Curable resin composition, adhesive, sealing material, cured product, semiconductor device and electronic component

Abstract

The present invention addresses the problem of providing: a curable resin composition capable of providing a cured product which exhibits excellent adhesive strength to an engineering plastic during thermal curing; an adhesive or a sealing material containing the same; a cured product thereof; and a semiconductor device and an electronic component containing the cured product.　The present invention provides: a curable resin composition which contains (A) a (meth)acrylate compound, (B) a polythiol compound, (C) an allyl compound and (D) a polymerization initiator, wherein the proportion which a compound having a heterocyclic ring and / or an aromatic ring constitutes in the polythiol compound (B) and the allyl compound (C) is 5% by mass or more; an adhesive or a sealing material which contains said curable resin composition; a cured product thereof; and a semiconductor device and an electronic component which contain said cured product.

Description

Curable resin composition, adhesive, sealing material, cured product, semiconductor device and electronic component

[0001] The present invention relates to a curable resin composition, an adhesive or a sealing material comprising the same, a cured product thereof, and a semiconductor device and an electronic component comprising the cured product.

[0002] Photo- and / or thermosetting adhesives are used in many fields (for example, Patent Documents 1 and 2), and are also used, for example, in the manufacture of optical sensor modules. Optical sensor modules are used as camera modules for mobile phones and smartphones. Adhesives used in the manufacture of optical sensor modules are used, for example, in the step of aligning optical axes such as adhesion between the sensor part and the lens part of an optical sensor module, and high curability is required.

[0003] As an adhesive that achieves high curability, curable resin compositions containing an acrylic resin and a thiol compound are known. For example, Patent Document 3 discloses a photo- and heat-curable resin composition having a sufficiently long pot life, which is characterized by containing (A) an acrylic resin, (B) a thiol compound, (C) a latent curing agent, (D) a radical polymerization inhibitor, and (E) an anionic polymerization inhibitor.

[0004] Japanese Unexamined Patent Application Publication No. 2009-51954, International Publication No. WO 2005 / 052021, Japanese Unexamined Patent Application Publication No. 2014-077024

[0005] From the viewpoint of the reliability of semiconductor devices and electronic components, the cured product of the curable resin composition used in assembly and mounting is required to have high adhesive strength to an adherend.

[0006] Engineering plastics have superior strength and heat resistance compared to general-purpose plastics, are lighter than metals, and are materials that facilitate mass production of the same shape by injection molding or the like, so they are widely used as components for semiconductor devices and electronic components. On the other hand, due to the high crystallinity of engineering plastics and their lower surface energy than metals, resulting in poor wettability with resin compositions, they are classified as difficult-to-adhere materials. There is a need for an adhesive or a sealing material that exhibits excellent adhesive strength to such difficult-to-adhere engineering plastics.

[0007] It has been found that while curable resin compositions containing acrylic resin and thiol compounds exhibit excellent low-temperature curing properties, the adhesive strength of the cured product to engineering plastics as the adherend may be insufficient after thermal curing.

[0008] The object of this invention is to provide a resin composition that can provide a cured product with excellent adhesive strength to engineering plastics in thermosetting, an adhesive or sealant containing the same, a cured product thereof, and a semiconductor device and electronic component containing the cured product thereof.

[0009] The specific means for solving the above problems are as follows. The embodiments of the present invention include the following curable resin compositions, adhesives or encapsulants, cured products, semiconductor devices or electronic components. [1] A curable resin composition comprising (A) a (meth)acrylate compound, (B) a polythiol compound, (C) an allyl compound, and (D) a polymerization initiator, wherein the proportion of compounds having heterocyclic and / or aromatic rings among the (B) polythiol compound and the (C) allyl compound is 5% by mass or more. [2] The curable resin composition according to [1], wherein the thiol equivalent of the (B) polythiol compound is 50 to 1000 g / eq. [3] The curable resin composition according to [1] or [2], wherein the allyl equivalent of the (C) allyl compound is 50 to 1000 g / eq. [4] The curable resin composition according to any one of [1] to [3], wherein the (C) allyl compound includes an allyl compound having a hydroxyl group. [5] The curable resin composition according to [4], wherein the hydroxyl group is a phenolic hydroxyl group. [6] The curable resin composition according to any one of [1] to [5], wherein the compound having a heterocyclic and / or aromatic ring in (B) a polythiol compound and / or (C) an allyl compound is a compound having a bisphenol skeleton, a glycoluryl skeleton, or an isocyanuric acid skeleton. [7] An adhesive or sealant comprising the curable resin composition according to any one of [1] to [6]. [8] The adhesive or sealant according to [7], used for fixing, bonding, or protecting components constituting an optical sensor module. [9] A cured product obtained by curing the curable resin composition according to any one of [1] to [6], or the adhesive or sealant according to [7] or [8].

[10] A semiconductor device or electronic component comprising the cured product according to [9].

[11] The semiconductor device or electronic component according to

[10] , which is an optical sensor module.

[0010] According to aspects of the present invention, a curable resin composition capable of providing a cured product with excellent adhesive strength to engineering plastics in thermosetting, an adhesive or encapsulant containing the same, the cured product thereof, and a semiconductor device and electronic component containing the cured product are provided. Furthermore, the curable resin composition and the adhesive or encapsulant containing the same of the present invention have the effect of good dispensability.

[0011] 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 to describe 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. In this specification, "(meth)acryloyl group" refers to both methacryloyl and acryloyl groups. Also, "(meth)acrylate compound" refers to both acrylate and methacrylate compounds. Furthermore, in this specification, "curable resin composition" may simply be referred to as "resin composition." In this specification, numerical ranges indicated using "~" include the numbers before and after "~" as the minimum and maximum values, respectively. In numerical ranges described stepwise in this specification, the upper or lower limit of one numerical range may be replaced by the upper or lower limit of another numerical range described stepwise. Furthermore, in the numerical ranges described herein, the upper or lower limits of those ranges may be replaced with the values ​​shown in the examples. 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.

[0012] [Curable Resin Composition] A curable resin composition according to one aspect of the present invention comprises (A) a (meth)acrylate compound, (B) a polythiol compound, (C) an allyl compound, and (D) a polymerization initiator, wherein the proportion of compounds having heterocyclic and / or aromatic rings among the (B) polythiol compound and the (C) allyl compound is 5% by mass or more. According to this aspect, a resin composition can be provided that can give a cured product with excellent adhesive strength to engineering plastics when heat-cured.

[0013] (A) (meth)acrylate compound The curable resin composition of this embodiment contains (A) a (meth)acrylate compound (hereinafter also referred to as "component (A)"). The (A) (meth)acrylate compound has a (meth)acryloyl group as a reactive group for curing, and gives the curable resin composition functions such as adhesive function and sealing function. The (A) (meth)acrylate compound is not particularly limited as long as it has at least one (meth)acryloyl group, and examples include monofunctional (meth)acrylate compounds having one (meth)acryloyl group and polyfunctional (meth)acrylate compounds having two or more (meth)acryloyl groups. From the viewpoint of curability, polyfunctional (meth)acrylate compounds having two or more (meth)acryloyl groups are preferred, compounds having two to six (meth)acryloyl groups are more preferred, and compounds having two (meth)acryloyl groups are even more preferred. Furthermore, in addition to polyfunctional (meth)acrylate compounds, monofunctional (meth)acrylate compounds can also be used to adjust viscosity and cured product properties (such as adhesive strength and flexibility).

[0014] 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, octyl (meth)acrylate, nonyl (meth)acrylate, isononyl (meth)acrylate, 3,3,5-Trimethylcyclohexyl (meth)acrylate, 2-ethyl-2-adamantyl (meth)acrylate, cyclic trimethylolpropane formal (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 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-adamantyl Adamantanyl (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 Propan-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.

[0015] Examples of polyfunctional (meth)acrylate compounds include di(meth)acrylate of tris(2-hydroxyethyl) isocyanurate, tris(2-hydroxyethyl) isocyanurate tri(meth)acrylate, trimethylolpropane tri(meth)acrylate, or their oligomers; pentaerythritol tri(meth)acrylate, or its oligomers; poly(meth)acrylate of dipentaerythritol; tris(acryloxyethyl) isocyanurate; caprolactone-modified tris((meth)acryloxyethyl) isocyanurate; alkyl-modified poly(meth)acrylate of dipentaerythritol; poly(meth)acrylate of caprolactone-modified dipentaerythritol; bisphenol A di(meth)acrylate Examples of (meth)acrylate compounds include, but are not limited to, polyester (meth)acrylate, dimethyl tricyclodecane di(meth)acrylate, tricyclodecane dimethanol diacrylate, ditrimethylolpropane poly(meth)acrylate, polycarbonate-based urethane acrylate oligomers, and polyurethanes having two or more (meth)acryloyl groups in one molecule, as well as polyesters having two or more (meth)acryloyl groups in one molecule, such as polyester (meth)acrylate, dimethylol-tricyclodecane di(meth)acrylate, tricyclodecane dimethanol diacrylate, ditrimethylolpropane poly(meth)acrylate, and polycarbonate-based urethane acrylate oligomers.

[0016] The (meth)acrylate compound may be any one of the (meth)acrylate compounds described above, or two or more may be used in combination.

[0017] Examples of commercially available (meth)acrylate compounds include polyester acrylate (product name: EBECRYL810) manufactured by Daicel Ornex Corporation, ditrimethylolpropanetetraacrylate (product name: EBECRYL140) manufactured by Daicel Ornex Corporation, polyester acrylate (product name: Aronics M7100) manufactured by Toagosei Co., Ltd., dimethylol-tricyclodecane diacrylate (product name: Light Acrylate DCP-A) manufactured by Kyoeisha Chemical Co., Ltd., tricyclodecanedimethanol diacrylate (product name: NK Ester A-DCP-K3) manufactured by Shin Nakamura Chemical Co., Ltd., polyethylene glycol acrylate (product names: NK Ester A-200, A-400, A-600, A-1000) manufactured by Shin Nakamura Chemical Industry Co., Ltd., and polypropylene glycol acrylate (product name: NK Ester APG-200, APG-400, APG-700), Neopentyl glycol-modified trimethylolpropane diacrylate (product name: Kayarad R-604) manufactured by Nippon Kayaku Co., Ltd., Trimethylolpropane trimethacrylate (product name: Light Ester TMP) manufactured by Kyoeisha Chemical Co., Ltd., Alkyl methacrylate (product names: HD-N, NOD-N, DOD-N, NPG) manufactured by Shin Nakamura Chemical Industry Co., Ltd., 2-hydroxy-1,3-dimethacryloxypropane (product name: 701) manufactured by Shin Nakamura Chemical Industry Co., Ltd., Trimethylolpropane Examples include, but are not limited to, pantrimethacrylate (product name: TMPT), ether-based urethane acrylate manufactured by Shin Nakamura Chemical Industry Co., Ltd. (product names: UA-160TM, UA-W2A), ether-based urethane acrylate manufactured by Negami Kogyo Co., Ltd. (product names: UN-6200, UN-6207, UN-6304, UN-6305, UN-6306, UN-6307, UN-6060S), and carbonate-based urethane acrylate manufactured by Negami Kogyo Co., Ltd. (product names: UN-5500, UN-5590, UN-9000PEP, UN9200A).

[0018] (A) The (meth)acrylate compound is preferably having a viscosity of 0.01 to 80 Pa·s, from the viewpoint of resin composition preparation and dispensability. In this specification, viscosity refers to the value measured at a measurement temperature of 25°C using an appropriate viscometer depending on the viscosity range.

[0019] (A) The content of the (meth)acrylate compound is preferably 10 to 70% by mass, and more preferably 20 to 60% by mass, relative to the total mass of the resin composition, from the viewpoint of the adhesive strength of the resin composition.

[0020] (B) Polythiol Compound The curable resin composition of this embodiment contains (B) a polythiol compound (hereinafter also referred to as "component (B)"). The thiol group of the polythiol compound can undergo a radical addition reaction (en-thiol reaction) with the unsaturated double bond of a compound having an unsaturated double bond under radical polymerization conditions, and curing proceeds. In addition, the thiol group of the polythiol compound can react with the (meth)acryloyl group of a (meth)acrylate compound under anionic polymerization conditions, and curing proceeds. The (B) polythiol compound is not particularly limited as long as it has two or more thiol groups. In one embodiment, the (B) polythiol compound contains a difunctional thiol compound. In one embodiment, the (B) polythiol compound contains a trifunctional or higher thiol compound. In one embodiment, the (B) polythiol compound contains a trifunctional and / or tetrafunctional thiol compound. In one embodiment, the (B) polythiol compound contains a combination of a difunctional thiol compound and a trifunctional or higher thiol compound. In one embodiment, (B) the polythiol compound comprises a combination of a difunctional thiol compound and a trifunctional and / or tetrafunctional thiol compound.

[0021] Examples of polythiol compounds include 1,2,3-(3-mercaptopropyloxy)propane, pentaerythritol tetrapropanthol (also known as 3-{3-(3-mercapto-propoxy)-2,2-bis-[(3-mercaptopropoxy)methyl]propoxy}-1-propanthol), 1,3,4,6-tetrakis(2-mercaptoethyl)glycoluryl, 1,3,4,6-tetrakis(3-mercaptopropyl)glycoluryl, 1,3,4,6-tetrakis(mercaptomethyl)glycoluryl, and 1,3,4,6-tetrakis(mercaptomethyl)-3 α-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, 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)eth [L]isocyanurate, pentaerythritol tripropanthol, 3-[2,3-bis(3-sulfanylpropoxy)propoxy]propane-1-thiol, 1,2,3-tris(3-mercaptopropyloxy)propane, 1,3-bis(3-mercaptopropyloxy)propane, 1,3-bis(3-mercaptopropyloxy)-2-propanol or derivative thereof, 3-[2,2-bis[(3-mercaptopropoxy)methyl]butoxy]-1-propanthol, 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(mercaptomethylthiomethyl)methane, tetrakis(2-mercaptomethylthio) (Ptoethylthiomethyl)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) Tris(2,2-bis(mercaptomethylthio)-2,5,8-trithianonane, 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) (Tomethylthio)-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-hexathiaheptadecane, 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(mercaptomethylthio)-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)-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]mercaptomethylthiomethyl-1,3- Various bifunctional thiol compounds disclosed in WO2019 / 082962, such as 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-dithiethanyl)]-3-mercapto-2-thiapropylthio}-5-[1,2-bis(mercaptomethylthio)-4-mercapto-3-thiabutylthio]-1,3-dithiolane, 2,2'-[cyclohexylidenebis(thio-2,1-ethanediylthio)]bis[ethanethiol], 4,4'-[(1,3-phenylene)bis(oxy)]bis[1-butanethiol], and dimers, trimers, and tetramers of the thiol compounds; 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, pentaerythritol tetrakis(3-mercaptobutyrate), 1,4-bis(3-mercaptobutyryloxy)butane, or 1,3,Examples include, but are not limited to, 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. Furthermore, these bifunctional or multifunctional polythiol compounds may include their derivatives and / or their monofunctional and / or difunctional forms as impurities or by-products in the synthesis.

[0022] Examples of commercially available (B) polythiol compounds include 1,3,4,6-tetrakis(2-mercaptoethyl) glycoluryl (product name: TS-G, manufactured by Shikoku Chemicals Co., Ltd.), 1,3,4,6-tetrakis(3-mercaptopropyl) glycoluryl (product name: C3 TS-G, manufactured by Shikoku Chemicals Co., Ltd.), and pentaerythritol tetrapropanthol (also known as 3-{3-(3-mercaptopropoxy)-2,2-bis-[(3-mercaptopropoxy)methyl]propoxy}-1-propanthol) (product name: Multiol) Y-4 (manufactured by Sakai Chemical Industry Co., Ltd.), pentaerythritol tripropanethol (product name: PEPT, manufactured by SC Organic Chemicals), trimethylolpropane tris(3-mercaptopropionate) (product name: TMMP, manufactured by SC Organic Chemicals Co., Ltd.), tris-[(3-mercaptopropionyloxy)-ethyl]-isocyanurate (product name: TEMPIC, manufactured by SC Organic Chemicals Co., Ltd.), pentaerythritol tetrakis(3-mercaptopropionate) (product name: PEMP, manufactured by SC Organic Chemicals Co., Ltd.), tetraethylene glycol bis(3-mercaptopropionate) (product name: EG Examples include, but are not limited to, MP-4 (manufactured by SC Organic Chemicals Co., Ltd.), dipentaerythritol hexakis(3-mercaptopropionate) (product name: DPMP, manufactured by SC Organic Chemicals Co., Ltd.), pentaerythritol tetrakis(3-mercaptobutyrate) (product name: Karenz MT® PE1, manufactured by Resonaq Corporation), 1,3,5-tris(3-mercaptobutyryloxyethyl)-1,3,5-triazine-2,4,6(1H,3H,5H)-trione (product name: Karenz MT® NR1, manufactured by Resonaq Corporation), and isocyanuric acid skeleton trithiol compounds (product name: ACTOCURE SS32, manufactured by Kawaguchi Chemical Industry Co., Ltd.).

[0023] (B) The thiol equivalent of the polythiol compound is preferably 50 to 1000 g / eq, more preferably 50 to 800 g / eq, even more preferably 50 to 600 g / eq, and particularly preferably 50 to 300 g / eq.

[0024] In this embodiment, the content of the (B) polythiol compound in the resin composition is preferably 1 to 70% by mass, more preferably 5 to 65% by mass, and even more preferably 10 to 60% by mass, based on the total mass of the resin composition.

[0025] (C) Allyl compound The curable resin composition of this embodiment contains (C) an allyl compound (hereinafter also referred to as "component (C)"). In this specification, an allyl compound is defined as an allyl group (-CH ２ -CH=CH ２ Allyl compounds are compounds having at least one allyl group, and if they have at least one allyl group, compounds having an allyl group plus a (meth)acryloyl group or a thiol group are also considered "allyl compounds." Examples of allyl compounds include monofunctional allyl compounds having one allyl group, and polyfunctional allyl compounds having two or more allyl groups. Polyfunctional allyl compounds having two or more allyl groups are preferred, allyl compounds having two to six allyl groups are more preferred, and allyl compounds having two to four allyl groups are even more preferred. The allyl group of an allyl compound can undergo a radical addition reaction (en-thiol reaction) with the thiol group of a polythiol compound under radical polymerization conditions. Allyl compounds can be broadly classified into allyl compounds having an aromatic ring skeleton, allyl compounds having a heterocyclic skeleton, and aliphatic allyl compounds, depending on the type of skeleton.

[0026] Examples of allyl compounds having an aromatic ring skeleton include, but are not limited to, 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), and other allylphenol compounds (e.g., allylphenol compounds described in Japanese Patent Publication No. 2019-052258). Examples of commercially available allylphenol compounds include, but are not limited to, diallylbisphenol A (e.g., BPA-CA manufactured by Konishi Chemical Industry Co., Ltd., DABPA manufactured by Yamato Chemical Industry Co., Ltd., and DA-BPA manufactured by Yokkaichi Synthetic Co., Ltd.), diallylbisphenol F (e.g., MEH-8000H and MEH-8005 manufactured by UBE Corporation), biphenylene resin (SBA series manufactured by Gun-ei Chemical Industry Co., Ltd.), allylphenol resin (APG series manufactured by Gun-ei Chemical Industry Co., Ltd.), allylphenol resin (LVA series manufactured by Gun-ei Chemical Industry Co., Ltd.), propenylated biphenylene resin (BPN series manufactured by Gun-ei Chemical Industry Co., Ltd.), allyl etherphenol resin (FTC-AE series manufactured by Gun-ei Chemical Industry Co., Ltd.), and polyfunctional allylphenol resin (FATC series manufactured by Gun-ei Chemical Industry Co., Ltd.).

[0027] Examples of allyl compounds having a heterocyclic skeleton include, but are not limited to, trialyl cyanurate, allyl cyanurate derivatives (e.g., MA-DGIC, DAMGIC, MeDAIC, L-DAIC, DD-1 from Shikoku Chemicals, Inc.), allyl compounds having an isocyanuric acid skeleton such as trialyl isocyanurate (e.g., TAIC from Shinryo Co., Ltd.), and allyl compounds having a glycoluryl skeleton such as 1,3,4,6-tetraallyl glycoluryl (TA-G from Shikoku Chemicals, Inc.).

[0028] Examples of aliphatic allyl compounds include, but are not limited to, glycerol monoallyl ether, allyl glycidyl ether, allyl hydroxyacetate, allyl hydroxypropanoate, allyl hydroxyhexanoate, 4-hydroxycyclohexylacetate, trimethylolpropanediallyl ether, pentaerythritol triallyl ether, pentaerythritol tetraallyl ether, and (meth)acrylates having an allyloxymethyl group.

[0029] (C) The allyl equivalent of the allyl compound is preferably 50 to 1000 g / eq, more preferably 50 to 800 g / eq, even more preferably 50 to 600 g / eq, and particularly preferably 50 to 300 g / eq.

[0030] From the viewpoint of further improving the adhesive strength to engineering plastics, the (C) allyl compound is preferably an allyl compound having an aromatic ring skeleton or an allyl compound having a heterocyclic skeleton, more preferably an allyl compound having an aromatic ring skeleton, and even more preferably an allyl compound having a bisphenol skeleton.

[0031] From the viewpoint of further improving the adhesive strength to engineering plastics, the (C) allyl compound preferably contains an allyl compound having a hydroxyl group, and more preferably contains an allyl compound having two or more hydroxyl groups. In particular, when the hydroxyl groups are phenolic hydroxyl groups, this is preferable because it further improves the adhesive strength to engineering plastics. In one embodiment, the (C) allyl compound contains an allyl compound having two or more phenolic hydroxyl groups. Under anionic polymerization conditions, the hydroxyl groups in the allyl compound react with epoxy groups (if present) and are incorporated into molecular crosslinking, thereby improving the adhesive strength to the adherend. In particular, when the hydroxyl groups in the allyl compound are phenolic hydroxyl groups, the reactivity under anionic polymerization conditions is high, and it is thought that the adhesive strength to the adherend is further improved. Furthermore, when epoxy groups are absent or under radical polymerization conditions, the hydroxyl groups in the allyl compound do not contribute to the crosslinking reaction, but because they are in a free state, they can form hydrogen bonds with the adherend, thereby improving the adhesive strength to the adherend.

[0032] In this embodiment, the content of the (C) allyl compound in the resin composition is preferably 0.5 to 30% by mass, more preferably 1 to 25% by mass, and even more preferably 1 to 20% by mass, based on the total mass of the resin composition. Alternatively, the content of the (C) allyl compound in the resin composition is preferably 1 to 30% by mass, more preferably 2 to 25% by mass, based on the total mass of the (A) (meth)acrylate compound and the (B) polythiol compound. Alternatively, the content of the (C) allyl compound in the resin composition is preferably 1 to 70% by mass, more preferably 3 to 60% by mass, and even more preferably 5 to 50% by mass, based on the total mass of the (B) polythiol compound.

[0033] In the curable resin composition of this embodiment, the proportion of compounds having heterocyclic and / or aromatic rings among (B) polythiol compounds and (C) allyl compounds is 5% by mass or more, for example, 6% by mass or more, and for example, 8% by mass. This provides a resin composition that can give a cured product with excellent adhesive strength to engineering plastics when heat-cured. In one embodiment, the proportion of compounds having heterocyclic and / or aromatic rings among (B) polythiol compounds and (C) allyl compounds is 100% by mass or less, for example, 95% by mass or less, and for example, 90% by mass or less. Engineering plastics are classified as difficult-to-adhere materials due to their high crystallinity, lower surface energy than metals, and poor wettability with resin compositions. Curable resin compositions containing acrylic resin and thiol compounds exhibit excellent low-temperature curing properties, but it has been found that the adhesive strength of the cured product to engineering plastics as the adherend after heat curing may be insufficient. This tendency was particularly observed when an aliphatic thiol compound was selected as the thiol compound considering the elastic modulus of the cured product. As a result of diligent research, it was found that this problem can be solved by including allyl compounds and ensuring that the proportion of compounds having heterocyclic and / or aromatic rings among the polythiol and allyl compounds exceeds a specific value. For example, if the thiol compound contains only aliphatic thiol compounds, it is sufficient to include 5% by mass or more of allyl compounds having heterocyclic and / or aromatic rings relative to the total amount of (B) polythiol compounds and (C) allyl compounds. Including a large amount of compounds having heterocyclic and / or aromatic rings may worsen the dispensability of the resin composition, but when (B) polythiol compounds and / or (C) allyl compounds have heterocyclic and / or aromatic rings, it was effective in that the dispensability of the resulting resin composition remained good while the adhesive strength to engineering plastics was improved. Preferably, the compounds having heterocyclic and / or aromatic rings in (B) polythiol compounds and / or (C) allyl compounds are compounds having a bisphenol skeleton, a glycoluryl skeleton, or an isocyanuric acid skeleton.

[0034] In the curable resin composition of this embodiment, the ratio of the number of thiol group equivalents of component (B) to the sum of the number of (meth)acryloyl group equivalents of component (A) and the number of allyl group equivalents of component (C) ([number of thiol group equivalents of component (B)] / ([number of (meth)acryloyl group equivalents of component (A)] + [number of allyl group equivalents of component (C)])) is preferably 0.1 to 10, more preferably 0.2 to 5, and even more preferably 0.5 to 3. In this specification, functional group equivalents such as thiol equivalents, (meth)acryloyl equivalents, and allyl equivalents represent the molecular weight of the compound per functional group, and functional group equivalent numbers such as the number of thiol group equivalents, (meth)acryloyl group equivalents, and allyl group equivalents represent the number of functional groups (equivalents) (moles) per unit mass (amount charged) of compound. (B) The thiol equivalent of a polythiol compound is theoretically equal to the molecular weight of the polythiol compound divided 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 number of thiol groups (equivalents) (moles) per mass (amount charged) of component (B), and is the quotient obtained by dividing the mass (g) of the polythiol compound (B) by the thiol equivalent of that polythiol compound (if multiple polythiol compounds are included, it is the sum of such quotients for each polythiol compound). (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 number of (meth)acryloyl groups (equivalents) (moles) per unit mass (amount charged) of component (A), 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).(C) The allyl equivalent of an allyl compound is theoretically equal to the molecular weight of the allyl compound divided by the number of allyl groups in one molecule. The actual allyl equivalent can be measured, for example, by NMR. The number of allyl group equivalents of component (C) is the number of allyl groups (equivalents) (moles) per unit mass (amount charged) of component (C), and is the quotient obtained by dividing the mass (g) of the allyl compound by the allyl equivalent of that allyl compound (if multiple allyl compounds are included, it is the sum of such quotients for each allyl compound). Setting [Number of thiol group equivalents of component (B)] / ([Number of (meth)acryloyl group equivalents of component (A)] + [Number of allyl group equivalents of component (C)]) within the above range allows for sufficient molecular crosslinking to be formed, thereby facilitating the development of high adhesive strength, as the (meth)acryloyl groups and allyl groups react with thiol groups in amounts greater than a certain amount.

[0035] The curable resin composition of this embodiment may contain polymerizable compounds other than (A) (meth)acrylate compounds, (B) polythiol compounds, and (C) allyl compounds, but the total mass of (A) (meth)acrylate compounds, (B) polythiol compounds, and (C) allyl compounds is preferably 60 to 100% by mass, more preferably 70 to 100% by mass, and even more preferably 80 to 100% by mass, relative to the total mass of all polymerizable compounds in the curable resin composition. Examples of other polymerizable compounds include epoxy compounds.

[0036] (D) Polymerization initiator The curable resin composition of this embodiment contains (D) a polymerization initiator (hereinafter also referred to as "component (D)"). In this embodiment, (D) a polymerization initiator includes (D1) a thermal polymerization initiator, and may also include a combination of (D1) a thermal polymerization initiator and (D2) a photopolymerization initiator.

[0037] (D1) Thermal polymerization initiator (D1) A thermal polymerization initiator is a compound that generates active species such as radicals, anions, or cations upon heat, and depending on the type of active species, examples include thermal radical polymerization initiators, thermal anionic polymerization initiators, and thermal cationic polymerization initiators. In this embodiment, the thermal polymerization initiator is preferably a thermal radical polymerization initiator or a thermal anionic polymerization initiator, more preferably a thermal anionic polymerization initiator, and a combination of a thermal radical polymerization initiator and a thermal anionic polymerization initiator may be used.

[0038] 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.

[0039] 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.

[0040] Examples of the thermal anionic polymerization initiator include, in addition to the above examples, a "thermally latent curing catalyst" which is a basic catalyst that is inactive at normal temperature, activated by heating, and functions as a polymerization catalyst. Examples of the thermally latent curing catalyst include amine compounds that are solid at normal temperature; amine adduct-based thermally latent curing catalysts such as reaction products of an amine compound and an epoxy compound (amine-epoxy adduct system), and reaction products of an amine compound and an isocyanate compound or a urea compound (urea-type adduct system); microcapsule-type thermally latent curing catalysts; solid dispersion-type thermally latent curing catalysts such as inclusion-type thermally latent curing catalysts. The amine compound includes aliphatic amines, aromatic amines, and heterocyclic amines. Note that the thermally latent curing catalyst may be in a form dispersed in an epoxy resin, or may be in a form dispersed in a thiol-based curing agent as disclosed in Japanese Patent Application Laid-Open No. 2017-082219.

[0041] Examples of the amine compound that is solid at normal temperature include, but are not limited to, 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, 2,4-diamino-6-(2'-methylimidazolyl-(1)')-ethyl-S-triazine isocyanuric acid adduct, 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, N,N'-(2-methylimidazolyl-(1)-ethyl)-adiboyldiamide, and the like.

[0042] 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; heterocyclic amine compounds containing nitrogen atoms such as 2-ethyl-4-methylimidazole, 2-ethyl-4-methylimidazoline, 2,4-dimethylimidazoline, piperidine, and piperazine.

[0043] 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 1-(2-hydroxy-3-butoxypropyl)-2-methylimidazole, 1-(2-hydroxy-3-butoxypropyl)-2-ethyl-4-methylimidazole, 1-(2-hydroxy-3-phenoxypropyl)-2-phenylimidazoline, 1-(2-hydroxy-3-butoxypropyl)-2-methylimidazole, 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.

[0044] As epoxy compounds used as one of the raw materials for producing amine-epoxy adduct-based thermally latent curing catalysts, examples include: 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, m-aminophenol and the like with epichlorohydrin; furthermore, polyfunctional epoxy compounds such as epoxidized phenol novolac resins, epoxidized cresol novolac resins, and epoxidized polyolefins, and monofunctional epoxy compounds such as butyl glycidyl ether, phenyl glycidyl ether, various phenylphenol glycidyl ethers, and glycidyl methacrylate. However, the epoxy compounds are not limited to these.

[0045] Examples of isocyanate compounds used as raw materials for the production of amine-urea type adduct-type 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.

[0046] Examples of urea compounds used as raw materials for the production of amine-urea type adduct-based thermal latent curing catalysts include, but are not limited to, urea and thiourea.

[0047] 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 (two or three components). 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.

[0048] 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.

[0049] 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), and "NovaCure HX-3721" (Asahi Kasei Corporation). Examples include, but are not limited to, Novacure HXA9322HP (Asahi Kasei Corporation product name), Novacure HXA3922HP (Asahi Kasei Corporation product name), Novacure HXA3932HP (Asahi Kasei Corporation product name), Novacure HX3722 (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 which 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 aforementioned 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), "Fujicure 1171" (T&K TOKA Corporation product name), and "Fujicure 2015" (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&K TOKA Co., Ltd.) and "Fujicure 2021" (product name of T&K TOKA Co., Ltd.).

[0050] A capillary-type thermal latent curing catalyst is a curing catalyst having a structure in which guest molecules, such as amine compounds, are trapped at the molecular level within the crystalline space formed by the host molecule. An example of a commercially available capillary-type thermal latent curing catalyst is "NISSOCURE TIC-188" (product name of Nippon Soda Co., Ltd.).

[0051] As a thermal latent curing catalyst used as a thermal anionic polymerization initiator, one type may be used, or two or more types may be used in combination.

[0052] In one embodiment, the resin composition comprises a thermal radical polymerization initiator or a thermal anionic polymerization initiator. In one embodiment, the resin composition comprises a thermal anionic polymerization initiator. In one embodiment, the resin composition comprises a thermal radical polymerization initiator and a thermal anionic polymerization initiator.

[0053] (D1) The content of the thermal polymerization initiator is preferably 0.5 to 30% by mass, more preferably 0.5 to 25% by mass, and even more preferably 0.5 to 20% by mass, based on the total mass of the resin composition.

[0054] (D2) Photopolymerization initiator 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. In this embodiment, the photopolymerization initiator is preferably a photoradical polymerization initiator or a photoanionic polymerization initiator, more preferably a photoradical polymerization initiator, and a combination of a photoradical polymerization initiator and a photoanionic polymerization initiator may be used.

[0055] Photoradical polymerization initiators are compounds that absorb light to generate radicals as active species, thereby promoting the polymerization of radically polymerizable compounds. Examples of photoradical polymerization initiators include, but are not limited to, alkylphenone compounds, acylphosphine oxide compounds, oxime ester compounds, and compounds having photosensitive sites and peroxide structures.

[0056] 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.). These may be used individually or in combination of two or more.

[0057] 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.). These may be used individually or in combination of two or more.

[0058] Examples of oxime ester compounds 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). These may be used individually or in combination of two or more.

[0059] Examples of compounds having a photosensitive site and a peroxide structure, or commercially available products thereof, include, but are not limited to, 3,3',4,4'-tetrakis(tert-butylperoxycarbonyl)benzophenone (BTTB), Perdual TA, and Perdual TX (all manufactured by NOF Corporation).

[0060] 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 benzyldimethyl Examples include, but are not limited to, ketal, 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. These may be used individually or in combination of two or more.

[0061] Any one type of photoradical polymerization initiator may be used, or two or more types may be used in combination.

[0062] Photo-anionic polymerization initiators are compounds that absorb light to generate anions as active species, thereby promoting the polymerization of anionic polymerizable compounds. Examples of photo-anionic polymerization initiators include, but are not limited to, various compounds that generate amines, amidines, guanidines, phosphazenes, carbenes, etc., as bases. Specific examples of photoanionic polymerization initiators include, for example, 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, and diaminomethaneiminium 2-(3-ben Zoylphenyl)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. The photo-anionic polymerization initiator may be used individually or in combination of two or more.

[0063] In one embodiment, the resin composition comprises a photoradical polymerization initiator or a photoanionic polymerization initiator. In one embodiment, the resin composition comprises a photoanionic polymerization initiator. In one embodiment, the resin composition comprises a photoradical polymerization initiator and a photoanionic polymerization initiator.

[0064] (D2) The content of the photopolymerization initiator is 0.01 to 10% by mass, preferably 0.01 to 7% by mass, more preferably 0.03 to 5% by mass, and even more preferably 0.05% to 5% by mass, based on the total mass of the resin composition.

[0065] In one embodiment, the resin composition comprises (D1) a thermal anionic polymerization initiator as a thermal polymerization initiator and (D2) a photoradical polymerization initiator as a photopolymerization initiator.

[0066] (E) Radical polymerization inhibitor The resin composition of this embodiment may contain (E) a radical polymerization inhibitor (hereinafter also referred to as "component (E)") to the extent that it does not impair the effects of the present invention. (E) The radical polymerization inhibitor is added to improve the stability of the resin composition during storage and to suppress the occurrence of unintended radical polymerization reactions. (Meth)acrylate compounds may generate radicals on their own with a low probability, and unintended radical polymerization reactions may occur starting from these radicals. By adding a radical polymerization inhibitor, the occurrence of such unintended radical polymerization reactions can be suppressed.

[0067] Known radical polymerization inhibitors can be used, for example, at least one selected from N-nitroso-N-phenylhydroxylamine aluminum, triphenylphosphine, p-methoxyphenol, and hydroquinone. Alternatively, known radical polymerization inhibitors disclosed in Japanese Patent Publication No. 2010-117545, Japanese Patent Publication No. 2008-184514, etc., can also be used.

[0068] (E) From the viewpoint of pot life, the content of the radical polymerization inhibitor is preferably 0.0001 to 5% by mass, and more preferably 0.001 to 3% by mass, based on the total mass of the resin composition.

[0069] The resin composition of this embodiment may, if desired, further contain other additives, such as fillers, thixotropes, conductive particles, elastomers, stabilizers, radical polymerization inhibitors, coupling agents, carbon black, titanium black, ion trapping agents, leveling agents, antioxidants, defoaming agents, surfactants, dispersants, viscosity modifiers, flame retardants, colorants, dehydrating agents, sensitizers such as thioxanthones, diethoxyanthracene, and dibutoxyanthracene, and other polymerizable compounds such as luminescent materials and epoxy compounds, to the extent that the spirit of this embodiment is not impaired. The type and amount of each additive are within the normal range in the field of curable resin compositions, but the total content of other additives may be, for example, 0 to 40% by mass of the total mass of the resin composition.

[0070] Fillers are broadly classified into inorganic fillers and organic fillers.

[0071] 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 include 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.

[0072] Examples of organic fillers include polytetrafluoroethylene (PTFE) fillers, silicone fillers, acrylic fillers, fillers with a urethane skeleton, fillers with a butadiene skeleton, and styrene fillers. Organic fillers may be surface-treated.

[0073] The shape of the filler is not particularly limited and may be spherical, flake-shaped, needle-shaped, irregular, or any other shape.

[0074] 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 (d) measured by laser diffraction in accordance with ISO-13320 (2009). ５０ This refers to the filler. By keeping the average particle size of the filler below the upper limit, the settling of the filler can be suppressed, and the formation of coarse particles can be suppressed, thereby suppressing wear of the jet dispenser nozzle and the scattering of the curable 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 curable resin composition, it is preferably 0.005 μm or more, and more preferably 0.1 μm or more. Fillers with different average particle sizes may be used in combination. When a filler is included, the filler content is preferably 0.5 to 50% by mass, and more preferably 1 to 40% by mass, based on the total mass of the resin composition.

[0075] • Swixer Examples of swixers 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 maintaining shape 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 10 to 750 nm is more preferred, and nanosilica with an average particle size of 20 to 600 nm is even more preferred. 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: AEROSIL® 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 nanotrack particle size analyzer. The quinotroper may be used alone or in combination of two or more types. When a quinotroper is included, the quinotroper 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.

[0076] Coupling agents have two or more different functional groups in their molecule, one of which is a functional group that chemically bonds with inorganic materials, and the other is a functional group that chemically bonds with organic materials.

[0077] 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.

[0078] Examples of coupling agents include, but are not limited to, various types of coupling agents such as epoxy, amino, vinyl, methacrylic, acrylic, and mercapto-based coupling agents, depending on the type of functional group that chemically bonds with the organic material.

[0079] The coupling agent may be any one type, or two or more types may be used in combination.

[0080] When a coupling agent is added, the amount of the coupling agent added is preferably 0.01 to 10 parts by mass, and more preferably 0.1 to 5 parts by mass, per 100 parts by mass of the total amount of the resin composition, from the viewpoint of improving adhesive strength.

[0081] Stabilizers: Stabilizers are used to enhance the stability of the resin composition during storage and may be added to suppress the occurrence of polymerization reactions due to unintended basic components. Various known acidic compounds can be used as stabilizers. Preferably, the acidic compound is at least one selected from the group consisting of boric acid ester compounds, phosphoric acid compounds, alkyl phosphoric acid ester compounds, sulfonic acid compounds, aluminum chelates, condensates of aluminum chelates and silanol compounds, and organic acids.

[0082] Examples of borate ester compounds include 2,2'-oxybis(5,5'-dimethyl-1,3,2-oxaborinane), trimethyl borate, triethyl borate, tri-n-propyl borate, triisopropyl borate, trimethoxyboroxine, tri-n-butyl borate, tripentyl borate, triallyl borate, trihexyl borate, tricyclohexyl borate, trioctyl borate, trinonyl borate, tridecyl borate, tridodecyl borate, trihexadecyl borate, trioctadecyl borate, tris(2-ethylhexyloxy)borane, tripenzyl borate, triphenyl borate, tri-o-tolyl borate, tri-m-tolyl borate, triethanolamine borate, and the like. Among borate ester compounds, those that are liquid at room temperature (25°C) are preferred because they can keep the viscosity of the formulation low. Examples of alkyl phosphate ester compounds include trimethyl phosphate and tributyl phosphate. Examples of sulfonic acid compounds include p-toluenesulfonic acid. As an aluminum chelate, for example, aluminum chelate A (manufactured by Kawaken Fine Chemicals Co., Ltd.) can be used. As a condensate of aluminum chelate and silanol compound, for example, a condensate of aluminum chelate and triphenylsilanol can be used. As an organic acid, for example, barbituric acid can be used. If a stabilizer is included, the content of the stabilizer is preferably 0.001 to 5% by mass, more preferably 0.01 to 3% by mass, based on the total mass of the resin composition.

[0083] • Radical polymerization inhibitors (meth)acrylate compounds may generate radicals on their own with a low probability, and unintended radical polymerization reactions may occur starting from these radicals. By adding a radical polymerization inhibitor, the occurrence of such unintended radical polymerization reactions can be suppressed. Note that products of polymerizable compounds such as (meth)acrylate compounds may contain radical polymerization inhibitors. The radical polymerization inhibitor that may be included in the resin composition of this embodiment may be a radical polymerization inhibitor that was included in the compounding materials of the resin composition, a radical polymerization inhibitor that was added independently to the resin composition, or a combination thereof. Known radical polymerization inhibitors can be used, for example, at least one selected from N-nitroso-N-phenylhydroxylamine aluminum, triphenylphosphine, p-methoxyphenol, and hydroquinone can be used. In addition, known radical polymerization inhibitors disclosed in Japanese Patent Application Publication No. 2010-117545, Japanese Patent Application Publication No. 2008-184514, etc. can also be used. When a radical polymerization inhibitor is included, the content of the radical polymerization inhibitor is preferably 0.0001 to 5% by mass, and more preferably 0.001 to 3% by mass, based on the total mass of the resin composition, from the viewpoint of pot life.

[0084] Epoxy Compounds: In this specification, an epoxy compound is a compound having at least one epoxy group in its molecule. Examples include monofunctional epoxy compounds having one epoxy group and polyfunctional epoxy compounds having two or more epoxy groups.

[0085] Specific examples of epoxy compounds include bisphenol A type epoxy compounds, bisphenol F type epoxy compounds, novolac type epoxy compounds, glycidyl ethers of tetra(hydrophenyl)alkanes, glycidyl ethers of tetrahydroxybenzophenone, 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, hydrogenated bisphenol F 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, 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 T, bis(3,4-epoxycyclohexylmethyl) adipate, 3,4-epoxy-6-methylcyclohexane carboxylate, methylenebis(3,4-epoxycyclohexane), propane-2,2-diyl-bis(3,4-epoxycyclohexane), 2,2-bis(3,4-epoxycyclohexyl)propane, dicyclopentadiene diepoxide, ethylenebis(3,4-epoxycyclohexane carboxylate), limonene dioxide (1,2:8,9-diepoxylimonene), (3,3',4,Examples include, but are not limited to, 4'-diepoxy)bicyclohexyl, dioctyl epoxyhexahydrophthalate, di-2-ethylhexyl epoxyhexahydrophthalate, 1-epoxyethyl-3,4-epoxycyclohexane, 1,2-epoxy-2-epoxyethylcyclohexane, 1,2-epoxy-4-vinylcyclohexane, α-pinene oxide, 1,2-epoxy-4-(2-oxyranyl)cyclohexane adduct of 2,2-bis(hydroxymethyl)-1-butanol, epoxidized polybutadiene, compounds in which some or all of the double bonds of styrene-butadiene copolymers are epoxidized, alkylene oxide-modified bisphenol A epoxy, alkylene oxide-modified bisphenol F epoxy, lauryl alcohol polyethylene glycol diglycidyl ether, diglycidyl ether of alicyclic diols, diglycidyl ether of alkylene oxide adducts of alicyclic diols, etc. These may be used alone or in combination of two or more.

[0086] Commercially available epoxy compounds include EPICLON® 850, 850-S, EXA-850CRP, EXA-8067 from DIC Corporation; AER9000 from Asahi Kasei Corporation; EP-4000S, EP-4003S, EP-4005, EP-4010S, EP-4088S, EP-4088L from ADEKA Corporation; Rikaresin BEO-60E from Shin Nippon Rika Co., Ltd.; EX-171 from Nagase ChemteX Corporation; and EPICLON® 830-S, EXA-8 from DIC Corporation. 30LVP, EXA-835LV; EPICLON® HP-4032D, HP-720H manufactured by DIC Corporation; 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.; 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, 8400 manufactured by Daicel Corporation; EHPE3150 manufactured by Daicel Corporation; EPOLEAD PB manufactured by Daicel Corporation; and EPOFRIEND manufactured by Daicel Corporation. These may be used individually or in combination of two or more.

[0087] Adhesives or sealants for semiconductor devices or electronic components are typically required to be insulating. In some embodiments, the curable resin composition is insulating. In some embodiments, the curable resin composition does not contain conductive particles.

[0088] 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 (D)) 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.).

[0089] Non-limiting formulation examples of the resin composition according to this embodiment are shown in the table below.

[0090] The viscosity of the resin composition in this embodiment at 25°C is preferably 0.5 to 80 Pa·s. The viscosity can be adjusted as appropriate depending on the application and application location of the resin composition. In one embodiment, the viscosity of the resin composition at 25°C may be 30 to 65 Pa·s. In one embodiment, the viscosity of the resin composition at 25°C may be 1.0 to 15 Pa·s. In this specification, unless otherwise specified, viscosity is expressed as a value measured in accordance with Japanese Industrial Standard JIS K6833. Specifically, it can be determined by measuring at 25°C and a rotation speed of 50 rpm using an HBDV or RV type viscometer depending on the viscosity range. There are no particular restrictions on the equipment, rotor, or measurement range used.

[0091] The thixotropic index (TI) value of the resin composition in this embodiment at 25°C is preferably 1.0 to 8.0. The thixotropic index value can be adjusted as appropriate depending on the application and application location of the resin composition. In one embodiment, the thixotropic index (TI) value of the resin composition at 25°C may be 3.0 to 7.0. In another embodiment, the thixotropic index (TI) value of the resin composition at 25°C may be 0.9 to 5.0. In this specification, the thixotropic index (TI) value can be determined by measuring the viscosity at 5 rpm and 50 rpm at 25°C using an HBDV or RV viscometer, depending on the viscosity range, and using the following formula: [TI value] = [Viscosity at 5 rpm] / [Viscosity at 50 rpm]

[0092] In one embodiment, the viscosity of the resin composition at 25°C is 0.5 to 80 Pa·s, and the thixotropic index (TI) value of the resin composition at 25°C is 1.0 to 8.0. In another embodiment, the viscosity of the resin composition at 25°C is 30 to 65 Pa·s, and the thixotropic index (TI) value of the resin composition at 25°C is 3.0 to 7.0. In yet another embodiment, the viscosity of the resin composition at 25°C is 1.0 to 15 Pa·s, and the thixotropic index (TI) value of the resin composition at 25°C is 0.9 to 5.0.

[0093] The resin composition can be obtained, for example, by stirring, melting, mixing, and / or dispersing components (A) to (D), and other additives as needed, simultaneously or separately, while applying heat treatment as necessary. The apparatus for these mixing, stirring, and dispersion processes is not particularly limited. Apparatus such as a Leikai mill, Henschel mixer, three-roll mill, ball mill, planetary mixer, and bead mill, all equipped with stirring and heating devices, can be used. These apparatuses may also be used in appropriate combinations.

[0094] 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 (D) 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 (D) 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 (D) and other optional components as needed may be contained in each liquid, components (A) to (D) may be contained in one liquid, or there may be a liquid consisting only of components (A) to (D) and / or other optional components as needed. For example, when dividing into liquid A and liquid B, the division may be as follows: liquid A: component (A), liquid B: component (B), component (C), and component (D); liquid A: component (A) and component (B), liquid B: component (C) and component (D); liquid A: component (A) and component (C), liquid B: component (B) and component (D); liquid A: component (A), component (B), and component (C), liquid B: component (D); liquid A: component (A), component (B), and component (D), liquid B: component (C); or liquid A: component (A), component (C), and component (D), liquid B: component (B). If components (A) to (D) are contained in liquid A and the other components are contained in liquid B, liquid A alone, or liquids A and B together, can be considered as the resin composition of this embodiment. On the other hand, if components (A) to (D) are each contained in separate liquids, the combined liquids can be considered as the resin composition of this embodiment. An example of a case where components (A) to (D) are each contained in separate liquids is a resin composition in which components (A) to (D) are divided into two or more containers, specifically a kit consisting of multiple liquids containing any of components (A) to (D).

[0095] The resin composition obtained in this manner is thermosetting if (D) the polymerization initiator contains (D1) the thermal polymerization initiator, is photocurable if (D) the polymerization initiator contains (D2) the photopolymerization initiator, and is photo- and thermosetting if (D) the polymerization initiator contains both (D1) the thermal polymerization initiator and (D2) the photopolymerization initiator.

[0096] When the resin composition is heat-cured, it can be cured by, for example, a heat treatment at 40 to 200°C for 0.1 to 300 minutes. Under conditions of 100°C, curing is preferably within 5 hours, more preferably within 3 hours, and even more preferably within 1 hour. When the resin composition of this embodiment is used in the manufacture of semiconductor devices or electronic components that include parts that degrade under high-temperature conditions, it is preferable to heat-cur the composition at a temperature of 40 to 90°C for 30 to 120 minutes. For example, when the resin composition is used in an optical sensor module, the curing temperature is preferably 40 to 90°C, and more preferably 60 to 90°C.

[0097] When a resin composition is photocured, the light used for irradiation is, for example, ultraviolet (UV) light. In this specification, ultraviolet light refers to light rays with a wavelength in the range of 200 nm to 410 nm. The resin composition of this embodiment can be cured by irradiation at any of the wavelengths of 365 nm, 385 nm, or 405 nm. The irradiation dose of the light is 50 mJ / cm². ２ ~2000mJ / cm ２ It is preferable that this be the case.

[0098] If the resin composition of this embodiment contains (D1) a thermal polymerization initiator and (D2) a photopolymerization initiator, the resin composition can be further cured by heat, for example, after or during light (UV) curing.

[0099] The resin composition of this embodiment can be used, for example, as an adhesive or sealant for fixing, joining, or protecting semiconductor devices or electronic components or the components that make them up, or as a raw material thereof.

[0100] [Adhesive or Sealant] An adhesive or sealant according to one aspect of the present invention comprises the resin composition of the above aspect. This adhesive or sealant enables good fixing, bonding, or protection of general-purpose plastics (e.g., PE, PS, PP, etc.), engineering plastics (e.g., LCP (liquid crystal polymer), polyphthalamide, polycarbonate, polyamide, polybutylene terephthalate, polyimide, etc.), glass, ceramics, metals (e.g., copper, nickel, SUS, etc.), organic substrates (e.g., FR4, etc.), flexible printed circuit boards (FPC), etc., and can be used to fix, bond, or protect components constituting semiconductor devices or electronic components. Examples of semiconductor devices include, but are not limited to, HDDs, semiconductor elements, optical sensor modules such as image sensor modules and TOF sensor modules, other semiconductor modules, and integrated circuits.

[0101] The adhesive or sealant of this embodiment may be a one-component adhesive or sealant contained in a single container, or a two-component (or multi-component) adhesive or sealant contained in two or more containers, depending on its application. When used as a two-component (or multi-component) adhesive or sealant, components (A) to (D) and other optional components as needed can be selected in the same way as for the one-component type, and the curing method is also the same as for the one-component type. Furthermore, when used as a two-component (or multi-component) adhesive or sealant, components (A) to (D) 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 (D) and other optional components as needed may be contained in each liquid, components (A) to (D) may be contained in one liquid, or there may be a liquid consisting only of components (A) to (D) and / or other optional components as needed. For example, when dividing into liquid A and liquid B, the division may be as follows: liquid A: component (A), liquid B: component (B), component (C), and component (D); liquid A: component (A) and component (B), liquid B: component (C) and component (D); liquid A: component (A) and component (C), liquid B: component (B) and component (D); liquid A: component (A), component (B), and component (C), liquid B: component (D); liquid A: component (A), component (B), and component (D), liquid B: component (C); or liquid A: component (A), component (C), and component (D), liquid B: component (B). If components (A) to (D) are contained in liquid A and the other components are contained in liquid B, liquid A alone, or liquids A and B together, can be considered as the adhesive or sealant of this embodiment. On the other hand, if components (A) to (D) are each contained in separate liquids, the combined liquids can be considered as the adhesive or sealant of this embodiment. An example of a case where components (A) to (D) are each contained in separate liquids is, for example, an adhesive or sealant in which components (A) to (D) are divided into two or more containers, specifically a kit consisting of multiple liquids containing any of components (A) to (D).

[0102] [Cured product of resin composition, adhesive or sealant] A cured product according to one aspect of the present invention is a cured product obtained by curing the resin composition, adhesive or sealant according to the above aspect.

[0103] [Semiconductor devices, electronic components] A semiconductor device or electronic component according to one aspect of the present invention includes a cured product according to the above aspect. Here, "semiconductor device" refers to all devices that can function by utilizing semiconductor properties, and includes electronic components, semiconductor circuits, modules incorporating these, electronic devices, etc. Examples of semiconductor devices or electronic components include, but are not limited to, HDDs, semiconductor elements, optical sensor modules such as image sensor modules and TOF sensor modules, other semiconductor modules, and integrated circuits.

[0104] 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.

[0105] [Preparation of Resin Composition] Resin compositions were prepared by mixing predetermined amounts of each component using a three-roll mill according to the formulations shown in Table 1. In Table 1, the amount of each component is expressed in mass %. The components used in the examples and comparative examples are as follows.

[0106] • (A) (meth)acrylate compounds (component (A)) (A-1): Dimethylol-tricyclodecanediaacrylate (product name: Light Acrylate DCP-A, manufactured by Kyoeisha Chemical Co., Ltd., (meth)acryloyl equivalent: 152 g / eq) (A-2): Polyester acrylate (product name: Aronics M7100, manufactured by Toagosei Co., Ltd., (meth)acryloyl equivalent: 188 g / eq) (A-3): Trimethylolpropane trimethacrylate (product name: TMPT, manufactured by Shin Nakamura Chemical Industry Co., Ltd., (meth)acryloyl equivalent: 112.8 g / eq) (A-4): Polycarbonate-based urethane acrylate (product name: Art Resin UN-9000PEP, manufactured by Negami Kogyo Co., Ltd., (meth)acryloyl equivalent: 2500 g / eq) • (B) Polythiol compounds (Component (B)) (B-1): Pentaerythritol tetrakis(3-mercaptopropionate) (Product name: PEMP, manufactured by SC Organic Chemicals, thiol equivalent: 122 g / eq) (B-2): 1,3,4,6-tetrakis(3-mercaptopropyl) glycoluryl (Product name: C3 TS-G, manufactured by Shikoku Chemicals, Inc., thiol equivalent: 110 g / eq) (B-3): 1,3,5-Tris[3-(2-mercaptoethylsulfanyl)propyl]isocyanurate (Product name: ACTOCURE® SS32, manufactured by Kawaguchi Chemical Industry Co., Ltd., thiol equivalent: 183 g / eq) • (C) Allyl compounds (Component (C)) (C-1): 2,2'-diallylbisphenol A (product name: BPA-CA, manufactured by Konishi Chemical Industry Co., Ltd., allyl equivalent: 160 g / eq) (C-2): Bisphenol A bisallyl ether (Fujifilm Wako Pure Chemical Industries, Ltd., allyl equivalent: 154 g / eq) (C-3): Trimethylolpropanediallyl ether (product name: Neoallyl ＴＭ(C-4): Allylphenol resin (product name: APG, manufactured by Gun-ei Kogyo Co., Ltd., allyl equivalent: 107 g / eq) (C-5): Polyfunctional allylphenol resin (product name: FATC, manufactured by Gun-ei Kogyo Co., Ltd., allyl equivalent: 586 g / eq) (C-6): Triallyl isocyanurate (product name: TAIC, manufactured by Tokyo Chemical Industry Co., Ltd., allyl equivalent: 83.1 g / eq) ・(C') Polymerizable compounds other than components (A) to (C) (C'-1): Bisphenol F type epoxy resin / Bisphenol A type epoxy resin mixture (aromatic epoxy resin) (product name: EXA835LV, manufactured by DIC Corporation, epoxy equivalent: 165 g / eq) ・(D) Polymerization initiator (component (D)) (D1-1): Amine-epoxy adduct-type thermal latent curing catalyst (Product name: Novacure HXA3922HP, core-shell type, manufactured by Asahi Kasei Corporation, thermal anionic polymerization initiator) (D1-2): Amine-epoxy adduct-type thermal latent curing catalyst (Product name: Novacure HX-3722, core-shell type, manufactured by Asahi Kasei Corporation, thermal anionic polymerization initiator) (D2-1): 1-Hydroxycyclohexyl-phenyl ketone (Product name: Omnirad 184, manufactured by IGM Resins B.V., photoradical polymerization initiator) (D2-2): 2,2-dimethoxy-2-phenylacetophenone (Product name: Omnirad 651, manufactured by IGM Resins B.V., photoradical polymerization initiator) ・(E) Radical polymerization inhibitor (Component (E)) (E-1) N-nitroso-N-phenylhydroxylamine aluminum (manufactured by Wako Pure Chemical Industries, Ltd.) • (F) Swixing agent (component (F)) (F-1): Hydrophobic fumed silica manufactured by CABOT (product name: CAB-O-SIL® TS720, average particle size: 12 nm) • (G) Coupling agent (component (G)) (G-1): Silane coupling agent with methacrylic group (product name: KBM-503, manufactured by Shin-Etsu Chemical Co., Ltd.)

[0107] The following measurements were performed on the samples obtained for the examples and comparative examples.

[0108] [Measurement of Adhesion Strength (Shear Strength) of Thermocured Products to Engineering Plastics] (1) On LCP substrates, polyphthalamide (PPA) substrates, and polycarbonate (PC) substrates, which are engineering plastic substrates, the resin compositions of Examples 1 to 16 and Comparative Example 1 were applied by stencil printing to a diameter of φ2 mm and a thickness of 100 μm, respectively. Alumina chips measuring 3.2 mm × 1.6 mm × 0.45 mm thick were laminated on the applied resin compositions, and test specimens were prepared by applying a light load. These test specimens were cured under thermocuring conditions. Under thermocuring conditions, the test specimens were left to stand in a forced-air dryer at 80°C for 60 minutes to thermocur. (2) The alumina chips on the LCP substrate, polyphthalamide (PPA) substrate, and polycarbonate (PC) substrate of the test specimens obtained in (1) above were punctured from the side with a bond tester (Dage Series 4000) at 23°C, and the stress (N) at which the alumina chip 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 is shown in Table 1 as the shear strength of the cured material (unit: N / Chip).

[0109] [Measurement of Adhesion Strength (Shear Strength) of Photocured and Thermocured Products to Engineering Plastics] (1) The resin compositions of the examples and comparative examples were applied to LCP substrates, polyphthalamide (PPA) substrates, and polycarbonate (PC) substrates, respectively, by stencil printing in a diameter of φ2 mm and a thickness of 100 μm. Alumina chips measuring 3.2 mm × 1.6 mm × 0.45 mm thick were then laminated on the applied resin compositions, and a light load was applied to create test specimens. These test specimens were cured under photocuring and thermocuring conditions. Under photocuring and thermocuring conditions, a single-wavelength UV LED light source (OmniCure® AC475, manufactured by Excelitas Technologies) was used to irradiate the test specimens at a height of 4 cm from the top surface of the test specimen to the light source, with a wavelength of 365 nm and an irradiation intensity of 500 mW / cm². ２ And the accumulated light intensity is 2000 mJ / cm ２(Measured using an ultraviolet integrated light meter UIT-250 and a photodetector UVD-S365 (manufactured by Ushio Inc.)) After continuous irradiation until the desired result was reached, the specimens were left to stand in a forced-air dryer at 80°C for 60 minutes to allow for photo- and thermal curing. (2) The alumina chips on the substrate of the test specimens obtained in (1) above 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 is shown in Tables 2 to 4 as the shear strength (unit: N / Chip) of the cured material.

[0110] [Measurement of Adhesion Strength (Shear Strength) of Thermo-cured and Photo-cured Products to Metals] The shear strength (unit: N / Chip) of thermo-cured and photo-cured products was determined in the same manner as above, except that a nickel substrate was used instead of an engineering plastic substrate. The results are shown in Table 5.

[0111] [Dispensability] The resin compositions of Examples 12 and 16 were continuously dispensed using a VERMES Microdispensing MDS 3200F jet dispenser. The number of shots that could be dispensed continuously was measured and evaluated using the following index. The dispensability of Examples 12 and 16 was evaluated as ○. ○: The number of shots that could be dispensed continuously was 100,000 or more. △: The number of shots that could be dispensed continuously was 10,000 or more but less than 100,000. ×: The number of shots that could be dispensed continuously was less than 10,000.

[0112]

[0113]

[0114]

[0115] The resin compositions of Examples 1 to 16, which satisfy the configuration of the present invention, exhibited high adhesive strength (shear strength) of the cured product to the engineering plastic substrate after thermosetting. On the other hand, the resin composition of Comparative Example 1, which does not satisfy the configuration of the present invention, exhibited lower adhesive strength (shear strength) of the cured product to the engineering plastic substrate than that of the resin compositions of Examples 1 to 16, which satisfy the configuration of the present invention.

[0116]

[0117]

[0118] As can be seen from Tables 2 to 4, the resin compositions of the examples tended to exhibit high adhesive strength (shear strength) to engineering plastic substrates, both in their photo-cured and heat-cured products. As can be seen from Table 5, the resin compositions of the examples also showed good adhesive strength (shear strength) to metals, both in their heat-cured products and in their photo-cured and heat-cured products.

[0119] The disclosure of Japanese Patent Application No. 2025-051668 (filing date: March 26, 2025) is incorporated herein by reference in its entirety. All documents, patent applications, and technical standards described herein are incorporated herein by reference to the same extent as if each individual document, patent application, and technical standard were specifically and individually noted to be incorporated by reference.

Claims

1. A curable resin composition comprising (A) a (meth)acrylate compound, (B) a polythiol compound, (C) an allyl compound, and (D) a polymerization initiator, wherein the proportion of compounds having heterocyclic and / or aromatic rings among the (B) polythiol compound and the (C) allyl compound is 5% by mass or more.

2. The curable resin composition according to claim 1, wherein the thiol equivalent of the (B) polythiol compound is 50 to 1000 g / eq.

3. The curable resin composition according to claim 1 or 2, wherein the allyl equivalent of the (C) allyl compound is 50 to 1000 g / eq.

4. The curable resin composition according to any one of claims 1 to 3, wherein the (C) allyl compound comprises an allyl compound having a hydroxyl group.

5. The curable resin composition according to claim 4, wherein the hydroxyl group is a phenolic hydroxyl group.

6. The curable resin composition according to any one of claims 1 to 5, wherein the compound having a heterocyclic and / or aromatic ring in (B) a polythiol compound and / or (C) an allyl compound is a compound having a bisphenol skeleton, a glycoluryl skeleton, or an isocyanuric acid skeleton.

7. An adhesive or sealant comprising the curable resin composition according to any one of claims 1 to 6.

8. The adhesive or sealant according to claim 7, used for fixing, bonding, or protecting components constituting an optical sensor module.

9. A cured product obtained by curing a curable resin composition according to any one of claims 1 to 6, or an adhesive or sealant according to claim 7 or 8.

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

11. The semiconductor device or electronic component according to claim 10, which is an optical sensor module.

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