester compounds) and groups that undergo a photodecomposition reaction (e.g., cyclobutane rings).

[0032] The photodimerizable structural moiety that the low molecular weight compound of component (A) can have as a photoalignment group is a moiety that forms a dimer upon irradiation with light, and specific examples thereof include a cinnamoyl group, a chalcone group, a coumarin group, an anthracene group, etc. Among these, a cinnamoyl group is preferred because of its high transparency in the visible light region and its high photodimerization reactivity.

[0033] Furthermore, the photoisomerizable structural moiety that the low molecular weight compound of component (A) can have as a photoalignment group refers to a structural moiety that changes between a cis form and a trans form upon irradiation with light, and specific examples thereof include moieties consisting of an azobenzene structure, a stilbene structure, etc. Among these, an azobenzene structure is preferred due to its high reactivity.

[0034] The low molecular weight compound having a photoalignable group and a thermally crosslinkable group (at least one group selected from the group consisting of a hydroxy group, a carboxy group, an amide group, an amino group, and an alkoxysilyl group) is, for example, a compound represented by the following formula:

[0035]

[0036] In the above formula, A １ and A ２ each independently represents a hydrogen atom or a methyl group.

[0037] X １１represents a structure in which 1 to 3 substituents selected from alkylene groups having 1 to 18 carbon atoms, phenylene groups, biphenylene groups, and combinations thereof are bonded via one or more bonds selected from a single bond, an ether bond, an ester bond, an amide bond, a urea bond, a urethane bond, an amino bond, a carbonyl bond, and combinations thereof, and the structure may be such that a plurality of the substituents are linked via the bonds.

[0038] X １２ represents a hydrogen atom, a halogen atom, a cyano group, an alkyl group having 1 to 18 carbon atoms, a phenyl group, a biphenyl group, or a cyclohexyl group. In this case, the alkyl group having 1 to 18 carbon atoms, the phenyl group, the biphenyl group, and the cyclohexyl group may be bonded to two or more groups via a covalent bond, an ether bond, an ester bond, an amide bond, or a urea bond.

[0039] X １３ represents a hydroxy group, a mercapto group, an alkoxy group having 1 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms, a phenoxy group, a biphenyloxy group, or a phenyl group.

[0040] X １４ 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.

[0041] X １５ represents a hydroxy group, a carboxy group, an amide group, an amino group, or an alkoxysilyl group, provided that X １４ When is a single bond, X １５ is a hydroxy group or an amino group.

[0042] X represents a single bond, an oxygen atom, or a sulfur atom. １４ is a single bond, then X is also a single bond.

[0043] When these substituents contain a benzene ring, the benzene ring may be substituted with one or more identical or different substituents selected from an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a halogen atom, a trifluoromethyl group, and a cyano group.

[0044] In the above formula, R １１ , R １２ , R １３ , R １４ , R １５ , R １６ , R １７ and R １８ each independently represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a halogen atom, a trifluoromethyl group, or a cyano group.

[0045] Specific examples of the low molecular weight compound having a photoalignable group and a hydroxy group, which is the component (A), include the compounds represented by the above formulas [A11] to [A15], and compounds other than these formulas include, for example, 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-hydroxymethyloxy ... Cinnamic 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-(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-hydroxy 4-(3-hydroxypropyloxy)cinnamic acid biphenyl ester, 4-(2-hydroxyethyloxy)cinnamic acid biphenyl ester, 4-hydroxymethyloxycinnamic acid biphenyl ester, 4-hydroxycinnamic acid biphenyl ester, 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, cinnamic acid hydroxymethyl ester,4-(8-hydroxyoctyloxy)azobenzene, 4-(6-hydroxyhexyloxy)azobenzene, 4-(4-hydroxybutyloxy)azobenzene, 4-(3-hydroxypropyloxy)azobenzene, 4-(2-hydroxyethyloxy)azobenzene, 4-hydroxymethyloxyazobenzene, 4-hydroxyazobenzene, 4-(8-hydroxyoctyloxy)chalcone, 4-(6-hydroxyhexyloxy)chalcone, 4-(4-hydroxybutyloxy)chalcone, 4-(3-hydroxypropyloxy)chalcone , 4-(2-hydroxyethyloxy)chalcone, 4-hydroxymethyloxychalcone, 4-hydroxychalcone, 4'-(8-hydroxyoctyloxy)chalcone, 4'-(6-hydroxyhexyloxy)chalcone, 4'-(4-hydroxybutyloxy)chalcone, 4'-(3-hydroxypropyloxy)chalcone, 4'-(2-hydroxyethyloxy)chalcone, 4'-hydroxymethyloxychalcone, 4'-hydroxychalcone, 7-(8-hydroxyoctyloxy)coumarin, 7-(6-hydroxyhexyloxy)coumarin coumarin, 7-(4-hydroxybutyloxy)coumarin, 7-(3-hydroxypropyloxy)coumarin, 7-(2-hydroxyethyloxy)coumarin, 7-hydroxymethyloxycoumarin, 7-hydroxycoumarin, 6-(8-hydroxyoctyloxycoumarin, 6-(6-hydroxyhexyloxycoumarin, 6-(4-hydroxybutyloxy)coumarin, 6-(3-hydroxypropyloxy)coumarin, 6-(2-hydroxyethyloxy)coumarin, 6-hydroxymethyloxycoumarin, 6-hydroxycoumarin, 4-[4-(8 4-[4-(6-hydroxyoctyloxy)benzoyl]cinnamic acid methyl ester, 4-[4-(6-hydroxyhexyloxy)benzoyl]cinnamic acid methyl ester, 4-[4-(4-hydroxybutyloxy)benzoyl]cinnamic acid methyl ester, 4-[4-(3-hydroxypropyloxy)benzoyl]cinnamic acid methyl ester, 4-[4-(2-hydroxyethyloxy)benzoyl]cinnamic acid methyl ester, 4-[4-hydroxymethyloxybenzoyl]cinnamic acid methyl ester, 4-[4-hydroxybenzoyl]cinnamic acid methyl ester,4-[4-(8-hydroxyoctyloxy)benzoyl]cinnamic acid ethyl ester, 4-[4-(6-hydroxyhexyloxy)benzoyl]cinnamic acid ethyl ester, 4-[4-(4-hydroxybutyloxy)benzoyl]cinnamic acid ethyl ester, 4-[4-(3-hydroxypropyloxy)benzoyl]cinnamic acid ethyl ester, 4-[4-(2-hydroxyethyloxy)benzoyl]cinnamic acid ethyl ester, 4-[4-hydroxymethyloxybenzoyl]cinnamic acid ethyl ester, 4-[4-hydroxybenzoyl] Cinnamic acid ethyl ester, 4-[4-(8-hydroxyoctyloxy)benzoyl]cinnamic acid tert-butyl ester, 4-[4-(6-hydroxyhexyloxy)benzoyl]cinnamic acid tert-butyl ester, 4-[4-(4-hydroxybutyloxy)benzoyl]cinnamic acid tert-butyl ester, 4-[4-(3-hydroxypropyloxy)benzoyl]cinnamic acid tert-butyl ester, 4-[4-(2-hydroxyethyloxy)benzoyl]cinnamic acid tert-butyl ester, 4-[4-hydroxy 4-[4-(methyloxybenzoyl)]cinnamic acid tert-butyl ester, 4-[4-hydroxybenzoyl]cinnamic acid tert-butyl ester, 4-[4-(8-hydroxyoctyloxy)benzoyl]cinnamic acid phenyl ester, 4-[4-(6-hydroxyhexyloxy)benzoyl]cinnamic acid phenyl ester, 4-[4-(4-hydroxybutyloxy)benzoyl]cinnamic acid phenyl ester, 4-[4-(3-hydroxypropyloxy)benzoyl]cinnamic acid phenyl ester, 4-[4-(2-hydroxyethyloxy)benzoyl]cinnamic acid phenyl ester 4-[4-hydroxybenzoyl]cinnamic acid phenyl ester, 4-[4-hydroxymethyloxybenzoyl]cinnamic acid phenyl ester, 4-[4-hydroxybenzoyl]cinnamic acid phenyl ester, 4-[4-(8-hydroxyoctyloxy)benzoyl]cinnamic acid biphenyl ester, 4-[4-(6-hydroxyhexyloxy)benzoyl]cinnamic acid biphenyl ester, 4-[4-(4-hydroxybutyloxy)benzoyl]cinnamic acid biphenyl ester, 4-[4-(3-hydroxypropyloxy)benzoyl]cinnamic acid biphenyl ester,4-[4-(2-hydroxyethyloxy)benzoyl]cinnamic acid biphenyl ester, 4-[4-hydroxymethyloxybenzoyl]cinnamic acid biphenyl ester, 4-[4-hydroxybenzoyl]cinnamic acid biphenyl ester, 4-benzoylcinnamic acid 8-hydroxyoctyl ester, 4-benzoylcinnamic acid 6-hydroxyhexyl ester, 4-benzoylcinnamic acid 4-hydroxybutyl ester, 4-benzoylcinnamic acid 3-hydroxypropyl ester, 4-benzoylcinnamic acid 2-hydroxyethyl ester, 4-benzoylcinnamic acid hydroxymethyl ester, 4-[4-(8-hydroxyoctyloxy)benzoyl]chalcone, 4-[4-(6-hydroxyhexyloxy)benzoyl]chalcone, 4-[4-(4-hydroxybutyloxy)benzoyl]chalcone [4-(4-hydroxymethyloxy)benzoyl]chalcone, 4-[4-(3-hydroxypropyloxy)benzoyl]chalcone, 4-[4-(2-hydroxyethyloxy)benzoyl]chalcone, 4-(4-hydroxymethyloxybenzoyl)chalcone, 4-(4-hydroxybenzoyl)chalcone, 4'-[4-(8-hydroxyoctyloxy)benzoyl]chalcone, 4'-[4-(6-hydroxyhexyloxy)benzoyl]chalcone, 4'-[4-(4-hydroxybutyloxy)benzoyl]chalcone, 4'-[4-(3-hydroxypropyloxy)benzoyl]chalcone, 4'-[4-(2-hydroxyethyloxy)benzoyl]chalcone, 4'-(4-hydroxymethyloxybenzoyl)chalcone, 4'-(4-hydroxybenzoyl)chalcone, and the like.

[0046] Specific examples of the low molecular weight compound having a photoalignable group and a carboxy group, which is component (A), include cinnamic acid, ferulic acid, 4-methoxycinnamic acid, 4-propoxycinnamic acid, 3,4-dimethoxycinnamic acid, coumarin-3-carboxylic acid, and 4-(N,N-dimethylamino)cinnamic acid.

[0047] Specific examples of the component (A), a low molecular weight compound having a photoalignable group and an amide group, include cinnamic acid amide, 4-methylcinnamic acid amide, 4-ethylcinnamic acid amide, 4-methoxycinnamic acid amide, and 4-ethoxycinnamic acid amide.

[0048] Specific examples of the component (A), a low molecular weight compound having a photoalignable group and an amino group, include 4-aminocinnamic acid methyl ester, 4-aminocinnamic acid ethyl ester, 3-aminocinnamic acid methyl ester, and 3-aminocinnamic acid ethyl ester.

[0049] Specific examples of the low molecular weight compound having a photoalignable group and an alkoxysilyl group, which is the component (A), 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.

[0050] The low molecular weight compound of component (A) is preferably a compound in which a polymerizable group is bonded via a spacer to a group in which a photoalignable moiety and a thermally crosslinkable moiety are bonded, as represented by the following formula (1): (In the formula, R １０１ represents a hydroxy group, an amino 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, or a bis(hydroxyalkyl)amino group; X １０１ represents a phenylene group which may be substituted with any substituent, and the benzene ring in these definitions may be substituted with a substituent.

[0051] When the benzene ring in the definition of formula (1) has a substituent, examples of the substituent include alkyl groups such as a methyl group, an ethyl group, a propyl group, a butyl group, and an isobutyl group; haloalkyl groups such as a trifluoromethyl group; alkoxy groups such as a methoxy group and an ethoxy group; halogen atoms such as an iodine atom, a bromine atom, a chlorine atom, and a fluorine atom; a cyano group; and a nitro group.

[0052] R in the above formula (1) １０１ As the alkyl group, a hydroxy group and an amino group are preferred, and a hydroxy group is particularly preferred.

[0053] Examples of the spacer include a divalent group selected from a linear alkylene group, a branched alkylene group, a cyclic alkylene group, and a phenylene group, or a group formed by bonding multiple divalent groups. Examples of the bond between the divalent groups constituting the spacer, the bond between the spacer and the group represented by formula (1), and the bond between the spacer and the polymerizable group include a single bond, an ester bond, an amide bond, a urea bond, and an ether bond. When multiple divalent groups are present, the divalent groups may be the same or different, and when multiple bonds are present, the bonds may be the same or different. Examples of the polymerizable group include a (meth)acryloyl group (also referred to as a (meth)acrylic group), a vinyl group, an allyl group, and a maleimide group.

[0054] Specific examples of such a low molecular weight compound in which a polymerizable group is bonded to a group in which a photoalignment moiety and a thermal crosslinking moiety are bonded, 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.

[0055] The low molecular weight photo-alignment component (A) can be exemplified by the above specific examples, but is not limited to these.

[0056] As described above, in the present invention, a low molecular weight compound can be used as component (A). Component (A) may also be a mixture of one or more low molecular weight compounds.

[0057] [Component (B)] The component (B) contained in the cured film-forming composition of the present embodiment is a polymer obtained using, as a monomer component, a monomer selected from N-hydroxymethyl(meth)acrylamide and N-alkoxymethyl(meth)acrylamide. The component (B) functions as a crosslinking agent.

[0058] Polymers containing a monomer selected from N-hydroxymethyl(meth)acrylamide and N-alkoxymethyl(meth)acrylamide compounds as a monomer component include polymers obtained by polymerizing a monomer such as N-alkoxymethyl(meth)acrylamide or N-hydroxymethyl(meth)acrylamide alone or copolymerizing it with a copolymerizable monomer. Examples of such polymers include poly(N-butoxymethylacrylamide), poly(N-ethoxymethylacrylamide), poly(N-methoxymethylacrylamide), poly(N-hydroxymethylacrylamide), copolymers of N-butoxymethylacrylamide and styrene, copolymers of N-butoxymethylacrylamide and methyl methacrylate, copolymers of N-ethoxymethylmethacrylamide and benzyl methacrylate, and copolymers of N-butoxymethylacrylamide, benzyl methacrylate, and 2-hydroxypropyl methacrylate. The weight-average molecular weight of the polymer of 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 50,000. The weight-average molecular weight is a value obtained by gel permeation chromatography (GPC) using polystyrene as a standard sample. The same applies hereinafter in this specification.

[0059] These polymers of component (B) can be used alone or in combination of two or more.

[0060] In the cured film-forming composition of the present embodiment, the content of the polymer obtained by containing, as a monomer component, a monomer selected from N-hydroxymethyl(meth)acrylamide and N-alkoxymethyl(meth)acrylamide, which is the component (B), is preferably 100 to 2,000 parts by mass, and more preferably 200 to 1,500 parts by mass, based on 100 parts by mass of the compound, which is the component (A).

[0061] [Component (C)] The cured film-forming composition of the present embodiment contains a polymer having a hydroxy group (hereinafter also referred to as a specific polymer) as component (C). This component is a polymer different from those included in the definition of component (B) above.

[0062] Examples of the polymer that is component (C) include acrylic polymers, polyamic acids, polyimides, polyvinyl alcohols, polyesters, polyester polycarboxylic acids, polyether polyols, polyester polyols, polycarbonate polyols, polycaprolactone polyols, polyalkyleneimines, polyallylamine, celluloses (cellulose or derivatives thereof), phenol novolac resins, melamine formaldehyde resins, and other polymers having a straight-chain or branched structure, and cyclic polymers such as cyclodextrins. Of these, the acrylic polymers that can be used include acrylic acid esters, methacrylic acid esters, and polymers obtained by (co)polymerizing these with monomers having an unsaturated double bond, such as styrene.

[0063] The specific polymer that is component (C) is preferably a cyclodextrin, a cellulose, a phenol novolac resin, an acrylic polymer having a hydroxyalkyl group on the side chain, a polyether polyol, a polyester polyol, a polycarbonate polyol, or a polycaprolactone polyol.

[0064] The acrylic polymer having a hydroxyalkyl group in the side chain, which is a preferred example of the specific polymer of component (C), is not particularly limited as long as it has such a structure, and the main chain skeleton and the type of side chain of the polymer constituting the acrylic polymer are not particularly limited. This acrylic polymer is a polymer having a repeating unit having a hydroxyalkyl group.

[0065] The acrylic polymer, which is an example of component (C), preferably has a weight-average molecular weight of 3,000 to 200,000, more preferably 4,000 to 150,000, and even more preferably 5,000 to 100,000. If the weight-average molecular weight is too high, exceeding 200,000, the solubility in solvents may decrease, resulting in poor handling, while if the weight-average molecular weight is too low, less than 3,000, the polymer may not cure sufficiently during heat curing, resulting in poor solvent resistance and heat resistance.

[0066] A simple method for synthesizing the acrylic polymer, which is an example of component (C), is to polymerize a (meth)acrylic monomer having a hydroxyalkyl group.

[0067] Examples of the (meth)acrylic monomer having a hydroxyalkyl group include 2-hydroxyethyl acrylate, 2-hydroxyethyl methacrylate, 2-hydroxypropyl acrylate, 2-hydroxypropyl methacrylate, 4-hydroxybutyl acrylate, 4-hydroxybutyl methacrylate, 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, and 5-methacryloyloxy-6-hydroxynorbornene-2-carboxylic-6-lactone.

[0068] Of these, 4-hydroxybutyl acrylate and 4-hydroxybutyl methacrylate are particularly preferred.

[0069] The specific polymer of component (C) can be a polymer having a repeating unit represented by the following formula (X) in addition to a repeating unit having a hydroxyalkyl group. If the specific polymer of component (C) has repeating units represented by the following formula (X) in an amount of 45 mass % or more of all repeating units, the resulting specific polymer can advantageously function as a component for improving adhesion to acrylic substrates. (In the above formula, R １ represents a hydrogen atom or a methyl group, R ２ represents a linear or branched alkyl group having 1 to 5 carbon atoms.) Hereinafter, a monomer that provides a repeating unit represented by the above formula (X) will be referred to as specific monomer X.

[0070] Examples of the alkyl acrylate or alkyl methacrylate monomer that is the specific monomer X include alkyl acrylate compounds such as methyl acrylate, ethyl acrylate, n-propyl acrylate, isopropyl acrylate, n-butyl acrylate, isobutyl acrylate, and tert-butyl acrylate, and alkyl methacrylate compounds such as methyl methacrylate, ethyl methacrylate, n-propyl methacrylate, isopropyl methacrylate, n-butyl methacrylate, isobutyl methacrylate, and tert-butyl methacrylate.

[0071] Among these specific monomers X, methyl methacrylate is particularly preferred from the viewpoints of availability and affinity with the acrylic film used as the substrate. That is, the polymer is obtained by using methyl methacrylate as a monomer, that is, in formula (X), R １ and R ２ is preferably a polymer having a unit structure in which all of the units represent a methyl group.

[0072] As a method for synthesizing an acrylic copolymer in which a specific monomer X, an alkyl acrylate ester or an alkyl methacrylate ester, is further copolymerized in addition to a monomer having a hydroxyalkyl group, a method in which a monomer having a hydroxyalkyl group is copolymerized with the specific monomer X is simple.

[0073] Furthermore, in the present invention, when obtaining the specific polymer, in addition to the specific monomer X and the (meth)acrylic monomer having a hydroxyalkyl group, a monomer (other monomer) copolymerizable with the specific monomer and not having the thermally crosslinkable group can be used in combination.

[0074] Specific examples of such other monomers include specific monomer X, and acrylic acid ester compounds or methacrylic acid ester compounds having a structure different from that of the monomer having a hydroxy group, maleimide compounds, acrylamide compounds, acrylonitrile, maleic anhydride, styrene compounds, and vinyl compounds.

[0075] Specific examples of the other monomers include, but are not limited to, the following: acrylic acid ester compounds having a structure different from that of the specific monomer X, etc., include benzyl acrylate, naphthyl acrylate, anthryl acrylate, anthrylmethyl acrylate, phenyl acrylate, phenoxyethyl acrylate, glycidyl acrylate, 2,2,2-trifluoroethyl acrylate, cyclohexyl acrylate, isobornyl acrylate, 2-methoxyethyl acrylate, methoxytriethylene glycol acrylate, 2-ethoxyethyl acrylate, tetrahydrofurfuryl acrylate, 3-methoxybutyl acrylate, γ-butyrolauton acrylate, 2-methyl-2-adamantyl acrylate, 2-propyl-2-adamantyl acrylate, 8-methyl-8-tricyclodecyl acrylate, and 8-ethyl-8-tricyclodecyl acrylate.

[0076] Examples of methacrylic acid ester compounds having a structure different from that of the specific monomer X include benzyl methacrylate, naphthyl methacrylate, anthryl methacrylate, anthrylmethyl methacrylate, phenyl methacrylate, phenoxyethyl methacrylate, glycidyl methacrylate, 2,2,2-trifluoroethyl methacrylate, cyclohexyl methacrylate, isobornyl methacrylate, 2-methoxyethyl methacrylate, methoxytriethylene glycol methacrylate, 2-ethoxyethyl methacrylate, tetrahydrofurfuryl methacrylate, 3-methoxybutyl methacrylate, 2-methyl-2-adamantyl methacrylate, γ-butyrolactone methacrylate, 2-propyl-2-adamantyl methacrylate, 8-methyl-8-tricyclodecyl methacrylate, and 8-ethyl-8-tricyclodecyl methacrylate.

[0077] Examples of the vinyl compound include methyl vinyl ether, benzyl vinyl ether, vinyl naphthalene, vinyl anthracene, vinyl biphenyl, vinyl carbazole, allyl glycidyl ether, phenyl vinyl ether, propyl vinyl ether, 3-ethenyl-7-oxabicyclo[4.1.0]heptane, 1,2-epoxy-5-hexene, and 1,7-octadiene monoepoxide.

[0078] Examples of the styrene compound include styrene, methylstyrene, chlorostyrene, and bromostyrene.

[0079] Examples of the maleimide compound include maleimide, N-methylmaleimide, N-phenylmaleimide, and N-cyclohexylmaleimide.

[0080] In the specific polymer, the proportion of repeating units having a hydroxyalkyl group is preferably 30 to 100 mol % based on the total amount (100 mol %) of monomers constituting the specific copolymer, i.e., 30 to 100 mol % based on the total amount (100 mol %) of all monomers used to obtain the specific polymer.

[0081] When the specific polymer contains a repeating unit represented by formula (X), the presence ratio thereof is preferably 45 to 70 mol % based on the total amount (100 mol %) of the monomers constituting the specific polymer of component (C). That is, the amount of specific monomer X used to obtain the specific polymer is preferably 45 to 70 mol % based on the total amount (100 mol %) of all the monomers used to obtain the specific polymer.

[0082] The method for obtaining the specific polymer is not particularly limited, but for example, the specific polymer can be obtained by a polymerization reaction at a temperature of 50 to 130°C in a solvent in which a monomer having a hydroxyalkyl group, specific monomer X, and optionally other monomers (other monomers), a polymerization initiator, etc. are present together. The solvent used in this case is not particularly limited as long as it dissolves the monomer having a hydroxyalkyl group, specific monomer X, optionally other monomers (other monomers), a polymerization initiator, etc. Specific examples of solvents used in the polymerization reaction are described in the section [Solvent] below.

[0083] The specific polymer obtained by the above method is usually in the form of a solution dissolved in a solvent, and the solution of the specific polymer can be used as is as the component (C) in the cured film-forming composition of the present invention.

[0084] Alternatively, the solution of the specific polymer obtained by the above method may be poured into diethyl ether, water, or the like under stirring to cause reprecipitation, and the resulting precipitate may be filtered and washed, followed by drying at room temperature or by heating under normal or reduced pressure to obtain a powder of the specific polymer. The above-described procedure can remove the polymerization initiator and unreacted monomers coexisting with the specific polymer, thereby obtaining a powder of the purified specific polymer. If the specific polymer cannot be sufficiently purified by a single procedure, the obtained powder may be redissolved in a solvent, and the above-described procedure may be repeated.

[0085] As the component (C) in the cured film-forming composition of the present invention, the specific polymer may be used in the form of a powder, or in the form of a solution obtained by redissolving the purified powder in a solvent described below.

[0086] Preferred examples of the specific polymer of component (C) include polyether polyols, such as polyethylene glycol, polypropylene glycol, and propylene glycol, as well as polyhydric alcohols such as bisphenol A, triethylene glycol, and sorbitol, which are either adducted or condensed with propylene oxide, polyethylene glycol, or polypropylene glycol. Specific examples of commercially available polyether polyols include the ADEKA Polyether P series, G series, EDP series, BPX series, FC series, and CM series manufactured by ADEKA Corporation, and UNIOX (registered trademark) HC-40, HC-60, ST-30E, ST-40E, G-450, and G-750, UNIOL (registered trademark) TG-330, TG-1000, TG-3000, TG-4000, HS-1600D, DA-400, DA-700, and DB-400, and NONION (registered trademark) LT-221, ST-221, and OT-221, all manufactured by NOF Corporation.

[0087]

[0033] Examples of polyester polyols, which are preferred examples of the specific polymer of component (C), include those obtained by reacting polycarboxylic acids such as succinic acid, glutaric acid, adipic acid, sebacic acid, phthalic acid, terephthalic acid, and isophthalic acid with diols such as ethylene glycol, propylene glycol, butylene glycol, polyethylene glycol, and polypropylene glycol. Specific examples of commercially available polyester polyols include Polylite (registered trademark) OD-X-286, OD-X-102, OD-X-355, OD-X-2330, OD-X-240, OD-X-668, OD-X-2108, OD-X-2376, OD-X-2044, OD-X-688, OD-X-2068, OD-X-2547, OD-X-2420, OD-X-2523, OD-X-2555, and OD-X-2560 manufactured by DIC Corporation, and Polyol manufactured by Kuraray Co., Ltd. Examples of suitable acrylic resins include P-510, P-1010, P-2010, P-3010, P-4010, P-5010, P-6010, F-510, F-1010, F-2010, F-3010, P-1011, P-2011, P-2013, P-2030, N-2010, PNNA-2016, and MAXIMOL (registered trademark) RDK-133, RFK-505, SDK-145, and RMK-342 manufactured by Air Water Performance Chemicals Inc. (formerly Kawasaki Kasei Kasei Chemicals Ltd.).

[0088] A preferred example of the specific polymer of component (C) is polycaprolactone polyol, which is obtained by ring-opening addition polymerization of ε-caprolactam with a polyhydric alcohol such as trimethylolpropane or ethylene glycol as an initiator. Specific examples of commercially available polycaprolactone polyols include Polylite (registered trademark) OD-X-2155, OD-X-640, and OD-X-2568 manufactured by DIC Corporation, and Plaxel (registered trademark) 205, L205AL, 205U, 208, 210, 212, L212AL, 220, 230, 240, 303, 305, 308, 312, and 320 manufactured by Daicel Corporation.

[0089] A preferred example of the specific polymer of component (C), polycarbonate polyol, is one obtained by reacting a polyhydric alcohol such as trimethylolpropane or ethylene glycol with diethyl carbonate, diphenyl carbonate, ethylene carbonate, etc. Specific examples of commercially available polycarbonate polyols include Plaxel (registered trademark) CD205, CD205PL, CD210, CD220, C-590, C-1050, C-2050, C-2090, C-3090, etc., manufactured by Daicel Corporation.

[0090] Preferred examples of the specific polymer of component (C) include celluloses, such as hydroxyalkyl celluloses, such as hydroxyethyl cellulose and hydroxypropyl cellulose, hydroxyalkyl alkyl celluloses, such as hydroxyethyl methyl cellulose, hydroxypropyl methyl cellulose and hydroxyethyl ethyl cellulose, and cellulose, and for example, hydroxyalkyl celluloses, such as hydroxyethyl cellulose and hydroxypropyl cellulose, are preferred.

[0091] Cyclodextrins, which are preferred examples of the specific polymer of component (C), include cyclodextrins such as α-cyclodextrin, β-cyclodextrin, and γ-cyclodextrin; methylated cyclodextrins such as methyl-α-cyclodextrin, methyl-β-cyclodextrin, and methyl-γ-cyclodextrin; hydroxymethyl-α-cyclodextrin, hydroxymethyl-β-cyclodextrin, hydroxymethyl-γ-cyclodextrin, 2-hydroxyethyl-α-cyclodextrin, 2-hydroxyethyl-β ... and hydroxyalkyl cyclodextrins such as 2-hydroxypropyl-γ-cyclodextrin, 2-hydroxypropyl-α-cyclodextrin, 2-hydroxypropyl-β-cyclodextrin, 2-hydroxypropyl-γ-cyclodextrin, 3-hydroxypropyl-α-cyclodextrin, 3-hydroxypropyl-β-cyclodextrin, 3-hydroxypropyl-γ-cyclodextrin, 2,3-dihydroxypropyl-α-cyclodextrin, 2,3-dihydroxypropyl-β-cyclodextrin, and 2,3-dihydroxypropyl-γ-cyclodextrin.

[0092] A preferred example of the specific polymer of component (C), phenol novolak resin, is, for example, a phenol-formaldehyde polycondensate.

[0093] In the cured film-forming composition of the present embodiment, the polymer of component (C) may be used in the form of a powder, or in the form of a solution obtained by redissolving a purified powder in a solvent described below.

[0094] In the cured film-forming composition of the present embodiment, the polymer of component (C) may be a mixture of multiple types of polymers of component (C).

[0095] The amount of the component (C) in the cured film-forming composition of the present invention is preferably 50 to 1,500 parts by mass, more preferably 100 to 1,000 parts by mass, and even more preferably 200 to 500 parts by mass, based on 100 parts by mass of the component (A).

[0096] [Component (D)] The component (D) contained in the cured film-forming composition of this embodiment is inorganic fine particles. Examples of the inorganic fine particles of component (D) include silica particles having a primary particle diameter of 1 to 200 nm. In particular, from the viewpoint of the storage stability of the varnish, silica particles whose surface has been modified with at least one silane coupling agent are preferred. Furthermore, from the viewpoint of not affecting the liquid crystal alignment, silica particles having a primary particle diameter of 1 nm to 100 nm, or 10 nm to 100 nm, whose surface has been modified with a silane coupling agent are preferred.

[0097] In the cured film-forming composition of the present invention, examples of the silane coupling agent used to modify the surface of the silica particles of component (D) include methyltrimethoxysilane, ethyltrimethoxysilane, n-propyltrimethoxysilane, isopropyltrimethoxysilane, n-butyltrimethoxysilane, isobutyltrimethoxysilane, n-pentyltrimethoxysilane, cyclopentyltrimethoxysilane, n-hexyltrimethoxysilane, cyclohexyltrimethoxysilane, isooctyltrimethoxysilane, vinyltrimethoxysilane, and allyltrimethoxysilane. Silane, 3-(meth)acryloyloxypropyltrimethoxysilane, phenyltrimethoxysilane, p-tolyltrimethoxysilane, p-styryltrimethoxysilane, benzyltrimethoxysilane, 1-naphthyltrimethoxysilane, trimethoxy[3-(phenylamino)propyl]silane, [3-(N,N-dimethylamino)propyl]trimethoxysilane, 3-(2-aminoethylamino)propyltrimethoxysilane, 8-(2-aminoethylamino)octyltrimethoxysilane, 3-aminopropyltrimethoxysilane, 3-mercapto Propyltrimethoxysilane, 3-isocyanatopropyltrimethoxysilane, tris[3-(trimethoxysilyl)propyl]isocyanurate, methyltriethoxysilane, ethyltriethoxysilane, n-propyltriethoxysilane, isopropyltriethoxysilane, n-butyltriethoxysilane, isobutyltriethoxysilane, n-pentyltriethoxysilane, cyclopentyltriethoxysilane, n-hexyltriethoxysilane, cyclohexyltriethoxysilane, isooctyltriethoxysilane, vinyltriethoxysilane trialkoxysilanes such as allyltriethoxysilane, 3-(meth)acryloyloxypropyltriethoxysilane, phenyltriethoxysilane, p-tolyltriethoxysilane, p-styryltriethoxysilane, benzyltriethoxysilane, 3-aminopropyltriethoxysilane, 3-mercaptopropyltriethoxysilane, 3-isocyanatopropyltriethoxysilane, and tris[3-(triethoxysilyl)propyl]isocyanurate; dimethyldimethoxysilane, diethyldimethoxysilane, and diisobutyldimethoxysilane;Cyclopentylmethyldimethoxysilane, dicyclopentyldimethoxysilane, cyclohexylmethyldimethoxysilane, vinylmethyldimethoxysilane, 3-(meth)acryloyloxypropylmethyldimethoxysilane, phenylmethyldimethoxysilane, diphenyldimethoxysilane, di-p-tolyldimethoxysilane, 3-aminopropylmethyldimethoxysilane, 3-mercaptopropylmethyldimethoxysilane, dimethyldiethoxysilane, diethyldiethoxysilane, diisobutyldiethoxysilane, cyclopentylmethyldiethoxysilane, dicyclopentyldiethoxysilane, cyclohexylmethyldiethoxysilane, vinylmethyldiethoxysilane, 3-(meth)acryloyloxypropylmethyldimethoxysilane Examples thereof include dialkoxysilanes such as acryloyloxypropylmethyldiethoxysilane, phenylmethyldiethoxysilane, diphenyldiethoxysilane, di-p-tolyldiethoxysilane, 3-(2-aminoethylamino)propylmethyldimethoxysilane, 3-aminopropylmethyldiethoxysilane, and 3-mercaptopropylmethyldiethoxysilane; monoalkoxysilanes such as trimethylmethoxysilane, triethylmethoxysilane, vinyldimethylmethoxysilane, 3-(meth)acryloyloxypropyldimethylmethoxysilane, phenyldimethylmethoxysilane, diphenylmethylmethoxysilane, and triphenylmethoxysilane; and polyfunctional silane coupling agents.

[0098] The silane coupling agents can be used alone or in combination of two or more.

[0099] When the silica particles are surface-modified using a silane coupling agent, the amount of the silane coupling agent used is preferably 0.1 to 2.0 mmol, more preferably 0.5 to 2.0 mmol, and even more preferably 0.5 to 1.7 mmol, per 1 g of the silica particles.

[0100] By using an amount of silane coupling agent greater than 0.1 millimoles, the affinity and adhesion between the surface of the silica particles and the organic resin are sufficient, the transmittance of the cured product and molded article obtained from the cured film-forming composition of the present invention is not reduced, and cracks can be prevented from occurring at the base of the cured product and molded article after the development process using an organic solvent.By using an amount of silane coupling agent less than 2.0 millimoles, the silane coupling agent is not excessive relative to the silica particles, and no silane coupling agent is left unused for surface modification of the silica particles, allowing the storage stability and mechanical properties of the cured product and molded article to be maintained.

[0101] In the cured film-forming composition of the present invention, the silica particles of component (D) are particles having a primary particle diameter of, for example, 1 to 100 nm, as described above. Here, primary particles are particles that constitute a powder, and particles formed by aggregation of these primary particles are called secondary particles. The primary particle diameter can be calculated from the relationship D = 6 / (ρS), which holds between the specific surface area (surface area per unit mass) S of the silica particles measured by gas adsorption (BET) method, the density ρ of the silica particles, and the primary particle diameter D. The primary particle diameter calculated from this relationship is the average particle diameter, which is the diameter of the primary particles. By using particles with a primary particle diameter of greater than 1 nm, aggregation of the silica particles can be suppressed, resulting in improved storage stability. Furthermore, by using particles with a primary particle diameter of less than 100 nm, the transparency of the cured product and molded article can be improved.

[0102] The silica particles of component (D) can be obtained by reacting surface-unmodified silica particles with the silane coupling agent by various known methods. As the surface-unmodified silica particles, for example, it is preferable to use the silica particles dispersed in an organic solvent (organosilica sol).

[0103] The organosilica sol may be a commercially available water-dispersed silica sol in which the water is replaced with an organic solvent by a known method such as vacuum distillation or ultrafiltration, or a commercially available powdered silica particle dispersed in an organic solvent.

[0104] The silica solid content concentration in the organosilica sol is not particularly limited, but is generally preferably 60% by mass or less.

[0105] The content of component (D) in the cured film-forming composition of the present invention is preferably 3 to 60 parts by mass, more preferably 3 to 45 parts by mass, and even more preferably 5 to 30 parts by mass, relative to 100 parts by mass of the total amount of components (A), (B), (C), and (E) described below contained in the cured film-forming composition. If the content of component (D) is less than 5 parts by mass, the heat resistance of the cured product and molded article obtained from the cured film-forming composition may be reduced. If the content of component (D) is more than 60 parts by mass, haze may occur in the cured product and molded article, and the transmittance may be reduced.

[0106] The component (D) can be used singly or in combination of two or more. For example, a plurality of silica particles having different primary particle sizes may be combined, or a plurality of silica particles having different types or amounts of silane coupling agents used for surface modification may be combined.

[0107] [Component (E)] The cured film-forming composition of the present invention further contains a crosslinking catalyst as component (E) in addition to the components (A), (B), (C) and (D) described above.

[0108] Examples of the crosslinking catalyst as component (E) include an acid or a thermal acid generator. This component (E) is effective in promoting the thermal curing reaction when a cured film is formed from the cured film-forming composition of the present invention (i.e., the composition that forms the cured film on the surface of the optical film of the present invention, which will be described later).

[0109] When an acid or thermal acid generator is used as component (E), component (E) is not particularly limited as long as it is a sulfonic acid group-containing compound, hydrochloric acid or a salt thereof, or a compound that undergoes thermal decomposition during pre-bake or post-bake to generate an acid, i.e., a compound that undergoes thermal decomposition at a temperature of 60 to 250°C to generate an acid.

[0110] Examples of such compounds include sulfonic acids such as hydrochloric acid, methanesulfonic acid, ethanesulfonic acid, propanesulfonic acid, butanesulfonic acid, pentanesulfonic acid, octanesulfonic acid, benzenesulfonic acid, p-toluenesulfonic acid, camphorsulfonic acid, trifluoromethanesulfonic acid, p-phenolsulfonic acid, 2-naphthalenesulfonic acid, mesitylenesulfonic acid, p-xylene-2-sulfonic acid, m-xylene-2-sulfonic acid, 4-ethylbenzenesulfonic acid, 1H,1H,2H,2H-perfluorooctanesulfonic acid, perfluoro(2-ethoxyethane)sulfonic acid, pentafluoroethanesulfonic acid, nonafluorobutane-1-sulfonic acid, dodecylbenzenesulfonic acid, 1,2-ethanedisulfonic acid, and methanesulfonic anhydride, as well as hydrates and salts thereof.

[0111] Examples of compounds that generate an acid by heat (by thermal decomposition) 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].

[0112]

[0113]

[0114]

[0115]

[0116]

[0117]

[0118]

[0119] The component (E) 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.).

[0120] The content of the component (E) in the cured film-forming composition of the present invention is preferably 0.01 to 100 parts by mass, more preferably 1 to 100 parts by mass, even more preferably 10 to 100 parts by mass, and particularly preferably 20 to 80 parts by mass, per 100 parts by mass of the component (A). By ensuring that the content of the component (E) is 0.01 parts 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 100 parts by mass or less, the storage stability of the cured film-forming composition can be improved.

[0121] [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.

[0122] 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.

[0123] These sensitizers are not particularly limited to those mentioned above, and these can be used alone or in combination of two or more compounds.

[0124] In an embodiment of the present invention, when a sensitizer is used, the proportion used is preferably 1 to 100 parts by mass, and more preferably 10 to 80 parts by mass, per 100 parts by mass of component (A). If this proportion is too small, the effect of the sensitizer may not be fully obtained, whereas if it is too large, the transmittance of the cured film formed may decrease, or the coating film may become rough.

[0125] 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.

[0126] [Solvent] The cured film-forming composition of the present invention can be used in the form of a solution dissolved in a solvent. The solvent used in this case dissolves the components (A), (B), (C), (D), and (E), and, if necessary, other additives, and the type and structure of the solvent are not particularly limited as long as it has the ability to dissolve the components.

[0127] 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, 3-methyl-2-pentanone, 2-pentanone, 2-heptanone, and the like. non, 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, methanol, ethanol, n-propanol, isopropanol, N,N-dimethylformamide, N,N-dimethylacetamide, and N-methyl-2-pyrrolidone.

[0128] The solvent is commercially available, and examples thereof 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.).

[0129] These solvents can be used singly or in combination of two or more. Among 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 because of their excellent film-forming properties and high safety.

[0130] <Preparation of Cured Film-Forming Composition> The cured film-forming composition of the present invention (i.e., the composition that forms the cured film on the surface of the optical film of the present invention) comprises, as described above, component (A) a low molecular weight compound having a photoalignable group and a thermally crosslinkable group (photoalignment component), component (B) a polymer containing, as a monomer component, a monomer selected from N-hydroxymethyl(meth)acrylamide and N-alkoxymethyl(meth)acrylamide compounds, component (C) a polymer having a hydroxy group, component (D) inorganic fine particles, and component (E) a crosslinking catalyst, and in one embodiment, can further contain a solvent, with the aforementioned components being dissolved in the solvent. The cured film-forming composition of the present invention can also contain other additives as long as they do not impair the effects of the present invention.

[0131] Preferred examples of the cured film-forming composition of the present invention are as follows.

[0132] [1]: A cured film-forming composition comprising: component (A); 100 to 2,000 parts by mass of component (B) based on 100 parts by mass of the compound that is component (A); 50 to 1,500 parts by mass of component (C) based on 100 parts by mass of component (A); 3 to 60 parts by mass of component (D) based on 100 parts by mass of the total amount of components (A), (B), (C), and (E); 0.01 to 100 parts by mass of component (E) based on 100 parts by mass of component (A); and a solvent. [2]: A cured film-forming composition comprising: component (A); 100 to 2,000 parts by mass of component (B) based on 100 parts by mass of the compound that is component (A); 100 to 1,000 parts by mass of component (C) based on 100 parts by mass of component (A); 3 to 60 parts by mass of component (D) based on 100 parts by mass of the total amount of components (A), (B), (C), and (E); 0.01 to 100 parts by mass of component (E) based on 100 parts by mass of component (A); and a solvent.

[0133] The blending ratios, preparation methods, 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 solids 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 preferably 1 to 80 mass %, more preferably 2 to 60 mass %, and even more preferably 3 to 40 mass %. Here, the solids content refers to all components of the cured film-forming composition excluding the solvent.

[0134] 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), (B), (D), and (E) are mixed in a predetermined ratio with a solution of component (C) dissolved in a solvent to obtain a homogeneous solution, or a method in which other additives are further added and mixed as necessary at an appropriate stage of this preparation method. Furthermore, component (E) may be added immediately before use in order to enhance the storage stability of the varnish.

[0135] In preparing the cured film-forming composition of the present invention, as described above, a solution of the specific polymer (component (C)) obtained by polymerization in a solvent can be used as is. In this case, for example, the component (A), the component (B), the component (D), the component (E), etc. can be added to a solution of the component (C) obtained by copolymerizing the above-mentioned hydroxyalkyl group-containing monomer, which is the monomer component of the polymer of the component (C), the specific monomer X, and, if desired, other monomers (other monomers), to prepare a homogeneous solution. 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 the component (C) and the solvent used to adjust the concentration of the cured film-forming composition may be the same or different.

[0136] 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.

[0137] <Optical Film> The optical film of the present invention is preferably obtained by applying the above-mentioned cured film-forming composition (a solution thereof) onto a film (for example, a resin film such as a triacetyl cellulose (TAC) film, a cycloolefin polymer film, a polyethylene terephthalate film, or an acrylic film) substrate 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 coating on a hot plate, in an oven, or the like to form a cured film.

[0138] As the acrylic film, a film made of a copolymer containing alkyl methacrylate and / or alkyl acrylate as the main monomer component can be suitably used.

[0139] The film used as the substrate preferably has a thickness of 20 to 100 μm.

[0140] 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 a heating time appropriately selected from the ranges of 50 to 99°C and 0.4 to 60 minutes are employed. The heating temperature and heating time are preferably 60 to 95°C and 0.5 to 10 minutes.

[0141] The thickness of the cured film on the surface of the optical film of the present invention is, for example, 0.05 to 5 μm, and can be appropriately selected in consideration of the step and optical and electrical properties of the film used as the substrate.

[0142] The optical film of the present invention produced in this manner can be irradiated with polarized UV light to cause the cured film formed on the substrate to function as a liquid crystal alignment film, i.e., as a component for aligning compounds having liquid crystal properties, including polymerizable liquid crystals, etc., and therefore the optical film can be used as an alignment material.

[0143] The polarized UV irradiation method generally uses ultraviolet to visible light with a wavelength of 150 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.

[0144] 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 after applying a retardation material made of a polymerizable liquid crystal solution onto this alignment material, the retardation material can be turned into a liquid crystal state by heating it to the phase transition temperature of the liquid crystal, and 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.

[0145] 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, since the substrate of the alignment material is a film, the retardation material of the present invention is useful as a retardation film.The retardation material forming 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 required.

[0146] Furthermore, when producing a patterned retardation material for use in a 3D display, the cured film on the surface of the optical film 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 angle of -45 degrees. This allows the cured film on the film surface to be converted 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 converted into an alignment material in which two types of liquid crystal distribution domains are formed. A retardation material made of a polymerizable liquid crystal solution is then applied to the alignment material, and the retardation material is then converted into 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 of the liquid crystal alignment domains. The retardation material in this oriented state is then cured as is, and the above-mentioned alignment state is fixed, thereby obtaining a patterned retardation material in which two types of retardation domains with different retardation characteristics are regularly arranged.

[0147] The optical film of the present invention can also be used as a liquid crystal alignment film for a liquid crystal display element. For example, the optical film of the present embodiment formed as described above can be used to laminate two optical films together via a spacer so that the alignment materials of the two films face each other, and then a liquid crystal can be injected between the substrates to produce a liquid crystal display element in which the liquid crystal is aligned. Therefore, the optical film of the present invention can be suitably used for producing various retardation materials (retardation films), liquid crystal display elements, etc.

[0148] The present invention will be described in more detail below with reference to examples, but the present invention is not limited to these examples.

[0149] [Abbreviations used in Examples] The meanings of the abbreviations used in the following examples are as follows: <Raw Materials> BMAA: N-butoxymethylacrylamide 4HBA: 4-hydroxybutyl acrylate HEMA: 2-hydroxyethyl methacrylate MMA: methyl methacrylate MAA: methacrylic acid AIBN: α,α'-azobisisobutyronitrile MAIB: 2,2'-azobis(isobutyrate) dimethyl

[0150] <Component A: low molecular weight compound having a photoalignment group and a thermal crosslinking group> M6CA:

[0151] 6CAM: (In the formula, Me represents a methyl group.)

[0152] <Component C: Polymer having a hydroxy group> RMK-342: Maximol RMK-342 (polyester polyol manufactured by Kawasaki Chemical Industries, Ltd.)

[0153] <Component D: inorganic fine particles> D-1: surface-unmodified organosilica sol D-2: methacrylic-modified organosilica sol D-3: alkylsilyl-modified organosilica sol

[0154] <Component E: Crosslinking catalyst> CSA: (±)-10-camphorsulfonic acid PTSA: p-toluenesulfonic acid monohydrate

[0155] <Others> HMM: A melamine crosslinking agent represented by the following structural formula [CYMEL (registered trademark) 303 (manufactured by Mitsui Cytec Co., Ltd.)] (In the formula, Me represents a methyl group.)

[0156] <Solvents> PM: Propylene glycol monomethyl ether IPM: Neoethanol (registered trademark) IPM (manufactured by Taishin Chemical Co., Ltd.) EA: Ethyl acetate CPN: Cyclopentanone MEK: Methyl ethyl ketone PGMEA: Propylene glycol monomethyl ether acetate

[0157] <Measurement of weight average molecular weight> Apparatus: GPC apparatus (HLC-8320) manufactured by Tosoh Corporation Column: Shodex (registered trademark) Asahipak GF-310HQ, GF-510HQ, and GF-710HQ manufactured by Showa Denko K.K. Column oven: 40°C Flow rate: 0.6 ml / min Eluent: N,N-dimethylformamide Standard sample: polystyrene

[0158] <Synthesis of Component B> <Synthesis Example 1> BMAA (145.5 g) and AIBN (4.6 g) as a polymerization catalyst were dissolved in PM (150.1 g), and this solution was then added dropwise over 30 minutes to a flask containing PM (200.1 g) maintained at 80°C. After completion of the addition, the mixture was reacted at 80°C for 5 hours to obtain an acrylic polymer solution (PB-1) (solids concentration 30% by mass). The weight average molecular weight Mw of the obtained acrylic polymer was 23,000.

[0159] <Synthesis of Component C> <Synthesis Example 2> 4HBA (197.0 g) and MAIB (3.1 g) as a polymerization catalyst were dissolved in PM (133.4 g), and this solution was then added dropwise over 2 hours to a flask containing PM (166.8 g) maintained at 70°C. After completion of the addition, the mixture was allowed to react at 70°C for 18 hours to obtain an acrylic polymer solution (PC-1) (solids concentration 40% by mass). The weight average molecular weight Mw of the obtained acrylic polymer was 22,700.

[0160] Synthesis Example 3 MMA (84.4 g), 4HBA (13.5 g), and MAIB (2.2 g) as a polymerization catalyst were dissolved in PM (150.1 g), and this solution was then added dropwise over 2 hours to a flask containing PM (250.2 g) maintained at 70°C. After completion of the addition, the mixture was allowed to react at 70°C for 18 hours to obtain an acrylic copolymer solution (PC-3) (solids concentration 20% by mass). The weight average molecular weight Mw of the obtained acrylic copolymer was 38,900.

[0161] Synthesis Example 4 MAA (2.5 g), MMA (9.2 g), HEMA (5.0 g), and AIBN (0.2 g) as a polymerization catalyst were dissolved in PM (50.7 g), and the mixture was reacted at 70° C. for 20 hours to obtain an acrylic copolymer solution (solid content concentration 25% by mass) (PC-4). The resulting acrylic copolymer had an Mn of 19,600 and an Mw of 45,200.

[0162] Preparation of Composition <Preparation Example 1> M6CA (0.062 g) as the component (A), a 30% by mass solution of the acrylic polymer (PB-1) (1.30 g) obtained in Synthesis Example 1 as the component (B), RMK-342 (0.21 g) as the component (C), D-1 (0.21 g) as the component (D), and PM (7.22 g) were added, stirred for 2 hours, and dissolution was confirmed visually. Thereafter, the mixture was filtered through a glass filter having a pore size of 1.0 μm to prepare a composition (A-1) having a solids concentration of 8.0% by mass.

[0163] Preparation Examples 2 to 9 Compositions (A-2) to (A-5) and (C-1) to (C-4) 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.

[0164] In Table 1, the numbers in parentheses for components (A) to (D) and other components indicate the mass ratio of each component (excluding the amount of solvent if diluted with a solvent).

[0165] <Preparation of Crosslinking Catalyst Solution> <Preparation Example 10> CSA (2.0 g) as a crosslinking catalyst and PM (18.0 g) as a solvent were added, stirred for 1 hour, and visually confirmed to be dissolved. The solution was filtered through a filter with a pore size of 0.2 μm to prepare a crosslinking catalyst solution (E-1).

[0166] Preparation Example 11: PTSA (2.0 g) as a crosslinking catalyst and PM (18.0 g) as a solvent were added, stirred for 1 hour, and visually confirmed to be dissolved. The solution was filtered through a filter with a pore size of 0.2 μm to prepare a crosslinking catalyst solution (E-2).

[0167] Preparation Example 12 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 BV (formerly BASF Japan Ltd.)) (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. The mixture was stirred for 2 hours, and dissolution was confirmed visually. The mixture was then filtered through a PTFE filter having a pore size of 0.2 μm, thereby obtaining a 20% by mass polymerizable liquid crystal solution (LC-1).

[0168] <Preparation of Cured Film-Forming Composition> <Example 1-1> A-1 (2.00 g) obtained in Preparation Example 1, E-1 (0.08 g) obtained in Preparation Example 10, EA (0.90 g) as a dilution solvent, and IPM (0.90 g) were mixed and stirred for 15 hours to obtain a cured film-forming composition (AL-1).

[0169] Examples 1-2 to 1-5 Cured film-forming compositions (AL-2) to (AL-5) were obtained in the same manner as in Example 1-1, except that A-2 to A-5 were used instead of A-1.

[0170] Comparative Examples 1-1 to 1-2 Cured film-forming compositions (CL-1) to (CL-2) were obtained in the same manner as in Example 1-1, except that C-1 to C-2 were used instead of A-1.

[0171] Comparative Example 1-3 C-3 (2.0 g) obtained in Preparation Example 8 and E-2 (0.04 g) obtained in Preparation Example 11 were added and stirred for 20 minutes to obtain a cured film-forming composition (CL-3).

[0172] Comparative Example 1-4 A cured film-forming composition (CL-4) was obtained in the same manner as in Comparative Example 1-3, except that C-4 was used instead of C-3.

[0173] <Formation of Liquid Crystal Alignment Film and Preparation of Retardation Film> <Example 2-1> The cured film-forming composition (AL-1) obtained in Example 1-1 was applied to an acrylic film substrate using a bar coater to a wet film thickness of 6 μm. The film was dried by heating at 90°C for 1 minute in a heat circulation oven to form a cured film on the film. Next, linearly polarized light with a wavelength of 313 nm was applied at 20 mJ / cm on the surface of this cured film. ２ The liquid crystal alignment film was then vertically irradiated with an exposure dose of 100 mJ / cm. A polymerizable liquid crystal solution LC-1 for horizontal alignment was applied to the liquid crystal alignment film to a wet thickness of 8 μm using a bar coater. The film was then dried by heating in an oven at 90°C for 1 minute, and then irradiated with unpolarized light at a wavelength of 365 nm at a dose of 500 mJ / cm under a nitrogen atmosphere. ２ The polymerizable liquid crystal was cured by vertical irradiation with an exposure amount of 1000 ppm to prepare a retardation film (S-1).

[0174] Examples 2-2 to 2-5, Comparative Examples 2-1 to 2-2 Retardation films (S-2) to (S-5) and (R-1) to (R-2) were produced in the same manner as in Example 2-1, except that AL-2 to AL-5 or CL-1 to CL-2 were used instead of the cured film-forming composition AL-1.

[0175] Comparative Examples 2-3 and 2-4: CL-3 or CL-4 was used instead of the cured film-forming composition AL-1, and the exposure dose of linearly polarized light was 30 mJ / cm ２ Retardation films (R-3) and (R-4) were produced in the same manner as in Example 2-1, except for the above change.

[0176] The retardation films obtained in Examples 2-1 to 2-5 and Comparative Examples 2-1 to 2-4 were sandwiched between a pair of polarizing plates, and the state of expression of retardation properties under crossed Nicols was visually observed. The films in which retardation was expressed without defects were evaluated as "○", and the films in which retardation was not expressed were evaluated as "×". The results are shown in Table 3.

[0177] [Evaluation of repelling] The retardation films obtained in Examples 2-1 to 2-5 and Comparative Examples 2-1 to 2-4 were sandwiched between a pair of polarizing plates, and the state of expression of retardation properties under crossed Nicols was visually observed. The films were evaluated as follows: those without repelling of the liquid crystal layer in a central 50 × 50 mm range were marked with "○", those with several to 20 repellings of the liquid crystal layer were marked with "△", and those with more than 20 repellings of the liquid crystal layer were marked with "×". The results are shown in Table 3.

[0178] As is clear from the results in Table 3, none of the retardation films obtained in Examples 2-1 to 2-5 had cissing and showed good alignment. On the other hand, none of the retardation films obtained in Comparative Examples 2-1 to 2-4 had cissing and good retardation films could be obtained.

[0179] 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 low molecular weight compound having a photoalignable group and a thermally crosslinkable group; (B) a polymer containing, as a monomer component, a monomer selected from N-hydroxymethyl(meth)acrylamide and N-alkoxymethyl(meth)acrylamide; (C) a polymer having a hydroxy group (excluding those included in the definition of component (B) above); (D) inorganic fine particles; and (E) a crosslinking catalyst.

2. The cured film-forming composition according to claim 1, wherein the photoalignable group of component (A) is a functional group having a structure that undergoes photodimerization or photoisomerization.

3. The cured film-forming composition according to claim 1, wherein the photoalignable group of component (A) is a cinnamoyl group.

4. The cured film-forming composition according to claim 1, wherein the photoalignable group of component (A) is a group having an azobenzene structure.

5. A cured film obtained from the cured film-forming composition according to any one of claims 1 to 4.

6. An optical film having the cured film according to claim 5.

7. An alignment material formed using the cured film according to claim 5.

8. A retardation material formed using the cured film according to claim 5.

Images