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

Abstract

This invention provides resin compositions exhibiting excellent low-gloss properties even when containing specific trithiols, adhesives or sealants comprising the resin composition, cured products, and semiconductor devices or electronic components. The invention provides a resin composition comprising: (A) a (meth)acrylate compound, (B) a thiol compound of formula (I), and (C) a thermally latent curing catalyst that is solid at room temperature, and provides adhesives or sealants comprising the resin composition, cured products, and semiconductor devices or electronic components.

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 have studied a curable composition with a (meth)acrylate compound as the main agent and a trithiol compound as the curing agent as described in Patent Document 3. They found that the gloss of the cured product tends to increase when cured by light or heat. When this curable composition, which produces a high-gloss product, is applied near optical components such as image sensor modules or TOF sensor modules, optical defects can easily occur due to light reflection. Therefore, to suppress optical defects, the resin composition used for fixing, bonding, or protecting components constituting optical sensor modules such as image sensor modules and TOF sensor modules must have low gloss.

[0012] The objective of this invention is to provide resin compositions that exhibit excellent low-gloss 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] as well as

[0021] (C) Thermally latent curing catalyst that is solid at room temperature.

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

[0023] [3] According to the resin composition described in [1] or [2] above, wherein the above (C) thermal latent curing catalyst, which is solid at room temperature, comprises at least one selected from amine adduct thermal latent curing catalysts and microcapsule thermal latent curing catalysts.

[0024] [4] According to the resin composition described in [3] above, wherein the above (C) thermally latent curing catalyst, which is solid at room temperature, contains a compound having at least one urea bond in its structure.

[0025] [5] The resin composition according to any one of [1] to [4] 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.

[0026] [6] The resin composition according to any one of [1] to [5] above, wherein the gloss of the cured product with a thickness of 300 μm obtained by curing the resin composition at 80°C for 60 minutes has an incident angle of 60° of less than 90°.

[0027] [7] The resin composition described in any one of [1] to [6] above is configured such that the above components (A) to (C) are packaged into 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 (C) 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 exhibit excellent low gloss even when containing specific trithiol compounds, adhesives or sealants containing the resin compositions, cured products obtained 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] In this specification, the term "resin composition with excellent low gloss" refers to a resin composition that provides a cured product with sufficiently low gloss. A cured product with "sufficiently low gloss" is, for example, a cured product with a gloss level of less than 90° at an incident angle of 60°, as measured according to JIS Z 8741.

[0036] [Resin Composition]

[0037] As one aspect of the present invention, the resin composition comprises:

[0038] (A) (meth)acrylate compounds,

[0039] (B) Thiol compounds represented by chemical formula (I):

[0040] [Chemistry 3]

[0041]

[0042] as well as

[0043] (C) Thermally latent curing catalyst that is solid at room temperature.

[0044] According to this method, it is possible to provide a resin composition that exhibits excellent low gloss even when containing a trithiol compound of formula (I).

[0045] (A) (Meth)acrylate compound

[0046] 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 group" includes both methacryloyl and acryloyl groups. Furthermore, "(meth)acrylate compound" includes both acrylate compounds and methacrylate compounds.

[0047] 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).

[0048] 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.

[0049] (A) Any one (meth)acrylate compound may be used, or two or more may be used in combination.

[0050] 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.

[0051] (B) Thiol compounds represented by chemical formula (I)

[0052] 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)"):

[0053] [Chemistry 4]

[0054]

[0055] 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.

[0056] (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.

[0057] [Chemistry 5]

[0058]

[0059] [Chemistry 6]

[0060]

[0061] 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.

[0062] 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.

[0063] 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.

[0064] 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.

[0065] 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.

[0066] 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.

[0067] 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.

[0068] 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).

[0069] (C) Thermally latent curing catalyst that is solid at room temperature

[0070] The resin composition of this method comprises (C) a thermally latent curing catalyst that is solid at room temperature (hereinafter also referred to as "component (C)"). A thermally latent curing catalyst is a compound or substance that is inert at room temperature and is activated by heating to function as a curing catalyst. The thermally latent curing catalyst of this method is solid at room temperature. Examples of thermally latent curing catalysts that are solid at room temperature include dicyandiamide; urea compounds that are solid at room temperature; amine compounds that are solid at room temperature; amine adduct system thermally 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 thermally latent curing catalysts; inclusion-type thermally latent curing catalysts, and other solid-dispersed thermally latent curing catalysts. The amine compounds include aliphatic amines, aromatic amines, and heterocyclic amines.

[0071] The inventors have studied a curable composition using a (meth)acrylate compound as the main agent and a trithiol compound represented by formula (I) as the curing agent. They found that the gloss of the cured product tends to increase when heat-cured. While not limited to the following explanation, the reason for this can be inferred as follows: It can be considered that in the curing of the (meth)acrylate compound and the trithiol compound represented by formula (I), the viscosity of the curable composition is lower due to the presence of a higher proportion of low-viscosity (meth)acrylate compounds and the very low viscosity of the trithiol compound represented by formula (I). Therefore, the surface smoothness of the resulting cured product is high, and gloss is easily produced. Furthermore, it can be considered that in the heat-based curing of the (meth)acrylate compound-thiol compound, the curing reaction can be promoted in an anionic polymerization system using an alkaline catalyst such as an amine. In the heat curing of such an anionic polymerization system, although the low number of functional groups in the trithiol compound represented by formula (I) leads to a lower crosslinking density, the structure with low steric hindrance results in less uneven curing, thus the surface becomes smooth and gloss is easily produced.

[0072] In this method, by including a thermally latent curing catalyst that is solid at room temperature in the resin composition, excellent low gloss can be achieved even in curable compositions with (meth)acrylate compounds as the main agent and trithiol compounds as the curing agent as shown in formula (I). While not limited to the explanations below, it can be inferred that this is due to various mechanisms, such as those described below:

[0073] (1) Because the strong alkalinity around the thermally latent curing catalyst particles, which are solid at room temperature, and the weak alkalinity away from the particles produce a slight difference in curing degree, moderate curing unevenness is produced, thereby suppressing gloss.

[0074] (2) Because the soft bulk of the trithiol compound shown in formula (I) solidifies around the thermally latent curing catalyst particles, which are solid at room temperature, it forms tiny irregularities on the surface, thereby suppressing surface gloss; and

[0075] (3) Since the trithiol compound shown in formula (I) has a low viscosity, the thermally latent curing catalyst, which is solid at room temperature, is easy to float to the surface of the polymerization system, thereby forming tiny bumps on the surface of the resulting cured product.

[0076] Examples of urea compounds that are solid at room temperature include 1,1'-(4-methyl-1,3-phenylene)bis(3,3-dimethylurea) (product name: U-CAT 3512T, manufactured by San-Apro Co., Ltd.) and 3-{3-[(3,3-dimethylureido)methyl]-3,5,5-trimethylcyclohexyl}-1,1-dimethylurea (product name: U-CAT 3513N, manufactured by San-Apro Co., Ltd.), but they are not limited to these.

[0077] 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.

[0078] 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.

[0079] 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.

[0080] 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.

[0081] 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.

[0082] 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.

[0083] 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.

[0084] 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.

[0085] So-called inclusion-type thermally latent curing catalysts are curing catalysts with a structure in which guest molecules such as amine compounds are encapsulated at the molecular level in the crystal cavities formed by the host molecules.

[0086] In this method, regarding the thermally latent curing catalyst (C), which is solid at room temperature, from the viewpoint of superior low gloss, it is preferable to include at least one selected from amine adduct-based thermally latent curing catalysts and microencapsulated thermally latent curing catalysts. Since amine adduct-based and microencapsulated thermally latent curing catalysts can moderately control the destruction and / or dissolution of thermally latent curing catalyst particles during heating in thermal curing, they are considered to readily form minute irregularities on the surface of the cured product. Among these, catalysts containing compounds having at least one urea bond in their structure are more preferred (e.g., catalysts containing reaction products of amine compounds and isocyanate compounds or urea compounds (amine-urea type adducts)). Because of the high polarity of urea bonds, they are considered to more readily form segments in the curing reaction system of resin compositions using trithiol compounds as curing agents, thereby more readily forming minute irregularities on the surface of the cured product.

[0087] Examples of commercially available thermally latent curing catalysts that are solid at room temperature 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.), and "Novacure HXA3922HP". The product names include "HXA3932HP" (Asahi Kasei Corporation), "NovacureHXA5945HP" (Asahi Kasei Corporation), "Novacure HXA5911HP" (Asahi Kasei Corporation), and "NovacureHXA9382HP" (Asahi Kasei Corporation), 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 "FujicureFXE-1000" (T&K TOKA Co., Ltd.), "Fujicure FXR1020" (T&K TOKA Co., Ltd.), "FujicureFXR-1030" (T&K TOKA Co., Ltd.), "Fujicure FXR-1110" (T&K TOKA Co., Ltd.), "FujicureFXR1121" (T&K TOKA Co., Ltd.), "Fujicure FXR1081" (T&K TOKA Co., Ltd.), "Fujicure1061" (T&K TOKA Co., Ltd.), and "Fujicure 1171" (T&K TOKA Co., Ltd.), but they are not limited to these. As a commercially available product of inclusion-type thermally latent curing catalyst, "NISSOCURE TIC-188" (a product name from Nippon Soda Co., Ltd.) can be cited.

[0088] (C) Any one of the heat-latent curing catalysts that is solid at room temperature can be used, or two or more can be used together.

[0089] 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 15% by weight relative to the total weight of the resin composition.

[0090] It should be noted that component (C) includes a dispersion in which particles of a thermally latent curing catalyst, which is solid at room temperature, are dispersed in an epoxy resin. The resin composition of this method may also contain such an epoxy resin.

[0091] If necessary, the resin composition of this method may also contain any component other than the components (A) to (C) above, such as the substances described below.

[0092] (D) Photopolymerization initiator

[0093] The resin composition of this method may include (D) a photopolymerization initiator (hereinafter also referred to as "component (D)") 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, after the resin composition has been cured by light (UV) curing, or further cured by heat under light irradiation. Interestingly, the resin composition of this method containing a photopolymerization initiator can exhibit low gloss even when used for photocuring. The reason for this is not limited to the following interpretation, but it can be considered that during photocuring, the (C) thermally latent curing catalyst, which is solid at room temperature, is not dissolved, but retains its particle shape. 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, compounds having photosensitive sites and peroxide structures, etc., but are not limited to them.

[0094] 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.

[0095] 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.

[0096] 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.

[0097] 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.

[0098] 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.

[0099] Photopolymerization initiators can be used alone or in combination of two or more.

[0100] 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.

[0101] (E) Packing

[0102] The resin composition of this invention may contain fillers (hereinafter also referred to as "component (E)") to a extent that does not impair the effects of the invention. By containing fillers in the resin composition, the coefficient of linear expansion of the cured product obtained by curing the resin composition can be reduced, and the thermal cycling resistance can be improved. In addition, if the filler is of low elastic modulus, the stress generated in the cured product can be relieved, and the long-term reliability can be improved. Fillers are broadly classified into inorganic fillers and organic fillers.

[0103] Inorganic fillers consist of granular bodies formed from inorganic materials. There are no particular limitations on any inorganic filler that reduces the coefficient of linear expansion through addition. Suitable 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 dioxide, zinc oxide, silicon carbide, silicon nitride, and boron nitride. Any one type of inorganic filler can be used, or two or more can be used in combination. Silica filler is preferred for increasing the filler volume. Amorphous silica is preferred. The surface of the inorganic filler can also be surface-treated with coupling agents such as silane coupling agents.

[0104] Examples of organic fillers include polytetrafluoroethylene (PTFE) fillers, silicone fillers, acrylic fillers, fillers with a urethane backbone, fillers with a butadiene backbone, and styrene fillers. Organic fillers can also be surface-treated.

[0105] The shape of the filler is not particularly limited and can be any shape, such as spherical, scaly, needle-like, or amorphous.

[0106] 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 term "average particle size" refers to the median diameter (d50) of the volume reference determined by laser diffraction according to ISO-13320 (2009). By setting the average particle size of the filler to the upper limit or below, filler sedimentation can be suppressed, and the formation of coarse particles can be suppressed, thereby suppressing wear of the nozzle of the jet dispensing machine and the dispersion of the resin composition ejected from the nozzle of the jet dispensing machine outside the desired area. The lower limit of the average particle size of the filler is not particularly limited; however, from the viewpoint of the viscosity of the resin composition, it is preferably 0.001 μm or more, more preferably 0.1 μm or more. In one embodiment of this method, the average particle size of the filler is preferably 0.01 μm to 5.0 μm, more preferably 0.1 μm to 3.0 μm. Fillers with different average particle sizes can also be used in combination. For example, fillers with an average particle size of 0.001 μm or more but less than 0.1 μm and fillers with an average particle size of 0.1 μm to 6.0 μm can be used in combination.

[0107] The filler content in the resin composition of this method is preferably 10 to 50% by weight relative to the total weight of the resin composition, more preferably 15 to 45% by weight, and even more preferably 15 to 40% by weight.

[0108] (F) Stabilizer

[0109] 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.

[0110] 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.

[0111] Stabilizers can be any one type, or two or more types can be used in combination.

[0112] 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.

[0113] (B') Thiol compounds other than component (B)

[0114] 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:

[0115] 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;

[0116] Aromatic thiols such as benzene dithiol, toluene dithiol, and xylene dithiol (p-xylene dithiol);

[0117] Cyclic sulfide compounds, such as polythiols containing a 1,4-dithiane ring;

[0118] 3-Thiapentane-1,5-dithiol, 4-mercaptomethyl-3,6-dithia-1,8-octanedithiol and other mercaptoalkyl sulfide compounds;

[0119] Mercaptopropionates such as pentaerythritol tetra(3-mercaptopropionate);

[0120] Terminal thiol compounds in epoxy resins;

[0121] 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;

[0122] Glycourea-type thiols such as 1,3,4,6-tetra(2-mercaptoethyl)glycourea and 1,3,4,6-tetra(3-mercaptopropyl)glycourea;

[0123] 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.

[0124] 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.

[0125] These other thiols can be used alone or in combination of two or more.

[0126] 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.

[0127] Reactive diluents

[0128] 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.

[0129] 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.

[0130] 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.

[0131] 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.

[0132] (G) Other additives

[0133] 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.

[0134] From the viewpoint of preventing a decrease in curing strength and sealing, and 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) and (B)). For example, the content of liquid components is preferably 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.

[0135] The method for manufacturing the resin composition of this method is not particularly limited. For example, components (A) to (C) 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 appropriately combined.

[0136] 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 (C) 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 (C) 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 (C) and any other components used as needed; a single liquid may contain the aforementioned components (A) to (C); or a liquid may consist only of the aforementioned components (A) to (C) and / or any other components used as needed. For example, when the composition consists of liquid A and liquid B, the distribution can be as follows: liquid A: component (A), liquid B: component (B) and component (C); liquid A: component (A) and component (C), liquid B: component (B); liquid A: component (A) and component (D), liquid B: component (B) and component (C); liquid A: component (A) and component (B) and component (C), liquid B: component (B'); liquid A: component (A) and component (B), liquid B: component (B') and component (C); or liquid A: component (A), liquid B: component (B) and component (C) and component (D). When components (A) to (C) 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 components (A) to (C) are each included in different liquids, each liquid can be considered as the resin composition of this method. As an example of the above components (A) to (C) being contained in different liquids, a resin composition can be provided in which the above components (A) to (C) are dispensed into two or more containers. More specifically, a kit can be provided consisting of multiple liquids containing any one of the above components (A) to (C).

[0137] The resin composition obtained in this way is thermosetting, and can be cured, for example, by heat treatment at 40–200°C for 0.1–300 minutes. At a temperature of 100°C, curing is preferably within 5 hours, more preferably within 3 hours, and even more preferably within 1 hour. 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 achieves low gloss regardless of whether it is cured at a lower temperature (e.g., 60–100°C) or a higher temperature (e.g., above 100°C).

[0138] When the resin composition of this embodiment contains a (D) 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. The resin composition containing the photopolymerization initiator of this embodiment can exhibit low gloss even when supplied for light curing.

[0139] In one embodiment, in the resin composition of this method, the gloss of a 300 μm thick cured product obtained by curing the resin composition at 80°C for 60 minutes has an incident angle of 60° that is preferably less than 90°, more preferably less than 85°, and even more preferably less than 80°. The gloss at an incident angle of 60° can be measured according to JIS Z 8741. It should be noted that, in this specification, regarding the gloss of the cured resin composition, in order to avoid the influence of substrate gloss on the measurement results, the value is obtained by measuring the cured resin composition prepared on a low-gloss substrate as a sample.

[0140] 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.

[0141] [Adhesive or sealant]

[0142] 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.

[0143] 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 (C), 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 (C), 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 manner, each liquid may contain one or more components selected from the above-mentioned components (A) to (C) and any other components used as needed. Alternatively, a single liquid may contain the above-mentioned components (A) to (C), or a liquid may consist only of the above-mentioned components (A) to (C) and / or any other components used as needed. For example, when the liquid is divided into liquid A and liquid B, the distribution may be as follows: liquid A: component (A), liquid B: component (B) and component (C), liquid A: component (A) and component (C), liquid B: component (B), liquid A: component (A) and component (D), liquid B: component (B) and component (C), liquid A: component (A) and component (B) and component (C), liquid B: component (B'), liquid A: component (A) and component (B), liquid B: component (B') and component (C), or liquid A: component (A), liquid B: component (B) and component (C). When components (A) to (C) are contained in liquid A, and all other components are contained in liquid B, liquid A alone, or liquid A and liquid B together, can be considered as the adhesive or sealing material of this method. On the other hand, when components (A) to (C) are contained in different liquids, each liquid can be considered as the adhesive or sealing material of this method. As an example of components (A) to (C) being contained in different liquids, an adhesive or sealing material constructed by dispensing components (A) to (C) into two or more containers can be given as an example. Specifically, a kit composed of multiple liquids containing any one of components (A) to (C) can be given as an example.

[0144] [Cure of resin composition, adhesive, or sealant]

[0145] Another aspect of the present invention is a cured product obtained by curing the resin composition, adhesive, or sealant described above.

[0146] [Semiconductor devices, electronic components]

[0147] 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.

[0148] Example

[0149] 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.

[0150] [Preparation of the resin composition]

[0151] 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 Table 1. In Table 1, the amount of each component is expressed in parts by weight (in g). The components used in the Examples and Comparative Examples are shown below.

[0152] ·(A) (meth)acrylate compound

[0153] (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)

[0154] (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)

[0155] (A-3): Dipropylene glycol diacrylate (Product name: M-408, manufactured by Toa Synthetic Co., Ltd., (meth)acryloyl equivalent: 117 g / eq, molecular weight: 468 g / mol)

[0156] • (B) Thiol compounds represented by formula (I)

[0157] (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.

[0158] • Other thiols besides component (B')

[0159] (B'-1): 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)

[0160] [Chemistry 7]

[0161]

[0162] (C) Thermally latent curing catalyst that is solid at room temperature

[0163] (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.)

[0164] (C-2): Amine-epoxy adduct-based thermally latent curing catalyst (Product name: NOVACURE HXA9322HP, core-shell type, manufactured by Asahi Kasei Corporation)

[0165] 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 the particulate latent curing catalyst, which is solid at room temperature, in epoxy resin (a mixture of bisphenol A type epoxy resin and bisphenol F type epoxy resin (epoxy equivalent: 180 g / eq)).

[0166] (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.)

[0167] (C-4): 2-Undecylimidazole (solid at room temperature, manufactured by Tokyo Chemical Industry Co., Ltd.)

[0168] (C-5): 2-Heptadecanylimidazole (solid at room temperature, manufactured by Tokyo Chemical Industry Co., Ltd.)

[0169] • (C') Thermally latent curing catalyst that is liquid at room temperature

[0170] (C'-1): N,N-Dimethylbenzylamine (manufactured by Fujifilm and Wako Pure Chemical Industries, Ltd.)

[0171] (C'-2): 1-Ethylimidazole (manufactured by Tokyo Chemical Industry Co., Ltd.)

[0172] (C'-3): 2-Ethyl-4-methylimidazole (manufactured by Tokyo Chemical Industry Co., Ltd.)

[0173] • (D) Photopolymerization initiator

[0174] (D-1): 1-Hydroxy-cyclohexyl-phenyl-one (Product name: Omnirad 184, manufactured by IGM Resins BV)

[0175] (E) Packing

[0176] (E-1): Silica filler (Product name: SE2300, manufactured by Admatechs Co., Ltd., specific surface area: 4.4 m²) 2 / g)

[0177] (F) Stabilizer

[0178] (F-1): Triisopropyl borate

[0179] (G) Other additives

[0180] (G-1): Silane coupling agent (3-epoxypropoxypropyltrimethoxysilane) (Product name: KBM-403, manufactured by Shin-Etsu Chemical Co., Ltd.)

[0181] 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.

[0182] [Evaluation of preservation stability]

[0183] 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 shown in Table 1.

[0184] ◎: No different from the initial state, able to be stably discharged.

[0185] ○: Although it can be drained, slight thickening and stringiness can be observed.

[0186] △: Difficult to drain and confirmed thickening

[0187] ×: Unable to be expelled; it has solidified inside the syringe.

[0188] [Evaluation of gloss]

[0189] On a 25mm × 75mm × 1.5mm polyamide plate, the resin compositions of the examples, comparative examples, and reference examples were printed into rectangles of 25mm × 50mm (0.3mm thickness) using stencil printing. The printed resin compositions were then cured under the following four curing conditions. The cured products on the resulting polyamide plates were used as test pieces.

[0190] Curing condition 1: Curing at 80°C for 60 minutes in a blower dryer.

[0191] Curing condition 2: Using an Excelitas Technologies AC475 UV LED irradiation device with a cumulative light intensity of 2000 mJ / cm². 2 (Measured using a UIT-250 (connected to a UVD-365 light receiver) manufactured by USHIO Electric Co., Ltd.) The resin was pre-cured by UV irradiation. Then, the pre-cured resin composition was fully cured in a blower dryer at 80°C for 60 minutes.

[0192] Curing condition 3: Curing at 150°C for 60 minutes in a blower dryer.

[0193] Curing condition 4: Using an Excelitas Technologies AC475 UV LED irradiation device with a cumulative light dose of 2000 mJ / cm². 2 (Measured using a UIT-250 (connected to a UVD-365 light receiver) manufactured by USHIO Electric Co., Ltd.) The resin was pre-cured by UV irradiation. Then, the pre-cured resin composition was fully cured in a blower dryer at 150°C for 60 minutes.

[0194] Using a gloss meter IG-331 (light source: LED (wavelength 890nm)) manufactured by Horiba Corporation, the specular gloss (%) of the test specimen surface was measured according to JIS Z 8741 under conditions of 20° incident angle and 20° received angle, and under conditions of 60° incident angle and 60° received angle. The results are shown in Table 1. It should be noted that the same evaluation was also performed on the two-component resin composition of Example 1, which consisted of liquid A: component (A), liquid B: component (B), and components (C) and (D).

[0195]

[0196]

[0197] In the table,

[0198] "Gloss UV+80℃ / 60min (20°)" refers to the gloss of the cured resin composition at an incident angle of 20° after curing under curing condition 2.

[0199] "Gloss UV+80℃ / 60min (60°)" refers to the gloss of the cured resin composition obtained under curing condition 2 at an incident angle of 60°.

[0200] "Gloss 80℃ / 60min (20°)" refers to the gloss of the cured resin composition at an incident angle of 20° under curing conditions 1.

[0201] "Gloss 80℃ / 60min (60°)" refers to the gloss of the cured resin composition obtained under curing condition 1 at an incident angle of 60°.

[0202] "Gloss UV+150℃ / 60min (20°)" refers to the gloss of the cured resin composition at an incident angle of 20° after curing under curing condition 4.

[0203] "Gloss UV+150℃ / 60min (60°)" refers to the gloss of the cured resin composition obtained under curing condition 4 at an incident angle of 60°.

[0204] "Gloss 150℃ / 60min (20°)" refers to the gloss of the cured resin composition at an incident angle of 20° after curing under curing condition 3.

[0205] "Gloss 150℃ / 60min (60°)" means the gloss of the cured resin composition obtained under curing condition 3 at an incident angle of 60°.

[0206] The resin compositions of Comparative Examples 1 to 3, which contain (A) (meth)acrylate compound, (B) trithiol compound of formula (I) and (C') heat-latent curing catalyst that is liquid at room temperature, all exhibit high gloss of cured products under any curing conditions.

[0207] On the other hand, it is known that the resin compositions of Examples 1-10, which contain (A) (meth)acrylate compound, (B) trithiol compound of formula (I), and (C) a heat-latent curing catalyst that is solid at room temperature, exhibit lower gloss suppression compared to the resin compositions of Comparative Examples 1-3, which replace the heat-latent curing catalyst that is solid at room temperature with (C) and contain a heat-latent curing catalyst that is liquid at room temperature. Furthermore, it is known that the resin compositions of Examples 1-8, which contain a heat-latent curing catalyst having urea bonds in their structure, exhibit lower gloss suppression regardless of whether they are cured at 80°C or 150°C.

[0208] It should be noted that, although not shown in Table 1, the two-component resin composition with components A, B, C, and D in Example 1 was also evaluated in the same way, and the result showed excellent low gloss properties.

[0209] Industrial availability

[0210] 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.

[0211] The entire contents of the disclosure of Japanese Patent Application No. 2024-032374 (filed on March 4, 2024) are incorporated herein by reference.

[0212] 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): as well as C is a thermally latent curing catalyst that is solid at room temperature.

2. The resin composition according to claim 1, further comprising a D-photopolymerization initiator.

3. The resin composition according to claim 1 or 2, wherein, The thermally latent curing catalyst C, which is a solid at room temperature, comprises at least one type selected from amine adduct-based thermally latent curing catalysts and microcapsule-type thermally latent curing catalysts.

4. The resin composition according to claim 3, wherein, The thermally latent curing catalyst, which is a solid at room temperature, comprises a compound having at least one urea bond in its structure.

5. The resin composition according to any one of claims 1 to 4, 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.

6. The resin composition according to any one of claims 1 to 5, wherein, The gloss of a cured material with a thickness of 300 μm obtained by curing the resin composition at 80°C for 60 minutes, with an incident angle of 60°, is less than 90°.

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

8. The resin composition according to any one of claims 1 to 6, wherein the components A to C 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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