Resin composition

Abstract

To provide a resin composition from which a cured product that exhibits good dielectric characteristics and has excellent adhesive strength to a conductor layer after exposure to high temperature and high humidity environment can be obtained; a resin sheet using the resin composition; a cured product of the resin composition; a circuit board including the cured product; and a semiconductor device including the circuit board.SOLUTION: A resin composition contains (A) an epoxy resin, (B) an active ester-based curing agent, and (C) a compound containing a structural unit represented by formula (C1) an a terminal group represented by formula (c1).SELECTED DRAWING: None

Description

Technical Field

[0001] The present invention relates to a resin composition. Further, it relates to a resin sheet, a cured product, a circuit board, and a semiconductor device.

Background Art

[0002] A resin composition containing an epoxy resin and its curing agent has been widely used as an insulating material for circuit boards such as printed wiring boards and redistribution substrates of semiconductor chip packages because it provides a cured product with excellent insulation, heat resistance, adhesion, etc.

[0003] On the other hand, with the recent increase in communication speed, an insulating material with excellent dielectric properties (low dielectric tangent) is required for the insulating material of circuit boards to reduce transmission loss when operating in a high-frequency environment. As such an insulating material, the resin described in Patent Document 1 is known.

Prior Art Documents

Patent Documents

[0004]

Patent Document 1

Summary of the Invention

Problems to be Solved by the Invention

[0005] When an insulating layer is formed using a resin composition adopting a composition contributing to good dielectric properties as described in Patent Document 1, it has been found that the adhesion strength of the insulating layer to the conductor layer tends to deteriorate after exposure to a high-temperature and high-humidity environment.

[0006] An object of the present invention is to provide a resin composition that can provide a cured product exhibiting good dielectric properties and excellent adhesion strength to a conductor layer after exposure to a high-temperature and high-humidity environment; a resin sheet using the resin composition; a cured product of the resin composition; a circuit board containing the cured product; and a semiconductor device containing the circuit board.

Means for Solving the Problems

[0007] In order to achieve the object of the present invention, the inventors of the present invention have conducted intensive studies. As a result, it has been found that the above problems can be solved by using a resin composition containing (A) an epoxy resin, (B) an active ester-based curing agent, and (C) a compound containing a specific structural unit and a specific terminal group, and the present invention has been completed. That is, the present invention includes the following.

[0008] <1> (A) An epoxy resin, (B) an active ester-based curing agent, and (C) a resin composition containing a compound containing a structural unit represented by the following formula (C1) and a terminal group represented by the following formula (c1).

Chemical formula

Chemical formula

Advantages of the Invention

[0009] According to the present invention, there can be provided a resin composition that exhibits good dielectric properties and provides a cured product having excellent adhesion strength to a conductor layer after exposure to a high-temperature and high-humidity environment; a resin sheet using the resin composition; a cured product of the resin composition; a circuit board containing the cured product; and a semiconductor device containing the circuit board.

Embodiments for Carrying Out the Invention

[0010] <Glossary of Terms> As used herein, the term "optionally substituted" with respect to a compound or group means both the case where a hydrogen atom of the compound or group is unsubstituted with a substituent and the case where some or all of the hydrogen atoms of the compound or group are substituted with a substituent.

[0011] As used herein, the term "substituent" means, unless otherwise specified, a halogen atom, an alkyl group, an alkenyl group, a cycloalkyl group, an alkoxy group, a cycloalkyloxy group, an aryl group, an aryloxy group, an arylalkyl group, an arylalkoxy group, a monovalent heterocyclic group, an alkylidene group, an amino group, a silyl group, a carboxy group, a sulfo group, a cyano group, a nitro group, a hydroxy group, a mercapto group, and an oxo group.

[0012] Examples of the halogen atom used as a substituent include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. The alkyl group used as a substituent may be either linear or branched. The number of carbon atoms of the alkyl group is preferably 1 to 12, more preferably 1 to 6, and still more preferably 1 to 3. The alkenyl group used as a substituent may be either linear or branched. The number of carbon atoms of the alkenyl group is preferably 2 to 12, more preferably 2 to 6, and still more preferably 2 or 3. The number of carbon atoms of the cycloalkyl group used as a substituent is preferably 3 to 12, more preferably 3 to 6. The alkoxy group used as a substituent may be either linear or branched. The number of carbon atoms of the alkoxy group is preferably 1 to 12, more preferably 1 to 6. The number of carbon atoms of the cycloalkyloxy group used as a substituent is preferably 3 to 12, more preferably 3 to 6. The aryl group used as a substituent is a group obtained by removing one hydrogen atom from the aromatic ring of an aromatic hydrocarbon. The number of carbon atoms of the aryl group used as a substituent is preferably 6 to 14, more preferably 6 to 10. The number of carbon atoms of the aryloxy group used as a substituent is preferably 6 to 14, more preferably 6 to 10. The number of carbon atoms of the arylalkyl group used as a substituent is preferably 7 to 15, more preferably 7 to 11. The number of carbon atoms of the arylalkoxy group used as a substituent is preferably 7 to 15, more preferably 7 to 11. The monovalent heterocyclic group used as a substituent refers to a group obtained by removing one hydrogen atom from the heterocycle of a heterocyclic compound. The number of carbon atoms of the monovalent heterocyclic group is preferably 3 to 15, more preferably 3 to 9. The aralkyl group used as a substituent refers to an alkyl group substituted with one or more aryl groups. The alkylidene group used as a substituent refers to a group obtained by removing two hydrogen atoms from the same carbon atom of an alkane. The number of carbon atoms of the alkylidene group is preferably 1 to 12, more preferably 1 to 6, and still more preferably 1 to 3. The above-mentioned substituents may further have substituents (hereinafter sometimes referred to as "secondary substituents"). Unless otherwise specified, the same substituents as those described above may be used as the secondary substituents.

[0013] In this specification, the term "aromatic group" refers to a group obtained by removing one or more hydrogen atoms from an aromatic ring of an aromatic compound. Specifically, a monovalent aromatic group refers to a group obtained by removing one hydrogen atom from an aromatic ring of an aromatic compound, and a divalent aromatic group refers to a group obtained by removing two hydrogen atoms from an aromatic ring of an aromatic compound. Further, the term "aromatic ring" means a ring that follows Hückel's rule where the number of electrons contained in the π electron system on the ring is 4n + 2 (n is a natural number), and includes a monocyclic aromatic ring and a condensed aromatic ring in which two or more monocyclic aromatic rings are condensed. The aromatic ring can be a carbocyclic ring or a heterocyclic ring. Examples of the monovalent aromatic group include an aryl group which may have a substituent and a heteroaryl group which may have a substituent, and examples of the divalent aromatic group include an arylene group which may have a substituent and a heteroarylene group which may have a substituent. In this specification, unless otherwise specified, the number of carbon atoms of the aromatic group is preferably 3 or more, more preferably 4 or more or 5 or more, still more preferably 6 or more, and the upper limit thereof is preferably 24 or less, more preferably 18 or less or 14 or less, still more preferably 10 or less. The number of carbon atoms of the substituent is not included in the number of carbon atoms.

[0014] As used herein, the term "aliphatic group" refers to a group obtained by removing one or more hydrogen atoms bonded to aliphatic carbon atoms of an aliphatic compound. Specifically, a monovalent aliphatic group refers to a group obtained by removing one hydrogen atom bonded to an aliphatic carbon atom of an aliphatic compound, and a divalent aliphatic group refers to a group obtained by removing two hydrogen atoms bonded to an aliphatic carbon atom of an aliphatic compound. Examples of the monovalent aliphatic group include an alkyl group which may have a substituent, a cycloalkyl group which may have a substituent, an alkenyl group which may have a substituent, and a cycloalkenyl group which may have a substituent. Examples of the divalent aliphatic group include an alkylene group which may have a substituent, a cycloalkylene group which may have a substituent, an alkenylene group which may have a substituent, and a cycloalkenylene group which may have a substituent. In the present specification, unless otherwise specified, the number of carbon atoms of the aliphatic group is preferably 1 or more, more preferably 2 or more, still more preferably 3 or more, 4 or more, 5 or more or 6 or more, and preferably 50 or less, more preferably 40 or less, still more preferably 30 or less, 20 or less, 18 or less, 16 or less, 14 or less or 12 or less. The number of carbon atoms of the substituent is not included in the number of carbon atoms of the aliphatic group.

[0015] Hereinafter, the present invention will be described in detail with reference to embodiments and examples. However, the present invention is not limited to the following embodiments and examples, and can be arbitrarily modified and implemented without departing from the scope of the claims of the present invention and its equivalent scope.

[0016] [Resin Composition] The resin composition of the present invention is characterized by containing (A) an epoxy resin, (B) an active ester-based curing agent, and (C) a compound containing a structural unit represented by the formula (C1) and a terminal group represented by the formula (c1).

[0017] As described above, the insulating material of the circuit board is required to exhibit good dielectric properties in order to reduce transmission loss when operating in a high-frequency environment. In this regard, when the compound described in Patent Document 1 is blended to such an extent that good dielectric properties are achieved, the present inventors have found that the resulting insulating material tends to deteriorate in adhesion strength with the conductor layer after exposure to a high-temperature and high-humidity environment.

[0018] On the other hand, according to the resin composition of the present invention that uses a combination of an epoxy resin, an active ester-based curing agent, and a compound containing a structural unit represented by the formula (C1) and an end group represented by the formula (c1), it exhibits good dielectric properties and can form a cured product having excellent adhesion strength with the conductor layer after exposure to a high-temperature and high-humidity environment. Therefore, the resin composition of the present invention significantly contributes to realizing a circuit board equipped with a circuit that advantageously reduces transmission loss when operating in a high-frequency environment and exhibits desired characteristics.

[0019] Hereinafter, each component contained in the resin composition will be described.

[0020] <(A) Epoxy resin> The resin composition of the present invention contains an epoxy resin as the component (A).

[0021] Examples of epoxy resins include bisphenol type epoxy resins, dicyclopentadiene type epoxy resins, trisphenol type epoxy resins, naphthol novolak type epoxy resins, phenol novolak type epoxy resins, tert-butyl-catechol type epoxy resins, naphthalene type epoxy resins, naphthol type epoxy resins, anthracene type epoxy resins, glycidylamine type epoxy resins, glycidyl ester type epoxy resins, cresol novolak type epoxy resins, biphenyl type epoxy resins, linear aliphatic epoxy resins, epoxy resins having a butadiene structure, alicyclic epoxy resins, heterocyclic epoxy resins, spiro ring-containing epoxy resins, cyclohexane type epoxy resins, cyclohexanedimethanol type epoxy resins, naphthylene ether type epoxy resins, trimethylol type epoxy resins, and tetraphenylethane type epoxy resins. Bisphenol type epoxy resins refer to epoxy resins having a bisphenol structure, and examples include bisphenol A type epoxy resins, bisphenol F type epoxy resins, bisphenol S type epoxy resins, and bisphenol AF type epoxy resins. Biphenyl type epoxy resins refer to epoxy resins having a biphenyl structure, and the biphenyl structure may have substituents such as an alkyl group, an alkoxy group, and an aryl group. Therefore, bixylenol type epoxy resins and biphenyl aralkyl type epoxy resins are also included in biphenyl type epoxy resins. The epoxy resin may be used alone or in combination of two or more.

[0022] As the epoxy resin, an aromatic epoxy resin is preferred. Here, the aromatic epoxy resin means an epoxy resin having an aromatic ring in its molecule.

[0023] The epoxy resin preferably has two or more epoxy groups in one molecule. When the non-volatile component of the epoxy resin is 100% by mass, the proportion of the epoxy resin having two or more epoxy groups in one molecule is preferably 50% by mass or more, more preferably 60% by mass or more, and still more preferably 70% by mass or more.

[0024] Epoxy resins include epoxy resins that are liquid at 20°C (hereinafter referred to as "liquid epoxy resins") and epoxy resins that are solid at 20°C (hereinafter referred to as "solid epoxy resins").

[0025] As the liquid epoxy resin, a liquid epoxy resin having two or more epoxy groups in one molecule is preferred.

[0026] Preferred liquid epoxy resins include bisphenol A type epoxy resins, bisphenol F type epoxy resins, bisphenol AF type epoxy resins, naphthalene type epoxy resins, glycidyl ester type epoxy resins, glycidyl amine type epoxy resins, phenol novolac type epoxy resins, alicyclic epoxy resins such as alicyclic epoxy resins having an ester skeleton, cyclohexane type epoxy resins, cyclohexanedimethanol type epoxy resins, and epoxy resins having a butadiene structure.

[0027] Specific examples of the liquid epoxy resin include "HP-4032", "HP-4032-D", "HP-4032-SS" (naphthalene type epoxy resin) manufactured by DIC Corporation; "828US", "jER828EL", "825", "Epicoat 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 novolac type epoxy resin) manufactured by Mitsubishi Chemical Corporation; "630", "630LSD" (glycidyl amine type epoxy resin) manufactured by Mitsubishi Chemical Corporation; "ZX1059" (a mixture of bisphenol A type epoxy resin and bisphenol F type epoxy resin) manufactured by Nippon Steel Chemical & Material Co., Ltd.; "EX-721" (glycidyl ester type epoxy resin) manufactured by Nagase ChemteX Corporation; "Celoxide 2021P" (alicyclic epoxy resin having an ester skeleton) manufactured by Daicel Corporation; "PB-3600" (epoxy resin having a butadiene structure) manufactured by Daicel Corporation; "ZX1658", "ZX1658GS" (liquid 1,4-glycidylcyclohexane type epoxy resin) manufactured by Nippon Steel Chemical & Material Co., Ltd., and the like.

[0028] As the solid epoxy resin, a solid epoxy resin having three or more epoxy groups in one molecule is preferred, and an aromatic solid epoxy resin having three or more epoxy groups in one molecule is more preferred.

[0029] As the solid epoxy resin, a bicyclol type epoxy resin, a naphthalene type epoxy resin, a naphthalene type tetrafunctional epoxy resin, a cresol novolak type epoxy resin, a dicyclopentadiene type epoxy resin, a trisphenol type epoxy resin, a naphthol type epoxy resin, a biphenyl type epoxy resin, a naphthylene ether type epoxy resin, an anthracene type epoxy resin, a bisphenol A type epoxy resin, a bisphenol AF type epoxy resin, a tetraphenylethane type epoxy resin are preferred.

[0030] Specific examples of the solid epoxy resin include "HP-4032H" (naphthalene-type epoxy resin) manufactured by DIC Corporation; "HP-4700" and "HP-4710" (naphthalene-type tetrafunctional epoxy resin) manufactured by DIC Corporation; "N-690" (cresol novolak-type epoxy resin) manufactured by DIC Corporation; "N-695" (cresol novolak-type epoxy resin) manufactured by DIC Corporation; "HP-7200HH", "HP-7200H", and "HP-7200" (dicyclopentadiene-type epoxy resin) manufactured by DIC Corporation; "EXA-7311", "EXA-7311-G3", "EXA-7311-G4", "EXA-7311-G4S", and "HP6000" (naphthylene ether-type epoxy resin) manufactured by DIC Corporation; "EPPN-502H" (trisphenol-type epoxy resin) manufactured by Nippon Kayaku Co., Ltd.; "NC-7000L" (naphthol novolak-type epoxy resin) manufactured by Nippon Kayaku Co., Ltd.; "NC-3000H", "NC-3000", "NC-3000L", and "NC-3100" (biphenyl-type epoxy resin) manufactured by Nippon Kayaku Co., Ltd.; "ESN-475V" (naphthol-type epoxy resin) manufactured by Nippon Steel Chemical & Material Co., Ltd.; "ESN-485" (naphthol novolak-type epoxy resin) manufactured by Nippon Steel Chemical & Material Co., Ltd.; "YX4000H", "YX4000", and "YL6121" (biphenyl-type epoxy resin) manufactured by Mitsubishi Chemical Corporation; "YX4000HK" (bixylenol-type epoxy resin) manufactured by Mitsubishi Chemical Corporation; "YX8800" (anthracene-type epoxy resin) manufactured by Mitsubishi Chemical Corporation; "PG-100" and "CG-500" manufactured by Osaka Gas Chemical Co., Ltd.; "YL7760" (bisphenol AF-type epoxy resin) manufactured by Mitsubishi Chemical Corporation; "YL7800" (fluorene-type epoxy resin) manufactured by Mitsubishi Chemical Corporation; "jER1010" (solid bisphenol A-type epoxy resin) manufactured by Mitsubishi Chemical Corporation; "jER1031S" (tetraphenylethane-type epoxy resin) manufactured by Mitsubishi Chemical Corporation, and the like.

[0031] The resin composition of the present invention may contain only a liquid epoxy resin, only a solid epoxy resin, or a combination of a liquid epoxy resin and a solid epoxy resin as the epoxy resin. When a liquid epoxy resin and a solid epoxy resin are used in combination, their quantitative ratio (liquid epoxy resin: solid epoxy resin) is preferably 1:0.01 to 1:50, more preferably 1:0.05 to 1:20, still more preferably 1:0.1 to 1:10, by mass ratio.

[0032] The epoxy equivalent of the epoxy resin is preferably 50 g / eq. to 5000 g / eq., more preferably 50 g / eq. to 3000 g / eq., still more preferably 80 g / eq. to 2000 g / eq., and even more preferably 110 g / eq. to 1000 g / eq. The epoxy equivalent is the mass of the epoxy resin containing 1 equivalent of epoxy groups. This epoxy equivalent can be measured according to JIS K7236.

[0033] The weight average molecular weight (Mw) of the epoxy resin is preferably 100 to 5000, more preferably 250 to 3000, still more preferably 400 to 1500. The Mw of the epoxy resin can be measured as a value in terms of polystyrene by gel permeation chromatography (GPC) method.

[0034] When the total content of the non-volatile components of components (A) to (C) in the resin composition is 100% by mass, the content of component (A) in the resin composition is preferably 10% by mass or more, more preferably 20% by mass or more, still more preferably 25% by mass or more, 30% by mass or more, or 35% by mass or more, and preferably 60% by mass or less, more preferably 50% by mass or less, still more preferably 45% by mass or less, or 40% by mass or less.

[0035] When the resin composition of the present invention contains components other than the components (A) to (C), the content of the component (A) in the resin composition is preferably 1% by mass or more, more preferably 3% by mass or more, still more preferably 5% by mass or more, 6% by mass or more, or 7% by mass or more, and preferably 50% by mass or less, more preferably 40% by mass or less, still more preferably 30% by mass or less, 20% by mass or less, or 10% by mass or less, based on 100% by mass of the non-volatile components in the resin composition.

[0036] When the resin composition of the present invention contains components other than the components (A) to (C), the content of the component (A) in the resin composition is preferably 10% by mass or more, more preferably 20% by mass or more, still more preferably 25% by mass or more, or 27% by mass or more, and preferably 60% by mass or less, more preferably 50% by mass or less, still more preferably 40% by mass or less, or 35% by mass, based on 100% by mass of the resin components in the resin composition.

[0037] In the present invention, the "resin component" referred to for the resin composition means the components excluding the (D) inorganic filler described below among the non-volatile components constituting the resin composition.

[0038] <(B) Active ester-based curing agent> The resin composition of the present invention contains an active ester-based curing agent as the component (B). The active ester-based curing agent may be used alone or in combination of two or more.

[0039] As the active ester-based curing agent, a compound having one or more active ester groups in one molecule can be used. Among them, as the active ester-based curing agent, compounds having two or more highly reactive ester groups in one molecule, such as phenolic esters, thiophenolic esters, N-hydroxyamine esters, esters of heterocyclic hydroxy compounds, etc., are preferred. The active ester-based curing agent is preferably obtained by a condensation reaction of a carboxylic acid compound and / or a thiocarboxylic acid compound with a hydroxy compound and / or a thiol compound. Further, from the viewpoint of improving heat resistance, an active ester-based curing agent derived from a carboxylic acid compound is preferred, an active ester-based curing agent obtained from a carboxylic acid compound and a hydroxy compound is more preferred, and an active ester-based curing agent obtained from a carboxylic acid compound and an aromatic hydroxy compound is even more preferred.

[0040] As the carboxylic acid compound, either an aromatic carboxylic acid compound or an aliphatic carboxylic acid compound may be used. For example, benzoic acid, acetic acid, succinic acid, maleic acid, itaconic acid, phthalic acid, isophthalic acid, terephthalic acid, pyromellitic acid, and their halides, etc. can be mentioned.

[0041] Examples of the aromatic hydroxy compound include (i) a polyaddition reaction product of an unsaturated aliphatic cyclic compound containing two double bonds in one molecule and phenols, (ii) various bisphenol compounds, (iii) an aromatic polyol having two or more hydroxy groups bonded to a carbon atom on the aromatic ring, (iv) an aromatic monool having one hydroxy group bonded to a carbon atom on the aromatic ring, etc. Examples of the polyaddition reaction product of the unsaturated aliphatic cyclic compound and phenols include polyaddition reaction products of unsaturated aliphatic cyclic compounds such as dicyclopentadiene, tetrahydroindene, norbornadiene, limonene, vinylcyclohexene, etc. and phenols which may have a substituent (for example, phenol, cresol, xylenol, ethylphenol, propylphenol, vinylphenol, allylphenol, phenylphenol, benzylphenol, halophenol, etc.), and specifically, for example, dicyclopentadiene-phenols polyaddition product, etc. Examples of the bisphenol compound include bisphenol A, bisphenol F, bisphenol AF, bisphenol AP, bisphenol B, bisphenol BP, bisphenol C, bisphenol M, etc. Examples of the aromatic polyol having two or more hydroxy groups bonded to a carbon atom on the aromatic ring include hydroquinone, resorcin, catechol, 1,5-dihydroxynaphthalene, 1,6-dihydroxynaphthalene, 2,6-dihydroxynaphthalene, dihydroxybenzophenone, trihydroxybenzophenone, tetrahydroxybenzophenone, phloroglucin, benzenetriol, phenol novolak, etc. Examples of the aromatic monool having one hydroxy group bonded to a carbon atom on the aromatic ring include phenol, cresol, xylenol, ethylphenol, propylphenol, vinylphenol, allylphenol, phenylphenol, benzylphenol, halophenol, naphthol, methylnaphthol, dimethylnaphthol, ethylnaphthol, propylnaphthol, vinylnaphthol, allylnaphthol, phenylnaphthol, benzylnaphthol, halonaphthol, etc.

[0042] Specific examples of the preferred active ester-based curing agent from the viewpoint of more enjoying the effects of the present invention include an active ester-based curing agent containing a dicyclopentadiene type diphenol structure, an active ester-based curing agent containing a naphthalene structure, an active ester-based curing agent containing an acetylated product of phenol novolac, and an active ester-based curing agent containing a benzoylated product of phenol novolac. Among them, from the viewpoint of realizing a cured product that exhibits both good dielectric properties and good adhesion strength to the conductor layer after exposure to a high-temperature and high-humidity environment in combination with the component (A) and the component (C), an active ester-based curing agent containing a naphthalene structure and an active ester-based curing agent containing a dicyclopentadiene type diphenol structure are more preferred. The "dicyclopentadiene type diphenol structure" represents a divalent structural unit composed of phenylene-dicyclopentylene-phenylene.

[0043] (B) component may be a commercially available product. Examples of the commercially available product include, as an active ester-based curing agent containing a dicyclopentadiene type diphenol structure, "EXB-9451", "EXB-9460", "EXB-9460S", "HPC-8000-65T", "HPC-8000H-65TM", "HPC-8000L-65TM" (manufactured by DIC Corporation); as an active ester-based curing agent containing a naphthalene structure, "EXB-8100L-65T", "EXB-8150-60T", "EXB-8150-62T", "EXB-9416-70BK", "HPC-8150-60T", "HPC-8150-62T", "HP-B-8151-62T" (manufactured by DIC Corporation); as a phosphorus-containing active ester-based curing agent, "EXB9401" (manufactured by DIC Corporation); as an active ester-based curing agent that is an acetylated product of phenol novolac, "DC808" (manufactured by Mitsubishi Chemical Corporation); as an active ester-based curing agent that is a benzoylated product of phenol novolac, "YLH1026", "YLH1030", "YLH1048" (manufactured by Mitsubishi Chemical Corporation); and as an active ester-based curing agent containing a styryl group and a naphthalene structure, "PC1300-02-65MA" (manufactured by Air Water, Inc.), etc.

[0044] (B) component's active ester group equivalent weight is preferably 50 g / eq. to 500 g / eq., more preferably 50 g / eq. to 400 g / eq., still more preferably 100 g / eq. to 300 g / eq. The active ester group equivalent weight is the mass of the active ester resin per 1 equivalent of the active ester group.

[0045] (A) component and (B) component's quantitative ratio, in the ratio of [total number of epoxy groups of (A) component]:[total number of active ester groups of (B) component], preferably ranges from 1:0.01 to 1:10, more preferably 1:0.05 to 1:8, still more preferably 1:0.1 to 1:5. Regarding the "total number of epoxy groups of the epoxy resin", it is as described above. Also, the "total number of active ester groups of (B) component" is the total value obtained by summing up the values obtained by dividing the mass of the non-volatile component of (B) component present in the resin composition by the active ester group equivalent weight. By setting the quantitative ratio of (A) component and (B) component within such a range, the effects of the present invention can be significantly obtained.

[0046] From the viewpoint of easily realizing a resin composition that provides good dielectric properties, when the total of the non-volatile components of (A) to (C) components in the resin composition is 100% by mass, the content of (B) component in the resin composition is preferably 10% by mass or more, more preferably 20% by mass or more, still more preferably 25% by mass or more, 30% by mass or more, or 35% by mass or more. The upper limit of the content is not particularly limited and may be determined according to the properties required for the resin composition. For example, it may be 80% by mass or less, 70% by mass or less, or 60% by mass or less.

[0047] From the viewpoint of providing a cured product with good dielectric properties, the mass ratio of (B) component to (A) component ((content of (B) component / content of (A) component)) in the resin composition of the present invention is preferably 0.6 or more, more preferably 0.8 or more, still more preferably 1.0 or more, and preferably 2.0 or less, more preferably 1.9 or less, still more preferably 1.8 or less, or 1.7 or less.

[0048] When the resin composition of the present invention contains components other than components (A) to (C), the content of component (B) in the resin composition is preferably 1% by mass or more, more preferably 3% by mass or more, still more preferably 5% by mass or more, 6% by mass or more, or 7% by mass or more, and preferably 50% by mass or less, more preferably 40% by mass or less, still more preferably 30% by mass or less, 20% by mass or less, or 15% by mass or less, when the non-volatile components in the resin composition are 100% by mass.

[0049] When the resin composition of the present invention contains components other than components (A) to (C), the content of component (B) in the resin composition is preferably 10% by mass or more, more preferably 20% by mass or more, still more preferably 25% by mass or more, or 30% by mass or more, and preferably 80% by mass or less, more preferably 70% by mass or less, still more preferably 60% by mass or less, or 55% by mass, when the resin components in the resin composition are 100% by mass.

[0050] <Compound containing a structural unit represented by formula (C1) and a terminal group represented by formula (c1)> The resin composition of the present invention contains, as component (C), a compound containing a structural unit represented by the following formula (C1) (also referred to as "specific structural unit") and a terminal group represented by formula (c1) (also referred to as "specific terminal group").

[0051]

Chemical formula

[0052] (In formula (C1), R 1 each independently represents a divalent organic group; R 2 each independently represents a divalent nitrogen-containing heteroaromatic group which may have a substituent; X each independently represents -O-, -S-, or -N(R 3 )-; R 3represents a hydrogen atom, a monovalent hydrocarbon group having 1 to 20 carbon atoms, a monovalent halogenated hydrocarbon group having 1 to 20 carbon atoms, or a group in which a part of the hydrocarbon group or the halogenated hydrocarbon group is substituted with at least one selected from an oxygen atom and a sulfur atom; * represents a bonding site.)

[0053] [Chemical formula]

[0054] (In formula (c1), Y represents a monovalent organic group having 3 to 50 carbon atoms containing a radically polymerizable group, a monovalent aromatic group having 8 to 50 carbon atoms which may have a substituent (provided that a hydroxy group and a radically polymerizable group are excluded), or a monovalent aliphatic group having 3 to 50 carbon atoms which may have a substituent (provided that a hydroxy group and a radically polymerizable group are excluded); * represents a bonding site.)

[0055] In formula (C1), R 1 represents a divalent organic group. The divalent organic group may contain heteroatoms such as an oxygen atom and a nitrogen atom. Among them, R 1 preferably contains a group represented by the following formula (C2).

[0056] [Chemical formula]

[0057] (In formula (C2), Ar 1 and Ar 2 each independently represent a divalent aromatic group which may have a substituent; L each independently represents a single bond or a divalent linking group; R 4 and R 5 each independently represent a single bond or an alkylene group having 1 to 4 carbon atoms; y represents 0 or an integer of 1 to 5; * represents a binding site.)

[0058] In formula (C2), Ar 1 and Ar 2 each independently represent a divalent aromatic group which may have a substituent. Among them, Ar 1 and Ar 2 are preferably divalent aromatic groups having 6 to 30 carbon atoms, more preferably a phenylene group, a naphthylene group, an anthracenylene group, or a biphenylene group (-C6H4-C6H4-), and still more preferably a phenylene group or a naphthylene group.

[0059] Ar 1 and Ar 2 The substituents that Ar

[0060] and Ar 1 and Ar 2 may have are not particularly limited. For example, a halogen atom, a monovalent hydrocarbon group having 1 to 20 carbon atoms, a halogenated hydrocarbon group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an alkylthio group having 1 to 20 carbon atoms, a nitro group, a cyano group, a carboxyl group, a sulfo group, a phosphono group, a phosphate group, a hydroxy group, or a primary to tertiary amino group can be mentioned. Among them, as the substituent, a monovalent hydrocarbon group having 1 to 20 carbon atoms is preferable, and one or more substituents selected from a methyl group, a vinyl group, and an allyl group are more preferable.

[0061] In formula (C2), L represents a single bond or a divalent linking group. Examples of the divalent linking group include divalent groups composed of one or more (for example, 1 to 3000, 1 to 1000, 1 to 100, 1 to 50) skeleton atoms selected from a carbon atom, an oxygen atom, a nitrogen atom, and a sulfur atom. Examples of the divalent linking group include, for example, an alkylene group, an alkenylene group, an arylene group, a heteroarylene group, -O-, -C(=O)-, -C(=O)-O-, -N(R 6 )- (wherein R 6represents a hydrogen atom, a monovalent hydrocarbon group having 1 to 20 carbon atoms, or a monovalent halogenated hydrocarbon group having 1 to 20 carbon atoms.), -C(=O)-NH-, -NC(=O)N-, -S-, -S(=O)-, -S(O)2-, etc. may be mentioned, and a group obtained by combining a plurality of these may also be used. Among them, L is preferably any one of a single bond, -O-, -C(=O)-, -C(=O)-O-, -S-, -S(O)2-, and a divalent group represented by the following formulas (C3-1) to (C3-4), and more preferably any one of a divalent group represented by the following formulas (C4-1) to (C4-3).

[0062]

Chemical formula

[0063] (In formulas (C3-1) to (C3-4), R A1 each independently represents a monovalent group selected from a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, an aryl group having 6 to 14 carbon atoms, and an arylalkyl group having 7 to 15 carbon atoms; R A2 each independently represents a monovalent group selected from a halogen atom, an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, a cycloalkoxy group having 3 to 12 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an aryl group having 6 to 14 carbon atoms, an aryloxy group having 6 to 14 carbon atoms, an arylalkyl group having 7 to 15 carbon atoms, and an arylalkyloxy group having 7 to 15 carbon atoms; m1 represents an integer of 1 to 10; m2 represents an integer of 2 to 7; m3 and m4 each independently represent 0 or an integer of 1 to 4; * represents a bonding site.)

[0064]

Chemical formula

[0065] (In formulas (C4-1) to (C4-3), R B1 each independently represents a monovalent group selected from a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, and an aryl group having 6 to 14 carbon atoms; R B2 each independently represents a monovalent group selected from an alkyl group having 1 to 4 carbon atoms and an aryl group having 6 to 14 carbon atoms; m5 and m6 each independently represent 0 or an integer of 1 to 4; * represents a bonding site.)

[0066] In formulas (C3-1) to (C3-4), R A1 each independently represents a monovalent group selected from a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, an aryl group having 6 to 14 carbon atoms, and an arylalkyl group having 7 to 15 carbon atoms. Also, R A2 each independently represents a monovalent group selected from a halogen atom, an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, a cycloalkoxy group having 3 to 12 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an aryl group having 6 to 14 carbon atoms, an aryloxy group having 6 to 14 carbon atoms, an arylalkyl group having 7 to 15 carbon atoms, and an arylalkyloxy group having 7 to 15 carbon atoms.

[0067] R A1 or R A2 Examples of the alkyl group having 1 to 12 carbon atoms represented by include a methyl group, an ethyl group, a propyl group, a butyl group, and the like.

[0068] R A1 or R A2 Examples of the aryl group having 6 to 14 carbon atoms represented by include a phenyl group, a naphthyl group, an anthracenyl group, a biphenyl group (-C6H4-C6H5), and the like.

[0069] R A1 or R A2Examples of the arylalkyl group having 7 to 15 carbon atoms represented by include a benzyl group, a phenylethyl group and the like.

[0070] R A2 Examples of the alkoxy group having 1 to 10 carbon atoms represented by include a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentoxy group, a hexoxy group, a heptoxy group, an octoxy group and the like.

[0071] R A2 Examples of the cycloalkyl group having 3 to 12 carbon atoms represented by include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group and the like.

[0072] R A2 Examples of the cycloalkoxy group having 3 to 12 carbon atoms represented by include a cyclopropyloxy group, a cyclobutyloxy group and the like.

[0073] R A2 Examples of the alkenyl group having 2 to 10 carbon atoms represented by include a methenyl group, an ethenyl group, a propenyl group and the like.

[0074] R A2 Examples of the aryloxy group having 6 to 14 carbon atoms represented by include a phenyloxy group, a naphthyloxy group and the like.

[0075] R A2 Examples of the arylalkyloxy group having 7 to 15 carbon atoms represented by include a benzyloxy group, a phenylethyloxy group and the like.

[0076] In formula (C3-1), m1 represents an integer of 1 to 10, preferably an integer of 1 to 6.

[0077] In formula (C3-3), m2 represents an integer of 2 to 7, preferably 4 or 5.

[0078] In formula (C3-4), m3 and m4 each independently represent an integer of 0 or 1 to 4, preferably 0 or 1, and more preferably 0.

[0079] In formulas (C4-1) to (C4-3), R B1 each independently represents a monovalent group selected from a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, and an aryl group having 6 to 14 carbon atoms. Also, R B2 each independently represents a monovalent group selected from an alkyl group having 1 to 4 carbon atoms, and an aryl group having 6 to 14 carbon atoms.

[0080] R B1 or R B2 Examples of the alkyl group having 1 to 4 carbon atoms represented by are a methyl group, an ethyl group, a propyl group, a butyl group, and the like.

[0081] R B1 or R B2 Examples of the aryl group having 6 to 14 carbon atoms represented by are a phenyl group, a naphthyl group, and the like.

[0082] In formula (C4-3), m5 and m6 each independently represent an integer of 0 or 1 to 4, preferably 0 or 1, and more preferably 0.

[0083] In formula (C2), R that the divalent linking group represented by L may have 6 represents a hydrogen atom, a monovalent hydrocarbon group having 1 to 20 carbon atoms, or a monovalent halogenated hydrocarbon group having 1 to 20 carbon atoms.

[0084] R 6Examples of the monovalent hydrocarbon group having 1 to 20 carbon atoms represented by include a monovalent group composed of a monovalent aliphatic group, a monovalent aromatic group, or a combination thereof. The monovalent aliphatic group may be either a monovalent saturated aliphatic group or a monovalent unsaturated aliphatic group. The monovalent aliphatic group may be a chain hydrocarbon group, a cyclic hydrocarbon group (i.e., an alicyclic hydrocarbon group), or a combination thereof. Further, the chain hydrocarbon group may be either linear or branched.

[0085] R 6Specific examples of the monovalent aliphatic group represented by include an alkyl group and the like. Examples of the alkyl group include a methyl group, an ethyl group, an n-propyl group, a 2-propyl group, an n-butyl group, an isobutyl group, a t-butyl group, an n-pentyl group, a 1-ethylpropyl group, a 1-methylbutyl group, a 2-methylbutyl group, a 3-methylbutyl group, an amyl group, a cyclopentyl group, a 2,2-dimethylpropyl group, a 1,1-dimethylpropyl group, an n-hexyl group, a cyclohexyl group, a 1-ethylbutyl group, a 2-ethylbutyl group, a 3-ethylbutyl group, a 1-methylpentyl group, a 2-methylpentyl group, a 3-methylpentylene group, a 4-methylpentylene group, a 1,1-dimethylbutylene group, a 2,2-dimethylbutylene group, a 3,3-dimethylbutyl group, a 1,2-dimethylbutyl group, a 1,3-dimethylbutyl group, a 2,3-dimethylbutyl group, an n-heptyl group, a 1-methylhexyl group, a 2-methylhexyl group, a 3-methylhexyl group, a 4-methylhexyl group, a 5-methylhexyl group, a 1-ethylpentyl group, a 2-ethylpentyl group, a 3-ethylpentyl group, a 1,1-dimethylpentyl group, a 2,2-dimethylpentyl group, a 3,3-dimethylpentyl group, a 4,4-dimethylpentyl group, a 1,2-dimethylpentyl group, a 1,3-dimethylpentyl group, a 1,4-dimethylpentyl group, a 2,3-dimethylpentyl group, a 2,4-dimethylpentyl group, a 3,4-dimethylpentyl group, a 2-methyl-3,3-dimethylbutyl group, a 1-methyl-3,3-dimethylbutyl group, a 1,2,3-trimethylbutyl group, a 1,3-dimethyl-2-pentyl group, a 2-isopropylbutyl group, a 2-methylcyclohexyl group, a 3-methylcyclohexyl group, a 4-methylcyclohexyl group, a 1-cyclohexylmethyl group, a 2-ethylcyclopentyl group, a 3-ethylcyclopentyl group, a 2,3-dimethylcyclopentyl group, a 2,4-dimethylcyclopentyl group, a 2-methylcyclopentylmethyl group, a 2-cyclopentylethyl group, a 1-cyclopentylethyl group, an n-octyl group, a 2-octyl group, a 3-octyl group, a 4-octyl group, a 2-methylheptyl group, a 3-methylheptyl group, a 4-methylheptyl group, a 5-methylheptyl group, a 6-methylheptyl group, a 2-ethylhexyl group, a 3-ethylhexyl group, a 4-ethylhexyl group, a 5-ethylhexyl group, a 1,1-dimethylhexyl group, a 2,2-dimethylhexyl group, 3,3-dimethylhexyl group, 4,4-dimethylhexyl group, 5,5-dimethylhexyl group, 1,2-dimethylhexyl group, 1,3-dimethylhexyl group, 1,4-dimethylhexyl group, 1,5-dimethylhexyl group, 2,3-dimethylhexyl group, 2,4-dimethylhexyl group, 2,5-dimethylhexyl group, 1,1-ethylmethylpentyl group, 2,2-ethylmethylpentyl group, 3,3-ethylmethylpentyl group, 4,4-ethylmethylpentyl group, 1-ethyl-2-methylpentyl group, 1-ethyl-3-methylpentyl group, 1-ethyl-4-methylpentyl group, 2-ethyl-1-methylpentyl group, 3-ethyl-1-methylpentyl group, 4-ethyl-1-methylpentyl group, 2-ethyl-3-methylpentyl group, 2-ethyl-4-methylpentyl group, 3-ethyl-2-methylpentyl group, 4-ethyl-3-methylpentyl group, 3-ethyl-4-methylpentyl group, 4-ethyl-3-methylpentyl group, 1-(2-methylpropyl)butyl group, 1-(2-methylpropyl)-2-methylbutyl group, 1,1-(2-methylpropyl)ethyl group, 1,1-(2-methylpropyl)ethylpropyl group, 1,1-diethylpropyl group, 2,2-diethylpropyl group, 1,1-ethylmethyl-2,2-dimethylpropyl group, 2,2-ethylmethyl-1,1-dimethylpropyl group, 2-ethyl-1,1-dimethylbutyl group, 2,3-dimethylcyclohexyl group, 2,3-dimethylcyclohexyl group, 2,5-dimethylcyclohexyl group, 2,6-dimethylcyclohexyl group, 3,5-dimethylcyclohexyl group, 2-methylcyclohexylmethyl group, 3-methylcyclohexylmethyl group, 4-methylcyclohexylmethyl group, 2-ethylcyclohexyl group, 3-ethylcyclohexyl group, 4-ethylcyclohexyl group, 2-cyclohexylethyl group, 1-cyclohexylethyl group, 1-cyclohexyl-2-ethylene group, nonyl group, isononyl group, decyl group, isodecyl group, undecyl group, dodecyl group, propargyl group, etc. are included.,

[0086] R 6Specific examples of the monovalent aromatic group represented by include aryl groups and the like. Examples of the aryl group include a phenyl group, a naphthyl group, an anthracenyl group, a biphenyl group (-C6H4-C6H5), and the like.

[0087] R 6 Examples of the "monovalent group composed of these combinations" represented by include a benzyl group, a 2-phenylethyl group, and the like.

[0088] R 6 Examples of the monovalent halogenated hydrocarbon group having 1 to 20 carbon atoms represented by include groups in which some or all of the hydrogen atoms of the above-mentioned "monovalent hydrocarbon group having 1 to 20 carbon atoms represented by " are substituted with halogen atoms. 6 Examples of the monovalent hydrocarbon group having 1 to 20 carbon atoms represented by include groups in which some or all of the hydrogen atoms of the above-mentioned "monovalent hydrocarbon group having 1 to 20 carbon atoms represented by " are substituted with halogen atoms.

[0089] In formula (C2), R 4 and R 5 each independently represent a single bond or an alkylene group having 1 to 4 carbon atoms. Examples of the alkylene group having 1 to 4 carbon atoms include a methylene group, an ethylene group, an n-propylene group, an isopropylene group, an n-butylene group, a sec-butylene group, and the like. R 4 and R 5 are preferably a single bond, a methylene group, or an ethylene group.

[0090] In formula (C2), y represents 0 or an integer of 1 to 5, preferably 0 or an integer of 1 to 4, and more preferably 0 or an integer of 1 to 3.

[0091] In formula (C1), R 2 each independently represents a divalent nitrogen-containing heteroaromatic group which may have a substituent. The divalent nitrogen-containing heteroaromatic group means a group obtained by removing two hydrogens from the nitrogen-containing heteroaromatic ring of a nitrogen-containing heteroaromatic compound. Examples of the nitrogen-containing heteroaromatic ring include a pyrrole ring, a pyridine ring, a pyrimidine ring, a pyrazine ring, a pyridazine ring, a triazine ring, a quinoline ring, an isoquinoline ring, a quinoxaline ring, a phthalazine ring, a quinazoline ring, a naphthyridine ring, a carbazole ring, an acridine ring, and a phenazine ring. R 2is preferably a divalent group consisting of a pyrimidine ring which may have a substituent.

[0092] R 2 Examples of the substituent that R may have include, for example, a halogen atom, a monovalent hydrocarbon group having 1 to 20 carbon atoms, a monovalent halogenated hydrocarbon group having 1 to 20 carbon atoms, or a group in which a part of the hydrocarbon group or the halogenated hydrocarbon group is substituted with at least one selected from an oxygen atom and a sulfur atom, a nitro group, a cyano group, an amino group, and the like.

[0093] In formula (C1), X independently represents -O-, -S-, or -N(R 3 )-. Further, R represented by the group represented by X 3 represents a hydrogen atom, a monovalent hydrocarbon group having 1 to 20 carbon atoms, a monovalent halogenated hydrocarbon group having 1 to 20 carbon atoms, or a group in which a part of the hydrocarbon group or the halogenated hydrocarbon group is substituted with at least one selected from an oxygen atom and a sulfur atom.

[0094] R 3 Examples of the monovalent hydrocarbon group having 1 to 20 carbon atoms represented by R 7 are the same as those of the monovalent hydrocarbon group having 1 to 20 carbon atoms represented by R

[0095] R 3 Examples of the monovalent halogenated hydrocarbon group having 1 to 20 carbon atoms represented by R 6 are the same as those of the monovalent halogenated hydrocarbon group having 1 to 20 carbon atoms represented by R

[0096] R 3 Examples of the "group in which a part of the hydrocarbon group or the halogenated hydrocarbon group is substituted with at least one selected from an oxygen atom and a sulfur atom" represented by R 3 include, for example, a monovalent hydrocarbon group having 1 to 20 carbon atoms represented by R 3Examples of the part of the monovalent halogenated hydrocarbon group having 1 to 20 carbon atoms represented by include groups substituted with groups such as -O-, -S-, -C(=O)-, -C(=O)-O-, -S(=O)-, and -S(O)2-.

[0097] In formula (c1), Y represents a monovalent organic group having 3 to 50 carbon atoms containing a radical polymerizable group, a monovalent aromatic group having 6 to 50 carbon atoms which may have a substituent (excluding a hydroxy group and a radical polymerizable group), or a monovalent aliphatic group having 3 to 50 carbon atoms which may have a substituent (excluding a hydroxy group and a radical polymerizable group). The group represented by Y preferably contains at least one of a monovalent aromatic group containing a radical polymerizable group and an unsubstituted monovalent aromatic group.

[0098] Examples of the radical polymerizable group that the group represented by Y may have include a vinyl group, an allyl group, an isopropenyl group, a vinylphenyl group, an acryloyl group, a methacryloyl group, a fumaroyl group, and a maleoyl group.

[0099] The "monovalent organic group having 3 to 50 carbon atoms containing a radical polymerizable group" represented by Y may contain only a radical polymerizable group, or may contain a radical polymerizable group via a divalent linking group. Examples of the divalent linking group include an alkylene group, an alkenylene group, an arylene group, a heteroarylene group, -O-, -C(=O)-, -C(=O)-O-, -NH-, -C(=O)-NH-, -NC(=O)N-, -S-, -S(=O)-, -S(O)2-, etc., and a group formed by combining a plurality of these may also be used. Among them, the divalent linking group is preferably an alkylene group, and more preferably a methylene group.

[0100] In a preferred embodiment, the "monovalent organic group having 3 to 50 carbon atoms containing a radical polymerizable group" represented by Y contains a monovalent aromatic group containing a radical polymerizable group. Among them, the organic group is preferably a monovalent group selected from a vinylphenyl group, an allylphenyl group, an isopropenylphenyl group, and a vinylbenzyl group, and more preferably a vinylbenzyl group.

[0101] In the “monovalent aromatic group having 6 to 50 carbon atoms which may have a substituent (excluding a hydroxy group and a radically polymerizable group)” represented by Y, the monovalent aromatic group is as described above.

[0102] In a preferred embodiment, the “monovalent aromatic group having 6 to 50 carbon atoms which may have a substituent (excluding a hydroxy group and a radically polymerizable group)” represented by Y is an unsubstituted monovalent aromatic group. Among them, the aromatic group is preferably an unsubstituted monovalent nitrogen-containing heteroaromatic group. The monovalent nitrogen-containing heteroaromatic group means a group obtained by removing one hydrogen from a nitrogen-containing heteroaromatic ring of a nitrogen-containing heteroaromatic compound. The nitrogen-containing heteroaromatic ring is as described above. The “monovalent aromatic group having 6 to 50 carbon atoms which may have a substituent (excluding a hydroxy group and a radically polymerizable group)” represented by Y is more preferably a monovalent group consisting of an unsubstituted pyrimidine ring.

[0103] In the “monovalent aliphatic group having 3 to 50 carbon atoms which may have a substituent (excluding a hydroxy group and a radically polymerizable group)” represented by Y, the monovalent aliphatic group is as described above. The aliphatic group is preferably a monovalent cyclic hydrocarbon group.

[0104] The substituent that the group represented by Y may have is a group other than a hydroxy group and a radically polymerizable group. Examples of the substituent include a halogen atom, a monovalent hydrocarbon group having 1 to 20 carbon atoms, a halogenated hydrocarbon group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an alkylthio group having 1 to 20 carbon atoms, a nitro group, a cyano group, a carboxyl group, a sulfo group, a phosphono group, a phosphoric acid group, a primary to tertiary amino group, and the like.

[0105] In a preferred embodiment, the component (C) contains a group represented by Y via a divalent linking group. Among them, the component (C) preferably contains at least one of the terminal groups represented by the following formula (c2-1) and the following formula (c2-2).

[0106] [Chemical formula]

[0107] (In formulas (c2-1) and (c2-2), X’ represents a single bond, -O-, -S-, or -N(R 3 )); Each of the other symbols is as defined above.)

[0108] In formulas (c2-1) and (c2-2), X’ represents a single bond, -O-, -S-, or -N(R 3 ). Regarding R that the group represented by X’ may have 3 it is as defined above.

[0109] In a preferred embodiment, component (C) is a compound represented by the following formula (C5-1) or the following formula (C5-2).

[0110] [Chemical formula]

[0111] (In formulas (C5-1) and (C5-2), n represents an integer of 0 or 1 to 100; Each of the other symbols is as defined above.)

[0112] In formulas (C5-1) and (C5-2), n represents an integer of 0 or 1 to 100, preferably an integer of 2 to 30.

[0113] Component (C) may be synthesized by a known method. Component (C) is, for example, a compound that is a raw material for a structure containing a group represented by R 1 and a compound that is a raw material for a structure containing a group represented by R 2A compound serving as a raw material for a structure containing a group represented by , a compound serving as a raw material for a structure containing a group represented by Y, and, if necessary, a compound for deriving other structural units can be synthesized by heating in an organic solvent together with an alkali metal, an alkali metal compound, or the like. The compound serving as a raw material for a structure containing a group represented by Y and the compound for deriving other structural units are R 1 After reacting the compound serving as a raw material for a structure containing a group represented by , and the compound serving as a raw material for a structure containing a group represented by R 2 They may be heated and mixed for reaction.

[0114] In the synthesis of the component (C), R 1Examples of the compound serving as a raw material for the structure containing the group represented by include dihydroxy phenyl compounds such as hydroquinone, resorcinol, catechol, phenylhydroquinone; 9,9-bis(4-hydroxyphenyl)fluorene, 9,9-bis(4-hydroxy-3-methylphenyl)fluorene, 9,9-bis(4-hydroxy-3-phenylphenyl)fluorene, 1,1-bis(4-hydroxyphenyl)-1-phenylethane, bis(4-hydroxyphenyl)diphenylmethane, 2,2-bis(4-hydroxyphenyl)propane, 2,2-bis(4-hydroxy-3-allylphenyl)propane, 2,2-bis(4-hydroxy-3-methylphenyl)propane, 2,2-bis(4-hydroxy-3-phenylphenyl)propane, 4,4'-(1,3-dimethylbutylidene)bisphenol, 1,1-bis(4-hydroxyphenyl)-nonane, bis(4-hydroxyphenyl)sulfone, 1,1-bis(4-hydroxyphenyl)cyclohexane, 1,1-bis(4-hydroxyphenyl)-3,3,5-trimethylcyclohexane, 1,1-bis(3-methyl-4-hydroxyphenyl)-3,3,5-trimethylcyclohexane, 1,1-bis(3-cyclohexyl-4-hydroxyphenyl)-3,3,5-trimethylcyclohexane, 1,4-bis[2-(4-hydroxyphenyl)-2-propyl]benzene, 1,3-bis[2-(4-hydroxyphenyl)-2-propyl]benzene, 4,4'-cyclododecylidene bisphenol, 4,4'-decylidene bisphenol and other bisphenol compounds; diol compounds such as "Preplast 1901", "Preplast 1838", "Preplast 3186", "Preplast 3192", "Preplast 3197", "Preplast 3199" manufactured by Kuraray Japan Co., Ltd.; etc. These compounds may be used alone or in combination of two or more.

[0115] (C) component synthesis, R 2Examples of the compound serving as a raw material for the structure containing the group represented by include pyrimidine compounds such as 4,6-dichloropyrimidine, 4,6-dibromopyrimidine, 2,4-dichloropyrimidine, 2,5-dichloropyrimidine, 2,5-dibromopyrimidine, 5-bromo-2-chloropyrimidine, 5-bromo-2-fluoropyrimidine, 5-bromo-2-iodopyrimidine, 2-chloro-5-fluoropyrimidine, 2-chloro-5-iodopyrimidine, 2-phenyl-4,6-dichloropyrimidine, 2-methylthio-4,6-dichloropyrimidine, 2-methylsulfonyl-4,6-dichloropyrimidine, 5-methyl-4,6-dichloropyrimidine, 2-amino-4,6-dichloropyrimidine, 5-amino-4,6-dichloropyrimidine, 2,5-diamino-4,6-dichloropyrimidine, 4-amino-2,6-dichloropyrimidine, 5-methoxy-4,6-dichloropyrimidine, 5-methoxy-2,4-dichloropyrimidine, 2-methyl-4,6-dichloropyrimidine, 6-methyl-2,4-dichloropyrimidine, 5-methyl-2,4-dichloropyrimidine, 5-nitro-2,4-dichloropyrimidine, 4-amino-2-chloro-5-fluoropyrimidine, 2-methyl-5-amino-4,6-dichloropyrimidine, 5-bromo-4-chloro-2-methylthiopyrimidine; pyridazine compounds such as 3,6-dichloropyridazine, 3,5-dichloropyridazine, 4-methyl-3,6-dichloropyridazine; pyrazine compounds such as 2,3-dichloropyrazine, 2,6-dichloropyrazine, 2,5-dibromopyrazine, 2,6-dibromopyrazine, 2-amino-3,5-dibromopyrazine, 5,6-dicyano-2,3-dichloropyrazine; and the like. These compounds may be used alone or in combination of two or more.

[0116] In the synthesis of component (C), examples of the compounds serving as raw materials for the structure containing the group represented by Y include monohydric phenol compounds such as t-butylphenol, nonylphenol, 4-isopropenylphenol, 4-vinylphenol, 2-allylphenol, isoeugenol, tocotrienol, α-tocopherol, 4-hydroxyphenylmaleimide, 2-phenylphenol; monohydric amine compounds such as 4-hexylaniline, diallylamine; monohydric thiol compounds such as 1-octanethiol; monohydric aliphatic halides such as allyl chloride, 4-(chloromethyl)styrene, 3-(chloromethyl)styrene, and monohydric acid halides such as acryloyl chloride, methacryloyl chloride, crotonoyl chloride, cinnamoyl chloride, and monohydric acid anhydrides such as acrylic anhydride, crotonic anhydride, methacrylic anhydride; etc. These compounds may be used alone or in combination of two or more.

[0117] In the synthesis of component (C), examples of the compounds for inducing other structural units include compounds for inducing structural units containing carbonate bonds, thiocarbonate bonds or selenocarbonate bonds such as diphenyl carbonate, diphenyl thiocarbonate, diphenyl selenocarbonate, phosgene, thiophosgene, selenophosgene; dihydroxy compounds such as benzenedimethanol, cyclohexanedimethanol; phosphine oxide compounds such as bis(fluorophenyl)phenylphosphine oxide, bis(fluorophenyl)naphthylphosphine oxide, bis(fluorophenyl)anthrylphosphine oxide; dihalides of dicarboxylic acids such as phthalic dichloride, isophthalic dichloride, terephthalic dichloride; etc. These compounds may be used alone or in combination of two or more.

[0118] In the synthesis of component (C), when an alkali metal and an alkali metal compound are used as raw materials in the case of using a compound having a hydroxy group such as a phenol compound, they react with the compound having a hydroxy group to form an alkali metal salt. Examples of such alkali metals and alkali metal compounds include alkali metals such as lithium, sodium, and potassium; alkali metal hydrides such as lithium hydride, sodium hydride, and potassium hydride; alkali metal hydroxides such as lithium hydroxide, sodium hydroxide, and potassium hydroxide; alkali metal carbonates such as lithium carbonate, sodium carbonate, and potassium carbonate; and alkali metal hydrogen carbonates such as lithium hydrogen carbonate, sodium hydrogen carbonate, and potassium hydrogen carbonate. Among them, alkali metal carbonates are preferred, and potassium carbonate is more preferred.

[0119] In the synthesis of component (C), examples of the organic solvent include ether solvents such as tetrahydrofuran (THF), dioxane, cyclopentyl methyl ether, anisole, phenetole, diphenyl ether, dialkoxybenzene, and trialkoxybenzene; nitrogen-containing solvents such as N,N-dimethylacetamide (DMAc), N,N-dimethylformamide, N-methyl-2-pyrrolidone, and 1,3-dimethyl-2-imidazolidinone; ester solvents such as γ-butyrolactone; sulfur-containing solvents such as sulfolane, dimethyl sulfoxide, diethyl sulfoxide, dimethyl sulfone, diethyl sulfone, diisopropyl sulfone, and diphenyl sulfone; ketone solvents such as benzophenone, 2-heptanone, cyclohexanone, and methyl ethyl ketone; halogen solvents such as methylene chloride, chloroform, and chlorobenzene; and aromatic hydrocarbon solvents such as benzene, toluene, and xylene. Among them, 2-heptanone, cyclohexanone, N-methyl-2-pyrrolidone, toluene, and xylene are preferred, and N-methyl-2-pyrrolidone, 2-heptanone, and cyclohexanone are more preferred.

[0120] In the synthesis of component (C), the reaction temperature is preferably 50 °C or higher, more preferably 80 °C or higher, and preferably 300 °C or lower, more preferably 200 °C or lower.

[0121] In the synthesis of component (C), the reaction time is preferably 1 hour or more, more preferably 2 hours or more, still more preferably 3 hours or more, and preferably 100 hours or less, more preferably 50 hours or less, still more preferably 25 hours or less.

[0122] In the synthesis of component (C), R 1 a compound serving as a raw material for a structure containing a group represented by, and R 2 When reacting a compound serving as a raw material for a structure containing a group represented by with a compound serving as a raw material for a structure containing a group represented by Y (and, if necessary, a compound for introducing other structural units), the reaction temperature is preferably 0 °C or higher, more preferably 10 °C or higher, and preferably 130 °C or lower, more preferably 110 °C or lower.

[0123] In the synthesis of component (C), R 1 a compound serving as a raw material for a structure containing a group represented by, and R 2 When reacting a compound serving as a raw material for a structure containing a group represented by with a compound serving as a raw material for a structure containing a group represented by Y (and, if necessary, a compound for introducing other structural units), the reaction time is preferably 1 hour or more, more preferably 2 hours or more, still more preferably 3 hours or more, and preferably 50 hours or less, more preferably 25 hours or less, still more preferably 15 hours or less.

[0124] The weight average molecular weight (Mw) of component (C) is, for example, 100 or more, preferably 1,000 or more, more preferably 2,000 or more, still more preferably 3,000 or more. The upper limit of Mw of component (C) is, for example, 500,000 or less, preferably 100,000 or less, more preferably 10,000 or less, still more preferably 5,000 or less, 4,500 or less, or 4,000 or less. The weight average molecular weight can be measured as a value in terms of polystyrene by the gel permeation chromatography (GPC) method.

[0125] When the content of component (C) in the resin composition is based on the total non-volatile components of components (A) to (C) in the resin composition being 100% by mass, it is preferably 0.1% by mass or more, more preferably 1.0% by mass or more, still more preferably 3.0% by mass or more, 4.0% by mass or more, or 5.0% by mass or more, and is preferably 50% by mass or less, more preferably 40% by mass or less, still more preferably 30% by mass or less, or 27% by mass or less.

[0126] When the resin composition of the present invention contains components other than components (A) to (C), the content of component (C) in the resin composition, when the non-volatile components in the resin composition are 100% by mass, is preferably 0.1% by mass or more, more preferably 0.5% by mass or more, still more preferably 1.0% by mass or more, and is preferably 30% by mass or less, more preferably 20% by mass or less, still more preferably 10% by mass or less, 8% by mass or less, or 7% by mass or less.

[0127] When the resin composition of the present invention contains components other than components (A) to (C), the content of component (C) in the resin composition, when the resin components in the resin composition are 100% by mass, is preferably 0.1% by mass or more, more preferably 1.0% by mass or more, still more preferably 3.0% by mass or more, 3.5% by mass or more, or 4.0% by mass or more, and is preferably 50% by mass or less, more preferably 40% by mass or less, still more preferably 30% by mass or less, or 25% by mass.

[0128] <(D) Inorganic filler> The resin composition may further contain an inorganic filler as component (D). By containing component (D), the coefficient of thermal expansion and the dielectric tangent tend to be further reduced.

[0129] Examples of the material for the component (D) include silica, alumina, glass, cordierite, silicon oxide, barium sulfate, barium carbonate, talc, clay, mica powder, zinc oxide, hydrotalcite, boehmite, aluminum silicate, 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 tungstate phosphate. Among these, silica is particularly preferred. Examples of silica include amorphous silica, fused silica, crystalline silica, synthetic silica, and hollow silica. Also, spherical silica is preferred as the silica. The component (D) may be used alone or in combination of two or more.

[0130] Examples of commercially available products of the component (D) include "SP60-05", "SP507-05" manufactured by Nippon Steel Chemical & Material Co., Ltd.; "YC100C", "YA050C", "YA050C-MJE", "YA010C", "SC2500SQ", "SO-C4", "SO-C2", "SO-C1" manufactured by Admatechs Co., Ltd.; "UFP-30", "DAW-03", "FB-105FD" manufactured by Denka Co., Ltd.; "Silfill NSS-3N", "Silfill NSS-4N", "Silfill NSS-5N" manufactured by Tokuyama Corporation; "Cels spheres", "MGH-005" manufactured by Pacific Cement Co., Ltd.; "Esferique", "BA-1" manufactured by JGC Catalysts & Chemicals Ltd.

[0131] (D) component's average particle size is not particularly limited, but preferably 10 μm or less, more preferably 5 μm or less, still more preferably 3 μm or less, 2 μm or less, 1 μm or less, or 0.7 μm or less. The lower limit of the average particle size is not particularly limited, but preferably 0.01 μm or more, more preferably 0.05 μm or more, still more preferably 0.07 μm or more, 0.1 μm or more, or 0.2 μm or more. The average particle size of the (D) component can be measured by the laser diffraction / scattering method based on the Mie scattering theory. Specifically, it can be measured by creating a particle size distribution of the inorganic filler on a volume basis with a laser diffraction / scattering type particle size distribution measuring device and taking the median diameter thereof as the average particle size. As the measurement sample, 100 mg of the inorganic filler and 10 g of methyl ethyl ketone can be weighed into a vial and dispersed by ultrasonic waves for 10 minutes. The measurement sample can be used to measure the volume-based particle size distribution of the inorganic filler in a flow cell method using a laser diffraction type particle size distribution measuring device with the wavelengths of the light sources used being blue and red, and the average particle size can be calculated as the median diameter from the obtained particle size distribution. Examples of the laser diffraction type particle size distribution measuring device include "LA-960" manufactured by Horiba, Ltd.

[0132] (D) component's specific surface area is not particularly limited, but preferably 0.1 m 2 / g or more, more preferably 0.5 m 2 / g or more, still more preferably 1 m 2 / g or more, 3 m 2 / g or more, or 5 m 2 / g or more. The upper limit of the specific surface area is not particularly limited, but preferably 100 m 2 / g or less, more preferably 80 m 2 / g or less, still more preferably 60 m 2 / g or less, 50 m 2 / g or less, or 40 m 2 / g or less. The specific surface area of the (D) component can be obtained by adsorbing nitrogen gas on the sample surface according to the BET method using a specific surface area measuring device ("Macsorb HM-1210" manufactured by Mountech Co., Ltd.) and calculating the specific surface area using the BET multipoint method.

[0133] (D) component is preferably surface-treated with an appropriate surface treatment agent. By being surface-treated, the moisture resistance and dispersibility of (D) component can be enhanced. Examples of the surface treatment agent include silane coupling agents such as vinyl-based silane coupling agent, epoxy-based silane coupling agent, styryl-based silane coupling agent, (meth)acrylic-based silane coupling agent, amino-based silane coupling agent, isocyanurate-based silane coupling agent, ureido-based silane coupling agent, mercapto-based silane coupling agent, isocyanate-based silane coupling agent, acid anhydride-based silane coupling agent; non-silane coupling - alkoxysilane compounds such as methyltrimethoxysilane and phenyltrimethoxysilane; silazane compounds and the like. The surface treatment agent may be used alone or in combination of two or more.

[0134] Examples of commercially available products of the surface treatment agent include, for example, "KBM403" (3-glycidoxypropyltrimethoxysilane) manufactured by Shin-Etsu Chemical Co., Ltd., "KBM803" (3-mercaptopropyltrimethoxysilane) manufactured by Shin-Etsu Chemical Co., Ltd., "KBE903" (3-aminopropyltriethoxysilane) manufactured by Shin-Etsu Chemical Co., Ltd., "KBM573" (N-phenyl-3-aminopropyltrimethoxysilane) manufactured by Shin-Etsu Chemical Co., Ltd., "SZ-31" (hexamethyldisilazane) manufactured by Shin-Etsu Chemical Co., Ltd., and the like.

[0135] From the viewpoint of improving the dispersibility of the inorganic filler, the degree of surface treatment with the surface treatment agent preferably falls within a predetermined range. Specifically, 100% by mass of the inorganic filler is preferably surface-treated with 0.2 to 5% by mass of the surface treatment agent.

[0136] The degree of surface treatment with the surface treatment agent can be evaluated by the amount of carbon per unit surface area of the inorganic filler. The amount of carbon per unit surface area of the inorganic filler is preferably 0.02 mg / m 2 or more from the viewpoint of improving the dispersibility of the inorganic filler, more preferably 0.1 mg / m 2 or more, and still more preferably 0.2 mg / m 2The above is more preferable. On the other hand, from the viewpoint of preventing an increase in the melt viscosity of the resin composition and the melt viscosity in the sheet form, 1.0 mg / m 2 or less is preferable, 0.8 mg / m 2 or less is more preferable, and 0.5 mg / m 2 or less is even more preferable. The amount of carbon per unit surface area of the component (D) can be measured after washing the surface-treated inorganic filler with a solvent (for example, methyl ethyl ketone (MEK)). Specifically, a sufficient amount of MEK as a solvent is added to the inorganic filler surface-treated with a surface treatment agent, and ultrasonic cleaning is performed at 25°C for 5 minutes. After removing the supernatant and drying the solid content, the amount of carbon per unit surface area of the inorganic filler can be measured using a carbon analyzer. As the carbon analyzer, "EMIA-320V" manufactured by Horiba, Ltd. can be used.

[0137] When the resin composition of the present invention contains the component (D), the content of the component (D) in the resin composition is, from the viewpoint of easily realizing a resin composition having a lower dielectric tangent and coefficient of thermal expansion, when the non-volatile components in the resin composition are 100% by mass, for example, 40% by mass or more, preferably 50% by mass or more, more preferably 60% by mass or more, 65% by mass or more, or 70% by mass or more. The upper limit of the content of the component (D) is not particularly limited, but can be, for example, 90% by mass or less, 85% by mass or less, 80% by mass or less, 77% by mass or less, or 75% by mass or less.

[0138] <Compound containing a (E) radical polymerizable group> The resin composition of the present invention may further contain, as the component (E), a compound containing a radical polymerizable group different from the component (C). The component (E) may be used alone or in combination of two or more.

[0139] (E) component, as long as it has one or more (preferably two or more) radically polymerizable groups in one molecule, is not particularly limited in terms of its type. Examples of the (E) component include compounds having, as the radically polymerizable group, one or more selected from a vinyl group, an allyl group, a vinylphenyl group, an acryloyl group, a methacryloyl group, a fumaroyl group, and a maleoyl group. When the (E) component contains two or more radically polymerizable groups, these two or more radically polymerizable groups may be the same or different.

[0140] (E) component, for example, includes allyl-based radically polymerizable compounds, (meth)acrylic-based radically polymerizable compounds, styrene-based radically polymerizable compounds, maleimide-based radically polymerizable compounds, and the like. Among them, styrene-based radically polymerizable compounds and maleimide-based radically polymerizable compounds are preferred.

[0141] An allyl radical polymerizable compound is, for example, a compound having one or more, preferably two or more allyl groups. Examples of the allyl radical polymerizable compound include aromatic carboxylic acid allyl ester compounds such as diallyl diphenate, triallyl trimellitate, diallyl phthalate, diallyl isophthalate, diallyl terephthalate, diallyl 2,6-naphthalenedicarboxylate, and diallyl 2,3-naphthalenecarboxylate; allyl ester compounds of isocyanuric acid such as 1,3,5-triallyl isocyanurate and 1,3-diallyl-5-glycidyl isocyanurate; epoxy-containing aromatic allyl compounds such as 2,2-bis[3-allyl-4-(glycidyloxy)phenyl]propane; benzoxazine-containing aromatic allyl compounds such as bis[3-allyl-4-(3,4-dihydro-2H-1,3-benzoxazin-3-yl)phenyl]methane; ether-containing aromatic allyl compounds such as 1,3,5-triallyl ether benzene; allyl silane compounds such as diallyl diphenylsilane; resins containing a plurality of benzene rings and allyl groups, and the like. Examples of commercially available allyl radical polymerizable compounds include "TAIC" (1,3,5-triallyl isocyanurate) manufactured by Nippon Kasei Co., Ltd.; "DAD" (diallyl diphenate) manufactured by Nisshu Techno Fine Chemical Co., Ltd.; "TRIAM-705" (triallyl trimellitate) manufactured by Fujifilm Wako Pure Chemical Corporation; "DAND" (diallyl 2,3-naphthalenecarboxylate) manufactured by Nisshu Techno Fine Chemical Co., Ltd.; "ALP-d" (bis[3-allyl-4-(3,4-dihydro-2H-1,3-benzoxazin-3-yl)phenyl]methane) manufactured by Shikoku Kasei Kogyo Co., Ltd.; "RE-810NM" (2,2-bis[3-allyl-4-(glycidyloxy)phenyl]propane) manufactured by Nippon Kayaku Co., Ltd.; "DA-MGIC" (1,3-diallyl-5-glycidyl isocyanurate) manufactured by Shikoku Kasei Kogyo Co., Ltd.; "NE-V-1100-70T" (resin containing a plurality of benzene rings and allyl groups each) manufactured by DIC Corporation, and the like.

[0142] (Meth)acrylic radical polymerizable compounds are, for example, compounds having one or more, preferably two or more acryloyl groups and / or methacryloyl groups. Examples of (meth)acrylic radical polymerizable compounds include low molecular weight (molecular weight less than 1000) aliphatic (meth)acrylate compounds such as cyclohexane-1,4-dimethanol di(meth)acrylate, cyclohexane-1,3-dimethanol di(meth)acrylate, tricyclodecane dimethanol di(meth)acrylate, neopentyl glycol di(meth)acrylate, 1,4-butanediol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, 1,8-octanediol di(meth)acrylate, 1,9-nonanediol di(meth)acrylate, 1,10-decanediol di(meth)acrylate, trimethylolpropane tri(meth)acrylate, trimethylolethane tri(meth)acrylate, glycerin tri(meth)acrylate, pentaerythritol tetra(meth)acrylate; low molecular weight (molecular weight less than 1000) ether-containing (meth)acrylate compounds such as dioxane glycol di(meth)acrylate, 3,6-dioxa-1,8-octanediol di(meth)acrylate, 3,6,9-trioxaundecane-1,11-diol di(meth)acrylate, polyethylene glycol di(meth)acrylate, polypropylene glycol di(meth)acrylate, 9,9-bis[4-(2-acryloyloxyethoxy)phenyl]fluorene, ethoxylated bisphenol A di(meth)acrylate, propoxylated bisphenol A di(meth)acrylate; low molecular weight (molecular weight less than 1000) isocyanurate-containing (meth)acrylate compounds such as tris(3-hydroxypropyl)isocyanurate tri(meth)acrylate, tris(2-hydroxyethyl)isocyanurate tri(meth)acrylate, ethoxylated isocyanuric acid tri(meth)acrylate; high molecular weight (molecular weight 1000 or more) acrylate compounds such as (meth)acrylic modified polyphenylene ether resin, and the like.Examples of commercially available (meth)acrylic radical polymerizable compounds include, for example, "A-DOG" (dioxane glycol diacrylate) manufactured by Shin-Nakamura Chemical Co., Ltd.; "DCP-A" (tricyclodecane dimethanol diacrylate) manufactured by Kyoeisha Chemical Co., Ltd.; "DCP" (tricyclodecane dimethanol dimethacrylate) manufactured by Kyoeisha Chemical Co., Ltd.; "KAYARAD R-684" (tricyclodecane dimethanol diacrylate) manufactured by Nippon Kayaku Co., Ltd.; "KAYARAD R-604" (dioxane glycol diacrylate) manufactured by Nippon Kayaku Co., Ltd.; "SA9000", "SA9000-111" (methacrylic modified polyphenylene ether) manufactured by SABIC, etc.

[0143] Styrene-based radical polymerizable compounds are, for example, compounds having one or more, preferably two or more vinyl groups directly bonded to aromatic carbon atoms. Examples of styrene-based radical polymerizable compounds include low molecular weight (molecular weight less than 1000) styrene-based compounds such as divinylbenzene, 2,4-divinyltoluene, 2,6-divinylnaphthalene, 1,4-divinylnaphthalene, 4,4'-divinylbiphenyl, 1,2-bis(4-vinylphenyl)ethane, 2,2-bis(4-vinylphenyl)propane, bis(4-vinylphenyl)ether; high molecular weight (molecular weight 1000 or more) styrene-based compounds such as vinylbenzyl modified polyphenylene ether resin, styrene-divinylbenzene copolymer, etc. Examples of commercially available styrene-based radical polymerizable compounds include "ODV-XET(X03)", "ODV-XET(X04)", "ODV-XET(X05)" (styrene-divinylbenzene copolymer) manufactured by Nippon Steel Chemical & Material Co., Ltd., "OPE-2St 1200", "OPE-2St 2200" (vinylbenzyl modified polyphenylene ether resin) manufactured by Mitsubishi Gas Chemical Co., Inc.

[0144] The maleimide-based radically polymerizable compound is, for example, a compound having one or more, preferably two or more maleimide groups (2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl groups). The maleimide-based radically polymerizable compound may be an aliphatic maleimide compound containing an aliphatic amine skeleton or an aromatic maleimide compound containing an aromatic amine skeleton. Examples of commercially available maleimide-based radically polymerizable compounds include "BMI-3000J", "BMI-5000", "BMI-1400", "BMI-1500", "BMI-1700", "BMI-689" manufactured by Designer Molecules Inc.; "SLK6895-T90", "SLK-6895", "SLK-1500" manufactured by Shin-Etsu Chemical Co., Ltd.; "MIR-3000-70MT" manufactured by Nippon Kayaku Co., Ltd.; "BMI-4000" manufactured by Daiwa Kasei Co., Ltd.; "BMI-80" manufactured by KAI Chemical Co., Ltd. Further, as the maleimide-based radically polymerizable compound, a maleimide resin (maleimide compound containing an indane ring skeleton) disclosed in the Invention Association Public Technical Report Publication No. 2020-500211 may be used.

[0145] (E) The ethylene unsaturated bond equivalent of the component is preferably 20 g / eq. to 3,000 g / eq., more preferably 50 g / eq. to 2,500 g / eq., still more preferably 70 g / eq. to 2,000 g / eq., and even more preferably 90 g / eq. to 1,500 g / eq. The ethylene unsaturated bond equivalent represents the mass of the radically polymerizable compound per equivalent of the ethylene unsaturated bond.

[0146] (E) The weight average molecular weight of the component is preferably 40,000 or less, more preferably 10,000 or less, still more preferably 5,000 or less, and even more preferably 3,000 or less. The lower limit is not particularly limited, but may be, for example, 150 or more. The weight average molecular weight can be measured as a value in terms of polystyrene by gel permeation chromatography (GPC) method.

[0147] When the resin composition of the present invention contains the component (E), the content of the component (E) in the resin composition is, when the non-volatile components in the resin composition are 100% by mass, for example, 0.01% by mass or more, preferably 0.1% by mass or more, more preferably 1% by mass or more, still more preferably 2% by mass or more, and for example, 15% by mass or less, preferably 10% by mass or less, more preferably 5% by mass or less, still more preferably 3% by mass or less.

[0148] When the resin composition of the present invention contains the component (E), the content of the component (E) in the resin composition is, when the resin components in the resin composition are 100% by mass, for example, 0.1% by mass or more, preferably 1% by mass or more, more preferably 3% by mass or more, still more preferably 5% by mass or more, 7% by mass or more or 8% by mass or more, and for example, 25% by mass or less, preferably 20% by mass or less, more preferably 15% by mass or less, still more preferably 10% by mass or less.

[0149] <(F) Other curing agents> The resin composition of the present invention may further contain, as the component (F), a curing agent other than the component (B) (also referred to as "other curing agent").

[0150] Examples of the component (F) include phenolic resins, naphtholic resins, acid anhydride resins, cyanate ester resins, carbodiimide resins, amine resins, etc. The component (F) may be used alone or in combination of two or more.

[0151] As the phenolic resin and naphtholic resin, those having a novolak structure are preferable from the viewpoints of heat resistance and water resistance. Further, from the viewpoint of adhesion to the conductor layer, nitrogen-containing phenolic resins and nitrogen-containing naphtholic resins are preferable, and triazine skeleton-containing phenolic resins and triazine skeleton-containing naphtholic resins are more preferable.

[0152] Specific examples of phenolic resins and naphthol resins include, for example, "MEH-7700", "MEH-7810", "MEH-7851", "MEH-8000H" manufactured by Meiwa Kasei Co., Ltd.; "NHN", "CBN", "GPH" manufactured by Nippon Kayaku Co., Ltd.; "SN-170", "SN-180", "SN-190", "SN-475", "SN-485", "SN-495", "SN-495V", "SN-375", "SN-395" manufactured by Nippon Steel Chemical & Material Co., Ltd.; "TD-2090", "TD-2090-60M", "LA-7052", "LA-7054", "LA-1356", "LA-3018", "LA-3018-50P", "EXB-9500", "HPC-9500", "KA-1160", "KA-1163", "KA-1165" manufactured by DIC Corporation; "GDP-6115L", "GDP-6115H", "ELPC75", etc. manufactured by Gunei Chemical Industry Co., Ltd.

[0153] Examples of acid anhydride resins include those having one or more acid anhydride groups in one molecule. Specific examples of acid anhydride resins include phthalic anhydride, tetrahydrophthalic anhydride, hexahydrophthalic anhydride, methyltetrahydrophthalic anhydride, methylhexahydrophthalic anhydride, methyl nadic anhydride, hydrogenated methyl nadic anhydride, trialkyltetrahydrophthalic anhydride, dodecenyl succinic anhydride, 5-(2,5-dioxotetrahydro-3-furanyl)-3-methyl-3-cyclohexene-1,2-dicarboxylic anhydride, trimellitic anhydride, pyromellitic anhydride, benzophenone tetracarboxylic dianhydride, biphenyltetracarboxylic dianhydride, naphthalenetetracarboxylic dianhydride, oxydiphthalic dianhydride, 3,3'-4,4'-diphenylsulfonetetracarboxylic dianhydride, 1,3,3a,4,5,9b-hexahydro-5-(tetrahydro-2,5-dioxo-3-furanyl)-naphtho[1,2-c]furan-1,3-dione, ethylene glycol bis(anhydrotrimellitate), and polymer-type acid anhydrides such as styrene-maleic acid resin copolymerized from styrene and maleic acid. Commercially available products of acid anhydride resins include "MH-700" manufactured by Shin Nippon Rika Co., Ltd.

[0154] Examples of the cyanate ester resin include bifunctional cyanate resins such as bisphenol A dicyanate, polyphenol cyanate, oligo(3-methylene-1,5-phenylene cyanate), 4,4'-methylenebis(2,6-dimethylphenyl cyanate), 4,4'-ethylidenediphenyl dicyanate, hexafluorobisphenol A dicyanate, 2,2-bis(4-cyanate)phenylpropane, 1,1-bis(4-cyanatephenylmethane), bis(4-cyanate-3,5-dimethylphenyl)methane, 1,3-bis(4-cyanatephenyl-1-(methylethylidene))benzene, bis(4-cyanatephenyl)thioether, and bis(4-cyanatephenyl)ether; polyfunctional cyanate resins derived from phenol novolac and cresol novolac; prepolymers in which part of these cyanate resins is triazine-formed; and the like. Specific examples of the cyanate ester resin include "PT30" and "PT60" (phenol novolac type polyfunctional cyanate ester resin), "ULL-950S" (polyfunctional cyanate ester resin), "BA230", and "BA230S75" (prepolymer in which part or all of bisphenol A dicyanate is triazine-formed to become a trimer), etc. manufactured by Lonza.

[0155] Specific examples of the carbodiimide resin include Carbodilite (registered trademark) V-03 (carbodiimide group equivalent: 216 g / eq.), V-05 (carbodiimide group equivalent: 262 g / eq.), V-07 (carbodiimide group equivalent: 200 g / eq.); V-09 (carbodiimide group equivalent: 200 g / eq.) manufactured by Nisshinbo Chemical Inc.; and Stabaxol (registered trademark) P (carbodiimide group equivalent: 302 g / eq.) manufactured by LANXESS.

[0156] Examples of amine resins include resins having one or more amino groups in one molecule, such as aliphatic amines, polyether amines, alicyclic amines, aromatic amines, and the like. Specific examples of amine resins include 4,4'-methylenebis(2,6-dimethylaniline), diphenyldiaminosulfone, 4,4'-diaminodiphenylmethane, 4,4'-diaminodiphenylsulfone, 3,3'-diaminodiphenylsulfone, m-phenylenediamine, m-xylylenediamine, diethyltoluenediamine, 4,4'-diaminodiphenyl ether, 3,3'-dimethyl-4,4'-diaminobiphenyl, 2,2'-dimethyl-4,4'-diaminobiphenyl, 3,3'-dihydroxybenzidine, 2,2-bis(3-amino-4-hydroxyphenyl)propane, 3,3-dimethyl-5,5-diethyl-4,4-diphenylmethanediamine, 2,2-bis(4-aminophenyl)propane, 2,2-bis(4-(4-aminophenoxy)phenyl)propane, 1,3-bis(3-aminophenoxy)benzene, 1,3-bis(4-aminophenoxy)benzene, 1,4-bis(4-aminophenoxy)benzene, 4,4'-bis(4-aminophenoxy)biphenyl, bis(4-(4-aminophenoxy)phenyl)sulfone, bis(4-(3-aminophenoxy)phenyl)sulfone, and the like. Commercially available products of amine resins may be used, for example, "KAYABOND C-200S", "KAYABOND C-100", "KAYAHARD A-A", "KAYAHARD A-B", "KAYAHARD A-S" manufactured by Nippon Kayaku Co., Ltd., "EPICURE W" manufactured by Mitsubishi Chemical Corporation, and the like.

[0157] When the resin composition of the present invention contains the component (F), the quantitative ratio of the component (A), the component (B) and the component (F) is preferably in the range of 1:0.01 to 1:10, more preferably 1:0.05 to 1:8, and even more preferably 1:0.1 to 1:5, in the ratio of [(total number of epoxy groups of the component (A))]:[(total number of active groups of the component (B) and the component (F))]. The "total number of epoxy groups of the epoxy resin" is as described above. Further, the "total number of active groups of the component (B) and the component (F)" is the value obtained by dividing the mass of the non-volatile component of the component (B) present in the resin composition by the active ester group equivalent, and the value obtained by dividing the mass of the non-volatile component of the component (F) by the active group equivalent, all added together. When the resin composition of the present invention contains the component (F), by setting the quantitative ratio of the component (B) and the component (F) to be within such a range with respect to the component (A), the effects of the present invention can be remarkably obtained.

[0158] When the resin composition of the present invention contains the component (F), the content of the component (F) in the resin composition is, for example, 0.01% by mass or more, preferably 0.1% by mass or more, more preferably 1% by mass or more, even more preferably 2% by mass or more, and for example, 15% by mass or less, preferably 10% by mass or less, more preferably 5% by mass or less, even more preferably 3% by mass or less, when the non-volatile component in the resin composition is 100% by mass.

[0159] When the resin composition of the present invention contains the component (F), the content of the component (F) in the resin composition is, for example, 0.1% by mass or more, preferably 1% by mass or more, more preferably 3% by mass or more, even more preferably 5% by mass or more, 7% by mass or more or 8% by mass or more, and for example, 25% by mass or less, preferably 20% by mass or less, more preferably 15% by mass or less, even more preferably 10% by mass or less, when the resin component in the resin composition is 100% by mass.

[0160] <(G) Organic filler> The resin composition of the present invention may further contain an organic filler as the component (G). The component (G) may be used alone or in combination of two or more.

[0161] As the organic filler, an organic filler containing a rubber component can be widely used. Examples of the rubber component contained in the organic filler include silicone-based elastomers such as polydimethylsiloxane; olefin-based thermoplastic elastomers such as polybutadiene, polyisoprene, polychlorobutadiene, ethylene-vinyl acetate copolymer, styrene-butadiene copolymer, styrene-isoprene copolymer, styrene-isobutylene copolymer, acrylonitrile-butadiene copolymer, isoprene-isobutylene copolymer, isobutylene-butadiene copolymer, ethylene-propylene-diene terpolymer, and ethylene-propylene-butene terpolymer; and thermoplastic elastomers such as acrylic-based thermoplastic elastomers like poly(propyl (meth)acrylate), poly(butyl (meth)acrylate), poly(cyclohexyl (meth)acrylate), and poly(octyl (meth)acrylate). Further, a silicone-based rubber such as polyorganosiloxane rubber may be mixed into the rubber component. The rubber component contained in the rubber particles has a Tg of, for example, 0°C or lower, preferably -10°C or lower, more preferably -20°C or lower, and even more preferably -30°C or lower.

[0162] In one embodiment, the organic filler is core-shell type rubber particles composed of core particles containing the rubber component listed above and a shell portion obtained by graft copolymerizing a monomer component copolymerizable with the rubber component contained in the core particles. Here, the core-shell type does not necessarily refer only to those in which the core particles and the shell portion can be clearly distinguished. It also includes those in which the boundary between the core particles and the shell portion is unclear, and the core particles do not have to be completely covered by the shell portion.

[0163] Specific examples of the organic filler containing a rubber component include, for example, "CHT" manufactured by Samsung SDI; "B602" manufactured by Techno UMG; "Paraloid EXL-2602", "Paraloid EXL-2603", "Paraloid EXL-2655", "Paraloid EXL-2311", "Paraloid-EXL2313", "Paraloid EXL-2315", "Paraloid KM-330", "Paraloid KM-336P", "Paraloid KCZ-201" manufactured by Dow; "Metablen C-223A", "Metablen E-901", "Metablen S-2001", "Metablen W-450A", "Metablen SRK-200" manufactured by Mitsubishi Rayon; "Kaneka Ace M-511", "Kaneka Ace M-600", "Kaneka Ace M-400", "Kaneka Ace M-580", "Kaneka Ace MR-01" manufactured by Kaneka; "Staffiloid AC3355", "Staffiloid AC3816", "Staffiloid AC3832", "Staffiloid AC4030", "Staffiloid AC3364" manufactured by Aika Industries, etc. These are core-shell type rubber particles.

[0164] When the resin composition of the present invention contains the component (G), the content of the component (G) in the resin composition is, when the non-volatile components in the resin composition are 100% by mass, for example, 0.01% by mass or more, preferably 0.1% by mass or more, more preferably 0.5% by mass or more, still more preferably 1% by mass or more, and for example, 15% by mass or less, preferably 10% by mass or less, more preferably 7% by mass or less, still more preferably 5% by mass or less, 4% by mass or less, or 3% by mass or less.

[0165] When the resin composition of the present invention contains the component (G), the content of the component (G) in the resin composition is, when the resin components in the resin composition are 100% by mass, for example, 0.1% by mass or more, preferably 1% by mass or more, more preferably 3% by mass or more, still more preferably 4% by mass or more, and for example, 15% by mass or less, preferably 10% by mass or less, more preferably 7% by mass or less, still more preferably 5% by mass or less.

[0166] <(H) Curing accelerator> The resin composition of the present invention may further contain a curing accelerator as the (H) component.

[0167] Examples of the (H) component include phosphorus-based curing accelerators, amine-based curing accelerators, imidazole-based curing accelerators, guanidine-based curing accelerators, metal-based curing accelerators, peroxide-based curing accelerators, and the like. The curing accelerator may be used alone or in combination of two or more.

[0168] Examples of phosphorus-based curing accelerators include 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-methylphenolate, di-tert-butyldimethylphosphonium tetraphenylborate; 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; aromatic phosphine-borane complexes such as triphenylphosphine·triphenylborane; aromatic phosphine-quinone addition reactants such as triphenylphosphine·p-benzoquinone addition reactant; aliphatic phosphines such as tributylphosphine, tri-tert-butylphosphine, trioctylphosphine, di-tert-butyl(2-butenyl)phosphine, di-tert-butyl(3-methyl-2-butenyl)phosphine, tricyclohexylphosphine;Aromatic phosphines such as dibutylphenylphosphine, di-tert-butylphenylphosphine, methyldiphenylphosphine, ethyldiphenylphosphine, butyldiphenylphosphine, diphenylcyclohexylphosphine, triphenylphosphine, tri-o-tolylphosphine, tri-m-tolylphosphine, tri-p-tolylphosphine, tris(4-ethylphenyl)phosphine, tris(4-propylphenyl)phosphine, tris(4-isopropylphenyl)phosphine, tris(4-butylphenyl)phosphine, tris(4-tert-butylphenyl)phosphine, tris(2,4-dimethylphenyl)phosphine, tris(2,5-dimethylphenyl)phosphine, tris(2,6-dimethylphenyl)phosphine, tris(3,5-dimethylphenyl)phosphine, tris(2,4,6-trimethylphenyl)phosphine, tris(2,6-dimethyl-4-ethoxyphenyl)phosphine, tris(2-methoxyphenyl)phosphine, tris(4-methoxyphenyl)phosphine, tris(4-ethoxyphenyl)phosphine, tris(4-tert-butoxyphenyl)phosphine, diphenyl-2-pyridylphosphine, 1,2-bis(diphenylphosphino)ethane, 1,3-bis(diphenylphosphino)propane, 1,4-bis(diphenylphosphino)butane, 1,2-bis(diphenylphosphino)acetylene, 2,2'-bis(diphenylphosphino)diphenyl ether, etc. are included.;

[0169] Examples of amine-based curing accelerators include trialkylamines such as triethylamine and tributylamine, 4-dimethylaminopyridine, benzyldimethylamine, 2,4,6-tris(dimethylaminomethyl)phenol, 1,8-diazabicyclo(5,4,0)-undecene, etc.

[0170] Commercially available products may be used as the amine-based curing accelerator. For example, "DMAP" manufactured by Tokyo Chemical Industry Co., Ltd., "MY-25" manufactured by Ajinomoto Fine-Techno Co., Inc., etc. are included.

[0171] Examples of imidazole-based curing accelerators include imidazole compounds such as 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, 1,3,5-triazine-2,4,6(1H,3H,5H)-trione, 6-2-(2-methyl-1H-imidazol-1-yl)ethyl-1,3,5-triazine-2,4-diamine, mixtures thereof, and adducts of the imidazole compounds and epoxy resins.

[0172] As the imidazole-based curing accelerator, commercially available products may be used. For example, "1B2PZ", "2MZA-PW", "2PHZ-PW", "C11Z-A", "2MAOK-PW", "2E4MZ" manufactured by Shikoku Kasei Kogyo Co., Ltd.; "P200-H50" manufactured by Mitsubishi Chemical Corporation, etc. can be mentioned.

[0173] As the guanidine-based curing accelerator, 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. can be mentioned.

[0174] As the metal-based curing accelerator, for example, organometallic complexes or organometallic salts of metals such as cobalt, copper, zinc, iron, nickel, manganese, tin, etc. can be mentioned. Specific examples of organometallic complexes include organocobalt complexes such as cobalt(II) acetylacetonate, cobalt(III) acetylacetonate, organocopper complexes such as copper(II) acetylacetonate, organozinc complexes such as zinc(II) acetylacetonate, organoiron complexes such as iron(III) acetylacetonate, organonickel complexes such as nickel(II) acetylacetonate, organomanganese complexes such as manganese(II) acetylacetonate, etc. Examples of organometallic salts include zinc octylate, tin octylate, zinc naphthenate, cobalt naphthenate, tin stearate, zinc stearate, etc.

[0175] Examples of the peroxide-based curing accelerator include cyclohexanone peroxide, tert-butyl peroxybenzoate, methyl ethyl ketone peroxide, dicumyl peroxide, tert-butyl cumyl peroxide, di-tert-butyl peroxide, diisopropylbenzene hydroperoxide, cumene hydroperoxide, and tert-butyl hydroperoxide. As the peroxide-based curing accelerator, commercially available products can be used, for example, "Perkyl D" manufactured by NOF Corporation.

[0176] When the resin composition of the present invention contains the component (H), the content of the component (H) in the resin composition is, for example, 0.01% by mass or more, preferably 0.1% by mass or more, more preferably 0.3% by mass or more, still more preferably 0.5% by mass or more, when the non-volatile components in the resin composition are 100% by mass, and is, for example, 10.0% by mass or less, preferably 5.0% by mass or less, more preferably 3.0% by mass or less, still more preferably 1.0% by mass or less, 0.9% by mass or less, or 0.7% by mass or less.

[0177] When the resin composition of the present invention contains the component (H), the content of the component (H) in the resin composition is, for example, 0.1% by mass or more, preferably 0.5% by mass or more, more preferably 1% by mass or more, still more preferably 2% by mass or more, when the resin components in the resin composition are 100% by mass, and is, for example, 15% by mass or less, preferably 10% by mass or less, more preferably 7% by mass or less, still more preferably 5% by mass or less, 4% by mass or less, or 3% by mass or less.

[0178] <(I) Optional additive> The resin composition of the present invention may further contain (I) an optional additive in combination with the above-described components (A) to (H). Examples of such additives include radical polymerization initiators such as peroxide-based radical polymerization initiators and azo-based radical polymerization initiators; thermoplastic resins such as phenoxy resins, polyvinyl acetal resins, polysulfone resins, polyether sulfone resins, polyether ether ketone resins, and polyester resins; organometallic compounds such as organic copper compounds, organic zinc compounds, and organic cobalt compounds; colorants such as phthalocyanine blue, phthalocyanine green, iodine green, diazo yellow, crystal violet, titanium oxide, and carbon black; polymerization inhibitors such as hydroquinone, catechol, pyrogallol, and phenothiazine; leveling agents such as silicone-based leveling agents and acrylic polymer-based leveling agents; thickeners such as benton and montmorillonite; antifoaming agents such as silicone-based antifoaming agents, acrylic-based antifoaming agents, fluorine-based antifoaming agents, and vinyl resin-based antifoaming agents; ultraviolet absorbers such as benzotriazole-based ultraviolet absorbers; adhesion improvers such as urea silane; adhesion imparting agents such as triazole-based adhesion imparting agents, tetrazole-based adhesion imparting agents, and triazine-based adhesion imparting agents; antioxidants such as hindered phenol-based antioxidants; fluorescent brighteners such as stilbene derivatives; surfactants such as fluorine-based surfactants and silicone-based surfactants; flame retardants such as phosphorus-based flame retardants (e.g., phosphate ester compounds, phosphazene compounds, phosphinic acid compounds, red phosphorus), nitrogen-based flame retardants (e.g., melamine sulfate), halogen-based flame retardants, and inorganic-based flame retardants (e.g., antimony trioxide); dispersants such as phosphate ester-based dispersants, polyoxyalkylene-based dispersants, acetylene-based dispersants, silicone-based dispersants, anionic dispersants, and cationic dispersants; stabilizers such as borate-based stabilizers, titanate-based stabilizers, aluminate-based stabilizers, zirconate-based stabilizers, isocyanate-based stabilizers, carboxylic acid-based stabilizers, and carboxylic anhydride-based stabilizers. The content of such additives may be determined according to the properties required for the resin composition. (I) The optional additive may be used alone or in combination of two or more.

[0179] <(J) Solvent> The resin composition of the present invention may further contain (J) a solvent as a volatile component in combination with the non-volatile components such as the above-described components (A) to (I).

[0180] (J) Usually, an organic solvent is used as the solvent. Examples of the (J) solvent include ketone solvents such as acetone, methyl ethyl ketone, methyl isobutyl ketone, and cyclohexanone; ester solvents such as methyl acetate, ethyl acetate, butyl acetate, isobutyl acetate, isoamyl acetate, methyl propionate, ethyl propionate, and γ-butyrolactone; ether solvents such as tetrahydropyran, tetrahydrofuran, 1,4-dioxane, diethyl ether, diisopropyl ether, dibutyl ether, and diphenyl ether; alcohol solvents such as methanol, ethanol, propanol, butanol, and ethylene glycol; ether ester solvents such as 2-ethoxyethyl acetate, propylene glycol monomethyl ether acetate, diethylene glycol monoethyl ether acetate, ethyl diglycol acetate, γ-butyrolactone, and methyl methoxypropionate; ester alcohol solvents such as methyl lactate, ethyl lactate, and methyl 2-hydroxyisobutyrate; ether alcohol solvents such as 2-methoxypropanol, 2-methoxyethanol, 2-ethoxyethanol, propylene glycol monomethyl ether, and diethylene glycol monobutyl ether (butyl carbitol); amide solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, and N-methyl-2-pyrrolidone; sulfoxide solvents such as dimethyl sulfoxide; nitrile solvents such as acetonitrile and propionitrile; aliphatic hydrocarbon solvents such as hexane, cyclopentane, cyclohexane, and methylcyclohexane; aromatic hydrocarbon solvents such as benzene, toluene, xylene, ethylbenzene, and trimethylbenzene. The (J) solvent may be used alone or in combination of two or more.

[0181] The resin composition of the present invention can be produced, for example, by adding components (A), (B), (C), and, if necessary, components (D), (E), (F), (G), (H), (I), or (J) to an arbitrary preparation container in an arbitrary order and / or partially or entirely simultaneously and mixing them. Further, during the process of adding and mixing each component, the temperature can be appropriately set, and heating and / or cooling may be performed temporarily or throughout the process. Further, during or after the process of adding and mixing, the resin composition may be stirred or shaken using a stirring device or a shaking device such as a mixer to be uniformly dispersed. Further, defoaming may be performed under low-pressure conditions such as under vacuum simultaneously with the stirring or shaking.

[0182] [Physical properties of the resin composition] As described above, the resin composition of the present invention containing an epoxy resin (A), an active ester-based curing agent (B), and a compound containing a structural unit represented by formula (C1) and a terminal group represented by formula (c1) exhibits good dielectric properties and provides a cured product excellent in adhesion strength to a conductor layer after exposure to a high-temperature and high-humidity environment.

[0183] The cured product of the resin composition of the present invention is characterized by having a low relative permittivity. Therefore, according to the cured product, an insulating layer having a low relative permittivity is provided. For example, when measured at 5.8 GHz and 23°C as described in <Test Example 1: Measurement of relative permittivity and dielectric tangent> described later, the relative permittivity (Dk value) of the cured product obtained by thermally curing the resin composition at 190°C for 90 minutes is preferably 4.0 or less, more preferably 3.8 or less, still more preferably 3.5 or less. The lower limit value of the relative permittivity can be 0.001 or more, etc.

[0184] The cured product of the resin composition of the present invention exhibits the characteristic of having a low dielectric loss tangent. Therefore, according to the cured product, an insulating layer with a low dielectric loss tangent is provided. For example, when measured at 5.8 GHz and 23°C as described in the <Test Example 1: Measurement of Relative Permittivity and Dielectric Loss Tangent> section to be described later, the dielectric loss tangent (Df value) of the cured product obtained by thermally curing the resin composition at 190°C for 90 minutes is preferably 0.0040 or less, more preferably 0.0030 or less, and even more preferably 0.0025 or less. The lower limit value of the dielectric loss tangent can be 0.001 or more, etc.

[0185] The insulating layer made of the cured product of the resin composition of the present invention exhibits the property of having excellent adhesion strength (peel strength) to the conductor layer after exposure to a high-temperature and high-humidity environment. The peel strength after exposure to a high-temperature and high-humidity environment is preferably 0.2 kgf / cm or more, more preferably 0.3 kgf / cm or more. The peel strength can be measured according to the method described in the <Test Example 3: Measurement of Adhesion Strength to the Conductor Layer Before and After Exposure to a High-Temperature and High-Humidity Environment (HAST)> section to be described later. The upper limit of the peel strength after exposure to a high-temperature and high-humidity environment is preferably as high as possible, and can be, for example, 2.00 kg / cm or less.

[0186] The insulating layer made of the cured product of the resin composition of the present invention may exhibit the property of having excellent adhesion strength (peel strength) to the conductor layer even before exposure to a high-temperature and high-humidity environment. The peel strength before exposure to a high-temperature and high-humidity environment is, for example, greater than 0.3 kgf / cm, preferably 0.4 kgf / cm or more, more preferably 0.4 kgf / cm or more, more preferably 0.5 kgf / cm or more, and even more preferably 0.5 kgf / cm or more. The upper limit of the peel strength before exposure to a high-temperature and high-humidity environment is preferably as high as possible, and can be, for example, 2.00 kg / cm or less.

[0187] The cured product obtained by curing the resin composition of the present invention at 130 °C for 30 minutes and then at 175 °C for 40 minutes can exhibit the property of excellent crack resistance. Therefore, it can provide an insulating layer with excellent crack resistance. The evaluation of crack resistance can be carried out according to the method described in <Test Example 2: Evaluation of Crack Resistance after Desmear Treatment> described later. Specifically, a layer made of the cured product of the resin composition is formed on a core material having 100 copper pad portions. The layer made of the cured product is roughened, 100 copper pad portions after the roughening treatment are observed, and the presence or absence of cracks is confirmed. In this case, the number of cracks is preferably 10 or less.

[0188] [Use of Resin Composition] As described above, the resin composition of the present invention exhibits good dielectric properties and can provide a cured product having excellent adhesion strength to the conductor layer after exposure to a high-temperature and high-humidity environment. Therefore, the resin composition of the present invention can be suitably used as a resin composition for forming an insulating layer of a printed wiring board (resin composition for insulating layer of printed wiring board), and more preferably as a resin composition for forming an interlayer insulating layer of a printed wiring board (resin composition for interlayer insulating layer of printed wiring board). The resin composition of the present invention can also be suitably used when the printed wiring board is a component-embedded circuit board. The resin composition of the present invention can also be suitably used as a resin composition for forming an insulating layer of a redistribution substrate of a semiconductor package (resin composition for insulating layer of redistribution substrate). In the present invention, a printed wiring board and a redistribution substrate are collectively referred to as a "circuit board". Therefore, the resin composition of the present invention can be suitably used for the insulating layer of a circuit board.

[0189] The resin composition of the present invention can be widely used in applications where a resin composition is required, such as resin sheets, sheet-like laminated materials such as prepregs, solder resists, underfill materials, die bonding materials, hole filling resins, encapsulating resins, component embedding resins, etc.

[0190] [Sheet-like Laminated Material (Resin Sheet, Prepreg)] The resin composition of the present invention can be used as it is, or it may be used in the form of a sheet-like laminated material containing the resin composition.

[0191] As the sheet-like laminated material, the resin sheets and prepregs shown below are preferable.

[0192] In one embodiment, the resin sheet includes a support and a layer of the resin composition provided on the support (hereinafter, simply referred to as "resin composition layer"), and the resin composition layer is formed from the resin composition of the present invention.

[0193] The thickness of the resin composition layer varies depending on the application, and may be appropriately determined according to the application. For example, from the viewpoint of thinning printed wiring boards and semiconductor packages, the thickness of the resin composition layer is preferably 100 μm or less, 80 μm or less, 60 μm or less, 50 μm or less, 40 μm or less, or 30 μm or less. The lower limit of the thickness of the resin composition layer is not particularly limited, but may usually be 1 μm or more, 5 μm or more, etc.

[0194] Examples of the support include thermoplastic resin films, metal foils, and release papers, and thermoplastic resin films and metal foils are preferable. Therefore, in a preferred embodiment, the support is a thermoplastic resin film or a metal foil.

[0195] When using a thermoplastic resin film as the support, examples of the thermoplastic resin include polyesters such as polyethylene terephthalate (PET) and polyethylene naphthalate (PEN), acrylics such as polycarbonate (PC) and polymethyl methacrylate (PMMA), cyclic polyolefins, triacetyl cellulose (TAC), polyethersulfide (PES), polyether ketone, polyimide, etc. Among them, polyethylene terephthalate and polyethylene naphthalate are preferable, and inexpensive polyethylene terephthalate is particularly preferable.

[0196] When using a metal foil as the support, examples of the metal foil include, for example, copper foil, aluminum foil, etc., and copper foil is preferred. As the copper foil, a foil made of single metal copper may be used, or a foil made of an alloy of copper and other metals (for example, tin, chromium, silver, magnesium, nickel, zirconium, silicon, titanium, etc.) may be used.

[0197] The support may be subjected to matting treatment, corona treatment, or antistatic treatment on the surface that joins the resin composition layer. Further, as the support, a support with a release layer having a release layer on the surface that joins the resin composition layer may be used. Examples of the release agent used for the release layer of the support with a release layer include one or more release agents selected from the group consisting of alkyd resin, polyolefin resin, urethane resin, and silicone resin. Examples of commercially available release agents include "SK-1", "AL-5", "AL-7", etc. manufactured by Lintec Corporation, which are alkyd resin-based release agents. Further, examples of commercially available supports with a release layer include "SK-1", "AL-5", "AL-7" manufactured by Lintec Corporation, which are PET films having a release layer mainly composed of an alkyd resin-based release agent; "Lumirror T60" manufactured by Toray Industries, Inc.; "Purex" manufactured by Teijin Limited; "Unipile" manufactured by Unitika Ltd., etc.

[0198] The thickness of the support is not particularly limited, but a range of 5 μm to 75 μm is preferred, and a range of 10 μm to 60 μm is more preferred. When using a support with a release layer, it is preferable that the total thickness of the support with a release layer is within the above range.

[0199] When using a metal foil as the support, a metal foil with a support substrate, in which a support substrate that can be peeled off is laminated on a thin metal foil, may be used. In one embodiment, the metal foil with a support substrate includes a support substrate, a release layer provided on the support substrate, and a metal foil provided on the release layer. When using a metal foil with a support substrate as the support, the resin composition layer is provided on the metal foil.

[0200] In the metal foil with a support substrate, the material of the support substrate is not particularly limited, and examples thereof include copper foil, aluminum foil, stainless steel foil, titanium foil, copper alloy foil, and the like. When using copper foil as the support substrate, it may be an electrolytic copper foil or a rolled copper foil. Further, the release layer is not particularly limited as long as the metal foil can be peeled off from the support substrate, and examples thereof include an alloy layer of an element selected from the group consisting of Cr, Ni, Co, Fe, Mo, Ti, W, and P; an organic film, and the like.

[0201] In the metal foil with a support substrate, as the material of the metal foil, for example, copper foil and copper alloy foil are preferable.

[0202] In the metal foil with a support substrate, the thickness of the support substrate is not particularly limited, but the range of 10 μm to 150 μm is preferable, and the range of 10 μm to 100 μm is more preferable. Further, the thickness of the metal foil may be, for example, in the range of 0.1 μm to 10 μm.

[0203] In one embodiment, the resin sheet may further include any layer as necessary. Examples of such an arbitrary layer include a protective film or the like provided on the surface of the resin composition layer that is not joined to the support (i.e., the surface opposite to the support). The thickness of the protective film is not particularly limited, but is, for example, 1 μm to 40 μm. By laminating the protective film, it is possible to suppress the adhesion of dust or the like and scratches on the surface of the resin composition layer.

[0204] The resin sheet can be produced, for example, by directly using a liquid resin composition or preparing a resin varnish in which the resin composition is dissolved in an organic solvent, applying this on a support using a die coater or the like, and further drying to form a resin composition layer.

[0205] Examples of the organic solvent include the same ones as the organic solvents described as components of the resin composition. The organic solvent may be used alone or in combination of two or more.

[0206] Drying may be carried out by known methods such as heating and hot air blowing. The drying conditions are not particularly limited, but drying is carried out so that the content of the organic solvent in the resin composition layer is 10% by mass or less, preferably 5% by mass or less. Although it also varies depending on the boiling point of the organic solvent in the resin composition or resin varnish, for example, when using a resin composition or resin varnish containing 30% by mass to 60% by mass of the organic solvent, the resin composition layer can be formed by drying at 50°C to 150°C for 3 minutes to 10 minutes.

[0207] The resin sheet can be wound up in a roll for storage. When the resin sheet has a protective film, it can be used by peeling off the protective film.

[0208] In one embodiment, the prepreg is formed by impregnating a sheet-like fiber base material with the resin composition of the present invention.

[0209] The sheet-like fiber base material used for the prepreg is not particularly limited, and those commonly used as prepreg base materials such as glass cloth, aramid nonwoven fabric, and liquid crystal polymer nonwoven fabric can be used. From the perspective of thinning printed wiring boards and semiconductor chip packages, the thickness of the sheet-like fiber base material is preferably 50 μm or less, more preferably 40 μm or less, still more preferably 30 μm or less, and particularly preferably 20 μm or less. The lower limit of the thickness of the sheet-like fiber base material is not particularly limited. Usually, it is 10 μm or more.

[0210] The prepreg can be manufactured by known methods such as the hot melt method and the solvent method.

[0211] The thickness of the prepreg can be in the same range as the resin composition layer in the above-mentioned resin sheet.

[0212] The sheet-like laminated material of the present invention can be suitably used for forming an insulating layer of a printed wiring board (for the insulating layer of a printed wiring board), and can be more suitably used for forming an interlayer insulating layer of a printed wiring board (for the interlayer insulating layer of a printed wiring board). The sheet-like laminated material of the present invention can also be suitably used for forming an insulating layer of a redistribution substrate of a semiconductor package (for the insulating layer of a redistribution substrate). That is, the sheet-like laminated material of the present invention can be suitably used as an insulating layer for a circuit board.

[0213] [Circuit board] An insulating layer of a circuit board can be formed using the resin composition of the present invention. The present invention also provides such a circuit board, that is, a circuit board including an insulating layer made of a cured product of the resin composition of the present invention.

[0214] [Printed wiring board] In one embodiment, the circuit board of the present invention is a printed wiring board.

[0215] A printed wiring board can be manufactured, for example, by a method including the following steps (I) and (II) using the above resin sheet. (I) A step of laminating a resin sheet on an inner layer substrate so that the resin composition layer of the resin sheet is joined to the inner layer substrate (II) A step of curing the resin composition layer (for example, thermosetting) to form an insulating layer

[0216] The "inner layer substrate" used in process (I) is a member that serves as the substrate of a printed wiring board. Examples thereof include glass epoxy substrates, metal substrates, polyester substrates, polyimide substrates, BT resin substrates, thermosetting polyphenylene ether substrates, and the like. Further, the substrate may have conductor layers on one or both of its surfaces, and these conductor layers may be pattern-processed. An inner layer substrate having conductor layers (circuits) formed on one or both surfaces of the substrate may be referred to as an "inner layer circuit board". Also, in the production of a printed wiring board, intermediate products on which an insulating layer and / or a conductor layer are to be further formed are also included in the "inner layer substrate" as referred to in the present invention. When the printed wiring board is a component-embedded circuit board, an inner layer substrate incorporating components may be used.

[0217] The lamination of the inner layer substrate and the resin sheet can be carried out, for example, by thermocompression bonding the resin sheet to the inner layer substrate from the support side. Examples of the member for thermocompression bonding the resin sheet to the inner layer substrate (hereinafter, also referred to as the "thermocompression bonding member") include a heated metal plate (such as a SUS mirror plate) or a metal roll (SUS roll). Note that the thermocompression bonding member may be pressed directly onto the resin sheet, or may be pressed through an elastic material such as heat-resistant rubber so that the resin sheet sufficiently follows the surface unevenness of the inner layer substrate.

[0218] The lamination of the inner layer substrate and the resin sheet may be carried out by the vacuum lamination method. In the vacuum lamination method, the thermocompression 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 thermocompression 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 thermocompression 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 can preferably be carried out under reduced pressure conditions of a pressure of 26.7 hPa or less.

[0219] The lamination can be carried out using a commercially available vacuum laminator. Examples of commercially available vacuum laminators include a vacuum pressure type laminator manufactured by Meiki Seisakusho Co., Ltd., a vacuum applicator manufactured by Nichco Materials Co., Ltd., a batch type vacuum pressure laminator, and the like.

[0220] After lamination, under normal pressure (atmospheric pressure), for example, the smoothed processing of the laminated resin sheet may be performed by pressing a heat-bonding member from the support side. The pressing conditions for the smoothed processing can be the same as the heat-bonding conditions for the above lamination. The smoothed processing can be performed by a commercially available laminator. Note that the lamination and the smoothed processing may be continuously performed using the above commercially available vacuum laminator.

[0221] The support may be removed between step (I) and step (II), or may be removed after step (II). Note that when a metal foil is used as the support, the conductor layer may be formed using the metal foil without peeling the support. Further, when a metal foil with a support substrate is used as the support, the support substrate (and the release layer) may be peeled off. And the conductor layer can be formed using the metal foil.

[0222] In step (II), the resin composition layer is cured (for example, thermally cured) to form an insulating layer made of a cured product of the resin composition. The curing conditions of the resin composition layer are not particularly limited, and the conditions usually adopted when forming an insulating layer of a printed wiring board may be used.

[0223] For example, the thermal curing conditions of the resin composition layer vary depending on the type of the resin composition and the like. In one embodiment, the curing temperature is preferably 140°C to 250°C, more preferably 150°C to 240°C, still more preferably 160°C to 230°C. The curing time can be preferably 5 minutes to 240 minutes, more preferably 10 minutes to 150 minutes, still more preferably 15 minutes to 120 minutes.

[0224] Before thermally curing the resin composition layer, the resin composition layer may be preheated at a temperature lower than the curing temperature. For example, prior to thermally curing the resin composition layer, the resin composition layer may be preheated at a temperature of 50°C to 140°C, preferably 60°C to 135°C, more preferably 70°C to 130°C for 5 minutes or more, preferably 5 minutes to 150 minutes, more preferably 15 minutes to 120 minutes, still more preferably 15 minutes to 100 minutes.

[0225] When manufacturing a printed wiring board, the steps of (III) drilling holes in the insulating layer, (IV) roughening the insulating layer, and (V) forming the conductor layer may be further performed. These steps (III) to (V) may be performed according to various methods known to those skilled in the art used for manufacturing printed wiring boards. When removing the support after step (II), the removal of the support may be performed between step (II) and step (III), between step (III) and step (IV), or between step (IV) and step (V). Further, if necessary, the formation of the insulating layer and the conductor layer in steps (I) to (V) may be repeated to form a multilayer wiring board.

[0226] In another embodiment, the printed wiring board of the present invention can be manufactured using the above-described prepreg. The manufacturing method is basically the same as the case of using a resin sheet.

[0227] Step (III) is a step of drilling holes in the insulating layer, by which holes such as via holes and through holes can be formed in the insulating layer. Step (III) may be performed using, for example, a drill, a laser, a plasma, etc., according to the composition of the resin composition used for forming the insulating layer. The dimensions and shapes of the holes may be appropriately determined according to the design of the printed wiring board.

[0228] Step (IV) is a step of roughening the insulating layer. Usually, in this step (IV), removal of smear (desmear) is also performed. The procedures and conditions for the roughening treatment are not particularly limited, and known procedures and conditions usually used when forming the insulating layer of a printed wiring board can be adopted. For example, the insulating layer can be roughened by performing swelling treatment with a swelling liquid, roughening treatment with an oxidizing agent, and neutralization treatment with a neutralizing liquid in this order.

[0229] The swelling liquid used for the roughening treatment is not particularly limited, and examples thereof include an alkaline solution and a surfactant solution. An alkaline solution is preferable, and as the alkaline solution, a sodium hydroxide solution and a potassium hydroxide solution are more preferable. Examples of commercially available swelling liquids include "Swelling Dip·Security Gun P" and "Swelling Dip·Security Gun SBU" manufactured by Atotech Japan Co., Ltd. The swelling treatment with the swelling liquid is not particularly limited, but for example, it can be performed by immersing the insulating layer in the swelling liquid at 30°C to 90°C for 1 minute to 20 minutes. From the viewpoint of suppressing 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.

[0230] The oxidizing agent used for the roughening treatment is not particularly limited, and examples thereof include an alkaline permanganate solution in which potassium permanganate or sodium permanganate is dissolved in an aqueous solution of sodium hydroxide. The roughening treatment with an oxidizing agent such as an 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. Also, the concentration of the permanganate in the alkaline permanganate solution is preferably 5% by mass to 10% by mass. Examples of commercially available oxidizing agents include alkaline permanganate solutions such as "Concentrate·Compact CP", "Concentrate·Compact P", and "Dosing Solution·Security Gun P" manufactured by Atotech Japan Co., Ltd.

[0231] Moreover, as the neutralizing liquid used for the roughening treatment, an acidic aqueous solution is preferable, and examples of commercially available products include "Reduction Solution·Security Tanto P" manufactured by Atotech Japan Co., Ltd.

[0232] The treatment with the neutralizing liquid can be performed by immersing the treated surface that has been roughened with the oxidizing agent in the neutralizing liquid at 30°C to 80°C for 5 minutes to 30 minutes. From the viewpoint of workability and the like, a method of immersing the object that has been roughened with the oxidizing agent in the neutralizing liquid at 40°C to 70°C for 5 minutes to 20 minutes is preferable.

[0233] Step (V) is a step of forming a conductor layer, and the conductor layer is formed on an insulating layer. The conductor material used for the conductor layer is not particularly limited. In a preferred embodiment, the conductor layer contains one or more metals selected from the group consisting of gold, platinum, palladium, silver, copper, aluminum, cobalt, chromium, zinc, nickel, titanium, tungsten, iron, tin, and indium. The conductor layer may be a single-metal layer or an alloy layer. Examples of the alloy layer include layers formed from alloys of two or more metals selected from the above group (for example, nickel-chromium alloy, copper-nickel alloy, and copper-titanium alloy). Among them, from the viewpoints of versatility, cost, ease of patterning, etc. of conductor layer formation, 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, or copper-titanium alloy is preferred, a single-metal layer of chromium, nickel, titanium, aluminum, zinc, gold, palladium, silver, or copper, or an alloy layer of nickel-chromium alloy is more preferred, and a single-metal layer of copper is even more preferred.

[0234] The conductor layer may have a single-layer structure or a multilayer structure in which two or more single-metal layers or alloy layers made of different types of metals or alloys are laminated. When the conductor layer has a 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.

[0235] The thickness of the conductor layer depends on the design of the desired printed wiring board, but is generally 3 μm to 35 μm, preferably 5 μm to 30 μm.

[0236] In one embodiment, the conductor layer may be formed by plating. From the viewpoint of easily forming fine wiring, it is preferably formed by a semi-additive method. Hereinafter, an example of forming the conductor layer by the semi-additive method is shown.

[0237] First, a plating seed layer is formed on the surface of the insulating layer by electroless plating. Next, a mask pattern is formed on the formed plating seed layer to expose a part of the plating seed layer corresponding to a desired wiring pattern. After forming a metal layer by electrolytic plating on the exposed plating seed layer, the mask pattern is removed. Thereafter, an unnecessary plating seed layer can be removed by etching or the like to form a conductor layer having a desired wiring pattern.

[0238] In another embodiment, the conductor layer may be formed using a metal foil. When forming the conductor layer using a metal foil, step (V) is preferably carried out between step (I) and step (II). For example, after step (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 may be carried out by a vacuum lamination method. The lamination conditions may be the same as those described for step (I). Next, step (II) is carried out to form an insulating layer. Thereafter, using the metal foil on the insulating layer, a conductor layer having a desired wiring pattern can be formed by a conventionally known technique such as the modified semi-additive method.

[0239] The metal foil can be manufactured by a known method such as an electrolytic method or a rolling method. Examples of commercially available metal foils include HLP foil, JXUT-III foil manufactured by JX Metals, 3EC-III foil, TP-III foil manufactured by Mitsui Mining & Smelting Co., Ltd., and the like.

[0240] Alternatively, as described above, when a metal foil or a metal foil with a support substrate is used as the support of the resin sheet, the conductor layer may be formed using the metal foil.

[0241] <Redistribution Substrate of Semiconductor Package> In one embodiment, the circuit board of the present invention is a redistribution substrate (redistribution layer) of a semiconductor package. Hereinafter, it will be described in accordance with the manufacturing method of the semiconductor package.

[0242] The semiconductor package includes an insulating layer made of a cured product of the resin composition of the present invention as an insulating layer of the redistribution substrate. Note that the semiconductor package may include a sealing layer made of a cured product of the resin composition of the present invention.

[0243] The semiconductor package can be manufactured, for example, by a method including the following steps (1) to (6) using the resin composition and resin sheet of the present invention. The resin composition and resin sheet of the present invention may be used to form the redistribution formation layer (insulating layer for forming the redistribution substrate) in step (5) or the sealing layer in step (3). Hereinafter, an example of forming the redistribution formation layer and the sealing layer using the resin composition and resin sheet is shown. However, the technology for forming the redistribution formation layer and the sealing layer of the semiconductor package is known, and those skilled in the art can manufacture the semiconductor package according to the known technology using the resin composition and resin sheet of the present invention. (1) Step of laminating a temporary fixing film on a base material (2) Step of temporarily fixing a semiconductor chip on the temporary fixing film (3) Step of forming a sealing layer on the semiconductor chip (4) Step of peeling the base material and the temporary fixing film from the semiconductor chip (5) Step of forming a redistribution formation layer as an insulating layer on the surface of the base material and the temporary fixing film of the semiconductor chip from which they are peeled, and (6) Step of forming a redistribution layer as a conductor layer on the redistribution formation layer

[0244] - Step (1) - The material used for the base material is not particularly limited. Examples of the base material include semiconductor wafers such as silicon wafers; glass wafers; glass substrates; metal substrates such as copper, titanium, stainless steel, and cold-rolled steel sheets (SPCC); substrates impregnated with epoxy resins or the like in glass fibers and subjected to thermosetting treatment (for example, FR-4 substrates); substrates made of bismaleimide triazine resins (BT resins), and the like.

[0245] The temporary fixing film can be peeled off from the semiconductor chip in step (4), and the material is not particularly limited as long as it can temporarily fix the semiconductor chip. Commercial products can be used as the temporary fixing film. Examples of commercial products include Rivar Alpha manufactured by Nitto Denko Corporation.

[0246] - Step (2)- The temporary fixing of the semiconductor chip can be performed using a known device such as a flip chip bonder or a die bonder. The layout and the number of arrangements of the semiconductor chips can be appropriately set according to the shape and size of the temporary fixing film, the production number of the target semiconductor package, etc. For example, they can be temporarily fixed in a matrix form arranged in multiple rows and multiple columns.

[0247] - Step (3)- The resin composition layer of the resin sheet of the present invention is laminated on the semiconductor chip, or the resin composition of the present invention is applied on the semiconductor chip and cured (for example, thermally cured) to form a sealing layer.

[0248] For example, the lamination of the semiconductor chip and the resin sheet can be performed by removing the protective film of the resin sheet and then thermocompression bonding the resin sheet to the semiconductor chip from the support side. Examples of the member for thermocompression bonding the resin sheet to the semiconductor chip (hereinafter, also referred to as "thermocompression bonding member") include a heated metal plate (such as a SUS mirror plate) or a metal roll (SUS roll). Note that it is preferable to press through an elastic material such as a heat-resistant rubber so that the resin sheet sufficiently follows the surface unevenness of the semiconductor chip instead of directly pressing the thermocompression bonding member against the resin sheet. The lamination of the semiconductor chip and the resin sheet may be carried out by the vacuum lamination method, and the lamination conditions are the same as the lamination conditions described in relation to the manufacturing method of the printed wiring board, and the preferable ranges are also the same.

[0249] After the lamination, the resin composition is thermally cured to form a sealing layer. The thermal curing conditions are the same as the thermal curing conditions described in relation to the manufacturing method of the printed wiring board.

[0250] The support of the resin sheet may be peeled off after laminating and thermosetting the resin sheet on the semiconductor chip, or the support may be peeled off before laminating the resin sheet on the semiconductor chip.

[0251] When forming the sealing layer by applying the resin composition of the present invention, the coating conditions are the same as those for forming the resin composition layer described in relation to the resin sheet of the present invention, and the preferable ranges are also the same.

[0252] - Step (4)- The method of peeling the base material and the temporary fixing film can be appropriately changed according to the material of the temporary fixing film, etc. For example, methods of peeling by heating and foaming (or expanding) the temporary fixing film, and methods of irradiating ultraviolet rays from the base material side to reduce the adhesive force of the temporary fixing film and peeling it off, etc. can be mentioned.

[0253] In the method of peeling by heating and foaming (or expanding) the temporary fixing film, the heating conditions are usually 100 to 250 °C for 1 to 90 seconds or 5 to 15 minutes. Also, in the method of irradiating ultraviolet rays from the base material side to reduce the adhesive force of the temporary fixing film and peeling it off, the irradiation amount of ultraviolet rays is usually 10 mJ / cm 2 ~1000 mJ / cm 2 is.

[0254] - Step (5)- The resin composition and resin sheet of the present invention are used to form a redistribution formation layer (insulating layer of the redistribution substrate).

[0255] After forming the redistribution formation layer, in order to layer-connect the semiconductor chip and the conductor layer described later, via holes may be formed in the redistribution formation layer. The via holes may be formed by a known method according to the material of the redistribution formation layer.

[0256] - Step (6)- The formation of the conductor layer on the rewiring formation layer may be carried out in the same manner as in step (V) described in relation to the method for manufacturing a printed wiring board. Note that steps (5) and (6) may be repeated to alternately stack (build up) the conductor layer (rewiring layer) and the rewiring formation layer (insulating layer).

[0257] In manufacturing a semiconductor package, (7) a step of forming a solder resist layer on the conductor layer (rewiring layer), (8) a step of forming bumps, and (9) a step of dicing a plurality of semiconductor packages into individual semiconductor packages and singulating them may be further carried out. These steps may be carried out according to various methods known to those skilled in the art used for manufacturing semiconductor packages.

[0258] By forming a rewiring formation layer (insulating layer) using the resin composition and resin sheet of the present invention, which exhibit good dielectric properties and can provide a cured product having excellent adhesion strength to the conductor layer after exposure to a high-temperature and high-humidity environment, a semiconductor package with extremely low transmission loss can be realized regardless of whether it is a Fan-In type package or a Fan-Out type package. In one embodiment, the semiconductor package of the present invention is a Fan-Out type package. The resin composition and resin sheet of the present invention can be applied regardless of whether it is a Fan-Out panel level package (FOPLP) or a Fan-Out wafer level package (FOWLP). In one embodiment, the semiconductor package of the present invention is a Fan-Out panel level package (FOPLP) or a Fan-Out wafer level package (FOWLP).

[0259] [Semiconductor device] The semiconductor device of the present invention includes a layer made of a cured product of the resin composition layer of the present invention. The semiconductor device of the present invention can be manufactured using the circuit board of the present invention.

[0260] Examples of semiconductor devices include various semiconductor devices used in electrical products (e.g., computers, mobile phones, digital cameras, televisions, etc.) and vehicles (e.g., motorcycles, automobiles, trains, ships, airplanes, etc.).

Example

[0261] Hereinafter, the present invention will be specifically described with reference to examples. However, the present invention is not limited to these examples. In the following description, "parts" and "%" representing amounts mean "parts by mass" and "mass %", respectively, unless otherwise specified. Also, the temperature conditions and pressure conditions in the absence of specific designation were room temperature (23 °C) and atmospheric pressure (1 atm).

[0262] <Synthesis Example 1: Synthesis of Compound C-a Containing a Specific Structural Unit and a Specific Terminal Group> Into a four-necked separable flask equipped with a stirrer, 2,2-bis(4-hydroxy-3-methylphenyl)propane (26.43 g), 4,6-dichloro-2-phenylpyrimidine (17.08 g), and potassium carbonate (19.23 g) were weighed, N-methyl-2-pyrrolidone (42.50 g) was added, and the reaction was carried out at 10.0 °C for 6 hours under a nitrogen atmosphere. After the reaction, while cooling the container to 10 °C, m,p-(chloromethyl)styrene (11.53 g) was added dropwise, and then the reaction was carried out at 100 °C for 4 hours.

[0263] To the obtained reaction solution, N-methyl-2-pyrrolidone (55.0 g) was added for dilution, and salts were removed by filtration. Then, the obtained solution was poured into methanol (6900 g). The precipitated solid was filtered off, washed with a small amount of methanol, filtered off again and recovered, and then dried under reduced pressure at 60 °C for 12 hours using a vacuum dryer to obtain Compound C-a represented by the following formula (1) (yield 44.10 g, yield 90%). The Mw of Compound C-a was 3,400.

[0264]

Chemical formula

[0265] <Synthesis Example 2: Synthesis of Compound C-b Containing a Specific Structural Unit and a Specific Terminal Group> The starting materials and the alkali metal compound used were changed to 1,1-bis(4-hydroxy-3-methylphenyl)-3,3,5-trimethylcyclohexane (33.85 g), 4,6-dichloro-2-phenylpyrimidine (16.66 g), m,p-(chloromethyl)styrene (8.680 g), potassium carbonate (18.66 g), and N-methyl-2-pyrrolidone (42.50 g), and the compound C-b represented by the following formula (2) was synthesized in the same procedure as in Synthesis Example 1 (yield 46.55 g, yield 90%). The Mw of compound C-b was 3,400.

[0266]

Chemical formula

[0267] <Synthesis Example 3: Synthesis of Compound C-b Containing a Specific Structural Unit and a Specific Terminal Group> The starting materials and the alkali metal compound used were changed to 2,2-bis(4-hydroxy-3-methylphenyl)propane (25.63 g), 9,9-bis(4-hydroxy-3-methylphenyl)fluorene (37.84 g), 4,6-dichloro-2-phenylpyrimidine (33.31 g), m,p-(chloromethyl)styrene (17.36 g), potassium carbonate (37.31 g), and N-methyl-2-pyrrolidone (181.4 g), and the compound C-c represented by the following formula (3) was synthesized in the same procedure as in Synthesis Example 1 (yield 89.30 g, yield 90%). The Mw of compound C-c was 4,000.

[0268]

Chemical formula

[0269] In formula (C-c), R X is a divalent group represented by the following formula (4) or the following formula (5). In formula (4) and formula (5), "*" represents the bonding site.

[0270]

Chem.

[0271] <Synthesis Example 4: Synthesis of Compound C-d Containing a Specific Structural Unit and a Hydroxyl Group at the Terminal> The starting materials and alkali metal compound used were changed to 1,1-bis(4-hydroxyphenyl)-3,3,5-trimethylcyclohexane (46.56 g), 4,6-dichloropyrimidine (21.45 g), and potassium carbonate (22.80 g), and the synthesis was carried out in the same procedure as in Synthesis Example 1 to obtain a polymer represented by the following formula (6) (yield 70.00 g, yield 90%).

[0272]

Chem.

[0273] <Synthesis Example 5: Synthesis of Active Ester Compound B1> A flask equipped with a thermometer, a dropping funnel, a condenser, a fractionating column, and a stirrer was charged with 320 g (2.0 mol) of 2,7-dihydroxynaphthalene, 184 g (1.7 mol) of benzyl alcohol, and 5.0 g of p-toluenesulfonic acid monohydrate, and stirred while blowing nitrogen at room temperature. Then, the temperature was raised to 150 °C and stirred for 4 hours while distilling off the generated water out of the system. After completion of the reaction, 900 g of methyl isobutyl ketone and 5.4 g of a 20% aqueous sodium hydroxide solution were added for neutralization, and then the aqueous layer was removed by liquid separation, followed by washing three times with 280 g of water, and methyl isobutyl ketone was removed under reduced pressure to obtain 460 g of a benzyl-modified naphthalene compound B'. The obtained benzyl-modified naphthalene compound B' was a black solid, and the hydroxyl group equivalent was 180 grams / equivalent.

[0274] A flask equipped with a thermometer, a dropping funnel, a condenser, a fractionating column, and a stirrer was charged with 203.0 g of isophthaloyl chloride (number of moles of acid chloride groups: 2.0 moles) and 1400 g of toluene, and the system was purged with nitrogen under reduced pressure and dissolved. Next, 113.9 g (0.67 moles) of ortho-phenylphenol and 240 g of benzyl-modified naphthalene compound B' (number of moles of phenolic hydroxyl groups: 1.33 moles) were charged, and the system was purged with nitrogen under reduced pressure and dissolved. Then, 0.70 g of tetrabutylammonium bromide was dissolved, and while purging with nitrogen gas, the temperature inside the system was controlled to 60 °C or lower, and 400 g of a 20% aqueous sodium hydroxide solution was added dropwise over 3 hours. Next, stirring was continued for 1.0 hour under these conditions. After completion of the reaction, the mixture was allowed to stand for liquid separation, and the aqueous layer was removed. Further, water was added to the toluene layer in which the reaction product was dissolved, stirred and mixed for 15 minutes, allowed to stand for liquid separation, and the aqueous layer was removed. This operation was repeated until the pH of the aqueous layer reached 7. Thereafter, water was removed by decanter dehydration to obtain an active ester compound B1 in the form of a toluene solution having a nonvolatile content of 65% by mass. The active ester group equivalent of the obtained active ester compound B1 was 238 g / eq.

[0275] <Synthesis Example 6: Synthesis of Vinyl Compound E2> According to Example 1 of International Publication No. 2017 / 115813, 3.0 moles (390.6 g) of divinylbenzene, 1.8 moles (229.4 g) of ethylvinylbenzene, 10.2 moles (1066.3 g) of styrene, and 15.0 moles (1532.0 g) of n-propyl acetate were charged into a 5.0 L reactor, and 600 mmol of boron trifluoride diethyl ether complex was added at 70 °C and reacted for 4 hours. After the polymerization solution was terminated with an aqueous sodium hydrogen carbonate solution, the oil layer was washed 3 times with pure water, and devolatilized under reduced pressure at 60 °C to recover the polymer. The obtained product was weighed to confirm that 896.7 g of vinyl compound E2 was obtained. The Mw of vinyl compound E2 was 41,300.

[0276] <Preparation of Resin Varnishes of Examples 1 to 12 and Comparative Examples 1 to 3> Weighed each component in the parts by mass shown in Table 1 below, further mixed 10 parts of MEK and 10 parts of cyclohexanone, and uniformly dispersed them using a high-speed rotary mixer to obtain a resin varnish. Note that the amounts of each component shown in Table 1 represent the amounts in terms of non-volatile components. Also, the details of each component shown in Table 1 are as follows.

[0277] (A) Epoxy resin · "ZX1059": Manufactured by Nippon Steel Chemical & Material Co., Ltd., a 1:1 mixture of bisphenol A type and bisphenol F type, epoxy equivalent about 169 g / eq. · "HP-4032-SS": Manufactured by DIC Corporation, naphthalene-type liquid epoxy resin, epoxy equivalent 144 g / eq. · "NC-3000L": Manufactured by Nippon Kayaku Co., Ltd., biphenyl-type epoxy resin, epoxy equivalent about 272 g / eq.

[0278] (B) Active ester-based curing agent · "Active ester compound B1": Active ester compound B1 obtained in Synthesis Example 5 · "HPC-8150-62T": Manufactured by DIC Corporation, active ester-based curing agent containing a naphthalene structure, toluene solution with a non-volatile component of 61.5% by mass, active ester group equivalent 223 g / eq. · "HPC-8000L-65TM": Manufactured by DIC Corporation, active ester-based curing agent containing a dicyclopentadiene-type diphenol structure, toluene / MEK mixed solution with a non-volatile component of 65% by mass

[0279] (C) Compound containing a specific structural unit and a specific terminal group · "C-a": Compound C-a obtained in Synthesis Example 1, containing a specific structural unit and a specific terminal group · "C-b": Compound C-b obtained in Synthesis Example 2, containing a specific structural unit and a specific terminal group · "C-c": Compound C-c obtained in Synthesis Example 3, containing a specific structural unit and a specific terminal group

[0280] (C’) Compound containing a specific structural unit and a hydroxyl group at the terminal · "C-d": Compound C-d obtained in Synthesis Example 4, containing a specific structural unit and a hydroxyl group at the terminal

[0281] (D) Inorganic filler · "SO-C2": Spherical silica (manufactured by Admatechs Co., Ltd.) surface-treated with an amine-based alkoxysilane compound ("KBM573" manufactured by Shin-Etsu Chemical Co., Ltd.), average particle size 0.5 μm, specific surface area 5.8 m 2 / g

[0282] (E) Compound containing a radically polymerizable group · "Maleimide compound E1": A compound represented by the following formula (M) (Mw / Mn = 1.81, t’’ = 1.47 (mainly 1, 2 or 3)) synthesized by the method described in Synthesis Example 1 of Publication No. 2020-500211 of the Invention Association Public Technical Report, MEK solution with a non-volatile component of 62% by mass

[0283]

Chemical formula

[0284] · "MIR-3000-70MT": A maleimide compound manufactured by Nippon Kayaku Co., Ltd., MEK / toluene mixed solution with a non-volatile content of 70% · "SLK-6895": A maleimide compound manufactured by Shin-Etsu Chemical Co., Ltd., · "SLK-1500": A maleimide compound manufactured by Shin-Etsu Chemical Co., Ltd. · "Vinyl compound E2": The vinyl compound obtained in Synthesis Example 6

[0285] (F) Other curing agents · "LA-3018-50P": A phenolic curing agent manufactured by DIC Corporation, 1-methoxy-2-propanol solution with a non-volatile content of 50% by mass, phenol equivalent 151 g / eq.

[0286] (G) Organic filler · "EXL-2655": Rubber particles manufactured by Dow Chemical Japan

[0287] (H) Curing accelerator · "1B2PZ": A product of Shikoku Kasei Kogyo Co., Ltd., an imidazole-based curing accelerator

[0288] <Test Example 1: Measurement of Relative Permittivity and Dissipation Factor> (1) Preparation of Resin Sheet A with a Resin Composition Layer Thickness of 40 μm As a support, a polyethylene terephthalate film with a release layer (「AL-5」manufactured by Lintec Corporation, thickness 38 μm) was prepared. On the release layer of this support, the resin varnishes obtained in the examples and comparative examples were uniformly coated so that the thickness of the resin composition layer after drying would be 40 μm. Then, the resin composition was dried at 80°C to 100°C (average 90°C) for 2 minutes to obtain Resin Sheet A including the support and the resin composition layer.

[0289] (2) Preparation of Cured Product The obtained Resin Sheet A was cured in an oven at 190°C for 90 minutes. By peeling off the support from the Resin Sheet A taken out of the oven, a cured product of the resin composition layer was obtained. The cured product was cut into pieces with a length of 80 mm and a width of 2 mm to obtain a cured product for evaluation.

[0290] (3) Measurement of Relative Permittivity and Dissipation Factor For each cured product for evaluation, using 「HP8362B」manufactured by Agilent Technologies, the values of relative permittivity and dissipation factor (Dk value and Df value) were measured at a measurement frequency of 5.8 GHz and a measurement temperature of 23°C by the cavity resonance perturbation method. The measurement of relative permittivity and dissipation factor was carried out twice, and the average value was calculated.

[0291] <Test Example 2: Evaluation of Crack Resistance after Desmear Treatment> (1) Preparation of Resin Sheet B with a Resin Composition Layer Thickness of 25 μm As a support, a polyethylene terephthalate film with a release layer (「AL-5」manufactured by Lintec Corporation, thickness 38 μm) was prepared. On the release layer of this support, the resin varnishes obtained in the examples and comparative examples were uniformly coated so that the thickness of the resin composition layer after drying would be 25 μm, and dried at 70°C to 80°C (average 75°C) for 2.5 minutes to obtain Resin Sheet B including the support and the resin composition layer.

[0292] (2) Lamination of Resin Sheet B onto the Core Material The obtained Resin Sheet B was laminated on both sides of a core material (manufactured by Resonac Co., Ltd., "E705GR", thickness 400 μm) with circular copper pads (copper thickness 35 μm) having a diameter of 350 μm formed in a lattice pattern at intervals of 400 μm so that the residual copper ratio was 60%, using a batch-type vacuum pressure laminator (two-stage build-up laminator "CVP700" manufactured by Nikko Materials Co., Ltd.) such that the resin composition layer of Resin Sheet B was in contact with the core material. The lamination was carried out by reducing the pressure for 30 seconds to make the atmospheric pressure 13 hPa or less, and then pressure-bonding at a temperature of 100 °C and a pressure of 0.74 MPa for 30 seconds.

[0293] (3) Curing of the Resin Composition Layer Thereafter, the core material laminated with Resin Sheet B was put into an oven at 130 °C and heated for 30 minutes, then transferred to an oven at 175 °C and heated for 40 minutes to thermally cure the resin composition layer and form an insulating layer. Thereafter, the support was peeled off to obtain a cured substrate having a structure of insulating layer / core material / insulating layer.

[0294] (4) Desmear Treatment The obtained cured substrate was immersed in a swelling solution ("Swelling Dip Securigant P" manufactured by Atotech Japan Co., Ltd.) at 60 °C for 10 minutes. Next, it was immersed in a roughening solution (aqueous solution of "Concentrate Compact P" manufactured by Atotech Japan Co., Ltd., KMnO4: 60 g / L, NaOH: 40 g / L) at 80 °C for 30 minutes. Finally, it was immersed in a neutralizing solution ("Reduction Solution Securigant P" manufactured by Atotech Japan Co., Ltd.) at 40 °C for 5 minutes.

[0295] (5) Evaluation of Crack Resistance Regarding the cured substrate after desmear treatment, 100 copper pad portions were observed to confirm the presence or absence of cracks in the resin composition layer, and evaluation was carried out according to the following criteria. ○: 10 cracks or less ×: More than 10 cracks

[0296] <Test Example 3: Measurement of Adhesion Strength with the Conductor Layer before and after Exposure to a High Temperature and High Humidity Environment (HAST)> (1) Lamination of Resin Sheet A onto the Inner Layer Substrate As the inner layer substrate, a glass cloth base epoxy resin double-sided copper-clad laminate having copper foil on the surface (copper foil thickness 18 μm, substrate thickness 0.8 mm, "R1515A" manufactured by Panasonic) was prepared. All of the copper foil on the surface of this inner layer substrate was removed by etching. Thereafter, drying was performed at 190 °C for 30 minutes.

[0297] The resin sheet A obtained above was laminated on both sides of the inner layer substrate using a batch-type vacuum pressure laminator (two-stage build-up laminator "CVP700" manufactured by Nichco Materials Co., Ltd.) such that the resin composition layer of the resin sheet A was in contact with the inner layer substrate. The lamination was carried out by reducing the pressure for 30 seconds to make the atmospheric pressure 13 hPa or less, and then pressure-bonding at a temperature of 100 °C and a pressure of 0.74 MPa for 30 seconds.

[0298] Next, the laminated resin sheet A was heat-pressed and smoothed at 100 °C and a pressure of 0.5 MPa for 60 seconds under atmospheric pressure. Thereafter, the support was peeled off to obtain an "intermediate multilayer body I" containing a resin composition layer / inner layer substrate / resin composition layer in this order.

[0299] (2) Lamination of Copper Foil Copper foil having a glossy surface (thickness 35 μm, "3EC-III" manufactured by Mitsui Mining & Smelting Co., Ltd.) was prepared. The glossy surface of this copper foil was etched using a micro-etching agent ("CZ8101" manufactured by Meck) with a copper etching amount of 1 μm to perform a roughening treatment. The copper foil thus obtained is referred to as "roughened copper foil".

[0300] This roughened copper foil was laminated on both sides of the intermediate multilayer body I such that the roughened surface of the roughened copper foil was joined to the resin composition layer of the intermediate multilayer body I. This lamination was carried out under the same conditions as the lamination of resin sheet A onto the inner layer substrate described above. Thereby, an "intermediate multilayer body II" containing roughened copper foil / resin composition layer / inner layer substrate / resin composition layer / roughened copper foil in this order was obtained.

[0301] (3) Thermal curing of the resin composition layer The obtained intermediate laminate II was placed in an oven at 100 °C and heated for 30 minutes, then transferred to an oven at 170 °C and heated for 30 minutes. Then, after taking out the intermediate laminate II from the oven to a room temperature atmosphere, it was further placed in an oven at 190 °C and additionally heated for 90 minutes. As a result, the thermal curing of the resin composition layer was carried out, and an "evaluation substrate C" was obtained which included a roughened copper foil / hardened product of the resin composition layer as an insulating layer / an inner layer substrate / hardened product of the resin composition layer as an insulating layer / a roughened copper foil in this order. In this evaluation substrate C, the roughened copper foil corresponds to the conductor layer.

[0302] (4) Measurement of the adhesion strength with the conductor layer Using the obtained evaluation substrate C, the peel strength between the roughened copper foil and the insulating layer was measured. The measurement of this peel strength was carried out in accordance with JIS C6481. Specifically, the peel strength was measured by the following operation.

[0303] A cut was made on the roughened copper foil of the evaluation substrate AC to surround a rectangular portion with a width of 10 mm and a length of 100 mm. One end of this rectangular portion was peeled off and grasped with a gripping tool (Auto Com type testing machine "AC-50C-SL" manufactured by T.S.E. Co., Ltd.). The range of 35 mm in length of this rectangular portion was peeled off vertically, and the load (kgf / cm) at the time of this peeling was measured as the peel strength. The above peeling was carried out at a speed of 50 mm / min at room temperature. Further, after performing an environmental test (HAST test) for 100 hours under the conditions of 130 °C and 85% RH, the same operation as above was performed and the peel strength was measured.

[0304] <Results> The results of the examples and comparative examples are shown in Table 1 below.

[0305]

Table 1

Claims

1. A resin composition comprising (A) an epoxy resin, (B) an active ester-based curing agent, and (C) a compound containing a structural unit represented by the following formula (C1) and a terminal group represented by the following formula (c1). 【Chemical 1】 (In formula (C1), R １ each independently represents a divalent organic group; R ２ each independently represents a divalent nitrogen-containing heteroaromatic group which may have a substituent; X is, independently of each other, —O—, —S—, or —N(R ３ )—; R ３ represents a hydrogen atom, a monovalent hydrocarbon group having 1 to 20 carbon atoms, a monovalent halogenated hydrocarbon group having 1 to 20 carbon atoms, or a group in which a part of the hydrocarbon group or the halogenated hydrocarbon group is substituted with at least one selected from an oxygen atom and a sulfur atom; * represents a bonding site.) [Chemical Formula 2] (In formula (c1), Y represents a monovalent organic group having 3 to 50 carbon atoms containing a radically polymerizable group, a monovalent aromatic group having 6 to 50 carbon atoms which may have a substituent (excluding a hydroxy group and a radically polymerizable group), or a monovalent aliphatic group having 3 to 50 carbon atoms which may have a substituent (excluding a hydroxy group and a radically polymerizable group); * represents a bonding site.)

2. In formula (C1), R １ The resin composition according to claim 1, wherein the group represented by is a group containing a group represented by the following formula (C2). 【Chemical Formula 3】 (In formula (C2), Ar １ and Ar ２ each independently represents a divalent aromatic group which may have a substituent; L each independently represents a single bond or a divalent linking group; R ４ and R ５ each independently represents a single bond or an alkylene group having 1 to 4 carbon atoms; y represents 0 or an integer of 1 to 5.)

3. The resin composition according to claim 2, wherein the group represented by L in formula (C2) is any of the divalent groups represented by the following formulas (C4-1) to (C4-3). [Chemical Formula 4] (In formulas (C4-1) to (C4-3), R Ｂ１ each independently represents a monovalent group selected from a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, and an aryl group having 6 to 14 carbon atoms; R Ｂ２ each independently represents a monovalent group selected from an alkyl group having 1 to 4 carbon atoms and an aryl group having 6 to 14 carbon atoms; m5 and m6 each independently represent 0 or an integer of 1 to 4; * represents a bonding site.)

4. The resin composition according to claim 1, wherein the group represented by Y in formula (c1) contains at least one of a monovalent aromatic group containing a radically polymerizable group and an unsubstituted monovalent aromatic group.

5. The resin composition according to claim 1, wherein the group represented by Y in formula (c1) is a vinylbenzyl group.

6. The resin composition according to claim 1, wherein the group represented by Y in formula (c1) is an unsubstituted monovalent nitrogen-containing heteroaromatic group.

7. The resin composition according to claim 1, wherein the weight average molecular weight (Mw) of component (C) is 5,000 or less.

8. The resin composition according to claim 1, further comprising (E) a compound containing a radically polymerizable group (excluding component (C)).

9. The resin composition according to claim 8, wherein component (E) contains a maleimide compound.

10. The resin composition according to claim 1, which is for forming an insulating layer.

11. A cured product of the resin composition according to any one of claims 1 to 10.

12. A resin sheet comprising a support and a resin composition layer formed on the support, wherein the resin composition layer contains the resin composition according to any one of claims 1 to 10.

13. A circuit board comprising a cured product of the resin composition according to any one of claims 1 to 10.

14. A semiconductor device comprising the circuit board according to claim 13.

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