Classifications

• • 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
  • 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
  • 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
  • C08G73/1003—Preparatory processes
  • C08G73/1007—Preparatory processes from tetracarboxylic acids or derivatives and diamines
• • 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
  • C08G73/1046—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
  • C08G73/1078—Partially aromatic polyimides wholly aromatic in the diamino moiety
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
  • C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
  • C08J5/18—Manufacture of films or sheets
• • 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
  • C09K19/542—Macromolecular compounds
• • 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
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
  • C08J2379/00—Characterised by the use 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 C08J2361/00 - C08J2377/00
  • C08J2379/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
  • C08J2379/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors

Definitions

• Liquid crystal aligning agent Liquid crystal aligning agent, liquid crystal aligning film and liquid crystal display device using the same
• the present invention relates to a liquid crystal aligning agent, a liquid crystal aligning film and a liquid crystal display device using the same.
• a liquid crystal device includes, for example, a liquid crystal layer sandwiched between an element substrate and a color filter substrate, a pixel electrode and a common electrode that apply an electric field to the liquid crystal layer, an alignment film that controls the alignment of liquid crystal molecules in the liquid crystal layer, It is equipped with a thin film transistor, etc. that switches the electrical signals supplied to the pixel electrodes.
• the liquid crystal molecules can be driven by vertical electric field methods such as the Ting method and the eight method, and method, (Fringe field switching) A horizontal electric field method such as a method is known.
• a photoalignment method As a liquid crystal alignment treatment method that replaces the rubbing treatment, a photoalignment method is known, which imparts liquid crystal alignment ability by irradiating polarized radiation.
• As liquid crystal alignment treatment by the photo-alignment method there have been proposed a photo-isomerization reaction, a photo-crosslinking reaction, and a photo-decomposition reaction (see Non-Patent Document 1 and Patent Document 1). ).
• ⁇ 2020/175559 2 (: 170? 2020/007779
• a liquid crystal alignment film which is a component of a liquid crystal display element, is a film for uniformly aligning liquid crystals, but various properties are required in addition to the alignment uniformity of liquid crystals. For example, charges are accumulated in the liquid crystal alignment film due to the voltage that drives the liquid crystal, and the afterimage or image sticking (hereinafter referred to as the residual aperture (hereinafter referred to as afterimage of 3)) affects the display, and the display quality of the liquid crystal display element is significantly degraded. Therefore, a liquid crystal aligning agent that overcomes these problems has been proposed (see Patent Document 2).
• Patent Document 3 discloses a specific liquid crystal aligning agent.
• Patent Document 4 discloses a liquid crystal aligner that maintains good liquid crystal orientation and has good adhesion to the sealant. ing.
• Patent Document 1 Japanese Patent Laid-Open No. 9-2 9 7 3 13
• Patent Document 2 International Publication No. 205/0 8 3 5 0 4 Panfret
• Patent Document 3 International Publication No. 2 0 15/0 5 0 1 3 5 Panfret
• Patent Document 4 International Publication No. 2 0 15/0 6 0 3 6 0 Pamphlet Non-Patent Document
• Non-Patent Document 1 "Liquid Crystal Photo-Alignment Film” Kidowaki, Ichimura Functional Materials 199 9 Jan. Jan. V ⁇ ⁇ . 17, N 0. Overview
• the present invention has been made in view of the above circumstances, and liquid crystal alignment film having good liquid crystal alignment property and good adhesiveness with a sealing agent, and adhesive property between liquid crystal alignment film and a sealing agent. It is a major object of the present invention to provide a liquid crystal aligning agent capable of obtaining a liquid crystal display device exhibiting good display quality because the frame can be narrowed because it is excellent.
• the present inventor has conducted extensive studies and found that the above problems can be solved by using a liquid crystal aligning agent containing a polymer component having a specific repeating unit, and completed the present invention. Came to do.
• the gist of the present invention is as follows.
• monovalent organic group having from 1 to 6, or Ri phenyl group der may be the same or different, and at least one of them represents a group other than a hydrogen atom in the above definition.
• the following formula (1 1) represents a divalent organic group having a partial structure represented by ⁇ 2020/175 559 4 (: 170? 2020/007779
• (Say yes 2 is a tetravalent organic group having 5 or more-membered ring alicyclic structure.
• the liquid crystal aligning film has good liquid crystal aligning property and good adhesiveness with the sealant, and the liquid crystal aligning film has good adhesiveness with the sealant. Since it is good, it is possible to further narrow the frame, and a liquid crystal display element having good display quality can be obtained.
• the liquid crystal aligning agent of the present invention contains a polymer () having a repeating unit represented by the above formula (1), the above formula (2), the above formula (3) and the above formula (4). With such a structure, a liquid crystal alignment film with less generation of afterimage can be obtained, and a liquid crystal display device having excellent contrast can be obtained.
• alkyl group having 1 to 6 carbon atoms in are a methyl group, an ethyl group, a propyl group, a propyl group, a 1-1 butyl group, a butyl group, a £-butyl group, a 1-butyl group. , —Pentyl group and the like.
• alkenyl group having 2 to 6 carbon atoms include a vinyl group, a propenyl group, afugyl group and the like, and these may be linear or branched.
• alkynyl group having 2 to 6 carbon atoms include an ethynyl group, a 1-propynyl group, a 2-propynyl group and the like. the above
• Examples of the halogen atom in 4 include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.
• Examples of the C 1-6 monovalent organic group containing a fluorine atom include a fluoromethyl group and a trifluoromethyl group. From the viewpoint of high photoreactivity, Is a hydrogen atom or a methyl group,
• At least one of is a methyl group, and more preferably at least two of are a methyl group. More preferred is This is the case.
• Specific examples of the monovalent organic group substituting any hydrogen atom on the benzene ring in the above formula (1 to 1) include a halogen atom, an alkyl group having 1 to 6 carbon atoms, and 2 to 2 carbon atoms. Examples thereof include an alkenyl group having 6 carbon atoms, an alkynyl group having 2 to 6 carbon atoms, and a monovalent organic group having 1 to 6 carbon atoms and containing a fluorine atom, and examples thereof include the structures exemplified in 1 to 4 above.
• the polymer (8) has a repeating unit represented by the above formula (2) from the viewpoint of improving heat resistance.
• the tetravalent organic group represented by formula (2) 2 is preferably a tetravalent organic group having a 5- to 8-membered alicyclic structure, and a 5- to 7-membered alicyclic structure. More preferably, it is a valent organic group.
• the alicyclic structure to which the imido group is bonded is a polycyclic structure
• the five-membered or more alicyclic structure means the atoms constituting the ring in each ring included in the polycyclic structure. It shows that all numbers are 5 or more.
• the alicyclic structure may be bonded to at least one of the two imido groups, and may have a chain hydrocarbon structure or an aromatic ring structure together with the alicyclic structure.
• Preferred examples of say yes 2 the following formula (say yes 2 - 1) - include tetravalent organic group represented by either Neu deviation - (1 2 say yes 2). ⁇ 2020/175 559 8 ⁇ (: 170? 2020/007779
• the two of (2) to (4) of (2) to (2) of (2) Is more preferable.
• Preferred specific examples of the second item in the above formula (2) are the same as the preferred specific examples of the second item in the above formula (1).
• the polymer () is (3) the total of the repeating units represented by the above formula (1) and the repeating units represented by the above formula (2) is defined as all repeating units from the viewpoint of less afterimage.
• the content is preferably 1 to 95 mol %, more preferably 5 to 90 mol %.
• the ratio ((1): (2)) of the repeating unit represented by the above formula (1) and the repeating unit represented by the above formula (2), which the polymer () has, is 70:3.
• ⁇ ⁇ 9 9: 1 is preferable, 7 5: 2 5 ⁇ 98: 2 is more preferable,
• the polymer (8) is represented by the repeating unit represented by the above formula (3) and the above formula (4) from the viewpoint of enhancing the contrast and seal adhesion of the liquid crystal display device. ⁇ 2020/175 559 9 (: 170? 2020/007779
• the polymer () is preferably (3) a total of repeating units represented by the above formula (3) and repeating units represented by the above formula (4), from the viewpoint of less afterimage, with respect to all repeating units. Is more preferably 5 to 99 mol %, and particularly preferably 10 to 95 mol %.
• the ratio ((3):(4)) of the repeating unit represented by the above formula (3) and the repeating unit represented by the above formula (4), which the polymer () has, is 70:30 to It is preferably 99:1, more preferably 75:25 to 98:2, and even more preferably 80:20 to 97:3.
• the polymer () has a repeating unit represented by the above formula (1) and the above formula (1)
• the ratio ((1):(3)) to the repeating unit represented by 3) is preferably 1:9 9 to 99:1, more preferably 5:95 to 80:20, It is more preferably 10:90 to 70:30.
• the ratio ((2): (4)) to the repeating unit represented by 4) is preferably 1:9 9 to 99:1, more preferably 5:95 to 80:20, It is more preferably 10:90 to 70:30.
• the polymer (8) is the total of repeating units represented by the above formula (1), formula (2), formula (3) and formula (4) On the other hand, the content is preferably 6 to 100 mol %, and particularly preferably 15 to 100 mol %.
• the polymer (8) is selected from the group consisting of repeating units represented by the following formula (5) and repeating units represented by the following formula (6). It may have at least one type of repeating unit selected. ⁇ 02020/175559 10 (: 17 2020 /007779
• 5 , 5 and 6 are each independently represented by a divalent organic group having a partial structure represented by the following formula (“ _ 1) or the following formula (“ _2) Ru
• X 6 in the formula (6) is Ru say yes 2 synonymous der of the formula (2).
• any (_ 0 1 to 1 2 ) of _ 0 1 to 1 2 — is not adjacent to each other, 10 1, 100 1, 1, 100 1, 1 -, -N0 900 _ , _ ⁇ ⁇ ⁇ 9 _ , _ ⁇ 9 ⁇ ⁇ ⁇ 10 _ , _ ⁇ 9 ⁇ ⁇ ⁇ _ , or _ ⁇ ⁇ ⁇ 001 is a group that can be replaced.
• ⁇ 9 and ⁇ 10 each independently represent a hydrogen atom or a monovalent organic group.
• [ 5 ] and [ 6 ] include:
• the polymer () further has the following formula: It may have at least one kind of repeating unit selected from the group consisting of the repeating unit represented by I — 8 — 1) and the repeating unit represented by (_ 1 ).
• tetravalent organic group represented by the following formula (9) other tetravalent organic groups exemplified by say yes 2 in the formula (2), the following formula (X ⁇ - 1) ⁇ ( 1 _ 1 3)), a tetravalent organic group represented by any one of (1) to (3), a tetravalent organic group derived from an aromatic tetracarboxylic acid dianhydride, and the like.
• the aromatic tetracarboxylic dianhydride that gives the tetravalent organic group of X ! is an acid obtained by intramolecular dehydration of a carboxyl group bonded to an aromatic ring such as a benzene ring or a naphthalene ring. It is a dianhydride.
• a tetravalent organic group represented by either can be mentioned.
• alkyl group having 1 to 5 carbon atoms include a methyl group, an ethyl group, a propyl group, a propyl group, a 1-1 _butyl group, a butyl group, a%-butyl group, I -Butyl group, clo-pentyl group and the like. From the viewpoint of ease of imidization by heating, Is preferably a hydrogen atom or a methyl group.
• alkyl group having 1 to 10 carbon atoms having 8 ⁇ and 8 12 above include
• alkenyl group having 8 to 12 carbon atoms and having 2 to 10 carbon atoms include vinyl group and propene group. ⁇ 2020/175559 17 ⁇ (: 170? 2020/007779 Ru group, Sanchezyl group, and the like, which may be linear or branched. Above / ⁇ ⁇ 2 of alkynyl group having 2 to 10 carbon atoms Specific examples include an ethynyl group, a 1-propynyl group, a 2-propynyl group and the like.
• a substituent May have a substituent, and examples of the substituent include a halogen atom (fluorine atom, chlorine atom, bromine atom, iodine atom), a hydroxyl group, a cyano group, an alkoxy group and the like.
• a halogen atom fluorine atom, chlorine atom, bromine atom, iodine atom
• a hydroxyl group a cyano group
• an alkoxy group and the like.
• the ratio ((5):(6)) of the polymer containing the repeating unit represented by the above formula (5) and the repeating unit represented by the above formula (6) is 7
• the ratio is preferably 0:30 to 99:1, more preferably 75:25 to 98:2, and even more preferably 80:20 to 97:3.
• the polymer () has the repeating unit represented by the formula (5) and the formula (5)
• the total of repeating units represented by 6) is preferably 1 to 40 mol%, more preferably 1 to 30 mol%, based on all the repeating units of the polymer (). It is preferably 5 to 30 mol %.
• the total number of repeating units represented by the above formula (1), formula (2), formula (3) and formula (4) is 6 to 99 mol based on all the repeating units of the polymer (). %, more preferably 15 to 99 mol%,
• the liquid crystal aligning agent of the present invention is a composition containing the polymer () and an organic solvent, and the polymer () having a different structure may contain two or more kinds. Further, the liquid crystal aligning agent of the present invention may contain a polymer other than the polymer () (hereinafter, also referred to as a second polymer) and various additives.
• the content ratio of the polymer () to all the polymer components is preferably 5% by mass or more, and preferably 5 to 95% by mass. , And more preferably 10 to 90% by mass.
• Examples of the second polymer include polyamic acid, polyimide, polyamic acid ester, polyester, polyamide, polyurea, and polyorganosiloxane. ⁇ 2020/175 559 18 ⁇ (: 170? 2020/007779
• a polyamic acid obtained from a tetracarboxylic dianhydride component and a diamine component (hereinafter, also referred to as a second polyamic acid) is preferable as the second polymer.
• the tetracarboxylic acid dianhydride component for obtaining the second polyamic acid a compound represented by the following formula (11) can be mentioned.
• the tetracarboxylic acid dianhydride component may be composed of two or more kinds of compounds.
• (81 1) and (81 2) are preferable from the viewpoint of further improving the photo-alignment property, and (81 4) is from the viewpoint of further improving the relaxation rate of accumulated charges.
• (81-15) to (81-17) and the like are preferable from the viewpoint of further improving the liquid crystal orientation and the relaxation rate of accumulated charges.
• the diamine component for obtaining the second polyamic acid can be appropriately determined according to the purpose, and for example, a diamine represented by the following formula (12) can be used.
• ( 9 represents a divalent organic group.
• the two 9 are each independently a hydrogen atom or an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, or 2 to 5 carbon atoms.
• 5 is a alkynyl group.
• eight 9 is a hydrogen atom or a methylation group.
• the carbon atom 9 is a divalent organic group having a secondary or tertiary nitrogen atom, or
• diamine represented by the formula (1 2) in the case where 9 is a divalent organic group having a secondary or tertiary nitrogen atom include any of the following (3) to ().
• the diamine of the above is mentioned.
• the two 2 are each independently a single bond or a group.
• ! _, _ ⁇ (01 ⁇ 1 2) m ⁇ _, _ Rei_rei_1 ⁇ 1 to 1 _, and _1 ⁇ 11-1 Represents a divalent organic group selected from _ ((01, 01 represents an integer of 1 to 5), *1 represents a site bonded to the benzene ring in the formula (
• a diamine having a carbazole structure described in ( ⁇ ) 0201 8/1 10354 preferably a diamine having a structure represented by the following formula ( ⁇ ).
• X is a biphenyl ring or a fluorene ring.
• ⁇ is a benzene ring, a biphenyl ring, or a group selected from the group consisting of 11 and 11 represents a phenylene group. It is a divalent group represented by 10 1 to 1 2 —, — 30 2 — % — 0 (0 1 to 1 3 ) 2 — or 1 0 (0 3 ) 2 —.
• 8 1 is 1 1 ⁇ 1 !--- ⁇ ⁇ 1 1 ⁇ 1 1 to 1 -, - ⁇ _1 ⁇ 1 2 alkylene group with carbon number 2-2 0 - at least _ one but one 1 ⁇ 1-hundred one 1-substituted group in the 1-, or an alkylene group having a carbon number of 2-2 0
• 1 ⁇ 1 1 ⁇ 1 _, and at least _ of the other _ 0 1 ⁇ 1 2 — are 101, _ ⁇ —, 100 001, 1 [3 ⁇ 4 ⁇ 001 ([ 3 ⁇ 4 represents a hydrogen atom or a methyl group.),
• Eighty- two represents a halogen atom, a hydroxy group, or an alkyl group or an alkoxy group having 1 to 5 carbon atoms (any hydrogen atom of the above alkyl group or alkoxy group may be substituted with a halogen atom).
• 3 is an integer from 0 to 4, and when 3 is 2 or more, 8 2 may be the same or different.
• 13 and ⁇ are integers of 1 or 2.
• ⁇ 02020/175559 25 (: 17 2020/007779 is a diamine represented by any one of the following formulas (closure 3-1) to (n 3-7), the following formula (1 ⁇ 4-1) ⁇ Examples include diamines represented by any of (1 ⁇ 4-6).
• a diamine having a carboxyl group (OO 1 to 1 group) or a hydroxyl group (O 1 to 1 group) can also be used. Specifically, 2,
• benzyl alcohol 2,4-diaminobenzyl alcohol, 4,6-diaminoresorcinol, 2,4-diaminobenzoic acid, 2,5-diaminobenzoic acid or 3,5-diaminobenzoic acid.
• 2,4-diaminobenzoic acid, 2,5-diaminobenzoic acid and 3,5-diaminobenzoic acid are preferable.
• diamines represented by the following formulas [313-1] to [31 ⁇ -4], or diamines in which these amino groups are secondary amino groups can also be used.
• 0 1 is a single bond, _ ⁇ 1 to 1 2 — , _ ⁇ 2 1 to 1 4 — , — 0 (01 to 1 3 )
• ⁇ 2 represents a linear or branched aralkyl Killen group 5 1 carbon atoms, 5 represents an integer of 1 to 5.
• 0 3 and 0 4 are each independently a single bond, Ten 2 1 - 1 4 -, -0 (Rei_1 ⁇ 1 3) 2 -
• the diamine component for obtaining the second polyamic acid the diamine used for obtaining the polymer (8) or a known diamine can be used in addition to the above.
• the diamine component for obtaining the second polyamic acid may be a combination of two or more kinds of diamines.
• Polyamic acid ester, polyamic acid, and polyimide which are the polyimide precursors used in the present invention, are, for example, It can be produced by a known method such as that described in No. 7586.
• the liquid crystal aligning agent of the present invention may contain the polymer () and, if desired, the second polymer, and in addition to these, other polymers.
• Other polymers include polyamic acid, polyimide, polyamic acid ester, polyester, polyamide, polyurea, polyorganosiloxane, cellulose derivative, polyacetal, polystyrene or its derivative, poly(styrene-phenylmaleimide) derivative, poly( (Meth) acrylate etc. can be mentioned.
• the liquid crystal aligning agent is used to prepare a liquid crystal aligning film, and takes the form of a coating liquid from the viewpoint of forming a uniform thin film.
• the liquid crystal director of the present invention is also preferably a coating liquid containing the above-mentioned polymer component and an organic solvent.
• the concentration (content) of the polymer in the liquid crystal aligning agent can be appropriately changed by setting the thickness of the coating film to be formed. From the viewpoint of forming a uniform and defect-free coating film, 1% by mass or more is preferable, and from the viewpoint of storage stability of the solution, 10% by mass or less is preferable. A particularly preferred polymer concentration is 2 to 8% by mass.
• the organic solvent contained in the liquid crystal aligning agent is not particularly limited as long as it is a solvent in which the polymer component is uniformly dissolved (also referred to as a good solvent).
• a solvent in which the polymer component is uniformly dissolved also referred to as a good solvent.
• the good solvent is preferably 20 to 99 mass% of the entire solvent contained in the liquid crystal aligning agent, more preferably 20 to 90 mass%, and particularly preferably 30 to 80 mass%. Is.
• the organic solvent contained in the liquid crystal aligning agent is, in addition to a good solvent, a solvent (also referred to as a poor solvent) that improves the coatability when applying the liquid crystal aligning agent and the surface smoothness of the coating film. It is preferable to use a mixed solvent used in combination. Specific examples of the poor solvent are shown below, but the invention is not limited to these examples.
• diisopropyl ether diisoptyl ether, diisoptyl carbinol (2, 6-dimethyl-4-heptanol), ethylene glycol dimethyl ether, ethylene glycol dityl ether, ethylene glycol dibutyl ether.
• diisoptyl carpinol propylene glycol monoptyl ether, propylene glycol diacetate, propylene glycol diethyl ether, dipropylene glycol monomethyl ether, and di propylene glycol dimethyl ether are preferred.
• Ether 4-hydroxy_4-methyl-2-pentanone, ethylene glycol monoptyl ether, ethylene glycol monoptyl ether acetate, and diisobutyl ketone are preferred.
• the amount of these poor solvents is preferably 1 to 80% by mass, more preferably 10 to 80% by mass, and particularly preferably 20 to 70% by mass, based on the whole solvent contained in the liquid crystal aligning agent.
• the type and content of such a solvent are appropriately selected depending on the coating apparatus for the liquid crystal aligning agent, coating conditions, coating environment, and the like.
• the liquid crystal aligning agent of the present invention may additionally contain components other than the polymer component and the organic solvent.
• additional component include an adhesion aid for increasing the adhesion between the liquid crystal alignment film and the substrate and the adhesion between the liquid crystal alignment film and the sealing material, and a compound for increasing the strength of the liquid crystal alignment film (hereinafter referred to as crosslinking Also referred to as a polar compound.), a dielectric or a conductive substance for adjusting the dielectric constant or electric resistance of the liquid crystal alignment film.
• crosslinkable compound examples include: oxiranyl group, oxetanyl group, protected isocyanate group, protected isothiocyanate group, oxazoline ring structure-containing group, and meldrumic acid, from the viewpoint of less afterimage generation and high effect of improving film strength.
• ( 871 is a hydrogen atom, an alkyl group having 1 to 3 carbon atoms or Is.
• [3 ⁇ 4 72 and [3 ⁇ 4 73 are each independently a hydrogen atom, an alkyl group having 1 to 3 carbon atoms or G*_CH 2 — ⁇ H]. * Indicates a bond. Represents an organic group having an aromatic ring and having a valence of 0. A door represents an integer from 0 to 4.
• Specific examples of the compound having a protected isocyanate group include compounds having two or more protected isocyanate groups described in JP-A No. 2014-224978, [0046] to [0047], No. 4 1 598, which has three or more protected isocyanate groups described in [01 19] to [01 20] ⁇ 02020/175 559 32 (: 17 2020 /007779
• Examples include compound. Of these, compounds represented by any of the following formulas (13-1) to (3-1) are preferable.
• Specific examples of the compound having a group containing an oxazoline ring structure include the compounds containing two or more oxazoline structures described in [01 15] of Japanese Patent Laid-Open No. 2007-286597.
• Examples thereof include compounds having two or more Meldrum's acid structures described in 2/09 1 088.
• Specific examples of the compound having a cyclocarbonate group include the compounds described in ⁇ / ⁇ 201 1/1 55577.
• Examples thereof include a methyl group, an ethyl group and a propyl group.
• Examples thereof include a (01+11)-valent organic group having an aromatic hydrocarbon group bonded directly or via a linking group, and a (111+11)-valent group having an aromatic heterocycle.
• the aromatic hydrocarbon group include benzene and naphthalene.
• the aromatic heterocycle include a pyrrole ring, an imidazole ring, a pyrazole ring, a pyridine ring, a pyrimidine ring, a quinoline ring, an isoquinoline ring, a carbazole ring, a pyridazine ring, a pyrazine ring, a benzimidazole ring, a benzimidazole ring, and an indole.
• linking group examples include an alkylene group having 1 to 10 carbon atoms, a group obtained by removing one hydrogen atom from the above alkylene group, a divalent or trivalent cyclohexane ring, and the like. Any hydrogen atom of the above alkylene group may be substituted with a fluorine atom or an organic group such as a trifluoromethyl group. Specific examples include the compounds described in ⁇ / ⁇ 201 0/074269. Preferred specific examples include any of the following formulas (6-1) to (6-9).
• the above compound is an example of a crosslinkable compound, and is not limited to these.
• components other than the above disclosed in [01 05] to [01 16] of ⁇ / ⁇ 201 5/060357 can be mentioned.
• the liquid crystal display of the present invention ⁇ 2020/175 559 35 ⁇ (: 170? 2020/007779
• Two or more kinds of the crosslinkable compounds contained in the stimulant may be combined.
• the content of the crosslinkable compound is preferably 0.5 to 20 parts by mass with respect to 100 parts by mass of the polymer component contained in the liquid crystal aligning agent. From the viewpoint that the reaction proceeds and the intended effect is exhibited, and the generation of afterimage is small, it is more preferably from 1 to 15 parts by mass.
• adhesion aid examples include, for example, 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, 3-aminopropylgetoxymethylsilane, 2-aminopropyltrimethoxysilane, 2-aminopropyltriethoxysilane, 1 ⁇ 1— (2-aminoethyl) 1-aminopropyltrimethoxysilane, 1 ⁇ !— (2-aminoethyl) 1 3-aminopropylmethyldimethoxysilane, 3-ureidopropyltrimethoxysilane, 3-ureidopropyltrie Toxylsilane, 1 ⁇ !—Ethoxycarbonyl-3-aminopropyl trimethyloxysilane, 1 ⁇ 1—Ethoxycarbonyl-3—aminopropyltrioxysilane, 1 ⁇ 1 _ Triethoxysilylpropyltriethylene triamine, 1 ⁇ 1 ⁇ 1
• Examples include silane coupling agents such as 3-mercaptopropylmethyldimethoxysilane, 3-mercaptopropyltrimethoxysilane, and 3-isocyanatopropyltriethoxysilane.
• the amount of these silane coupling agents used is preferably from 0.1 to 30 parts by mass with respect to 100 parts by mass of the polymer component contained in the liquid crystal aligning agent, from the viewpoint of less occurrence of afterimages. More preferably, it is 0.1 to 20 parts by mass.
• the liquid crystal alignment film using the liquid crystal alignment agent of the present invention can be produced by the known method for obtaining a liquid crystal alignment film from the liquid crystal alignment agent using the liquid crystal alignment agent of the present invention.
• the liquid crystal alignment film using the liquid crystal aligning agent of the present invention is more efficient by sequentially performing the following step (1), step (2), step (3), and preferably step (4) Can be manufactured in a simple manner.
• the substrate to which the liquid crystal aligning agent is applied is not particularly limited as long as it is a highly transparent substrate, and a glass substrate, a silicon nitride substrate, a plastic substrate such as an acrylic substrate or a polycarbonate substrate, or the like can also be used. At that time, it is preferable to use a substrate on which electrodes for driving the liquid crystal are formed in order to simplify the process.
• an opaque material such as a silicon wafer can be used for the substrate on one side, and in this case, a material that reflects light such as aluminum can also be used for the electrode.
• the liquid crystal aligning agent is generally applied industrially by screen printing, offset printing, flexographic printing or ink jet method. That ⁇ 2020/175 559 37 ⁇ (: 170? 2020 /007779
• coating methods include a dip method, a mouth coater method, a slit coater method, a spinner method or a spray method, and these may be used depending on the purpose.
• Step (2) is a step of heating the coating film of the liquid crystal aligning agent obtained in step (1).
• the solvent can be evaporated and the amic acid or amic acid ester in the polymer can be thermally imidized by a heating means such as an (infrared) type oven.
• the drying and baking steps after applying the liquid crystal aligning agent can be performed at any temperature and time, and may be performed plural times.
• the temperature at which the organic solvent of the liquid crystal aligning agent is removed can be, for example, 40 to 150 ° . From the viewpoint of shortening the process, it may be carried out at 40 to 120 ° .
• the firing time is not particularly limited, but may be 1 to 10 minutes or 1 to 5 minutes.
• the amic acid or amic acid ester in the polymer is subjected to thermal imidization, after the step of removing the above organic solvent, it is baked at , for example, 1 90 to 250 ° ⁇ or 200 to 240 ° ⁇ . be able to.
• the firing time is not particularly limited, but may be 5 to 40 minutes or 5 to 30 minutes.
• Step (3) is the step of irradiating the film obtained in step (2) with polarized ultraviolet light.
• the wavelength of ultraviolet rays is 200 to 400 n And more preferably 200 ⁇ 300 n m.
• the substrate coated with the liquid crystal alignment film may be irradiated with ultraviolet rays while being heated at 50 to 250 ° .
• the dose of the above radiation is 1 to 10,000. Is preferred, 100 to 5, 0 Is more preferable.
• the liquid crystal alignment film thus produced can stably align liquid crystal molecules in a certain direction.
• the extinction ratio of linearly polarized ultraviolet light is preferably 10:1 or more, more preferably 20:1 or more. ⁇ 2020/175 559 38 ⁇ (: 170? 2020 /007779
• Step (4) is a step of baking the film obtained in step (3) at a temperature of 100 ° C. or higher and higher than that in step (2).
• Firing temperature, in 1 0 0 ° ⁇ As, and, higher than the firing temperature in step (2) is not particularly limited, but is preferably 1 5 0 to 3 0 0 ° ⁇ , 1 5 0-2 5 0° is more preferable, and 200 to 250° is further preferable.
• the firing time is preferably 5 to 120 minutes, more preferably 5 to 60 minutes, and further preferably 5 to 30 minutes.
• the thickness of the liquid crystal alignment film after firing is too thin, the reliability of the liquid crystal display element may decrease, so Is preferable, and 10 to 200 n is more preferable.
• the obtained liquid crystal alignment film may be subjected to contact treatment with water and/or a solvent.
• the solvent used in the above contact treatment is not particularly limited as long as it is a solvent that dissolves the decomposition product generated from the liquid crystal alignment film by irradiation with ultraviolet rays. Specific examples include water, methanol, ethanol, 2-propanol, acetone, methyl ethyl ketone, 1-methoxy_2-propanol, 1-methoxy-2-propanol acetate, butyl cellosolve, ethyl lactate, methyl lactate, diethyl.
• Acetone alcohol, methyl 3-methoxypropionate, ethyl 3-ethoxypropionate, propyl acetate, butyl acetate, cyclohexyl acetate and the like can be mentioned.
• water, 2-propanol, 1-methoxy-2-propanol or ethyl lactate is preferable from the viewpoint of versatility and solvent safety. More preferred is water, 1-methoxy-2-propanol or ethyl lactate.
• Two or more kinds of solvents may be combined.
• an immersing treatment or a spraying treatment (also referred to as a spraying treatment) can be mentioned.
• the treatment time in these treatments is preferably 10 seconds to 1 hour from the viewpoint of efficiently dissolving the decomposition product generated from the liquid crystal alignment film by ultraviolet rays.
• the solvent at the time of the contact treatment may be heated at room temperature or may be heated, but is preferably 10 to 80°C. Above all, 20 to 50°C is preferable.
• ultrasonic treatment may be performed if necessary.
• rinsing also referred to as rinsing
• a low-boiling-point solvent such as water, methanol, ethanol, 2-propanol, acetone or methyl ethyl ketone
• the firing temperature is preferably 150 to 300° C., preferably 180 to 250° C., and more preferably 200 to 230° C.
• the firing time is preferably 10 seconds to 30 minutes, more preferably 1 to 10 minutes.
• the liquid crystal alignment film of the present invention is suitable as a liquid crystal alignment film of a horizontal electric field type liquid crystal display device such as a PS system or a FFS system, and is particularly useful as a liquid crystal alignment film of a FFS system liquid crystal display device. is there.
• a liquid crystal display device is obtained by preparing a liquid crystal cell by a known method after obtaining a substrate having a liquid crystal alignment film obtained from a liquid crystal aligning agent.
• a liquid crystal display element having a passive matrix structure As an example of a method for manufacturing a liquid crystal cell, a liquid crystal display element having a passive matrix structure will be described as an example.
• a liquid crystal display element having an active matrix structure in which a switching element such as TFT (Thin Fiber Transistor) is provided in each pixel portion that constitutes image display may be used.
• TFT Thin Fiber Transistor
• a transparent glass substrate is prepared, a common electrode is provided on one substrate, and a segment electrode is provided on the other substrate.
• These electrodes can be ITO electrodes, for example, and are patterned to display a desired image.
• an insulating film is provided on each substrate so as to cover the common electrode and the segment electrode.
• the insulating film can be, for example, a S i 0 2 -T i O 2 film formed by a sol-gel method.
• a liquid crystal alignment film is formed on each substrate, one substrate is overlaid with the other liquid crystal alignment film surface facing each other, and the periphery is bonded with a sealant. Spacers are usually added to the sealant to control the substrate gap. ⁇ 2020/175 559 40 ⁇ (: 170? 2020 /007779
• the liquid crystal material is injected into the space surrounded by the two substrates and the sealing agent through the opening provided in the sealing agent, and then the opening is sealed with an adhesive.
• a vacuum injection method may be used, or a method utilizing a capillary phenomenon in the air may be used.
• the liquid crystal material either a positive type liquid crystal material or a negative type liquid crystal material may be used.
• install the polarizing plate Specifically, a pair of polarizing plates are attached to the surfaces of the two substrates opposite to the liquid crystal layer.
• the step (3) is carried out, so that the liquid crystal alignment film can be obtained in a smaller number of steps than in the past.
• the liquid crystal aligning agent of the present invention is particularly preferably used in the method for producing a liquid crystal aligning film, which comprises the step of carrying out step (3) after removing the organic solvent at 40 to 150 ° in step (2). be able to.
• liquid crystal aligning agent of the present invention it is possible to obtain a liquid crystal aligning film having a high seal adhesiveness with less generation of afterimages and 80 afterimages derived from the residual port 0.
• liquid crystal display element which is excellent in contrast and which suppresses variations in brightness in the plane during black display, and a liquid crystal display element having good display quality is obtained.
• 3-1 a compound represented by the following formula (3_1),
• Polyimide powder 2 Into an IV! sample tube (IV! Sampling tube standard, ⁇ 5 (Kusano Scientific Co., Ltd.)) and add deuterated dimethyl sulfoxide. ⁇ .05% Ding 1 ⁇ /13 (Tetramethylsilane) mixed product) (0.53 1_) was added, and ultrasonic waves were applied to completely dissolve it. This solution was used to measure 50 protons 1 ⁇ /
• the imidization rate is determined by using the proton derived from the structure that does not change before and after imidization as the reference proton, and the peak integrated value of this proton and 1 ⁇ 11 ⁇ 1 ⁇ of the amide acid appearing around 9.5 0 ⁇ 1 0.0. It was determined by the following formula using the integrated value of the proton peak derived from the group.
• X is the proton peak integrated value derived from the 1 ⁇ 11 to 1 group of amide acid, so is the peak integrated value of the reference proton, and ⁇ is the amino acid in the case of polyamidic acid (imidization rate is 0%). This is the ratio of the number of standard protons to one 1 ⁇ 11 to 1 group proton of acid.
• ⁇ is poly ⁇ 2020/175 559 43 ⁇ (: 170? 2020 /007779
• 0-8-1 is 2.059 (0. 0084 0101), and 081-1 is 4.1 69 ( 0.01 9601_Rei I) weighed, 1 ⁇ / 1? 88.6 9 by the addition of such feed the nitrogen but was stirred et al dissolved. While stirring this diamine solution Add 1 to 5.52 9 ( ⁇ 0.0246 ⁇ 101), and ⁇ 81 2 to ⁇ .359 ( ⁇ . 001 40 ⁇ 10 I), stir at 40° ⁇ for 24 hours, and mix with polyamic acid solution. (81) (Viscosity: 2 1 301 8 3) was obtained. ⁇ 2020/175 559 44 ⁇ (: 170? 2020 /007779
• the resulting reaction solution was poured into 150O!I of methanol while stirring, the deposited precipitate was collected by filtration, and the same operation was repeated twice to wash the resin powder, and then at 60 ° C. By drying for 12 hours, a polyimide resin powder was obtained. The imidation ratio of this polyimide resin powder was 71%.
• the obtained polyimide resin powder 3.609 Into an Erlenmeyer flask I, 26.49 of IV! was added so that the solid content concentration was 12%, and the mixture was stirred and dissolved at 70 ° ⁇ for 24 hours to obtain a polyimide solution (_ 1 _ I).
• the values in parentheses in Table 1 are, for the tetracarboxylic acid component, the compounding ratio (mol part) of each compound to 100 mol parts of the total amount of the tetracarboxylic acid derivative used in the synthesis, and the diamine With regard to the components, the compounding ratio (mol part) of each compound to 100 mol parts of the total amount of diamine used in the synthesis is shown. For organic solvents, the compounding ratio (parts by mass) of each organic solvent to the total amount of 100 parts by mass of organic solvent contained in the polyamic acid solution or the polyimide solution is shown.
• Examples 2 to 5 and Comparative Examples 2 and 3 were carried out in the same manner as Comparative Example 1 and Example 1 except that each polyimide solution, additive and organic solvent described in Table 2 below were used. Each liquid crystal aligning agent was obtained. The specifications of the obtained liquid crystal aligning agents are shown in Table 1 together with the liquid crystal aligning agents of Example 1 and Comparative Example 1.
• the numerical value in parentheses represents the mixing ratio (mass %) of each component to 100 parts by mass of the total amount of the liquid crystal aligning agent.
• a substrate with electrodes was prepared.
• the board is 30 ⁇ 35 in size and has a thickness of 0.7. It is a glass substrate.
• a first electrode is formed as a counter electrode, which is provided with a solid pattern and has a solid pattern. 1st layer ⁇ 2020/175 559 48 ⁇ (: 170? 2020/007779
• a 3 1 1 ⁇ 1 (silicon nitride) film formed by the XX method is formed on the counter electrode of the eye.
• the film thickness of the second layer 3 ⁇ 1 ⁇ 1 film is 5 0 0 n m, and functions as an interlayer insulating film.
• a comb-teeth-shaped pixel electrode formed by patterning the 0st film is arranged as the 3rd layer. Form one pixel. The size of each pixel is Is.
• the counter electrode of the first layer and the pixel electrode of the third layer are electrically insulated by the action of the 3rd 1 ⁇ ! film of the second layer.
• the pixel electrode of the third layer has a comb-tooth shape formed by arranging a plurality of "dogleg” shaped electrode elements each having a bent central portion.
• the width of each electrode element in the lateral direction is 30! and the spacing between the electrode elements is 60!.
• the pixel electrode that forms each pixel is configured by arranging a plurality of curved "dogleg” shaped electrode elements in the central part, so the shape of each pixel is not rectangular, but is similar to that of the electrode element. It has a shape similar to the bold "dogleg” that bends at some parts.
• Each pixel is divided into an upper part and a lower part with a central bent portion as a boundary, and has a first region on the upper side and a second region on the lower side of the bent portion.
• each substrate with a liquid crystal alignment film having a film thickness of 100 n was baked for 30 minutes in a hot-air circulation type oven at 230 °C to obtain each substrate with a liquid crystal alignment film having a film thickness of 100 n.
• the liquid crystal alignment agent prepared above was applied to a 30 ⁇ 40 substrate by spin coating. After drying for 2 minutes on a hot plate of 80 ° ⁇ , the coated surface is irradiated with 254 n of ultraviolet rays through a polarizing plate, and then heated in a hot air circulation oven at 230 ° ⁇ for 20 minutes. Firing was carried out for 1 minute to form a coating film having a film thickness of 100 nm. After preparing the two substrates thus obtained, applying a 4-bead spacer on the surface of the liquid crystal alignment film of one of the substrates, and then applying a sealant (XN-1500 ) Was added dropwise.
• the overlapping width of the substrate is 1 Were pasted together so that At that time, the diameter of the sealant after bonding
• the dropping amount of the sealing agent was adjusted so that After fixing the two bonded substrates with a clip, they were heat-cured at 150° for 1 hour to prepare a sample for evaluation of adhesion.
• the liquid crystal aligning agent of the present invention is useful for forming a liquid crystal aligning film in a wide range of liquid crystal display devices such as a three-drive system and a three-drive system.

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