WO2020175620A1 - Composition de résine de photo-alignement, film de photo-alignement et stratifié - Google Patents

Composition de résine de photo-alignement, film de photo-alignement et stratifié Download PDF

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WO2020175620A1
WO2020175620A1 PCT/JP2020/008033 JP2020008033W WO2020175620A1 WO 2020175620 A1 WO2020175620 A1 WO 2020175620A1 JP 2020008033 W JP2020008033 W JP 2020008033W WO 2020175620 A1 WO2020175620 A1 WO 2020175620A1
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group
photo
composition
alignment film
repeating unit
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PCT/JP2020/008033
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English (en)
Japanese (ja)
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一茂 中川
賢謙 前田
太朗 橋爪
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富士フイルム株式会社
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Priority to JP2021502365A priority Critical patent/JP7212136B2/ja
Priority to KR1020217025661A priority patent/KR102525275B1/ko
Publication of WO2020175620A1 publication Critical patent/WO2020175620A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
    • C08F220/32—Esters containing oxygen in addition to the carboxy oxygen containing epoxy radicals
    • C08F220/325—Esters containing oxygen in addition to the carboxy oxygen containing epoxy radicals containing glycidyl radical, e.g. glycidyl (meth)acrylate
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B27/00—Layered products comprising a layer of synthetic resin
    • B32B27/06—Layered products comprising a layer of synthetic resin as the main or only constituent of a layer, which is next to another layer of the same or of a different material
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B7/00—Layered products characterised by the relation between layers; Layered products characterised by the relative orientation of features between layers, or by the relative values of a measurable parameter between layers, i.e. products comprising layers having different physical, chemical or physicochemical properties; Layered products characterised by the interconnection of layers
    • B32B7/02—Physical, chemical or physicochemical properties
    • B32B7/023—Optical properties
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2/00—Processes of polymerisation
    • C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
    • C08F220/32—Esters containing oxygen in addition to the carboxy oxygen containing epoxy radicals
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/34—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/52—Amides or imides
    • C08F220/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
    • C08F220/58—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide containing oxygen in addition to the carbonamido oxygen, e.g. N-methylolacrylamide, N-(meth)acryloylmorpholine
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/52—Amides or imides
    • C08F220/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
    • C08F220/60—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide containing nitrogen in addition to the carbonamido nitrogen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/17—Amines; Quaternary ammonium compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • C08L33/04—Homopolymers or copolymers of esters
    • C08L33/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, which oxygen atoms are present only as part of the carboxyl radical
    • C08L33/062—Copolymers with monomers not covered by C08L33/06
    • C08L33/068—Copolymers with monomers not covered by C08L33/06 containing glycidyl groups
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/30—Polarising elements
    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
    • G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
    • G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
    • G02F1/1333—Constructional arrangements; Manufacturing methods
    • G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
    • G02F1/13363—Birefringent elements, e.g. for optical compensation
    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
    • G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
    • G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
    • G02F1/1333—Constructional arrangements; Manufacturing methods
    • G02F1/1337—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers
    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
    • G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
    • G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
    • G02F1/1333—Constructional arrangements; Manufacturing methods
    • G02F1/1337—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers
    • G02F1/133711—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers by organic films, e.g. polymeric films

Definitions

  • the present invention relates to a composition for photo-alignment film, a photo-alignment film, and a laminate.
  • Optically anisotropic layers formed using liquid crystal compounds are used in various applications such as optical compensation sheets and retardation films.
  • An optical alignment film is known as an alignment film for forming such an optically anisotropic layer.
  • Patent Document 1 discloses a composition for a photo-alignment film containing a polymer 8 having a structural unit 3 1 containing a photocinnamate group, a low molecular weight compound having a cinnamate group and having a smaller molecular weight than the polymer 8. Is disclosed.
  • Patent Document 1 International Publication No. 2 0 1 7/0 6 9 2 5 2
  • the present inventors have a structural unit 3 1 having a photoalignable group-containing structural unit 3 1 and a crosslinkable group-containing structural unit 3 2 described in Patent Document 1, and a crosslinkable group-containing structural unit 3
  • the characteristics of the composition for a photo-alignment film containing a copolymer having a high ratio of 2 and an acid generator were measured.
  • a photo-alignment film formed using the composition for photo-alignment film stored for several days (for example, about 1 week) after preparation and a photo-alignment film formed using the composition for photo-alignment film immediately after preparation An alignment film was prepared, and an optically anisotropic layer was formed on both of them using a composition containing a liquid crystal compound, and the alignment property of the liquid crystal compound was evaluated. As a result, it was found that the orientation of the liquid crystal compound was deteriorated when the composition for photoalignment film stored for several days after preparation was used.
  • the excellent alignment of the liquid crystal compound in the optically anisotropic layer is also referred to as “excellent liquid crystal alignment”.
  • An object of the present invention is to provide a composition for a photo-alignment film capable of forming a photo-alignment film in which an optically anisotropic layer formed thereon has excellent liquid crystal alignment even after storage for a predetermined period.
  • this invention also makes it a subject to provide a photo-alignment film and a laminated body. Means for solving the problem
  • a composition for a photo-alignment film which comprises an amine compound having a boiling point of 50 to 230 ° and having no proton on a nitrogen atom.
  • composition for a photo-alignment film according to (1) or (2) wherein the content of the amine compound is 5 to 400 mol% with respect to the content molar amount of the acid generator.
  • the repeating unit containing a photoalignable group contains a repeating unit represented by the formula () described below,
  • composition for a photo-alignment film according to any one of (1) to (3), wherein the repeating unit containing a crosslinkable group contains a repeating unit represented by the following formula (Mi).
  • the repeating unit including a crosslinkable group contains a crosslinkable group represented by any of the formulas (XI) to (3) described below, and the repeating unit according to any one of (1) to (4) Composition for photo-alignment film.
  • An optical anisotropic layer formed using a liquid crystal composition containing a liquid crystal compound, and a laminate.
  • composition for a photo-alignment film which can form a photo-alignment film having excellent liquid crystal alignment of the optically anisotropic layer formed thereon even after storage for a predetermined period.
  • a photo-alignment film and a laminated body can be provided.
  • 6 (s) and [3 ⁇ 4 1: (s) represent in-plane retardation and thickness-direction retardation at wavelengths, respectively. Unless otherwise specified, the wavelength is 550 nm.
  • ⁇ ⁇ (s) and The value in (s) is the value measured by the wavelength value in Yachibu 0380 1/1/1 (manufactured by Optoscience). Average refractive index ( / 3) and film thickness ( ⁇ 1 )) by typing
  • [3 ⁇ 4 ⁇ (s) is displayed as the value calculated by Yachibu ⁇ 03 ⁇ ⁇ 1 ⁇ /1-1 and means (s ).
  • — 1 ⁇ /1 2 manufactured by ATAGO Co., Ltd.
  • — 1 ⁇ /1 2 manufactured by ATAGO Co., Ltd.
  • Cycloolefin polymer (1.52), polycarbonate (1.59), polymethylmethacrylate (1.49), polystyrene (1.59).
  • the (meth)acryloyl group is a concept including both an acryloyl group and a methacryloyl group.
  • a feature of the composition for a photo-alignment film of the present invention is that it contains a predetermined amine compound.
  • the inventors of the present invention used the composition for photoalignment film after storage for a predetermined period of time to perform the It has been found that when an alignment film is formed and an optically anisotropic layer is formed thereon, the liquid crystal alignment property of the obtained optically anisotropic layer is inferior.
  • the reaction of the crosslinkable group by the acid generated from the acid generator during the storage of the composition for photoalignment film when the content of the repeating unit containing a crosslinkable group is large, the reaction of the crosslinkable group by the acid generated from the acid generator during the storage of the composition for photoalignment film. It has been found that the liquid crystal progresses, and as a result, the liquid crystal alignment is affected. Then, they have found that the use of a predetermined amine compound in order to suppress the reaction of such a crosslinkable group can reduce the influence of the acid generator and obtain a desired effect.
  • optically anisotropic layer formed on the photo-alignment film is also excellent in durability evaluated in the Example section described later.
  • composition for a photo-alignment film of the present invention comprises a repeating unit containing a photo-alignable group and a repeating unit containing a cross-linkable group, a predetermined photo-alignable copolymer, an acid generator, and a predetermined And an amine compound.
  • composition for photo-alignment film has a boiling point of 50 to 230 ° and an amine compound having no proton on the nitrogen atom (hereinafter, also referred to as “specific amine compound”).
  • the boiling point of the specific amine compound is 50 to 230 ° ⁇ , and the liquid crystal alignment property of the optically anisotropic layer formed on the photo-alignment film is more excellent (hereinafter, simply “the effect of the present invention It is also referred to as "excellent point.”), 80 to 225 ° is preferable, and 100 to 220 ° is more preferable.
  • excellent point means the boiling point at 1 atm.
  • composition for photo-alignment film contains an amine compound having a partial structure represented by >1 ⁇ ]_!!, the liquid crystal alignment property is not improved, and the composition for photo-alignment film may gel. is there.
  • the specific amine is not particularly limited as long as it satisfies the above characteristics, and examples thereof include secondary amines and tertiary amines.
  • the specific amine may be linear or cyclic.
  • Examples of the case where the specific amine is cyclic include the case where the specific amine has a heterocycle.
  • the heterocycle may be an aromatic heterocycle or an aliphatic heterocycle. Examples of the heterocycle include a pyridine ring.
  • the heterocycle may have a substituent.
  • substituents include an alkyl group and an alkoxy group.
  • the compound represented by the formula (2) is preferable because the effect of the present invention is more excellent.
  • R 1 , R 2 and R 3 each independently represent a linear, branched or cyclic alkyl group having 1 to 20 carbon atoms.
  • the alkyl group has 1 to 20 carbon atoms, and from the viewpoint that the effect of the present invention is more excellent, 1 to 10 is preferable, and 2 to 5 is more preferable.
  • alkyl group examples include a methyl group, an ethyl group, a propyl group (for example, an n_propyl group and an isopropyl group), a butyl group, and a pentyl group.
  • Examples of the specific amine include diisopropylethylamine and triptylamine.
  • composition for photo-alignment film contains a photo-alignable copolymer having a predetermined repeating unit.
  • the photoalignable copolymer has a repeating unit A containing a photoalignable group.
  • the “photoalignable group” refers to a group having a photoalignment function in which rearrangement or an anisotropic chemical reaction is induced by irradiation with light having anisotropy (for example, plane polarized light).
  • a photo-alignment group capable of undergoing at least one of dimerization and isomerization under the action of light is preferable because it has excellent alignment uniformity and also has favorable thermal stability or chemical stability.
  • Examples of the photo-orienting group that dimerizes by the action of light include cinnamic acid derivatives (M. Schadt et a 1., J. App 1. Phys., vo l. 31, No. 7, page 2155 (1992)), coumarin derivative (M. Schadt et a 1., Nature., vo l. 381, page 212 (1996) ), chalcone derivative (Toshihiro Ogawa et al., Proceedings of the Liquid Crystal Conference, 2AB03 (1997)), maleimide derivative, and benzophenone derivative (YK Jang et al., SI D Int. Symposium Digest, P-53 (1997))
  • examples of the photo-orienting group that is isomerized by the action of light include an azobenzene compound (K. Ichimura et al., Mol. Cryst. Liq. Cryst 298, 221 (1997)) and a stilbene compound (G. Victor and B. M. Torke Ison, Macromolecules, 20, 2241 (1987)), Spiropyran compounds (K. Ichimura et a 1., Chemistry Letters, page 1063 (1992); K. Ichimura et al., Thin Solid Films, vol. 23 5, page 101 (1993)), cinnamic acid compound (K.
  • the photo-alignment group is at least one selected from the group consisting of cinnamic acid derivatives, coumarin derivatives, chalcone derivatives, maleimide derivatives, azobenzene compounds, stilbene compounds, and spiropyran compounds.
  • a group having a derivative skeleton is preferable, and a group having a cinnamic acid derivative skeleton or a coumarin derivative skeleton is more preferable.
  • repeating unit A a repeating unit represented by the following formula (A) is preferable because the effect of the present invention is more excellent.
  • [3 ⁇ 4 5 represents a hydrogen atom or a methyl group.
  • 1_ 1 represents a divalent linking group containing a nitrogen atom and a cycloalkane ring, and some of the carbon atoms constituting the cycloalkane ring are selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom. It may be substituted with a carbon atom.
  • 8 6 , 8 7 , 8 8 Each independently represents a hydrogen atom or a substituent, and two adjacent groups of [3 ⁇ 4 6 , [3 ⁇ 4 7 , [3 ⁇ 4 8 , [3 ⁇ 4 9 and [3 ⁇ 4 10] are bonded to each other to form a ring. May be.
  • represented 1_ 1 have One divalent linking group will be described that includes a nitrogen atom and a cycloalkane ring.
  • some of the carbon atoms constituting the cycloalkane ring may be substituted with a hetero atom selected from the group consisting of nitrogen atom, oxygen atom and sulfur atom.
  • the nitrogen atom may not be present separately from the cycloalkane ring.
  • the cycloalkane ring is preferably a cycloalkane ring having 6 or more carbon atoms, and examples thereof include a cyclohexane ring, a cyclopeptane ring, a cyclooctane ring, a cyclododecane ring, and a cyclodocosane ring.
  • the divalent linking group represented by any one of 1) to (10) is preferable.
  • *1 represents the bonding position with the carbon atom constituting the main chain in the above formula (8)
  • *2 represents the above formula (). Represents the bonding position with the carbon atom constituting the carbonyl group.
  • the solubility in the solvent used for forming the light-alignment film and the photo-alignment film obtained are
  • the divalent linking group represented by any one of the above formulas (2), (3), (7) and (8) is preferable from the viewpoint of achieving a good balance with the solvent resistance.
  • substitution group will be described.
  • the above equation (8) As described above, and 10 may be hydrogen atoms instead of substituents.
  • the substituents represented by one embodiment are, independently of each other, a halogen atom and a straight chain having 1 to 20 carbon atoms in that the photo-alignment group easily interacts with the liquid crystal compound and the effect of the present invention is more excellent.
  • Kill group alkoxy group having 1 to 20 carbon atoms, aryl group having 6 to 20 carbon atoms, aryloxy group having 6 to 20 carbon atoms, cyano group, amino group or represented by the following formula (11) It is preferable that the group is
  • ⁇ represents a bonding position with the benzene ring in the formula (8)
  • [3 ⁇ 4 12 represents a monovalent organic group.
  • halogen atom examples include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom, and a fluorine atom or a chlorine atom is preferable.
  • the linear alkyl group having 1 to 20 carbon atoms is preferably an alkyl group having 1 to 6 carbon atoms, and examples thereof include a methyl group, an ethyl group, and a propyl group.
  • the branched alkyl group having 1 to 20 carbon atoms is preferably an alkyl group having 3 to 6 carbon atoms, and examples thereof include an isopropyl group and I 6 A butyl group may be mentioned.
  • the cyclic alkyl group having 1 to 20 carbon atoms is preferably an alkyl group having 3 to 6 carbon atoms, and examples thereof include a cyclopropyl group, a cyclopentyl group, and a cyclohexyl group.
  • the linear halogenated alkyl group having 1 to 20 carbon atoms is preferably a fluoroalkyl group having 1 to 4 carbon atoms, and examples thereof include a trifluoromethyl group, a perfluoroethyl group, a perfluoropropyl group, and And a perfluorobutyl group. Of these, a trifluoromethyl group is preferable.
  • the alkoxy group having 1 to 20 carbon atoms is preferably an alkoxy group having 1 to 18 carbon atoms, more preferably an alkoxy group having 6 to 18 carbon atoms, and an alkoxy group having 6 to 14 carbon atoms. More preferable.
  • Radecyloxy group hexyloxy group, door-octyloxy group, decyloxy group, dodecyloxy group, or A tetradecyloxy group is preferred.
  • the aryl group having 6 to 20 carbon atoms is preferably an aryl group having 6 to 12 carbon atoms, and examples thereof include a phenyl group, a ⁇ -methylphenyl group, and a naphthyl group. preferable.
  • the aryloxy group having 6 to 20 carbon atoms is preferably an aryloxy group having 6 to 12 carbon atoms, and examples thereof include a phenyloxy group and a 2-naphthyloxy group, and a phenyloxy group is preferable.
  • amino group for example, primary amino group (an 1 ⁇ 1 11 2); a secondary amino group such as methylamino group, dimethylamino group, diethylamino group, dibenzyl amino group, and a A tertiary amino group such as a group having a nitrogen atom as a bond of a nitrogen-containing heterocyclic compound (eg, pyrrolidine, piperidine, piperazine, etc.).
  • a nitrogen-containing heterocyclic compound eg, pyrrolidine, piperidine, piperazine, etc.
  • the monovalent organic group represented by [3 ⁇ 4 12 in the above formula (11) is, for example, a straight chain having 1 to 20 carbon atoms. Alternatively, a cyclic alkyl group may be mentioned.
  • an alkyl group having 1 to 6 carbon atoms is preferable, and examples thereof include a methyl group, an ethyl group, and a propyl group, and a methyl group or an ethyl group is preferable.
  • cyclic alkyl group an alkyl group having 3 to 6 carbon atoms is preferable, and examples thereof include a cyclopropyl group, a cyclopentyl group, and a cyclohexyl group, and a cyclohexyl group is preferable.
  • the photo-alignment group easily interacts with the liquid crystal compound, and the effect of the present invention is more excellent. And out of ⁇ 0 2020/175 620 12 ((17 2020/008033
  • 8 in the above formula (8) is an electron-donating substituent because the reaction efficiency is improved when irradiated with light.
  • the electron-donating substituent is the Hammett value.
  • ⁇ et 1 A substituent having a substituent constant ⁇ 7) of 0 or less, and examples thereof include an alkyl group, a halogenated alkyl group, and an alkoxy group.
  • an alkoxy group is preferable, and an alkoxy group having 6 to 16 carbon atoms is more preferable because the effect of the present invention is more excellent, and a carbon number of 7 to
  • repeating unit 8 containing a photo-alignable group examples include repeating units 81 1 to 81 5 shown below.
  • IV! 6 represents a methyl group
  • M represents an ethyl group.
  • the “1,4-cyclohexyl group” contained in the divalent linking group of repeating units 8 — 1 to 8 — 10 may be either a cis isomer or a trans isomer. , Preferably in trans form.
  • the photoalignable copolymer has a repeating unit including a crosslinkable group.
  • the crosslinkable group include an epoxy group, an epoxycyclohexyl group, a xenonyl group, and a functional group having an ethylenically unsaturated double bond, and a cationically polymerizable group is preferable, and the following formula (XI) More preferred is at least one crosslinkable group selected from the group consisting of (3).
  • Ai represents a bond
  • repeating unit a repeating unit represented by the following formula (M) is preferable because the effect of the present invention is more excellent.
  • Examples of the divalent linking group 2 represented in terms the effect of the present invention is more excellent, linear optionally carbon atoms, which may 1-1 8 have a substituent, branched or cyclic An alkylene group, an optionally substituted arylene group having 6 to 12 carbon atoms, an ether group (101), a carbonyl group (10 ( ⁇ ) 1), and a substituent An imino group which may have a group A divalent linking group combining at least two groups selected from the group consisting of (for example, O-alkylene group 1) is preferred.
  • examples of the substituent that the alkylene group, the arylene group and the imino group may have include, for example, a halogen atom, an alkyl group, an alkoxy group, an aryl group, an aryloxy group, a cyano group and a carboxy group. Group, an alkoxycarbonyl group, and a hydroxyl group.
  • halogen atom examples include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom, and a fluorine atom or a chlorine atom is preferable.
  • alkyl group for example, a linear, branched, or cyclic alkyl group having 1 to 18 carbon atoms is preferable, and an alkyl group having 1 to 8 carbon atoms (for example, methyl group, ethyl group, propyl group, isopropyl group Base, _Butyl group, isoptyl group, 360-butyl group, 1_butyl group, and cyclohexyl group) are more preferable, an alkyl group having 1 to 4 carbon atoms is further preferable, and a methyl group or ethyl group. ⁇ 2020/175 620 17 ⁇ (:171? 2020/008033
  • Ru groups are particularly preferred.
  • an alkoxy group having 1 to 18 carbon atoms is preferable, and an alkoxy group having 1 to 8 carbon atoms (eg, methoxy group, ethoxy group, n-butoxy group, and methoxetoxy group) Is more preferable, an alkoxy group having 1 to 4 carbon atoms is further preferable, and a methoxy group or an ethoxy group is particularly preferable.
  • aryl group examples include an aryl group having 6 to 12 carbon atoms, examples of which include a phenyl group, ⁇ -methylphenyl group, and naphthyl group, with a phenyl group being preferred.
  • aryloxy group examples include phenoxy, naphthoxy, imidazoyloxy, benzimidazoyloxy, pyridin-4-yloxy, pyrimidinyloxy, quinazolinyloxy, purinyloxy, and thiophen-3-yloxy.
  • alkoxycarbonyl groups include methoxycarbonyl and ethoxycarbonyl.
  • Examples of the linear alkylene group having 1 to 18 carbon atoms include, for example, a methylene group, an ethylene group, a propylene group, a butylene group, a pentylene group, a hexylene group, a decylene group, an undecylene group, a dodecylene group, and a tridecylene group.
  • Examples of the branched chain alkylene group having 1 to 18 carbon atoms include a dimethylmethylene group, a methylethylene group, a 2,2-dimethylpropylene group, and a 2-ethyl-2-methylpropylene group.
  • Examples of the cyclic alkylene group having 1 to 18 carbon atoms include a cyclopropylene group, a cyclobutylene group, a cyclopentylene group, a cyclohexylene group, a cyclooctylene group, a cyclodecylene group, an adamantane-diyl group, a norbornane-diyl group, And a 6 X O -tetrahydrodicyclopentadienyl group, and a cyclohexylene group is preferable.
  • Examples of the arylene group having 6 to 12 carbon atoms include a phenylene group, a xylylene group, a biphenylene group, a naphthylene group, and a 2,2′-methylenebisphenyl group, and a phenylene group is preferable.
  • Examples of the crosslinkable group represented by X in the above formula (M) include the above-mentioned crosslinkable groups.
  • repeating unit that includes a crosslinkable group examples include the following repeating units: Miichi 1 to Miichi 17.
  • repeating unit including a crosslinkable group examples include the following repeating units: Michi 18 to Michi 47.
  • the photoalignable copolymer may have other repeating units in addition to the above-described repeating unit and repeating unit, as long as the effects of the present invention are not impaired.
  • the content 3 of the repeating unit and the content of the repeating unit M in the photoalignable copolymer satisfy the following formula (1) in mass ratio.
  • the relationship of the formula (1) represents the ratio of the content 13 to the total of the content 3 of the repeating unit and the content 13 of the repeating unit.
  • the range / (3 + 13) is preferably 0.75 to 0.95, more preferably 0.80 to 0.993.
  • the content of the repeating unit is not particularly limited, but from the viewpoint that the effect of the present invention is more excellent, it is preferably 3 to 30 mass% with respect to all repeating units in the photoalignable copolymer, and 5 to 25% by mass is more preferable.
  • the content of the repeating unit is not particularly limited, but from the viewpoint that the effect of the present invention is more excellent, it is preferably 70 to 97% by mass, and 75 to 95% by mass with respect to all repeating units in the photoalignable copolymer. % Is more preferable.
  • Weight average molecular weight of photoalignable copolymer Is preferably from 100,000 to 500,000, more preferably from 30,000 to 30,000, from the viewpoint that the effect of the present invention is more excellent.
  • the weight average molecular weight and the number average molecular weight in the present invention are values measured by the gel permeation chromatography ( ⁇ ) method under the following conditions.
  • the composition for photo-alignment film contains an acid generator.
  • the acid generator has a function of initiating the polymerization of the above-mentioned crosslinkable group.
  • the acid generator is not particularly limited, and examples thereof include a thermal acid generator and a photoacid generator.
  • the thermal acid generator is not particularly limited in its structure as long as it is a compound capable of decomposing by heat to generate a specific acid. Usually, it is composed of an anion obtained by removing hydrogen ion from a predetermined acid and a cation. Composed.
  • Examples of the acid include compounds represented by the formulas (8) to (M), and ⁇ .
  • the number of carbon atoms in the perfluoroalkyl group is not particularly limited, but is preferably 1 to 10 and more preferably 1 to 5.
  • the number of carbon atoms in the perfluoroalkylene group is not particularly limited, but is preferably 2 to 10 and more preferably 3 to 5.
  • the number of carbon atoms in the perfluoroalkyl group is not particularly limited, but 1 to 10 is preferable.
  • aryl group which may have a substituent.
  • the aryl group include a phenyl group and a naphthyl group.
  • the type of the substituent is not particularly limited, but examples thereof include an alkyl group and a halogen atom (preferably a fluorine atom).
  • the number of carbon atoms in the perfluoroalkyl group is not particularly limited, but 1 to 10 is preferable, and 1 to 5 is more preferable.
  • n represents an integer of 1 to 6. Among them, n is preferably an integer of 3 to 6,
  • Examples of the anion include the following.
  • the cation a known cation that is decomposed by heat can be used.
  • the cation preferably has a skeleton in which thermal decomposition starts at 30 to 200°, and more preferably has a skeleton in which thermal decomposition starts at 40 to 150°.
  • the sulfonium cation represented by the formula () or the iodonium cation represented by the formula ( ⁇ ) is preferable from the viewpoint of handleability.
  • [0078] and [3 ⁇ 4 9 1 and [3 ⁇ 4 9 2 each independently represent a hydrocarbon group which may have a substituent.
  • a hydrocarbon group an alkyl group (for example, a methyl group, an ethyl group) or an aryl group (for example, a phenyl group) is preferable.
  • the kind of the substituent is not particularly limited, and examples thereof include an alkyl group, an aryl group, a hydroxy group, an amino group, a carboxy group, a sulfone amide group, a 1 ⁇ 1-sulfonyl amide group, an acyl group, an acyloxy group, an alkoxy group. , An alkyl group, a halogen atom, an alkoxycarbonyl group, an alkoxycarbonyloxy group, an ester carbonate group, and a cyano group.
  • Examples of the cation include the following.
  • the photo-acid generator is a compound that decomposes by light to generate a specific acid. ⁇ 2020/175 620 24 ⁇ (:171? 2020 /008033
  • the structure is not particularly limited, but a compound that reacts with an actinic ray having a wavelength of 300 n or more, preferably 300 0 to 450 n and generates an acid is preferable.
  • the wavelength 300 The above photoacid generators that are not directly sensitive to actinic rays can also be used in combination with sensitizers to generate wavelengths of 300 Any compound capable of reacting with the above-mentioned actinic rays and generating an acid can be preferably used in combination with a sensitizer.
  • Examples of the photoacid generator include onium salt compounds, trichloromethyl-3-triazines, sulfonium salts, iodonium salts, quaternary ammonium salts, diazomethane compounds, imidsulfonate compounds, and oximesulphonate compounds. Is mentioned.
  • composition for photo-alignment film may contain components other than the components described above.
  • Other components include solvents.
  • Solvents include water and organic solvents.
  • organic solvent examples include ketones (eg, acetone, 2-butanone, methylisoeptylketone, and cyclohexanone), ethers (eg, dioxane and tetrahydrofuran), aliphatic hydrocarbons (eg, For example, hexane), alicyclic hydrocarbons (eg, cyclohexane), aromatic hydrocarbons (eg, toluene, xylene, and trimethylbenzene)
  • ketones eg, acetone, 2-butanone, methylisoeptylketone, and cyclohexanone
  • ethers eg, dioxane and tetrahydrofuran
  • aliphatic hydrocarbons eg, For example, hexane
  • alicyclic hydrocarbons eg, cyclohexane
  • aromatic hydrocarbons eg, toluene, xylene, and trimethylbenzene
  • Halogenated carbons eg dichloromethane, dichloroethane, dichlorobenzene and chlorotoluene
  • esters eg methyl acetate, ethyl acetate and butyl acetate
  • water alcohols
  • alcohols eg ethanol, isopropanol, Butanol and cyclohexanol
  • cellosolves eg, methylcellosolve and ethylcellosolve
  • cellosolve acetates eg, methylcellosolve and ethylcellosolve
  • sulfoxides eg, dimethylsulfoxide
  • amides eg, dimethylformamid
  • the solvent may be used alone or in combination of two or more. ⁇ 2020/175 620 25 ⁇ (: 171? 2020 /008033
  • composition for photo-alignment film may contain components other than the above, and examples thereof include a crosslinking catalyst, an adhesion improver, a leveling agent, a surfactant, and a plasticizer.
  • composition for photo-alignment film contains the above-mentioned photo-alignable copolymer, an acid generator, and a specific amine compound.
  • the method for preparing the composition for a photo-alignment film is not particularly limited, and the above components may be mixed at once or may be mixed stepwise.
  • the content of the photoalignable copolymer in the composition for photoalignment film is not particularly limited, but when the composition for photoalignment film contains a solvent, relative to 100 parts by mass of the solvent, O.1 to 50 parts by mass is preferable, and 0.5 to 20 parts by mass is more preferable.
  • the content of the acid generator in the composition for the photo-alignment film is not particularly limited, but in terms of the effect of the present invention being more excellent, with respect to the total mass of the photo-alignment copolymer, 0.1 to 30 mass% Is preferable, and 0.5 to 2.0 mass% is more preferable.
  • the content of the specific amine in the composition for a photo-alignment film is not particularly limited, but it is often 1 to 100 mol% with respect to the content molar amount of the acid generator (total molar amount). From the viewpoint that the above effect is more excellent, 5 to 400 mol% is preferable, and 10 to 300 mol% is more preferable.
  • a photo-alignment film can be formed using the composition for photo-alignment film.
  • the photo-alignment film can be produced by a conventionally known production method except that the composition for photo-alignment film described above is used.
  • a step of forming a precursor film using the composition for photo-alignment film described above can be produced by a manufacturing method including a polarized light or a precursor film and a light irradiation step of irradiating the surface of the precursor film with non-polarized light from an oblique direction.
  • the precursor film forming step is a step of forming a precursor film using the composition for photo-alignment film.
  • the precursor film means a film that is subjected to photo-alignment treatment. ⁇ 0 2020/175 620 26 ⁇ (: 17 2020 /008033
  • the procedure of the above steps is not limited as long as the precursor film can be formed.
  • the composition for a light directing film is applied onto a support to form a coating film, and the coating film is subjected to a curing treatment (heat treatment and Light irradiation treatment) to form a precursor film.
  • the support to which the composition for a photo-alignment film is applied is not particularly limited, and examples thereof include a glass substrate and a polymer film.
  • Materials for the polymer film include cellulose-based polymers; acrylic-based polymers having acrylic acid ester polymers such as polymethylmethacrylate and lactone ring-containing polymers; thermoplastic norbornene-based polymers; polycarbonate-based polymers; polyethylene terephthalate and polyethylene naphthalate.
  • Polyester polymers polystyrene, acrylonitrile styrene copolymers and other styrene polymers; polyethylene, polypropylene and ethylene-propylene copolymers and other polyolefin polymers; vinyl chloride polymers; nylon and aromatic polyamides Polymers; Imide polymers; Sulfone polymers; Polyethersulfone polymers; Polyetheretherketone polymers; Polyphenylene sulfide polymers; Vinylidene chloride polymers; Vinyl alcohol polymers; Vinyl ptillal polymers; Examples thereof include arylate-based polymers; polyoxymethylen-based polymers; epoxy-based polymers; and polymers obtained by mixing these polymers.
  • the thickness of the support is not particularly limited, but is preferably 5 to 200, and 10 to
  • the method for applying the composition for a photo-alignment film is not particularly limited, but for example, spin coating, die coating, gravure coating, flexo printing! ⁇ , and inkjet printing.
  • the method of curing the coating film of the composition for a photo-alignment film is not particularly limited, and examples thereof include heat treatment and light irradiation treatment.
  • the acid generator is a thermal acid generator, ⁇ 2020/175 620 27 ⁇ (:171? 2020 /008033
  • heat treatment is preferable as the curing treatment
  • the acid generator is a photoacid generator
  • light irradiation treatment is preferable as the curing treatment.
  • the conditions for heat treatment are not particularly limited, and optimal conditions are selected as appropriate depending on the material used, but the heating temperature is preferably 50 to 150 ° ⁇ , and 80 to 140° O is more preferable.
  • the heating time is preferably 0.1 to 60 minutes, more preferably 0.5 to 30 minutes.
  • the conditions of the light irradiation treatment are not particularly limited, and it is preferable to use ultraviolet rays.
  • the procedure for separately performing the coating film forming treatment and the curing treatment has been described above, they may be performed simultaneously. That is, the curing treatment may be carried out at the time of forming the coating film. Specifically, a method of heating (or irradiating with light) while applying the composition for a photo-alignment film on a support can be mentioned.
  • the light irradiation treatment is a step of irradiating the surface of the polarized film or the precursor film with non-polarized light from an oblique direction.
  • the polarized light with which the precursor film of the composition for a photo-alignment film is irradiated is not particularly limited, and examples thereof include linearly polarized light, circularly polarized light, and elliptically polarized light, and linearly polarized light is preferable.
  • the “oblique direction” for irradiating non-polarized light is not particularly limited as long as it is a direction inclined by a polar angle 0 ( ⁇ ⁇ 0 ⁇ 90 ° ) with respect to the normal direction of the precursor film surface.
  • the polar angle 0 is preferably 20 to 80 ° .
  • the wavelength of polarized light or non-polarized light is not particularly limited as long as it can impart the orientation control ability to the liquid crystal compound in the precursor film, and examples thereof include ultraviolet rays, near ultraviolet rays, and visible rays. Rays can be mentioned. Of these, near-ultraviolet rays of 250 to 450 are preferable.
  • a light source for irradiating polarized light or non-polarized light for example, a xenon lamp, a high pressure mercury lamp, an ultrahigh pressure mercury lamp, and a metal halide ⁇ 2020/175 620 28 ⁇ (:171? 2020 /008033
  • the wavelength range for irradiation can be limited.
  • linearly polarized light can be obtained by using a polarizing filter or a polarizing prism for the light from these light sources.
  • the cumulative amount of polarized or unpolarized light is not particularly limited,
  • the illuminance of polarized light or non-polarized light is not particularly limited.
  • the film thickness of the photo-alignment film is not particularly limited, and is preferably 10 to 100 nm, more preferably 10 to 700 nm.
  • the laminate of the present invention has the above-mentioned photo-alignment film and an optically anisotropic layer formed using a liquid crystal composition containing a liquid crystal compound.
  • the laminate of the present invention preferably further has a support, and specifically, it preferably has a support, a photo-alignment film and an optically anisotropic layer in this order. ..
  • the support and the photo-alignment film are as described above.
  • optically anisotropic layer will be described in detail.
  • the optically anisotropic layer of the laminate may be an optically anisotropic layer formed using a liquid crystal composition containing a liquid crystal compound (hereinafter, also referred to as “composition for optically anisotropic layer”).
  • composition for optically anisotropic layer a liquid crystal compound
  • examples include conventionally known optically anisotropic layers.
  • the optically anisotropic layer is preferably a layer obtained by curing a liquid crystal composition containing a liquid crystal compound having a polymerizable group.
  • the optically anisotropic layer may have a single-layer structure or a structure in which a plurality of layers are laminated (laminate).
  • liquid crystal compound and optional additives will be described below.
  • the liquid crystal compound can be classified into a rod-shaped type and a disc-shaped type according to its shape. ⁇ 2020/175 620 29 ⁇ (:171? 2020 /008033
  • Polymers generally refer to polymers with a degree of polymerization of 100 or more (Polymer physics/Phase transition dynamics, Masao Doi,
  • any liquid crystal compound can be used, but it is preferable to use a rod-shaped liquid crystal compound or a discotic liquid crystal compound, and it is more preferable to use a rod-shaped liquid crystal compound.
  • the liquid crystal compound preferably has a polymerizable group.
  • the liquid crystal compound preferably has two or more polymerizable groups in one molecule. Incidentally, after the liquid crystal compound is fixed by polymerization, it is no longer necessary to exhibit liquid crystallinity.
  • the type of the polymerizable group is not particularly limited, a functional group capable of addition polymerization reaction is preferable, a polymerizable ethylenically unsaturated group or a ring polymerizable group is preferable, and a (meth)acryloyl group, vinyl Group, styryl group, or allyl group is more preferable, and (meth)acryloyl group is further preferable.
  • Examples of the rod-shaped liquid crystal compound are those described in claim 1 of Japanese Patent Publication No. 11-513109 or in paragraphs [0026] to [098] of Japanese Patent Laid-Open No. 2005-289980.
  • As the discotic liquid crystal compound for example, paragraphs [00 20] to [0067] of JP 2007 _ 1 08732 or paragraph [0000 1 of JP 2010-244038 A can be used.
  • ] To [01 08] can be preferably used.
  • liquid crystal compound a reverse wavelength dispersion liquid crystal compound can be used.
  • the “reverse wavelength dispersion” liquid crystal compound means an in-plane retardation ([3 ⁇ 4 6) value at a specific wavelength (visible light range) of a retardation film produced by using the liquid crystal compound. In this case, the 6 value becomes equal or higher as the measurement wavelength increases.
  • the liquid crystal compound is preferably a liquid crystal compound represented by the formula (3).
  • ⁇ ⁇ ⁇ 2, eight 1 and eight 2 each independently may have a substituent, a divalent aromatic hydrocarbon group having the number 6-1 2 carbons, or a 5-8 carbon atoms represents a divalent alicyclic hydrocarbon group, ⁇ _ ⁇ _1 constituting the alicyclic hydrocarbon group 1 2 - of one or more on the one hundred and one, May be substituted with.
  • 3 1 and 3 2 are each independently a single bond, a linear or branched alkylene group having 1 to 12 carbons, or a linear or branched chain having 1 to 12 carbons. At least one of _ 01 to 1 2 — constituting the alkylene group of
  • a plurality of Snake 3 are the same - or different and a plurality of eight 1 may each become different, even the same.
  • ⁇ represents an integer of ⁇ _ ⁇ 2, when n is 2, a plurality of snake 4 are the same - or different and a plurality of eight 2 can be the respective same different It may be.
  • Eight represents an organic group having at least one aromatic ring selected from the group consisting of an aromatic hydrocarbon ring and an aromatic heterocycle, which may have a substituent.
  • 1 1 and 1_ 2 each independently represents a monovalent organic group.
  • 1,2-phenylene group 1,3-phenylene group, 1,4-phenylene group, 1,4-naphthylene group, 1,5-naphthylene group, and
  • 2,6-naphthylene group is mentioned, and among them, 1,4-phenylene group is preferred.
  • 1,4-phenylene group is preferred.
  • trans-1,4-phenylene group is more preferable.
  • the divalent alicyclic hydrocarbon group having 5 to 8 carbon atoms represented by 0 1 , 0 2 % 1 and 2 is preferably a 5-membered ring group or a 6-membered ring group.
  • the alicyclic hydrocarbon group may be saturated or unsaturated, but a saturated alicyclic hydrocarbon group is preferable. Examples of the divalent alicyclic hydrocarbon group include those described in JP-A No. 20 1 2 _ 210 6 8
  • 3 1 and 3 2 are shown a linear or branched alkylene group of from 1 to 1 2 carbon atoms, for example, methylene group, ethylene group, propylene group, Puchire down, pentylene, hexylene Group, a methylhexylene group, and a heptylene group.
  • 3 1 and 3 2 are as described above, constitute a straight chain or branched chain alkylene group having 1 to 2 carbon atoms
  • the top is 101, 13-, It may be a monovalent (0) — or a divalent linking group substituted with 1001, and a substituent represented by 0 is a group in the formula (8 “1 1) described later. Examples of the substituent which 1 may have include
  • Examples of the monovalent organic group represented by !_ 1 and !_ 2 include an alkyl group, an aryl group, and a heteroaryl group.
  • the alkyl group may be linear, branched or cyclic, but linear is preferred.
  • the alkyl group preferably has 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and even more preferably 1 to 10 carbon atoms.
  • the aryl group may be monocyclic or polycyclic, but monocyclic is preferred.
  • the carbon number of the aryl group is preferably 6 to 25, more preferably 6 to 10 ⁇ 2020/175 620 32 units (: 171-1? 2020 /008033
  • the heteroaryl group may be monocyclic or polycyclic.
  • the number of heteroatoms constituting the heteroaryl group is preferably 1 to 3.
  • the hetero atom constituting the heteroaryl group is preferably a nitrogen atom, a sulfur atom or an oxygen atom.
  • the heteroaryl group preferably has 4 to 18 carbon atoms, and more preferably 4 to 12 carbon atoms.
  • the alkyl group, aryl group and heteroaryl group may be unsubstituted or may have a substituent. Examples of the substituent include the same substituents as the substituent that may be possessed by Ogura 1 in the formula (8 "-1 1") to be described later.
  • At least one of !_ 1 and 1_ 2 is preferably a polymerizable group.
  • the polymerizable group is not particularly limited, but a polymerizable group capable of radical polymerization or cationic polymerization is preferable.
  • radically polymerizable group a generally known radically polymerizable group can be used, and an acryloyl group or a methacryloyl group is preferable.
  • an acryloyl group is generally known to have a higher polymerization rate, and an acryloyl group is preferable from the viewpoint of improving productivity, but a methacryloyl group can be used as a polymerizable group in the same manner.
  • cationically polymerizable groups As the cationically polymerizable group, generally known cationically polymerizable groups can be used. Examples thereof include alicyclic ether group, cyclic acetal group, cyclic lactone group, cyclic thioether group, spiro orthoester group, and vinyloxy group. Is mentioned. Of these, an alicyclic ether group or a vinyloxy group is preferable, and an epoxy group, an oxetanyl group, or a vinyloxy group is more preferable.
  • Examples of preferable polymerizable groups include the following.
  • Both !_ 1 and 1_ 2 are preferably a polymerizable group, and more preferably an acryloyl group or a methacryloyl group.
  • [0111] represents an organic group having at least one aromatic ring which may have a substituent and is selected from the group consisting of an aromatic hydrocarbon ring and an aromatic heterocycle.
  • the aromatic hydrocarbon ring may be a monocyclic ring or a polycyclic ring.
  • the carbon number of the aromatic hydrocarbon ring is preferably 6 to 25, more preferably 6 to 10.
  • the aromatic heterocycle may be a monocycle or a polycycle.
  • the hetero atom forming the aromatic compound ring is preferably a nitrogen atom, a sulfur atom or an oxygen atom.
  • the aromatic heterocycle preferably has 4 to 18 carbon atoms, more preferably 4 to 12 carbon atoms.
  • substituents examples include known substituents.
  • the above-mentioned " 1 " is preferably any aromatic ring selected from the group consisting of groups represented by the following formulas (8"-1" to (8"-15).
  • ⁇ represents the bonding position with 0 1 or 0 2 .
  • 0 1 represents 1 ⁇ 1 or 0 1 to 1.
  • 0 2 represents 1-, 101, or 1 ([3 ⁇ 4 5 )-, Represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.
  • Reference 1 represents an optionally substituted aromatic hydrocarbon group having 6 to 12 carbon atoms, or an aromatic heterocyclic group having 3 to 12 carbon atoms.
  • Examples of the aromatic heterocyclic group having 3 to 12 carbon atoms represented by 1 include a heteroaryl group such as a cenyl group, a thiazolyl group, a furyl group, a pyridyl group, and a benzofuryl group.
  • the aromatic heterocyclic group also includes a group in which a benzene ring and an aromatic heterocycle are condensed.
  • substituent which may be possessed ⁇ 1, for example, an alkyl group, alkoxy group, a nitro group, an alkylsulfonyl group, an alkyloxycarbonyl group, a cyano group, and, a halogen atom.
  • alkyl group for example, a linear, branched, or cyclic alkyl group having 1 to 18 carbon atoms is preferable, and an alkyl group having 1 to 8 carbon atoms (for example, methyl group, ethyl group, propyl group, isopropyl group Base, _Butyl group, isoptyl group, 360-butyl group, 1_butyl group, and cyclohexyl group) are more preferable, an alkyl group having 1 to 4 carbon atoms is more preferable, and a methyl group or an ethyl group is Particularly preferred.
  • an alkyl group having 1 to 8 carbon atoms for example, methyl group, ethyl group, propyl group, isopropyl group Base, _Butyl group, isoptyl group, 360-butyl group, 1_butyl group, and cyclohexyl group
  • an alkyl group having 1 to 4 carbon atoms is more preferable
  • an alkoxy group having 1 to 18 carbon atoms is preferable, and an alkoxy group having 1 to 8 carbon atoms (eg, methoxy group, ethoxy group, n-butoxy group, and methoxetoxy group) Is more preferable, an alkoxy group having 1 to 4 carbon atoms is further preferable, and a methoxy group or an ethoxy group is particularly preferable.
  • halogen atom examples include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom, and a fluorine atom or a chlorine atom is preferable.
  • 1 , 2, and 3 are each independently a hydrogen atom, a monovalent aliphatic hydrocarbon group having 1 to 20 carbon atoms, and a monovalent alicyclic carbon group having 3 to 20 carbon atoms.
  • an alkyl group having 1 to 15 carbon atoms is preferable, an alkyl group having 1 to 8 carbon atoms is more preferable, and a methyl group ⁇ 2020/175 620 36 ⁇ (: 171-1? 2020 /008033
  • Ethyl group isopropyl group, 6 "-pentyl group (1, 1-dimethylpropyl group), I 6 "I-butyl group, or 1, 1-dimethyl-3,3-dimethylbutyl group is more preferable, methyl group, Ethyl group, or 1 6 ”
  • the I-butyl group is particularly preferred.
  • Examples of the monovalent alicyclic hydrocarbon group having 3 to 20 carbon atoms include cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, cyclodecyl group, methylcyclohexyl group, and , A monocyclic saturated hydrocarbon group such as an ethyl cyclohexyl group; a cyclobutenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a cyclooctenyl group, a cyclodecenyl group, a cyclopentenyl group, a cyclohexagenyl group, a cyclooctagenenyl group Group and monocyclic unsaturated hydrocarbon group such as cyclodecadiene group; bicyclo [2.
  • Examples of the monovalent aromatic hydrocarbon group having 6 to 20 carbon atoms include a phenyl group, a 2,6-ditylphenyl group, a naphthyl group, and a biphenyl group, and an aryl group having 6 to 12 carbon atoms.
  • a group (particularly a phenyl group) is preferred.
  • halogen atom examples include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom, and a fluorine atom, a chlorine atom or a bromine atom is preferable.
  • alkyl group having 1 to 6 carbon atoms examples include, for example, methyl group, ethyl group, propyl group, isopropyl group, _Butyl group, isoptyl group, 360-butyl group, ⁇ “-butyl group, And 11-hexyl groups.
  • eighty three and eighty four are, independently, 101 and ([3 ⁇ 4 10 )-, -3 —, and, Represents a group selected from the group consisting of ⁇ 2020/175 620 37 ⁇ (:171? 2020/008033
  • Examples thereof include the same substituents as the substituent 1 may have in the above formula (8 “_ 1 ).
  • X is a hydrogen atom or a Group 14 to Group 1 to which a substituent may be bonded.
  • examples of the non-metal atom of Groups 14 to 16 represented by X include an oxygen atom, a sulfur atom, a nitrogen atom having a substituent, and a carbon atom having a substituent.
  • the group, the formula (eight "one 1) those in ⁇ 1 is similar to the substituent which may have the like.
  • 0 3 and 0 4 are, independently of each other, a single bond, a 10101, a 10 (
  • 3 3 and 3 4 are each independently a single bond, a linear or branched alkylene group of number 1-1 2 carbons or straight-chain carbon number of 1-1 2 or ⁇ _ 01 constituting the branched chain alkylene group having 1 2 - of one or more one hundred and one,
  • [0122] represents an organic group having 2 to 30 carbon atoms, which has at least one aromatic ring selected from the group consisting of an aromatic hydrocarbon ring and an aromatic heterocycle.
  • the aromatic ring in X and V may have a substituent, and 8X and 8so may be bonded to each other to form a ring.
  • 0 3 represents a hydrogen atom or an optionally substituted alkyl group having 1 to 6 carbon atoms.
  • composition for the optically anisotropic layer may contain a component other than the above-mentioned liquid crystal compound.
  • the composition for the optically anisotropic layer may contain a polymerization initiator.
  • the polymerization initiator used is selected according to the type of polymerization reaction, and examples thereof include a thermal polymerization initiator and a photopolymerization initiator.
  • examples of the photopolymerization initiator include ⁇ -carbonyl compound, acyloin ether, Examples include a hydrocarbon-substituted aromatic acylloin compound, a polynuclear quinone compound, and a combination of a triarylimidazole dimer and an aminophenyl ketone.
  • the amount of the polymerization initiator used is preferably 0.01 to 20% by mass, and more preferably 0.5 to 5% by mass, based on the total solid content of the composition.
  • the composition for the optically anisotropic layer may contain a polymerizable monomer.
  • the polymerizable monomer include radically polymerizable or cationically polymerizable compounds.
  • a polyfunctional radically polymerizable monomer is preferable, and one that is copolymerizable with the above-mentioned polymerizable group-containing liquid crystal compound is preferable.
  • those described in paragraphs [0 0 1 8] to [0 0 2 0] of JP-A-2000-2296423 can be mentioned.
  • the content of the polymerizable monomer is preferably 1 to 50 mass% and more preferably 2 to 30 mass% with respect to the total mass of the liquid crystal compound.
  • composition for the optically anisotropic layer may contain a surfactant from the viewpoint of the uniformity of the coating film and the strength of the film.
  • a fluorine compound is particularly preferable.
  • composition for an optically anisotropic layer may contain a dichroic substance from the viewpoint of causing the optically anisotropic layer to function as a polarizer.
  • the above-mentioned dichroic substance is not particularly limited, and visible light absorbing substance (dichroic dye), light emitting substance (fluorescent substance, phosphorescent substance), ultraviolet ray absorbing substance, infrared absorbing substance, non-linear optical substance, carbon nanotube,
  • inorganic substances for example, quantum rods
  • dichroic substances dichroic dyes
  • composition for the optically anisotropic layer may contain an organic solvent.
  • organic solvent include the same ones as described in the above-mentioned composition for photoalignment film of the present invention.
  • the composition for the optically anisotropic layer includes a vertical alignment promoter such as a polarizer interface side vertical aligning agent and an air interface side vertical aligning agent, and a polarizer interface side horizontal aligning agent and an air interface.
  • a vertical alignment promoter such as a polarizer interface side vertical aligning agent and an air interface side vertical aligning agent
  • a polarizer interface side horizontal aligning agent and an air interface include aligning agents such as a horizontal alignment promoting agent such as a side horizontal aligning agent.
  • composition for an optically anisotropic layer may contain an adhesion improver, a plasticizer, a polymer and the like in addition to the above components.
  • the method for forming the optically anisotropic layer using the composition for optically anisotropic layer is not particularly limited.
  • the composition for optically anisotropic layer may be applied onto the above-mentioned photo-alignment film.
  • Examples include a method of forming a coating film and subjecting the obtained coating film to a curing treatment (irradiation with ultraviolet rays (light irradiation treatment) or heat treatment) to form an optically anisotropic layer.
  • composition for the optically anisotropic layer can be applied by a known method (eg, wire bar coating method, extrusion coating method, direct gravure coating method, reverse gravure coating method, die coating method).
  • a known method eg, wire bar coating method, extrusion coating method, direct gravure coating method, reverse gravure coating method, die coating method.
  • the film thickness of the optically anisotropic layer is not particularly limited, and is preferably 0.1 to 10 and more preferably 0.5 to 5.
  • the in-plane retardation of the optically anisotropic layer at a wavelength of 550 n is not particularly limited, but 110 to 160 is preferable. ⁇ 2020/175 620 40 ⁇ (: 171? 2020 /008033
  • the laminated body can be applied to various uses.
  • an image display device including a display element and a laminated body can be mentioned.
  • the display element used in the image display device of the present invention is not particularly limited, and examples thereof include a liquid crystal cell, an organic electroluminescence (hereinafter, abbreviated as “M!”) display panel, and a plasma display panel. Liquid crystal cells or organic display panels are preferred. That is, the image display device of the present invention is preferably a liquid crystal display device using a liquid crystal cell as a display element, and an organic date display device using an organic semiconductor display panel as a display element.
  • An organic semiconductor display device which is an example of the image display device of the present invention includes, for example, a polarizer, the laminate of the present invention, and an organic solar display panel in this order from the viewing side. Aspects are preferred.
  • the above-mentioned polarizer is not particularly limited as long as it is a member having a function of converting light into a specific linearly polarized light, and as an absorption-type polarizer that can utilize a conventionally known absorption-type polarizer and reflection-type polarizer, An iodine-based polarizer, a dye-based polarizer using a dichroic dye, and a polyene-based polarizer are used.
  • the iodine-based polarizer and the dye-based polarizer include a coating-type polarizer and a stretch-type polarizer, both of which are applicable.
  • Patent No. 50481 2 0 Publication Patent 5 1 439 18 Publication
  • Patent No. 469 1 205 Japanese Patent No. 475 1 481 and Japanese Patent No. 475 1 486 can be mentioned.
  • ⁇ 2020/175 620 41 Japanese Patent No. 475 620 41 ⁇ (:171? 2020/008033
  • Examples of reflective polarizers include a polarizer in which thin films having different birefringence are laminated, a wire-grid polarizer, and a polarizer in which a cholesteric liquid crystal having a selective reflection region and a 1/4 wavelength plate are combined. Is mentioned.
  • polyvinyl alcohol resin In particular, a polarizer containing at least one selected from the group consisting of polyvinyl alcohol and ethylene-vinyl alcohol copolymer is preferable.
  • the thickness of the polarizer is not particularly limited and is preferably 3 to 60, more preferably 5 to 30.
  • An organic semiconductor display panel is a member in which a light emitting layer or a plurality of organic compound thin films including the light emitting layer are formed between a pair of electrodes of an anode and a cathode.
  • the organic display panel may have a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, a protective layer, and the like, and each of these layers is different. It may have the function of.
  • reaction solution was cooled to room temperature (23 ° C)
  • the reaction solution was suction filtered to remove the precipitated salt.
  • the obtained organic layer was stirred with a stirring blade, a thermometer, a dropping port and a reflux tube. It was transferred to a 2 1_3 flask equipped with it and stirred under water cooling.
  • the following monomer 8_1 corresponds to the monomer forming the above-mentioned repeating unit 8_1.
  • the following monomer, which forms the repeating unit, Minichi 1, is used as (Manufactured by Daicel) was used.
  • Polymer 1 having a photoalignable group was obtained by drying with air blowing for a period of time.
  • Composition 1 for photo-alignment film was prepared as follows. Composition for photo-alignment film 1 Polymer _ 1 1 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 Part by mass Thermal acid generator port _ 1 3.0 0 parts by mass Diisopropylethylamine 0.60 parts by mass Putyl acetate 9 5 3.1 2 parts by mass ⁇ 2020/175 620 44 ⁇ (:171? 2020 /008033
  • the prepared composition for photo-alignment film 1 was sealed in a glass bottle and stored in a sealed state at normal temperature for 7 days.
  • the cellulose acylate film As the cellulose acylate film, the same film as that used in Example 6 of Japanese Patent Laid-Open No. 20 1 2-2 15 6 8 9 was used. On one surface of this film, the composition for photo-alignment film 1 stored for 7 days was applied by a bar coater. Then, the film coated with the composition for photo-alignment film 1 was dried on a hot plate at 125° for 2 minutes to remove the solvent, and a precursor film having a thickness of 0.3 was formed. Irradiation of the obtained precursor film with polarized ultraviolet light By using an ultra-high pressure mercury lamp), a photo-alignment film was formed.
  • the following coating solution 1 for optically anisotropic layer was coated on the photo-alignment film using a bar coater.
  • the coating film formed on the photo-alignment film is heated to 120 ° ⁇ with warm air and then cooled to 60 ° ⁇ , and then a high-pressure mercury lamp is used in a nitrogen atmosphere for a wavelength of 1 20 ° ⁇
  • a high-pressure mercury lamp is used in a nitrogen atmosphere for a wavelength of 1 20 ° ⁇
  • a laminate was produced in the same manner as in Example 1 except that the composition 2 for a photo-alignment film was changed to the composition 2 for a photo-alignment film.
  • Composition for photo-alignment film 2 Polymer _ 1 1 00.00 parts by weight The above thermal acid generator port _ 1 3.00 parts by weight Diisopropylethylamine 0.011 3 parts by weight Putyl acetate 953.1.2 parts by weight Methyl Tyrketone 238. 28 parts by mass
  • a laminate was produced in the same manner as in Example 1 except that the composition 3 for a photo-alignment film was changed to the composition 3 for a photo-alignment film.
  • Polymer _ 1 10.00 0.00 parts by mass
  • Thermal acid generator port _ 1 3.00 parts by mass Diisopropylethylamine 2.03 parts by mass Putyl acetate 953.
  • An optical layered body was produced in the same manner as in Example 1 except that the composition 4 for the photo-alignment film was changed to the composition 4 for the photo-alignment film.
  • This optical laminate was used as the optical laminate of Example 4.
  • Composition for photo-alignment film 4 Polymer _ 1 1 00.00 parts by mass Thermal acid generator mouth _ 1 3.00 parts by mass Triptylamine ⁇ .86 parts by mass Putyl acetate 953.1.2 parts by mass Methyl ethyl ketone 238. 28 parts by mass
  • optically anisotropic layer coating liquid 2 instead of the optically anisotropic layer coating liquid 1 used in Example 1, the following optically anisotropic layer coating liquid 2 was used, and following the same procedure as in Example 1, using a bar coater, Coating solution 2 for optically anisotropic layer was applied.
  • the coating film formed on the alignment film was heated to 1 0_Rei ° ⁇ with warm air, then, using a high pressure mercury lamp under a nitrogen atmosphere was cooled to 90 ° ⁇ ,
  • Coating liquid for optically anisotropic layer 2 Polymerizable liquid crystal compound 1-_ 4 40.00 parts by mass Polymerizable liquid crystal compound 1-_ 5 40.00 part by mass Polymerizable liquid crystal compound-1-20.00 part by mass Above Polymerization initiator 3 _ 1 ⁇ .60 parts by mass Polymerizable compound below _ 1 7.00 parts by mass Leveling agent (above compound _ 1) ⁇ .1 ⁇ parts by mass Methyl ethyl ketone 200.00 parts by mass Cyclopentanone 200.00 parts by mass
  • a laminate was produced in the same manner as in Example 1 except that the composition for photoalignment film 1 was changed to the following composition for photoalignment film 5.
  • Composition for photo-alignment film 5 Polymer _ 1 1 00.00 parts by mass The above thermal acid generator mouth _ 1 3.00 parts by mass Putyl acetate 953. 1 2 parts by mass Methyl ethyl ketone 238. 28 parts by mass
  • a laminate was produced in the same manner as in Example 1 except that the composition for photoalignment film 1 was changed to the composition for photoalignment film 6 below.
  • Composition for photo-alignment film 6 Polymer _ 1 1 00.00 parts by mass The above thermal acid generator mouth _ 1 3.00 parts by mass — Butylamine ⁇ .34 parts by mass Putyl acetate 953.1.2 parts by mass ⁇ 2020/175 620 50 ⁇ (: 171? 2020 /008033
  • Minami There is very little light leakage in the observation field of view.
  • a pressure-sensitive adhesive was attached to the laminate obtained in each of the examples and comparative examples, the adhesive surface was attached to glass, and the laminate and the glass were attached to each other at a temperature of 85 ° C and a humidity of 85%. 6 (550) of the laminate after holding for 72 hours in the above environment was evaluated based on the following criteria.
  • Min When the ratio of 8 ⁇ (550) after holding is less than 98% under 6 (550) before holding in an environment of temperature 85 ° and humidity 85%.
  • the "addition amount” column of "acid generator” represents the content (% by mass) of the acid generator with respect to the total mass of the photoalignable copolymer.
  • the "addition amount” column of "amine compound” represents the content (molar amount) of the amine compound with respect to the total moles of the acid generator.
  • Liquid crystal 1 means that the coating liquid 1 for optically anisotropic layer was used, ⁇ 2020/175 620 51 ⁇ (: 171? 2020/008033
  • Liquid crystal 2 means that the coating liquid 2 for optically anisotropic layer was used.
  • composition for photo-alignment film 1 was applied to the cellulose acylate film 1 with a slit die coater so as to have a coating width of 1310. Then photo-alignment ⁇ 2020/175 620 52 ⁇ (:171? 2020 /008033
  • the film coated with the film composition 1 was blown with hot air at 125 ° to dry for 2 minutes to remove the solvent and form a precursor film having a thickness of 0.3. Irradiation of the obtained precursor film with polarized ultraviolet light By using an ultra-high pressure mercury lamp), a long photo-alignment film was formed.
  • a slit die coater was used to apply the coating liquid 2 for optically anisotropic layer with a coating width of 1320 so as to completely cover both sides of the photo-alignment film.
  • a coating film with hot air heated to 1 0_Rei ° ⁇ , then using a high-pressure mercury lamp under a nitrogen atmosphere and the mixture was cooled to 9 0 ° ⁇ at wavelength 3 6 5 nm
  • the coating film was irradiated with UV of 50,000"/ ⁇ 2 while heating it to 125°.
  • the orientation of the liquid crystal compound was fixed, and the laminate (long film) of Example 6 was produced.
  • the thickness of the 140 optically anisotropic layer was 2.5 ⁇ Ji rr ⁇ s (meth)acryloyl reaction rate was 85 %.
  • Example 7 was applied so as to completely cover both sides of the photo-alignment film. While the coating liquid was in an undried state, a scraper was pressed against both ends of the film as a scraping member to thin the coating liquid 2 for the optically anisotropic layer. In addition, in the present Example 7, from one end of the substrate to 10 ⁇ 3 The range is lightly coated. Subsequently, the coating film was dried and the orientation was fixed in the same manner as in Example 6 to produce the laminate of Example 7. Of the obtained laminate (5 5 0) 1 4 0 n m, 2 is the center thickness of the optical anisotropic layer. 5 "1, part of the thickness 1 interest thin coating in the manner described above at the end of the optically anisotropic layer, (Meth) acryloyl reaction rate was 85%
  • the coating liquid 2 for optically anisotropic layer was applied to the photo-alignment film in the same manner as in Example 6. After that, the coating film formed on the orientation film is heated to 100 ° with hot air and cooled to 90 ° , and then the web edge part to 30 To the left and right Using a high-pressure mercury lamp equipped with a shading plate, irradiate the coating film with 100 mJ / cm 2 of ultraviolet light at a wavelength of 365 nm, and then do not heat it to 125 °C for the second irradiation. The entire surface of the coating film was irradiated with ultraviolet rays of 500 m J / cm 2 without providing a light shielding plate.
  • the alignment of the liquid crystal compound was fixed, and the laminate of Example 8 was produced.
  • the R e (550) of the obtained laminate was 140 nm, the thickness was 2.5 ⁇ m, and the (meth)acryloyl reaction rate was 85%.
  • the coating liquid 2 for optically anisotropic layer was applied to the photo-alignment film.
  • the coating film formed on the alignment film was heated to 100 ° C with warm air, cooled to 90 ° C, and then, under a nitrogen atmosphere, a high pressure mercury lamp was used to set a wavelength of 100 nm. Irradiate the entire surface of the coating with mJ/cm 2 of UV light, and then heat it to 125°C while using a high pressure mercury lamp equipped with a light shield plate at a position of 3 Omm from the edge of the web to 50 OmJ/cm 2 .
  • the coating film was irradiated with ultraviolet rays.
  • Example 9 the orientation of the liquid crystal compound was fixed, and the laminate of Example 9 was produced.
  • the region where the second layer was not irradiated with UV light from the light-shielding plate of the obtained laminate had a Re (550) of 140 nm, an optically anisotropic layer thickness of 2.5 Mm, and a (meth)acryloyl reaction. The rate was 60%.
  • the edge of the support during transportation was visually evaluated.
  • Mami The unsupported area between the transport ports, where the web edge is
  • Example 6 in the long film coated with the composition for a photo-alignment film of the present invention, a force is likely to be generated at the end portion, but as shown in Examples 7 to 9, It can be improved by partial processing.

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  • Chemical & Material Sciences (AREA)
  • Physics & Mathematics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Nonlinear Science (AREA)
  • Optics & Photonics (AREA)
  • General Physics & Mathematics (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Mathematical Physics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Liquid Crystal (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Polarising Elements (AREA)

Abstract

La présente invention concerne : une composition de film de photo-alignement capable de former, même après avoir été préservée pendant une période de temps prédéterminée, un film de photo-alignement ayant une excellente capacité d'alignement de cristaux liquides par rapport à une couche anisotrope optique formée sur celui-ci ; un film de photo-alignement ; et un stratifié. Cette composition de film de photo-alignement contient : un copolymère de photo-alignement qui a une unité de répétition A comprenant un groupe de photo-alignement et une unité de répétition B comprenant un groupe de réticulation et dans laquelle un contenu a de l'unité de répétition A et un contenu b de l'unité de répétition B satisfont la formule (1) en rapport de masse ; un générateur d'acide ; et un composé amine ayant un point d'ébullition de 50 à 230 °C et n'ayant pas de proton sur un atome d'azote. (1) : 0,70 ≤ b/ (a + b) ≤ 0,97
PCT/JP2020/008033 2019-02-28 2020-02-27 Composition de résine de photo-alignement, film de photo-alignement et stratifié WO2020175620A1 (fr)

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WO2023189884A1 (fr) * 2022-03-29 2023-10-05 富士フイルム株式会社 Élément de diffraction à cristaux liquides, élément optique, unité d'affichage d'image, visiocasque, orientation de faisceau et capteur
WO2024057812A1 (fr) * 2022-09-12 2024-03-21 富士フイルム株式会社 Composition de cristaux liquides, couche durcie de cristaux liquides, film optique, plaque de polarisation, dispositif d'affichage d'image, monomère et copolymère

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JPH06509889A (ja) * 1992-06-19 1994-11-02 エフ・ホフマン−ラ　ロシュ　アーゲー 光学的非線形ポリマー
JP2010149323A (ja) * 2008-12-24 2010-07-08 Nippon Zeon Co Ltd 積層フィルムの製造方法及び積層フィルム
WO2018173727A1 (fr) * 2017-03-24 2018-09-27 富士フイルム株式会社 Copolymère à alignement optique, film d'alignement optique et corps stratifié optique
WO2019003682A1 (fr) * 2017-06-30 2019-01-03 富士フイルム株式会社 Copolymère photo-alignable, fil photo-aligné, stratifié optique et dispositif d'affichage d'image
WO2019225632A1 (fr) * 2018-05-25 2019-11-28 富士フイルム株式会社 Copolymère photo-alignable, film de photo-alignement et stratifié optique

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JPH06509889A (ja) * 1992-06-19 1994-11-02 エフ・ホフマン−ラ　ロシュ　アーゲー 光学的非線形ポリマー
JP2010149323A (ja) * 2008-12-24 2010-07-08 Nippon Zeon Co Ltd 積層フィルムの製造方法及び積層フィルム
WO2018173727A1 (fr) * 2017-03-24 2018-09-27 富士フイルム株式会社 Copolymère à alignement optique, film d'alignement optique et corps stratifié optique
WO2019003682A1 (fr) * 2017-06-30 2019-01-03 富士フイルム株式会社 Copolymère photo-alignable, fil photo-aligné, stratifié optique et dispositif d'affichage d'image
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WO2023189884A1 (fr) * 2022-03-29 2023-10-05 富士フイルム株式会社 Élément de diffraction à cristaux liquides, élément optique, unité d'affichage d'image, visiocasque, orientation de faisceau et capteur
WO2024057812A1 (fr) * 2022-09-12 2024-03-21 富士フイルム株式会社 Composition de cristaux liquides, couche durcie de cristaux liquides, film optique, plaque de polarisation, dispositif d'affichage d'image, monomère et copolymère

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