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

Abstract

The present application provides a resin composition having good storage stability and low-temperature curing properties even when a specific trithiol compound is included, an adhesive or sealing material containing the resin composition, a cured product, and a semiconductor device or electronic component. The present application provides a resin composition containing: (A) a (meth)acrylate compound, (B) a thiol compound represented by Chemical Formula (I), (C) a thermolatent curing catalyst, and (D) an inorganic filler having a specific surface area of 4 m 2 / g or more, and an adhesive or sealing material containing the resin composition, a cured product, and a semiconductor device or electronic component.

Description

Technical Field

[0001] This invention relates to resin compositions, adhesives or sealants comprising the resin compositions, cured products thereof, semiconductor devices comprising the cured products, and electronic components. Background Technology

[0002] Currently, adhesives and sealants containing curable resin compositions are frequently used in the assembly and installation of components used in semiconductor devices, such as semiconductor chips, to maintain reliability. Among such resin compositions are known curable compositions that use epoxy compounds or (meth)acrylate compounds as the main agents and thiol compounds as the curing agents (e.g., Patent Document 1 or 2).

[0003] Patent document 3 discloses a trithiol compound that can be used as a curing agent for various resins and has the following structural formula:

[0004] [Chemistry 1]

[0005]

[0006] Existing technical documents

[0007] Patent documents

[0008] Patent Document 1: Japanese Patent Application Publication No. 6-211969

[0009] Patent Document 2: Japanese Patent Application Publication No. 2009-51954

[0010] Patent Document 3: Japanese Patent Application Publication No. 2022-180364 Summary of the Invention

[0011] The inventors investigated curable compositions using (meth)acrylate compounds as the main agent and trithiol compounds described in Patent Document 3 as the curing agent. The results showed that, from the viewpoint of preservation stability, when using a heat-latent curing catalyst as the curing catalyst, the curing performance was insufficient, especially at low temperatures (e.g., 80°C). In the case of semiconductor devices and electronic components containing parts that deteriorate under high-temperature conditions, the manufacturing processes must be carried out at low temperatures. Therefore, adhesives and sealing materials used in the manufacture of such devices and components must exhibit sufficient curing performance even at low temperatures.

[0012] The objective of this invention is to provide resin compositions that exhibit good storage stability and low-temperature curing properties even when containing specific trithiol compounds, adhesives or sealants containing the resin compositions, cured products, and semiconductor devices or electronic components.

[0013] The specific methods used to solve the above problems are as follows.

[0014] The present invention includes resin compositions, adhesives or sealants, cured products, and semiconductor devices or electronic components in the following ways.

[0015] [1] A resin composition comprising:

[0016] (A) (meth)acrylate compounds,

[0017] (B) Thiol compounds represented by chemical formula (I):

[0018] [Chemistry 2]

[0019]

[0020] (C) Thermally latent curing catalysts, and

[0021] (D) Specific surface area is 4m² 2 Inorganic fillers of / g or higher.

[0022] [2] The resin composition described in [1] above further comprises (E) a photopolymerization initiator.

[0023] [3] According to the resin composition described in [1] or [2] above, wherein the content of the inorganic filler (D) above is 1 to 90% by weight relative to the total weight of the resin composition.

[0024] [4] The resin composition according to any one of [1] to [3] above, wherein the ratio of the total surface area of ​​the inorganic filler (D) in the resin composition to the content of the heat-latent curing catalyst (C) in the resin composition is 7 to 400 m². 2 / g.

[0025] [5] The resin composition according to any one of [1] to [4] above, wherein the content of (meth)acrylate compound with an average molecular weight of less than 250 in the resin composition is 0 to 90 by weight relative to the content of component (B) in the resin composition.

[0026] [6] The resin composition according to any one of [1] to [5] above further comprises a thiol compound other than component (B) (B), wherein the ratio of the number of (meth)acryloyl equivalents of component (A) to the total number of thiol equivalents of component (B) and component (B') ([number of (meth)acryloyl equivalents of component (A)] / ([number of thiol equivalents of component (B)] + [number of thiol equivalents of component (B')])) is 0.1 to 10.

[0027] [7] The resin composition described in any one of [1] to [6] above is configured such that the above components (A) to (D) are packaged in a single container.

[0028] [8] The resin composition described in any one of [1] to [6] above is configured such that the above components (A) to (D) are packaged in two or more containers.

[0029] [9] An adhesive or sealant comprising the resin composition described in any one of [1] to [8] above.

[0030]

[10] The adhesive or sealing material described in [9] above is used in semiconductor devices or electronic components.

[0031]

[11] A cured product obtained by curing the resin composition described in any one of [1] to [8] above, or the adhesive or sealant described in [9] or

[10] above.

[0032]

[12] A semiconductor device or electronic component comprising the cured material described in

[11] above.

[0033] According to the present invention, it is possible to provide resin compositions that have good storage stability and low-temperature curing properties even when containing specific trithiol compounds, adhesives or sealants containing the resin compositions, cured products formed by curing them, and semiconductor devices or electronic components containing the cured products. Detailed Implementation

[0034] In accordance with convention in the field of synthetic resins, the term "resin," which generally refers to a polymer (especially a synthetic polymer), is sometimes used for components constituting a curable resin composition before curing, even if the components are not polymers, such as prepolymer compounds before curing.

[0035] [Resin Composition]

[0036] As one aspect of the present invention, the resin composition comprises:

[0037] (A) (meth)acrylate compounds,

[0038] (B) Thiol compounds represented by chemical formula (I):

[0039] [Chemistry 3]

[0040]

[0041] (C) Thermally latent curing catalysts, and

[0042] (D) Specific surface area is 4m² 2 Inorganic fillers of / g or higher.

[0043] According to this method, it is possible to provide resin compositions that have good storage stability and low-temperature curing properties even when containing trithiol compounds of formula (I).

[0044] (A) (Meth)acrylate compound

[0045] The resin composition of this method comprises (A) (meth)acrylate compound (hereinafter also referred to as "component (A)"). (A) (meth)acrylate compound imparts curability and adhesiveness to the resin composition. There is no particular limitation on the (meth)acrylate compound used as component (A), as long as it comprises a polyfunctional (meth)acrylate compound having at least two (meth)acryloyl groups. From the viewpoint of adhesion and reactivity, the polyfunctional (meth)acrylate compound is preferably a compound having 2 to 6 (meth)acryloyl groups, and more preferably a compound having 2 (meth)acryloyl groups. In this specification, "(meth)acryloyl" means both methacryloyl and acryloyl groups. Furthermore, "(meth)acrylate compound" means both acrylate compound and methacrylate compound.

[0046] Examples of (meth)acrylate compounds include di(meth)acrylates of tri(2-hydroxyethyl) isocyanurate, tri(2-hydroxyethyl) isocyanurate tri(meth)acrylate, trimethylolpropane tri(meth)acrylate, or oligomers thereof; pentaerythritol tri(meth)acrylate, or oligomers thereof; dipentaerythritol poly(meth)acrylates; tri(acryloyloxyethyl) isocyanurate; caprolactone-modified tri((meth)acryloyloxyethyl) isocyanurate; alkyl-modified dipentaerythritol poly(meth)acrylates; caprolactone-modified dipentaerythritol poly(meth)acrylates; ethoxylated bisphenol A di(meth)acrylates; (meth)propane The products include, but are not limited to, dihydrocyclopentadienyl acrylates, polyester (meth)acrylates, dimethyloltricyclodecane di(meth)acrylates, bis(trimethylolpropane) poly(meth)acrylates, polyurethanes having two or more (meth)acryloyl groups in one molecule, polyesters having two or more (meth)acryloyl groups in one molecule, phenoxyethyl methacrylate, isobornyl methacrylate, phenoxydiethylene glycol (meth)acrylate, 4-tert-butylcyclohexyl methacrylate, epoxy resin hemi(meth)acrylates, and (meth)acrylates having allyloxymethyl groups (see Japanese Patent Application Publication No. 2024-009452).

[0047] Commercially available (meth)acrylate compounds include, for example, polyester acrylate (product name: EBECRYL810) manufactured by Daicel Allnex Co., Ltd., bis(trimethylolpropane)tetraacrylate (product name: EBECRYL140) manufactured by Daicel Allnex Co., Ltd., polyester acrylate (product name: M7100) manufactured by Toa Synthetic Co., Ltd., dimethylol-tricyclodecane diacrylate (product name: Light Acrylate DCP-A) manufactured by Kyoei Chemical Co., Ltd., and neopentyl glycol-modified trimethylolpropane diacrylate (product name: KAYARAD R-604) manufactured by Nippon Kayaku Co., Ltd., but are not limited to these.

[0048] (A) Any one (meth)acrylate compound may be used, or two or more may be used in combination.

[0049] In this method, the content of (A) (meth)acrylate compound in the resin composition is preferably 10 to 90% by weight relative to the total weight of the resin composition, more preferably 15 to 85% by weight, further preferably 20 to 80% by weight, and particularly preferably 25 to 70% by weight.

[0050] The content of (meth)acrylate compounds with an average molecular weight of less than 250 in the resin composition can be 0 to 150% by weight relative to the content of the thiol compound represented by chemical formula (I) in (B) of the resin composition. From the viewpoint of suppressing the aggregation of the heat-latent curing catalyst (C) described later and from the viewpoint of the adhesive strength of the cured resin composition, the content of (meth)acrylate compounds with an average molecular weight of less than 250 in the resin composition is preferably 0 to 90% by weight relative to the content of the thiol compound represented by chemical formula (I) in (B) of the resin composition, more preferably 0 to 50% by weight, further preferably 0 to 30% by weight, and particularly preferably 0 to 10% by weight.

[0051] In addition, the total content of (meth)acrylate compounds with an average molecular weight of less than 250 and the content of thiol compounds represented by chemical formula (I) in the resin composition is preferably 5 to 90% by weight relative to the total amount of the resin composition, more preferably 10 to 80% by weight, and even more preferably 15 to 70% by weight.

[0052] It should be noted that, from the viewpoint of more easily obtaining the above-mentioned effects, it is most preferable that the resin composition does not substantially contain (meth)acrylate compounds with an average molecular weight of less than 250.

[0053] (B) Thiol compounds represented by chemical formula (I)

[0054] The resin composition of this method comprises (B) a thiol compound (1,2,3-tris(3-mercaptopropoxy)propane) of formula (I) (hereinafter also referred to as "the trithiol compound of formula (I)" or "component (B)"):

[0055] [Chemistry 4]

[0056]

[0057] The trithiol compound represented by formula (I) functions as a curing agent for (meth)acrylate compounds. The thiol compound represented by formula (I) can be synthesized, for example, by reacting 1,2,3-trienylpropoxypropane with a thiocarboxylic acid and then solvating the resulting thioester body according to the method described in Patent Document 3 (Japanese Patent Application Publication No. 2022-180364) or Japanese Patent Application Publication No. 2023-126883.

[0058] (B) The thiol compound represented by chemical formula (I) functions as a curing agent for (meth)acrylate compounds; however, this curing agent may be included as a byproduct generated during the synthesis of the thiol compound of chemical formula (I). Examples of byproducts include, for instance, the compounds represented by chemical formulas (I-1) to (I-9) as described in Japanese Patent Application Publication No. 2022-180364, but are not limited to them.

[0059] [Chemistry 5]

[0060]

[0061] [Chemistry 6]

[0062]

[0063] Other examples of byproducts include, for instance, the thiols with chemical formulas (I-1) to (I-45) as described in Japanese Patent Application Publication No. 2023-126883, (1) polymers of these thiols (e.g., dimers, trimers, etc.), (2) condensates selected from two or more of these thiols, and (3) condensates selected from one or more of these thiols and one or more of the thiols with chemical formulas (IV-1) to (IV-6) as described in Japanese Patent Application Publication No. 2023-126883, but are not limited to these.

[0064] When component (B) contains a byproduct of the compound represented by chemical formula (I), such as compounds (I-1) to (I-9) disclosed in Japanese Patent Application Publication No. 2022-180364, or compounds disclosed in Japanese Patent Application Publication No. 2023-126883, the ratio of the content of the byproduct of the compound represented by chemical formula (I) to the content of the compound represented by chemical formula (I) is preferably 0.02 to 0.3, more preferably 0.02 to 0.25, further preferably 0.05 to 0.25, and most preferably 0.05 to 0.20.

[0065] The ratio of the contents of each compound in the curing agent is calculated by using the peak area of ​​each component when performing liquid chromatography analysis on the curing agent.

[0066] In this method, the content of component (B) in the resin composition is preferably 1 to 70% by weight, more preferably 5 to 60% by weight, and even more preferably 10 to 50% by weight, relative to the total weight of the resin composition.

[0067] In this method, the ratio of the number of (meth)acryloyl equivalents of component (A) to the number of thiol equivalents of component (B) ([number of (meth)acryloyl equivalents of component (A)] / [number of thiol equivalents of component (B)]) is preferably 0.1 to 10, more preferably 0.2 to 10, and even more preferably 0.2 to 5.0.

[0068] In this specification, the terms "thiol equivalent," "(meth)acryloyl equivalent," and other functional group equivalents refer to the molecular weight of the compound with each functional group, while the terms "thiol equivalent number," "(meth)acryloyl equivalent number," and other functional group equivalent number refer to the number of functional groups (equivalents) per unit weight (feed amount) of the compound.

[0069] Theoretically, the methacryloyl equivalent of a meth)acrylate compound is obtained by dividing the molecular weight of the meth)acrylate compound by the number of methacryloyl groups in one molecule. The actual methacryloyl equivalent can be determined, for example, by NMR. The methacryloyl equivalent number of a meth)acrylate compound is the number of methacryloyl groups (equivalents) per unit weight (feed amount) of the meth)acrylate compound, which is the quotient obtained by dividing the weight (g) of the meth)acrylate compound by its methacryloyl equivalent (in the case of multiple meth)acrylate compounds, it is the sum of such quotients obtained for each meth)acrylate compound.

[0070] The thiol equivalent of a thiol compound is theoretically obtained by dividing the molecular weight of the thiol compound by the number of thiol groups in one molecule. In practice, the thiol equivalent can be determined, for example, by measuring the thiol value using a potentiometric method. This method is well-known, for example, as disclosed in Japanese Patent Application Publication No. 2012-153794, paragraph 0079. The thiol group equivalent number of a thiol compound is the number of thiol groups per unit weight (feed amount) of the thiol compound (equivalent number), which is the quotient obtained by dividing the weight (g) of the thiol compound by its thiol equivalent (in the case of multiple thiol compounds, it is the sum of such quotients obtained for each thiol compound).

[0071] (C) Thermally Latent Curing Catalyst

[0072] The resin composition of this method includes (C) a heat-latent curing catalyst (hereinafter also referred to as "component (C)"). A heat-latent curing catalyst is a compound or substance that is inert at room temperature but is activated by heating and functions as a curing catalyst. Examples of heat-latent curing catalysts include dicyandiamide; amine compounds that are solid at room temperature; amine adduct-type heat-latent curing catalysts such as reaction products of amine compounds and epoxy compounds (amine-epoxy adduct systems), reaction products of amine compounds and isocyanate compounds or urea compounds (amine-urea type adduct systems), and combinations thereof; microencapsulated heat-latent curing catalysts; and inclusion-type heat-latent curing catalysts, etc., which are solid-dispersed heat-latent curing catalysts. As component (C), from the viewpoint of the storage stability and curability of the resin composition, amine adduct-type heat-latent curing catalysts, microencapsulated heat-latent curing catalysts, and inclusion-type heat-latent curing catalysts are preferred. The amine compounds include aliphatic amines, aromatic amines, and heterocyclic amines.

[0073] Examples of amine compounds that are solid at room temperature include 2-heptadecylimidazole, 2-phenyl-4,5-dihydroxymethylimidazole, 2-undecylimidazole, 2-phenyl-4-methyl-5-hydroxymethylimidazole, 2-phenyl-4-benzyl-5-hydroxymethylimidazole, 2,4-diamino-6-(2-methyl-1-imidazolyl-(1))-ethyl-S-triazine, and 2,4-diamino-6-(2′-methylimidazolyl-(1)′)-ethyl-S-triazine. The adducts include methyl-S-triazine isocyanuric acid, 2-methylimidazolium, 2-phenylimidazolium, 2-phenyl-4-methylimidazolium, 1-cyanoethyl-2-phenylimidazolium, 1-cyanoethyl-2-methylimidazolium-trimethoxylate, 1-cyanoethyl-2-phenylimidazolium-trimethoxylate, N-(2-methylimidazolium-1-ethyl)-urea, N,N′-(2-methylimidazolium-(1)-ethyl)-hexamethylenediamine, etc., but are not limited to them.

[0074] Amine compounds used as one of the raw materials for manufacturing thermally latent curing catalysts for amine adducts only need to have one or more active hydrogen atoms capable of undergoing addition reactions with epoxy or isocyanate groups within the molecule, and at least one functional group selected from primary, secondary, and tertiary amines within the molecule. Examples of such amine compounds, in addition to the aforementioned amine compounds that are solid at room temperature, include aliphatic amines such as diethylenetriamine, triethylenetetramine, n-propylamine, 2-hydroxyethylaminopropylamine, cyclohexylamine, and 4,4′-diamino-dicyclohexylmethane; aromatic amine compounds such as 4,4′-diaminodiphenylmethane and 2-methylaniline; and heterocyclic amine compounds containing nitrogen atoms such as 2-ethyl-4-methylimidazolium, 2-ethyl-4-methylimidazoline, 2,4-dimethylimidazoline, piperidine, and piperazine; etc., but are not limited to these.

[0075] In addition, compounds, especially those containing tertiary amino groups within the molecule and imidazole derivatives, are raw materials for providing latent curing catalysts with excellent curing-promoting capabilities. Examples of such compounds include amine compounds such as dimethylaminopropylamine, diethylaminopropylamine, di-n-propylaminopropylamine, dibutylaminopropylamine, dimethylaminoethylamine, diethylaminoethylamine, and N-methylpiperazine; imidazole compounds such as 2-methylimidazole, 2-ethylimidazole, 2-ethyl-4-methylimidazole, 2-phenylimidazole, 2-phenyl-4,5-dihydroxymethylimidazole, 2-phenyl-4-methyl-5-hydroxymethylimidazole, 2-phenyl-4-methylimidazole, and 1-(2-aminoethyl)-2-methylimidazole; and imidazole compounds such as 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, and 1-(2-... 1-(2-hydroxy-3-butoxypropyl)-2-methylimidazol, 1-(2-hydroxy-3-butoxypropyl)-2-ethyl-4-methylimidazol, 1-(2-hydroxy-3-phenoxypropyl)-2-phenylimidazoline, 1-(2-hydroxy-3-butoxypropyl)-2-methylimidazoline, 2-(dimethylaminomethyl)phenol, 2,4,6-tris(dimethylaminomethyl)phenol, N-β-hydroxyethylmorpholine, 2-dimethylaminoethanethiol, 2 Alcohols, phenols, thiols, carboxylic acids, and acyl hydrazides, such as β-mercaptopyridine, benzimidazole, 2-mercaptobenzimidazole, 2-mercaptobenzothiazole, 4-mercaptopyridine, N,N-dimethylaminobenzoic acid, N,N-dimethylglycine, nicotinic acid, isonicotinic acid, pyridinecarboxylic acid, N,N-dimethylglycine hydrazide, N,N-dimethylpropionic acid hydrazide, nicotinic acid hydrazide, and isonicotinic acid hydrazide, are not limited to these categories.

[0076] Epoxy compounds used as raw materials for manufacturing thermally latent curing catalysts for amine-epoxy adduct systems include, but are not limited to, polyglycidyl ethers obtained by reacting polyphenols such as bisphenol A, bisphenol F, catechol, and resorcinol, or polyols such as glycerol 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; glycidyl amine compounds obtained by reacting 4,4′-diaminodiphenylmethane, m-aminophenol, etc., with epichlorohydrin; and polyfunctional epoxy compounds such as epoxidized phenol linear phenolic resins, epoxidized cresol linear phenolic resins, and epoxidized polyolefins, as well as monofunctional epoxy compounds such as butyl glycidyl ether, phenyl glycidyl ether, various phenylphenol glycidyl ethers, and glycidyl methacrylate.

[0077] Isocyanate compounds used as raw materials for manufacturing latent curing catalysts for amine-urea adduct systems include, for example, 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, phenylenediamine diisocyanate, p-phenylene diisocyanate, 1,3,6-hexamethylene triisocyanate, and dicycloheptane triisocyanate; and compounds containing terminal isocyanate groups obtained by reacting these polyfunctional isocyanate compounds with active hydrogen compounds. Examples of such compounds containing a terminal isocyanate group include addition compounds with a terminal isocyanate group obtained by the reaction of toluene diisocyanate with trimethylolpropane, and addition compounds with a terminal isocyanate group obtained by the reaction of toluene diisocyanate with pentaerythritol, but are not limited to these.

[0078] Urea compounds that can be used as raw materials for manufacturing latent curing catalysts for amine-urea adduct systems include, but are not limited to, urea and thiourea.

[0079] Amine adduct-based thermally latent curing catalysts are, for example, the above-mentioned (a) two components of an amine compound and an epoxy compound, (b) three components of the two components and an active hydrogen compound, or (c) combinations of two or three components of an amine compound and an isocyanate compound and / or a urea compound. They can be readily prepared by collecting and mixing the components, reacting them at a temperature from room temperature to 200°C, cooling and curing them, and then pulverizing them; or by reacting them in solvents such as methyl ethyl ketone, dioxane, or tetrahydrofuran, removing the solvent, and then pulverizing the solid components. Amine adduct-based thermally latent curing catalysts include combinations of amine-epoxy adduct-based curing catalysts and amine-urea type adduct-based curing catalysts.

[0080] A microencapsulated, thermally latent curing catalyst is a curing catalyst having a core composed of an amine adduct obtained by reacting an amine compound with an epoxy compound, an isocyanate compound, or a urea compound, and coated with a shell made of a synthetic resin or an inorganic oxide. Examples of amine compounds include the aforementioned amine compounds. From the perspective of exhibiting suitable latency, imidazole derivatives are preferred. Examples of imidazole derivatives include 2-methylimidazolium, 2-phenylimidazolium, 2-phenyl-4-methylimidazolium, 2-phenyl-4,5-dihydroxymethylimidazolium, and 2-phenyl-4-methyl-5-hydroxymethylimidazolium. Examples of synthetic resins used as the shell include phenolic resins, melamine resins, epoxy resins, polyurethane resins, and urea-formaldehyde resins; these resins can also be used in combination. Examples of inorganic oxides used as the shell include silica, alumina, titanium dioxide, and magnesium oxide.

[0081] Examples of commercially available thermally latent curing catalysts include the following products, but are not limited to them. Examples of 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 Co., Ltd.), "Novacure HX-3721" (Asahi Kasei Co., Ltd.), "Novacure HXA9322HP" (Asahi Kasei Co., Ltd.), "Novacure HXA3922HP" (Asahi Kasei Co., Ltd.), "Novacure HXA3932HP" (Asahi Kasei Co., Ltd.), and "Novacure HXA3932HP". HXA5945HP (Asahi Kasei Corporation product name), Novacure HXA5911HP (Asahi Kasei Corporation product name), Novacure HXA9382HP (Asahi Kasei Corporation product name), etc., but are not limited to these. The aforementioned "Novacure" series are also microencapsulated thermally latent curing catalysts. In addition, examples of amine-urea type adduct curing catalysts include "Fujicure FXE-1000" (T&K TOKA Co., Ltd.), "Fujicure FXR1020" (T&K TOKA Co., Ltd.), "Fujicure FXR-1030" (T&K TOKA Co., Ltd.), "Fujicure FXR-1110" (T&K TOKA Co., Ltd.), "Fujicure FXR1121" (T&K TOKA Co., Ltd.), "Fujicure FXR1081" (T&K TOKA Co., Ltd.), "Fujicure 1061" (T&K TOKA Co., Ltd.), and "Fujicure 1171" (T&K TOKA Co., Ltd.), but they are not limited to these.

[0082] So-called inclusion-type latent curing catalysts are curing catalysts with a structure in which guest molecules such as amine compounds are encapsulated at the molecular level in crystal cavities formed by the host molecules. As a commercially available example of an inclusion-type latent curing catalyst, "NISSOCURE TIC-188" (product name of Nippon Soda Co., Ltd.) can be cited.

[0083] (C) Any one of the thermally latent curing catalysts may be used, or two or more may be used in combination.

[0084] The content of component (C) in the resin composition is preferably 0.1 to 30% by weight, more preferably 0.5 to 20% by weight, and even more preferably 1 to 10% by weight, relative to the total weight of the resin composition.

[0085] It should be noted that component (C) includes components provided in the form of a dispersion of particles of a heat-latent curing catalyst dispersed in an epoxy resin. The resin composition of this method may also contain such an epoxy resin.

[0086] (D) Specific surface area is 4m² 2 / g or more of inorganic fillers

[0087] The resin composition of this method contains (D) a specific surface area of ​​4m². 2 / g or more of inorganic filler (hereinafter also referred to as "component (D)"). In a resin composition comprising (A) (meth)acrylate compound, (B) thiol compound represented by chemical formula (I) and (C) heat-latent curing catalyst, by further comprising (D) a specific surface area of ​​4m² 2 With inorganic fillers of / g or higher, the low-temperature curability of the resin composition is improved. In this specification, unless otherwise specified, specific surface area refers to the BET specific surface area determined by the BET method.

[0088] The inventors have studied curable compositions using (meth)acrylate compounds as the main agent and trithiol compounds represented by chemical formula (I) as the curing agent. The results showed that, when using a heat-latent curing catalyst as the curing catalyst, the curing performance, especially at low temperatures (e.g., 80°C), was insufficient compared to using a curing catalyst that had not undergone latency treatment. While not limited to the explanations below, the reasons for this can be inferred as follows: It can be considered that in the heat-based curing of (meth)acrylate compounds and thiols, basic catalysts such as amines can be used to advance the curing reaction through an anionic polymerization system. From the viewpoint of maintaining stability, various powder-type (including dispersions in epoxy resins) solidify at room temperature among heat-latent curing catalysts. When using such powdered, latent heat-curing catalysts, in polymerization systems of (meth)acrylate compounds with low viscosity and trithiols of formula (I) with very low viscosity, the powdered latent heat-curing catalyst agglomerates due to the lower viscosity of the curable composition, or the once dispersed latent heat-curing catalyst agglomerates again, resulting in reduced curability. Furthermore, it can be considered that trithiols of formula (I) with very few polar portions within their structure are particularly difficult to deprotonate at low temperatures. For example, in the case of ester-based thiols such as pentaerythritol tetra(3-mercaptopropionate), a six-membered ring structure is easily formed, thus facilitating the deprotonation (H). Additionally, for thiols containing OH groups, the OH group facilitates the deprotonation of the thiol.

[0089] In this method, the resin composition contains a specific surface area of ​​4m². 2 Even when using a thermally latent curing catalyst as the curing catalyst, the heat-based curability of the (meth)acrylate compound—the trithiol compound represented by chemical formula (I)—is improved with inorganic fillers of 4 m² / g or more. The reason for this, while not limited to the following explanation, can be attributed to complex mechanisms such as (1) a specific surface area of ​​4 m² / g. 2 / g or more of inorganic fillers inhibit the agglomeration or re-agglomeration of thermally latent curing catalysts; (2) Inorganic fillers with polar groups on the surface become reaction sites for the protons of the thiol groups of trithiol compounds of formula (I) that are easy to remove.

[0090] From the perspective of suppressing the aggregation or reaggregation of latent solidification catalysts and considering that the surface of inorganic fillers with polar groups can serve as a reaction site for the easy removal of protons from the thiol groups of trithiol compounds of formula (I), it is crucial that inorganic particles possess a certain specific surface area. (D) Specific surface area of ​​4m² 2There is no particular limit to the upper limit of the specific surface area of ​​inorganic fillers of / g or more; however, from the viewpoint of moderate thickening and flowability of the resulting resin composition, 400m² is preferred. 2 / g or less, more preferably 300m 2 / g or less.

[0091] Inorganic fillers consist of granular bodies formed from inorganic materials, provided their specific surface area is 4m². 2 There are no particular limitations for materials of / g or above. 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. Inorganic fillers can be surface-treated with coupling agents such as silane coupling agents without impairing the effects of the present invention. It should be noted that even when inorganic fillers are surface-treated, the effect of inhibiting the agglomeration or re-agglomeration of thermally latent curing catalysts described in paragraph (1) above can still be obtained. In addition, even when inorganic fillers are surface-treated, since polar groups usually remain on the surface of the surface-treated particles, the effect described in paragraph (2) above can still be obtained, that is, the inorganic filler becomes a reaction site for the easy removal of protons of the thiol groups of the trithiol compound of formula (I).

[0092] The shape of inorganic fillers is not particularly limited and can be any shape, such as spherical, scaly, needle-like, or amorphous.

[0093] Specific surface area is 4m² 2 Inorganic fillers with a specific surface area of ​​less than 4 m² / g can be used, either one or more in combination. It should be noted that the resin composition may include fillers with a specific surface area of ​​less than 4 m² / g, without impairing the effects of the present invention. 2 / g of inorganic filler. From the viewpoint of inhibiting the agglomeration or re-agglomeration of (C) thermally latent solidification catalysts, the specific surface area is less than 4m². 2 The content of inorganic filler in g is relative to the specific surface area of ​​(D) which is 4m². 2 The content of inorganic filler of / g or more is preferably 0-90% by weight, more preferably 0-50% by weight, even more preferably 0-30% by weight, and particularly preferably 0-10% by weight. From the viewpoint of more easily obtaining the above-mentioned effects, it is most preferable that the resin composition does not substantially contain any filler with a specific surface area of ​​less than 4m². 2 / g of inorganic filler.

[0094] The content of (D) inorganic filler in the resin composition of this method is preferably 1 to 90% by weight relative to the total weight of the resin composition, more preferably 1 to 80% by weight, and even more preferably 3 to 70% by weight.

[0095] In this method, the ratio of the total surface area of ​​the (D) inorganic filler in the resin composition to the content of the (C) heat-latent curing catalyst in the resin composition is preferably 7 to 400 m². 2 / g, more preferably 10-400m 2 / g.

[0096] In this method, the ratio of the total surface area of ​​the (D) inorganic filler in the resin composition to the content of the (A) (meth)acrylate compound in the resin composition is preferably 0.7 to 50 m². 2 / g, more preferably 1-50m 2 / g.

[0097] If necessary, the resin composition of this method may also contain any component other than the components (A) to (D) mentioned above, such as the substances described below.

[0098] (E) Photopolymerization initiator

[0099] The resin composition of this method may include (E) a photopolymerization initiator (hereinafter also referred to as "component (E)") without impairing the effects of the present invention. In this specification, a photopolymerization initiator refers to a reactant that absorbs light to generate free radicals, thereby promoting polymerization. By including a photopolymerization initiator, the photocuring (e.g., UV curing) of the resin composition is promoted, for example, by curing the resin composition using light (UV) or by further curing it by heat under light irradiation. The type of photopolymerization initiator is not particularly limited, and known materials can be used. Examples of photopolymerization initiators include alkyl phenyl ketone compounds, acylphosphine oxide compounds, oxime ester compounds, and compounds having photosensitive sites and peroxide structures, but are not limited to these.

[0100] Examples of alkyl phenyl ketone compounds include benzoyladium dimethyl ketals such as 2,2-dimethoxy-1,2-diphenylethane-1-one (commercially available as Omnirad 651 manufactured by IGM Resins BV); α-aminoalkyl phenyl ketones such as 2-methyl-2-morpholino(4-methylthiophenyl)-1-propanone (commercially available as Omnirad 907 manufactured by IGM Resins BV); α-hydroxyalkyl phenyl ketones such as 1-hydroxy-cyclohexyl-phenyl-one (commercially available as Omnirad 184 manufactured by IGM Resins BV); and 2-dimethylamino-2-(4-methyl-benzyl)-1-(4-morpholino-4-yl-phenyl)-1-butanone (commercially available as Omnirad 651 manufactured by IGM Resins BV). 379EG), 2-benzyl-2-(dimethylamino)-4'-morpholinophenylbutanone (commercially available as Omnirad 369 manufactured by IGM Resins BV), etc., but not limited to them.

[0101] Examples of acylphosphine oxide compounds include 2,4,6-trimethylbenzoyl-diphenylphosphine oxide (commercially available as Omnirad TPO H manufactured by IGM Resins BV) and bis(2,4,6-trimethylbenzoyl)-phenylphosphine oxide (commercially available as Omnirad 819 manufactured by IGM Resins BV), but are not limited to these.

[0102] Examples of oxime ester compounds include 1-[4-(phenylthio)]-1,2-octanedione-2-(O-benzoyl oxime) (trade name: IRGACURE OXE-01, manufactured by BASF), 1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazole-3-yl]-ethyl ketone-1-(O-acetyl oxime) (trade name: IRGACURE OXE-02, manufactured by BASF), 1-[9-ethyl-6-(1,3-dioxolane,4-(2-methoxyphenoxy)-9H-carbazole-3-yl]-methyl ketone, ethyl ketone-1-(O-acetyl oxime) (trade name: ADEKA OPT-N-1919, manufactured by ADEKA), etc., but are not limited to these.

[0103] Examples of compounds or their commercially available products that have photosensitive sites and peroxide structures include 3,3',4,4'-tetra(tert-butylperoxycarbonyl)benzophenone (BTTB), Perdual TA, and Perdual TX (all manufactured by Nippon Oil Co., Ltd.), but are not limited to these.

[0104] Other examples of photopolymerization initiators include 2-hydroxy-2-methyl-1-phenyl-1-propanone, diethoxyacetophenone, 1-(4-isopropylphenyl)-2-hydroxy-2-methyl-1-propanone, 1-(4-dodecylphenyl)-2-hydroxy-2-methyl-1-propanone, 4-(2-hydroxyethoxy)-phenyl(2-hydroxy-2-propyl)one, 2-methyl-1-[4-(methylthio)phenyl]-2-morpholino-1-propanone, benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin n-butyl ether, benzoin phenyl ether, and benzoin dimethyl ketal. Benzophenone, benzoylbenzoic acid, methyl benzoylbenzoate, 4-phenylbenzophenone, hydroxybenzophenone, benzoylacrylated benzophenone, 4-benzoyl-4'-methyldiphenyl sulfide, 3,3'-dimethyl-4-methoxybenzophenone, thioxanone, 2-chlorothioxanone, 2-methylthioxanone, 2,4-dimethylthioxanone, isopropylthioxanone, 2,4-dichlorothioxanone, 2,4-diethylthioxanone, 2,4-diisopropylthioxanone, 2,4,6-trimethylbenzoyldiphenylphosphine oxide, methyl benzoylformate, benzoyl, camphorquinone, etc., but not limited to these.

[0105] Photopolymerization initiators can be used alone or in combination of two or more.

[0106] Regarding the content of the photopolymerization initiator, from the viewpoint of the photocuring speed and storage stability of the resin composition, it is preferably 0.01 to 10% by weight, more preferably 0.04 to 8% by weight, relative to the total weight of the resin composition.

[0107] (F) Stabilizer

[0108] If desired, the resin composition of this embodiment may include a stabilizer (hereinafter also referred to as "component (F)") without impairing the effects of the present invention. The stabilizer can further improve the storage stability of the resin composition of this embodiment and extend its shelf life. Various known stabilizers can be used as stabilizers; however, from the viewpoint of highly improving storage stability, at least one selected from liquid borate ester compounds, aluminum chelates, and organic acids is preferred.

[0109] Examples of liquid borate esters include 2,2'-oxybis(5,5'-dimethyl-1,3,2-oxaborane), trimethyl borate, triethyl borate, tri-n-propyl borate, triisopropyl borate, tri-n-butyl borate, tripentyl borate, triallyl borate, trihexyl borate, tricyclohexyl borate, trioctyl borate, trinonyl borate, tridecyl borate, tri(dodecyl) borate, tri(hexadecyl) borate, tri(octadecyl) borate, tri(2-ethylhexyloxy)borane, bis(1,4,7,10-tetraoxaundecyl)(1,4,7,10,13-pentaoxatetradecyl)(1,4,7-trioxaundecyl)borane, tribenzyl borate, triphenyl borate, tri-o-toluene borate, tri-m-toluene borate, triethanolamine borate, etc. Since the liquid borate ester compound is liquid at room temperature (25°C), it can reduce the viscosity of the resin composition, and is therefore preferred. For example, aluminum chelate A (manufactured by Kawaken Fine Chemical Co., Ltd.) can be used as the aluminum chelate. For example, barbituric acid can be used as the organic acid.

[0110] Stabilizers can be any one type, or two or more types can be used in combination.

[0111] When a stabilizer is added, the amount added is preferably 0.01 to 30% by weight, more preferably 0.05 to 25% by weight, and even more preferably 0.1 to 20% by weight, relative to the total weight of the resin composition.

[0112] (B') Thiol compounds other than component (B)

[0113] The resin composition of this method may also contain thiols other than component (B') (hereinafter also referred to as "component (B')", "other thiols (B')", or "other thiols"). Examples of other thiols include:

[0114] Aliphatic thiols such as ethylenedithiol, propylenedithiol, hexamethylenedithiol, decamethyldithiol, toluene-2,4-dithiol, 2,2-bis(mercaptomethyl)-1,3-propanedithiol, 2-(mercaptomethyl)-2-methyl-1,3-propanedithiol, and 2-ethyl-2-(mercaptomethyl)-1,3-propanedithiol;

[0115] Aromatic thiols such as benzene dithiol, toluene dithiol, and xylene dithiol (p-xylene dithiol);

[0116] Cyclic sulfide compounds, such as polythiols containing a 1,4-dithiane ring;

[0117] 3-Thiapentane-1,5-dithiol, 4-mercaptomethyl-3,6-dithia-1,8-octanedithiol and other mercaptoalkyl sulfide compounds;

[0118] Mercaptopropionates such as pentaerythritol tetra(3-mercaptopropionate);

[0119] Terminal thiol compounds in epoxy resins;

[0120] 3,6-Dioxa-1,8-octanedithiol, mercaptoalkyl ether disulfide compounds, 2,2′-[[2,2-bis[(2-mercaptoethoxy)methyl]-1,3-propanediyl]bis(oxy)]bisethanethiol, 3,3′-[[2,2-bis[(3-mercaptopropoxy)methyl]-1,3-propanediyl]bis(oxy)]bis-1-propanethiol, 3-[2,2-bis[(3-mercaptopropoxy)methyl]butoxy]-1-propanethiol, 3-(3-mercaptopropoxy)-2,2-bis[(3-mercaptopropoxy)methyl]-1-propanol, 2,2-bis[(3-mercaptopropoxy)methyl]-1-butanol and other mercaptoalkyl ether compounds;

[0121] Glycourea-type thiols such as 1,3,4,6-tetra(2-mercaptoethyl)glycourea and 1,3,4,6-tetra(3-mercaptopropyl)glycourea;

[0122] Triazine thiols, such as 2-{2,4,6-trioxo-3,5-bis[2-(3-thioalkylpropionyloxy)ethyl]-1,3,5-triazine-1-yl}ethyl=3-thioalkylpropionate, 1,3,5-tris[3-(2-mercaptoethylthioalkyl)propyl]isocyanurate, and tri(3-mercaptopropyl)isocyanurate.

[0123] Other examples of thiols include trimethylolpropane tris(3-mercaptopropionate), tris-[(3-mercaptopropionyloxy)-ethyl]-isocyanurate, tetraethylene glycol bis(3-mercaptopropionate), dipentaerythritol hexa(3-mercaptopropionate), pentaerythritol tetra(3-mercaptobutyrate), 1,3,5-tris(3-mercaptobutyryloxyethyl)-1,3,5-triazine-2,4,6(1H,3H,5H)-trione, 1,3,4,6-tetra(mercaptomethyl)glyurea, 1,3,4,6-tetra(mercaptomethyl)-3a-methylglyurea, 1,3,4,6-tetra(2-mercaptoethyl)-3a-methylglyurea, 1,3,4,6-tetra(3-mercaptopropyl)-3a-methylglyurea, 1,3, 4,6-Tetra(mercaptomethyl)-3a,6a-dimethylglyurea, 1,3,4,6-Tetra(2-mercaptoethyl)-3a,6a-dimethylglyurea, 1,3,4,6-Tetra(3-mercaptopropyl)-3a,6a-dimethylglyurea, 1,3,4,6-Tetra(mercaptomethyl)-3a,6a-diphenylglyurea, 1,3,4,6-Tetra(2-mercaptoethyl)-3a,6a-diphenylglyurea, 1,3,4,6-Tetra(3-mercaptopropyl)-3a,6a-diphenylglyurea, 1,3,5-Tris[2-(3-mercaptopropoxy)ethyl]isocyanurate, pentaerythritol tripropanethiol, 3-[2,3-bis(3-thioalkylpropoxy)propoxy]propane-1-thiol, pentaerythritol tetrapropanethiol, 1,2,3-tris[2-(3-mercaptopropyl)propanethiol]propane-1-thiol, pentaerythritol tetrapropanethiol, 1,2,3-tris[2-(3-thioalkylpropoxy)propoxy)propanethiol]propane-1-thiol, pentaerythritol tetrapropanethiol, 1,2,3-tris[2-(3-thioalkyl ... (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, tetra(mercaptomethylthiomethyl)methane, tetra(2-mercaptoethylthiomethyl)methane, tetra(3-mercaptopropylthiomethyl)methane, 1,1,3,3-tetra(mercaptomethylthio)propane, 1,1,2,2-tetra(mercaptomethylthio)ethane, 1, 1,5,5-Tetra(mercaptomethylthio)-3-thiapentane, 1,1,6,6-Tetra(mercaptomethylthio)-3,4-dithiahexane, 2,2-bis(mercaptomethylthio)ethanethiol, 3-mercaptomethylthio-1,7-dimercapto-2,6-dithiaheptane, 3,6-bis(mercaptomethylthio)-1,9-dimercapto-2,5,8-trithianonane, 3-Mercaptomethylthio-1,6-dimercapto-2,5-dithiahexane, 1,1,9,9-tetra(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, tetra(2,2-Bis(mercaptomethylthio)ethyl)methane, tetra(4,4-bis(mercaptomethylthio)-2-thiabutyl)methane, 3,5,9,11-tetra(mercaptomethylthio)-1,13-dimercapto-2,6,8,12-tetrathiatridecane, 3,5,9,11,15,17-hexa(mercaptomethylthio)-1,19-dimercapto-2,6,8,12,14,18-hexathianonadecane, 9-(2,2-bis(mercaptomethylthio)ethyl)-3,5,13,15-tetra(mercaptomethylthio)-1,17-dimercapto-2,6,8,10,12,16-hexathiaheptadecane, 3,4,8,9-tetra(mercaptomethylthio)-1,11-dimercapto-2,5,7,10-tetrathiaundecane Alkane, 3,4,8,9,13,14-hexa(mercaptomethylthio)-1,16-dimercapto-2,5,7,10,12,15-hexathazahexadecane, 8-[bis(mercaptomethylthio)methyl]-3,4,12,13-tetra(mercaptomethylthio)-1,15-dimercapto-2,5,7,9,11,14-hexathazapentadecane, 4,6- bis[3,5-bis(mercaptomethylthio)-7-mercapto-2,6-dithiaheptylthio]-1,3-dithiaane, 4-[3,5-bis(mercaptomethylthio)-7-mercapto-2,6-dithiaheptylthio]-6-mercaptomethylthio-1,3-dithiaane, 1,1-bis[4-(6-mercaptomethylthio)-1,3-dithiaanethio]-1,3-bis( Mercaptomethylthio)propane, 1-[4-(6-mercaptomethylthio)-1,3-dithiacarbthio]-3-[2,2-bis(mercaptomethylthio)ethyl]-7,9-bis(mercaptomethylthio)-2,4,6,10-tetrathiaundecane, 3-[2-(1,3-dithiacyclobutyl)]methyl-7,9-bis(mercaptomethylthio)-1,11-dimercapto-2,4,6,10-tetrathiaundecane, 9-[2-(1,3-dithiacyclobutyl)]methyl-3,5,13,15-tetra(mercaptomethylthio)-1,17-dimercapto-2,6,8,10,12,16-hexaheptadecane, 3-[2-(1,3-dithiacyclobutyl)]methyl-7,9,13,15-tetra(mercaptomethylthio) 4,6-Bis[4-(6-mercaptomethylthio)-1,3-dithiacarbylthio]-6-[4-(6-mercaptomethylthio)-1,3-dithiacarbylthio]-1,3-dithiacarbylthio]-1,3-dithiacarbylthio],4-[3,4,8,9-tetra(mercaptomethylthio)-11-mercapto] [-2,5,7,10-tetrathiaundecyl]-5-mercaptomethylthio-1,3-dithiopentane, 4,5-bis[3,4-bis(mercaptomethylthio)-6-mercapto-2,5-dithiahexylthio]-1,3-dithiopentane, 4-[3,4-bis(mercaptomethylthio)-6-mercapto-2,5-dithiahexylthio]-5-mercaptomethylthio-1,3-Dithiopentane, 4-[3-bis(mercaptomethylthio)methyl-5,6-bis(mercaptomethylthio)-8-mercapto-2,4,7-trithiaoctyl]-5-mercaptomethylthio-1,3-dithiopentane, 2-{bis[3,4-bis(mercaptomethylthio)-6-mercapto-2,5-dithiahexylthio]methyl}-1,3-dithiacyclobutane, 2-[3,4-bis(mercaptomethylthio)-6-mercapto-2,5-dithiahexylthio]mercaptomethylthiomethyl-1,3-dithiacyclobutane, 2-[3,4,8,9-tetra(mercaptomethyl)methyl] [Thioyl)-11-mercapto-2,5,7,10-tetrathiaundecylthio] mercaptomethylthiomethyl-1,3-dithiacyclobutane, 2-[3-bis(mercaptomethylthio)methyl-5,6-bis(mercaptomethylthio)-8-mercapto-2,4,7-trithiaoctyl] mercaptomethylthiomethyl-1,3-dithiacyclobutane, 4-{1-[2-(1,3-dithiacyclobutyl)]-3-mercapto-2-thiapropylthio}-5-[1,2-bis(mercaptomethylthio)-4-mercapto-3-thiabutylthio]-1,3-dithiopentane, etc.

[0124] These other thiols can be used alone or in combination of two or more.

[0125] In the case of a thiol compound other than component (B), it is preferable to add the thiol equivalent number of component (B) to the thiol equivalent number of the thiol compound other than component (B) and calculate the ratio of the (meth)acryloyl equivalent number of component (A) to the total thiol equivalent number of the thiol compound ([(meth)acryloyl equivalent number of component (A)] / [total thiol equivalent number of the thiol compound]). In this embodiment, the ratio of the (meth)acryloyl equivalent number of component (A) to the total of the thiol equivalent number of component (B) and the thiol equivalent number of component (B') ([(meth)acryloyl equivalent number of component (A)] / ([thiol equivalent number of component (B)] + [thiol equivalent number of component (B')])) is preferably 0.1 to 10, more preferably 0.2 to 8, further preferably 0.3 to 6, particularly preferably 0.4 to 2, and most preferably 0.5 to 1.5.

[0126] Reactive diluents

[0127] If necessary, the resin composition of this method may include a reactive diluent to a extent that does not impair the effects of the present invention. In this specification, a reactive diluent refers to a compound having a reactive group that reacts with the thiol group of a thiol compound and has a low viscosity at room temperature. Examples of reactive diluents include monofunctional maleimide compounds, monofunctional (meth)acrylate compounds, monofunctional acrylamide compounds, and monofunctional epoxy compounds.

[0128] Monofunctional maleimide compounds are compounds that have one maleimide group as a reactive group with a thiol group. Examples of such compounds include maleimides; maleimides containing aliphatic hydrocarbon groups such as methylmaleimide, ethylmaleimide, propylmaleimide, butylmaleimide, hexylmaleimide, octylmaleimide, dodecylmaleimide, stearylmaleimide, and cyclohexylmaleimide; and maleimides containing aromatic rings such as phenylmaleimide.

[0129] Monofunctional (meth)acrylate compounds are compounds having one (meth)acryloyl group as a reactive group with a thiol group. 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, isodecanyl (meth)acrylate, isobornyl (meth)acrylate, stearyl (meth)acrylate, lauryl (meth)acrylate, and phenoxyethyl (meth)acrylate. Esters of monohydric alcohols and (meth)acrylic acid, including benzyl methacrylate, tetrahydrofurfuryl methacrylate, ethoxydiethylene glycol (meth)acrylate, phenoxydiethylene glycol (meth)acrylate, phenoxypolyethylene 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 methacrylate, and m-phenoxybenzyl methacrylate.2-Hydroxyethyl (meth)acrylate, 2-Hydroxypropyl (meth)acrylate, 2-Hydroxybutyl (meth)acrylate, 2-Hydroxy-3-phenoxypropyl (meth)acrylate, Octyl acrylate, Nonyl acrylate, Isononyl acrylate, 3,3,5-Trimethylcyclohexyl acrylate, Cyclomethylolpropane methyl acetal acrylate, 1-Naphthyl (meth)acrylate, 1-Ethylcyclohexyl (meth)acrylate, 1-Methylcyclohexyl (meth)acrylate, 1-Ethylcyclopentyl (meth)acrylate, 1-Methylcyclopentyl (meth)acrylate, Dicyclopentadienyl (meth)acrylate, (methyl) Dicyclopentadienyloxyethyl acrylate, dicyclopentyl acrylate, nonylphenoxy polyethylene glycol (meth)acrylate, tetrahydrodicyclopentadienyl acrylate, 2-(o-phenylphenoxy)ethyl acrylate, isobornylcyclohexyl acrylate, methyl methacrylate (2-methyl-2-ethyl-1,3-dioxacyclopentan-4-yl)acrylate, 1-adamantyl acrylate, 3-hydroxy-1-adamantyl acrylate, 2-methyl-2-adamantyl acrylate, 2-ethyl-2-adamantyl acrylate 2-Isopropyl-2-adamantyl ester of (meth)acrylate, 3-hydroxy-1-adamantyl ester of (meth)acrylate, (adamantyl-1-yloxy)methyl ester of (meth)acrylate, 2-Isopropyl-2-adamantyl ester of (meth)acrylate, 1-Methyl-1-ethyl-1-adamantyl methanol (meth)acrylate, 1,1-Diethyl-1-adamantyl methanol (meth)acrylate, 2-Cyclohexylpropane-2-yl ester of (meth)acrylate, 1-Isopropylcyclohexyl ester of (meth)acrylate, 1-Methylcyclohexyl ester of (meth)acrylate, 1-Ethylcyclopentyl ester of (meth)acrylate Mono(meth)acrylates or esters of monohydric alcohols and (meth)acrylic acid, including 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-1,3-dioxacyclopentan-4-yl)methyl (meth)acrylate, N-acryloyloxyethyl hexahydrophthalimide, α-acryloyl-ω-methoxypoly(oxyethylene), and 1-ethoxyethyl (meth)acrylate.

[0130] Monofunctional epoxy compounds are compounds that have one epoxy group as the reactive group with a thiol group. Examples of monofunctional epoxy compounds include monoepoxides such as n-butyl glycidyl ether, 2-ethylhexyl glycidyl ether, phenyl glycidyl ether, tolyl glycidyl ether, p-sec-butylphenyl glycidyl ether, styrene oxide, and α-pinene oxide; and monoepoxides with other functional groups such as allyl glycidyl ether, glycidyl methacrylate, and 1-vinyl-3,4-epoxycyclohexane.

[0131] Other additives

[0132] If necessary, the resin composition of this method may further contain other additives, such as coupling agents, carbon black, titanium black, ion trapping agents, leveling agents, antioxidants, defoamers, viscosity modifiers, flame retardants, colorants, solvents, etc., without prejudice to the main principles of this method. The types and amounts of each additive are as shown in the conventional method.

[0133] From the viewpoint of preventing a decrease in curing strength and sealing, preventing gas leakage and seepage, the resin composition of this method preferably does not contain liquid components such as water, solvents, and ionic liquids (excluding liquid components (A) to (C)). For example, it is preferable that the content of liquid components is 3% by weight or less relative to the total weight of the resin composition, and more preferably 1% by weight or less. Examples of solvents include 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, terpineol, isobornyl acetate, etc.), and halogen solvents (dichloromethane, chloroform, etc.), which are commonly used organic solvents in the field of curable compositions.

[0134] The method for manufacturing the resin composition of this method is not particularly limited. For example, components (A) to (D) and any other components used as needed can be simultaneously or separately introduced into a suitable mixer, and if necessary, mixed by heating and stirring to form a homogeneous composition, thereby obtaining the resin composition of this method. The mixer is not particularly limited, and a mortar and pestle mixer, Henschel mixer, three-roll mill, ball mill, planetary mixer, and bead mill equipped with a stirring and heating device can be used. In addition, these devices can be used in appropriate combinations.

[0135] The resin composition of this method can be formulated as a one-liquid resin composition that is packaged in a single container, or as a two-liquid (or multi-liquid) resin composition that is packaged in two or more containers, depending on its intended use. When formulating a two-liquid (or multi-liquid) resin composition, the aforementioned components (A) to (D) and any other components used as needed can be selected in the same manner as in the one-liquid composition. Furthermore, when formulating a two-liquid (or multi-liquid) resin composition, the aforementioned components (A) to (D) and any other components used as needed can be divided into two or more liquids in any dispensing manner without particular restriction. When divided into two or more liquids in any dispensing manner, each liquid may contain one or more components selected from the aforementioned components (A) to (D) and any other components used as needed; a single liquid may contain the aforementioned components (A) to (D); or a liquid may consist only of the aforementioned components (A) to (D) and / or any other components used as needed. For example, when the mixture is divided into liquid A and liquid B, the distribution can be as follows: liquid A: component (A), liquid B: component (B), component (C), and component (D); liquid A: component (A) and component (C), liquid B: component (B) and component (D); liquid A: component (A) and component (D), liquid B: component (B) and component (C); liquid A: component (B), liquid B: component (A), component (C), and component (D); liquid A: component (A), component (B), and component (D), liquid B: component (A), component (C), and component (D); or liquid A: component (A), component (B), component (C), and component (D), liquid B: component (B'). When components (A) to (D) are included in liquid A, and all other components are included in liquid B, liquid A alone, or liquid A and liquid B together, can be considered as the resin composition of this method. On the other hand, when the aforementioned components (A) to (D) are contained in different liquids, each liquid can be considered as a resin composition of this method. As an example of the aforementioned components (A) to (D) being contained in different liquids, a resin composition constructed by dispensing the aforementioned components (A) to (D) into two or more containers can be cited as an example. Specifically, a kit composed of multiple liquids containing any one of the aforementioned components (A) to (D) can be cited as an example.

[0136] The resin composition obtained in this way is thermosetting and preferably cures within 5 hours, more preferably within 3 hours, and even more preferably within 1 hour at a temperature of 100°C. When using the resin composition of this manner in the manufacture of a semiconductor device containing components that deteriorate under high-temperature conditions, it is preferable to heat-cure the composition at a temperature of 40–90°C for 30–120 minutes. The resin composition of this manner exhibits particularly excellent curability at low temperatures (e.g., 80°C).

[0137] When the resin composition of this method contains a (E) photopolymerization initiator, the resin composition can also be cured by light (UV). For example, it can be cured by light (UV) or further cured by heat under light irradiation.

[0138] The resin composition of this method can be used, for example, as an adhesive or sealant for fixing, joining or protecting semiconductor devices or electronic components or components constituting them, or as a raw material thereof.

[0139] [Adhesive or sealant]

[0140] As another aspect of the present invention, the adhesive or sealing material comprises the resin composition described above. This adhesive or sealing material can achieve good fixation, bonding, or protection for general-purpose plastics (e.g., PE, PS, PP, etc.), engineering plastics (e.g., LCP (liquid crystal polymer), polyamide, polycarbonate, etc.), ceramics, and metals (e.g., copper, nickel, etc.), and can be used for fixing, bonding, or protecting components constituting semiconductor devices or electronic parts. Examples of semiconductor devices include, but are not limited to, HDDs, semiconductor elements, image sensor modules, optical sensor modules such as TOF sensor modules, other semiconductor modules, and integrated circuits.

[0141] The adhesive or sealant of this method can be formulated as a one-component adhesive or sealant that can be packaged in a single container, or as a two-component (or multi-component) adhesive or sealant that can be packaged in two or more containers, depending on its intended use. When used as a two-component (or multi-component) adhesive or sealant, the aforementioned components (A) to (D), and any other components used as needed, can be selected in the same manner as in the one-component type, and the curing method is also the same as in the one-component type. Furthermore, when used as a two-component (or multi-component) adhesive or sealant, the aforementioned components (A) to (D), and any other components used as needed, can be divided into two-component or multi-component forms in any manner without particular restriction. When the liquid is divided into two or more liquids in any way, each liquid may contain one or more of the components (A) to (D) mentioned above and any other components used as needed. Alternatively, one liquid may contain the components (A) to (D) mentioned above. Alternatively, there may be a liquid consisting only of the components (A) to (D) mentioned above and / or any other components used as needed. For example, when the solution is divided into liquid A and liquid B, the distribution can be as follows: liquid A: component (A), liquid B: component (B), component (C), and component (D); liquid A: component (A) and component (C), liquid B: component (B) and component (D); liquid A: component (A) and component (D), liquid B: component (B) and component (C); liquid A: component (B), liquid B: component (A), component (C), and component (D); liquid A: component (A), component (B), and component (D), liquid B: component (A), component (C), and component (D); or liquid A: component (A), component (B), component (C), and component (D), liquid B: component (B'). When components (A) to (D) are included in liquid A, and all other components are included in liquid B, liquid A alone, or liquid A and liquid B together, can be considered as the adhesive or sealant of this method. On the other hand, when the aforementioned components (A) to (D) are contained in different liquids, each liquid can be considered as an adhesive or sealing material of this method. Examples of components (A) to (D) being contained in different liquids include adhesives or sealing materials constructed by dispensing components (A) to (D) into two or more containers; specifically, examples include kits composed of multiple liquids containing any one of the aforementioned components (A) to (D).

[0142] [Cure of resin composition, adhesive, or sealant]

[0143] Another aspect of the present invention is a cured product obtained by curing the resin composition, adhesive, or sealant described above.

[0144] [Semiconductor devices, electronic components]

[0145] As another aspect of the present invention, a semiconductor device or electronic component includes a cured product of the above-described manner. Here, "semiconductor device" refers to any device capable of functioning by utilizing the properties of semiconductors, including electronic components, semiconductor circuits, modules assembled thereon, electronic devices, etc. Examples of semiconductor devices or electronic components include, but are not limited to, HDDs, semiconductor elements, image sensor modules, optical sensor modules such as TOF sensor modules, other semiconductor modules, integrated circuits, etc.

[0146] Example

[0147] The present invention will be further described in detail below through embodiments and comparative examples; however, the present invention is not limited to these embodiments. It should be noted that in the following embodiments, unless otherwise specified, parts and percentages refer to parts by weight and percentage by weight.

[0148] [Preparation of the resin composition]

[0149] The resin compositions of the Examples, Comparative Examples, and Reference Examples were prepared by mixing the given amounts of each component using a three-roll mill according to the formulations shown in Tables 1 and 2. In Tables 1 and 2, the amounts of each component are expressed in parts by weight (in g). The components used in the Examples and Comparative Examples are shown below.

[0150] ·(A) (meth)acrylate compound

[0151] (A-1): Dihydroxymethyl-tricyclodecane diacrylate (Product name: Light Acrylate DCP-A, manufactured by Kyoei Chemical Co., Ltd., (meth)acryloyl equivalent: 152 g / eq, molecular weight: 304 g / mol)

[0152] (A-2): 2-functionalized alkoxylated bisphenol A acrylate (Product name: ABE-300, manufactured by Shin-Nakamura Chemical Industry Co., Ltd., (meth)acryloyl equivalent: 236 g / eq, molecular weight: 472 g / mol)

[0153] (A-3): Dipropylene glycol diacrylate (Product name: DPGDA, manufactured by Daicel Allnex Co., Ltd., (meth)acryloyl equivalent: 121 g / eq, molecular weight: 242 g / mol)

[0154] (A-4): Dipropylene glycol diacrylate (Product name: M-408, manufactured by Toa Synthetic Co., Ltd., (meth)acryloyl equivalent: 117 g / eq, molecular weight: 468 g / mol)

[0155] • (B) Thiol compounds represented by formula (I)

[0156] (B-1): The thiol compound shown in formula (I) (1,2,3-(3-mercaptopropoxy)propane) (obtained from Shikoku Chemical Industry Co., Ltd., thiol equivalent: 106 g / eq). It should be noted that this thiol equivalent is the average value measured by a known method, such as the method disclosed in paragraph 0079 of Japanese Patent Application Publication No. 2012-153794.

[0157] • Other thiols besides component (B')

[0158] (B'-1): Pentaerythritol tripropanethiol as shown in the following formula (product name: Multhiol Y-3, manufactured by SC Organic Chemicals Co., Ltd., thiol equivalent: 124 g / eq)

[0159] [Chemistry 7]

[0160]

[0161] (B'-2): 1,3,4,6-tetra(3-mercaptopropyl)glycourea as shown in the following formula (product name: C3 TS-G, manufactured by Shikoku Chemical Industry Co., Ltd., thiol equivalent: 110 g / eq)

[0162] [Chemistry 8]

[0163]

[0164] (C) Thermally Latent Curing Catalyst

[0165] (C-1): Amine adduct-based thermally latent curing catalyst (Product name: FUJICURE FXR-1121, a mixture of epoxy-modified imidazole and urea-modified amine, solid at room temperature, manufactured by T&K TOKA Co., Ltd.)

[0166] (C-2): Amine-epoxy adduct-based thermally latent curing catalyst (product name: NOVACURE HXA9322HP, manufactured by Asahi Kasei Corporation)

[0167] The thermally latent curing catalyst (C-2) is provided in the form of a dispersion (latent curing catalyst / mixture of bisphenol A type epoxy resin and bisphenol F type epoxy resin = 33 / 67 (weight ratio)) formed by dispersing particulate latent curing catalyst in epoxy resin (a mixture of bisphenol A type epoxy resin and bisphenol F type epoxy resin (epoxy equivalent: 180 g / eq)).

[0168] (C-3): Amine-urea type adduct system thermally latent curing catalyst (product name: FUJICURE FXR-1020, solid at room temperature, manufactured by T&K TOKA Co., Ltd.)

[0169] (D) Specific surface area is 4m² 2 / g or more of inorganic fillers

[0170] (D-1): Silica filler 1 (Product name: SEAHOSTAR (registered trademark) KE-S-30HG, amorphous silica, manufactured by Nippon Shokubai Co., Ltd., specific surface area: 12m³) 2 / g)

[0171] (D-2): Silica filler 2 (Product name: SE2300, manufactured by Admatechs Co., Ltd., specific surface area: 4.4 m²) 2 / g)

[0172] (D-3): Silica filler 3 (Product name: CAB-O-SIL (registered trademark) TS-720, polydimethylsiloxane surface-treated pyrolysis silica, manufactured by Cabot Corporation, specific surface area: 200m²) 2 / g)

[0173] (D-4): Alumina filler (Product name: ASFP-03S, manufactured by DENKA Corporation, specific surface area: 6.0 m²) 2 / g)

[0174] (D-5): Magnesium oxide filler (Product name: STARMAG PSF-150, manufactured by Shinjima Chemical Industry Co., Ltd., specific surface area: 145 m²) 2 / g)

[0175] • (D') Specific surface area less than 4m² 2 / g of inorganic filler

[0176] (D'-1): Silica filler 5 (Product name: FB-7SDX, manufactured by DENKA Corporation, specific surface area: 2.4m²) 2 / g)

[0177] (D'-2): Silica filler 6 (Product name: KYKLOS (registered trademark) MSV 25, manufactured by Ryusei Co., Ltd., specific surface area: 0.11 m²) 2 / g, average particle size: 25μm)

[0178] The specific surface area of ​​component (D'-2) is calculated using the following formula.

[0179] S=6 / Dρ

[0180] In the formula, S is the specific surface area (m²). 2 / g), D is particle size (diameter) (μm), ρ is density (g / cm³). 3 ).

[0181] • (E) Photopolymerization initiator

[0182] (E-1): 1-Hydroxy-cyclohexyl-phenyl-one (Product name: Omnirad 184, manufactured by IGM Resins BV)

[0183] (F) Stabilizer

[0184] (F-1): Triisopropyl borate

[0185] In Tables 1 and 2, "Specific surface area of ​​filler (m²)" 2 " / g)" represents the specific surface area of ​​the inorganic filler.

[0186] In Tables 1 and 2, "Total packing surface area (m²)" 2 ")" indicates the specific surface area (m²) of the inorganic filler. 2 The value is obtained by multiplying (g) by the weight of the inorganic filler in 100 parts by weight of the resin composition.

[0187] In Tables 1 and 2, "Total packing surface area / catalyst amount (m²)" is used. 2 " / g)" indicates the total surface area (m²) of the inorganic fillers in the resin composition. 2 The ratio of (C) to the content (g) of the heat-latent curing catalyst in the resin composition.

[0188] In Tables 1 and 2, "Total filler surface area / resin quantity (m²)" is used to indicate the total filler surface area / resin quantity. 2 " / g)" indicates the total surface area (m²) of the inorganic fillers in the resin composition. 2 The ratio of (A) (meth)acrylate compound to the content (g) of the resin composition.

[0189] In the examples, comparative examples, and reference examples, the properties of the resin composition and the cured product obtained by curing the resin composition were determined as follows.

[0190] [Evaluation of curing properties at 80℃]

[0191] Each resin composition was added dropwise at a rate of approximately 5 mm φ on a hot plate at 80±2°C. While stirring in a circular motion with a stirring rod and simultaneously lifting the stirring rod to detach the resin composition, the time until no more stringing occurred was measured using a stopwatch (gel time, unit: seconds). For Examples 1-5 and Comparative Examples 1-3, the relative gel time when the gel time of the resin composition of Comparative Example 1 (excluding inorganic fillers) was set to 1 was determined. The results are shown in Tables 1 and 2.

[0192] [Evaluation of preservation stability]

[0193] The resin compositions of the examples, comparative examples, and reference examples were added to a syringe with a tip diameter of 5 mm and frozen at -20°C for 24 hours. After being left to stand at room temperature (25°C) for 1 hour, the storage stability of the resin compositions was confirmed by checking whether they could be manually extruded from the tip of the syringe. The evaluation was performed according to the following criteria. The test results are given in Tables 1 and 2.

[0194] 〇: No different from the initial state, able to be discharged stably.

[0195] △: Although it can be drained, slight thickening and stringiness can be observed.

[0196] ×: Difficult to drain and confirmed thickening

[0197] ××: Unable to be expelled; it has solidified inside the syringe.

[0198] [Adhesion strength]

[0199] A resin composition was stencil-printed onto a nickel substrate with a diameter of 2 mm and a thickness of 125 μm. An alumina chip with a thickness of 3.2 mm × 1.6 mm × 0.45 mm was then mounted on the printed resin composition and a load was applied to cure the material, creating test pieces (n = 10). The curing conditions were set at 80°C for 60 minutes in a blower dryer. The alumina chip on the nickel substrate was pushed off the side using an AIKOH ENGINEERING MODEL-1605HTP strength tester. The shear strength (in N) was calculated based on the value at which the alumina chip peeled off. The average value of n = 10 was taken as the test result. The test results are given in Tables 1 and 2.

[0200]

[0201]

[0202]

[0203] Based on a comparison of the resin compositions of Reference Examples 1 and 2, which contain other thiol compounds (B') as curing agents and contain a heat-latent curing catalyst, with Comparative Examples 1, 3, 4, and 5, which contain a trithiol compound of formula (I) (B) as curing agents and contain a heat-latent curing catalyst, it can be seen that the problem of insufficient low-temperature curability when using a heat-latent curing catalyst is a problem unique to the trithiol compound of formula (I) (B).

[0204] In addition to components (A) to (C), it also contains (D) with a specific surface area of ​​4m². 2 The resin compositions of Examples 1-10, which contain inorganic fillers of 1 g or more, exhibit good storage stability and curability at 80°C.

[0205] In addition to components (A) to (C), it also includes (D') with a specific surface area of ​​less than 4m². 2 / g of inorganic filler, and does not contain (D) with a specific surface area of ​​4m² 2 No improvement in low-temperature curing properties was observed in the resin compositions of Comparative Example 2 and Comparative Example 3, which contained inorganic fillers of 1 g or more.

[0206] It should be noted that, although not shown in Table 1, the same evaluation was also performed on the two-component resin composition in Example 1, which was set as liquid A: component (A) and component (D) and liquid B: component (B), component (C) and component (E). The results showed that the storage stability and curing properties at 80°C were good.

[0207] Industrial availability

[0208] The resin compositions of the present invention are highly practical, for example, as adhesives or sealants for fixing, joining or protecting semiconductor devices or electronic components or components constituting them.

[0209] The entire contents of the disclosure of Japanese Patent Application No. 2024-032373 (filed on March 4, 2024) are incorporated herein by reference.

[0210] All documents, patent applications and technical standards described in this specification are incorporated herein by reference to the same extent as the specific and individually described documents, patent applications and technical standards are incorporated herein by reference.

Claims

1. A resin composition comprising: A (meth)acrylate compound, B is the thiol compound represented by chemical formula (I): C thermal latent curing catalyst, and The specific surface area of ​​D is 4m² 2 Inorganic fillers of / g or higher.

2. The resin composition according to claim 1, further comprising an E-photopolymerization initiator.

3. The resin composition according to claim 1 or 2, wherein, The content of the inorganic filler D is 1% to 90% by weight relative to the total weight of the resin composition.

4. The resin composition according to any one of claims 1 to 3, wherein, The ratio of the total surface area of ​​the inorganic filler D in the resin composition to the content of the thermally latent curing catalyst C in the resin composition is 7m². 2 / g~400m 2 / g.

5. The resin composition according to any one of claims 1 to 4, wherein, The content of (meth)acrylate compounds with an average molecular weight of less than 250 in the resin composition is 0% to 90% by weight relative to the content of component B in the resin composition.

6. The resin composition according to any one of claims 1 to 5, further comprising component B', i.e., a thiol compound other than component B, wherein the ratio of the (meth)acryloyl equivalent number of component A to the total of the thiol equivalent number of component B and the thiol equivalent number of component B', i.e., [(meth)acryloyl equivalent number of component A] / ([thiol equivalent number of component B] + [thiol equivalent number of component B']) is 0.1 to 10.

7. The resin composition according to any one of claims 1 to 6, wherein the components A to D are contained in a single container.

8. The resin composition according to any one of claims 1 to 6, wherein the components A to D are dispensed into two or more containers.

9. An adhesive or sealant comprising the resin composition according to any one of claims 1 to 8.

10. The adhesive or sealant according to claim 9, used in a semiconductor device or electronic component.

11. A cured product obtained by curing the resin composition of any one of claims 1 to 8, or the adhesive or sealant of claim 9 or 10.

12. A semiconductor device or electronic component comprising the cured material of claim 11.

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