WO2016076407A1 - 硬化体、電子部品、及び、表示素子 - Google Patents
硬化体、電子部品、及び、表示素子 Download PDFInfo
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- WO2016076407A1 WO2016076407A1 PCT/JP2015/081917 JP2015081917W WO2016076407A1 WO 2016076407 A1 WO2016076407 A1 WO 2016076407A1 JP 2015081917 W JP2015081917 W JP 2015081917W WO 2016076407 A1 WO2016076407 A1 WO 2016076407A1
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- WIPO (PCT)
- Prior art keywords
- meth
- moisture curable
- curable resin
- acrylate
- resin composition
- Prior art date
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- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 230000000475 sunscreen effect Effects 0.000 description 1
- 239000000516 sunscreening agent Substances 0.000 description 1
- 239000012756 surface treatment agent Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- HQHCYKULIHKCEB-UHFFFAOYSA-N tetradecanedioic acid Chemical compound OC(=O)CCCCCCCCCCCCC(O)=O HQHCYKULIHKCEB-UHFFFAOYSA-N 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 238000006227 trimethylsilylation reaction Methods 0.000 description 1
- AMJYHMCHKZQLAY-UHFFFAOYSA-N tris(2-isocyanatophenoxy)-sulfanylidene-$l^{5}-phosphane Chemical compound O=C=NC1=CC=CC=C1OP(=S)(OC=1C(=CC=CC=1)N=C=O)OC1=CC=CC=C1N=C=O AMJYHMCHKZQLAY-UHFFFAOYSA-N 0.000 description 1
- 229920000785 ultra high molecular weight polyethylene Polymers 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
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
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- 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
-
- 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
- C08G18/40—High-molecular-weight compounds
- C08G18/62—Polymers of compounds having carbon-to-carbon double bonds
- C08G18/6216—Polymers of alpha-beta ethylenically unsaturated carboxylic acids or of derivatives thereof
- C08G18/622—Polymers of esters of alpha-beta ethylenically unsaturated carboxylic acids
- C08G18/6225—Polymers of esters of acrylic or methacrylic acid
-
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
- G02F1/1339—Gaskets; Spacers; Sealing of cells
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/02—Details
- H05B33/04—Sealing arrangements, e.g. against humidity
Definitions
- the present invention relates to a cured product excellent in flexibility and reliability in a high temperature and high humidity environment. Moreover, this invention relates to the electronic component and display element which use this hardening body.
- 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 cause problems due to 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 should be a cured body excellent in both flexibility and reliability (particularly creep resistance) in a high temperature and high humidity environment. It was difficult.
- An object of this invention is to provide the hardening body which is excellent in a softness
- the present invention is a cured product of a light moisture curable resin composition containing a radical polymerizable compound and a moisture curable resin, and has a storage elastic modulus at 0 ° C. of 1.0 ⁇ 10 7 Pa or more, and , A cured product having a storage elastic modulus at 50 ° C. of 5.0 ⁇ 10 6 Pa or less.
- the present invention is described in detail below.
- the present inventors obtained a cured product obtained by photo moisture curing the composition at 0 ° C. and 50 ° C. in storage elasticity. It was found that the cured product would be excellent in both flexibility and reliability in a high temperature and high humidity environment by setting the ratio to be in a specific range, and the present invention was completed. .
- the cured product of the present invention has a storage elastic modulus at 0 ° C. of 1.0 ⁇ 10 7 Pa or more.
- the storage elastic modulus at 0 ° C. is less than 1.0 ⁇ 10 7 Pa, when the substrate or the like is bonded using the cured body of the present invention, the cured body may be crushed due to being too soft. In such a case, the width of the adhesive applied at the time of bonding becomes thick, so that the narrow frame design cannot be supported.
- the storage elastic modulus at 0 ° C. is preferably 2.0 ⁇ 10 7 Pa or more, and more preferably 3.0 ⁇ 10 7 Pa or more.
- the upper limit of the storage elastic modulus at 0 ° C. is not particularly limited, but is usually 1.0 ⁇ 10 8 Pa or less.
- the cured product of the present invention has a storage elastic modulus at 50 ° C. of 5.0 ⁇ 10 6 Pa or less.
- the storage elastic modulus at 50 ° C. exceeds 5.0 ⁇ 10 6 Pa, flexibility may be lost even at high temperatures, and the substrate may not be used for bonding.
- the storage elastic modulus at 50 ° C. is preferably 3.0 ⁇ 10 6 Pa or less, more preferably 2.0 ⁇ 10 6 Pa or less, and 1.0 ⁇ 10 6 Pa or less. Further preferred.
- the storage elastic modulus at 50 ° C. is preferably 5.0 ⁇ 10 5 Pa or more because it does not become too soft under high temperature and high humidity conditions and is excellent in reliability.
- the storage elastic modulus at 50 ° C. are the adjustment of the crosslinking density of the cured product, the control of the phase structure in the composition, the selection of the radical polymerizable compound and the moisture curable resin, and the adjustment of the blending amount. It can be easily controlled by selecting a filler and adjusting the blending amount, which will be described later.
- the “storage elastic modulus” can be measured by using a dynamic viscoelasticity measuring apparatus (for example, “DVA-200” manufactured by IT Measurement Control Co., Ltd.).
- the cured body of the present invention preferably has two or more glass transition temperatures, and each has one or more glass transition temperatures of 0 ° C. or less and one or more glass transition temperatures exceeding 0 ° C. Especially, it is more preferable that the glass transition temperature exceeding 0 degreeC is 30 degrees C or less, and it is still more preferable that it is 25 degrees C or less.
- the cured product of the present invention can achieve both flexibility and reliability in a high temperature and high humidity environment.
- Examples of a method for making the cured body have two or more glass transition temperatures include a method for preventing the radical polymerizable compound and the moisture curable resin from being completely incompatible in the composition.
- the radical polymerizable compound and the moisture curable resin are selected based on their respective glass transition temperatures (in the case of a radical polymerizable compound, the glass transition temperature of the homopolymer of the radical polymerizable compound). By doing so, two or more glass transition temperatures can be adjusted to the above-mentioned range.
- the “glass transition temperature” means a temperature at which a maximum due to micro-Brownian motion appears, among the maximum of loss tangent (tan ⁇ ) obtained by dynamic viscoelasticity measurement. It can be measured by a conventionally known method using an elasticity measuring device.
- 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.
- the light moisture curable resin composition that becomes the cured product of the present invention by being light moisture cured is also referred to as “the light moisture curable resin composition according to the present invention”.
- the light moisture curable resin composition according to 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) acryl” means acryl or methacryl.
- Examples of the (meth) acrylic compound include urethane (meth) acrylate obtained by reacting an isocyanate compound with a (meth) acrylic acid derivative having a hydroxyl group, and reacting a compound having a hydroxyl group with (meth) acrylic acid.
- the said radically polymerizable compound contains aliphatic urethane (meth) acrylate.
- 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.
- the aliphatic urethane (meth) acrylate can be obtained, for example, by reacting an aliphatic (meth) acrylic acid derivative having a hydroxyl group with an aliphatic isocyanate compound in the presence of a catalytic amount of a tin compound. .
- Examples of the aliphatic isocyanate compound used as the raw material for the aliphatic urethane (meth) acrylate include alkyl monoisocyanates such as n-butyl isocyanate, isophorone diisocyanate, hexamethylene diisocyanate, trimethylhexamethylene diisocyanate, and dicyclohexylmethane-4,4. Examples include '-diisocyanate, norbornane diisocyanate, cyclohexane-1,2-diylbis (methylene) diisocyanate, lysine diisocyanate, 1,6,11-undecane triisocyanate and the like.
- alkyl monoisocyanates such as n-butyl isocyanate, isophorone diisocyanate, hexamethylene diisocyanate, trimethylhexamethylene diisocyanate, and dicyclohexylmethane-4,4. Examples include '-di
- aliphatic isocyanate compound a reaction between a polyol such as ethylene glycol, propylene glycol, glycerin, sorbitol, trimethylolpropane, carbonate diol, polyether diol, polyester diol, polycaprolactone diol, and an excess aliphatic isocyanate compound. It is also possible to use chain-extended aliphatic isocyanate compounds obtained by
- Examples of the aliphatic (meth) acrylic acid derivative having a hydroxyl group as a raw material for the aliphatic urethane (meth) acrylate include ethylene glycol, propylene glycol, 1,3-propanediol, 1,3-butanediol, 1, Mono (meth) acrylates of divalent aliphatic alcohols such as 4-butanediol and polyethylene glycol, and mono (meth) acrylates or di (meth) of trivalent aliphatic alcohols such as trimethylolethane, trimethylolpropane, and glycerin. ) Acrylate and aliphatic epoxy (meth) acrylate such as hydrogenated bisphenol type epoxy (meth) acrylate.
- Examples of commercially available aliphatic urethane (meth) acrylates include EBECRYL230, EBECRYL270, EBECRYL1290, EBECRYL4858, EBECRYL5129, EBECRYL8402, EBECRYL8411, EBECRYL8804, EBECRYL8804, EBECRYL8804, and EBECRYL8804. (Manufactured by Rahn).
- the radical polymerizable compound can easily adjust the storage elastic modulus of the obtained cured product to the above-described range, and thus has a glass transition temperature of 0 ° C. or lower. It is more preferable to contain the monofunctional aliphatic urethane (meth) acrylate having.
- the content of the monofunctional aliphatic urethane (meth) acrylate having a glass transition temperature of 0 ° C. or lower is preferably 5% by weight with respect to a total of 100 parts by weight of the radical polymerizable compound and the moisture curable resin. Parts, and the preferred upper limit is 30 parts by weight.
- the content of the monofunctional aliphatic urethane (meth) acrylate having a glass transition temperature of 0 ° C. or lower is within this range, it becomes easy to adjust the storage elastic modulus of the obtained cured product to the above-described range. .
- a more preferable lower limit of the content of the monofunctional aliphatic urethane (meth) acrylate having a glass transition temperature of 0 ° C. or lower is 10 parts by weight, and a more preferable upper limit is 25 parts by weight.
- urethane (meth) acrylates other than the above aliphatic urethane (meth) acrylates, the above aliphatic urethanes (except the above-mentioned aliphatic isocyanate compounds are used instead of the above aliphatic isocyanate compounds). It can be obtained in the same manner as meth) acrylate.
- Examples of the other isocyanate compounds include 2,4-tolylene diisocyanate, 2,6-tolylene diisocyanate, diphenylmethane-4,4′-diisocyanate (MDI), hydrogenated MDI, polymeric MDI, and 1,5-naphthalene.
- MDI diphenylmethane-4,4′-diisocyanate
- Examples include diisocyanate, tolidine diisocyanate, xylylene diisocyanate (XDI), hydrogenated XDI, triphenylmethane triisocyanate, tris (isocyanatophenyl) thiophosphate, tetramethylxylylene diisocyanate, and the like.
- Examples of the monofunctional (meth) acrylic acid ester compound obtained by reacting the above (meth) acrylic acid with a compound having a hydroxyl group include, for example, phthalimide acrylates such as N-acryloyloxyethyl hexahydrophthalimide, Various imide acrylate, methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, n-butyl (meth) acrylate, isobutyl (meth) acrylate, t-butyl (meth) acrylate, 2-ethylhexyl (meth) Acrylate, isooctyl (meth) acrylate, n-octyl (meth) acrylate, isononyl (meth) acrylate, isodecyl (meth) acrylate, lauryl (meth) acrylate, isomyristyl (meth) acryl
- 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.
- Examples of the (meth) acrylic acid ester compound having three or more functional groups include, for example, pentaerythritol tri (meth) acrylate, trimethylolpropane tri (meth) acrylate, propylene oxide-added trimethylolpropane tri (meth) acrylate.
- Examples of the epoxy (meth) acrylate include those obtained by reacting an epoxy compound and (meth) acrylic acid in the presence of a basic catalyst according to a conventional method.
- Examples of the epoxy compound 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 resins 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
- 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 according to 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 preferably has a group containing an ethylenically unsaturated double bond and / or an alkoxysilyl group, and a group containing an ethylenically unsaturated double bond and / or an alkoxysilyl group is bonded to a molecule. More preferably at the end.
- the moisture curable urethane resin is not included in the radical polymerizable compound even if it has a radical polymerizable group, and is treated as a moisture curable urethane resin.
- 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.
- 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 diisocyanate (MDI), a liquid modified product of MDI, polymeric MDI, tolylene diisocyanate, naphthalene-1,5-diisocyanate, and the like. Of these, MDI and its modified products are preferred from the viewpoint of low vapor pressure and toxicity and ease of handling.
- MDI diphenylmethane diisocyanate
- 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 made 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 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 optical moisture curable resin composition according to the present invention usually 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.
- 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. When the content of the radical photopolymerization initiator is within this range, the resulting optical moisture curable resin composition is more excellent in photocurability and storage stability.
- 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 according to the present invention is a monofunctional fat having a glass transition temperature of 0 ° C. or lower as the radical polymerizable compound from the viewpoint of setting the storage elastic modulus of the obtained cured product to a suitable range.
- acyl phosphine oxide photopolymerization initiator is contained as an initiator in a proportion of 0.5 to 1.5 parts by weight. It is preferred.
- the light moisture curable resin composition according to the present invention preferably contains a filler.
- the light moisture curable resin composition according to 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 optical moisture curable resin composition according to the present invention, and the particle diameter of such secondary particles is preferable.
- the lower limit is 5 nm
- the preferred upper limit is 500 nm
- the more preferred lower limit is 10 nm
- 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 according to the present invention or the cured product of the present invention 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 preferably 0.1 parts by weight with a preferred lower limit and 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.
- a more preferred lower limit of the content of the filler is 1 part by weight, a more preferred upper limit is 15 parts by weight, a still more preferred lower limit is 2 parts by weight, a still more preferred upper limit is 10 parts by weight, and a particularly preferred lower limit is 3 parts by weight.
- a preferred upper limit is 5 parts by weight.
- the light moisture curable resin composition according to the present invention may contain a light shielding agent.
- the optical moisture hardening type resin composition concerning this invention becomes excellent in light-shielding property, and can prevent the light leak of a 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.
- the light-shielding agent may not be black, and the materials mentioned as fillers such as silica, talc, titanium oxide, etc., as long as the material has the ability to hardly transmit light in the visible light region. Included in sunscreen. 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 providing light shielding properties to the light moisture curable resin composition according to the present invention, while transmitting light having a wavelength in the vicinity of the ultraviolet region. It is a light-shielding agent having properties.
- the photo moisture curable resin composition according to the present invention can be used. Photocurability can be further increased.
- the light-shielding agent contained in the light moisture curable resin composition according to 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.
- the display device manufactured using the light moisture curable resin composition according to the present invention has a high contrast without light leakage because the light moisture curable resin composition has sufficient light shielding properties, It has excellent image display quality.
- 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 ⁇ / ⁇ .
- 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 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.
- 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 concerning this invention is 0.05 weight%, and a preferable upper limit is 10 weight%.
- a preferable upper limit is 10 weight%.
- the content of the light-shielding agent is within this range, the obtained light moisture-curable resin composition is excellent in drawing properties, adhesion to a substrate or the like, strength after curing, and light-shielding properties.
- 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 according to the present invention may further contain additives such as a colorant, an ionic liquid, a solvent, metal-containing particles, a reactive diluent, and a coupling agent as necessary. .
- the optical moisture hardening type resin composition concerning this invention contains a coupling agent.
- the coupling agent By containing the coupling agent, the light moisture curable resin composition according to the present invention is more excellent in creep resistance.
- a silane coupling agent, a titanate coupling agent, a zirconate coupling agent etc. are mentioned, for example.
- a silane coupling agent is preferable because it is particularly excellent in the effect of improving adhesiveness and creep resistance.
- the content of the coupling agent is preferably 0.05 parts by weight and preferably 5 parts by weight with respect to a total of 100 parts by weight of the radical polymerizable compound and the moisture curable resin.
- Examples of the method for producing the light moisture curable resin composition according to the present invention include a radical polymerizable compound using a mixer such as a homodisper, a homomixer, a universal mixer, a planetary mixer, a kneader, and a three roll. And a method of mixing a moisture curable resin, a radical photopolymerization initiator, and an additive added as necessary, such as a filler.
- a mixer such as a homodisper, a homomixer, a universal mixer, a planetary mixer, a kneader, and a three roll.
- a method of mixing a moisture curable resin, a radical photopolymerization initiator, and an additive added as necessary, such as a filler such as a filler.
- 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.
- 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 optical moisture curable resin composition according to 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 according to 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, polynitrile such as methacrylonitrile / styrene / butadiene copolymer Resin, polycarbonate, polymethacrylate resin such as polymethyl methacrylate (PMMA), polyethyl methacrylate vinyl acetate (EVA), polyvinyl alcohol (PVA), vinyl alcohol / ethylene copolymer (EVOH), polyvinylidene chloride (PVDC), polyvinyl chloride (PVC), vinyl / vinylidene chloride copolymers chloride, polyvinyl resins such as vinylidene chloride / methyl acrylate copolymer.
- PMMA polymethyl methacrylate
- EVA polyethyl methacrylate vinyl acetate
- EVA polyvin
- 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.
- Examples of the method for bonding an adherend using the light moisture curable resin composition according to the present invention include, for example, a step of applying the light moisture curable resin composition according to the present invention to a first member, A step of irradiating the light moisture curable resin composition according to the present invention applied to the member 1 with light to cure the radical polymerizable compound in the light moisture curable resin composition according to the present invention (first curing step) ), A step (bonding step) of bonding the first member and the second member via the optical moisture curable resin composition after the first curing step, and after the bonding step, the present invention Examples include a method including a step (second curing step) in which the first member and the second member are bonded by moisture curing of the moisture curable resin in the optical moisture curable resin composition, It is preferable to include a step of irradiating light after the bonding step.
- the adhesiveness (initial adhesiveness) immediately after bonding to the adherend can be improved.
- the first member and / or the second member is made of a material that transmits 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 according to the present invention can be particularly suitably used as an adhesive for electronic components and an adhesive for display elements.
- Examples of the method for producing the cured product of the present invention by curing the light moisture curable resin composition according to the present invention with light moisture include, for example, 500 to 3000 mJ / cm 2 of the light moisture curable resin composition according to the present invention.
- a step of photo-curing by irradiating light, and a photo-cured photo-moisture curable resin composition according to the present invention is exposed to an environment of 20 to 30 ° C. and 40 to 60% RH for 8 to 24 hours to cure the moisture. And a method having a process.
- 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 of the cured product of the present invention can be measured using an optical densitometer.
- the preferable lower limit of the tensile modulus at 25 ° C. is 0.5 kgf / cm 2
- the preferable upper limit is 5 kgf / cm 2
- the adhesive strength is not greatly reduced, and the flexibility is further improved.
- a more preferable lower limit of the tensile modulus is 1 kgf / cm 2
- a more preferable upper limit is 4 kgf / cm 2 .
- the above “tensile modulus” is a tensile tester (for example, “EZ-Graph” manufactured by Shimadzu Corporation), and the cured body was pulled at a speed of 10 mm / min and stretched by 10%. It means the value measured as the force of time.
- 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 the reliability in a high temperature, high humidity environment can be provided.
- the electronic component and display element which use this hardening body can be provided.
- FIG. 1A is a schematic diagram showing a case where a sample for creep resistance evaluation is viewed from above
- FIG. 1B is a schematic diagram showing a case where the sample for creep resistance evaluation is viewed from the side. is there.
- Examples 1 to 7, Comparative Examples 1 to 5 In accordance with the blending ratios described in Tables 1 and 2, each material was stirred with a planetary stirrer ("Shinky”, “Awatori Nertaro”), and then mixed uniformly with a ceramic three roll. A moisture curable resin composition was 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
- the photo-moisture curable resin composition is photo-cured by irradiating it with 1000 mJ / cm 2 of ultraviolet rays using a high-pressure mercury lamp, and then cured by moisture for more than one night to obtain a cured product. It was.
- FIG. 1 is a schematic diagram showing a case where a creep resistance evaluation sample is viewed from above (FIG.
- FIG. 1A a schematic diagram showing a case where a creep resistance evaluation sample is viewed from the side
- FIG. 1B a schematic diagram showing a case where a creep resistance evaluation sample is viewed from the side
- flexibility and the reliability in a high-temperature, high-humidity environment can be provided.
- the electronic component and display element which use this hardening body can be provided.
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Abstract
Description
ところで、携帯電話、携帯ゲーム機等、各種表示素子付きモバイル機器が普及している現代において、表示素子の小型化は最も求められている課題であり、小型化の手法として、画像表示部を狭額縁化することが行われている(以下、狭額縁設計ともいう)。しかしながら、狭額縁設計においては、充分に光の届かない部分に光硬化型樹脂組成物が塗布されることがあり、その結果、光の届かない部分に塗布された光硬化型樹脂組成物は硬化が不充分となるという問題があった。そこで、光の届かない部分に塗布された場合でも充分に硬化できる樹脂組成物として光熱硬化型樹脂組成物を用い、光硬化と熱硬化とを併用することも行われているが、高温での加熱により素子等に悪影響を与えるおそれがあった。
このような電子部品の接着に用いられる接着剤として、例えば、特許文献1には、数平均分子量が600~1000であるエポキシ化合物を含有する熱硬化型の接着剤が開示されている。しかしながら、特許文献1に開示されているような熱硬化型の接着剤は、熱により不具合を生じる可能性のある電子部品の接着には適さないものであった。
以下に本発明を詳述する。
また、本発明の硬化体は、50℃における貯蔵弾性率が5.0×106Pa以下である。上記50℃における貯蔵弾性率が5.0×106Paを超えると、高温時においても柔軟性が失われ、基板等の接着に用いることができなくなることがある。上記50℃における貯蔵弾性率は、3.0×106Pa以下であることが好ましく、2.0×106Pa以下であることがより好ましく、1.0×106Pa以下であることが更に好ましい。また、高温高湿条件下で柔らかくなりすぎず、信頼性により優れるものとなることから、50℃における貯蔵弾性率は、5.0×105Pa以上であることが好ましい。
上記0℃における貯蔵弾性率及び上記50℃における貯蔵弾性率は、硬化体の架橋密度の調整、組成物中の相構造の制御、ラジカル重合性化合物や湿気硬化型樹脂の選定及び配合量の調整、後述する充填剤の選定及び配合量の調整等によって容易に制御できる。
なお、上記「貯蔵弾性率」は、動的粘弾性測定装置(例えば、IT計測制御社製、「DVA-200」等)を用いることで測定できる。
上記硬化体を2つ以上のガラス転移温度を有するものとする方法としては、組成物中において上記ラジカル重合性化合物と上記湿気硬化型樹脂とを完全に相溶しないようにする方法等が挙げられ、上記ラジカル重合性化合物と上記湿気硬化型樹脂とを、それぞれ単独のガラス転移温度(ラジカル重合性化合物の場合はラジカル重合性化合物の単独重合体のガラス転移温度を指す)をもとにして選定することで、2つ以上のガラス転移温度を上述した範囲に調整できる。
なお、本明細書において上記「ガラス転移温度」とは、動的粘弾性測定により得られる損失正接(tanδ)の極大のうち、ミクロブラウン運動に起因する極大が現れる温度を意味し、動的粘弾性測定装置を用いた従来公知の方法により測定することができる。
上記ラジカル重合性化合物としては、光重合性を有するラジカル重合性化合物であればよく、分子中にラジカル反応性官能基を有する化合物であれば特に限定されないが、ラジカル反応性官能基として不飽和二重結合を有する化合物が好適であり、特に反応性の面から(メタ)アクリロイル基を有する化合物(以下、「(メタ)アクリル化合物」ともいう)が好適である。
なお、本明細書において、上記「(メタ)アクリル」は、アクリル又はメタクリルを意味する。
なお、本明細書において、上記「(メタ)アクリレート」とは、アクリレート又はメタクリレートを意味する。また、上記ウレタン(メタ)アクリレートの原料となるイソシアネート化合物のイソシアネート基は、全てウレタン結合の形成に用いられ、上記ウレタン(メタ)アクリレートは、残存イソシアネート基を有さない。
上記ビスフェノールF型エポキシ樹脂のうち市販されているものとしては、例えば、jER806、jER4004(いずれも三菱化学社製)等が挙げられる。
上記ビスフェノールS型エポキシ樹脂のうち市販されているものとしては、例えば、エピクロンEXA1514(DIC社製)等が挙げられる。
上記2,2’-ジアリルビスフェノールA型エポキシ樹脂のうち市販されているものとしては、例えば、RE-810NM(日本化薬社製)等が挙げられる。
上記水添ビスフェノール型エポキシ樹脂のうち市販されているものとしては、例えば、エピクロンEXA7015(DIC社製)等が挙げられる。
上記プロピレンオキシド付加ビスフェノールA型エポキシ樹脂のうち市販されているものとしては、例えば、EP-4000S(ADEKA社製)等が挙げられる。
上記レゾルシノール型エポキシ樹脂のうち市販されているものとしては、例えば、EX-201(ナガセケムテックス社製)等が挙げられる。
上記ビフェニル型エポキシ樹脂のうち市販されているものとしては、例えば、jER YX-4000H(三菱化学社製)等が挙げられる。
上記スルフィド型エポキシ樹脂のうち市販されているものとしては、例えば、YSLV-50TE(新日鉄住金化学社製)等が挙げられる。
上記ジフェニルエーテル型エポキシ樹脂のうち市販されているものとしては、例えば、YSLV-80DE(新日鉄住金化学社製)等が挙げられる。
上記ジシクロペンタジエン型エポキシ樹脂のうち市販されているものとしては、例えば、EP-4088S(ADEKA社製)等が挙げられる。
上記ナフタレン型エポキシ樹脂のうち市販されているものとしては、例えば、エピクロンHP4032、エピクロンEXA-4700(いずれもDIC社製)等が挙げられる。
上記フェノールノボラック型エポキシ樹脂のうち市販されているものとしては、例えば、エピクロンN-770(DIC社製)等が挙げられる。
上記オルトクレゾールノボラック型エポキシ樹脂のうち市販されているものとしては、例えば、エピクロンN-670-EXP-S(DIC社製)等が挙げられる。
上記ジシクロペンタジエンノボラック型エポキシ樹脂のうち市販されているものとしては、例えば、エピクロンHP7200(DIC社製)等が挙げられる。
上記ビフェニルノボラック型エポキシ樹脂のうち市販されているものとしては、例えば、NC-3000P(日本化薬社製)等が挙げられる。
上記ナフタレンフェノールノボラック型エポキシ樹脂のうち市販されているものとしては、例えば、ESN-165S(新日鉄住金化学社製)等が挙げられる。
上記グリシジルアミン型エポキシ樹脂のうち市販されているものとしては、例えば、jER630(三菱化学社製)、エピクロン430(DIC社製)、TETRAD-X(三菱ガス化学社製)等が挙げられる。
上記アルキルポリオール型エポキシ樹脂のうち市販されているものとしては、例えば、ZX-1542(新日鉄住金化学社製)、エピクロン726(DIC社製)、エポライト80MFA(共栄社化学社製)、デナコールEX-611(ナガセケムテックス社製)等が挙げられる。
上記ゴム変性型エポキシ樹脂のうち市販されているものとしては、例えば、YR-450、YR-207(いずれも新日鉄住金化学社製)、エポリードPB(ダイセル社製)等が挙げられる。
上記グリシジルエステル化合物のうち市販されているものとしては、例えば、デナコールEX-147(ナガセケムテックス社製)等が挙げられる。
上記ビスフェノールA型エピスルフィド樹脂のうち市販されているものとしては、例えば、jER YL-7000(三菱化学社製)等が挙げられる。
上記エポキシ樹脂のうちその他に市販されているものとしては、例えば、YDC-1312、YSLV-80XY、YSLV-90CR(いずれも新日鉄住金化学社製)、XAC4151(旭化成社製)、jER1031、jER1032(いずれも三菱化学社製)、EXA-7120(DIC社製)、TEPIC(日産化学社製)等が挙げられる。
上記その他のラジカル重合性化合物としては、例えば、N,N-ジメチル(メタ)アクリルアミド、N-(メタ)アクリロイルモルホリン、N-ヒドロキシエチル(メタ)アクリルアミド、N,N-ジエチル(メタ)アクリルアミド、N-イソプロピル(メタ)アクリルアミド、N,N-ジメチルアミノプロピル(メタ)アクリルアミド等の(メタ)アクリルアミド化合物、スチレン、α-メチルスチレン、N-ビニルピロリドン、N-ビニル-ε-カプロラクタム等のビニル化合物等が挙げられる。
上記湿気硬化型樹脂としては、湿気硬化型ウレタン樹脂及び架橋性シリル基を有する樹脂等が挙げられる。なかでも、湿気硬化時の速硬化性に優れることから、湿気硬化型ウレタン樹脂が好ましい。上記湿気硬化型ウレタン樹脂は、ウレタン結合とイソシアネート基とを有し、分子内のイソシアネート基が空気中又は被着体中の水分と反応して硬化する。
上記湿気硬化型ウレタン樹脂は、上記イソシアネート基を分子の末端に有することが好ましい。
なお、上記湿気硬化型ウレタン樹脂は、ラジカル重合性基を有していても上記ラジカル重合性化合物には含まず、湿気硬化型ウレタン樹脂として扱う。
なかでも、プロピレングリコールや、テトラヒドロフラン(THF)化合物の開環重合化合物、又は、メチル基等の置換基を有するテトラヒドロフラン化合物の開環重合化合物からなるポリエーテルポリオールを用いたものが好ましい。
なお、Lが0の場合とは、Rと結合した炭素が直接酸素と結合している場合を意味する。
なお、本明細書において上記重量平均分子量は、ゲルパーミエーションクロマトグラフィー(GPC)で測定を行い、ポリスチレン換算により求められる値である。GPCによってポリスチレン換算による重量平均分子量を測定する際のカラムとしては、例えば、Shodex LF-804(昭和電工社製)等が挙げられる。また、GPCで用いる溶媒としては、テトラヒドロフラン等が挙げられる。
上記架橋性シリル基を有する樹脂のうち市販されているものとしては、例えば、エクスターS2410、S2420、S3430(いずれも旭硝子社製)、XMAP SA-100S(カネカ社製)等が挙げられる。
上記光ラジカル重合開始剤としては、例えば、ベンゾフェノン系化合物、アセトフェノン系化合物、アシルフォスフィンオキサイド系化合物、チタノセン系化合物、オキシムエステル系化合物、ベンゾインエーテル系化合物、チオキサントン等が挙げられる。
上記充填剤を含有することにより、本発明にかかる光湿気硬化型樹脂組成物は、好適なチクソ性を有するものとなり、塗布後の形状を充分に保持することができる。
なお、上記充填剤の一次粒子径は、NICOMP 380ZLS(PARTICLE SIZING SYSTEMS社製)等の粒度分布測定装置を用いて、上記充填剤を溶媒(水、有機溶媒等)に分散させて測定することができる。
また、上記充填剤は、本発明にかかる光湿気硬化型樹脂組成物中において二次粒子(一次粒子が複数集まったもの)として存在する場合があり、このような二次粒子の粒子径の好ましい下限は5nm、好ましい上限は500nm、より好ましい下限は10nm、より好ましい上限は100nmである。上記充填剤の二次粒子の粒子径は、本発明にかかる光湿気硬化型樹脂組成物又は本発明の硬化体を、透過型電子顕微鏡(TEM)を用いて観察することにより測定することができる。
上記疎水性表面処理としては、シリル化処理、アルキル化処理、エポキシ化処理等が挙げられる。なかでも、形状保持性を向上させる効果に優れることから、シリル化処理が好ましく、トリメチルシリル化処理がより好ましい。
具体的には例えば、上記トリメチルシリル化処理シリカは、例えば、シリカをゾルゲル法等の方法で合成し、シリカを流動させた状態でヘキサメチルジシラザンを噴霧する方法、アルコール、トルエン等の有機溶媒中にシリカを加え、更に、ヘキサメチルジシラザンと水とを加えた後、水と有機溶媒とをエバポレーターで蒸発乾燥させる方法等により作製することができる。
なお、本明細書において、上記「遮光剤」は、可視光領域の光を透過させ難い能力を有する材料を意味する。
上記チタンブラックは、光学濃度(OD値)が、3以上であることが好ましく、4以上であることがより好ましい。また、上記チタンブラックは、黒色度(L値)が9以上であることが好ましく、11以上であることがより好ましい。上記チタンブラックの遮光性は高ければ高いほど良く、上記チタンブラックのOD値に好ましい上限は特に無いが、通常は5以下となる。
また、本発明にかかる光湿気硬化型樹脂組成物を用いて製造した表示素子は、光湿気硬化型樹脂組成物が充分な遮光性を有するため、光の漏れ出しがなく高いコントラストを有し、優れた画像表示品質を有するものとなる。
なお、上記遮光剤の粒子径は、NICOMP 380ZLS(PARTICLE SIZING SYSTEMS社製)を用いて、上記遮光剤を溶媒(水、有機溶媒等)に分散させて測定することができる。
上記カップリング剤としては、例えば、シランカップリング剤、チタネート系カップリング剤、ジルコネート系カップリング剤等が挙げられる。なかでも、接着性や耐クリープ性を向上させる効果に特に優れることから、シランカップリング剤が好ましい。
上記カップリング剤の含有量は、上記ラジカル重合性化合物と上記湿気硬化型樹脂との合計100重量部に対して、好ましい下限が0.05重量部、好ましい上限が5重量部である。
なお、本明細書において上記チクソトロピックインデックスとは、コーンプレート型粘度計を用いて25℃、1rpmの条件で測定した粘度を、コーンプレート型粘度計を用いて25℃、10rpmの条件で測定した粘度で除した値を意味する。
上記被着体の形状としては、例えば、フィルム状、シート状、板状、パネル状、トレイ状、ロッド(棒状体)状、箱体状、筐体状等が挙げられる。
上記ガラスとしては、例えば、アルカリガラス、無アルカリガラス、石英ガラス等が挙げられる。
上記プラスチックとしては、例えば、高密度ポリエチレン、超高分子量ポリエチレン、アイソタクチックポリプロピレン、シンジオタクチックポリプロピレン、エチレンプロピレン共重合体樹脂等のポリオレフィン系樹脂、ナイロン6(N6)、ナイロン66(N66)、ナイロン46(N46)、ナイロン11(N11)、ナイロン12(N12)、ナイロン610(N610)、ナイロン612(N612)、ナイロン6/66共重合体(N6/66)、ナイロン6/66/610共重合体(N6/66/610)、ナイロンMXD6(MXD6)、ナイロン6T、ナイロン6/6T共重合体、ナイロン66/PP共重合体、ナイロン66/PPS共重合体等のポリアミド系樹脂、ポリブチレンテレフタレート(PBT)、ポリエチレンテレフタレート(PET)、ポリエチレンイソフタレート(PEI)、PET/PEI共重合体、ポリアリレート(PAR)、ポリブチレンナフタレート(PBN)、液晶ポリエステル、ポリオキシアルキレンジイミドジ酸/ポリブチレンテレフタレート共重合体等の芳香族ポリエステル系樹脂、ポリアクリロニトリル(PAN)、ポリメタクリロニトリル、アクリロニトリル/スチレン共重合体(AS)、メタクリロニトリル/スチレン共重合体、メタクリロニトリル/スチレン/ブタジエン共重合体等のポリニトリル系樹脂、ポリカーボネート、ポリメタクリル酸メチル(PMMA)、ポリメタクリル酸エチル酢酸ビニル(EVA)等のポリメタクリレート系樹脂、ポリビニルアルコール(PVA)、ビニルアルコール/エチレン共重合体(EVOH)、ポリ塩化ビニリデン(PVDC)、ポリ塩化ビニル(PVC)、塩化ビニル/塩化ビニリデン共重合体、塩化ビニリデン/メチルアクリレート共重合体等のポリビニル系樹脂等が挙げられる。
更に、上記被着体としては、金属表面を不動態化処理することにより不動態皮膜を形成した材料も挙げられ、該不動態化処理としては、例えば、加熱処理、陽極酸化処理等が挙げられる。特に、国際アルミニウム合金名が6000番台の材質であるアルミニウム合金等の場合は、上記不動態化処理として硫酸アルマイト処理又はリン酸アルマイト処理を行うことで、接着性を向上させることができる。
上記OD値は高いほど良いが、上記OD値を高くするために遮光剤を多く配合しすぎると、増粘による作業性の低下等が生じることから、遮光剤の配合量とのバランスをとるため、上記硬化体のOD値の好ましい上限は4である。
なお、本発明の硬化体のOD値は、光学濃度計を用いて測定することができる。
なお、本明細書において上記「引張弾性率」は、引張り試験機(例えば、島津製作所社製、「EZ-Graph」)を用いて、硬化体を10mm/minの速度で引張り、10%伸びた時の力として測定される値を意味する。
ポリオール化合物として100重量部のポリテトラメチレンエーテルグリコール(三菱化学社製、「PTMG-2000」)と、0.01重量部のジブチル錫ジラウレートとを500mL容のセパラブルフラスコに入れ、真空下(20mmHg以下)、100℃で30分間撹拌し、混合した。その後常圧とし、ポリイソシアネート化合物としてジフェニルメタンジイソシアネート(日曹商事社製、「Pure MDI」)26.5重量部を入れ、80℃で3時間撹拌し、反応させ、両末端にイソシアネート基を有する湿気硬化型ウレタン樹脂A(重量平均分子量2700)を得た。
ポリオール化合物として100重量部のポリプロピレングリコール(旭硝子社製、「EXCENOL 2020」)と、0.01重量部のジブチル錫ジラウレートとを500mL容のセパラブルフラスコに入れ、真空下(20mmHg以下)、100℃で30分間撹拌し、混合した。その後常圧とし、ポリイソシアネート化合物としてジフェニルメタンジイソシアネート(日曹商事社製、「Pure MDI」)26.5重量部を入れ、80℃で3時間撹拌し、反応させ、両末端にイソシアネート基を有する湿気硬化型ウレタン樹脂B(重量平均分子量2900)を得た。
合成例1と同様にして得られた湿気硬化型ウレタン樹脂A100重量部の入った反応容器に、3-メルカプトプロピルトリメトキシシラン(信越化学工業社製、「KBM-803」)9.8重量部を添加し、80℃で1時間撹拌混合し、有機シリル基含有ウレタン樹脂として、分子末端にイソシアネート基とトリメトキシシリル基とを有する湿気硬化型ウレタン樹脂C(重量平均分子量3100)を得た。
表1、2に記載された配合比に従い、各材料を、遊星式撹拌装置(シンキー社製、「あわとり練太郎」)にて撹拌した後、セラミック3本ロールにて均一に混合して光湿気硬化型樹脂組成物を得た。
得られた光湿気硬化型樹脂組成物の一部を、幅3mm、長さ50mm、高さ1mmのテフロン(登録商標)製の型枠に埋めた。その後、高圧水銀ランプを用いて、紫外線を1000mJ/cm2照射することによって、光湿気硬化型樹脂組成物を光硬化させた後、一晩以上静置することにより湿気硬化させ、硬化体を得た。
実施例及び比較例で得られた各光湿気硬化型樹脂組成物及び各硬化体について以下の評価を行った。結果を表1、2に示した。
実施例及び比較例で得られた各硬化体を、幅3mm、長さ20mm、厚さ0.8mmに切り出して、動的粘弾性測定装置(IT計測制御社製、「DVA-200」)を用いて、変形モード:引っぱり、設定ひずみ1%、測定周波数1Hz、昇温速度5℃/minの条件で-70℃~100℃の範囲で動的粘弾性を測定し、0℃及び50℃における貯蔵弾性率を求めた。また、損失正接(tanδ)の極大値の温度をガラス転移温度として求めた。
実施例及び比較例で得られた各光湿気硬化型樹脂組成物を、ディスペンス装置を用いて、ポリカーボネート基板に約2mmの幅で塗布した。次いで、UV-LED(波長365nm)を用いて、紫外線を1000mJ/cm2照射することによって、光湿気硬化型樹脂組成物を光硬化させた。その後、ポリカーボネート基板にガラス板を貼り合わせ、20gの重りを置き、一晩放置することにより湿気硬化させて、耐クリープ性評価用サンプルを得た。
図1に耐クリープ性評価用サンプルを上から見た場合を示す模式図(図1(a))、及び、耐クリープ性評価用サンプルを横から見た場合を示す模式図(図1(b))を示した。得られた耐クリープ性評価用サンプルを地面に対して垂直にぶら下げ、ポリカーボネート基板の端に100gの重りを吊るした状態で50℃、80%RHの恒温恒湿機に入れ、24時間静置した。24時間静置後、ポリカーボネート基板とガラス板とが剥がれていなかった場合を「○」、ポリカーボネート基板とガラス板とが部分的に剥がれていた場合を「△」、ポリカーボネート基板とガラス板とが完全に剥がれていた場合を「×」として、光湿気硬化型樹脂組成物の耐クリープ性を評価した。
実施例及び比較例で得られた各硬化体をダンベル状(「JIS K 6251」で規定される6号形)に打ち抜いて得られた試験片を、引張り試験機(島津製作所社製、「EZ-Graph」)を用いて、10mm/minの速度で引張り、10%伸びた時の力を引張弾性率として求めた。
2 光湿気硬化型樹脂組成物
3 ガラス板
Claims (11)
- ラジカル重合性化合物と湿気硬化型樹脂とを含有する光湿気硬化型樹脂組成物の硬化体であって、
0℃における貯蔵弾性率が1.0×107Pa以上であり、かつ、50℃における貯蔵弾性率が5.0×106Pa以下であることを特徴とする硬化体。 - ガラス転移温度を2つ以上有し、かつ、0℃以下のガラス転移温度及び0℃を超え30℃以下のガラス転移温度をそれぞれ1つ以上有することを特徴とする請求項1記載の硬化体。
- ラジカル重合性化合物は、脂肪族ウレタン(メタ)アクリレートを含有することを特徴とする請求項1又は2記載の硬化体。
- 湿気硬化型樹脂は、湿気硬化型ウレタン樹脂であることを特徴とする請求項1、2又は3記載の硬化体。
- 湿気硬化型ウレタン樹脂は、エチレン性不飽和二重結合を含む基及び/又はアルコキシシリル基を有することを特徴とする請求項4記載の硬化体。
- 光湿気硬化型樹脂組成物は、一次粒子径が1~50nmの充填剤を含有することを特徴とする請求項1、2、3、4又は5記載の硬化体。
- 光湿気硬化型樹脂組成物は、遮光剤を含有することを特徴とする請求項1、2、3、4、5又は6記載の硬化体。
- 光湿気硬化型樹脂組成物は、光ラジカル重合開始剤を含有することを特徴とする請求項1、2、3、4、5、6又は7記載の硬化体。
- 光湿気硬化型樹脂組成物は、カップリング剤を含有することを特徴とする請求項1、2、3、4、5、6、7又は8記載の硬化体。
- 基板と請求項1、2、3、4、5、6、7、8又は9記載の硬化体とを有する電子部品。
- 基板と請求項1、2、3、4、5、6、7、8又は9記載の硬化体とを有する表示素子。
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KR (2) | KR20210127820A (ja) |
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JP2017215585A (ja) * | 2016-05-26 | 2017-12-07 | 日本精化株式会社 | 樹脂基材のハードコート形成用組成物、ハードコートの形成方法およびそれを用いた物品 |
JP2018002925A (ja) * | 2016-07-05 | 2018-01-11 | 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 |
JP2020059788A (ja) * | 2018-10-09 | 2020-04-16 | Dic株式会社 | 樹脂組成物及び該樹脂組成物から形成される物品 |
JP2020059790A (ja) * | 2018-10-09 | 2020-04-16 | Dic株式会社 | 樹脂組成物及び該樹脂組成物から形成される物品 |
EP3913028A4 (en) * | 2019-01-18 | 2022-09-21 | Sekisui Chemical Co., Ltd. | CURABLE RESIN COMPOSITION AND CURED BODY |
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JP2020158197A (ja) * | 2019-03-28 | 2020-10-01 | オート化学工業株式会社 | 硬化性組成物の充填方法 |
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Also Published As
Publication number | Publication date |
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KR20210127820A (ko) | 2021-10-22 |
KR102323646B1 (ko) | 2021-11-08 |
CN106232634A (zh) | 2016-12-14 |
TWI687444B (zh) | 2020-03-11 |
JP6023359B2 (ja) | 2016-11-09 |
CN106232634B (zh) | 2019-08-16 |
JP6243969B2 (ja) | 2017-12-06 |
TW201629107A (zh) | 2016-08-16 |
JPWO2016076407A1 (ja) | 2017-04-27 |
JP2016172878A (ja) | 2016-09-29 |
KR20170083964A (ko) | 2017-07-19 |
JP2018021209A (ja) | 2018-02-08 |
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