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

Abstract

To provide a resin composition that enables formation of a cured product having superior stress relaxation properties.SOLUTION: A resin composition comprises: a component (A): a specific bismaleimide compound; a component (B): one or more kinds of compounds selected from the group consisting of a specific furan ring-containing compound and a specific anthracene compound; and a component (C): one or more kinds of compounds selected from the group consisting of acrylate compounds and methacrylate compounds excluding the component (B).SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present disclosure relates to a resin composition, a cured product obtained by curing the resin composition, a method for producing the cured product, and a compound. [Background technology]

[0002] BACKGROUND ART Polymer materials have excellent moldability, electrical properties, moisture resistance, heat resistance, mechanical properties, and the like, and have therefore been used in the fields of molding materials, adhesive materials, electronic parts, ink materials, and the like.

[0003] Polymer 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, the incorporation of various additives into polymer materials has been investigated (see, for example, Patent Document 1). However, the cured product of the resin composition described in Patent Document 1 has the problem of insufficient stress relaxation performance. [Prior art documents] [Patent documents]

[0004] [Patent Document 1] Japanese Patent Application Laid-Open No. 2003-183348 Summary of the Invention [Problem to be solved by the invention]

[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. [Means for solving the problem]

[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 characterized by 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): one or more compounds selected from the group consisting of methacrylate compounds and acrylate compounds different from component (B).

[0008] [ka]

[0009] (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 - represents Ar 1 represents an unsubstituted phenylene group, a phenylene group substituted with 1 to 4 methyl groups or 1 to 4 ethyl groups, an unsubstituted biphenylene group, or a biphenylene group substituted with 1 to 8 methyl groups or 1 to 8 ethyl groups, Ar 2 represent an unsubstituted phenylene group, a phenylene group substituted with 1 to 4 methyl groups or 1 to 4 ethyl groups, an unsubstituted biphenylene group, or a biphenylene group substituted with 1 to 8 methyl groups or 1 to 8 ethyl groups, respectively; R 2 is -(CH2) d represents -, -O-, -S-, -SO-, -SO2- or -CO-, and d is an integer of 1 to 8.

[0010] [ka]

[0011] (In general formula (2), R 21represents an unsubstituted aliphatic hydrocarbon group having 1 to 20 carbon atoms, or an unsubstituted aliphatic hydrocarbon group having 1 to 20 carbon atoms in which one or more methylene groups have been substituted with a divalent group selected from -OCONH-, -NHCOO-, -NHCO-, -CONH-, -O-, -S-, -SO-, or -SO2-; R 22 , R 23 and R 24 each independently represents a hydrogen atom or an unsubstituted aliphatic hydrocarbon group having 1 to 20 carbon atoms, R 25 is a hydrogen atom or a methyl group.

[0012] [ka]

[0013] (In general formula (3), R 31 represents an unsubstituted aliphatic hydrocarbon group having 1 to 20 carbon atoms, or an unsubstituted aliphatic hydrocarbon group having 1 to 20 carbon atoms in which one or more methylene groups are -OCONH-, -NHCOO-, -NHCO-, -CONH-, -O-, -S-, -SO-, or -SO 2 - represents a group substituted with a divalent group selected from R 32 , R 33 , R 34 , R 35 , R 36 , R 37 , R 38 , R 39 and R 40 each independently represents a hydrogen atom or an unsubstituted aliphatic hydrocarbon group having 1 to 20 carbon atoms, R 41 is a hydrogen atom or a methyl group.

[0014] The resin composition of the present disclosure preferably contains one or more selected from the group consisting of component (D): a thermal polymerization initiator and component (E): a photopolymerization initiator.

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

[0016] In the resin composition of the present disclosure, in the general formula (2), R 21 is preferably an unsubstituted aliphatic hydrocarbon group having 1 to 10 carbon atoms or an unsubstituted aliphatic hydrocarbon group having 1 to 10 carbon atoms in which one or more methylene groups have been substituted with a divalent group selected from -OCONH- or -NHCOO-.

[0017] In the resin composition of the present disclosure, in the general formula (2), R 25 is preferably a methyl group.

[0018] The present disclosure relates to a cured product obtained by curing the above-mentioned resin composition.

[0019] The present disclosure is a method for producing a cured product, which includes curing the above-described resin composition.

[0020] The present disclosure relates to a compound represented by general formula (I).

[0021] [ka]

[0022] (In general formula (I), R 201 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-, -Ar 201 -or-Ar 202 -R 202 -Ar 202 - represents Ar 201 represents an unsubstituted phenylene group, a phenylene group substituted with 1 to 4 methyl groups or 1 to 4 ethyl groups, an unsubstituted biphenylene group, or a biphenylene group substituted with 1 to 8 methyl groups or 1 to 8 ethyl groups, Ar 202 represent an unsubstituted phenylene group, a phenylene group substituted with 1 to 4 methyl groups or 1 to 4 ethyl groups, an unsubstituted biphenylene group, or a biphenylene group substituted with 1 to 8 methyl groups or 1 to 8 ethyl groups, respectively; R 202 is -(CH2) d represents -, -O-, -S-, -SO-, -SO2-, or -CO-, and d is an integer of 1 to 8; R 221 represents an unsubstituted aliphatic hydrocarbon group having 1 to 20 carbon atoms, or an unsubstituted aliphatic hydrocarbon group having 1 to 20 carbon atoms in which one or more methylene groups have been substituted with a divalent group selected from -OCONH-, -NHCOO-, -S-, -SO-, or -SO2-; R 222 , R 223 and R 224 each independently represents a hydrogen atom or an unsubstituted aliphatic hydrocarbon group having 1 to 20 carbon atoms, R 225 represents a hydrogen atom or a methyl group.

[0023] In the compound represented by general formula (I) of the present disclosure, 221 is preferably an unsubstituted aliphatic hydrocarbon group having 1 to 10 carbon atoms or an unsubstituted aliphatic hydrocarbon group having 1 to 10 carbon atoms in which one or more methylene groups have been substituted with a divalent group selected from -OCONH- or -NHCOO-.

[0024] In the compound represented by general formula (I) of the present disclosure, 225 is preferably a methyl group. [Effects of the Invention]

[0025] According to the present disclosure, it is possible to provide a resin composition capable of forming a cured product with excellent stress relaxation performance. DETAILED DESCRIPTION OF THE INVENTION

[0026] A. Resin Composition The resin composition of the present disclosure comprises: 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): one or more compounds selected from the group consisting of methacrylate compounds and acrylate compounds different from 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.

[0027] The elements constituting the resin composition of the present disclosure will be described in detail below. 1. (A) Component The resin composition of the present disclosure contains component (A): a bismaleimide compound represented by general formula (1).

[0028] [ka]

[0029] 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 - represents. Ar 1 represents an unsubstituted phenylene group, a phenylene group substituted with 1 to 4 methyl groups or 1 to 4 ethyl groups, an unsubstituted biphenylene group, or a biphenylene group substituted with 1 to 8 methyl groups or 1 to 8 ethyl groups. Ar 2respectively represent an unsubstituted phenylene group, a phenylene group substituted with 1 to 4 methyl groups or 1 to 4 ethyl groups, an unsubstituted biphenylene group, or a biphenylene group substituted with 1 to 8 methyl groups or 1 to 8 ethyl groups. R 2 is -(CH2) d represents -, -O-, -S-, -SO-, -SO2- or -CO-. d is an integer of 1 to 8.

[0030] In the present disclosure, in general formula (1), R 1 From the viewpoint of being able to form a cured product with excellent stress relaxation performance, -Ar 2 -R 2 -Ar 2 - is preferred.

[0031] In general formula (1), R 1 Ga-Ar 2 -R 2 -Ar 2 -, if Ar 2 From the viewpoint of forming a cured product having excellent stress relaxation performance, each of R1 is preferably an unsubstituted phenylene group or a phenylene group substituted with 1 to 4 methyl groups or 1 to 4 ethyl groups, more preferably a phenylene group substituted with 1 to 4 methyl groups or 1 to 4 ethyl groups, and most preferably a phenylene group substituted with two methyl groups, a phenylene group substituted with two ethyl groups, or a phenylene group substituted with one methyl group and one ethyl group. 2 -R 2 -Ar 2 When R2 is -, it is preferable that R2 is -(CH2) from the viewpoint of forming a cured product having excellent stress relaxation properties. d It is preferably -, and more preferably -CH2-.

[0032] 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.

[0033] Specific examples of the compound represented by general formula (1) include the following compounds, but the present disclosure is not limited to these compounds. Among these, compound No. 1-1 is preferred from the viewpoint of forming a cured product with excellent stress relaxation properties.

[0034] [ka]

[0035] The resin composition of the present disclosure may contain only one type of component (A), or may contain two or more types.

[0036] From the viewpoint of forming a cured product with excellent stress relaxation performance, the content of the (A) component is preferably 1 to 50 parts by mass, more preferably 2 to 35 parts by mass, even more preferably 2 to 20 parts by mass, and most preferably 2 to 10 parts by mass, per 100 parts by mass of the (A), (B), and (C) components combined.

[0037] 2.(B) Component The resin composition of the present disclosure contains component (B): one or more compounds selected from the group consisting of furan ring-containing compounds represented by general formula (2) and anthracene compounds represented by general formula (3).

[0038] [ka]

[0039] In general formula (2), R 21represents an unsubstituted aliphatic hydrocarbon group having 1 to 20 carbon atoms, or an unsubstituted aliphatic hydrocarbon group having 1 to 20 carbon atoms in which one or more methylene groups have been substituted with a divalent group selected from -OCONH-, -NHCOO-, -NHCO-, -CONH-, -O-, -S-, -SO-, or -SO2-. In general formula (2), R 22 , R 23 and R 24 each independently represents a hydrogen atom or an unsubstituted aliphatic hydrocarbon group having 1 to 20 carbon atoms. In general formula (2), R 25 is a hydrogen atom or a methyl group.

[0040] In general formula (3), R 31 represents an unsubstituted aliphatic hydrocarbon group having 1 to 20 carbon atoms, or an unsubstituted aliphatic hydrocarbon group having 1 to 20 carbon atoms in which one or more methylene groups are -OCONH-, -NHCOO-, -NHCO-, -CONH-, -O-, -S-, -SO-, or -SO 2 - represents a group substituted with a divalent group selected from In general formula (3), R 32 , R 33 , R 34 , R 35 , R 36 , R 37 , R 38 , R 39 and R 40 each independently represents a hydrogen atom or an unsubstituted aliphatic hydrocarbon group having 1 to 20 carbon atoms. In general formula (3), R 41 is a hydrogen atom or a methyl group.

[0041] 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.

[0042] In the present disclosure, in general formula (2), R 21From the viewpoint of being able to form a cured product having excellent stress relaxation performance, is preferably an unsubstituted aliphatic hydrocarbon group having 1 to 20 carbon atoms or an unsubstituted aliphatic hydrocarbon group having 1 to 20 carbon atoms in which one or more methylene groups have been substituted with a divalent group selected from -OCONH-, -NHCOO-, -NHCO-, -CONH-, or -O-, more preferably an unsubstituted aliphatic hydrocarbon group having 1 to 10 carbon atoms or an unsubstituted aliphatic hydrocarbon group having 1 to 10 carbon atoms in which one or more methylene groups have been substituted with a divalent group selected from -OCONH- or -NHCOO-, even more preferably an unsubstituted aliphatic hydrocarbon group having 1 to 5 carbon atoms or an unsubstituted aliphatic hydrocarbon group having 1 to 5 carbon atoms in which one or more methylene groups have been substituted with -NHCOO-, and most preferably an unsubstituted aliphatic hydrocarbon group having 1 to 5 carbon atoms.

[0043] In the present disclosure, in general formula (2), R 25 is preferably a methyl group from the viewpoint of forming a cured product having excellent stress relaxation properties.

[0044] 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 with excellent stress relaxation performance.

[0045] 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 properties under high temperature conditions.

[0046] 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 an unsubstituted aliphatic hydrocarbon group having 1 to 20 carbon atoms or an unsubstituted aliphatic hydrocarbon group having 1 to 20 carbon atoms in which one or more methylene groups have been substituted with a divalent group selected from -OCONH-, -NHCOO-, -NHCO-, -CONH-, or -O-, more preferably an unsubstituted aliphatic hydrocarbon group having 1 to 10 carbon atoms or an unsubstituted aliphatic hydrocarbon group having 1 to 10 carbon atoms in which one or more methylene groups have been substituted with a divalent group selected from -OCONH- or -NHCOO-, and even more preferably an unsubstituted aliphatic hydrocarbon group having 1 to 10 carbon atoms.

[0047] In the present disclosure, in general formula (3), R 41 is preferably a methyl group from the viewpoint of forming a cured product having excellent stress relaxation properties.

[0048] 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 with excellent stress relaxation performance.

[0049] Specific examples of the compound represented by general formula (2) or general formula (3) include the following compounds, but the present disclosure is not limited to these compounds. Among these, one or more compounds selected from the group consisting of compounds No. 2-1 and No. 2-2 are preferred from the viewpoint of forming a cured product having excellent stress relaxation properties.

[0050] [ka]

[0051] The resin composition of the present disclosure may contain only one type of component (B), or may contain two or more types.

[0052] From the viewpoint of forming a cured product with excellent stress relaxation performance, the content of the (B) component is preferably 1 to 50 parts by mass, more preferably 2 to 35 parts by mass, even more preferably 2 to 20 parts by mass, and most preferably 2 to 10 parts by mass, per 100 parts by mass of the total of the (A), (B), and (C) components.

[0053] 3.(C) Component The resin composition of the present disclosure contains component (C): one or more compounds selected from the group consisting of methacrylate compounds and acrylate compounds that are different from component (B). In the present disclosure, "one or more compounds selected from the group consisting of methacrylate compounds and acrylate compounds that are different from component (B)" refers to one or more compounds selected from the group consisting of methacrylate compounds and acrylate compounds, and is different from both the compound represented by general formula (2) and the compound represented by general formula (3).

[0054] Examples of acrylate compounds that can be used in the resin composition of the present disclosure include monofunctional acrylate compounds, difunctional acrylate compounds, and trifunctional or higher functional acrylate compounds. Examples of methacrylate compounds that can be used in the resin composition of the present disclosure include monofunctional methacrylate compounds, difunctional methacrylate compounds, and trifunctional or higher functional methacrylate compounds.

[0055] From the viewpoint of being able to form a cured product with excellent stress relaxation performance, component (C) is preferably one or more compounds selected from the group consisting of monofunctional methacrylate compounds, bifunctional methacrylate compounds, trifunctional or higher functional polyfunctional methacrylate compounds, bifunctional acrylate compounds, and trifunctional or higher functional polyfunctional acrylate compounds, and is more preferably a monofunctional methacrylate compound.

[0056] The resin composition of the present disclosure may contain only one type of component (C), or may contain two or more types.

[0057] In the present disclosure, examples of the monofunctional acrylate compound include alkyl acrylates such as methyl acrylate, ethyl acrylate, n-propyl acrylate, isopropyl acrylate, n-butyl acrylate, isobutyl acrylate, tert-butyl acrylate, n-pentyl acrylate, isopentyl acrylate, tert-pentyl acrylate, neopentyl acrylate, hexyl acrylate, octyl acrylate, dodecyl acrylate, and stearyl acrylate, benzyl acrylate, alkylphenols (butylphenol, octylphenol, nonylphenol, dodecylphenol, and the like), acrylates of ethylene oxide adducts, isobornyl acrylate, cyclohexyl acrylate, tricyclodecane monomethylol acrylate, 2-hydroxyethyl acrylate, 2-hydroxypropyl acrylate, 3-hydroxypropyl acrylate, and 2-hydroxybutyl acrylate. Examples of the acrylic acid acrylate include acrylate, 4-hydroxybutyl acrylate, hydroxypentyl acrylate, 2-hydroxy-3-phenoxypropyl acrylate, 2-hydroxy-3-butoxypropyl acrylate, 2-hydroxy-3-methoxypropyl acrylate, diethylene glycol monoacrylate, triethylene glycol monoacrylate, polyethylene glycol monoacrylate, dipropylene glycol monoacrylate, polypropylene glycol monoacrylate, glycerin monoacrylate, acryloyloxyethyl phthalate, 2-acryloyloxyethyl-2-hydroxyethyl phthalate, 2-acryloyloxypropyl phthalate, β-carboxyethyl acrylate, acrylic acid dimer, ω-carboxy-polycaprolactone monoacrylate, dimethylaminoethyl acrylate, diethylaminoethyl acrylate, N-vinylpyrrolidone, N-vinylformamide, and acryloylmorpholine.

[0058] In the present disclosure, examples of the bifunctional acrylate compound include ethylene glycol diacrylate, diethylene glycol diacrylate, triethylene glycol diacrylate, polyethylene glycol diacrylate, propylene glycol diacrylate, dipropylene glycol diacrylate, tripropylene glycol diacrylate, polypropylene glycol diacrylate, butylene glycol diacrylate, pentyl glycol diacrylate, neopentyl glycol diacrylate, and hydroxypivalyl hydroxypivalate. Diacrylate, Hydroxypivalyl Hydroxypivalate Dicaprolactonate Diacrylate, 1,6-Hexanediol Diacrylate, 1,2-Hexanediol Diacrylate, 1,5-Hexanediol Diacrylate, 2,5-Hexanediol Diacrylate, 1,7-Heptanediol Diacrylate, 1,8-Octanediol Diacrylate, 1,2-Octanediol Diacrylate, 1,9-Nonanediol Diacrylate, 1,2-Decanediol Diacrylate, 1,10-Decanediol Diacrylate, 1,2-Decanediol Diacrylate Diol diacrylate, 1,12-dodecanediol diacrylate, 1,2-dodecanediol diacrylate, 1,14-tetradecanediol diacrylate, 1,2-tetradecanediol diacrylate, 1,16-hexadecanediol diacrylate, 1,2-hexadecanediol diacrylate, 2-methyl-2,4-pentanediol diacrylate, 3-methyl-1,5-pentanediol diacrylate, 2-methyl-2-propyl-1,3-propanediol diacrylate, 2,4-dimethyl-2,4-pentanediol diacrylate Acrylates, 2,2-diethyl-1,3-propanediol diacrylate, 2,2,4-trimethyl-1,3-pentanediol diacrylate, dimethylol octane diacrylate, 2-ethyl-1,3-hexanediol diacrylate, 2,5-dimethyl-2,5-hexanediol diacrylate, 2-methyl-1,8-octanediol diacrylate, 2-butyl-2-ethyl-1,3-propanediol diacrylate, 2,4-diethyl-1,5-pentanediol diacrylate, 1,2-hexanediol diacrylate, 1,5-Hexanediol diacrylate, 2,5-Hexanediol diacrylate, 1,7-Heptanediol diacrylate, 1,8-Octanediol diacrylate, 1,2-Octanediol diacrylate, 1,9-Nonanediol diacrylate, 1,2-Decanediol diacrylate, 1,10-Decanediol diacrylate, 1,2-Decanediol diacrylate, 1,12-Dodecanediol diacrylate, 1,2-Dodecanediol diacrylate, 1,14-Tetradecanediol diacrylate Acrylates, 1,2-tetradecanediol diacrylate, 1,16-hexadecanediol diacrylate, 1,2-hexadecanediol diacrylate, 2-methyl-2,4-pentane diacrylate, 3-methyl-1,5-pentanediol diacrylate, 2-methyl-2-propyl-1,3-propanediol diacrylate, 2,4-dimethyl-2,4-pentanediol diacrylate, 2,2-diethyl-1,3-propanediol diacrylate, 2,2,4-trimethyl-1,3-pentane Examples of the diol diacrylate include dimethylol octane diacrylate, 2-ethyl-1,3-hexanediol diacrylate, 2,5-dimethyl-2,5-hexanediol diacrylate, 2-butyl-2-ethyl-1,3-propanediol diacrylate, 2,4-diethyl-1,5-pentanediol diacrylate, tricyclodecane dimethylol diacrylate, tricyclodecane dimethylol dicaprolactonate diacrylate, bisphenol A ethylene oxide adduct diacrylate, bisphenol F ethylene oxide adduct diacrylate, bisphenol S ethylene oxide adduct diacrylate, water-added bisphenol A ethylene oxide adduct diacrylate, water-added bisphenol F ethylene oxide adduct diacrylate, water-added bisphenol A diacrylate, water-added bisphenol F diacrylate, bisphenol A ethylene oxide adduct dicaprolactonate diacrylate, and bisphenol F ethylene oxide adduct dicaprolactonate diacrylate.

[0059] In the present disclosure, examples of the polyfunctional acrylate compound include glycerin triacrylate, trimethylolpropane triacrylate, trimethylolpropane tricaprolactonate triacrylate, trimethylolethane triacrylate, trimethylolhexane triacrylate, trimethyloloctane triacrylate, pentaerythritol triacrylate, pentaerythritol tetraacrylate, pentaerythritol tetracaprolactonate tetraacrylate, diglycerin tetraacrylate, ditrimethylolpropane tetraacrylate, ditrimethylolpropane tri ... Examples of the alkyl acrylate include ethylolpropane tetracaprolactonate tetraacrylate, ditrimethylolethane tetraacrylate, ditrimethylolbutane tetraacrylate, ditrimethylolhexane tetraacrylate, ditrimethyloloctane tetraacrylate, dipentaerythritol pentamethacrylate, dipentaerythritol hexaacrylate, tripentaerythritol hexaacrylate, tripentaerythritol hepmethacrylate, tripentaerythritol octamethacrylate, and tripentaerythritol polyalkylene oxide hepmethacrylate.

[0060] In the present disclosure, the bifunctional acrylate compound and the polyfunctional acrylate compound also include epoxy acrylate. Epoxy acrylate is obtained by an addition reaction between acrylic acid and a polyfunctional epoxy compound. The polyfunctional epoxy compound may have two or more epoxy groups in one molecule. Examples of such polyfunctional epoxy compounds include bisphenol-type epoxy resins such as bisphenol A-type epoxy resins, bisphenol F-type epoxy resins, and bisphenol AD-type epoxy resins; rubber-modified epoxy resins such as biphenyl-type epoxy resins, naphthalene-type epoxy resins, dicyclopentadiene-type epoxy resins, and silicone-modified epoxy resins; ε-caprolactone-modified epoxy resins; phenol novolac-type epoxy resins such as bisphenol A-type, bisphenol F-type, and bisphenol AD-type; cresol novolac-type epoxy resins such as o-cresol novolac-type; cycloaliphatic polyfunctional epoxy resins; glycidyl ester-type polyfunctional epoxy resins; glycidyl amine-type polyfunctional epoxy resins; heterocyclic polyfunctional epoxy resins; bisphenol-modified novolac-type epoxy resins; polyfunctionally modified novolac-type epoxy resins; and condensation products of phenols and aromatic aldehydes having phenolic hydroxyl groups. Furthermore, these resins containing halogen atoms such as Br and Cl can also be used. The polyfunctional epoxy compound may be a glycidyl-type epoxy compound having a glycidyl group, or may be an epoxy compound having a cycloalkene oxide structure.

[0061] In the present disclosure, examples of the monofunctional methacrylate compound include alkyl methacrylates such as methacrylic acid, methyl methacrylate, ethyl methacrylate, n-propyl methacrylate, isopropyl methacrylate, n-butyl methacrylate, isobutyl methacrylate, tert-butyl methacrylate, n-pentyl methacrylate, isopentyl methacrylate, tert-pentyl methacrylate, neopentyl methacrylate, hexyl methacrylate, octyl methacrylate, dodecyl methacrylate, and stearyl methacrylate, benzyl methacrylate, alkylphenols (butylphenol, octylphenol, nonylphenol, dodecylphenol, and the like), methacrylates of ethylene oxide adducts, isobornyl methacrylate, cyclohexyl methacrylate, tricyclodecane monomethylol methacrylate, 2-hydroxyethyl methacrylate, 2-hydroxypropyl methacrylate, 3-hydroxypropyl methacrylate, 2 ... Examples of suitable monofunctional methacrylate compounds include 2-hydroxybutyl methacrylate, 4-hydroxybutyl methacrylate, hydroxypentyl methacrylate, 2-hydroxy-3-phenoxypropyl methacrylate, 2-hydroxy-3-butoxypropyl methacrylate, 2-hydroxy-3-methoxypropyl methacrylate, diethylene glycol monomethacrylate, triethylene glycol monomethacrylate, polyethylene glycol monomethacrylate, dipropylene glycol monomethacrylate, polypropylene glycol monomethacrylate, glycerin monomethacrylate, acryloyloxyethyl phthalate, 2-acryloyloxyethyl-2-hydroxyethyl phthalate, 2-acryloyloxypropyl phthalate, β-carboxyethyl methacrylate, acrylic acid dimer, ω-carboxy-polycaprolactone monomethacrylate, dimethylaminoethyl methacrylate, diethylaminoethyl methacrylate, N-vinylpyrrolidone, N-vinylformamide, and acryloylmorpholine. In the present disclosure, the monofunctional methacrylate compound is preferably hexyl methacrylate, from the viewpoint of forming a cured product with excellent stress relaxation properties.

[0062] In the present disclosure, examples of the bifunctional methacrylate compound include ethylene glycol dimethacrylate, diethylene glycol dimethacrylate, triethylene glycol dimethacrylate, polyethylene glycol dimethacrylate, propylene glycol dimethacrylate, dipropylene glycol dimethacrylate, tripropylene glycol dimethacrylate, polypropylene glycol dimethacrylate, butylene glycol dimethacrylate, pentyl glycol dimethacrylate, neopentyl glycol dimethacrylate, and hydroxypivalate. Hydroxypivalyl Hydroxypivalate Dimethacrylate, Hydroxypivalyl Hydroxypivalate Dicaprolactonate Dimethacrylate, 1,6-Hexanediol Dimethacrylate, 1,2-Hexanediol Dimethacrylate, 1,5-Hexanediol Dimethacrylate, 2,5-Hexanediol Dimethacrylate, 1,7-Heptanediol Dimethacrylate, 1,8-Octanediol Dimethacrylate, 1,2-Octanediol Dimethacrylate, 1,9-Nonanediol Dimethacrylate, 1,2-Decanediol Dimethacrylate, 1,10-Decanediol Dimethacrylate 1,2-Decanediol dimethacrylate, 1,12-Dodecanediol dimethacrylate, 1,2-Dodecanediol dimethacrylate, 1,14-Tetradecanediol dimethacrylate, 1,2-Tetradecanediol dimethacrylate, 1,16-Hexadecanediol dimethacrylate, 1,2-Hexadecanediol dimethacrylate, 2-Methyl-2,4-pentanediol dimethacrylate, 3-Methyl-1,5-pentanediol dimethacrylate, 2-Methyl-2-propyl-1,3-propanediol Dimethacrylate, 2,4-dimethyl-2,4-pentanediol dimethacrylate, 2,2-diethyl-1,3-propanediol dimethacrylate, 2,2,4-trimethyl-1,3-pentanediol dimethacrylate, dimethylol octane dimethacrylate, 2-ethyl-1,3-hexanediol dimethacrylate, 2,5-dimethyl-2,5-hexanediol dimethacrylate, 2-methyl-1,8-octanediol dimethacrylate, 2-butyl-2-ethyl-1,3-propanediol dimethacrylate, 2,4-diethyl-1,5-Pentanediol dimethacrylate, 1,2-Hexanediol dimethacrylate, 1,5-Hexanediol dimethacrylate, 2,5-Hexanediol dimethacrylate, 1,7-Heptanediol dimethacrylate, 1,8-Octanediol dimethacrylate, 1,2-Octanediol dimethacrylate, 1,9-Nonanediol dimethacrylate, 1,2-Decanediol dimethacrylate, 1,10-Decanediol dimethacrylate, 1,2-Decanediol dimethacrylate, 1,12-Dodecanediol dimethacrylate, 1,2-Dodecanediol dimethacrylate, 1,14-Tetradecanediol dimethacrylate, 1,2-Tetradecanediol dimethacrylate, 1,16-Hexadecanediol Dimethacrylate, 1,2-hexadecanediol dimethacrylate, 2-methyl-2,4-pentanediol dimethacrylate, 3-methyl-1,5-pentanediol dimethacrylate, 2-methyl-2-propyl-1,3-propanediol dimethacrylate, 2,4-dimethyl-2,4-pentanediol dimethacrylate, 2,2-diethyl-1,3-propanediol dimethacrylate, 2,2,4-trimethyl-1,3-pentanediol dimethacrylate, dimethylol octane dimethacrylate, 2-ethyl-1,3-hexanediol dimethacrylate, 2,5-dimethyl-2,5-hexanediol dimethacrylate, 2-butyl-2-ethyl-1,3-propanediol dimethacrylate, 2,4-diethyl-1,Examples of suitable dimethacrylates include 5-pentanediol dimethacrylate, tricyclodecane dimethylol dimethacrylate, tricyclodecane dimethylol dicaprolactonate dimethacrylate, bisphenol A ethylene oxide adduct dimethacrylate, bisphenol F ethylene oxide adduct dimethacrylate, bisphenol S ethylene oxide adduct dimethacrylate, hydrated bisphenol A tetraethylene oxide adduct dimethacrylate, hydrated bisphenol F ethylene oxide adduct dimethacrylate, hydrated bisphenol A dimethacrylate, hydrated bisphenol F dimethacrylate, bisphenol A ethylene oxide adduct dicaprolactonate dimethacrylate, and bisphenol F ethylene oxide adduct dicaprolactonate dimethacrylate.

[0063] In the present disclosure, examples of the polyfunctional methacrylate compound include glycerin trimethacrylate, trimethylolpropane trimethacrylate, trimethylolpropane tricaprolactonate trimethacrylate, trimethylolethane trimethacrylate, trimethylolhexane trimethacrylate, trimethyloloctane trimethacrylate, pentaerythritol trimethacrylate, pentaerythritol tetramethacrylate, pentaerythritol tetracaprolactonate tetramethacrylate, diglycerin tetramethacrylate, ditrimethylolpropane tetramethacrylate, ditrimethylolpropane tri ... Examples of the methacrylate include ethylolpropane tetracaprolactonate tetramethacrylate, ditrimethylolethane tetramethacrylate, ditrimethylolbutane tetramethacrylate, ditrimethylolhexane tetramethacrylate, ditrimethyloloctane tetramethacrylate, dipentaerythritol pentamethacrylate, dipentaerythritol hexamethacrylate, tripentaerythritol hexamethacrylate, tripentaerythritol heptamethacrylate, tripentaerythritol octamethacrylate, and tripentaerythritol polyalkylene oxide heptamethacrylate. Other methacrylates that can be used include urethane methacrylate and polyester methacrylate.

[0064] In the present disclosure, the bifunctional methacrylate compound and the polyfunctional methacrylate compound also include epoxy methacrylate. Epoxy methacrylate is obtained by an addition reaction between methacrylic acid and a polyfunctional epoxy compound. The polyfunctional epoxy compound may have two or more epoxy groups in one molecule. The polyfunctional epoxy compound may be the same as the compounds exemplified for the epoxy acrylate, and therefore, a description thereof will be omitted here.

[0065] In the present disclosure, the bifunctional methacrylate compounds, trifunctional or higher polyfunctional methacrylate compounds, bifunctional acrylate compounds, and trifunctional or higher polyfunctional acrylate compounds also include compounds containing a urethane bond in the molecule, i.e., compounds having a urethane bond and a methacryl group or an acrylic group in the same molecule (hereinafter, these may be referred to as a urethane methacrylate compound and a urethane acrylate compound, respectively).

[0066] The urethane methacrylate compound and the urethane acrylate compound are not particularly limited as long as they are compounds having a urethane bond and a methacryl group or an acrylic group in the same molecule, and can be obtained by reacting an alcohol containing a methacryl group or an acrylic group with an isocyanate compound.

[0067] In the present disclosure, examples of the urethane methacrylate compound and the urethane acrylate compound include pentaerythritol triacrylate hexamethylene diisocyanate urethane prepolymer, pentaerythritol triacrylate toluene diisocyanate urethane prepolymer, pentaerythritol triacrylate isophorone diisocyanate urethane prepolymer, and dipentaerythritol pentamethacrylate hexamethylene diisocyanate urethane prepolymer.

[0068] As the urethane methacrylate compound and the urethane acrylate compound, commercially available products can also be used. Specific examples include NK Oligo U-4HA, U-6HA, U-108A (all manufactured by Shin-Nakamura Chemical Co., Ltd.), AH-600, UA-306H, UA-306T, UA-306I, UA-510H (all manufactured by Kyoeisha Chemical Co., Ltd.), Art Resin (registered trademark) UN-904, UN-9000PE, UN-9200A, UN-9000, UN-1255, UN-2601, UN-2310, UN-5200, UN-330, UN-333, UN-3320HA, UN-3320HB, UN-3320H, UN-3320H, UN-6060P, UN-6060P™, SH-500 (all manufactured by Negami Chemical Industries, Ltd.).

[0069] From the viewpoint of forming a cured product with excellent stress relaxation performance, the content of the (C) component is preferably 20 to 99 parts by mass, more preferably 40 to 98 parts by mass, even more preferably 60 to 98 parts by mass, and most preferably 70 to 98 parts by mass, relative to 100 parts by mass of the total of the (A), (B), and (C) components.

[0070] 4. Other ingredients In the present disclosure, the resin composition may contain, in addition to the components described above, various additives appropriate for improving various properties such as thermal polymerization initiators, photopolymerization initiators, organic solvents, flux activators for increasing the activity of compounds having a fluxing effect, stress reducing agents, antioxidants, leveling agents, and other resin compatibility, stability, and workability. From the viewpoint of improving curability and ensuring storage stability, the resin composition of the present disclosure preferably contains one or more selected from the group consisting of component (D): a thermal polymerization initiator and component (E): a photopolymerization initiator, and more preferably contains component (D): a thermal polymerization initiator.

[0071] When the resin composition of the present disclosure contains one or more selected from the group consisting of a (D) component: a thermal polymerization initiator and a (E) component: a photopolymerization initiator, the total content of the (D) component: the thermal polymerization initiator and the (E) component: the photopolymerization initiator is preferably 0.1 to 30 parts by mass, more preferably 0.1 to 15 parts by mass, and even more preferably 0.2 to 10 parts by mass, per 100 parts by mass of the total of the (A) component, the (B) component, and the (C) component.

[0072] When the resin composition of the present disclosure contains component (D): a thermal polymerization initiator, the content of component (D): a thermal polymerization initiator is preferably 0.1 to 30 parts by mass, more preferably 0.1 to 15 parts by mass, and even more preferably 0.2 to 10 parts by mass, relative to 100 parts by mass of the total of components (A), (B), and (C).

[0073] 4-1.(D) Component Component (D): As the thermal polymerization initiator, conventionally known compounds can be used, including, for example, azo polymerization initiators such as 2,2'-azobisisobutyronitrile, 2,2'-azobis(methyl isobutyrate), 2,2'-azobis(2,4-dimethylvaleronitrile), and 1,1'-azobis(1-acetoxy-1-phenylethane); peroxide polymerization initiators such as benzoyl peroxide, di-t-butylbenzoyl peroxide, t-butyl peroxypivalate, and di(4-t-butylcyclohexyl)peroxydicarbonate; and persulfates such as ammonium persulfate, sodium persulfate, and potassium persulfate. These can be used alone or in combination of two or more.

[0074] Among the above thermal polymerization initiators, azo-based polymerization initiators are preferred, and azobis-based compounds are more preferred, from the viewpoint of heat resistance.

[0075] 4-2.(E) Component Component (E): The photopolymerization initiator includes a radical polymerization initiator that initiates radical polymerization upon exposure to light.

[0076] Preferred examples of the radical polymerization initiator include ketone compounds such as acetophenone compounds, benzyl compounds, benzophenone compounds, and thioxanthone compounds, and oxime compounds.

[0077] Examples of the acetophenone compounds include diethoxyacetophenone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, 4'-isopropyl-2-hydroxy-2-methylpropiophenone, 2-hydroxymethyl-2-methylpropiophenone, 2,2-dimethoxy-1,2-diphenylethan-1-one, p-dimethylaminoacetophenone, p-tert-butyldichloroacetophenone, p-tert-butyltrichloroacetophenone, p-azidobenzalacetophenone, 1-hydroxy ... Examples of such methyl ethers include 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropanone-1, 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butanone-1, benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin-n-butyl ether, benzoin isobutyl ether, and 1-[4-(2-hydroxyethoxy)-phenyl]-2-hydroxy-2-methyl-1-propan-1-one.

[0078] Examples of the benzyl compounds include benzyl and anisyl.

[0079] Examples of the benzophenone compounds include benzophenone, methyl o-benzoylbenzoate, Michler's ketone, 4,4'-bisdiethylaminobenzophenone, 4,4'-dichlorobenzophenone, and 4-benzoyl-4'-methyldiphenyl sulfide.

[0080] Examples of the thioxanthone compounds include thioxanthone, 2-methylthioxanthone, 2-ethylthioxanthone, 2-chlorothioxanthone, 2-isopropylthioxanthone, and 2,4-diethylthioxanthone.

[0081] Examples of the oxime compounds include 1,2-octanedione, 1-[4-(phenylthio)-, 2-(O-benzoyloxime)], ethanone, 1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-, 1-(O-acetyloxime), methanone, (2-methylphenyl)[6-nitro-9-[3-(trimethylsilyl)propyl]-9H-carbazol-3-yl]-, 1-(O-acetyloxime), Methanone, (9-ethyl-6-nitro-9H-carbazol-3-yl) (2-methylphenyl), O-acetyloxime, Methanone, (9-ethyl-6-nitro-9H-carbazol-3-yl) [2-methyl-4-(4-morpholinyl)phenyl], O-acetyloxime, Methanone, (3,5-dinitrophenyl) (9-ethyl-6-nitro-9H-carbazol-3-yl) (2-methylphenyl), O-acetyloxime, Methanone Tanone, (9-ethyl-6-nitro-9H-carbazol-3-yl)(3-nitrophenyl), O-acetyloxime, 1,3,5-triazine-2,4,6(1H,3H,5H)-trione, 1,3,5-tris[2-(acetyloxy)-3-[3-[(1E)-1-[(acetyloxy)iminoethyl]-6-nitro-9H-carbazol-9-yl]propyl], 1,2-butanedione, 1-[4-(phenylthio)phenyl ]-, 2-(O-acetyloxime), 1,2-butanedione, 1-[4-[[4-(2-hydroxyethoxy)phenyl]thio]phenyl]-, 2-(O-acetyloxime), 1,2-butanedione, 1,1'-(thiodi-4,1-phenylene)bis-, 2,2-bis(O-acetyloxime), 1,2-octanedione, 1-[4-(phenylthio)phenyl]-, 2-[O-(4-methylbenzoyl)oxime], and the like.

[0082] Other examples of the radical polymerization initiator include 2,4,6-trimethylbenzoyldiphenylphosphine oxide and bis(cyclopentadienyl)-bis[2,6-difluoro-3-(pyr-1-yl)]titanium.

[0083] As the photopolymerization initiator, commercially available products may be used, and commercially available radical polymerization initiators include ADEKA OPTOMER N-1414, N-1717, N-1919, PZ-408, NCI-831, and NCI-930 (all manufactured by ADEKA CORPORATION), DAROCUR 1173, IRGACURE (registered trademark) 184, IRGACURE (registered trademark) 369, IRGACURE (registered trademark) 907, IRGACURE (registered trademark) 819, IRGACURE (registered trademark) OXE01, and IRGACURE (registered trademark) OXE02 (all manufactured by BASF), and ESACURE KIP150, ESACURE KTO46, ESACURE TZT, and ESACURE KB1 (all manufactured by Lamberti).

[0084] 4-3. Organic solvents 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 methoxyethyl acetate; 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-cyanobutane, 1-cyanohexane, cyanocyclohexane, cyanobenzene, 1,3-dicyanopropane, 1,4-dicyanobutane, 1,6-dicyanohexane, 1,4-dicyanocyclohexane, and 1,4-dicyanobenzene; pyridine; and lutidine.

[0085] 5. Compounds represented by general formula (I) The resin composition of the present disclosure may produce a compound represented by general formula (I) when heated, for example.

[0086] [ka]

[0087] In general formula (I), R 201 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-, -Ar 201 -or-Ar 202 -R 202 -Ar 202 - represents. Ar 201 represents an unsubstituted phenylene group, a phenylene group substituted with 1 to 4 methyl groups or 1 to 4 ethyl groups, an unsubstituted biphenylene group, or a biphenylene group substituted with 1 to 8 methyl groups or 1 to 8 ethyl groups. Ar 202 respectively represent an unsubstituted phenylene group, a phenylene group substituted with 1 to 4 methyl groups or 1 to 4 ethyl groups, an unsubstituted biphenylene group, or a biphenylene group substituted with 1 to 8 methyl groups or 1 to 8 ethyl groups. R 202 is -(CH2) d represents -, -O-, -S-, -SO-, -SO2- or -CO-. d is an integer of 1 to 8. In general formula (I), R 221 represents an unsubstituted aliphatic hydrocarbon group having 1 to 20 carbon atoms, or an unsubstituted aliphatic hydrocarbon group having 1 to 20 carbon atoms in which one or more methylene groups have been substituted with a divalent group selected from -OCONH-, -NHCOO-, -S-, -SO-, or -SO2-. In general formula (I), R 222 , R 223 and R 224 each independently represents a hydrogen atom or an unsubstituted aliphatic hydrocarbon group having 1 to 20 carbon atoms. In general formula (I), R 225represents a hydrogen atom or a methyl group.

[0088] In the present disclosure, in general formula (I), R 201 From the viewpoint of being able to form a cured product with excellent stress relaxation performance, -Ar 202 -R 202 -Ar 202 - is preferred.

[0089] In general formula (I), R 201 Ga-Ar 202 -R 202 -Ar 202 -, if Ar 202 From the viewpoint of being able to form a cured product having excellent stress relaxation performance, each of the groups is preferably an unsubstituted phenylene group or a phenylene group substituted with 1 to 4 methyl groups or 1 to 4 ethyl groups, more preferably a phenylene group substituted with 1 to 4 methyl groups or 1 to 4 ethyl groups, and most preferably a phenylene group substituted with two methyl groups, a phenylene group substituted with two ethyl groups, or a phenylene group substituted with one methyl group and one ethyl group.

[0090] In addition, in the general formula (I), R 201 Ga-Ar 202 -R 202 -Ar 202 -If R 202 From the viewpoint of forming a cured product having excellent stress relaxation properties, -(CH2) d It is preferably -, and more preferably -CH2-.

[0091] In the present disclosure, in general formula (I), R 221From the viewpoint of being able to form a cured product having excellent stress relaxation performance, is preferably an unsubstituted aliphatic hydrocarbon group having 1 to 20 carbon atoms or an unsubstituted aliphatic hydrocarbon group having 1 to 20 carbon atoms in which one or more methylene groups have been substituted with a divalent group selected from -OCONH-, -NHCOO-, -NHCO-, -CONH-, or -O-, more preferably an unsubstituted aliphatic hydrocarbon group having 1 to 10 carbon atoms or an unsubstituted aliphatic hydrocarbon group having 1 to 10 carbon atoms in which one or more methylene groups have been substituted with a divalent group selected from -OCONH- or -NHCOO-, even more preferably an unsubstituted aliphatic hydrocarbon group having 1 to 5 carbon atoms or an unsubstituted aliphatic hydrocarbon group having 1 to 5 carbon atoms in which one or more methylene groups have been substituted with -NHCOO-, and most preferably an unsubstituted aliphatic hydrocarbon group having 1 to 5 carbon atoms.

[0092] In the present disclosure, in general formula (I), R 225 is preferably a methyl group from the viewpoint of forming a cured product having excellent stress relaxation properties.

[0093] In the present disclosure, in general formula (I), R 222 , R 223 and R 224 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 with excellent stress relaxation performance.

[0094] Specific examples of the compound represented by general formula (I) include the following compounds, but the present disclosure is not limited to these compounds. Among these, one or more compounds selected from the group consisting of compounds No. 3-1 and No. 3-2 are preferred from the viewpoint of forming a cured product having excellent stress relaxation properties.

[0095] [ka]

[0096] The compound represented by general formula (I) is produced, for example, by the Diels-Alder reaction of component (A) having a maleimide structure and component (B) having a conjugated diene structure.

[0097] The reason why the resin composition of the present disclosure exhibits excellent stress relaxation performance is not clear, but it is presumed that this is because the stress accumulated in the cured product is resolved by the Diels-Alder reaction and the rearrangement of bonds due to the reverse reaction.

[0098] 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, the cured product 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 coating materials.

[0099] The shape of the cured product of the present disclosure is not particularly limited, but examples thereof include a sheet shape and a molded product shape.

[0100] 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. Curing a resin composition containing an organic solvent can result in a cured product that contains the organic solvent, or 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 that contain an organic solvent and those that are substantially free of the organic solvent.

[0101] C. Manufacturing method of cured product The method for producing a cured product of the present disclosure includes curing the resin composition of the present disclosure. 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 method for producing a cured product of the present disclosure preferably includes adding a thermal polymerization initiator, etc., to the resin composition of the present disclosure, if necessary, and then heating the composition at a temperature ranging from 20°C to 170°C for 5 minutes to 10 hours to cure the composition. When producing a sheet-shaped 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 a 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.

[0102] D. Other The present disclosure includes the following aspects. [1] 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); (C) component: one or more compounds selected from the group consisting of methacrylate compounds and acrylate compounds different from the (B) component; A resin composition comprising:

[0103] [ka]

[0104] (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 - represents Ar 1 represents an unsubstituted phenylene group, a phenylene group substituted with 1 to 4 methyl groups or 1 to 4 ethyl groups, an unsubstituted biphenylene group, or a biphenylene group substituted with 1 to 8 methyl groups or 1 to 8 ethyl groups, Ar 2 represent an unsubstituted phenylene group, a phenylene group substituted with 1 to 4 methyl groups or 1 to 4 ethyl groups, an unsubstituted biphenylene group, or a biphenylene group substituted with 1 to 8 methyl groups or 1 to 8 ethyl groups, respectively; R 2 is -(CH2) d represents -, -O-, -S-, -SO-, -SO2- or -CO-, and d is an integer of 1 to 8.

[0105] [ka]

[0106] (In general formula (2), R 21 represents an unsubstituted aliphatic hydrocarbon group having 1 to 20 carbon atoms, or an unsubstituted aliphatic hydrocarbon group having 1 to 20 carbon atoms in which one or more methylene groups have been substituted with a divalent group selected from -OCONH-, -NHCOO-, -NHCO-, -CONH-, -O-, -S-, -SO-, or -SO2-; R 22 , R 23 and R 24 each independently represents a hydrogen atom or an unsubstituted aliphatic hydrocarbon group having 1 to 20 carbon atoms, R 25 is a hydrogen atom or a methyl group.

[0107] [ka]

[0108] (In general formula (3), R 31 represents an unsubstituted aliphatic hydrocarbon group having 1 to 20 carbon atoms, or an unsubstituted aliphatic hydrocarbon group having 1 to 20 carbon atoms in which one or more methylene groups are -OCONH-, -NHCOO-, -NHCO-, -CONH-, -O-, -S-, -SO-, or -SO 2 - represents a group substituted with a divalent group selected from R 32 , R 33 , R 34 , R 35 , R 36 , R 37 , R 38 , R 39 and R 40 each independently represents a hydrogen atom or an unsubstituted aliphatic hydrocarbon group having 1 to 20 carbon atoms, R 41 is a hydrogen atom or a methyl group.

[0109] [2] The resin composition according to [1], further comprising one or more selected from the group consisting of a component (D): a thermal polymerization initiator and a component (E): a photopolymerization initiator.

[0110] [3] The resin composition according to [1] or [2], wherein the component (B) contains a compound represented by the general formula (2).

[0111] [4] In the above general formula (2), R 21 is an unsubstituted aliphatic hydrocarbon group having 1 to 10 carbon atoms, or an unsubstituted aliphatic hydrocarbon group having 1 to 10 carbon atoms in which one or more methylene groups are substituted with a divalent group selected from -OCONH- or -NHCOO-.

[0112] [5] In the above general formula (2), R 25 The resin composition according to any one of [1] to [4], wherein is a methyl group.

[0113] [6] A cured product obtained by curing the resin composition according to any one of [1] to [5].

[0114] [7] A method for producing a cured product, comprising curing the resin composition according to any one of [1] to [5].

[0115] [8] A compound represented by general formula (I):

[0116] [ka]

[0117] (In general formula (I), R 201 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-, -Ar 201 -or-Ar 202 -R 202 -Ar 202 - represents Ar 201 represents an unsubstituted phenylene group, a phenylene group substituted with 1 to 4 methyl groups or 1 to 4 ethyl groups, an unsubstituted biphenylene group, or a biphenylene group substituted with 1 to 8 methyl groups or 1 to 8 ethyl groups, Ar 202 represent an unsubstituted phenylene group, a phenylene group substituted with 1 to 4 methyl groups or 1 to 4 ethyl groups, an unsubstituted biphenylene group, or a biphenylene group substituted with 1 to 8 methyl groups or 1 to 8 ethyl groups, respectively; R 202 is -(CH2) drepresents -, -O-, -S-, -SO-, -SO2-, or -CO-, and d is an integer of 1 to 8; R 221 represents an unsubstituted aliphatic hydrocarbon group having 1 to 20 carbon atoms, or an unsubstituted aliphatic hydrocarbon group having 1 to 20 carbon atoms in which one or more methylene groups have been substituted with a divalent group selected from -OCONH-, -NHCOO-, -S-, -SO-, or -SO2-; R 222 , R 223 and R 224 each independently represents a hydrogen atom or an unsubstituted aliphatic hydrocarbon group having 1 to 20 carbon atoms, R 225 represents a hydrogen atom or a methyl group.

[0118] [9] In the above general formula (I), R 221 is an unsubstituted aliphatic hydrocarbon group having 1 to 10 carbon atoms, or 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 -OCONH- or -NHCOO-.

[0119]

[10] In the above general formula (I), R 225 is a methyl group.

[0120] 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. [Example]

[0121] 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.

[0122] <Preparation of cured product> (Examples 1 and 2 and Comparative Example 1) A 1.0 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 according to the formulation 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 sheet-like cured products.

[0123] The components used in Table 1 are as follows:

[0124] The following was prepared as component (A): A-1: Compound No. 1-1

[0125] The following was prepared as component (B): B-1: Compound No. 2-1 B-2: Compound No. 2-2

[0126] The following was prepared as component (C): C-1: Hexyl methacrylate C-2: BPE-200 (ethoxylated bisphenol A dimethacrylate, manufactured by Shin-Nakamura Chemical Co., Ltd.)

[0127] The following was prepared as component (D): D-1: 2,2'-azobis(2,4-dimethylvaleronitrile) (Fujifilm Wako Pure Chemical Industries, Ltd.)

[0128] (Stress relaxation performance) The cured products of Examples 1 and 2 and Comparative Example 1 were evaluated using a thermomechanical analyzer (Hitachi High-Technologies TMA-7100). Each cured product was elongated by 5% at 120°C, and the rate of change between the stress (σ1) measured immediately after elongation and the stress (σ2) 30 minutes later was calculated using the following formula. The results are shown in Table 1. Stress change rate (%) = (σ1-σ2) / σ1×100

[0129] [Table 1]

[0130] Example 3 A reaction apparatus equipped with a stirrer, reflux condenser, thermometer, and nitrogen inlet tube was charged with 22.1 g (0.05 mol) of compound No. 1-1 (bis(3-ethyl-5-methyl-4-maleimidophenyl)methane, manufactured by Tokyo Chemical Industry Co., Ltd.) and 34.1 g (0.2 mol) of compound No. 2-1 (furfuryl methacrylate, manufactured by Tokyo Chemical Industry Co., Ltd.), and the mixture was kept at 90°C in an oil bath and stirred for 3 hours to carry out the reaction. The reaction product was then diluted with ethyl acetate and separated by column to obtain the reaction product. 1 H-NMR analysis was performed and the compound was identified as No. 3-1. 1 The results of H-NMR analysis are shown below. 1 H-NMR(CDCL3) δ / ppm:1.02-1.17(6H,m),1.88-2.15(12H,m),2.25-2.46(4H,m),3.07-3.24(4H,m),3.84 -3.98(2H,m),4.53-5.17(6H,m),5.37-5.68(4H,m),6.46-6.71(4H,m),6.86-7.09(4H,m) Total 46H

[0131] The above results demonstrate that the resin compositions of Examples 1 and 2, which contain components (A), (B), and (C), can form cured products with excellent stress relaxation performance, compared to the resin composition of Comparative Example 1, which does not contain components (A) and (B). Considering the comparison of Examples 1 and 2 with Comparative Example 1 and the analysis results of Example 3, it is presumed that the reason for the improved stress relaxation performance in Examples 1 and 2 is that the Diels-Alder reaction between components (A) and (B) produced a compound corresponding to general formula (I).

Claims

1. 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), (C) component: one or more compounds selected from the group consisting of methacrylate compounds and acrylate compounds different from the (B) component; A resin composition comprising: 【Chemical 1】 (In general formula (1), R １ represents an unsubstituted aliphatic hydrocarbon group having 1 to 10 carbon atoms, wherein one or more methylene groups in the aliphatic hydrocarbon group are -O-, -S-, -SO-, or -SO ２ a group substituted with a divalent group selected from -Ar １ -or-Ar ２ -R ２ -Ar ２ represents -, Ar １ represents an unsubstituted phenylene group, a phenylene group substituted with 1 to 4 methyl groups or 1 to 4 ethyl groups, an unsubstituted biphenylene group, or a biphenylene group substituted with 1 to 8 methyl groups or 1 to 8 ethyl groups, Ar ２ represent an unsubstituted phenylene group, a phenylene group substituted with 1 to 4 methyl groups or 1 to 4 ethyl groups, an unsubstituted biphenylene group, or a biphenylene group substituted with 1 to 8 methyl groups or 1 to 8 ethyl groups, respectively; R ２ is -(CH ２ ) ｄ -, -O-, -S-, -SO-, -SO ２ - or -CO-, and d is an integer of 1 to 8. 【Chemistry 2】 (In general formula (2), R ２１ represents an unsubstituted aliphatic hydrocarbon group having 1 to 20 carbon atoms, or an unsubstituted aliphatic hydrocarbon group having 1 to 20 carbon atoms in which one or more methylene groups are -OCONH-, -NHCOO-, -NHCO-, -CONH-, -O-, -S-, -SO-, or -SO ２ represents a group substituted with a divalent group selected from R ２２ , R ２３ and R ２４ each independently represents a hydrogen atom or an unsubstituted aliphatic hydrocarbon group having 1 to 20 carbon atoms, R ２５ is a hydrogen atom or a methyl group. 【Chemistry 3】 (In general formula (3), R ３１ represents an unsubstituted aliphatic hydrocarbon group having 1 to 20 carbon atoms, or an unsubstituted aliphatic hydrocarbon group having 1 to 20 carbon atoms in which one or more methylene groups are -OCONH-, -NHCOO-, -NHCO-, -CONH-, -O-, -S-, -SO-, or -SO ２ represents a group substituted with a divalent group selected from R ３２ , R ３３ , R ３４ , R ３５ , R ３６ , R ３７ , R ３８ , R ３９ and R ４０ each independently represents a hydrogen atom or an unsubstituted aliphatic hydrocarbon group having 1 to 20 carbon atoms, R ４１ is a hydrogen atom or a methyl group.

2. The resin composition according to claim 1, further comprising at least one selected from the group consisting of a component (D): a thermal polymerization initiator and a component (E): a photopolymerization initiator.

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 an unsubstituted aliphatic hydrocarbon group having 1 to 10 carbon atoms, or 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 -OCONH- or -NHCOO-.

5. In the general formula (2), R ２５ The resin composition according to claim 4, wherein is a methyl group.

6. A cured product obtained by curing the resin composition according to any one of claims 1 to 5.

7. A method for producing a cured product, comprising curing the resin composition according to any one of claims 1 to 5.

8. A compound represented by general formula (I): 【Chemistry 4】 (In general formula (I), R ２０１ represents an unsubstituted aliphatic hydrocarbon group having 1 to 10 carbon atoms, and one or more methylene groups in the unsubstituted aliphatic hydrocarbon group having 1 to 10 carbon atoms are -O-, -S-, -SO- or -SO ２ a group substituted with a divalent group selected from -Ar ２０１ -or-Ar ２０２ -R ２０２ -Ar ２０２ represents -, Ar ２０１ represents an unsubstituted phenylene group, a phenylene group substituted with 1 to 4 methyl groups or 1 to 4 ethyl groups, an unsubstituted biphenylene group, or a biphenylene group substituted with 1 to 8 methyl groups or 1 to 8 ethyl groups, Ar ２０２ represent an unsubstituted phenylene group, a phenylene group substituted with 1 to 4 methyl groups or 1 to 4 ethyl groups, an unsubstituted biphenylene group, or a biphenylene group substituted with 1 to 8 methyl groups or 1 to 8 ethyl groups, respectively; R ２０２ is -(CH ２ ) ｄ -, -O-, -S-, -SO-, -SO ２ - or -CO-, and d is an integer from 1 to 8; R ２２１ represents an unsubstituted aliphatic hydrocarbon group having 1 to 20 carbon atoms, or an unsubstituted aliphatic hydrocarbon group having 1 to 20 carbon atoms in which one or more methylene groups are -OCONH-, -NHCOO-, -S-, -SO-, or -SO ２ represents a group substituted with a divalent group selected from R ２２２ , R ２２３ and R ２２４ each independently represents a hydrogen atom or an unsubstituted aliphatic hydrocarbon group having 1 to 20 carbon atoms, R ２２５ represents a hydrogen atom or a methyl group.

9. In the general formula (I), R ２２１ is an unsubstituted aliphatic hydrocarbon group having 1 to 10 carbon atoms, or an unsubstituted aliphatic hydrocarbon group having 1 to 10 carbon atoms in which one or more methylene groups are substituted with a divalent group selected from -OCONH- or -NHCOO-.

10. In the general formula (I), R ２２５ The compound according to claim 9, characterized in that is a methyl group.

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