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WO2015111570A1 - Composition de résine durcissable par exposition à la lumière/humidité, adhésif pour composants électroniques, et adhésif pour éléments d'affichage - Google Patents

Composition de résine durcissable par exposition à la lumière/humidité, adhésif pour composants électroniques, et adhésif pour éléments d'affichage Download PDF

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Publication number
WO2015111570A1
WO2015111570A1 PCT/JP2015/051354 JP2015051354W WO2015111570A1 WO 2015111570 A1 WO2015111570 A1 WO 2015111570A1 JP 2015051354 W JP2015051354 W JP 2015051354W WO 2015111570 A1 WO2015111570 A1 WO 2015111570A1
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Prior art keywords
resin composition
light
meth
curable resin
moisture curable
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PCT/JP2015/051354
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English (en)
Japanese (ja)
Inventor
高橋　徹
良隆 国広
彰 結城
拓身 木田
Original Assignee
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 CN201580001617.8A priority Critical patent/CN105473631A/zh
Priority to KR1020157033386A priority patent/KR102242601B1/ko
Priority to CN202210318888.8A priority patent/CN114702631A/zh
Priority to JP2015508352A priority patent/JP5845377B1/ja
Priority to KR1020217011028A priority patent/KR102372448B1/ko
Publication of WO2015111570A1 publication Critical patent/WO2015111570A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
    • C08L75/04—Polyurethanes
    • C08L75/14—Polyurethanes having carbon-to-carbon unsaturated bonds
    • C08L75/16—Polyurethanes having carbon-to-carbon unsaturated bonds having terminal carbon-to-carbon unsaturated bonds
    • 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
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    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
    • C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
    • C08F290/06—Polymers provided for in subclass C08G
    • C—CHEMISTRY; METALLURGY
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    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
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    • C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
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    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/16—Catalysts
    • C08G18/22—Catalysts containing metal compounds
    • C08G18/24—Catalysts containing metal compounds of tin
    • C08G18/244—Catalysts containing metal compounds of tin tin salts of carboxylic acids
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    • C—CHEMISTRY; METALLURGY
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    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/30—Low-molecular-weight compounds
    • C08G18/302—Water
    • C08G18/307—Atmospheric humidity
    • C—CHEMISTRY; METALLURGY
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    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
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    • C08G18/48—Polyethers
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    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
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    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/48—Polyethers
    • C08G18/4854—Polyethers containing oxyalkylene groups having four carbon atoms in the alkylene group
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    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/67—Unsaturated compounds having active hydrogen
    • C08G18/671—Unsaturated compounds having only one group containing active hydrogen
    • C08G18/672—Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen
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    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
    • C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
    • C08G18/7657—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings
    • C08G18/7664—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups
    • C08G18/7671—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups containing only one alkylene bisphenyl group
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    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
    • C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
    • C08G18/7657—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings
    • C08G18/7678—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing condensed aromatic rings
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    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/49—Phosphorus-containing compounds
    • C08K5/51—Phosphorus bound to oxygen
    • C08K5/53—Phosphorus bound to oxygen bound to oxygen and to carbon only
    • C08K5/5313—Phosphinic compounds, e.g. R2=P(:O)OR'
    • 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
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    • C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
    • C09J175/04—Polyurethanes
    • C09J175/14—Polyurethanes having carbon-to-carbon unsaturated bonds
    • C09J175/16—Polyurethanes having carbon-to-carbon unsaturated bonds having terminal carbon-to-carbon unsaturated bonds
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    • 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
    • C09J2203/00—Applications of adhesives in processes or use of adhesives in the form of films or foils
    • C09J2203/318—Applications of adhesives in processes or use of adhesives in the form of films or foils for the production of liquid crystal displays
    • 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
    • C09J2203/00—Applications of adhesives in processes or use of adhesives in the form of films or foils
    • C09J2203/326—Applications of adhesives in processes or use of adhesives in the form of films or foils for bonding electronic components such as wafers, chips or semiconductors

Definitions

  • the present invention relates to a light moisture curable resin composition having excellent light shielding properties and adhesiveness. Moreover, this invention relates to the adhesive agent for electronic components and the adhesive agent for display elements which use this optical moisture hardening type resin composition.
  • liquid crystal display elements In recent years, liquid crystal display elements, organic EL display elements, and the like are widely used as display elements having features such as thinness, light weight, and low power consumption.
  • a photocurable resin composition is usually used for sealing a liquid crystal or a light emitting layer, bonding a substrate, an optical film, a protective film, or various members.
  • a frame is being made (hereinafter also referred to as a narrow frame design).
  • a photocurable resin composition may be applied to a portion where light does not reach sufficiently, and as a result, the photocurable resin composition applied to a portion where light does not reach is cured. There was a problem that was insufficient.
  • Patent Document 1 discloses a method of blending a light-shielding agent into a photothermosetting resin composition that can be sufficiently cured by heating even when photocuring is insufficient. There was a risk of adverse effects.
  • the present invention is a light moisture curable resin composition containing a radical polymerizable compound, a moisture curable urethane resin, a photo radical polymerization initiator, and a light shielding agent.
  • the present invention is described in detail below.
  • the present inventors As a method for curing a resin composition containing a light-shielding agent without heating at a high temperature, the present inventors have used optical moisture containing a radical polymerizable compound, a moisture curable urethane resin, and a radical photopolymerization initiator. It has been found that a light-moisture curable resin composition excellent in both light shielding properties and adhesiveness can be obtained by blending a light shielding agent into the curable resin composition, and the present invention has been completed.
  • the light moisture curable resin composition of the present invention contains a light-shielding agent.
  • the light moisture curable resin composition of the present invention has excellent light shielding properties and can prevent light leakage of the display element.
  • the “light-shielding agent” means a material having an ability of hardly transmitting light in the visible light region.
  • the light-shielding agent examples include iron oxide, titanium black, aniline black, cyanine black, fullerene, carbon black, and resin-coated carbon black. Further, the light-shielding agent does not have to be black, and a material such as silica or talc, which will be described later as a filler, may be used as long as it has a capability of hardly transmitting light in the visible light region. Included in the agent. Of these, titanium black is preferable.
  • Titanium black is a substance having a higher transmittance in the vicinity of the ultraviolet region, particularly for light having a wavelength of 370 to 450 nm, compared to the average transmittance for light having a wavelength of 300 to 800 nm. That is, the above-described titanium black sufficiently shields light having a wavelength in the visible light region, thereby imparting light shielding properties to the light moisture curable resin composition of the present invention, while transmitting light having a wavelength in the vicinity of the ultraviolet region. Is a light-shielding agent.
  • the light of the photo moisture curable resin composition of the present invention can be used. Curability can be further increased.
  • the light-shielding agent contained in the light moisture curable resin composition of the present invention is preferably a highly insulating material, and titanium black is also preferable as the highly insulating light-shielding agent.
  • the titanium black preferably has an optical density (OD value) of 3 or more, and more preferably 4 or more.
  • the titanium black preferably has a blackness (L value) of 9 or more, more preferably 11 or more. The higher the light shielding property of the titanium black, the better. There is no particular upper limit to the OD value of the titanium black, but it is usually 5 or less.
  • the above-mentioned titanium black exhibits a sufficient effect even if it is not surface-treated, but the surface is treated with an organic component such as a coupling agent, silicon oxide, titanium oxide, germanium oxide, aluminum oxide, oxidized Surface-treated titanium black such as those coated with an inorganic component such as zirconium or magnesium oxide can also be used. Especially, what is processed with the organic component is preferable at the point which can improve insulation more.
  • the display element manufactured using the light moisture curable resin composition of the present invention has a high contrast because there is no light leakage because the light moisture curable resin composition has sufficient light shielding properties. Image display quality.
  • titanium black examples include 12S, 13M, 13M-C, 13R-N (all manufactured by Mitsubishi Materials Corporation), Tilak D (manufactured by Ako Kasei Co., Ltd.), and the like.
  • the preferable lower limit of the specific surface area of the titanium black is 5 m 2 / g
  • the preferable upper limit is 40 m 2 / g
  • the more preferable lower limit is 10 m 2 / g
  • the more preferable upper limit is 25 m 2 / g.
  • the preferable lower limit of the sheet resistance of the titanium black is 10 9 ⁇ / ⁇ when mixed with a resin (70% blending), and the more preferable lower limit is 10 11 ⁇ / ⁇ .
  • the primary particle diameter of the light-shielding agent is appropriately selected depending on the application, such as the distance between the substrates of the display element, but the preferable lower limit is 30 nm and the preferable upper limit is 500 nm. It is. When the primary particle diameter of the light-shielding agent is less than 30 nm, the viscosity and thixotropy of the obtained light moisture-curable resin composition are greatly increased, and workability may be deteriorated.
  • the primary particle diameter of the light-shielding agent exceeds 500 nm, the dispersibility of the light-shielding agent in the obtained light moisture curable resin composition may be lowered, and the light-shielding property may be lowered.
  • the more preferable lower limit of the primary particle diameter of the light shielding agent is 50 nm, and the more preferable upper limit is 200 nm.
  • a preferable minimum is 0.05 weight% and a preferable upper limit is 10 weight%. If the content of the light shielding agent is less than 0.05% by weight, sufficient light shielding properties may not be obtained. When the content of the light-shielding agent is more than 10% by weight, the adhesiveness of the obtained light moisture curable resin composition to the substrate or the strength after curing may be lowered, or the drawing property may be lowered.
  • the more preferable lower limit of the content of the light shielding agent is 0.1% by weight, the more preferable upper limit is 2% by weight, the still more preferable lower limit is 0.3% by weight, and the still more preferable upper limit is 1% by weight.
  • the light moisture curable resin composition of the present invention contains a radically polymerizable compound.
  • the radical polymerizable compound is not particularly limited as long as it is a compound having a radical reactive functional group in the molecule, but a compound having an unsaturated double bond as the radical reactive functional group is suitable, and particularly reactive.
  • a resin having a (meth) acryloyl group (hereinafter, also referred to as “(meth) acrylic resin”) is preferable.
  • the “(meth) acryloyl group” means an acryloyl group or a methacryloyl group
  • the “(meth) acryl” means acryl or methacryl.
  • Examples of the (meth) acrylic resin include an ester compound obtained by reacting a compound having a hydroxyl group with (meth) acrylic acid, and an epoxy (meta) obtained by reacting (meth) acrylic acid with an epoxy compound.
  • the “(meth) acrylate” means acrylate or methacrylate.
  • Examples of the monofunctional compounds of the ester compounds include phthalimide acrylates such as N-acryloyloxyethyl hexahydrophthalimide, various imide acrylates, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, isobutyl (meth) acrylate, t-butyl (meth) acrylate, isooctyl (meth) acrylate, lauryl (meth) acrylate, stearyl (meth) acrylate, Isobornyl (meth) acrylate, cyclohexyl (meth) acrylate, 2-methoxyethyl (meth) acrylate, methoxyethylene glycol (meth) acrylate, 2-ethoxyethyl (Meth) acrylate, tetrahydrofurfuryl (me
  • bifunctional ester compound examples include 1,4-butanediol di (meth) acrylate, 1,3-butanediol di (meth) acrylate, and 1,6-hexanediol di (meth).
  • ester compound having three or more functional groups examples include pentaerythritol tri (meth) acrylate, trimethylolpropane tri (meth) acrylate, propylene oxide-added trimethylolpropane tri (meth) acrylate, and ethylene oxide-added trimethylol.
  • 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 as a raw material for synthesizing the epoxy (meth) acrylate include bisphenol A type epoxy resin, bisphenol F type epoxy resin, bisphenol S type epoxy resin, and 2,2′-diallyl bisphenol A type epoxy resin. , Hydrogenated bisphenol type epoxy resin, propylene oxide added bisphenol A type epoxy resin, resorcinol type epoxy resin, biphenyl type epoxy resin, sulfide type epoxy resin, diphenyl ether type epoxy resin, dicyclopentadiene type epoxy resin, naphthalene type epoxy resin, phenol Novolac epoxy resin, orthocresol novolac epoxy resin, dicyclopentadiene novolac epoxy resin, biphenyl novolac epoxy resin, naphtha Ren phenol novolak type epoxy resin, glycidyl amine type epoxy resin, alkyl polyol type epoxy resin, rubber modified epoxy resin, glycidyl ester compounds, bisphenol A type episulfide resins.
  • Examples of commercially available bisphenol A type epoxy resins include jER828EL, jER1001, jER1004 (all manufactured by Mitsubishi Chemical Corporation), Epicron 850-S (manufactured by DIC Corporation), and the like.
  • As what is marketed among the said bisphenol F-type epoxy resins jER806, jER4004 (all are the Mitsubishi Chemical company make) etc. are mentioned, for example.
  • As what is marketed among the said bisphenol S-type epoxy resins, Epicron EXA1514 (made by DIC Corporation) etc. are mentioned, for example.
  • Examples of commercially available 2,2′-diallylbisphenol A type epoxy resins include RE-810NM (manufactured by Nippon Kayaku Co., Ltd.).
  • Examples of commercially available diphenyl ether type epoxy resins include YSLV-80DE (manufactured by Nippon Steel & Sumikin Chemical Co., Ltd.).
  • Examples of commercially available dicyclopentadiene type epoxy resins include EP-4088S (manufactured by ADEKA).
  • Examples of commercially available naphthalene type epoxy resins include Epicron HP4032, Epicron EXA-4700 (both manufactured by DIC) and the like.
  • Examples of commercially available phenol novolac epoxy resins include Epicron N-770 (manufactured by DIC).
  • Examples of the ortho-cresol novolac type epoxy resin that are commercially available include epiclone N-670-EXP-S (manufactured by DIC).
  • Examples of commercially available glycidylamine type epoxy resins include jER630 (manufactured by Mitsubishi Chemical), Epicron 430 (manufactured by DIC), and TETRAD-X (manufactured by Mitsubishi Gas Chemical).
  • Examples of commercially available alkyl polyol type epoxy resins include ZX-1542 (manufactured by Nippon Steel & Sumikin Chemical Co., Ltd.), Epiklon 726 (manufactured by DIC), Epolite 80MFA (manufactured by Kyoeisha Chemical Co., Ltd.), Denacol EX-611. (Manufactured by Nagase ChemteX Corporation).
  • Examples of commercially available rubber-modified epoxy resins include YR-450, YR-207 (both manufactured by Nippon Steel & Sumikin Chemical Co., Ltd.), Epolide PB (manufactured by Daicel Corporation), and the like.
  • Examples of commercially available glycidyl ester compounds include Denacol EX-147 (manufactured by Nagase ChemteX Corporation).
  • Examples of commercially available bisphenol A type episulfide resins include jERYL-7000 (manufactured by Mitsubishi Chemical Corporation).
  • epoxy resins include, for example, YDC-1312, YSLV-80XY, YSLV-90CR (all manufactured by NS Also, Mitsubishi Chemical Corporation), EXA-7120 (DIC Corporation), TEPIC (Nissan Chemical Corporation) and the like.
  • Examples of commercially available epoxy (meth) acrylates include EBECRYL860, EBECRYL3200, EBECRYL3201, EBECRYL3412, EBECRYL3600, EBECRYL3700, EBECRYL3701, EBECRYL3702, EBECRY370R ), EA-1010, EA-1020, EA-5323, EA-5520, EA-CHD, EMA-1020 (all manufactured by Shin-Nakamura Chemical Co., Ltd.), epoxy ester M-600A, epoxy ester 40EM, epoxy ester 70PA, Epoxy ester 200PA, Epoxy ester 80MF Epoxy ester 3002M, Epoxy ester 3002A, Epoxy ester 1600A, Epoxy ester 3000M, Epoxy ester 3000A, Epoxy ester 200EA, Epoxy ester 400EA (all manufactured by Kyoeisha Chemical Co., Ltd.), Denacol acrylate DA-141, Denacol acrylate DA-3
  • the urethane (meth) acrylate is obtained, for example, by reacting 2 equivalents of a (meth) acrylic acid derivative having a hydroxyl group with 1 equivalent of a compound having two isocyanate groups in the presence of a catalytic amount of a tin-based compound. be able to.
  • Examples of the isocyanate used as a raw material for the urethane (meth) acrylate include isophorone diisocyanate, 2,4-tolylene diisocyanate, 2,6-tolylene diisocyanate, hexamethylene diisocyanate, trimethylhexamethylene diisocyanate, and diphenylmethane-4,4 ′.
  • MDI Diisocyanate
  • XDI xylylene diisocyanate
  • XDI hydrogenated XDI
  • lysine diisocyanate triphenylmethane triisocyanate
  • Thiophosphate tetramethylxylene diisocyanate, 1,6,11-undecane triisocyanate Doors and the like.
  • isocyanate examples include, for example, a reaction between a polyol such as ethylene glycol, glycerin, sorbitol, trimethylolpropane, (poly) propylene glycol, carbonate diol, polyether diol, polyester diol, polycaprolactone diol and excess isocyanate.
  • a polyol such as ethylene glycol, glycerin, sorbitol, trimethylolpropane, (poly) propylene glycol, carbonate diol, polyether diol, polyester diol, polycaprolactone diol and excess isocyanate.
  • a polyol such as ethylene glycol, glycerin, sorbitol, trimethylolpropane, (poly) propylene glycol, carbonate diol, polyether diol, polyester diol, polycaprolactone diol and excess isocyanate.
  • the resulting chain-extended isocyanate compound
  • Examples of the (meth) acrylic acid derivative having a hydroxyl group, which is a raw material of the urethane (meth) acrylate include, for example, ethylene glycol, propylene glycol, 1,3-propanediol, 1,3-butanediol, and 1,4-butane.
  • Examples include epoxy (meth) acrylates such as epoxy (meth) acrylate.
  • Examples of commercially available urethane (meth) acrylates include M-1100, M-1200, M-1210, M-1600 (all manufactured by Toagosei Co., Ltd.), EBECRYL230, EBECRYL270, EBECRYL4858, EBECRYL8402, EBECRYL8411, EBECRYL8412, EBECRYL8413, EBECRYL8804, EBECRYL8803, EBECRYL8807, EBECRYL9260, EBECRYL1290, EBECRYL5129, EBECRYL4842, EBECRYL210, EBECRYL4827, EBECRYL6700, EBECRYL220, EBECRYL2220, KRM7735, KRM-8295 (both manufactured by Daicel Orunekusu, Inc.
  • radical polymerizable compounds other than those described above can be used as appropriate.
  • the other radical polymerizable compounds include N, N-dimethyl (meth) acrylamide, N- (meth) acryloylmorpholine, N-hydroxyethyl (meth) acrylamide, N, N-diethyl (meth) acrylamide, Examples include (meth) acrylamide compounds such as N-isopropyl (meth) acrylamide and N, N-dimethylaminopropyl (meth) acrylamide, and vinyl compounds such as styrene, ⁇ -methylstyrene, N-pyropidone, and N-vinylcaprolactone. .
  • the radical polymerizable compound preferably contains a monofunctional radical polymerizable compound and a polyfunctional radical polymerizable compound from the viewpoint of adjusting curability.
  • a monofunctional radical polymerizable compound When only a monofunctional radically polymerizable compound is used, the resulting light moisture curable resin composition may be inferior in curability, and when only a polyfunctional radically polymerizable compound is used, the resulting light moisture cured
  • the mold resin composition may be inferior in tackiness.
  • the polyfunctional radically polymerizable compound is preferably bifunctional or trifunctional, and more preferably bifunctional.
  • the radical polymerizable compound contains the monofunctional radical polymerizable compound and the polyfunctional radical polymerizable compound
  • the content of the polyfunctional radical polymerizable compound is the same as the monofunctional radical polymerizable compound and the polyfunctional radical polymerizable compound.
  • a preferable lower limit is 2 parts by weight and a preferable upper limit is 30 parts by weight with respect to a total of 100 parts by weight with the functional radical polymerizable compound.
  • the content of the polyfunctional radically polymerizable compound is less than 2 parts by weight, the resulting light moisture curable resin composition may be inferior in curability.
  • content of the said polyfunctional radically polymerizable compound exceeds 30 weight part, the optical moisture hardening type resin composition obtained may become inferior to tackiness.
  • the minimum with more preferable content of the said polyfunctional radically polymerizable compound is 5 weight part, and a more preferable upper limit is 20 weight part.
  • the optical moisture curable resin composition of the present invention contains a moisture curable urethane resin.
  • the isocyanate group in the molecule is cured by reacting with moisture in the air or in the adherend.
  • the obtained optical moisture hardening type resin composition is excellent in quick-curing property.
  • the moisture curable urethane resin may have only one isocyanate group in one molecule, or may have two or more. Of these, urethane prepolymers having isocyanate groups at both ends are preferred.
  • the urethane prepolymer can be obtained by reacting a polyol compound having two or more hydroxyl groups in one molecule with a polyisocyanate compound having two or more isocyanate groups in one molecule.
  • polyol compound the well-known polyol compound normally used for manufacture of a polyurethane can be used, For example, polyester polyol, polyether polyol, polyalkylene polyol, polycarbonate polyol etc. are mentioned. These polyol compounds may be used independently and may be used in combination of 2 or more type.
  • polyester polyol examples include a polyester polyol obtained by a reaction between a polyvalent carboxylic acid and a polyol, and a poly- ⁇ -caprolactone polyol obtained by ring-opening polymerization of ⁇ -caprolactone.
  • polyvalent carboxylic acid used as a raw material for the polyester polyol examples include terephthalic acid, isophthalic acid, 1,5-naphthalic acid, 2,6-naphthalic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, and suberin.
  • examples include acid, azelaic acid, sebacic acid, decamethylene dicarboxylic acid, dodecamethylene dicarboxylic acid and the like.
  • polyester polyol examples include ethylene glycol, propylene glycol, 1,3-propanediol, 1,4-butanediol, neopentyl glycol, 1,5-pentanediol, and 1,6-hexane.
  • Diol, diethylene glycol, cyclohexanediol, etc. are mentioned.
  • polyether polyol examples include ring-opening polymers of ethylene glycol, propylene glycol, tetrahydrofuran, 3-methyltetrahydrofuran, random copolymers or block copolymers of these and their derivatives, and bisphenol-type polyoxy An alkylene modified body etc. are mentioned.
  • the modified bisphenol-type polyoxyalkylene is a polyether polyol obtained by addition reaction of alkylene oxide (for example, ethylene oxide, propylene oxide, butylene oxide, isobutylene oxide, etc.) to the active hydrogen portion of the bisphenol-type molecular skeleton, A random copolymer or a block copolymer may be used.
  • the modified bisphenol-type polyoxyalkylene preferably has one or more alkylene oxides added to both ends of the bisphenol-type molecular skeleton. It does not specifically limit as a bisphenol type, A type, F type, S type etc. are mentioned, Preferably it is bisphenol A type.
  • polyalkylene polyol examples include polybutadiene polyol, hydrogenated polybutadiene polyol, and hydrogenated polyisoprene polyol.
  • polycarbonate polyol examples include polyhexamethylene carbonate polyol and polycyclohexane dimethylene carbonate polyol.
  • polyisocyanate compound examples include diphenylmethane diisocyanate, a liquid modified product of diphenylmethane diisocyanate, polymeric MDI (methane diisocyanate), tolylene diisocyanate, naphthalene-1,5-diisocyanate, and the like.
  • diphenylmethane diisocyanate and its modified products are preferred from the viewpoint of low vapor pressure, low toxicity, and ease of handling.
  • the said polyisocyanate compound may be used independently and may be used in combination of 2 or more type.
  • the said moisture hardening type urethane resin is obtained using the polyol compound which has a structure represented by following formula (1).
  • a polyol compound having a structure represented by the following formula (1) it is possible to obtain a composition excellent in adhesiveness and a cured product that is flexible and has good elongation, and is compatible with the radical polymerizable compound. It will be excellent.
  • a polyether polyol composed of a ring-opening polymerization compound of propylene glycol, a tetrahydrofuran (THF) compound, or a ring-opening polymerization compound of a tetrahydrofuran compound having a substituent such as a methyl group.
  • R represents hydrogen, a methyl group, or an ethyl group
  • n is an integer of 1 to 10
  • L is an integer of 0 to 5
  • m is an integer of 1 to 500.
  • n is preferably 1 to 5
  • L is preferably 0 to 4
  • m is preferably 50 to 200.
  • L is 0 means the case where carbon bonded to R is directly bonded to oxygen.
  • the moisture curable urethane resin may have a radical polymerizable functional group.
  • the radical polymerizable functional group that the moisture curable urethane resin may have is preferably a group having an unsaturated double bond, and more preferably a (meth) acryloyl group from the viewpoint of reactivity.
  • the moisture curable urethane resin having a radical polymerizable functional group is not included in the radical polymerizable compound and is treated as a moisture curable urethane resin.
  • the preferable lower limit of the weight average molecular weight of the moisture curable urethane resin is 800, and the preferable upper limit is 10,000.
  • the weight average molecular weight of the moisture curable urethane resin is less than 800, the crosslink density increases and flexibility may be impaired.
  • the weight average molecular weight of the moisture curable urethane resin exceeds 10,000, the resulting light moisture curable resin composition may have poor applicability.
  • the more preferable lower limit of the weight average molecular weight of the moisture curable urethane resin is 2000, the more preferable upper limit is 8000, the still more preferable lower limit is 3000, and the more preferable upper limit is 6000.
  • the said weight average molecular weight is a value calculated
  • GPC gel permeation chromatography
  • Examples of the column for measuring the weight average molecular weight in terms of polystyrene by GPC include Shodex LF-804 (manufactured by Showa Denko KK). Moreover, tetrahydrofuran etc. are mentioned as a solvent used by GPC.
  • the content of the moisture curable urethane resin is preferably 20 parts by weight with a preferred lower limit and 90 parts by weight with respect to a total of 100 parts by weight of the radical polymerizable compound and the moisture curable urethane resin.
  • the resulting optical moisture curable resin composition may be inferior in moisture curable property. If the content of the moisture curable urethane resin exceeds 90 parts by weight, the resulting light moisture curable resin composition may be inferior in photocurability.
  • a more preferable lower limit of the content of the moisture curable urethane resin is 30 parts by weight, a more preferable upper limit is 75 parts by weight, a still more preferable lower limit is 41 parts by weight, and a still more preferable upper limit is 70 parts by weight.
  • the light moisture curable resin composition of the present invention contains a radical photopolymerization initiator.
  • the photo radical polymerization initiator include benzophenone compounds, acetophenone compounds, acylphosphine oxide compounds, titanocene compounds, oxime ester compounds, benzoin ether compounds, thioxanthones, and the like.
  • Acylphosphine oxide compounds are preferred because a composition that is particularly excellent in (deep part curability) can be obtained.
  • the photo radical polymerization initiator is preferably one that can be sensitized by irradiation with light in a wavelength region of 370 to 450 nm as described above.
  • acylphosphine oxide compound examples include bis (2,4,6-trimethylbenzoyl) -phenylphosphine oxide, 2,4,6-trimethylbenzoyldiphenylphosphine oxide, and the like.
  • Examples of the commercially available photo radical polymerization initiators include IRGACURE 184, IRGACURE 369, IRGACURE 379, IRGACURE 651, IRGACURE 784, IRGACURE 907, IRGACURE 907, IRGACURE 2959, IRGACURE4, IRGACUREO1P
  • Examples include benzoin methyl ether, benzoin ethyl ether, and benzoin isopropyl ether (all manufactured by Tokyo Chemical Industry Co., Ltd.).
  • the content of the photo radical polymerization initiator is preferably 0.01 parts by weight and preferably 10 parts by weight with respect to 100 parts by weight of the radical polymerizable compound.
  • the content of the radical photopolymerization initiator is less than 0.01 part by weight, the resulting light moisture curable resin composition may not be sufficiently photocured.
  • content of the said radical photopolymerization initiator exceeds 10 weight part, the storage stability of the obtained optical moisture hardening type resin composition may fall.
  • the minimum with more preferable content of the said radical photopolymerization initiator is 0.1 weight part, and a more preferable upper limit is 5 weight part.
  • the light moisture curable resin composition of the present invention may contain a sensitizer.
  • the sensitizer By containing the sensitizer, the light moisture curable resin composition of the present invention can provide a light moisture curable resin composition having high sensitivity and excellent photocurability.
  • the sensitizer preferably exhibits a sensitizing effect when irradiated with light in a wavelength region of 370 to 450 nm.
  • the sensitizer is preferably selected from the group consisting of a benzophenone skeleton, an anthracene skeleton, an anthraquinone skeleton, a coumarin skeleton, a thioxanthone skeleton, and a phthalocyanine skeleton because it preferably has a sufficient light absorption band in the ultraviolet / visible region. It is preferable to contain a compound having at least one skeleton, and it is more preferable to contain a compound having at least one skeleton selected from the group consisting of an anthracene skeleton, an anthraquinone skeleton, and a thioxanthone skeleton. These compounds can also be used as the photo radical polymerization initiator.
  • Examples of the compound having a benzophenone skeleton include benzophenone, 2,4-dichlorobenzophenone, 4,4′-bis (dimethylamino) benzophenone, 4,4′-bis (diethylamino) benzophenone, and the like.
  • Examples of the compound having an anthracene skeleton include 9,10-dibutoxyanthracene, 9,10-diproxyanthraquinone, and 9,10-ethoxyanthraquinone.
  • Examples of the compound having an anthraquinone skeleton include 2-ethylanthraquinone, 1-methylanthraquinone, 1,4-dihydroxyanthraquinone, 2- (2-hydroxyethoxy) -anthraquinone and the like.
  • Examples of the compound having a coumarin skeleton include 7-diethylamino-4-methylcoumarin.
  • Examples of the compound having a thioxanthone skeleton include 2,4-diethylthioxanthone, 2-chlorothioxanthone, 4-isopropylthioxanthone, 1-chloro-4-propylthioxanthone, and the like.
  • Examples of the compound having a phthalocyanine skeleton include phthalocyanine.
  • the resulting light moisture curable resin composition is particularly excellent in curability of the light-shielding part. Therefore, 4,4′-bis (dimethylamino) benzophenone and 4,4′- At least one of bis (diethylamino) benzophenone is preferably used.
  • the content of the sensitizer is such that a preferred lower limit is 2 parts by weight and a preferred upper limit is 50 parts by weight with respect to 100 parts by weight of the photopolymerization initiator.
  • a preferred lower limit is 2 parts by weight
  • a preferred upper limit is 50 parts by weight with respect to 100 parts by weight of the photopolymerization initiator.
  • the sensitizing effect may not be sufficiently exhibited.
  • content of the said sensitizer exceeds 50 weight part, the storage stability of the obtained optical moisture hardening type resin composition may fall.
  • the minimum with more preferable content of the said sensitizer is 5 weight part, and a more preferable upper limit is 40 weight part.
  • the light moisture curable resin composition of the present invention may contain a filler from the viewpoint of adjusting the applicability and shape retention of the resulting light moisture curable resin composition.
  • the light moisture curable resin composition of the present invention has suitable thixotropy and can sufficiently retain the shape after coating.
  • the filler preferably has a primary particle diameter with a preferred lower limit of 1 nm and a preferred upper limit of 50 nm.
  • the primary particle diameter of the filler is less than 1 nm, the resulting light moisture curable resin composition may be inferior in applicability.
  • the primary particle diameter of the filler exceeds 50 nm, the resulting light moisture curable resin composition may be inferior in shape retention after coating.
  • the more preferable lower limit of the primary particle diameter of the filler is 5 nm, the more preferable upper limit is 30 nm, the still more preferable lower limit is 10 nm, and the still more preferable upper limit is 20 nm.
  • the primary particle size of the filler can be measured by dispersing the filler in a solvent (water, organic solvent, etc.) using NICOMP 380ZLS (manufactured by PARTICS SIZING SYSTEMS).
  • the filler may be present as secondary particles (a collection of a plurality of primary particles) in the light moisture curable resin composition of the present invention, and the preferred lower limit of the particle diameter of such secondary particles. Is 5 nm, the preferred upper limit is 500 nm, the more preferred lower limit is 10 nm, and the more preferred upper limit is 100 nm.
  • the particle diameter of the secondary particles of the filler can be measured by observing the optical moisture curable resin composition of the present invention or a cured product thereof using a transmission electron microscope (TEM).
  • TEM transmission electron microscope
  • an inorganic filler is preferable, and examples thereof include silica, talc, titanium oxide, zinc oxide, calcium carbonate and the like. Among these, silica is preferable because the obtained light moisture curable resin composition is excellent in UV light transmittance.
  • These fillers may be used independently and may be used in combination of 2 or more type.
  • the filler is preferably subjected to a hydrophobic surface treatment.
  • a hydrophobic surface treatment By the hydrophobic surface treatment, the resulting optical moisture curable resin composition is more excellent in shape retention after application.
  • the hydrophobic surface treatment include silylation treatment, alkylation treatment, and epoxidation treatment. Especially, since it is excellent in the effect which improves shape retainability, a silylation process is preferable and a trimethylsilylation process is more preferable.
  • Examples of the method for treating the filler with a hydrophobic surface include a method for treating the surface of the filler with a surface treatment agent such as a silane coupling agent.
  • a surface treatment agent such as a silane coupling agent.
  • the trimethylsilylated silica is prepared by, for example, synthesizing silica by a method such as a sol-gel method and spraying hexamethyldisilazane in a state where the silica is fluidized, or an organic solvent such as alcohol or toluene. It can be produced by a method in which silica is added, hexamethyldisilazane and water are added, and then water and an organic solvent are evaporated and dried with an evaporator.
  • the content of the filler is preferably 0.1 parts by weight with a preferable lower limit and 20 parts by weight with respect to 100 parts by weight of the entire optical moisture-curable resin composition of the present invention.
  • the content of the filler is less than 0.1 parts by weight, the obtained light moisture curable resin composition may be inferior in shape retention after coating.
  • content of the said filler exceeds 20 weight part, the optical moisture hardening type resin composition obtained may become inferior to applicability
  • the more preferred lower limit of the content of the filler is 0.5 parts by weight, the more preferred upper limit is 15 parts by weight, the still more preferred lower limit is 1 part by weight, the still more preferred upper limit is 12 parts by weight, and the particularly preferred lower limit is 2 parts by weight. It is.
  • the light moisture curable resin composition of the present invention may further contain additives such as an ionic liquid, a solvent, metal-containing particles, and a reactive diluent as necessary.
  • a method for producing the light moisture curable resin composition of the present invention for example, using a mixer such as a homodisper, a homomixer, a universal mixer, a planetary mixer, a kneader, a three roll, And a method of mixing a moisture curable urethane resin, a radical photopolymerization initiator, a light shielding agent, and an additive to be added as necessary.
  • a mixer such as a homodisper, a homomixer, a universal mixer, a planetary mixer, a kneader, a three roll, And a method of mixing a moisture curable urethane resin, a radical photopolymerization initiator, a light shielding agent, and an additive to be added as necessary.
  • the light moisture curable resin composition of the present invention is rapidly cured by light irradiation and can be sufficiently cured by moisture curing.
  • a light source used when photocuring the optical moisture curable resin composition of the present invention not only a generally used high pressure mercury lamp and metal halide lamp but also an LED light source can be used. .
  • the optical density (OD value) of a cured product having a thickness of 1 mm after curing is preferably 1 or more.
  • the OD value is less than 1, the light shielding property is insufficient, and when used in a display element, light leaks out and high contrast may not be obtained.
  • the OD value is more preferably 1.5 or more. The higher the OD value, the better.
  • the preferable upper limit of the OD value of the cured product is 4.
  • the OD value after hardening of the said optical moisture curable resin composition can be measured using an optical densitometer.
  • cured material which measures the said OD value can be obtained by irradiating an ultraviolet ray of 500 mJ / cm ⁇ 2 > using a high pressure mercury lamp etc.
  • the preferable lower limit of the viscosity measured at 25 ° C. and 1 rpm using a cone plate viscometer is 50 Pa ⁇ s
  • the preferable upper limit is 500 Pa ⁇ s.
  • the viscosity is less than 50 Pa ⁇ s or more than 500 Pa ⁇ s
  • the light moisture curable resin composition is applied to an adherend such as a substrate when used as an adhesive for electronic parts or an adhesive for display elements. The workability when doing so may deteriorate.
  • a more preferred lower limit of the viscosity is 80 Pa ⁇ s
  • a more preferred upper limit is 300 Pa ⁇ s
  • a still more preferred upper limit is 200 Pa ⁇ s.
  • the preferable lower limit of the thixotropic index of the light moisture curable resin composition of the present invention is 1.3, and the preferable upper limit is 5.0.
  • the thixotropic index is less than 1.3 or exceeds 5.0, an adherend such as a substrate is used when the optical moisture curable resin composition is used as an adhesive for electronic parts or an adhesive for display elements. The workability at the time of applying to may be deteriorated.
  • the more preferable lower limit of the thixotropic index is 1.5, and the more preferable upper limit is 4.0.
  • the thixotropic index is a viscosity measured at 25 ° C. and 1 rpm using a cone plate viscometer, and measured at 25 ° C. and 10 rpm using a cone plate viscometer. It means the value divided by the viscosity.
  • the light moisture curable resin composition of the present invention can be particularly suitably used as an adhesive for electronic parts or an adhesive for display elements.
  • An adhesive for electronic components using the light moisture curable resin composition of the present invention and a display element adhesive using the light moisture curable resin composition of the present invention are also included in the present invention. It is.
  • the optical moisture hardening type resin composition excellent in light-shielding property and adhesiveness can be provided.
  • (A) is a schematic diagram which shows the case where the sample for adhesive evaluation is seen from the top
  • (b) is the schematic diagram which shows the case where the sample for adhesive evaluation is seen from the side.
  • the present invention will be described in more detail with reference to examples. However, the present invention is not limited to these examples. Moreover, according to this invention, the adhesive for electronic components and the adhesive for display elements which use this optical moisture hardening type resin composition can be provided.
  • Example 1 to 16 Comparative Examples 1 and 2
  • each material was stirred with a planetary stirrer (manufactured by Shinky Co., Ltd., “Awatori Netaro”) and then mixed uniformly with a ceramic three roll.
  • the optical moisture curable resin compositions of Examples 1 to 16 and Comparative Examples 1 and 2 were obtained.
  • “urethane prepolymer A” is a urethane prepolymer having isocyanate groups at both ends described in Synthesis Example 1
  • urethane prepolymer B is an isocyanate at both ends described in Synthesis Example 2.
  • the “urethane prepolymer C” is a urethane prepolymer having an isocyanate group and a methacryloyl group at the molecular end described in Synthesis Example 3.
  • OD value Light shielding (OD value)
  • Each of the light moisture curable resin compositions obtained in the examples and comparative examples was coated on release polyethylene terephthalate (PET) using 1 mm thick Teflon (registered trademark) pieces as a gap agent, and further released thereon.
  • PET polyethylene terephthalate
  • Teflon registered trademark
  • the mold PET was stacked and pressed with glass to a uniform thickness, and then the light moisture curable resin composition was photocured by irradiating with 500 mJ / cm 2 of ultraviolet rays using a high pressure mercury lamp. Thereafter, the sample was allowed to stand overnight to be moisture-cured to obtain a 1 mm thick sample for evaluating light shielding properties.
  • optical density (OD value) was measured using the optical densitometer (the product made from X-rite, "spectrometer").
  • FIG. 1 is a schematic diagram (FIG. 1 (a)) showing a case where an adhesive evaluation sample is viewed from above, and a schematic diagram showing a case where the adhesive evaluation sample is viewed from the side (FIG. 1 (b)). showed that.
  • the produced adhesive evaluation sample was pulled at a rate of 5 mm / sec in the shear direction using a tensile tester, and the strength when the substrate was peeled was measured.
  • ⁇ means that a part of the cured product remains on the substrate (partially deep-cured part), and “ ⁇ ” indicates that the cured substance almost remains on the substrate (substantially deep-cured part).
  • the hard part was not removed from the substrate (the hard part was hard), and the deep part curability was evaluated as “ ⁇ ”.
  • the optical moisture hardening type resin composition excellent in light-shielding property and adhesiveness can be provided.
  • the adhesive for electronic components and the adhesive for display elements which use this optical moisture hardening type resin composition can be provided.

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Abstract

L'objet de la présente invention est de pourvoir à une composition de résine durcissable par exposition à la lumière/humidité qui manifeste d'excellents propriétés de protection contre la lumière et d'excellentes propriétés adhésives. Un autre objet de la présente invention est de pourvoir à un adhésif pour composants électroniques et à un adhésif pour éléments d'affichage, lesdits adhésifs comprenant ladite composition de résine durcissable par exposition à la lumière/humidité. La solution selon l'invention porte sur une composition de résine durcissable par exposition à la lumière/humidité qui contient un composé polymérisable par voie radicalaire, une résine uréthanne durcissable par exposition à l'humidité, un amorceur de polymérisation photoradicalaire, et un agent de protection contre la lumière.
PCT/JP2015/051354 2014-01-21 2015-01-20 Composition de résine durcissable par exposition à la lumière/humidité, adhésif pour composants électroniques, et adhésif pour éléments d'affichage WO2015111570A1 (fr)

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KR1020157033386A KR102242601B1 (ko) 2014-01-21 2015-01-20 광 습기 경화형 수지 조성물, 전자 부품용 접착제, 및 표시 소자용 접착제
CN202210318888.8A CN114702631A (zh) 2014-01-21 2015-01-20 光湿气固化型树脂组合物、电子部件用粘接剂和显示元件用粘接剂
JP2015508352A JP5845377B1 (ja) 2014-01-21 2015-01-20 電子部品用接着剤、及び、表示素子用接着剤
KR1020217011028A KR102372448B1 (ko) 2014-01-21 2015-01-20 광 습기 경화형 수지 조성물, 전자 부품용 접착제, 및 표시 소자용 접착제

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WO2023153514A1 (fr) * 2022-02-14 2023-08-17 積水化学工業株式会社 Composition de résine photodurcissable/durcissable à l'humidité, adhésif pour composant électronique et adhésif pour élément d'affichage

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KR102410694B1 (ko) * 2014-06-11 2022-06-17 세키스이가가쿠 고교가부시키가이샤 광 습기 경화형 수지 조성물, 전자 부품용 접착제 및 표시 소자용 접착제
JP6510788B2 (ja) * 2014-10-03 2019-05-08 積水化学工業株式会社 光湿気硬化型樹脂組成物
CN110105530B (zh) * 2019-05-10 2021-05-11 广州回天新材料有限公司 一种uv湿气双固化树脂制备方法
JPWO2022114186A1 (fr) * 2020-11-30 2022-06-02
CN115353810B (zh) * 2022-09-08 2024-01-30 杭州之江有机硅化工有限公司 一种uv和湿气双重固化胶粘剂及其制备方法和应用

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