WO2016167305A1 - Corps durci, composant électronique, élément d'affichage, et composition de résine durcissable à la lumière/l'humidité - Google Patents

Corps durci, composant électronique, élément d'affichage, et composition de résine durcissable à la lumière/l'humidité Download PDF

Info

Publication number
WO2016167305A1
WO2016167305A1 PCT/JP2016/061958 JP2016061958W WO2016167305A1 WO 2016167305 A1 WO2016167305 A1 WO 2016167305A1 JP 2016061958 W JP2016061958 W JP 2016061958W WO 2016167305 A1 WO2016167305 A1 WO 2016167305A1
Authority
WO
WIPO (PCT)
Prior art keywords
curable resin
light
meth
resin composition
moisture curable
Prior art date
Application number
PCT/JP2016/061958
Other languages
English (en)
Japanese (ja)
Inventor
高橋　徹
彰 結城
拓身 木田
Original Assignee
積水化学工業株式会社
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
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 JP2016526962A priority Critical patent/JP6698524B2/ja
Priority to KR1020177007155A priority patent/KR102260532B1/ko
Priority to CN201680003536.6A priority patent/CN107108772A/zh
Publication of WO2016167305A1 publication Critical patent/WO2016167305A1/fr

Links

Images

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
    • C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
    • 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
    • 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
    • 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
    • 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
    • C09J201/00—Adhesives based on unspecified macromolecular compounds
    • C09J201/02—Adhesives based on unspecified macromolecular compounds characterised by the presence of specified groups, e.g. terminal or pendant functional groups
    • 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
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
    • H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
    • H01L21/04—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer
    • H01L21/50—Assembly of semiconductor devices using processes or apparatus not provided for in a single one of the subgroups H01L21/06 - H01L21/326, e.g. sealing of a cap to a base of a container
    • H01L21/52—Mounting semiconductor bodies in containers
    • 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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step

Definitions

  • the present invention relates to a cured product having excellent flexibility and reliability. Moreover, this invention relates to the electronic component and display element which use this hardening body. Furthermore, the present invention relates to a light moisture curable resin composition that is suitable for production of the cured product and is excellent in coating property, shape retention property, and adhesiveness.
  • 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, adhering various members such as a substrate, an optical film, and a protective film.
  • 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.
  • a photothermosetting resin composition is used as a resin composition that can be sufficiently cured even when applied to a portion where light does not reach, and photocuring and thermosetting are also used in combination. There was a possibility of adversely affecting the elements and the like by heating.
  • Patent Document 1 discloses a thermosetting adhesive containing an epoxy compound having a number average molecular weight of 600 to 1,000.
  • the thermosetting adhesive as disclosed in Patent Document 1 is not suitable for bonding electronic components that may be damaged by heat.
  • Patent Documents 2 and 3 contain a urethane prepolymer having at least one isocyanate group and at least one (meth) acryloyl group in the molecule.
  • a method of using both photocuring and moisture curing using a photomoisture curable resin composition is disclosed.
  • the optical moisture curable resin composition as disclosed in Patent Documents 2 and 3 is used, the resin composition after application cannot be maintained in shape and spreads or adheres to an adherend such as a substrate. There has been a problem that the adhesiveness is insufficient.
  • An object of this invention is to provide the hardening body excellent in a softness
  • the present invention is a cured product of an optical moisture curable resin composition containing a radical polymerizable compound and a moisture curable resin, and has a tensile strength at 400% elongation at 25 ° C. of 3 kgf / cm 2 or more, 20 kgf. It is a cured body that is / cm 2 or less.
  • the present invention is described in detail below.
  • the inventors of the present invention provide a light moisture curable resin composition containing a radical polymerizable compound and a moisture curable resin, and a cured product obtained by light moisture curing the composition at 25 ° C.
  • a light moisture curable resin composition containing a radical polymerizable compound and a moisture curable resin
  • a cured product obtained by light moisture curing the composition at 25 ° C.
  • the cured product of the present invention has a lower limit of tensile strength at 400% elongation at 25 ° C. of 3 kgf / cm 2 and an upper limit of 20 kgf / cm 2 .
  • the cured product of the present invention is heated by a change in temperature when a force is applied to the adherend in the shear direction or the bending direction. Even when stress is generated, excellent adhesion and flexibility can be maintained.
  • a preferred lower limit of the tensile strength at 400% elongation in the 25 ° C. is 5 kgf / cm 2, a preferred upper limit 17 kgf / cm 2, more preferred lower limit is 8 kgf / cm 2.
  • the tensile strength at 400% elongation at 25 ° C. means a force when the tensile strength is extended to 4 times that before the tensile test.
  • an optical moisture curable resin composition is photocured by irradiating ultraviolet light with a wavelength of 365 nm using an ultraviolet LED (UV-LED) or the like at 1000 mJ / cm 2 , and then 25 ° C., 50% RH.
  • UV-LED ultraviolet LED
  • a tensile tester for example, “EZ-Graph” manufactured by Shimadzu Corporation
  • EZ-Graph manufactured by Shimadzu Corporation
  • the measurement of the tensile strength and the tensile elongation at break described later is the state in which the bonded substrates are peeled off. Do. Even when it does not become a dumbbell shape, it can be obtained in the same manner by converting the thickness and width of the cured body in the peeled state.
  • the preferred lower limit of the tensile elongation at break at 25 ° C. is 500%.
  • the cured product of the present invention generates thermal stress due to temperature change when force is applied to the adherend in the shearing direction or bending direction. In such a case, the effect of maintaining excellent adhesiveness and flexibility is superior.
  • a more preferable lower limit of the tensile elongation at break at 25 ° C. is 600%. The tensile elongation at break at 25 ° C.
  • the light moisture curable resin composition was specifically obtained by photocuring the light moisture curable resin composition by, for example, irradiating ultraviolet light having a wavelength of 365 nm with 1000 mJ / cm 2 using an ultraviolet LED lamp or the like. After that, it is cured by dampening by allowing it to stand for 72 hours or more at 25 ° C. and 50% RH, and the resulting cured product is punched into a dumbbell shape (No. 6 as defined in “JIS K 6251”). The elongation at break when the test piece was pulled at a rate of 5 mm / min using a tensile tester (eg, “EZ-Graph” manufactured by Shimadzu Corporation) at 25 ° C. can be obtained.
  • a tensile tester eg, “EZ-Graph” manufactured by Shimadzu Corporation
  • the preferred lower limit of the tensile shear adhesive strength to polycarbonate and glass measured at 25 ° C. according to JIS K 6850 is 10 kgf / cm 2 .
  • the cured product of the present invention is subjected to a temperature change when a force is applied to the adherend in the shear direction or the bending direction. In the case where thermal stress is generated, the effect of maintaining excellent adhesiveness is improved.
  • a more preferred lower limit of the tensile shear bond strength to the polycarbonate and glass is 15 kgf / cm 2 .
  • the tensile shear bond strength to the polycarbonate and glass is specifically, for example, by applying a light moisture curable resin composition on a polycarbonate substrate with a width of about 1 mm, and using an ultraviolet LED lamp or the like at a wavelength of 365 nm. After photocuring the light moisture curable resin composition by irradiating with 1000 mJ / cm 2 of ultraviolet rays, the glass substrate is overlaid, a 20 g weight is placed, and it is allowed to stand for 72 hours or more at 25 ° C. and 50% RH.
  • the test piece obtained by moisture-curing the optical moisture-curable resin composition was 10 mm in the shear direction at 25 ° C. using a tensile tester (for example, “EZ-Graph” manufactured by Shimadzu Corporation). It can be measured by pulling at a rate of / min.
  • the cured product of the present invention has a preferred lower limit of storage modulus at 80 ° C. of 1 ⁇ 10 5 Pa and a preferred upper limit of 1 ⁇ 10 7 Pa.
  • the storage elastic modulus at 80 ° C. is within this range, the cured product of the present invention has suitable flexibility even at high temperatures and is excellent in reliability.
  • the more preferable lower limit of the storage elastic modulus at 80 ° C. is 8 ⁇ 10 5 Pa, and the more preferable upper limit is 5 ⁇ 10 6 Pa.
  • the storage elastic modulus at 80 ° C. can be measured by using a dynamic viscoelasticity measuring apparatus (for example, “DVA-200” manufactured by IT Measurement Control Co., Ltd.).
  • the cured product of the present invention is a cured product of an optical moisture curable resin composition containing a radical polymerizable compound and a moisture curable resin.
  • a light moisture curable resin composition that becomes a cured product of the present invention by light moisture curing that is, a light moisture curable resin composition containing a radical polymerizable compound and a moisture curable resin.
  • An optical moisture curable resin composition having a tensile strength at 400% elongation at 25 ° C. of 3 to 20 kgf / cm 2 is also one aspect of the present invention.
  • the radical polymerizable compound has a high flexibility of the cured product (low tensile strength), weak adhesive strength, and tends to stretch well (high elongation at break).
  • the moisture curable resin has a low flexibility of the cured product, a strong adhesive force, and tends to grow well. Therefore, the tensile strength and the like of the cured product can be adjusted to the above-described range by adjusting the types of compounds used as these components, the blending ratio thereof, the glass transition temperature, the crosslinking density, and the like. Moreover, if it is the range which does not inhibit the objective of this invention, the tensile strength of a hardening body etc. can be adjusted to the range mentioned above also by adjusting the kind and compounding quantity of a filler etc. which are mentioned later.
  • 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 radical polymerizable compound having photopolymerizability, and is a compound having a radical reactive functional group in the molecule.
  • a compound having a heavy bond is preferable, and a compound having a (meth) acryloyl group (hereinafter also referred to as “(meth) acrylic compound”) is particularly preferable from the viewpoint of reactivity.
  • the “(meth) acryloyl” means acryloyl or methacryloyl
  • the “(meth) acryl” means acryl or methacryl.
  • (meth) acrylic compound for example, (meth) acrylic acid ester compound obtained by reacting (meth) acrylic acid with a compound having a hydroxyl group, (meth) acrylic acid and epoxy compound are reacted.
  • examples include epoxy (meth) acrylates obtained, urethane (meth) acrylates obtained by reacting an isocyanate compound with a (meth) acrylic acid derivative having a hydroxyl group.
  • the “(meth) acrylate” means acrylate or methacrylate.
  • all the isocyanate groups of the isocyanate compound used as the raw material of the said urethane (meth) acrylate are used for formation of a urethane bond, and the said urethane (meth) acrylate does not have a residual isocyanate group.
  • monofunctional ones include, for example, phthalimide acrylates such as N-acryloyloxyethyl hexahydrophthalimide, various imide acrylates, methyl (meth) acrylate, ethyl (meth) acrylate, propyl (Meth) acrylate, n-butyl (meth) acrylate, isobutyl (meth) acrylate, t-butyl (meth) acrylate, n-octyl (meth) acrylate, isooctyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, isononyl (Meth) acrylate, isodecyl (meth) acrylate, lauryl (meth) acrylate, isomyristyl (meth) acrylate, stearyl (meth) acrylate, cyclohexyl (
  • Examples of the bifunctional compound among the (meth) acrylic acid ester compounds include 1,3-butanediol di (meth) acrylate, 1,4-butanediol di (meth) acrylate, and 1,6-hexane.
  • those having three or more functions include, for example, trimethylolpropane tri (meth) acrylate, ethylene oxide-added trimethylolpropane tri (meth) acrylate, propylene oxide-added trimethylolpropane tri ( (Meth) acrylate, caprolactone-modified trimethylolpropane tri (meth) acrylate, pentaerythritol tri (meth) acrylate, ethylene oxide-added isocyanuric acid tri (meth) acrylate, glycerol tri (meth) acrylate, propylene oxide-added glycerol tri (meth) acrylate, Tris (meth) acryloyloxyethyl phosphate, ditrimethylolpropane tetra (meth) acrylate, pentaerythritol tetra Meth) acrylate, dipentaerythritol pen
  • 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 jER YL-7000 (manufactured by Mitsubishi Chemical Corporation).
  • epoxy compounds include, for example, YDC-1312, YSLV-80XY, YSLV-90CR (all manufactured by Nippon Steel & Sumikin Chemical Co., Ltd.), XAC4151 (manufactured by Asahi Kasei Co., Ltd.), jER1031, jER1032 (all 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 can be obtained, for example, by reacting a (meth) acrylic acid derivative having a hydroxyl group with an isocyanate compound in the presence of a catalytic amount of a tin-based compound.
  • isocyanate compound used as the raw material for the urethane (meth) acrylate examples include isophorone diisocyanate, 2,4-tolylene diisocyanate, 2,6-tolylene diisocyanate, hexamethylene diisocyanate, trimethylhexamethylene diisocyanate, and diphenylmethane-4,4.
  • MDI '-Diisocyanate
  • hydrogenated MDI polymeric MDI, 1,5-naphthalene diisocyanate, norbornane diisocyanate, tolidine diisocyanate, xylylene diisocyanate (XDI), hydrogenated XDI, lysine diisocyanate, triphenylmethane triisocyanate, tris (isocyanate) Phenyl) thiophosphate, tetramethylxylylene diisocyanate, 1,6,11-undecantrie Cyanate, and the like.
  • MDI '-Diisocyanate
  • XDI xylylene diisocyanate
  • XDI hydrogenated XDI
  • lysine diisocyanate triphenylmethane triisocyanate
  • tris (isocyanate) Phenyl) thiophosphate tetramethylxylylene diisocyanate, 1,6,11-und
  • the isocyanate compound is obtained by, for example, reacting a polyol such as ethylene glycol, propylene glycol, glycerin, sorbitol, trimethylolpropane, carbonate diol, polyether diol, polyester diol, polycaprolactone diol and an excess isocyanate compound. It is also possible to use chain-extended isocyanate compounds.
  • 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.
  • Mono (meth) acrylates of dihydric alcohols such as diol and polyethylene glycol mono (meth) acrylates or di (meth) acrylates of trivalent alcohols such as trimethylolethane, trimethylolpropane and glycerin, bisphenol A type epoxy ( Examples include epoxy (meth) acrylates such as (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, N -(Meth) acrylamide compounds such as isopropyl (meth) acrylamide, N, N-dimethylaminopropyl (meth) acrylamide, vinyl compounds such as styrene, ⁇ -methylstyrene, N-vinylpyrrolidone, N-vinyl- ⁇ -caprolactam, etc. Is mentioned.
  • the radical polymerizable compound preferably contains a monofunctional radical polymerizable compound and a polyfunctional radical polymerizable compound from the viewpoint of adjusting curability.
  • the monofunctional radical polymerizable compound and the polyfunctional radical polymerizable compound By containing the monofunctional radical polymerizable compound and the polyfunctional radical polymerizable compound, the resulting optical moisture curable resin composition becomes more excellent in curability and 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 45 parts by weight with respect to a total of 100 parts by weight with the functional radical polymerizable compound.
  • the content of the polyfunctional radical polymerizable compound is within this range, the resulting optical moisture curable resin composition is more excellent in curability and 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 35 weight part.
  • the content of the radical polymerizable compound is such that a preferred lower limit is 10 parts by weight and a preferred upper limit is 80 parts by weight with respect to a total of 100 parts by weight of the radical polymerizable compound and the moisture curable resin.
  • a preferred lower limit of the content of the radical polymerizable compound is 25 parts by weight
  • a more preferred upper limit is 70 parts by weight
  • a still more preferred lower limit is 30 parts by weight
  • a still more preferred upper limit is 59 parts by weight.
  • the optical moisture curable resin composition of the present invention contains a moisture curable resin.
  • the moisture curable resin include a moisture curable urethane resin and a resin having a crosslinkable silyl group.
  • a moisture hardening type urethane resin is preferable.
  • the moisture curable urethane resin has a urethane bond and an isocyanate group, and the isocyanate group in the molecule is cured by reacting with moisture in the air or the adherend.
  • the moisture curable urethane resin preferably has the isocyanate group at the end of the molecule.
  • the moisture curable urethane resin may have only one isocyanate group in one molecule, or may have two or more. Especially, it is preferable to have an isocyanate group at both ends.
  • the moisture curable urethane resin 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.
  • the range is 2.5.
  • 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 alone or in combination of two or more.
  • polyester polyol examples include a polyester polyol obtained by a reaction between a polyvalent carboxylic acid and a polyol compound, a poly- ⁇ -caprolactone polyol obtained by ring-opening polymerization of ⁇ -caprolactone, and the like.
  • 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.
  • polyol compound used as a raw material for the polyester polyol examples include ethylene glycol, propylene glycol, 1,3-propanediol, 1,4-butanediol, neopentyl glycol, 1,5-pentanediol, 1,6- Examples include hexanediol, diethylene glycol, and cyclohexanediol.
  • polyether polyol examples include ethylene glycol, propylene glycol, ring-opening polymer of tetrahydrofuran, ring-opening polymer of 3-methyltetrahydrofuran, and random copolymers or block copolymers of these or derivatives thereof, bisphenol Type polyoxyalkylene modified products.
  • 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-4,4′-diisocyanate (MDI), a liquid modified product of MDI, polymeric MDI, tolylene diisocyanate, naphthalene-1,5-diisocyanate, and the like.
  • MDI diphenylmethane-4,4′-diisocyanate
  • polymeric MDI polymeric MDI
  • tolylene diisocyanate polymeric MDI
  • naphthalene-1,5-diisocyanate and the like.
  • diphenylmethane diisocyanate and its modified products are preferred from the viewpoints of low vapor pressure and toxicity, and ease of handling.
  • the said polyisocyanate compound may be used independently and 2 or more types may be used in combination.
  • 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 are preferable.
  • 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 weight average molecular weight of the moisture curable urethane resin is not particularly limited, but a preferable lower limit is 800 and a preferable upper limit is 10,000. When the weight average molecular weight of the moisture curable urethane resin is within this range, the crosslinking density does not become too high, the obtained cured product is more excellent in flexibility, and the resulting optical moisture curable resin composition has applicability. It will be better.
  • 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 2500, and the further 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 resin having a crosslinkable silyl group preferably has a crosslinkable silyl group at the terminal.
  • examples of commercially available resins having a crosslinkable silyl group include Exter S2410, S2420, S3430 (all manufactured by Asahi Glass Co., Ltd.), XMAP SA-100S (manufactured by Kaneka Corp.), and the like.
  • a preferable lower limit is 20 parts by weight and a preferable upper limit is 90 parts by weight with respect to a total of 100 parts by weight of the radical polymerizable compound and the moisture curable resin.
  • the content of the moisture curable resin is within this range, the obtained light moisture curable resin composition is more excellent in moisture curable property and photo curable property.
  • a more preferred lower limit of the content of the moisture curable resin is 30 parts by weight, a more preferred upper limit is 75 parts by weight, a still more preferred lower limit is 41 parts by weight, and a still more preferred upper limit is 70 parts by weight.
  • the light moisture curable resin composition of the present invention usually contains a radical photopolymerization initiator.
  • a radical photopolymerization initiator examples include benzophenone compounds, acetophenone compounds, acylphosphine oxide compounds, titanocene compounds, oxime ester compounds, benzoin ether compounds, thioxanthones, and the like.
  • photo radical polymerization initiators examples include IRGACURE 184, IRGACURE 369, IRGACURE 379, IRGACURE 651, IRGACURE 784, IRGACURE 819, IRGACURE 907, IRGACURE 2959, IRGACUREO BASF), benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether (all manufactured by Tokyo Chemical Industry Co., Ltd.) and the like.
  • 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 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 preferably contains a filler.
  • 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 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
  • the still more preferable upper limit is 20 nm.
  • the primary particle size of the filler may be measured by dispersing the filler in a solvent (water, organic solvent, etc.) using a particle size distribution measuring device such as NICOMP 380ZLS (manufactured by PARTICS SIZING SYSTEMS). it can.
  • 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 resulting light moisture curable resin composition is excellent in ultraviolet transmittance. These fillers may be used alone or in combination of two or more.
  • 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, in an organic solvent such as alcohol or toluene. Silica is added to the mixture, and further, 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 such that the preferred lower limit is 1 part by weight and the preferred upper limit is 20 parts by weight with respect to a total of 100 parts by weight of the radical polymerizable compound and the moisture curable resin.
  • the content of the filler is within this range, the obtained light moisture curable resin composition is more excellent in coating properties and shape retention after coating.
  • the more preferred lower limit of the filler content is 2 parts by weight, the more preferred upper limit is 15 parts by weight, the still more preferred lower limit is 3 parts by weight, the still more preferred upper limit is 10 parts by weight, and the particularly preferred upper limit is 5 parts by weight. .
  • the light moisture curable resin composition of the present invention preferably contains a compound having at least one group selected from the group consisting of an isocyanate group, an isothiocyanate group, and a carbodiimide group.
  • the compound having at least one group selected from the group consisting of the isocyanate group, isothiocyanate group, and carbodiimide group is highly reactive with moisture, and reacts with moisture-curable resin and moisture during storage. It has a role to prevent.
  • the compound which has a urethane bond and an isocyanate group is handled as the said moisture hardening type urethane resin.
  • the compound having at least one group selected from the group consisting of the isocyanate group, the isothiocyanate group, and the carbodiimide group needs to move through the system and rapidly react with moisture, and therefore has a low molecular weight.
  • the preferable upper limit of the molecular weight is 500, and the more preferable upper limit is 300.
  • a compound having an isocyanate group having an aromatic ring and a compound having an isothiocyanate group having an aromatic ring are suitable.
  • the compound which has a carbodiimide group there is no restriction
  • a compound having at least one group selected from the group consisting of an isocyanate group, an isothiocyanate group, and a carbodiimide group that did not react with moisture contributes to the curing of the moisture curable resin, and the crosslinking density is improved. By doing so, the cured product of the obtained light moisture curable resin composition is excellent in adhesiveness.
  • the compound having at least one group selected from the group consisting of the isocyanate group, isothiocyanate group, and carbodiimide group may be monofunctional or polyfunctional, It is preferable that it is bifunctional because it has moderate reactivity.
  • the compound having at least one group selected from the group consisting of the isocyanate group, the isothiocyanate group, and the carbodiimide group is for chemically removing moisture, but the light moisture curable type of the present invention.
  • the crosslink density is improved, and the cured product of the resulting light moisture curable resin composition is obtained.
  • a compound having an isocyanate group is preferred because it is excellent in the effect of having excellent adhesiveness.
  • the compound having an isocyanate group may be the same as or different from the polyisocyanate compound that is a raw material for the moisture-curable resin.
  • the compound having an isocyanate group include isophorone diisocyanate, 2,4-tolylene diisocyanate, 2,6-tolylene diisocyanate, hexamethylene diisocyanate, trimethylhexamethylene diisocyanate, and diphenylmethane-4,4′-.
  • MDI Diisocyanate
  • NDI 1,5-naphthalene diisocyanate
  • NDI norbornane diisocyanate
  • tolidine diisocyanate xylylene diisocyanate
  • XDI hydrogenated XDI
  • lysine diisocyanate triphenylmethane triisocyanate
  • tris Isocyanatophenyl) thiophosphate, tetramethylxylene diisocyanate, 1,6,11-undecane triisocyanate, etc. Is mentioned.
  • the compound having an isothiocyanate group include benzyl isothiocyanate, phenyl isothiocyanate, 4-phenylbutyl isothiocyanate, and 3-phenylpropyl isothiocyanate.
  • the compound having a carbodiimide group examples include N, N-dicyclohexylcarbodiimide, N, N-diisopropylcarbodiimide, 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride, bis (2 , 6-diisopropylphenyl) carbodiimide, and examples of commercially available products include carbodilite LA-1 (manufactured by Nisshinbo Co., Ltd.). These may be used alone or in combination of two or more.
  • the content of the compound having at least one group selected from the group consisting of the isocyanate group, isothiocyanate group, and carbodiimide group is preferable in 100 parts by weight of the entire optical moisture-curable resin composition of the present invention.
  • the lower limit is 0.05 parts by weight, and the preferred upper limit is 10 parts by weight.
  • the degree of crosslinking during curing of the moisture curable resin is increased.
  • the resulting light moisture curable resin composition is more excellent in storage stability and adhesiveness while preventing it from becoming too hard and brittle.
  • the more preferable lower limit of the content of the compound having at least one group selected from the group consisting of the isocyanate group, the isothiocyanate group, and the carbodiimide group is 0.1 parts by weight, and the more preferable upper limit is 3.0 parts by weight.
  • a more preferred lower limit is 0.2 parts by weight, and a more preferred upper limit is 1.5 parts by weight.
  • the light moisture curable resin composition of the present invention may contain a light shielding agent.
  • the light moisture curable resin composition of the present invention has excellent light-shielding properties. For example, when used in a display element, light leakage can be prevented.
  • the display element manufactured using the light moisture curable resin composition of the present invention containing the above light shielding agent is high because the light moisture curable resin composition has sufficient light shielding properties, and does not leak light. It has contrast and has excellent image display quality.
  • 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 materials such as silica, talc, titanium oxide, and the like mentioned as fillers can be used as long as they have the ability to hardly transmit light in the visible light region. Included in the light shielding 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, zirconium oxide
  • an organic component such as a coupling agent, silicon oxide, titanium oxide, germanium oxide, aluminum oxide, zirconium oxide
  • Surface-treated titanium black such as those coated with an inorganic component such as magnesium oxide can also be used.
  • what is processed with the organic component is preferable at the point which can improve insulation more.
  • 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 within this range, the resulting optical moisture-curable resin composition is more excellent in coating properties and workability without significantly increasing viscosity and thixotropy.
  • 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.
  • the particle size of the light-shielding agent can be measured by dispersing the light-shielding agent in a solvent (water, organic solvent, etc.) using NICOMP 380ZLS (manufactured by PARTICS SIZING SYSTEMS).
  • the minimum with preferable content of the said light shielding agent in the whole optical moisture hardening type resin composition of this invention is 0.05 weight%, and a preferable upper limit is 10 weight%.
  • the content of the light-shielding agent is within this range, the resulting light moisture-curable resin composition has excellent light-drawing properties, adhesion to a substrate, etc., and light-shielding properties while maintaining strength after curing. It will be excellent.
  • a more preferable lower limit of the content of the light shielding agent is 0.1% by weight, a more preferable upper limit is 2% by weight, and a still more preferable upper limit is 1% by weight.
  • the light moisture curable resin composition of the present invention may further contain additives such as a colorant, an ionic liquid, a solvent, metal-containing particles, and a reactive diluent as necessary.
  • additives such as a colorant, 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 resin, a radical photopolymerization initiator, 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 resin, a radical photopolymerization initiator, and an additive to be added as necessary.
  • the moisture content of the light moisture curable resin composition of the present invention is 100 ppm or less.
  • the water content is 100 ppm or less, the reaction between the moisture curable resin and moisture during storage is suppressed, and the optical moisture curable resin composition is more excellent in storage stability.
  • the water content is more preferably 80 ppm or less.
  • the water content can be measured by a Karl Fischer moisture measuring device.
  • the preferable lower limit of the viscosity measured at 25 ° C. and 1 rpm using a cone plate viscometer is 50 Pa ⁇ s, and the preferable upper limit is 500 Pa ⁇ s.
  • the viscosity is within this range, when the light moisture curable resin composition is used as an adhesive for electronic components or an adhesive for display elements, it is more excellent in workability when applied to an adherend such as a substrate.
  • 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.
  • paintability can be improved by heating at the time of application
  • 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 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.
  • Examples of adherends that can be bonded using the light moisture curable resin composition of the present invention include various adherends such as metal, glass, and plastic.
  • Examples of the shape of the adherend include a film shape, a sheet shape, a plate shape, a panel shape, a tray shape, a rod (rod-like body) shape, a box shape, and a housing shape.
  • Examples of the metal include steel, stainless steel, aluminum, copper, nickel, chromium, and alloys thereof.
  • Examples of the glass include alkali glass, non-alkali glass, and quartz glass.
  • Examples of the plastic include polyolefin resins such as high density polyethylene, ultra high molecular weight polyethylene, isotactic polypropylene, syndiotactic polypropylene, and ethylene propylene copolymer resin, nylon 6 (N6), nylon 66 (N66), Nylon 46 (N46), Nylon 11 (N11), Nylon 12 (N12), Nylon 610 (N610), Nylon 612 (N612), Nylon 6/66 copolymer (N6 / 66), Nylon 6/66/610 Polymer (N6 / 66/610), nylon MXD6 (MXD6), nylon 6T, nylon 6 / 6T copolymer, nylon 66 / PP copolymer, polyamide 66 resin such as nylon 66 / PPS copo
  • Aromatic polyester resins polyacrylonitrile (PAN), polymethacrylonitrile, acrylonitrile / styrene copolymer (AS), methacrylonitrile / styrene copolymer, methacrylonitrile / styrene / butadiene copolymer, etc.
  • polycarbonate polymethacrylate resin such as polymethyl methacrylate (PMMA), polyethyl methacrylate, ethylene / vinyl acetate copolymer (EVA), polyvinyl alcohol (PVA), vinyl alcohol And polyvinyl resins such as vinyl / ethylene copolymer (EVOH), polyvinylidene chloride (PVDC), polyvinyl chloride (PVC), vinyl chloride / vinylidene chloride copolymer, vinylidene chloride / methyl acrylate copolymer, and the like.
  • PMMA polymethyl methacrylate
  • EVA polyvinyl alcohol
  • PVDC polyvinylidene chloride
  • PVDC polyvinyl chloride
  • PVDC polyvinyl chloride
  • PVDC polyvinyl chloride
  • PVDC polyvinyl chloride
  • vinyl chloride / vinylidene chloride copolymer vinylidene chloride / methyl acrylate copolymer
  • Examples of the adherend include a composite material having a metal plating layer on the surface, and examples of the base material for plating the composite material include the metal, glass, and plastic described above. Furthermore, examples of the adherend include materials in which a passivation film is formed by passivating a metal surface. Examples of the passivating treatment include heat treatment and anodizing treatment. . In particular, in the case of an aluminum alloy or the like whose material is an international aluminum alloy name in the 6000 series, the adhesiveness can be improved by performing a sulfuric acid alumite treatment or a phosphoric acid alumite treatment as the passivation treatment.
  • a step of applying the light moisture curable resin composition of the present invention to a first member a step of applying the light moisture curable resin composition of the present invention to a first member
  • the step of irradiating the light moisture curable resin composition of the present invention applied to the member with light to cure the radical polymerizable compound in the light moisture curable resin composition of the present invention first curing step
  • first curing step a step of bonding the first member and the second member via the light moisture curable resin composition after the first curing step
  • bonding step the light moisture curing of the present invention after the bonding step.
  • the first member and / or the second member is made of a material that transmits light, it is preferable to irradiate light through the first member and / or the second member that transmits light.
  • the first member and / or the second member is a material that does not easily transmit light, the first member and the second member are interposed via the light moisture curable resin composition. It is preferable to irradiate the side surface of the bonded structure, that is, the portion where the light moisture curable resin composition is exposed.
  • 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.
  • a method for producing the cured product of the present invention by curing the light moisture curable resin composition of the present invention with light moisture for example, light of 500 to 3000 mJ / cm 2 is applied to the light moisture curable resin composition of the present invention.
  • the cured body of the present invention preferably has an optical density (OD value) of 1 or more when the thickness is 1 mm.
  • OD value optical density
  • 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.
  • the cured body of the present invention can be particularly suitably used for electronic parts and display element applications.
  • An electronic component having the substrate and the cured body of the present invention and a display element having the substrate and the cured body of the present invention are also one aspect of the present invention.
  • flexibility and reliability can be provided.
  • the electronic component and display element which use this hardening body can be provided.
  • it is suitable for manufacture of this hardening body and can provide the optical moisture hardening type resin composition which is excellent in applicability
  • FIG.1 (a) is a schematic diagram which shows the case where a test piece is seen from the top
  • FIG.1 (b) is a schematic diagram which shows the case where a test piece is seen from the side.
  • Examples 1 to 7, Comparative Examples 1 to 3 In accordance with the blending ratio described in Table 1, each material was stirred with a planetary stirrer (“Shinky Co., Ltd.,“ Awatori Netaro ”), and then uniformly mixed with a ceramic three roll. To 7 and Comparative Examples 1 to 3 were obtained. A part of the obtained light moisture curable resin composition was embedded in a Teflon (registered trademark) mold having a width of 3 mm, a length of 50 mm, and a height of 1 mm.
  • Teflon registered trademark
  • UV-LED microwave 365 nm
  • Each of the light moisture curable resin compositions obtained in Examples and Comparative Examples is applied on a polycarbonate substrate with a width of about 1 mm, and irradiated with UV light at 1000 mJ / cm 2 using a UV-LED (wavelength 365 nm).
  • Each photo-moisture curable resin composition is photocured, and then a glass substrate is stacked, a 20 g weight is placed, and light is left by standing at 25 ° C. and 50% RH for 3 days (72 hours or more).
  • the moisture curable resin composition was moisture cured to obtain a test piece.
  • the schematic diagram (FIG. 1 (a)) which shows the case where a test piece is seen from the top in FIG.
  • FIG. 1 (b) the schematic diagram which shows the case where a test piece is seen from the side were shown.
  • Tensile shear strength was measured by pulling the obtained test piece at 25 ° C. using a tensile tester (“EZ-Graph” manufactured by Shimadzu Corporation) at a rate of 10 mm / min in the shear direction.
  • flexibility and reliability can be provided.
  • the electronic component and display element which use this hardening body can be provided.
  • it is suitable for manufacture of this hardening body and can provide the optical moisture hardening type resin composition which is excellent in applicability

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Condensed Matter Physics & Semiconductors (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Manufacturing & Machinery (AREA)
  • Computer Hardware Design (AREA)
  • Microelectronics & Electronic Packaging (AREA)
  • Power Engineering (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Macromonomer-Based Addition Polymer (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Polymerisation Methods In General (AREA)
  • Graft Or Block Polymers (AREA)

Abstract

La présente invention a pour objet de fournir un corps durci présentant une souplesse et une fiabilité excellentes. La présente invention a en outre pour objet de fournir un composant électronique et un élément d'affichage formés en utilisant ledit corps durci. La présente invention a également pour objet de fournir une composition de résine durcissable à la lumière/l'humidité convenant à la production dudit corps durci et présentant des propriétés de revêtement, des propriétés de rétention de forme, et une adhérence excellentes. La présente invention concerne un corps durci d'une composition de résine durcissable à la lumière/l'humidité qui contient un composé polymérisable par voie radicalaire et une résine durcissable à l'humidité, où la résistance à la traction du corps durci sous un allongement de 400 % à 25°C est de 3 à 20 kgf/cm2, inclus.
PCT/JP2016/061958 2015-04-17 2016-04-14 Corps durci, composant électronique, élément d'affichage, et composition de résine durcissable à la lumière/l'humidité WO2016167305A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
JP2016526962A JP6698524B2 (ja) 2015-04-17 2016-04-14 硬化体、電子部品、表示素子、及び、光湿気硬化型樹脂組成物
KR1020177007155A KR102260532B1 (ko) 2015-04-17 2016-04-14 경화체, 전자 부품, 표시 소자 및 광 습기 경화형 수지 조성물
CN201680003536.6A CN107108772A (zh) 2015-04-17 2016-04-14 固化体、电子部件、显示元件及光湿固化型树脂组合物

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2015-085158 2015-04-17
JP2015085158 2015-04-17

Publications (1)

Publication Number Publication Date
WO2016167305A1 true WO2016167305A1 (fr) 2016-10-20

Family

ID=57127110

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2016/061958 WO2016167305A1 (fr) 2015-04-17 2016-04-14 Corps durci, composant électronique, élément d'affichage, et composition de résine durcissable à la lumière/l'humidité

Country Status (5)

Country Link
JP (2) JP6698524B2 (fr)
KR (1) KR102260532B1 (fr)
CN (1) CN107108772A (fr)
TW (1) TWI701310B (fr)
WO (1) WO2016167305A1 (fr)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20170335144A1 (en) * 2016-03-07 2017-11-23 Nitto Denko Corporation Optical adhesive sheet, polarizing film with adhesive layer and liquid crystal display device
JP2018173613A (ja) * 2017-03-31 2018-11-08 シチズンファインデバイス株式会社 画像表示装置及びその製造方法
WO2019203277A1 (fr) * 2018-04-19 2019-10-24 積水化学工業株式会社 Composition de résine durcissable, article durci, pièce électronique et pièce d'assemblage
WO2020241803A1 (fr) * 2019-05-30 2020-12-03 積水化学工業株式会社 Composition de résine durcissable, objet durci et composant électronique
WO2022004416A1 (fr) * 2020-06-29 2022-01-06 積水化学工業株式会社 Composition de résine photodurcissable/durcissable à l'humidité et corps durci
WO2022114186A1 (fr) * 2020-11-30 2022-06-02 積水化学工業株式会社 Composition de résine durcissable à l'humidité et adhésif pour appareil électronique

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR102574109B1 (ko) * 2022-10-18 2023-09-06 (주)중앙종합안전기술연구원 구조물 안전 점검 및 진단용 균열 폭 측정기

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013016133A2 (fr) * 2011-07-22 2013-01-31 H.B. Fuller Company Adhésif monocomposant à polymérisation double à utiliser en électronique
JP5844504B1 (ja) * 2014-05-13 2016-01-20 積水化学工業株式会社 光湿気硬化型樹脂組成物、電子部品用接着剤、及び、表示素子用接着剤
JP2016074783A (ja) * 2014-10-03 2016-05-12 積水化学工業株式会社 光湿気硬化型樹脂組成物

Family Cites Families (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19800676A1 (de) * 1998-01-10 1999-07-15 Henkel Kgaa Verwendung ausgewählter Klebstoffgemische für die Überlappungsverklebung von Rundumetiketten bei ihrem Auftrag auf Kunststoff-Flaschen
JP2000178342A (ja) 1998-12-17 2000-06-27 Sumitomo Bakelite Co Ltd 絶縁ペースト
US6828355B1 (en) * 1999-07-19 2004-12-07 Henkel Corporation Resin-reinforced UV, moisture and UV/moisture dual curable silicone compositions
JP2001064543A (ja) * 1999-08-27 2001-03-13 Nippon Shokubai Co Ltd 硬化型被覆材用樹脂組成物
JP2001220569A (ja) * 2000-02-09 2001-08-14 Sekisui Chem Co Ltd 反応性接着剤組成物
JP2001240811A (ja) * 2000-03-01 2001-09-04 Sekisui Chem Co Ltd 反応性接着剤組成物及び部材の接合方法
JP2004047415A (ja) * 2002-05-24 2004-02-12 Sekisui Chem Co Ltd フレキシブルフラットケーブル、接着剤及びその接合体
JP2004018621A (ja) * 2002-06-14 2004-01-22 Nippon Shokubai Co Ltd ラジカル硬化性ウレタン樹脂組成物
US7189781B2 (en) * 2003-03-13 2007-03-13 H.B. Fuller Licensing & Finance Inc. Moisture curable, radiation curable sealant composition
JP5013585B2 (ja) 2006-09-06 2012-08-29 日立化成ポリマー株式会社 反応性ホットメルト接着剤組成物及びそれを用いた接着方法
JP5228370B2 (ja) 2007-04-27 2013-07-03 東亞合成株式会社 一液湿気硬化型ウレタン系ホットメルト接着剤組成物及びその使用方法
KR101414090B1 (ko) * 2008-02-27 2014-07-02 디아이씨 가부시끼가이샤 투습 필름, 그 제조 방법 및 그것을 사용한 적층체
JP5488386B2 (ja) * 2010-10-14 2014-05-14 Ｄｉｃ株式会社 活性エネルギー線硬化性ホットメルトウレタン樹脂組成物、それを用いた電子機器用部材、及びパッキン
CN104031598A (zh) * 2014-06-30 2014-09-10 江苏华程光电科技有限公司 高导热性led密封胶

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013016133A2 (fr) * 2011-07-22 2013-01-31 H.B. Fuller Company Adhésif monocomposant à polymérisation double à utiliser en électronique
JP5844504B1 (ja) * 2014-05-13 2016-01-20 積水化学工業株式会社 光湿気硬化型樹脂組成物、電子部品用接着剤、及び、表示素子用接着剤
JP2016074783A (ja) * 2014-10-03 2016-05-12 積水化学工業株式会社 光湿気硬化型樹脂組成物

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20170335144A1 (en) * 2016-03-07 2017-11-23 Nitto Denko Corporation Optical adhesive sheet, polarizing film with adhesive layer and liquid crystal display device
JP2018173613A (ja) * 2017-03-31 2018-11-08 シチズンファインデバイス株式会社 画像表示装置及びその製造方法
WO2019203277A1 (fr) * 2018-04-19 2019-10-24 積水化学工業株式会社 Composition de résine durcissable, article durci, pièce électronique et pièce d'assemblage
WO2020241803A1 (fr) * 2019-05-30 2020-12-03 積水化学工業株式会社 Composition de résine durcissable, objet durci et composant électronique
WO2022004416A1 (fr) * 2020-06-29 2022-01-06 積水化学工業株式会社 Composition de résine photodurcissable/durcissable à l'humidité et corps durci
WO2022114186A1 (fr) * 2020-11-30 2022-06-02 積水化学工業株式会社 Composition de résine durcissable à l'humidité et adhésif pour appareil électronique

Also Published As

Publication number Publication date
KR102260532B1 (ko) 2021-06-03
JPWO2016167305A1 (ja) 2018-02-15
CN107108772A (zh) 2017-08-29
JP2020111764A (ja) 2020-07-27
KR20170137691A (ko) 2017-12-13
TW201704394A (zh) 2017-02-01
TWI701310B (zh) 2020-08-11
JP6698524B2 (ja) 2020-05-27

Similar Documents

Publication Publication Date Title
JP6243969B2 (ja) 硬化体、電子部品、及び、表示素子
JP6698524B2 (ja) 硬化体、電子部品、表示素子、及び、光湿気硬化型樹脂組成物
JP6039080B2 (ja) 狭額縁設計表示素子用接着剤
JP6641255B2 (ja) 電子部品用接着剤、及び、表示素子用接着剤
WO2015174371A1 (fr) Composition de resine photopolymerisable et reticulables a l'humidite, adhesif pour pieces electroniques, et adhesif pour element d'affichage
JP5989902B2 (ja) 光湿気硬化型樹脂組成物、電子部品用接着剤、及び、表示素子用接着剤
JP2016148034A (ja) 光湿気硬化型樹脂組成物及び熱伝導性接着剤
JP2016089174A (ja) 光湿気硬化型樹脂組成物、電子部品用接着剤、及び、表示素子用接着剤
JP6798791B2 (ja) 電子部品用接着剤、及び、表示素子用接着剤
JP6789014B2 (ja) 光湿気硬化型樹脂組成物、電子部品用接着剤、及び、表示素子用接着剤
JP5824597B1 (ja) 光湿気硬化型樹脂組成物、電子部品用接着剤、及び、表示素子用接着剤
JP6921535B2 (ja) 光湿気硬化型樹脂組成物、電子部品用接着剤、及び、表示素子用接着剤
JP2016147969A (ja) 光湿気硬化型樹脂組成物、電子部品用接着剤、及び、表示素子用接着剤
JP2017190360A (ja) 光湿気硬化型樹脂組成物、電子部品用接着剤、及び、表示素子用接着剤

Legal Events

Date Code Title Description
ENP Entry into the national phase

Ref document number: 2016526962

Country of ref document: JP

Kind code of ref document: A

121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 16780096

Country of ref document: EP

Kind code of ref document: A1

ENP Entry into the national phase

Ref document number: 20177007155

Country of ref document: KR

Kind code of ref document: A

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 16780096

Country of ref document: EP

Kind code of ref document: A1