Resin composition

Abstract

The present invention provides a resin composition which can provide a cured product having a small arithmetic average roughness (Ra) and low relative dielectric constant (Dk) and dielectric loss tangent (Df). The present invention is a resin composition comprising (A) a maleimide compound containing a divalent group represented by formula (1), and a divalent group represented by formula (2) and / or a divalent group represented by formula (3) in one molecule, (B) an epoxy resin, and (C) an inorganic filler, wherein the content of the component (C) exceeds 30 mass% when the non-volatile content of the resin composition is taken as 100 mass% (the definitions of the symbols are described in the specification).

Description

TECHNICAL FIELD

[0001] The present application relates to a resin composition containing a maleimide compound. Further, it relates to a cured product, a sheet-like laminated material, a resin sheet, a printed wiring board, and a semiconductor device obtained using the resin composition. BACKGROUND

[0002] As a manufacturing technique of a printed wiring board, a manufacturing method based on a buildup method of alternately laminating an insulating layer and a conductor layer is known. In the manufacturing method using the buildup method, generally, the insulating layer is formed by curing a resin composition.

[0003] In recent years, along with the progress of miniaturization and high performance of electronic devices, high frequency of signals has been caused, and low dielectric constant and low dielectric loss tangent of the insulating layer of a multilayer printed wiring board have been demanded. In addition, in order to improve adhesion to fine and high-density wiring, an insulating layer having a smaller surface roughness has been demanded.

[0004] In Patent Literatures 1 and 2, resin compositions using various maleimide compounds are disclosed.

[0005] PRIOR ART DOCUMENTS

[0006] PATENT LITERATURE

[0007] Patent Literature 1: International Publication No. 2018 / 212116

[0008] Patent Literature 2: International Publication No. 2020 / 045489. SUMMARY

[0009] PROBLEMS TO BE SOLVED BY THE INVENTION

[0010] An object of the present application is to provide a resin composition which can obtain a cured product having a small arithmetic average roughness (Ra) and low relative dielectric constant (Dk) and dielectric loss tangent (Df).

[0011] MEANS FOR SOLVING THE PROBLEMS

[0012] In order to solve the object of the present application, the present inventors and others have made earnest research, and as a result, have found that by using a specific maleimide compound as a component of a resin composition, a cured product having a small arithmetic average roughness (Ra) and low relative dielectric constant (Dk) and dielectric loss tangent (Df) is unexpectedly obtained, thereby completing the present application.

[0013] That is, the present application contains the following;

[0014] [1] A resin composition comprising:

[0015] (A) a maleimide compound containing "a bivalent group represented by Formula (1)", and "a bivalent group represented by Formula (2) and / or a bivalent group represented by Formula (3)" in one molecule,

[0016] (B) an epoxy resin, and

[0017] (C) an inorganic filler.

[0018] [Chemical Formula 1]

[0019]

[0020] [In the formula, X 1 represents a single bond, -C(R 10 )2-, -0-, -CO-, -S-, -SO-, -S02-, -CONH-, -NHCO-, -COO-, or -OCO-; R 10 each independently represents a hydrogen atom, an alkyl group, an alkenyl group, an aryl-alkyl group, or an aryl group; for R 11 , R 12 , R 13 , R 14 , R 21 , R 22 , R 23 , and R 24 , at least one of them each independently represents an alkyl group, an alkenyl group, an aryl-alkyl group, or an aryl group, and the others (the rest) represent a hydrogen atom; and * represents a bonding site].

[0021] [Chemical Formula 2]

[0022]

[0023] [In the formula, R 31 , R 32 , and R 33 each independently represents a hydrogen atom, an alkyl group, an alkenyl group, an aryl-alkyl group, or an aryl group; and * represents a bonding site].

[0024] [Chemical Formula 3]

[0025]

[0026] [In the formula, R 41 and R 42 each independently represents a hydrogen atom, an alkyl group, an alkenyl group, an aryl-alkyl group, or an aryl group; and * represents a bonding site].

[0027] wherein the content of the (C) component is greater than 30 mass% when the non-volatile component in the resin composition is taken as 100 mass%.

[0028] [2] The resin composition according to the above [1], wherein X 1 is -C(R 10 )2-; R 11 , R 12 , R 21 , and R 22 are each independently an alkyl group; and R 10 , R 13 , R 14 , R 23 , R 24 , R 31 , R 32 , R 33 , R 41 , and R 42 are hydrogen atoms;

[0029] [3] The resin composition according to the above [1] or [2], wherein,

[0030] (A) the component further contains a divalent group represented by formula (4) in one molecule,

[0031] [Chemical Formula 4]

[0032]

[0033] [In the formula, X 2 , X 3 , and X 4 each independently represent a single bond, -C(R 50 )2-, -O-, -CO-, -S-, -SO-, -SO2-, -CONH-, -NHCO-, -COO-, or -OCO-; R 50 , R 51 , R 52 , R 53 , R 54 , R 61 , R 62 , R 63 , R 64 , R 71 , R 72 , R 73 , R 74 , R 81 , R 82 , R 83 , and R 84 each independently represent a hydrogen atom, an alkyl group, an alkenyl group, an aryl-alkyl group, or an aryl group; and * represents a bonding site.]

[0034] [4] The resin composition according to the above [3], wherein X 2 and X 4 are -O-; and X 3-C(R 50 )2-; R 50 each independently alkyl; and R 51 , R 52 , R 53 , R 54 , R 61 , R 62 , R 63 , R 64 , R 71 , R 72 , R 73 , R 74 , R 81 , R 82 , R 83 , and R 84 is a hydrogen atom;

[0035] [5] The resin composition according to any one of the above [1] to [4], wherein the content of the (A) component is 1 to 40 mass% when the nonvolatile component in the resin composition is taken as 100 mass%;

[0036] [6] The resin composition according to any one of the above [1] to [5], wherein further comprising an (A') radical polymerizable compound other than the (A) component;

[0037] [7] The resin composition according to any one of the above [1] to [6], wherein the (B) component comprises: (B-1) an epoxy resin containing a condensed ring structure;

[0038] [8] The resin composition according to the above [7], wherein the (B-1) component comprises a naphthol aralkyl type epoxy resin;

[0039] [9] The resin composition according to any one of the above [1] to [8], wherein the content of the (B) component is 1 to 50 mass% when the nonvolatile component in the resin composition is taken as 100 mass%;

[0040]

[10] The resin composition according to any one of the above [1] to [9], wherein the mass ratio of the (A) component to the (B) component ((A) component / (B) component) is 0.3 to 3;

[0041]

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

[10] , wherein the content of the (C) component is 50 mass% or more when the nonvolatile component in the resin composition is taken as 100 mass%;

[0042]

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

[11] , wherein the mass ratio of the (A) component to the (C) component ((A) component / (C) component) is 0.05 to 0.5.

[0043]

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

[12] , wherein further comprising (D) an active ester compound.

[0044]

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

[13] , wherein the cured product of the resin composition has a dielectric loss tangent of 0.005 or less when measured at 5.8 GHz at 23°C.

[0045]

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

[14] , wherein the cured product of the resin composition has a relative dielectric constant of 3.0 or less when measured at 5.8 GHz at 23°C.

[0046]

[16] A cured product, which is a cured product of the resin composition according to any one of the above [1] to

[15] .

[0047]

[17] A sheet-shaped laminated material, which contains the resin composition according to any one of the above [1] to

[15] .

[0048]

[18] A resin sheet, which has:

[0049] a support body, and

[0050] a resin composition layer formed of the resin composition according to any one of the above [1] to

[15] provided on the support body.

[0051]

[19] A printed wiring board, which has an insulating layer formed of the cured product of the resin composition according to any one of the above [1] to

[15] .

[0052]

[20] A semiconductor device, which includes the printed wiring board according to the above

[19] .

[0053] Effects of the Invention

[0054] According to the resin composition of the present application, a cured product having a small arithmetic average roughness (Ra) and low relative dielectric constant (Dk) and dielectric loss tangent (Df) can be obtained. DETAILED DESCRIPTION

[0055] Hereinafter, the present application will be described in detail according to its preferred embodiments. However, the present application is not limited to the following embodiments and examples, and can be arbitrarily changed without departing from the scope of the claims of the present application and equivalents thereof.

[0056] <Resin composition>

[0057] The resin composition of the present application contains: (A) a maleimide compound containing a divalent group represented by formula (1), and a divalent group represented by formula (2) and / or a divalent group represented by formula (3) in one molecule, (B) an epoxy resin, and (C) an inorganic filler, and the content of the (C) component exceeds 30 mass% when the nonvolatile content in the resin composition is taken as 100 mass%. By using such a resin composition, a cured product having a small arithmetic average roughness (Ra) and low relative dielectric constant (Dk) and dielectric loss tangent (Df) can be obtained.

[0058] The resin composition of the present application can further contain an arbitrary component in addition to (A) a maleimide compound containing a divalent group represented by formula (1), and a divalent group represented by formula (2) and / or a divalent group represented by formula (3) in one molecule, (B) an epoxy resin, and (C) an inorganic filler. As the arbitrary component, for example, (A') another maleimide compound, (D) an active ester compound, (E) a curing accelerator, (F) another additive, and (G) an organic solvent can be mentioned. Hereinafter, each component contained in the resin composition will be described in detail.

[0059] <(A) Specific maleimide compound>

[0060] The resin composition of the present application contains (A) a maleimide compound containing a divalent group represented by formula (1), and a divalent group represented by formula (2) and / or a divalent group represented by formula (3) in one molecule (hereinafter also referred to as "specific maleimide compound"). The maleimide compound refers to an organic compound containing at least one maleimide group (2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl) in a molecule. The (A) specific maleimide compound can be used alone or two or more kinds thereof can be used in combination at an arbitrary ratio.

[0061] The (A) specific maleimide compound contains a divalent group represented by formula (1) in one molecule.

[0062] [Chemical formula 5]

[0063]

[0064] [In the formula, * indicates a bonding site, and the other symbols are described below].

[0065] In formula (1), X 1 represents a single bond, -C(R 10-2-, -O-, -CO-, -S-, -SO-, -SO2-, -CONH-, -NHCO-, -COO-, or -OCO-. X 1 It is better to be -C(R) 10 -2-, -O-, -CO-, -S-, -SO-, or -SO2-; preferably -C(R) 10 )2- or -O-; especially good is -C(R) 10 )2-.

[0066] In equation (1), R 10 Each can independently represent a hydrogen atom, alkyl, alkenyl, aryl-alkyl (an alkyl group whose substituted position is replaced by one aryl group), or aryl. R 10 It is preferable that each atom is a hydrogen atom or an alkyl group; it is especially preferable that each atom is a hydrogen atom.

[0067] Alkyl groups refer to straight-chain, branched, and / or cyclic monovalent aliphatic saturated hydrocarbon groups. Preferably, alkyl groups have 1 to 14 carbon atoms, more preferably 1 to 10 carbon atoms, and even more preferably 1 to 6 or 4 to 10 carbon atoms. Examples of alkyl groups include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopentyl, cyclohexyl, methylcyclohexyl, dimethylcyclohexyl, trimethylcyclohexyl, cyclopentylmethyl, and cyclohexylmethyl. Alkenyl groups refer to straight-chain, branched, and / or cyclic monovalent aliphatic unsaturated hydrocarbon groups having at least one carbon-carbon double bond. Preferably, alkenyl groups have 2 to 14 carbon atoms, more preferably 2 to 10 carbon atoms, and even more preferably 2 to 6 or 4 to 10 carbon atoms. Examples of alkenyl groups include vinyl, propenyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, and cyclohexenyl. Aryl groups refer to monovalent aromatic hydrocarbon groups. Preferably, aryl groups have 6 to 14 carbon atoms. Examples of aryl groups include phenyl, 1-naphthyl, and 2-naphthyl.

[0068] In equation (1), for R 11 R 12 R 13 R 14 R 21 R 22 R 23 and R 24 In this context, at least one of them (preferably at least two, more preferably at least four) independently represents an alkyl, alkenyl, aryl-alkyl, or aryl group; and the others represent hydrogen atoms. Preferably, R 11 R 12 R 13 and R 14 At least one of them (preferably at least two), and R 21 R22 23 24 at least one (more preferably at least two) of R 11 12 21 22 R 13 14 23 24 R 11 12 21 22 R 13 14 23 24 R

[0069] The divalent group represented by formula (1) is particularly preferably a divalent group represented by formula (1').

[0070] [Chemical Formula 6]

[0071]

[0072] [in the formula, * indicates a bonding site].

[0073] (A) A specific maleimide compound contains, in one molecule, a divalent group represented by formula (1), and also contains a divalent group represented by formula (2) and / or a divalent group represented by formula (3).

[0074] [Chemical Formula 7]

[0075]

[0076] [in the formula, * indicates a bonding site, and other symbols are described below].

[0077] [Chemical Formula 8]

[0078]

[0079] [in the formula, * indicates a bonding site, and other symbols are described below]. Preferably, (A) A specific maleimide compound contains, in one molecule, a divalent group represented by formula (1), and also contains a divalent group represented by formula (2).

[0080] in formula (2), R 31 32 and R​​​​​​​​​​​​​​​33 each independently represents a hydrogen atom, an alkyl group, an alkenyl group, an aryl-alkyl group, or an aryl group. R 31 , R 32 , and R 33 are preferably each independently a hydrogen atom, or an alkyl group; particularly preferably a hydrogen atom.

[0081] In formula (3), R 41 , and R 42 each independently represents a hydrogen atom, an alkyl group, an alkenyl group, an aryl-alkyl group, or an aryl group. R 41 , and R 42 are preferably each independently a hydrogen atom, or an alkyl group; particularly preferably a hydrogen atom.

[0082] (A) A specific maleimide compound, preferably, a compound containing, in one molecule, a bivalent group represented by formula (1), and a bivalent group represented by formula (2) and / or a bivalent group represented by formula (3), and further containing a bivalent group represented by formula (4).

[0083] [Chemical Formula 9]

[0084]

[0085] [In the formula, * indicates a binding site, and the other symbols are described below.]

[0086] In formula (4), X 2 , X 3 , and X 4 each independently represents a single bond, -C(R 50 )2-, -O-, -CO-, -S-, -SO-, -SO2-, -CONH-, -NHCO-, -COO-, or -OCO-. Preferably, X 2 , X 3 , and X 4 each independently is -C(R 50 )2-, -O-, -CO-, -S-, -SO-, or -SO2-. Further preferably, X 2 , X 3 , and X 4 each independently is -C(R 50 )2-, or -O-. Particularly preferably, X 2 and X 4 is -O-; and X 3 is -C(R 50 )2-.

[0087] In formula (4), R 50 each independently represents a hydrogen atom, an alkyl group, an alkenyl group, an aryl-alkyl group, or an aryl group. R 50R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, R12, R13, R14, R15, R16, R17, and R18each independently represent a hydrogen atom, an alkyl group, an alkenyl group, an aryl-alkyl group, or an aryl group. R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, R12, R13, R14, R15, R16, R17, and R18are preferably each independently a hydrogen atom, or an alkyl group; particularly preferably a hydrogen atom.

[0088] In formula (4), R 51 , R 52 , R 53 , R 54 , R 61 , R 62 , R 63 , R 64 , R 71 , R 72 , R 73 , R 74 , R 81 , R 82 , R 83 , and R 84 each independently represent a hydrogen atom, an alkyl group, an alkenyl group, an aryl-alkyl group, or an aryl group. R 51 , R 52 , R 53 , R 54 , R 61 , R 62 , R 63 , R 64 , R 71 , R 72 , R 73 , R 74 , R 81 , R 82 , R 83 , and R 84 are preferably each independently a hydrogen atom, or an alkyl group; particularly preferably a hydrogen atom.

[0089] The divalent group represented by formula (4) is particularly preferably a divalent group represented by formula (4').

[0090] [Chemical Formula 10]

[0091]

[0092] [In the formula, * indicates a binding site].

[0093] In one embodiment, the (A) specific maleimide compound is preferably a maleimide-terminated polyimide containing, in one molecule, a divalent group represented by formula (1), and a divalent group represented by formula (2) and / or a divalent group represented by formula (3) (hereinafter also referred to as "specific maleimide-terminated polyimide"). The maleimide-terminated polyimide refers to a chain-like polyimide (chain-like polymer containing an imide structure in a repeating unit) having a maleimide group at both terminals. It is known that a maleimide-terminated polyimide can be obtained by, for example, subjecting components including a diamine compound, maleic anhydride, and a tetracarboxylic dianhydride to an imidization reaction.

[0094] In one embodiment, the specific maleimide compound (A) is preferably a maleimide compound represented by formula (Al).

[0095] [Chemical Formula 11]

[0096]

[0097] [In the formula, A 1 Each independently represents a divalent organic group formed from 2 or more (e.g., 2 to 3000, 2 to 1000, 2 to 100, 2 to 50) skeletal atoms selected from a carbon atom, an oxygen atom, a nitrogen atom, and a sulfur atom; A 2 Each independently represents a single bond, or a divalent organic group formed from 1 or more (e.g., 1 to 3000, 1 to 1000, 1 to 100, 1 to 50) skeletal atoms selected from a carbon atom, an oxygen atom, a nitrogen atom, and a sulfur atom; nl represents an integer of 1 or more; n2 represents an integer of 0 or more; either one of nl' and n2' represents 1 and the other represents 0; each of m independently represents 0 or 1; and other symbols are the same as in formula (1).

[0098] In formula (Al) and formula (A2) to (A5) described below, the order and arrangement of the nl units and the n2 units are not particularly limited, and include an alternating copolymer, a block copolymer, a random copolymer, and the like. In formula (Al) and formula (A2) to (A4) described below, each unit can be the same or different, for each of the nl units and the n2 units.

[0099] A 1 is preferably a divalent group represented by the following formula (Yl), each independently.

[0100] [Chemical Formula 12]

[0101]

[0102] [In the formula, Y 11 Each independently represents a single bond, an alkylene group, or an alkenylene group; Y 12 Each independently represents a single bond, an alkylene group, an alkenylene group, -0-, -CO-, -S-, -SO-, -S02-, -CONH-, -NHCO-, -COO-, or -OCO-; Z 1 Each independently represents an optionally substituted non-aromatic ring, or an optionally substituted aromatic ring; a represents 0 or an integer of 1 or more (preferably 0 or an integer of 1 to 5); and * represents a bonding site. It should be noted that each unit can be the same or different, for the a units.

[0103] In the present specification, as "substituent", there is no particular limitation, and monovalent substituents such as alkyl group, alkenyl group, aryl group, aryl-alkyl group, alkyl-oxy group, alkenyl-oxy group, aryl-oxy group, alkyl-carbonyl group, alkenyl-carbonyl group, aryl-carbonyl group, alkyl-oxy-carbonyl group, alkenyl-oxy-carbonyl group, aryl-oxy-carbonyl group, alkyl-carbonyl-oxy group, alkenyl-carbonyl-oxy group, aryl-carbonyl-oxy group, and the like, and divalent substituents such as oxo group (=0) and the like, if substitutable, can be included.

[0104] Alkylene group refers to a divalent aliphatic saturated hydrocarbon group which is straight chain or branched chain. Alkylene group is preferably alkylene group having 1 to 14 carbon atoms. As alkylene group, straight chain alkylene groups such as methylene group, ethylene group, trimethylene group, tetramethylene group, pentamethylene group, hexamethylene group, heptamethylene group, octamethylene group, octamethylene group, nonamethylene group, decamethylene group, and the like; branched chain alkylene groups such as ethylidene group (-CH(CH3)-), propylidene group (-CH(CH2CH3)-), propylidene group (-C(CH3)2-), ethylmethylmethylene group (-C(CH3)(CH2CH3)-), diethylmethylene group (-C(CH2CH3)2-), 2-methyltetramethylene group, 2,3-dimethyltetramethylene group, 1,3-dimethyltetramethylene group, 2-methylpentamethylene group, 2,2-dimethylpentamethylene group, 2,4-dimethylpentamethylene group, 1,3,5-methylpentamethylene group, 2-methylhexamethylene group, 2,2-dimethylhexamethylene group, 2,4-dimethylhexamethylene group, 1,3,5-trimethylhexamethylene group, 2,2,4-trimethylhexamethylene group, 2,4,4-trimethylhexamethylene group, and the like; and the like can be mentioned. Alkenylene group refers to a divalent aliphatic unsaturated hydrocarbon group which is straight chain or branched chain and has at least one carbon-carbon double bond. Alkenylene group is preferably alkenylene group having 2 to 14 carbon atoms. As alkenylene group, groups in which any of the carbon-carbon single bonds of the groups exemplified as alkylene group are replaced with carbon-carbon double bond can be mentioned.

[0105] Aromatic ring refers to a ring which complies with Hückel's rule in which the number of electrons contained in the π electron system of the ring is 4n+2 (n is a natural number), and includes not only monocyclic aromatic ring and condensed aromatic ring in which 2 or more monocyclic aromatic rings are condensed, but also condensed aromatic ring in which 1 or more monocyclic non-aromatic rings are condensed on 1 or more monocyclic aromatic rings. Aromatic ring can be carbocyclic or heterocyclic, and in one embodiment, is preferably carbocyclic. As aromatic ring, monocyclic aromatic ring (preferably 5 or 6-membered) such as benzene ring, pyridine ring, condensed aromatic ring (preferably 8 to 15-membered) such as indane ring, fluorene ring, naphthalene ring, and the like can be mentioned.

[0106] The non-aromatic ring refers to a ring other than an aromatic ring, and includes a monocyclic non-aromatic ring, and a fused non-aromatic ring in which two or more monocyclic non-aromatic rings are fused. The non-aromatic ring can be a carbocyclic ring or a heterocyclic ring, and in one embodiment, is preferably a carbocyclic ring. The non-aromatic ring can be a saturated ring or an unsaturated ring, and in one embodiment, is preferably a saturated ring. As the non-aromatic ring, there can be mentioned, for example, monocyclic alkanes such as a cyclopropane ring, a cyclobutane ring, a cyclopentane ring, a cyclohexane ring, a cycloheptane ring, a cyclooctane ring, and the like; monocyclic alkenes such as a cyclopentene ring, a cyclohexene ring, a cycloheptene ring, and the like; monocyclic non-aromatic heterocyclic rings such as a pyrrolidine ring, a tetrahydrofuran ring, a dioxane ring, a tetrahydropyran ring, and the like; and the like (preferably 3 to 10-membered). As the non-aromatic ring, there can be mentioned, for example, fused non-aromatic rings of two or more rings such as a norbornane ring, a decalin ring, an adamantane ring, a tetrahydrodicyclopentadiene ring, and the like (preferably 8 to 15-membered).

[0107] As specific examples of the divalent group represented by formula (Y1), there is no particular limitation, but there can be mentioned divalent organic groups represented by the following formulae.

[0108] [Chemical Formula 13]

[0109]

[0110] [in the formula, * indicates a bonding site].

[0111] A 2 Each independently is preferably a divalent group (including a single bond) represented by formula (Y2).

[0112] [Chemical Formula 14]

[0113]

[0114] [in the formula, Y 2 Each independently represents a single bond, an alkylene group, an alkenylene group, -O-, -CO-, -S-, -SO-, -SO2-, -CONH-, -NHCO-, -COO-, or -OCO-; Z 2 Each independently represents a non-aromatic ring optionally having a substituent, or an aromatic ring optionally having a substituent; b represents an integer of 0 or 1 or more (preferably 0 or an integer of 1 to 5); and * represents a bonding site. Note that the units for b can be the same or different.

[0115] As specific examples of the divalent group represented by formula (Y2), there is no particular limitation, and there can be mentioned -CH2-, -CH(CH3)-, -CH(CH2CH3)-, -C(CH3)2-, -C(CH3)(CH2CH3)-, -C(CH2CH3)2-, -O-, -CO-, -S-, -SO-, and -SO2-, and also divalent organic groups represented by the following formulae.

[0116] [Chemical Formula 15]

[0117]

[0118] [In the formula, * indicates a binding site].

[0119] n1 is preferably an integer of 1 to 100, more preferably an integer of 5 to 50, further preferably an integer of 10 to 35, and particularly preferably an integer of 15 to 25. n2 is preferably an integer of 1 to 100, more preferably an integer of 5 to 50, further preferably an integer of 10 to 35, and particularly preferably an integer of 15 to 25.

[0120] In the above embodiment, the specific maleimide compound (A) is more preferably a maleimide compound represented by formula (A2) (a binding bond between the n1 unit and the n2 unit).

[0121] [Chemical Formula 16]

[0122]

[0123] [In the formula, each symbol is the same as in formula (1), (4), and (Al)].

[0124] The specific maleimide compound (A) is further preferably a maleimide compound represented by formula (A3) (a binding bond between the n1 unit and the n2 unit).

[0125] [Chemical Formula 17]

[0126]

[0127] [In the formula, X 5 , X 6 , and X 7 each independently represents a single bond, -C(R 90 )2-, -0-, -CO-, -S-, -SO-, -S02-, -CONH-, -NHCO-, -COO-, or -OCO- (preferably, X 5 and X 7 are -0-, X 6 is -C(R 90 )2-); R 90 , R 91 , R 92 , R 93 , R 94 , R 01 , R 02 , R 03 , and R 04each independently represents a hydrogen atom, an alkyl group, an alkenyl group, an aryl-alkyl group, or an aryl group (preferably R 90 is an alkyl group, and the others are hydrogen atoms); other symbols are the same as in formulae (1), (4), and (Al),

[0128] (A) The specific maleimide compound is particularly preferably a maleimide compound represented by formula (A4) (a bond between the n1 unit and the n2 unit).

[0129] [Chemical Formula 18]

[0130]

[0131] [In the formula, each symbol is the same as in formula (4), (Al), and (A3)].

[0132] In one embodiment, the weight average molecular weight of the (A) specific maleimide compound is not particularly limited, but is preferably 3,000 or more, more preferably 4,000 or more, and further preferably 5,000 or more. The upper limit of the weight average molecular weight of the (A) specific maleimide compound is not particularly limited, but is preferably 500,000 or less, more preferably 200,000 or less, and further preferably 100,000 or less. The weight average molecular weight of the maleimide compound can be measured as a value converted to polystyrene by a gel permeation chromatography (GPC) method.

[0133] In one embodiment, the functional group equivalent weight of the maleimide group of the (A) specific maleimide compound is not particularly limited, but is preferably 1,000 g / eq. to 200,000 g / eq., more preferably 1,500 g / eq. to 100,000 g / eq., and further preferably 2,000 g / eq. to 50,000 g / eq. The functional group equivalent weight of the maleimide group is the mass of the compound per 1 equivalent of the maleimide group.

[0134] As a specific example of the (A) specific maleimide compound, a maleimide compound represented by the following formula (A5) (a bond between the n1 unit and the n2 unit) can be given.

[0135] [Chemical Formula 19]

[0136]

[0137] [In the formula, each symbol is the same as in formula (Al)].

[0138] As a commercially available product of the (A) specific maleimide compound, for example, "BMI-6100" manufactured by Designer Molecules, Inc., and the like can be given.

[0139] The content of the specific maleimide compound (A) in the resin composition is not particularly limited, and is preferably 50% by mass or less, more preferably 40% by mass or less, further preferably 30% by mass or less, further more preferably 20% by mass or less, and particularly preferably 15% 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 specific maleimide compound (A) in the resin composition is not particularly limited, and is preferably 0.1% by mass or more, more preferably 1% by mass or more, further preferably 3% by mass or more, further more preferably 5% by mass or more, and particularly preferably 7% by mass or more, based on 100% by mass of the nonvolatile components in the resin composition.

[0140] <(A') Other Radical Polymerizable Compound>

[0141] In the resin composition of the present application, as an arbitrary component, an (A') radical polymerizable compound other than the (A) component is sometimes further included. The (A') radical polymerizable compound can be used alone or in combination of two or more.

[0142] The (A') radical polymerizable compound can be, for example, a compound having a radical polymerizable unsaturated group. As the radical polymerizable unsaturated group, there is no particular limitation as long as it is radical polymerizable, and it is preferably an ethylenically unsaturated group having a carbon-carbon double bond at the terminal or in the interior, and specifically, it can be an unsaturated aliphatic group such as an allyl group, a 3-cyclohexenyl group, or the like; an aromatic group containing an unsaturated aliphatic group such as a p-vinylphenyl group, a m-vinylphenyl group, a styryl group, or the like; an α,β-unsaturated carbonyl group such as an acryloyl group, a methacryloyl group, a maleimido group, a fumarylidene group, or the like. The (A') radical polymerizable compound preferably has one or more radical polymerizable unsaturated groups, and more preferably has two or more radical polymerizable unsaturated groups.

[0143] As the (A') other radical polymerizable compound, a publicly known radical polymerizable compound can be widely used, and there is no particular limitation, and examples thereof include, for example, (A'-1) maleimide-based radical polymerizable compounds, (A'-2) vinylphenyl-based radical polymerizable compounds, (A'-3) (meth)acrylic acid-based radical polymerizable compounds, and the like other than the (A) component.

[0144] <(A'-1) Maleimide-Based Radical Polymerizable Compound>

[0145] (A'-1) Maleimide-based radical polymerizable compound is a compound other than the (A) component, and is an organic compound containing one or more (preferably two or more) maleimide groups in one molecule. The (A'-1) maleimide-based radical polymerizable compound can be used alone or two or more kinds thereof can be used in combination at an arbitrary ratio. The (A'-1) maleimide-based radical polymerizable compound is preferably, for example, a maleimide compound containing at least one selected from the group consisting of (A'-1-1) maleimide-terminated polyimide, (A'-1-2) aromatic maleimide compound, and (A'-1-3) aliphatic maleimide compound, other than the (A) component.

[0146] (A'-1-1) Maleimide-terminated polyimide

[0147] (A'-1-1) Maleimide-terminated polyimide is a maleimide compound other than the (A) component, and is a chain-like polyimide having a maleimide group at both terminals. The (A'-1-1) maleimide-terminated polyimide can be, for example, a component obtained by subjecting a component containing a diamine compound, maleic anhydride, and tetracarboxylic dianhydride to an imidization reaction.

[0148] In one embodiment, the (A'-1-1) maleimide-terminated polyimide is, for example, a maleimide compound represented by the following formula (B).

[0149] [Chemical Formula 20]

[0150]

[0151] [In the formula, n represents an integer of 1 or more (preferably an integer of 1 to 100, more preferably an integer of 1 to 50, and particularly preferably an integer of 1 to 20); the other symbols are the same as in formula (Al).] It should be noted that the units for n can be the same or different.

[0152] The weight average molecular weight (Mw) of the (A'-1-1) maleimide-terminated polyimide is preferably 500 to 500,000, and more preferably 1,000 to 200,000. The weight average molecular weight of the maleimide compound can be measured as a value converted to polystyrene by a gel permeation chromatography (GPC) method.

[0153] The functional group equivalent of the maleimide group of the (A'-1-1) maleimide-terminated polyimide is preferably 300 g / eq. to 200,000 g / eq., and more preferably 500 g / eq. to 100,000 g / eq.

[0154] As a commercially available product of the maleimide-terminated polyimide of (A'-1-1), for example, "BMI-1500", "BMI-1700", "BMI-3000J", etc. manufactured by Designer Molecules, Inc. can be mentioned.

[0155] <(A'-1-2) Aromatic Maleimide Compound>

[0156] The (A'-1-2) aromatic maleimide compound is a maleimide compound which does not belong to the components of (A) and (A'-1-1), and refers to a maleimide compound which contains 1 or more aromatic rings in 1 molecule and contains 2 or more maleimide groups. In one embodiment, the (A'-2) aromatic maleimide compound can be a polyaddition type aromatic maleimide compound. The (A'-2) aromatic maleimide compound can be a maleimide having 1 aromatic ring such as N,N'-1,3-phenylene dimaleimide, N,N'-1,4-phenylene dimaleimide, etc., or a polymaleimide having 2 or more aromatic rings, and preferably a maleimide having 2 or more aromatic rings.

[0157] In one embodiment, the (A'-1-2) aromatic maleimide compound is, for example, a maleimide compound represented by formula (C).

[0158] [Chemical Formula 21]

[0159]

[0160] [In the formula, R c each independently represents a substituent; X c each independently represents a single bond, an alkylene group, an alkenylene group, -O-, -CO-, -S-, -SO-, -SO2-, -CONH-, -NHCO-, -COO-, or -OCO- (preferably a single bond or an alkylene group); Z c each independently represents a non-aromatic ring optionally having a substituent, or an aromatic ring optionally having a substituent (preferably an aromatic ring optionally having a substituent, and particularly preferably a benzene ring optionally having a substituent); s represents an integer of 1 or more (preferably an integer of 1 to 100, more preferably an integer of 1 to 50, and further preferably an integer of 1 to 20); each of t independently represents 0 or an integer of 1 or more; and each of u independently represents an integer of 0 to 2 (preferably 0),

[0161] The (A'-1-2) aromatic maleimide compound is particularly preferably a maleimide compound represented by formula (C1-1) to (C1-4).

[0162] [Chemical Formula 22]

[0163]

[0164] [In the formula, R c1 , R c2 , and R c3 each independently represent an alkyl group; X c1 , and X c2 each independently represent a single bond or an alkylene group; s represents an integer of 1 or more (preferably an integer of 1 to 100, more preferably an integer of 1 to 50, further preferably an integer of 1 to 20); t' represents an integer of 1 to 5; u1, u2, and u3 each independently represent an integer of 0 to 2 (preferably 0). Note that each of the s unit, the t unit, the t' unit, the u unit, the u1 unit, the u2 unit, and the u3 unit can be the same or different.

[0165] The weight average molecular weight (Mw) of the aromatic maleimide compound (A'-1-2) is preferably 150 to 5000, more preferably 300 to 2500.

[0166] The functional group equivalent of the maleimide group of the aromatic maleimide compound (A'-1-2) is preferably 50 g / eq. to 2000 g / eq., more preferably 100 g / eq. to 1000 g / eq., further preferably 150 g / eq. to 500 g / eq., particularly preferably 200 g / eq. to 300 g / eq.

[0167] As commercially available products of the aromatic maleimide compound (A'-1-2), for example, "MIR-3000-70MT" manufactured by Japan Eubchem Co., Ltd., "BMI-50P" manufactured by KI-Chemical Co., Ltd., "BMI-1000", "BMI-1000H", "BMI-1100", "BMI-1100H", "BMI-4000", "BMI-5100" manufactured by Dainippon Ink and Chemicals, Inc., "BMI-4,4'-BPE", "BMI-70" manufactured by KI-Chemical Co., Ltd., "BMI-80" manufactured by KI-Chemical Co., Ltd., and the like can be given.

[0168] <(A'-1-3) Aliphatic Maleimide Compound>

[0169] The aliphatic maleimide compound (A'-1-3) refers to a compound having 2 or more (preferably 2) maleimide groups in one molecule with a non-aromatic hydrocarbon (preferably a hydrocarbon having 2 to 50 carbon atoms) as a basic skeleton.

[0170] In one embodiment, the aliphatic maleimide compound (A'-1-3) is, for example, a maleimide compound represented by the following formula (D).

[0171] [Chemical Formula 23]

[0172]

[0173] (In the formula, X d each independently represents a single bond, an alkylene group or an alkenylene group (preferably an alkylene group or an alkenylene group); Z d each independently represents a non-aromatic ring optionally having a group selected from the group consisting of an alkyl group and an alkenyl group (preferably a monocyclic alkane ring or a monocyclic alkene ring optionally having a group selected from the group consisting of an alkyl group and an alkenyl group); x represents 0 or an integer of 1 or more (preferably an integer of 1 or more, particularly preferably 1). Note that the x units can be the same or different.

[0174] As specific examples of the (A'-1-3) aliphatic maleimide compound, there can be mentioned chain aliphatic bismaleimide compounds such as N,N'-ethylenedimaleimide, N,N'-tetramethylenedimaleimide, N,N'-hexamethylenedimaleimide, and the like; alicyclic bismaleimide compounds such as 1-maleimido-3-maleimido methyl-3,5,5-trimethylcyclohexane (IPBM), 1,1'-(cyclohexane-1,3-diylbis(methylene))bis(1H-pyrrole-2,5-dione) (CBM), 1,1'-(4,4'-methylenebis(cyclohexane-4,1-diyl))bis(1H-pyrrole-2,5-dione) (MBCM), and the like; and bismaleimides containing a dimer acid skeleton, and the like.

[0175] The bismaleimide containing a dimer acid skeleton refers to a bismaleimide compound in which both of the terminal carboxyl groups (-COOH) of a dimer acid are replaced with a maleimide group or a maleimido methyl group (2,5-dihydro-2,5-dioxo-1H-pyrrol-1-ylmethyl). The dimer acid is a known compound which can be obtained by dimerizing an unsaturated fatty acid (preferably an unsaturated fatty acid having 11 to 22 carbon atoms, particularly preferably an unsaturated fatty acid having 18 carbon atoms), and the industrial production process thereof has almost been standardized in the industry. As the dimer acid, in particular, a substance containing a dimer acid having 36 carbon atoms as a main component, which is obtained by dimerizing an unsaturated fatty acid having 18 carbon atoms such as oleic acid, linoleic acid, and the like, is readily available. Furthermore, depending on the production method, the degree of purification, and the like, the dimer acid sometimes contains an arbitrary amount of monomeric acid, trimeric acid, other polymeric fatty acid, and the like. Furthermore, a double bond remains after the polymerization reaction of the unsaturated fatty acid, but in the present specification, a hydrogenated product in which the degree of unsaturation is reduced by further performing a hydrogenation reaction is also included in the dimer acid.

[0176] The molecular weight of the (A'-1-3) aliphatic maleimide compound is preferably 150 to 5000, more preferably 300 to 1000.

[0177] The functional group equivalent of the maleimide group of the (A'-l-3) aliphatic maleimide compound is preferably 50 g / eq. to 2000 g / eq., more preferably 100 g / eq. to 1000 g / eq., further preferably 200 g / eq. to 600 g / eq., and particularly preferably 300 g / eq. to 400 g / eq.

[0178] As a commercially available product of the (A'-l-3) aliphatic maleimide compound, "BMI-689" manufactured by Designer Molecules, Inc., and the like can be given.

[0179] (A'-2) Vinylphenyl-based radical polymerizable compound

[0180] The (A'-2) vinylphenyl-based radical polymerizable compound is a radical polymerizable compound having a vinylphenyl group. The vinylphenyl-based radical polymerizable compound preferably has two or more vinylphenyl groups per one molecule.

[0181] In one embodiment, the (A'-2) vinylphenyl-based radical polymerizable compound is preferably a vinylbenzyl-modified polyphenylene ether having a vinylbenzyl group and a polyphenylene ether skeleton, and particularly preferably a vinylbenzyl-modified polyphenylene ether having a repeating unit represented by formula (E-l) (the number of repeating units is preferably 2 to 300, and more preferably 2 to 100) and a vinylbenzyl group (particularly a vinylbenzyl-modified polyphenylene ether in which the hydrogen atoms of both terminal hydroxyl groups of the polyphenylene ether are substituted with vinylbenzyl groups).

[0182] [Chemical Formula 24]

[0183]

[0184] [In the formula, R e1 , R e2 , R e3 , and R e4 each independently represent a hydrogen atom or a substituent (preferably a hydrogen atom or an alkyl group, and particularly preferably a hydrogen atom or a methyl group)].

[0185] In other embodiments, the (A'-2) vinylphenyl-based radical polymerizable compound is preferably a divinylbenzene polymer having a repeating unit represented by formula (E-2) (the number of repeating units is preferably 2 to 200).

[0186] [Chemical Formula 25]

[0187]

[0188] [In the formula, R e5 , R e6 , and Re7 each independently represents a hydrogen atom or a substituent (preferably a hydrogen atom). The divinylbenzene polymer can also be a copolymer further having styrene units, ethylstyrene units, and the like. In the case of having other styrene skeleton units, the proportion of the repeating unit of formula (E-2) is preferably 5 to 70 mol% with respect to the total styrene skeleton units.

[0189] The number average molecular weight of the (A'-2) vinylphenyl-based radical polymerizable compound is preferably 500 to 100,000, more preferably 700 to 80,000. The functional group equivalent of the vinyl group of the (A'-2) vinylphenyl-based radical polymerizable compound is preferably 200 g / eq. to 3,000 g / eq., more preferably 200 g / eq. to 2,000 g / eq.

[0190] As commercially available products of the (A'-2) vinylphenyl-based radical polymerizable compound, for example, "OPE-2St 1200", "OPE-2St 2200" (vinylbenzyl-modified polyphenylene ether) manufactured by Mitsubishi Gas Chemical Company, Inc.; "ODV-XET-X03", "ODV-XET-X04", "ODV-XET-X05" (divinylbenzene polymer) manufactured by Nippon Steel Chemical Co., Ltd., and the like can be given.

[0191] <(A'-3) (METH) ACRYLATE-BASED RADICAL POLYMERIZABLE COMPOUND>

[0192] The (A'-3) (meth)acrylate-based radical polymerizable compound is a radical polymerizable compound having an acryloyl group and / or a methacryloyl group. The (A'-3) (meth)acrylate-based radical polymerizable compound is preferably one having two or more acryloyl groups and / or methacryloyl groups per molecule. The (A'-3) (meth)acrylate-based radical polymerizable compound is preferably a (meth)acrylate-modified polyphenylene ether having "an acryloyl group and / or a methacryloyl group" and "a polyphenylene ether skeleton", and particularly preferably a (meth)acrylate-modified polyphenylene ether having a repeating unit represented by formula (F) (the number of repeating units is preferably 2 to 300, more preferably 2 to 100) and an acryloyl group and / or a methacryloyl group (particularly a terminal (meth)acrylate-modified polyphenylene ether in which the hydrogen atoms of both terminal hydroxyl groups of a polyphenylene ether are substituted with acryloyl groups and / or methacryloyl groups).

[0193] [Chemical Formula 26]

[0194]

[0195] [In the formula, R f1 , R f2 , R f3 , and R f4each independently represents a hydrogen atom or a substituent (preferably a hydrogen atom or an alkyl group, particularly preferably a hydrogen atom or a methyl group).

[0196] The number average molecular weight of the (A'-3) (meth)acryl-based radical polymerizable compound is preferably from 500 to 10,000, more preferably from 700 to 5,000. The functional group equivalent of the acryloyl group and the methacryloyl group of the (A'-3) (meth)acryl-based radical polymerizable compound is preferably from 200 g / eq. to 3,000 g / eq., more preferably from 300 g / eq. to 2,000 g / eq.

[0197] As the (A'-3) (meth)acryl-based radical polymerizable compound, for example, "SA9000", "SA9000-111" (methacrylic acid-modified polyphenylene ether) manufactured by SABIC Innovative Plastics Co., Ltd. and the like can be mentioned.

[0198] The content of the (A') other radical polymerizable compound in the resin composition is not particularly limited, and is preferably 50% by mass or less, more preferably 40% by mass or less, further preferably 30% by mass or less, further more preferably 20% by mass or less, particularly preferably 10% by mass or less, based on 100% by mass of the nonvolatile content in the resin composition. The lower limit of the content of the (A') other radical polymerizable compound in the resin composition is not particularly limited, and can be, for example, 0% by mass or more, 0.1% by mass or more, 1% by mass or more, 2% by mass or more, or the like, based on 100% by mass of the nonvolatile content in the resin composition.

[0199] The content of the (A) specific maleimide compound in the resin composition is preferably 10% by mass or more, more preferably 30% by mass or more, further preferably 40% by mass or more, particularly preferably 50% by mass or more, based on 100% by mass of the total of the radical polymerizable compounds ((A) component and (A') component) in the resin composition.

[0200] (B) Epoxy Resin

[0201] The resin composition of the present application contains a (B) epoxy resin. The (B) epoxy resin refers to a curable resin having an epoxy group. The (B) epoxy resin is preferably a (B-1) epoxy resin containing a condensed ring structure.

[0202] (B-1) Epoxy Resin Containing a Condensed Ring Structure

[0203] (B-1) The epoxy resin having a condensed ring structure is a resin having one or more condensed rings and one or more (preferably two or more) epoxy groups in one molecule. The epoxy resin having a condensed ring structure (B-1) can be used alone or in combination of two or more at an arbitrary ratio.

[0204] The condensed ring contained in the epoxy resin having a condensed ring structure (B-1) is preferably a condensed aromatic carbon ring. The condensed aromatic carbon ring is a two or more ring aromatic carbon ring obtained by condensing two or more benzene rings, and the number of carbon atoms is preferably 10 to 18, more preferably 10 to 14. Examples include naphthalene ring, anthracene ring, phenanthrene ring, and the like, and naphthalene ring is particularly preferred.

[0205] The epoxy resin having a condensed ring structure (B-1) can be any of glycidyl ether type, glycidyl amine type, glycidyl ester type, olefin oxidation (alicyclic) type, and the like, and the glycidyl ether type is preferred.

[0206] The epoxy resin having a condensed ring structure (B-1) can be a monomer type or a repeating structure type. Here, the repeating structure type refers to a high molecular structure having three or more repeating units containing one or two or more condensed rings, and the monomer type refers to a molecular structure having no repeating unit or two repeating units containing one or two or more condensed rings. The epoxy resin having a condensed ring structure (B-1) is an epoxy resin selected from the group consisting of (B-1-1) a monomer type epoxy resin having a condensed ring structure and (B-1-2) a repeating structure type epoxy resin having a condensed ring structure, and the repeating structure type epoxy resin having a condensed ring structure (B-1-2) is preferred.

[0207] Examples of the monomer type epoxy resin having a condensed ring structure (B-1-1) include monomer type epoxy resins having one condensed ring in one molecule such as 1,6-bis(glycidyloxy)naphthalene, 1,5-bis(glycidyloxy)naphthalene, 2,7-bis(glycidyloxy)naphthalene, 2,6-bis(glycidyloxy)naphthalene, and the like; and monomer type epoxy resins having two condensed rings in one molecule such as bis[2-(glycidyloxy)-1-naphthyl]methane, 2,2-bis[2-(glycidyloxy)-1-naphthyl]propane, bis[2,7-bis(glycidyloxy)-1-naphthyl]methane, 2,2-bis[2,7-bis(glycidyloxy)-1-naphthyl]propane, [2,7-bis(glycidyloxy)-1-naphthyl][2-(glycidyloxy)-1-naphthyl]methane, 2-[2,7-bis(glycidyloxy)-1-naphthyl]-2-[2-(glycidyloxy)-1-naphthyl]propane, and the like.

[0208] In one embodiment, the epoxy resin having a condensed ring structure of (B-1-1) is preferably a 2-functional to 4-functional epoxy resin, more preferably a 2-functional or 3-functional epoxy resin, and particularly preferably a 2-functional epoxy resin.

[0209] The epoxy equivalent weight of the epoxy resin having a condensed ring structure of (B-1-1) is not particularly limited, and is preferably 50 g / eq. or more, more preferably 80 g / eq. or more, further preferably 100 g / eq. or more, further more preferably 120 g / eq. or more, and particularly preferably 130 g / eq. or more. The upper limit of the epoxy equivalent weight of the epoxy resin having a condensed ring structure of (B-1-1) is not particularly limited, and is preferably 1000 g / eq. or less, more preferably 500 g / eq. or less, further preferably 300 g / eq. or less, further more preferably 200 g / eq. or less, and particularly preferably 160 g / eq. or less. The epoxy equivalent weight is the mass of the resin per 1 equivalent of epoxy group. The epoxy equivalent weight can be measured according to JIS K7236.

[0210] The molecular weight of the epoxy resin having a condensed ring structure of (B-1-1) is not particularly limited, but is preferably 2000 or less, more preferably 1000 or less, further preferably 700 or less, further more preferably 600 or less, and particularly preferably 500 or less.

[0211] As the commercially available product of the epoxy resin having a condensed ring structure of (B-1-1), for example, "HP-4032D", "HP-4032SS" (epoxy resin having one naphthalene ring in one molecule) manufactured by DIC Corporation; "EXA-4750", "HP-4770", "HP-4700", "HP-4710" (epoxy resin having two naphthalene rings in one molecule) manufactured by DIC Corporation; and the like can be mentioned.

[0212] As the epoxy resin having a condensed ring structure of (B-1-2) having a repeating structure, for example, a naphthol novolac type epoxy resin, a naphthol-phenol co-condensation novolac type epoxy resin, a naphthol-cresol co-condensation novolac type epoxy resin, a naphthol aralkyl type epoxy resin, a naphthalenediol aralkyl type epoxy resin, a naphthalene ether type epoxy resin, and the like having a repeating structure of three or more condensed rings in one molecule can be mentioned. In one embodiment, the epoxy resin having a condensed ring structure of (B-1-2) having a repeating structure is preferably a naphthol aralkyl type epoxy resin.

[0213] The epoxy equivalent weight of the epoxy resin having a condensed ring structure of a repeating structure type is not particularly limited, but is preferably 50 g / eq. or more, more preferably 100 g / eq. or more, further preferably 200 g / eq. or more, further more preferably 250 g / eq. or more, particularly preferably 300 g / eq. or more. The upper limit of the epoxy equivalent weight of the epoxy resin having a condensed ring structure of a repeating structure type is not particularly limited, but is preferably 2000 g / eq. or less, more preferably 1000 g / eq. or less, further preferably 500 g / eq. or less, further more preferably 400 g / eq. or less.

[0214] As commercially available products of the epoxy resin having a condensed ring structure of a repeating structure type (B-1-2), for example, "ESN-155", "ESN-185V", "ESN-175", "ESN-475V", "ESN-485", "TX-1507B" (naphthol aralkyl type epoxy resin) manufactured by Nippon Steel Chemical Co., Ltd.; "EXA-7311", "EXA-7311-G3", "EXA-7311-G4", "EXA-7311-G4S", "HP-6000", "HP-6000-L" (naphthalene ether type epoxy resin) manufactured by DIC Corporation; "NC7000L" (naphthol novolak type epoxy resin) manufactured by Japan Epoxy Resin Co., Ltd.; and the like can be given.

[0215] In one embodiment, the epoxy resin having a condensed ring structure (B-1) is preferably a naphthol aralkyl type epoxy resin.

[0216] The resin composition can contain, in addition to the epoxy resin having a condensed ring structure (B-1), another epoxy resin (B-2), and the content of the epoxy resin having a condensed ring structure (B-1) in the resin composition is preferably 50% by mass or more, 60% by mass or more, more preferably 70% by mass or more, 80% by mass or more, further preferably 90% by mass or more, 95% by mass or more, further more preferably 98% by mass or more, 99% by mass or more, particularly preferably 100% by mass, based on the total epoxy resin in the resin composition, from the viewpoint of significantly obtaining the desired effects of the present application.

[0217] <(B-2) Another Epoxy Resin>

[0218] As the other epoxy resins (B-2), for example, the following can be given: 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, triphenol type epoxy resins, phenol novolac type epoxy resins, t-butylcatechol type epoxy resins, glycidyl amine type epoxy resins, glycidyl ester type epoxy resins, 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 type epoxy resins, epoxy resins containing a spiro ring, cyclohexane type epoxy resins, cyclohexane dimethanol type epoxy resins, trimethylol type epoxy resins, tetraphenyl ethane type epoxy resins, isocyanurate type epoxy resins, phenolphthalimidine type epoxy resins, phenolphthalein type epoxy resins, and the like. The other epoxy resins (B-2) can be used singly or in combination of two or more.

[0219] It is preferable that the resin composition contain an epoxy resin having 2 or more epoxy groups in one molecule as the other epoxy resin (B-2). The proportion of the epoxy resin having 2 or more epoxy groups in one molecule is preferably 50% by mass or more, more preferably 60% by mass or more, and particularly preferably 70% by mass or more, relative to 100% by mass of the nonvolatile components of the other epoxy resin (B-2).

[0220] There are epoxy resins which are liquid at 20°C (hereinafter sometimes referred to as "liquid epoxy resins") and epoxy resins which are solid at 20°C (hereinafter sometimes referred to as "solid epoxy resins"). In the resin composition of the present application, the other epoxy resin (B-2) can contain only liquid epoxy resins, or only solid epoxy resins, or both liquid and solid epoxy resins.

[0221] As the liquid epoxy resins, it is preferable that an epoxy resin having 2 or more epoxy groups in one molecule.

[0222] As the liquid epoxy resins, it is preferable that bisphenol A type epoxy resins, bisphenol F type epoxy resins, bisphenol AF 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.

[0223] As specific examples of the liquid epoxy resin, there are "828US", "828EL", "jER828EL", "825", "EPIKOTE 828EL" (bisphenol A type epoxy resin) manufactured by Mitsubishi Chemical Corporation; "jER807", "1750" (bisphenol F type epoxy resin) manufactured by Mitsubishi Chemical Corporation; "jER152" (phenol novolak type epoxy resin) manufactured by Mitsubishi Chemical Corporation; "630", "630LSD", "604" (glycidyl amine type epoxy resin) manufactured by Mitsubishi Chemical Corporation; "ED-523T" (glycirol type epoxy resin) manufactured by ADEKA Corporation; "EP-3950L", "EP-3980S" (glycidyl amine type epoxy resin) manufactured by ADEKA Corporation; "EP-4088S" (dicyclopentadiene type epoxy resin) manufactured by ADEKA Corporation; "ZX1059" (mixture of bisphenol A type epoxy resin and bisphenol F type epoxy resin) manufactured by Nippon Steel Chemical Co., Ltd.; "EX-721" (glycidyl ester type epoxy resin) manufactured by Nagase Chemtex Corporation; "CELLOXIDE 2021P" (alicyclic epoxy resin having an ester skeleton) manufactured by Daicel Corporation; "PB-3600" manufactured by Daicel Corporation, "JP-100", "JP-200" (epoxy resin having a butadiene structure) manufactured by Nippon Carbide Industries, Ltd.; "ZX1658", "ZX1658GS" (liquid 1,4-glycidyl cyclohexane type epoxy resin) manufactured by Nippon Steel Chemical Co., Ltd., and the like. These liquid epoxy resins can be used singly or in combination of two or more.

[0224] As the solid epoxy resin, it is preferable that the solid epoxy resin having three or more epoxy groups in one molecule, and more preferable that the solid epoxy resin of aromatic series having three or more epoxy groups in one molecule.

[0225] As the solid epoxy resin, it is preferable that the solid epoxy resin of resorcinol type, cresol novolak type, dicyclopentadiene type, triphenol type, biphenyl type, bisphenol A type, bisphenol AF type, phenol aralkyl type, tetraphenyl ethane type, phenol benzopyrrolone type, and phenolphthalein type.

[0226] As specific examples of the solid epoxy resin, there are "N-690" (a cresol novolak type epoxy resin) manufactured by DIC Corporation; "N-695" (a cresol novolak type epoxy resin) manufactured by DIC Corporation; "HP-7200", "HP-7200HH", "HP-7200H", "HP-7200L" (a dicyclopentadiene type epoxy resin) manufactured by DIC Corporation; "EPPN-502H" (a triphenol type epoxy resin) manufactured by Japan Epoxy Resin Co., Ltd.; "NC3000H", "NC3000", "NC3000L", "NC3000FH", "NC3100" (a biphenyl type epoxy resin) manufactured by Japan Epoxy Resin Co., Ltd.; "YX4000H", "YX4000", "YX4000HK", "YL7890" (a dinocresol type epoxy resin) manufactured by Mitsubishi Chemical Corporation; "YL6121" (a biphenyl type epoxy resin) manufactured by Mitsubishi Chemical Corporation; "YX7700" (a phenol aralkyl type epoxy resin) manufactured by Mitsubishi Chemical Corporation; "PG-100", "CG-500" manufactured by Osaka Gas Chemicals Co., Ltd.; "YL7760" (a bisphenol AF type epoxy resin) manufactured by Mitsubishi Chemical Corporation; "YL7800" (a fluorene type epoxy resin) manufactured by Mitsubishi Chemical Corporation; "jER1010" (a bisphenol A type epoxy resin) manufactured by Mitsubishi Chemical Corporation; "jER1031S" (a tetraphenyl ethane type epoxy resin) manufactured by Mitsubishi Chemical Corporation; "WHR991S" (a phenol benzopyrrolone type epoxy resin) manufactured by Japan Epoxy Resin Co., Ltd.; and the like. These solid epoxy resins can be used singly or in combination of two or more.

[0227] The epoxy equivalent weight of the epoxy resin (B) is preferably 50 g / eq. to 5000 g / eq., more preferably 60 g / eq. to 2000 g / eq., further preferably 70 g / eq. to 1000 g / eq., and further more preferably 80 g / eq. to 500 g / eq.

[0228] The weight average molecular weight (Mw) of the epoxy resin (B) is preferably 100 to 5000, more preferably 250 to 3000, and further preferably 400 to 1500. The weight average molecular weight of the resin can be measured as a value converted to polystyrene by a gel permeation chromatography (GPC) method.

[0229] The content of the (B) epoxy 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 is preferably 60% by mass or less, more preferably 50% by mass or less, further preferably 40% by mass or less, further more preferably 30% by mass or less, and particularly preferably 20% by mass or less. The lower limit of the content of the (B) epoxy 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 is preferably 0.01% by mass or more, more preferably 0.1% by mass or more, further preferably 1% by mass or more, further more preferably 1% by mass or more, and particularly preferably 10% by mass or more.

[0230] The mass ratio of the (A) specific maleimide compound to the (B) epoxy resin ((A) component / (B) component) in the resin composition is preferably 0.1 or more, more preferably 0.3 or more, and particularly preferably 0.5 or more. The upper limit of the mass ratio of the (A) specific maleimide compound to the (B) epoxy resin ((A) component / (B) component) in the resin composition is preferably 10 or less, more preferably 3 or less, and particularly preferably 1 or less.

[0231] (C) Inorganic Filler

[0232] The resin composition of the present application contains a (C) inorganic filler. The (C) inorganic filler is contained in the resin composition in the form of particles.

[0233] As the material of the (C) inorganic filler, an inorganic compound is used. As the material of the (C) inorganic filler, for example, the following can be given: 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 zirconate titanate, barium zirconate, calcium zirconate, zirconium phosphate, and zirconium tungstophosphate, and the like. Among them, silica is particularly preferred. As the silica, for example, the following can be given: amorphous silica, fused silica, crystalline silica, synthetic silica, hollow silica, and the like. Further, as the silica, spherical silica is preferred. The (C) inorganic filler can be used singly or in combination of two or more kinds in an arbitrary ratio.

[0234] As a commercially available product of the (C) inorganic filler, for example, "UFP-30" manufactured by Kureha Chemical Industry Co., Ltd.; "SP60-05", "SP507-05" manufactured by Nippon Steel & Sumikin Materials Co., Ltd.; "YC100C", "YA050C", "YA050C-MJE", "YA010C" manufactured by Admatechs Co., Ltd.; "UFP-30" manufactured by Denka Co., Ltd.; "Silfil (シルフィル) NSS-3N", "Silfil NSS-4N", "Silfil NSS-5N" manufactured by Tokuyama Co., Ltd.; "SC2500SQ", "SO-C4", "SO-C2", "SO-C1" manufactured by Admatechs Co., Ltd.; "DAW-03", "FB-105FD" manufactured by Denka Co., Ltd., and the like can be given.

[0235] The average particle diameter of the (C) inorganic filler is not particularly limited, but it is preferably 10 μm or less, more preferably 5 μm or less, further preferably 2 μm or less, further more preferably 1 μm or less, and particularly preferably 0.7 μm or less. The lower limit of the average particle diameter of the (C) inorganic filler is not particularly limited, but it is preferably 0.01 μm or more, more preferably 0.05 μm or more, further preferably 0.1 μm or more, and particularly preferably 0.2 μm or more. The average particle diameter of the (C) inorganic filler can be measured by a laser diffraction-scattering method based on Mie scattering theory. Specifically, the particle diameter distribution of the inorganic filler is made on a volume basis by a laser diffraction scattering type particle diameter distribution measuring device, and the median particle diameter is measured as the average particle diameter. The measurement sample can be obtained by weighing 100 mg of the inorganic filler and 10 g of methyl ethyl ketone into a tube, and dispersing by ultrasonic waves for 10 minutes. For the measurement sample, a laser diffraction type particle diameter distribution measuring device is used, blue and red light source wavelengths are used, the particle diameter distribution of the inorganic filler is measured in a flow cell, and the average particle diameter is calculated from the obtained particle diameter distribution as the median particle diameter. As the laser diffraction type particle diameter distribution measuring device, for example, "LA-960" manufactured by Horiba Ltd., and the like can be given.

[0236] The specific surface area of the (C) inorganic filler is not particularly limited, but it is preferably 0.1 m 2 / g or more, more preferably 0.5 m 2 / g or more, further preferably 1 m 2 / g or more, particularly preferably 3 m 2 / g or more. The upper limit of the specific surface area of the (C) inorganic filler is not particularly limited, but it is preferably 100 m 2 / g or less, more preferably 70 m 2 / g or less, further preferably 50 m 2 / g or less, particularly preferably 30 m 2 / g or less. The specific surface area of the inorganic filler can be obtained by the BET method using a specific surface area measuring device (Macsorb HM-1210 manufactured by Mountech) to adsorb nitrogen gas to the surface of the sample, and calculating the specific surface area by the BET multipoint method.

[0237] (C) The inorganic filler material is preferably surface treated with a suitable surface treatment agent. By surface treating, the moisture resistance and dispersibility of the inorganic filler material (C) can be improved. As the surface treatment agent, there can be mentioned, for example, vinyl silane coupling agents such as vinyltrimethoxysilane, vinyltriethoxysilane, and the like; epoxy silane coupling agents such as 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropylmethyldiethoxysilane, 3-glycidoxypropyltriethoxysilane, and the like; styryl silane coupling agents such as p-styryltrimethoxysilane, and the like; methacrylic silane coupling agents such as 3-methacryloyloxypropylmethyldimethoxysilane, 3-methacryloyloxypropyltrimethoxysilane, 3-methacryloyloxypropylmethyldiethoxysilane, 3-methacryloyloxypropyltriethoxysilane, and the like; acrylic silane coupling agents such as 3-acryloyloxypropyltrimethoxysilane, and the like; amino silane coupling agents such as N-2-(aminoethyl)-3-aminopropylmethyldimethoxysilane, N-2-(aminoethyl)-3-aminopropyltrimethoxysilane, 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, 3-triethoxysilyl-N-(l,3-dimethyl-butylidene)propylamine, N-phenyl-3-aminopropyltrimethoxysilane, N-phenyl-8-aminooctyltrimethoxysilane, N-(vinylbenzyl)-2-aminoethyl-3-aminopropyltrimethoxysilane, and the like; isocyanurate silane coupling agents such as tris(trimethoxysilylpropyl)isocyanurate, and the like; ureido silane coupling agents such as 3-ureidopropyltrialkoxysilane, and the like; mercapto silane coupling agents such as 3-mercaptopropylmethyldimethoxysilane, 3-mercaptopropyltrimethoxysilane, and the like; isocyanate silane coupling agents such as 3-isocyanatopropyltriethoxysilane, and the like; anhydride silane coupling agents such as 3-trimethoxysilylpropyl succinic anhydride, and the like; and the like. In addition, the surface treatment agent can be used singly or in combination of two or more kinds in any proportion.

[0238] As commercially available products of the surface treatment agent, there are, for example, "KBM-1003", "KBE-1003" (vinyl-based silane coupling agent) ; "KBM-303", "KBM-402", "KBM-403", "KBE-402", "KBE-403" (epoxy-based silane coupling agent) ; "KBM-1403" (styryl-based silane coupling agent) ; "KBM-502", "KBM-503", "KBE-502", "KBE-503" (methacrylic acid-based silane coupling agent) ; "KBM-5103" (acrylic acid-based silane coupling agent) ; "KBM-602", "KBM-603", "KBM-903", "KBE-903", "KBE-9103P", "KBM-573", "KBM-575" (amino-based silane coupling agent) ; "KBM-9659" (isocyanurate-based silane coupling agent) ; "KBE-585" (ureido-based silane coupling agent) ; "KBM-802", "KBM-803" (mercapto-based silane coupling agent) ; "KBE-9007N" (isocyanate-based silane coupling agent) ; "X-12-967C" (anhydride-based silane coupling agent) ; "KBM-13", "KBM-22", "KBM-103", "KBE-13", "KBE-22", "KBE-103", "KBM-3033", "KBE-3033", "KBM-3063", "KBE-3063", "KBE-3083", "KBM-3103C", "KBM-3066", "KBM-7103" (non-silane coupling-alkoxysilane compound), and the like.

[0239] From the viewpoint of improving the dispersibility of the inorganic filler material, the degree of surface treatment by the surface treatment agent is preferably within a prescribed range. Specifically, it is preferable that the surface treatment be performed by 0.2 to 5% by mass of the surface treatment agent with respect to 100% by mass of the inorganic filler material, more preferable that the surface treatment be performed by 0.2 to 3% by mass of the surface treatment agent, and further preferable that the surface treatment be performed by 0.3 to 2% by mass of the surface treatment agent.

[0240] The degree of surface treatment by the surface treatment agent can be evaluated by the amount of carbon per unit surface area of the inorganic filler material. From the viewpoint of improving the dispersibility of the inorganic filler material, the amount of carbon per unit surface area of the inorganic filler material is preferably 0.02 mg / m 2 More preferably, it is 0.1 mg / m 2 Further preferably, it is 0.2 mg / m 2 More preferably, it is 0.1 mg / m On the other hand, from the viewpoint of preventing an increase in the melt viscosity of the resin composition, the melt viscosity in the sheet form, it is preferable that the amount of carbon be 1.0 mg / m2 Further preferably 0.8 mg / m 2 Further preferably 0.5 mg / m 2 Further preferably 0.5 mg / m

[0241] (C) The amount of carbon per unit surface area of the inorganic filler can be measured after the inorganic filler subjected to surface treatment is subjected to a cleaning treatment with a solvent (e.g., methyl ethyl ketone (MEK)). Specifically, a sufficient amount of MEK as a solvent is added to the inorganic filler subjected to surface treatment with a surface treatment agent, and the mixture is subjected to ultrasonic cleaning 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. As the carbon analyzer, "EMIA-320V" manufactured by HORIBA, Ltd., or the like can be used.

[0242] When the nonvolatile content in the resin composition is taken as 100% by mass, the content of (C) the inorganic filler in the resin composition is preferably more than 30% by mass, more preferably more than 40% by mass, further more preferably more than 45% by mass, further more preferably more than 50% by mass, and particularly preferably more than 55% by mass, from the viewpoint of further suppressing the coefficient of thermal expansion. The upper limit of the content of (C) the inorganic filler in the resin composition is not particularly limited, but can be preferably 90% by mass or less, more preferably 80% by mass or less, further more preferably 75% by mass or less, and particularly preferably 70% by mass or less, when the nonvolatile content in the resin composition is taken as 100% by mass.

[0243] The mass ratio of (A) the specific maleimide compound to (C) the inorganic filler ((A) component / (C) component) in the resin composition is preferably 0.01 or more, more preferably 0.05 or more, and particularly preferably 0.1 or more. The upper limit of the mass ratio of (A) the specific maleimide compound to (C) the inorganic filler ((A) component / (C) component) in the resin composition is preferably 1 or less, more preferably 0.5 or less, and particularly preferably 0.3 or less.

[0244] (D) Active Ester Compound

[0245] In the resin composition of the present application, as an arbitrary component, (D) an active ester compound can be contained. (D) The active ester compound can be used alone or two or more kinds thereof can be used in combination at an arbitrary ratio. In one embodiment, (D) the active ester compound can have a function of reacting with (B) the epoxy resin to cure the resin composition.

[0246] As the (D) active ester compound, it is generally preferable to use a compound having two or more ester groups with high reactivity in one molecule, such as phenol esters, thiol esters, N-hydroxy amine esters, esters of heterocyclic hydroxyl compounds. The active ester compound is preferably a compound obtained by condensation reaction of a carboxylic acid compound and / or a thiocarboxylic acid compound with a hydroxyl compound and / or a mercaptan compound. In particular, from the viewpoint of improving heat resistance, it is preferable to use an active ester curing agent obtained from a carboxylic acid compound and a hydroxyl compound, and more preferably an active ester curing agent obtained from a carboxylic acid compound and a phenol compound and / or a naphthol compound. As the carboxylic acid compound, for example, benzoic acid, acetic acid, succinic acid, maleic acid, itaconic acid, phthalic acid, isophthalic acid, terephthalic acid, pyromellitic acid, and the like can be given. As the phenol compound or naphthol compound, for example, hydroquinone, resorcinol, bisphenol A, bisphenol F, bisphenol S, phenolphthalein, methylated bisphenol A, methylated bisphenol F, methylated bisphenol S, phenol, o-cresol, m-cresol, p-cresol, catechol, a-naphthol, β-naphthol, 1,5-dihydroxynaphthalene, 1,6-dihydroxynaphthalene, 2,6-dihydroxynaphthalene, dihydroxybenzophenone, trihydroxybenzophenone, tetrahydroxybenzophenone, phloroglucinol, pyrogallol, dicyclopentadiene-type bisphenol compounds, phenol novolacs, and the like can be given. Here, the "dicyclopentadiene-type bisphenol compound" refers to a bisphenol compound obtained by condensing 2 molecules of phenol with 1 molecule of dicyclopentadiene.

[0247] Specifically, as the (D) component, it is preferable to use a dicyclopentadiene-type active ester compound, a naphthalene-type active ester compound containing a naphthalene structure, an acetyl compound active ester compound containing a phenol novolac, a benzoyl compound active ester compound containing a phenol novolac, and more preferably at least one selected from a dicyclopentadiene-type active ester compound and a naphthalene-type active ester compound, and further preferably a dicyclopentadiene-type active ester compound. As the dicyclopentadiene-type active ester compound, it is preferable to use an active ester compound containing a dicyclopentadiene-type bisphenol structure. The "dicyclopentadiene-type bisphenol structure" represents a divalent structural unit formed by phenylene-dicyclopentylene-phenylene.

[0248] As commercially available products of the (D) active ester compound, an active ester compound containing a dicyclopentadiene type diphenol structure can be exemplified by "EXB9451", "EXB9460", "EXB9460S", "EXB-8000L", "EXB-8000L-65M", "EXB-8000L-65TM", "HPC-8000L-65TM", "HPC-8000", "HPC-8000-65T", "HPC-8000H", "HPC-8000H-65TM" (manufactured by DIC Corporation); an active ester compound containing a naphthalene structure can be exemplified by "EXB-8100L-65T", "EXB-8150-60T", "EXB-8150-62T", "EXB-9416-70BK", "HPC-8150-60T", "HPC-8150-62T" (manufactured by DIC Corporation); a phosphorus-containing active ester compound can be exemplified by "EXB9401" (manufactured by DIC Corporation); an active ester compound of an acetylated product of a linear phenol formaldehyde resin can be exemplified by "DC808" (manufactured by Mitsubishi Chemical Corporation); an active ester compound of a benzoylated product of a linear phenol formaldehyde resin can be exemplified by "YLH1026", "YLH1030", "YLH1048" (manufactured by Mitsubishi Chemical Corporation); an active ester compound containing a styryl group and a naphthalene structure can be exemplified by "PC1300-02-65MA" (manufactured by AIR & WATER Corporation), and the like.

[0249] The active ester group equivalent of the (D) active ester compound is preferably 50 g / eq. to 500 g / eq., more preferably 50 g / eq. to 400 g / eq., and further preferably 100 g / eq. to 300 g / eq.. The active ester group equivalent is the mass of the active ester compound per 1 equivalent of the active ester group.

[0250] The content of the (D) active ester compound in the resin composition is not particularly limited, but when the nonvolatile component in the resin composition is taken as 100% by mass, it is preferably 50% by mass or less, more preferably 40% by mass or less, further preferably 30% by mass or less, further more preferably 20% by mass or less, and particularly preferably 15% by mass or less. The lower limit of the content of the (D) active ester compound in the resin composition is not particularly limited, but when the nonvolatile component in the resin composition is taken as 100% by mass, it can be, for example, 0% by mass or more, 0.01% by mass or more, and the like, and is preferably 0.1% by mass or more, more preferably 1% by mass or more, further preferably 3% by mass or more, further more preferably 5% by mass or more, and particularly preferably 7% by mass or more.

[0251] The mass ratio of the specific maleimide compound (A) to the active ester compound (D) in the resin composition ((A) component / (D) component) is preferably 0.1 or more, more preferably 0.5 or more, and particularly preferably 0.8 or more. The upper limit of the mass ratio of the specific maleimide compound (A) to the active ester compound (D) in the resin composition ((A) component / (D) component) is preferably 10 or less, more preferably 3 or less, and particularly preferably 1.5 or less.

[0252] <(E) Curing Accelerator>

[0253] In the resin composition of the present application, as an optional component, (E) a curing accelerator is sometimes contained.

[0254] As the curing accelerator, for example, a phosphorus-based curing accelerator, a urea-based curing accelerator, a guanidine-based curing accelerator, an imidazole-based curing accelerator, a metal-based curing accelerator, an amine-based curing accelerator, and the like can be given. One kind of (E) a curing accelerator can be used alone, or two or more kinds thereof can be used in combination.

[0255] As the phosphorus-based curing accelerator, aliphatic phosphonium salts such as tetrabutylphosphonium bromide, tetrabutylphosphonium chloride, tetrabutylphosphonium acetate, tetrabutylphosphonium decanoate, tetrabutylphosphonium laurate, bis(tetrabutylphosphonium) pyromellitate, tetrabutylphosphonium hydrogen hexahydrophthalate, tetrabutylphosphonium 2,6-bis[(2-hydroxy-5-methylphenyl)methyl]-4-methylphenol, di-t-butylmethylphosphonium tetraphenylborate, and the like; aromatic phosphonium salts such as methyltriphenylphosphonium bromide, ethyltriphenylphosphonium bromide, propyltriphenylphosphonium bromide, butyltriphenylphosphonium bromide, benzyltriphenylphosphonium chloride, tetraphenylphosphonium bromide, p-tolyltriphenylphosphonium tetra-p-tolylborate, tetraphenylphosphonium tetraphenylborate, tetraphenylphosphonium tetra-p-tolylborate, triphenylethylphosphonium tetraphenylborate, tris(3-methylphenyl)ethylphosphonium tetraphenylborate, tris(2-methoxyphenyl)ethylphosphonium tetraphenylborate, (4-methylphenyl)triphenylphosphonium thiocyanate, tetraphenylphosphonium thiocyanate, butyltriphenylphosphonium thiocyanate, and the like; aromatic phosphine-borane complexes such as triphenylphosphine-triphenylborane and the like; aromatic phosphine-quinone adducts such as triphenylphosphine-p-benzoquinone adduct and the like; aliphatic phosphines such as tributylphosphine, tri-t-butylphosphine, trioctylphosphine, di-t-butyl(2-butenyl)phosphine, di-t-butyl(3-methyl-2-butenyl)phosphine, tricyclohexylphosphine, and the like; aromatic phosphines such as dibutylphenylphosphine, di-t-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-t-butylphenyl)phosphine, tris(2,4-dimethylphenyl)phosphine, tris(2,5-dimethylphenyl)phosphine, tris(2,6-dimethylphenyl)phosphine, 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-t-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, 2,2'-bis(diphenylphosphino)diphenyl ether, and the like, and the like.

[0256] As the urea-based curing accelerator, there can be mentioned, for example, aliphatic dimethyl ureas such as 1,1-dimethyl urea, 1,1,3-trimethyl urea, 3-ethyl-1,1-dimethyl urea, 3-cyclohexyl-1,1-dimethyl urea, 3-cyclooctyl-1,1-dimethyl urea, etc.; aromatic dimethyl ureas such as 3-phenyl-1,1-dimethyl urea, 3-(4-chlorophenyl)-1,1-dimethyl urea, 3-(3,4-dichlorophenyl)-1,1-dimethyl urea, 3-(3-chloro-4-methylphenyl)-1,1-dimethyl urea, 3-(2-methylphenyl)-1,1-dimethyl urea, 3-(4-methylphenyl)-1,1-dimethyl urea, 3-(3,4-dimethylphenyl)-1,1-dimethyl urea, 3-(4-isopropylphenyl)-1,1-dimethyl urea, 3-(4-methoxyphenyl)-1,1-dimethyl urea, 3-(4-nitrophenyl)-1,1-dimethyl urea, 3-[4-(4-methoxyphenoxy)phenyl]-1,1-dimethyl urea, 3-[4-(4-chlorophenoxy)phenyl]-1,1-dimethyl urea, 3-[3-(trifluoromethyl)phenyl]-1,1-dimethyl urea, N,N-(1,4-phenylene)bis(N',N'-dimethyl urea), N,N-(4-methyl-1,3-phenylene)bis(N',N'-dimethyl urea) (toluene bisdimethyl urea), etc.

[0257] As the guanidine-based curing accelerator, there can be mentioned, for example, 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, 1-(o-tolyl)biguanide, etc.

[0258] As the imidazole-based curing accelerator, for example, 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, 1-benzyl-2-phenylimidazole, 1-cyanoethyl-2-methylimidazole, 1-cyanoethyl-2-undecylimidazole, 1-cyanoethyl-2-ethyl-4-methylimidazole, 1-cyanoethyl-2-phenylimidazole, 1-cyanoethyl-2-undecylimidazolium 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 the like imidazole compounds, and adducts of the imidazole compounds with epoxy resins.

[0259] As the imidazole-based curing accelerator, commercially available products can be used, and for example, "1B2PZ", "2MZA-PW", "2PHZ-PW" manufactured by Shikoku Chemicals Corporation, "P200-H50" manufactured by Mitsubishi Chemical Corporation and the like can be mentioned.

[0260] As the metal-based curing accelerator, for example, organic metal complexes or organic metal salts of metals such as cobalt, copper, zinc, iron, nickel, manganese, tin and the like can be mentioned. As specific examples of the organic metal complexes, for example, organic cobalt complexes such as acetylacetone cobalt (II), acetylacetone cobalt (III), organic copper complexes such as acetylacetone copper (II), organic zinc complexes such as acetylacetone zinc (II), organic iron complexes such as acetylacetone iron (III), organic nickel complexes such as acetylacetone nickel (II), organic manganese complexes such as acetylacetone manganese (II) and the like can be mentioned. As the organic metal salts, for example, zinc octoate, tin octoate, zinc naphthenate, cobalt naphthenate, tin stearate, zinc stearate and the like can be mentioned.

[0261] As the amine-based curing accelerator, for example, trialkyl amines such as triethylamine, tributylamine, 4-dimethylaminopyridine, benzyldimethylamine, 2,4,6-tris(dimethylaminomethyl)phenol, 1,8-diazabicyclo(5,4,0)-undecene and the like can be mentioned.

[0262] As the amine-based curing accelerator, commercially available products can be used, and examples thereof include "MY-25" manufactured by Ajinomoto Fine-Techno.

[0263] The content of the (E) curing accelerator in the resin composition is not particularly limited, but when the non-volatile component in the resin composition is taken as 100% by mass, it is preferably 15% by mass or less, more preferably 10% by mass or less, further preferably 5% by mass or less, and particularly preferably 3% by mass or less. The lower limit of the content of the (E) curing accelerator in the resin composition is not particularly limited, but when the non-volatile component in the resin composition is taken as 100% by mass, it can be, for example, 0% by mass or more, 0.001% by mass or more, 0.01% by mass or more, 0.1% by mass or more, 0.5% by mass or more, or the like.

[0264] (F) Other additives

[0265] As the nonvolatile component, the resin composition of the present application can further contain any additive. As such an additive, there can be mentioned, for example, a radical polymerization initiator such as a peroxide-based radical polymerization initiator, an azo-based radical polymerization initiator, and the like; an epoxy curing agent other than an active ester compound such as a phenol-based curing agent, a naphthol-based curing agent, an acid anhydride-based curing agent, a mercaptan-based curing agent, a benzoxazine-based curing agent, a cyanate-based curing agent, a carbodiimide-based curing agent, an imidazole-based curing agent, and the like; a thermoplastic resin such as a phenoxy resin, a polyvinyl acetal resin, a polyolefin resin, a polysulfone resin, a polyethersulfone resin, a polyphenylene ether resin, a polycarbonate resin, a polyether ether ketone resin, a polyester resin, and the like; an organic filler such as a rubber particle; an organic metal compound such as an organic copper compound, an organic zinc compound, an organic cobalt compound, and the like; a colorant such as phthalocyanine blue, phthalocyanine green, iodine green, diazonium yellow, crystal violet, titanium oxide, carbon black, and the like; a polymerization inhibitor such as hydroquinone, catechol, pyrogallol, phenothiazine, and the like; a leveling agent such as a silicone-based leveling agent, an acrylic polymer-based leveling agent, and the like; a thickening agent such as Benton, montmorillonite, and the like; a defoaming agent such as a silicone-based defoaming agent, an acrylic-based defoaming agent, a fluorine-based defoaming agent, a vinyl resin-based defoaming agent, and the like; an ultraviolet absorber such as a benzotriazole-based ultraviolet absorber, and the like; an adhesion improver such as urea silane, and the like; an adhesion imparting agent such as a triazole-based adhesion imparting agent, a tetrazole-based adhesion imparting agent, a triazine-based adhesion imparting agent, and the like; an antioxidant such as a hindered phenol-based antioxidant, a hindered amine-based antioxidant, and the like; a fluorescent brightener such as stilbene derivative, and the like; a surfactant such as a fluorine-based surfactant, a silicone-based surfactant, and the like; a flame retardant such as a phosphorus-based flame retardant (e.g., phosphate compound, phosphazene compound, phosphinic acid compound, red phosphorus), a nitrogen-based flame retardant (e.g., melamine sulfate), a halogen-based flame retardant, an inorganic-based flame retardant (e.g., antimony trioxide), and the like; a dispersant such as a phosphate-based dispersant, a polyoxyalkylene-based dispersant, an acetylene-based dispersant, a silicone-based dispersant, an anionic dispersant, a cationic dispersant, and the like; a stabilizer such as a borate-based stabilizer, a titanate-based stabilizer, an aluminate-based stabilizer, a zirconate-based stabilizer, an isocyanate-based stabilizer, a carboxylic acid-based stabilizer, a carboxylic anhydride-based stabilizer, and the like; and the like. (F) Other additives can be used singly or in combination of two or more kinds in any ratio. The content of (F) other additives can be appropriately set by those skilled in the art.

[0266] (G) Organic solvent

[0267] For the resin composition of the present application, in addition to the nonvolatile component described above, an arbitrary organic solvent is sometimes contained as a volatile component. As the (G) organic solvent, a publicly known organic solvent can be appropriately used, and the kind thereof is not particularly limited. As the (G) organic solvent, for example, a ketone-based solvent such as acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, and the like; an ester-based solvent such as methyl acetate, ethyl acetate, butyl acetate, isobutyl acetate, isoamyl acetate, methyl propionate, ethyl propionate, γ-butyrolactone, and the like; an ether-based solvent such as tetrahydropyran, tetrahydrofuran, 1,4-dioxane, diethyl ether, diisopropyl ether, dibutyl ether, diphenyl ether, and the like; an alcohol-based solvent such as methanol, ethanol, propanol, butanol, ethylene glycol, and the like; an ether ester-based solvent such as 2-ethoxyethyl acetate, propylene glycol monomethyl ether acetate, diethylene glycol monoethyl ether acetate, carbitol acetate (ethyl diglycol acetate), γ-butyrolactone, methyl methoxypropionate, and the like; an ester alcohol-based solvent such as methyl lactate, ethyl lactate, methyl 2-hydroxyisobutyrate, and the like; an ether alcohol-based solvent such as 2-methoxypropanol, 2-methoxyethanol, 2-ethoxyethanol, propylene glycol monomethyl ether, diethylene glycol monobutyl ether (butyl carbitol), and the like; an amide-based solvent such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone, and the like; a sulfoxide-based solvent such as dimethyl sulfoxide, and the like; a nitrile-based solvent such as acetonitrile, propionitrile, and the like; an aliphatic hydrocarbon-based solvent such as hexane, cyclopentane, cyclohexane, methylcyclohexane, and the like; an aromatic hydrocarbon-based solvent such as benzene, toluene, xylene, ethylbenzene, mesitylene, and the like, and the like can be used. The (G) organic solvent can be used alone or in combination of two or more kinds at an arbitrary ratio.

[0268] In one embodiment, the content of the (G) organic solvent is not particularly limited, but when the total content of all components in the resin composition is 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, and the like.

[0269] <Method for producing resin composition>

[0270] The resin composition of the present application can be produced, for example, by adding (A) the specific maleimide compound, (B) the epoxy resin, (C) the inorganic filler, (A') the other maleimide compound used as necessary, (D) the active ester compound used as necessary, (E) the curing accelerator used as necessary, (F) the other additive used as necessary, and (G) the organic solvent used as necessary, in any order and / or all at once or in parts, in any production vessel, and mixing them. Further, the temperature can be set as appropriate during the addition of the components and the mixing, and heating and / or cooling can be performed temporarily or throughout. Further, the resin composition can be stirred or shaken using a stirring device or a shaking device such as a mixer, or the like, during or after the addition and the mixing, to uniformly disperse it. Further, the degassing can be performed under a low pressure condition such as under vacuum, while stirring or shaking.

[0271] <Properties of the resin composition>

[0272] The resin composition of the present application contains (A) the specific maleimide compound, (B) the epoxy resin, and (C) the inorganic filler, and the content of the component (C) exceeds 30 mass% when the nonvolatile content of the resin composition is taken as 100 mass%. By using such a resin composition, a cured product having a small arithmetic average roughness (Ra) and low relative dielectric constant (Dk) and dielectric loss tangent (Df) can be obtained.

[0273] The cured product of the resin composition of the present application can have a low dielectric loss tangent (Df). Therefore, in one embodiment, the dielectric loss tangent (Df) of the cured product of the resin composition when measured under the conditions of 5.8 GHz and 23°C as in Test Example 1 below can preferably be 0.020 or less, more preferably 0.010 or less, still more preferably 0.009 or less, 0.008 or less, further more preferably 0.007 or less, 0.006 or less, particularly more preferably 0.005 or less, 0.004 or less.

[0274] The cured product of the resin composition of the present application can have a low relative dielectric constant (Dk). Therefore, in one embodiment, the relative dielectric constant (Dk) of the cured product of the resin composition when measured under the conditions of 5.8 GHz and 23°C as in Test Example 1 below can preferably be 5.0 or less, more preferably 4.0 or less, still more preferably 3.5 or less, particularly more preferably 3.0 or less.

[0275] In one embodiment, the cured product of the resin composition of the present application can have a surface after roughening treatment with a low arithmetic mean roughness (Ra). Thus, in one embodiment, the arithmetic mean roughness (Ra) of the surface of the cured product after roughening treatment, as measured in Test Example 2 described below, can preferably be 300 nm or less, more preferably 200 nm or less, further preferably 150 nm or less, further more preferably 100 nm or less, and particularly preferably 80 nm or less. There is no particular limitation on the lower limit, and for example, it can be 1 nm or more, 2 nm or more, or the like.

[0276] For the cured product of the resin composition of the present application, in one embodiment, the peel strength of the copper plating layer, as calculated from the load when the copper plating conductor layer is peeled off in the vertical direction after forming the copper plating conductor layer on the cured product, as measured in Test Example 2 described below, can preferably be 0.2 kgf / cm or more, more preferably 0.3 kgf / cm or more, further preferably 0.35 kgf / cm or more, and particularly preferably 0.4 kgf / cm or more. There is no particular limitation on the upper limit, and for example, it can be 10 kgf / cm or less or the like.

[0277] <Usage of the resin composition>

[0278] The resin composition of the present application can be suitably used as a resin composition for insulating use, particularly a resin composition for forming an insulating layer. Specifically, it can be suitably used as: a resin composition for forming an insulating layer (insulating layer-forming resin composition for forming a conductor layer) which is an insulating layer for forming a conductor layer (including a rewiring layer) formed on the insulating layer. Furthermore, in the printed wiring board described later, it can be suitably used as: a resin composition for forming an insulating layer of a printed wiring board (insulating layer-forming resin composition for a printed wiring board). The resin composition of the present application can also be widely used for resin sheets, sheet-like laminated materials such as prepregs, solder resists, underfill materials, die bonding materials, semiconductor sealing materials, filling resins (via filling resins), part embedding resins, and the like, for which a resin composition is required.

[0279] Furthermore, for example, in the case of manufacturing a semiconductor chip package by the following (1) to (6) processes, the resin composition of the present application can also be suitably used as: a resin composition for a rewiring layer-forming layer which is an insulating layer for forming a rewiring layer (resin composition for forming a rewiring layer-forming layer), and a resin composition for sealing a semiconductor chip (resin composition for sealing a semiconductor chip). In the manufacturing of a semiconductor chip package, a rewiring layer can be further formed on the sealing layer;

[0280] (1) a process of laminating a temporary fixing film on a substrate,

[0281] (2) a process of temporarily fixing the semiconductor chip on the temporary fixing film,

[0282] (3) a process of forming a sealing layer on the semiconductor chip,

[0283] (4) a process of peeling the substrate and the temporary fixing film from the semiconductor chip,

[0284] (5) a process of forming a rewiring formation layer as an insulating layer on a surface of the semiconductor chip from which the substrate and the temporary fixing film are peeled, and

[0285] (6) a process of forming a rewiring layer as a conductor layer on the rewiring formation layer.

[0286] Further, for the resin composition of the present application, since an insulating layer with good component burying property is obtained, it can be suitably used even in the case where the printed wiring board is a component-embedded circuit board.

[0287] <Sheet-shaped Laminated Material>

[0288] The resin composition of the present application can be used by being applied in a varnish state, but in industry, it is generally preferable to be used in the form of a sheet-shaped laminated material containing the resin composition.

[0289] As the sheet-shaped laminated material, a resin sheet, a prepreg, and the like are preferable.

[0290] In one embodiment, the resin sheet contains a support and a resin composition layer provided on the support, and the resin composition layer is formed of the resin composition of the present application.

[0291] From the viewpoint of thinning of the printed wiring board and the fact that an excellent insulating property can be provided even when the cured product of the resin composition is a thin film, the thickness of the resin composition layer is preferably 50 μm or less, more preferably 40 μm or less. The lower limit of the thickness of the resin composition layer is not particularly limited, but it can be generally 5 μm or more, 10 μm or more, or the like.

[0292] As the support, a film formed of a plastic material, a metal foil, a release paper, and the like can be given, and a film formed of a plastic material, a metal foil, and the like are preferable.

[0293] In the case of using a film formed of a plastic material as the support, as the plastic material, for example, polyethylene terephthalate (hereinafter sometimes referred to as "PET"), polyethylene naphthalate (hereinafter sometimes referred to as "PEN"), and the like polyester, polycarbonate (hereinafter sometimes referred to as "PC"), polymethyl methacrylate (PMMA), and the like acrylic polymer, cyclic polyolefin, triacetyl cellulose (TAC), polyethersulfide (PES), polyetherketone, polyimide, and the like can be mentioned. Among them, polyethylene terephthalate and polyethylene naphthalate are preferable, and inexpensive polyethylene terephthalate is particularly preferable.

[0294] In the case of using a metal foil as the support, as the metal foil, for example, a copper foil, an aluminum foil, and the like can be mentioned, and a copper foil is preferable. As the copper foil, a foil formed of a single metal of copper, or a foil formed of an alloy of copper and another metal (for example, tin, chromium, silver, magnesium, nickel, zirconium, silicon, titanium, and the like) can be used.

[0295] The surface of the support to which the resin composition layer is joined can be subjected to a mat treatment, a corona treatment, an antistatic treatment.

[0296] Further, as the support, a support with a release layer having a release layer on the surface to which the resin composition layer is joined can be used. As the release agent for the release layer of the support with a release layer, for example, a release agent selected from one or more of an alkyd resin, a polyolefin resin, a polyurethane resin, and a silicone resin can be mentioned. The support with a release layer can use a commercially available product, and for example, "SK-1", "AL-5", "AL-7" manufactured by Lindce Co., Ltd., "Lumirror T60" manufactured by Toray Co., Ltd., "Purex" manufactured by Teijin Co., Ltd., "Unipeel" manufactured by UNITIKA Co., Ltd., and the like as a PET film having a release layer in which an alkyd resin-based release agent is a main component can be mentioned.

[0297] The thickness of the support is not particularly limited, and is preferably in the range of 5 μm to 75 μm, and more preferably in the range of 10 μm to 60 μm. Note that in the case of using a support with a release layer, the thickness of the entire support with a release layer is preferably in the above range.

[0298] In one embodiment, the resin sheet can further include an arbitrary layer as needed. As the arbitrary layer, for example, a protective film and the like according to the selection of the support can be provided on the surface of the resin composition layer which is not joined to the support (i.e., the surface on the side opposite to the support). The thickness of the protective film is not particularly limited, and is, for example, 1 μm to 40 μm. By laminating the protective film, it is possible to suppress the adhesion of dust and the like to the surface of the resin composition layer or the occurrence of damage on the surface of the resin composition layer.

[0299] The resin sheet can be produced, for example, by directly applying a liquid resin composition to a support using a die coater or the like, or by preparing a resin varnish in which the resin composition is dissolved in an organic solvent, applying the resin varnish to a support using a die coater or the like, and further drying it to form a resin composition layer.

[0300] As the organic solvent, the same organic solvents as those described as the components of the resin composition can be mentioned. One kind of organic solvent can be used alone, or two or more kinds of organic solvents can be used in combination.

[0301] Drying can be performed by a publicly known method such as heating or blowing hot air. The drying conditions are not particularly limited, but the drying is performed in such a manner that the content of the organic solvent in the resin composition layer becomes 10% by mass or less, preferably 5% by mass or less. The drying conditions differ depending on the boiling point of the organic solvent in the resin composition or the resin varnish, and for example, when a resin composition or a resin varnish containing 30 to 60% by mass of an organic solvent is used, the resin composition layer can be formed by drying at 50 to 150°C for 3 to 10 minutes.

[0302] The resin sheet can be stored in a roll shape by being wound into a roll. When the resin sheet has a protective film, the protective film can be peeled off to use it.

[0303] In one embodiment, the prepreg is formed by impregnating the resin composition of the present application in a sheet-shaped fibrous base material.

[0304] The sheet-shaped fibrous base material used in the prepreg is not particularly limited, and a material commonly used as a base material for a prepreg, such as a glass cloth, an aramid nonwoven fabric, a liquid crystal polymer nonwoven fabric, or the like, can be used. From the viewpoint of thinning of the printed wiring board, the thickness of the sheet-shaped fibrous base material is preferably 50 μm or less, more preferably 40 μm or less, further preferably 30 μm or less, and particularly preferably 20 μm or less. The lower limit of the thickness of the sheet-shaped fibrous base material is not particularly limited. It is usually 10 μm or more.

[0305] The prepreg can be produced by a publicly known method such as a hot melt method or a solvent method.

[0306] The thickness of the prepreg can be in the same range as that of the resin composition layer in the resin sheet described above.

[0307] The sheet-shaped laminated material of the present application can be suitably used to form an insulating layer of a printed wiring board (for an insulating layer of a printed wiring board), and can be more suitably used to form an interlayer insulating layer of a printed wiring board (for an interlayer insulating layer of a printed wiring board).

[0308] <Printed wiring board>

[0309] The printed wiring board of the present application comprises an insulating layer formed of a cured product of the resin composition of the present application.

[0310] With respect to the printed wiring board, for example, the above-described resin sheet can be used, and the printed wiring board can be manufactured by a method comprising the following (I) and (II);

[0311] (I) a step of laminating the resin sheet on the inner layer substrate in such a manner that the resin composition layer of the resin sheet is joined to the inner layer substrate,

[0312] (II) a step of curing (for example, thermally curing) the resin composition layer to form an insulating layer.

[0313] The "inner layer substrate" used in the step (I) refers to a member that becomes a substrate of the printed wiring board, and examples thereof include a glass epoxy substrate, a metal substrate, a polyester substrate, a polyimide substrate, a BT resin substrate, a thermosetting polyphenylene ether substrate, and the like. In addition, the substrate can have a conductor layer on one or both surfaces thereof, and the conductor layer can be subjected to pattern processing. Sometimes, the inner layer substrate in which the conductor layer (circuit) is formed on one or both surfaces of the substrate is referred to as an "inner layer circuit substrate". In addition, an intermediate product to be further formed with an insulating layer and / or a conductor layer at the time of manufacturing the printed wiring board is also included in the "inner layer substrate" in the present application. When the printed wiring board is a component-embedded circuit board, the inner layer substrate in which a component is embedded can be used.

[0314] The lamination of the inner layer substrate and the resin sheet can be performed, for example, by heat-press bonding the resin sheet to the inner layer substrate from the support side. As a member for heat-press bonding the resin sheet to the inner layer substrate (hereinafter also referred to as a "heat-press bonding member"), for example, a heated metal plate (SUS end plate or the like) or a metal roller (SUS roller) or the like can be used. Note that, preferably, the heat-press bonding member is not directly pressed against the resin sheet, but is pressed through an elastic material such as heat-resistant rubber, so that the resin sheet sufficiently follows the surface irregularities of the inner layer substrate.

[0315] The lamination of the inner layer substrate and the resin sheet can be performed by a vacuum lamination method. In the vacuum lamination method, the heat-press bonding temperature is preferably in the range of 60°C to 160°C, more preferably in the range of 80°C to 140°C, the heat-press bonding pressure is preferably in the range of 0.098 MPa to 1.77 MPa, more preferably in the range of 0.29 MPa to 1.47 MPa, and the heat-press bonding time is preferably in the range of 20 seconds to 400 seconds, more preferably in the range of 30 seconds to 300 seconds. The lamination is preferably performed under reduced pressure of 26.7 hPa or less.

[0316] The lamination can be performed by a commercially available vacuum laminator. As the commercially available vacuum laminator, for example, a vacuum press-type laminator manufactured by Seiko Instruments & Electronics Co., Ltd., a vacuum applicator manufactured by Nikko-Materials Co., Ltd., and an intermittent vacuum press laminator can be mentioned.

[0317] After the lamination, the smoothing treatment of the laminated resin sheet can be performed by, for example, pressing the heat-pressing member from the support side under normal pressure (atmospheric pressure). The pressing conditions for the smoothing treatment can be set to the same conditions as the above-mentioned heat-pressing conditions for the lamination. The smoothing treatment can be performed by a commercially available laminator. Note that the lamination and the smoothing treatment can be continuously performed using the above-mentioned commercially available vacuum laminator.

[0318] The support can be removed between the process (I) and the process (II), or can be removed after the process (II).

[0319] In the process (II), the resin composition layer is cured (for example, thermally cured) to form an insulating layer formed of a cured product of the resin composition. The curing conditions of the resin composition layer are not particularly limited, and conditions generally used when forming an insulating layer of a printed wiring board can be used.

[0320] For example, the thermal curing conditions of the resin composition layer differ depending on the kind of the resin composition, and in one embodiment, the curing temperature is preferably 120°C to 240°C, more preferably 150°C to 220°C, and further preferably 170°C to 210°C. The curing time can be preferably set to 5 minutes to 120 minutes, more preferably to 10 minutes to 100 minutes, and further preferably to 15 minutes to 100 minutes.

[0321] The resin composition layer can be preheated at a temperature lower than the curing temperature before the resin composition layer is thermally cured. For example, the resin composition layer can 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 further preferably 15 minutes to 100 minutes, before the resin composition layer is thermally cured.

[0322] In the production of the printed wiring board, the process (III) of forming a hole in the insulating layer, the process (IV) of performing a roughening treatment on the insulating layer, and the process (V) of forming a conductor layer can be further performed. These processes (III) to (V) can be performed according to various methods that can be used in the production of the printed wiring board and are known to those skilled in the art. Note that, when the support is removed after the process (II), the removal of the support can be performed between the process (II) and the process (III), between the process (III) and the process (IV), or between the process (IV) and the process (V). Further, the formation of the insulating layer and the conductor layer of the processes (II) to (V) can be repeatedly performed as necessary to form a multilayer wiring board.

[0323] In other embodiments, the printed wiring board of the present application can be produced using the prepreg described above. The production method is basically the same as in the case of using a resin sheet.

[0324] The process (III) is a process of forming a hole in the insulating layer, and thereby a via hole, a through hole, or the like can be formed in the insulating layer. For the process (III), a drill, a laser, plasma, or the like can be used according to the composition of the resin composition used in the formation of the insulating layer, or the like. The size and shape of the hole can be appropriately determined according to the design of the printed wiring board.

[0325] The process (IV) is a process of performing a roughening treatment on the insulating layer. In this process (IV), removal of smear is also generally performed. The step and conditions of the roughening treatment are not particularly limited, and known steps and conditions generally used in the formation of the insulating layer of the printed wiring board can be employed. For example, the insulating layer can be subjected to a roughening treatment by sequentially performing a swelling treatment based on a swelling liquid, a roughening treatment based on an oxidizing agent, and a neutralization treatment based on a neutralizing liquid.

[0326] The swelling liquid used in the roughening treatment is not particularly limited, and an alkali solution, a surfactant solution, or the like can be given, and an alkali solution is preferable, and a sodium hydroxide solution, a potassium hydroxide solution, or the like is more preferable. As commercially available swelling liquids, "Swelling Dip Securiganth P", "Swelling Dip Securiganth SBU", or the like manufactured by ATOTECH JAPAN Co., Ltd. can be given. The swelling treatment based on the swelling liquid is not particularly limited, and for example, the insulating layer can be immersed in the swelling liquid at 30°C to 90°C for 1 minute to 20 minutes. From the viewpoint of inhibiting the swelling of the resin of the insulating layer to an appropriate level, it is preferable to immerse the insulating layer in the swelling liquid at 40°C to 80°C for 5 minutes to 15 minutes.

[0327] As the oxidizing agent used in the roughening treatment, there is no particular limitation, and examples include an alkaline permanganate solution prepared by dissolving potassium permanganate or sodium permanganate in an aqueous solution of sodium hydroxide. The roughening treatment based on the oxidizing agent such as the alkaline permanganate solution is preferably performed by immersing the insulating layer in the oxidizing agent solution heated to 60°C to 100°C for 10 minutes to 30 minutes. In addition, the concentration of the permanganate in the alkaline permanganate solution is preferably 5% by mass to 10% by mass. As commercially available oxidizing agents, examples include alkaline permanganate solutions such as "Concentrate Compact CP" and "Dosing Solution Securiganth P" manufactured by Asahi Denka Kogyo K.K.

[0328] In addition, as the neutralizing liquid used in the roughening treatment, an aqueous acid solution is preferable, and as commercially available products, examples include "Reduction Solution Securiganth P" manufactured by Asahi Denka Kogyo K.K.

[0329] The treatment based on the neutralizing liquid can be performed by immersing the treatment surface on which the roughening treatment based on the oxidizing agent has been performed in the neutralizing liquid at 30°C to 80°C for 5 minutes to 30 minutes. From the viewpoint of workability and the like, it is preferable to immerse the object on which the roughening treatment based on the oxidizing agent has been performed in the neutralizing liquid at 40°C to 70°C for 5 minutes to 20 minutes.

[0330] In one embodiment, the arithmetic average roughness (Ra) of the surface of the insulating layer after the roughening treatment is not particularly limited, and is preferably 500 nm or less, more preferably 400 nm or less, and further preferably 300 nm or less. There is no particular limitation on the lower limit, and it can be set to 1 nm or more, 2 nm or more, or the like. In addition, the root mean square roughness (Rq) of the surface of the insulating layer after the roughening treatment is preferably 500 nm or less, more preferably 400 nm or less, and further preferably 300 nm or less. There is no particular limitation on the lower limit, and it can be set to 1 nm or more, 2 nm or more, or the like. The arithmetic average roughness (Ra) and the root mean square roughness (Rq) of the surface of the insulating layer can be measured using a non-contact surface roughness meter.

[0331] The step (V) is a step of forming a conductor layer, and the conductor layer is formed on the insulating layer. The conductor material used in 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 can be a single metal layer or an alloy layer, and as the alloy layer, a layer formed of an alloy of two or more metals selected from the above metals (for example, nickel-chromium alloy, copper-nickel alloy, and copper-titanium alloy) can be given. Among them, from the viewpoint of the versatility of the conductor layer formation, cost, easiness of patterning, and the like, a single metal layer of chromium, nickel, titanium, aluminum, zinc, gold, palladium, silver, or copper, or an alloy layer of nickel-chromium alloy, copper-nickel alloy, copper-titanium alloy is preferable, a single metal layer of chromium, nickel, titanium, aluminum, zinc, gold, palladium, silver, or copper, or an alloy layer of nickel-chromium alloy is more preferable, and a single metal layer of copper is further preferable.

[0332] The conductor layer can be a single layer structure or a multilayer structure in which two or more single metal layers or alloy layers of different kinds of metals or alloys are stacked. When the conductor layer is a multilayer 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 nickel-chromium alloy.

[0333] The thickness of the conductor layer depends on the design of the printed wiring board desired, and is usually 3 μm to 35 μm, and preferably 5 μm to 30 μm.

[0334] In one embodiment, the conductor layer can be formed by plating. For example, a previously known technique such as a semi-additive method, a full-additive method, or the like can be used to perform plating on the surface of the insulating layer, and form a conductor layer having a desired wiring pattern. From the viewpoint of the easiness of manufacturing, it is preferable to form the conductor layer using the semi-additive method. Hereinafter, an example of forming the conductor layer using the semi-additive method will be shown.

[0335] First, a plating seed layer is formed on the surface of the insulating layer using electroless plating. Next, a mask pattern is formed on the formed plating seed layer so as to expose a part of the plating seed layer corresponding to a desired wiring pattern. A metal layer is formed on the exposed plating seed layer using electrolytic plating, and then the mask pattern is removed. Then, the unnecessary plating seed layer is removed by etching or the like, and a conductor layer having a desired wiring pattern can be formed.

[0336] In other embodiments, the conductor layer can be formed using a metal foil. In the case where the conductor layer is formed using a metal foil, process (V) is preferably carried out between process (I) and process (II). For example, after process (I), the support is removed, and a metal foil is laminated on the surface of the exposed resin composition layer. The lamination of the resin composition layer and the metal foil can be carried out using a vacuum lamination method. The conditions for the lamination can be the same as those described for process (I). Next, process (II) is carried out to form the insulating layer. Then, using the metal foil on the insulating layer, a conductor layer having a desired wiring pattern can be formed using a technology known in the art such as a subtractive method, a modified semi-additive method, and the like.

[0337] The metal foil can be manufactured, for example, using a known method such as an electrolytic method, a rolling method, and the like. As commercially available products of the metal foil, for example, HLP foil, JX UT-III foil, 3EC-III foil, TP-III foil, and the like manufactured by JX Nippon Mining & Metal Corporation can be mentioned.

[0338] <semiconductor device>

[0339] The semiconductor device of the present application includes the printed wiring board of the present application. The semiconductor device of the present application can be manufactured using the printed wiring board of the present application.

[0340] As the semiconductor device, various semiconductor devices for use in electrical products (for example, computers, mobile phones, digital cameras, televisions, and the like) and vehicles (for example, motorcycles, automobiles, electric cars, ships, aircraft, and the like), and the like can be mentioned.

[0341] Examples

[0342] Hereinafter, the present application will be specifically described by way of examples. The present application is not limited by these examples. It should be noted that hereinafter, "parts" and "%" representing amounts mean "mass parts" and "mass %", respectively, unless otherwise explicitly stated. The temperature conditions in the case where no temperature is specifically designated are room temperature (25°C).

[0343] <Example 1>

[0344] Maleimide-terminated polyimide ("BMI-6100" manufactured by Designer Molecules) 10 parts, naphthol aralkyl-type epoxy resin ("ESN-475V" manufactured by JFE Chemical Corporation) 18 parts, spherical silica ( "SO-C2" manufactured by Admatechs Corporation, average particle diameter 0.5 μm, specific surface area 5.8 m 2(g) 60 parts of an active ester compound ("HPC-8150-60T" manufactured by DIC Corporation, toluene solution of 60 mass% of solid content) 18.3 parts, and an imidazole-based curing accelerator ("1B2PZ" manufactured by Shikoku Chemicals Corporation, 1-benzyl-2-phenylimidazole) 1 part were mixed, uniformly dispersed with a high-speed rotation mixer, and a resin composition was prepared.

[0345] Example 2

[0346] The use amount of a naphthol aralkyl type epoxy resin ("ESN-475V" manufactured by Nippon Steel Chemical Co., Ltd.) was changed from 18 parts to 15 parts, the use amount of an active ester compound ("HPC-8150-60T" manufactured by DIC Corporation, toluene solution of 60 mass% of solid content) was changed from 18.3 parts to 16.7 parts, and further, an aromatic maleimide ("MIR-3000-70MT" manufactured by Japan Epoxy Resin Co., Ltd., MEK / toluene mixed solution of 70% of solid content) 5.7 parts was used, and otherwise, the same operation as in Example 1 was performed to prepare a resin composition.

[0347] Example 3

[0348] An MEK solution (70 mass% of non-volatile content) of a maleimide compound A (Mw / Mn = 1.81, t" = 1.47 (mainly 1, 2, or 3)) represented by the following formula (X) synthesized by the method described in Synthesis Example 1 of Japanese Patent Application Laid-Open No. 2020-500211 was prepared.

[0349] [Chemical Formula 27]

[0350]

[0351] The use amount of a naphthol aralkyl type epoxy resin ("ESN-475V" manufactured by Nippon Steel Chemical Co., Ltd.) was changed from 18 parts to 15 parts, the use amount of an active ester compound ("HPC-8150-60T" manufactured by DIC Corporation, toluene solution of 60 mass% of solid content) was changed from 18.3 parts to 16.7 parts, and further, an aromatic maleimide (maleimide compound A, MEK solution of 70% of solid content) 5.7 parts was used, and otherwise, the same operation as in Example 1 was performed to prepare a resin composition.

[0352] Example 4

[0353] A resin composition was produced in the same manner as in Example 1, except that the amount of naphthol aralkyl type epoxy resin ("ESN-475V" manufactured by Nitto Echemicals Co., Ltd.) was changed from 18 parts to 15 parts, the amount of active ester compound ("HPC-8150-60T" manufactured by DIC Corporation, toluene solution of 60 mass% solid content) was changed from 18.3 parts to 16.7 parts, and further, divinylbenzene / styrene copolymer ("ODV-XET-X04" manufactured by Nitto Echemicals Co., Ltd., toluene solution of 65% solid content) was used in an amount of 6.2 parts.

[0354] Example 5

[0355] A resin composition was produced in the same manner as in Example 1, except that the amount of naphthol aralkyl type epoxy resin ("ESN-475V" manufactured by Nitto Echemicals Co., Ltd.) was changed from 18 parts to 15 parts, the amount of active ester compound ("HPC-8150-60T" manufactured by DIC Corporation, toluene solution of 60 mass% solid content) was changed from 18.3 parts to 16.7 parts, and further, vinylbenzyl-modified polyphenyl ether ("OPE-2St 2200" manufactured by Mitsubishi Gas Chemical Co., Inc., toluene solution of 65% solid content) was used in an amount of 6.2 parts.

[0356] Example 6

[0357] A resin composition was produced in the same manner as in Example 1, except that the amount of naphthol aralkyl type epoxy resin ("ESN-475V" manufactured by Nitto Echemicals Co., Ltd.) was changed from 18 parts to 15 parts, the amount of active ester compound ("HPC-8150-60T" manufactured by DIC Corporation, toluene solution of 60 mass% solid content) was changed from 18.3 parts to 16.7 parts, and further, methacrylic acid-modified polyphenyl ether (a material prepared by making "SA9000-111" manufactured by Sabo Basic Innovative Plastics Co., Ltd. into a toluene solution of 50% solid content) was used in an amount of 8 parts.

[0358] Comparative Example 1

[0359] A resin composition was produced in the same manner as in Example 1, except that aromatic maleimide ("MIR-3000-70MT" manufactured by Japan Epoxy Resin Co., Ltd., MEK / toluene mixed solution of 70% solid content) was used in an amount of 14.3 parts instead of maleimide-terminated polyimide ("BMI-6100" manufactured by Designer Molecules) in an amount of 10 parts.

[0360] Comparative Example 2

[0361] A resin composition was produced in the same manner as in Example 1, except that no maleimide-terminated polyimide (Designer Molecules, "BMI-6100") was used, the amount of naphthol aralkyl-type epoxy resin (Nippon Steel Chemical Co., "ESN-475V") was changed from 18 parts to 23 parts, and the amount of active ester compound (DIC, "HPC-8150-60T", toluene solution of 60 mass% solid content) was changed from 18.3 parts to 26.7 parts.

[0362] <Measurement Example 1: Measurement of Relative Dielectric Constant (Dk) and Dielectric Loss Tangent (Df)>

[0363] As a support, a polyethylene terephthalate film (Lindner, "AL5", thickness 38 μm) having a release layer was prepared. On the release layer of the support, the resin composition obtained in the Examples and Comparative Examples was uniformly applied so that the thickness of the dried resin composition layer would be 40 μm. Then, the resin composition was dried at 80 to 100°C (average 90°C) for 4 minutes to obtain a resin sheet A comprising the support and the resin composition layer.

[0364] The obtained resin sheet A was cured in an oven at 190°C for 90 minutes. The resin sheet A was taken out of the oven, and the support was peeled off from the resin sheet A, whereby a cured product of the resin composition layer was obtained. The cured product was cut into a length of 80 mm and a width of 2 mm, and was set as a cured product B for evaluation.

[0365] For the cured product B for evaluation, the value of the dielectric constant (Dk value) and the value of the dielectric loss tangent (Df value) were measured by the resonant cavity perturbation method using "HP 8362B" (Agilent Technologies) at a measurement frequency of 5.8 GHz and a measurement temperature of 23°C. The measurement was performed on two test pieces, and the average value was calculated.

[0366] <Measurement Example 2: Measurement of Peel Strength and Arithmetic Mean Roughness (Ra)>

[0367] (1) Preparation of Inner Layer Substrate

[0368] Both surfaces of a glass cloth substrate epoxy resin two-sided copper clad laminate (thickness of copper foil 18 μm, thickness of substrate 0.4 mm, "R1515A" (Panasonic)) having an inner layer circuit formed thereon were subjected to roughening treatment of the copper surface by etching 1 μm with a micro-etching agent ("CZ8101" (MEC)).

[0369] (2) Lamination of Resin Sheet A

[0370] Using an intermittent vacuum pressure laminator (Nikko-Materials, 2-Stage Buildup Laminator, "CVP700"), the resin sheet A obtained in Test Example 1 was laminated onto both sides of the inner layer substrate in such a manner that the resin composition layer was in contact with the inner layer substrate. Lamination was performed as follows: a 30-second depressurization was applied, and after adjusting the pressure to below 13 hPa, a 30-second pressing was performed at 120°C and 0.74 MPa. Next, a 60-second hot-press was performed at 100°C and 0.5 MPa.

[0371] (3) Thermosetting of the resin composition layer

[0372] Then, the inner substrate with resin sheet A laminated is placed in an oven at 130°C and heated for 30 minutes, followed by heating in an oven at 170°C for 30 minutes to thermally cure the resin composition layer, forming an insulating layer. Then, the support is peeled off to obtain a cured substrate A having an insulating layer, an inner substrate, and an insulating layer in sequence.

[0373] (4) Roughening treatment

[0374] For the cured substrate A, a decontamination treatment as a roughening process is performed. As a decontamination treatment, the following wet decontamination treatment is performed.

[0375] (Wet decontamination treatment)

[0376] The cured substrate A was immersed in a swelling solution (Swelling Dip Securiganth P, manufactured by Amtec Japan, an aqueous solution of diethylene glycol monobutyl ether and sodium hydroxide) at 60°C for 5 minutes, followed by immersion in an oxidizing agent solution (Concentrate Compact CP, manufactured by Amtec Japan, an aqueous solution of approximately 6% potassium permanganate and approximately 4% sodium hydroxide) at 80°C for 20 minutes. Next, it was immersed in a neutralizing solution (Reduction Solution Securiganth P, an aqueous solution of sulfuric acid, manufactured by Amtec Japan) at 40°C for 5 minutes, and then dried at 80°C for 15 minutes.

[0377] (5) Determination of the arithmetic mean roughness (Ra) of the surface of the insulation layer after roughening treatment

[0378] Using a non-contact surface roughness measuring instrument (Bruker WYKO NT3300), with VSI mode, a 50x lens, and a measurement range set to 121 μm × 92 μm, the arithmetic mean roughness (Ra) of the insulating layer surface of the roughened substrate A was calculated. The measurement was performed by averaging 10 points.

[0379] (6) Formation of conductor layer

[0380] A conductor layer was formed on the roughened surface of the insulating layer of the cured substrate A according to a semi-additive method. That is, the substrate after the roughening treatment was immersed in an electroless plating solution containing PdCl2at 40°C for 5 minutes, and then immersed in an electroless copper plating solution at 25°C for 20 minutes. Subsequently, after annealing treatment at 150°C for 30 minutes, a resist layer was formed, and patterning was performed using etching. Then, copper electrolytic plating was performed, and a conductor layer having a thickness of 25 μm was formed. Annealing treatment was performed at 190°C for 60 minutes. The obtained substrate was referred to as "evaluation substrate B".

[0381] (7) Measurement of peeling strength of plated conductor layer

[0382] The peeling strength of the insulating layer from the conductor layer was measured according to Japanese Industrial Standard (JIS C6481). Specifically, a cut was made on the conductor layer of the evaluation substrate B to a width of 10 mm and a length of 100 mm, one end was peeled and held with a jig, and the load (kgf / cm) at the time of peeling 35 mm in the vertical direction at a speed of 50 mm / minute was measured at room temperature to obtain the peeling strength. A tensile testing machine ("AC-50C-SL" manufactured by TSE Corporation) was used in the measurement.

[0383] The amounts of use of non-volatile components of the resin compositions of the examples and comparative examples, and the measurement results of the test examples are shown in Table 1 below.

[0384] [Table 1]

[0385]

[0386] As is clear from the above, by using the resin composition described below, a cured product having a small arithmetic average roughness (Ra) and low relative dielectric constant (Dk) and dielectric loss tangent (Df) can be obtained; the resin composition is a resin composition comprising (A) a maleimide compound containing a divalent group represented by formula (1), and a divalent group represented by formula (2) and / or a divalent group represented by formula (3) in one molecule, (B) an epoxy resin, and (C) an inorganic filler, wherein the content of the component (C) exceeds 30 mass% when the non-volatile components in the resin composition are taken as 100 mass%.

Claims

1. A resin composition, which is a resin composition comprising the following (A) to (D) components, (A) a maleimide compound containing a divalent group represented by formula (1), and a divalent group represented by formula (2) and / or a divalent group represented by formula (3) in one molecule, In formula (1), X 1 represents a single bond, -C(R 10 )2-, -0-, -CO-, -S-, -SO-, -S02-, -CONH-, -NHCO-, -COO-, or -OCO-; R 10 each independently represents a hydrogen atom, an alkyl group, an alkenyl group, an arylalkyl group, or an aryl group; for R 11 , R 12 , R 13 , R 14 , R 21 , R 22 , R 23 , and R 24 , at least one of them each independently represents an alkyl group, an alkenyl group, an arylalkyl group, or an aryl group, and the others represent a hydrogen atom; and * represents a bonding site, In formula (2), R 31 , R 32 , and R 33 each independently represent a hydrogen atom, an alkyl group, an alkenyl group, an arylalkyl group, or an aryl group; and * represents a bonding site. In formula (3), R 41 and R 42 each independently represents a hydrogen atom, an alkyl group, an alkenyl group, an arylalkyl group, or an aryl group; and * represents a bonding site, (B) an epoxy resin, (C) an inorganic filler, and (D) an active ester compound, wherein the content of the (C) component is 50 mass% or more and 90 mass% or less when the nonvolatile components in the resin composition are taken as 100 mass%, the mass ratio of the (A) component to the (B) component, that is, (A) component / (B) component is 0.1 or more and 2 / 3 or less, the mass ratio of the (A) component to the (D) component, that is, (A) component / (D) component is 0.5 or more and 1.5 or less.

2. The resin composition according to claim 1, wherein, X 1 -C(R 10 )2-; R 11 , R 12 , R 21 , and R 22 are each independently an alkyl group; and R 10 , R 13 , R 14 , R 23 , R 24 , R 31 , R 32 , R 33 , R 41 , and R 42 are hydrogen atoms.

3. The resin composition according to claim 1, wherein the (A) component further contains a divalent group represented by formula (4) in one molecule, In formula (4), X 2 , X 3 , and X 4 each independently represents a single bond, -C(R 50 )2-, -0-, -CO-, -S-, -SO-, -S02-, -CONH-, -NHCO-, -COO-, or -OCO-; R 50 , R 51 , R 52 , R 53 , R 54 , R 61 , R 62 , R 63 , R 64 , R 71 , R 72 , R 73 , R 74 , R 81 , R 82 , R 83 , and R 84 each independently represents a hydrogen atom, an alkyl group, an alkenyl group, an arylalkyl group, or an aryl group; and * represents a bonding site.

4. The resin composition according to claim 3, wherein, X 2 and X 4 is -O-; X 3 is -C(R 50 )2-; R 50 each independently is alkyl; and R 51 , R 52 , R 53 , R 54 , R 61 , R 62 , R 63 , R 64 , R 71 , R 72 , R 73 , R 74 , R 81 , R 82 , R 83 and R 84 are hydrogen atoms.

5. The resin composition according to claim 1, wherein, the content of the (A) component is 0.1 mass% or more when the nonvolatile components in the resin composition are taken as 100 mass%.

6. The resin composition according to claim 1, wherein, the content of the (A) component is 1 mass% or more and 15 mass% or less when the nonvolatile components in the resin composition are taken as 100 mass%.

7. The resin composition according to claim 1, wherein the content of the (A) component is 7 mass% or more when the nonvolatile components in the resin composition are taken as 100 mass%.

8. The resin composition according to claim 1, further comprising an (A') radical polymerizable compound other than the (A) component.

9. The resin composition according to claim 8, wherein, the content of the (A') component is 0.1 mass% or more when the nonvolatile components in the resin composition are taken as 100 mass%.

10. The resin composition according to claim 8, wherein, the content of the (A') component is 2 mass% or more when the nonvolatile components in the resin composition are taken as 100 mass%.

11. The resin composition according to claim 8, wherein, the content of the (A') component is 40 mass% or less when the nonvolatile components in the resin composition are taken as 100 mass%.

12. The resin composition according to claim 8, wherein, the content of the (A') component is 10 mass% or less when the nonvolatile components in the resin composition are taken as 100 mass%.

13. The resin composition according to claim 1, wherein, the content of the (A) component is 10 mass% or more when the total radical polymerizable compounds in the resin composition are taken as 100 mass%.

14. The resin composition according to claim 1, wherein, the content of the (A) component is 50 mass% or more when the total radical polymerizable compounds in the resin composition are taken as 100 mass%.

15. The resin composition according to claim 1, wherein, the (B) component contains a (B-1) epoxy resin containing a condensed ring structure.

16. The resin composition according to claim 15, wherein, the (B-1) component contains a naphthol aralkyl type epoxy resin.

17. The resin composition according to claim 15, wherein, the content of the (B-1) component is 50 mass% or more when the total epoxy resins in the resin composition are taken as 100 mass%.

18. The resin composition of claim 15, wherein, the content of the (B-1) component is 90 mass% or more when the total epoxy resins in the resin composition are taken as 100 mass%.

19. The resin composition according to claim 1, wherein, the content of the (B) component is 0.01 mass% or more when the nonvolatile components in the resin composition are taken as 100 mass%.

20. The resin composition according to claim 1, wherein, the content of the (B) component is 1 mass% or more and 40 mass% or less when the nonvolatile components in the resin composition are taken as 100 mass%.

21. The resin composition according to claim 1, wherein, the content of the (B) component is 10 mass% or more when the nonvolatile components in the resin composition are taken as 100 mass%.

22. The resin composition according to claim 1, wherein, The content of the (B) component is 20 mass% or less, based on 100 mass% of the nonvolatile components in the resin composition.

23. The resin composition of claim 1, wherein, The mass ratio of the (A) component to the (B) component, i.e., (A) component / (B) component, is 0.3 or more and 2 / 3 or less.

24. The resin composition according to claim 1, wherein, The mass ratio of the (A) component to the (B) component, i.e., (A) component / (B) component, is 0.5 or more and 2 / 3 or less.

25. The resin composition according to claim 1, wherein, The content of the (C) component is 55 mass% or more, based on 100 mass% of the nonvolatile components in the resin composition.

26. The resin composition of claim 1, wherein, The content of the (C) component is 70 mass% or less, based on 100 mass% of the nonvolatile components in the resin composition.

27. The resin composition of claim 1, wherein, The mass ratio of the (A) component to the (C) component, i.e., (A) component / (C) component, is 0.01 or more.

28. The resin composition of claim 1, wherein, The mass ratio of the (A) component to the (C) component, i.e., (A) component / (C) component, is 0.05 or more and 0.3 or less.

29. The resin composition of claim 1, wherein, The mass ratio of the (A) component to the (C) component, i.e., (A) component / (C) component, is 0.1 or more.

30. The resin composition of claim 1, wherein, The content of the (D) component is 0.01 mass% or more, based on 100 mass% of the nonvolatile components in the resin composition.

31. The resin composition of claim 1, wherein, The content of the (D) component is 7 mass% or more, based on 100 mass% of the nonvolatile components in the resin composition.

32. The resin composition of claim 1, wherein, The content of the (D) component is 20 mass% or less, based on 100 mass% of the nonvolatile components in the resin composition.

33. The resin composition of claim 1, wherein, The content of the (D) component is 15 mass% or less, based on 100 mass% of the nonvolatile components in the resin composition.

34. The resin composition of claim 1, wherein, The mass ratio of the (A) component to the (D) component, i.e., (A) component / (D) component, is 0.8 or more and 1.5 or less.

35. The resin composition of claim 1, wherein, The cured product of the resin composition has a dielectric loss tangent of 0.020 or less when measured at 5.8 GHz at 23°C.

36. The resin composition of claim 1, wherein, The cured product of the resin composition has a dielectric loss tangent of 0.005 or less when measured at 5.8 GHz at 23°C.

37. The resin composition of claim 1, wherein, The cured product of the resin composition has a dielectric loss tangent of 0.004 or less when measured at 5.8 GHz at 23°C.

38. The resin composition of claim 1, wherein, The cured product of the resin composition has a relative dielectric constant of 5.0 or less when measured at 5.8 GHz at 23°C.

39. The resin composition of claim 1, wherein, The cured product of the resin composition has a relative dielectric constant of 3.0 or less when measured at 5.8 GHz at 23°C.

40. A cured product, which is a cured product of the resin composition described in any one of claims 1 to 39.

41. A sheet-like laminated material, which contains the resin composition described in any one of claims 1 to 39.

42. A resin sheet, which has: a support body, and a resin composition layer formed of the resin composition described in any one of claims 1 to 39, provided on the support body.

43. A printed wiring board, which has an insulating layer formed of a cured product of the resin composition described in any one of claims 1 to 39.

44. A semiconductor device, which includes the printed wiring board described in claim 43.

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