WO2021177316A1 - Composition de résine durcissable, agent d'étanchéité pour éléments d'affichage, agent d'étanchéité pour éléments d'affichage à cristaux liquides, matériau conducteur vertical, élément d'affichage, adhésif pour composants électroniques, et composant électronique - Google Patents

Composition de résine durcissable, agent d'étanchéité pour éléments d'affichage, agent d'étanchéité pour éléments d'affichage à cristaux liquides, matériau conducteur vertical, élément d'affichage, adhésif pour composants électroniques, et composant électronique Download PDF

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Publication number
WO2021177316A1
WO2021177316A1 PCT/JP2021/007996 JP2021007996W WO2021177316A1 WO 2021177316 A1 WO2021177316 A1 WO 2021177316A1 JP 2021007996 W JP2021007996 W JP 2021007996W WO 2021177316 A1 WO2021177316 A1 WO 2021177316A1
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Prior art keywords
group
curable resin
resin composition
meth
liquid crystal
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PCT/JP2021/007996
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English (en)
Japanese (ja)
Inventor
剛 大浦
信烈 梁
大輝 山脇
秀幸 林
慶枝 松井
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積水化学工業株式会社
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Application filed by 積水化学工業株式会社 filed Critical 積水化学工業株式会社
Priority to CN202180006366.8A priority Critical patent/CN114667302B/zh
Priority to JP2021515229A priority patent/JP7084550B2/ja
Priority to KR1020227012228A priority patent/KR20220149651A/ko
Publication of WO2021177316A1 publication Critical patent/WO2021177316A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2/00—Processes of polymerisation
    • C08F2/46—Polymerisation initiated by wave energy or particle radiation
    • C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
    • C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F299/00—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers
    • C08F299/02—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates
    • 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
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
    • C08G59/50—Amines
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
    • C09J11/02—Non-macromolecular additives
    • C09J11/06—Non-macromolecular additives organic
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
    • 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
    • C09K3/00—Materials not provided for elsewhere
    • C09K3/10—Materials in mouldable or extrudable form for sealing or packing joints or covers
    • 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
    • G02F1/1339—Gaskets; Spacers; Sealing of cells

Definitions

  • the present invention comprises a curable resin composition, a sealant for a display element using the curable resin composition, a sealant for a liquid crystal display element, a vertical conductive material, a display element, an adhesive for an electronic component, and the like.
  • a curable resin composition a sealant for a display element using the curable resin composition
  • a sealant for a liquid crystal display element a sealant for a liquid crystal display element
  • a vertical conductive material a vertical conductive material
  • a display element an adhesive for an electronic component, and the like.
  • liquid crystal display elements In recent years, liquid crystal display elements, organic EL display elements, and the like have been widely used as display elements having features such as thinness, light weight, and low power consumption.
  • a curable resin composition is usually used for sealing a liquid crystal display or a light emitting layer, adhering various electronic components, or the like.
  • a curable resin composition As disclosed in Patent Documents 1 and 2 as a sealing agent.
  • a liquid crystal dropping method called a construction method is used. In the dropping method, first, a frame-shaped seal pattern is formed on one of the two transparent substrates with electrodes by dispensing.
  • a narrowing of the frame of the liquid crystal display unit can be mentioned.
  • the position of the seal portion is arranged under the black matrix (hereinafter, also referred to as a narrow frame design).
  • the sealant is placed directly under the black matrix, so when the dropping method is performed, the light emitted when the sealant is photocured is blocked, and the light does not reach the inside of the sealant. There was a problem that the curing was insufficient.
  • the element when irradiating the sealant with light, the element is usually exposed by covering the element with a mask so as not to damage the display element, but in recent years, the exposure can be performed without the mask.
  • a sealing agent that can be cured by irradiating visible light with low energy.
  • An object of the present invention is to provide a curable resin composition having excellent visible light curability and adhesiveness, and also excellent in low liquid crystal contamination when used as a sealant for a liquid crystal display element. Further, the present invention relates to a sealant for a display element containing the curable resin composition, a sealant for a liquid crystal display element, a vertical conductive material, a cured product of the sealant for the display element, and the liquid crystal display element. It is an object of the present invention to provide a display element having a cured product of a sealant for use or a cured product of the vertically conductive material. A further object of the present invention is to provide an adhesive for electronic components containing the curable resin composition and an electronic component bonded with a cured product of the adhesive for electronic components.
  • the present invention is a curable resin composition containing a curable resin and a photopolymerization initiator, wherein the photopolymerization initiator is a curable resin composition containing a compound represented by the following formula (1). be.
  • R 1 has an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group, an aralkyl group, a heterocyclic group, or an ether, which may independently have an ether bond or an amide bond. It is an aryl group that may have a bond or an amide bond, and the alkyl group having 1 to 20 carbon atoms, the cycloalkyl group, the aralkyl group, the heterocyclic group, and the aryl group have a polar group. You may have.
  • R 2 has an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group, an aralkyl group, a heterocyclic group, or an ether, which may independently have an ether bond or an amide bond, respectively. It is an aryl group that may have a bond or an amide bond, and the alkyl group having 1 to 20 carbon atoms, the cycloalkyl group, the aralkyl group, the heterocyclic group, and the aryl group have a polar group. You may have.
  • R 3 has an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group, an aralkyl group, a heterocyclic group, or an ether, which may independently have an ether bond or an amide bond. It is an aryl group that may have a bond or an amide bond, and the alkyl group having 1 to 20 carbon atoms, the cycloalkyl group, the aralkyl group, the heterocyclic group, and the aryl group have a polar group. You may have.
  • R 4 has the structure having a bond, an arylene group, or a structure having a hetero arylene group. The present invention will be described in detail below.
  • the curable resin composition of the present invention contains a photopolymerization initiator.
  • the photopolymerization initiator contains a compound represented by the above formula (1).
  • the curable resin composition of the present invention has excellent visible light curability and adhesiveness, and can be used as a sealant for a liquid crystal display element. When used, it is also excellent in low liquid crystal contamination.
  • R 1 is an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group, an aralkyl group, a heterocyclic group, or an alkyl group which may independently have an ether bond or an amide bond. It is an aryl group that may have an ether bond or an amide bond, and the alkyl group having 1 to 20 carbon atoms, the cycloalkyl group, the aralkyl group, the heterocyclic group, and the aryl group are polar groups. May have.
  • the alkyl group is preferably a methyl group or an ethyl group.
  • examples of the cycloalkyl group include a cyclohexyl group and a cyclobutyl group.
  • examples of the aralkyl group include a phenylmethyl group and a 2-naphthylmethyl group.
  • examples of the heterocyclic group include a 2-benzofuranyl group and the like.
  • examples of the aryl group include a phenyl group and a 1-naphthyl group. Of these, a phenyl group is preferable.
  • Examples of the polar group include a hydroxy group, a carboxyl group, an amino group and the like. Among them, when the curable resin composition of the present invention is used for adhesion of electronic parts or the like, a carboxyl group is preferable from the viewpoint that the cation component can be supplemented because the cation component increases in the surrounding environment.
  • R 2 is an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group, an aralkyl group, a heterocyclic group, or an alkyl group which may independently have an ether bond or an amide bond. It is an aryl group that may have an ether bond or an amide bond, and the alkyl group having 1 to 20 carbon atoms, the cycloalkyl group, the aralkyl group, the heterocyclic group, and the aryl group are polar groups. May have.
  • R 2 is an alkyl group
  • examples of the alkyl group include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a 2-ethylhexyl group and the like. Of these, a methyl group, an ethyl group, a propyl group, a butyl group and a pentyl group are preferable.
  • examples of the cycloalkyl group include a cyclopentyl group and a cyclohexyl group.
  • the cycloalkyl group may have an alkyl group.
  • examples of the aralkyl group include a phenylmethyl group and the like.
  • examples of the heterocyclic group include a 2-benzothiophenyl group and the like.
  • examples of the aryl group include a phenyl group and the like.
  • Examples of the polar group include a hydroxy group, a carboxyl group, an amino group and the like.
  • examples of the alkyl group having the polar group include a carboxymethyl group and a 2-carboxyethyl group.
  • examples of the cycloalkyl group having the polar group include a 2-carboxycyclohexyl group and a 2-carboxy-4-methylcyclohexyl group.
  • R 3 is an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group, an aralkyl group, a heterocyclic group, or an alkyl group which may independently have an ether bond or an amide bond. It is an aryl group that may have an ether bond or an amide bond, and the alkyl group having 1 to 20 carbon atoms, the cycloalkyl group, the aralkyl group, the heterocyclic group, and the aryl group are polar groups. May have.
  • examples of the alkyl group include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a 2-ethylhexyl group and the like. Of these, a methyl group, an ethyl group, a propyl group, a butyl group and a pentyl group are preferable.
  • the alkyl group may have an aryl group.
  • examples of the cycloalkyl group include a cyclohexyl group.
  • examples of the aralkyl group include a 2-naphthylmethyl group and the like.
  • examples of the heterocyclic group include a 2-thienyl group and the like.
  • examples of the aryl group include a phenyl group and the like.
  • Examples of the polar group include a hydroxy group, a carboxyl group, an amino group and the like.
  • a carboxyl group is preferable from the viewpoint that the cation component can be supplemented because the cation component increases in the surrounding environment.
  • R 3 is an alkyl group having a polar group
  • examples of the alkyl group having the polar group include 1-carboxyethyl group, 2-carboxyethyl group, 1-carboxypropyl group and 3-carboxypropyl group. Examples thereof include 1-carboxypentyl group and carboxy (phenyl) methyl group.
  • R 4 has the structure having a bond, an arylene group, or a structure having a hetero arylene group.
  • examples of the arylene group include a 1,3-phenylene group, a 1,4-phenylene group, a 1,4-naphthylene group and the like.
  • Specific examples of the structure having an arylene group include structures represented by the following formulas (2-1) to (2-5).
  • examples of the heteroarylene group include a thienylene group, a furanylene group, a pyridylene group and the like. Of these, a thienylene group is preferable.
  • Specific examples of the structure having a heteroarylene group include structures represented by the following formulas (3-1) to (3-6).
  • the compounds represented by the following formulas (4) to (9) are used in the above formula (1).
  • R 5 has an alkylene group having 1 to 20 carbon atoms, a cycloalkylene group, an aralkylene group, a heterocyclic group, or an ether bond or an amide bond which may have an ether bond or an amide bond. It is an arylene group that may have, and * represents a bond position.
  • the preferable lower limit is 0.01 part by weight and the preferable upper limit is 5 parts by weight with respect to 100 parts by weight of the curable resin.
  • the content of the compound represented by the above formula (1) is 0.01 parts by weight or more, the obtained curable resin composition becomes more excellent in visible light curability.
  • the content of the compound represented by the above formula (1) is 5 parts by weight or less, the obtained curable resin composition is more excellent in low liquid crystal contamination when used as a sealant for a liquid crystal display element.
  • the more preferable lower limit of the content of the compound represented by the above formula (1) is 0.1 parts by weight, and the more preferable upper limit is 2 parts by weight.
  • the curable resin composition of the present invention contains a curable resin.
  • the curable resin preferably contains a (meth) acrylic compound.
  • the (meth) acrylic compound include (meth) acrylic acid ester compounds, epoxy (meth) acrylates, urethane (meth) acrylates, and the like. Of these, epoxy (meth) acrylate is preferable.
  • the (meth) acrylic compound preferably has two or more (meth) acryloyl groups in one molecule from the viewpoint of reactivity.
  • the above-mentioned "(meth) acrylic” means acrylic or methacryl
  • the above-mentioned “(meth) acrylic compound” means a compound having a (meth) acryloyl group
  • Metala) acryloyl means acryloyl or methacryloyl.
  • the above-mentioned “(meth) acrylate” means acrylate or methacrylate.
  • the above-mentioned “epoxy (meth) acrylate” refers to a compound in which all epoxy groups in the epoxy compound are reacted with (meth) acrylic acid.
  • monofunctional ones include, for example, methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, n-butyl (meth) acrylate, and isobutyl (meth) acrylate.
  • bifunctional ones include, for example, 1,3-butanediol di (meth) acrylate, 1,4-butanediol di (meth) acrylate, and 1,6-hexane.
  • those having trifunctionality or higher include, for example, trimetyl propanetri (meth) acrylate, ethylene oxide-added trimethyl propanetri (meth) acrylate, and propylene oxide-added trimethyl propantri (meth) acrylate.
  • Examples of the epoxy (meth) acrylate include those obtained by reacting an epoxy compound and (meth) acrylic acid in the presence of a basic catalyst according to a conventional method.
  • Examples of the epoxy compound used as a raw material for synthesizing the epoxy (meth) acrylate include a bisphenol A type epoxy compound, a bisphenol F type epoxy compound, a bisphenol S type epoxy compound, and a 2,2'-diallyl bisphenol A type epoxy compound.
  • Hydrogenated bisphenol type epoxy compound Hydrogenated bisphenol type epoxy compound, propylene oxide added bisphenol A type epoxy compound, resorcinol type epoxy compound, biphenyl type epoxy compound, sulfide type epoxy compound, diphenyl ether type epoxy compound, dicyclopentadiene type epoxy compound, naphthalene type epoxy compound, phenol Novolac type epoxy compound, orthocresol novolac type epoxy compound, dicyclopentadiene novolac type epoxy compound, biphenyl novolac type epoxy compound, naphthalenephenol novolac type epoxy compound, glycidylamine type epoxy compound, alkyl polyol type epoxy compound, rubber modified epoxy compound , Epoxy ester compounds and the like.
  • Examples of commercially available bisphenol A type epoxy compounds include jER828EL, jER1004 (all manufactured by Mitsubishi Chemical Corporation), EPICLON EXA-850CRP (manufactured by DIC Corporation), and the like.
  • Examples of commercially available bisphenol F-type epoxy compounds include jER806 and jER4004 (both manufactured by Mitsubishi Chemical Corporation).
  • Examples of commercially available bisphenol S-type epoxy compounds include EPICLON EXA1514 (manufactured by DIC Corporation) and the like.
  • Examples of commercially available 2,2'-diallyl bisphenol A type epoxy compounds include RE-810NM (manufactured by Nippon Kayaku Co., Ltd.).
  • Examples of commercially available hydrogenated bisphenol type epoxy compounds include EPICLON EXA7015 (manufactured by DIC Corporation) and the like.
  • Examples of commercially available propylene oxide-added bisphenol A type epoxy compounds include EP-4000S (manufactured by ADEKA Corporation) and the like.
  • Examples of commercially available resorcinol-type epoxy compounds include EX-201 (manufactured by Nagase ChemteX Corporation) and the like.
  • Examples of commercially available biphenyl type epoxy compounds include jER YX-4000H (manufactured by Mitsubishi Chemical Corporation) and the like.
  • Examples of commercially available sulfide-type epoxy compounds include YSLV-50TE (manufactured by Nittetsu Chemical & Materials Co., Ltd.). Examples of commercially available diphenyl ether type epoxy compounds include YSLV-80DE (manufactured by Nittetsu Chemical & Materials Co., Ltd.) and the like. Examples of commercially available dicyclopentadiene type epoxy compounds include EP-4088S (manufactured by ADEKA Corporation) and the like. Examples of commercially available naphthalene-type epoxy compounds include EPICLON HP4032 and EPICLON EXA-4700 (both manufactured by DIC Corporation).
  • Examples of commercially available phenol novolac type epoxy compounds include EPICLON N-770 (manufactured by DIC Corporation) and the like.
  • Examples of commercially available orthocresol novolac type epoxy compounds include EPICLON N-670-EXP-S (manufactured by DIC Corporation) and the like.
  • Examples of commercially available dicyclopentadiene novolac type epoxy compounds include EPICLON HP7200 (manufactured by DIC Corporation) and the like.
  • Examples of commercially available biphenyl novolac type epoxy compounds include NC-3000P (manufactured by Nippon Kayaku Co., Ltd.) and the like.
  • Examples of commercially available naphthalene phenol novolac type epoxy compounds include ESN-165S (manufactured by Nittetsu Chemical & Materials Co., Ltd.).
  • Examples of commercially available glycidylamine type epoxy compounds include jER630 (manufactured by Mitsubishi Chemical Corporation), EPICLON 430 (manufactured by DIC Corporation), TETRAD-X (manufactured by Mitsubishi Gas Chemical Company, Inc.) and the like.
  • alkyl polyol type epoxy compounds include, for example, ZX-1542 (manufactured by Nittetsu Chemical & Materials Co., Ltd.), EPICLON 726 (manufactured by DIC Corporation), Epolite 80MFA (manufactured by Kyoeisha Chemical Co., Ltd.), and Denacol EX. -611 (manufactured by Nagase ChemteX Corporation) and the like.
  • Examples of commercially available rubber-modified epoxy compounds include YR-450, YR-207 (all manufactured by Nittetsu Chemical & Materials Co., Ltd.), and Epolide PB (manufactured by Daicel Co., Ltd.).
  • Examples of commercially available glycidyl ester compounds include Denacol EX-147 (manufactured by Nagase ChemteX Corporation) and the like.
  • Other commercially available epoxy compounds include, for example, YDC-1312, YSLV-80XY, YSLV-90CR (all manufactured by Nittetsu Chemical & Materials Co., Ltd.), XAC4151 (manufactured by Asahi Kasei Corporation), jER1031 and jER1032. (All manufactured by Mitsubishi Chemical Corporation), EXA-7120 (manufactured by DIC Corporation), TEPIC (manufactured by Nissan Chemical Industries, Ltd.) and the like.
  • epoxy (meth) acrylates commercially available ones include, for example, epoxy (meth) acrylate manufactured by Daicel Ornex, epoxy (meth) acrylate manufactured by Shin-Nakamura Chemical Industry Co., Ltd., and epoxy (meth) acrylate manufactured by Kyoeisha Chemical Co., Ltd. Examples thereof include meta) acrylate and epoxy (meth) acrylate manufactured by Nagase ChemteX Corporation.
  • Examples of the epoxy (meth) acrylate manufactured by Daicel Ornex include EBECRYL860, EBECRYL3200, EBECRYL3201, EBECRYL3412, EBECRYL3600, EBECRYL3700, EBECRYL3701, EBECRYL3702, EBECRYL3702, EBECRYL3702, EBECRYL3702, EBECRYL3701, EBECRYL3701
  • Examples of the epoxy (meth) acrylate manufactured by Shin Nakamura Chemical Industry Co., Ltd. include EA-1010, EA-1020, EA-5323, EA-5520, EA-CHD, and EMA-1020.
  • Examples of the epoxy (meth) acrylate manufactured by Kyoeisha Chemical Co., Ltd. include epoxy ester M-600A, epoxy ester 40EM, epoxy ester 70PA, epoxy ester 200PA, epoxy ester 80MFA, epoxy ester 3002M, epoxy ester 3002A, and epoxy ester 1600A. Examples thereof include epoxy ester 3000M, epoxy ester 3000A, epoxy ester 200EA, and epoxy ester 400EA. Examples of the epoxy (meth) acrylate manufactured by Nagase ChemteX include Denacol acrylate DA-141, Denacol acrylate DA-314, and Denacol acrylate DA-911.
  • the urethane (meth) acrylate can be obtained, for example, by reacting a (meth) acrylic acid derivative having a hydroxyl group with a polyfunctional isocyanate compound in the presence of a catalytic amount of a tin-based compound.
  • polyfunctional isocyanate compound examples include isophorone diisocyanate, 2,4-tolylene diisocyanate, 2,6-tolylene diisocyanate, hexamethylene diisocyanate, trimethylhexamethylene diisocyanate, diphenylmethane-4,4'-diisocyanate (MDI), and the like.
  • Hydrogenated MDI Polymeric MDI, 1,5-naphthalenediocyanate, Norbornan diisocyanate, Trizine diisocyanate, Xylylene diisocyanate (XDI), Hydrogenated XDI, Lysine diisocyanate, Triphenylmethane triisocyanate, Tris (isocyanatephenyl) thiophosphate, Tetramethyl Examples thereof include xylylene diisocyanate and 1,6,11-undecantry isocyanate.
  • polyfunctional isocyanate compound a chain-extended polyfunctional isocyanate compound obtained by reacting a polyol with an excess polyfunctional isocyanate compound can also be used.
  • the polyol include ethylene glycol, propylene glycol, glycerin, sorbitol, trimethylolpropane, carbonate diol, polyether diol, polyester diol, and polycaprolactone diol.
  • Examples of the (meth) acrylic acid derivative having a hydroxyl group include hydroxyalkyl mono (meth) acrylate, mono (meth) acrylate of dihydric alcohol, mono (meth) acrylate of trihydric alcohol, and di (meth) acrylate. , Epoxy (meth) acrylate and the like.
  • Examples of the hydroxyalkyl mono (meth) acrylate include 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, and 4-hydroxybutyl (meth) acrylate. Can be mentioned.
  • Examples of the divalent alcohol include ethylene glycol, propylene glycol, 1,3-propanediol, 1,3-butanediol, 1,4-butanediol, polyethylene glycol and the like.
  • Examples of the trihydric alcohol include trimethylolethane, trimethylolpropane, and glycerin.
  • Examples of the epoxy (meth) acrylate include bisphenol A type epoxy acrylate and the like.
  • urethane (meth) acrylates commercially available ones include, for example, urethane (meth) acrylate manufactured by Toa Synthetic Co., Ltd., urethane (meth) acrylate manufactured by Daicel Ornex, and urethane (meth) manufactured by Negami Kogyo Co., Ltd. Examples thereof include acrylate, urethane (meth) acrylate manufactured by Shin-Nakamura Chemical Co., Ltd., urethane (meth) acrylate manufactured by Kyoeisha Chemical Co., Ltd., and the like. Examples of the urethane (meth) acrylate manufactured by Toagosei Co., Ltd.
  • the urethane (meth) acrylate manufactured by the Daicel Orunekusu Inc. for example, EBECRYL210, EBECRYL220, EBECRYL230, EBECRYL270, EBECRYL1290, EBECRYL2220, EBECRYL4827, EBECRYL4842, EBECRYL4858, EBECRYL5129, EBECRYL6700, EBECRYL8402, EBECRYL8803, EBECRYL8804, EBECRYL8807, EBECRYL9260 etc. Can be mentioned.
  • Examples of the urethane (meth) acrylate manufactured by Negami Kogyo Co., Ltd. include Art Resin UN-330, Art Resin SH-500B, Art Resin UN-1200TPK, Art Resin UN-1255, Art Resin UN-3320HB, and Art Resin UN-. 7100, Art Resin UN-9000A, Art Resin UN-9000H and the like can be mentioned.
  • Examples of the urethane (meth) acrylate manufactured by Shin-Nakamura Chemical Industry Co., Ltd. include U-2HA, U-2PHA, U-3HA, U-4HA, U-6H, U-6HA, U-6LPA, U-10H, and the like.
  • Examples of the urethane (meth) acrylate manufactured by Kyoeisha Chemical Co., Ltd. include AH-600, AI-600, AT-600, UA-101I, UA-101T, UA-306H, UA-306I, and UA-306T. Be done.
  • the curable resin may contain an epoxy compound for the purpose of improving the adhesiveness of the obtained curable resin composition.
  • the epoxy compound include an epoxy compound used as a raw material for synthesizing the above-mentioned epoxy (meth) acrylate, a partially (meth) acrylic-modified epoxy compound, and the like.
  • the above-mentioned partial (meth) acrylic-modified epoxy compound means, for example, reacting a part of epoxy groups of an epoxy compound having two or more epoxy groups in one molecule with (meth) acrylic acid. It means a compound having one or more epoxy groups and one or more (meth) acryloyl groups in one molecule.
  • the curable resin contains the (meth) acrylic compound and the epoxy compound, or when the partial (meth) acrylic-modified epoxy compound is contained, the (meth) acryloyl group and the epoxy in the curable resin It is preferable that the ratio of the (meth) acryloyl group in the total with the groups is 30 mol% or more and 95 mol% or less. When the ratio of the (meth) acryloyl group is in this range, the obtained curable resin composition is excellent in adhesiveness while suppressing the occurrence of liquid crystal contamination when used as a sealant for a liquid crystal display element. It becomes.
  • the curable resin has -OH group, -NH- group, and -NH 2 groups from the viewpoint of making the obtained curable resin composition more excellent in low liquid crystal contamination when used as a sealant for a liquid crystal display element.
  • Those having a hydrogen-bonding unit such as the above are preferable.
  • the curable resin may be used alone or in combination of two or more.
  • the curable resin composition of the present invention may contain a sensitizer, but does not contain the sensitizer from the viewpoint of low liquid crystal contamination when used as a sealant for a liquid crystal display element. Is preferable.
  • the curable resin composition of the present invention has excellent visible light curability even if it does not contain a sensitizer. ..
  • sensitizer examples include ethyl 4- (dimethylamino) benzoate, 9,10-dibutoxyanthracene, 2,4-diethylthioxanthone, and 2,2-dimethoxy-1,2-diphenylethane-1-one.
  • the content of the sensitizer is preferably 0.01 part by weight and a preferable upper limit is 3 parts by weight with respect to 100 parts by weight of the curable resin.
  • a preferable upper limit is 3 parts by weight with respect to 100 parts by weight of the curable resin.
  • the sensitizing effect is more exerted.
  • the content of the sensitizer is 3 parts by weight or less, light can be transmitted to a deep part without excessive absorption.
  • the more preferable lower limit of the content of the sensitizer is 0.1 parts by weight, and the more preferable upper limit is 1 part by weight.
  • the curable resin composition of the present invention may contain a thermosetting initiator as long as the object of the present invention is not impaired.
  • the thermal polymerization initiator include those made of an azo compound, an organic peroxide and the like. Of these, a polymer azo initiator composed of a polymer azo compound is preferable.
  • the thermal polymerization initiator may be used alone or in combination of two or more.
  • the above-mentioned "polymer azo compound” refers to a compound having an azo group and having a number average molecular weight of 300 or more, which generates a radical capable of curing a (meth) acryloyloxy group by heat. means.
  • the preferable lower limit of the number average molecular weight of the polymer azo compound is 1000, and the preferable upper limit is 300,000.
  • the number average molecular weight of the polymer azo compound is in this range, it can be easily mixed with the curable resin.
  • the obtained curable resin composition is used as a sealant for a liquid crystal display element, it can be easily mixed with the curable resin while suppressing liquid crystal contamination.
  • the more preferable lower limit of the number average molecular weight of the polymer azo compound is 5000, the more preferable upper limit is 100,000, the further preferable lower limit is 10,000, and the further preferable upper limit is 90,000.
  • Examples of the polymer azo compound include those having a structure in which a plurality of units such as polyalkylene oxide and polydimethylsiloxane are bonded via an azo group.
  • the polymer azo compound having a structure in which a plurality of units such as polyalkylene oxide are bonded via the azo group those having a polyethylene oxide structure are preferable.
  • Specific examples of the polymer azo compound include a polycondensate of 4,4'-azobis (4-cyanopentanoic acid) and polyalkylene glycol, and 4,4'-azobis (4-cyanopentanoic acid). And a polycondensate of polydimethylsiloxane having a terminal amino group and the like.
  • Examples of commercially available polymer azo compounds include VPE-0201, VPE-0401, VPE-0601, VPS-0501, and VPS-1001 (all manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.). Be done.
  • Examples of the azo compound that is not a polymer include V-65 and V-501 (both manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.).
  • organic peroxide examples include ketone peroxides, peroxyketals, hydroperoxides, dialkyl peroxides, peroxyesters, diacyl peroxides, peroxydicarbonates and the like.
  • the preferable lower limit is 0.05 parts by weight and the preferable upper limit is 10 parts by weight with respect to 100 parts by weight of the curable resin.
  • the content of the thermosetting initiator is 0.05 parts by weight or more
  • the curable resin composition of the present invention becomes more excellent in thermosetting property.
  • the content of the thermal polymerization initiator is 10 parts by weight or less
  • the curable resin composition of the present invention becomes more excellent in storage stability, and when used as a sealant for a liquid crystal display element, low liquid crystal contamination It will also be superior in sex.
  • the more preferable lower limit of the content of the thermal polymerization initiator is 0.1 parts by weight, and the more preferable upper limit is 5 parts by weight.
  • the curable resin composition of the present invention may contain a thermosetting agent.
  • the heat-curing agent include organic acid hydrazide, imidazole derivatives, amine compounds, polyhydric phenolic compounds, acid anhydrides and the like. Of these, organic acid hydrazide is preferably used.
  • the thermosetting agent may be used alone or in combination of two or more.
  • Examples of the organic acid hydrazide include sebacic acid dihydrazide, isophthalic acid dihydrazide, adipic acid dihydrazide, malonic acid dihydrazide and the like.
  • Examples of commercially available organic acid hydrazides include organic acid hydrazides manufactured by Otsuka Chemical Co., Ltd., organic acid hydrazides manufactured by Ajinomoto Fine-Techno Co., Ltd., and the like.
  • Examples of the organic acid hydrazide manufactured by Otsuka Chemical Co., Ltd. include SDH and ADH.
  • Examples of the organic acid hydrazide manufactured by Ajinomoto Fine-Techno Co., Ltd. include Amicure VDH, Amicure VDH-J, Amicure UDH, Amicure UDH-J and the like.
  • the content of the thermosetting agent is preferably 1 part by weight and a preferable upper limit of 50 parts by weight with respect to 100 parts by weight of the curable resin.
  • the thermosetting property can be made more excellent without deteriorating the coatability of the obtained curable resin composition.
  • a more preferable upper limit of the content of the thermosetting agent is 30 parts by weight.
  • the curable resin composition of the present invention preferably contains a filler for the purpose of improving viscosity, improving adhesiveness due to stress dispersion effect, improving linear expansion coefficient, and the like.
  • an inorganic filler or an organic filler can be used as the filler.
  • the inorganic filler include silica, talc, glass beads, asbestos, gypsum, diatomaceous soil, smectite, bentonite, montmorillonite, sericite, active white clay, alumina, zinc oxide, iron oxide, magnesium oxide, tin oxide and titanium oxide. , Calcium carbonate, magnesium carbonate, magnesium hydroxide, aluminum hydroxide, aluminum nitride, silicon nitride, barium sulfate, calcium silicate and the like.
  • the organic filler include polyester fine particles, polyurethane fine particles, vinyl polymer fine particles, acrylic polymer fine particles, and the like. The filler may be used alone or in combination of two or more.
  • the preferable lower limit is 30 parts by weight and the preferable upper limit is 80 parts by weight with respect to 100 parts by weight of the curable resin.
  • the content of the filler is in this range, the effect of improving the adhesiveness and the like is excellent without deteriorating the coatability and the like.
  • the more preferable lower limit of the content of the filler is 45 parts by weight, and the more preferable upper limit is 65 parts by weight.
  • the curable resin composition of the present invention preferably contains a silane coupling agent.
  • the silane coupling agent mainly has a role as an adhesive auxiliary for satisfactorily adhering the curable resin composition to a substrate or the like.
  • silane coupling agent for example, 3-aminopropyltrimethoxysilane, 3-mercaptopropyltrimethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-isocyanatepropyltrimethoxysilane and the like are preferably used. These are excellent in the effect of improving the adhesiveness to the substrate and the like, and when the obtained curable resin composition is used as a sealant for a liquid crystal display element, they are chemically bonded to the curable resin into the liquid crystal. The outflow of the curable resin can be suppressed.
  • the silane coupling agent may be used alone or in combination of two or more.
  • the preferable lower limit of the content of the silane coupling agent in 100 parts by weight of the curable resin composition of the present invention is 0.1 parts by weight, and the preferable upper limit is 10 parts by weight.
  • the content of the silane coupling agent is in this range, the obtained curable resin composition becomes more excellent in adhesiveness.
  • the adhesiveness is improved while suppressing the occurrence of liquid crystal contamination.
  • the more preferable lower limit of the content of the silane coupling agent is 0.3 parts by weight, and the more preferable upper limit is 5 parts by weight.
  • the curable resin composition of the present invention further contains additives such as a reactive diluent, a rocking agent, a spacer, a curing accelerator, a defoaming agent, a leveling agent, and a polymerization inhibitor, if necessary. May be good.
  • a mixer such as a homodisper, a homomixer, a universal mixer, a planetary mixer, a kneader, or a three-roll mixer is used to photopolymerize the curable resin with the curable resin.
  • a mixer such as a homodisper, a homomixer, a universal mixer, a planetary mixer, a kneader, or a three-roll mixer is used to photopolymerize the curable resin with the curable resin.
  • examples thereof include a method of mixing the initiator and a silane coupling agent or the like to be added as needed.
  • the curable resin composition of the present invention is suitably used as a sealant for a display element, and more preferably used as a sealant for a liquid crystal display element.
  • a sealant for a display element containing the curable resin composition of the present invention and a sealant for a liquid crystal display element containing the curable resin composition of the present invention are also one of the present inventions, respectively.
  • a vertically conductive material By blending the conductive fine particles with the curable resin composition of the present invention, a vertically conductive material can be produced.
  • a vertically conductive material containing the curable resin composition of the present invention and conductive fine particles is also one of the present inventions.
  • the conductive fine particles metal balls, those having a conductive metal layer formed on the surface of the resin fine particles, and the like can be used.
  • the one in which the conductive metal layer is formed on the surface of the resin fine particles is preferable because the excellent elasticity of the resin fine particles enables conductive connection without damaging the transparent substrate or the like.
  • a display element having a cured product of the sealant for a display element of the present invention, a cured product of the sealant for a liquid crystal display element of the present invention, or a cured product of a vertically conductive material of the present invention is also one of the present inventions. ..
  • a liquid crystal display element using the sealant for the liquid crystal display element of the present invention is preferable, and a liquid crystal display element having a narrow frame design is more preferable.
  • the width of the frame portion around the liquid crystal display unit is preferably 2 mm or less.
  • the coating width of the sealant for the liquid crystal display element of the present invention is preferably 1 mm or less.
  • a liquid crystal dropping method is preferably used, and specific examples thereof include a method having the following steps. First, a step of applying the sealant for a liquid crystal display element of the present invention to one of two transparent substrates having an electrode such as an ITO thin film and an alignment film by screen printing, dispenser application, or the like to form a frame-shaped seal pattern. I do. Next, in a state where the sealant for a liquid crystal display element of the present invention is uncured, fine droplets of liquid crystal are dropped and applied into the frame of the seal pattern of the substrate, and the other transparent substrate is superposed under vacuum.
  • the liquid crystal display element can be obtained by a method of performing a step of photocuring the sealant by irradiating the seal pattern portion of the sealant for the liquid crystal display element of the present invention with light through a cut filter or the like. Further, in addition to the step of photocuring the sealant, a step of heating the sealant to heat cure it may be performed.
  • the curable resin composition of the present invention is also suitably used for bonding electronic components.
  • the curable resin composition of the present invention is used as an adhesive for electronic parts, low-energy light can be used for light irradiation during curing, so that deterioration of other members can be suppressed.
  • An adhesive for electronic components containing the curable resin composition of the present invention and an electronic component bonded with a cured product of the adhesive for electronic components of the present invention are also one of the present inventions, respectively.
  • a curable resin composition having excellent visible light curability and adhesiveness, and also having excellent low liquid crystal contamination property when used as a sealant for a liquid crystal display element.
  • a display element having a cured product of a sealant for a display element or a cured product of the vertically conductive material.
  • the extracted solution was washed with saturated aqueous sodium hydrogen carbonate solution and brine, dried over anhydrous magnesium sulfate and concentrated to obtain the product (A1).
  • 3 parts by weight of the obtained product (A1), 0.76 parts by weight of hydroxylammonium chloride, and 0.86 parts by weight of pyridine were added to 30 mL of ethanol and stirred under reflux for 10 hours.
  • the obtained reaction solution was poured into ice water and then filtered. The filter was washed with water, dissolved in ethyl acetate, dried over anhydrous magnesium sulfate and concentrated to give the product (B1).
  • the extracted solution was washed with saturated aqueous sodium hydrogen carbonate solution and brine, dried over anhydrous magnesium sulfate and concentrated to obtain the product (A2).
  • 3 parts by weight of the obtained product (A2), 0.76 parts by weight of hydroxylammonium chloride, and 0.86 parts by weight of pyridine were added to 30 mL of ethanol and stirred under reflux for 10 hours.
  • the obtained reaction solution was poured into ice water and then filtered.
  • the filter was washed with water, dissolved in ethyl acetate, dried over anhydrous magnesium sulfate and concentrated to give the product (B2).
  • the extracted solution was washed with saturated aqueous sodium hydrogen carbonate solution and brine, dried over anhydrous sodium sulfate and concentrated to give the product (A3).
  • Examples 1 to 11 and Comparative Examples 1 to 3 The curable resins of Examples 1 to 11 and Comparative Examples 1 to 3 were mixed by using a planetary stirrer and then further mixing using three rolls according to the compounding ratios shown in Table 1. The composition was prepared. As a planetary stirrer, Awatori Rentaro (manufactured by Shinky Co., Ltd.) was used.
  • UV curability 1 part by weight of spacer fine particles was dispersed in 100 parts by weight of each curable resin composition obtained in Examples and Comparative Examples.
  • spacer fine particles Micropearl SI-H050 (manufactured by Sekisui Chemical Co., Ltd.) was used.
  • the sealant was filled in a syringe for dispensing, defoamed, and then applied onto a glass substrate with a dispenser.
  • PSY-10E manufactured by Musashi Engineering Co., Ltd.
  • SHOTMASTER 300 manufactured by Musashi Engineering Co., Ltd.
  • a glass substrate of the same size was bonded to the substrate coated with the sealant under a reduced pressure of 5 Pa using a vacuum bonding device.
  • a metal halide lamp was used to irradiate the sealing agent portion of the bonded glass substrate with light of 100 mW / cm 2 for 10 seconds.
  • the light irradiation was performed through a cut filter (340 nm cut filter) that cuts light having a wavelength of 340 m or less.
  • the FT-IR measurement of the sealant was performed using an infrared spectroscope, and the amount of change in the peak derived from the (meth) acryloyl group before and after light irradiation was measured.
  • FTS3000 manufactured by BIORAD
  • ⁇ when the peak derived from the (meth) acryloyl group decreased by 95% or more after light irradiation
  • ⁇ when it decreased by 90% or more and less than 95%
  • ⁇ when it decreased by 70% or more and less than 90%.
  • the UV curability was evaluated as "x" when the decrease in the peak derived from the (meth) acryloyl group after light irradiation was less than 70%.
  • Spacer fine particles 1 part by weight of spacer fine particles was dispersed in 100 parts by weight of each curable resin composition obtained in Examples and Comparative Examples.
  • spacer fine particles Micropearl SI-H050 (manufactured by Sekisui Chemical Co., Ltd.) was used.
  • the sealant was filled in a syringe for dispensing, defoamed, and then applied onto a glass substrate with a dispenser.
  • PSY-10E manufactured by Musashi Engineering Co., Ltd.
  • SHOTMASTER 300 manufactured by Musashi Engineering Co., Ltd.
  • a glass substrate of the same size was bonded to the substrate coated with the sealant under a reduced pressure of 5 Pa using a vacuum bonding device.
  • a metal halide lamp was used to irradiate the sealing agent portion of the bonded glass substrate with light of 100 mW / cm 2 for 10 seconds.
  • the light irradiation was performed through a cut filter (420 nm cut filter) that cuts light having a wavelength of 420 m or less.
  • the FT-IR measurement of the sealant was performed using an infrared spectroscope, and the amount of change in the peak derived from the (meth) acryloyl group before and after light irradiation was measured.
  • FTS3000 manufactured by BIORAD
  • ⁇ when the peak derived from the (meth) acryloyl group decreased by 95% or more after light irradiation
  • ⁇ when it decreased by 90% or more and less than 95%
  • ⁇ when it decreased by 70% or more and less than 90%.
  • the UV curability was evaluated as "x" when the decrease in the peak derived from the (meth) acryloyl group after light irradiation was less than 70%.
  • Spacer fine particles 1 part by weight of spacer fine particles was dispersed in 100 parts by weight of each curable resin composition obtained in Examples and Comparative Examples, and finely dropped onto one of two glass substrates with ITO thin films (30 ⁇ 40 mm).
  • spacer fine particles Micropearl SI-H050 (manufactured by Sekisui Chemical Co., Ltd.) was used.
  • the other glass substrate with an ITO thin film was attached to this in a cross shape, irradiated with light of 100 mW / cm 2 for 30 seconds with a metal halide lamp, and then heated at 120 ° C. for 60 minutes to obtain an adhesive test piece. ..
  • the obtained adhesive test piece was subjected to a tensile test (5 mm / sec) with chucks arranged one above the other.
  • a tensile test 5 mm / sec
  • the seal coating cross-sectional area (cm 2 ) is 1.5 kgf / cm 2 or more, it is “ ⁇ ”, and when it is less than 1.5 kgf / cm 2.
  • x was evaluated as “x” to evaluate the adhesiveness.
  • a curable resin composition having excellent visible light curability and adhesiveness, and also excellent in low liquid crystal contamination when used as a sealant for a liquid crystal display element.
  • a display element having a cured product of a sealant for a display element or a cured product of the vertically conductive material.

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Abstract

La présente invention vise à fournir une composition de résine durcissable qui présente une excellente aptitude au durcissement à la lumière visible et une excellente adhésivité, tout en présentant un faible risque de contamination de cristaux liquides si elle est utilisée dans un agent d'étanchéité pour des éléments d'affichage à cristaux liquides. La présente invention vise également à fournir : un agent d'étanchéité pour des éléments d'affichage, un agent d'étanchéité pour des éléments d'affichage à cristaux liquides, et un matériau conducteur verticalement, chacun contenant cette composition de résine durcissable ; et un élément d'affichage qui comprend un produit durci de cet agent d'étanchéité pour des éléments d'affichage, un produit durci de cet agent d'étanchéité pour des éléments d'affichage à cristaux liquides ou un produit durci de ce matériau conducteur verticalement. La présente invention en outre à fournir : un adhésif pour composants électroniques, ledit adhésif contenant cette composition de résine durcissable ; et un composant électronique qui est lié au moyen d'un produit durci de cet adhésif pour composants électroniques. La présente invention concerne par conséquent une composition de résine durcissable qui contient une résine durcissable et un initiateur de photopolymérisation, l'initiateur de photopolymérisation contenant un composé qui est représenté par la formule (1). Dans la formule (1), chaque R1 représente indépendamment un groupe alkyle ayant de 1 à 20 atomes de carbone, ledit groupe alkyle ayant facultativement une liaison éther ou une liaison amide, un groupe cycloalkyle, un groupe aralkyle, un groupe hétérocyclique, ou un groupe aryle qui a facultativement une liaison éther ou une liaison amide ; et le groupe alkyle ayant de 1 à 20 atomes de carbone, le groupe cycloalkyle, le groupe aralkyle, le groupe hétérocyclique et le groupe aryle pouvant avoir un groupe polaire. Dans la formule (1), chaque R2 représentant indépendamment un groupe alkyle ayant de 1 à 20 atomes de carbone, ledit groupe alkyle ayant facultativement une liaison éther ou une liaison amide, un groupe cycloalkyle, un groupe aralkyle, un groupe hétérocyclique, ou un groupe aryle qui a facultativement une liaison éther ou une liaison amide ; et le groupe alkyle ayant de 1 à 20 atomes de carbone, le groupe cycloalkyle, le groupe aralkyle, le groupe hétérocyclique et le groupe aryle pouvant avoir un groupe polaire. Dans la formule (1), chaque R3 représente indépendamment un groupe alkyle ayant de 1 à 20 atomes de carbone, ledit groupe alkyle ayant facultativement une liaison éther ou une liaison amide, un groupe cycloalkyle, un groupe aralkyle, un groupe hétérocyclique, ou un groupe aryle qui a facultativement une liaison éther ou une liaison amide ; et le groupe alkyle ayant de 1 à 20 atomes de carbone, le groupe cycloalkyle, le groupe aralkyle, le groupe hétérocyclique et le groupe aryle pouvant avoir un groupe polaire. Dans la formule (1), R1 représente une main de liaison, une structure ayant un groupe arylène ou une structure ayant un groupe hétéroarylène.
PCT/JP2021/007996 2020-03-03 2021-03-02 Composition de résine durcissable, agent d'étanchéité pour éléments d'affichage, agent d'étanchéité pour éléments d'affichage à cristaux liquides, matériau conducteur vertical, élément d'affichage, adhésif pour composants électroniques, et composant électronique WO2021177316A1 (fr)

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CN202180006366.8A CN114667302B (zh) 2020-03-03 2021-03-02 固化性树脂组合物、显示元件用密封剂、液晶显示元件用密封剂、上下导通材料、显示元件、电子部件用粘接剂和电子部件
JP2021515229A JP7084550B2 (ja) 2020-03-03 2021-03-02 液晶表示素子用シール剤、上下導通材料、表示素子
KR1020227012228A KR20220149651A (ko) 2020-03-03 2021-03-02 경화성 수지 조성물, 표시 소자용 시일제, 액정 표시 소자용 시일제, 상하 도통 재료, 표시 소자, 전자 부품용 접착제, 및, 전자 부품

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WO2022255452A1 (fr) * 2021-06-04 2022-12-08 積水化学工業株式会社 Agent d'étanchéité pour éléments d'affichage à cristaux liquides et élément d'affichage à cristaux liquides associé
WO2023032543A1 (fr) * 2021-09-03 2023-03-09 積水化学工業株式会社 Matériau d'étanchéité d'élément d'affichage à cristaux liquides et élément d'affichage à cristaux liquides

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WO2022255452A1 (fr) * 2021-06-04 2022-12-08 積水化学工業株式会社 Agent d'étanchéité pour éléments d'affichage à cristaux liquides et élément d'affichage à cristaux liquides associé
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