TWI807068B - Cured film, alignment material and retardation material - Google Patents

Abstract

The subject of the present invention is to provide a cured film that can obtain solvent resistance to various solvents in which liquid crystals are soluble, and can obtain good alignment, and at the same time, even a thick film with a film thickness of 3 μm or more has excellent transparency and resistance to good solvents, and provides an alignment material for photo-alignment and a phase difference material formed using the alignment material. The solution of the present invention is a cured film having an optical alignment group, an alignment material, and a retardation material. The cured film having an optical alignment group is a dry fired film formed from a coating of a cured film forming composition, and its film thickness is not less than 3 μm and not more than 20 μm. The coating of the cured film forming composition is characterized in that it contains a cured film forming composition. The cured film forming composition is characterized by containing: (A) A compound having a photoalignment group and any substituent selected from hydroxyl, carboxyl and amino groups, (B) a polyester polyol having an aromatic ring, and (C) Crosslinking agent.

Description

Hardened film, alignment material and retardation material

The present invention relates to a cured film for forming an alignment material for aligning liquid crystal molecules, an alignment material, and a retardation material. In particular, the present invention relates to a cured film, an alignment material, and a retardation material that can be used for a patterned retardation material that can be used to manufacture a circular polarizer-type 3D display, and a circular polarizing plate that can be used as an antireflection film of an organic EL display.

In the case of a circular polarizer-type 3D display, a retardation material is usually disposed on a display element such as a liquid crystal panel that forms an image. The phase difference material is plurally and regularly arranged with two types of phase difference regions with different phase difference characteristics, and constitutes a patterned phase difference material. In addition, below, in this specification, the phase difference material patterned so that such a phase difference region which differs in phase difference characteristic is arrange|positioned is called a patterned phase difference material.

The patterned retardation material is, for example, disclosed in Patent Document 1, which can be produced by optically patterning the retardation material composed of polymerizable liquid crystals. The optical patterning of the retardation material made of polymeric liquid crystals utilizes the known photo-alignment technology in the formation of alignment materials of liquid crystal panels. That is, a coating film made of a photo-alignment material is provided on a substrate, and two types of polarized light having different polarization directions are irradiated thereon. Furthermore, a photo-alignment film is obtained in the form of alignment materials of two types of liquid crystal alignment regions having different alignment control directions of liquid crystals. A solution phase retardation material containing polymerizable liquid crystals is coated on the photo-alignment film to realize the alignment of the polymerizable liquid crystals. Thereafter, the aligned polymerizable liquid crystal is cured to form a patterned retardation material.

The anti-reflection film of the organic EL display is composed of a linear polarizer and a 1/4 wavelength retardation plate. The external light facing the panel surface of the image display panel is converted into linear polarized light by the linear polarizer, and then converted into circular polarized light by the 1/4 wavelength retardation plate. Here, the external light caused by the circularly polarized light is reflected on the surface of the image display panel, etc., but the rotation direction of the polarization plane is reversed during the reflection. As a result, the reflected light is opposite to the arrival time, and after being converted into linearly polarized light in the direction blocked by the linear polarizer by the 1/4 wavelength retarder, it is then blocked by the linear polarizer, and as a result, the emission to the outside is significantly suppressed.

Regarding this 1/4 wavelength retardation plate, Patent Document 2 proposes a method of combining a 1/2 wavelength plate and a 1/4 wavelength plate to form a 1/4 wavelength retardation plate, thereby forming the optical film by utilizing inverse dispersion characteristics. In the case of this method, in a wide wavelength band for display of color images, it is possible to use a liquid crystal material due to a positive dispersion characteristic and form an optical film with an inverse dispersion characteristic.

Furthermore, in recent years, as a liquid crystal material that can be applied to this retardation layer, those having inverse dispersion characteristics have been proposed (Patent Documents 3 and 4). Based on such a liquid crystal material with inverse dispersion characteristics, instead of forming a 1/4 wavelength retardation plate by combining two retardation layers composed of a 1/2 wavelength plate and a 1/4 wavelength plate, the retardation layer can be constituted by a single layer and ensure reverse dispersion characteristics, thereby realizing an optical film that can ensure a desired retardation in a wide wavelength band with a simple configuration.

In order to align the liquid crystals, an alignment layer can be used. As a method for forming an alignment layer, for example, a rubbing method and a photo-alignment method are known, and the photo-alignment method is useful in that it does not generate static electricity or dust, which are problems of the rubbing method, and can quantitatively control the alignment process.

In forming an alignment material using a photo-alignment method, acrylic resins and polyimide resins having photodimerization sites such as cinnamoyl groups and chalcone groups in side chains are known as photo-alignment materials that can be used. It is pointed out that these resins exhibit the ability to control the alignment of liquid crystals (hereinafter also referred to as liquid crystal alignment) by polarized UV irradiation (see Patent Document 5 to Patent Document 7).

In addition, the alignment layer is required to have solvent resistance in addition to liquid crystal alignment ability. For example, the alignment layer may be exposed to heat or solvent during the manufacturing process of the retardation material. When the alignment layer is exposed to a solvent, there is a possibility that the alignment ability of liquid crystals will be significantly lowered.

Therefore, for example, in Patent Document 8, a liquid crystal alignment agent is proposed, which contains a polymer component in order to obtain stable liquid crystal alignment energy, and the polymer component has a structure capable of crosslinking reaction by light and a structure capable of crosslinking by heat; [Prior Art Literature] [Patent Document]

[Patent Document 1] Japanese Unexamined Patent Publication No. 2005-49865 [Patent Document 2] Japanese Patent Application Laid-Open No. 10-68816 [Patent Document 3] Specification of US Patent No. 8119026 [Patent Document 4] Japanese Unexamined Patent Publication No. 2009-179563 [Patent Document 5] Japanese Patent No. 3611342 [Patent Document 6] Japanese Patent Laid-Open No. 2009-058584 [Patent Document 7] Japanese National Publication No. 2001-517719 [Patent Document 8] Japanese Patent No. 4207430

[Problems to be Solved by the Invention]

As described above, the retardation material is formed by laminating a cured polymerizable liquid crystal layer on a photo-alignment film that is an alignment material. Therefore, it is necessary to develop an alignment material that can balance excellent liquid crystal alignment and solvent resistance.

However, according to the studies of the present inventors, it is known that an acrylic resin having a photodimerization site such as a cinnamonyl group or a chalcone group in a side chain cannot obtain sufficient characteristics when applied to the formation of a retardation material. In particular, in order to form an alignment material by irradiating polarized light UV to such a resin, and to use the alignment material to produce a retardation material composed of polymerizable liquid crystals, a large amount of polarized light UV exposure is required. This amount of polarized UV exposure is remarkably greater than the amount of polarized UV exposure (for example, about 30 mJ/cm ² ) sufficient for aligning liquid crystals for ordinary liquid crystal panels.

The reason why the amount of polarized UV exposure increases is that when forming a phase difference material, unlike liquid crystals for liquid crystal panels, polymerizable liquid crystals can be used in a solution state and coated on an alignment material.

When an acrylic resin or the like having a photodimerization site such as a cinnamoyl group in a side chain is used to form an alignment material and align a polymerizable liquid crystal, photocrosslinking by a photodimerization reaction proceeds in the acrylic resin or the like. Furthermore, before the resistance to the polymerizable liquid crystal solution is developed, it is necessary to perform polarized light irradiation with a large amount of exposure. In order to align the liquid crystals of the liquid crystal panel, generally, only the surface of the photo-alignment alignment material needs to be dimerized. However, in order to make the alignment material exhibit solvent resistance using conventional materials such as the above-mentioned acrylic resin, it is necessary to react the alignment material to the inside, which requires a larger amount of exposure. As a result, there is a problem that the alignment sensitivity of conventional materials becomes very small.

Furthermore, a technique of adding a crosslinking agent in order to express such solvent resistance to the above-mentioned conventional material resin is known. However, it is known that after the thermosetting reaction by the crosslinking agent progresses, a three-dimensional structure is formed inside the formed coating film, and photoreactivity decreases. That is, the alignment sensitivity will be greatly reduced, and even if a crosslinking agent is added to the conventional material, the desired effect cannot be obtained.

Furthermore, various organic solvents are used in liquid crystal inks, and thin films with low resistance to organic solvents are sometimes used in terms of optical properties. For the reason of so-called protective films, alignment films with a film thickness of 3 μm or more are required. In particular, when reverse dispersed liquid crystal is used as the liquid crystal, in order to ensure the solubility, it is necessary to use a good solvent such as N-methylpyrrolidone, and therefore solvent resistance to such a good solvent is required.

Based on the above, there is a demand for a photo-alignment technology that can improve the alignment sensitivity of the alignment material, reduce the amount of polarized UV exposure, and at the same time impart resistance to good solvents, and a liquid crystal alignment agent for photo-alignment that can be used in the formation of the alignment material. Furthermore, a technique capable of efficiently providing a retardation material is required.

The object of the present invention is accomplished based on the above knowledge and research results. That is, the object of the present invention is to provide a cured film for providing an alignment material which has excellent alignment sensitivity, pattern formability, and transparency even when the film thickness is 3 μm or more, is resistant to good solvents, and has excellent alignment uniformity.

Other objects and advantages of the present invention will be clearly understood from the following description. [Means used to solve the problem]

The first aspect of the present invention relates to a cured film having a photoalignment group, which is a dried and fired film formed from a coating of a cured film forming composition, and has a film thickness of 3 μm or more and 20 μm or less. The cured film forming composition is characterized in that it contains: (A) A compound having a photoalignment group and any substituent selected from hydroxyl, carboxyl and amino groups, (B) a polyester polyol having an aromatic ring, and (C) Crosslinking agent.

In the 1st aspect of this invention, it is preferable that the photoalignment group of (A) component is the functional group of the structure which performs photodimerization or photoisomerization.

In the first aspect of the present invention, it is preferable that the photoalignment group of the component (A) is a cinnamyl group.

In the first aspect of the present invention, it is preferable that the photo-alignment group of the (A) component is a group of an azobenzene structure.

In the 1st aspect of this invention, it is preferable that (A) component has 2 or more hydroxyl groups.

In the 1st aspect of this invention, it is preferable to further contain a crosslinking catalyst as (D)component.

In the 1st aspect of this invention, it is preferable that the ratio of (A) component and (B) component is 5:95-60:40 by mass ratio.

In the 1st aspect of this invention, it is preferable to contain (C)component of 5 mass parts - 500 mass parts based on 100 mass parts of total amounts of (A) component and (B) component.

In the first aspect of the present invention, it is preferable to contain 0.01 mass parts to 20 mass parts of (D) component with respect to 100 mass parts of the total amount of the compound of (A) component and the polymer of (B) component.

The second aspect of the present invention relates to an alignment material, which is obtained by using the cured film of the first aspect of the present invention.

A third aspect of the present invention relates to a phase difference material formed using the cured film of the first aspect of the present invention. [Invention effect]

According to the first aspect of the present invention, it is possible to provide a cured film for providing an alignment material having excellent alignment sensitivity, pattern formability, and transparency even when the film thickness is 3 μm or more, and also excellent in alignment uniformity.

According to the second aspect of the present invention, it is possible to provide an alignment material having excellent alignment sensitivity, pattern formability, and transparency even at a film thickness of 3 μm or more, resistance to good solvents, and excellent alignment uniformity.

According to the third aspect of the present invention, it is possible to provide a retardation material which can be efficiently formed even on alkali glass and which can be optically patterned.

[Mode for Carrying Out the Invention] ＜Cured film forming composition＞

The cured film-forming composition (hereinafter also referred to simply as the cured film-forming composition) that can be used in the present invention contains: (A) a low-molecular photo-alignment component, (B) a polyester polyol having an aromatic ring, and (C) a cross-linking agent. The cured film forming composition usable in the present invention may further contain, in addition to (A) component, (B) component, and (C) component, a crosslinking catalyst as (D) component, and a component that improves the adhesiveness of the cured film as (E) component. Furthermore, other additives may be contained as long as the effects of the present invention are not impaired.

Hereinafter, details of each component will be described. ＜(A)Ingredient＞ The (A) component contained in the cured film forming composition of this embodiment is the above-mentioned low molecular weight photo-alignment component.

Furthermore, the low-molecular photo-alignment component of the component (A) may be a compound having a photo-alignment group and any one substituent selected from a hydroxyl group, a carboxyl group, and an amino group. In a compound having a photoalignment group and any one substituent selected from hydroxyl, carboxyl, and amino, the photoreactive group constitutes the hydrophobic photoreactive part of the photoreactive component, and the hydroxyl group constitutes the hydrophilic thermally reactive part. In addition, in this invention, as a photoalignment group, it means the functional group of the structural part which performs photodimerization or photoisomerization.

The photodimerization structural site refers to a site that forms a dimer by light irradiation, and specific examples thereof include cinnamoyl, chalcone, coumarin, and anthracenyl. Among them, a cinnamoyl group having high transparency and photodimerization reactivity in the visible light region is preferable. In addition, the structural site undergoing photoisomerization is a site where the cis-isomer and trans-isomer are converted by light irradiation, and specific examples thereof include a site composed of an azobenzene structure, a toluene structure, and the like. Among them, an azobenzene structure is preferable because of its high reactivity. The compound which has a photoalignment group and a hydroxyl group is represented by following formula [A1] - [A5], for example.

In the aforementioned formulas [A1] to [A5], ^A1 and ^A2 each independently represent a hydrogen atom or a methyl group, ^{and X1} represents a structure in which 1 to 3 units selected from alkylene, phenylene, biphenylene, or a combination thereof with 1 to 18 carbon atoms are combined through one or more bonds selected from a single bond, an ether bond, an ester bond, an amide bond, a urethane bond, an amine bond, or a combination thereof. ^X2 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. Among them, an alkyl group having 1 to 18 carbon atoms, a phenyl group, a biphenyl group and a cyclohexyl group may be bonded via a covalent bond, an ether bond, an ester bond, an amide bond or a urea bond. ^X5 represents a hydroxyl group, a carboxyl group, an amino group or an alkoxysilyl group. X ⁶ represents a hydroxyl group, a mercapto group, an alkoxy group having 1 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms, or a phenyl group. ^X7 represents a single bond, an alkylene group having 1 to 20 carbon atoms, an aromatic ring group or an alicyclic group. Among them, the alkylene group having 1 to 20 carbon atoms may be branched or linear. ^X8 represents a single bond, an oxygen atom or a sulfur atom.

In addition, among these substituents, phenylene, phenyl, biphenylene and biphenyl may also be substituted by one or more substituents selected from the group consisting of 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.

In the above formula, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ each independently represent 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.

Specific examples of compounds having photoalignment groups and hydroxyl groups as component (A) include, for example, methyl 4-(8-hydroxyoctyloxy)cinnamate, methyl 4-(6-hydroxyhexyloxy)cinnamate, methyl 4-(4-hydroxybutoxy)cinnamate, methyl 4-(3-hydroxypropoxy)cinnamate, methyl 4-(2-hydroxyethoxy)cinnamate, methyl 4-hydroxymethoxycinnamate, methyl 4-hydroxycinnamate, (8-Hydroxyoctyloxy)ethyl cinnamate, 4-(6-hydroxyhexyloxy)ethyl cinnamate, 4-(4-hydroxybutoxy)ethyl cinnamate, 4-(3-hydroxypropoxy)ethyl cinnamate, 4-(2-hydroxyethoxy)ethyl cinnamate, 4-hydroxymethoxyethyl cinnamate, 4-hydroxyethyl cinnamate, 4-(8-hydroxyoctyloxy)phenyl cinnamate, 4-(6-hydroxyhexyloxy)phenyl cinnamate, 4-(4-Hydroxybutoxy)phenyl cinnamate, 4-(3-hydroxypropoxy)phenyl cinnamate, 4-(2-hydroxyethoxy)phenyl cinnamate, 4-hydroxymethoxyphenyl cinnamate, 4-hydroxyphenyl cinnamate, 4-(8-hydroxyoctyloxy)biphenyl cinnamate, 4-(6-hydroxyhexyloxy)biphenyl cinnamate, 4-(4-hydroxybutoxy)biphenyl cinnamate, 4-(3-hydroxypropoxy)cinnamate Diphenyl cinnamate, 4-(2-hydroxyethoxy) biphenyl cinnamate, 4-hydroxymethoxybiphenyl cinnamate, 4-hydroxybiphenyl cinnamate, 8-hydroxyoctyl cinnamate, 6-hydroxyhexyl cinnamate, 4-hydroxybutyl cinnamate, 3-hydroxypropyl cinnamate, 2-hydroxyethyl cinnamate, hydroxymethyl cinnamate, 4-(8-hydroxyoctyloxy)azobenzene, 4-(6-hydroxyhexyloxy)azobenzene, 4 -(4-hydroxybutoxy)azobenzene, 4-(3-hydroxypropoxy)azobenzene, 4-(2-hydroxyethoxy)azobenzene, 4-hydroxymethoxyazobenzene, 4-hydroxyazobenzene, 4-(8-hydroxyoctyloxy)chalcone, 4-(6-hydroxyhexyloxy)chalcone, 4-(4-hydroxybutoxy)chalcone, 4-(3-hydroxypropoxy)chalcone, 4-(2-hydroxyethoxy)chalcone, 4-hydroxymethanol Oxychalcone, 4-hydroxychalcone, 4'-(8-hydroxyoctyloxy)chalcone, 4'-(6-hydroxyhexyloxy)chalcone, 4'-(4-hydroxybutoxy)chalcone, 4'-(3-hydroxypropoxy)chalcone, 4'-(2-hydroxyethoxychalcone), 4'-hydroxymethoxychalcone, 4'-hydroxychalcone, 7-(8-hydroxyoctyloxy)coumarin, 7-(6-hydroxyhexyloxy)chalcone Beanin, 7-(4-hydroxybutoxy)coumarin, 7-(3-hydroxypropoxy)coumarin, 7-(2-hydroxyethoxy)coumarin, 7-hydroxymethoxycoumarin, 7-hydroxycoumarin, 6-hydroxyoctyloxycoumarin, 6-hydroxyhexyloxycoumarin, 6-(4-hydroxybutoxy)coumarin, 6-(3-hydroxypropoxy)coumarin, 6-(2-hydroxyethoxy)coumarin, 6-hydroxymethoxycoumarin , 6-hydroxycoumarin, etc.

Specific examples of compounds having a photoalignment group and a carboxyl group include cinnamic acid, ferulic acid, 4-nitrocinnamic acid, 4-methoxycinnamic acid, 3,4-dimethoxycinnamic acid, coumarin-3-carboxylic acid, 4-(N,N-dimethylamino)cinnamic acid, and the like.

Specific examples of the compound having a photoalignment group and an amino group include methyl 4-aminocinnamate, ethyl 4-aminocinnamate, methyl 3-aminocinnamate, ethyl 3-aminocinnamate, and the like. The low-molecular photo-alignment component that is the component (A) includes the above specific examples, but is not limited thereto.

And when the photo-alignment component of the (A) component is a compound having a photo-alignment group and a hydroxyl group, as the (A) component, a compound having two or more photo-alignment groups and/or two or more hydroxyl groups in the molecule can be used. Specifically, as the (A) component, a compound having one hydroxyl group and two or more photoalignment groups in the molecule, a compound having one photoalignment group and two or more hydroxyl groups in the molecule, and a compound having two or more photoalignment groups and two or more hydroxyl groups in the molecule can be used. For example, a compound represented by the following formula can be illustrated as an example of a compound having two or more photoalignment groups and hydroxyl groups in the molecule.

By appropriately selecting such a compound, it becomes possible to control the molecular weight of the photo-alignment component of the (A) component to a value within a desired range. As a result, as described later, when the photo-alignment component (A) component and the polymer (B) component thermally react with the crosslinking agent (C) component, sublimation of the photo-alignment component (A) component can be suppressed. Furthermore, the cured film forming composition of this embodiment can form an alignment material with high photoreaction efficiency as a cured film.

Moreover, as a compound of (A)component in a cured film formation composition, the mixture of the compound which has the photoalignment group and any one substituent selected from a hydroxyl group, a carboxyl group, and an amino group may be sufficient as it.

＜Component (B)＞ (B) component contained in the cured film formation composition of this embodiment is polyester polyol which has an aromatic ring.

Polyester polyols as a preferable example of the specific polymer of the component (B) include those in which aromatic polycarboxylic acids such as phthalic acid, isophthalic acid, and terephthalic acid are reacted with diols such as ethylene glycol, propylene glycol, butylene glycol, diethylene glycol, dipropylene glycol, triethylene glycol, trimethylene glycol, polyethylene glycol, and polypropylene glycol. Specific examples of polyester polyols having aromatic rings include RX-4800 manufactured by DIC Corporation, polyols P-520, P-1020, P-2020, P-1012, and P-2012 manufactured by Kuraray Corporation, NIPPOLAN 121E, 134, 179P, 131, 800, and 1100 manufactured by Tosoh Corporation, and MAXIMOL RDK-12 manufactured by Kawasaki Chemical Industry Co., Ltd. 1. RDK-133, RDK-142, RMK-342, RFK-505, RFK-506, RFK-509, RLK-087, RLK-035, etc.

The preferred molecular weight of the specific polymer of the component (B) is preferably 100 to 20,000 in terms of weight average molecular weight, and is preferably 100 to 10,000 in order to increase the degree of crosslinking, and is further preferably 100 to 5,000.

(B) The hydroxyl value of the specific polymer of the component is preferably from 50 to 1,000, and is preferably from 100 to 600 in terms of increasing the degree of crosslinking.

The preferable aromatic ring concentration of the specific polymer of the component (B) is preferably 5 mol % to 50 mol %, and is preferably 5 mol % to 30 mol % in terms of solubility.

In the cured film formation composition of this embodiment, the polymer of (B) component can also be used in the form of the solution which redissolved the powder form or the refined powder in the solvent mentioned later.

Moreover, in the cured film forming composition of this embodiment, the polymer of (B) component may be the mixture of several types of polymer of (B) component.

＜(C)Ingredient＞ The cured film forming composition of this embodiment contains a crosslinking agent as (C)component. More specifically, (C)component is a crosslinking agent which reacts with said (A)component and (B)component. (C) Component is bonded with the thermal crosslinkable group of the compound which is (A) component, and the hydroxyl group contained in (B) component. Furthermore, the cured film forming composition of this embodiment can form an alignment material with high photoreaction efficiency as a cured film.

As a crosslinking agent of (C)component, compounds, such as an epoxy compound, a methylol compound, and an isocyanate compound, are mentioned, Preferably a methylol compound is mentioned. Among them, the crosslinking agent of the component (C) is preferably a compound having two or more groups that form a crosslink with the thermally crosslinkable functional group in the component (A), for example, a crosslinking agent having two or more methylol or alkoxymethyl groups is preferred. Examples of compounds having such groups include methylol compounds such as alkoxymethylated acetylene carbamide, alkoxymethylated benzoguanidine, and alkoxymethylated melamine.

Specific examples of the methylol compound include compounds such as alkoxymethylated acetylene carbamide, alkoxymethylated benzoguanidine, alkoxymethylated melamine, tetrakis(alkoxymethyl)bisphenol, and tetrakis(methylol)bisphenol.

Specific examples of alkoxymethylated acetylene carbamide include, for example, 1,3,4,6-tetra(methoxymethyl)acetylene carbamide, 1,3,4,6-tetra(butoxymethyl)acetylene carbamide, 1,3,4,6-tetra(hydroxymethyl)acetylene carbamide, 1,3-bis(hydroxymethyl)urea, 1,1,3,3-tetra(butoxymethyl)urea, 1,1,3,3-tetra(methoxymethyl)urea, 1,3-bis(hydroxymethyl)- 4,5-dihydroxy-2-imidazolinone, 1,3-bis(methoxymethyl)-4,5-dimethoxy-2-imidazolinone, and the like. Commercially available products include compounds such as acetylene carbamide compounds (trade names: CYMEL (registered trademark) 1170, POWDERLINK (registered trademark) 1174) manufactured by Allnex Japan Co., Ltd. (formerly Mitsui Cytec Co., Ltd.), methylated urea resin (trade name: UFR (registered trademark) 65), butylated urea resin (trade name: UFR (registered trademark) 300, U-VAN10S60, U-VAN 10R, U-VAN11HV), urea/formaldehyde resin (high condensation type, trade name: BECKAMINE (registered trademark) J-300S, same P-955, same N) manufactured by DIC Co., Ltd. (formerly known as Dainippon Ink Chemical Industry Co., Ltd.).

Specific examples of alkoxymethylated benzoguanidine include, for example, tetramethoxymethylbenzoguanidine. Commercially available products include Allnex Japan Co., Ltd. (formerly Mitsui Cytec Co., Ltd.) (trade name: CYMEL (registered trademark) 1123), Sanwa Chemical Co., Ltd. (trade name: NIKALAC (registered trademark) BX-4000, DON BX-37, DON BL-60, DON BX-55H).

As a specific example of alkoxymethylated melamine, hexamethoxymethylmelamine etc. are mentioned, for example. Examples of commercially available products include methoxymethyl melamine compounds (trade names: CYMEL (registered trademark) 300, 301, 303, and 350) manufactured by Allnex Japan Co., Ltd. (formerly Mitsui Cytec Co., Ltd.), butoxymethyl melamine compounds (trade names: MYCOAT (registered trademark) 506, 508), and methoxymethyl melamine compounds manufactured by Sanwa Chemical Co., Ltd. (trade name: NIKALAC (registered trademark) MW-30, same MW-22, same MW-11, same MW-100LM, same MS-001, same MX-002, same MX-730, same MX-750, same MX-035), butoxymethyl-type melamine compound (trade name: NIKALAC (registered trademark) MX-45, same MX-410, same MX-302), etc.

As an example of tetrakis (alkoxymethyl) bisphenol and tetrakis (hydroxymethyl) bisphenol, tetrakis (alkoxymethyl) bisphenol A, tetrakis (hydroxymethyl) bisphenol A, etc. are mentioned.

Furthermore, as the crosslinking agent of the (C) component, a compound obtained by condensing a melamine compound, a urea compound, an acetylene carbamide compound, and a benzoguanidine compound in which the hydrogen atom of such an amino group is substituted by a methylol group or an alkoxymethyl group may be used. Examples thereof include high molecular weight compounds produced from melamine compounds and benzoguanidine compounds described in US Pat. No. 6,323,310. Commercially available products of the above-mentioned melamine compound include trade name: CYMEL (registered trademark) 303 (Allnex Japan Co., Ltd. (former name Mitsui Cytec Co., Ltd.), etc., and examples of commercially available products of the aforementioned benzoguanidine compound include trade name: CYMEL (registered trademark) 1123 (Allnex Japan Co., Ltd. (former name Mitsui Cytec Co., Ltd.)).

Furthermore, as the cross-linking agent of component (C), polymers produced by using acrylamide compounds or methacrylamide compounds in which N-hydroxyl is substituted by hydroxymethyl (that is, hydroxymethyl) or alkoxymethyl groups such as methacrylamide, N-methoxymethylmethacrylamide, N-ethoxymethacrylamide, N-butoxymethylmethacrylamide, etc. can also be used.

Examples of such polymers include poly(N-butoxymethacrylamide), copolymers of N-butoxymethacrylamide and styrene, copolymers of N-hydroxymethylmethacrylamide and methyl methacrylate, copolymers of N-ethoxymethylmethacrylamide and benzyl methacrylate, and copolymers of N-butoxymethacrylamide, benzyl methacrylate, and 2-hydroxypropyl methacrylate.

The polymer has a weight average molecular weight (in terms of polystyrene) of 1,000 to 500,000, preferably 2,000 to 200,000, more preferably 3,000 to 150,000, and still more preferably 3,000 to 50,000.

These crosslinking agents can be used alone or in combination of two or more.

The content of the crosslinking agent of component (C) in the cured film forming composition of this embodiment is preferably 5 to 500 parts by mass, more preferably 10 to 400 parts by mass based on 100 parts by mass of the total of components (A) and (B) .

＜(D)Ingredient＞ The cured film forming composition of this embodiment may contain a crosslinking catalyst as (D) component other than (A) component, (B) component, and (C) component. As a crosslinking catalyst which is (D)component, an acid or a thermal acid generator can be used, for example. This (D) component is effective in promoting the thermosetting reaction of the cured film forming composition of this embodiment.

The component (D) is not particularly limited as long as it is a compound containing a sulfonic acid group, hydrochloric acid or a salt thereof, and a compound that generates an acid by thermally decomposing during pre-baking or post-baking, that is, a compound that generates an acid by thermally decomposing at a temperature of 80° C. to 250° C.

Examples of such compounds include 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, 1,3,5-trimethylbenzenesulfonic acid, p-xylene-2-sulfonic acid, m-xylene-2-sulfonic acid, 4-ethylbenzenesulfonic acid, 1H,1 Sulfonic acids such as H,2H,2H-perfluorooctanesulfonic acid, perfluoro(2-ethoxyethane)sulfonic acid, pentafluoroethanesulfonic acid, nonafluorobutane-1-sulfonic acid, dodecylbenzenesulfonic acid, or their hydrates or salts, etc.

In addition, examples of compounds that generate acid by heat include bis(toluenesulfonyloxy)ethane, bis(toluenesulfonyloxy)propane, bis(toluenesulfonyloxy)butane, p-nitrobenzyl toluenesulfonate, o-nitrobenzyl toluenesulfonate, 1,2,3-phenylene ginseng (methylsulfonate), pyridinium p-toluenesulfonate, morpholinium p-toluenesulfonate, ethyl p-toluenesulfonate, Propyl toluenesulfonate, butyl p-toluenesulfonate, isobutyl p-toluenesulfonate, methyl p-toluenesulfonate, phenylethyl p-toluenesulfonate, p-cyanomethyl toluenesulfonate, 2,2,2-trifluoroethyl p-toluenesulfonate, 2-hydroxybutyl p-toluenesulfonate, N-ethyl-p-toluenesulfonamide, and compounds represented by the following formula, etc.

The content of the component (D) in the cured film forming composition of this embodiment is preferably 0.01 to 20 parts by mass, more preferably 0.1 to 18 parts by mass, and still more preferably 0.5 to 15 parts by mass based on 100 parts by mass of the total amount of the compound of the component (A) and the polymer of the component (B). By making content of (D)component 0.01 mass part or more, sufficient thermosetting property and solvent resistance can be provided to the cured film forming composition of this embodiment, and also high sensitivity to light irradiation can be provided.

<Solvent> The cured film forming composition of this embodiment can be used mainly in the state of the solution which melt|dissolved in the solvent. The solvent used at this time should just dissolve (A) component, (B) component, (C) component, (D) component as needed, and/or other additives mentioned later, and its type and structure etc. are not specifically limited.

Specific examples of the solvent include, for example, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, methyl celuxoacetate, ethyl cyrusuree acetate, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, propylene glycol, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, propylene glycol propyl ether acetate, toluene, xylene, methyl ethyl ketone, cyclopentanone, cyclohexanone, 2-butanone, 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-methylbutyrate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, ethyl 3-ethoxypropionate, methyl 3-ethoxypropionate, methyl pyruvate, ethyl pyruvate, ethyl acetate, butyl acetate, ethyl lactate, butyl lactate , N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone, etc.

These solvents may be used alone or in combination of two or more.

＜Other additives＞ Furthermore, the cured film forming composition of this embodiment may contain a sensitizer, a silane coupling agent, a surfactant, a rheology modifier, a pigment, a dye, a storage stabilizer, an antifoaming agent, an antioxidant, etc. as needed, as long as the effect of the present invention is not impaired.

For example, a sensitizer is effective in promoting a photoreaction after forming a thermosetting film using the cured film forming composition of this embodiment.

A sensitizer as an example of other additives includes benzophenone, anthracene, anthraquinone, 9-oxosulfur etc. and their derivatives, as well as nitrophenyl compounds, etc. Among these, benzophenone derivatives and nitrophenyl compounds are preferable. Specific examples of preferred compounds include N,N-diethylaminobenzophenone, 2-nitrobenzyl, 2-nitroperimone, 5-nitroacenaphthene, 4-nitrobiphenyl, 4-nitrocinnamic acid, 4-nitrostilbene, 4-nitrobenzophenone, and 5-nitroindole. Particularly preferred is N,N-diethylaminobenzophenone, which is a derivative of benzophenone.

These sensitizers are not limited to those mentioned above. Moreover, a sensitizer can be used individually or in combination of 2 or more types.

The proportion of the sensitizer used in the cured film forming composition of this embodiment is preferably 0.1 to 20 parts by mass, more preferably 0.2 to 10 parts by mass based on 100 parts by mass of the total mass of the compound of the component (A) and the polyester polyol having an aromatic ring as the component (B).

<Preparation of cured film forming composition> The cured film forming composition of this embodiment contains the low molecular weight photo-alignment component which is (A) component, the polyester polyol which has an aromatic ring which is (B) component, and the crosslinking agent which is (C) component. Furthermore, other additives may be contained as long as the effects of the present invention are not impaired.

It is preferable that the blending ratio of (A) component and (B) component is 5:95-60:40 by mass ratio.

A preferable example of a cured film is as follows. [1]: A sclerosis film with light -oriented group, which is a dry and burned film formed by the coating of the hardening film formed, and its membrane thickness is more than 3 m and less than 20 μm. The incorporate ratio of the composition of the composition (A) composition of the component and the (B) composition of the component of the component is 5:95 to 60:40, and the (A) ingredients and (B) components are based on The 100 -mass portion of the component contains (C) components of 5 to 500 mass.

[2]: A cured film having a photoalignment group, which is a dried and fired film formed from a coating of a cured film forming composition, and has a film thickness of not less than 3 μm and not more than 20 μm. The cured film forming composition contains 5 to 500 parts by mass of component (C) and a solvent based on 100 parts by mass of the total amount of component (A) and component (B).

[3]: A cured film having a photoalignment group, which is a dried and fired film formed from a coating of a cured film-forming composition, and has a film thickness of not less than 3 μm and not more than 20 μm. The cured film-forming composition contains 5 to 500 parts by mass of component (C), 0.01 to 20 parts by mass of component (D), and a solvent based on 100 parts by mass of the total amount of component (A) and component (B).

When using the cured film forming composition of this embodiment as a solution, the mixing ratio, a preparation method, etc. are detailed below. The ratio of solid components in the cured film forming composition of this embodiment is not particularly limited as long as each component is uniformly dissolved in the solvent, but is 1% by mass to 80% by mass, preferably 3% by mass to 60% by mass, more preferably 5% by mass to 40% by mass. Here, the solid content means what removed the solvent from all the components of the cured film forming composition.

The manufacturing method of the cured film forming composition of this embodiment is not specifically limited. As a production method, for example, in a solution in which component (B) is dissolved in a solvent, the method of mixing (A) component, (C) component, and optionally (D) component in a predetermined ratio to form a uniform solution; or, in an appropriate stage of the production method, a method of further adding other additives and mixing as necessary.

In addition, the prepared solution of the cured film forming composition is preferably used after being filtered with a filter having a pore diameter of about 0.2 μm or the like.

＜Cured film, alignment material and retardation material＞ By bar coating, spin coating, flow coating, roll coating, slit coating, spin coating after slit, inkjet coating, printing, etc., the solution of the cured film forming composition of this embodiment is applied to a substrate (for example, a silicon/silicon dioxide-coated substrate, a silicon nitride substrate, a substrate coated with a metal such as aluminum, molybdenum, chromium, etc., a glass substrate, a quartz substrate, an ITO substrate, etc.) or a film (for example, a triacetyl cellulose (TAC) film, a cycloolefin polymer film, Form a coating film on resin films such as ethylene phthalate film and acrylic film), and then heat and dry with a hot plate or oven to form a cured film.

As the conditions for heating and drying, it is only necessary to carry out the curing reaction to such an extent that the components of the alignment material formed by the cured film do not dissolve into the polymerizable liquid crystal solution coated thereon. For example, the heating temperature and heating time are appropriately selected from the range of temperature 60°C to 200°C and time 0.4 minutes to 60 minutes. The heating temperature and heating time are preferably 70° C. to 160° C. and 0.5 minutes to 10 minutes.

The film thickness of the cured film formed using the cured film-forming composition of this embodiment is, for example, not less than 3 μm and not more than 20 μm, and can be appropriately selected in consideration of the step difference, optical properties, and electrical properties of the substrate used.

The cured film formed in this way can function as an alignment material, that is, as a member for aligning a compound having liquid crystallinity such as a polymerizable liquid crystal, by irradiating polarized light UV.

As a method of irradiating polarized UV light, ultraviolet light to visible light with a wavelength of 150 nm to 450 nm can be generally used, and it is performed by irradiating linearly polarized light from a vertical or oblique direction at room temperature or in a heated state.

The alignment material formed by the cured film of this embodiment has solvent resistance and heat resistance, so after coating the phase difference material composed of a polymerizable liquid crystal solution on the alignment material, it is heated to the phase transition temperature of liquid crystal, thereby making the phase difference material into a liquid crystal state, and aligning it on the alignment material. Furthermore, the retardation material in an aligned state can be directly cured to form the retardation material as a layer having optical anisotropy.

As the phase difference material, for example, a liquid crystal monomer having a polymerizable group, a composition containing the same, and the like can be used. Furthermore, when the substrate on which the alignment material is formed is a thin film, the thin film having the retardation material of this embodiment is useful as a retardation film. The retardation material forming this kind of retardation material is in a liquid crystal state, and there are alignment materials such as horizontal alignment, cholesteric alignment, vertical alignment, and mixed alignment on the alignment material, which can be flexibly used according to the required retardation.

In addition, in the case of producing a patterned retardation material that can be used in a 3D display, for the cured film formed from the cured film composition of this embodiment by the above method, through a mask of a line and space pattern, polarized UV exposure is performed in a direction of +45 degrees according to a specified reference, and then the mask is removed, and polarized UV exposure is performed in a direction of -45 degrees to obtain an alignment material formed with two types of liquid crystal alignment regions with different alignment control directions of liquid crystals. Thereafter, after coating the retardation material composed of a polymerizable liquid crystal solution, the retardation material is made into a liquid crystal state by heating to the phase transition temperature of liquid crystal, and aligned on the alignment material. Furthermore, by directly hardening the phase difference material in an aligned state, a patterned phase difference material in which two types of phase difference regions with different phase difference characteristics are arranged in plural numbers and regularly can be obtained.

In addition, two substrates having the alignment material of the present embodiment formed as described above are bonded together so that the alignment materials on the two substrates face each other through a spacer, and liquid crystal is injected between the substrates to form a liquid crystal display element in which the liquid crystal has been aligned. Therefore, the cured film of this embodiment can be used suitably for manufacture of various phase difference materials (retardation film), a liquid crystal display element, etc. [Example]

Hereafter, although the Example of this invention is given and this invention is concretely demonstrated, this invention is not interpreted limitedly by these.

[abbreviation used in the examples] The meanings of the abbreviations used in the following examples are as follows.

＜Materials＞ BMAA: N-Butoxymethacrylamide AIBN: α,α'-azobisisobutyronitrile

<Component A> MCA: 4-methoxycinnamic acid

<Component B> APEPO: Aromatic polyester polyol (liquid ester oligomer obtained from polycarboxylic acid and polyol having the following structural units) (In the above formula, R ¹¹ represents a C ₁ to C ₈ alkylene group, and R ¹² represents an aromatic ring).

<Component C> PC-1: represented by the following structural formula (n is the number of repeating units).

＜Component D＞ PTSA: p-toluenesulfonic acid monohydrate

<Solvent> Each resin composition of Examples and Comparative Examples contains a solvent, and as the solvent, propylene glycol monomethyl ether (PM), butyl acetate (BA), ethyl acetate (EA), N-methylpyrrolidone (NMP), cyclopentanone (CPN), and methyl ethyl ketone (MEK) were used.

＜Measurement of molecular weight of polymer＞ The molecular weight of the acrylic acid copolymer in the polymerization example was measured as follows using a normal temperature gel permeation chromatography (GPC) device (GPC-101) and a column (KD-803, KD-805) manufactured by Shodex Co., Ltd. manufactured by Shodex Co., Ltd. In addition, the following number average molecular weight (hereinafter referred to as Mn) and weight average molecular weight (hereinafter referred to as Mw) are represented by polystyrene conversion values. Column temperature: 40°C Eluent: Tetrahydrofuran Flow rate: 1.0mL/min Standard sample for calibration curve preparation: Showa Denko standard polystyrene (molecular weight: about 197,000, 55,100, 12,800, 3,950, 1,260, 580).

＜Synthesis of Component C＞ ＜Polymerization example＞ An acrylic acid polymer solution was obtained by dissolving 100.0 g of BMAA and 1.0 g of AIBN as a polymerization catalyst in 193.5 g of PM and reacting at 80° C. for 20 hours. Mn of the obtained acrylic polymer was 10,000, and Mw was 23,000. The acrylic acid polymer solution was dripped slowly to 2000.0 g of hexane, a solid was deposited, it filtered, and it dried under reduced pressure, and the polymer (PC-1) was obtained.

＜Preparation of liquid crystal alignment agent＞ <Example 1> 0.047 g of MCA as the component (A), 0.065 g of APEPO-1 (RDK-133 manufactured by Kawasaki Chemical Industry Co., Ltd.) as the component (B), 0.248 g of the polymer (PC-1) obtained in the polymerization example as the component (C), and 0.012 g of PTSA as the component (D) were mixed, and 0.764 g of PM and 0.984 g of BA were added as a solvent. A solution was obtained by visually confirming the dissolution. Next, the resulting solution was filtered through a filter with a pore size of 0.2 μm, thereby preparing a liquid crystal alignment agent (A-1). In addition, the liquid crystal alignment agent here has the same meaning as a cured film forming composition.

<Example 2 to Example 4> Each liquid crystal alignment agent (A-2) to (A-4) was prepared in the same manner as in Example 1, except that the types and blending amounts of the components shown in the following Table 1 were used. APEPO-2: RFK-505 (manufactured by Kawasaki Chemical Industry Co., Ltd.) APEPO-3: RFK-509 (manufactured by Kawasaki Chemical Industry Co., Ltd.) APEPO-4: RMK-342 (manufactured by Kawasaki Chemical Industry Co., Ltd.)

<Comparative example 1 to comparative example 2> Except for using PEPO (polyester polyol) that does not contain aromatic rings in component (B), and using the types and blending amounts of the components shown in the following Table 1, the same operation was performed as in Example 1 to prepare liquid crystal alignment agents (B-1) to (B-2). PEPO-1: POLYLITE 8651 (manufactured by DIC Corporation) PEPO-2: PLACCEL410 (manufactured by DAICEL Co., Ltd.)

＜Preparation of polymerizable liquid crystal solution for horizontal alignment＞ <Example 5> Add 1.463 g of LC-242 (manufactured by BASF Corporation) as a polymerizable liquid crystal for horizontal alignment, 0.029 g of Irgacure 907 (manufactured by BASF Corporation) as a photoradical initiator, and 0.075 g of BYK-361N as a leveling material, and add 2.776 g of N-methylpyrrolidone as a solvent, stir for 2 hours, and visually confirm that it is dissolving to obtain a 30 mass % polymerizable liquid crystal solution LC- 1.

<Example 6> In the same manner as in Example 5, except that the solvent was changed from N-methylpyrrolidone to cyclopentanone, a polymerizable liquid crystal solution LC-2 was obtained.

<Example 7> In the same manner as in Example 5, except that the solvent was changed from N-methylpyrrolidone to MEK, a polymerizable liquid crystal solution LC-3 was obtained.

<Formation of liquid crystal alignment film and production of retardation film><Example8> Using a bar coater, the liquid crystal alignment agent (A-1) prepared in Example 1 was coated on a TAC film as a substrate with a Wet film thickness of 30 μm. Heat drying was performed at 120° C. for 1 minute in a heat circulation oven to form a cured film on the film. Next, the surface of the cured film was vertically irradiated with 313 nm linearly polarized light at an exposure dose of 10 mJ/cm ² to form a liquid crystal alignment film. Using a bar coater, the polymerizable liquid crystal solution LC-1 for horizontal alignment was coated on the above-mentioned liquid crystal alignment film with a Wet film thickness of 6 μm. Next, after heat-drying at 90°C for 1 minute on a hot plate, 365 nm non-polarized light was irradiated vertically at an exposure dose of 300 mJ/cm ² to harden the polymerizable liquid crystal to prepare a retardation film.

<Example 9 to Example 11> Using (A-2) to (A-4) as a liquid crystal alignment agent, it carried out similarly to Example 8, and each retardation film of Example 9 to Example 11 was produced.

<Comparative Example 3 and Comparative Example 4> Using (B-1) and (B-2) as a liquid crystal aligning agent, it carried out similarly to Example 8, and produced each retardation film of the comparative example 3 and the comparative example 4.

<Example 12 to Example 15> Using (A-1) to (A-4) and the polymerizable liquid crystal solution LC-2 for horizontal alignment as a liquid crystal alignment agent, the same operation as in Example 8 was performed to produce each retardation film of Examples 12 to 15.

<Comparative Example 5 and Comparative Example 6> Using (B-1), (B-2), and the polymerizable liquid crystal solution LC-2 for horizontal alignment as a liquid crystal alignment agent, it was performed in the same manner as in Example 8 to produce retardation films of Comparative Example 3 and Comparative Example 4.

<Example 16 to Example 19> Using (A-1) to (A-4) and the polymerizable liquid crystal solution LC-3 for horizontal alignment as a liquid crystal alignment agent, the same operation as in Example 8 was performed to produce each retardation film of Examples 16 to 19.

<Comparative Example 7 and Comparative Example 8> Using (B-1), (B-2), and the polymerizable liquid crystal solution LC-3 for horizontal alignment as a liquid crystal alignment agent, the same operation as in Example 8 was carried out to prepare the retardation films of Comparative Example 7 and Comparative Example 8.

Each retardation film produced above was evaluated by the following method. The evaluation results are shown in Table 2.

＜Evaluation of Orientation＞ The produced retardation film on the substrate was sandwiched between a pair of polarizing plates, and the behavior of the retardation characteristics under crossed Nicolas was observed visually. In the column of "orientation", the case where the phase difference was expressed without defects was described as ◯, and the case where the phase difference was not expressed was described as ×.

As is clear from the results in Table 2, by using polyester polyols containing aromatic rings, solvent resistance to various solvents in which liquid crystals are soluble can be obtained, resistance to NMP, which is a good solvent, and good alignment can be obtained. At the same time, even thick films with a film thickness of 3 μm or more have excellent transparency. On the other hand, resistance to NMP was not obtained in Comparative Example. [industrial availability]

The cured film resulting from the present invention is very useful as a liquid crystal alignment film of a liquid crystal display element, or a film capable of forming an alignment material, wherein the alignment material is used to form an optically anisotropic film disposed inside or outside of a liquid crystal display element; especially, it is suitable as a material for forming a patterned retardation material for a 3D display. Furthermore, it is also suitable as a hardening film such as a protective film, a planarizing film, and an insulating film in various displays such as a thin-film transistor (TFT) liquid crystal display element or an organic EL element, especially an interlayer insulating film of a TFT liquid crystal element, a protective film of a color filter, or an insulating film of an organic EL element.

Claims (11)

A cured film having a photoalignment group, which is a dried and baked film formed from a coating of a cured film forming composition, and has a film thickness of not less than 3 μm and not more than 20 μm. The cured film forming composition is characterized in that it contains: (A) a compound having a photoalignment group and any one substituent selected from hydroxyl, carboxyl, and amino; (B) a polyester polyol having an aromatic ring; and (C) a crosslinking agent. The cured film according to claim 1, wherein the photoalignment group of the component (A) is a functional group of a structure that undergoes photodimerization or photoisomerization. The cured film according to claim 1 or 2, wherein the photoalignment group of component (A) is a cinnamonyl group. The cured film according to claim 1 or 2, wherein the photoalignment group of the component (A) is a group of an azobenzene structure. The cured film according to claim 1 or 2, wherein the component (A) has two or more hydroxyl groups. The cured film according to Claim 1 or 2, which further contains a crosslinking catalyst as (D) component. The cured film according to Claim 1 or 2, wherein the ratio of (A) component to (B) component is 5:95 to 60:40 by mass ratio. The cured film according to Claim 1 or 2, which contains 5 to 500 parts by mass of (C)component based on 100 parts by mass of the total amount of (A) component and (B)component. The cured film according to claim 6, which contains 0.01 to 20 parts by mass of the component (D) with respect to 100 parts by mass of the total amount of the compound of the component (A) and the polymer of the component (B). An alignment material, which is obtained by using the cured film according to any one of claims 1 to 9. A retardation material characterized by being formed using the cured film according to any one of claims 1 to 9.