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WO2018043325A1 - Agent d'alignement de cristaux liquides, film d'alignement de cristaux liquides, et élément d'affichage à cristaux liquides mettant en œuvre celui-ci - Google Patents

Agent d'alignement de cristaux liquides, film d'alignement de cristaux liquides, et élément d'affichage à cristaux liquides mettant en œuvre celui-ci Download PDF

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Publication number
WO2018043325A1
WO2018043325A1 PCT/JP2017/030518 JP2017030518W WO2018043325A1 WO 2018043325 A1 WO2018043325 A1 WO 2018043325A1 JP 2017030518 W JP2017030518 W JP 2017030518W WO 2018043325 A1 WO2018043325 A1 WO 2018043325A1
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Prior art keywords
liquid crystal
group
diamine
aligning agent
crystal aligning
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PCT/JP2017/030518
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English (en)
Japanese (ja)
Inventor
尚士 鉄谷
早紀 相馬
尚宏 野田
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Nissan Chemical Corp
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Nissan Chemical Corp
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Application filed by Nissan Chemical Corp filed Critical Nissan Chemical Corp
Priority to JP2018537222A priority Critical patent/JP6996509B2/ja
Priority to KR1020197008285A priority patent/KR102469387B1/ko
Priority to CN201780066004.1A priority patent/CN109863449A/zh
Priority to CN202510039108.XA priority patent/CN119620472A/zh
Publication of WO2018043325A1 publication Critical patent/WO2018043325A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/52—Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
    • C09K19/54—Additives having no specific mesophase characterised by their chemical composition
    • C09K19/56—Aligning agents
    • 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
    • G02F1/133723—Polyimide, polyamide-imide
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • C08G73/1042—Copolyimides derived from at least two different tetracarboxylic compounds or two different diamino compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • C08G73/1067—Wholly aromatic polyimides, i.e. having both tetracarboxylic and diamino moieties aromatically bound
    • C08G73/1071—Wholly aromatic polyimides containing oxygen in the form of ether bonds in the main chain
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • C08G73/1075—Partially aromatic polyimides
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L79/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
    • C08L79/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
    • C08L79/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D179/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen, with or without oxygen, or carbon only, not provided for in groups C09D161/00 - C09D177/00
    • C09D179/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
    • C09D179/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • 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

Definitions

  • the liquid crystal alignment film is a constituent member of a liquid crystal display element widely used as a display device, and plays a role of aligning liquid crystals in a certain direction.
  • the main liquid crystal alignment film used industrially is formed from a liquid crystal aligning agent made of a polyimide precursor polyamic acid (also referred to as polyamic acid) or a polyimide solution. Specifically, it is obtained by applying a liquid crystal alignment agent to a substrate, heating and baking, and then performing a liquid crystal alignment treatment.
  • an alignment process using a photoreaction has been proposed as an alignment process method instead of the rubbing method.
  • a method of imparting liquid crystal alignment ability by forming a polymer film having a specific site causing a photoreaction such as polyvinyl cinnamate on the substrate surface and irradiating with polarized or non-polarized radiation ( The photo-alignment method) is known. According to this method, uniform liquid crystal alignment can be realized without generating static electricity or dust, and viewing angle can be improved by alignment division (see Patent Documents 1 and 2).
  • the liquid crystal alignment film needs to have a function of tilting and aligning liquid crystal molecules at a predetermined angle (pretilt angle) with respect to the substrate surface.
  • pretilt angle a liquid crystal alignment film using a polyamic acid or polyimide having an alkyl side chain, a side chain of a steroid skeleton, a side chain having a ring structure, or the like is known (Patent Documents 3 and 4). 5).
  • the pretilt angle is usually given by irradiation with radiation whose incident direction to the substrate surface is inclined with respect to the normal direction of the substrate (see Patent Document 1).
  • the main liquid crystal alignment film is formed of a liquid crystal alignment agent composed of a polyamic acid or polyimide solution which is a polyimide precursor.
  • a polyamic acid obtained by reacting a diamine represented by the following formula (DA-3) with a tetracarboxylic dianhydride component, and / or Or the liquid crystal aligning agent containing the polyimide obtained by imidating this polyamic acid is proposed.
  • a liquid crystal display device provided with a liquid crystal alignment film obtained from such a liquid crystal aligning agent has excellent characteristics in terms of electrical characteristics (such as loss of accumulated charge).
  • electrical characteristics such as loss of accumulated charge.
  • the obtained liquid crystal aligning film is colored black brown and loses transparency, and as a result, the liquid crystal aligning element having the liquid crystal aligning film may be adversely affected. did.
  • the present invention while maintaining the excellent characteristics due to the use of the diamine compound as a raw material of the polyamic acid that is a polymer contained in the liquid crystal alignment agent, while the obtained liquid crystal alignment film is colored black brown and It aims at providing the liquid crystal aligning agent which does not have a bad influence on liquid crystal aligning elements, such as loss of transparency.
  • the present invention includes a polyamic acid obtained by a reaction of a diamine component containing a diamine having a structure represented by the following formula [1] and a tetracarboxylic dianhydride component, and a polyimide obtained by imidizing the polyamic acid.
  • the gist of the present invention is a liquid crystal aligning agent containing at least one polymer selected from the group consisting of: (In the formula, A represents a heat-eliminable group that is replaced with a hydrogen atom by heating at a temperature of 150 to 300 ° C.
  • the hydrogen atom of the benzene ring is an alkyl group having 1 to 5 carbon atoms, or a carbon atom having 1 to 5 carbon atoms. (It may be substituted with an alkoxy group or a halogen group. * Represents a bond.)
  • the liquid crystal aligning agent of this invention contains the polyamic acid which uses the diamine represented by Formula [1] (henceforth a specific diamine) as a raw material, and / or the polyimide obtained by imidating this polyamic acid.
  • a polymer has a very high solubility in a polar solvent such as N-methylpyrrolidone (NMP) and has good handling during polymerization, and a liquid crystal aligning agent containing such a polymer is coated.
  • NMP N-methylpyrrolidone
  • the liquid crystal aligning agent of the present invention is a liquid crystal aligning film obtained as compared with a liquid crystal aligning agent containing a polyamic acid or a polyimide thereof using a diamine compound (DA-3) described later having a structure similar to a specific amine as a raw material.
  • DA-3 diamine compound
  • the diamine of the above formula (DA-3) having the same structure of the same diphenylamine skeleton as the specific diamine has a secondary amino group that is more reactive than the primary amino group in the structure.
  • the secondary amino group reacts in a reaction process with a tetracarboxylic dianhydride component for obtaining a polyamic acid, and an undesirable three-dimensional reaction occurs.
  • the obtained reaction product causes a coloring phenomenon and the characteristics as a liquid crystal aligning agent are deteriorated.
  • the specific diamine of the present invention has, in its structure, a secondary amino group that is highly reactive as in the above formula (DA-3), but the secondary amino group is protected with a thermally desorbable group. Therefore, in the reaction process with the tetracarboxylic dianhydride component to obtain a polyamic acid, an undesirable three-dimensional reaction does not occur, resulting in no coloring phenomenon and characteristics as a liquid crystal aligning agent. Seems not to decline. Further, in the liquid crystal aligning agent of the present invention, the polyamic acid or polyimide which is a polymer to be contained has an amino group protected with a thermally detachable group, but is protected with this thermally detachable group.
  • the heat-releasable group is deprotected and converted into an amino group by heating in the baking process. Can be made.
  • the deprotected amino group regains the reactivity again, and the amino group generated by the elimination reacts in the molecule to form a heterocyclic ring and the like, thereby generating a rigid side chain. It will function as a good induction site for the pretilt angle.
  • not all of the amino groups from which the heat-eliminable group is removed are used for the cyclization reaction, and some of them are also used for intermolecular reactions.
  • Crosslinking with molecular components contributes to improved reliability.
  • the polyamic acid or polyimide using the specific diamine of the present invention is less prone to scraping during rubbing treatment, and even when exposed to high temperature, backlight irradiation, etc. for a long period of time, the voltage holding ratio decreases and the ion density The increase of is difficult to occur.
  • the diamine used as a raw material for the liquid crystal aligning agent of the present invention is a diamine having a structure represented by the following formula [1].
  • A is a thermally desorbable group that is replaced with hydrogen by heating at 150 to 300 ° C., which is the firing temperature of the liquid crystal aligning agent of the present invention.
  • This thermally leaving group is preferably 170 to 300 ° C., particularly preferably 180 to 250 ° C. if it can be removed. * Represents a bond.
  • thermal leaving group examples include carbamate organic compounds represented by benzyloxycarbonyl group, 9-fluorenylmethyloxycarbonyl group, allyloxycarbonyl group, tertiary butoxycarbonyl group (also referred to as Boc group), and the like.
  • a Boc group or a 9-fluorenylmethoxycarbonyl group is particularly preferred from the viewpoint that the elimination efficiency is high and the gas is harmless at the time of elimination at a relatively low temperature.
  • the hydrogen atom of the benzene ring in the formula [1] is optionally substituted with an alkyl group or alkoxy group having 1 to 5, preferably 1 to 3 carbon atoms, or a halogen group such as chlorine, bromine or fluorine. May be.
  • the amino group possessed by the specific diamine is preferably a primary amino group. Further, for example, it may be a secondary amino group substituted with an alkyl group having a relatively small molecular weight such as a methyl group, an ethyl group, a propyl group, or a butyl group.
  • Specific examples of the specific diamine include, but are not limited to, the following.
  • Boc represents a tert-butoxycarbonyl group.
  • a tetracarboxylic dianhydride (also referred to as a specific tetracarboxylic dianhydride) represented by the following formula [7] is used as a part of the tetracarboxylic dianhydride component. It is preferable to use it.
  • Z 1 is a tetravalent organic group having 4 to 13 carbon atoms and has an aromatic cyclic hydrocarbon group. Specifically, a group represented by any of the following formulas [7a] to [7k] is preferable.
  • a preferred group represented by Z 1 is a group represented by the formula [7a] or the formula [7g] in view of polymerization reactivity and ease of synthesis. Of these, the formula [7a] is most preferable.
  • the tetracarboxylic dianhydride having the structure of the formula [7a] it is preferably 20% by mass or more of the total tetracarboxylic dianhydride component, more preferably 30% by mass or more. is there. All of the tetracarboxylic acid components used for the production of the polyimide precursor may be tetracarboxylic dianhydrides having the structure of the formula [7a].
  • an aliphatic tetracarboxylic dianhydride other than the specific tetracarboxylic dianhydride and other tetracarboxylic acid components can be used.
  • examples of the aliphatic tetracarboxylic dianhydride include 1,2,3,4-butanetetracarboxylic dianhydride.
  • Examples of the alicyclic tetracarboxylic dianhydride include 1,2,3,4-cyclobutanetetracarboxylic dianhydride, 1,2,3,4-tetramethyl-1,2,3,4- Cyclobutanetetracarboxylic dianhydride, 1,2-dimethyl-1,2,3,4-cyclobutanetetracarboxylic dianhydride, 1,3-dimethyl-1,2,3,4-cyclobutanetetracarboxylic dianhydride 1,3-diphenyl-1,2,3,4-cyclobutanetetracarboxylic dianhydride, 1,2,3,4-cyclopentanetetracarboxylic dianhydride, 1,2,4,5-cyclohexane Tetracarboxylic dianhydride, 1,2,3,4-cycloheptanetetracarboxylic dianhydride, 2,3,4,5-tetrahydrofurantetracarboxylic dianhydride, 3,4-dicarboxy-1-cycl Hexyl
  • the above-mentioned other tetracarboxylic acid components can be used alone or in combination of two or more kinds in consideration of characteristics such as liquid crystal alignment properties, voltage holding characteristics and accumulated charges of the liquid crystal alignment film to be formed.
  • the polymer in the present invention means a polyamic acid and / or a polyimide obtained by imidizing the polyamic acid.
  • the diamine other than the specific diamine (hereinafter also referred to as other diamine) used in combination when the specific diamine is less than 100 mol% includes an alicyclic diamine, an aromatic-aliphatic diamine, a heterocyclic ring.
  • Formula diamine, aliphatic diamine, etc. are mentioned.
  • alicyclic diamines examples include 1,4-diaminocyclohexane, 1,3-diaminocyclohexane, 4,4′-diaminodicyclohexylmethane, 4,4′-diamino-3,3′-dimethyldicyclohexylamine, isophorone diamine Etc.
  • aromatic diamines examples include o-phenylenediamine, m-phenylenediamine, p-phenylenediamine, 2,4-diaminotoluene, 2,5-diaminotoluene, 3,5-diaminotoluene, 1,4-diamino -2-methoxybenzene, 2,5-diamino-p-xylene, 1,3-diamino-4-chlorobenzene, 3,5-diaminobenzoic acid, 1,4-diamino-2,5-dichlorobenzene, 4,4 '-Diamino-1,2-diphenylethane, 4,4'-diamino-2,2'-dimethylbibenzyl, 4,4'-diaminodiphenylmethane, 3,3'-diaminodiphenylmethane, 3,4'-diaminodiphenylmethane 4,4′-diamin
  • aromatic-aliphatic diamines include 3-aminobenzylamine, 4-aminobenzylamine, 3-amino-N-methylbenzylamine, 4-amino-N-methylbenzylamine, 3-aminophenethylamine, 4-aminobenzylamine, Aminophenethylamine, 3-amino-N-methylphenethylamine, 4-amino-N-methylphenethylamine, 3- (3-aminopropyl) aniline, 4- (3-aminopropyl) aniline, 3- (3-methylaminopropyl) Aniline, 4- (3-methylaminopropyl) aniline, 3- (4-aminobutyl) aniline, 4- (4-aminobutyl) aniline, 3- (4-methylaminobutyl) aniline, 4- (4-methyl Aminobutyl) aniline, 3- (5-aminopentyl) aniline, 4- (5-aminopentyl) Aniline, 3- (5-methyl)
  • heterocyclic diamines examples include 2,6-diaminopyridine, 2,4-diaminopyridine, 2,4-diamino-1,3,5-triazine, 2,7-diaminodibenzofuran, 3,6-diaminocarbazole 2,4-diamino-6-isopropyl-1,3,5-triazine, 2,5-bis (4-aminophenyl) -1,3,4-oxadiazole and the like.
  • aliphatic diamines examples include 1,2-diaminoethane, 1,3-diaminopropane, 1,4-diaminobutane, 1,5-diaminopentane, 1,6-diaminohexane, 1,7-diaminoheptane, 1,8-diaminooctane, 1,9-diaminononane, 1,10-diaminodecane, 1,3-diamino-2,2-dimethylpropane, 1,6-diamino-2,5-dimethylhexane, 1,7- Diamino-2,5-dimethylheptane, 1,7-diamino-4,4-dimethylheptane, 1,7-diamino-3-methylheptane, 1,9-diamino-5-methylheptane, 1,12-diaminododecane 1,18-diaminooctadecan
  • diamine compound which has an alkyl group, a fluorine-containing alkyl group, an aromatic ring, an aliphatic ring, a heterocyclic ring, or the macrocyclic substituent which consists of them in a side chain.
  • diamines represented by the following formulas [DA1] to [DA26] are exemplified.
  • R 6 is an alkyl group or a fluorine-containing alkyl group having 1 to 22 carbon atoms.
  • R 6 represents 1 to 22 carbon atoms. It has an alkyl group or a fluorine-containing alkyl group.
  • R 7 represents an alkyl group or alkoxy group having 1 to 22 carbon atoms.
  • R 6 represents —O—, —OCH 2 —, —CH 2 O—, —COOCH 2 —, or —CH 2 OCO—
  • R 7 represents an alkyl group or alkoxy group having 1 to 22 carbon atoms.
  • R 8 represents an alkyl group, an alkoxy group, a fluorine-containing alkyl group or a fluorine-containing alkoxy group having 1 to 22 carbon atoms.
  • R 9 represents a fluorine group, a cyano group, a trifluoromethane group, a nitro group, an azo group, a formyl group, an acetyl group, an acetoxy group, or a hydroxyl group.
  • R 10 is an alkyl group having 3 to 12 carbon atoms, and the cis-trans isomerism of 1,4-cyclohexylene is a trans isomer.
  • a specific diamine in combination with the diamines [DA-1] to [DA-26] because a more stable pretilt angle can be obtained.
  • More preferred diamines that can be used in combination are those represented by the formulas [DA-10] to [DA-26], more preferably diamines of [DA-10] to [DA-16].
  • the preferred content of these diamines is not particularly limited, but is preferably 5 to 50 mol% in the diamine component, and is preferably 5 to 30 mol% in terms of printability. Moreover, you may use the following diamine together.
  • diaminosiloxanes represented by the following formula [DA-35] can also be mentioned as other diamines.
  • M is an integer from 1 to 10.
  • Other diamines can be used singly or in combination of two or more depending on properties such as liquid crystal alignment properties, voltage holding properties, and accumulated charges when the liquid crystal alignment film is formed.
  • ⁇ Production of polyamic acid> As a method for obtaining the polyamic acid of the present invention by the reaction of the tetracarboxylic dianhydride component and the diamine component, a known method can be used. In general, the tetracarboxylic dianhydride component and the diamine component are reacted in an organic solvent. The reaction between the tetracarboxylic dianhydride component and the diamine is advantageous in that it proceeds relatively easily in an organic solvent and no by-products are generated.

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Abstract

L'invention fournit un agent d'alignement de cristaux liquides qui présente d'excellentes propriétés électriques en un point d'extraction de charge stockée, ou similaire, et qui est destiné à former un film d'alignement de cristaux liquides non coloré et transparent. Plus précisément, cet agent d'alignement de cristaux liquides est caractéristique en ce qu'il comprend au moins un polymère choisi dans un groupe constitué d'un acide polyamique obtenu par réaction d'un composant diamine comprenant une diamine possédant une structure de formule ［1］ et d'un composant dianhydride d'acide tétracarboxylique, et d'un polyimide obtenu par imidation de cet acide polyamique. (A représente un groupe clivable thermiquement substitué par un atome d'hydrogène sous l'effet d'un chauffage de température comprise entre 150 et 300°C. L'atome d'hydrogène possédant un cycle benzène peut être substitué soit par un groupe alkyle ou un groupe alcoxy de 1 à 5 atomes de carbone, soit par un groupe halogène. ＊ représente une liaison atomique.)
PCT/JP2017/030518 2016-08-30 2017-08-25 Agent d'alignement de cristaux liquides, film d'alignement de cristaux liquides, et élément d'affichage à cristaux liquides mettant en œuvre celui-ci Ceased WO2018043325A1 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
JP2018537222A JP6996509B2 (ja) 2016-08-30 2017-08-25 液晶配向剤、液晶配向膜及びそれを用いた液晶表示素子
KR1020197008285A KR102469387B1 (ko) 2016-08-30 2017-08-25 액정 배향제, 액정 배향막 및 그것을 사용한 액정 표시 소자
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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111971617A (zh) * 2018-04-09 2020-11-20 日产化学株式会社 液晶取向剂、液晶取向膜和使用其的液晶表示元件
CN115343886A (zh) * 2022-10-18 2022-11-15 广州华星光电半导体显示技术有限公司 一种液晶配向层及其制备方法、液晶显示装置

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN117866199B (zh) * 2024-03-11 2024-05-28 烟台三月科技有限责任公司 一种液晶取向剂、液晶取向膜及其液晶显示元件

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2015166844A (ja) * 2014-02-13 2015-09-24 Jsr株式会社 液晶配向剤、液晶配向膜、液晶表示素子、位相差フィルム、位相差フィルムの製造方法、重合体及び化合物
JP2016095488A (ja) * 2014-11-05 2016-05-26 Jsr株式会社 液晶配向剤、液晶配向膜、液晶表示素子、重合体及び化合物

Family Cites Families (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2780183B2 (ja) 1989-02-27 1998-07-30 セイコーエプソン株式会社 配向膜および液晶装置
JP2893671B2 (ja) 1991-03-11 1999-05-24 ジェイエスアール株式会社 液晶配向剤
JP3097702B2 (ja) 1991-08-13 2000-10-10 日産化学工業株式会社 新規な液晶配向処理剤
US5539074A (en) 1993-02-17 1996-07-23 Hoffmann-La Roche Inc. Linear and cyclic polymers or oligomers having a photoreactive ethene group
JP3893659B2 (ja) 1996-03-05 2007-03-14 日産化学工業株式会社 液晶配向処理方法
JP5223775B2 (ja) * 2009-05-25 2013-06-26 セントラル硝子株式会社 液浸レジスト用撥水性添加剤
JP5884258B2 (ja) * 2009-09-18 2016-03-15 Jnc株式会社 液晶配向剤、液晶配向膜、液晶配向膜の製造方法および液晶表示素子
TWI501998B (zh) * 2010-03-15 2015-10-01 Nissan Chemical Ind Ltd A liquid crystal aligning agent containing a polyamic acid ester, and a liquid crystal alignment film
WO2012023570A1 (fr) * 2010-08-17 2012-02-23 日産化学工業株式会社 Procédé de préparation d'un composé précurseur diamine
WO2012053525A1 (fr) * 2010-10-19 2012-04-26 日産化学工業株式会社 Agent d'alignement de cristaux liquides utilisé pour un processus de photo-alignement, et film d'alignement de cristaux liquides le comprenant
JP5929298B2 (ja) 2011-03-02 2016-06-01 Jnc株式会社 ジアミン、これを用いた液晶配向剤、液晶表示素子および液晶配向膜の形成方法
JP6578948B2 (ja) * 2013-10-23 2019-09-25 日産化学株式会社 熱脱離性基を有するポリイミド前駆体及び／又はポリイミドを含む液晶配向剤
JP2016138236A (ja) * 2014-12-26 2016-08-04 Jsr株式会社 組成物、液晶配向剤、液晶配向膜及び液晶表示素子

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2015166844A (ja) * 2014-02-13 2015-09-24 Jsr株式会社 液晶配向剤、液晶配向膜、液晶表示素子、位相差フィルム、位相差フィルムの製造方法、重合体及び化合物
JP2016095488A (ja) * 2014-11-05 2016-05-26 Jsr株式会社 液晶配向剤、液晶配向膜、液晶表示素子、重合体及び化合物

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111971617A (zh) * 2018-04-09 2020-11-20 日产化学株式会社 液晶取向剂、液晶取向膜和使用其的液晶表示元件
CN115343886A (zh) * 2022-10-18 2022-11-15 广州华星光电半导体显示技术有限公司 一种液晶配向层及其制备方法、液晶显示装置
CN115343886B (zh) * 2022-10-18 2023-01-10 广州华星光电半导体显示技术有限公司 一种液晶配向层及其制备方法、液晶显示装置

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