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WO2017111117A1 - Agent et film d'alignement de cristaux liquides, et élément d'affichage à cristaux liquides - Google Patents

Agent et film d'alignement de cristaux liquides, et élément d'affichage à cristaux liquides Download PDF

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Publication number
WO2017111117A1
WO2017111117A1 PCT/JP2016/088539 JP2016088539W WO2017111117A1 WO 2017111117 A1 WO2017111117 A1 WO 2017111117A1 JP 2016088539 W JP2016088539 W JP 2016088539W WO 2017111117 A1 WO2017111117 A1 WO 2017111117A1
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Prior art keywords
liquid crystal
carbon atoms
group
diamine
aligning agent
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PCT/JP2016/088539
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English (en)
Japanese (ja)
Inventor
崇明 杉山
耕平 後藤
亮一 芦澤
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Nissan Chemical Corp
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Nissan Chemical Corp
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Priority to KR1020187021109A priority Critical patent/KR102802267B1/ko
Priority to JP2017558303A priority patent/JP7027890B2/ja
Priority to CN201680082511.XA priority patent/CN108700777A/zh
Publication of WO2017111117A1 publication Critical patent/WO2017111117A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • 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
    • 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
    • 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
    • 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
    • G02F1/133723—Polyimide, polyamide-imide

Definitions

  • the present invention relates to a liquid crystal aligning agent, a liquid crystal aligning film, and a liquid crystal display element using the liquid crystal aligning agent used when a liquid crystal aligning film is produced.
  • a liquid crystal display element As a liquid crystal display element, the major axis of nematic liquid crystal having positive dielectric anisotropy between two electrode substrates in which a liquid crystal alignment film is formed on an electrode is continuous from one substrate to the other substrate.
  • IPS in-plane switching
  • VA vertical
  • a liquid crystal alignment film used in these liquid crystal display elements a polyimide-based liquid crystal alignment film is mainly used, and polyimide-based alignment films having various structures (for example, see Patent Document 1) have been developed.
  • liquid crystal filling has been generally performed by a vacuum injection method in which a liquid crystal is filled between two substrates using a pressure difference between atmospheric pressure and vacuum.
  • the liquid crystal injection port is provided only on one side of the substrate, it takes a long time to fill the liquid crystal between the substrates having a cell gap of 3 to 5 ⁇ m. It was difficult to simplify the manufacturing process. This has been a big problem especially in the production of liquid crystal TVs and large monitors.
  • a liquid crystal dropping method ODF method
  • a liquid crystal is dropped on a substrate on which a liquid crystal alignment film is formed, bonded to the other substrate in a vacuum, and then the sealing material is UV cured to fill the liquid crystal.
  • the liquid crystal dropping method has been solved by optimizing the manufacturing process so as to reduce the influence of adsorbed water and impurities, such as reducing the dropping amount of liquid crystal and improving the degree of vacuum at the time of bonding.
  • the liquid crystal display element production line becomes larger, it has become impossible to suppress display unevenness by optimizing the manufacturing process so far, and a liquid crystal alignment film that can reduce alignment unevenness more than before has been demanded.
  • This alignment unevenness is caused by the adsorbed water and impurities adhering to the surface of the liquid crystal alignment film formed on the substrate being swept away by the liquid crystal dropped in the ODF process, so that the liquid crystal dropping part and the liquid crystal droplets are in contact with each other. It is thought to be generated by the amount of adsorbed water and impurities.
  • the present invention has been made in view of the above circumstances, and the problem to be solved by the present invention is to provide a liquid crystal aligning agent that forms a liquid crystal alignment film that can reduce liquid crystal alignment unevenness that occurs in the ODF method.
  • An object of the present invention is to provide a liquid crystal display element with reduced display unevenness caused by liquid crystal alignment unevenness generated in the ODF method.
  • the present invention has the following gist.
  • a polyamic acid obtained by reacting a diamine component containing a diamine containing a crown ether structure and an aromatic ring and a diamine having a side chain that develops a pretilt angle of liquid crystal, and a tetracarboxylic dianhydride component, and A liquid crystal aligning agent comprising at least one polymer selected from the group consisting of polyimides which are imidized products of the polyamic acid.
  • a liquid crystal alignment film obtained from the liquid crystal alignment agent described above.
  • a liquid crystal display device comprising the liquid crystal alignment film as described above.
  • the liquid crystal aligning film which can reduce the liquid crystal aligning nonuniformity which generate
  • the crown ether used as the raw material of the liquid crystal aligning agent of the present invention is a macrocycle.
  • Such a diamine containing a crown ether structure and an aromatic ring (hereinafter also referred to as a specific diamine 1) is not limited as long as it has a crown ether structure and an aromatic ring structure. However, if it has an excessively bulky structure or a ring with a large molecular weight, the liquid crystal alignment may be disturbed, so the molecular weight is preferably 250 to 1500, and more preferably 250 to 1000.
  • the aromatic ring may be either an allocyclic ring or a heterocyclic ring.
  • the aromatic ring is a residue obtained by removing one hydrogen atom from an allocyclic aromatic compound.
  • a nitrogen atom-containing heterocyclic aromatic compound it means a residue obtained by removing one hydrogen atom from a nitrogen atom-containing heterocyclic aromatic compound.
  • homocyclic aromatic compound examples include cyclopentadiene, benzene, azulene, naphthalene, anthracene, phenanthrene, pyrene, naphthacene, benzopyrene, perylene, pentacene, phenalene, indene, fluorene, biphenylene, and the like.
  • the N—H site in pyrrole, pyrazole, imidazole and the like may be as it is or may be alkylated such as methylation.
  • the hydrogen atom on the carbon atom or nitrogen atom constituting the ring in the above homocyclic aromatic compound or nitrogen atom-containing heterocyclic aromatic compound may be substituted.
  • the type and number of substituents are not particularly limited, but electron-donating substituents having a relatively low molecular weight such as methyl, ethyl, alkoxyl, methoxy, ethoxy, amino, and dimethylamino groups, and carboxyl groups.
  • an electron-withdrawing substituent having a relatively small molecular weight such as a nitro group or a cyano group is preferable because it activates electron transfer.
  • the position of the substituent in the homocyclic aromatic compound or heterocyclic aromatic compound is not particularly limited, but in the case of a nitrogen-containing heterocyclic aromatic compound, the position of the substituent is preferably not adjacent to the nitrogen atom.
  • X 1 and X 2 each independently represents a single bond or — (OCH 2 CH 2 ) n —.
  • n represents an integer of 1 to 6, preferably an integer of 1 to 4.
  • R 1 represents one of the following two structures. Two R 1 may be the same or different.
  • R 1 , R 2 and R 4 each independently represent a single bond or an alkylene group having 1 to 5 carbon atoms
  • R 3 represents a single bond, an alkylene group having 1 to 5 carbon atoms or a carbonyl group.
  • X represents an aromatic ring.
  • aromatic ring benzene, pyridine, pyridazine, pyrimidine, pyrazine, triazine pyrrole, oxazole, oxadiazole, thiazole, thiadiazole, imidazole, pyrazole, or triazole are preferable. Of these, benzene is preferred.
  • specific examples of the specific diamine 1 include the following DA-1 to DA-10. Of these, DA-2, DA-3, DA-6 or DA-7 is preferred.
  • the specific diamine 1 is preferably 10 to 80 mol%, more preferably 10 to 70 mol%, and particularly preferably 20 to 50 mol% with respect to the diamine component (1 mol) used for the synthesis of the polyamic acid.
  • Examples of the diamine having a side chain that develops the pretilt angle of liquid crystal include a long-chain alkyl group, a perfluoroalkyl group, an aromatic cyclic group, an aliphatic cyclic group, or a combination thereof.
  • Examples include diamines having a group or a steroid skeleton group, which can be represented by the following general formula.
  • X 1 is —O—, —CH 2 O—, —COO—, — (CH 2 ) a— (a is an integer of 1 to 10), —NH—, —N (CH 3 ) —, —CONH A divalent organic group selected from-, -NHCO-, -OCO-, -CON (CH 3 )-, -N (CH 3 ) CO-, or a single bond.
  • X 2 is a single bond or a divalent organic group selected from — (CH 2 ) b — (b is an integer of 1 to 10).
  • X 3 is a single bond, — (CH 2 ) c — (c is an integer of 1 to 10), —O—, —NH—, —N (CH 3 ) —, —CONH—, —NHCO—, — A divalent organic group selected from CH 2 O—, —COO—, —OCO—, —CON (CH 3 ) —, or —N (CH 3 ) CO—.
  • X 4 represents a divalent cyclic group selected from a benzene ring, a cyclohexyl ring, or a heterocyclic ring, or a divalent organic group having 12 to 25 carbon atoms having a steroid skeleton, and any arbitrary group on the cyclic group
  • the hydrogen atom is selected from an alkyl group having 1 to 3 carbon atoms, an alkoxyl group having 1 to 3 carbon atoms, a fluorine-containing alkyl group having 1 to 3 carbon atoms, a fluorine-containing alkoxyl group having 1 to 3 carbon atoms, and a fluorine atom. It may be replaced with a thing.
  • X 5 represents a divalent cyclic group selected from a cyclohexyl ring, a benzene ring, or a heterocyclic ring, and an arbitrary hydrogen atom on these cyclic groups is an alkyl group having 1 to 3 carbon atoms, or 1 to 3 carbon atoms.
  • 3 alkoxyl groups, a fluorine-containing alkyl group having 1 to 3 carbon atoms, a fluorine-containing alkoxyl group having 1 to 3 carbon atoms, or a fluorine atom may be substituted.
  • n is an integer of 0-4.
  • X 6 is an alkyl group having 1 to 18 carbon atoms, a fluorine-containing alkyl group having 1 to 18 carbon atoms, an alkoxyl group having 1 to 18 carbon atoms, a fluorine-containing alkoxyl group having 1 to 18 carbon atoms, or a hydrogen atom. It is an integer from 1 to 4.
  • X 1 is a single bond, — (CH 2 ) a — (a is an integer of 1 to 10), —O—, —CONH—, —CH 2 O—, or —COO—
  • the chain structure is preferred because it is easy to synthesize. More preferably, it is a single bond, — (CH 2 ) a — (a is an integer of 1 to 10), —O—, —CONH—, —CH 2 O—, or —COO—. More preferably, they are a single bond, — (CH 2 ) a — (a is an integer of 1 to 10), —O—, —CH 2 O— or —COO—.
  • X 2 is preferably a single bond or — (CH 2 ) b — (b is an integer of 1 to 10).
  • X 3 is, inter alia, a single bond, - (CH 2) c - (c is an integer of 1 ⁇ 10), - O - , - CH 2 O -, - COO-, or -OCO- is synthesized It is preferable because it is easy to do. More preferably, they are a single bond, — (CH 2 ) c — (c is an integer of 1 to 10), —O—, —CH 2 O—, —COO—, or —OCO—.
  • X 4 is preferably a benzene ring, a cyclohexyl ring, that is, a phenylene group, a cyclohexylene group, or an organic group having 12 to 25 carbon atoms having a steroid skeleton.
  • X 5 is preferably a benzene ring or a cyclohexyl ring.
  • X 6 is preferably an alkyl group having 1 to 18 carbon atoms, a fluorine-containing alkyl group having 1 to 10 carbon atoms, an alkoxyl group having 1 to 18 carbon atoms, or a fluorine-containing alkoxyl group having 1 to 10 carbon atoms.
  • n is preferably an integer of 0 to 2.
  • m is preferably an integer of 1 to 2.
  • a preferred combination of X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , and n in the formula [1] is described on pages 11 to 32 of International Publication No. WO2011 / 132752 (published 2011.10.27). Examples thereof include the same combinations as (1-1) to (1-629) listed in Tables 1 to 42. Specific examples of the diamine compound having a side chain that develops the pretilt angle of the liquid crystal are given below, but the present invention is not limited thereto.
  • R 1 represents —O—, —OCH 2 —, —CH 2 O—, —COOCH 2 —, —CH 2 OCO—
  • R 2 Is an alkyl group having 1 to 22 carbon atoms, an alkoxy group, a fluorine-containing alkyl group, or a fluorine-containing alkoxy group).
  • R 3 represents —COO—, —OCO—, —CONH—, —NHCO—, —COOCH 2 —, —CH 2 OCO—, —CH 2 O—, —OCH 2 —, or —CH 2 —, wherein R 4 is an alkyl group having 1 to 22 carbon atoms, an alkoxy group, a fluorine-containing alkyl group, or a fluorine-containing alkoxy group).
  • R 5 is, -COO -, - OCO -, - CONH -, - NHCO -, - COOCH 2 -, - CH 2 OCO -, - CH 2 O—, —OCH 2 —, —CH 2 —, —O—, or —NH—
  • R 6 is fluorine, cyano, trifluoromethane, nitro, azo, formyl, acetyl, acetoxy Group or hydroxyl group).
  • R 7 is an alkyl group having 3 to 12 carbon atoms, and the cis-trans isomerism of 1,4-cyclohexylene is a trans isomer. is there.
  • R 8 is an alkyl group having 3 to 12 carbon atoms, and the cis-trans isomerism of 1,4-cyclohexylene is a trans isomer. is there.
  • a 4 is an alkyl group having 3 to 20 carbon atoms which may be substituted with a fluorine atom
  • a 3 is a 1,4-cyclohexylene group or 1,4 -Phenylene group
  • a 2 is an oxygen atom or —COO— * (where a bond marked with “*” is bonded to A 3 )
  • a 1 is an oxygen atom or —COO— * (However, "*", a bond was given the (CH 2) a 2) is a bond to).
  • a 1 is an integer of 0 or 1
  • a 2 is an integer of 2 to 10
  • a 3 is an integer of 0 or 1.
  • the diamine having a side chain that develops the pretilt angle of the liquid crystal used in the liquid crystal aligning agent of the present invention is preferably 10 to 80 mol%, more preferably 20 to 80 mol%, more preferably 20 to 70 mol% is particularly preferred.
  • ⁇ Other diamines> When obtaining the liquid crystal aligning agent of this invention, other diamines other than specific diamine 1 and 2 can be used.
  • examples of such other diamines include alicyclic diamines, aromatic diamines, heterocyclic diamines, aliphatic diamines, and aromatic-aliphatic diamines. Specific examples of such diamines are shown below.
  • Examples of alicyclic diamines 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, 3,5-diamino- N, N-diallylaniline, 2,4-diamino-N, N-diallylaniline, 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'-dimethylbi Benzyl, 4,4'-diaminodiphenylmethane, 3,3'
  • 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
  • aromatic-aliphatic diamine examples include a diamine represented by the formula [3].
  • Ar ′ is phenylene or naphthylene
  • R 5 is an alkylene group having 1 to 5 carbon atoms, preferably 1 to 3 carbon atoms
  • R 6 is a hydrogen atom or an alkyl group having 1 to 5 carbon atoms, Preferably they are a hydrogen atom or a methyl group.
  • diamine represented by the formula [3] examples include 3-aminobenzylamine, 4-aminobenzylamine, 3-amino-N-methylbenzylamine, 4-amino-N-methylbenzylamine, 3-amino Phenethylamine, 4-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-Methylaminobutyl) aniline, 3- (5-aminopentyl) aniline, 4- (5-aminopentyl) ) Aniline, 3- (5-amin
  • the tetracarboxylic dianhydride component to be reacted with the above-described diamine component is not particularly limited, and one kind or two or more kinds of tetracarboxylic dianhydrides may be used in combination.
  • a tetracarboxylic dianhydride to be reacted with the diamine component a tetracarboxylic dianhydride having an alicyclic structure or an aliphatic structure is used from the viewpoint that the voltage holding ratio of the liquid crystal cell can be further improved. preferable.
  • Examples of the tetracarboxylic dianhydride having an alicyclic structure or an aliphatic structure include 1,2,3,4-cyclobutanetetracarboxylic dianhydride, 1,2-dimethyl-1,2,3,4-cyclobutane.
  • Tetracarboxylic dianhydride 1,3-dimethyl-1,2,3,4-cyclobutanetetracarboxylic dianhydride, 1,2,3,4-tetramethyl-1,2,3,4-cyclobutanetetra Carboxylic dianhydride, 1,2,3,4-cyclopentanetetracarboxylic dianhydride, 2,3,4,5-tetrahydrofurantetracarboxylic dianhydride, 1,2,4,5-cyclohexanetetracarboxylic Acid dianhydride, 3,4-dicarboxy-1-cyclohexylsuccinic dianhydride, 3,4-dicarboxy-1,2,3,4-tetrahydro-1-naphthalene succinic dianhydride, [ -(2,5-dioxotetrahydrofuran-3-yl) -1,2,3,4-tetrahydronaphthalene-1,2-dicarboxylic anhydride], 1,2,3,4-butanetetracarbox
  • Aromatic tetracarboxylic dianhydrides include pyromellitic dianhydride, 3,3 ′, 4,4′-biphenyltetracarboxylic dianhydride, 2,2 ′, 3,3′-biphenyltetracarboxylic acid Dianhydride, 2,3,3 ′, 4-biphenyltetracarboxylic dianhydride, 3,3 ′, 4,4′-benzophenonetetracarboxylic dianhydride, 2,3,3 ′, 4-benzophenonetetra Carboxylic dianhydride, bis (3,4-dicarboxyphenyl) ether dianhydride, bis (3,4-dicarboxyphenyl) sulfone dianhydride, 1,2,5,6-naphthalenetetracarboxylic dianhydride, 1,2,5,6-naphthalenetetracarboxylic dianhydride, 1,2,5,6-naphthalenetetracarboxylic dian
  • pyromellitic dianhydride is particularly preferable.
  • the tetracarboxylic dianhydride having an alicyclic structure or an aliphatic structure and an aromatic tetra from the balance of the properties such as solubility of the polyamic acid or polyimide, orientation of the liquid crystal, voltage holding ratio, accumulated charge, etc.
  • the combined use with carboxylic dianhydride is preferable, and the use ratio of the former / the latter is preferably 90/10 to 50/50, more preferably 80/20 to 60/40 in terms of molar ratio.
  • a known polymerization method can be used for the polyamic acid used in the present invention.
  • the tetracarboxylic dianhydride component and the diamine component are reacted in an organic solvent.
  • the reaction of tetracarboxylic dianhydride and diamine is advantageous in that it proceeds relatively easily in an organic solvent and no by-product is produced.
  • the organic solvent used in that case will not be specifically limited if the produced
  • the solvent may be used alone or in combination.
  • it may be used by mixing with the above solvent as long as the produced polyamic acid does not precipitate.
  • water in the organic solvent inhibits the polymerization reaction and further causes hydrolysis of the generated polyamic acid, it is preferable to use a dehydrated and dried organic solvent as much as possible.
  • a solution in which diamine is dispersed or dissolved in an organic solvent is stirred, and tetracarboxylic dianhydride is dispersed as it is or in an organic solvent.
  • examples include a method of adding by dissolving, a method of adding diamine to a solution in which tetracarboxylic dianhydride is dispersed or dissolved in an organic solvent, and a method of adding tetracarboxylic dianhydride and diamine alternately. Any of these methods may be used.
  • tetracarboxylic dianhydride or diamine when tetracarboxylic dianhydride or diamine is composed of a plurality of compounds, they may be reacted in a premixed state, individually reacted sequentially, and further individually reacted low molecular weight substances. It is good also as a high molecular weight body by carrying out mixing reaction.
  • the temperature at the time of synthesizing the polyamic acid can be selected from -20 ° C. to 150 ° C., but is preferably in the range of ⁇ 5 ° C. to 100 ° C.
  • the reaction can be carried out at any concentration, but if the concentration is too low, it is difficult to obtain a high molecular weight polymer, and if the concentration is too high, the viscosity of the reaction solution becomes too high and uniform stirring is difficult. Therefore, the content is preferably 1 to 50% by mass, more preferably 5 to 30% by mass.
  • the initial stage of the reaction is carried out at a high concentration, and then an organic solvent can be added.
  • the ratio of the number of moles of the diamine component to the number of moles of tetracarboxylic dianhydride is preferably 0.8 to 1.2. Similar to the normal polycondensation reaction, the closer the molar ratio is to 1.0, the higher the molecular weight of the polyamic acid produced.
  • the polyimide used in the present invention is a polyimide obtained by dehydrating and ring-closing the above polyamic acid, and is useful as a polymer for obtaining a liquid crystal alignment film.
  • the dehydration cyclization rate (imidation rate) of the amic acid group is not necessarily 100%, and can be arbitrarily adjusted according to the application and purpose.
  • Examples of the method for imidizing the polyamic acid include thermal imidization in which the polyamic acid solution is heated as it is, and catalytic imidization in which a catalyst is added to the polyamic acid solution.
  • the temperature at which the polyamic acid is thermally imidized in the solution is 100 to 400 ° C., preferably 120 to 250 ° C., and it is preferable to carry out while removing water generated by the imidation reaction from the system.
  • the catalytic imidation of the polyamic acid can be carried out by adding a basic catalyst and an acid anhydride to the polyamic acid solution and stirring at ⁇ 20 ° C. to 250 ° C., preferably 0 to 180 ° C.
  • the amount of the basic catalyst is 0.5 to 30 mol times, preferably 2 to 20 mol times of the amic acid group, and the amount of the acid anhydride is 1 to 50 mol times, preferably 3 to 30 mol of the amido acid group. Is double.
  • the basic catalyst include pyridine, triethylamine, trimethylamine, tributylamine, trioctylamine and the like. Among them, pyridine is preferable because it has an appropriate basicity for proceeding with the reaction.
  • the acid anhydride include acetic anhydride, trimellitic anhydride, pyromellitic anhydride, and the like. Among them, use of acetic anhydride is preferable because purification after completion of the reaction is facilitated.
  • the imidization rate by catalytic imidation can be controlled by adjusting the amount of catalyst, reaction temperature, and reaction time.
  • the imidation ratio of the polyimide used in the liquid crystal aligning agent of the present invention is not particularly limited, but a liquid crystal alignment film having a higher voltage holding ratio can be obtained. Therefore, the imidation ratio is preferably 40 to 90%, and 50 to 90 % Is more preferable, and 60 to 90% is particularly preferable.
  • the reaction solution may be poured into a poor solvent and precipitated.
  • Examples of the poor solvent used for precipitation include methanol, acetone, hexane, butyl cellosolve, heptane, methyl ethyl ketone, methyl isobutyl ketone, ethanol, toluene, benzene, and water.
  • the polymer precipitated in a poor solvent and collected by filtration can be dried by normal temperature or reduced pressure at room temperature or by heating.
  • impurities in the polymer can be reduced.
  • the molecular weights of the polyamic acid and polyimide used in the present invention are weight average molecular weights measured by GPC (Gel Permeation Chromatography) method in consideration of the strength of the coating film, workability when forming the coating film, and uniformity of the coating film.
  • GPC Gel Permeation Chromatography
  • the liquid crystal aligning agent of this invention is a coating liquid for producing a liquid crystal aligning film
  • the main component consists of the resin component for forming a resin film, and the organic solvent which dissolves this resin component.
  • the resin component is a resin component containing polyamic acid and / or polyimide.
  • the content of the resin component is 1 to 20% by mass, preferably 2 to 10% by mass.
  • the resin component may be a polymer using specific diamines 1 and 2 as a diamine component to be reacted with tetracarboxylic dianhydride (hereinafter also referred to as a specific polymer). Further, other polymers that do not use the specific diamines 1 and 2 may be contained.
  • the content of the specific polymer in the resin component is preferably 0.5 to 15% by mass, and preferably 1 to 10% by mass.
  • the organic solvent for dissolving the resin component is not particularly limited. Specific examples include N, N′-dimethylformamide, N, N′-dimethylacetamide, N-methyl-2-pyrrolidone, N-methylcaprolactam, 2-pyrrolidone, N-ethylpyrrolidone, N-vinylpyrrolidone, dimethyl sulfoxide.
  • Tetramethylurea pyridine, dimethylsulfone, hexamethylsulfoxide, ⁇ -butyrolactone, 1,3-dimethyl-2-imidazolidinone, dipentene, ethyl amyl ketone, methyl nonyl ketone, methyl ethyl ketone, methyl isoamyl ketone, methyl isopropyl ketone, Examples include cyclohexanone, ethylene carbonate, propylene carbonate, diglyme, 4-hydroxy-4-methyl-2-pentanone, and the like. Two or more kinds of these solvents may be mixed and used.
  • the concentration of the specific polyimide solution is not particularly limited. However, since it is easy to mix uniformly with the specific amine, the specific polyimide concentration in the solution is preferably 1 to 20% by mass, more preferably 3 to 15% by mass, and particularly preferably. Is 3 to 10% by mass.
  • the liquid crystal aligning agent of this invention may contain components other than the above.
  • examples thereof may include a solvent and a compound that improve the film thickness uniformity and surface smoothness when a liquid crystal aligning agent is applied, a compound that improves the adhesion between the liquid crystal aligning film and the substrate, and the like.
  • Specific examples of the solvent (poor solvent) that improves the uniformity of the film thickness and the surface smoothness include the following.
  • butyl cellosolve propylene glycol monomethyl ether, propylene glycol monobutyl ether, and ethyl lactate are more preferable.
  • These poor solvents may be used alone or in combination.
  • the above solvent it is preferably 5 to 80% by mass, more preferably 20 to 60% by mass, based on the total amount of the solvent contained in the liquid crystal aligning agent.
  • examples of compounds that improve film thickness uniformity and surface smoothness include fluorine-based surfactants, silicone-based surfactants, and nonionic surfactants.
  • F-top EF301, EF303, EF352 product name of Tokem Products
  • MegaFuck F171, F173, R-30 product name of Dainippon Ink
  • Florard FC430, FC431 Suditomo 3M Manufactured by Asahi Guard AG710, Surflon S-382, SC101, SC102, SC103, SC104, SC105, SC106 (trade name of Asahi Glass Co., Ltd.).
  • the use ratio of these surfactants is preferably 0.01 to 2 parts by mass, more preferably 0.01 to 1 part by mass with respect to 100 parts by mass of the resin component contained in the liquid crystal aligning agent.
  • the compound that improves the adhesion between the liquid crystal alignment film and the substrate include the following functional silane-containing compounds and epoxy group-containing compounds.
  • the amount is preferably 0.1 to 30 parts by mass, more preferably 1 to 20 parts by mass with respect to 100 parts by mass of the resin component contained in the liquid crystal aligning agent. It is. If the amount is less than 0.1 part by mass, the effect of improving the adhesion cannot be expected, and if it exceeds 30 parts by mass, the orientation of the liquid crystal may deteriorate.
  • the liquid crystal aligning agent of the present invention includes a dielectric or conductive material for changing the electrical properties such as dielectric constant and conductivity of the liquid crystal aligning film, and also the hardness of the film when it is used as the liquid crystal aligning film. Alternatively, a crosslinkable compound for the purpose of increasing the density may be added.
  • the concentration of the solid content in the liquid crystal aligning agent of the present invention can be appropriately changed depending on the film thickness of the target liquid crystal aligning film. From the reason that it can be obtained, the content is preferably 1 to 20% by mass, more preferably 2 to 10% by mass.
  • the liquid crystal aligning agent of the present invention can be used as a liquid crystal alignment film after being applied and baked on a substrate and then subjected to alignment treatment by rubbing treatment, light irradiation or the like, or without alignment treatment in vertical alignment applications.
  • the substrate to be used is not particularly limited as long as it is a highly transparent substrate, and a glass substrate, a plastic substrate such as an acrylic substrate or a polycarbonate substrate, or the like can be used.
  • an opaque material such as a silicon wafer can be used as long as the substrate is only on one side, and in this case, a material that reflects light such as aluminum can be used.
  • the application method of the liquid crystal aligning agent is not particularly limited, but industrially, a method of screen printing, offset printing, flexographic printing, ink jet, or the like is common. Other coating methods include dip, roll coater, slit coater, spinner and the like, and these may be used depending on the purpose.
  • Firing after applying the liquid crystal aligning agent on the substrate can form a coating film by evaporating the solvent at 50 to 200 ° C., preferably 80 to 150 ° C., by a heating means such as a hot plate. If the thickness of the coating film after baking is too thick, it is disadvantageous in terms of power consumption of the liquid crystal display element, and if it is too thin, the reliability of the liquid crystal display element may be lowered. Therefore, it is preferably 5 to 300 nm, more preferably 10 to 100 nm. When the liquid crystal is horizontally or tilted, the fired coating film is treated by rubbing or irradiation with polarized ultraviolet rays.
  • the liquid crystal display device of the present invention is a device in which a liquid crystal cell is prepared by a known method after obtaining a substrate with a liquid crystal alignment film using the liquid crystal aligning agent of the present invention by the above-described method.
  • a liquid crystal cell is prepared by a known method after obtaining a substrate with a liquid crystal alignment film using the liquid crystal aligning agent of the present invention by the above-described method.
  • prepare a pair of substrates on which a liquid crystal alignment film is formed spray spacers on the liquid crystal alignment film of one substrate, and make the liquid crystal alignment film surface inside. Examples include a method of bonding the other substrate and injecting the liquid crystal under reduced pressure, or a method of sealing the liquid crystal after dropping the liquid crystal on the liquid crystal alignment film surface on which the spacers are dispersed, and the like. .
  • the thickness of the spacer at this time is preferably 1 to 30 ⁇ m, more preferably 2 to 10 ⁇ m.
  • the liquid crystal display element produced using the liquid crystal aligning agent of the invention becomes a liquid crystal display element with reduced display unevenness caused by liquid crystal alignment unevenness generated in the ODF method.
  • ⁇ Additives> 3AMP 3-picolylamine.
  • NMP N-methyl-2-pyrrolidone.
  • BCS Butyl cellosolve.
  • N N′-dimethylformamide (as additives, lithium bromide-hydrate (LiBr ⁇ H 2 O) 30 mmol / L, phosphoric acid / anhydrous crystal (o-phosphoric acid) 30 mmol / L, tetrahydrofuran ( THF) is 10 ml / L),
  • Flow rate 1.0 ml / min
  • Standard sample for preparing a calibration curve TSK standard polyethylene oxide (molecular weight: about 9,000,150,000, 100,000, 30,000) manufactured by Tosoh Corporation, and polyethylene glycol (molecular weight: about 12,000, 4) manufactured by Polymer Laboratory , 1,000, 1,000).
  • the imidation rate is determined based on protons derived from structures that do not change before and after imidation as reference protons, and the peak integrated value of these protons and proton peaks derived from NH groups of amic acid appearing in the vicinity of 9.5 to 10.0 ppm. It calculated
  • x is the proton peak integrated value derived from the NH group of the amic acid
  • y is the peak integrated value of the reference proton
  • ⁇ is the proton of the NH group of the amic acid in the case of polyamic acid (imidation rate is 0%). This is the ratio of the number of reference protons to one.
  • Imidization rate (%) (1 ⁇ ⁇ x / y) ⁇ 100
  • a liquid crystal aligning agent is spin-coated on the ITO surface of the ITO electrode substrate on which an ITO electrode pattern having a pixel size of 100 ⁇ m ⁇ 300 ⁇ m and a line / space of 5 ⁇ m is formed, and dried on an 80 ° C. hot plate for 90 seconds, and then 200 Baking was performed for 20 minutes in a hot air circulation oven at 0 ° C. to form a liquid crystal alignment film having a thickness of 100 nm. Further, a liquid crystal aligning agent was spin-coated on the ITO surface of an ITO electrode substrate (with no electrode pattern formed) with a 3.3 ⁇ m photo spacer, dried on a hot plate at 80 ° C. for 90 seconds, and then heated at 200 ° C. Baking was performed for 20 minutes in a hot-air circulating oven to form a liquid crystal alignment film having a thickness of 100 nm.
  • a sealant (solvent type photocuring type) is applied on the liquid crystal alignment film of one of the two substrates using a dispenser device (manufactured by Musashi Engineering Co., Ltd., FAD630), and PSA negative liquid crystal MLC-3023 (Merck's product name) was dropped 6 points on the liquid crystal alignment film.
  • this substrate and the other substrate were bonded together in a vacuum, and the sealing material was UV cured to fill the liquid crystal. Thereafter, with a DC voltage of 15 V applied, UV through a cut filter of 325 nm or less was irradiated at 15 J / cm 2 to produce a liquid crystal cell for evaluating liquid crystal alignment unevenness.
  • the sealing compound (solvent type thermosetting type epoxy resin) was printed from on it.
  • the surface of the other substrate on which the liquid crystal alignment film was formed was faced inward and bonded to the previous substrate, and then the sealing agent was cured to produce an empty cell.
  • MLC-3023 was injected into this empty cell by a reduced pressure injection method to produce a liquid crystal cell.
  • the voltage holding ratio (VHR) of this liquid crystal cell was measured.
  • Example 1 BODA (3.15 g, 12.6 mmol), DA-1 (4.00 g, 10.5 mmol), DA-2 (0.45 g, 4.2 mmol), DA-3 (2.46 g, 6.30 mmol), was dissolved in NMP (40.2 g) and reacted at 60 ° C. for 3 hours. Then, CBDA (1.58 g, 8.06 mmol) and NMP (6.4 g) were added, and the mixture was reacted at 40 ° C. for 10 hours. An acid solution was obtained.
  • NMP 29.0 g
  • polyimide powder A 3.0 g
  • 3AMP 1 mass% NMP solution
  • BCS 15.0g
  • NMP 29.0 g
  • polyimide powder B 3.0 g
  • 3AMP 1 mass% NMP solution
  • BCS 15.0g
  • NMP 29.0 g
  • 3AMP 1 mass% NMP solution
  • BCS 15.0g
  • NMP 29.0 g
  • polyimide powder D 3.0 g
  • 3AMP 1 mass% NMP solution
  • BCS 15.0g
  • the liquid crystal alignment film obtained from the liquid crystal aligning agent of the example is more uneven in the liquid crystal alignment generated in the liquid crystal cell than the liquid crystal alignment film obtained from the liquid crystal aligning agent of the comparative example. Is reduced and the voltage holding ratio is high.
  • the liquid crystal aligning agent of the present invention can reduce display unevenness caused by liquid crystal alignment unevenness because the liquid crystal alignment film obtained in the above has a wide range of high-definition liquid crystal TVs, large or small display monitors, smartphones, tablets, etc. It is useful in the display element.

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Abstract

L'invention concerne un agent d'alignement de cristaux liquides servant à obtenir un film d'alignement de cristaux liquides permettant de réduire des irrégularités de cristaux liquides générées dans un système ODF et analogue. Un agent d'alignement de cristaux liquides est caractérisé en ce qu'il contient au moins un type de polymère sélectionné dans le groupe constitué par : un acide polyamique obtenu par réaction d'un constituant dianhydride d'acide tétracarboxylique et un constituant diamine contenant une diamine ayant une structure d'éther couronne et un anneau aromatique, et une diamine ayant une chaîne latérale pour exprimer un angle de pré-inclinaison de cristaux liquides ; et un polyimide obtenu par imidisation de l'acide polyamique.
PCT/JP2016/088539 2015-12-25 2016-12-22 Agent et film d'alignement de cristaux liquides, et élément d'affichage à cristaux liquides Ceased WO2017111117A1 (fr)

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CN114958393A (zh) * 2022-06-16 2022-08-30 长沙道尔顿电子材料有限公司 一种含氮芳香环结构聚酰胺酸液晶取向剂和液晶取向膜及其制备方法

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WO2019189632A1 (fr) * 2018-03-30 2019-10-03 日産化学株式会社 Agent d'alignement de cristaux liquides, film d'alignement de cristaux liquides et élément d'affichage à cristaux liquides
CN110643374B (zh) * 2019-09-27 2023-01-13 江苏三月科技股份有限公司 一种液晶取向剂、液晶取向膜以及液晶显示元件
CN111763518B (zh) * 2020-06-12 2021-11-12 江苏三月科技股份有限公司 一种液晶取向剂、液晶取向膜及其液晶显示元件
CN112877079A (zh) * 2020-12-03 2021-06-01 深圳清荷科技有限公司 一种液晶取向剂、液晶取向膜以及液晶显示元件
CN116478396B (zh) * 2022-01-14 2024-05-07 天津工业大学 一种用于盐湖提锂的二苯并-14-冠-4聚酰胺的制备方法
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CN117987155A (zh) * 2024-02-02 2024-05-07 深圳市道尔顿电子材料股份有限公司 低温固化液晶取向剂、液晶取向膜及其制备方法和液晶表示元件

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