Resin composition, cured article, and method for producing cured article

Abstract

Provided is a resin composition comprising: a component (A) that is a specific bismaleimide compound; a component (B) that is one or more compounds selected from the group consisting of a specific furan ring-containing compound and a specific anthracene compound; and a component (C) that is an epoxy compound excluding the component (B).

Description

Resin composition, cured product, and method for producing the cured product

[0001] The present disclosure relates to a resin composition, a cured product, and a method for producing the same.

[0002] Epoxy compounds have excellent moldability, electrical properties, moisture resistance, heat resistance, mechanical properties, etc., and have therefore been used in the fields of molding materials, adhesive materials, electronic components, ink materials, etc. Epoxy compounds are also used as encapsulating materials for electronic component elements such as semiconductor devices.

[0003] Epoxy compounds used as sealing materials are required to be free from cracking and peeling due to stresses such as thermal expansion and thermal contraction when cured. In order to suppress cracking and peeling due to thermal stress, blending various additives into epoxy compounds has been investigated (see, for example, Patent Document 1). However, the cured product of the resin composition described in Patent Document 1 has a problem in that its stress relaxation performance is insufficient.

[0004] Japanese Patent Application Laid-Open No. 2003-183348

[0005] The present disclosure has been made in view of the above circumstances, and has an object to provide a resin composition capable of forming a cured product having excellent stress relaxation performance.

[0006] In order to solve the above problems, the present inventors have conducted extensive research into the causes of the above problems and have found that a resin composition containing a specific compound can solve the above problems.

[0007] That is, the present disclosure is a resin composition comprising: component (A): a compound represented by general formula (1); component (B): one or more compounds selected from the group consisting of compounds represented by general formula (2) and compounds represented by general formula (3); and component (C): an epoxy compound excluding component (B).

[0008]

[0009] (In general formula (1), R 1represents an unsubstituted aliphatic hydrocarbon group having 1 to 10 carbon atoms, a group in which one or more methylene groups in the aliphatic hydrocarbon group are substituted with a divalent group selected from -O-, -S-, -SO-, or -SO2-, 1 -or-Ar 2 -R 2 -Ar 2 - and Ar 1 is an unsubstituted phenylene group, a phenylene group substituted with 1 to 4 methyl or ethyl groups, an unsubstituted biphenyl group, or a biphenyl group substituted with 1 to 8 methyl or ethyl groups, and Ar 2 are each an unsubstituted phenylene group, a phenylene group substituted with 1 to 4 methyl groups or ethyl groups, an unsubstituted biphenylene group, or a biphenylene group substituted with 1 to 8 methyl groups or ethyl groups, and R 2 is -(CH2) d -, -O-, -S-, -SO-, -SO2- or -CO-, and d is an integer of 1 to 8.

[0010]

[0011] (In general formula (2), R 21 is an unsubstituted aliphatic hydrocarbon group having 1 to 20 carbon atoms or a group in which one or more methylene groups in the aliphatic hydrocarbon group have been substituted with a divalent group selected from -O-, -S-, -SO-, or -SO2-; R 22 , R 23 and R 24 are each independently a hydrogen atom or an unsubstituted aliphatic hydrocarbon group having 1 to 20 carbon atoms.

[0012]

[0013] (In general formula (3), R 31 is an unsubstituted aliphatic hydrocarbon group having 1 to 20 carbon atoms or a group in which one or more methylene groups in the aliphatic hydrocarbon group have been substituted with a divalent group selected from -O-, -S-, -SO-, or -SO2-; R 32 , R 33 , R 34 , R 35 , R 36 , R37 , R 38 , R 39 and R 40 are each independently a hydrogen atom or an unsubstituted aliphatic hydrocarbon group having 1 to 20 carbon atoms.

[0014] The resin composition of the present disclosure preferably further contains (D) a curing agent.

[0015] In the resin composition of the present disclosure, the component (B) preferably contains a compound represented by the general formula (2).

[0016] In the resin composition of the present disclosure, in the general formula (2), R 21 is preferably a group in which one or more methylene groups in the above aliphatic hydrocarbon group have been substituted with a divalent group selected from -O-, -S-, -SO-, or -SO2-.

[0017] In the resin composition of the present disclosure, the component (B) preferably contains a compound represented by the general formula (3).

[0018] In the resin composition of the present disclosure, in the general formula (3), R 31 is preferably a group in which one or more methylene groups in the above aliphatic hydrocarbon group have been substituted with a divalent group selected from -O-, -S-, -SO-, or -SO2-.

[0019] The present disclosure relates to a cured product obtained by curing the above-mentioned resin composition.

[0020] The present disclosure is a method for producing a cured product, which includes curing the above-described resin composition.

[0021] According to the present disclosure, it is possible to provide a resin composition capable of forming a cured product with excellent stress relaxation performance.

[0022] The present disclosure relates to a resin composition, a cured product, and a method for producing the same.

[0023] The present disclosure will be described in detail below. A. Resin Composition

[0024] First, the resin composition of the present disclosure will be described. The resin composition of the present disclosure includes: component (A): a compound represented by general formula (1) (hereinafter, sometimes referred to as "component (A)"); component (B): one or more compounds selected from the group consisting of compounds represented by general formula (2) and compounds represented by general formula (3) (hereinafter, sometimes referred to as "component (B)"); and component (C): an epoxy compound other than component (B) (hereinafter, sometimes referred to as "component (C)"). The resin composition of the present disclosure can form a cured product with excellent stress relaxation performance.

[0025] The elements constituting the resin composition of the present disclosure will be described in detail below. 1. Component (A) The resin composition of the present disclosure contains component (A): a compound represented by general formula (1) as an essential component.

[0026]

[0027] In general formula (1), R 1 represents an unsubstituted aliphatic hydrocarbon group having 1 to 10 carbon atoms, a group in which one or more methylene groups in an unsubstituted aliphatic hydrocarbon group having 1 to 10 carbon atoms are substituted with a divalent group selected from -O-, -S-, -SO-, or -SO2-, 1 -or-Ar 2 -R 2 -Ar 2 -. Ar 1 is an unsubstituted phenylene group, a phenylene group substituted with 1 to 4 methyl or ethyl groups, an unsubstituted biphenylene group, or a biphenylene group substituted with 1 to 8 methyl or ethyl groups. 2 R is an unsubstituted phenylene group, a phenylene group substituted with 1 to 4 methyl or ethyl groups, an unsubstituted biphenylene group, or a biphenylene group substituted with 1 to 8 methyl or ethyl groups, respectively. 2 is -(CH2) d -, -O-, -S-, -SO-, -SO2- or -CO-. d is an integer of 1 to 8.

[0028] In the present disclosure, in general formula (1), R 1is preferably -Ar from the viewpoint of forming a cured product having excellent stress relaxation properties. 2 -R 2 -Ar 2 It is preferable that −.

[0029] In general formula (1), R 1 Ga-Ar 2 -R 2 -Ar 2 -, Ar 2 From the viewpoint of forming a cured product having excellent stress relaxation properties, each of R is preferably an unsubstituted phenylene group or a phenylene group substituted with 1 to 4 methyl groups or ethyl groups, and more preferably a phenylene group substituted with 1 to 4 methyl groups or ethyl groups. 1 Ga-Ar 2 -R 2 -Ar 2 -, then R 2 is —(CH) from the viewpoint of being able to form a cured product having excellent stress relaxation performance. d It is preferably -, and more preferably -(CH2)-.

[0030] In the present disclosure, the number of carbon atoms in a group in which a methylene group in a group having a predetermined number of carbon atoms is substituted with a divalent group is defined as the same as the number of carbon atoms in the group before the substitution. For example, in this specification, the number of carbon atoms in a group in which a methylene group in an alkyl group having 1 to 20 carbon atoms is substituted with a divalent group is defined as 1 to 20.

[0031] Specific examples of the compound represented by general formula (1) include the following compounds No. 1-1 to No. 1-5, but the present disclosure is not limited to these compounds. Among these, compound No. 1-1 is preferred from the viewpoint of being able to form a cured product with excellent stress relaxation performance.

[0032]

[0033] The resin composition of the present disclosure may contain only one type of component (A), or may contain two or more types.

[0034] From the viewpoint of being able to form a cured product with excellent stress relaxation performance, the content of the (A) component is preferably 1 to 80 parts by mass, more preferably 5 to 70 parts by mass, even more preferably 10 to 60 parts by mass, and most preferably 10 to 50 parts by mass, relative to 100 parts by mass of the total of the (A), (B), and (C) components.

[0035] 2. Component (B) The resin composition of the present disclosure contains, as an essential component, component (B): one or more compounds selected from the group consisting of compounds represented by general formula (2) and compounds represented by general formula (3):

[0036]

[0037] In general formula (2), R 21 is an unsubstituted aliphatic hydrocarbon group having 1 to 20 carbon atoms or a group in which one or more methylene groups in an unsubstituted aliphatic hydrocarbon group having 1 to 20 carbon atoms have been substituted with a divalent group selected from -O-, -S-, -SO-, or -SO2-. 22 , R 23 and R 24 are each independently a hydrogen atom or an unsubstituted aliphatic hydrocarbon group having 1 to 20 carbon atoms. 31 is an unsubstituted aliphatic hydrocarbon group having 1 to 20 carbon atoms or a group in which one or more methylene groups in an unsubstituted aliphatic hydrocarbon group having 1 to 20 carbon atoms have been substituted with a divalent group selected from -O-, -S-, -SO-, or -SO2-. 32 , R 33 , R 34 , R 35 , R 36 , R 37 , R 38 , R 39 and R 40 are each independently a hydrogen atom or an unsubstituted aliphatic hydrocarbon group having 1 to 20 carbon atoms.

[0038] In the present disclosure, the component (B) preferably contains a compound represented by general formula (2) from the viewpoint of being able to form a cured product with excellent stress relaxation performance.

[0039] In the present disclosure, in general formula (2), R 21 From the viewpoint of being able to form a cured product having excellent stress relaxation performance, is preferably a group in which one or more methylene groups in an unsubstituted aliphatic hydrocarbon group having 1 to 20 carbon atoms have been substituted with a divalent group selected from -O-, -S-, -SO-, or -SO2-, more preferably a group in which one or more methylene groups in an unsubstituted aliphatic hydrocarbon group having 1 to 10 carbon atoms have been substituted with a divalent group selected from -O-, -S-, -SO-, or -SO2-, even more preferably a group in which one or more methylene groups in an unsubstituted aliphatic hydrocarbon group having 1 to 10 carbon atoms have been substituted with a divalent group selected from -O- or -S-, and most preferably a group in which one or more methylene groups in an unsubstituted aliphatic hydrocarbon group having 1 to 10 carbon atoms have been substituted with -O-.

[0040] In the present disclosure, in general formula (2), R 22 , R 23 and R 24 are each preferably independently a hydrogen atom or an unsubstituted aliphatic hydrocarbon group having 1 to 10 carbon atoms, and more preferably a hydrogen atom, from the viewpoint of being able to form a cured product having excellent stress relaxation performance.

[0041] In the present disclosure, the component (B) preferably contains a compound represented by general formula (3) from the viewpoint of being able to form a cured product that has excellent stress relaxation performance under high temperature conditions.

[0042] In the present disclosure, in general formula (3), R 31From the viewpoint of being able to form a cured product having excellent stress relaxation performance, is preferably a group in which one or more methylene groups in an unsubstituted aliphatic hydrocarbon group having 1 to 20 carbon atoms have been substituted with a divalent group selected from -O-, -S-, -SO-, or -SO2-, more preferably a group in which one or more methylene groups in an unsubstituted aliphatic hydrocarbon group having 1 to 10 carbon atoms have been substituted with a divalent group selected from -O-, -S-, -SO-, or -SO2-, even more preferably a group in which one or more methylene groups in an unsubstituted aliphatic hydrocarbon group having 1 to 10 carbon atoms have been substituted with a divalent group selected from -O- or -S-, and most preferably a group in which one or more methylene groups in an unsubstituted aliphatic hydrocarbon group having 1 to 10 carbon atoms have been substituted with -O-.

[0043] In the present disclosure, in general formula (3), R 32 , R 33 , R 34 , R 35 , R 36 , R 37 , R 38 , R 39 and R 40 are each preferably independently a hydrogen atom or an unsubstituted aliphatic hydrocarbon group having 1 to 10 carbon atoms, and more preferably a hydrogen atom, from the viewpoint of being able to form a cured product having excellent stress relaxation performance.

[0044] Specific examples of the compound represented by general formula (2) or general formula (3) include the following compounds No. 2-1 to No. 2-10, but the present disclosure is not limited to these compounds. Among these, from the viewpoint of being able to form a cured product with excellent stress relaxation performance, one or more compounds selected from the group consisting of compounds No. 2-1 and No. 2-2 are preferred.

[0045]

[0046] The resin composition of the present disclosure may contain only one type of component (B), or may contain two or more types.

[0047] From the viewpoint of being able to form a cured product with excellent stress relaxation performance, the content of the (B) component is preferably 1 to 80 parts by mass, more preferably 3 to 60 parts by mass, even more preferably 5 to 50 parts by mass, and most preferably 5 to 45 parts by mass, relative to a total of 100 parts by mass of the (A), (B), and (C) components.

[0048] 3. Component (C) The resin composition of the present disclosure contains component (C): an epoxy compound other than component (B) as an essential component. In the present disclosure, the epoxy compound may be any compound that has at least one epoxy group in one molecule and does not fall under component (B), and there are no particular limitations on the molecular structure, molecular weight, etc. of the epoxy compound.

[0049] Examples of monofunctional epoxy compounds having one epoxy group per molecule include ethylene oxide, propylene oxide, 2,3-butylene oxide, isobutylene oxide, 1,2-butylene oxide, 1,2-epoxyhexane, 1,2-epoxyheptane, 1,2-epoxypentane, 1,2-epoxyoctane, 1,2-epoxydecane, 1,3-butadiene monoxide, 1,2-epoxytetradecane, glycidyl methyl ether, 1,2-epoxyoctadecane, 1,2-epoxyhexadecane, ...propylene oxide, propylene oxide, propylene oxide, propylene oxide, propylene oxide, propylene oxide, propylene oxide, propylene oxide, propylene oxide, propylene oxide, propylene oxide, propylene oxide, propylene oxide, propylene oxide, propylene oxide, propylene oxide, propylene oxide, propylene glycidyl ether, glycidyl isopropyl ether, tert-butyl glycidyl ether, 1,2-epoxyeicosane, 2-(chloromethyl)-1,2-epoxypropane, glycidol, epichlorohydrin, epibromohydrin, butyl glycidyl ether, 1,2-epoxyhexane, 1,2-epoxy-9-decane, 2-(chloromethyl)-1,2-epoxybutane, 2-ethylhexyl glycidyl ether, 1,2-epoxy-1H,1H,2H,2H,3H,3H-trifluorobutane, allyl glycidyl ether, tetracyanoethylene oxide, glycidyl butyrate, 1,2-epoxycyclooctane, glycidyl methacrylate, 1,2-epoxycyclododecane, 1-methyl-1,2-epoxycyclohexane, 1,2-epoxycyclopentadecane, 1,2-epoxycyclopentane, 1,2-epoxycyclohexane, 1,2-epoxy-1H,1H,2H,2H,3H,3H-heptadecafluorobutane, 3,4-epoxytetrahydrofuran, glycidyl stearate, 3-glycidyloxypropyl trimer thoxysilane, epoxysuccinic acid, glycidyl phenyl ether, isophorone oxide, α-pinene oxide, 2,3-epoxynorbornene, benzyl glycidyl ether, diethoxy(3-glycidyloxypropyl)methylsilane, 3-[2-(perfluorohexyl)ethoxy]-1,2-epoxypropane, 1,1,1,3,5,5,5-heptamethyl-3-(3-glycidyloxypropyl)trisiloxane, 9,10-epoxy-1,5-cyclododecadiene, glycidyl 4-tert-butylbenzoate, 2,2-bis(4-glycidyloxyphenyl)propane, 2-tert-butyl-2-[2-(4-chlorophenyl)]ethyloxirane, styrene oxide, glycidyl trityl ether, 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, 2-phenylpropylene oxide, cholesterol-5α,6α-epoxide, stilbene oxide, glycidyl p-toluenesulfonate, ethyl 3-methyl-3-phenylglycidate, N-propyl-N-(2,3-epoxypropyl)perfluoro-n-ol Examples of such glycidyl ethers include octyl sulfonamide, (2S,3S)-1,2-epoxy-3-(tert-butoxycarbonylamino)-4-phenylbutane, (R)-glycidyl 3-nitrobenzenesulfonate, glycidyl 3-nitrobenzenesulfonate, parthenolide, N-glycidylphthalimide, endrin, dieldrin, 4-glycidyloxycarbazole, 7,7-dimethyloctanoate [oxiranylmethyl], 1,2-epoxy-4-vinylcyclohexane, and higher alcohol glycidyl ethers having 10 to 16 carbon atoms.

[0050] Examples of polyfunctional epoxy compounds having two or more epoxy groups in one molecule include polyglycidyl ether compounds of mononuclear polyhydric phenol compounds such as hydroquinone, resorcinol, pyrocatechol, and phloroglucinol; dihydroxynaphthalene, biphenol, methylene bisphenol (bisphenol F), methylene bis(ortho-cresol), ethylidene bisphenol, isopropylidene bisphenol (bisphenol A), isopropylidene bis(ortho-cresol), tetrabromobisphenol A, 1,3-bis(4-hydroxycumylbenzene), 1,4-bis(4-hydroxycumylbenzene), 1,1,3-tris(4-hydroxyphenyl)butane, 1,1,2,2-tetra(4-hydroxyphenyl)ethane, thiobisphenol, sulfobisphenol, oxybisphenol, phenol novolac, orthocresol novolac, ethylphenol novolac, butylphenol novolac, octylphenol novolac, resorcinol novolac, and terpene phenols. polyglycidyl ether compounds of polynuclear polyhydric phenols such as ethylene glycol, propylene glycol, 1,4-butanediol, butylene glycol, hexanediol, polyethylene glycol, polypropylene glycol, thioglycol, dicyclopentadiene dimethanol, 2,2-bis(4-hydroxycyclohexyl)propane (hydrogenated bisphenol A), glycerin, trimethylolpropane, pentaerythritol, sorbitol, bisphenol A-alkylene ether compounds; polyglycidyl ether compounds of polyhydric alcohol compounds such as oxide adducts; glycidyl ester compounds of aliphatic, aromatic or alicyclic polybasic acids such as maleic acid, fumaric acid, itaconic acid, succinic acid, glutaric acid, suberic acid, adipic acid, azelaic acid, sebacic acid, dimer acid, trimer acid, phthalic acid, isophthalic acid, terephthalic acid, trimellitic acid, trimesic acid, pyromellitic acid, tetrahydrophthalic acid, and endomethylenetetrahydrophthalic acid; homopolymers or copolymers of glycidyl methacrylate;Epoxy compounds having a glycidylamino group such as N,N-diglycidylaniline, bis(4-(N-methyl-N-glycidylamino)phenyl)methane, diglycidyl orthotoluidine, N,N-bis(2,3-epoxypropyl)-4-(2,3-epoxypropoxy)-2-methylaniline, N,N-bis(2,3-epoxypropyl)-4-(2,3-epoxypropoxy)aniline, and N,N,N',N'-tetra(2,3-epoxypropyl)-4,4-diaminodiphenylmethane; vinylcyclohexene diepoxide Epoxidized compounds of cyclic olefin compounds such as cyclopentanediene diepoxide, 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate, 3,4-epoxy-6-methylcyclohexylmethyl-6-methylcyclohexanecarboxylate, and bis(3,4-epoxy-6-methylcyclohexylmethyl)adipate; epoxidized conjugated diene polymers such as epoxidized polybutadiene and epoxidized styrene-butadiene copolymers; and heterocyclic compounds such as triglycidyl isocyanurate. These epoxy compounds may also be internally crosslinked with a prepolymer having an isocyanate group at the terminal, or may be polymerized with a polyvalent active hydrogen compound (such as a polyhydric phenol, a polyamine, a carbonyl group-containing compound, or a polyphosphate ester).

[0051] In the resin composition of the present disclosure, the component (C) may contain only one type or two or more types. In the present disclosure, from the viewpoint of being able to form a cured product with excellent stress relaxation performance, the component (C) preferably contains two or more types.

[0052] In the present disclosure, from the viewpoint of being able to form a cured product with excellent stress relaxation performance, the component (C) is preferably a polyfunctional epoxy compound having two or more epoxy groups in one molecule.

[0053] In the present disclosure, from the viewpoint of being able to form a cured product with excellent stress relaxation performance, among polyfunctional epoxy compounds having two or more epoxy groups in one molecule, component (C) preferably includes one or more compounds selected from the group consisting of polyglycidyl ether compounds of polyhydric alcohol compounds and polyglycidyl ether compounds of polynuclear polyhydric phenol compounds, and more preferably includes both a polyglycidyl ether compound of a polyhydric alcohol compound and a polyglycidyl ether compound of a polynuclear polyhydric phenol compound.

[0054] In the present disclosure, among the polyglycidyl ether compounds of polynuclear polyhydric phenol compounds, polyglycidyl ether compounds of isopropylidenebisphenol (bisphenol A) are preferred from the viewpoint of being able to form a cured product with excellent stress relaxation performance.

[0055] In the present disclosure, among the polyglycidyl ether compounds of polyhydric alcohol compounds, polyglycidyl ether compounds of 1,4-butanediol are preferred from the viewpoint of being able to form a cured product with excellent stress relaxation performance.

[0056] In the present disclosure, from the viewpoint of being able to form a cured product with excellent stress relaxation performance, the component (C) preferably includes one or more compounds selected from the group consisting of the following compounds No. 3-1 and No. 3-2, and more preferably includes both the following compounds No. 3-1 and No. 3-2.

[0057]

[0058] From the viewpoint of being able to form a cured product with excellent stress relaxation performance, the content of the (C) component is preferably 20 to 98 parts by mass, more preferably 25 to 90 parts by mass, even more preferably 30 to 85 parts by mass, and most preferably 35 to 80 parts by mass, relative to 100 parts by mass of the total of the (A), (B), and (C) components.

[0059] 4. Other Components In the present disclosure, in addition to the components described above, the resin composition may contain, as appropriate, a curing agent, an organic solvent, a flux activator for increasing the activity of a compound having a fluxing effect, a stress reducing agent, an antioxidant, a leveling agent, and various other additives for improving various properties such as compatibility, stability, and workability of the resin.

[0060] In the present disclosure, from the viewpoint of improving curability and ensuring storage stability, it is preferable that the resin composition further contains component (D): a curing agent.

[0061] 4-1. Component (D) The curing agent is not particularly limited as long as it can be used to cure an epoxy compound. Examples include latent curing agents, acid anhydrides, polyamine compounds, polyphenol compounds, and cationic photoinitiators.

[0062] Examples of the latent curing agent include dicyandiamide, hydrazide, imidazole compounds, amine adducts, sulfonium salts, onium salts, ketimines, and tertiary amines. When these latent curing agents are used, the resin composition can be made into a one-component curable resin composition that is easy to handle, which is preferable.

[0063] Examples of acid anhydrides include phthalic anhydride, trimellitic anhydride, pyromellitic anhydride, tetrahydrophthalic anhydride, hexahydrophthalic anhydride, maleic anhydride, succinic anhydride, and 2,2-bis(3,4-dicarboxyphenyl)-1,1,1,3,3,3-hexafluoropropane dianhydride.

[0064] Examples of polyamine compounds include aliphatic polyamines such as ethylenediamine, diethylenetriamine, and triethylenetetramine; alicyclic polyamines such as menthenediamine, isophoronediamine, bis(4-amino-3-methylcyclohexyl)methane, 1,3-bis(aminomethyl)cyclohexane, and 3,9-bis(3-aminopropyl)2,4,8,10-tetraoxaspiro[5,5]undecane; aliphatic amines having an aromatic ring such as M-xylenediamine; and aromatic polyamines such as M-phenylenediamine, 2,2-bis(4-aminophenyl)propane, diaminodiphenylmethane, diaminodiphenylsulfone, α,α-bis(4-aminophenyl)-p-diisopropylbenzene, and 2,2-bis(4-aminophenyl)-1,1,1,3,3,3-hexafluoropropane.

[0065] Examples of polyphenol compounds include phenol novolac, o-cresol novolac, t-butylphenol novolac, dicyclopentadiene cresol, terpene diphenol, terpene dicatechol, 1,1,3-tris(3-tert-butyl-4-hydroxy-6-methylphenyl)butane, butylidenebis(3-tert-butyl-4-hydroxy-6-methylphenyl), and 2,2-bis(4-hydroxyphenyl)-1,1,1,3,3,3-hexafluoropropane.

[0066] Examples of the cationic photoinitiator include compounds described in Japanese Patent No. 5234584.

[0067] Examples of the imidazole compound include 2-phenyl-4,5-dihydroxymethylimidazole, 2-phenyl-4-methyl-5-hydroxymethylimidazole, 2-methylimidazole, 2-phenylimidazole, 2-undecylimidazole, 2-heptadecylimidazole, 2-phenyl-4-methylimidazole, 2-phenyl-4-methyl-5-hydroxymethylimidazole, 1-benzyl-2-phenylimidazole, 1-benzyl-2-methylimidazole, 1-cyanoethyl-2-methylimidazole, 1-cyanoethyl-2-phenylimidazole, 1-cyanoethyl-2-undecylimidazole, 2,4-diamino-6(2'-methylimidazole(1'))ethyl-S-triazine, 2,4-diamino-6(2'-undecylimidazole(1'))ethyl- Examples of imidazoles include S-triazine, 2,4-diamino-6(2'-ethyl,4-methylimidazole(1'))ethyl-S-triazine, 2,4-diamino-6(2'-methylimidazole(1'))ethyl-S-triazine isocyanuric acid adduct, 2-methylimidazole isocyanuric acid 2:3 adduct, 2-phenylimidazole isocyanuric acid adduct, 2-phenyl-3,5-dihydroxymethylimidazole, 2-phenyl-4-hydroxymethyl-5-methylimidazole, and 1-cyanoethyl-2-phenyl-3,5-dicyanoethoxymethylimidazole; and salts of these imidazoles with polycarboxylic acids such as phthalic acid, isophthalic acid, terephthalic acid, trimellitic acid, pyromellitic acid, naphthalenedicarboxylic acid, maleic acid, and oxalic acid.

[0068] In the present disclosure, from the viewpoint of being able to form a cured product with excellent stress relaxation performance, the component (D) is preferably a polyamine compound, more preferably an alicyclic polyamine, and even more preferably 1,3-bis(aminomethyl)cyclohexane.

[0069] From the viewpoint of improving curability and ensuring storage stability, the content of the (D) component is preferably 0.1 to 200 parts by mass, more preferably 0.2 to 100 parts by mass, and most preferably 0.5 to 50 parts by mass, per 100 parts by mass of the total of the (A), (B), and (C) components.

[0070] 4-2. Organic Solvent The organic solvent is not particularly limited, and any organic solvent known in the art can be used. Examples of the organic solvent include acetates such as ethyl acetate, butyl acetate, and ethyl methoxyacetate; ethers such as tetrahydrofuran, tetrahydropyran, ethylene glycol dimethyl ether, triethylene glycol dimethyl ether, and dibutyl ether; ketones such as methyl butyl ketone, methyl isobutyl ketone, ethyl butyl ketone, dipropyl ketone, diisobutyl ketone, methyl amyl ketone, cyclohexanone, and methylcyclohexanone; hydrocarbons such as hexane, cyclohexane, methylcyclohexane, dimethylcyclohexane, ethylcyclohexane, heptane, octane, toluene, and xylene; hydrocarbons having a cyano group such as 1-cyanopropane, 1-cyanonobutane, 1-cyanohexane, cyanocyclohexane, cyanobenzene, 1,3-dicyanopropane, 1,4-dicyanobutane, 1,6-dicyanohexane, 1,4-dicyanocyclohexane, and 1,4-dicyanobenzene; pyridine; and lutidine.

[0071] B. Cured Product The cured product of the present disclosure can be obtained by curing the resin composition of the present disclosure described above. The cured product obtained by curing the resin composition of the present disclosure has excellent stress relaxation performance. Therefore, the cured product obtained by curing the resin composition of the present disclosure can be widely used as a resin substrate for various components in the electrical and electronic fields, such as printed wiring boards, semiconductor encapsulation insulating materials, power semiconductors, LED lighting, LED backlights, power LEDs, and solar cells. Specifically, it is useful as a curable component for refractive index adjustment layers, prepregs, encapsulating materials, laminated substrates, coatable adhesives, adhesive sheets, and the like, as well as a curable component for various paints.

[0072] The shape of the cured product of the present disclosure is not particularly limited, but examples thereof include a sheet, a film, and a plate.

[0073] A sheet-like cured product can be produced, for example, by applying a resin composition to a support such as a carrier film or metal foil and curing the resulting coating layer. Alternatively, a sheet-like cured product can be produced by transferring a coating layer made of the resin composition from the support to a substrate and then curing the resulting layer. Examples of substrates include silicon wafers and aluminum wafers. Examples of substrate shapes include sheet, film, and plate shapes. Curing a resin composition containing an organic solvent can result in a cured product containing the organic solvent, or in a cured product in which the organic solvent has evaporated and substantially no organic solvent remains (is not contained). The cured products of the present disclosure include both those containing an organic solvent and those substantially free of the organic solvent.

[0074] C. Manufacturing Method of Cured Product The manufacturing method of the cured product of the present disclosure includes curing the resin composition of the present disclosure described above. Well-known methods can be used for curing the resin composition, and the method is not particularly limited. From the viewpoint of obtaining a cured product with superior stress relaxation performance, the manufacturing method of the cured product of the present disclosure preferably includes adding a curing agent to the resin composition of the present disclosure described above, if necessary, and then heating the composition at a temperature ranging from 20°C to 170°C for 5 minutes to 5 hours to cure the composition. When producing a sheet-like cured product, the resin composition of the present disclosure may be applied to a support using various coating devices, or the resin composition of the present disclosure may be sprayed onto the support using a spray device. Examples of coating devices that can be used include a roll coater, a bar coater, a knife coater, a gravure coater, a die coater, a comma coater, a curtain coater, and a screen printing device. The resin composition of the present disclosure may also be applied to a support by brush coating.

[0075] D. Other

[0076] The present disclosure includes the following aspects: [1] A resin composition comprising: a component (A): a compound represented by general formula (1), a component (B): one or more compounds selected from the group consisting of compounds represented by general formula (2) and compounds represented by general formula (3), and a component (C): an epoxy compound other than component (B).

[0077]

[0078] (In general formula (1), R 1 represents an unsubstituted aliphatic hydrocarbon group having 1 to 10 carbon atoms, a group in which one or more methylene groups in the aliphatic hydrocarbon group are substituted with a divalent group selected from -O-, -S-, -SO-, or -SO2-, 1 -or-Ar 2 -R 2 -Ar 2 - and Ar 1 is an unsubstituted phenylene group, a phenylene group substituted with 1 to 4 methyl or ethyl groups, an unsubstituted biphenyl group, or a biphenyl group substituted with 1 to 8 methyl or ethyl groups, and Ar 2 are each an unsubstituted phenylene group, a phenylene group substituted with 1 to 4 methyl or ethyl groups, an unsubstituted biphenylene group, or a biphenylene group substituted with 1 to 8 methyl or ethyl groups, and R 2 is -(CH2) d -, -O-, -S-, -SO-, -SO2- or -CO-, and d is an integer of 1 to 8.

[0079]

[0080] (In general formula (2), R 21 is an unsubstituted aliphatic hydrocarbon group having 1 to 20 carbon atoms or a group in which one or more methylene groups in the aliphatic hydrocarbon group have been substituted with a divalent group selected from -O-, -S-, -SO-, or -SO2-; R 22 , R 23 and R 24 are each independently a hydrogen atom or an unsubstituted aliphatic hydrocarbon group having 1 to 20 carbon atoms.

[0081]

[0082] (In general formula (3), R 31 is an unsubstituted aliphatic hydrocarbon group having 1 to 20 carbon atoms or a group in which one or more methylene groups in the aliphatic hydrocarbon group have been substituted with a divalent group selected from -O-, -S-, -SO-, or -SO2-; R 32 , R 33 , R 34 , R 35 , R 36 , R 37 , R 38 , R 39 and R 40 are each independently a hydrogen atom or an unsubstituted aliphatic hydrocarbon group having 1 to 20 carbon atoms.

[0083] [2] The resin composition according to [1], further comprising a curing agent as component (D).

[0084] [3] The resin composition according to [1] or [2], wherein the component (B) contains a compound represented by the general formula (2).

[0085] [4] In the general formula (2), R 21 The resin composition according to any one of [1] to [3], characterized in that one or more methylene groups in the aliphatic hydrocarbon group are substituted with a divalent group selected from -O-, -S-, -SO-, or -SO2-.

[0086] [5] The resin composition according to any one of [1] to [4], wherein the component (B) contains a compound represented by the general formula (3).

[0087] [6] In the general formula (3), R 31 The resin composition according to any one of [1] to [5], characterized in that one or more methylene groups in the aliphatic hydrocarbon group are substituted with a divalent group selected from -O-, -S-, -SO-, or -SO2-.

[0088] [7] A cured product obtained by curing the resin composition according to any one of [1] to [6].

[0089] [8] A method for producing a cured product, comprising curing the resin composition according to any one of [1] to [6].

[0090] The present disclosure is not limited to the above-described embodiments. The above-described embodiments are merely examples, and any embodiment that has substantially the same configuration as the technical idea described in the claims and exhibits similar effects is included within the technical scope of the present disclosure.

[0091] The present disclosure will be described in more detail below with reference to examples, but the present disclosure is not limited to the following examples in any way.

[0092] (Production Example 1) A reaction apparatus equipped with a stirrer, a reflux condenser, a thermometer, and a nitrogen inlet tube was charged with 4.43 g (0.01 mol) of bis(3-ethyl-5-methyl-4-maleimidophenyl)methane (manufactured by Tokyo Chemical Industry Co., Ltd.) and 6.17 g (0.04 mol) of furfuryl glycidyl ether (manufactured by Sigma-Aldrich), and the temperature was raised to 80°C while introducing nitrogen gas, followed by stirring for 2 hours. The reaction product was cooled to room temperature and then purified by medium-pressure preparative liquid chromatography to obtain the following compound.

[0093]

[0094] <Preparation of Cured Products> (Examples 1 and 2 and Comparative Examples 1 to 4)

[0095] A 0.4 mm thick Teflon (registered trademark) spacer was sandwiched between glass plates coated with a release agent, and the resin compositions of the Examples and Comparative Examples, each obtained by mixing the components shown in Table 1, were poured through the gap between the spacers. The resin compositions were heated at 80°C for 5 hours and then at 120°C for 3 hours to cure, yielding cured product sheets.

[0096] The components shown in Table 1 were as follows: As component (A), the following was prepared: A-1: ​​Compound No. 1-1

[0097] The following compounds were prepared as component (B): B-1: Compound No. 2-1

[0098] The following compounds were prepared as component (C): C-1: Compound No. 3-1 C-2: Compound No. 3-2 C-3: Compound represented by the following chemical formula

[0099]

[0100] The following components were prepared as component (D): D-1: 1,3-bis(aminomethyl)cyclohexane

[0101] The following compounds were prepared as the component (X) in the resin composition of the comparative example: X-1: Compound prepared in Preparation Example 1

[0102] <Evaluation> (Stress relaxation performance) The cured products of Examples 1 and 2 and Comparative Examples 1 to 4 were evaluated using a thermomechanical analyzer (TMA-7100 manufactured by Hitachi High-Technologies). Each cured product was brought to a predetermined temperature and then stretched by 5%, and the rate of change between the stress measured initially (σ1) and the stress after 30 minutes (σ2) was calculated using the following formula, and stress relaxation performance was evaluated according to the following evaluation criteria. The results are shown in Table 1. Stress change rate (%) = (σ1 - σ2) / σ1 x 100

[0103] [Evaluation criteria for resin compositions in which the total of C-1 and C-2 is 50 parts by mass per 100 parts by mass of the resin composition excluding component (D)] ◯: Stress change rate (%) is 40% or more △: Stress change rate (%) is 30% or more to less than 40% ×: Stress change rate (%) is less than 30%

[0104] [Evaluation criteria for resin compositions in which the total of C-1 and C-2 is 70 parts by mass per 100 parts by mass of the resin composition excluding component (D)] ◯: Stress change rate (%) is 20% or more △: Stress change rate (%) is 10% or more to less than 20% ×: Stress change rate (%) is less than 10%

[0105]

Claims

1. A resin composition comprising: component (A): a compound represented by general formula (1); component (B): one or more compounds selected from the group consisting of compounds represented by general formula (2) and compounds represented by general formula (3); and component (C): an epoxy compound other than component (B). (In general formula (1), R 1 represents an unsubstituted aliphatic hydrocarbon group having 1 to 10 carbon atoms, a group in which one or more methylene groups in the aliphatic hydrocarbon group are substituted with a divalent group selected from -O-, -S-, -SO-, or -SO2-, 1 -or-Ar 2 -R 2 -Ar 2 - and Ar 1 is an unsubstituted phenylene group, a phenylene group substituted with 1 to 4 methyl or ethyl groups, an unsubstituted biphenyl group, or a biphenyl group substituted with 1 to 8 methyl or ethyl groups; Ar 2 are each an unsubstituted phenylene group, a phenylene group substituted with 1 to 4 methyl groups or ethyl groups, an unsubstituted biphenylene group, or a biphenylene group substituted with 1 to 8 methyl groups or ethyl groups, 2 is -(CH2) d -, -O-, -S-, -SO-, -SO2- or -CO-, and d is an integer of 1 to 8. (In general formula (2), R 21 represents an unsubstituted aliphatic hydrocarbon group having 1 to 20 carbon atoms or a group in which one or more methylene groups in the aliphatic hydrocarbon group are substituted with a divalent group selected from -O-, -S-, -SO-, or -SO2-; 22 , R 23 and R 24 are each independently a hydrogen atom or an unsubstituted aliphatic hydrocarbon group having 1 to 20 carbon atoms. (In general formula (3), R 31 represents an unsubstituted aliphatic hydrocarbon group having 1 to 20 carbon atoms or a group in which one or more methylene groups in the aliphatic hydrocarbon group are substituted with a divalent group selected from -O-, -S-, -SO-, or -SO2-; 32 , R 33 , R 34 , R 35 , R 36 , R 37 , R 38 , R 39 and R 40 are each independently a hydrogen atom or an unsubstituted aliphatic hydrocarbon group having 1 to 20 carbon atoms.

2. The resin composition according to claim 1, further comprising component (D): a curing agent.

3. The resin composition according to claim 1, wherein the component (B) contains a compound represented by the general formula (2).

4. In the general formula (2), R 21 is a group in which one or more methylene groups in the aliphatic hydrocarbon group are substituted with a divalent group selected from -O-, -S-, -SO-, or -SO2-.

5. The resin composition according to claim 1, wherein the component (B) contains a compound represented by the general formula (3).

6. In the general formula (3), R 31 is a group in which one or more methylene groups in the aliphatic hydrocarbon group are substituted with a divalent group selected from -O-, -S-, -SO-, or -SO2-.

7. A cured product obtained by curing the resin composition according to any one of claims 1 to 6.

8. A method for producing a cured product, comprising curing the resin composition according to any one of claims 1 to 6.

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