WO2015174371A1 - Photo- and moisture-curing resin composition, adhesive for electronic parts, and adhesive for display element - Google Patents

Abstract

The objective of the present invention is to provide a photo- and moisture-curing resin composition that has excellent adhesiveness and reliability in a high temperature/high humidity environment. The objective of the present invention is also to provide an adhesive for electronic parts and an adhesive for a display element which are made using the photo- and moisture-curing resin composition. This photo- and moisture-curing resin composition includes a radical polymerizable compound, a moisture-curing urethane resin, and a photo-radical polymerization initiator, wherein the moisture-curing urethane resin includes a compound having an urethane bond, a group represented by formula (1), and an isocyanate group. In formula (1), R¹ and R² are a hydrogen, an alkyl group having 1 to 5 carbon atoms, or an aryl group, and R¹ and R² may be the same or different, and x is 0 to 2.

Description

Light moisture curable resin composition, adhesive for electronic parts, and adhesive for display elements

The present invention relates to a light moisture curable resin composition having excellent adhesiveness and reliability in a high temperature and high humidity environment. Moreover, this invention relates to the adhesive agent for electronic components and the adhesive agent for display elements which use this optical moisture hardening type resin composition.

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. In these display elements, a photocurable resin composition is usually used for sealing a liquid crystal or a light emitting layer, bonding a substrate, an optical film, a protective film, or various members.
By the way, in the present age when mobile devices with various display elements such as mobile phones and portable game machines are widespread, downsizing of the display elements is the most demanded issue. A frame is being made (hereinafter also referred to as a narrow frame design). However, in a narrow frame design, a photocurable resin composition may be applied to a portion where light does not reach sufficiently, and as a result, the photocurable resin composition applied to a portion where light does not reach is cured. There was a problem that was insufficient. Therefore, 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.

As a method for curing a resin composition without heating at a high temperature, Patent Document 1 discloses a light containing a urethane prepolymer having at least one isocyanate group and at least one (meth) acryloyl group in the molecule. A method of using a moisture curable resin composition in combination with photocuring and moisture curing is disclosed. However, when the optical moisture curable resin composition as disclosed in Patent Document 1 is used, the adhesiveness when an adherend such as a substrate is adhered and the reliability in a high-temperature and high-humidity environment (especially withstand resistance) Creepability) may be insufficient.

JP 2008-274131 A

An object of the present invention is to provide an optical moisture curable resin composition having excellent adhesiveness and reliability in a high temperature and high humidity environment. Another object of the present invention is to provide an adhesive for electronic parts and an adhesive for display elements using the light moisture curable resin composition.

The present invention includes a radical polymerizable compound, a moisture curable urethane resin, and a photo radical polymerization initiator, and the moisture curable urethane resin includes a urethane bond and a group represented by the following formula (1): And an optical moisture curable resin composition containing a compound having an isocyanate group.

In formula (1), R ¹ and R ² are hydrogen, an alkyl group having 1 to 5 carbon atoms, or an aryl group, and R ¹ and R ² may be the same or different. Also good. x is 0-2.
The present invention is described in detail below.

Surprisingly, the inventors of the present invention have a specific functional group as a moisture curable urethane resin in a light moisture curable resin composition containing a radical polymerizable compound, a moisture curable urethane resin, and a photo radical polymerization initiator. It has been found that a light moisture curable resin composition excellent in adhesiveness and reliability in a high temperature and high humidity environment can be obtained by using a compound having the above, and the present invention has been completed.

The optical moisture curable resin composition of the present invention contains a moisture curable urethane resin. In the moisture-curable urethane resin, the isocyanate group in the molecule is cured by reacting with moisture in the air or in the adherend.

The moisture curable urethane resin contains a compound having a urethane bond, a group represented by the above formula (1), and an isocyanate group (hereinafter also referred to as “organic silyl group-containing urethane resin”). By containing the organic silyl group-containing urethane resin as the moisture curable urethane resin, the optical moisture curable resin composition of the present invention is excellent in adhesiveness and reliability in a high temperature and high humidity environment.

The organic silyl group-containing urethane resin has a group represented by the above formula (1).
In the above formula (1), R ¹ and R ² are preferably alkyl groups having 1 to 5 carbon atoms because they are excellent in adhesiveness and the effect of improving reliability in a high temperature and high humidity environment. More preferred are a methyl group and an ethyl group.
When R ¹ and R ² are an aryl group, examples of the aryl group include a phenyl group, a naphthyl group, and a 2-methylphenyl group.
The case where x in the above formula (1) is 0 means that the silicon atom is bonded to three —OR ² groups without being bonded to the atom or group represented by R ¹ .

The organic silyl group-containing urethane resin has an isocyanate group.
The organic silyl group-containing urethane resin may have only one isocyanate group in one molecule, or may have two or more.

The organic silyl group-containing urethane resin preferably has a group represented by the above formula (1) and the isocyanate group at each end.

The organic silyl group-containing urethane resin is 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, and an isocyanate. It can be obtained by reacting a compound having a group with a compound having a reactive functional group and a group represented by the formula (1). The “reactive functional group” means a group capable of reacting with the compound having the urethane bond and the isocyanate group.

The reaction between the polyol compound and the polyisocyanate compound is usually such that the molar ratio of the hydroxyl group (OH) in the polyol compound to the isocyanate group (NCO) in the polyisocyanate compound is [NCO] / [OH] = 2. It is performed in the range of 0.0 to 2.5.

As said polyol compound, the well-known polyol compound normally used for manufacture of a polyurethane can be used, For example, polyester polyol, polyether polyol, polyalkylene polyol, polycarbonate polyol etc. are mentioned. These polyol compounds may be used independently and may be used in combination of 2 or more type.

Examples of the polyester polyol include a polyester polyol obtained by a reaction between a polyvalent carboxylic acid and a polyol, and a poly-ε-caprolactone polyol obtained by ring-opening polymerization of ε-caprolactone.

Examples of the polyvalent carboxylic acid used as a raw material for the polyester polyol 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.

Examples of the polyol used as a raw material for the polyester polyol include ethylene glycol, propylene glycol, 1,3-propanediol, 1,4-butanediol, neopentyl glycol, 1,5-pentanediol, and 1,6-hexane. Diol, diethylene glycol, cyclohexanediol, etc. are mentioned.

Examples of the polyether polyol include ring-opening polymerization compounds of ethylene glycol, propylene glycol, tetrahydrofuran, 3-methyltetrahydrofuran, random copolymers or block copolymers of these and derivatives thereof, and bisphenol type polyoxy An alkylene modified body etc. are mentioned.

The modified bisphenol-type polyoxyalkylene is a polyether polyol obtained by addition reaction of alkylene oxide (for example, ethylene oxide, propylene oxide, butylene oxide, isobutylene oxide, etc.) to the active hydrogen portion of the bisphenol-type molecular skeleton, A random copolymer or a block copolymer may be used. The modified bisphenol-type polyoxyalkylene preferably has one or more alkylene oxides added to both ends of the bisphenol-type molecular skeleton.
It does not specifically limit as a bisphenol type, A type, F type, S type etc. are mentioned, Preferably it is bisphenol A type.

Examples of the polyalkylene polyol include polybutadiene polyol, hydrogenated polybutadiene polyol, and hydrogenated polyisoprene polyol.

Examples of the polycarbonate polyol include polyhexamethylene carbonate polyol and polycyclohexane dimethylene carbonate polyol.

Examples of the polyisocyanate compound include diphenylmethane diisocyanate, a liquid modified product of diphenylmethane diisocyanate, polymeric MDI (methane diisocyanate), tolylene diisocyanate, naphthalene-1,5-diisocyanate, and the like. Of these, diphenylmethane diisocyanate and its modified products are preferred from the viewpoint of low vapor pressure, low toxicity, and ease of handling. The said polyisocyanate compound may be used independently and may be used in combination of 2 or more type.

Examples of the compound having the reactive functional group and the group represented by the formula (1) include 3-mercaptopropyltrimethoxysilane, 3-mercaptopropyltriethoxysilane, 3-mercaptopropylmethyldimethoxysilane, 3- Mercaptopropylmethyldiethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropyltriethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 3-glycidoxypropylmethyldiethoxysilane, 2- (3,4-epoxycyclohexyl) ethyltrimethoxysilane, 3-glycidoxypropylmethyldiethoxysilane, 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, 3- (2-aminoethyl) aminopropyl bird Toxisilane, 3- (2-aminoethyl) aminopropyltriethoxysilane, 3- (2-aminoethyl) aminopropylmethyldimethoxysilane, 3- (meth) acryloyloxypropyltrimethoxysilane, 3- (meth) acryloyloxypropyl Examples include triethoxysilane, 3- (meth) acryloyloxypropylmethyldimethoxysilane, 3- (meth) acryloyloxypropylmethyldiethoxysilane, vinyltrimethoxysilane, vinyltriethoxysilane, and 3-isocyanatopropyltrimethoxysilane. . Especially, what has a thiol group as a reactive functional group from a reactive viewpoint is preferable.
In the present specification, the “(meth) acryloyl” means acryloyl or methacryloyl.

The content of the organic silyl group-containing urethane resin is preferably 1 part by weight with a preferred lower limit and 50 parts by weight with respect to a total of 100 parts by weight of the radical polymerizable compound and the moisture curable urethane resin. When the content of the organic silyl group-containing urethane resin is less than 1 part by weight, the effect of improving the adhesiveness and the reliability in a high temperature and high humidity environment may not be sufficiently exhibited. If the content of the organic silyl group-containing urethane resin exceeds 50 parts by weight, the reaction of the moisture curable urethane resin may be inhibited, the elastic modulus of the cured product may be reduced, and sufficient adhesive strength may not be ensured. The more preferred lower limit of the content of the organic silyl group-containing urethane resin is 2 parts by weight, the more preferred upper limit is 30 parts by weight, the still more preferred lower limit is 5 parts by weight, and the still more preferred upper limit is 25 parts by weight.

The optical moisture curable resin composition of the present invention preferably further contains other moisture curable urethane resin other than the organic silyl group-containing urethane resin. By containing other moisture curable urethane resins other than the organic silyl group-containing urethane resin, it becomes easy to adjust the curability.
As said other moisture hardening type urethane resin, the compound which has the urethane bond mentioned above and an isocyanate group is used suitably.
Hereinafter, matters common to the entire moisture curable urethane resin including the organic silyl group-containing urethane resin are simply treated as “moisture curable urethane resin”.

The moisture curable urethane resin is preferably obtained using a polyol compound having a structure represented by the following formula (2). By using a polyol compound having a structure represented by the following formula (2), 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. The moisture curable urethane resin preferably has a branched chain.
Among these, those using a polyether polyol made of propylene glycol, a ring-opening polymerization compound of a tetrahydrofuran (THF) compound, or a ring-opening polymerization compound of a tetrahydrofuran compound having a substituent such as a methyl group are preferable.

In formula (2), 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, and m is an integer of 1 to 500. n is preferably 1 to 5, L is preferably 0 to 4, and m is preferably 50 to 200.
The case where L is 0 means the case where carbon bonded to R is directly bonded to oxygen.

Furthermore, the moisture curable urethane resin may have a radical polymerizable group.
The radical polymerizable 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 group is not included in the radical polymerizable compound and is treated as a moisture curable urethane resin.

The preferable lower limit of the weight average molecular weight of the moisture curable urethane resin is 800, and the preferable upper limit is 10,000. When the weight average molecular weight of the moisture curable urethane resin is less than 800, the crosslink density increases and flexibility may be impaired. When the weight average molecular weight of the moisture curable urethane resin exceeds 10,000, the resulting light moisture curable resin composition may have poor applicability. The more preferable lower limit of the weight average molecular weight of the moisture curable urethane resin is 2000, the more preferable upper limit is 8000, the still more preferable lower limit is 2500, and the further preferable upper limit is 6000.
In addition, the said weight average molecular weight is a value calculated | required by polystyrene conversion by measuring with a gel permeation chromatography (GPC) in this specification. Examples of the column for measuring the weight average molecular weight in terms of polystyrene by GPC include Shodex LF-804 (manufactured by Showa Denko KK). Moreover, tetrahydrofuran etc. are mentioned as a solvent used by GPC.

The content of the moisture curable urethane resin is preferably 20 parts by weight with a preferred lower limit and 90 parts by weight with respect to a total of 100 parts by weight of the radical polymerizable compound and the moisture curable urethane resin. When the content of the moisture curable urethane resin is less than 20 parts by weight, the resulting optical moisture curable resin composition may be inferior in moisture curable property. If the content of the moisture curable urethane resin exceeds 90 parts by weight, the resulting light moisture curable resin composition may be inferior in photocurability. The more preferable lower limit of the content of the moisture curable urethane resin is 30 parts by weight, the more preferable upper limit is 75 parts by weight, the still more preferable lower limit is 41 parts by weight, and the still more preferable upper limit is 70 parts by weight.

The light moisture curable resin composition of the present invention contains a radically polymerizable compound.
The radical polymerizable compound is not particularly limited as long as it is a photopolymerizable radical polymerizable compound and is a compound having a radical polymerizable group in the molecule, but the radical polymerizable group is an unsaturated double bond. A compound having a (meth) acryloyl group (hereinafter, also referred to as “(meth) acrylic compound”) is preferable from the viewpoint of reactivity.
In the present specification, the “(meth) acryl” means acryl or methacryl.

Examples of the (meth) acrylic compound include an ester compound obtained by reacting a compound having a hydroxyl group with (meth) acrylic acid, and an epoxy (meth) acrylic obtained by reacting (meth) acrylic acid with an epoxy compound. ) Urethane (meth) acrylate obtained by reacting a (meth) acrylic acid derivative having a hydroxyl group with an acrylate or isocyanate compound.
In the present specification, the “(meth) acrylate” means acrylate or methacrylate. Moreover, 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.

Examples of the monofunctional compounds of the ester compounds include 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, Isobutyl (meth) acrylate, t-butyl (meth) acrylate, isooctyl (meth) acrylate, lauryl (meth) acrylate, stearyl (meth) acrylate, isobornyl (meth) acrylate, cyclohexyl (meth) acrylate, 2-methoxyethyl (meth) ) Acrylate, methoxyethylene glycol (meth) acrylate, 2-ethoxyethyl (meth) acrylate, tetrahydrofurfuryl (meth) acrylate, benzyl (meth) acrylate, ethylcal Tall (meth) acrylate, phenoxyethyl (meth) acrylate, phenoxydiethylene glycol (meth) acrylate, phenoxypolyethylene glycol (meth) acrylate, methoxypolyethylene glycol (meth) acrylate, 2,2,2-trifluoroethyl (meth) acrylate, 2,2,3,3-tetrafluoropropyl (meth) acrylate, 1H, 1H, 5H-octafluoropentyl (meth) acrylate, imide (meth) acrylate, methyl (meth) acrylate, ethyl (meth) acrylate, n- Butyl (meth) acrylate, propyl (meth) acrylate, cyclohexyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, n-octyl (meth) acrylate, isononyl (Meth) acrylate, isomyristyl (meth) acrylate, 2-butoxyethyl (meth) acrylate, 2-phenoxyethyl (meth) acrylate, bicyclopentenyl (meth) acrylate, isodecyl (meth) acrylate, diethylaminoethyl (meth) acrylate, dimethyl Aminoethyl (meth) acrylate, 2- (meth) acryloyloxyethyl succinic acid, 2- (meth) acryloyloxyethyl hexahydrophthalic acid, 2- (meth) acryloyloxyethyl 2-hydroxypropyl phthalate, glycidyl ( Examples thereof include phthalimide acrylates such as (meth) acrylate, 2- (meth) acryloyloxyethyl phosphate, N-acryloyloxyethyl hexahydrophthalimide, and various imide acrylates.

Examples of the bifunctional ester compound include 1,4-butanediol di (meth) acrylate, 1,3-butanediol di (meth) acrylate, and 1,6-hexanediol di (meth). Acrylate, 1,9-nonanediol di (meth) acrylate, 1,10-decandiol di (meth) acrylate, 2-n-butyl-2-ethyl-1,3-propanediol di (meth) acrylate, dipropylene Glycol di (meth) acrylate, tripropylene glycol di (meth) acrylate, polypropylene glycol (meth) acrylate, ethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, tetraethylene glycol di (meth) acrylate, polyethylene glycol (Meth) acrylate, propylene oxide-added bisphenol A di (meth) acrylate, ethylene oxide-added bisphenol A di (meth) acrylate, ethylene oxide-added bisphenol F di (meth) acrylate, dimethylol dicyclopentadienyl di (meth) acrylate, 1 , 3-butylene glycol di (meth) acrylate, neopentyl glycol di (meth) acrylate, ethylene oxide modified isocyanuric acid di (meth) acrylate, 2-hydroxy-3- (meth) acryloyloxypropyl (meth) acrylate, carbonate diol Di (meth) acrylate, polyether diol di (meth) acrylate, polyester diol di (meth) acrylate, polycaprolactone diol di (meth) acrylate Over DOO, polybutadiene di (meth) acrylate.

Examples of the ester compound having three or more functional groups include pentaerythritol tri (meth) acrylate, trimethylolpropane tri (meth) acrylate, propylene oxide-added trimethylolpropane tri (meth) acrylate, and ethylene oxide-added trimethylol. Propane tri (meth) acrylate, caprolactone-modified trimethylolpropane tri (meth) acrylate, ethylene oxide-added isocyanuric acid tri (meth) acrylate, dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa (meth) acrylate, ditrimethylolpropane tetra (Meth) acrylate, pentaerythritol tetra (meth) acrylate, glycerin tri (meth) acrylate, propylene Oxide addition glycerin tri (meth) acrylate, tris (meth) acryloyloxyethyl phosphate, and the like.

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 Epicoat 828EL, Epicoat 1001, Epicoat 1004 (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, Epicoat 806, Epicoat 4004 (all are Mitsubishi Chemical Corporation 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.).
As what is marketed among the said hydrogenated bisphenol type | mold epoxy resins, Epicron EXA7015 (made by DIC Corporation) etc. are mentioned, for example.
Examples of commercially available propylene oxide-added bisphenol A type epoxy resins include EP-4000S (manufactured by ADEKA).
Examples of commercially available resorcinol type epoxy resins include EX-201 (manufactured by Nagase ChemteX Corporation).
Examples of commercially available biphenyl type epoxy resins include Epicoat YX-4000H (manufactured by Mitsubishi Chemical Corporation).
Examples of commercially available sulfide type epoxy resins include YSLV-50TE (manufactured by Nippon Steel & Sumikin Chemical 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).
As what is marketed among the said dicyclopentadiene novolak-type epoxy resins, epiclone HP7200 (made by DIC) etc. are mentioned, for example.
Examples of commercially available biphenyl novolac epoxy resins include NC-3000P (manufactured by Nippon Kayaku Co., Ltd.).
Examples of commercially available naphthalene phenol novolac type epoxy resins include ESN-165S (manufactured by Nippon Steel & Sumikin Chemical Co., Ltd.).
Examples of commercially available glycidylamine epoxy resins include Epicoat 630 (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.) and Epolide PB (manufactured by Daicel Chemical Industries, Ltd.).
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 Epicoat YL-7000 (manufactured by Mitsubishi Chemical Corporation).
Other commercially available 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.), Epicoat 1031 and Epicoat 1032. (All manufactured by Mitsubishi Chemical), EXA-7120 (manufactured by DIC), TEPIC (manufactured by Nissan Chemical) 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-314 And Denacol acrylate DA-911 (all manufactured by Nagase ChemteX Corporation).

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.

Examples of the isocyanate compound used as the raw material for the urethane (meth) acrylate include isophorone diisocyanate, 2,4-tolylene diisocyanate, 2,6-tolylene diisocyanate, hexamethylene diisocyanate, trimethylhexamethylene diisocyanate, and diphenylmethane-4,4. '-Diisocyanate (MDI), 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, tetramethylxylene diisocyanate, 1,6,11-undecanetriiso Aneto and the like.

Examples of the isocyanate compound include ethylene glycol, glycerin, sorbitol, trimethylolpropane, (poly) propylene glycol, carbonate diol, polyether diol, polyester diol, polycaprolactone diol, and other polyols and excess isocyanate compounds. Chain-extended isocyanate compounds obtained by the reaction can also be used.

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. Di (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, glycerin, and bisphenol A type Examples include epoxy (meth) acrylates such as epoxy (meth) acrylate.

Examples of commercially available urethane (meth) acrylates include M-1100, M-1200, M-1210, M-1600 (all manufactured by Toagosei Co., Ltd.), EBECRYL230, EBECRYL270, EBECRYL4858, EBECRYL8402, EBECRYL8411, EBECRYL8412, EBECRYL8413, EBECRYL8804, EBECRYL8803, EBECRYL8807, EBECRYL9260, EBECRYL1290, EBECRYL5129, EBECRYL4842, EBECRYL210, EBECRYL4827, EBECRYL6700, EBECRYL220, EBECRYL2220, KRM7735, KRM-8295 (both manufactured by Daicel Orunekusu, Inc. ), Art Resin UN-9000H, Art Resin UN-9000A, Art Resin UN-7100, Art Resin UN-1255, Art Resin UN-330, Art Resin UN-3320HB, Art Resin UN-1200TPK, Art Resin SH-500B ( All are manufactured by Negami Kogyo Co., Ltd.), U-2HA, U-2PHA, U-3HA, U-4HA, U-6H, U-6LPA, U-6HA, U-10H, U-15HA, U-122A, U- 122P, U-108, U-108A, U-324A, U-340A, U-340P, U-1084A, U-2061BA, UA-340P, UA-4100, UA-4000, UA-4200, UA-4400, UA-5201P, UA-7100, UA-7200, UA-W2A (all Shin-Nakamura Manabu Industries, Ltd.), AI-600, AH-600, AT-600, UA-101I, UA-101T, UA-306H, UA-306I, UA-306T (all manufactured by Kyoeisha Chemical Co., Ltd.).

In addition, other radical polymerizable compounds other than those described above can be used as appropriate.
Examples of 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 and N, N-dimethylaminopropyl (meth) acrylamide, and vinyl compounds such as styrene, α-methylstyrene, N-vinylpyrrolidone and N-vinylcaprolactone. It is done.

The content of the radical polymerizable compound is such that the preferred lower limit is 10 parts by weight and the 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 urethane resin. When the content of the radical polymerizable compound is less than 10 parts by weight, the resulting light moisture curable resin composition may be inferior in photocurability. When the content of the radical polymerizable compound exceeds 80 parts by weight, the resulting optical moisture curable resin composition may be inferior in moisture curability. A more 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, and a still more preferred upper limit is 59 parts by weight.

The radical polymerizable compound preferably contains a monofunctional radical polymerizable compound and a polyfunctional radical polymerizable compound from the viewpoint of adjusting curability. When only a monofunctional radically polymerizable compound is used, the resulting light moisture curable resin composition may be inferior in curability, and when only a polyfunctional radically polymerizable compound is used, the resulting light moisture cured The mold resin composition may be inferior in tackiness. Among these, it is more preferable to use a combination of a compound having a nitrogen atom in the molecule as the monofunctional radical polymerizable compound and a urethane (meth) acrylate as the polyfunctional radical polymerizable compound. The polyfunctional radically polymerizable compound is preferably bifunctional or trifunctional, and more preferably bifunctional.

When 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. When the content of the polyfunctional radically polymerizable compound is less than 2 parts by weight, the resulting light moisture curable resin composition may be inferior in curability. When content of the said polyfunctional radically polymerizable compound exceeds 45 weight part, the optical moisture hardening type resin composition obtained may become inferior to tack property. 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 light moisture curable resin composition of the present invention contains a radical photopolymerization initiator.
Examples of 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.

Examples of commercially available photoradical polymerization initiators include IRGACURE 184, IRGACURE 369, IRGACURE 379, IRGACURE 651, IRGACURE 784, IRGACURE 819, IRGACURE 907, IRGACURE 2959, IRGACUREOXE01, and Benzylin TPO from Benzylin SPO Benzoin ethyl ether, benzoin isopropyl ether (both 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 less than 0.01 part by weight, the resulting light moisture curable resin composition may not be sufficiently photocured. When content of the said radical photopolymerization initiator exceeds 10 weight part, the storage stability of the obtained optical moisture hardening type resin composition may fall. The minimum with more preferable content of the said radical photopolymerization initiator is 0.1 weight part, and a more preferable upper limit is 5 weight part.

The light moisture curable resin composition of the present invention may contain a filler from the viewpoint of adjusting the applicability and shape retention of the resulting light moisture curable resin composition.
The filler preferably has a primary particle diameter with a preferred lower limit of 1 nm and a preferred upper limit of 50 nm. When the primary particle diameter of the filler is less than 1 nm, the resulting light moisture curable resin composition has poor applicability. When the primary particle diameter of the filler exceeds 50 nm, the resulting light moisture curable resin composition is inferior in shape retention after application. The more preferable lower limit of the primary particle diameter of the filler is 5 nm, the more preferable upper limit is 30 nm, the still more preferable lower limit is 10 nm, and the still more preferable upper limit is 20 nm.
The primary particle size of the filler can be measured by dispersing the filler in a solvent (water, organic solvent, etc.) using NICOMP 380ZLS (manufactured by PARTICS SIZING SYSTEMS).
In addition, 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 size of such secondary particles is 5 nm, a preferable upper limit is 500 nm, a more preferable lower limit is 10 nm, and a more preferable 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).

Examples of the filler include silica, talc, titanium oxide, and zinc oxide. Among these, silica is preferable because the obtained light moisture curable resin composition is excellent in UV light transmittance. These fillers may be used independently and may be used in combination of 2 or more type.

The filler is preferably subjected to a hydrophobic surface treatment. By the hydrophobic surface treatment, the resulting optical moisture curable resin composition is more excellent in shape retention after application.
Examples of 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.
Specifically, for example, the trimethylsilylated silica is prepared by, for example, synthesizing silica by a method such as a sol-gel method and spraying hexamethyldisilazane in a state where the silica is fluidized, or an organic solvent such as alcohol or toluene. It can be produced by a method in which silica is added, hexamethyldisilazane and water are added, and then water and an organic solvent are evaporated and dried with an evaporator.

The content of the filler is preferably 1 part by weight at a preferable lower limit and 20 parts by weight at a preferable upper limit in 100 parts by weight of the entire light moisture curable resin composition of the present invention. When the content of the filler is less than 1 part by weight, the resulting light moisture curable resin composition may be inferior in shape retention after coating. When content of the said filler exceeds 20 weight part, the optical moisture hardening type resin composition obtained may become inferior to applicability | paintability. The more preferred lower limit of the content of the filler 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 lower limit is 4 parts by weight. .

The light moisture curable resin composition of the present invention may contain a light shielding agent. By containing the said light-shielding agent, the optical moisture hardening type resin composition of this invention becomes the thing excellent in light-shielding property, and can prevent the light leak of a display element.
In the present specification, the “light-shielding agent” means a material having an ability of hardly transmitting light in the visible light region.

Examples of the light-shielding agent include iron oxide, titanium black, aniline black, cyanine black, fullerene, carbon black, and resin-coated carbon black. In addition, 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 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. Therefore, by using a photo radical polymerization initiator that can initiate a reaction with light having a wavelength (370 to 450 nm) at which the transmittance of titanium black is high, the light of the photo moisture curable resin composition of the present invention can be used. Curability can be further increased. On the other hand, the light-shielding agent contained in the light moisture curable resin composition of the present invention is preferably a highly insulating material, and titanium black is also preferable as the highly insulating light-shielding agent.
The titanium black preferably has an optical density (OD value) of 3 or more, and more preferably 4 or more. The titanium black preferably has a blackness (L value) of 9 or more, more preferably 11 or more. The higher the light shielding property of the titanium black, the better. There is no particular upper limit to the OD value of the titanium black, but it is usually 5 or less.

The above-mentioned titanium black exhibits a sufficient effect even if it is not surface-treated, but the surface is treated with an organic component such as a coupling agent, silicon oxide, titanium oxide, germanium oxide, aluminum oxide, oxidized Surface-treated titanium black such as those coated with an inorganic component such as zirconium or magnesium oxide can also be used. Especially, what is processed with the organic component is preferable at the point which can improve insulation more.
In addition, the display element manufactured using the light moisture curable resin composition of the present invention has a high contrast because there is no light leakage because the light moisture curable resin composition has sufficient light shielding properties. Image display quality.

Examples of commercially available titanium black 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, and the more preferable upper limit is 25 m ² / g.
Moreover, the preferable lower limit of the sheet resistance of the titanium black is 10 ⁹ Ω / □ when mixed with a resin (70% blending), and the more preferable lower limit is 10 ¹¹ Ω / □.

In the light-moisture curable resin composition of the present invention, the primary particle diameter of the light-shielding agent is appropriately selected depending on the application, such as the distance between the substrates of the display element, but the preferable lower limit is 30 nm and the preferable upper limit is 500 nm. It is. When the primary particle diameter of the light-shielding agent is less than 30 nm, the viscosity and thixotropy of the obtained light moisture-curable resin composition are greatly increased, and workability may be deteriorated. When the primary particle diameter of the light-shielding agent exceeds 500 nm, the dispersibility of the light-shielding agent in the obtained light moisture curable resin composition may be lowered, and the light-shielding property may be lowered. The more preferable lower limit of the primary particle diameter of the light shielding agent is 50 nm, and the more preferable upper limit is 200 nm.
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 PARTICLE SIZING SYSTEMS) and determining the average particle size. it can.

Although content of the said light shielding agent in the whole optical moisture hardening type resin composition of this invention is not specifically limited, A preferable minimum is 0.05 weight% and a preferable upper limit is 10 weight%. If the content of the light shielding agent is less than 0.05% by weight, sufficient light shielding properties may not be obtained. When the content of the light-shielding agent is more than 10% by weight, the adhesiveness of the obtained light moisture curable resin composition to the substrate or the strength after curing may be lowered, or the drawing property may be lowered. 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.

As a method for producing the light moisture curable resin composition of the present invention, for example, using a mixer such as a homodisper, a homomixer, a universal mixer, a planetary mixer, a kneader, a three roll, And a method of mixing a moisture curable urethane resin, a radical photopolymerization initiator, and an additive to be added as necessary.

In the light moisture curable resin composition of the present invention, 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. When the viscosity is less than 50 Pa · s or more than 500 Pa · s, the light moisture curable resin composition is applied to an adherend such as a substrate when used as an adhesive for electronic parts or an adhesive for display elements. The workability when doing so may deteriorate. A more preferred lower limit of the viscosity is 80 Pa · s, a more preferred upper limit is 300 Pa · s, and a still more preferred upper limit is 200 Pa · s.

The preferable lower limit of the thixotropic index of the light moisture curable resin composition of the present invention is 1.3, and the preferable upper limit is 5.0. When the thixotropic index is less than 1.3 or exceeds 5.0, an adherend such as a substrate is used when the optical moisture curable resin composition is used as an adhesive for electronic parts or an adhesive for display elements. The workability at the time of applying to may be deteriorated. The more preferable lower limit of the thixotropic index is 1.5, and the more preferable upper limit is 4.0.
In the present specification, 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.

Light moisture-curable resin composition of the present invention has a tensile preferred lower limit is 0.5 kgf / cm ² in elastic modulus at 25 ° C. of the cured product, the desirable upper limit is 6 kgf / cm ^2. If the tensile elastic modulus is less than 0.5 kgf / cm ^2, it is too soft, the cohesive force is weak, and the adhesive force may be low. When the tensile elastic modulus exceeds 6 kgf / cm ² , flexibility may be impaired. A more preferable lower limit of the tensile modulus is 1 kgf / cm ² , and a more preferable upper limit is 4 kgf / cm ² .
In the present specification, the above “tensile modulus” is 50% elongation by pulling the cured product at a speed of 10 mm / min using a tensile tester (for example, “EZ-Graph” manufactured by Shimadzu Corporation). It means the value measured as the force of time.

The light moisture curable resin composition of the present invention can be particularly suitably used as an adhesive for electronic parts or an adhesive for display elements. An adhesive for electronic components using the light moisture curable resin composition of the present invention and a display element adhesive using the light moisture curable resin composition of the present invention are also included in the present invention. It is.

ADVANTAGE OF THE INVENTION According to this invention, the optical moisture hardening type resin composition excellent in adhesiveness and the reliability in a high-temperature, high-humidity environment can be provided. Moreover, according to this invention, the adhesive for electronic components and the adhesive for display elements which use this optical moisture hardening type resin composition can be provided.

(A) is a schematic diagram which shows the case where the sample for adhesive evaluation is seen from the top, (b) is a schematic diagram which shows the case where the sample for adhesive evaluation is seen from the side.

Hereinafter, the present invention will be described in more detail with reference to examples. However, the present invention is not limited to these examples.

(Synthesis Example 1 (Production of Urethane Prepolymer A))
As a polyol compound, 100 parts by weight of polytetramethylene ether glycol (manufactured by Mitsubishi Chemical Corporation, “PTMG-2000”) and 0.01 part by weight of dibutyltin dilaurate were placed in a 500-mL separable flask and subjected to vacuum (20 mmHg The following was stirred for 30 minutes at 100 ° C. and mixed. Thereafter, normal pressure was applied, and 26.5 parts by weight of diphenylmethane diisocyanate (manufactured by Nisso Shoji Co., Ltd., “Pure MDI”) was added as a polyisocyanate compound, stirred at 80 ° C. for 3 hours, reacted, and urethane prepolymer A (weight average molecular weight). 2700).

(Synthesis Example 2 (Production of Urethane Prepolymer B))
As a polyol compound, 100 parts by weight of polypropylene glycol (manufactured by Asahi Glass Co., Ltd., “EXCENOL 2020”) and 0.01 part by weight of dibutyltin dilaurate are placed in a 500 mL separable flask, and are placed under vacuum (20 mmHg or less) at 100 ° C. For 30 minutes and mixed. Thereafter, normal pressure was applied and 26.5 parts by weight of diphenylmethane diisocyanate (“Pure MDI”, manufactured by Nissho Shoji Co., Ltd.) was added as a polyisocyanate compound, stirred at 80 ° C. for 3 hours, reacted, and urethane prepolymer B (weight average molecular weight) 2900).

(Synthesis Example 3 (Production of Urethane Prepolymer C))
In a reaction vessel containing 100 parts by weight of urethane prepolymer A obtained in the same manner as in Synthesis Example 1, 1.3 parts by weight of hydroxyethyl methacrylate and N-nitrosophenylhydroxylamine aluminum salt as a polymerization inhibitor (Wako Pure Chemical Industries, Ltd.) 0.14 parts by weight of “Q-1301” manufactured by the same company, and stirred and mixed at 80 ° C. for 1 hour under a nitrogen stream, and a urethane prepolymer C having an isocyanate group and a methacryloyl group at the molecular end (weight average) Molecular weight 2900) was obtained.

(Synthesis Example 4 (Production of Urethane Prepolymer D))
To a reaction vessel containing 100 parts by weight of urethane prepolymer A obtained in the same manner as in Synthesis Example 1, 9.8 parts by weight of 3-mercaptopropyltrimethoxysilane (“KBM-803” manufactured by Shin-Etsu Chemical Co., Ltd.) was added. The mixture was stirred and mixed at 80 ° C. for 1 hour to obtain a urethane prepolymer D (weight average molecular weight 3100) having an isocyanate group and a trimethoxysilyl group at the molecular end as an organic silyl group-containing urethane resin.

(Examples 1 to 15, Comparative Examples 1 and 2)
In accordance with the blending ratios described in Tables 1 and 2, each material was stirred with a planetary stirrer (manufactured by Shinky Co., Ltd., “Awatori Netaro”) and then mixed uniformly with a ceramic three roll. The optical moisture curable resin compositions of Examples 1 to 15 and Comparative Examples 1 and 2 were obtained.
In Tables 1 and 2, “urethane prepolymer A” is a urethane prepolymer having an isocyanate group at both ends described in Synthesis Example 1, and “urethane prepolymer B” is both ends described in Synthesis Example 2. Is a urethane prepolymer having an isocyanate group at the end, “urethane prepolymer C” is the urethane prepolymer having an isocyanate group and a methacryloyl group at the molecular end described in Synthesis Example 3, and “urethane prepolymer D” is Synthesis Example 4 And a urethane prepolymer having an isocyanate group and a trimethoxysilyl group at the molecular end.

<Evaluation>
The following evaluation was performed about each light moisture hardening type resin composition obtained by the Example and the comparative example. The results are shown in Tables 1 and 2.
In addition, about the optical moisture curable resin composition obtained in Comparative Example 2, the optical moisture curable resin composition was crushed when the substrates were bonded together, and the samples in each evaluation could not be prepared. It was.

(Adhesiveness)
Each optical moisture curable resin composition obtained in Examples and Comparative Examples was applied to a polycarbonate substrate with a width of about 2 mm using a dispensing apparatus. Thereafter, the light-moisture curable resin composition was photocured by irradiating ultraviolet rays with 1000 mJ / cm ² using a UV-LED (wavelength 365 nm). Thereafter, a glass plate was bonded to the polycarbonate substrate, a weight of 20 g was placed, and the sample was allowed to stand overnight to be moisture cured to obtain a sample for evaluating adhesiveness. FIG. 1 is a schematic diagram (FIG. 1 (a)) showing a case where an adhesive evaluation sample is viewed from above, and a schematic diagram showing a case where the adhesive evaluation sample is viewed from the side (FIG. 1 (b)). showed that.
Using the tensile tester (manufactured by Shimadzu Corporation, “Ez-Grapf”), the prepared adhesive evaluation sample is pulled at a rate of 5 mm / sec in the shear direction, and the strength when the polycarbonate substrate and the glass plate are peeled off. Was measured.

(High temperature and high humidity reliability (creep resistance))
A sample for evaluating high temperature and high humidity reliability was produced in the same manner as the sample for evaluating adhesiveness in the evaluation of “(adhesiveness)”. The obtained sample for high-temperature and high-humidity reliability evaluation was hung perpendicularly to the ground, and a weight of 120 g was hung on the end of the polycarbonate substrate, placed in a constant temperature and humidity oven at 60 ° C. and 95% RH, and left for 24 hours. did. After standing for 24 hours, the case where the polycarbonate substrate and the glass plate were not peeled was “◯”, the case where the polycarbonate substrate and the glass plate were partially peeled was “△”, and the polycarbonate substrate and the glass plate were completely The case where it was peeled off was evaluated as “x”, and the high-temperature and high-humidity reliability (creep resistance) of the light moisture-curable resin composition was evaluated.

(Flexibility)
Using a high-pressure mercury lamp, ultraviolet light is irradiated at 1000 mJ / cm ² to light-cure each light-moisture-curable resin composition obtained in the examples and comparative examples, and then left overnight to cure the moisture. I let you. Using a tensile tester (“EZ-Graph” manufactured by Shimadzu Corporation), a test piece obtained by punching the obtained cured product into a dumbbell shape (No. 6 defined by “JIS K 6251”) was obtained. Tensile force at a speed of 10 mm / min and the force at 50% elongation were determined as the elastic modulus.

ADVANTAGE OF THE INVENTION According to this invention, the optical moisture hardening type resin composition excellent in adhesiveness and the reliability in a high-temperature, high-humidity environment can be provided. Moreover, according to this invention, the adhesive for electronic components and the adhesive for display elements which use this optical moisture hardening type resin composition can be provided.

1 Polycarbonate substrate 2 Light moisture curable resin composition 3 Glass plate

Claims (9)

1. Containing a radical polymerizable compound, a moisture curable urethane resin, and a photo radical polymerization initiator,
   The moisture-curable urethane resin contains a compound having a urethane bond, a group represented by the following formula (1), and an isocyanate group.
   

   

   In formula (1), R ¹ and R ² are hydrogen, an alkyl group having 1 to 5 carbon atoms, or an aryl group, and R ¹ and R ² may be the same or different. Also good. x is 0-2.
2. The content of the compound having a urethane bond, a group represented by the formula (1), and an isocyanate group is 1 to 50 weights with respect to 100 parts by weight in total of the radical polymerizable compound and the moisture curable urethane resin. The light moisture curable resin composition according to claim 1, wherein the composition is a part.
3. Furthermore, moisture-curable urethane resin other than the compound which has a urethane bond, group represented by Formula (1), and an isocyanate group is contained, The optical moisture hardening of Claim 1 or 2 characterized by the above-mentioned. Mold resin composition.
4. The photo-moisture curable resin composition according to claim 1, 2 or 3, wherein the radical polymerizable compound contains a monofunctional radical polymerizable compound and a polyfunctional radical polymerizable compound.
5. 5. The content of the polyfunctional radical polymerizable compound is 2 to 45 parts by weight with respect to 100 parts by weight in total of the monofunctional radical polymerizable compound and the polyfunctional radical polymerizable compound. Light moisture curable resin composition.
6. 6. The photo-moisture curable resin composition according to claim 1, comprising a filler having a primary particle size of 1 to 50 nm.
7. The light moisture curable resin composition according to claim 1, further comprising a light-shielding agent.
8. An adhesive for electronic parts, comprising the optical moisture-curable resin composition according to claim 1, 2, 3, 4, 5, 6 or 7.
9. A light-moisture curable resin composition according to claim 1, 2, 3, 4, 5, 6, or 7.

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