resin composition

Abstract

To provide a resin composition capable of obtaining a cured product which has a low dielectric dissipation factor (Df) and is excellent in breaking point elongation and ground copper adhesion strength (copper foil peeling strength) after accelerated environment test (HAST).SOLUTION: There is provided a resin composition which comprises (A) an allyl compound having an alicyclic structure, (B) an epoxy resin, (C) an active ester compound and (D) an inorganic filler, wherein the content the component (C) is 10 mass% or more when a nonvolatile component in the resin composition is defined as 100 mass% and the content of the component (D) is 60 mass% or more when a nonvolatile component in the resin composition is defined as 100 mass%.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to a resin composition containing an epoxy resin, and further to a cured product, a sheet-like laminate material, a resin sheet, a printed wiring board, and a semiconductor device obtained using the resin composition. [Background technology]

[0002] A known manufacturing technique for printed wiring boards is the build-up method, in which insulating layers and conductor layers are alternately stacked. In build-up manufacturing methods, the insulating layers are generally formed by curing a resin composition. In recent years, there has been a demand for lowering the dielectric loss tangent of the insulating layer.

[0003] It has been known that the dielectric loss tangent of an insulating layer can be reduced by using an epoxy resin composition containing a high content of an active ester compound and an inorganic filler as the resin composition for forming the insulating layer (Patent Document 1). [Prior art documents] [Patent documents]

[0004] [Patent Document 1] Japanese Patent Publication No. 2020-23714 [Patent Document 2] Japanese Patent Application Publication No. 2019-89967 [Patent Document 3] Japanese Patent Application Publication No. 2020-136311 Summary of the Invention [Problem to be solved by the invention]

[0005] However, when an epoxy resin composition containing a high content of an active ester compound and an inorganic filler is used, problems arise, such as a decrease in elongation at break and a decrease in adhesion strength to the copper substrate (copper foil peel strength) after accelerated environmental testing (HAST). Incidentally, allyl compounds having an alicyclic structure have been known (Patent Documents 2 and 3).

[0006] An object of the present invention is to provide a resin composition that can give a cured product having a low dielectric dissipation factor (Df), excellent elongation at break, and excellent copper substrate adhesion strength (copper foil peel strength) after accelerated environmental testing (HAST). [Means for solving the problem]

[0007]

[0009] In order to achieve the objects of the present invention, the present inventors have conducted extensive research and have unexpectedly found that by using an allyl compound (A) having an alicyclic structure in an epoxy resin composition containing a high content of (C) an active ester compound and (D) an inorganic filler, respectively, at 10% by mass or more and 60% by mass or more, it is possible to obtain a cured product having a low dielectric dissipation factor (Df), excellent elongation at break, and excellent copper substrate adhesion strength (copper foil peel strength) after accelerated environmental testing (HAST), and have completed the present invention.

[0008] That is, the present invention includes the following. [1] A resin composition comprising (A) an allyl compound having an alicyclic structure, (B) an epoxy resin, (C) an active ester compound, and (D) an inorganic filler, The content of the (C) component is 10% by mass or more, where the total amount of nonvolatile components in the resin composition is 100% by mass, A resin composition, wherein the content of component (D) is 60% by mass or more, assuming that the total nonvolatile components in the resin composition is 100% by mass. [2] The component (A) is a compound represented by the formula (a-1):

[0009] [ka]

[0010] [wherein * indicates a binding site.] The resin composition according to the above [1], which has a group represented by the following formula: [3] The component (A) is a compound represented by the formula (A3):

[0011] [ka]

[0012] [Wherein X is a single bond, -C(R 5 )2-, -O-, -CO-, -S-, -SO-, or -SO2-; R 2 and R 5 each independently represents a hydrogen atom or a hydrocarbon group, and R 3 and R 4 each independently represents a hydrocarbon group, and one R 2 and b R 3 At least one of the groups is an allyl group, b and c each independently represent an integer of 0 to 3, and * represents a binding site. The resin composition according to the above [1] or [2], which has a group represented by the following formula: [4] The resin composition according to any one of the above [1] to [3], wherein the weight average molecular weight of the component (A) is 1,000 to 20,000. [5] The resin composition according to any one of the above [1] to [4], wherein the allyl equivalent of the component (A) is 200 g / eq. to 2000 g / eq. [6] The resin composition according to any one of the above [1] to [5], wherein the content of component (A) is 0.01% by mass or more, based on 100% by mass of the non-volatile components in the resin composition. [7] The resin composition according to any one of the above [1] to [6], wherein the content of component (A) is 5% by mass or less, when the total amount of non-volatile components in the resin composition is 100% by mass. [8] The resin composition according to any one of the above [1] to [7], wherein the content of component (B) is 1% by mass to 20% by mass, where the total amount of non-volatile components in the resin composition is 100% by mass. [9] The resin composition according to any one of the above [1] to [8], wherein the mass ratio of the component (B) to the component (A) (component (B) / component (A)) is 1.5 to 100.

[10] The resin composition according to any one of the above [1] to [9], wherein the component (D) is silica.

[11] The resin composition according to any one of the above [1] to

[10] , wherein the content of component (D) is 70% by mass or more, assuming that the non-volatile components in the resin composition are 100% by mass.

[12] The resin composition according to any one of the above [1] to

[11] , further comprising an imidazole-based curing accelerator.

[13] The resin composition according to any one of the above [1] to

[12] , further comprising a curing agent selected from the group consisting of phenol-based curing agents and carbodiimide-based curing agents.

[14] The resin composition according to any one of the above [1] to

[13] , wherein the elongation at break of a cured product of the resin composition is 1.0% or more when measured at 23°C.

[15] The resin composition according to any one of the above [1] to

[14] , wherein the dielectric loss tangent (Df) of a cured product of the resin composition is 0.0030 or less when measured at 5.8 GHz and 23°C.

[16] A cured product of the resin composition according to any one of [1] to

[15] above.

[17] A sheet-like laminate material containing the resin composition according to any one of the above [1] to

[15] .

[18] A resin sheet comprising a support and a resin composition layer formed on the support from the resin composition according to any one of [1] to

[15] above.

[19] A printed wiring board having an insulating layer made of a cured product of the resin composition according to any one of [1] to

[15] above.

[20] A semiconductor device comprising the printed wiring board according to

[19] above. [Effects of the Invention]

[0013] The resin composition of the present invention can provide a cured product that has a low dielectric dissipation factor (Df), excellent elongation at break, and excellent copper substrate adhesion strength (copper foil peel strength) after accelerated environmental testing (HAST). DETAILED DESCRIPTION OF THE INVENTION

[0014] The present invention will be described in detail below with reference to preferred embodiments thereof. However, the present invention is not limited to the following embodiments and examples, and can be implemented with any modifications within the scope of the claims of the present invention and their equivalents.

[0015] <Resin composition> The resin composition of the present invention comprises (A) an allyl compound having an alicyclic structure, (B) an epoxy resin, (C) an active ester compound, and (D) an inorganic filler, wherein the content of the (C) active ester compound is 10% by mass or more and the content of the (D) inorganic filler is 60% by mass or more. By using such a resin composition, it is possible to obtain a cured product having a low dielectric loss tangent (Df), excellent elongation at break, and excellent copper substrate adhesion strength (copper foil peel strength) after accelerated environmental testing (HAST).

[0016] The resin composition of the present invention may contain optional components in addition to (A) an allyl compound having an alicyclic structure, (B) an epoxy resin, (C) an active ester compound, and (D) an inorganic filler. Examples of optional components include (C') other curing agents, (E) radically polymerizable compounds, (F) curing accelerators, (G) thermoplastic resins, (H) other additives, and (I) organic solvents. Each component contained in the resin composition will be described in detail below.

[0017] <(A) Allyl Compound Having an Alicyclic Structure> The resin composition of the present invention contains (A) an allyl compound having an alicyclic structure. The (A) allyl compound having an alicyclic structure may be used alone or in combination of two or more kinds in any ratio.

[0018] (A) Allyl compound having an alicyclic structure preferably has two or more allyl groups per molecule. (A) Allyl compound having an alicyclic structure preferably has an aromatic ring, and the allyl group is preferably bonded to the aromatic ring directly or via a heteroatom (preferably an oxygen atom) selected from oxygen, nitrogen, and sulfur atoms.

[0019] The aromatic ring refers to a ring conforming to Hückel's rule, in which the number of electrons contained in the π-electron system on the ring is 4p+2 (p is a natural number). The aromatic ring may be an aromatic carbocyclic ring having carbon atoms as ring-constituting atoms, or an aromatic heterocyclic ring having heteroatoms such as oxygen atoms, nitrogen atoms, and sulfur atoms in addition to carbon atoms as ring-constituting atoms. In one embodiment, the aromatic ring is preferably an aromatic carbocyclic ring. In one embodiment, the aromatic ring is preferably a 5- to 14-membered aromatic ring, and more preferably a 5- to 10-membered aromatic ring. Specific examples of suitable aromatic rings include a benzene ring, a naphthalene ring, an anthracene ring, and a phenanthrene ring. A benzene ring or a naphthalene ring is more preferred, and a benzene ring is particularly preferred.

[0020] (A) In one embodiment, the allyl compound having an alicyclic structure is represented by the formula (A1):

[0021] [ka]

[0022] [In the formula, R 1 each independently represents a substituent, and a number of R 1 At least one of the groups is an allyl group or an allyloxy group, a represents an integer of 1 to 4, and * represents a bonding site. It is preferable that the compound has a group represented by formula (A2):

[0023] [ka]

[0024] [In the formula, R 2 represents a hydrogen atom or a hydrocarbon group, and R 3 each independently represents a hydrocarbon group, and one R 2 and b R 3 At least one of the groups is an allyl group, b represents an integer of 0 to 3, and * represents a binding site. It is more preferable that the compound has a group represented by formula (A3):

[0025] [ka]

[0026] [Wherein X is a single bond, -C(R 5 )2-, -O-, -CO-, -S-, -SO-, or -SO2-; R 2 and R 5 each independently represents a hydrogen atom or a hydrocarbon group, and R 3 and R 4 each independently represents a hydrocarbon group, and one R 2 and b R 3 At least one of the groups is an allyl group, b and c each independently represent an integer of 0 to 3, and * represents a binding site. It is more preferable that (A) the allyl compound having an alicyclic structure has two or more groups represented by formula (A1), (A2) or (A3) in one molecule, and it is particularly preferable that it has two groups represented by formula (A1), (A2) or (A3).

[0027] R 1 R each independently represents a substituent. 1 are each independently preferably an allyl group, an allyloxy group, a hydroxy group, an alkyl group, an aryl group, an alkyl-oxy group, or an aryl-oxy group, and more preferably an allyl group, an allyloxy group, or a hydroxy group.

[0028] In the present specification, the term "substituent" is not particularly limited, and examples thereof include monovalent substituents such as an allyl group, an allyloxy group, an amino group, a hydroxy group, an alkyl group, an aryl group, an alkyl-aryl group (an aryl group substituted with an alkyl group), an aryl-alkyl group (an alkyl group substituted with an aryl group), an alkyl-oxy group, an aryl-oxy group, an alkyl-carbonyl group, an aryl-carbonyl group, an alkyl-oxy-carbonyl group, an aryl-oxy-carbonyl group, an alkyl-carbonyl-oxy group, an aryl-carbonyl-oxy group, a mono- or di(alkyl)amino group, and a mono- or di(aryl)amino group.

[0029] The term "alkyl group" refers to a linear and / or branched monovalent aliphatic saturated hydrocarbon group. Unless otherwise specified, the alkyl group is preferably an alkyl group having 1 to 6 carbon atoms. Examples of the alkyl group include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, a hexyl group, a cyclopentyl group, and a cyclohexyl group. The term "aryl group" refers to a monovalent aromatic hydrocarbon group. Unless otherwise specified, the aryl group is preferably an aryl group having 6 to 14 carbon atoms. Examples of the aryl group include a phenyl group, a 1-naphthyl group, and a 2-naphthyl group. The halogen atom is a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom.

[0030] a represents an integer of 1 to 4. a is preferably 1, 2 or 3, and more preferably 1 or 2.

[0031] R 2 represents a hydrogen atom or a hydrocarbon group. 2 is preferably a hydrogen atom, an allyl group, or an alkyl group, and more preferably a hydrogen atom or an allyl group. 3 R each independently represents a hydrocarbon group. 3 is preferably an allyl group or an alkyl group, and more preferably an allyl group.

[0032] In this specification, the term "hydrocarbon group" is not particularly limited, but examples thereof include monovalent hydrocarbon groups such as an allyl group, an alkyl group, an aryl group, an alkyl-aryl group, and an aryl-alkyl group.

[0033] b represents an integer of 0 to 3. b is preferably 0, 1 or 2, and more preferably 0 or 1.

[0034] In the first embodiment, preferably R 2 is an allyl group, and R 3 are each independently a hydrocarbon group and b is 0, 1 or 2; more preferably, R 2 is an allyl group, and R 3 are each independently an alkyl group, and b is 0 or 1; particularly preferably, R 2 is an allyl group and b is 0.

[0035] In the second embodiment, preferably R 2 is a hydrogen atom, and R 3 are each independently a hydrocarbon group, b is 1 or 2, and b R 3 At least one of R is an allyl group; more preferably, R 2 is a hydrogen atom, and R 3 are each independently an aryl group or an alkyl group, b is 1 or 2, and b R 3 At least one of R is an allyl group; particularly preferably, R 2 is a hydrogen atom, and R 3 is an allyl group and b is 1.

[0036] X is a single bond, -C(R 5 )2-, -O-, -CO-, -S-, -SO-, or -SO2-. X is preferably a single bond, -C(R 5 )2-, or —O—; more preferably, a single bond, or —C(R 5 )2-; particularly preferably -C(R 5 )2-.

[0037] R 5 R each independently represents a hydrogen atom or a hydrocarbon group. 5 are each independently preferably a hydrogen atom, an alkyl group, or an aryl group, more preferably a hydrogen atom or an alkyl group, and particularly preferably a hydrogen atom.

[0038] R 4 R each independently represents a hydrocarbon group. 4 is preferably an allyl group or an alkyl group, and more preferably an allyl group.

[0039] c represents an integer of 0 to 3. c is preferably 0, 1, or 2, and more preferably 0 or 1. In the first embodiment, c is particularly preferably 0. In the second embodiment, c is particularly preferably 1.

[0040] The alicyclic structure in the (A) allyl compound having an alicyclic structure is a ring skeleton structure of a non-aromatic ring. The non-aromatic ring in the alicyclic structure of the (A) allyl compound having an alicyclic structure may have a substituent at a substitutable position. The non-aromatic ring may be a saturated ring consisting of only single bonds, or a non-aromatic unsaturated ring having either a double bond or a triple bond, but is preferably a saturated ring consisting of only single bonds. The saturated ring may be a saturated carbocyclic ring containing carbon atoms as ring-constituting atoms, or a saturated heterocyclic ring containing heteroatoms such as oxygen atoms, nitrogen atoms, and sulfur atoms as ring-constituting atoms in addition to carbon atoms.

[0041] The saturated ring is preferably a saturated ring having 3 to 18 carbon atoms, more preferably a saturated ring having 5 to 16 carbon atoms. Examples of the saturated ring include monocyclic saturated carbocyclic rings such as monocycloalkane rings such as a cyclobutane ring, a cyclopentane ring, a cyclohexane ring, a cycloheptane ring, a cyclooctane ring, a cyclononane ring, a cyclodecane ring, a cycloundecane ring, and a cyclododecane ring; bicyclic saturated carbocyclic rings such as a bicyclo[2.2.1]heptane ring (norbornane ring), a bicyclo[4.4.0]decane ring (decalin ring), a bicyclo[5.3.0]decane ring, a bicyclo[4.3.0]nonane ring (hydrindane ring), a bicyclo[3.2.1]octane ring, a bicyclo[5.4.0]undecane ring, a bicyclo[3.3.0]octane ring, and a bicyclo[3.3.1]nonane ring; and tricyclo[5.2.1.0 2,6 ] Decane ring (tetrahydrodicyclopentadiene ring), tricyclo[3.3.1.1 3,7 ] Decane ring (adamantane ring), tricyclo[6.2.1.0 2,7 ]undecane ring and other saturated tricyclic carbocyclic rings, tetracyclo[6.2.1.1 3,6 .0 2,7 ] dodecane ring and other saturated tetracyclic carbocyclic rings, pentacyclo[9.2.1.1 4,7 .0 2,1 0.0 3,8 ] Pentadecane ring, pentacyclo[6.5.1.1 3,6 .0 2,7 .0 9,13 saturated carbocyclic rings such as a pentadecane ring (tetrahydrotricyclopentadiene ring) ring; saturated monocyclic heterocyclic rings such as a pyrrolidine ring, a pyrazolidine ring, an imidazolidine ring, a tetrahydrofuran ring, a 1,3-dioxolane ring, a piperidine ring, a piperazine ring, a tetrahydropyran ring, a 1,3-dioxane ring, a 1,4-dioxane ring, a thiane ring, a 1,3-dithiane ring, a morpholine ring, a thiomorpholine ring, and an oxazolidine ring; saturated bicyclic heterocyclic rings such as a 7-oxabicyclo[4.1.0]heptane ring (1,2-epoxycyclohexane ring), a 1-azabicyclo[2.2.2]octane (quinuclidine ring), a decahydroquinoline ring, and a decahydroisoquinoline ring; saturated 1-azatricyclo[3.3.1.1 3,7]decane (1-azaadamantane ring), 2-azatricyclo[3.3.1.1 3,7 ] decane (2-azaadamantane ring) and other saturated heterocyclic rings such as tricyclic saturated heterocyclic rings.

[0042] In (A) an allyl compound having an alicyclic structure, the non-aromatic ring is preferably a saturated carbocyclic ring, more preferably a bicyclic or higher saturated carbocyclic ring, and even more preferably a bicyclic saturated carbocyclic ring, a tricyclic saturated carbocyclic ring, a tetracyclic saturated carbocyclic ring, or a pentacyclic saturated carbocyclic ring.

[0043] In one embodiment, the allyl compound (A) having an alicyclic structure is a compound represented by any one of the formulae (a-1) to (a-8) containing two or more saturated carbocyclic rings:

[0044] [ka]

[0045] [wherein * indicates a binding site.] It is preferable that the alkyl group has a group represented by the formula (a-1).

[0046] In one embodiment, the allyl compound (A) having an alicyclic structure preferably includes a carbonate resin having an alicyclic structure and an allyl group, and is not particularly limited to, but is preferably a compound represented by the formula (A):

[0047] [ka]

[0048] [In the formula, A 1 each independently represents a group represented by formula (A3) described above; A 2 are each independently represented by the formula (Aa):

[0049] [ka]

[0050] (In the formula, each Y independently represents a single bond or an alkylene group, each Cy ring independently represents a non-aromatic ring which may have a substituent, and * represents a binding site.) or a group represented by formula (Ab):

[0051] [ka]

[0052] (wherein Z is a single bond, -C(R 8 )2-, -O-, -CO-, -S-, -SO-, or -SO2-; R 6 and R 7 each independently represents a hydrocarbon group, and R 8 each independently represents a hydrogen atom or a hydrocarbon group, e and d each independently represent an integer of 0 to 3, and * represents a bonding site. represents a group represented by n A 2 at least one of which is a group represented by formula (Aa); n is an integer equal to or greater than 0. It is particularly preferable that the resin contains a carbonate resin represented by the following formula:

[0053] Each Y independently represents a single bond or an alkylene group. Each Y independently represents a single bond or a methylene group, and more preferably a methylene group.

[0054] The alkylene group refers to a straight-chain and / or branched-chain divalent saturated hydrocarbon group. The alkylene group is preferably an alkylene group having 1 to 6 carbon atoms. Examples of the alkylene group include straight-chain alkylene groups such as methylene, ethylene, trimethylene, tetramethylene, pentamethylene, hexamethylene, heptamethylene, octamethylene, nonamethylene, and decamethylene; and branched-chain alkylene groups such as ethylidene, propylidene, isopropylidene, ethylmethylmethylene, and diethylmethylene.

[0055] Each ring Cy independently represents a non-aromatic ring which may have a substituent. Each ring Cy independently represents a saturated bicyclic or higher ring carbocyclic ring which may have a substituent, and particularly preferably represents a tricyclo[5.2.1.0 2,6 ]Decane ring (tetrahydrodicyclopentadiene ring).

[0056] R 6 and R 7 R each independently represents a hydrocarbon group. 6 and R 7 are each independently preferably an allyl group or an alkyl group, and more preferably an allyl group.

[0057] e and d each independently represent an integer of 0 to 3. e and d each independently are preferably 0, 1 or 2, and more preferably 0 or 1.

[0058] Z is a single bond, -C(R 8 )2-, -O-, -CO-, -S-, -SO-, or -SO2-. Z is preferably a single bond, -C(R 8 )2-, or —O—; more preferably, a single bond, or —C(R 8 )2-; particularly preferably -C(R 8 )2-.

[0059] R 8 R each independently represents a hydrogen atom or a hydrocarbon group. 8 are each independently preferably a hydrogen atom, an alkyl group, or an aryl group, more preferably a hydrogen atom or an alkyl group, and particularly preferably a hydrogen atom.

[0060] n represents an integer of 0 or more. n is preferably an integer of 0 to 200, more preferably an integer of 0 to 100. 2 At least one of n A is a group represented by formula (Aa). 2The proportion of groups represented by formula (Aa) in the above is preferably 20 mol % or more, more preferably 50 mol % or more.

[0061] The weight-average molecular weight of (A) the allyl compound having an alicyclic structure is preferably not more than 20,000, more preferably not more than 15,000. The lower limit of the weight-average molecular weight of (A) the allyl compound having an alicyclic structure is not particularly limited, but is preferably not less than 1,000, more preferably not less than 1,500, and particularly preferably not less than 2,000. The weight-average molecular weight of the resin can be measured as a polystyrene-equivalent value by gel permeation chromatography (GPC).

[0062] The allyl equivalent of the (A) allyl compound having an alicyclic structure is preferably 150 g / eq. to 5000 g / eq., more preferably 200 g / eq. to 2000 g / eq., even more preferably 250 g / eq. to 1500 g / eq., and still more preferably 300 g / eq. to 1200 g / eq. The allyl equivalent is the mass of the allyl compound per equivalent of an allyl group.

[0063] (A) Commercially available allyl compounds having an alicyclic structure include, for example, "FTC809AE" and "FATC809" manufactured by Gun-ei Chemical Industry Co., Ltd., and one or more of these can be used.

[0064] The content of the (A) allyl compound having an alicyclic structure in the resin composition is not particularly limited, but from the viewpoint of further reducing the dielectric loss tangent of the cured product, it is preferably 10% by mass or less, more preferably 7% by mass or less, even more preferably 5% by mass or less, even more preferably 4% by mass or less, and particularly preferably 3% by mass or less, based on 100% by mass of the nonvolatile components in the resin composition. The lower limit of the content of the (A) allyl compound having an alicyclic structure in the resin composition is not particularly limited, but from the viewpoint of further improving the elongation at break and the copper substrate adhesion strength (copper foil peel strength) after accelerated environmental testing (HAST), it is preferably 0.01% by mass or more, more preferably 0.05% by mass or more, even more preferably 0.1% by mass or more, even more preferably 0.2% by mass or more, and particularly preferably 0.3% by mass or more, based on 100% by mass of the nonvolatile components in the resin composition.

[0065] <(B) Epoxy resin> The resin composition of the present invention contains (B) an epoxy resin, which is a curable resin having an epoxy group.

[0066] (B) Epoxy resins include, for example, bixylenol type epoxy resins, bisphenol A type epoxy resins, bisphenol F type epoxy resins, bisphenol S type epoxy resins, bisphenol AF type epoxy resins, dicyclopentadiene type epoxy resins, trisphenol type epoxy resins, naphthol novolac type epoxy resins, phenol novolac type epoxy resins, tert-butyl-catechol type epoxy resins, naphthalene type epoxy resins, naphthol type epoxy resins, anthracene type epoxy resins, glycidylamine type epoxy resins, and glycidyl ester type epoxy resins. Examples of the epoxy resins include cresol novolac type epoxy resins, phenol aralkyl type epoxy resins, biphenyl type epoxy resins, linear aliphatic epoxy resins, epoxy resins having a butadiene structure, alicyclic epoxy resins, heterocyclic epoxy resins, spiro ring-containing epoxy resins, cyclohexane type epoxy resins, cyclohexane dimethanol type epoxy resins, naphthylene ether type epoxy resins, trimethylol type epoxy resins, tetraphenylethane type epoxy resins, isocyanurate type epoxy resins, phenolphthalimidine type epoxy resins, and phenolphthalein type epoxy resins. The (B) epoxy resins may be used alone or in combination of two or more.

[0067] The resin composition preferably contains, as the (B) epoxy resin, an epoxy resin having two or more epoxy groups per molecule. The proportion of the epoxy resin having two or more epoxy groups per molecule relative to 100% by mass of the non-volatile components of the (B) epoxy resin is preferably 50% by mass or more, more preferably 60% by mass or more, and particularly preferably 70% by mass or more.

[0068] Epoxy resins include epoxy resins that are liquid at a temperature of 20°C (hereinafter sometimes referred to as "liquid epoxy resins") and epoxy resins that are solid at a temperature of 20°C (hereinafter sometimes referred to as "solid epoxy resins"). The resin composition of the present invention may contain only a liquid epoxy resin as the epoxy resin, or may contain only a solid epoxy resin, or may contain a combination of a liquid epoxy resin and a solid epoxy resin.

[0069] The liquid epoxy resin is preferably a liquid epoxy resin having two or more epoxy groups in one molecule.

[0070] Preferred liquid epoxy resins include bisphenol A type epoxy resins, bisphenol F type epoxy resins, bisphenol AF type epoxy resins, naphthalene type epoxy resins, glycidyl ester type epoxy resins, glycidyl amine type epoxy resins, phenol novolac type epoxy resins, alicyclic epoxy resins having an ester skeleton, cyclohexane type epoxy resins, cyclohexane dimethanol type epoxy resins, and epoxy resins having a butadiene structure.

[0071] Specific examples of liquid epoxy resins include "HP4032", "HP4032D", and "HP4032SS" (naphthalene type epoxy resins) manufactured by DIC Corporation; "828US", "828EL", "jER828EL", "825", and "Epikote 828EL" (bisphenol A type epoxy resins) manufactured by Mitsubishi Chemical Corporation; "jER807" and "1750" (bisphenol F type epoxy resins) manufactured by Mitsubishi Chemical Corporation; "jER152" (phenol novolac type epoxy resin) manufactured by Mitsubishi Chemical Corporation; "630", "630LSD", and "604" (glycidylamine type epoxy resins) manufactured by Mitsubishi Chemical Corporation; "ED-523T" (glycyrol type epoxy resin) manufactured by ADEKA Corporation; and "EP-3950L" and "EP-3980S" ( Examples of epoxy resins include glycidylamine epoxy resins, ADEKA's "EP-4088S" (dicyclopentadiene epoxy resin), Nippon Steel Chemical & Material's "ZX1059" (a mixture of bisphenol A and bisphenol F epoxy resins), Nagase ChemteX's "EX-721" (glycidyl ester epoxy resin), Daicel's "Celloxide 2021P" (alicyclic epoxy resin with an ester structure), Daicel's "PB-3600," Nippon Soda's "JP-100" and "JP-200" (epoxy resins with a butadiene structure), and Nippon Steel Chemical & Material's "ZX1658" and "ZX1658GS" (liquid 1,4-glycidylcyclohexane epoxy resin). These may be used alone or in combination.

[0072] As the solid epoxy resin, a solid epoxy resin having three or more epoxy groups in one molecule is preferred, and an aromatic solid epoxy resin having three or more epoxy groups in one molecule is more preferred.

[0073] Preferred solid epoxy resins include bixylenol-type epoxy resins, naphthalene-type epoxy resins, naphthalene-type tetrafunctional epoxy resins, naphthol novolac-type epoxy resins, cresol novolac-type epoxy resins, dicyclopentadiene-type epoxy resins, trisphenol-type epoxy resins, naphthol-type epoxy resins, biphenyl-type epoxy resins, naphthylene ether-type epoxy resins, anthracene-type epoxy resins, bisphenol A-type epoxy resins, bisphenol AF-type epoxy resins, phenol aralkyl-type epoxy resins, tetraphenylethane-type epoxy resins, phenolphthalimidine-type epoxy resins, and phenolphthalein-type epoxy resins.

[0074] Specific examples of solid epoxy resins include DIC Corporation's "HP4032H" (naphthalene-type epoxy resin); DIC Corporation's "HP-4700" and "HP-4710" (naphthalene-type tetrafunctional epoxy resins); DIC Corporation's "N-690" (cresol novolac-type epoxy resin); DIC Corporation's "N-695" (cresol novolac-type epoxy resin); DIC Corporation's "HP-7200," "HP-7200HH," "HP-7200H," and "HP-7200L" (dicyclopentadiene-type epoxy resins); and DIC Corporation's "EXA-7311." "EXA-7311-G3", "EXA-7311-G4", "EXA-7311-G4S", "HP6000" (naphthylene ether type epoxy resin); "EPPN-502H" (trisphenol type epoxy resin) manufactured by Nippon Kayaku Co., Ltd.; "NC7000L" (naphthol novolac type epoxy resin) manufactured by Nippon Kayaku Co., Ltd.; "NC3000H", "NC3000", "NC3000L", "NC3000FH", "NC3100" (biphenyl type epoxy resin) manufactured by Nippon Kayaku Co., Ltd.; "ESN475V", "ESN4" manufactured by Nippon Steel Chemical & Material Co., Ltd. 100V" (naphthalene-type epoxy resin); "ESN485" (naphthol-type epoxy resin) manufactured by Nippon Steel Chemical & Material Co., Ltd.; "ESN375" (dihydroxynaphthalene-type epoxy resin) manufactured by Nippon Steel Chemical & Material Co., Ltd.; "YX4000H", "YX4000", "YX4000HK", and "YL7890" (bixylenol-type epoxy resin) manufactured by Mitsubishi Chemical Corporation; "YL6121" (biphenyl-type epoxy resin) manufactured by Mitsubishi Chemical Corporation; "YX8800" (anthracene-type epoxy resin) manufactured by Mitsubishi Chemical Corporation; "Y" manufactured by Mitsubishi Chemical Corporation Examples include "X7700" (phenol aralkyl type epoxy resin); "PG-100" and "CG-500" manufactured by Osaka Gas Chemicals Co., Ltd.; "YL7760" (bisphenol AF type epoxy resin) manufactured by Mitsubishi Chemical Corporation; "YL7800" (fluorene type epoxy resin) manufactured by Mitsubishi Chemical Corporation; "jER1010" (bisphenol A type epoxy resin) manufactured by Mitsubishi Chemical Corporation; "jER1031S" (tetraphenylethane type epoxy resin) manufactured by Mitsubishi Chemical Corporation; and "WHR991S" (phenolphthalimidine type epoxy resin) manufactured by Nippon Kayaku Co., Ltd.These may be used alone or in combination of two or more.

[0075] When a liquid epoxy resin and a solid epoxy resin are used in combination as the (B) epoxy resin, the mass ratio thereof (liquid epoxy resin:solid epoxy resin) is preferably 20:1 to 1:20, more preferably 10:1 to 1:10, and particularly preferably 7:1 to 1:7.

[0076] The epoxy equivalent of the (B) epoxy resin is preferably 50 g / eq. to 5,000 g / eq., more preferably 60 g / eq. to 2,000 g / eq., even more preferably 70 g / eq. to 1,000 g / eq., and even more preferably 80 g / eq. to 500 g / eq. The epoxy equivalent is the mass of the resin per equivalent of epoxy groups. This epoxy equivalent can be measured according to JIS K7236.

[0077] The weight average molecular weight (Mw) of the (B) epoxy resin is preferably 100 to 5,000, more preferably 250 to 3,000, and even more preferably 400 to 1,500. The weight average molecular weight of the resin can be measured by gel permeation chromatography (GPC) as a polystyrene-equivalent value.

[0078] The content of the (B) epoxy resin in the resin composition is not particularly limited, but is preferably less than 30% by mass, more preferably 25% by mass or less, even more preferably 20% by mass or less, even more preferably 25% by mass or less, and particularly preferably 10% by mass or less, based on 100% by mass of the nonvolatile components in the resin composition. The lower limit of the content of the (B) epoxy resin in the resin composition is not particularly limited, but is preferably 0.1% by mass or more, more preferably 0.5% by mass or more, even more preferably 1% by mass or more, even more preferably 3% by mass or more, and particularly preferably 5% by mass or more, based on 100% by mass of the nonvolatile components in the resin composition.

[0079] The mass ratio of the epoxy resin (B) to the allyl compound (A) having an alicyclic structure in the resin composition (component (B) / component (A)) is preferably 1 or more, more preferably 1.5 or more, and particularly preferably 2 or more. The upper limit of the mass ratio of the epoxy resin (B) to the allyl compound (A) having an alicyclic structure in the resin composition (component (B) / component (A)) is preferably 1,000 or less, more preferably 100 or less, and particularly preferably 50 or less.

[0080] <(C) Active ester compound> The resin composition of the present invention contains an active ester compound (C). The active ester compound (C) may be used alone or in combination of two or more in any ratio. The active ester compound (C) can function as an epoxy resin curing agent that reacts with the epoxy resin (B) to cure the epoxy resin.

[0081] As the (C) active ester compound, compounds having two or more highly reactive ester groups per molecule, such as phenol esters, thiophenol esters, N-hydroxyamine esters, and esters of heterocyclic hydroxy compounds, are generally preferred. The active ester compound is preferably one obtained by a condensation reaction between a carboxylic acid compound and / or a thiocarboxylic acid compound and a hydroxy compound and / or a thiol compound. From the viewpoint of improving heat resistance, active ester compounds obtained from a carboxylic acid compound and a hydroxy compound are preferred, and active ester compounds obtained from a carboxylic acid compound and a phenol compound and / or a naphthol compound are more preferred. Examples of carboxylic acid compounds include benzoic acid, acetic acid, succinic acid, maleic acid, itaconic acid, phthalic acid, isophthalic acid, terephthalic acid, and pyromellitic acid. Examples of phenol compounds or naphthol compounds include hydroquinone, resorcinol, bisphenol A, bisphenol F, bisphenol S, phenolphthalene, methylated bisphenol A, methylated bisphenol F, methylated bisphenol S, phenol, o-cresol, m-cresol, p-cresol, catechol, α-naphthol, β-naphthol, 1,5-dihydroxynaphthalene, 1,6-dihydroxynaphthalene, 2,6-dihydroxynaphthalene, dihydroxybenzophenone, trihydroxybenzophenone, tetrahydroxybenzophenone, phloroglucin, benzenetriol, dicyclopentadiene-type diphenol compounds, and phenol novolak. Here, "dicyclopentadiene-type diphenol compounds" refers to diphenol compounds obtained by condensing one dicyclopentadiene molecule with two phenol molecules.

[0082] Specifically, the (C) active ester compound is preferably a dicyclopentadiene-type active ester compound, a naphthalene-type active ester compound containing a naphthalene structure, an active ester compound containing an acetylated product of phenol novolac, or an active ester compound containing a benzoylated product of phenol novolac, and among these, at least one selected from dicyclopentadiene-type active ester compounds and naphthalene-type active ester compounds is more preferred, with dicyclopentadiene-type active ester compounds being even more preferred. As the dicyclopentadiene-type active ester compound, an active ester compound containing a dicyclopentadiene-type diphenol structure is preferred.

[0083] (C) Commercially available active ester compounds include, for example, "EXB9451," "EXB9460," "EXB9460S," "EXB-8000L," "EXB-8000L-65M," "EXB-8000L-65TM," "HPC-8000L-65TM," "HPC-8000," "HPC-8000-65T," "HPC-8000H," and "HPC-8000H-65TM" (manufactured by DIC Corporation) as active ester compounds containing a dicyclopentadiene-type diphenol structure; and "HP-B-8151-62T," "EXB-8100L-65T," "EXB-8150-60T," and "EXB-815 Examples of such compounds include "EXB-9416-70BK," "HPC-8150-60T," "HPC-8150-62T," and "EXB-8" (manufactured by DIC Corporation); an example of a phosphorus-containing active ester compound is "EXB9401" (manufactured by DIC Corporation); an example of an active ester compound which is an acetylated product of phenol novolac is "DC808" (manufactured by Mitsubishi Chemical Corporation); an example of an active ester compound which is a benzoylated product of phenol novolac is "YLH1026," "YLH1030," and "YLH1048" (manufactured by Mitsubishi Chemical Corporation); and an example of an active ester compound containing a styryl group and a naphthalene structure is "PC1300-02-65MA" (manufactured by Air Water Inc.).

[0084] The active ester group equivalent of the (C) active ester compound is preferably 50 g / eq. to 500 g / eq., more preferably 50 g / eq. to 400 g / eq., and even more preferably 100 g / eq. to 300 g / eq. The active ester group equivalent is the mass of the active ester compound per equivalent of the active ester group.

[0085] The content of the (C) active ester compound in the resin composition is 10% by mass or more, preferably 11% by mass or more, more preferably 12% by mass or more, even more preferably 13% by mass or more, and particularly preferably 14% by mass or more, based on 100% by mass of the nonvolatile components in the resin composition. The upper limit of the content of the (C) active ester compound in the resin composition is not particularly limited, but is preferably 50% by mass or less, more preferably 40% by mass or less, even more preferably 30% by mass or less, even more preferably 25% by mass or less, and particularly preferably 20% by mass or less, based on 100% by mass of the nonvolatile components in the resin composition.

[0086] The mass ratio of the active ester compound (C) to the allyl compound (A) having an alicyclic structure in the resin composition (component (C) / component (A)) is preferably 2 or more, more preferably 3 or more, and particularly preferably 4 or more. The upper limit of the mass ratio of the active ester compound (C) to the allyl compound (A) having an alicyclic structure in the resin composition (component (C) / component (A)) is preferably 2000 or less, more preferably 200 or less, and particularly preferably 100 or less.

[0087] <(C') Other hardeners> The resin composition of the present invention may further contain, as an optional component, a (C') curing agent other than the component (C). The (C') other curing agent may be used alone or in any combination of two or more. The (C') other curing agent, like the (C) active ester compound, may function as an epoxy resin curing agent that reacts with and cures the (B) epoxy resin.

[0088] (C') Other curing agents are not particularly limited, but examples thereof include phenolic curing agents, carbodiimide curing agents, acid anhydride curing agents, amine curing agents, benzoxazine curing agents, cyanate ester curing agents, and thiol curing agents. It is particularly preferable that the resin composition of the present invention contains a curing agent selected from the group consisting of phenolic curing agents and carbodiimide curing agents.

[0089] As the phenolic curing agent, a phenolic curing agent having a novolac structure is preferred from the viewpoint of heat resistance and water resistance. Also, from the viewpoint of adhesion to an adherend, a nitrogen-containing phenolic curing agent is preferred, and a triazine skeleton-containing phenolic curing agent is more preferred. Among them, a triazine skeleton-containing phenolic novolac resin is preferred from the viewpoint of highly satisfying heat resistance, water resistance, and adhesion. Specific examples of phenolic curing agents include "MEH-7700," "MEH-7810," and "MEH-7851" manufactured by Meiwa Chemical Industry Co., Ltd.; "NHN," "CBN," and "GPH" manufactured by Nippon Kayaku Co., Ltd.; "SN-170," "SN-180," "SN-190," "SN-475," "SN-485," "SN-495," "SN-375," and "SN-395" manufactured by Nippon Steel Chemical & Material Co., Ltd.; and "LA-7052," "LA-7054," "LA-3018," "LA-3018-50P," "LA-1356," "TD2090," and "TD-2090-60M" manufactured by DIC Corporation.

[0090] Examples of carbodiimide curing agents include curing agents having one or more, preferably two or more, carbodiimide structures in one molecule, such as aliphatic biscarbodiimides such as tetramethylene-bis(t-butylcarbodiimide) and cyclohexane-bis(methylene-t-butylcarbodiimide); aromatic biscarbodiimides such as phenylene-bis(xylylcarbodiimide); and aliphatic polycarbodiimides such as polyhexamethylenecarbodiimide, polytrimethylhexamethylenecarbodiimide, polycyclohexylenecarbodiimide, poly(methylenebiscyclohexylenecarbodiimide), and poly(isophoronecarbodiimide). ; aromatic polycarbodiimides such as poly(phenylenecarbodiimide), poly(naphthylenecarbodiimide), poly(tolylenecarbodiimide), poly(methyldiisopropylphenylenecarbodiimide), poly(triethylphenylenecarbodiimide), poly(diethylphenylenecarbodiimide), poly(triisopropylphenylenecarbodiimide), poly(diisopropylphenylenecarbodiimide), poly(xylylenecarbodiimide), poly(tetramethylxylylenecarbodiimide), poly(methylenediphenylenecarbodiimide), and poly[methylenebis(methylphenylene)carbodiimide].

[0091] Commercially available carbodiimide curing agents include, for example, "Carbodilite V-02B," "Carbodilite V-03," "Carbodilite V-04K," "Carbodilite V-07," and "Carbodilite V-09" manufactured by Nisshinbo Chemical Inc.; and "Stavaxol P," "Stavaxol P400," and "Hykasil 510" manufactured by Rhein Chemie.

[0092] The acid anhydride curing agent may be a curing agent having one or more acid anhydride groups in one molecule, and a curing agent having two or more acid anhydride groups in one molecule is preferred. Specific examples of the acid anhydride curing agent include phthalic anhydride, tetrahydrophthalic anhydride, hexahydrophthalic anhydride, methyltetrahydrophthalic anhydride, methylhexahydrophthalic anhydride, methylnadic anhydride, hydrogenated methylnadic anhydride, trialkyltetrahydrophthalic anhydride, dodecenyl succinic anhydride, 5-(2,5-dioxotetrahydro-3-furanyl)-3-methyl-3-cyclohexene-1,2-dicarboxylic anhydride, trimellitic anhydride, pyromellitic anhydride, and benzophenonetetracarboxylic dianhydride. Examples of suitable anhydrides include anhydrides, biphenyltetracarboxylic dianhydride, naphthalenetetracarboxylic dianhydride, oxydiphthalic dianhydride, 3,3'-4,4'-diphenylsulfonetetracarboxylic dianhydride, 1,3,3a,4,5,9b-hexahydro-5-(tetrahydro-2,5-dioxo-3-furanyl)-naphtho[1,2-C]furan-1,3-dione, ethylene glycol bis(anhydrotrimellitate), and polymeric anhydrides such as styrene-maleic acid resins, which are copolymers of styrene and maleic acid. Commercially available acid anhydride curing agents include "HNA-100," "MH-700," "MTA-15," "DDSA," and "OSA" manufactured by New Japan Chemical Co., Ltd.; "YH-306" and "YH-307" manufactured by Mitsubishi Chemical Corporation; "HN-2200" and "HN-5500" manufactured by Hitachi Chemical Co., Ltd.; and "EF-30," "EF-40," "EF-60," and "EF-80" manufactured by Clay Valley.

[0093] Examples of the amine curing agent include curing agents having one or more, preferably two or more, amino groups in one molecule, such as aliphatic amines, polyether amines, alicyclic amines, and aromatic amines, among which aromatic amines are preferred from the viewpoint of achieving the desired effects of the present invention. The amine curing agent is preferably a primary amine or a secondary amine, and more preferably a primary amine. Specific examples of amine-based curing agents include 4,4'-methylenebis(2,6-dimethylaniline), 4,4'-diaminodiphenylmethane, 4,4'-diaminodiphenyl sulfone, 3,3'-diaminodiphenyl sulfone, m-phenylenediamine, m-xylylenediamine, diethyltoluenediamine, 4,4'-diaminodiphenyl ether, 3,3'-dimethyl-4,4'-diaminobiphenyl, 2,2'-dimethyl-4,4'-diaminobiphenyl, 3,3'-dihydroxybenzidine, and 2,2-bis(3-amino-4-hydroxyphenyl)propane. propane, 3,3-dimethyl-5,5-diethyl-4,4-diphenylmethanediamine, 2,2-bis(4-aminophenyl)propane, 2,2-bis(4-(4-aminophenoxy)phenyl)propane, 1,3-bis(3-aminophenoxy)benzene, 1,3-bis(4-aminophenoxy)benzene, 1,4-bis(4-aminophenoxy)benzene, 4,4'-bis(4-aminophenoxy)biphenyl, bis(4-(4-aminophenoxy)phenyl)sulfone, bis(4-(3-aminophenoxy)phenyl)sulfone, and the like. Commercially available amine-based curing agents may be used, and examples thereof include "SEIKACURE-S" manufactured by Seika Corporation, "KAYABOND C-200S", "KAYABOND C-100", "KAYAHARD AA", "KAYAHARD AB", and "KAYAHARD AS" manufactured by Nippon Kayaku Co., Ltd., and "Epicure W" manufactured by Mitsubishi Chemical Corporation.

[0094] Specific examples of benzoxazine curing agents include "JBZ-OP100D" and "ODA-BOZ" manufactured by JFE Chemical Corporation; "HFB2006M" manufactured by Showa Polymer Co., Ltd.; and "Pd" and "Fa" manufactured by Shikoku Chemicals Corporation.

[0095] Examples of cyanate ester curing agents include bifunctional cyanate resins such as bisphenol A dicyanate, polyphenol cyanate (oligo(3-methylene-1,5-phenylene cyanate)), 4,4'-methylenebis(2,6-dimethylphenyl cyanate), 4,4'-ethylidene diphenyl dicyanate, hexafluorobisphenol A dicyanate, 2,2-bis(4-cyanate)phenylpropane, 1,1-bis(4-cyanatephenylmethane), bis(4-cyanate-3,5-dimethylphenyl)methane, 1,3-bis(4-cyanatephenyl-1-(methylethylidene))benzene, bis(4-cyanatephenyl)thioether, and bis(4-cyanatephenyl)ether; multifunctional cyanate resins derived from phenol novolac and cresol novolac; and prepolymers in which these cyanate resins are partially converted to triazine. Specific examples of cyanate ester curing agents include "PT30" and "PT60" (both phenol novolac type multifunctional cyanate ester resins) manufactured by Lonza Japan Co., Ltd., "BA230" and "BA230S75" (prepolymers in which part or all of bisphenol A dicyanate has been triazine converted to a trimer).

[0096] Examples of thiol-based curing agents include trimethylolpropane tris(3-mercaptopropionate), pentaerythritol tetrakis(3-mercaptobutyrate), and tris(3-mercaptopropyl)isocyanurate.

[0097] The reactive group equivalent of the (C') other curing agent is preferably 50 g / eq. to 3000 g / eq., more preferably 100 g / eq. to 1000 g / eq., even more preferably 100 g / eq. to 500 g / eq., and particularly preferably 100 g / eq. to 300 g / eq. The reactive group equivalent is the mass of the curing agent per equivalent of the reactive group.

[0098] The content of (C') other curing agent in the resin composition is not particularly limited, but is preferably 15% by mass or less, more preferably 10% by mass or less, even more preferably 7% by mass or less, and particularly preferably 5% by mass or less, based on 100% by mass of the nonvolatile components in the resin composition. The lower limit of the content of (C') other curing agent in the resin composition is not particularly limited, but may be, for example, 0% by mass or more, 0.01% by mass or more, 0.1% by mass or more, 1% by mass or more, 2% by mass or more, based on 100% by mass of the nonvolatile components in the resin composition.

[0099] The content of the (C) active ester compound in the resin composition is preferably 10% by mass or more, more preferably 30% by mass or more, even more preferably 40% by mass or more, and particularly preferably 50% by mass or more, when the total of the (C) active ester compound and the (C') other curing agent in the resin composition is 100% by mass.

[0100] <(D) Inorganic filler> The resin composition of the present invention contains (D) an inorganic filler. (D) The inorganic filler is contained in the resin composition in the form of particles.

[0101] (D) Inorganic fillers are inorganic compounds. Examples of (D) inorganic filler materials include silica, alumina, glass, cordierite, silicon oxide, barium sulfate, barium carbonate, talc, clay, mica powder, zinc oxide, hydrotalcite, boehmite, aluminum hydroxide, magnesium hydroxide, calcium carbonate, magnesium carbonate, magnesium oxide, boron nitride, aluminum nitride, manganese nitride, aluminum borate, strontium carbonate, strontium titanate, calcium titanate, magnesium titanate, bismuth titanate, titanium oxide, zirconium oxide, barium titanate, barium titanate zirconate, barium zirconate, calcium zirconate, zirconium phosphate, and zirconium tungstate phosphate. Among these, silica is particularly preferred. Examples of silica include amorphous silica, fused silica, crystalline silica, synthetic silica, and hollow silica. Spherical silica is preferred. The (D) inorganic filler may be used alone or in combination of two or more kinds in any ratio.

[0102] (D) Examples of commercially available inorganic fillers include "UFP-30" manufactured by Denka Chemical Industry Co., Ltd.; "SP60-05" and "SP507-05" manufactured by Nippon Steel & Sumikin Materials Co., Ltd.; "YC100C", "YA050C", "YA050C-MJE", and "YA010C" manufactured by Admatechs Co., Ltd.; "UFP-30" manufactured by Denka Company Limited; "Silfil NSS-3N", "Silfil NSS-4N", and "Silfil NSS-5N" manufactured by Tokuyama Corporation; "SC2500SQ", "SO-C4", "SO-C2", and "SO-C1" manufactured by Admatechs Co., Ltd.; and "DAW-03" and "FB-105FD" manufactured by Denka Company Limited.

[0103] The average particle size of the (D) inorganic filler is not particularly limited, but is preferably 10 μm or less, more preferably 5 μm or less, even more preferably 2 μm or less, even more preferably 1 μm or less, and particularly preferably 0.7 μm or less. The lower limit of the average particle size of the (D) inorganic filler is not particularly limited, but is preferably 0.01 μm or more, more preferably 0.05 μm or more, even more preferably 0.1 μm or more, and particularly preferably 0.2 μm or more. The average particle size of the (D) inorganic filler can be measured by a laser diffraction / scattering method based on Mie scattering theory. Specifically, a particle size distribution of the inorganic filler is created on a volume basis using a laser diffraction / scattering particle size distribution analyzer, and the median diameter is used as the average particle size. A measurement sample can be prepared by weighing 100 mg of inorganic filler and 10 g of methyl ethyl ketone into a vial and ultrasonically dispersing for 10 minutes. The measurement sample was measured using a laser diffraction particle size distribution analyzer, with blue and red light source wavelengths used, and the particle size distribution of the inorganic filler on a volume basis was measured using a flow cell system, and the average particle size was calculated as the median diameter from the particle size distribution obtained. An example of a laser diffraction particle size distribution analyzer is the "LA-960" manufactured by Horiba, Ltd.

[0104] The specific surface area of ​​the (D) inorganic filler is not particularly limited, but is preferably 0.1 m 2 / g or more, more preferably 0.5m 2 / g or more, more preferably 1m 2 / g or more, particularly preferably 3m 2 The upper limit of the specific surface area of ​​the (D) inorganic filler is not particularly limited, but is preferably 100 m 2 / g or less, more preferably 70m 2 / g or less, more preferably 50m 2 / g or less, particularly preferably 40m 2 The specific surface area of ​​the inorganic filler is obtained according to the BET method by adsorbing nitrogen gas onto the surface of the sample using a specific surface area measuring device (Macsorb HM-1210 manufactured by Mountech Co., Ltd.) and calculating the specific surface area using the BET multipoint method.

[0105] (D) The inorganic filler is preferably treated with a surface treatment agent from the viewpoint of improving moisture resistance and dispersibility. Examples of the surface treatment agent include a fluorine-containing silane coupling agent, an aminosilane coupling agent, an epoxysilane coupling agent, a mercaptosilane coupling agent, a silane coupling agent, an alkoxysilane, an organosilazane compound, and a titanate coupling agent. The surface treatment agent may be used alone or in any combination of two or more.

[0106] Examples of commercially available surface treatment agents include Shin-Etsu Chemical Co., Ltd.'s "KBM403" (3-glycidoxypropyltrimethoxysilane), Shin-Etsu Chemical Co., Ltd.'s "KBM803" (3-mercaptopropyltrimethoxysilane), Shin-Etsu Chemical Co., Ltd.'s "KBE903" (3-aminopropyltriethoxysilane), Shin-Etsu Chemical Co., Ltd.'s "KBM573" (N-phenyl-3-aminopropyltrimethoxysilane), Shin-Etsu Chemical Co., Ltd.'s "SZ-31" (hexamethyldisilazane), Shin-Etsu Chemical Co., Ltd.'s "KBM103" (phenyltrimethoxysilane), Shin-Etsu Chemical Co., Ltd.'s "KBM-4803" (long-chain epoxy-type silane coupling agent), and Shin-Etsu Chemical Co., Ltd.'s "KBM-7103" (3,3,3-trifluoropropyltrimethoxysilane).

[0107] The degree of surface treatment with the surface treatment agent is preferably within a predetermined range from the viewpoint of improving the dispersibility of the inorganic filler. Specifically, 100% by mass of the inorganic filler is preferably surface-treated with 0.2% to 5% by mass of the surface treatment agent, more preferably 0.2% to 3% by mass, and even more preferably 0.3% to 2% by mass.

[0108] The degree of surface treatment with the surface treatment agent can be evaluated by the amount of carbon per unit surface area of ​​the inorganic filler. From the viewpoint of improving the dispersibility of the inorganic filler, the amount of carbon per unit surface area of ​​the inorganic filler is set to 0.02 mg / m 2 More than 0.1 mg / m is preferable.2 More preferably, 0.2 mg / m or more 2 On the other hand, from the viewpoint of preventing an increase in the melt viscosity of the resin composition or the melt viscosity in the form of a sheet, it is more preferable that the melt viscosity is 1.0 mg / m 2 Preferably less than 0.8 mg / m 2 Less than 0.5 mg / m is more preferable. 2 The following is even more preferred:

[0109] (D) The amount of carbon per unit surface area of ​​the inorganic filler can be measured after the surface-treated inorganic filler is washed with a solvent (e.g., methyl ethyl ketone (MEK)). Specifically, a sufficient amount of MEK as a solvent is added to the inorganic filler that has been surface-treated with a surface treatment agent, and ultrasonic cleaning is performed at 25°C for 5 minutes. After removing the supernatant and drying the solid content, the amount of carbon per unit surface area of ​​the inorganic filler can be measured using a carbon analyzer. An "EMIA-320V" manufactured by Horiba, Ltd., or the like can be used as the carbon analyzer.

[0110] The content of the (D) inorganic filler in the resin composition is 60% by mass or more, preferably 63% by mass or more, more preferably 66% by mass or more, even more preferably 68% by mass or more, and particularly preferably 70% by mass or more, based on 100% by mass of the nonvolatile components in the resin composition. The upper limit of the content of the (D) inorganic filler in the resin composition is not particularly limited, but is preferably 90% by mass or less, more preferably 85% by mass or less, even more preferably 80% by mass or less, and particularly preferably 75% by mass or less, based on 100% by mass of the nonvolatile components in the resin composition.

[0111] The mass ratio of the inorganic filler (D) to the allyl compound (A) having an alicyclic structure in the resin composition (component (D) / component (A)) is preferably 10 or more, more preferably 15 or more, and particularly preferably 20 or more. The upper limit of the mass ratio of the inorganic filler (D) to the allyl compound (A) having an alicyclic structure in the resin composition (component (D) / component (A)) is preferably 10,000 or less, more preferably 1,000 or less, and particularly preferably 400 or less.

[0112] <(E) Radical Polymerizable Compound> The resin composition of the present invention may contain (E) a radically polymerizable compound as an optional component. The (E) radically polymerizable compound may be used alone or in any combination of two or more.

[0113] In one embodiment, the (E) radical polymerizable compound is a radical polymerizable compound having an ethylenically unsaturated bond. The (E) radical polymerizable compound is not particularly limited, but may have a radical polymerizable group such as an unsaturated hydrocarbon group such as an allyl group, a 3-cyclohexenyl group, a 3-cyclopentenyl group, a p-vinylphenyl group, a m-vinylphenyl group, or an o-vinylphenyl group; or an α,β-unsaturated carbonyl group such as an acryloyl group, a methacryloyl group, or a maleimide group (2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl group). The (E) radical polymerizable compound preferably has two or more radical polymerizable groups.

[0114] The (E) radically polymerizable compound may be, for example, a (meth)acrylic radically polymerizable compound, a styrene radically polymerizable compound, an allyl radically polymerizable compound, or a maleimide radically polymerizable compound.

[0115] The (meth)acrylic radical polymerizable compound is, for example, a compound having one or more, preferably two or more, acryloyl groups and / or methacryloyl groups. Examples of the (meth)acrylic radical polymerizable compound include cyclohexane-1,4-dimethanol di(meth)acrylate, cyclohexane-1,3-dimethanol di(meth)acrylate, tricyclodecane dimethanol di(meth)acrylate, neopentyl glycol di(meth)acrylate, 1,4-butanediol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, 1,8-octanediol di(meth)acrylate, 1,9-octanediol di(meth)acrylate, 1,6-octanedi ...8-octanediol di(meth)acrylate, 1,8-octanediol di(meth)acrylate, 1,8-octanediol di(meth)acrylate, 1,8-octanediol di(meth)acrylate, 1,8-octanediol di(meth)acrylate, 1,8-octanediol di(meth)acrylate, 1,8-octanediol di(meth)acrylate, 1 Low molecular weight (molecular weight less than 1000) aliphatic (meth)acrylic acid ester compounds such as nanediol di(meth)acrylate, 1,10-decanediol di(meth)acrylate, trimethylolpropane tri(meth)acrylate, trimethylolethane tri(meth)acrylate, glycerin tri(meth)acrylate, and pentaerythritol tetra(meth)acrylate; dioxane glycol di(meth)acrylate, 3,6-dioxa-1,8-octanediol di(meth)acrylate, Examples of the ether-containing (meth)acrylic acid ester compounds include low molecular weight (molecular weight less than 1000) ether-containing (meth)acrylic acid ester compounds such as bis(meth)acrylate, 3,6,9-trioxaundecane-1,11-diol di(meth)acrylate, polyethylene glycol di(meth)acrylate, polypropylene glycol di(meth)acrylate, 9,9-bis[4-(2-acryloyloxyethoxy)phenyl]fluorene, ethoxylated bisphenol A di(meth)acrylate, and propoxylated bisphenol A di(meth)acrylate; low molecular weight (molecular weight less than 1000) isocyanurate-containing (meth)acrylic acid ester compounds such as tris(3-hydroxypropyl)isocyanurate tri(meth)acrylate, tris(2-hydroxyethyl)isocyanurate tri(meth)acrylate, and ethoxylated isocyanuric acid tri(meth)acrylate; and high molecular weight (molecular weight 1000 or more) acrylic acid ester compounds such as (meth)acrylic-modified polyphenylene ether resins.Examples of commercially available (meth)acrylic radically polymerizable compounds include "A-DOG" (dioxane glycol diacrylate) manufactured by Shin-Nakamura Chemical Co., Ltd., "DCP-A" (tricyclodecane dimethanol diacrylate) and "DCP" (tricyclodecane dimethanol dimethacrylate) manufactured by Kyoeisha Chemical Co., Ltd., "KAYARAD R-684" (tricyclodecane dimethanol diacrylate) and "KAYARAD R-604" (dioxane glycol diacrylate) manufactured by Nippon Kayaku Co., Ltd., and "SA9000" and "SA9000-111" (methacrylic-modified polyphenylene ether) manufactured by SABIC Innovative Plastics.

[0116] The styrene radical polymerizable compound is, for example, a compound having one or more, preferably two or more, vinyl groups directly bonded to an aromatic carbon atom. Examples of the styrene radical polymerizable compound include low molecular weight (molecular weight less than 1000) styrene compounds such as divinylbenzene, 2,4-divinyltoluene, 2,6-divinylnaphthalene, 1,4-divinylnaphthalene, 4,4'-divinylbiphenyl, 1,2-bis(4-vinylphenyl)ethane, 2,2-bis(4-vinylphenyl)propane, and bis(4-vinylphenyl)ether; and high molecular weight (molecular weight 1000 or more) styrene compounds such as vinylbenzyl-modified polyphenylene ether resin and styrene-divinylbenzene copolymer. Examples of commercially available styrene-based radically polymerizable compounds include "ODV-XET(X03)", "ODV-XET(X04)", and "ODV-XET(X05)" (styrene-divinylbenzene copolymers) manufactured by Nippon Steel Chemical & Material Co., Ltd., and "OPE-2St 1200" and "OPE-2St 2200" (vinylbenzyl-modified polyphenylene ether resins) manufactured by Mitsubishi Gas Chemical Company, Inc.

[0117] The allyl radical polymerizable compound is, for example, a compound having one or more, preferably two or more, allyl groups. Examples of allyl radical polymerizable compounds include aromatic carboxylic acid allyl ester compounds such as diallyl diphenate, triallyl trimellitate, diallyl phthalate, diallyl isophthalate, diallyl terephthalate, diallyl 2,6-naphthalenedicarboxylate, and diallyl 2,3-naphthalenecarboxylate; isocyanuric acid allyl ester compounds such as 1,3,5-triallyl isocyanurate and 1,3-diallyl-5-glycidyl isocyanurate; epoxy-containing aromatic allyl compounds such as 2,2-bis[3-allyl-4-(glycidyloxy)phenyl]propane; benzoxazine-containing aromatic allyl compounds such as bis[3-allyl-4-(3,4-dihydro-2H-1,3-benzoxazin-3-yl)phenyl]methane; ether-containing aromatic allyl compounds such as 1,3,5-triallyl ether benzene; and allyl silane compounds such as diallyldiphenylsilane. Commercially available allyl radical polymerizable compounds include "TAIC" (1,3,5-triallyl isocyanurate) manufactured by Nippon Kasei Chemical Industry Co., Ltd., "DAD" (diallyl diphenate) manufactured by Nisshoku Techno Fine Chemical Co., Ltd., "TRIAM-705" (triallyl trimellitate) manufactured by Wako Pure Chemical Industries, Ltd., "DAND" (2,3-diallyl naphthalenecarboxylate) manufactured by Nippon Distillation Industry Co., Ltd., "ALP-d" (bis[3-allyl-4-(3,4-dihydro-2H-1,3-benzoxazin-3-yl)phenyl]methane) manufactured by Shikoku Chemical Industry Co., Ltd., "RE-810NM" (2,2-bis[3-allyl-4-(glycidyloxy)phenyl]propane) manufactured by Nippon Kayaku Co., Ltd., and "DA-MGIC" (1,3-diallyl-5-glycidyl isocyanurate) manufactured by Shikoku Chemical Industry Co., Ltd.

[0118] The maleimide radical polymerizable compound is, for example, a compound having one or more, preferably two or more maleimide groups. The maleimide-based radical polymerizable compound may be an aliphatic maleimide compound containing an aliphatic amine skeleton, or an aromatic maleimide compound containing an aromatic amine skeleton. Commercially available products include, for example, "SLK-2600" manufactured by Shin-Etsu Chemical Co., Ltd.; "BMI-1500," "BMI-1700," "BMI-3000J," "BMI-689," and "BMI-2500" (maleimide compounds containing a dimer diamine structure) manufactured by Designer Molecules, Inc.; "BMI-6100" (aromatic maleimide compound) manufactured by Designer Molecules, Inc.; "MIR-5000-60T" and "MIR-3000-70MT" (biphenylaralkyl maleimide compounds) manufactured by Nippon Kayaku Co., Ltd.; "BMI-70" and "BMI-80" manufactured by K.I. Chemical Industry Co., Ltd.; and "BMI-2300" and "BMI-TMH" manufactured by Daiwa Kasei Kogyo Co., Ltd. Furthermore, as the maleimide-based radical polymerizable compound, a maleimide resin (maleimide compound containing an indane ring skeleton) disclosed in the Japan Institute of Invention and Innovation's Technical Disclosure No. 2020-500211 may be used.

[0119] The ethylenically unsaturated bond equivalent of the (E) radically polymerizable compound is preferably 20 g / eq. to 3000 g / eq., more preferably 50 g / eq. to 2500 g / eq., even more preferably 70 g / eq. to 2000 g / eq., and particularly preferably 90 g / eq. to 1500 g / eq. The ethylenically unsaturated bond equivalent is the mass of the radically polymerizable compound per equivalent of the ethylenically unsaturated bond.

[0120] The weight average molecular weight (Mw) of the radically polymerizable compound (E) is preferably 40,000 or less, more preferably 10,000 or less, even more preferably 5,000 or less, and particularly preferably 3,000 or less. The lower limit is not particularly limited, but can be, for example, 150 or more.

[0121] The content of the radical polymerizable compound (E) in the resin composition is not particularly limited, but is preferably 25% by mass or less, more preferably 15% by mass or less, even more preferably 10% by mass or less, even more preferably 5% by mass or less, and particularly preferably 3% by mass or less, based on 100% by mass of the nonvolatile components in the resin composition. The lower limit of the content of the radical polymerizable compound (E) in the resin composition is not particularly limited, but is, for example, 0% by mass or more, 0.001% by mass or more, preferably 0.01% by mass or more, more preferably 0.05% by mass or more, even more preferably 0.1% by mass or more, and particularly preferably 0.5% by mass or more, based on 100% by mass of the nonvolatile components in the resin composition.

[0122] <(F) Curing accelerator> The resin composition of the present invention may contain, as an optional component, (F) a curing accelerator, which functions as a curing catalyst that accelerates the curing of (B) the epoxy resin.

[0123] Examples of the curing accelerator include phosphorus-based curing accelerators, urea-based curing accelerators, guanidine-based curing accelerators, imidazole-based curing accelerators, metal-based curing accelerators, and amine-based curing accelerators. From the viewpoint of improving crosslinkability, the resin composition of the present invention preferably contains an imidazole-based curing accelerator. (F) The curing accelerators may be used alone or in combination of two or more.

[0124] Examples of the phosphorus-based curing accelerator include aliphatic phosphonium salts such as tetrabutylphosphonium bromide, tetrabutylphosphonium chloride, tetrabutylphosphonium acetate, tetrabutylphosphonium decanoate, tetrabutylphosphonium laurate, bis(tetrabutylphosphonium)pyromellitate, tetrabutylphosphonium hydrogenhexahydrophthalate, tetrabutylphosphonium 2,6-bis[(2-hydroxy-5-methylphenyl)methyl]-4-methylphenolate, and di-tert-butyldimethylphosphonium tetraphenylborate; methyltriphenylphosphonium bromide, ethyltriphenylphosphonium bromide, propyltriphenylphosphonium bromide, butyltriphenylphosphonium bromide, benzyltriphenylphosphonium chloride, tetraphenylphosphonium bromide, p-tolyltriphenylphosphonium tetra-p-tolylborate, and tetraphenylphosphonium tetra-p-tolylborate. aromatic phosphonium salts such as tetraphenylborate, tetraphenylphosphonium tetra-p-tolylborate, triphenylethylphosphonium tetraphenylborate, tris(3-methylphenyl)ethylphosphonium tetraphenylborate, tris(2-methoxyphenyl)ethylphosphonium tetraphenylborate, (4-methylphenyl)triphenylphosphonium thiocyanate, tetraphenylphosphonium thiocyanate, and butyltriphenylphosphonium thiocyanate; aromatic phosphine-borane complexes such as triphenylphosphine-triphenylborane; aromatic phosphine-quinone adducts such as triphenylphosphine-p-benzoquinone adduct; aliphatic phosphines such as tributylphosphine, tri-tert-butylphosphine, trioctylphosphine, di-tert-butyl(2-butenyl)phosphine, di-tert-butyl(3-methyl-2-butenyl)phosphine, and tricyclohexylphosphine;Dibutylphenylphosphine, di-tert-butylphenylphosphine, methyldiphenylphosphine, ethyldiphenylphosphine, butyldiphenylphosphine, diphenylcyclohexylphosphine, triphenylphosphine, tri-o-tolylphosphine, tri-m-tolylphosphine, tri-p-tolylphosphine, tris(4-ethylphenyl)phosphine, tris(4-propylphenyl)phosphine, tris(4-isopropylphenyl)phosphine, tris(4-butylphenyl)phosphine, tris(4-tert-butylphenyl)phosphine, tris(2,4-dimethylphenyl)phosphine, tris(2,5-dimethylphenyl)phosphine, tris(2,6-dimethylphenyl)phosphine aromatic phosphines such as benzene, tris(3,5-dimethylphenyl)phosphine, tris(2,4,6-trimethylphenyl)phosphine, tris(2,6-dimethyl-4-ethoxyphenyl)phosphine, tris(2-methoxyphenyl)phosphine, tris(4-methoxyphenyl)phosphine, tris(4-ethoxyphenyl)phosphine, tris(4-tert-butoxyphenyl)phosphine, diphenyl-2-pyridylphosphine, 1,2-bis(diphenylphosphino)ethane, 1,3-bis(diphenylphosphino)propane, 1,4-bis(diphenylphosphino)butane, 1,2-bis(diphenylphosphino)acetylene, and 2,2'-bis(diphenylphosphino)diphenyl ether;

[0125] Examples of the urea-based curing accelerator include 1,1-dimethylurea; aliphatic dimethylureas such as 1,1,3-trimethylurea, 3-ethyl-1,1-dimethylurea, 3-cyclohexyl-1,1-dimethylurea, and 3-cyclooctyl-1,1-dimethylurea; 3-phenyl-1,1-dimethylurea, 3-(4-chlorophenyl)-1,1-dimethylurea, 3-(3,4-dichlorophenyl)-1,1-dimethylurea, 3-(3-chloro-4-methylphenyl)-1,1-dimethylurea, 3-(2-methylphenyl)-1,1-dimethylurea, 3-(4-methylphenyl)-1,1-dimethylurea, and 3-(3,4-dimethylphenyl)-1,1-dimethylurea. aromatic dimethylureas such as toluene bis(dimethylurea), 3-(4-isopropylphenyl)-1,1-dimethylurea, 3-(4-methoxyphenyl)-1,1-dimethylurea, 3-(4-nitrophenyl)-1,1-dimethylurea, 3-[4-(4-methoxyphenoxy)phenyl]-1,1-dimethylurea, 3-[4-(4-chlorophenoxy)phenyl]-1,1-dimethylurea, 3-[3-(trifluoromethyl)phenyl]-1,1-dimethylurea, N,N-(1,4-phenylene)bis(N',N'-dimethylurea), and N,N-(4-methyl-1,3-phenylene)bis(N',N'-dimethylurea) [toluene bisdimethylurea].

[0126] Examples of guanidine curing accelerators include dicyandiamide, 1-methylguanidine, 1-ethylguanidine, 1-cyclohexylguanidine, 1-phenylguanidine, 1-(o-tolyl)guanidine, dimethylguanidine, diphenylguanidine, trimethylguanidine, tetramethylguanidine, pentamethylguanidine, 1,5,7-triazabicyclo[4.4.0]dec-5-ene, 7-methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene, 1-methylbiguanide, 1-ethylbiguanide, 1-n-butylbiguanide, 1-n-octadecylbiguanide, 1,1-dimethylbiguanide, 1,1-diethylbiguanide, 1-cyclohexylbiguanide, 1-allylbiguanide, 1-phenylbiguanide, and 1-(o-tolyl)biguanide.

[0127] Examples of the imidazole curing accelerator include 2-methylimidazole, 2-undecylimidazole, 2-heptadecylimidazole, 1,2-dimethylimidazole, 2-ethyl-4-methylimidazole, 1,2-dimethylimidazole, 2-ethyl-4-methylimidazole, 2-phenylimidazole, 2-phenyl-4-methylimidazole, 1-benzyl-2-methylimidazole, and 1-benzyl-2-methylimidazole. Phenylimidazole, 1-cyanoethyl-2-methylimidazole, 1-cyanoethyl-2-undecylimidazole, 1-cyanoethyl-2-ethyl-4-methylimidazole, 1-cyanoethyl-2-phenylimidazole, 1-cyanoethyl-2-undecylimidazole, 1-cyanoethyl-2-phenylimidazolium trimellitate, 1-cyanoethyl-2-phenylimidazolium trimellitate, 2,4-diamino-6-[2'-methylimidazolyl -(1')]-ethyl-s-triazine, 2,4-diamino-6-[2'-undecylimidazolyl-(1')]-ethyl-s-triazine, 2,4-diamino-6-[2'-ethyl-4'-methylimidazolyl-(1')]-ethyl-s-triazine, 2,4-diamino-6-[2'-methylimidazolyl-(1')]-ethyl-s-triazine isocyanuric acid adduct, 2-phenylimidazole isocyanuric acid adduct , 2-phenyl-4,5-dihydroxymethylimidazole, 2-phenyl-4-methyl-5-hydroxymethylimidazole, 2,3-dihydro-1H-pyrrolo[1,2-a]benzimidazole, 1-dodecyl-2-methyl-3-benzylimidazolium chloride, 2-methylimidazoline, 2-phenylimidazoline, and other imidazole compounds, as well as adducts of imidazole compounds with epoxy resins.

[0128] As the imidazole-based curing accelerator, commercially available products may be used, such as "1B2PZ", "2MZA-PW", and "2PHZ-PW" manufactured by Shikoku Chemical Industry Co., Ltd., and "P200-H50" manufactured by Mitsubishi Chemical Corporation.

[0129] Examples of metal-based curing accelerators include organometallic complexes or organometallic salts of metals such as cobalt, copper, zinc, iron, nickel, manganese, and tin. Specific examples of organometallic complexes include organic cobalt complexes such as cobalt(II) acetylacetonate and cobalt(III) acetylacetonate, organic copper complexes such as copper(II) acetylacetonate, organic zinc complexes such as zinc(II) acetylacetonate, organic iron complexes such as iron(III) acetylacetonate, organic nickel complexes such as nickel(II) acetylacetonate, and organic manganese complexes such as manganese(II) acetylacetonate. Examples of organometallic salts include zinc octoate, tin octoate, zinc naphthenate, cobalt naphthenate, tin stearate, and zinc stearate.

[0130] Examples of the amine-based curing accelerator include trialkylamines such as triethylamine and tributylamine, 4-dimethylaminopyridine, benzyldimethylamine, 2,4,6-tris(dimethylaminomethyl)phenol, and 1,8-diazabicyclo(5,4,0)-undecene.

[0131] As the amine-based curing accelerator, commercially available products may be used, for example, "MY-25" manufactured by Ajinomoto Fine-Techno Co., Ltd.

[0132] The content of the (F) curing accelerator in the resin composition is not particularly limited, but is preferably 15% by mass or less, more preferably 10% by mass or less, even more preferably 5% by mass or less, and particularly preferably 1% by mass or less, based on 100% by mass of the nonvolatile components in the resin composition. The lower limit of the content of the (F) curing accelerator in the resin composition is not particularly limited, but may be, for example, 0% by mass or more, 0.001% by mass or more, 0.01% by mass or more, 0.05% by mass or more, based on 100% by mass of the nonvolatile components in the resin composition.

[0133] <(G)Thermoplastic resin> The resin composition of the present invention may contain a (G) thermoplastic resin. The (G) thermoplastic resin described here is a component other than the (A) allyl compound having an alicyclic structure and the (E) radically polymerizable compound described above.

[0134] Examples of (G) thermoplastic resins include polyimide resins, phenoxy resins, polyvinyl acetal resins, polyolefin resins, polybutadiene resins, polyamideimide resins, polyetherimide resins, polysulfone resins, polyethersulfone resins, polyphenylene ether resins, polycarbonate resins, polyetheretherketone resins, and polyester resins. In one embodiment, the (G) thermoplastic resin preferably contains a thermoplastic resin selected from the group consisting of polyimide resins and phenoxy resins, and more preferably contains a phenoxy resin. Furthermore, one type of thermoplastic resin may be used alone, or two or more types may be used in combination.

[0135] Specific examples of polyimide resins include "SLK-6100" manufactured by Shin-Etsu Chemical Co., Ltd., and "Rikacoat SN20" and "Rikacoat PN20" manufactured by New Japan Chemical Co., Ltd.

[0136] Examples of phenoxy resins include phenoxy resins having one or more skeletons selected from the group consisting of bisphenol A, bisphenol F, bisphenol S, bisphenolacetophenone, novolac, biphenyl, fluorene, dicyclopentadiene, norbornene, naphthalene, anthracene, adamantane, terpene, and trimethylcyclohexane. The terminal of the phenoxy resin may be any functional group such as a phenolic hydroxyl group or an epoxy group.

[0137] Specific examples of phenoxy resins include "1256" and "4250" manufactured by Mitsubishi Chemical Corporation (both of which are phenoxy resins containing a bisphenol A skeleton); "YX8100" manufactured by Mitsubishi Chemical Corporation (phenoxy resin containing a bisphenol S skeleton); "YX6954" manufactured by Mitsubishi Chemical Corporation (phenoxy resin containing a bisphenol acetophenone skeleton); "FX280" and "FX293" manufactured by Nippon Steel & Sumikin Chemical Co., Ltd.; and "YL7500BH30," "YX6954BH30," "YX7553," "YX7553BH30," "YL7769BH30," "YL6794," "YL7213," "YL7290," "YL7482," and "YL7891BH30" manufactured by Mitsubishi Chemical Corporation.

[0138] Examples of polyvinyl acetal resins include polyvinyl formal resins and polyvinyl butyral resins, with polyvinyl butyral resins being preferred. Specific examples of polyvinyl acetal resins include Denka Butyral 4000-2, Denka Butyral 5000-A, Denka Butyral 6000-C, and Denka Butyral 6000-EP, manufactured by Denki Kagaku Kogyo Co., Ltd.; and S-LEC BH series, BX series (e.g., BX-5Z), KS series (e.g., KS-1), BL series, and BM series, manufactured by Sekisui Chemical Co., Ltd.

[0139] Examples of polyolefin resins include ethylene copolymer resins such as low-density polyethylene, very low-density polyethylene, high-density polyethylene, ethylene-vinyl acetate copolymer, ethylene-ethyl acrylate copolymer, and ethylene-methyl acrylate copolymer; and polyolefin polymers such as polypropylene and ethylene-propylene block copolymer.

[0140] Examples of polybutadiene resins include hydrogenated polybutadiene skeleton-containing resins, hydroxy group-containing polybutadiene resins, phenolic hydroxy group-containing polybutadiene resins, carboxy group-containing polybutadiene resins, acid anhydride group-containing polybutadiene resins, epoxy group-containing polybutadiene resins, isocyanate group-containing polybutadiene resins, urethane group-containing polybutadiene resins, and polyphenylene ether-polybutadiene resins.

[0141] Specific examples of polyamide-imide resins include "Vylomax HR11NN" and "Vylomax HR16NN" manufactured by Toyobo Co., Ltd. Specific examples of polyamide-imide resins also include modified polyamide-imides such as "KS9100" and "KS9300" (polysiloxane skeleton-containing polyamide-imides) manufactured by Hitachi Chemical Co., Ltd.

[0142] A specific example of the polyethersulfone resin is "PES5003P" manufactured by Sumitomo Chemical Co., Ltd.

[0143] Specific examples of polysulfone resins include polysulfones "P1700" and "P3500" manufactured by Solvay Advanced Polymers.

[0144] A specific example of the polyphenylene ether resin is NORYL SA90 manufactured by SABIC, etc. A specific example of the polyetherimide resin is ULTEM manufactured by GE, etc.

[0145] Examples of polycarbonate resins include hydroxyl group-containing carbonate resins, phenolic hydroxyl group-containing carbonate resins, carboxyl group-containing carbonate resins, acid anhydride group-containing carbonate resins, isocyanate group-containing carbonate resins, and urethane group-containing carbonate resins. Specific examples of polycarbonate resins include "FPC0220" manufactured by Mitsubishi Gas Chemical Company, Inc., "T6002" and "T6001" (polycarbonate diols) manufactured by Asahi Kasei Chemicals Corporation, and "C-1090," "C-2090," and "C-3090" (polycarbonate diols) manufactured by Kuraray Co., Ltd. Specific examples of polyether ether ketone resins include "Sumiploy K" manufactured by Sumitomo Chemical Co., Ltd.

[0146] Examples of polyester resins include polyethylene terephthalate resin, polyethylene naphthalate resin, polybutylene terephthalate resin, polybutylene naphthalate resin, polytrimethylene terephthalate resin, polytrimethylene naphthalate resin, and polycyclohexane dimethyl terephthalate resin.

[0147] From the viewpoint of significantly achieving the effects of the present invention, the weight average molecular weight (Mw) of the (G) thermoplastic resin is preferably 5,000 or more, more preferably 8,000 or more, even more preferably 10,000 or more, and particularly preferably 20,000 or more, and is preferably 100,000 or less, more preferably 70,000 or less, even more preferably 60,000 or less, and particularly preferably 50,000 or less.

[0148] The content of the (G) thermoplastic resin in the resin composition is not particularly limited, but from the viewpoint of significantly achieving the desired effects of the present invention, when the nonvolatile components in the resin composition are taken as 100% by mass, it is preferably 20% by mass or less, more preferably 10% by mass or less, even more preferably 5% by mass or less, even more preferably 3% by mass or less, and particularly preferably 1% by mass or less. The lower limit of the content of the (G) thermoplastic resin in the resin composition is not particularly limited, but when the nonvolatile components in the resin composition are taken as 100% by mass, it may be, for example, 0% by mass or more, 0.01% by mass or more, 0.1% by mass or more, 0.3% by mass or more, etc.

[0149] <(H) Other Additives> The resin composition of the present invention may further contain any additives as a non-volatile component. Examples of such additives include radical polymerization initiators such as peroxide radical polymerization initiators and azo radical polymerization initiators; thermosetting resins other than epoxy resins such as epoxy acrylate resins, urethane acrylate resins, urethane resins, cyanate resins, benzoxazine resins, unsaturated polyester resins, phenolic resins, melamine resins, and silicone resins; organic fillers such as rubber particles; organometallic compounds such as organocopper compounds, organozinc compounds, and organocobalt compounds; colorants such as phthalocyanine blue, phthalocyanine green, iodine green, diazo yellow, crystal violet, titanium oxide, and carbon black; polymerization inhibitors such as hydroquinone, catechol, pyrogallol, and phenothiazine; leveling agents such as silicone leveling agents and acrylic polymer leveling agents; thickeners such as bentone and montmorillonite; and defoamers such as silicone defoamers, acrylic defoamers, fluorine-based defoamers, and vinyl resin defoamers. surfactants such as fluorine-based surfactants and silicone-based surfactants; flame retardants such as phosphorus-based flame retardants (e.g., phosphate ester compounds, phosphazene compounds, phosphinic acid compounds, red phosphorus), nitrogen-based flame retardants (e.g., melamine sulfate), halogen-based flame retardants, and inorganic flame retardants (e.g., antimony trioxide); dispersants such as phosphate ester-based dispersants, polyoxyalkylene-based dispersants, acetylene-based dispersants, silicone-based dispersants, anionic dispersants, and cationic dispersants; stabilizers such as borate-based stabilizers, titanate-based stabilizers, aluminate-based stabilizers, zirconate-based stabilizers, isocyanate-based stabilizers, carboxylic acid-based stabilizers, and carboxylic acid anhydride-based stabilizers. The (H) other additives may be used singly or in any combination of two or more kinds in any ratio. The content of the (H) other additives can be appropriately determined by a person skilled in the art.

[0150] <(I) Organic solvent> The resin composition of the present invention may further contain an arbitrary organic solvent as a volatile component in addition to the nonvolatile components described above. (I) As the organic solvent, any known organic solvent can be used appropriately, and the type thereof is not particularly limited. (I) Examples of the organic solvent include ketone-based solvents such as acetone, methyl ethyl ketone, methyl isobutyl ketone, and cyclohexanone; ester-based solvents such as methyl acetate, ethyl acetate, butyl acetate, isobutyl acetate, isoamyl acetate, methyl propionate, ethyl propionate, and γ-butyrolactone; ether-based solvents such as tetrahydropyran, tetrahydrofuran, 1,4-dioxane, diethyl ether, diisopropyl ether, dibutyl ether, diphenyl ether, and anisole; alcohol-based solvents such as methanol, ethanol, propanol, butanol, and ethylene glycol; 2-ethoxyethyl acetate, propylene glycol monomethyl ether acetate, diethylene glycol monoethyl ether acetate, ethyl diglycol acetate, γ-butyrolactone, and methoxypropionic acid. Examples of suitable organic solvents include ether ester solvents such as methyl ether, ester alcohol solvents such as methyl lactate, ethyl lactate, and methyl 2-hydroxyisobutyrate, ether alcohol solvents such as 2-methoxypropanol, 2-methoxyethanol, 2-ethoxyethanol, propylene glycol monomethyl ether, and diethylene glycol monobutyl ether (butyl carbitol), amide solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, and N-methyl-2-pyrrolidone, sulfoxide solvents such as dimethyl sulfoxide, nitrile solvents such as acetonitrile and propionitrile, aliphatic hydrocarbon solvents such as hexane, cyclopentane, cyclohexane, and methylcyclohexane, and aromatic hydrocarbon solvents such as benzene, toluene, xylene, ethylbenzene, and trimethylbenzene. (I) The organic solvent may be used alone or in combination of two or more solvents in any ratio.

[0151] In one embodiment, the content of (I) the organic solvent is not particularly limited, but when all components in the resin composition are taken as 100% by mass, it can be, for example, 60% by mass or less, 40% by mass or less, 30% by mass or less, 20% by mass or less, 15% by mass or less, 10% by mass or less, etc.

[0152] <Method of manufacturing resin composition> The resin composition of the present invention can be produced, for example, by adding (A) an allyl compound having an alicyclic structure, (B) an epoxy resin, (C) an active ester compound, (D) an inorganic filler, optionally (C') other curing agents, optionally (E) a radically polymerizable compound, optionally (F) a curing accelerator, optionally (G) a thermoplastic resin, optionally (H) other additives, and optionally (I) an organic solvent to an arbitrary preparation vessel in any order and / or simultaneously in part or in whole, and mixing them. Furthermore, during the process of adding and mixing each component, the temperature can be appropriately set, and heating and / or cooling may be performed temporarily or throughout the process. Furthermore, during or after the process of adding and mixing, the resin composition may be stirred or shaken using a stirring or shaking device such as a mixer to uniformly disperse the resin composition. Furthermore, degassing may be performed under low-pressure conditions, such as under vacuum, simultaneously with stirring or shaking.

[0153] <Characteristics of resin composition> The resin composition of the present invention comprises (A) an allyl compound having an alicyclic structure, (B) an epoxy resin, (C) an active ester compound, and (D) an inorganic filler, wherein the content of the (C) active ester compound is 10% by mass or more and the content of the (D) inorganic filler is 60% by mass or more. By using such a resin composition, it is possible to obtain a cured product having a low dielectric loss tangent (Df), excellent elongation at break, and excellent copper substrate adhesion strength (copper foil peel strength) after accelerated environmental testing (HAST).

[0154] A cured product of the resin composition of the present invention may be characterized by a low dielectric loss tangent (Df). Thus, in one embodiment, the dielectric loss tangent (Df) of the cured product of the resin composition, as measured at 5.8 GHz and 23°C as in Test Example 2 below, may be preferably 0.0200 or less, 0.0100 or less, more preferably 0.0080 or less, 0.0070 or less, 0.0060 or less, 0.0050 or less, even more preferably 0.0040 or less, 0.0035 or less, 0.0030 or less, and particularly preferably 0.0028 or less, 0.0027 or less.

[0155] A cured product of the resin composition of the present invention may be characterized by a high copper substrate adhesion strength (copper foil peel strength) after accelerated environmental testing (HAST). Thus, in one embodiment, the copper substrate adhesion strength (copper foil peel strength) after accelerated environmental testing (HAST) measured in accordance with JIS C6481 as in Test Example 1 below may be preferably 0.1 kgf / cm or more, more preferably 0.13 kgf / cm or more, 0.15 kgf / cm or more, even more preferably 0.16 kgf / cm or more, 0.17 kgf / cm or more, even more preferably 0.18 kgf / cm or more, 0.19 kgf / cm or more, and particularly preferably 0.20 kgf / cm or more. Furthermore, the copper substrate adhesion strength (copper foil peel strength) before the accelerated environmental testing (HAST) measured in the same manner is preferably 0.2 kgf / cm or more, more preferably 0.3 kgf / cm or more, even more preferably 0.4 kgf / cm or more, still more preferably 0.5 kgf / cm or more, and particularly preferably 0.6 kgf / cm or more.

[0156] A cured product of the resin composition of the present invention may be characterized by excellent elongation at break. Thus, in one embodiment, the elongation at break measured at 23°C as in Test Example 3 below may be preferably 0.5% or more, more preferably 0.8% or more, even more preferably 1.0% or more, and particularly preferably 1.2% or more. The upper limit of the elongation at break may typically be 10% or less, 5% or less, etc.

[0157] <Applications of resin composition> The resin composition of the present invention can be suitably used as a resin composition for insulating applications, particularly as a resin composition for forming an insulating layer. Specifically, it can be suitably used as a resin composition for forming an insulating layer (resin composition for forming an insulating layer) for forming a conductor layer (including a rewiring layer) formed on the insulating layer. It can also be suitably used as a resin composition for forming an insulating layer of a printed wiring board (resin composition for forming an insulating layer of a printed wiring board) in the printed wiring board described below. The resin composition of the present invention can also be used in a wide range of applications requiring a resin composition, such as sheet-like laminate materials such as resin sheets and prepregs, solder resists, underfill materials, die bonding materials, semiconductor encapsulants, hole-filling resins, and component-embedding resins.

[0158] Furthermore, for example, when a semiconductor chip package is manufactured through the following steps (1) to (6), the resin composition of the present invention can be suitably used as a resin composition for a rewiring formation layer (resin composition for forming a rewiring formation layer) as an insulating layer for forming a rewiring layer, and as a resin composition for encapsulating a semiconductor chip (resin composition for encapsulating a semiconductor chip). When a semiconductor chip package is manufactured, a rewiring layer may be further formed on the encapsulating layer. (1) a step of laminating a temporary fixing film on a substrate; (2) a step of temporarily fixing a semiconductor chip on a temporary fixing film; (3) forming an encapsulation layer on the semiconductor chip; (4) peeling the substrate and the temporary fixing film from the semiconductor chip; (5) forming a rewiring formation layer as an insulating layer on the surface of the semiconductor chip from which the base material and the temporary fixing film have been peeled off; and (6) A step of forming a rewiring layer as a conductor layer on the rewiring formation layer.

[0159] Furthermore, the resin composition of the present invention provides an insulating layer with good component embedding properties, and therefore can be suitably used when the printed wiring board is a circuit board with built-in components.

[0160] <Sheet-type laminated material> The resin composition of the present invention can be used by applying it in the form of a varnish, but industrially it is generally preferred to use it in the form of a sheet-like laminate material containing the resin composition.

[0161] As the sheet-like laminate material, the following resin sheets and prepregs are preferred.

[0162] In one embodiment, the resin sheet includes a support and a resin composition layer provided on the support, and the resin composition layer is formed from the resin composition of the present invention.

[0163] The thickness of the resin composition layer is preferably 50 μm or less, more preferably 40 μm or less, from the viewpoint of thinning the printed wiring board and providing a cured product of the resin composition with excellent insulating properties even when the cured product is thin. The lower limit of the thickness of the resin composition layer is not particularly limited, but can usually be 5 μm or more, 10 μm or more, etc.

[0164] Examples of the support include films made of plastic materials, metal foils, and release papers, with films made of plastic materials and metal foils being preferred.

[0165] When a film made of a plastic material is used as the support, examples of the plastic material include polyesters such as polyethylene terephthalate (hereinafter sometimes abbreviated as "PET") and polyethylene naphthalate (hereinafter sometimes abbreviated as "PEN"), polycarbonate (hereinafter sometimes abbreviated as "PC"), acrylics such as polymethyl methacrylate (PMMA), cyclic polyolefins, triacetyl cellulose (TAC), polyether sulfide (PES), polyether ketone, polyimide, etc. Among these, polyethylene terephthalate and polyethylene naphthalate are preferred, with inexpensive polyethylene terephthalate being particularly preferred.

[0166] When a metal foil is used as the support, examples of the metal foil include copper foil and aluminum foil, with copper foil being preferred. The copper foil may be a foil made of a single metal, copper, or an alloy of copper and another metal (e.g., tin, chromium, silver, magnesium, nickel, zirconium, silicon, titanium, etc.).

[0167] The surface of the support that is to be bonded to the resin composition layer may be subjected to a matte treatment, a corona treatment, or an antistatic treatment.

[0168] The support may also be a support with a release layer, which has a release layer on the surface that bonds to the resin composition layer. Examples of the release agent used in the release layer of the support with a release layer include one or more release agents selected from the group consisting of alkyd resins, polyolefin resins, urethane resins, and silicone resins. Commercially available products may also be used as the support with a release layer, including, for example, "SK-1," "AL-5," and "AL-7" manufactured by Lintec Corporation, "Lumirror T60" manufactured by Toray Industries, Inc., "Purex" manufactured by Teijin Limited, and "Uni-Peel" manufactured by Unitika Limited, which are PET films having a release layer primarily composed of an alkyd resin-based release agent.

[0169] The thickness of the support is not particularly limited, but is preferably in the range of 5 μm to 75 μm, more preferably 10 μm to 60 μm. When a support with a release layer is used, it is preferable that the thickness of the entire support with a release layer is in the above range.

[0170] In one embodiment, the resin sheet may further include an optional layer as needed. Examples of such optional layers include a protective film conforming to the support and provided on the surface of the resin composition layer that is not bonded to the support (i.e., the surface opposite the support). The thickness of the protective film is not particularly limited, but is, for example, 1 μm to 40 μm. By laminating the protective film, adhesion of dust and the like to the surface of the resin composition layer and scratches can be suppressed.

[0171] The resin sheet can be produced, for example, by preparing a liquid resin composition as is or a resin varnish by dissolving the resin composition in an organic solvent, applying this onto a support using a die coater or the like, and then drying to form a resin composition layer.

[0172] The organic solvent may be the same as the organic solvent described as a component of the resin composition. The organic solvent may be used alone or in combination of two or more.

[0173] Drying may be carried out by known methods such as heating or hot air blowing. Drying conditions are not particularly limited, but drying is carried out so that the content of organic solvent in the resin composition layer becomes 10% by mass or less, preferably 5% by mass or less. Although this varies depending on the boiling point of the organic solvent in the resin composition or resin varnish, for example, when a resin composition or resin varnish containing 30% by mass to 60% by mass of organic solvent is used, the resin composition layer can be formed by drying at 50°C to 150°C for 3 to 10 minutes.

[0174] The resin sheet can be stored in a rolled state. When the resin sheet has a protective film, it can be used by peeling off the protective film.

[0175] In one embodiment, the prepreg is formed by impregnating a sheet-like fiber substrate with the resin composition of the present invention.

[0176] The sheet-like fiber substrate used for the prepreg is not particularly limited, and commonly used prepreg substrates such as glass cloth, aramid nonwoven fabric, and liquid crystal polymer nonwoven fabric can be used. From the viewpoint of thinning the printed wiring board, the thickness of the sheet-like fiber substrate is preferably 50 μm or less, more preferably 40 μm or less, even more preferably 30 μm or less, and particularly preferably 20 μm or less. The lower limit of the thickness of the sheet-like fiber substrate is not particularly limited. It is usually 10 μm or more.

[0177] The prepreg can be produced by a known method such as a hot melt method or a solvent method.

[0178] The thickness of the prepreg may be in the same range as that of the resin composition layer in the resin sheet described above.

[0179] The sheet-like laminate material of the present invention can be suitably used for forming an insulating layer of a printed wiring board (for an insulating layer of a printed wiring board), and can be more suitably used for forming an interlayer insulating layer of a printed wiring board (for an interlayer insulating layer of a printed wiring board).

[0180] <Printed wiring board> The printed wiring board of the present invention includes an insulating layer made of a cured product obtained by curing the resin composition of the present invention.

[0181] The printed wiring board can be produced, for example, by using the above-mentioned resin sheet by a method including the following steps (I) and (II). (I) A step of laminating a resin sheet on an inner layer substrate so that the resin composition layer of the resin sheet is bonded to the inner layer substrate. (II) A step of curing (e.g., thermally curing) the resin composition layer to form an insulating layer.

[0182] The "inner layer substrate" used in step (I) is a member that will become the substrate of a printed wiring board, and examples thereof include glass epoxy substrates, metal substrates, polyester substrates, polyimide substrates, BT resin substrates, and thermosetting polyphenylene ether substrates. The substrate may have a conductor layer on one or both sides, and this conductor layer may be patterned. An inner layer substrate having a conductor layer (circuit) formed on one or both sides of the substrate may be referred to as an "inner layer circuit board." Furthermore, the "inner layer substrate" of the present invention also includes intermediate products on which an insulating layer and / or a conductor layer is to be further formed during the production of a printed wiring board. When the printed wiring board is a circuit board with built-in components, an inner layer substrate with built-in components may be used.

[0183] The inner layer substrate and the resin sheet can be laminated, for example, by thermocompression bonding the resin sheet to the inner layer substrate from the support side. Examples of a member for thermocompression bonding the resin sheet to the inner layer substrate (hereinafter also referred to as a "thermocompression bonding member") include a heated metal plate (such as a SUS end plate) or a metal roll (SUS roll). Note that rather than pressing the thermocompression bonding member directly onto the resin sheet, it is preferable to press it via an elastic material such as heat-resistant rubber so that the resin sheet can sufficiently conform to the surface irregularities of the inner layer substrate.

[0184] The lamination of the inner layer substrate and the resin sheet may be carried out by a vacuum lamination method. In the vacuum lamination method, the thermocompression temperature is preferably in the range of 60°C to 160°C, more preferably 80°C to 140°C, the thermocompression pressure is preferably in the range of 0.098MPa to 1.77MPa, more preferably 0.29MPa to 1.47MPa, and the thermocompression time is preferably in the range of 20 seconds to 400 seconds, more preferably 30 seconds to 300 seconds. The lamination may be carried out under reduced pressure conditions, preferably at a pressure of 26.7hPa or less.

[0185] The lamination can be performed using a commercially available vacuum laminator, such as a vacuum pressure laminator manufactured by Meiki Seisakusho Co., Ltd., a vacuum applicator manufactured by Nikko Materials Co., Ltd., or a batch vacuum pressure laminator.

[0186] After lamination, the laminated resin sheets may be smoothed under normal pressure (atmospheric pressure), for example, by pressing a thermocompression member from the support side. The pressing conditions for the smoothing treatment may be the same as the thermocompression conditions for lamination. The smoothing treatment may be performed using a commercially available laminator. Note that lamination and smoothing treatment may be performed consecutively using the commercially available vacuum laminator.

[0187] The support may be removed between step (I) and step (II), or may be removed after step (II).

[0188] In step (II), the resin composition layer is cured (for example, by heat curing) to form an insulating layer made of a cured product of the resin composition. The curing conditions for the resin composition layer are not particularly limited, and conditions typically employed for forming insulating layers for printed wiring boards may be used.

[0189] For example, the thermal curing conditions for the resin composition layer vary depending on the type of resin composition, but in one embodiment, the curing temperature is preferably 120° C. to 240° C., more preferably 150° C. to 220° C., and even more preferably 170° C. to 210° C. The curing time is preferably 5 minutes to 120 minutes, more preferably 10 minutes to 100 minutes, and even more preferably 15 minutes to 100 minutes.

[0190] Before thermally curing the resin composition layer, the resin composition layer may be preheated at a temperature lower than the curing temperature. For example, prior to thermally curing the resin composition layer, the resin composition layer may be preheated at a temperature of 50°C to 120°C, preferably 60°C to 115°C, more preferably 70°C to 110°C for 5 minutes or more, preferably 5 minutes to 150 minutes, more preferably 15 minutes to 120 minutes, and even more preferably 15 minutes to 100 minutes.

[0191] When manufacturing a printed wiring board, the following steps may be further performed: (III) drilling holes in the insulating layer, (IV) roughening the insulating layer, and (V) forming a conductor layer. These steps (III) to (V) may be performed according to various methods known to those skilled in the art and used in manufacturing printed wiring boards. When the support is removed after step (II), the removal of the support may be performed between steps (II) and (III), between steps (III) and (IV), or between steps (IV) and (V). Furthermore, if necessary, the formation of the insulating layer and the conductor layer in steps (II) to (V) may be repeated to form a multilayer wiring board.

[0192] In another embodiment, the printed wiring board of the present invention can be produced using the above-mentioned prepreg. The production method is basically the same as when a resin sheet is used.

[0193] Step (III) is a step of drilling holes in the insulating layer, thereby forming holes such as via holes and through holes in the insulating layer. Step (III) may be performed using, for example, a drill, a laser, plasma, or the like, depending on the composition of the resin composition used to form the insulating layer. The dimensions and shape of the holes may be determined appropriately depending on the design of the printed wiring board.

[0194] Step (IV) is a step of roughening the insulating layer. Typically, smear removal is also performed in this step (IV). The roughening treatment procedure and conditions are not particularly limited, and known procedures and conditions commonly used in forming insulating layers for printed wiring boards can be adopted. For example, the insulating layer can be roughened by performing a swelling treatment with a swelling liquid, a roughening treatment with an oxidizing agent, and a neutralization treatment with a neutralizing liquid in this order.

[0195] The swelling liquid used in the roughening treatment is not particularly limited, but examples thereof include alkaline solutions and surfactant solutions, and is preferably an alkaline solution, with sodium hydroxide solution and potassium hydroxide solution being more preferred. Commercially available swelling liquids include "Swelling Dip Securigance P" and "Swelling Dip Securigance SBU" manufactured by Atotech Japan. The swelling treatment using a swelling liquid is not particularly limited, but can be carried out by, for example, immersing the insulating layer in a swelling liquid at 30°C to 90°C for 1 to 20 minutes. To keep the swelling of the resin in the insulating layer to an appropriate level, it is preferable to immerse the insulating layer in a swelling liquid at 40°C to 80°C for 5 to 15 minutes.

[0196] The oxidizing agent used in the roughening treatment is not particularly limited, but examples thereof include alkaline permanganate solutions prepared by dissolving potassium permanganate or sodium permanganate in an aqueous solution of sodium hydroxide. Roughening treatment using an oxidizing agent such as alkaline permanganate solution is preferably carried out by immersing the insulating layer in an oxidizing agent solution heated to 60°C to 100°C for 10 to 30 minutes. The concentration of permanganate in the alkaline permanganate solution is preferably 5% by mass to 10% by mass. Commercially available oxidizing agents include alkaline permanganate solutions such as "Concentrate Compact CP" and "Dosing Solution Securigance P" manufactured by Atotech Japan.

[0197] The neutralizing solution used in the roughening treatment is preferably an acidic aqueous solution, and examples of commercially available products include "Reduction Solution Securigant P" manufactured by Atotech Japan.

[0198] Treatment with a neutralizing solution can be carried out by immersing the surface that has been roughened with an oxidizing agent in a neutralizing solution at 30° C. to 80° C. for 5 to 30 minutes. From the standpoint of workability, etc., a method in which the object that has been roughened with an oxidizing agent is immersed in a neutralizing solution at 40° C. to 70° C. for 5 to 20 minutes is preferred.

[0199] In one embodiment, the arithmetic mean roughness (Ra) of the insulating layer surface after the roughening treatment is preferably 400 nm or less, more preferably 350 nm or less, and even more preferably 300 nm or less. There is no particular limitation on the lower limit, but it may be preferably 0.5 nm or more, more preferably 1 nm or more, etc. Furthermore, the root mean square roughness (Rq) of the insulating layer surface after the roughening treatment is preferably 400 nm or less, more preferably 350 nm or less, and even more preferably 300 nm or less. There is no particular limitation on the lower limit, but it may be preferably 0.5 nm or more, more preferably 1 nm or more, etc. The arithmetic mean roughness (Ra) and root mean square roughness (Rq) of the insulating layer surface can be measured using a non-contact surface roughness meter.

[0200] Step (V) is a step of forming a conductor layer, and the conductor layer is formed on the insulating layer. The conductor material used for the conductor layer is not particularly limited. In a preferred embodiment, the conductor layer contains one or more metals selected from the group consisting of gold, platinum, palladium, silver, copper, aluminum, cobalt, chromium, zinc, nickel, titanium, tungsten, iron, tin, and indium. The conductor layer may be a single metal layer or an alloy layer. Examples of alloy layers include layers formed from alloys of two or more metals selected from the above group (e.g., nickel-chromium alloys, copper-nickel alloys, and copper-titanium alloys). Among these, from the viewpoints of versatility in forming the conductor layer, cost, ease of patterning, etc., a single metal layer of chromium, nickel, titanium, aluminum, zinc, gold, palladium, silver, or copper, or an alloy layer of a nickel-chromium alloy, a copper-nickel alloy, or a copper-titanium alloy is preferred, a single metal layer of chromium, nickel, titanium, aluminum, zinc, gold, palladium, silver, or copper, or an alloy layer of a nickel-chromium alloy is more preferred, and a single metal layer of copper is even more preferred.

[0201] The conductor layer may have a single layer structure or a multi-layer structure in which two or more single metal layers or alloy layers made of different types of metals or alloys are laminated. When the conductor layer has a multi-layer structure, the layer in contact with the insulating layer is preferably a single metal layer of chromium, zinc, or titanium, or an alloy layer of a nickel-chromium alloy.

[0202] The thickness of the conductor layer depends on the desired design of the printed wiring board, but is generally 3 μm to 35 μm, preferably 5 μm to 30 μm.

[0203] In one embodiment, the conductor layer may be formed by plating. For example, a conductor layer having a desired wiring pattern can be formed by plating the surface of the insulating layer using a conventionally known technique such as a semi-additive method or a full-additive method. From the viewpoint of ease of production, it is preferable to form the conductor layer by a semi-additive method. An example of forming the conductor layer by a semi-additive method will be described below.

[0204] First, a plating seed layer is formed on the surface of an insulating layer by electroless plating. Next, a mask pattern is formed on the formed plating seed layer, exposing a portion of the plating seed layer corresponding to the desired wiring pattern. After a metal layer is formed on the exposed plating seed layer by electrolytic plating, the mask pattern is removed. Thereafter, unnecessary plating seed layer is removed by etching or the like, thereby forming a conductor layer having the desired wiring pattern.

[0205] In another embodiment, the conductor layer may be formed using a metal foil. When a metal foil is used to form the conductor layer, step (V) is preferably performed between steps (I) and (II). For example, after step (I), the support is removed, and a metal foil is laminated on the exposed surface of the resin composition layer. The resin composition layer and the metal foil may be laminated by a vacuum lamination method. The lamination conditions may be the same as those described for step (I). Next, step (II) is performed to form an insulating layer. Thereafter, a conductor layer having a desired wiring pattern can be formed using the metal foil on the insulating layer by a conventionally known technique such as a subtractive method or a modified semi-additive method.

[0206] The metal foil can be produced by a known method such as an electrolytic method, a rolling method, etc. Examples of commercially available metal foils include HLP foil and JXUT-III foil manufactured by JX Nippon Mining & Metals Corporation, and 3EC-III foil and TP-III foil manufactured by Mitsui Mining & Smelting Co., Ltd.

[0207] <Semiconductor device> The semiconductor device of the present invention includes the printed wiring board of the present invention. The semiconductor device of the present invention can be manufactured using the printed wiring board of the present invention.

[0208] Examples of semiconductor devices include various semiconductor devices used in electrical appliances (for example, computers, mobile phones, digital cameras, and televisions) and vehicles (for example, motorcycles, automobiles, trains, ships, and aircraft). [Example]

[0209] The present invention will be described in more detail below with reference to examples. The present invention is not limited to these examples. In the following, "parts" and "%" representing amounts mean "parts by mass" and "% by mass", respectively, unless otherwise specified. Unless otherwise specified, the temperature and pressure conditions are room temperature (23°C) and atmospheric pressure (1 atm), respectively.

[0210] Example 1 Two parts of an allyl compound having an alicyclic structure ("FATC-809" manufactured by Gun-ei Chemical Industry Co., Ltd., weight-average molecular weight approximately 10,000, allyl equivalent approximately 400 g / eq.) and 10 parts of a naphthalene-type epoxy resin ("HP-4032-SS" manufactured by DIC Corporation, 1,6-bis(glycidyloxy)naphthalene, epoxy equivalent approximately 145 g / eq.) were heated and dissolved in 20 parts of MEK with stirring. The mixture was cooled to room temperature, and the resulting solution was mixed with 30 parts of an active ester compound ("HPC-8000-65T" manufactured by DIC Corporation, active ester group equivalent approximately 223 g / eq., toluene solution with a non-volatile content of 65%) and spherical silica ("SO-C2" manufactured by Admatechs Co., Ltd., average particle size 0.5 μm, specific surface area 5.8 m) surface-treated with a silane coupling agent ("KBM-573" manufactured by Shin-Etsu Chemical Co., Ltd.). 2 90 parts of hydroxybenzoate (1 / g), 2 parts of a triazine skeleton-containing phenolic curing agent (DIC Corporation's "LA-3018-50P", active group equivalent weight approximately 151 g / eq., 2-methoxypropanol solution with a non-volatile content of 50%), 5 parts of a carbodiimide curing agent (Nisshinbo Chemical Inc.'s "V-03", active group equivalent weight approximately 216 g / eq., toluene solution with a non-volatile content of 50%), 0.1 parts of an imidazole curing accelerator (Shikoku Chemical Industries Co., Ltd.'s "1B2PZ", 1-benzyl-2-phenylimidazole), and 2 parts of a phenoxy resin (Mitsubishi Chemical Corporation's "YX7553BH30", a 1:1 solution of MEK and cyclohexanone with a non-volatile content of 30% by mass) were mixed and uniformly dispersed using a high-speed rotating mixer to prepare a resin composition (resin varnish).

[0211] <Example 2> A resin composition (resin varnish) was prepared in the same manner as in Example 1, except that 2 parts of an allyl compound having an alicyclic structure ("FTC-809AE" manufactured by Gun-ei Chemical Industry Co., Ltd., allyl equivalent: approximately 1000 g / eq.) was used instead of 2 parts of an allyl compound having an alicyclic structure ("FATC-809" manufactured by Gun-ei Chemical Industry Co., Ltd.), and 30 parts of an active ester compound ("HPC-8000-65T" manufactured by DIC Corporation) were used instead of 30 parts of an active ester compound ("HPC-8150-62T" manufactured by DIC Corporation, active ester group equivalent: approximately 220 g / eq., non-volatile component ratio: 62% by mass in toluene solution).

[0212] Example 3 A resin composition (resin varnish) was prepared in the same manner as in Example 1, except that 10 parts of a biphenyl-type epoxy resin ("NC3000L" manufactured by Nippon Kayaku Co., Ltd., epoxy equivalent: approximately 269 g / eq.) was used instead of 10 parts of a naphthalene-type epoxy resin ("HP-4032-SS" manufactured by DIC Corporation).

[0213] Example 4 A resin composition (resin varnish) was prepared in the same manner as in Example 3, except that the amount of allyl compound having an alicyclic structure ("FATC-809" manufactured by Gunei Chemical Industry Co., Ltd.) used was changed from 2 parts to 0.5 parts.

[0214] <Example 5> A resin composition (resin varnish) was prepared in the same manner as in Example 3, except that 4 parts of an allyl compound having an alicyclic structure ("FTC-809AE" manufactured by Gun-ei Chemical Industry Co., Ltd., weight-average molecular weight of about (to be described later), allyl equivalent of about 1000 g / eq.) were used instead of 2 parts of an allyl compound having an alicyclic structure ("FATC-809" manufactured by Gun-ei Chemical Industry Co., Ltd.).

[0215] Example 6 A resin composition (resin varnish) was prepared in the same manner as in Example 1, except that the amount of spherical silica ("SO-C2" manufactured by Admatechs Co., Ltd.) surface-treated with a silane coupling agent ("KBM-573" manufactured by Shin-Etsu Chemical Co., Ltd.) was changed from 90 parts to 93 parts, and 2 parts of biphenylaralkyl novolac maleimide ("MIR-3000-70MT" manufactured by Nippon Kayaku Co., Ltd., MEK / toluene mixed solution with a non-volatile content of 70%) was used, and 30 parts of an active ester compound ("HPC-8000-65T" manufactured by DIC Corporation) was replaced with 30 parts of an active ester compound ("HPC-8150-62T" manufactured by DIC Corporation, active ester group equivalent weight approximately 220 g / eq., toluene solution with a non-volatile content of 62% by mass).

[0216] Example 7 A resin composition (resin varnish) was prepared in the same manner as in Example 6, except that 2 parts of methacrylic-modified polyphenylene ether (SA9000-111 manufactured by SABIC Innovative Plastics) was used instead of 2 parts of biphenylaralkyl novolac maleimide (MIR-3000-70MT manufactured by Nippon Kayaku Co., Ltd.).

[0217] Example 8 A resin composition (resin varnish) was prepared in the same manner as in Example 6, except that 2 parts of vinylbenzyl-modified polyphenylene ether ("OPE-2St 2200" manufactured by Mitsubishi Gas Chemical Co., Ltd., a toluene solution with a non-volatile content of 65%) was used instead of 2 parts of biphenylaralkyl novolac maleimide ("MIR-3000-70MT" manufactured by Nippon Kayaku Co., Ltd.), and the amount of imidazole-based curing accelerator ("1B2PZ" manufactured by Shikoku Chemical Industry Co., Ltd.) used was changed from 0.1 part to 0.5 parts.

[0218] <Comparative Example 1> A resin composition (resin varnish) was prepared in the same manner as in Example 3, except that the amount of spherical silica ("SO-C2" manufactured by Admatechs Co., Ltd.) surface-treated with a silane coupling agent ("KBM-573" manufactured by Shin-Etsu Chemical Co., Ltd.) was changed from 90 parts to 85 parts, and 2 parts of an allyl compound having an alicyclic structure ("FATC-809" manufactured by Gun-ei Chemical Industry Co., Ltd.) was not used.

[0219] <Comparative Example 2> A resin composition (resin varnish) was prepared in the same manner as in Example 2, except that the amount of spherical silica ("SO-C2" manufactured by Admatechs Co., Ltd.) surface-treated with a silane coupling agent ("KBM-573" manufactured by Shin-Etsu Chemical Co., Ltd.) was changed from 90 parts to 85 parts, and 2 parts of an allyl compound having an alicyclic structure ("FTC-809AE" manufactured by Gun-ei Chemical Industry Co., Ltd.) was not used.

[0220] <Comparative Example 3> A resin composition was prepared in the same manner as in Example 1, except that the amount of spherical silica ("SO-C2" manufactured by Admatechs Co., Ltd.) surface-treated with a silane coupling agent ("KBM-573" manufactured by Shin-Etsu Chemical Co., Ltd.) used was changed from 90 parts to 52 parts, the amount of active ester compound ("HPC-8000-65T" manufactured by DIC Corporation) used was changed from 30 parts to 10 parts, and 2 parts of an allyl compound having an alicyclic structure ("FATC-809" manufactured by Gun-ei Chemical Industry Co., Ltd.) were not used.

[0221] <Comparative Example 4> A resin composition was prepared in the same manner as in Example 1, except that the amount of spherical silica ("SO-C2" manufactured by Admatechs Co., Ltd.) surface-treated with a silane coupling agent ("KBM-573" manufactured by Shin-Etsu Chemical Co., Ltd.) was changed from 90 parts to 40 parts, and 2 parts of an allyl compound having an alicyclic structure ("FATC-809" manufactured by Gun-ei Chemical Industry Co., Ltd.) was not used.

[0222] <Test Example 1: Measurement of copper substrate adhesion strength (copper foil peel strength)> (1) Preparation of resin sheet A polyethylene terephthalate film ("AL5" manufactured by Lintec Corporation, thickness 38 μm) with a release layer was prepared as a support. The resin compositions obtained in the Examples and Comparative Examples were uniformly applied onto the release layer of this support so that the thickness of the resin composition layer after drying would be 40 μm. Thereafter, the resin composition was dried at 80°C to 100°C (average 90°C) for 4 minutes to obtain a resin sheet including the support and the resin composition layer.

[0223] (2) Copper foil surface treatment The shiny side of Mitsui Mining & Smelting Co., Ltd.'s "3EC-III" (electrolytic copper foil, 35 μm) was roughened by etching it to 1 μm with MEC's ​​"CZ8101" to roughen the copper surface, followed by a rust-proofing treatment (CL8300). This copper foil is called CZ copper foil. It was then heated in an oven at 130°C for 30 minutes to obtain a CZ copper foil with a treated surface.

[0224] (3) Preparation of inner layer board: Both sides of a glass cloth-based epoxy resin double-sided copper-clad laminate (copper foil thickness 18 μm, substrate thickness 0.4 mm, Panasonic "R1515A") with an inner layer circuit formed thereon were etched by 1 μm using MEC "CZ8101" to roughen the copper surface, thereby obtaining an inner layer substrate.

[0225] (4) Lamination of resin composition layer The protective film was peeled off from the resin sheet prepared in (1) above to expose the resin composition layer. Using a batch-type vacuum pressure laminator (Nikko Materials Co., Ltd., two-stage build-up laminator "CVP700"), the resin composition layer was laminated on both sides of the inner layer substrate so that it was in contact with the inner layer substrate. Lamination was performed by reducing the pressure for 30 seconds to 13 hPa or less, followed by pressure bonding at 120°C and a pressure of 0.74 MPa for 30 seconds. Next, a heat press was performed at 100°C and a pressure of 0.5 MPa for 60 seconds. The support was then peeled off to expose the resin composition layer.

[0226] (5) Lamination of copper foil and curing of resin composition layer The treated surface of the CZ copper foil was laminated onto the exposed resin composition layer under the same conditions as in (4) above, and the resin composition layer was cured at 200°C for 90 minutes to form a cured product (insulating layer), thereby producing evaluation substrate A with CZ copper foil laminated on both sides.

[0227] (6) Measurement of copper substrate adhesion strength (copper foil peel strength) before HAST The evaluation board A prepared in (5) above was cut into small pieces measuring 150 mm × 30 mm. A cutter was used to make a 10 mm wide, 100 mm long cut in the copper foil portion of each small piece, and one end of the cut piece was peeled off and gripped with the gripping tool of the tensile tester described below. The load (kgf / cm) when 35 mm was peeled off vertically at a rate of 50 mm / min at room temperature (23°C) was measured using a tensile tester (TSE Autocom Universal Tester "AC-50C-SL") in accordance with Japanese Industrial Standard JIS C6481.

[0228] (7) Measurement of copper substrate adhesion strength (copper foil peel strength) after HAST The evaluation substrate A prepared in (5) above was subjected to an accelerated environmental test for 100 hours under high-temperature and high-humidity conditions of 130°C and 85%RH using a highly accelerated life tester ("PM422" manufactured by Kusumoto Chemicals Co., Ltd.). After the HAST, a notch was made in the evaluation substrate A in the same manner as above, and one end of the notch was peeled off and gripped with the gripper of the tensile tester in the same manner as in the measurement in (6) above. The load (kgf / cm) when 35 mm was peeled off vertically at room temperature (normal temperature) at a rate of 50 mm / min was measured in accordance with Japanese Industrial Standard JIS C6481.

[0229] <Test Example 2: Measurement of dielectric loss tangent> The protective film was peeled off from the resin sheet prepared in Test Example 1 (1), and the resin composition layer was thermally cured by heating at 200°C for 90 minutes. The support was then peeled off to obtain a cured film formed from the cured product of the resin composition. The cured film was cut into a piece 2 mm wide and 80 mm long to obtain a cured product A for evaluation.

[0230] The dielectric loss tangent (Df value) of the obtained cured evaluation material A was measured by the cavity resonance perturbation method using an "HP8362B" manufactured by Agilent Technologies at a measurement frequency of 5.8 GHz and a measurement temperature of 23°C. Measurements were performed on three test pieces, and the average value was calculated.

[0231] <Test Example 3: Measurement of elongation at break> The cured product A for evaluation obtained in Test Example 2 was subjected to a tensile test in accordance with Japanese Industrial Standards JIS K7127 using a Tensilon universal testing machine ("RTC-1250A" manufactured by Orientec Co., Ltd.) to measure the elongation at break (%) at room temperature (23°C).

[0232] The amounts of raw materials used and the contents of nonvolatile components in the resin compositions of the Examples and Comparative Examples, as well as the measurement results of the Test Examples, are shown in Table 1 below.

[0233] [Table 1]

[0234] As shown in Table 1, Comparative Example 3, which had a low content of (C) active ester compound, and Comparative Example 4, which had a low content of (D) inorganic filler, had relatively high dielectric loss tangents. Comparative Examples 1 and 2, which had high contents of (C) active ester compound and (D) inorganic filler, had low dielectric loss tangents, but also low elongation at break and low copper substrate adhesion strength (copper foil peel strength) after accelerated environmental testing (HAST). In contrast, when the resin composition of the present invention containing (A) an allyl compound having an alicyclic structure was used, the dielectric loss tangent (Df) was low, the elongation at break was high, and the copper substrate adhesion strength (copper foil peel strength) after accelerated environmental testing (HAST) was also high.

Claims

1. A resin composition comprising (A) an allyl compound having an alicyclic structure, (B) an epoxy resin, (C) an active ester compound, and (D) an inorganic filler, The component (A) is represented by formula (A), and the weight average molecular weight of the component (A) is 1,000 to 20,000; The content of the component (C) is 10% by mass or more, relative to 100% by mass of the nonvolatile components in the resin composition; A resin composition, wherein the content of component (D) is 60% by mass or more, based on 100% by mass of nonvolatile components in the resin composition. 【Chemistry 1】 [In the formula, A 1 s each independently represent a group represented by formula (A3); A 2 s each independently represent a group represented by formula (Aa); n represents an integer of 0 or more. 【Chemistry 2】 [Wherein, X is a single bond, —C(R ５ ) ２ -, -O-, -CO-, -S-, -SO-, or -SO ２ - indicates R ２ represents a hydrogen atom, and R ５ each independently represents a hydrogen atom or a hydrocarbon group, R ３ and R ４ each independently represents a hydrocarbon group, and b R ３ At least one of the R ４ At least one of the groups is an allyl group, b and c each independently represent an integer of 0 to 3, and * represents a binding site. 【Transformation 3】 [In the formula, each Y independently represents a single bond or an alkylene group, the ring Cy represents a tricyclo[5.2.1.0 2,6 ]decane ring represented by formula (a-1), and * represents a bonding site.] 【Chemistry 4】 [wherein * indicates a binding site.]

2. A resin composition comprising (A) an allyl compound having an alicyclic structure, (B) an epoxy resin, (C) an active ester compound, and (D) an inorganic filler, The component (A) is represented by formula (A), and the weight average molecular weight of the component (A) is 1,000 to 20,000; The content of the component (C) is 10% by mass or more, relative to 100% by mass of the nonvolatile components in the resin composition; A resin composition, wherein the content of component (D) is 60% by mass or more, based on 100% by mass of nonvolatile components in the resin composition. 【Transformation 5】 [In the formula, A 1 s each independently represent a group represented by formula (A3); A 2 s each independently represent a group represented by formula (Aa); n represents an integer of 0 or more. 【Transformation 6】 [Wherein, X is a single bond, —C(R ５ ) ２ -, -O-, -CO-, -S-, -SO-, or -SO ２ - indicates R ２ represents an allyl group, and R ５ each independently represents a hydrogen atom or a hydrocarbon group, R ３ and R ４ each independently represents a hydrocarbon group, b and c each independently represent an integer of 0 to 3, and * represents a bonding site. 【Transformation 7】 [In the formula, each Y independently represents a single bond or an alkylene group, the ring Cy represents a tricyclo[5.2.1.0 2,6 ]decane ring represented by formula (a-1), and * represents a bonding site.] 【Transformation 8】 [wherein * indicates a binding site.]

3. 3. The resin composition according to claim 1, wherein the allyl equivalent of component (A) is 200 g / eq. to 2000 g / eq.

4. The resin composition according to any one of claims 1 to 3, wherein the content of component (A) is 0.01 mass% or more, when the total amount of non-volatile components in the resin composition is 100 mass%.

5. The resin composition according to any one of claims 1 to 4, wherein the content of component (A) is 5% by mass or less, when the total amount of non-volatile components in the resin composition is 100% by mass.

6. The resin composition according to any one of claims 1 to 5, wherein the content of the component (B) is 1% by mass to 20% by mass, where the total amount of non-volatile components in the resin composition is 100% by mass.

7. The resin composition according to any one of claims 1 to 6, wherein the mass ratio of the component (B) to the component (A) (component (B) / component (A)) is 1.5 to 100.

8. The resin composition according to any one of claims 1 to 7, wherein the component (D) is silica.

9. The resin composition according to any one of claims 1 to 8, wherein the content of the component (D) is 70% by mass or more, when the total amount of non-volatile components in the resin composition is 100% by mass.

10. The resin composition according to any one of claims 1 to 9, further comprising an imidazole-based curing accelerator.

11. The resin composition according to any one of claims 1 to 10, further comprising a curing agent selected from the group consisting of phenolic curing agents and carbodiimide curing agents.

12. The resin composition according to any one of claims 1 to 11, wherein the elongation at break of a cured product of the resin composition is 1.0% or more when measured at 23°C.

13. The resin composition according to any one of claims 1 to 12, wherein the dielectric loss tangent (Df) of a cured product of the resin composition is 0.0030 or less when measured at 5.8 GHz and 23 ° C.

14. A cured product of the resin composition according to any one of claims 1 to 13.

15. A sheet-like laminate material comprising the resin composition according to any one of claims 1 to 13.

16. A resin sheet comprising: a support; and a resin composition layer formed from the resin composition according to any one of claims 1 to 13 provided on the support.

17. A printed wiring board comprising an insulating layer made of a cured product of the resin composition according to any one of claims 1 to 13.

18. A semiconductor device comprising the printed wiring board according to claim 17.

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