Resin composition, adhesive agent, cured product, electronic component, and semiconductor device

Abstract

Provided is a resin composition that can be cured at a low temperature and in a short time, and exhibits excellent adhesive strength.　This resin composition includes (A) a (meth)acrylate compound, (B) a polyfunctional thiol compound, and (C) a curing catalyst system that includes at least one type of latent curing catalyst, wherein the component (C) has the following characteristic (1). Characteristic (1): In a DSC chart from when a mixed solution resulting from mixing 1.0 g of the component (C) and 9.0 g of 1,3,4,6-tetrakis(3-mercaptopropyl)glycoluril is subjected to differential scanning calorimetry, the temperature of the endothermic peak top is 50-70°C, and the slope of the line segment connecting the onset of the endothermic peak and the peak top is –0.0007 mW / mg∙°C or less.

Description

Resin compositions, adhesives, cured products, electronic components, and semiconductor devices

[0001] The present invention relates to resin compositions, adhesives, cured products, electronic components, and semiconductor devices comprising (meth)acrylate compounds and thiol compounds.

[0002] Adhesives for electronic materials, which are made from resin compositions, are required to be able to cure at low temperatures to reduce environmental impact and to cure in a short time to improve productivity. Furthermore, adhesives for electronic materials also require excellent adhesion.

[0003] Patent Document 1 describes a curable composition used as a low-temperature, short-time curing adhesive, comprising (1) a compound having a (meth)acryloyl group, (2) a polythiol compound having two or more mercapto groups in one molecule, (3) a photoradical generator, and (4) a latent curing agent.

[0004] International Publication No. 2018 / 181421

[0005] However, with conventional resin compositions, heating for a long time was required to cure at low temperatures, and heating at high temperatures was required to cure in a short time.

[0006] The present invention aims to provide a resin composition that can be cured at low temperatures and in a short time, and exhibits excellent adhesive strength.

[0007] To achieve the above objective, the resin composition of the present disclosure comprises (A) a (meth)acrylate compound, (B) a polyfunctional thiol compound, and (C) a curing catalyst system comprising at least one latent curing catalyst, wherein component (C) has the following characteristic (1): Characteristic (1): In a DSC chart obtained by differential scanning calorimetry of a mixed solution of 1.0 g of component (C) and 9.0 g of 1,3,4,6-tetrakis(3-mercaptopropyl) glycoluryl, the temperature of the endothermic peak top is 50 to 70°C, and the slope of the line segment connecting the onset of the endothermic peak and the peak top is -0.0007 mW / mg·°C or less.

[0008] According to the resin composition of the present invention, by including the (C) curing catalyst system having the characteristic (1), it is possible to cure at a low temperature and in a short time, and the adhesive strength can be made excellent.

[0009] Hereinafter, embodiments of the present invention (hereinafter, this embodiment) will be described. This embodiment relates to a resin composition, an adhesive, a cured product of the adhesive, an electronic component including the cured product, and a semiconductor device. Note that the present invention is not limited by this embodiment. Further, the present disclosure can be implemented in various modified and improved forms based on the knowledge of those skilled in the art.

[0010] [Definitions] In this specification, ○ to △ (for example, ○ parts by mass to △ parts by mass) means ○ or more and △ or less (○ parts by mass or more and △ parts by mass or less). Also in this specification, the terms "includes" or "contains" mean that the specified components are included, but do not exclude the existence of other components. Also in this specification, the expression "A and / or B" includes "A only," "B only," and "both A and B." Also in this specification, "room temperature" means 25°C. Also in this specification, following convention in the field of synthetic resins, the term "resin," which usually refers to a polymer (especially a synthetic polymer), may be used for components constituting a curable resin composition before curing, even if the component is not a polymer, for example, a prepolymer compound before curing. Conversely, even if the component is a polymer, the term "compound" may be used, focusing on the functional group. Also in this specification, "(meth)acryloyl group" refers to both a methacryloyl group and an acryloyl group. Furthermore, "(meth)acrylate compound" refers to both acrylate compounds and methacrylate compounds. In addition, in numerical ranges described stepwise in this specification, the upper or lower limit of one numerical range may be replaced with the upper or lower limit of another numerical range described stepwise. In addition, in numerical ranges described in this disclosure, the upper or lower limit of that numerical range may be replaced with the value shown in the examples. Furthermore, in this specification, each component may contain multiple types of the corresponding substance. If multiple types of the substance corresponding to each component are present in the composition, the content or amount of each component means the total content or amount of the multiple types of substances present in the composition, unless otherwise specified.

[0011] [Resin Composition] The resin composition of the present embodiment includes (A) a (meth)acrylate compound, (B) a polyfunctional thiol compound, and (C) a curing catalyst system containing at least one type of latent curing catalyst, and the component (C) has the following characteristic (1). Characteristic (1): When a mixed solution of 1.0 g of the component (C) and 9.0 g of 1,3,4,6-tetrakis(3-mercaptopropyl)glycoluril is subjected to differential scanning calorimetry, in the DSC chart, the temperature at the top of the endothermic peak is 50 to 70°C, and the slope of the line segment connecting the onset and the top of the endothermic peak is -0.0007 mW / mg·°C or less.

[0012] <(A) (Meth)acrylate Compound> The resin composition of the present embodiment includes (A) a (meth)acrylate compound (hereinafter also referred to as the "component (A)"). The (A) (meth)acrylate compound can impart transparency and appropriate hardness to the cured resin composition. The (A) (meth)acrylate compound is not particularly limited as long as it has one or more (meth)acryloyl groups, and examples include monofunctional (meth)acrylate compounds having one (meth)acryloyl group and polyfunctional (meth)acrylate compounds having two or more (meth)acryloyl groups. Considering the aspect of ensuring heat resistance, polyfunctional (meth)acrylate compounds having two or more (meth)acryloyl groups are preferred, compounds having 2 to 6 (meth)acryloyl groups are more preferred, and compounds having two (meth)acryloyl groups are even more preferred. Also, in order to adjust the viscosity and physical properties of the cured product (such as adhesion strength and flexibility), in addition to the polyfunctional (meth)acrylate compound, a monofunctional (meth)acrylate compound can also be used.

[0013] Examples of monofunctional (meth)acrylate compounds include ethyl (meth)acrylate, trifluoroethyl (meth)acrylate, diethylaminoethyl (meth)acrylate, dimethylaminoethyl (meth)acrylate, glycidyl (meth)acrylate, n-butyl (meth)acrylate, isobutyl (meth)acrylate, tert-butyl (meth)acrylate, isoamyl (meth)acrylate, cyclohexyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, isodecyl (meth)acrylate, isobornyl (meth)acrylate, stearyl (meth)acrylate, lauryl (meth)acrylate, phenoxyethyl (meth)acrylate, benzyl (meth)acrylate, tetrahydrofurfuryl (meth)acrylate, ethoxydiethylene glycol (meth)acrylate, phenoxydiethylene glycol (meth)acrylate, phenoxypropyl Esters of monohydric alcohols and (meth)acrylic acid, such as ethylene glycol (meth)acrylate, butoxydiethylene glycol (meth)acrylate, methoxydipropylene glycol (meth)acrylate, methoxypolyethylene glycol (meth)acrylate, methoxytriethylene glycol (meth)acrylate, methoxypolyethylene glycol (meth)acrylate, 2-ethylhexyldiethylene glycol (meth)acrylate, 4-tert-butylcyclohexyl (meth)acrylate, 3-phenoxybenzyl (meth)acrylate, etc.; 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 2-hydroxybutyl (meth)acrylate, 2-hydroxy-3-phenoxypropyl (meth)acrylate, (meth)octyl acrylate, (meth)nonyl acrylate, (meth)acrylate, isononyl (meth)acrylate, 3,3,5-Trimethylcyclohexyl (meth)acrylate, 2-ethyl-2-adamantyl (meth)acrylate, cyclic trimethylolpropaneformal (meth)acrylate, 1-naphthalenemethyl (meth)acrylate, 1-ethylcyclohexyl (meth)acrylate, 1-methylcyclohexyl (meth)acrylate, 1-ethylcyclopentyl (meth)acrylate, 1-methylcyclopentyl (meth)acrylate, dicyclopentenyl (meth)acrylate, dicyclopentenyloxyethyl (meth)acrylate Adamantyl(meth)acrylate, dicyclopentanyl(meth)acrylate, nonylphenoxypolyethylene glycol(meth)acrylate, tetrahydrodicyclopentadienyl(meth)acrylate, 2-(o-phenylphenoxy)ethyl(meth)acrylate, isobornylcyclohexyl(meth)acrylate, (2-methyl-2-ethyl-1,3-dioxolan-4-yl)methyl(meth)acrylate, 1-adamantyl(meth)acrylate, 3-hydroxy-1-adamantyl(meth)acrylate, 2-methyl-2-ada Mantanyl (meth)acrylate, 2-ethyl-2-adamantanyl (meth)acrylate, 2-isopropyladamantan-2-yl (meth)acrylate, 3-hydroxy-1-adamantyl (meth)acrylate, (adamantan-1-yloxy)methyl (meth)acrylate, 2-isopropyl-2-adamantyl (meth)acrylate, 1-methyl-1-ethyl-1-adamantylmethanol (meth)acrylate, 1,1-diethyl-1-adamantylmethanol (meth)acrylate, 2-cyclohexyl Lupropan-2-yl (meth)acrylate, 1-isopropylcyclohexyl (meth)acrylate, 1-methylcyclohexyl (meth)acrylate, 1-ethylcyclopentyl (meth)acrylate, 1-methylcyclohexyl (meth)acrylate, tetrahydropyranyl (meth)acrylate, tetrahydro-2-furanyl (meth)acrylate, 2-oxotetrahydrofuran-3-yl (meth)acrylate, (5-oxotetrahydrofuran-2-yl)methyl (meth)acrylate, (2-oxo-1,Examples include, but are not limited to, mono(meth)acrylates of polyhydric alcohols or esters of monohydric alcohols and (meth)acrylic acid, such as 3-dioxolan-4-yl)methyl(meth)acrylate, N-acryloyloxyethylhexahydrophthalimide, α-(meth)acryloyl-ω-methoxypoly(oxyethylene), and 1-ethoxyethyl(meth)acrylate. These may be used individually or in combination of two or more.

[0014] Examples of polyfunctional (meth)acrylate compounds include diacrylate and / or dimethacrylate of tris(2-hydroxyethyl) isocyanurate; triacrylate and / or trimethacrylate of tris(2-hydroxyethyl) isocyanurate; trimethylolpropane triacrylate and / or trimethacrylate, or their oligomers; pentaerythritol triacrylate and / or trimethacrylate, or their oligomers; polyacrylate and / or polymethacrylate of dipentaerythritol; tris(hydroxyethyl) Liloxyethyl isocyanurate; Caprolactone-modified tris(acryloxyethyl) isocyanurate; Caprolactone-modified tris(methacryloxyethyl) isocyanurate; Alkyl-modified dipentaerythritol polyacrylate and / or polymethacrylate; Caprolactone-modified dipentaerythritol polyacrylate and / or polymethacrylate; Bisphenol A di(meth)acrylate; Bisphenol F di(meth)acrylate; Polyalkylene oxide-modified bisphenol A diacrylate and / or poly Real alkylene oxide-modified bisphenol A dimethacrylate; polyalkylene oxide-modified bisphenol F di(meth)acrylate; dihydrocyclopentadiethyl acrylate and / or dihydrocyclopentadiethyl methacrylate, as well as polyester acrylate and / or polyester methacrylate, dimethylol-tricyclodecane di(meth)acrylate, tricyclodecane dimethanol diacrylate, poly(meth)acrylate of ditrimethylolpropane, neopentyl glycol diacrylate and / Alternatively, examples include polyurethanes having two or more (meth)acryloyl groups in one molecule, such as dimethacrylate and polycarbonate-based urethane acrylate oligomers; polyesters having two or more (meth)acryloyl groups in one molecule; phenoxyethyl (meth)acrylate; isobornyl (meth)acrylate; phenoxydiethylene glycol (meth)acrylate; 4-tert-butylcyclohexyl (meth)acrylate; epoxy resin half (meth)acrylate; and (meth)acrylate having an allyloxymethyl group.Other (meth)acrylate compounds include epoxy resin half-(meth)acrylate and (meth)acrylate having an allyloxymethyl group (see Japanese Patent Publication No. 2024-009452), but are not limited to these. These may be used individually or in combination of two or more.

[0015] The (meth)acrylate compound may be any one of the (meth)acrylate compounds mentioned above, or two or more may be used in combination. Examples of commercially available (meth)acrylate compounds include polyester acrylate (product name: EBECRYL810) manufactured by Daicel Ornex Co., Ltd., ditrimethylolpropanetetraacrylate (product name: EBECRYL140) manufactured by Daicel Ornex Co., Ltd., polyester acrylate (product name: Aronics M7100) manufactured by Toagosei Co., Ltd., and dimethylol-tricyclodecanediaacrylate (product name: Light Acrylate DCP-A) manufactured by Kyoeisha Chemical Co., Ltd. Examples include, but are not limited to, neopentyl glycol-modified trimethylolpropane diacrylate (product name: Kayarad R-604) manufactured by Honkayaku Co., Ltd., tricyclodecanedimethanol diacrylate (product name: A-DCP) manufactured by Shin Nakamura Kogyo Co., Ltd., neopentyl glycol diacrylate (product name: Light Acrylate NP-A) manufactured by Kyoeisha Chemical Co., Ltd., and non-yellowing polyether skeleton urethane acrylate (product name: Artresin UN-6200) manufactured by Negami Kogyo Co., Ltd.

[0016] Component (A) preferably has a viscosity of 0.01 to 80 Pa·s, from the viewpoint of preparing the resin composition and dispensability. In this specification, viscosity refers to the value measured at a measurement temperature of 25°C using an appropriate viscometer according to the viscosity range.

[0017] Component (A) preferably contains a compound having an (A1) (meth)acryloyl equivalent of 300 g / eq or less and / or a compound having an (A2) (meth)acryloyl equivalent of 1000 g / eq or more, and more preferably contains at least a compound having an (A1) (meth)acryloyl equivalent of 300 g / eq or less.

[0018] The (meth)acryloyl equivalent of component (A1) may be 300 g / eq or less, preferably 90 to 300 g / eq, and more preferably 100 to 250 g / eq. By including component (A1) within the above numerical range in the resin composition, excellent reactivity can be achieved.

[0019] The (meth)acryloyl equivalent of component (A2) should be 1000 g / eq or more, preferably 1000 to 5000 g / eq, and more preferably 2000 to 4000 g / eq. By including component (A2) within the above numerical range in the resin composition, it becomes easy to adjust the viscosity ratio of the resin composition to a suitable range.

[0020] From the viewpoint of the adhesive strength of the resin composition, the content of component (A) is preferably 10 to 70% by mass, more preferably 20 to 65% by mass, and even more preferably 25 to 60% by mass, relative to the total mass of the resin composition. Similarly, from the same viewpoint, the content of component (A) relative to 100 parts by mass of the total of component (A) and component (B) described later is preferably 20 to 90% by mass, more preferably 30 to 80% by mass, and even more preferably 35 to 75% by mass.

[0021] <(B) Polyfunctional Thiol Compound> The resin composition of this embodiment contains (B) polyfunctional thiol compound (hereinafter also referred to as "component (B)"). In this embodiment, (B) polyfunctional thiol compound is a compound containing two or more thiol groups. (B) polyfunctional thiol compound imparts high thermal and / or photocurability to the resin composition. In this embodiment, it is preferable that (B) polyfunctional thiol compound contains a trifunctional or higher thiol compound having three or more thiol groups. It is more preferable that (B) polyfunctional thiol compound contains a difunctional thiol compound and a trifunctional or higher thiol compound. A difunctional thiol compound is a thiol compound having two thiol groups. It is more preferable that (B) polyfunctional thiol compound contains a trifunctional thiol compound and / or a tetrafunctional thiol compound. A trifunctional and a tetrafunctional thiol compound are thiol compounds having three and four thiol groups, respectively.

[0022] Polyfunctional thiol compounds can be broadly classified into thiol compounds that have hydrolyzable substructures such as ester bonds in their molecule (i.e., hydrolyzable) and thiol compounds that do not have such substructures (i.e., non-hydrolyzable).

[0023] Examples of hydrolyzable polyfunctional thiol compounds include trimethylolpropane tris(3-mercaptopropionate), tris-[(3-mercaptopropionyloxy)-ethyl]-isocyanurate, pentaerythritol tetrakis(3-mercaptopropionate), tetraethylene glycol bis(3-mercaptopropionate), dipentaerythritol hexakis(3-mercaptopropionate), butanediol bisthioglycolate, hexanediol bisthioglycolate, trimethylolpropane tristhioglycolate, pentaerythritol tetrakisthioglycolate, and pentaerythritol. Examples include, but are not limited to, tetrakis(3-mercaptobutyrate), 1,4-bis(3-mercaptobutyryloxy)butane, or 1,3,5-tris(3-mercaptobutyryloxyethyl)-1,3,5-triazine-2,4,6(1H,3H,5H)-trione. These may be used individually or in combination of two or more.

[0024] Commercially available hydrolyzable polyfunctional thiol compounds include trimethylolpropane tris(3-mercaptopropionate) (manufactured by SC Organic Chemicals Co., Ltd.: TMMP), tris-[(3-mercaptopropionyloxy)-ethyl]-isocyanurate (manufactured by SC Organic Chemicals Co., Ltd.: TEMPIC), pentaerythritol tetrakis(3-mercaptopropionate) (manufactured by SC Organic Chemicals Co., Ltd.: PEMP), and tetraethylene glycol bis(3-mercaptopropionate) (manufactured by SC Organic Chemicals Co., Ltd.). Examples include EGMP-4 (manufactured by SC Organic Chemicals Co., Ltd.), dipentaerythritol hexakis(3-mercaptopropionate) (DPMP, manufactured by SC Organic Chemicals Co., Ltd.), pentaerythritol tetrakis(3-mercaptobutyrate) (Kalenz MT® PE1, manufactured by Showa Denko K.K.), and 1,3,5-tris(3-mercaptobutyryloxyethyl)-1,3,5-triazine-2,4,6(1H,3H,5H)-trione (Kalenz MT® NR1, manufactured by Showa Denko K.K.). These may be used individually or in combination of two or more.

[0025] On the other hand, examples of non-hydrolyzable polyfunctional thiol compounds include 1,2,3-(3-mercaptopropyloxy)propane, pentaerythritol tetrapropanthol, 3-{3-(3-mercapto-propoxy)-2,2-bis-[(3-mercaptopropoxy)methyl]propoxy}propan-1-ol, 1,3,4,6-tetrakis(2-mercaptoethyl)glycoluryl, 1,3,4,6-tetrakis(3-mercaptopropyl)glycoluryl, 1,3,4,6-tetrakis(mercaptomethyl)glycoluryl, 1,3,4, 6-Tetrakis(mercaptomethyl)-3a-methylglycoluryl, 1,3,4,6-Tetrakis(2-mercaptoethyl)-3a-methylglycoluryl, 1,3,4,6-Tetrakis(3-mercaptopropyl)-3a-methylglycoluryl, 1,3,4,6-Tetrakis(mercaptomethyl)-3a,6a-dimethylglycoluryl, 1,3,4,6-Tetrakis(2-mercaptoethyl)-3a,6a-dimethylglycoluryl, 1,3,4,6-Tetrakis(3-mercaptopropyl)-3a,6a-dimethylglycoluryl Lyl, 1,3,4,6-tetrakis(mercaptomethyl)-3a,6a-diphenylglycoluryl, 1,3,4,6-tetrakis(2-mercaptoethyl)-3a,6a-diphenylglycoluryl, 1,3,4,6-tetrakis(3-mercaptopropyl)-3a,6a-diphenylglycoluryl, tris(2-mercaptoethyl)isocyanurate, tris(3-mercaptopropyl)isocyanurate, 1,3,5-tris[3-(2-mercaptoethylsulfanyl)propyl]isocyanurate, 1,3,5-tris[2-(3 -Mercaptopropoxy)ethyl]isocyanurate, pentaerythritol trippropanthol, 3-[2,3-bis(3-sulfanylpropoxy)propoxy]propane-1-thiol, 3-thiapentane-1,5-dithiol, 1,2,3-tris(3-mercaptopropyloxy)propane, 1,3-bis(3-mercaptopropyloxy)-2-propanol or derivative thereof, 3-[2,2-bis[(3-mercaptopropoxy)methyl]butoxy]-1-propanthol, pentaerythritol tetrapropanthol, 1,2,3-Tris(mercaptomethylthio)propane, 1,2,3-Tris(2-mercaptoethylthio)propane, 1,2,3-Tris(3-mercaptopropylthio)propane, 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane, 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, tetrakis(mercapto Methylthiomethyl)methane, tetrakis(2-mercaptoethylthiomethyl)methane, tetrakis(3-mercaptopropylthiomethyl)methane, 1,1,3,3-tetrakis(mercaptomethylthio)propane, 1,1,2,2-tetrakis(mercaptomethylthio)ethane, 1,1,5,5-tetrakis(mercaptomethylthio)-3-thiapentane, 1,1,6,6-tetrakis(mercaptomethylthio)-3,4-dithiahexane, 2,2-bis(mercaptomethylthio)ethanethiol, 3-mercaptomethylthio-1,7-dimercapto-2, 6-Dithiaheptane, 3,6-Bis(mercaptomethylthio)-1,9-Dimercapto-2,5,8-Tritianonane, 3-Mercaptomethylthio-1,6-Dimercapto-2,5-Dithiahexane, 1,1,9,9-Tetrakis(mercaptomethylthio)-5-(3,3-Bis(mercaptomethylthio)-1-Thiapropyl)3,7-Dithianonane, Tris(2,2-Bis(mercaptomethylthio)ethyl)methane, Tris(4,4-Bis(mercaptomethylthio)-2-Thiabutyl)methane, Tetrakis(2,2-Bis(mercaptomethylthio)ethyl) )methane, tetrakis(4,4-bis(mercaptomethylthio)-2-thiabutyl)methane, 3,5,9,11-tetrakis(mercaptomethylthio)-1,13-dimercapto-2,6,8,12-tetrathiatridecane, 3,5,9,11,15,17-hexakis(mercaptomethylthio)-1,19-dimercapto-2,6,8,12,14,18-hexathianonadecane, 9-(2,2-bis(mercaptomethylthio)ethyl)-3,5,13,15-tetrakis(mercaptomethylthio)-1,17-dimercapto-2,6,8,10,12,16-Hexatiaheptadecane, 3,4,8,9-Tetrakis(mercaptomethylthio)-1,11-Dimercapto-2,5,7,10-Tetrathiaundecane, 3,4,8,9,13,14-Hexakis(mercaptomethylthio)-1,16-Dimercapto-2,5,7,10,12,15-Hexatiahexadecane, 8-[Bis(mercaptomethylthio)methyl]-3,4,12,13-Tetrakis(mercaptomethylthio)-1,15-Dimercapto-2,5,7,9,11,14-Hexatiapentadecane, 4,6-Bis[3,5-Bis(M Lucaptomethylthio)-7-mercapto-2,6-dithiaheptylthio]-1,3-dithiane, 4-[3,5-bis(mercaptomethylthio)-7-mercapto-2,6-dithiaheptylthio]-6-mercaptomethylthio-1,3-dithiane, 1,1-bis[4-(6-mercaptomethylthio)-1,3-dithianylthio]-1,3-bis(mercaptomethylthio)propane, 1-[4-(6-mercaptomethylthio)-1,3-dithianylthio]-3-[2,2-bis(mercaptomethylthio)ethyl]-7,9-bis(mercaptomethylthio)- 2,4,6,10-tetrathiaundecane, 3-[2-(1,3-dithiethanyl)]methyl-7,9-bis(mercaptomethylthio)-1,11-dimercapto-2,4,6,10-tetrathiaundecane, 9-[2-(1,3-dithiethanyl)]methyl-3,5,13,15-tetrakis(mercaptomethylthio)-1,17-dimercapto-2,6,8,10,12,16-hexathiaheptadecane, 3-[2-(1,3-dithiethanyl)]methyl-7,9,13,15-tetrakis(mercaptomethylthio)-1,17-dimercapto-2,4, 6,10,12,16-Hexathiaheptadecane, 4,6-Bis[4-(6-mercaptomethylthio)-1,3-Dithianylthio]-6-[4-(6-mercaptomethylthio)-1,3-Dithianylthio]-1,3-Dithiane, 4-[3,4,8,9-Tetrakis(mercaptomethylthio)-11-Mercapto-2,5,7,10-Tetrathiaundecyl]-5-Mercaptomethylthio-1,3-Dithiolane, 4,5-Bis[3,4-Bis(mercaptomethylthio)-6-Mercapto-2,5-Dithiahexylthio]-1,3-Dithiolane, 4-[3,4-bis(mercaptomethylthio)-6-mercapto-2,5-dithiahexylthio]-5-mercaptomethylthio-1,3-dithiolane, 4-[3-bis(mercaptomethylthio)methyl-5,6-bis(mercaptomethylthio)-8-mercapto-2,4,7-trithiaoctyl]-5-mercaptomethylthio-1,3-dithiolane, 2-{bis[3,4-bis(mercaptomethylthio) 2-[3,4-bis(mercaptomethylthio)-6-mercapto-2,5-dithiahexylthio]methyl}-1,3-dithiethane, 2-[3,4-bis(mercaptomethylthio)-6-mercapto-2,5-dithiahexylthio]mercaptomethylthiomethyl-1,3-dithiethane, 2-[3,4,8,9-tetrakis(mercaptomethylthio)-11-mercapto-2,5,7,10-tetrathiaundecylthio]mercaptomethylthio Methyl-1,3-dithiethane, 2-[3-bis(mercaptomethylthio)methyl-5,6-bis(mercaptomethylthio)-8-mercapto-2,4,7-trithiaoctyl]mercaptomethylthiomethyl-1,3-dithiethane, 4-{1-[2-(1,3-dithietanyl)]-3-mercapto-2-thiapropylthio}-5-[1,2-bis(mercaptomethylthio)-4-mercapto-3 Examples include various bifunctional thiol compounds disclosed in WO2019 / 082962, such as [-thiabutylthio]-1,3-dithiolane, 2,2'-[cyclohexylidenebis(thio-2,1-ethanediylthio)]bis[ethanethiol], and 4,4'-[(1,3-phenylene)bis(oxy)]bis[1-butanethiol], as well as dimers, trimers, and tetramers of the said thiol compounds. These may be used individually or in combination of two or more.

[0026] Commercially available non-hydrolyzable polyfunctional thiol compounds include 1,3,4,6-tetrakis(2-mercaptoethyl) glycoluryl (manufactured by Shikoku Chemicals, Inc.: TS-G), (1,3,4,6-tetrakis(3-mercaptopropyl) glycoluryl (manufactured by Shikoku Chemicals, Inc.: C3 TS-G), pentaerythritol trippropanthol (manufactured by SC Organic Chemicals, Inc.: PEPT), 2,2-bis[(3-sulfanylpropoxy)methyl]butan-1-ol (manufactured by Sakai Chemicals, Inc.: Multiol Y-2), 3-(3-mercapto-propoxy)-2,2-bis-(3-mercapto-propoxymethyl)-propan-1-ol (manufactured by Sakai Chemicals, Inc.: Multiol Y-3), pentaerythritol tetrapropanthol (manufactured by SC Organic Chemicals, Inc.: Multiol Examples include Y-4), but are not limited to these. These may be used individually or in combination of two or more.

[0027] (B) The total thiol equivalent of the polyfunctional thiol compound is preferably 80 to 200 g / eq, more preferably 80 to 150 g / eq, even more preferably 85 to 150 g / eq, and particularly preferably 85 to 140 g / eq.

[0028] In this specification, functional group equivalents such as (meth)acryloyl equivalents and thiol equivalents represent the molecular weight of the compound per functional group, and functional group equivalent numbers such as thiol group equivalents and (meth)acryloyl group equivalents represent the mass of the compound (amount charged) per functional group (equivalent number).

[0029] In the resin composition of this embodiment, the ratio of the number of (meth)acryloyl group equivalents of component (A) to the number of thiol group equivalents of component (B) ([number of (meth)acryloyl group equivalents of component (A)] / [number of thiol group equivalents of component (B)]) is preferably 0.1 to 10, more preferably 0.25 to 9, even more preferably 0.3 to 8, and still more preferably 0.5 to 5.

[0030] The thiol equivalent of component (B) is theoretically the number obtained by dividing the molecular weight of component (B) by the number of thiol groups in one molecule. The actual thiol equivalent can be determined, for example, by determining the thiol value by potentiometric measurement. This method is widely known and is disclosed, for example, in paragraph 0079 of Japanese Patent Application Publication No. 2012-153794. The number of thiol group equivalents of component (B) is the mass (amount charged) of component (B) per number of thiol groups (equivalent number), and is the quotient obtained by dividing the mass (g) of the polyfunctional thiol compound (B) by the thiol equivalent of that thiol compound (if multiple thiol compounds are included, it is the sum of such quotients for each thiol compound).

[0031] Furthermore, the total thiol equivalent of a polyfunctional thiol compound (B), when it contains two types of thiol compounds, is the weighted average of the thiol equivalent a of thiol compound A and the thiol equivalent b of thiol compound B. Specifically, if the content of thiol compound A is α and the content of thiol compound B is β, the total thiol equivalent of the polyfunctional thiol compound (B) is calculated as (thiol equivalent a × content α + thiol equivalent b × content β) / (content α + content β). Similarly, the total thiol equivalent of a polyfunctional thiol compound (B), when it contains n types of thiol compounds, is the sum of the thiol equivalents × content of each thiol compound and divided by the sum of the contents of each thiol compound.

[0032] (A) The (meth)acryloyl equivalent of a (meth)acrylate compound is theoretically equal to the molecular weight of the (meth)acrylate compound divided by the number of acryloyl groups (or methacryloyl groups) in one molecule. The actual (meth)acryloyl equivalent can be measured, for example, by NMR. The number of (meth)acryloyl group equivalents of component (A) is the mass (amount charged) of component (A) per number of (meth)acryloyl groups (equivalents), and is the quotient obtained by dividing the mass (g) of the (meth)acrylate compound by the (meth)acryloyl equivalent of that (meth)acrylate compound (if multiple (meth)acrylate compounds are included, it is the sum of such quotients for each (meth)acrylate compound).

[0033] Furthermore, the total (meth)acryloyl equivalent of the (A)(meth)acrylate compound is the weighted average of the (meth)acryloyl equivalent c of (meth)acrylate compound C and the (meth)acryloyl equivalent d of (meth)acryloyl compound D, when two types of (A)(meth)acrylate compounds are included. Specifically, if the content of (meth)acryloyl compound C is γ and the content of (meth)acryloyl compound D is δ, the total (meth)acryloyl equivalent of the (A)(meth)acrylate compound is calculated as ((meth)acryloyl equivalent c × content γ + (meth)acryloyl equivalent d × content δ) / (content γ + content δ). Similarly, (A) the total (meth)acryloyl equivalent of a (meth)acrylate compound is the sum of the (meth)acryloyl equivalents × content of each (meth)acryloyl compound, divided by the sum of the content of each (meth)acryloyl compound, when n types of (meth)acryloyl compounds are included.

[0034] Setting the ratio of [(meth)acryloyl group equivalents of component (A)] / [(thiol group equivalents of component (B)] to 0.1 to 10 allows the (meth)acryloyl groups and thiol groups to react in sufficient quantities, thereby enabling the formation of sufficient molecular crosslinks, which facilitates the development of high adhesive strength and allows for the creation of a resin composition with excellent curability.

[0035] From the viewpoint of the adhesive strength of the resin composition, the content of component (B) is preferably 10 to 65% by mass, more preferably 15 to 60% by mass, and even more preferably 25 to 55% by mass, relative to the total mass of the resin composition. Similarly, from the same viewpoint, the content of component (B) relative to 100 parts by mass of the total of components (A) and (B) is preferably 10 to 70% by mass, more preferably 15 to 65% by mass, and even more preferably 20 to 60% by mass.

[0036] <(C) Curing Catalyst System> The curing catalyst system included in the resin composition of this embodiment includes at least one latent curing catalyst and has the following characteristic (1). Characteristic (1): In the DSC chart obtained by differential scanning calorimetry of a mixed solution of 1.0 g of component (C) and 9.0 g of 1,3,4,6-tetrakis(3-mercaptopropyl) glycoluryl, the temperature of the endothermic peak top is 50 to 70°C, and the slope of the line segment connecting the onset of the endothermic peak and the peak top is -0.0007 mW / mg·°C or less.

[0037] The differential scanning calorimetry in feature (1) shall be performed under the conditions described in the examples. (C) The curing catalyst system, which includes at least one type of latent curing catalyst, is not particularly limited as long as it satisfies feature (1) above. In feature (1), the curing catalyst system has an endothermic peak top temperature of 50 to 70°C, preferably 50 to 65°C, and more preferably 55 to 65°C. In some embodiments, the curing catalyst system has an endothermic peak top temperature of 55 to 70°C in the DSC chart in feature (1). In addition, in feature (1), the curing catalyst system has a slope from the onset to the peak top of the endothermic peak in the DSC chart of -0.0007 mW / mg·°C or less, preferably -0.0008 mW / mg·°C or less, and more preferably -0.0012 mW / mg·°C or less.

[0038] The resin composition of this embodiment can be cured at low temperatures and in a short time by including a curing catalyst system having feature (1) (C) at least one type of latent curing catalyst. Specifically, the curing catalyst system has the maximum value of its endothermic peak in the temperature range of 50 to 70°C, so the curing reaction proceeds sufficiently even at low temperatures. Furthermore, the curing catalyst system cures in a short time because, in differential scanning calorimetry, the slope of the line segment connecting the onset and peak top of the endothermic peak is -0.0007 mW / mg·°C or less.

[0039] Examples of commercially available latent curing catalysts having characteristic (1) include Fujicure-2015, a modified aliphatic polyamine latent curing catalyst manufactured by T&K TOKA Corporation, and Fujicure-2021, an amine-based powdered latent curing agent manufactured by T&K TOKA Corporation, but are not particularly limited as long as characteristic (1) is satisfied. Note that (C) The curing catalyst system only needs to satisfy characteristic (1), and may include curing catalysts that do not satisfy characteristic (1) on their own. The curing catalyst can be any compound that generates active species such as radicals, anions, or cations upon heating, and depending on the type of active species, examples include thermal radical polymerization initiators, thermal anionic polymerization initiators, and thermal cationic polymerization initiators.

[0040] Examples of thermal radical polymerization initiators include methyl ethyl ketone peroxide, methylcyclohexanone peroxide, methyl acetacetate peroxide, acetylacetone peroxide, 1,1-bis(t-butylperoxy)3,3,5-trimethylcyclohexane, 1,1-bis(t-hexylperoxy)cyclohexane, 1,1-bis(t-hexylperoxy)3,3,5-trimethylcyclohexane, 1,1-bis(t-butylperoxy)cyclohexane, and 2,2-bis(4,4-di-t- (Tyl peroxycyclohexyl)propane, 1,1-bis(t-butylperoxy)cyclododecane, n-butyl 4,4-bis(t-butylperoxy)valerate, 2,2-bis(t-butylperoxy)butane, 1,1-bis(t-butylperoxy)-2-methylcyclohexane, t-butyl hydroperoxide, p-menthane hydroperoxide, 1,1,3,3-tetramethylbutyl hydroperoxide, t-hexyl hydroperoxide, dicumyl peroxide, 2,5-dimethyl- 2,5-bis(t-butylperoxy)hexane, α,α'-bis(t-butylperoxy)diisopropylbenzene, t-butylcumyl peroxide, di-t-butyl peroxide, 2,5-dimethyl-2,5-bis(t-butylperoxy)hexyn-3, isobutyryl peroxide, 3,5,5-trimethylhexanoyl peroxide, octanoyl peroxide, lauroyl peroxide, cinnamate peroxide, m-toluyl peroxide, benzoyl peroxide, diisopropyl Peroxydicarbonate, bis(4-t-butylcyclohexyl)peroxydicarbonate, di-3-methoxybutyl peroxydicarbonate, di-2-ethylhexyl peroxydicarbonate, di-sec-butyl peroxydicarbonate, di(3-methyl-3-methoxybutyl)peroxydicarbonate, di(4-t-butylcyclohexyl)peroxydicarbonate, α,α'-bis(neodecanoylperoxy)diisopropylbenzene, cumylperoxyneodecanoate, 1,1,3,3,-Tetramethylbutyl peroxyneodecanoate, 1-cyclohexyl-1-methylethyl peroxyneodecanoate, t-hexyl peroxyneodecanoate, t-butyl peroxyneodecanoate, t-hexyl peroxypivalate, t-butyl peroxypivalate, 2,5-dimethyl-2,5-bis(2-ethylhexanoylperoxy)hexane, 1,1,3,3-tetramethylbutyl peroxy-2-ethylhexanoate, 1-cyclohexyl-1-methylethyl peroxy-2-ethylhexanoate, t-hexyl peroxy-2-ethylhexanoate, t-butyl peroxy-2-ethylhexanoate, t-butyl peroxyisobutyrate, t-butyl peroxy Examples include, but are not limited to, ray acid, t-butyl peroxylaurate, t-butyl peroxy-3,5,5-trimethylhexanoate, t-butyl peroxyisopropyl monocarbonate, t-butyl peroxy-2-ethylhexyl monocarbonate, 2,5-dimethyl-2,5-bis(benzoylperoxy)hexane, t-butyl peroxyacetate, t-hexyl peroxybenzoate, t-butyl peroxy-m-toluylbenzoate, t-butyl peroxybenzoate, bis(t-butylperoxy)isophthalate, t-butyl peroxyallyl monocarbonate, 3,3',4,4'-tetra(t-butylperoxycarbonyl)benzophenone, etc. These may be used individually or in combination of two or more.

[0041] Examples of thermal anionic polymerization initiators include amines such as 2-methylimidazole, 2-ethylimidazole, 2-phenylimidazole, 2-ethyl-4-methylimidazole, 2-undecylimidazole, 1-cyanoethyl-2-ethyl-4-methylimidazole, triethylamine, triethylenediamine, 2-(dimethylaminomethyl)phenol, 1,8-diazabicyclo[5,4,0]undecene-7, tris(dimethylaminomethyl)phenol, and benzyldimethylamine, as well as phosphines such as triphenylphosphine, tributylphosphine, and trioctylphosphine.

[0042] Examples of thermal anionic polymerization initiators include, in addition to the above examples, "thermal latent curing catalysts," which are basic catalysts that are inert at room temperature and become activated by heating to function as polymerization catalysts. Examples of thermal latent curing catalysts include amine compounds that are solid at room temperature; amine adduct-type thermal latent curing catalysts such as reaction products of amine compounds and epoxy compounds (amine-epoxy adduct systems) and reaction products of amine compounds and isocyanate compounds or urea compounds (urea-type adduct systems); solid-disperse thermal latent curing catalysts such as microcapsule-type thermal latent curing catalysts and inclusion-type thermal latent curing catalysts. Amine compounds include aliphatic amines, aromatic amines, and heterocyclic amines.

[0043] Examples of amine compounds that are solid at room temperature include dicyandiamide, 2-heptadecylimidazole, 2-phenyl-4,5-dihydroxymethylimidazole, 2-undecylimidazole, 2-phenyl-4-methyl-5-hydroxymethylimidazole, 2-phenyl-4-benzyl-5-hydroxymethylimidazole, 2,4-diamino-6-(2-methyl-1-imidazolyl-(1))-ethyl-S-triazine, and 2,4-diamino-6-(2′-methylimidazolyl-(1)′)-ethyl-S- Examples include, but are not limited to, triazine isocyanuric acid adducts, 2-methylimidazole, 2-phenylimidazole, 2-phenyl-4-methylimidazole, 1-cyanoethyl-2-phenylimidazole, 1-cyanoethyl-2-methylimidazole trimellitate, 1-cyanoethyl-2-phenylimidazole trimellitate, N-(2-methylimidazolyl-1-ethyl)-urea, and N,N'-(2-methylimidazolyl-(1)-ethyl)-azivoyldiamide.

[0044] The amine compound used as one of the raw materials for the production of amine adduct-type thermal latent curing catalysts is one that has one or more active hydrogen atoms in its molecule that can undergo addition reactions with epoxy groups or isocyanate groups, and has at least one functional group selected from primary amino groups, secondary amino groups, and tertiary amino groups in its molecule. Examples of such amine compounds include, but are not limited to, the above-mentioned amine compounds that are solid at room temperature, as well as aliphatic amines such as diethylenetriamine, triethylenetetramine, n-propylamine, 2-hydroxyethylaminopropylamine, cyclohexylamine, and 4,4'-diamino-dicyclohexylmethane; aromatic amine compounds such as 4,4'-diaminodiphenylmethane and 2-methylaniline; and heterocyclic amine compounds containing nitrogen atoms such as 2-ethyl-4-methylimidazole, 2-ethyl-4-methylimidazoline, 2,4-dimethylimidazoline, piperidine, and piperazine.

[0045] Furthermore, among these, compounds having a tertiary amino group in the molecule and imidazole derivatives are particularly useful as raw materials for providing thermal latent curing catalysts with excellent curing acceleration capabilities.Examples of such compounds include amine compounds such as dimethylaminopropylamine, diethylaminopropylamine, di-n-propylaminopropylamine, dibutylaminopropylamine, dimethylaminoethylamine, diethylaminoethylamine, and N-methylpiperazine, as well as 2-methylimidazole, 2-ethylimidazole, 2-ethyl-4-methylimidazole, 2-phenylimidazole, 2-phenyl-4,5-dihydroxymethylimidazole, 2-phenyl-4-methyl-5-hydroxymethylimidazole, and 2-phenyl- Imidazole compounds such as phenyl-4-methylimidazole and 1-(2-aminoethyl)-2-methylimidazole; 2-dimethylaminoethanol, 1-methyl-2-dimethylaminoethanol, 1-phenoxymethyl-2-dimethylaminoethanol, 2-diethylaminoethanol, 1-butoxymethyl-2-dimethylaminoethanol, 1-(2-hydroxy-3-phenoxypropyl)-2-methylimidazole, 1-(2-hydroxy-3-phenoxypropyl)-2-ethyl-4-methylimidazole, 1-(2-hydroxy- 3-Butoxypropyl)-2-Methylimidazole, 1-(2-Hydroxy-3-Butoxypropyl)-2-Ethyl-4-Methylimidazole, 1-(2-Hydroxy-3-Phenoxypropyl)-2-Phenylimidazolin, 1-(2-Hydroxy-3-Butoxypropyl)-2-Methylimidazolin, 2-(Dimethylaminomethyl)phenol, 2,4,6-Tris(Dimethylaminomethyl)phenol, N-β-Hydroxyethylmorpholine, 2-Dimethylaminoethanethiol, 2-Mercaptopyridine, Benzimidazole, 2 Examples include, but are not limited to, alcohols, phenols, thiols, carboxylic acids, and hydrazides having a tertiary amino group or imidazole skeleton in the molecule, such as mercaptobenzimidazole, 2-mercaptobenzothiazole, 4-mercaptopyridine, N,N-dimethylaminobenzoic acid, N,N-dimethylglycine, nicotinic acid, isonicotinic acid, picolinic acid, N,N-dimethylglycine hydrazide, N,N-dimethylpropionic acid hydrazide, nicotinic acid hydrazide, and isonicotinic acid hydrazide.

[0046] Examples of epoxy compounds used as raw materials for the production of amine-epoxy adduct-type thermal latent curing catalysts include, but are not limited to, polyglycidyl ethers obtained by reacting polyhydric phenols such as bisphenol A, bisphenol F, catechol, and resorcinol, or polyhydric alcohols such as glycerin and polyethylene glycol with epichlorohydrin; glycidyl ether esters obtained by reacting hydroxycarboxylic acids such as p-hydroxybenzoic acid and β-hydroxynaphthoic acid with epichlorohydrin; polyglycidyl esters obtained by reacting polycarboxylic acids such as phthalic acid and terephthalic acid with epichlorohydrin; glycidylamine compounds obtained by reacting 4,4'-diaminodiphenylmethane and m-aminophenol with epichlorohydrin; and polyfunctional epoxy compounds such as epoxidized phenol novolac resins, epoxidized cresol novolac resins, and epoxidized polyolefins, as well as monofunctional epoxy compounds such as butyl glycidyl ether, phenyl glycidyl ether, various phenylphenol glycidyl ethers, and glycidyl methacrylate.

[0047] Examples of isocyanate compounds used as raw materials for the production of amine-urea type adduct-based thermal latent curing catalysts include monofunctional isocyanate compounds such as n-butyl isocyanate, isopropyl isocyanate, phenyl isocyanate, and benzyl isocyanate; polyfunctional isocyanate compounds such as hexamethylene diisocyanate, toluene diisocyanate, 1,5-naphthalene diisocyanate, diphenylmethane-4,4'-diisocyanate, isophorone diisocyanate, xylylene diisocyanate, paraphenylene diisocyanate, 1,3,6-hexamethylene triisocyanate, and bicycloheptane triisocyanate; and compounds containing terminal isocyanate groups obtained by the reaction of these polyfunctional isocyanate compounds with active hydrogen compounds. Examples of such terminal isocyanate group-containing compounds include, but are not limited to, addition compounds having terminal isocyanate groups obtained by the reaction of toluene diisocyanate and trimethylolpropane, and addition compounds having terminal isocyanate groups obtained by the reaction of toluene diisocyanate and pentaerythritol. Examples of urea compounds used as raw materials for the production of amine-urea type adduct-type thermal latent curing catalysts include, but are not limited to, urea and thiourea.

[0048] Amine adduct-based thermal latent curing catalysts are, for example, combinations of (a) an amine compound and an epoxy compound, (b) these two components and an active hydrogen compound, or (c) an amine compound and an isocyanate compound and / or urea compound. These can be easily prepared by taking and mixing each component, reacting them at a temperature from room temperature to 200°C, then cooling and solidifying them before pulverizing, or by reacting them in a solvent such as methyl ethyl ketone, dioxane, or tetrahydrofuran, removing the solvent, and then pulverizing the solid.

[0049] A microencapsulated thermal latent curing catalyst is a curing catalyst having a structure in which an amine compound, or an amine adduct compound obtained by the reaction of an amine compound with an epoxy compound, isocyanate compound, or urea compound, serves as the core, and is coated with a shell made of a synthetic resin or inorganic oxide. Examples of amine compounds include the aforementioned amine compounds. The amine compound is preferably an imidazole derivative because it exhibits suitable latent properties. Examples of imidazole derivatives include 2-methylimidazole, 2-phenylimidazole, 2-phenyl-4-methylimidazole, 2-phenyl-4,5-dihydroxymethylimidazole, and 2-phenyl-4-methyl-5-hydroxymethylimidazole. Examples of synthetic resins that serve as the shell include phenolic resins, melamine resins, epoxy resins, urethane resins, and urea resins, and these resins can also be used in combination. Examples of inorganic oxides that serve as the shell include silica, alumina, titania, and magnesia.

[0050] Representative examples of commercially available thermal latent curing catalysts include, but are not limited to, the following: Amine-epoxy adduct curing catalysts include "Amicure PN-23" (Ajinomoto Fine Techno Co., Ltd.), "Amicure PN-40" (Ajinomoto Fine Techno Co., Ltd.), "Amicure PN-50" (Ajinomoto Fine Techno Co., Ltd.), "Hardener X-3661S" (ACR Co., Ltd.), "Hardener X-3670S" (ACR Co., Ltd.), "NovaCure HX-3742" (Asahi Kasei Corporation), "NovaCure Examples include, but are not limited to, "HX-3721" (Asahi Kasei Corporation product name), "NovaCure HXA9322HP" (Asahi Kasei Corporation product name), "NovaCure HXA3922HP" (Asahi Kasei Corporation product name), "NovaCure HXA3932HP" (Asahi Kasei Corporation product name), "NovaCure HXA5945HP" (Asahi Kasei Corporation product name), "NovaCure HXA5911HP" (Asahi Kasei Corporation product name), and "NovaCure HXA9382HP" (Asahi Kasei Corporation product name). All Novacure products are supplied in a state where microcapsule particles are dispersed in epoxy resin. When Novacure is used as a thermal latent curing catalyst, the resin composition will contain epoxy resin. Examples of the amine-urea type adduct curing catalysts include, but are not limited to, "Fujicure-FXE-1000" (T&K TOKA Corporation product name), "Fujicure-FXR1020" (T&K TOKA Corporation product name), "Fujicure-FXR-1030" (T&K TOKA Corporation product name), "Fujicure-FXR1121" (T&K TOKA Corporation product name), "Fujicure-FXR1081" (T&K TOKA Corporation product name), "Fujicure-1061" (T&K TOKA Corporation product name), and "Fujicure-1171" (T&K TOKA Corporation product name). Other commercially available thermal latent curing catalysts include, but are not limited to, "Fujicure-7550" (product name of T&KTOKA Co., Ltd.).

[0051] The inclusion-type thermally latent curing catalyst is a curing catalyst having a structure in which guest molecules such as amine compounds are confined in the crystal space formed by host molecules in molecular units. As a commercially available product of the inclusion-type thermally latent curing catalyst, "NISSOCURE TIC-188" (product name of Nippon Soda Co., Ltd.) can be mentioned.

[0052] As the thermally latent curing catalyst as a thermal anionic polymerization initiator, any one kind may be used, or two or more kinds may be used in combination. The thermal cationic polymerization initiator generates a cation as an active species by heat and promotes the polymerization of the cationically polymerizable compound. Examples of the thermal cationic polymerization initiator include BF ３ , － － , SbF ６ -, AsF ６ － , B(C ６ F ５ ) ４ － , Ga(C ６ F ５ ) ４ － , C(CF ３ SO ２ ) ３ － , [P(R １ ) ａ F ６－ａ ) － , [C(R １ SO ２ ) ３ ) － , or [N(R １ SO ２ ) ２ ) － (wherein, each R １ is independently an alkyl group in which at least a part of hydrogen atoms is substituted with fluorine atoms, a is an integer of 0 to 5, and when a is an integer of 2 or more, a plurality of R １ may be the same as or different from each other.) etc. are used as counter anions, and various onium salts having an iodonium cation, a sulfonium cation, an ammonium cation, a phosphonium cation, etc. as the cation part can be mentioned.

[0053] Examples of iodonium cations include, but are not limited to, iodonium ions such as diphenyliodonium, di-p-tolyliodonium, bis(4-dodecylphenyl)iodonium, bis(4-methoxyphenyl)iodonium, (4-octyloxyphenyl)phenyliodonium, bis(4-decyloxy)phenyliodonium, 4-(2-hydroxytetradecyloxy)phenylphenyliodonium, 4-isopropylphenyl(p-tolyl)iodonium, and 4-isobutylphenyl(p-tolyl)iodonium. Thermal cationic polymerization initiators whose countercation is an iodonium cation can also function as photocationic polymerization initiators.

[0054] Examples of sulfonium cations include diarylsulfonium such as diphenylphenacylsulfonium, diphenyl-4-nitrophenacylsulfonium, diphenylbenzylsulfonium, and diphenylmethylsulfonium, phenylmethylbenzylsulfonium, 4-hydroxyphenylmethylbenzylsulfonium, 4-methoxyphenylmethylbenzylsulfonium, 4-acetocarbonyloxyphenylmethylbenzylsulfonium, 4-hydroxyphenyl(2-naphthylmethyl)methylsulfonium, 2-naphthylmethylbenzylsulfonium, 2-naphthylmethyl(1-ethoxycarbonyl)ethylsulfonium, and phenylmethylphenacylsulfonium. Examples of monoaryl sulfoniums such as ruphonium, 4-hydroxyphenylmethylphenacylsulfonium, 4-methoxyphenylmethylphenacylsulfonium, 4-acetocarbonyloxyphenylmethylphenacylsulfonium, 2-naphthylmethylphenacylsulfonium, 2-naphthyloctadecylphenacylsulfonium, and 9-anthracenylmethylphenacylsulfonium, as well as trialkylsulfoniums such as dimethylphenacylsulfonium, phenacyltetrahydrothiophenium, dimethylbenzylsulfonium, benzyltetrahydrothiophenium, and octadecylmethylphenacylsulfonium, are not limited to these.

[0055] Examples of ammonium cations include, but are not limited to, dimethylphenyl(4-methoxybenzyl)ammonium, dimethylphenyl(4-methylbenzyl)ammonium, methylphenyldibenzylammonium, phenyltribenzylammonium, and dimethylphenyl(3,4-dimethylbenzyl)ammonium.

[0056] Examples of phosphonium cations include, but are not limited to, tetraalkylphosphoniums such as triethylbenzylphosphonium, tributylbenzylphosphonium, tetraethylphosphonium, tetrabutylphosphonium, tetrahexylphosphonium, triethylphenacylphosphonium, and tributylphenacylphosphonium.

[0057] Examples of thermal cationic polymerization initiators include dimethylphenyl(4-methoxybenzyl)ammonium tetrakis(pentafluorophenyl) borate, a borate-based quaternary ammonium salt (e.g., product name: CXC-1821, manufactured by King Industries, Inc.), and 4-isopropyl-4'-methyldiphenyliodonium tetrakis(pentafluorophenyl) borate, a borate-based iodonium salt (e.g., product name: BLUESIL® PI, manufactured by ELKEM SILICONES). Examples include, but are not limited to, 2074), 4-methylphenyl-4-(1-methylethyl)phenyliodonium tri(pentafluoroethyl)trifluorophosphate (for example, product name: IK-1 manufactured by Sunapro Co., Ltd.), a phosphate-based sulfonium salt thermal cationic polymerization initiator represented by the following formula (1), an iodonium salt-based thermal acid generator represented by the following formula (2) (see Japanese Patent Publication No. 2022-080366), and a sulfonium salt-based thermal cationic polymerization initiator represented by the following formula (3) (see WO2018 / 020974).

[0058]

[0059]

[0060]

[0061] The content of (C) the curing catalyst system containing at least one latent curing catalyst in the resin composition is preferably 0.5 to 30 parts by mass, more preferably 1.0 to 25 parts by mass, and even more preferably 1.5 to 20 parts by mass, based on 100 parts by mass of the total of components (A) and (B). Furthermore, the content of (C) the curing catalyst system containing at least one latent curing catalyst in the resin composition is preferably 0.1 to 25% by mass, more preferably 1.0 to 20% by mass, and even more preferably 1.5 to 18% by mass, based on the total mass of the resin composition.

[0062] <Other Components> In addition to components (A) to (C), the resin composition of this embodiment may also contain optional components such as (D) polymerizable compounds other than component (A), (E) photoradical initiators, (F) stabilizers, and (G) other additives.

[0063] <(D) and other polymerizable compounds> The resin composition of this embodiment may contain polymerizable compounds other than components (D) and (A) (hereinafter also referred to as "component (D)"), to the extent that the effects of the present invention are not impaired. The polymerizable compound of component (D) can be appropriately selected from radical polymerizable compounds, cationic polymerizable compounds, anionic polymerizable compounds, or any combination thereof. Examples of radical polymerizable compounds include maleimide compounds, (meth)acrylamide compounds, cyanoacrylate compounds, vinyl ether compounds, styrene compounds, methylene malonates (2-methylene-1,3-dicarbonyl compounds and their derivatives), allyl compounds, and other compounds having unsaturated double bonds. These resins may be used individually or in mixtures of two or more types.

[0064] Maleimide compounds include monofunctional maleimide compounds having one maleimide group and polyfunctional maleimide compounds having two or more maleimide groups. Maleimide compounds having two maleimide groups are sometimes called bismaleimide compounds. Examples of bismaleimide compounds include N,N'-(4,4'-diphenylmethane)bismaleimide and bisphenol A. Diphenyl ether bismaleimide, 3,3'-dimethyl-5,5'-diethyl-4,4'-diphenylmethane bismaleimide, 4-methyl-1,3-phenylene bismaleimide, 1,6'-bismaleimide-(2,2,4-trimethyl)hexane, bis-(3-ethyl-5-methyl-4-maleimidophenyl)methane, m-phenylene bismaleimide (N,N'-1,3-phenylene bismaleimide), 1,6-bismaleimide hexane, 1,2-bismaleimide ethane (N,N'-ethylene Examples include, but are not limited to, dimaleimide, N,N'-(1,2-phenylene)bismaleimide, N,N-1,3-phenylenedimaleimide, N,N'-1,4-phenylenedimaleimide, N,N'-(sulfonyldi-p-phenylene)dimaleimide, N,N'-[3,3'-(1,3-phenylenedioxy)diphenyl]bismaleimide, N,N'-[4,4'-(1,3-phenylenedioxy)diphenyl]bismaleimide, and 4,4'-dimaleimide phenyl ether. These may be used individually or in combination of two or more.

[0065] When a low room-temperature modulus is required for the cured resin composition, a bismaleimide compound having hydrocarbon groups derived from dimer acid can be used. Such bismaleimides are described, for example, in Japanese Patent Application Publication No. 2015-193725. Examples of commercially available bismaleimides having hydrocarbon groups derived from dimer acid include, but are not limited to, "BMI-689," "BMI-1500," "BMI-1700," which are liquid at 25°C, or "BMI-3000," which is solid at 25°C (all manufactured by Designer Molecules Inc.). These may be used individually or in combination of two or more.

[0066] Examples of monofunctional maleimide compounds include, but are not limited to, monofunctional aliphatic maleimide compounds such as N-n-butylmaleimide, N-hexylmaleimide, 2-maleimidoethyl-ethyl carbonate, 2-maleimidoethyl-propyl carbonate, and N-ethyl-(2-maleimidoethyl)carbamate; alicyclic monofunctional maleimide compounds such as N-cyclohexylmaleimide; N-arylmaleimides such as N-phenylmaleimide; and N-aralkylmaleimides such as N-benzylmaleimide. The aliphatic maleimides and alicyclic maleimides may have substituents, such as phenyl groups, benzyl groups, and hydroxyl groups. The N-arylmaleimides and N-aralkylmaleimides may have substituents, such as alkyl groups, nitro groups, hydroxyl groups, alkoxy groups, carboxyl groups, and halogen groups. Examples of commercially available single-tube maleimides include Imilex(R)-C, Imilex(R)-P (both manufactured by Nippon Shokubai Co., Ltd.), and O-CPMI (manufactured by Yamato Kasei Kogyo Co., Ltd.), but are not limited to these. These may be used individually or in combination of two or more types.

[0067] (meth)acrylamide compounds contain an acrylamide group (H ２ C=CHCONH-) or methacrylamide group (H ２ C = C(CH) ３ The compound has at least one (meth)acrylamide group (CONH-). Examples of (meth)acrylamide compounds include, but are not limited to, N,N'-methylenebis(meth)acrylamide, N,N'-ethylenebis(meth)acrylamide, and 1,2-di(meth)acrylamide ethylene glycol.

[0068] Cyanoacrylate compounds are H ２Known compounds represented by C=C(CN)-COOR can be used. In the formula, R is an ester residue such as an alkyl group, cycloalkyl group, alkenyl group, cycloalkenyl group, alkynyl group, or aryl group. The number of carbon atoms in the ester residue is not particularly limited, but typically those with 1 to 8 carbon atoms can be used. Ester residues consisting of substituted hydrocarbon groups such as alkoxyalkyl groups and trialkylsilylalkyl groups can also be used.

[0069] Examples of cyanoacrylate compounds include, but are not limited to, alkyl and cycloalkyl cyanoacrylates such as methyl cyanoacrylate, ethyl cyanoacrylate, propyl cyanoacrylate, butyl cyanoacrylate, and cyclohexyl cyanoacrylate; alkenyl and cycloalkenyl cyanoacrylates such as allyl cyanoacrylate, methallyl cyanoacrylate, and cyclohexenyl cyanoacrylate; alkynyl cyanoacrylates such as propangyl cyanoacrylate; aryl cyanoacrylates such as phenyl cyanoacrylate and toluyl cyanoacrylate; methoxyethyl cyanoacrylate, ethoxyethyl cyanoacrylate, and furfuryl cyanoacrylate containing heteroatoms; trimethylsilylmethyl cyanoacrylate, trimethylsilylethyl cyanoacrylate, trimethylsilylpropyl cyanoacrylate, and dimethylvinylsilylmethyl cyanoacrylate containing silicon. These may be used individually or in combination of two or more.

[0070] Vinyl ether compounds include vinyl ether groups (H ２The compound has at least one C=CH-O- group. Examples of vinyl ether compounds include, but are not limited to, ethyl vinyl ether, triethylene glycol divinyl ether, trimethylolpropane trivinyl ether, hydroxybutyl vinyl ether, dodecyl vinyl ether, cyclohexyl vinyl ether, 1,4-butanediol divinyl ether, nonanediol divinyl ether, cyclohexanediol divinyl ether, and cyclohexanedimethanol divinyl ether. These may be used individually or in combination of two or more.

[0071] Styrene compounds, styrene group (H ２ C = CH - C ６ H ５ The compound has at least one (-). Examples of styrene compounds include, but are not limited to, styrene, α-methylstyrene, 2-methylstyrene, 3-methylstyrene, 4-methylstyrene, 4-propylstyrene, 4-t-butylstyrene, 4-cyclohexylstyrene, 4-dodecylstyrene, 2,4-dimethylstyrene, 2,4-diisopropylstyrene, 2,4,6-trimethylstyrene, 2-ethyl-4-benzylstyrene, 4-(phenylbutyl)styrene, N,N-diethyl-4-aminoethylstyrene, 4-methoxystyrene, etc. These may be used alone or in combination of two or more.

[0072] Methylene malonates are malonates having at least one methylene group in their molecule, and include monofunctional methylene malonates having one methylene group and polyfunctional methylene malonates having two or more methylene groups. Methylene malonates preferably have a molecular weight of 220 or higher. There are no particular restrictions on the types of methylene malonates that can be used; in addition to compounds described in WO2018 / 212330A1, etc., various disclosed methylene malonates can be used. Methylene malonates may be used individually or in combination of two or more types.

[0073] In this specification, an allyl compound means a compound having at least one allyl group (-CH2-CH=CH2). Examples of allyl compounds include monofunctional allyl compounds having one allyl group and polyfunctional allyl compounds having two or more allyl groups. When a radical polymerizable compound contains an allyl compound, the allyl compound is preferably a polyfunctional allyl compound, or a combination of a polyfunctional allyl compound and a monofunctional allyl compound.

[0074] Examples of allyl compounds include diallyl terephthalate ether, diallyl isophthalate ether, triallyl trimellitate ether, tetraallyl pyromellitate ether, diallyl biphenyl-2,2'-dicarboxylic acid ether, allyl compounds having a bisphenol skeleton (e.g., bisphenol A bisallyl ether, bisphenol C bisallyl ether), allylphenol compounds having a bisphenol skeleton (e.g., 2,2'-diallylbisphenol A, 2,2'-diallylbisphenol C), other allylphenol compounds (e.g., allylphenol compounds described in Japanese Patent Publication No. 2019-052258), and cyanuric acid. Examples include, but are not limited to, allyl compounds having an isocyanuric acid skeleton such as trialyl, allyl cyanurate derivatives, and trialyl isocyanurate; allyl compounds having a glycoluryl skeleton such as 1,3,4,6-tetraallyl glycoluryl; glycerin monoallyl ether, allyl glycidyl ether, allyl hydroxyacetate, allyl hydroxypropanoate, allyl hydroxyhexanoate, allyl 4-hydroxycyclohexylacetate, trimethylolpropanediallyl ether, pentaerythritol trialyl ether, pentaerythritol tetraallyl ether, and (meth)acrylates having an allyloxymethyl group.Examples of commercially available allyl compounds include diallylbisphenol A (e.g., BPA-CA from Konishi Chemical Industry Co., Ltd., DABPA from Yamato Chemical Industry Co., Ltd., DA-BPA from Yokkaichi Synthetic Co., Ltd.), diallylbisphenol F (e.g., MEH-8000H, MEH-8005 from UBE Corporation), biphenylene resin (SBA series from Gun-ei Chemical Industry Co., Ltd.), allylphenol resin (APG series from Gun-ei Chemical Industry Co., Ltd.), allylphenol resin (LVA series from Gun-ei Chemical Industry Co., Ltd.), propenylated biphenylene resin (Gun-ei Chemical Industry Co., Ltd.) Examples include, but are not limited to, the BPN series manufactured by Gyogyo Co., Ltd., allyl etherphenol resin (FTC-AE series manufactured by Gun-ei Chemical Industry Co., Ltd.), polyfunctional allylphenol resin (FATC series manufactured by Gun-ei Chemical Industry Co., Ltd.), allyl cyanurate derivatives (e.g., MA-DGIC, DAMGIC, MeDAIC, L-DAIC, DD-1 manufactured by Shikoku Chemicals, Inc.), triallyl isocyanurate (e.g., TAIC manufactured by Shinryo Co., Ltd.), and 1,3,4,6-tetraallyl glycoluryl (TA-G manufactured by Shikoku Chemicals, Inc.). These may be used individually or in combination of two or more.

[0075] Cationic polymerizable compounds are compounds having one or more cationic polymerizable groups in their molecule. Examples of cationic polymerizable compounds include, but are not limited to, compounds having epoxy groups, compounds having oxetanyl groups, compounds having vinyl ether groups, compounds having other cationic polymerizable groups, and compounds having any combination of these cationic polymerizable groups.

[0076] In this specification, a compound having an epoxy group is a compound having at least one epoxy group in its molecule, and is also referred to as an epoxy resin. Examples include monofunctional epoxy compounds having one epoxy group and polyfunctional epoxy compounds having two or more epoxy groups. In one embodiment, the epoxy compound preferably contains at least a polyfunctional epoxy compound, and may contain a combination of a polyfunctional epoxy compound and a monofunctional epoxy compound. Epoxy compounds can be broadly classified into epoxy compounds having an aromatic ring skeleton, aliphatic epoxy compounds, and alicyclic epoxy compounds depending on the type of skeleton. Epoxy resins are preferably liquid at room temperature (25°C ± 5°C). However, it is also possible to use an epoxy resin that is solid at room temperature by diluting it with a diluent or the like to make it liquid.

[0077] Examples of polyfunctional epoxy compounds having an aromatic ring skeleton include bisphenol A type epoxy resins (e.g., EPICLON® 850, 850-S, EXA-850CRP, EXA-8067, etc., manufactured by DIC Corporation), polyalkylene oxide modified bisphenol A type epoxy resins (e.g., polypropylene alkylene oxide modified bisphenol A type epoxy resins, e.g., AER9000, manufactured by Asahi Kasei Corporation, EP-4000S, EP-4003S, EP-4005, EP-4010S, manufactured by ADEKA Corporation), polyethylene oxide modified bisphenol A type epoxy resins (e.g., Rikaresin BEO-60E, manufactured by Shin Nippon Rika Co., Ltd.), and bisphenol F type epoxy resins (e.g., EPICLON® 830-S, EXA-830LVP, EXA-835LV, manufactured by DIC Corporation, Nippon Steel Corporation). Examples include, but are not limited to, YDF-8170 (manufactured by Sumikin Chemical Co., Ltd.), polyalkylene oxide-modified bisphenol F type epoxy resin, bisphenol AD ​​type epoxy resin, bisphenol S type epoxy resin, naphthalene type epoxy resin (e.g., EPICLON® HP-4032D, HP-720H, etc., manufactured by DIC Corporation), phenol novolac type epoxy resin (e.g., EPICLON® N-740, N-770, etc., manufactured by DIC Corporation), cresol novolac type epoxy resin (e.g., EPICLON® N-660, N-670, N-655-EXP-S, etc., manufactured by DIC Corporation), polyfunctional epoxy compounds such as glycidyl ethers of tetra(hydrophenyl)alkanes and glycidyl ethers of tetrahydroxybenzophenone, and epoxidized polyvinylphenols.

[0078] Examples of monofunctional epoxy compounds having an aromatic ring skeleton include, but are not limited to, p-tert-butylphenylglycidyl ether (e.g., ADEKA glycirol® ED-509E, ED-509S, etc., manufactured by ADEKA Corporation) and 2-phenylphenol glycidyl ether (e.g., OPP-G, etc., manufactured by Sanko Co., Ltd.).

[0079] Aliphatic epoxy compounds are epoxy compounds that do not have either an aromatic ring skeleton or an alicyclic epoxy group. Examples include glycidyl ethers of aliphatic alcohols (including chain alcohols and alicyclic alcohols) or their polyalkylene oxide adducts, and hydrogenated bisphenol-type epoxy resins obtained by hydrogenating bisphenol-type epoxy resins such as bisphenol A-type epoxy resins and bisphenol F-type epoxy resins. Examples of aliphatic epoxy compounds include ethylene glycol diglycidyl ether, diethylene glycol diglycidyl ether, propylene glycol diglycidyl ether, 1,4-butanediol diglycidyl ether, neopentyl glycol diglycidyl ether, 1,6-hexanediol diglycidyl ether, glycerin diglycidyl ether, trimethylolpropane triglycidyl ether (e.g., Epolite 100MF manufactured by Kyoeisha Chemical Co., Ltd.), polyethylene glycol diglycidyl ether, and polybutylene glycol diglycidyl ether (e.g., jER manufactured by Mitsubishi Chemical Corporation). Examples include, but are not limited to, YX7400N, lauryl alcohol polyethylene glycol glycidyl ether (e.g., Denacol EX-171 manufactured by Nagase ChemteX Corporation), diglycidyl ethers of alicyclic diols (e.g., Adeka Resin EP-4088S and EP-4088L manufactured by ADEKA Corporation), diglycidyl ethers of polyalkylene oxide adducts of alicyclic diols, and hydrogenated bisphenol A diglycidyl ether (e.g., jER YX8000 manufactured by Mitsubishi Chemical Corporation). (C) Any one of the epoxy compounds other than alicyclic epoxy compounds may be used, or two or more may be used in combination.

[0080] Examples of alicyclic epoxy compounds include 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate (e.g., Celoxide® 2021P manufactured by Daicel Corporation), 3,4-epoxy-1-methylcyclohexyl-3,4-epoxy-1-methylhexanecarboxylate, 6-methyl-3,4-epoxycyclohexylmethyl-6-methyl-3,4-epoxycyclohexanecarboxylate, 3,4-epoxy-3-methylcyclohexylmethyl-3,4-epoxy-3-methylcyclohexanecarboxylate, 3,4-epoxy-5-methylcyclohexylmethyl-3,4-epoxy-5-methylcyclohexanecarboxylate, bis(3,4-epoxycyclohexylmethyl) adipate, 3,4-epoxy-6-methylcyclohexanecarboxylate, methylenebis(3,4-epoxycyclohexane), propane-2,2-diylbis(3,4-epoxycyclohexane), and 2,2-bis(3,4 -Epoxycyclohexyl)propane, dicyclopentadiene diepoxide, ethylenebis(3,4-epoxycyclohexanecarboxylate), limonene dioxide (1,2:8,9-diepoxylimonene), (3,3',4,4'-diepoxy)bicyclohexyl (e.g., Celoxide® 8010 manufactured by Daicel Corporation), dioctyl epoxyhexahydrophthalate, di-2-ethylhexyl epoxyhexahydrophthalate, 1-epoxyethyl-3,4- Examples include, but are not limited to, epoxycyclohexane, 1,2-epoxy-2-epoxyethylcyclohexane, 1,2-epoxy-4-vinylcyclohexane, α-pinene oxide, 2,2-bis(3,4-epoxycyclohexyl)propane, 1,2-bis(3,4-epoxycyclohexane-1-yl)ethane, 1,2-epoxy-1,2-bis(3,4-epoxycyclohexane-1-yl)ethane, and bis(3,4-epoxycyclohexylmethyl) ether. Any one of the alicyclic epoxy compounds may be used, or two or more may be used in combination.

[0081] In this specification, a compound having an oxetanyl group is a compound having at least one oxetane ring (e.g., a 3-oxetanyl group) in its molecule, and is also referred to as an oxetane compound. Although the polymerization initiation reaction of oxetane compounds is slower than that of epoxy compounds, they polymerize rapidly once the polymerization initiation species reaches a certain concentration or higher, thus contributing to the rapid curing reaction of resin compositions at low temperatures. In some embodiments, the oxetane compound preferably has 1 to 6 oxetane rings in its molecule, and more preferably has 1 to 2 oxetane rings in its molecule.

[0082] In this specification, a compound having a vinyl ether group is a compound having at least one vinyl ether group in its molecule. Examples of oxetane compounds include bis[1-ethyl(3-oxetanyl)]methyl ether (also known as (3-ethyl-3{[(3-ethyloxetan-3-yl)methoxy]methyl}oxetane)), xylylenebisoxetane, 4,4'-bis[3-ethyl-(3-oxetanyl)methoxymethyl]biphenyl, 1,4-bis(3-ethyl-3-oxetanylmethoxy)methylbenzene, (bis[(3-ethyl-3-oxetanyl)methyl]isophthalate), 3-ethyl-3-hydroxymethyloxetane, 2-ethylhexyloxetane, (3-ethyloxetane-3- Examples of oxetane compounds include, but are not limited to, methyl methacrylate (yl), 3-ethyl-3-[(2-ethylhexyloxy)methyl]oxetane, 3-ethyl-3-(4-hydroxybutyl)oxymethyl oxetane, 3-ethyl-3-phenoxymethyl oxetane, oxetanylsilsesquioxetane (e.g., OXT-191 manufactured by Toagosei Co., Ltd.), 3-ethyl-3{[(3-ethyloxetane-3-yl)methoxy]methyl}oxetane (e.g., OXT-221 manufactured by Toagosei Co., Ltd.), and phenol novolac oxetane (e.g., PHOX manufactured by Toagosei Co., Ltd.). One of these oxetane compounds may be used, or two or more may be used in combination.

[0083] Specific examples of cationic polymerizable compounds include tetra(hydrophenyl)alkane glycidyl ethers, tetrahydroxybenzophenone glycidyl ethers, epoxidized polyvinylphenol, p-tert-butylphenyl glycidyl ether, ethylene glycol diglycidyl ether, diethylene glycol diglycidyl ether, propylene glycol diglycidyl ether, 1,4-butanediol diglycidyl ether, neopentyl glycol diglycidyl ether, 1,6-hexanediol diglycidyl ether, glycerin diglycidyl ether, trimethylolpropane triglycidyl ether, polyethylene glycol diglycidyl ether, hydrogenated bisphenol A diglycidyl ether, n-butyl glycidyl ether, 2-ethylhexyl glycidyl ether, 1,2-epoxytetradecane, 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate, 3,4-epoxy-1-methylcyclohexyl-3,4-epoxy-1-methylhexanecarboxylate, and 6-methyl-3,4-e Poxycyclohexylmethyl-6-methyl-3,4-epoxycyclohexanecarboxylate, 3,4-epoxy-3-methylcyclohexylmethyl-3,4-epoxy-3-methylcyclohexanecarboxylate, 3,4-epoxy-5-methylcyclohexylmethyl-3,4-epoxy-5-methylcyclohexanecarboxylate, bis(3,4-epoxycyclohexylmethyl) adipate, 3,4-epoxy-6-methylcyclohexanecarboxylate, methylenebis(3,4-epoxycyclohexane), pro Pan-2,2-diyl-bis(3,4-epoxycyclohexane), 2,2-bis(3,4-epoxycyclohexyl)propane, dicyclopentadiene diepoxide, ethylenebis(3,4-epoxycyclohexanecarboxylate), limonene dioxide (1,2:8,9-diepoxylimonene), (3,3',4,4'-diepoxy)bicyclohexyl, dioctyl epoxyhexahydrophthalate, di-2-ethylhexyl epoxyhexahydrophthalate, 1-epoxyethyl-3,4-epoxycyclohexane, 1,Compounds in which some or all of the double bonds of 2-epoxy-2-epoxyethylcyclohexane, 1,2-epoxy-4-vinylcyclohexane, α-pinene oxide, 1,2-epoxy-4-(2-oxyranyl)cyclohexane adducts of 2,2-bis(hydroxymethyl)-1-butanol, epoxidized polybutadiene, styrene-butadiene copolymers are epoxidized, bis[1-ethyl(3-oxetanyl)]methyl ether (also known as (3-ethyl-3{[(3-ethyloxetan-3-yl)methoxy]methyl 3-ethyl-(3-oxetanyl)methyl oxetane, xylylene bisoxetane, 4,4'-bis[3-ethyl-3-oxetanyl methoxymethyl]biphenyl, 1,4-bis(3-ethyl-3-oxetanyl methoxy)methylbenzene, (bis[(3-ethyl-3-oxetanyl)methyl]isophthalate), 3-ethyl-3-hydroxymethyl oxetane, 2-ethylhexyl oxetane, (3-ethyloxetane-3-yl)methyl methacrylate, 3-ethyl-3-[(2-ethylhexyloxy)methyl]oxetane, 3-ethyl-3- Examples include, but are not limited to, (4-hydroxybutyl)oxymethyl oxetane, 3-ethyl-3-phenoxymethyl oxetane, oxetanylsilsesquioxetane, 3-ethyl-3{[(3-ethyloxetan-3-yl)methoxy]methyl}oxetane, phenol novolac oxetane, 1,4-butanediol divinyl ether, diethylene glycol divinyl ether, triethylene glycol divinyl ether, tetraethylene glycol divinyl ether, n-propyl vinyl ether, isopropyl vinyl ether, n-butyl vinyl ether, isobutyl vinyl ether, 2-ethylhexyl vinyl ether, cyclohexyl vinyl ether, 2-hydroxyethyl vinyl ether, diethylene glycol monovinyl ether, 4-hydroxybutyl vinyl ether, 2-(2-vinyloxyethoxy)ethyl acrylate, 2-(2-vinyloxyethoxy)ethyl methacrylate, 1,4-cyclohexanedimethanol monovinyl ether, and 1,4-cyclohexanedimethanol divinyl ether.

[0084] Commercially available cationic polymerizable compounds include EPICLON® 850, 850-S, EXA-850CRP, EXA-8067 from DIC Corporation; AER9000 from Asahi Kasei Corporation; EP-4000S, EP-4003S, EP-4010S from ADEKA Corporation; EPICLON® 830-S, EXA-830LVP, EXA-835LV from DIC Corporation; and EPICLON® HP-40 from DIC Corporation. 32D, HP-720H; EPICLON® N-740, N-770 manufactured by DIC Corporation; EPICLON® N-660, N-670, N-655-EXP-S manufactured by DIC Corporation; Adekaglycirol® ED-509E, ED-509S manufactured by ADEKA Corporation; OPP-G manufactured by Sanko Co., Ltd.; Epolite 100MF manufactured by Kyoeisha Chemical Co., Ltd.; AER-9000 manufactured by Asahi Kasei Corporation; jER manufactured by Mitsubishi Chemical Corporation Examples include, but are not limited to, YX7400N; jER YX8000 manufactured by Mitsubishi Chemical Corporation; Celoxide® 2021P manufactured by Daicel Corporation; Celoxide® 8010 manufactured by Daicel Corporation; EHPE3150 manufactured by Daicel Corporation; EPOLEAD PB manufactured by Daicel Corporation; EPOFRIEND manufactured by Daicel Corporation; HiREM-1 and HiREM-2 manufactured by Shikoku Chemicals, Inc.; OXT-191 manufactured by Toagosei Co., Ltd.; OXT-221 manufactured by Toagosei Co., Ltd.; and PHOX manufactured by Toagosei Co., Ltd. Any one of these cationic polymerizable compounds may be used, or two or more may be used in combination.

[0085] Examples of anionic polymerizable compounds include epoxy group compounds, as shown in the examples of cationic polymerizable compounds, and their curing agents, such as thiol-based curing agents, phenol-based curing agents, acid anhydride-based curing agents, and amine-based curing agents. Methylene malonates, as shown in the examples of radical polymerizable compounds, can also be cited as anionic polymerizable compounds. These may be used individually or in combination of two or more.

[0086] The polymerizable compound of component (D) may be one of the radical polymerizable compound, cationic polymerizable compound, or anionic polymerizable compound, or a combination of these may be used as desired. The resin composition of this embodiment preferably contains an epoxy resin as component (D). The inclusion of an epoxy resin in component (D) results in good adhesion.

[0087] The content of the polymerizable compound of component (D) in the resin composition is preferably 0.1 to 30% by mass, more preferably 0.5 to 25% by mass, and even more preferably 1.0 to 20% by mass, based on the total mass of the resin composition.

[0088] <(E) Photopolymerization Initiator> The resin composition of this embodiment may contain (E) a photopolymerization initiator (hereinafter also referred to as "component (E)") to the extent that it does not impair the effects of the present invention. A photopolymerization initiator is a reagent that absorbs light to generate active species such as radicals, cations, and anions, thereby promoting the polymerization of polymerizable compounds. The (E) photopolymerization initiator can be appropriately selected from photoradical polymerization initiators, photoacid generators, photobase generators, or any combination thereof. By including the (E) photopolymerization initiator, the reaction with component (A) by light irradiation is promoted.

[0089] Photoradical polymerization initiators absorb light and generate radicals as active species, thereby promoting the polymerization of radically polymerizable compounds. Examples of photoradical initiators include alkylphenone compounds, acylphosphine oxide compounds, oxime ester compounds, and compounds having a photosensitive site and a peroxide structure.

[0090] Examples of alkylphenone compounds include benzyldimethyl ketals such as 2,2-dimethoxy-1,2-diphenylethane-1-one (commercially available as Omnirad 651 from IGM Resins B.V.); α-aminoalkylphenones such as 2-methyl-2-morpholino(4-thiomethylphenyl)propan-1-one (commercially available as Omnirad 907 from IGM Resins B.V.); α-hydroxyalkylphenones such as 1-hydroxycyclohexylphenyl-ketone (commercially available as Omnirad 184 from IGM Resins B.V.); and 2-dimethylamino-2-(4-methylbenzyl)-1-(4-morpholin-4-ylphenyl)-butan-1-one (commercially available as Omnirad from IGM Resins B.V.) Examples include, but are not limited to, 379EG), 2-benzyl-2-(dimethylamino)-4'-morpholinobtyrophenone (commercially available as Omnirad 369 from IGM Resins B.V.).

[0091] Examples of acylphosphine oxide compounds include, but are not limited to, 2,4,6-trimethylbenzoyl-diphenylphosphine oxide (commercially available as Omnirad TPO H from IGM Resins B.V.) and bis(2,4,6-trimethylbenzoyl)-phenylphosphine oxide (commercially available as Omnirad 819 from IGM Resins B.V.).

[0092] Examples of oxime ester-based photoradical polymerization initiators include, but are not limited to, 1,2-octanedione, 1-[4-(phenylthio)-,2-(O-benzoyl oxime)] (trade name: Irgacure OXE-01, manufactured by BASF), ethanone, 1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazole-3-yl]-,1-(O-acetyloxime) (trade name: Irgacure OXE-02, manufactured by BASF), methanone, ethanone, 1-[9-ethyl-6-(1,3-dioxolane,4-(2-methoxyphenoxy)-9H-carbazole-3-yl]-,1-(O-acetyloxime) (trade name: ADEKA OPT-N-1919, manufactured by ADEKA).

[0093] Examples of compounds having a photosensitive site and a peroxide structure, or commercially available products thereof, include 3,3',4,4'-tetrakis(tert-butylperoxycarbonyl)benzophenone (BTTB), Perdual TA, and Perdual TX (all manufactured by NOF Corporation). In addition to the photoradical polymerization initiators mentioned above, other examples of photoradical polymerization initiators include 2-hydroxy-2-methyl-1-phenylpropan-1-one, diethoxyacetophenone, 1-(4-isopropylphenyl)-2-hydroxy-2-methylpropan-1-one, 1-(4-dodecylphenyl)-2-hydroxy-2-methylpropan-1-one, 4-(2-hydroxyethoxy)-phenyl(2-hydroxy-2-propyl)ketone, 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one, benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin n-butyl ether, benzoin phenyl ether, and benzyl dimethyl Examples of photoradical polymerization initiators include, but are not limited to, Luketal, benzophenone, benzoylbenzoic acid, methyl benzoylbenzoate, 4-phenylbenzophenone, hydroxybenzophenone, acrylic benzophenone, 4-benzoyl-4'-methyldiphenyl sulfide, 3,3'-dimethyl-4-methoxybenzophenone, thioxanthone, 2-chlorthioxanthone, 2-methylthioxanthone, 2,4-dimethylthioxanthone, isopropylthioxanthone, 2,4-dichlorothioxanthone, 2,4-diethylthioxanthone, 2,4-diisopropylthioxanthone, 2,4,6-trimethylbenzoyldiphenylphosphine oxide, methylphenylglyoxylate, benzyl, and camphorquinone. One of these photoradical polymerization initiators may be used, or two or more may be used in combination.

[0094] From the viewpoint of photoirradiation reactivity, the content of the photoradical polymerization initiator is preferably 0.1 to 10 parts by mass, and more preferably 0.2 to 8 parts by mass, per 100 parts by mass of the total (A) (meth)acrylate compound.

[0095] Photoacid generators absorb light and generate acid as an active species, which promotes the polymerization of cationic polymerizable compounds. Examples of photoacid generators include BF ４ － SbF ６ － AsF ６ － , B (C ６ F ５ ) ４ － Ga(C) ６ F ５ ) ４ － , C (CF ３ SO ２ ) ３ － [P(R １ ) ａ F ６－ａ ] － [C(R １ SO ２ ) ３ ] － , or [N(R １ SO ２ ) ２ ] － (In the formula, R １ Each of these is an alkyl group in which at least some of the hydrogen atoms are substituted with fluorine atoms, and a is an integer from 0 to 5. If a is an integer of 2 or more, there are multiple R groups. １ These may be the same or different from each other.) Various onium salts can be used, but are not limited to these, with the counter anion being a sulfonium cation, iodonium cation, ammonium cation, phosphonium cation, etc., and the cation moiety being sulfonium cation, iodonium cation, ammonium cation, etc.

[0096] Examples of iodonium cations include, but are not limited to, iodonium ions such as diphenyliodonium, di-p-tolyliodonium, bis(4-dodecylphenyl)iodonium, bis(4-methoxyphenyl)iodonium, (4-octyloxyphenyl)phenyliodonium, bis(4-decyloxy)phenyliodonium, 4-(2-hydroxytetradecyloxy)phenylphenyliodonium, 4-isopropylphenyl(p-tolyl)iodonium, and 4-isobutylphenyl(p-tolyl)iodonium.

[0097] Examples of sulfonium ions include triphenylsulfonium, tri-p-tolylsulfonium, tri-o-tolylsulfonium, tris(4-methoxyphenyl)sulfonium, 1-naphthyldiphenylsulfonium, 2-naphthyldiphenylsulfonium, tris(4-fluorophenyl)sulfonium, tri-1-naphthylsulfonium, tri-2-naphthylsulfonium, tris(4-hydroxyphenyl)sulfonium, 4-(phenylthio)phenyldiphenylsulfonium, 4-(p-tolylthio)phenyldi-p-tolylsulfonium, 4-(4-methoxyphenylthio)phenylbis(4-methoxyphenyl)sulfonium, and 4-(phenylthio)phenylbis(4-fluorophenyl (L) sulfonium, 4-(phenylthio)phenylbis(4-methoxyphenyl)sulfonium, 4-(phenylthio)phenyldi-p-tolylsulfonium, [4-(4-biphenylylthio)phenyl]-4-biphenylylphenylsulfonium, [4-(2-thioxanthonylthio)phenyl]diphenylsulfonium, bis[4-(diphenylsulfonio)phenyl]sulfide, bis[4-{bis[4-(2-hydroxyethoxy)phenyl]sulfonio}phenyl]sulfide, bis{4-[bis(4-fluorophenyl)sulfonio]phenyl}sulfide, bis{4-[bis(4-methylphenyl)sulfonio]phenyl}sulfide, bis{4-[bis(4-methoxyphenyl)sulfonio] Phenyl sulfide, bis(2-mercaptoethyl) sulfide, 4-(4-benzoyl-2-chlorophenylthio)phenylbis(4-fluorophenyl)sulfonium, 4-(4-benzoyl-2-chlorophenylthio)phenyldiphenylsulfonium, 4-(4-benzoylphenylthio)phenylbis(4-fluorophenyl)sulfonium, 4-(4-benzoylphenylthio)phenyldiphenylsulfonium, 7-isopropyl-9-oxo-10-thia-9,10-dihydroanthracene-2-yldi-p-tolylsulfonium, 7-isopropyl-9-oxo-10-thia-9,10-dihydroanthracene-2-yldiphenylsulfonium, 2-[(di-p-tolyl)sulfonio]thioxanthone, 2-[(diphenyl)sulfonio]thioxanthone, 4-(9-oxo-9H-thioxanthene-2-yl)thiophenyl-9-oxo-9H-thioxanthene-2-ylphenylsulfonium, 4-[4-(4-t-butylbenzoyl)phenylthio]phenyldi-p-tolylsulfonium, 4-[4-(4-t-butylbenzoyl)phenylthio]phenyldiphenyl Examples of triarylsulfonium include triarylsulfonium such as triarylsulfonium, 4-[4-(benzoylphenylthio)]phenyldi-p-tolylsulfonium, 4-[4-(benzoylphenylthio)]phenyldiphenylsulfonium, 5-(4-methoxyphenyl)thiaanthurenium, 5-phenylthiaanthurenium, 5-tolylsulfonium, 5-(4-ethoxyphenyl)thiaanthurenium, and 5-(2,4,6-trimethylphenyl)thiaanthurenium.

[0098] Examples of ammonium cations include pyrrolidinium such as N,N-dimethylpyrrolidinium, N-ethyl-N-methylpyrrolidinium, and N,N-diethylpyrrolidinium; imidazolinium such as N,N'-dimethylimidazolinium, N,N'-diethylimidazolinium, N-ethyl-N'-methylimidazolinium, 1,3,4-trimethylimidazolinium, and 1,2,3,4-tetramethylimidazolinium; tetrahydropyrimidinium such as N,N'-dimethyltetrahydropyrimidinium; and morpholinium such as N,N'-dimethylmorpholinium. Examples include, but are not limited to, piperidinium such as N,N'-diethylpiperidinium, pyridinium such as N-methylpyridinium, N-benzylpyridinium and N-phenacylpyridium, imidazolium such as N,N'-dimethylimidazolium, quinorium such as N-methylquinolium, N-benzylquinolium and N-phenacylquinolium, isoquinolium such as N-methylisoquinolium, thiazonium such as benzylbenzothiazonium and phenacylbenzothiazonium, and acridium such as benzylacridium and phenacylacridium.

[0099] Examples of phosphonium cations include tetraarylphosphoniums such as tetraphenylphosphonium, tetra-p-tolylphosphonium, tetrakis(2-methoxyphenyl)phosphonium, tetrakis(3-methoxyphenyl)phosphonium, and tetrakis(4-methoxyphenyl)phosphonium; triarylphosphoniums such as triphenylbenzylphosphonium, triphenylphenacylphosphonium, triphenylmethylphosphonium, and triphenylbutylphosphonium; and tetraalkylphosphoniums such as triethylbenzylphosphonium, tributylbenzylphosphonium, tetraethylphosphonium, tetrabutylphosphonium, tetrahexylphosphonium, triethylphenacylphosphonium, and tributylphenacylphosphonium.

[0100] Specific examples of iodonium salt-based photoacid generators include photoacid generators that are arsenate-type iodonium salts such as diphenyliodonium hexafluoroarsenate, di(4-chlorophenyl)iodonium hexafluoroarsenate, di(4-bromphenyl)iodonium hexafluoroarsenate, and phenyl(4-methoxyphenyl)iodonium hexafluoroarsenate; 4-methylphenyl-4-(1-methylethyl)phenyliodonium hexafluorophosphate, 4-methylphenyl-4-(1-methylethyl)phenyliodonium tri(pentafluoroethyl)trifluorophosphate (e.g., IK-1 manufactured by Sunapro Co., Ltd.), 4-methylphenyl-4-(2-methylpropyl)phenyliodonium hexafluorophosphate (e.g., IRGACURE® 250 manufactured by BASF), and bis(C) １０～１４Photoacid generators that are phosphate-based iodonium salts such as alkylphenyl)iodonium hexafluorophosphate (e.g., WPI-113 manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.); photoacid generators that are antimonate-based iodonium salts such as 4-methylphenyl-4-(1-methylethyl)phenyliodonium hexafluoroantimonate (e.g., WPI-116 manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.); iodonium salt-based photoacid generators such as IK-1FG (manufactured by Sunapro Co., Ltd.); 4-methylphenyl-4-(1-methylethyl)phenyliodonium tetrakis(pentafluorophenyl) borate, 4-isopropyl-4'-methyldiphenyliodonium tetrakis(pentafluorophenyl) borate (e.g., BLUESIL® PI manufactured by ELKEM SILICONES). Examples include photoacid generators such as borate-based iodonium salts (e.g., 2074), but are not limited to these.

[0101] Specific examples of sulfonium salt-based photoacid generators include, but are not limited to, borate-based sulfonium salt photoacid generators (e.g., products manufactured by Sunapro Co., Ltd.: CPI-110B, CPI-310B, CPI-410B, etc., and Omnirad 290 manufactured by IGM Resins B.V., etc.), phosphate-based sulfonium salt photoacid generators (products manufactured by Sunapro Co., Ltd.: CPI-210S, VC-1S, CPI-410S, etc.), and other sulfonium salt-based photoacid generators (products manufactured by Sunapro Co., Ltd.: CPI-310FG, VC-1FG, etc.).

[0102] Any one type of photoacid generator may be used, or two or more types may be used in combination. The content of the photoacid generator in the resin composition is preferably 0.5 to 15 parts by mass, more preferably 1 to 10 parts by mass, based on 100 parts by mass of the total amount of cationic polymerizable compounds.

[0103] Photobase generators absorb light and generate bases as active species, thereby promoting the polymerization of anionic polymerizable compounds. Examples of photobase generators include, but are not limited to, various compounds that generate bases such as amines, amidines, guanidines, phosphazenes, and carbenes.Specific examples of photobase generators include, for example, 2-benzyl-2-(dimethylamino)-1-[4-(morpholino)phenyl]-1-butanone, 2-(dimethylamino)-2-(4-methylbenzyl)-1-(4-morpholinophenyl)butan-1-one, 2-nitrobenzyl 4-hydroxypiperidine-1-carboxylate, 4,5-dimethoxy-2-nitrobenzyl 2,6-dimethylpiperidine-1-carboxylate, 1-(9,10-dioxo-9,10-dihydroanthracene-2-yl)ethylcyclohexylcarbamate, 1-(9,10-dioxo-9,10-dihydroanthracene-2-yl)ethyl 1H-imidazole-1-carboxylate, 3,4,6,7,8,9-hexahydro-2H-pyrimido[1,2-a]pyrimidine-1- Ium 2-(3-benzoylphenyl)propanoate, diaminomethaneiminium 2-(3-benzoylphenyl)propanoate, (Z)-N-(((bis(dimethylamino)methylene)amino)(isopropylamino)methylene)propane-2-aminium 2-(3-benzoylphenyl)propanoate, 1,2-dicyclohexyl-4,4,5,5-tetramethylbiguanidium n-butyltriphenylborate, (Z)-{[bis(dimethylamino)methylidene]amino}-N-cyclohexyl(cyclohexylamino)methaniminium tetrakis(3-fluorophenyl)borate, 1,2-diisopropyl-3-[bis(dimethylamino)methylene]guanidium 2-(3-benzoylphenyl)propionate, 9-antrylmethyl Examples include, but are not limited to, N,N-diethylcarbamate, (E)-1-piperidino-3-(2-hydroxyphenyl)-2-propen-1-one, 2-nitrophenylmethyl 4-methacryloyloxypiperidine-1-carboxylate, tetramethylguanidium tetrakis(3-fluorophenyl)borate, tetramethylguanidium tetrakis(4-fluorophenyl)borate, salts containing protonated DBU and tetrakis(3-fluorophenyl)borate anion, and salts containing benzylated DBU and tetrakis(3-fluorophenyl)borate anion. These may be used individually or in combination of two or more.

[0104] Any one type of photobase generator may be used, or two or more types may be used in combination. The content of the photobase generator in the resin composition is preferably 0.5 to 15 parts by mass, more preferably 1 to 10 parts by mass, per 100 parts by mass of the total anionic polymerizable compounds. Any one of a photoradical polymerization initiator, a photoacid generator, or a photobase generator may be used as the photopolymerization initiator, or these may be used in any combination.

[0105] <(F) Stabilizer> The resin composition of this embodiment may optionally contain (F) stabilizer (hereinafter also referred to as "component (F)"), to the extent that it does not impair the effects of the present invention. The stabilizer can improve the storage stability of the resin composition of this embodiment and extend its pot life. Various known stabilizers such as borate compounds (e.g., liquid borate ester compounds), titanate compounds, aluminate compounds (e.g., aluminum chelates), zirconate compounds, isocyanate compounds, and organic acids (e.g., barbituric acid, carboxylic acids, acid anhydrides, and mercapto organic acids) can be used as stabilizers, but at least one selected from the group consisting of liquid borate ester compounds, aluminum chelates, and organic acids is preferred due to its high effectiveness in improving storage stability.

[0106] Examples of liquid borate ester compounds include 2,2'-oxybis(5,5'-dimethyl-1,3,2-oxaborinane), trimethyl borate, triethyl borate, tri-n-propyl borate, triisopropyl borate (TIPB), tri-n-butyl borate, tripentyl borate, triallyl borate, trihexyl borate, tricyclohexyl borate, trioctyl borate, trinonyl borate, tridecyl borate, and tridodecyl borate. Examples of suitable borates include, but are not limited to, borate, trihexadecylborate, trioctadecylborate, tris(2-ethylhexyloxy)borane, bis(1,4,7,10-tetraoxaundecyl)(1,4,7,10,13-pentaoxatetradecyl)(1,4,7-trioxaundecyl)borane, trybenzylborate, triphenylborate, tri-o-tolylborate, tri-m-tolylborate, triethanolamineborate, etc. Liquid borate ester compounds are preferred because they are liquid at room temperature (25°C), thus keeping the viscosity of the formulation low. As an aluminum chelate, for example, aluminum chelate A (manufactured by Kawaken Fine Chemicals Co., Ltd.) can be used. As an organic acid, for example, barbituric acid can be used. Any one stabilizer may be used, or two or more may be used in combination.

[0107] When a stabilizer is added, the amount added is preferably 0.01 to 10% by mass, more preferably 0.05 to 8% by mass, and even more preferably 0.1 to 6% by mass, relative to the total mass of the resin composition.

[0108] (G) Other optional components The resin composition of this embodiment may, if desired, contain other optional components, such as those described below, as necessary, as long as they do not impair the spirit of this embodiment.

[0109] The resin composition of this embodiment may, if desired, contain a filler, to the extent that it does not impair the effects of this embodiment. By including a filler, the fluidity, injectability, coatability, adhesion, etc., of the resin composition can be improved. Fillers are broadly classified into inorganic fillers and organic fillers.

[0110] Inorganic fillers consist of granular bodies formed from inorganic materials and are not particularly limited as long as they have the effect of lowering the coefficient of thermal expansion when added. Examples of inorganic materials that can be used include, but are not limited to, silica, talc, alumina, aluminum nitride, calcium carbonate, aluminum silicate, magnesium silicate, magnesium carbonate, barium sulfate, barium carbonate, lime sulfate, aluminum hydroxide, calcium silicate, potassium titanate, titanium oxide, zinc oxide, silicon carbide, silicon nitride, and boron nitride. One or more inorganic fillers may be used, or two or more may be used in combination. As an inorganic filler, silica filler is preferred because it allows for a high filling amount. Amorphous silica is preferred. The surface of the inorganic filler may be surface-treated with a coupling agent such as a silane coupling agent.

[0111] Examples of organic fillers include, but are not limited to, polytetrafluoroethylene (PTFE) fillers, silicone fillers, acrylic fillers, fillers with a urethane skeleton, fillers with a butadiene skeleton, and styrene fillers. Organic fillers may also be surface-treated.

[0112] The shape of the filler is not particularly limited and may be spherical, flake-shaped, needle-shaped, irregular, or any other shape.

[0113] The average particle size of the filler is preferably 6.0 μm or less, more preferably 5.0 μm or less, and even more preferably 4.0 μm or less. In this specification, unless otherwise specified, the average particle size refers to the volume-based median diameter (d50) measured by laser diffraction in accordance with ISO-13320 (2009). By keeping the average particle size of the filler below the upper limit, the settling of the filler can be suppressed, as can the formation of coarse particles, thereby suppressing wear of the jet dispenser nozzle and the scattering of the resin composition discharged from the jet dispenser nozzle outside the desired area. The lower limit of the average particle size of the filler is not particularly limited, but from the viewpoint of the viscosity of the resin composition, it is preferably 0.005 μm or more, and more preferably 0.01 μm or more. In one embodiment of this specification, the average particle size of the filler is preferably 0.01 μm to 5.0 μm, and more preferably 0.1 μm to 3.0 μm. Fillers with different average particle sizes may be used in combination. For example, a combination of fillers with an average particle size of 0.005 μm or more and less than 0.1 μm may be used, along with fillers with an average particle size of 0.1 μm to 6.0 μm.

[0114] Any one type of filler may be used, or two or more types may be used in combination. When the resin composition of this embodiment contains a filler, the filler content in the resin composition is preferably 5 to 60 parts by weight, and more preferably 10 to 50 parts by weight, per 100 parts by weight of the total amount of the resin composition.

[0115] The resin composition of this embodiment may optionally contain a coupling agent, provided that it does not impair the effects of this embodiment. The coupling agent has two or more different functional groups in its molecule, one of which is a functional group that chemically bonds with an inorganic material, and the other is a functional group that chemically bonds with an organic material. The inclusion of a coupling agent in the resin composition improves the adhesive strength of the resin composition to an adherend such as a substrate.

[0116] Examples of coupling agents include, but are not limited to, silane coupling agents, aluminum coupling agents, and titanium coupling agents, depending on the type of functional group that chemically bonds with the inorganic material.

[0117] Examples of coupling agents include, but are not limited to, various types such as epoxy, amino, vinyl, methacrylic, acrylic, and mercapto coupling agents, depending on the type of functional group that chemically bonds with the organic material. Among these, epoxy coupling agents containing epoxy groups are preferred from the viewpoint of moisture resistance reliability.

[0118] Any one type of coupling agent may be used, or two or more types may be used in combination. When a coupling agent is added, the amount of coupling agent added is preferably 0.01 to 10 parts by weight, and more preferably 0.1 to 5 parts by weight, per 100 parts by weight of the total amount of the resin composition, from the viewpoint of improving adhesive strength.

[0119] The resin composition of this embodiment may contain a thixotrope, to the extent that it does not impair the effects of this embodiment. Examples of thixotropes include silica such as colloidal silica, hydrophobic silica, fine silica, and nanosilica, as well as bentonite, acetylene black, and Ketjenblack. Nanosilica is preferred from the viewpoint of shape retention after coating. Furthermore, from the viewpoint of preventing the resin composition from getting stuck during bonding and improving moisture resistance and adhesion, nanosilica with an average particle size of 5 to 750 nm is more preferred, and nanosilica with an average particle size of 10 to 600 nm is even more preferred. Examples of commercially available products include, but are not limited to, hydrophobic fumed silica manufactured by CABOT (product name: CAB-O-SIL® TS720, average particle size: 12 nm), hydrophobic fumed silica manufactured by Nippon Aerosil (product name: R805, average particle size: 12 nm), and amorphous silica manufactured by Nippon Shokubai (product name: Seahostar KE-P10, average particle size: 100 nm). Here, the average particle size of the nanosilica particles is measured using a dynamic light scattering nanotrac particle size analyzer. The thixotrope may be used alone or in combination of two or more types.

[0120] If a quivistatement is included, the quivistatement content is preferably 0.01 to 30% by mass, more preferably 0.05 to 25% by mass, and even more preferably 0.1 to 20% by mass, based on the total mass of the resin composition.

[0121] The resin composition of this embodiment may contain a light-shielding agent, to the extent that it does not impair the effects of this embodiment. Depending on the application of the cured product of the resin composition, light-shielding properties may be required. In such cases, the photocurable resin composition of this embodiment may contain a light-shielding agent. Examples of light-shielding agents include, but are not limited to, carbon black and titanium black. Furthermore, these light-shielding agents can also be used as photothermal conversion materials that convert long-wavelength light into heat.

[0122] The resin composition of this embodiment may contain a radical polymerization inhibitor, to the extent that it does not impair the effects of this embodiment. Known radical polymerization inhibitors can be used, including, but are not limited to, N-nitroso-N-phenylhydroxylamine aluminum, triphenylphosphine, p-methoxyphenol, hydroquinone, p-benzoquinone, and 2,6-di-tert-butyl-p-cresol. Known polymerization inhibitors disclosed in Japanese Patent Publication No. 2010-117545 and Japanese Patent Publication No. 2008-184514, etc., can also be used. One radical polymerization inhibitor may be used, or two or more may be used in combination.

[0123] The resin composition of this embodiment may, if desired, further contain additives other than the above-mentioned optional components, such as photosensitizers, conductive fillers, anionic polymerization inhibitors, ion trapping agents, leveling agents, antioxidants, defoaming agents, viscosity modifiers, flame retardants, plasticizers, solvents, and dispersants, to the extent that the spirit of this embodiment is not impaired. The type and amount of each additive are as per conventional methods.

[0124] The resin composition of this embodiment is preferably substantially free of liquid components such as water, solvents, and ionic liquids (excluding liquid components (A) to (G)) from the viewpoint of preventing reduced curing strength and adhesion due to curing, and preventing outgassing and bleeding. For example, the content of liquid components is preferably 3% by mass or less, and more preferably 1% by mass or less, relative to the total mass of the resin composition. Examples of solvents include common organic solvents in the field of curable compositions, such as hydrocarbons (benzene, toluene, xylene, cyclohexane, etc.), aprotic polar solvents (N,N-dimethylformamide, dimethyl sulfoxide, N-methyl-2-pyrrolidone, etc.), nitriles (acetonitrile, etc.), ketones (acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, etc.), esters (ethyl acetate, butyl acetate, etc.), ethers (cyclopentyl methyl ether, diethyl ether, tetrahydrofuran, dimethoxyethane, etc.), alcohols (methanol, ethanol, propanol, butanol, etc.), terpenes (turpentine oil, terpineol, isobornyl acetate, etc.), and halogenated solvents (dichloromethane, chloroform, etc.).

[0125] The method for producing the resin composition of this embodiment is not particularly limited. For example, components (A) to (C), and optionally components (D), (E), (F), (G), and other optional components, can be introduced simultaneously or separately into a suitable mixer, and mixed by stirring while melting by heating if necessary, to obtain a homogeneous composition. The mixer is not particularly limited, but a Leikai mixer, Henschel mixer, three-roll mill, ball mill, planetary mixer, and bead mill, etc., equipped with a stirring device and a heating device, can be used. These devices may also be used in appropriate combinations.

[0126] The resin composition of this embodiment can be a one-component resin composition contained in a single container, or a two-component (or multi-component) resin composition contained in two or more containers, depending on its intended use. In the case of a two-component (or multi-component) resin composition, components (A) to (C) and other optional components as needed can be selected in the same way as for a one-component composition. Also, in the case of a two-component (or multi-component) resin composition, components (A) to (C) and other optional components as needed can be divided into two or multiple liquids in any way without particular restriction. When divided into two or multiple liquids in any way, one or more components selected from components (A) to (C) and other optional components as needed may be contained in each liquid, components (A) to (C) may be contained in one liquid, or there may be a liquid consisting only of components (A) to (C) and / or other optional components as needed.

[0127] [Physical Properties of the Resin Composition] The resin composition of this embodiment can be suitably cured under the conditions of 80°C for 10 minutes. Furthermore, the viscosity increase ratio of the resin composition of this embodiment 24 hours after preparation relative to the viscosity immediately after preparation is preferably 0.5 to 10 times, more preferably 0.8 to 9 times, and even more preferably 0.9 to 8 times. When the viscosity increase ratio is within this numerical range, it is possible to provide an adhesive with excellent storage stability.

[0128] In the DSC chart obtained by differential scanning calorimetry of the resin composition of this embodiment, the temperature of the exothermic peak top is preferably 60 to 125°C, more preferably 65 to 120°C, and even more preferably 67 to 115°C. This numerical range facilitates the low-temperature, rapid curing of the resin composition.

[0129] [Applications] The resin composition of this embodiment can be used, for example, as an adhesive, sealant, or coating agent, or as a raw material thereof, for fixing, joining, or protecting components that constitute a semiconductor device or electronic component.

[0130] [Adhesives, sealants, or coatings] The adhesives, sealants, or coatings of this embodiment enable good fixing, bonding, or protection of general-purpose plastics (e.g., PE, PS, PP, etc.), engineering plastics (e.g., LCP (liquid crystal polymer), polyamide, polycarbonate, polyphthalamide, polybutylene terephthalate, polyimide, etc.), glass, ceramics, metals (e.g., copper, nickel, SUS, etc.), organic substrates (e.g., FR4, etc.), and flexible printed circuit boards (FPCs), etc., and can be used to fix, bond, or protect components constituting semiconductor devices or electronic components. Examples of semiconductor devices or electronic components include, but are not limited to, HDDs, semiconductor elements, sensor modules such as image sensor modules, camera modules, semiconductor modules, and integrated circuits.

[0131] The adhesive, sealant, or coating agent of this embodiment can cure at low temperatures and in a short time, and provide a cured product with excellent adhesive properties, resulting in high productivity. For example, it is suitable for use in the manufacturing of semiconductor devices and electronic components where multiple parts made of different materials are joined and assembled. Furthermore, because the self-heating temperature during the curing reaction of the adhesive, sealant, or coating agent of this embodiment is low, it is suitable for use in the manufacturing of semiconductor modules equipped with miniaturized electronic components, for example.

[0132] [Cured product of resin composition, adhesive, sealant, or coating agent] The cured product of this embodiment is a cured product obtained by curing the above-mentioned resin composition, adhesive, sealant, or coating agent. This cured product has excellent adhesive properties.

[0133] [Semiconductor Devices, Electronic Components] The semiconductor devices or electronic components of this embodiment include the cured product of this embodiment described above, and therefore have high reliability, especially in semiconductor devices or electronic components assembled by joining multiple components made of different materials. Here, "semiconductor device" refers to all devices that can function by utilizing semiconductor properties, and includes electronic components, semiconductor circuits, modules incorporating these, electronic equipment, etc. Examples of semiconductor devices or electronic components include, but are not limited to, HDDs, semiconductor elements, sensor modules such as image sensor modules, camera modules, semiconductor modules, integrated circuits, etc.

[0134] [Method for Manufacturing Semiconductor Devices or Electronic Components] The resin composition of this embodiment is preferably used in the manufacture of semiconductor devices and / or electronic components. That is, the method for manufacturing a semiconductor device of this embodiment is a method for manufacturing a semiconductor device having electronic components and a circuit board, comprising the steps of preparing the electronic components and the circuit board, applying the resin composition onto the surface of the electronic components or the circuit board, and bringing the electronic components and the circuit board into contact, wherein the resin composition comprises (A) a (meth)acrylate compound, (B) a polyfunctional thiol compound, and (C) a curing catalyst system including at least one type of latent curing catalyst, and the (C) component has the following characteristic (1), the method for manufacturing a semiconductor device. Feature (1): In a DSC chart obtained by differential scanning calorimetry of a mixed solution of 1.0 g of component (C) and 9.0 g of 1,3,4,6-tetrakis(3-mercaptopropyl) glycoluryl, the temperature of the endothermic peak top is 50 to 70°C, and the slope of the line segment connecting the onset of the endothermic peak and the peak top is -0.0007 mW / mg·°C or less.

[0135] Furthermore, the method for manufacturing electronic components of this embodiment is a method for manufacturing sealed electronic components, comprising the steps of preparing electronic components and a circuit board, and sealing the electronic components on the circuit board using a resin composition, wherein the resin composition comprises (A) a (meth)acrylate compound, (B) a polyfunctional thiol compound, and (C) a curing catalyst system including at least one type of latent curing catalyst, and the component (C) has the above-described characteristic (1), thus providing a method for manufacturing electronic components.

[0136] Furthermore, the method for manufacturing an electronic component of this embodiment is a method for manufacturing an electronic component, comprising the steps of preparing an electronic component and a circuit board, applying a resin composition onto the surface of the electronic component and / or the circuit board, and bringing the electronic component and the circuit board into contact, wherein the resin composition comprises (A) a (meth)acrylate compound, (B) a polyfunctional thiol compound, and (C) a curing catalyst system including at least one latent curing catalyst, and the (C) component has the above-described characteristic (1).

[0137] The present invention will be described in more detail below with reference to examples and comparative examples, but the present invention is not limited to these examples. In the following examples, parts and % refer to parts by mass and mass%, respectively, unless otherwise specified.

[0138] <Experiment 1: Measurement of Feature (1)> [Preparation of Differential Scanning Calorimetry (DSC) Sample for Feature (1)] 1.0 g of latent curing catalyst system (component (C)) and 9.0 g of 1,3,4,6-tetrakis(3-mercaptopropyl) glycoluryl were weighed. After weighing, the mixed solution was mixed and subjected to differential scanning calorimetry (DSC 204 F1 Phoenix®) (manufactured by NETZSCH) within 2 hours of mixing, and the features were determined according to the following procedure.

[0139] First, 5.0 mg of the mixed solution was weighed into an aluminum pan, sealed with an aluminum lid, and then a hole was made in the center of the lid with a needle to prepare the measurement sample. Next, the heat flow (mW / mg) of this measurement sample was measured while it was heated under nitrogen atmosphere (100 mL / min), in a temperature range of -25°C to 150°C, and at a heating rate of 10°C / min. The temperature at which the peak top was obtained on the graph was calculated using analysis software (NETZSCH Proteus-Thermal Analysis version 6.1.0B), and the maximum value was defined as the onset temperature of the endothermic peak, and the minimum value was defined as the endothermic peak temperature. The slope was calculated from the X and Y coordinates of the endothermic peak and the X and Y coordinates of the onset.

[0140] The component (C) used in Experiment 1 is as follows: (C1) Modified aliphatic polyamine latent curing catalyst (product name: Fujicure-2015, manufactured by T&K TOKA Corporation) (C2) Mixture of modified aliphatic polyamine latent curing catalyst (product name: Fujicure-2015, manufactured by T&K TOKA Corporation) and urea-type adduct latent curing catalyst (product name: Fujicure-FXR1020, manufactured by T&K TOKA Corporation) (mass ratio 7:3) (C3) Mixture of modified aliphatic polyamine latent curing catalyst (product name: Fujicure-2015, manufactured by T&K TOKA Corporation) and urea-type adduct latent curing catalyst (product name: Fujicure-FXR1020, manufactured by T&K TOKA Corporation) (mass ratio 4:6) (C4) Modified aliphatic polyamine latent curing catalyst (product name: Fujicure-2015, manufactured by T&K A mixture (mass ratio 3:7) of (C5) an amine-based powder-type latent curing agent (product name: Fujicure-FXR1020, manufactured by T&K TOKA Corporation) and a urea-type adduct-type latent curing catalyst (product name: Fujicure-2021, manufactured by T&K TOKA Corporation) (C'1) a urea-type adduct-type latent curing catalyst (product name: Fujicure-FXR1020, manufactured by T&K TOKA Corporation) (C'2) an epoxy resin amine adduct-type latent curing agent (product name: Amicure PN-23J, manufactured by Ajinomoto Co., Inc.) (C'3) 1-cyanoethyl-2-undecylimidazole (product name: Curesol C11Z-CN, manufactured by Shikoku Chemicals Co., Ltd.)

[0141] [Results of Experiment 1] The results are shown in Table 1. As shown in Table 1, the curing catalyst systems (C1), (C2), (C3), (C4), and (C5) all met characteristic (1) in the DSC chart obtained by differential scanning calorimetry, with the endothermic peak top temperature being between 50 and 70°C and the slope of the line segment connecting the onset of the endothermic peak and the peak top being -0.0007 mW / mg·°C or less.

[0142]

[0143] <Experiment 2: Characterization> [Preparation of Resin Composition] Each component in Tables 2 to 4 was weighed and mixed using a hybrid mixer to prepare the resin compositions for the examples and comparative examples. In Tables 2 to 4, the amount of each component is expressed in parts by mass (unit: g). The components used in the examples and comparative examples are as follows.

[0144] • (A) Components: (meth)acrylate compounds and (A1-1) Tricyclodecanedimethanol diacrylate (product name: A-DCP-3K, manufactured by Shin Nakamura Kogyo Co., Ltd., (meth)acryloyl equivalent: 182 g / eq) (A1-2) Neopentyl glycol diacrylate (product name: Light Acrylate NP-A, manufactured by Kyoeisha Chemical Co., Ltd., (meth)acryloyl equivalent: 106 g / eq) (A1-3) Ethoxylated bisphenol A diacrylate (product name: ABE-300, manufactured by Shin Nakamura Chemical Industry Co., Ltd., (meth)acryloyl equivalent: 236 g / eq) (A2-1) Non-yellowing polyether skeleton urethane acrylate (product name: Art Resin UN-6200, manufactured by Negami Kogyo Co., Ltd., (meth)acryloyl equivalent: 3000 g / eq)

[0145] • (B) Components: Polyfunctional thiol compounds and (B1) 1,3,4,6-tetrakis(3-mercaptopropyl) glycoluryl (product name: C3 TS-G, manufactured by Shikoku Chemicals, thiol equivalent: 110 g / eq) (B2) bis(2-mercaptoethyl) sulfide (manufactured by Tokyo Chemical Industries, Ltd., thiol equivalent: 75 g / eq) (B3) pentaerythritol tetrakis(3-mercaptopropionate) (product name: PEMP, manufactured by SC Organic Chemicals Co., Ltd., thiol equivalent: 122.2 g / eq) (B4) 1,3,5-tris(3-mercaptobutyryloxyethyl)-1,3,5-triazine-2,4,6(1H,3H,5H)-trione (product name: Karenz MT® NR1, manufactured by Showa Denko K.K., thiol equivalent: 189 g / eq)

[0146] • (C) Component: Latent curing catalyst (C1) Modified aliphatic polyamine latent curing catalyst (product name: Fujicure-2015, manufactured by T&K TOKA Corporation) (C2) Mixture of modified aliphatic polyamine latent curing catalyst (product name: Fujicure-2015, manufactured by T&K TOKA Corporation) and urea-type adduct latent curing catalyst (product name: Fujicure-FXR1020, manufactured by T&K TOKA Corporation) (mass ratio 7:3) (C3) Mixture of modified aliphatic polyamine latent curing catalyst (product name: Fujicure-2015, manufactured by T&K TOKA Corporation) and urea-type adduct latent curing catalyst (product name: Fujicure-FXR1020, manufactured by T&K TOKA Corporation) (mass ratio 4:6) (C4) A mixture of a modified aliphatic polyamine-based latent curing catalyst (product name: Fujicure-2015, manufactured by T&K Toka Corporation) and a urea-type adduct-based latent curing catalyst (product name: Fujicure-FXR1020, manufactured by T&K Toka Corporation) (mass ratio 3:7) (C'1) Urea-type adduct-based latent curing catalyst (product name: Fujicure-FXR1020, manufactured by T&K Toka Corporation) (C'2) Epoxy resin amine adduct-type latent curing agent (product name: Amicure PN-23J, manufactured by Ajinomoto Co., Inc.) (C'3) 1-cyanoethyl-2-undecylimidazole (product name: CureZol C11Z-CN, manufactured by Shikoku Chemicals Co., Ltd.)

[0147] • Component (D): Polymerizable compounds other than component (A) (D1) Bisphenol F type epoxy resin / Bisphenol A type epoxy resin mixture (product name: Epiclon EXA835LV, manufactured by DIC Corporation)

[0148] • (E) Component: Photoradical initiator (E1): α-aminoalkylphenone; 1-hydroxycyclohexylphenyl ketone (trade name: Omnirad 184, manufactured by IGM Resins B.V.)

[0149] • (F) Ingredient: Stabilizer (F1) TIPB: Triisopropyl borate, manufactured by Tokyo Chemical Industry Co., Ltd.

[0150] [Method for Measuring Thickness Increase] The viscosity of the resin composition at room temperature (25°C) immediately after preparation and after 24 hours was measured at 10 rpm using an EHD viscometer (manufactured by Toki Sangyo Co., Ltd., 3° ​​cone / R9.7). The viscosity increase ratio was calculated by taking the initial viscosity immediately after preparation of the resin composition as 1.0 and dividing it by the viscosity of the sample after 24 hours (Pa·s) / initial viscosity (Pa·s).

[0151] [Gel Time] The gel time of the resin composition was obtained by supplying 5 ± 1 mg of the resin composition onto a hot plate heated to 80°C, stirring it in a circular motion with a stirring rod, and then lifting and separating the stirring rod, and measuring the time until the stringiness became 5 mm or less.

[0152] [Adhesive Strength] The adhesive strength was evaluated using the following procedure. A resin composition was applied to a nickel-plated substrate by stencil printing to a diameter of φ2 mm and a thickness of 125 μm. Alumina chips measuring 3.2 mm × 1.6 mm × 0.45 mm thick were then laminated onto the applied resin composition, and the resin composition was cured under light load to prepare test specimens. The curing conditions at this time were 80°C for 10 minutes in a forced-air dryer. The alumina chips on the nickel-plated substrate were punctured from the side with a bond tester (Dage series 4000) at 23°C, and the stress (N) at which the alumina chips peeled off was measured. This measurement was performed on 10 test specimens, and the average value of the obtained stresses was calculated. This average value was defined as the shear strength of the cured material (unit: N / Chip).

[0153]

[0154]

[0155]

[0156] [Results of Experiment 2] As shown in Table 2, Examples 1 to 3, which included the curing catalyst system (C) satisfying characteristic (1), had a viscosity increase ratio of 10 or less and exhibited excellent pot life. Furthermore, in Examples 1 to 4, the gel time at 80°C was less than 400 seconds, demonstrating that curing was possible at low temperatures and in a short time. In addition, Examples 1 to 4 had an adhesive strength of 60 N or more, indicating excellent adhesive strength. Moreover, in Examples 1 to 4, the temperature of the exothermic peak top in the DSC chart was between 67 and 116°C, demonstrating that low-temperature rapid curing was achieved.

[0157] As shown in Table 2, Example 5, which does not contain component (A2), and Example 6, which does not contain components (D) and (E), also exhibited excellent pot life, could be cured at low temperatures and in a short time, and had excellent adhesive strength.

[0158] As shown in Table 3, in Examples 7 and 8, where component (A) was changed, in Example 9, which did not contain component (F), and in Examples 10 and 11, where a different component (B) was used, excellent pot life was observed, curing was possible at low temperatures and in a short time, and adhesive strength was also excellent.

[0159] Furthermore, as shown in Table 4, Examples 12 to 14, which included the curing catalyst system (C) satisfying characteristic (1), also exhibited excellent pot life, enabling curing at low temperatures and in a short time, and demonstrating excellent adhesive strength.

[0160] As shown in Table 4, in Comparative Examples 1 to 4, which included the curing catalyst system (C) that did not satisfy characteristic (1), the pot life was poor, curing could not be achieved in a short time at low temperatures, and the adhesive strength was also inferior.

[0161] Although not shown in the table, a resin composition with the same composition as Examples 1-4, except for containing curing catalyst system (C5) instead of curing catalyst system (C1), can also be cured at low temperature and in a short time, and exhibits excellent adhesive strength, similar to Examples 1-4.

[0162] Conventional low-temperature curing catalysts result in poor pot life. To prevent poor pot life of the resin composition, it was necessary to incorporate stabilizers, but the inclusion of stabilizers can cause bleeding. The curing catalyst system (C) that satisfies characteristic (1) shown in the examples can be cured at low temperatures and in a short time, and has excellent pot life, so the amount of stabilizer to be incorporated can be reduced, and as a result, bleeding can be suppressed.

[0163] Although the present invention has been described above with reference to embodiments and examples, the present invention is not limited to the above embodiments and examples. Various modifications to the configuration and details of the present invention can be understood by those skilled in the art within the scope of the present invention.

[0164] The patents, patent applications, and documents cited herein are incorporated herein by reference in the same manner as their contents are specifically described herein.

[0165] <Note> Some or all of the above embodiments and examples may be described as follows, but are not limited to the following. <Resin composition> (Note 1) A resin composition comprising: (A) a (meth)acrylate compound; (B) a polyfunctional thiol compound; and (C) a curing catalyst system comprising at least one latent curing catalyst, wherein component (C) has the following characteristic (1). Feature (1): When a mixed solution of 1.0 g of component (C) and 9.0 g of 1,3,4,6-tetrakis(3-mercaptopropyl) glycoluryl is measured by differential scanning calorimetry, the temperature of the endothermic peak top in the DSC chart is 50 to 70°C, and the slope of the line segment connecting the onset of the endothermic peak and the peak top is -0.0007 mW / mg·°C or less. (Note 2) The resin composition according to Note 1, wherein component (A) contains a compound having an (A1) (meth)acryloyl equivalent of 300 g / eq or less. (Note 3) The resin composition according to Note 1 or 2, wherein component (A) contains a compound having an (A2) (meth)acryloyl equivalent of 1000 g / eq or more. (Note 4) The resin composition according to any one of Notes 1 to 3, wherein the total thiol equivalent of component (B) is 80 to 200 g / eq. (Note 5) The resin composition according to any one of Notes 1 to 4, wherein the ratio of the number of (meth)acryloyl group equivalents of component (A) to the number of thiol group equivalents of component (B) ([number of (meth)acryloyl group equivalents of component (A)] / [number of thiol group equivalents of component (B)]) is 0.1 to 10. (Note 6) The resin composition according to any one of Notes 1 to 5, wherein the viscosity increase ratio of the resin composition 24 hours after preparation to the viscosity immediately after preparation is 0.5 to 10 times. (Note 7) The resin composition according to any one of Notes 1 to 6, wherein the temperature of the exothermic peak top in the DSC chart when the resin composition is subjected to differential scanning calorimetry is 70 to 120°C. (Note 8) An adhesive containing the resin composition according to any one of Notes 1 to 7. (Note 9) A cured product of the resin composition according to any one of Notes 1 to 7, or the adhesive according to Note 8. (Note 10) A semiconductor device or electronic component containing the cured product described in Note 9.

[0166] The resin composition of the present invention can be cured at low temperatures and in a short time, and exhibits excellent adhesive strength, making it useful as an adhesive.

Claims

1. A resin composition comprising (A) a (meth)acrylate compound, (B) a polyfunctional thiol compound, and (C) a curing catalyst system comprising at least one latent curing catalyst, wherein component (C) has the following characteristic (1). Feature (1): In a DSC chart obtained by differential scanning calorimetry of a mixed solution of 1.0 g of component (C) and 9.0 g of 1,3,4,6-tetrakis(3-mercaptopropyl) glycoluryl, the temperature of the endothermic peak top is 50 to 70°C, and the slope of the line segment connecting the onset of the endothermic peak and the peak top is -0.0007 mW / mg·°C or less.

2. The resin composition according to claim 1, wherein the component (A) comprises a compound having an (A1) (meth)acryloyl equivalent of 300 g / eq or less.

3. The resin composition according to claim 1 or 2, wherein the component (A) comprises a compound having an (A2) (meth)acryloyl equivalent of 1000 g / eq or more.

4. The resin composition according to any one of claims 1 to 3, wherein the total thiol equivalent of component (B) is 80 to 200 g / eq.

5. The resin composition according to any one of claims 1 to 4, wherein the ratio of the number of (meth)acryloyl group equivalents of component (A) to the number of thiol group equivalents of component (B) ([number of (meth)acryloyl group equivalents of component (A)] / [number of thiol group equivalents of component (B)]) is 0.1 to 10.

6. The resin composition according to any one of claims 1 to 5, wherein the viscosity increase ratio of the resin composition 24 hours after preparation is 0.5 to 10 times the viscosity of the resin composition immediately after preparation.

7. The resin composition according to any one of claims 1 to 6, wherein the temperature of the exothermic peak top in the DSC chart obtained by differential scanning calorimetry of the resin composition is 70 to 120°C.

8. An adhesive comprising the resin composition according to any one of claims 1 to 7.

9. A resin composition according to any one of claims 1 to 7, or a cured product of the adhesive according to claim 8.

10. A semiconductor device or electronic component comprising the cured product described in claim 9.

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