Resin composition

Abstract

The present invention provides: a resin composition capable of providing a cured product exhibiting good dielectric properties and having excellent adhesion strength with a conductor layer after exposure to a high-temperature, high-humidity environment; 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. A resin composition containing (A) an epoxy resin, (B) an active ester-based curing agent, and (C) a compound containing a structural unit represented by formula (C1) and a terminal group represented by formula (c1).

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] Since a resin composition containing an epoxy resin and its curing agent provides a cured product with excellent insulation, heat resistance, adhesion, etc., it is widely used as an insulating material for circuit boards such as printed wiring boards or rewiring substrates for semiconductor chip packages.

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

[0004] Prior Art Documents

[0005] Patent Documents

[0006] Patent Document 1: International Publication No. 2022 / 210095. Summary of the Invention

[0007] Problems to be Solved by the Invention

[0008] It has been found that when an insulating layer is formed using a resin composition having a composition that contributes to good dielectric properties as described in Patent Document 1, the adhesion strength between the insulating layer and the conductor layer tends to deteriorate after exposure to a high-temperature and high-humidity environment.

[0009] The subject of the present invention is to provide: a resin composition that can provide a cured product having 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.

[0010] Means for Solving the Problems

[0011] To achieve the subject of the present invention, the present inventors conducted in-depth research and found that 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, the above problems can be solved, and thus the present invention was completed.

[0012] That is, the present invention includes the following content.

[0013] <1> A resin composition comprising: (A) an epoxy resin, (B) an active ester 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),

[0014]

[0015] In formula (C1),

[0016] R 1 Each independently represents a divalent organic group;

[0017] R 2 Each independently represents a divalent nitrogen-containing heteroaromatic group which may have a substituent;

[0018] X each independently represents -O-, -S- or -N(R 3 )-;

[0019] 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;

[0020] * represents a bonding site,

[0021] *-Y (c1)

[0022] In formula (c1),

[0023] Y represents a monovalent organic group having 3 to 50 carbon atoms having a radical polymerizable group, a monovalent aromatic group having 6 to 50 carbon atoms which may have a substituent (excluding a hydroxyl group and a radical polymerizable group), or a monovalent aliphatic group having 3 to 50 carbon atoms which may have a substituent (excluding a hydroxyl group and a radical polymerizable group);

[0024] * represents a bonding site.

[0025] <2> The resin composition according to <1>, in formula (C1), the group represented by R 1 Contains a group represented by the following formula (C2),

[0026]

[0027] In formula (C2),

[0028] Ar 1 And Ar 2 Each independently represents a divalent aromatic group which may have a substituent;

[0029] L each independently represents a single bond or a divalent linking group;

[0030] R 4 and R 5 each independently represents a single bond or an alkylene group having 1 to 4 carbon atoms;

[0031] y represents an integer of 0 or 1 to 5.

[0032] <3><2> In the resin composition described above, in formula (C2), the group represented by L is any one of the divalent groups represented by the following formulas (C4-1) to (C4-3),

[0033]

[0034] In formulas (C4-1) to (C4-3),

[0035] 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;

[0036] 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;

[0037] m5 and m6 each independently represent an integer of 0 or 1 to 4;

[0038] * represents a bonding site.

[0039] <4><1> - <3> In the resin composition according to any one of the above, in formula (c1), the group represented by Y includes at least one of a monovalent aromatic group containing a radically polymerizable group and an unsubstituted monovalent aromatic group.

[0040] <5><1> - <4> In the resin composition according to any one of the above, in formula (c1), the group represented by Y is vinylbenzyl.

[0041] <6><1> - <4> In the resin composition according to any one of the above, in formula (c1), the group represented by Y is an unsubstituted monovalent nitrogen-containing heteroaromatic group.

[0042] <7><1> - <6> In the resin composition according to any one of the above, the weight average molecular weight (Mw) of the component (C) is 5,000 or less.

[0043] <8><1> - <7> In the resin composition according to any one of the above, it further comprises: (E) a compound having a radically polymerizable group (wherein the component (C) is not included).

[0044] <9><8> In the resin composition described above, the component (E) includes a maleimide compound.

[0045] <10>The resin composition according to any one of <1> to <9>, which is used for forming an insulating layer.

[0046] <11>A cured product of the resin composition according to any one of <1> to <10>.

[0047] <12>A resin sheet, which includes: a support and a resin composition layer formed on the support,

[0048] The resin composition layer contains the resin composition according to any one of <1> to <10>.

[0049] <13>A circuit board, which includes a cured product of the resin composition according to any one of <1> to <10>.

[0050] <14>A semiconductor device, which includes the circuit board described in <13>.

[0051] Advantages of the Invention

[0052] According to the present invention, it is possible to provide: a resin composition that can bring a cured product having good dielectric properties and excellent adhesion strength to a conductor layer after being exposed 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 including the cured product; and a semiconductor device including the circuit board. Detailed Embodiments

[0053] <Explanation of Terms>

[0054] In this specification, the term "may have a substituent" when referring to a compound or a group means both the case where the hydrogen atom of the compound or group is not substituted by a substituent and the case where a part or all of the hydrogen atoms of the compound or group are substituted by a substituent.

[0055] In this specification, unless otherwise specified, the term "substituent" means 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 carboxyl group, a sulfo group, a cyano group, a nitro group, a hydroxyl group, a mercapto group, and an oxo group.

[0056] 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 from 1 to 12, more preferably from 1 to 6, and still more preferably from 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 from 2 to 12, more preferably from 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 from 3 to 12, more preferably from 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 from 1 to 12, more preferably from 1 to 6. The number of carbon atoms of the cycloalkyloxy group used as a substituent is preferably from 3 to 12, more preferably from 3 to 6. The aryl group used as a substituent is a group obtained by removing one hydrogen atom from an aromatic ring of an aromatic hydrocarbon. The number of carbon atoms of the aryl group used as a substituent is preferably from 6 to 14, more preferably from 6 to 10. The number of carbon atoms of the aryloxy group used as a substituent is preferably from 6 to 14, more preferably from 6 to 10. The number of carbon atoms of the arylalkyl group used as a substituent is preferably from 7 to 15, more preferably from 7 to 11. The number of carbon atoms of the arylalkoxy group used as a substituent is preferably from 7 to 15, more preferably from 7 to 11. The monovalent heterocyclic group used as a substituent is a group obtained by removing one hydrogen atom from a heterocyclic ring of a heterocyclic compound. The number of carbon atoms of the monovalent heterocyclic group is preferably from 3 to 15, more preferably from 3 to 9. The aralkyl group used as a substituent is an alkyl group substituted with one or more aryl groups. The alkylidene group used as a substituent is 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 from 1 to 12, more preferably from 1 to 6, and still more preferably from 1 to 3. The above-mentioned substituents may further have substituents (hereinafter sometimes referred to as "secondary substituents"). As the secondary substituents, the same substituents as those described above may be used unless otherwise specified.

[0057] In this specification, the term "aromatic group" refers to a group formed by removing one or more hydrogen atoms from an aromatic ring of an aromatic compound. Specifically, a monovalent aromatic group refers to a group formed by removing one hydrogen atom from an aromatic ring of an aromatic compound, and a divalent aromatic group refers to a group formed by removing two hydrogen atoms from an aromatic ring of an aromatic compound. In addition, the term "aromatic ring" refers to a ring that follows Hückel's rule and has 4n + 2 electrons (where n is a natural number) in the π-electron system of the ring, including monocyclic aromatic rings and fused aromatic rings formed by fusing two or more monocyclic aromatic rings. The aromatic ring can be a carbocyclic ring or a heterocyclic ring. Examples of the monovalent aromatic group include an aryl group that may have a substituent and a heteroaryl group that may have a substituent. Examples of the divalent aromatic group include an arylene group that may have a substituent and a heteroarylene group that 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, further preferably 6 or more, and the upper limit is preferably 24 or less, more preferably 18 or less or 14 or less, further preferably 10 or less. The number of carbon atoms of the substituent is not included in this number of carbon atoms.

[0058] In this specification, the term "aliphatic group" refers to a group formed by removing one or more hydrogen atoms bonded to an aliphatic carbon of an aliphatic compound. Specifically, a monovalent aliphatic group refers to a group formed by removing one hydrogen atom bonded to an aliphatic carbon of an aliphatic compound, and a divalent aliphatic group refers to a group formed by removing two hydrogen atoms bonded to an aliphatic carbon of an aliphatic compound. Examples of the monovalent aliphatic group include an alkyl group that may have a substituent, a cycloalkyl group that may have a substituent, an alkenyl group that may have a substituent, and a cycloalkenyl group that may have a substituent. Examples of the divalent aliphatic group include an alkylene group that may have a substituent, a cycloalkylene group that may have a substituent, an alkenylene group that may have a substituent, and a cycloalkenylene group that may have a substituent. In this specification, unless otherwise specified, the number of carbon atoms of the aliphatic group is preferably 1 or more, more preferably 2 or more, further preferably 3 or more, 4 or more, 5 or more or 6 or more, and preferably 50 or less, more preferably 40 or less, further 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 this number of carbon atoms.

[0059] In this specification, the "non-volatile component" mentioned with respect to the resin composition refers to the components of the resin composition other than the solvent described below. In addition, the "resin component" mentioned with respect to the resin composition refers to the components of the non-volatile components of the resin composition other than the inorganic filler described below.

[0060] Hereinafter, embodiments and examples will be shown to describe the present invention in detail. However, the present invention is not limited to the following embodiments and examples, and can be arbitrarily modified and implemented within the scope of the claims of the present invention and their equivalents.

[0061] [Resin composition]

[0062] 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 formula (C1) and a terminal group represented by formula (c1).

[0063] As described above, it is required that the insulating material of the circuit board exhibits good dielectric properties to reduce the transmission loss when operating in a high-frequency environment. In this regard, the present inventors have found that when the compound described in Patent Document 1 is blended to an extent that achieves good dielectric properties, the adhesion strength between the resulting insulating material and the conductor layer tends to deteriorate after exposure to a high-temperature and high-humidity environment.

[0064] In contrast, according to the resin composition of the present invention that combines an epoxy resin, an active ester-based curing agent, and a compound containing a structural unit represented by formula (C1) and a terminal group represented by formula (c1), a cured product can be formed that exhibits good dielectric properties and has 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 advantageously reduces the transmission loss when operating in a high-frequency environment and significantly contributes to realizing a circuit board having a circuit that exhibits expected characteristics.

[0065] Hereinafter, each component contained in the resin composition will be described.

[0066] <(A) Epoxy resin>

[0067] The resin composition of the present invention contains an epoxy resin as component (A).

[0068] As epoxy resins, for example, the following can be cited: bisphenol type epoxy resins, dicyclopentadiene type epoxy resins, triphenol 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, epoxy resins containing a spiro ring, cyclohexane type epoxy resins, cyclohexanedimethanol type epoxy resins, naphthalene 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 for example, the following can be cited: 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 here, the biphenyl structure may have substituents such as alkyl groups, alkoxy groups, and aryl groups. Therefore, xylylol type epoxy resins and biphenyl aralkyl type epoxy resins are also included in the biphenyl type epoxy resins. The epoxy resin can be used alone or in combination of two or more kinds.

[0069] As the epoxy resin, an aromatic epoxy resin is preferred. Here, the aromatic epoxy resin refers to an epoxy resin having an aromatic ring in its molecule.

[0070] The epoxy resin preferably has two or more epoxy groups in one molecule. When 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, still more preferably 70% by mass or more, and usually 100% by mass or less.

[0071] The epoxy resin includes an epoxy resin that is liquid at a temperature of 20°C (hereinafter referred to as "liquid epoxy resin") and an epoxy resin that is solid at a temperature of 20°C (hereinafter referred to as "solid epoxy resin").

[0072] As the liquid epoxy resin, a liquid epoxy resin having two or more epoxy groups in one molecule is preferred.

[0073] As the liquid epoxy resin, bisphenol A type epoxy resins, bisphenol F type epoxy resins, bisphenol AF type epoxy resins, naphthalene type epoxy resins, glycidyl ester type epoxy resins, glycidylamine type epoxy resins, phenol novolak 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 are preferred.

[0074] As specific examples of the liquid epoxy resin, the following can be cited: "HP-4032", "HP-4032-D", "HP-4032-SS" (naphthalene-type epoxy resin) manufactured by DIC Corporation; "828US", "jER828EL", "825", "Epikote 828EL" (bisphenol A-type epoxy resin) manufactured by Mitsubishi Chemical Corporation; "jER807", "1750" (bisphenol F-type epoxy resin) manufactured by Mitsubishi Chemical Corporation; "jER152" (phenol novolac-type epoxy resin) manufactured by Mitsubishi Chemical Corporation; "630", "630LSD" (glycidylamine-type epoxy resin) manufactured by Nippon Steel Chemical Co., Ltd.; "ZX1059" (a mixture of bisphenol A-type epoxy resin and bisphenol F-type epoxy resin) manufactured by Nippon Steel Chemical Co., Ltd.; "EX-721" (glycidyl ester-type epoxy resin) manufactured by Nagase ChemteX Corporation; "Celloxide 2021P" (alicyclic epoxy resin having an ester skeleton) manufactured by Daicel Corporation; "PB-3600" (epoxy resin having a butadiene structure) manufactured by Daicel Corporation; "ZX1658", "ZX1658GS" (liquid 1,4-glycidylcyclohexane-type epoxy resin) manufactured by Nippon Steel Chemical Co., Ltd., etc.

[0075] As the solid epoxy resin, a solid epoxy resin having 3 or more epoxy groups in 1 molecule is preferred, and an aromatic solid epoxy resin having 3 or more epoxy groups in 1 molecule is more preferred.

[0076] As the solid epoxy resin, xylenol-type epoxy resin, naphthalene-type epoxy resin, naphthalene-type tetrafunctional epoxy resin, cresol novolac-type epoxy resin, dicyclopentadiene-type epoxy resin, triphenol-type epoxy resin, naphthol-type epoxy resin, biphenyl-type epoxy resin, naphthalene ether-type epoxy resin, anthracene-type epoxy resin, bisphenol A-type epoxy resin, bisphenol AF-type epoxy resin, and tetraphenylethane-type epoxy resin are preferred.

[0077] As specific examples of the solid epoxy resin, the following can be cited: "HP-4032H" (naphthalene-type epoxy resin) manufactured by DIC Corporation; "HP-4700", "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", "HP-7200" (dicyclopentadiene-type epoxy resin) manufactured by DIC Corporation; "EXA-7311", "EXA-7311-G3", "EXA-7311-G4", "EXA-7311-G4S", "HP6000" (naphthalene ether-type epoxy resin) manufactured by DIC Corporation; "EPPN-502H" (triphenol-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", "NC-3100" (biphenyl-type epoxy resin) manufactured by Nippon Kayaku Co., Ltd.; "ESN-475V" (naphthol-type epoxy resin) manufactured by Nippon Steel Chemical Co., Ltd.; "ESN-485" (naphthol novolak-type epoxy resin) manufactured by Nippon Steel Chemical Co., Ltd.; "YX4000H", "YX4000", "YL6121" (biphenyl-type epoxy resin) manufactured by Mitsubishi Chemical Corporation; "YX4000HK" (xylenol-type epoxy resin) manufactured by Mitsubishi Chemical Corporation; "YX8800" (anthracene-type epoxy resin) manufactured by Mitsubishi Chemical Corporation; "PG-100", "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, etc.

[0078] The resin composition of the present invention may contain only a liquid epoxy resin, only a solid epoxy resin, or may contain a liquid epoxy resin and a solid epoxy resin in combination as the epoxy resin. When a liquid epoxy resin and a solid epoxy resin are used in combination, the ratio of their amounts (liquid epoxy resin: solid epoxy resin) is preferably 1:0.01 to 1:50, more preferably 1:0.05 to 1:20, and still more preferably 1:0.1 to 1:10 by mass ratio.

[0079] 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 in accordance with JIS K7236.

[0080] The weight-average molecular weight (Mw) of the epoxy resin is preferably 100 to 5000, more preferably 250 to 3000, and still more preferably 400 to 1500. The Mw of the epoxy resin can be measured by gel permeation chromatography (GPC) as a polystyrene conversion value.

[0081] When the total of the components (A) to (C) in the resin composition is 100% by mass, 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, 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.

[0082] When the resin composition of the present invention contains components other than the components (A) to (C), when the non-volatile components in the resin composition are 100% by mass, 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.

[0083] When the resin composition of the present invention contains components other than the components (A) to (C), when the resin components in the resin composition are 100% by mass, 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.

[0084] <(B) Active ester curing agent>

[0085] The resin composition of the present invention contains an active ester curing agent as the component (B). The active ester curing agent can be used alone as 1 type, or 2 types or more can be used in combination.

[0086] 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. This active ester-based curing agent is preferably a curing agent 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. In addition, 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 further preferred.

[0087] As the carboxylic acid compound, either an aromatic carboxylic acid compound or an aliphatic carboxylic acid compound can 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 cited.

[0088] As the aromatic hydroxy compound, for example, (i) an addition polymer of an unsaturated aliphatic cyclic compound having two double bonds in one molecule and a phenol; (ii) various bisphenol compounds; (iii) an aromatic polyol having two or more hydroxy groups bonded to carbon atoms on the aromatic ring; (iv) an aromatic monool having one hydroxy group bonded to a carbon atom on the aromatic ring, etc. As the addition polymer of an unsaturated aliphatic cyclic compound and a phenol, for example, addition polymers of unsaturated aliphatic cyclic compounds such as dicyclopentadiene, tetrahydroindene, norbornadiene, limonene, vinylcyclohexene, etc., and phenols which may have substituents (for example, phenol, cresol, xylenol, ethylphenol, propylphenol, vinylphenol, allylphenol, phenylphenol, benzylphenol, halogenated phenols, etc.) can be cited. Specifically, for example, dicyclopentadiene-phenol addition polymers, etc., can be cited. As the bisphenol compounds, for example, bisphenol A, bisphenol F, bisphenol AF, bisphenol AP, bisphenol B, bisphenol BP, bisphenol C, bisphenol M, etc., can be cited. As the aromatic polyol having two or more hydroxy groups bonded to carbon atoms on the aromatic ring, for example, hydroquinone, resorcinol, catechol, 1,5-dihydroxynaphthalene, 1,6-dihydroxynaphthalene, 2,6-dihydroxynaphthalene, dihydroxybenzophenone, trihydroxybenzophenone, tetrahydroxybenzophenone, phloroglucinol, pyrogallol, phenol novolac, etc., can be cited. As the aromatic monool having one hydroxy group bonded to a carbon atom on the aromatic ring, for example, phenol, cresol, xylenol, ethylphenol, propylphenol, vinylphenol, allylphenol, phenylphenol, benzylphenol, halogenated phenols, naphthol, methylnaphthol, dimethylnaphthol, ethylnaphthol, propylnaphthol, vinylnaphthol, allylnaphthol, phenylnaphthol, benzylnaphthol, halogenated naphthols, etc., can be cited.

[0089] From the viewpoint of more effectively enjoying the effects of the present invention, specific examples of preferred active ester-based curing agents include: active ester-based curing agents containing a dicyclopentadiene-type diphenol structure, active ester-based curing agents containing a naphthalene structure, active ester-based curing agents containing an acetylated product of phenol novolac, and active ester-based curing agents containing a benzoylated product of phenol novolac. Among them, in the combination of component (A) and component (C), from the viewpoint of obtaining a cured product that can simultaneously exhibit good dielectric properties and good adhesion strength to the conductor layer after exposure to a high-temperature and high-humidity environment, active ester-based curing agents containing a naphthalene structure and active ester-based curing agents containing a dicyclopentadiene-type diphenol structure are more preferred. The "dicyclopentadiene-type diphenol structure" refers to a divalent structural unit composed of phenylene-dicyclopentylene-phenylene.

[0090] (B) component can use commercially available products. As examples of such commercially available products, as active ester-based curing agents containing a dicyclopentadiene-type diphenol structure, "EXB-9451", "EXB-9460", "EXB-9460S", "HPC-8000-65T", "HPC-8000L-65TM" (manufactured by DIC Corporation) can be cited; as active ester-based curing agents containing a naphthalene structure, "EXB-8100L-65T", "EXB-8150-60T", "EXB-8150-62T", "EXB-9416-70BK", "HPC-8150-62T" (manufactured by DIC Corporation) can be cited; as phosphorus-containing active ester-based curing agents, "EXB9401" (manufactured by DIC Corporation) can be cited; regarding active ester-based curing agents that are acetylated products of phenol novolac, "DC808" (manufactured by Mitsubishi Chemical Corporation) can be cited; regarding active ester-based curing agents that are benzoylated products of phenol novolac, "YLH1026", "YLH1030", "YLH1048" (manufactured by Mitsubishi Chemical Corporation) can be cited; as active ester-based curing agents containing a styryl group and a naphthalene structure, "PC1300-02-65MA" (manufactured by AIRWATER Corporation), etc. can be cited.

[0091] (B) The active ester group equivalent of the component is preferably 50 g / eq. to 500 g / eq., more preferably 50 g / eq. to 400 g / eq., and further preferably 100 g / eq. to 300 g / eq. The active ester group equivalent is the mass of the active ester resin per 1 equivalent of the active ester group.

[0092] In terms of the ratio of [total count of epoxy groups of component (A)] : [total count of active ester groups of component (B)], the amount ratio of component (A) to component (B) is preferably in the range of 1:0.01 to 1:10, more preferably 1:0.05 to 1:8, and still more preferably 1:0.1 to 1:5. The “total count of epoxy groups of component (A)” is the value obtained by totally summing up the values obtained by dividing the mass of component (A) present in the resin composition by the epoxy equivalent. In addition, the “total count of active ester groups of component (B)” is the value obtained by totally summing up the values obtained by dividing the mass of component (B) present in the resin composition by the active ester group equivalent. By setting the amount ratio of component (A) to component (B) within the above-mentioned range, the effects of the present invention can be significantly obtained.

[0093] From the viewpoint of easily realizing a resin composition that brings good dielectric properties, when the total of components (A) to (C) in the resin composition is 100% by mass, 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, 30% by mass or more, or 35% by mass or more. There is no particular limitation on the upper limit of this content, and it can be determined according to the properties required for the resin composition. For example, it can be 80% by mass or less, 70% by mass or less, or 60% by mass or less, etc.

[0094] From the viewpoint of bringing a cured product that exhibits good dielectric properties, the mass ratio of component (B) to component (A) ((content of component (B)) / (content of component (A))) 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, preferably 2.0 or less, more preferably 1.9 or less, still more preferably 1.8 or less, or 1.7 or less.

[0095] When the resin composition of the present invention contains components other than components (A) to (C), when the non-volatile components in the resin composition are 100% by mass, 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, 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.

[0096] When the resin composition of the present invention contains components other than components (A) to (C), when the resin components in the resin composition are set to 100% by mass, the content of component (B) in the resin composition is preferably 10% by mass or more, more preferably 20% by mass or more, further preferably 25% by mass or more or 30% by mass or more, preferably 80% by mass or less, more preferably 70% by mass or less, further preferably 60% by mass or less or 55% by mass or less.

[0097] <(C) Compound Containing the Structural Unit Represented by Formula (C1) and the Terminal Group Represented by Formula (c1)>

[0098] 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"). Component (C) can be used alone or in combination of two or more.

[0099]

[0100] In formula (C1),

[0101] R 1 each independently represents a divalent organic group;

[0102] R 2 each independently represents a divalent nitrogen-containing heteroaromatic group which may have a substituent;

[0103] X each independently represents -O-, -S- or -N(R 3 );

[0104] 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 by at least one selected from an oxygen atom and a sulfur atom;

[0105] * represents a bonding site.

[0106] *-Y (c1)

[0107] In formula (c1),

[0108] 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 (excluding a hydroxyl group and a radically polymerizable group), or a monovalent aliphatic group having 3 to 50 carbon atoms which may have a substituent (excluding a hydroxyl group and a radically polymerizable group);

[0109] * represents a bonding site.

[0110] In formula (C1), R 1 represents a divalent organic group. The divalent organic group may contain heteroatoms such as oxygen atoms and nitrogen atoms. Among them, R 1 preferably contains a group represented by the following formula (C2).

[0111]

[0112] In formula (C2),

[0113] Ar 1 and Ar 2 each independently represent a divalent aromatic group which may have a substituent;

[0114] L each independently represents a single bond or a divalent linking group;

[0115] R 4 and R 5 each independently represent a single bond or an alkylene group having 1 to 4 carbon atoms;

[0116] y represents an integer of 0 or 1 to 5;

[0117] * represents a bonding site.

[0118] 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 phenylene, naphthylene, anthrylene or biphenylene (-C6H4-C6H4-), and still more preferably phenylene or naphthylene.

[0119] As the substituents that Ar 1 and Ar 2 may have, there is no particular limitation, and examples thereof include: halogen atoms, monovalent hydrocarbon groups having 1 to 20 carbon atoms, halogenated hydrocarbon groups having 1 to 20 carbon atoms, alkoxy groups having 1 to 20 carbon atoms, alkylthio groups having 1 to 20 carbon atoms, nitro groups, cyano groups, carboxyl groups, sulfo groups, phosphonyl groups, phosphate groups, hydroxyl groups or primary to tertiary amino groups. Among them, as the substituent, a monovalent hydrocarbon group having 1 to 20 carbon atoms is preferred, and more preferably one or more substituents selected from methyl, vinyl and allyl are preferred.

[0120] Ar 1 and Ar 2 The number of substituents that may be present is preferably 0 to 8, more preferably 0 to 4, and still more preferably 0 to 2.

[0121] 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 (e.g., 1 to 3000, 1 to 1000, 1 to 100, 1 to 50) skeleton atoms selected from carbon atoms, oxygen atoms, nitrogen atoms, and sulfur atoms. Examples of the divalent linking group include, for example, alkylene, alkenylene, arylene, heteroarylene, -O-, -C(=O)-, -C(=O)-O-, -N(R 6 )- (wherein R 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), -C(=O)-NH-, -NC(=O)N-, -S-, -S(=O)-, -S(O)2-, etc., and may be a group obtained by combining a plurality of them. Among them, L is preferably any one of a single bond, -O-, -C(=O)-, -C(=O)-O-, -S-, -S(O)2-, and divalent groups represented by the following formulas (C3-1) to (C3-4), and more preferably any one of divalent groups represented by the following formulas (C4-1) to (C4-3).

[0122]

[0123] In formulas (C3-1) to (C3-4),

[0124] 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;

[0125] 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;

[0126] m1 represents an integer of 1 to 10;

[0127] m2 represents an integer of 2 to 7;

[0128] m3 and m4 each independently represent 0 or an integer of 1 to 4;

[0129] * represents a bonding site.

[0130]

[0131] In formulas (C4-1) to (C4-3),

[0132] 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;

[0133] 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;

[0134] m5 and m6 each independently represent 0 or an integer of 1 to 4;

[0135] * represents a bonding site.

[0136] 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. Further, 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.

[0137] As the alkyl group having 1 to 12 carbon atoms represented by R A1 or R A2 examples thereof include methyl, ethyl, propyl, butyl, and the like.

[0138] As the aryl group having 6 to 14 carbon atoms represented by R A1 or R A2 examples thereof include phenyl, naphthyl, anthryl, biphenyl (-C6H4-C6H5), and the like.

[0139] As the arylalkyl group having 7 to 15 carbon atoms represented by R A1 or R A2 examples thereof include benzyl, phenylethyl, and the like.

[0140] As the alkoxy group having 1 to 10 carbon atoms represented by R A2 examples thereof include methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, heptyloxy, octyloxy, and the like.

[0141] As the cycloalkyl group having 3 to 12 carbon atoms represented by R A2 examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and the like.

[0142] As R A2 represents a cycloalkyloxy group having 3 to 12 carbon atoms, examples thereof include: cyclopropyloxy, cyclobutyloxy, cyclobutyloxy, and the like.

[0143] As R A2 represents an alkenyl group having 2 to 10 carbon atoms, examples thereof include: methylene, vinyl, propenyl, and the like.

[0144] As R A2 represents an aryloxy group having 6 to 14 carbon atoms, examples thereof include: phenyloxy, naphthyloxy, and the like.

[0145] As R A2 represents an arylalkyloxy group having 7 to 15 carbon atoms, examples thereof include: benzyl oxy, phenylethyl oxy, and the like.

[0146] In formula (C3-1), m1 represents an integer of 1 to 10, preferably an integer of 1 to 6.

[0147] In formula (C3-3), m2 represents an integer of 2 to 7, preferably 4 or 5.

[0148] In formula (C3-4), m3 and m4 each independently represent 0 or an integer of 1 to 4, preferably 0 or 1, more preferably 0.

[0149] 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. In addition, 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.

[0150] As R B1 or R B2 represents an alkyl group having 1 to 4 carbon atoms, examples thereof include: methyl, ethyl, propyl, butyl, and the like.

[0151] As R B1 or R B2 represents an aryl group having 6 to 14 carbon atoms, examples thereof include: phenyl, naphthyl, and the like.

[0152] In formula (C4-3), m5 and m6 each independently represent 0 or an integer of 1 to 4, preferably 0 or 1, more preferably 0.

[0153] In formula (C2), the divalent linking group represented by L may have R 6 representing 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.

[0154] As R 6 The monovalent hydrocarbon group having 1 to 20 carbon atoms represented by R includes, for example: a monovalent aliphatic group, a monovalent aromatic group, or a monovalent group composed of 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. Moreover, the chain hydrocarbon group may be either linear or branched.

[0155] As R 6Specific examples of the monovalent aliphatic group represented include: alkyl groups and the like. As alkyl groups, for example, there may be mentioned: methyl, ethyl, n-propyl, 2-propyl, n-butyl, isobutyl, tert-butyl, n-pentyl, 1-ethylpropyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, pentyl, cyclopentyl, 2,2-dimethylpropyl, 1,1-dimethylpropyl, n-hexyl, cyclohexyl, 1-ethylbutyl, 2-ethylbutyl, 3-ethylbutyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 2,2-dimethylbutyl, 3,3-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,3-dimethylbutyl, n-heptyl, 1-methylhexyl, 2-methylhexyl, 3-methylhexyl, 4-methylhexyl, 5-methylhexyl, 1-ethylpentyl, 2-ethylpentyl, 3-ethylpentyl, 1,1-dimethylpentyl, 2,2-dimethylpentyl, 3,3-dimethylpentyl, 4,4-dimethylpentyl, 1,2-dimethylpentyl, 1,3-dimethylpentyl, 1,4-dimethylpentyl, 2,3-dimethylpentyl, 2,4-dimethylpentyl, 3,4-dimethylpentyl, 2-methyl-3,3-dimethylbutyl, 1-methyl-3,3-dimethylbutyl, 1,2,3-trimethylbutyl, 1,3-dimethyl-2-pentyl, 2-isopropylbutyl, 2-methylcyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 1-cyclohexylmethyl, 2-ethylcyclopentyl, 3-ethylcyclopentyl, 2,3-dimethylcyclopentyl, 2,4-dimethylcyclopentyl, 2-methylcyclopentylmethyl, 2-cyclopentylethyl, 1-cyclopentylethyl, n-octyl, 2-octyl, 3-octyl, 4-octyl, 2-methylheptyl, 3-methylheptyl, 4-methylheptyl, 5-methylheptyl, 6-methylheptyl, 2-ethylhexyl, 3-ethylhexyl, 4-ethylhexyl, 5-ethylhexyl, 1,1-dimethylhexyl, 2,2-dimethylhexyl, 3,3-dimethylhexyl, 4,4-dimethylhexyl, 5,5-dimethylhexyl, 1,2-dimethylhexyl, 1,3-dimethylhexyl, 1,4-dimethylhexyl, 1,5-dimethylhexyl, 2,3-dimethylhexyl, 2,4-dimethylhexyl, 2,5-dimethylhexyl, 1,1-ethylmethylpentyl, 2,2-ethylmethylpentyl, 3,3-ethylmethylpentyl, 4,4-ethylmethylpentyl, 1-ethyl-2-methylpentyl, 1-ethyl-3-methylpentyl, 1-ethyl-4-methylpentyl, 2-ethyl-1-methylpentyl, 3-ethyl-1-methylpentyl, 4-ethyl-1-methylpentyl, 2-ethyl-3-methylpentyl, 2-ethyl-4-methylpentyl, 3-ethyl-2-methylpentyl, 4-ethyl-3-methylpentyl, 3-ethyl-4-methylpentyl, 4-ethyl-3-methylpentyl, 1-(2-methylpropyl)butyl, 1-(2-methylpropyl)-2-methylbutyl, 1,1-(2-methylpropyl)ethyl, 1,1-(2-methylpropyl)ethylpropyl, 1,1-diethylpropyl, 2,2-diethylpropyl, 1,1-ethylmethyl-2,2-dimethylpropyl, 2,2-ethylmethyl-1,1-dimethylpropyl, 2-ethyl-1,1-dimethylbutyl, 2,3-dimethylcyclohexyl, 2,3-dimethylcyclohexyl, 2,5-dimethylcyclohexyl, 2,6-dimethylcyclohexyl, 3,5-dimethylcyclohexyl, 2-methylcyclohexylmethyl, 3-methylcyclohexylmethyl, 4-methylcyclohexylmethyl, 2-ethylcyclohexyl, 3-ethylcyclohexyl, 4-ethylcyclohexyl, 2-cyclohexylethyl, 1-cyclohexylethyl, 1-cyclohexyl-2-ethylidene, nonyl, isononyl, decyl, isodecyl, undecyl, dodecyl, propargyl, etc.,

[0156] As R 6 Specific examples of the monovalent aromatic group represented by include: aryl groups, etc. As the aryl group, for example, phenyl, naphthyl, anthryl, biphenyl (-C6H4-C6H5), etc. can be cited.

[0157] As R 6 Examples of the "monovalent group composed of their combinations" represented by include: benzyl, 2-phenylethyl, etc.

[0158] As R 6 Examples of the monovalent halogenated hydrocarbon group having 1 to 20 carbon atoms represented by include: the group obtained by substituting part or all of the hydrogen atoms of the above-mentioned "monovalent hydrocarbon group having 1 to 20 carbon atoms represented by R 6 with halogen atoms.

[0159] 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: methylene, ethylene, n-propylene, isopropylene, n-butylene, sec-butylene, etc. R 4 and R 5 are preferably a single bond, methylene or ethylene.

[0160] In formula (C2), y represents 0 or an integer of 1 to 5, preferably 0 or an integer of 1 to 4, more preferably 0 or an integer of 1 to 3.

[0161] In formula (C1), R 2 each independently represent a divalent nitrogen-containing heteroaromatic group which may have a substituent. The divalent nitrogen-containing heteroaromatic group refers to the group obtained by removing 2 hydrogens from the nitrogen-containing heteroaromatic ring of a nitrogen-containing heteroaromatic compound. Examples of the nitrogen-containing heteroaromatic ring include: pyrrole ring, pyridine ring, pyrimidine ring, pyrazine ring, pyridazine ring, triazine ring, quinoline ring, isoquinoline ring, quinoxaline ring, phthalazine ring, quinazoline ring, naphthyridine ring, carbazole ring, acridine ring, phenazine ring. R2 Preferably a divalent group composed of a pyrimidine ring which may have substituents.

[0162] As R 2 Examples of the substituents that may be present include: 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, etc.

[0163] In formula (C1), each X independently represents -O-, -S- or -N(R 3 ). Additionally, the R that the group represented by X may have 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.

[0164] As the monovalent hydrocarbon group having 1 to 20 carbon atoms represented by R 3 , it is the same as the monovalent hydrocarbon group having 1 to 20 carbon atoms represented by the above-mentioned R 7 .

[0165] As the monovalent halogenated hydrocarbon group having 1 to 20 carbon atoms represented by R 3 , it is the same as the monovalent halogenated hydrocarbon group having 1 to 20 carbon atoms represented by the above-mentioned R 6 .

[0166] As 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 , examples include: a group obtained by substituting a part of the monovalent hydrocarbon group having 1 to 20 carbon atoms represented by R 3 or the monovalent halogenated hydrocarbon group having 1 to 20 carbon atoms represented by R 3 with groups such as -O-, -S-, -C(=O)-, -C(=O)-O-, -S(=O)-, -S(O)2-.

[0167] 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 substituents (excluding hydroxyl groups and radically polymerizable groups), or a monovalent aliphatic group having 3 to 50 carbon atoms which may have substituents (excluding hydroxyl groups and radically polymerizable groups). The group represented by Y preferably includes at least one of a monovalent aromatic group containing a radically polymerizable group and an unsubstituted monovalent aromatic group.

[0168] Examples of the radically polymerizable group that the group represented by Y may have include: vinyl, allyl, isopropenyl, vinylphenyl, acryloyl, methacryloyl, fumaroyl, maleoyl, and the like.

[0169] The "monovalent organic group having 3 to 50 carbon atoms containing a radically polymerizable group" represented by Y may contain only the radically polymerizable group, or may contain the radically polymerizable group via a divalent linking group. Examples of the divalent linking group include: alkylene, alkenylene, arylene, heteroarylene, -O-, -C(=O)-, -C(=O)-O-, -NH-, -C(=O)-NH-, -NC(=O)N-, -S-, -S(=O)-, -S(O)2-, etc., and may be a group obtained by combining a plurality of them. Among them, the divalent linking group is preferably alkylene, more preferably methylene.

[0170] In a suitable embodiment, the "monovalent organic group having 3 to 50 carbon atoms containing a radically polymerizable group" represented by Y includes: a monovalent aromatic group containing a radically polymerizable group. Among them, the organic group is preferably a monovalent group selected from vinylphenyl, allylphenyl, isopropenylphenyl, and vinylbenzyl, more preferably vinylbenzyl.

[0171] Regarding the "monovalent aromatic group having 6 to 50 carbon atoms that may have substituents (excluding hydroxyl and radically polymerizable groups)" represented by Y, the monovalent aromatic group is as described above.

[0172] In a suitable embodiment, the "monovalent aromatic group having 6 to 50 carbon atoms that may have substituents (excluding hydroxyl and radically polymerizable groups)" 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 refers to a group obtained by removing one hydrogen from the nitrogen-containing heteroaromatic ring of a nitrogen-containing heteroaromatic compound. Regarding the nitrogen-containing heteroaromatic ring, it is as described above. The "monovalent aromatic group having 6 to 50 carbon atoms that may have substituents (excluding hydroxyl and radically polymerizable groups)" represented by Y is more preferably a monovalent group composed of an unsubstituted pyrimidine ring.

[0173] Regarding the "monovalent aliphatic group having 3 to 50 carbon atoms that may have substituents (excluding hydroxyl and radically polymerizable groups)" represented by Y, the monovalent aliphatic group is as described above. The aliphatic group is preferably a monovalent cyclic hydrocarbon group.

[0174] The substituent that the group represented by Y can have is a group other than a hydroxyl group and a radically polymerizable group. Examples of such a 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 phosphonyl group, a phosphoric acid group, a primary to tertiary amino group, etc.

[0175] In a suitable embodiment, component (C) contains the group represented by Y via a divalent linking group. Among them, component (C) preferably contains at least one of the terminal groups represented by the following formula (c2-1) and the following formula (c2-2).

[0176] *-X′-R 1 -X-Y (c2-1)

[0177] *-X′-R 2 -X-Y (c2-2)

[0178] In formulas (c2-1) and (c2-2),

[0179] X’ represents a single bond, -O-, -S- or -N(R 3 )-;

[0180] Each of the other symbols is as described above.

[0181] 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’ can have 3 , it is as described above.

[0182] In a suitable embodiment, component (C) is a compound represented by the following formula (C5-1) or the following formula (C5-2).

[0183]

[0184] In formulas (C5-1) and (C5-2),

[0185] n represents an integer of 0 or 1 to 100;

[0186] Each of the other symbols is as described above.

[0187] In formulas (C5-1) and (C5-2), n represents an integer of 0 or 1 to 100, preferably an integer of 2 to 30.

[0188] Component (C) can use a substance synthesized by a known method. Component (C) can be synthesized, for example, as follows: A raw material compound containing the structure of the group represented by R 1 and a raw material compound containing R2 The starting compound having the structure of the group represented by 2 , the starting compound having the structure of the group represented by Y, and the compound obtained by derivatizing other structural units as needed are heated together with an alkali metal or an alkali metal compound in an organic solvent. Regarding the starting compound having the structure of the group represented by Y and the compound obtained by derivatizing other structural units, after reacting the starting compound having the structure of the group represented by R 1 with the starting compound having the structure of the group represented by R 2 , the reaction mixture is heated to effect reaction.

[0189] In the synthesis of component (C), examples of the starting compound having the structure of the group represented by R 1 include: dihydroxybenzene 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-dimethylbutylene)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'-cyclododecylene bisphenol, 4,4'-decylene bisphenol and other bisphenol compounds; diol compounds such as "Priplast 1901", "Priplast 1838", "Priplast 3186", "Priplast 3192", "Priplast 3197", "Priplast 3199" manufactured by Croda Japan Co., Ltd. It should be noted that these compounds can be used alone or in combination of two or more.

[0190] In the synthesis of component (C), as the starting compound having the structure of the group represented by R 2Raw material compounds of the structure of the group represented, for example, 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, etc.; pyridazine compounds such as 3,6-dichloropyridazine, 3,5-dichloropyridazine, 4-methyl-3,6-dichloropyridazine, etc.; 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, etc. It should be noted that these compounds can be used alone or in combination of two or more.

[0191] (C) In the synthesis of the component, as the raw material compound containing the structure of the group represented by Y, for example, include: monovalent phenol compounds such as tert-butylphenol, nonylphenol, 4-isopropenylphenol, 4-vinylphenol, 2-allylphenol, isoeugenol, tocotrienol, α-tocopherol, 4-hydroxyphenylmaleimide, 2-phenylphenol, etc.; monovalent amine compounds such as 4-hexylaniline, diallylamine, etc.; monovalent thiol compounds such as 1-octanethiol, etc.; monovalent aliphatic halides such as allyl chloride, 4-(chloromethyl)styrene, 3-(chloromethyl)styrene, etc.; monovalent acid halides such as acryloyl chloride, methacryloyl chloride, crotonyl chloride, cinnamoyl chloride, etc.; monovalent acid anhydrides such as acrylic anhydride, crotonic anhydride, methacrylic anhydride, etc. It should be noted that these compounds can be used alone or in combination of two or more.

[0192] In the synthesis of component (C), compounds derived from other structural units include, for example: compounds derived from structural units including carbonate bonds, thiocarbonate bonds or selenocarbonate bonds, such as diphenyl carbonate, diphenyl thiocarbonate, diphenyl selenocarbonate, phosgene, thiophosgene, and selenophene; dihydroxy compounds such as benzyl alcohol and cyclohexanedimethanol; phosphine oxide compounds such as bis(fluorophenyl)phenylphosphine oxide, bis(fluorophenyl)naphthylphosphine oxide, and bis(fluorophenyl)anthracenephosphine oxide; dihalides of dicarboxylic acids such as phthaloyl dichloride, isophthaloyl dichloride, and terephthaloyl dichloride, etc. It should be noted that these compounds can be used alone or in combination of two or more.

[0193] In the synthesis of component (C), when a compound having a hydroxyl group such as a phenol compound is used as a raw material, an alkali metal and an alkali metal compound react with the compound having a hydroxyl 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; 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.

[0194] In the synthesis of the component (C), examples of the organic solvent include tetrahydrofuran (THF), dihydrofuran (DHF), Ether solvents such as alkane, cyclopentyl methyl ether, anisole, phenethyl ether, diphenyl ether, dialkoxybenzene, trialkoxybenzene; nitrogen-containing solvents such as N,N-dimethylacetamide (DMAc), N,N-dimethylformamide, N-methyl-2-pyrrolidone, 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, diphenyl sulfone; ketone solvents such as benzophenone, 2-heptanone, cyclohexanone, methyl ethyl ketone; halogen solvents such as dichloromethane, chloroform, chlorobenzene; aromatic hydrocarbon solvents such as benzene, toluene, xylene, etc. Among them, 2-heptanone, cyclohexanone, N-methyl-2-pyrrolidone, toluene, xylene are preferred, and N-methyl-2-pyrrolidone, 2-heptanone, cyclohexanone are more preferred.

[0195] In the synthesis of the component (C), the reaction temperature is preferably 50°C or higher, more preferably 80°C or higher, and is preferably 300°C or lower, more preferably 200°C or lower.

[0196] In the synthesis of component (C), the reaction time is preferably 1 hour or longer, more preferably 2 hours or longer, and even more preferably 3 hours or longer, and is preferably 100 hours or shorter, more preferably 50 hours or shorter, and even more preferably 25 hours or shorter.

[0197] In the synthesis of component (C), when after reacting a raw material compound having a structure of a group represented by R 1 and a raw material compound having a structure of a group represented by R 2 and then reacting a raw material compound having a structure of a group represented by Y (and a compound for derivatizing other structural units as needed), the reaction temperature is preferably 0 °C or higher, more preferably 10 °C or higher, preferably 130 °C or lower, and more preferably 110 °C or lower.

[0198] In the synthesis of component (C), when after reacting a raw material compound having a structure of a group represented by R 1 and a raw material compound having a structure of a group represented by R 2 and then reacting a raw material compound having a structure of a group represented by Y (and a compound for derivatizing other structural units as needed), the reaction time is preferably 1 hour or longer, more preferably 2 hours or longer, further preferably 3 hours or longer, preferably 50 hours or shorter, more preferably 25 hours or shorter, and further preferably 15 hours or shorter.

[0199] 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, and further 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, and further preferably 5,000 or less, 4,500 or less, or 4,000 or less. The weight average molecular weight can be measured as a polystyrene conversion value by gel permeation chromatography (GPC) method.

[0200] When the total of components (A) to (C) in the resin composition is 100% by mass, the content of component (C) in the resin composition is preferably 0.1% by mass or more, more preferably 1.0% by mass or more, further preferably 3.0% by mass or more, 4.0% by mass or more, or 5.0% by mass or more, and preferably 50% by mass or less, more preferably 40% by mass or less, and further preferably 30% by mass or less or 27% by mass or less.

[0201] When the resin composition of the present invention contains components other than components (A) to (C), when the non-volatile components in the resin composition are 100% by mass, the content of component (C) in the resin composition is preferably 0.1% by mass or more, more preferably 0.5% by mass or more, further preferably 1.0% by mass or more, and preferably 30% by mass or less, more preferably 20% by mass or less, and further preferably 10% by mass or less, 8% by mass or less, or 7% by mass or less.

[0202] When the resin composition of the present invention contains components other than the components (A) to (C), when the resin components in the resin composition are set to 100% by mass, the content of the component (C) in the resin composition is preferably 0.1% by mass or more, more preferably 1.0% by mass or more, further preferably 3.0% by mass or more, 3.5% by mass or more, or 4.0% by mass or more, preferably 50% by mass or less, more preferably 40% by mass or less, further preferably 30% by mass or less, or 25% by mass or less.

[0203] <(D) Inorganic filler>

[0204] The resin composition may further contain an inorganic filler as the component (D). By containing the component (D), there is a tendency to further reduce the thermal expansion rate or the dielectric loss tangent.

[0205] Examples of the material as 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, etc. Among these, silica is particularly suitable. Examples of silica include: amorphous silica, fused silica, crystalline silica, synthetic silica, hollow silica, etc. In addition, as silica, spherical silica is preferred. The component (D) can be used alone or in combination of two or more.

[0206] Examples of commercially available products as the component (D) include: "SP60-05", "SP507-05" manufactured by Nippon Steel Chemical Materials 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.; "SILFIL NSS-3N", "SILFIL NSS-4N", "SILFIL NSS-5N" manufactured by Tokuyama Corporation; "CellSpheres", "MGH-005", etc. manufactured by Taiheiyo Cement Corporation.

[0207] There is no particular limitation on the average particle diameter of the component (D), and it is preferably 10 μm or less, more preferably 5 μm or less, and further preferably 3 μm or less, 2 μm or less, 1 μm or less, or 0.7 μm or less. There is no particular limitation on the lower limit of the average particle diameter, and it is preferably 0.01 μm or more, more preferably 0.05 μm or more, and further preferably 0.07 μm or more, 0.1 μm or more, or 0.2 μm or more. The average particle diameter of the component (D) can be measured by the laser diffraction / scattering method based on the Mie scattering theory. Specifically, a particle size distribution of the inorganic filler can be produced on a volume basis by a laser diffraction scattering type particle size distribution measuring device, and the median diameter thereof can be used as the average particle diameter for measurement. As the measurement sample, a sample obtained by weighing 100 mg of the inorganic filler and 10 g of methyl ethyl ketone into a test tube and dispersing them ultrasonically for 10 minutes can be used. For the measurement sample, using a laser diffraction type particle size distribution measuring device, the light source wavelength is set to blue and red, and the particle size distribution of the inorganic filler on a volume basis is measured in a flow cell manner, and the average particle diameter as the median diameter is calculated from the obtained particle size distribution. As the laser diffraction type particle size distribution measuring device, for example, "LA-960" manufactured by Horiba, Ltd. can be mentioned.

[0208] There is no particular limitation on the specific surface area of the component (D), and it is preferably 0.1 m 2 / g or more, more preferably 0.5 m 2 / g or more, and further preferably 1 m 2 / g or more, 3 m 2 / g or more, or 5 m 2 / g or more. There is no particular limitation on the upper limit of the specific surface area, and it is preferably 100 m 2 / g or less, more preferably 80 m 2 / g or less, and further 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 component (D) can be obtained by the following method: According to the BET method, using a specific surface area measuring device ("Macsorb HM-1210" manufactured by Mountech Co., Ltd.), nitrogen is adsorbed on the surface of the sample, and the specific surface area is calculated by the BET multi-point method.

[0209] Component (D) is preferably surface-treated with a suitable surface treatment agent. By performing the surface treatment, the moisture resistance and dispersibility of component (D) can be improved. Examples of the surface treatment agent include: silane coupling agents such as vinyl-based silane coupling agents, epoxy-based silane coupling agents, styryl-based silane coupling agents, (meth)acrylic acid-based silane coupling agents, amino-based silane coupling agents, isocyanurate-based silane coupling agents, urea-based silane coupling agents, mercapto-based silane coupling agents, isocyanate-based silane coupling agents, and anhydride-based silane coupling agents; non-silane coupling - alkoxysilane compounds such as methyltrimethoxysilane and phenyltrimethoxysilane; and silazane compounds. The surface treatment agent can be used alone or in combination of two or more kinds.

[0210] Examples of commercially available products of the surface treatment agent include: "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., etc.

[0211] From the viewpoint of improving the dispersibility of the inorganic filler, the degree of the surface treatment by the surface treatment agent is preferably limited within a specified range. Specifically, with respect to 100% by mass of the inorganic filler, it is preferably surface-treated with 0.2% to 5% by mass of the surface treatment agent.

[0212] The degree of the surface treatment by the surface treatment agent can be evaluated by the carbon amount per unit surface area of the inorganic filler. From the viewpoint of improving the dispersibility of the inorganic filler, the carbon amount per unit surface area of the inorganic filler is preferably 0.02 mg / m 2 or more, more preferably 0.1 mg / m 2 or more, and further preferably 0.2 mg / m 2 or more. On the other hand, from the viewpoint of preventing an increase in the melt viscosity of the resin composition or the melt viscosity in the sheet form, the carbon amount per unit surface area of the inorganic filler is preferably 1.0 mg / m 2 or less, more preferably 0.8 mg / m 2 or less, and further preferably 0.5 mg / m 2Hereinafter, after cleaning the surface-treated inorganic filler with a solvent (e.g., methyl ethyl ketone (MEK)), the carbon amount per unit surface area of the component (D) can be measured. Specifically, an adequate 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 component, the carbon amount 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. etc. can be used.

[0213] When the resin composition of the present invention contains the component (D), from the viewpoint of easily achieving a resin composition with a lower dielectric loss tangent or coefficient of thermal expansion, when the non-volatile components in the resin composition are set to 100% by mass, the content of the component (D) in the resin composition is, 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. There is no particular limitation on the upper limit of the content of the component (D), and it 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, etc.

[0214] <(E) Compound Containing a Radical Polymerizable Group>

[0215] The resin composition of the present invention may further contain a compound containing a radical polymerizable group different from the component (C) as the component (E). The component (E) can be used alone or in combination of two or more.

[0216] As the component (E), it is sufficient that there is one or more (preferably two or more) radical polymerizable groups in one molecule, and there is no particular limitation on its type. As the component (E), for example, compounds having one or more selected from vinyl, allyl, vinylphenyl, acryloyl, methacryloyl, fumaroyl, and maleoyl as radical polymerizable groups can be cited. When the component (E) contains two or more radical polymerizable groups, these two or more radical polymerizable groups can be the same or different.

[0217] As the component (E), for example, allyl-based radical polymerizable compounds, (meth)acrylic acid-based radical polymerizable compounds, styrene-based radical polymerizable compounds, maleimide-based radical polymerizable compounds, etc. can be cited. Among them, styrene-based radical polymerizable compounds and maleimide-based radical polymerizable compounds are preferred.

[0218] Allyl-based radically polymerizable compounds are, for example, compounds having one or more, preferably two or more allyl groups. Examples of allyl-based radically polymerizable compounds include: aromatic carboxylic acid allyl ester compounds such as diallyl phthalate, diallyl isophthalate, diallyl terephthalate, diallyl 2,6-naphthalenedicarboxylate, and diallyl 2,3-naphthoate; allyl isocyanurate compounds such as 1,3,5-triallyl isocyanurate and 1,3-diallyl-5-glycidyl isocyanurate; aromatic allyl compounds containing epoxy groups such as 2,2-bis[3-allyl-4-(glycidyloxy)phenyl]propane; aromatic allyl compounds containing benz oxazine such as bis[3-allyl-4-(3,4-dihydro-2H-1,3-benz oxazin-3-yl)phenyl]methane; aromatic allyl compounds containing ether such as 1,3,5-triallyl ether benzene; allyl silane compounds such as diallyl diphenylsilane; resins containing multiple benzene rings and allyl groups, etc. Examples of commercially available products of allyl-based radically polymerizable compounds include: "TAIC" (1,3,5-triallyl isocyanurate) manufactured by Nippon Kayaku Co., Ltd.; "DAD" (diallyl phthalate) manufactured by Nisshu Techno Fine Chemical Co., Ltd.; "TRIAM-705" (triallyl trimellitate) manufactured by Fujifilm Wako Pure Chemical Corporation; "DAND" (diallyl 2,3-naphthoate) manufactured by Nisshu Techno Fine Chemical Co., Ltd.; "ALP-d" (bis[3-allyl-4-(3,4-dihydro-2H-1,3-benz oxazin-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" (resins containing multiple benzene rings and allyl groups) manufactured by DIC Corporation, etc.

[0219] (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 the (meth)acrylic radical polymerizable compounds include: cyclohexane-1,4-dimethanol di(meth)acrylate, cyclohexane-1,3-dimethanol di(meth)acrylate, tricyclodecane dimethanol di(meth)acrylate, neopentyl glycol di(meth)acrylate, 1,4-butanediol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, 1,8-octanediol di(meth)acrylate, 1,9-nonanediol di(meth)acrylate, 1,10-decanediol di(meth)acrylate, trimethylolpropane tri(meth)acrylate, trimethylolethane tri(meth)acrylate, glycerol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate and other low molecular weight (molecular weight less than 1000) aliphatic (meth)acrylate compounds; di alkylene 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 and other low molecular weight (molecular weight less than 1000) ether-containing (meth)acrylate compounds; tris(3-hydroxypropyl)isocyanurate group tri(meth)acrylate, tris(2-hydroxyethyl)isocyanurate group tri(meth)acrylate, ethoxylated isocyanuric acid tri(meth)acrylate and other low molecular weight (molecular weight less than 1000) isocyanurate group-containing (meth)acrylate compounds; (meth)acrylic acid modified polyphenylene ether resin and other high molecular weight (molecular weight 1000 or more) acrylate compounds. Examples of commercially available products of the (meth)acrylic radical polymerizable compounds include: "A-DOG" (di alkylene 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" (di alkylene glycol diacrylate) manufactured by Nippon Kayaku Co., Ltd.; "SA9000", "SA9000-111" (methacrylic acid modified polyphenylene ether) manufactured by SABIC Corporation, etc.

[0220] Styrene-based free-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 free-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, and bis(4-vinylphenyl) ether; high-molecular-weight (molecular weight 1000 or more) styrene-based compounds such as vinylbenzyl-modified polyphenylene ether resin and styrene-divinylbenzene copolymer. Examples of commercially available products of styrene-based free-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-2St2200" (vinylbenzyl-modified polyphenylene ether resin) manufactured by Mitsubishi Gas Chemical Company, Inc.

[0221] Maleimide-based free-radical polymerizable compounds are, for example, compounds having one or more, preferably two or more maleimide groups (2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl). Maleimide-based free-radical polymerizable compounds can be aliphatic maleimide compounds containing an aliphatic amine skeleton or aromatic maleimide compounds containing an aromatic amine skeleton. Examples of commercially available products of maleimide-based free-radical polymerizable compounds include: "BMI-3000J", "BMI-5000", "BMI-1400", "BMI-1500", "BMI-1700", "BMI-689" manufactured by DesignerMolecules 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 KI Kasei Co., Ltd. In addition, as maleimide-based free-radical polymerizable compounds, maleimide resins (maleimide compounds containing an indane ring skeleton) described in Japanese Invention Association Publication Technical Report Public Technical Number 2020-500211 can be used.

[0222] The equivalent weight of the ethylenically unsaturated bond in component (E) is preferably from 20 g / eq. to 3,000 g / eq., more preferably from 50 g / eq. to 2,500 g / eq., still more preferably from 70 g / eq. to 2,000 g / eq., and even more preferably from 90 g / eq. to 1,500 g / eq. The equivalent weight of the ethylenically unsaturated bond represents the mass of the radically polymerizable compound per 1 equivalent of the ethylenically unsaturated bond.

[0223] The weight-average molecular weight of component (E) 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. There is no particular limitation on the lower limit, and for example, it may be 150 or more, etc. The weight-average molecular weight can be measured by gel permeation chromatography (GPC) as a polystyrene conversion value.

[0224] When the resin composition of the present invention contains component (E), when the non-volatile components in the resin composition are set to 100% by mass, the content of component (E) 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, still more preferably 2% by mass or more, for example, 15% by mass or less, preferably 10% by mass or less, more preferably 5% by mass or less, and still more preferably 3% by mass or less.

[0225] When the resin composition of the present invention contains component (E), when the resin components in the resin composition are set to 100% by mass, the content of component (E) 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, still more preferably 5% by mass or more, 7% by mass or more, or 8% by mass or more, for example, 25% by mass or less, preferably 20% by mass or less, more preferably 15% by mass or less, and still more preferably 10% by mass or less.

[0226] <(F) Other curing agents>

[0227] The resin composition of the present invention may further contain a curing agent other than component (B) (also referred to as "other curing agent") as component (F).

[0228] Examples of component (F) include: phenol resins, naphthol resins, acid anhydride resins, cyanate ester resins, carbodiimide resins, amine resins, etc. Component (F) can be used alone or in combination of two or more.

[0229] As phenol resins and naphthol resins, resins having a novolak structure are preferred from the viewpoints of heat resistance and water resistance. Further, from the viewpoint of adhesion to the conductor layer, nitrogen-containing phenol resins and nitrogen-containing naphthol resins are preferred, and phenol resins having a triazine skeleton and naphthol resins having a triazine skeleton are more preferred.

[0230] Specific examples of the phenol resins and naphthol resins include, for example, "MEH-7700", "MEH-7810", "MEH-7851", "MEH-8000H" manufactured by Meiko 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.

[0231] Examples of the acid anhydride resins include resins having one or more acid anhydride groups in one molecule. Specific examples of the acid anhydride resins include phthalic anhydride, tetrahydrophthalic anhydride, hexahydrophthalic anhydride, methyltetrahydrophthalic anhydride, methylhexahydrophthalic anhydride, methylnadic anhydride, hydrogenated methylnadic anhydride, trialkyltetrahydrophthalic anhydride, dodecenyl succinic anhydride, 5-(2,5-dioxotetrahydro-3-furanyl)-3-methyl-3-cyclohexene-1,2-dicarboxylic anhydride, trimellitic anhydride, pyromellitic anhydride, benzophenone tetracarboxylic dianhydride, biphenyltetracarboxylic dianhydride, naphthalenetetracarboxylic dianhydride, oxydiphthalic dianhydride, 3,3'-4,4'-diphenylsulfone tetracarboxylic 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(trimellitic anhydride), polymer-type acid anhydrides such as styrene-maleic acid resin copolymerized from styrene and maleic acid, etc. Commercially available products of the acid anhydride resins include "MH-700", etc. manufactured by Shin Nippon Rika Co., Ltd.

[0232] As cyanate ester resins, for example, the following can be cited: difunctional cyanate ester resins such as bisphenol A dicyanate, polyphenol cyanate, oligomeric (3-methylmethylene-1,5-phenylene cyanate), 4,4'-methylenebis(2,6-dimethylphenyl cyanate), 4,4'-ethylenediphenyl dicyanate, hexafluorobisphenol A dicyanate, 2,2-bis(4-cyanatephenyl)propane, 1,1-bis(4-cyanatephenyl)methane, bis(4-cyanate-3,5-dimethylphenyl)methane, 1,3-bis(4-cyanatephenyl-1-(methylethylene))benzene, bis(4-cyanatephenyl) sulfide, and bis(4-cyanatephenyl) ether; polyfunctional cyanate ester resins derived from phenol novolac and cresol novolac; prepolymers obtained by partially triazine-forming these cyanate ester resins, etc. As specific examples of cyanate ester resins, the following can be cited: "PT30" and "PT60" (phenol novolac type polyfunctional cyanate ester resins), "ULL-950S" (polyfunctional cyanate ester resin), "BA230", "BA230S75" (prepolymers in which part or all of bisphenol A dicyanate is triazine-formed into trimers), etc., manufactured by arxada.

[0233] As specific examples of carbodiimide resins, the following can be cited: CARBODILITE (registered trademark) V-03 (carbodiimide equivalent: 216 g / eq.), V-05 (carbodiimide equivalent: 262 g / eq.), V-07 (carbodiimide equivalent: 200 g / eq.), V-09 (carbodiimide equivalent: 200 g / eq.) manufactured by Nisshinbo Chemical Inc.; Stabaxol (registered trademark) P (carbodiimide equivalent: 302 g / eq.) manufactured by LANXESS.

[0234] As the amine-based resin, examples include resins having one or more amino groups in one molecule, such as aliphatic amines, polyether amines, alicyclic amines, aromatic amines, etc. Specific examples of the amine-based resin include 4,4'-methylenebis(2,6-dimethylaniline), diphenylsulfone diamine, 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, etc. The amine-based resin can be a commercially available product, such as "KAYABOND C-200S", "KAYABOND C-100", "KAYAHARDA-A", "KAYAHARDA-B", "KAYAHARDA-S" manufactured by Nippon Kayaku Co., Ltd.; "EPICURE W" manufactured by Mitsubishi Chemical Corporation, etc.

[0235] 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 further preferably 1:0.1 to 1:5, based on the ratio of [(total count of epoxy groups of the component (A))]:[(total count of active groups of the component (B) and the component (F))]. Regarding the "total count of epoxy groups of the component (A)", as described above. In addition, the "total count of active groups of the component (B) and the component (F)" means the value obtained by dividing the mass 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 component (F) by the active group equivalent, all totaled. When the resin composition of the present invention contains the component (F), by making the quantitative ratio of the component (B) and the component (F) to the component (A) within the range involved, the effects of the present invention can be significantly obtained.

[0236] When the resin composition of the present invention contains the component (F), when the non-volatile components in the resin composition are set to 100% by mass, 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, still more preferably 2% by mass or more, 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.

[0237] When the resin composition of the present invention contains the component (F), when the resin components in the resin composition are set to 100% by mass, 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, still more preferably 5% by mass or more, 7% by mass or more, or 8% by mass or more, 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.

[0238] <(G) Organic filler>

[0239] 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.

[0240] 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, polychloroprene, ethylene-vinyl acetate copolymer, styrene-butadiene copolymer, styrene-isoprene copolymer, styrene-isobutene copolymer, acrylonitrile-butadiene copolymer, isoprene-isobutene copolymer, isobutene-butadiene copolymer, ethylene-propylene-diene terpolymer, ethylene-propylene-butene terpolymer; thermoplastic elastomers such as acrylic-based thermoplastic elastomers like poly(propyl) (meth)acrylate, poly(butyl) (meth)acrylate, poly(cyclohexyl) (meth)acrylate, poly(octyl) (meth)acrylate. Moreover, silicone-based rubbers such as polyorganosiloxane rubber can also be mixed in the rubber component. The Tg of the rubber component contained in the rubber particles is, for example, 0°C or lower, preferably -10°C or lower, more preferably -20°C or lower, still more preferably -30°C or lower.

[0241] In one embodiment, the organic filler is a core-shell rubber particle, which is composed of a core particle containing the above-exemplified rubber component and a shell portion formed by graft copolymerization of a monomer component copolymerizable with the rubber component contained in the core particle. Here, the core-shell type does not necessarily refer only to a substance in which the core particle and the shell portion can be clearly distinguished, but also includes a substance in which the boundary between the core particle and the shell portion is unclear, and the core particle may not be completely covered by the shell portion.

[0242] Specific examples of the organic filler containing a rubber component include, for example: "CHT" manufactured by Samsung SDI Co., Ltd.; "B602" manufactured by Techno UMG Co., Ltd.; "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 Chemical Company; "METABLEN C-223A", "METABLEN E-901", "METABLEN S-2001", "METABLEN W-450A", "METABLEN SRK-200" manufactured by Mitsubishi Rayon Co., Ltd.; "Kane Ace M-511", "Kane Ace M-600", "Kane Ace M-400", "Kane Ace M-580", "Kane Ace MR-01" manufactured by Kaneka Corporation; "Staphyloid AC3355", "Staphyloid AC3816", "Staphyloid AC3832", "Staphyloid AC4030", "Staphyloid AC3364" manufactured by Aika Industries Co., Ltd., etc. They are core-shell rubber particles.

[0243] When the resin composition of the present invention contains the component (G), when the non-volatile components in the resin composition are set to 100% by mass, the content of the component (G) in the resin composition is, 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, 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.

[0244] When the resin composition of the present invention contains the component (G), when the resin component in the resin composition is set to 100% by mass, the content of the component (G) 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, further preferably 4% by mass or more, for example, 15% by mass or less, preferably 10% by mass or less, more preferably 7% by mass or less, further preferably 5% by mass or less.

[0245] <(H) Curing Accelerator>

[0246] The resin composition of the present invention may further contain a curing accelerator as the component (H).

[0247] Examples of the component (H) 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, etc. The curing accelerator may be used alone or in combination of two or more.

[0248] Examples of the phosphorus-based curing accelerator include aliphatic phosphonium salts such as tetrabutylphosphonium bromide, tetrabutylphosphonium chloride, tetrabutylphosphonium acetate, tetrabutylphosphonium decanoate, tetrabutylphosphonium laurate, bis(tetrabutylphosphonium)pyromellitic acid salt, tetrabutylphosphonium hexahydrophthalate, tetrabutylphosphonium 2,6-bis[(2-hydroxy-5-methylphenyl)methyl]-4-methylphenolate, and di-tert-butyldimethylphosphonium tetraphenylborate; methyltriphenylphosphonium bromide, ethyltriphenylphosphonium bromide, propyltriphenylphosphonium bromide, butyltriphenylphosphonium bromide, benzyltriphenylphosphonium chloride, and tetraphenylphosphonium bromide. Aromatic phosphonium salts such as phosphonium, 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 reactants; tributylphosphine, tri-tert-butylphosphine aliphatic phosphines such as trioctylphosphine, di-tert-butyl(2-butenyl)phosphine, di-tert-butyl(3-methyl-2-butenyl)phosphine and tricyclohexylphosphine; aliphatic phosphines such as dibutylphenylphosphine, di-tert-butylphenylphosphine, methyldiphenylphosphine, ethyldiphenylphosphine, butyldiphenylphosphine, diphenylcyclohexylphosphine, triphenylphosphine, tri-o-tolylphosphine, tri-m-tolylphosphine, tri-p-tolylphosphine, tri(4-ethylphenyl)phosphine, tri(4-propylphenyl)phosphine, tri(4-isopropylphenyl)phosphine, tri(4-butylphenyl)phosphine, tri(4-tert-butylphenyl)phosphine, tri(2,4-dimethylphenyl)phosphine, tri(2,5-dimethylphenyl)phosphine, tri( Aromatic phosphines such as 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, and 2,2'-bis(diphenylphosphino)diphenyl ether may be used.

[0249] Examples of the amine-based curing accelerator include trialkylamines such as triethylamine and tributylamine, 4-dimethylaminopyridine, benzyldimethylamine, 2,4,6-tris(dimethylaminomethyl)phenol, and 1,8-diazabicyclo(5,4,0)-undecene.

[0250] As the amine-based curing accelerator, commercially available products can be used. For example, "DMAP" manufactured by Tokyo Chemical Industry Co., Ltd.; "MY-25" manufactured by Ajinomoto Fine-Techno Co., Inc., etc. can be cited.

[0251] As the imidazole-based curing accelerator, for example, 2-methylimidazole, 2-undecylimidazole, 2-heptadecylimidazole, 1,2-dimethylimidazole, 2-ethyl-4-methylimidazole, 1,2-dimethylimidazole, 2-ethyl-4-methylimidazole, 2-phenylimidazole, 2-phenyl-4-methylimidazole, 1-benzyl-2-methylimidazole, 1-benzyl-2-phenylimidazole, 1-cyanoethyl-2-methylimidazole, 1-cyanoethyl-2-undecylimidazole, 1-cyanoethyl-2-ethyl-4-methylimidazole, 1-cyanoethyl-2-phenylimidazole, 1-cyanoethyl-2-undecylimidazolium trimellitate, 1-cyanoethyl-2-phenylimidazolium trimellitate, 2,4-diamino-6-[2'-methylimidazolyl-(1')]-ethyl-s-triazine, 2,4-diamino-6-[2'-undecylimidazolyl-(1')]-ethyl-s-triazine, 2,4-diamino-6-[2'-ethyl-4'-methylimidazolyl-(1')]-ethyl-s-triazine, 2,4-diamino-6-[2'-methylimidazolyl-(1')]-ethyl-s-triazine isocyanuric acid adduct, 2-phenylimidazole isocyanuric acid adduct, 2-phenyl-4,5-dihydroxymethylimidazole, 2-phenyl-4-methyl-5-hydroxymethylimidazole, 2,3-dihydro-1H-pyrrolo[1,2-a]benzimidazole, 1-dodecyl-2-methyl-3-benzylimidazolium chloride, 2-methylimidazoline, 2-phenylimidazoline, 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 and other imidazole compounds, their mixtures, and adducts of imidazole compounds and epoxy resins.

[0252] As the imidazole-based curing accelerator, commercially available products can be used. For example, "1B2PZ", "2MZA-PW", "2PHZ-PW", "C11Z-A", "2MAOK-PW", "2E4MZ" manufactured by Shikoku Chemicals Corporation; "P200-H50" manufactured by Mitsubishi Chemical Corporation, etc. can be cited.

[0253] As guanidine-based curing accelerators, examples include: dicyandiamide, 1-methylguanidine, 1-ethylguanidine, 1-cyclohexylguanidine, 1-phenylguanidine, 1-(o-tolyl)guanidine, dimethylguanidine, diphenylguanidine, trimethylguanidine, tetramethylguanidine, pentamethylguanidine, 1,5,7-triazabicyclo[4.4.0]dec-5-ene, 7-methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene, 1-methylbiguanide, 1-ethylbiguanide, 1-n-butylbiguanide, 1-n-octadecylbiguanide, 1,1-dimethylbiguanide, 1,1-diethylbiguanide, 1-cyclohexylbiguanide, 1-allylbiguanide, 1-phenylbiguanide, 1-(o-tolyl)biguanide, etc.

[0254] As metal-based curing accelerators, examples include: organometallic complexes or organometallic salts of metals such as cobalt, copper, zinc, iron, nickel, manganese, tin, etc. 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. As organometallic salts, examples include: zinc octoate, tin octoate, zinc naphthenate, cobalt naphthenate, tin stearate, zinc stearate, etc.

[0255] As peroxide-based curing accelerators, examples include: cyclohexanone peroxide, tert-butyl perbenzoate, methyl ethyl ketone peroxide, dicumyl peroxide, tert-butyl cumyl peroxide, di-tert-butyl peroxide, diisopropylbenzene hydroperoxide, cumene hydroperoxide, tert-butyl hydroperoxide. As peroxide-based curing accelerators, commercially available products can be used, for example, "PERCUMYL D" manufactured by NOF Corporation.

[0256] When the resin composition of the present invention contains the component (H), when the non-volatile components in the resin composition are set to 100% by mass, 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, further preferably 0.5% by mass or more, for example, 10.0% by mass or less, preferably 5.0% by mass or less, more preferably 3.0% by mass or less, further preferably 1.0% by mass or less, 0.9% by mass or less, or 0.7% by mass or less.

[0257] When the resin composition of the present invention contains the component (H), when the resin component in the resin composition is set to 100% by mass, 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, 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.

[0258] <(I) Optional Additives>

[0259] In the resin composition of the present invention, an (I) optional additive may be further contained in combination with the above 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, polyethersulfone resins, polyetheretherketone 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; homogenizers such as silicone-based homogenizers and acrylic polymer-based homogenizers; thickeners such as Benton and montmorillonite; defoamers such as silicone-based defoamers, acrylic-based defoamers, fluorine-based defoamers, and vinyl resin-based defoamers; ultraviolet absorbers such as benzotriazole-based ultraviolet absorbers; adhesion improvers such as ureidosilanes; 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 compounds, phosphazene compounds, hypophosphorous acid compounds, red phosphorus), nitrogen-based flame retardants (e.g., melamine sulfate), halogen-based flame retardants, and inorganic flame retardants (e.g., antimony trioxide); dispersants such as phosphate ester-based dispersants, polyoxyalkylene-based dispersants, acetylene-based dispersants, silicone-based dispersants, anionic dispersants, and cationic dispersants; stabilizers such as borate ester-based stabilizers, titanate-based stabilizers, aluminate-based stabilizers, zirconate-based stabilizers, isocyanate-based stabilizers, carboxylic acid-based stabilizers, and carboxylic anhydride-based stabilizers, etc. The content of the additives involved can be determined according to the properties required for the resin composition. The (I) optional additive can be used alone or in combination of two or more.

[0260] <(J) Solvent>

[0261] In the resin composition of the present invention, (J) a solvent can be further contained as a volatile component in combination with non-volatile components such as the above-described components (A) to (I).

[0262] As the (J) solvent, an organic solvent is usually used. 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, ethyldiglycol 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 can be used alone or in combination of two or more. The resin composition of the present invention can be produced, for example, as follows: The components (A), (B), (C), and, if necessary, the components (D), (E), (F), (G), (H), (I), or (J) are added to an arbitrary mixing container in an arbitrary order and / or partially or entirely simultaneously and mixed. In addition, during the process of adding each component and mixing, the temperature can be appropriately set, and heating and / or cooling can be performed temporarily or throughout. In addition, during or after the process of adding each component and mixing, for example, a stirring device such as a mixer or a shaking device can be used to stir or shake the resin composition to disperse it uniformly. In addition, while stirring or shaking, defoaming can be performed under low-pressure conditions such as under vacuum.

[0263]

[0264] [Physical Properties of Resin Composition]

[0265] ​As described above, the resin composition of the present invention contains (A) an epoxy resin, (B) an active ester-based curing agent, and (C) a compound containing a structural unit represented by formula (C1) and an end group represented by formula (c1), and provides a cured product having good dielectric properties and excellent adhesion strength to a conductor layer after being exposed to a high-temperature and high-humidity environment.

[0266] The cured product of the resin composition of the present invention is characterized by a low relative dielectric constant. Therefore, according to this cured product, an insulating layer with a low relative dielectric constant is provided. For example, as described in the <Test Example 1: Measurement of Relative Dielectric Constant and Dissipation Factor> column described later, when measured under the conditions of 5.8 GHz and 23 °C, the relative dielectric constant (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, and further preferably 3.5 or less. The lower limit value of the relative dielectric constant can be 0.001 or more, etc.

[0267] The cured product of the resin composition of the present invention is characterized by a low dissipation factor. Therefore, according to this cured product, an insulating layer with a low dissipation factor is provided. For example, as described in the <Test Example 1: Measurement of Relative Dielectric Constant and Dissipation Factor> column described later, when measured under the conditions of 5.8 GHz and 23 °C, the dissipation factor (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 further preferably 0.0025 or less. The lower limit value of the dissipation factor can be 0.001 or more, etc.

[0268] The insulating layer composed of the cured product of the resin composition of the present invention exhibits the following characteristics: excellent adhesion strength (peel strength) to the conductor layer after being exposed to a high-temperature and high-humidity environment. As the peel strength after being exposed to a high-temperature and high-humidity environment, it is preferably 0.2 kgf / cm or more, more preferably 0.3 kgf / cm or more. The measurement of the peel strength can be carried out according to the method described in the <Test Example 3: Measurement of Adhesion Strength to Conductor Layer Before and After Exposure to High-Temperature and High-Humidity Environment (HAST)> column described later. The higher the upper limit of the peel strength after being exposed to a high-temperature and high-humidity environment, the more preferable it is. For example, it can be 2.00 kg / cm or less.

[0269] The cured product of the resin composition of the present invention can exhibit the following characteristics: even before exposure to a high-temperature and high-humidity environment, the adhesion strength (peel strength) to the conductor layer is excellent. As the peel strength before exposure to a high-temperature and high-humidity environment, for example, it is 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 further preferably 0.5 kgf / cm or more. The higher the upper limit of the peel strength before exposure to a high-temperature and high-humidity environment, the more preferable it is. For example, it can be 2.00 kg / cm or less.

[0270] 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 excellent crack resistance. Therefore, an insulating layer with excellent crack resistance can be obtained. The evaluation of crack resistance can be carried out according to the method described in the <Test Example 2: Evaluation of Crack Resistance after Cleaning Treatment> column described later. Specifically, a layer composed of the cured product of the resin composition is formed on a core material having 100 copper pad portions. The layer composed of the cured product is roughened, and 100 roughened copper pad portions are observed to confirm the presence or absence of cracks. In this case, the number of cracks is preferably 10 or less. The lower limit of the number of cracks can be 0, or more than 0.

[0271] [Use of the resin composition]

[0272] As described above, the resin composition of the present invention can provide a cured product that exhibits good dielectric properties and has 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 the insulating layer of a printed wiring board), and can be more suitably used as a resin composition for forming an interlayer insulating layer of a printed wiring board (resin composition for the interlayer insulating layer of a 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 the insulating layer of a redistribution substrate). It should be noted that in the present invention, the printed wiring board or the redistribution substrate is also 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.

[0273] Moreover, the resin composition of the present invention can be widely used in applications that require a resin composition, such as sheet-like laminated materials such as resin sheets and prepregs, solder masks, underfill materials, chip bonding materials, via filling resins, encapsulation resins, and component-embedded resins.

[0274] [Sheet-like laminated materials (resin sheets, prepregs)]

[0275] The resin composition of the present invention can be used directly or in the form of a sheet-like laminate containing the resin composition.

[0276] As the sheet-like laminate, a resin sheet, a prepreg, etc. shown below are preferable.

[0277] 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 is characterized in that the resin composition layer is formed of the resin composition of the present invention.

[0278] The suitable value of the thickness of the resin composition layer varies depending on the use and can be appropriately determined according to the use. For example, from the viewpoint of thinning of printed wiring boards or 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. There is no particular limitation on the lower limit of the thickness of the resin composition layer, and it can generally be 1 μm or more, 5 μm or more, etc.

[0279] Examples of the support include: a thermoplastic resin film, a metal foil, a release paper, and a thermoplastic resin film and a metal foil are preferable. Therefore, in a suitable embodiment, the support is a thermoplastic resin film or a metal foil.

[0280] When using a thermoplastic resin film as the support, examples of the thermoplastic resin include: polyesters such as polyethylene terephthalate (PET), polyethylene naphthalate (PEN), polycarbonate (PC), acrylics such as polymethyl methacrylate (PMMA), cyclic polyolefins, triacetyl cellulose (TAC), polyethyl sulfide (PES), polyether ketone, polyimide, etc. Among them, polyethylene terephthalate and polyethylene naphthalate are preferable, and inexpensive polyethylene terephthalate is particularly preferable.

[0281] When using a metal foil as the support, examples of the metal foil include: copper foil, aluminum foil, etc., and copper foil is preferable. As the copper foil, a foil made of single metal of copper or a foil made of an alloy of copper and other metals (for example, tin, chromium, silver, magnesium, nickel, zirconium, silicon, titanium, etc.) can be used.

[0282] The surface of the support that is joined to the resin composition layer can be subjected to matting treatment, corona treatment, or antistatic treatment. Additionally, as the support, a support with a release layer on the surface joined to the resin composition layer can be used. Examples of the release agent in the release layer of the support with a release layer include one or more release agents selected from alkyd resins, polyolefin resins, urethane resins, and silicone resins. Examples of commercially available products of the release agent include "SK-1", "AL-5", "AL-7", etc. manufactured by LINTEC Corporation as alkyd resin-based release agents. Additionally, examples of commercially available products of the support with a release layer include "SK-1", "AL-5", "AL-7" manufactured by LINTEC Corporation as 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; "Unipeel" manufactured by UNITIKA Ltd., etc.

[0283] There is no particular limitation on the thickness of the support, and the range of 5 μm to 75 μm is preferred, and the range of 10 μm to 60 μm is more preferred. It should be noted that when using a support with a release layer, it is preferred that the overall thickness of the support with a release layer is within the above range.

[0284] When using a metal foil as the support, a metal foil with a support substrate that can be peeled off and adhered to a thin metal foil can 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.

[0285] In the metal foil with a support substrate, there is no particular limitation on the material of the support substrate, and examples include: copper foil, aluminum foil, stainless steel foil, titanium foil, copper alloy foil, etc. When using a copper foil as the support substrate, it can be an electrolytic copper foil or a rolled copper foil. Additionally, the release layer only needs to be able to peel the metal foil from the support substrate, and there is no particular limitation. Examples include: alloy layers of elements selected from Cr, Ni, Co, Fe, Mo, Ti, W, P; organic films, etc.

[0286] In the metal foil with a support substrate, as the material of the metal foil, copper foil and copper alloy foil are preferred, for example.

[0287] In the metal foil with a support substrate, there is no particular limitation on the thickness of the support substrate, and the range of 10 μm to 150 μm is preferred, and the range of 10 μm to 100 μm is more preferred. Additionally, the thickness of the metal foil can be in the range of 0.1 μm to 10 μm, for example.

[0288] In one embodiment, if necessary, the resin sheet may further include an optional layer. Examples of the optional layer involved include a protective film provided on the surface of the resin composition layer that is not bonded to the support (i.e., the surface opposite to the support). There is no particular limitation on the thickness of the protective film, for example, it is 1 μm to 40 μm. By laminating the protective film, it is possible to suppress the adhesion of dust, etc. to the surface of the resin composition layer or damage to the surface of the resin composition layer.

[0289] The resin sheet can be manufactured, for example, as follows: using a die coater or the like, directly coat a liquid resin composition on a support, or prepare a resin varnish in which the resin composition is dissolved in an organic solvent, and coat the prepared resin varnish on the support, and further dry to form a resin composition layer.

[0290] Examples of the organic solvent include the same organic solvents as those described as components of the resin composition. The organic solvent can be used alone or in combination of two or more.

[0291] Drying can be carried out by known methods such as heating and blowing hot air. There is no particular limitation on the drying conditions, and drying is carried out in such a way that the content of the organic solvent in the resin composition layer reaches 10% by mass or less, preferably 5% by mass or less. Although it 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% to 60% by mass of an organic solvent, a resin composition layer can be formed by drying at 50°C to 150°C for 3 minutes to 10 minutes.

[0292] The resin sheet can be wound into a roll for storage. When the resin sheet has a protective film, the resin sheet can be used by peeling off the protective film.

[0293] In one embodiment, the prepreg is formed by impregnating a sheet-like fiber substrate with the resin composition of the present invention.

[0294] There is no particular limitation on the sheet-like fiber substrate used for the prepreg, and sheet-like fiber substrates commonly used as prepreg substrates such as glass cloth, aramid nonwoven fabric, and liquid crystal polymer nonwoven fabric can be used. From the viewpoint of thinning of printed wiring boards or semiconductor chip packages, the thickness of the sheet-like fiber substrate is preferably 50 μm or less, more preferably 40 μm or less, further preferably 30 μm or less, and particularly preferably 20 μm or less. There is no particular limitation on the lower limit of the thickness of the sheet-like fiber substrate. Usually, it is 10 μm or more.

[0295] The prepreg can be manufactured by known methods such as the hot melt method and the solvent method.

[0296] The thickness of the prepreg may be in the same range as the resin composition layer in the resin sheet described above.

[0297] The sheet-like laminate of the present invention can be suitably used for forming an insulating layer of a printed wiring board (insulating layer for printed wiring board), and can be more suitably used for forming an interlayer insulating layer of a printed wiring board (interlayer insulating layer for printed wiring board). The sheet-like laminate of the present invention can also be suitably used for forming an insulating layer of a rewiring substrate of a semiconductor package (insulating layer for rewiring substrate). That is, the sheet-like laminate of the present invention can be suitably used for an insulating layer of a circuit board.

[0298] [Circuit board]

[0299] The insulating layer of a circuit board can be formed using the resin composition of the present invention. The present invention also provides a circuit board related thereto, that is, a circuit board including an insulating layer composed of a cured product of the resin composition of the present invention.

[0300] <Printed wiring board>

[0301] In one embodiment, the circuit board of the present invention is a printed wiring board.

[0302] The printed wiring board can be manufactured, for example, by the method including the following steps (I) and (II) using the resin sheet described above.

[0303] Step (I): Stack the resin sheet on the inner layer substrate in such a manner that the resin composition layer of the resin sheet is bonded to the inner layer substrate.

[0304] Step (II): Cure the resin composition layer (for example, thermally cure) to form an insulating layer.

[0305] The "inner layer substrate" used in step (I) is a member that becomes the substrate of the printed wiring board. For example, it can be cited: glass epoxy substrate, metal substrate, polyester substrate, polyimide substrate, BT resin substrate, thermosetting polyphenylene ether substrate, etc. In addition, the substrate may have a conductor layer on one or both sides thereof, and the conductor layer can also be patterned. Sometimes the inner layer substrate having a conductor layer (circuit) formed on one or both sides of the substrate is called an "inner layer circuit substrate". In addition, in the manufacture of a printed wiring board, an intermediate product to which an insulating layer and / or a conductor layer are to be further formed is also included in the "inner layer substrate" mentioned in the present invention. In the case where the printed wiring board is a component-embedded circuit board, an inner layer substrate having components embedded therein can also be used.

[0306] The lamination of the inner substrate and the resin sheet can be performed, for example, by heat-pressing the resin sheet to the inner substrate from the support body side. As a member for heat-pressing the resin sheet to the inner substrate (hereinafter, also referred to as a "heat-pressing member"), for example, a heated metal plate (SUS end plate, etc.) or a metal roller (SUS roller) can be cited. It should be noted that the heat-pressing member and the resin sheet are not directly pressed, but pressed through an elastic material such as heat-resistant rubber so that the resin sheet can fully follow the surface unevenness of the inner substrate.

[0307] The lamination of the inner substrate and the resin sheet can be implemented by vacuum lamination. In the vacuum lamination method, the heating and pressing temperature is preferably 60°C to 160°C, more preferably in the range of 80°C to 140°C, the heating and pressing pressure is preferably 0.098MPa to 1.77MPa, more preferably in the range of 0.29MPa to 1.47MPa, and the heating and pressing time is preferably 20 seconds to 400 seconds, more preferably in the range of 30 seconds to 300 seconds. Lamination can be preferably implemented under reduced pressure conditions of 26.7hPa or less.

[0308] Lamination can be performed by a commercially available vacuum laminator. Examples of the commercially available vacuum laminator include a vacuum pressure laminator manufactured by Meiki Manufacturing Co., Ltd., a vacuum applicator manufactured by Nikko-Materials Co., Ltd., and a batch vacuum pressure laminator.

[0309] After lamination, the laminated resin sheet can also be smoothed by pressing the heated pressing member at normal pressure (atmospheric pressure), for example, from the support side. The pressing conditions for the smoothing treatment can be set to the same conditions as the heated pressing conditions for the above-mentioned lamination. The smoothing treatment can be performed using a commercially available laminator. It should be noted that the lamination and smoothing treatment can be performed continuously using the above-mentioned commercially available vacuum laminator.

[0310] The support may be removed between step (I) and step (II), or after step (II). It should be noted that, when a metal foil is used as the support, the metal foil may be used to form the conductor layer without peeling off the support. In addition, when a metal foil with a supporting substrate is used as the support, the supporting substrate (and the peeling layer) may be peeled off. Furthermore, the conductor layer may be formed using a metal foil.

[0311] In step (II), the resin composition layer is cured (for example, thermally cured) to form an insulating layer composed of a cured product of the resin composition. The curing conditions of the resin composition layer are not particularly limited, and conditions commonly used in forming an insulating layer of a printed wiring board can be used.

[0312] 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, and still more preferably 160°C to 230°C. The curing time is preferably 5 minutes to 240 minutes, more preferably 10 minutes to 150 minutes, and still more preferably 15 minutes to 120 minutes.

[0313] Before thermally curing the resin composition layer, the resin composition layer can be preheated at a temperature lower than the curing temperature. For example, before thermally curing the resin composition layer, the resin composition layer can 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, and still more preferably 15 minutes to 100 minutes.

[0314] When manufacturing a printed wiring board, the following steps can be further implemented: (III) a step of opening holes in the insulating layer; (IV) a step of roughening the insulating layer; (V) a step of forming a conductor layer. These steps (III) to (V) can be implemented by various methods known to those skilled in the art for manufacturing printed wiring boards. It should be noted that when the support is removed after step (II), the removal of the support can be carried out between step (II) and step (III), between step (III) and step (IV), or between step (IV) and step (V). Additionally, if necessary, the formation of the insulating layer and the conductor layer in steps (I) to (V) can be repeatedly implemented to form a multilayer wiring board.

[0315] 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 that in the case of using a resin sheet.

[0316] Step (III) is a step of opening holes in the insulating layer. Thereby, holes such as via holes and through holes can be formed in the insulating layer. For step (III), depending on the composition of the resin composition used to form the insulating layer and the like, for example, a drill bit, a laser, a plasma, etc. can be used to implement it. The size or shape of the holes can be appropriately determined according to the design of the printed wiring board.

[0317] Step (IV) is a step of roughening the insulating layer. Generally, in this step (IV), the removal of contaminants (decontamination) is also carried out. There are no particular limitations on the steps and conditions of the roughening treatment, and known steps and conditions commonly used when forming the insulating layer of a printed wiring board can be adopted. For example, a swelling treatment based on a swelling liquid, a roughening treatment based on an oxidant, and a neutralization treatment based on a neutralizing liquid can be sequentially implemented to roughen the insulating layer.

[0318] The swelling liquid for roughening treatment is not particularly limited, and examples thereof include: an alkali solution, a surfactant solution, etc. An alkali solution is preferred, and as the alkali solution, a sodium hydroxide solution or a potassium hydroxide solution is more preferred. As commercially available swelling liquids, for example, "Swelling Dip Securiganth P", "Swelling Dip Securiganth SBU", etc. manufactured by Atotech Japan Co., Ltd. can be cited. The swelling treatment based on the swelling liquid is not particularly limited. For example, it can be carried out 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 preferred to immerse the insulating layer in the swelling liquid at 40°C to 80°C for 5 minutes to 15 minutes.

[0319] The oxidizing agent for roughening treatment is not particularly limited. For example, an alkaline permanganic acid solution obtained by dissolving potassium permanganate or sodium permanganate in an aqueous solution of sodium hydroxide can be cited. The roughening treatment based on an oxidizing agent such as an alkaline permanganic acid solution is preferably carried out by immersing the insulating layer in the oxidizing agent solution heated to 60°C to 100°C for 10 minutes to 30 minutes. In addition, the concentration of the permanganate in the alkaline permanganic acid solution is preferably 5% by mass to 10% by mass. As commercially available oxidizing agents, for example, alkaline permanganic acid solutions such as "Concentrate Compact CP", "Concentrate Compact P", "Dosing Solution Securiganth P", etc. manufactured by Atotech Japan Co., Ltd. can be cited.

[0320] In addition, as the neutralizing liquid for roughening treatment, an acidic aqueous solution is preferred. As commercially available products, for example, "Reduction Solution Securiganth P" manufactured by Atotech Japan Co., Ltd. can be cited.

[0321] The treatment based on the neutralizing liquid can be carried out by immersing the treated surface that has undergone roughening treatment based on the oxidizing agent in the neutralizing liquid at 30°C to 80°C for 5 minutes to 30 minutes. From the viewpoints of operability and the like, a method of immersing the object that has undergone roughening treatment based on the oxidizing agent in the neutralizing liquid at 40°C to 70°C for 5 minutes to 20 minutes is preferred.

[0322] Step (V) is a step of forming a conductor layer, which is formed on an insulating layer. There is no particular limitation on the conductor material used for the conductor layer. In a suitable embodiment, the conductor layer contains one or more metals selected from 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. As the alloy layer, for example, a layer formed of an alloy of two or more metals selected from the above (for example, nickel-chromium alloy, copper-nickel alloy, and copper-titanium alloy) can be cited. Among them, from the viewpoints of the versatility of forming the conductor layer, cost, ease of patterning, etc., a single-metal layer of chromium, nickel, titanium, aluminum, zinc, gold, palladium, silver, or copper, or an alloy layer of 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 further preferred.

[0323] The conductor layer may have a single-layer structure, or may be a multilayer structure obtained by laminating two or more single-metal layers or alloy layers composed of different kinds of metals or alloys. In the case where the conductor layer has a multilayer structure, it is preferred that the layer in contact with the insulating layer is a single-metal layer of chromium, zinc, or titanium, or an alloy layer of nickel-chromium alloy.

[0324] The thickness of the conductor layer depends on the design of the desired printed wiring board, and is usually 3 μm to 35 μm, preferably 5 μm to 30 μm.

[0325] In one embodiment, the conductor layer can be formed by electroplating. From the viewpoint of easy formation of fine wiring, formation by the semi-additive method is preferred. Hereinafter, an example of forming a conductor layer by the semi-additive method is shown.

[0326] First, an electroless plating seed layer is formed on the surface of the insulating layer by electroless plating. Next, a mask pattern corresponding to the desired wiring pattern and exposing a part of the electroless plating seed layer is formed on the formed electroless plating seed layer. After forming a metal layer on the exposed electroless plating seed layer by electrolytic plating, the mask pattern is removed. After that, the unnecessary electroless plating seed layer is removed by etching or the like, and a conductor layer having the desired wiring pattern can be formed.

[0327] In other embodiments, a metal foil may be used to form the conductor layer. In the case of using a metal foil to form the conductor layer, step (V) is suitably 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). Then, step (II) is carried out to form the 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 a modified semi-additive method.

[0328] The metal foil can be manufactured by a conventionally known method such as an electrolytic method or a rolling method. As commercially available products of the metal foil, for example, there can be mentioned: HLP foil and JXUT-III foil manufactured by JX Metals Co., Ltd.; 3EC-III foil and TP-III foil manufactured by Mitsui Mining & Smelting Co., Ltd.

[0329] Alternatively, as described above, in the case of using a metal foil or a metal foil with a support substrate as the support of the resin sheet, the metal foil can be used to form the conductor layer.

[0330] <Redistribution Substrate of Semiconductor Package>

[0331] In one embodiment, the circuit substrate of the present invention is a redistribution substrate (redistribution layer) of a semiconductor package. Hereinafter, a method for manufacturing a semiconductor package will be described.

[0332] The semiconductor package includes an insulating layer made of a cured product of the resin composition of the present invention as the insulating layer of the redistribution substrate. It should be noted that the semiconductor package may include a sealing layer made of a cured product of the resin composition of the present invention.

[0333] The semiconductor package can be manufactured, for example, by a method including the following steps (1) to (6) using the resin composition and the resin sheet of the present invention. In order to form the redistribution formation layer (for forming the insulating layer of the redistribution substrate) of step (5) or the sealing layer of step (3), the resin composition and the resin sheet of the present invention can be used. Hereinafter, an example of forming the redistribution formation layer or the sealing layer using the resin composition or the resin sheet is shown. The technique for forming the redistribution formation layer or the sealing layer of the semiconductor package is conventionally known, and those skilled in the art can manufacture the semiconductor package using the resin composition or the resin sheet of the present invention according to the conventionally known technique.

[0334] Step (1), laminating a temporary fixing film on a substrate;

[0335] Step (2), temporarily fixing a semiconductor chip on the temporary fixing film;

[0336] Step (3), forming a sealing layer on the semiconductor chip;

[0337] Step (4), peeling the base material and the temporary fixing film from the semiconductor chip;

[0338] Step (5), forming a rewiring formation layer as an insulating layer on the surface of the semiconductor chip from which the base material and the temporary fixing film have been peeled; and

[0339] Step (6), forming a rewiring layer as a conductor layer on the rewiring formation layer.

[0340] - Step (1) -

[0341] There is no particular limitation on the material for the base material. Examples of the base material include: semiconductor wafers such as silicon wafers; glass wafers; glass substrates; metal substrates such as copper, titanium, stainless steel, cold-rolled steel sheets (SPCC); substrates obtained by impregnating glass fibers with epoxy resins or the like and performing a heat curing treatment (e.g., FR-4 substrates); substrates made of bismaleimide triazine resin (BT resin), etc.

[0342] The temporary fixing film can be peeled from the semiconductor chip in Step (4), and there is no particular limitation on the material as long as it can temporarily fix the semiconductor chip. Commercially available products can be used as the temporary fixing film. Examples of commercially available products include REVALPHA manufactured by Nitto Denko Corporation.

[0343] - Step (2) -

[0344] The temporary fixing of the semiconductor chip can be performed using known devices such as a flip chip bonder or a die bonder. The layout and the number of configurations 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 arranged in a matrix of multiple rows and multiple columns for temporary fixing.

[0345] - Step (3) -

[0346] Laminate the resin sheet resin composition layer of the present invention on the semiconductor chip, or coat the resin composition of the present invention on the semiconductor chip and cure it (e.g., thermally cure) to form a sealing layer.

[0347] For example, the stacking of the semiconductor chip and the resin sheet can be performed by heating and pressing the resin sheet on the semiconductor chip from the support body side after removing the protective film of the resin sheet. As a component for heating and pressing the resin sheet on the semiconductor chip (hereinafter, also referred to as "heating and pressing component"), for example, a heated metal plate (SUS end plate, etc.) or a metal roller (SUS roller) etc. can be cited. It should be noted that it is preferred that the heating and pressing component is not directly pressed on the resin sheet, but is pressed through an elastic material such as heat-resistant rubber so that the resin sheet fully follows the surface unevenness of the semiconductor chip. The stacking of the semiconductor chip and the resin sheet can be implemented by a vacuum lamination method, and the stacking conditions can be the same as the stacking conditions described in the method for manufacturing a printed wiring board, and the preferred range can also be the same.

[0348] After lamination, the resin composition is thermally cured to form a sealing layer. The thermal curing conditions are the same as those described in the method for producing a printed wiring board.

[0349] The support of the resin sheet may be peeled off after the resin sheet is laminated on the semiconductor chip and thermally cured, or the support may be peeled off before the resin sheet is laminated on the semiconductor chip.

[0350] When the resin composition of the present invention is applied to form a sealant layer, the coating conditions may be the same as those for forming the resin composition layer described with respect to the resin sheet of the present invention, and the preferred ranges may also be the same.

[0351] -Process (4)-

[0352] The method of peeling off the substrate and the temporary fixing film can be appropriately changed according to the material of the temporary fixing film, for example, there can be mentioned: a method of peeling off by heating the temporary fixing film to make it foam (or expand); and a method of peeling off by irradiating ultraviolet rays from the substrate side to reduce the adhesive force of the temporary fixing film, etc.

[0353] In the method of peeling off by heating the temporary fixing film to make it foam (or expand), the heating conditions are usually 100 to 250°C for 1 to 90 seconds or 5 to 15 minutes. In the method of peeling off by irradiating ultraviolet rays from the substrate side to reduce the adhesive force of the temporary fixing film, the irradiation amount of ultraviolet rays is usually 10 mJ / cm 2 ~1000mJ / cm 2 .

[0354] -Process (5)-

[0355] The resin composition and the resin sheet of the present invention are used to form a rewiring formation layer (insulating layer of a rewiring board).

[0356] After forming the redistribution formation layer, in order to make an interlayer connection between the semiconductor chip and the conductor layer described later, vias can be formed on the redistribution formation layer. The vias can be formed by known methods according to the material of the redistribution formation layer.

[0357] - Process (6)-

[0358] Forming the conductor layer on the redistribution formation layer can be carried out in the same manner as Process (V) described in the manufacturing method of the printed wiring board. It should be noted that Processes (5) and (6) can be repeated to alternately stack (build-up, laminate) the conductor layer (redistribution layer) and the redistribution formation layer (insulating layer).

[0359] When manufacturing a semiconductor chip package, the following processes can be further carried out: (7) a process of forming a solder resist layer on the conductor layer (redistribution layer); (8) a process of forming bumps; (9) a process of dicing a plurality of semiconductor chip packages into individual semiconductor chip packages and singulating them. These processes can be carried out according to various methods well-known to those skilled in the art used in the manufacturing of semiconductor chip packages.

[0360] By using the resin composition and resin sheet of the present invention that can bring about a cured product having good dielectric properties and excellent adhesion strength to the conductor layer after being exposed to a high-temperature and high-humidity environment to form the redistribution formation layer (insulating layer), a semiconductor package with extremely low transmission loss can be achieved regardless of whether the semiconductor package 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. Whether it is a Fan-Out Panel-Level Package (FO-PLP) or a Fan-Out Wafer-Level Package (FO-WLP), the resin composition and resin sheet of the present invention can be applied. 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).

[0361] [Semiconductor Device]

[0362] The semiconductor device of the present invention includes a layer composed 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.

[0363] Examples of semiconductor devices include various semiconductor devices for electrical products (such as computers, mobile phones, digital cameras, and televisions, etc.) and transportation means (such as motorcycles, automobiles, trams, ships, and airplanes, etc.).

[0364] Examples

[0365] Hereinafter, examples are shown to specifically illustrate the present invention. However, the present invention is not limited to these examples. In the following description, unless otherwise specified, "parts" and "%" indicating amounts refer to "parts by mass" and "% by mass", respectively. In addition, the temperature conditions and pressure conditions are room temperature (23 °C) and atmospheric pressure (1 atm) when not particularly specified.

[0366] <Synthesis Example 1: Synthesis of Compound C-a Containing a Specific Structural Unit and a Specific Terminal Group>

[0367] Weigh 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) into a four-necked separable flask equipped with a stirring device, add N-methyl-2-pyrrolidone (42.50 g), and react it at 10.0 °C for 6 hours under a nitrogen atmosphere. After the reaction, while cooling the container to 10 °C, add m,p-(chloromethyl)styrene (11.53 g) dropwise, and then react it at 100 °C for 4 hours.

[0368] Add N-methyl-2-pyrrolidone (55.0 g) to the resulting reaction solution. After removing salts by filtration from the diluted liquid, pour the resulting solution into methanol (6900 g). Filter out the precipitated solid, wash the solid with a small amount of methanol, filter it again and recover it, and then dry it 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 is 3,400.

[0369]

[0370] <Synthesis Example 2: Synthesis of Compound C-b Containing a Specific Structural Unit and a Specific Terminal Group>

[0371] Change the raw materials and alkali metal compounds used 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). Except for this, carry out the synthesis according to the same steps as in Synthesis Example 1 to obtain Compound C-b represented by the following formula (2) (yield 46.55 g, yield 90%). The Mw of Compound C-b is 3,400.

[0372]

[0373] <Synthesis Example 3: Synthesis of Compound C-c Containing Specific Structural Units and Specific Terminal Groups>

[0374] The raw materials and alkali metal compounds 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). Otherwise, the synthesis was carried out in the same manner as in Synthesis Example 1 to obtain Compound C-c represented by the following formula (3) (yield 89.30 g, yield 90%). The Mw of Compound C-c was 4,000.

[0375]

[0376] In formula (C-c), R X is a divalent group represented by the following formula (4) or the following formula (5). It should be noted that in formula (4) and formula (5), "*" represents the bonding site.

[0377]

[0378] <Synthesis Example 4: Synthesis of Compound C-d Containing Specific Structural Units and Terminal Hydroxyl Groups>

[0379] The raw materials and alkali metal compounds 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). Otherwise, the synthesis was carried out in the same manner as in Synthesis Example 1 to obtain the polymer represented by the following formula (6) (yield 70.00 g, yield 90%).

[0380]

[0381] <Synthesis Example 5: Synthesis of Active Ester Compound B1>

[0382] In a flask equipped with a thermometer, a dropping funnel, a condenser, a fractionating column, and a stirrer, 2,7-dihydroxynaphthalene (320 g, 2.0 moles), benzyl alcohol (184 g, 1.7 moles), and p-toluenesulfonic acid monohydrate (5.0 g) were charged, and the mixture was stirred while blowing nitrogen at room temperature. Then, the temperature was raised to 150 °C, and the mixture was stirred for 4 hours while distilling the generated water out of the system. After completion of the reaction, methyl isobutyl ketone (900 g) and 20% aqueous sodium hydroxide solution (5.4 g) were added for neutralization, and then the aqueous layer was removed by liquid separation. The organic layer was washed three times with water (280 g), and methyl isobutyl ketone was removed under reduced pressure to obtain a benzyl-modified naphthalene compound B’ (460 g). The obtained benzyl-modified naphthalene compound B’ was a black solid, and the hydroxyl equivalent was 180 g / equivalent.

[0383] In a flask equipped with a thermometer, a dropping funnel, a condenser, a fractionating column, and a stirrer, isophthaloyl chloride (203.0 g, number of moles of acyl chloride group: 2.0 moles) and toluene (1400 g) were charged, and the system was purged with nitrogen under reduced pressure and dissolved. Then, o-phenylphenol (113.9 g, 0.67 mole) and benzyl-modified naphthalene compound B’ (240 g, number of moles of phenolic hydroxyl group: 1.33 moles) were charged, and the system was purged with nitrogen under reduced pressure and dissolved. Then, tetrabutylammonium bromide (0.70 g) was dissolved, and while purging with nitrogen, the temperature inside the system was controlled below 60 °C, and 20% aqueous sodium hydroxide solution (400 g) was added dropwise over 3 hours. Then, the mixture was continuously stirred under these conditions for 1.0 hour. 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 reactants were dissolved, and the mixture was 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. Then, the water was removed by decantation to obtain an active ester compound B1 in the form of a toluene solution containing 65% by mass of non-volatile components. The active ester group equivalent of the obtained active ester compound B1 was 238 g / eq.

[0384] <Synthesis Example 6: Synthesis of Vinyl Compound E2>

[0385] According to Example 1 of International Publication No. 2017 / 115813, divinylbenzene (390.6 g, 3.0 moles), ethyl vinylbenzene (229.4 g, 1.8 moles), styrene (1066.3 g, 10.2 moles), and n-propyl acetate (1532.0 g, 15.0 moles) were charged into a 5.0 L reactor, and 600 mmol of boron trifluoride diethyl ether complex was added at 70 °C, and the mixture was reacted for 4 hours. After stopping the polymerization solution with an aqueous sodium bicarbonate solution, the oil layer was washed three times with pure water, and volatile components were removed under reduced pressure at 60 °C to recover the polymer. The obtained product was weighed, and it was confirmed that vinyl compound E2 (896.7 g) was obtained. The Mw of vinyl compound E2 was 41,300.

[0386] <Preparation of Resin Varnishes of Examples 1 to 12 and Comparative Examples 1 to 3>

[0387] Weighed each component according to the parts by mass described 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. It should be noted that the amounts of the components described in Table 1 represent the amounts in terms of non-volatile components. In addition, the details of each component described in Table 1 are as follows.

[0388] (A) Epoxy resin

[0389] · "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.

[0390] · "HP-4032-SS": Manufactured by DIC Corporation, naphthalene-type liquid epoxy resin, epoxy equivalent 144 g / eq.

[0391] · "NC-3000L": Manufactured by Nippon Kayaku Co., Ltd., biphenyl-type epoxy resin, epoxy equivalent about 272 g / eq.

[0392] (B) Active ester-based curing agent

[0393] · "Active ester compound B1": Active ester compound B1 obtained in Synthesis Example 5

[0394] · "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.

[0395] · "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

[0396] (C) Compound containing a specific structural unit and a specific terminal group

[0397] · "C-a": Compound C-a containing a specific structural unit and a specific terminal group obtained in Synthesis Example 1

[0398] · "C-b": Compound C-b containing a specific structural unit and a specific terminal group obtained in Synthesis Example 2

[0399] · "C-c": Compound C-c containing a specific structural unit and a specific terminal group obtained in Synthesis Example 3

[0400] (C’) A compound containing a specific structural unit and a terminal hydroxyl group

[0401] · “C-d”: Compound C-d containing a specific structural unit and a terminal hydroxyl group obtained in Synthesis Example 4

[0402] (D) Inorganic filler

[0403] · “SO-C2”: Spherical silica (manufactured by Admatechs) surface-treated with an amine-based alkoxysilane compound (“KBM573” manufactured by Shin-Etsu Chemical Co., Ltd.), average particle diameter 0.5 μm, specific surface area 5.8 m 2 / g

[0404] (E) Compound containing a radically polymerizable group

[0405] · “Maleimide compound E1”: A compound represented by the following formula (M) (Mw / Mn = 1.81, t” = 1.47 (mainly 1, 2 or 3)), a MEK solution with a non-volatile content of 62% by mass, synthesized by the method described in Synthesis Example 1 of Japanese Invention Association Publication No. 2020-500211

[0406]

[0407] · “MIR-3000-70MT”: Manufactured by Nippon Kayaku Co., Ltd., a maleimide compound, a MEK / toluene mixed solution with a non-volatile content of 70%

[0408] · “SLK-6895”: Manufactured by Shin-Etsu Chemical Co., Ltd., a maleimide compound

[0409] · “SLK-1500”: Manufactured by Shin-Etsu Chemical Co., Ltd., a maleimide compound

[0410] · “Vinyl compound E2”: Vinyl compound obtained in Synthesis Example 6

[0411] (F) Other curing agents

[0412] · “LA-3018-50P”: Manufactured by DIC Corporation, a phenol-based curing agent, a 1-methoxy-2-propanol solution with a non-volatile content of 50% by mass, phenol equivalent 151 g / eq.

[0413] (G) Organic filler

[0414] · “EXL-2655”: Manufactured by Dow Chemical Japan Co., Ltd., rubber particles

[0415] (H) Curing accelerator

[0416] · "1B2PZ": Manufactured by Shikoku Kasei Kogyo Co., Ltd., an imidazole-based curing accelerator

[0417] <Test Example 1: Measurement of Relative Dielectric Constant and Dissipation Factor>

[0418] (1) Preparation of Resin Sheet A with a Resin Composition Layer Thickness of 40 μm

[0419] As a support, a polyethylene terephthalate film with a release layer ("AL-5" manufactured by LINTEC Corporation, thickness 38 μm) was prepared. The resin varnishes obtained in the examples and comparative examples were uniformly coated on the release layer of this support, and the thickness of the dried resin composition layer was made 40 μm. Thereafter, the resin composition was dried at 80°C to 100°C (average 90°C) for 2 minutes to obtain resin sheet A comprising a support and a resin composition layer.

[0420] (2) Preparation of Cured Product

[0421] 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. This cured product was cut into a length of 80 mm and a width of 2 mm and used as the cured product for evaluation.

[0422] (3) Measurement of Relative Dielectric Constant and Dissipation Factor

[0423] For each cured product for evaluation, using "HP8362B" manufactured by Agilent Technologies, the values of relative dielectric constant and dissipation factor (Dk value, Df value) were measured by the cavity resonator perturbation method under the conditions of a measurement frequency of 5.8 GHz and a measurement temperature of 23°C. The measurement of relative dielectric constant and dissipation factor was carried out 2 times, and their average values were calculated.

[0424] <Test Example 2: Evaluation of Crack Resistance after Decontamination Treatment>

[0425] (1) Preparation of Resin Sheet B with a Resin Composition Layer Thickness of 25 μm

[0426] As a support, a polyethylene terephthalate film with a release layer ("AL-5" manufactured by LINTEC Corporation, thickness 38 μm) was prepared. The resin varnishes obtained in the examples and comparative examples were uniformly coated on the release layer of this support, and the thickness of the dried resin composition layer was made 25 μm, and it was dried at 70°C to 80°C (average 75°C) for 2.5 minutes to obtain resin sheet B comprising a support and a resin composition layer.

[0427] (2) Lamination of Resin Sheet B and Core Material

[0428] Using an intermittent vacuum compression laminator (manufactured by Nikko-Materials Co., Ltd., two-stage laminator "CVP700"), the obtained resin sheet B was laminated on both sides of a core material (Resonac Co., Ltd.'s "E705GR", thickness 400 μm) with a residual copper rate of 60% in a grid pattern with a 400-μm interval and circular copper pads (copper thickness 35 μm, diameter 350 μm) such that the resin composition layer of the 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 air pressure 13 hPa or less, and then pressing at a temperature of 100 °C and a pressure of 0.74 MPa for 30 seconds.

[0429] (3) Curing of the resin composition layer

[0430] After that, the core material laminated with the resin sheet B was put into an oven at 130 °C and heated for 30 minutes, and 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. After that, the support was peeled off to obtain a cured substrate having a structure of insulating layer / core material / insulating layer.

[0431] (4) Cleaning treatment

[0432] The obtained cured substrate was immersed in a swelling solution ("Swelling DipSecuriganth P" manufactured by Atotech Japan Co., Ltd.) at 60 °C for 10 minutes. Then, it was immersed in a roughening solution ("Concentrate Compact CP" manufactured by Atotech Japan Co., Ltd., aqueous solution of KMnO4: 60 g / L, NaOH: 40 g / L) at 80 °C for 30 minutes. Finally, it was immersed in a neutralizing solution ("Reduction Solution Securiganth P" manufactured by Atotech Japan Co., Ltd.) at 40 °C for 5 minutes.

[0433] (5) Evaluation of crack resistance

[0434] For the cured substrate after the cleaning treatment, 100 copper pad portions were observed to confirm the presence or absence of cracks in the resin composition layer, and the evaluation was carried out according to the following criteria.

[0435] ○: The number of cracks is 10 or less;

[0436] ×: The number of cracks is more than 10.

[0437] <Test Example 3: Measurement of the adhesion strength with the conductor layer before and after exposure to a high-temperature and high-humidity environment (HAST)>

[0438] (1) Lamination of resin sheet A and inner layer substrate

[0439] As the inner substrate, a glass cloth base epoxy resin double-sided copper-clad laminate having a copper foil on the surface was prepared (the thickness of the copper foil was 18 μm, the thickness of the substrate was 0.8 mm, "R1515A" manufactured by Panasonic Corporation). All of the copper foil on the surface of the inner substrate was etched away. After that, drying was performed at 190 °C for 30 minutes.

[0440] Using an intermittent vacuum pressure laminator (manufactured by Nikko-Materials Company, two-stage laminator "CVP700"), the resin sheet A obtained above was laminated on both sides of the inner substrate such that the resin composition layer of the resin sheet A was in contact with the inner substrate. The lamination was carried out by reducing the pressure for 30 seconds to make the air pressure 13 hPa or less, and then press-bonding at a temperature of 100 °C and a pressure of 0.74 MPa for 30 seconds.

[0441] Next, the laminated resin sheet A was hot-pressed at atmospheric pressure, 100 °C, and a pressure of 0.5 MPa for 60 seconds for smoothing. Then, the support was peeled off, and "intermediate multilayer body I" including a resin composition layer / inner substrate / resin composition layer in sequence was obtained.

[0442] (2) Lamination of copper foil

[0443] A copper foil having a glossy surface was prepared (thickness 35 μm, "3EC-III" manufactured by Mitsui Mining & Smelting Co., Ltd.). Using a micro-etchant ("CZ8101" manufactured by MEC Company), the glossy surface of the copper foil was etched with a copper etching amount of 1 μm to perform roughening treatment. The copper foil thus obtained was called "roughened copper foil".

[0444] The roughened copper foil was laminated on both sides of the intermediate multilayer body I, and 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 the resin sheet A to the inner substrate. Thus, "intermediate multilayer body II" including roughened copper foil / resin composition layer / inner substrate / resin composition layer / roughened copper foil in sequence was obtained.

[0445] (3) Thermal curing of resin composition layer

[0446] The obtained intermediate multilayer body II was put into an oven at 100 °C and heated for 30 minutes, then transferred to an oven at 170 °C and heated for 30 minutes. Next, after the intermediate multilayer body II was taken out of the oven to a room temperature atmosphere, it was put into an oven at 190 °C and additionally heated for 90 minutes. Thus, thermal curing of the resin composition layer was carried out, and "evaluation substrate C" including roughened copper foil / insulating layer as the cured product of the resin composition layer / inner substrate / insulating layer as the cured product of the resin composition layer / roughened copper foil in sequence was obtained. In this evaluation substrate C, the roughened copper foil corresponded to the conductor layer.

[0447] (4) Measurement of the adhesion strength with the conductor layer

[0448] Using the obtained evaluation substrate C, the peel strength between the roughened copper foil and the insulating layer was measured. The measurement of the peel strength was carried out in accordance with JIS C6481. Specifically, the peel strength was measured through the following operations.

[0449] On the roughened copper foil of the evaluation substrate C, a cut was made to enclose a rectangular portion with a width of 10 mm and a length of 100 mm. One end of the rectangular portion was peeled off and clamped with a jig (manufactured by TSE Corporation, Autocom type testing machine "AC-50C-SL"). The length of the rectangular portion was peeled in the vertical direction within a range of 35 mm, and the load (kgf / cm) at the time of peeling was measured as the peel strength. The above peeling was carried out at a speed of 50 mm / minute at room temperature. Moreover, after conducting an environmental test (HAST test) at 130 °C and 85% RH for 100 hours, the same operation as above was performed, and the peel strength was measured.

[0450] <Results>

[0451] The results of the examples and comparative examples are shown in Table 1 below.

[0452]

Claims

1. A resin composition comprising: (A) an epoxy resin, (B) an active ester 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), 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 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; * indicates the binding site, *-Y (c1) In formula (c1), Y represents: a monovalent organic group having 3 to 50 carbon atoms and containing a free radical polymerizable group; a monovalent aromatic group having 6 to 50 carbon atoms and optionally having a substituent, wherein: The substituent does not include a hydroxyl group and a free radical polymerizable group; or a monovalent aliphatic group having 3 to 50 carbon atoms which may have a substituent, wherein the substituent does not include a hydroxyl group and a free radical polymerizable group; *Indicates the binding site.

2. The resin composition according to claim 1, wherein in formula (C1), R 1 The group represented by contains a group represented by the following formula (C2), 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 1-5.

3. The resin composition according to claim 2, wherein in formula (C2), the group represented by L is any one of the divalent groups represented by the following formulae (C4-1) to (C4-3), 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 an integer of 0 or 1 to 4; *Indicates the binding site. 4 . The resin composition according to claim 1 , wherein in formula (c1), the group represented by Y comprises at least one of a monovalent aromatic group containing a radical polymerizable group and an unsubstituted monovalent aromatic group.

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

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

8. The resin composition according to claim 1, further comprising: (E) a compound containing a free radical polymerizable group, wherein: The compound does not include the (C) component.

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

10. The resin composition according to claim 1, which is used 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, 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 claim 1 .

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

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