Resin composition

Abstract

To provide a resin composition that enables formation of a cured product having low dielectric characteristics and a low linear thermal expansion coefficient, while exhibiting high adhesion both before and after a HAST test and a high glass transition temperature.SOLUTION: A resin composition comprising (A) an epoxy resin, (B) an active ester compound, and (C) an inorganic filler, wherein the component (B) includes (B-1) an active ester compound represented by the following formula (B-1a), and (B-2) an active ester compound other than the component (B-1).SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to a resin composition, a resin sheet, a circuit board, and a semiconductor device. [Background technology]

[0002] Circuit boards such as printed wiring boards are widely used in various electronic devices. A known method for manufacturing circuit boards is a build-up method in which insulating layers and conductor layers are alternately stacked on an inner layer substrate. The insulating layer is formed, for example, from a cured product of a resin composition (Patent Documents 1 and 2). To give a specific example, a resin composition layer containing a resin composition is formed, and then the resin composition layer is cured to form an insulating layer containing a cured product of the resin composition. [Prior art documents] [Patent documents]

[0003] [Patent Document 1] Japanese Patent Application Publication No. 2022-100697 [Patent Document 2] Japanese Patent Publication No. 2023-037522 Summary of the Invention [Problem to be solved by the invention]

[0004] In recent years, there has been an increasing demand for resin compositions that can form insulating layers having low dielectric constants and dielectric loss tangents, good adhesion to conductor layers before and after HAST (High Accelerated Stress Test; accelerated environmental testing), high glass transition temperatures (Tg), and low coefficients of linear thermal expansion (CTE). The dielectric constant and dielectric loss tangent are sometimes collectively referred to as dielectric properties.

[0005] The present invention has been made in view of the above-mentioned problems, and has an object to provide a resin composition capable of forming a cured product having low dielectric properties and a low coefficient of linear thermal expansion, and having high adhesion before and after a HAST test and a high glass transition temperature; a resin sheet containing the resin composition; a cured product of the resin composition; a circuit board containing the cured product of the resin composition; and a semiconductor device including the circuit board. [Means for solving the problem]

[0006] As a result of extensive investigations into the above-mentioned problems, the present inventors have found that the above-mentioned problems can be solved by incorporating, as component (B), a combination of an active ester compound represented by formula (B-1a) and another active ester compound, which comprises (A) an epoxy resin, (B) an active ester compound, and (C) an inorganic filler, and have thus completed the present invention.

[0007] That is, the present invention includes the following. [1] (A) epoxy resin, (B) an active ester compound, and (C) an inorganic filler, A resin composition, wherein the component (B) comprises (B-1) an active ester compound represented by the following formula (B-1a), and (B-2) an active ester compound other than the component (B-1): [ka] In the formula, R 11 each independently represents a monovalent aromatic group which may have a substituent, R 12 each independently represents a divalent aromatic group which may have a substituent, and R 13 each independently represents a divalent aromatic group having a fused ring structure, which may have a substituent; R 14 each independently represents a divalent hydrocarbon group which may have a substituent, and n1 represents an integer of 0 or greater. [2] The resin composition according to [1], wherein the component (B-2) includes (B-2-i) an active ester compound containing a carbon-carbon double bond. [3] The resin composition according to [1] or [2], wherein the component (B-2-i) contains any one of an active ester compound represented by formula (Bi), an active ester compound represented by formula (B-ii), and an active ester compound represented by formula (B-iii). [ka] In formula (Bi), Ar 11 each independently represents a monovalent aromatic group which may have a substituent, Ar 12 each independently represents a divalent aromatic group which may have a substituent, Ar 13 each independently represents a divalent aromatic group which may have a substituent, a divalent aliphatic group which may have a substituent, an oxygen atom, a sulfur atom, or a divalent group consisting of a combination thereof. mi and ni each independently represent an integer of 0 or more. However, Ar 11 , Ar 12 , and Ar 13 At least one of has a substituent containing a carbon-carbon double bond. In formula (B-ii), Ar 11 each independently represents a monovalent aromatic group which may have a substituent, Ar 12 each independently represents a divalent aromatic group which may have a substituent, Ar 13 each independently represents a divalent aromatic group which may have a substituent, a divalent aliphatic group which may have a substituent, an oxygen atom, a sulfur atom, or a divalent group consisting of a combination thereof. mii and nii each independently represent an integer of 0 or more. However, Ar 11 , Ar 12 , and Ar 13 At least one of has a substituent containing a carbon-carbon double bond. In formula (B-iii), Ar 1 each independently represents a monovalent aromatic group which may have a substituent, Ar 2 each independently represents a divalent aromatic group which may have a substituent, and R 1 each independently represents a divalent aliphatic group which may have a substituent, and R 2each independently represents a butadiene structure, and m and n each independently represent an integer greater than 0. [4] The resin composition according to any one of [1] to [3], wherein the component (B-2) includes (B-2-ii) an active ester compound that does not contain a carbon-carbon double bond. [5] The resin composition according to any one of [1] to [4], further comprising (D) a radically polymerizable compound. [6] The resin composition according to [5], wherein the component (D) contains a maleimide resin. [7] The resin composition according to any one of [1] to [6], further comprising (E) another curing agent. [8] The resin composition according to any one of [1] to [7], wherein the content of the component (B-1) is 20% by mass or more and 90% by mass or less, when the total amount of the component (B) is taken as 100% by mass. [9] In formula (B-1a), R 14 represents a divalent group formed by combining a divalent aromatic group and a divalent aliphatic group.

[10] A resin sheet comprising a support and a resin composition layer provided on the support, the resin composition layer comprising the resin composition according to any one of [1] to [9].

[11] A circuit board comprising an insulating layer formed from a cured product of the resin composition according to any one of [1] to [9].

[12] A semiconductor device comprising the circuit board according to

[11] . [Effects of the Invention]

[0008] According to the present invention, it is possible to provide a resin composition capable of forming a cured product having low dielectric properties and a low coefficient of linear thermal expansion, and having high adhesion before and after a HAST test and a high glass transition temperature; a resin sheet containing the resin composition; a cured product of the resin composition; a circuit board containing the cured product of the resin composition; and a semiconductor device including the circuit board. DETAILED DESCRIPTION OF THE INVENTION

[0009] The present invention will be described below with reference to embodiments and examples. However, the present invention is not limited to the embodiments and examples shown below, and may be modified and implemented within the scope of the claims and their equivalents.

[0010] [Resin composition] The resin composition comprises (A) an epoxy resin, (B) an activated ester compound, and (C) an inorganic filler, wherein the (B) component comprises (B-1) an activated ester compound having a structure represented by formula (B-1a), and (B-2) an activated ester compound other than the (B-1) component. In the present invention, by incorporating a combination of the (A) component, the (B) components (B-1) and (B-2), and the (C) component, a cured product can be obtained that exhibits low dielectric properties and a low linear thermal expansion coefficient, as well as high adhesion before and after the HAST test and a high glass transition temperature. Furthermore, a cured product that typically exhibits excellent smear removal properties can also be obtained.

[0011] The resin composition may further contain optional components in addition to the components (A) to (C). Examples of optional components include (D) a radically polymerizable compound, (E) a curing agent (excluding those corresponding to (B) an active ester compound), (F) a curing accelerator, (G) a thermoplastic resin, (H) other additives, and (I) a solvent. Each component contained in the resin composition will be described in detail below.

[0012] <(A) Epoxy resin> The resin composition contains an epoxy resin (A) as component (A). The epoxy resin (A) can be a curable resin having an epoxy group. By including the epoxy resin (A) in the resin composition, a cured product exhibiting good mechanical strength and insulating reliability can be obtained. The epoxy resin (A) may be used singly or in combination of two or more.

[0013] (A) Epoxy resins include, for example, bixylenol type epoxy resins, bisphenol A type epoxy resins, bisphenol F type epoxy resins, bisphenol S type epoxy resins, bisphenol AF type epoxy resins, dicyclopentadiene type epoxy resins, trisphenol type epoxy resins, naphthol novolac type epoxy resins, phenol novolac type epoxy resins, tert-butyl-catechol type epoxy resins, naphthalene type epoxy resins, naphthol type epoxy resins, anthracene type epoxy resins, glycidylamine type epoxy resins, and glycidyl ester type Examples of epoxy resins include epoxy resins, glycidyl cyclohexane-type epoxy resins, alkyl diglycidyl ether-type epoxy resins, cresol novolac-type epoxy resins, biphenyl-type epoxy resins, linear aliphatic epoxy resins, epoxy resins having a butadiene structure, alicyclic epoxy resins, heterocyclic epoxy resins, spiro ring-containing epoxy resins, cyclohexane-type epoxy resins, cyclohexane dimethanol-type epoxy resins, naphthylene ether-type epoxy resins, trimethylol-type epoxy resins, tetraphenylethane-type epoxy resins, and phenolphthalimidine-type epoxy resins.

[0014] The resin composition preferably contains, as component (A), an epoxy resin having two or more epoxy groups per molecule. From the viewpoint of significantly achieving the desired effects of the present invention, the proportion of the epoxy resin having two or more epoxy groups per molecule relative to 100% by mass of the epoxy resin (A) is preferably 50% by mass or more, more preferably 60% by mass or more, and particularly preferably 70% by mass or more.

[0015] Epoxy resins include epoxy resins that are liquid at a temperature of 20°C (hereinafter sometimes referred to as "liquid epoxy resins") and epoxy resins that are solid at a temperature of 20°C (hereinafter sometimes referred to as "solid epoxy resins"). The resin composition may contain, as component (A), only a liquid epoxy resin, only a solid epoxy resin, or a combination of a liquid epoxy resin and a solid epoxy resin.

[0016] The liquid epoxy resin is preferably a liquid epoxy resin having two or more epoxy groups in one molecule.

[0017] Preferred liquid epoxy resins include bisphenol A type epoxy resins, bisphenol F type epoxy resins, bisphenol AF type epoxy resins, naphthalene type epoxy resins, glycidyl ester type epoxy resins, glycidyl amine type epoxy resins, phenol novolac type epoxy resins, alicyclic epoxy resins having an ester skeleton, cyclohexane type epoxy resins, cyclohexane dimethanol type epoxy resins, glycidyl amine type epoxy resins, and epoxy resins having a butadiene structure, glycidyl cyclohexane type epoxy resins, phenolphthalimidine type epoxy resins, and alkyl diglycidyl ether type epoxy resins, with naphthalene type epoxy resins being more preferred.

[0018] Specific examples of liquid epoxy resins include "HP4032", "HP4032D", and "HP4032SS" (naphthalene type epoxy resins) manufactured by DIC Corporation; "828US", "jER828EL", "825", and "Epikote 828EL" (bisphenol A type epoxy resins) manufactured by Mitsubishi Chemical Corporation; "jER807" and "1750" (bisphenol F type epoxy resins) manufactured by Mitsubishi Chemical Corporation; "jER152" (phenol novolac type epoxy resin) manufactured by Mitsubishi Chemical Corporation; "630" and "630LSD" (glycidyl amine type epoxy resins) manufactured by Mitsubishi Chemical Corporation; and "ZX1" manufactured by Nippon Steel Chemical & Material Co., Ltd. Examples of epoxy resins that can be used include "EX-721" (a glycidyl ester epoxy resin) manufactured by Nagase ChemteX Corporation, "Celloxide 2021P" (an alicyclic epoxy resin having an ester skeleton) manufactured by Daicel Corporation, "PB-3600" (an epoxy resin having a butadiene structure) manufactured by Daicel Corporation, "ZX1658" and "ZX1658GS" (liquid 1,4-glycidylcyclohexane epoxy resins) manufactured by Nippon Steel Chemical & Material Co., Ltd., and "YED216D" (an alkyl diglycidyl ether epoxy resin) manufactured by Mitsubishi Chemical Corporation. These may be used alone or in combination of two or more.

[0019] As the solid epoxy resin, a solid epoxy resin having two or more epoxy groups in one molecule is preferred, a solid epoxy resin having three or more epoxy groups in one molecule is more preferred, and an aromatic solid epoxy resin having three or more epoxy groups in one molecule is even more preferred.

[0020] Preferred solid epoxy resins include bixylenol-type epoxy resins, naphthalene-type epoxy resins, naphthalene-type tetrafunctional epoxy resins, cresol novolac-type epoxy resins, dicyclopentadiene-type epoxy resins, trisphenol-type epoxy resins, naphthol-type epoxy resins, biphenyl-type epoxy resins, naphthylene ether-type epoxy resins, anthracene-type epoxy resins, bisphenol A-type epoxy resins, bisphenol AF-type epoxy resins, and tetraphenylethane-type epoxy resins, and biphenyl-type epoxy resins are more preferred.

[0021] Specific examples of solid epoxy resins include "HP4032H" (naphthalene type epoxy resin), "HP-4700", "HP-4710" (naphthalene type tetrafunctional epoxy resin), "N-690" (cresol novolac type epoxy resin), "N-695" (cresol novolac type epoxy resin), "HP-7200", "HP-7200HH", "HP-7200H" (dicyclopentadiene type epoxy resin), "EXA-7311", "EXA-7311-G3", "EXA-7311-G4", "EXA-7311-G4S", "HP6000", "HP6000L" (naphthylene ether type epoxy resin), manufactured by DIC Corporation; "EPPN-502H" (trisphenol type epoxy resin), "NC7000L" (naphthol novolac type epoxy resin), "NC3000H", "NC3000", "NC3000L" manufactured by Nippon Kayaku Co., Ltd.; Examples include "NC3100" (biphenyl-type epoxy resin); "ESN475V" (naphthalene-type epoxy resin) and "ESN485" (naphthol novolac-type epoxy resin) manufactured by Nippon Steel Chemical & Material Co., Ltd.; "YX4000H", "YL6121" (biphenyl-type epoxy resin), "YX4000HK" (bixylenol-type epoxy resin), and "YX8800" (anthracene-type epoxy resin) manufactured by Mitsubishi Chemical Corporation; "PG-100" and "CG-500" manufactured by Osaka Gas Chemical Co., Ltd.; "YL7760" (bisphenol AF-type epoxy resin), "YL7800" (fluorene-type epoxy resin), "jER1010" (solid bisphenol A-type epoxy resin), and "jER1031S" (tetraphenylethane-type epoxy resin) manufactured by Mitsubishi Chemical Corporation; and "WHR-991S" (phenolphthalimidine-type epoxy resin) manufactured by Nippon Kayaku Co., Ltd. These may be used alone or in combination of two or more.

[0022] When a liquid epoxy resin and a solid epoxy resin are used in combination as component (A), the ratio by mass between them (liquid epoxy resin:solid epoxy resin) is preferably 1:0.1 to 1:20, more preferably 1:0.15 to 1:10, and particularly preferably 1:0.2 to 1:5.

[0023] The epoxy equivalent of component (A) is preferably 50 g / eq to 5000 g / eq, more preferably 50 g / eq to 3000 g / eq, even 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 an epoxy resin containing one equivalent of epoxy groups. This epoxy equivalent can be measured according to JIS K7236.

[0024] The weight average molecular weight (Mw) of the component (A) is preferably 100 to 5000, more preferably 150 to 3000, and even more preferably 200 to 1500. The weight average molecular weight of the epoxy resin is a weight average molecular weight in terms of polystyrene measured by gel permeation chromatography (GPC).

[0025] The content of component (A) is preferably 1% by mass or more, more preferably 3% by mass or more, and even more preferably 5% by mass or more, based on 100% by mass of the nonvolatile components in the resin composition, and the upper limit is preferably 20% by mass or less, more preferably 15% by mass or less, and even more preferably 10% by mass or less.

[0026] The content of component (A) is preferably 20% by mass or more, more preferably 25% by mass or more, and even more preferably 30% by mass or more, based on 100% by mass of the resin component in the resin composition, and the upper limit is preferably 50% by mass or less, more preferably 45% by mass or less, and even more preferably 40% by mass or less.

[0027] In the present invention, the content of each component in the resin composition is a value when the nonvolatile components in the resin composition are 100 mass % unless otherwise specified, and the nonvolatile components refer to all nonvolatile components in the resin composition excluding the solvent. Furthermore, the resin components of the resin composition refer to the nonvolatile components of the resin composition excluding the (C) inorganic filler.

[0028] <(B) Active ester compound> The resin composition contains an active ester compound (B) as component (B). The active ester compound (B) as component (B) does not include compounds corresponding to the aforementioned component (A). The resin composition contains a combination of (B-1) an active ester compound represented by the following formula (B-1a) and (B-2) an active ester compound other than the component (B-1). This allows for the production of a cured product with low dielectric properties and a low coefficient of linear thermal expansion, as well as high adhesion before and after HAST testing and a high glass transition temperature. Furthermore, it is usually possible to produce a cured product with excellent smear removal properties. The component (B) may be used alone, or two or more types may be used in any combination in any ratio.

[0029] Component (B) contains an active ester moiety in one molecule. The active ester moiety contained in component (B) is preferably an aromatic ester skeleton. The aromatic ester skeleton represents a skeleton having an ester bond and an aromatic ring bonded to one end or both ends of the ester bond. Among these, aromatic ester skeletons having aromatic rings at both ends of the ester bond are preferred. Examples of groups having such a skeleton include an arylcarbonyloxy group, an aryloxycarbonyl group, an arylenecarbonyloxy group, an aryleneoxycarbonyl group, an arylcarbonyloxyarylene group, an aryloxycarbonylarylene group, an arylenecarbonyloxyarylene group, an aryleneoxycarbonylarylene group, a heteroarylcarbonyloxy group, a heteroaryloxycarbonyl group, a heteroarylenecarbonyloxy group, a heteroaryleneoxycarbonyl group, a heteroarylcarbonyloxyarylene group, a heteroaryloxycarbonylar ... Examples of such a group include a heterocarbonylarylene group, a heteroarylenecarbonyloxyarylene group, a heteroaryleneoxycarbonylarylene group, a heteroarylcarbonyloxyheteroarylene group, a heteroaryloxycarbonylheteroarylene group, a heteroarylenecarbonyloxyheteroarylene group, a heteroaryleneoxycarbonylheteroarylene group, an arylcarbonyloxyheteroarylene group, an arylenecarbonyloxyheteroarylene group, and an aryleneoxycarbonylheteroarylene group. The number of carbon atoms in the group having such a skeleton is preferably 7 to 20, more preferably 7 to 15, and even more preferably 7 to 11.

[0030] The aryl group is preferably an aryl group having 6 to 30 carbon atoms, more preferably an aryl group having 6 to 20 carbon atoms, and even more preferably an aryl group having 6 to 10 carbon atoms. Examples of such aryl groups include a phenyl group, a 1-methylphenyl group, a naphthyl group, and an anthracenyl group. Here, the naphthyl group is a concept that includes a 1-naphthyl group and a 2-naphthyl group.

[0031] The heteroaryl group refers to a monovalent group obtained by removing one hydrogen atom from an aromatic heterocycle having, in addition to carbon atoms, heteroatoms such as oxygen, nitrogen, or sulfur as ring-constituting atoms. The heteroaryl group is preferably a heteroaryl group having 3 to 30 carbon atoms, more preferably a heteroaryl group having 4 to 20 carbon atoms, and even more preferably a heteroaryl group having 6 to 10 carbon atoms. Examples of such heteroaryl groups include a furyl group, a thienyl group, a pyrrolyl group, a pyrazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an imidazolyl group, a pyridyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, and a triazinyl group (e.g., 1,3,5-triazin-2-yl).

[0032] The arylene group is preferably an arylene group having 6 to 30 carbon atoms, more preferably an arylene group having 6 to 20 carbon atoms, and even more preferably an arylene group having 6 to 10 carbon atoms. Examples of such arylene groups include a phenylene group, a naphthylene group, an anthracenylene group, and a biphenylene group (-C6H4-C6H4-). Here, the phenylene group is a concept that includes a 1,2-phenylene group, a 1,3-phenylene group, and a 1,4-phenylene group, and the naphthylene group is a concept that includes a 1,2-naphthylene group, a 1,3-naphthylene group, a 1,4-naphthylene group, a 1,5-naphthylene group, a 1,6-naphthylene group, a 1,7-naphthylene group, and a 1,8-naphthylene group.

[0033] The heteroarylene group means a divalent group formed by removing one hydrogen atom from an aromatic heterocyclic ring having, as ring-constituting atoms, in addition to carbon atoms, heteroatoms such as oxygen atoms, nitrogen atoms, sulfur atoms, etc. As the heteroarylene group, a heteroarylene group having 3 to 30 carbon atoms is preferable, a heteroarylene group having 4 to 20 carbon atoms is more preferable, and a heteroarylene group having 6 to 10 carbon atoms is even more preferable. Examples of such heteroarylene groups include a pyrrolediyl group, a furandiyl group, a thiophenediyl group, a pyridinediyl group, a pyridazinediyl group, a pyrimidinediyl group, a pyrazinediyl group, a triazinediyl group, a piperidinediyl group, a triazolediyl group, a purinediyl group, a carbazolediyl group, a quinolinediyl group, an isoquinolinediyl group, etc.

[0034] The aromatic ester skeleton and aromatic groups such as aryl groups, arylene groups, heteroaryl groups, and heteroarylene groups may have substituents. There is no particular limitation on the substituents. For example, halogen atoms, -OH, -O-C 1-6 alkyl group, -N(C 1-10 alkyl group)2, an alkyl group having 1 to 20 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, an alkynyl group having 2 to 30 carbon atoms, an aryl group having 6 to 10 carbon atoms, an aralkyl group having 7 to 10 carbon atoms, -NH2, -CN, -C(O)O-C 1-10 alkyl group, -COOH, -C(O)H, -NO2, substituents containing a carbon-carbon double bond, etc. Here, the term "C p-q "(p and q are positive integers and satisfy p < q.) represents that the number of carbon atoms of the organic group described immediately after this term is p to q. For example, the expression "C 1-10 alkyl group" indicates an alkyl group having 1 to 10 carbon atoms. These substituents may be bonded to each other to form a ring, and the ring structure includes spiro rings and fused rings. Details of the substituents containing a carbon-carbon double bond will be described later.

[0035] The term "aromatic group" refers to a group in which one or more hydrogen atoms have been removed from the aromatic ring of an aromatic compound. The term "aromatic ring" refers to a ring that conforms to Hückel's rule, in which the number of electrons in the π-electron system of the ring is 4n+2 (n is a natural number), and includes monocyclic aromatic rings and fused polycyclic aromatic rings in which two or more monocyclic aromatic rings are fused together. The aromatic ring may be a carbon ring or a heterocyclic ring containing a heteroatom such as an oxygen atom, a nitrogen atom, or a sulfur atom.

[0036] -(B-1) Compound represented by formula (B-1a)- In the resin composition, the component (B) contains, as the component (B-1), a compound represented by formula (B-1a): The component (B-1) may be used singly or in combination of two or more. [ka] In the formula, R 11 each independently represents a monovalent aromatic group which may have a substituent, R 12 each independently represents a divalent aromatic group which may have a substituent, and R 13 each independently represents a divalent aromatic group having a fused ring structure, which may have a substituent; R 14 each independently represents a divalent hydrocarbon group which may have a substituent, and n1 represents an integer of 0 or greater.

[0037] R 11 each independently represents a monovalent aromatic group which may have a substituent. A monovalent aromatic group refers to a group in which one hydrogen atom has been removed from the aromatic ring of an aromatic compound. The number of carbon atoms in the monovalent aromatic group is preferably 6 to 30, more preferably 6 to 20, and even more preferably 6 to 10. The number of carbon atoms in the substituent is not included in this number of carbon atoms. Examples of the monovalent aromatic group include an aryl group and a heteroaryl group, with an aryl group being preferred.

[0038] The aryl group and heteroaryl group are as described above. 11is preferably a naphthyl group, more preferably a 1-naphthyl group or a 2-naphthyl group, and even more preferably a 1-naphthyl group.

[0039] R 11 The monovalent aromatic group represented by may have a substituent. The substituent is the same as the substituent that the aromatic ester skeleton may have.

[0040] R 12 each independently represents a divalent aromatic group which may have a substituent. A divalent aromatic group refers to a group obtained by removing two hydrogen atoms from the aromatic ring of an aromatic compound. Examples of the divalent aromatic group include an arylene group and a heteroarylene group, with an arylene group being preferred. The divalent aromatic group preferably has 6 to 24 carbon atoms, more preferably 6 to 18, and even more preferably 6 to 14 carbon atoms.

[0041] The arylene group and heteroarylene group are as described above. 12 is preferably a phenylene group, more preferably a 1,3-phenylene group.

[0042] R 12 The divalent aromatic group represented by may have a substituent. The substituent is the same as the substituent that the aromatic ester skeleton may have.

[0043] R 13 each independently represents a divalent aromatic group having a fused ring structure, which may have a substituent. Examples of the divalent aromatic group having a fused ring structure include an arylene group having a fused ring structure and a heteroarylene group having a fused ring structure, with an arylene group having a fused ring structure being preferred. The number of carbon atoms in the divalent aromatic group having a fused ring structure is preferably 6 or more, more preferably 7 or more, and even more preferably 8 or more, and is preferably 24 or less, more preferably 18 or less, and even more preferably 14 or less.

[0044] Examples of the arylene group having a fused ring structure include naphthylene groups such as a 1,2-naphthylene group, a 1,3-naphthylene group, a 1,4-naphthylene group, a 1,5-naphthylene group, a 1,6-naphthylene group, a 1,7-naphthylene group, and a 1,8-naphthylene group; an anthracenylene group; and a phenanthrenediyl group, among which a naphthylene group is preferred and a 1,5-phenylene group is more preferred.

[0045] Examples of the heteroarylene group having a fused ring structure include a carbazolediyl group, a quinolinediyl group, and an isoquinolinediyl group.

[0046] R 13 The divalent aromatic group having a fused ring structure represented by may have a substituent. The substituent is the same as the substituent that the aromatic ester skeleton may have.

[0047] R 14 each independently represents a divalent hydrocarbon group which may have a substituent. Examples of the divalent hydrocarbon group include a divalent aromatic group, a divalent aliphatic group, and a divalent group consisting of a combination thereof. A divalent hydrocarbon group refers to a group obtained by removing two hydrogen atoms from a hydrocarbon compound, and a divalent aliphatic group refers to a group obtained by removing two hydrogen atoms bonded to an aliphatic carbon of an aliphatic compound. Among these, R 14 preferably represents a divalent aromatic group.

[0048] R 14 The divalent aromatic group represented by R 12 is the same as the divalent aromatic group represented by

[0049] R 14 The divalent aliphatic group represented by may be linear, branched, or cyclic. The number of carbon atoms in the divalent aliphatic group is preferably 1 to 12, more preferably 1 to 6, and even more preferably 1 to 4. The number of carbon atoms in the substituent is not included in this number of carbon atoms. Examples of the divalent aliphatic group include an alkylene group and an alkenylene group, with an alkylene group being preferred.

[0050] The alkylene group may be linear, branched, or cyclic. Examples of the alkylene group include a methylene group, an ethylene group, a propylene group, a 2-propylene group, a 1,1-dimethyl-3-methylpropylene group, a butylene group, a pentylene group, a hexylene group, a cyclopropylene group, a cyclobutylene group, a cyclopentylene group, a cyclohexylene group, a decahydronaphthalene group, a norbornanylene group, a dicyclopentanylene group, an adamantanylene group, a 1-methylmethylene group, a 1,1-dimethylmethylene group, a 1-methylethylene group, a 1,1-dimethylethylene group, a 1,2-dimethylethylene group, a butylene group, a 1-methylpropylene group, and a 2-methylpropylene group. Among these, a methylene group is preferred as the alkylene group.

[0051] The alkenylene group may be linear, branched, or cyclic. Examples of the alkenylene group include an ethenylene group, a propenylene group, a butenylene group, a pentenylene group, a hexenylene group, a cyclopropenylene group, a cyclobutenylene group, a cyclopentenylene group, a cyclohexenylene group, and a norbornenylene group.

[0052] Examples of the divalent group formed by combining a divalent aromatic group and a divalent aliphatic group include an alkylene-arylene group and an alkylene-arylene-alkylene group. An alkylene-arylene-alkylene group is preferred, a methylene-phenylene-methylene group is more preferred, and a methylene-1,4-phenylene-methylene group is even more preferred.

[0053] R 14 The divalent hydrocarbon group, divalent aromatic group, and divalent aliphatic group represented by may have a substituent. The substituent is the same as the substituent that the aromatic ester skeleton may have.

[0054] n1 represents an integer of 0 or more, preferably an integer of 1 or more, more preferably an integer of 2 or more, and is preferably an integer of 15 or less, more preferably an integer of 10 or less, and even more preferably an integer of 8 or less.

[0055] The active ester compound represented by formula (B-1a) is preferably an active ester compound represented by formula (B-1b). [ka] In the formula, R 21 each independently represents a monovalent aromatic group which may have a substituent, R 22 each independently represents a divalent aromatic group which may have a substituent, and R 24 each independently represents a divalent hydrocarbon group which may have a substituent, and n2 represents an integer of 0 or greater.

[0056] R 21 each independently represents a monovalent aromatic group which may have a substituent, and R in formula (B-1a) 11 is the same as

[0057] R 22 each independently represents a divalent aromatic group which may have a substituent, and R in formula (B-1a) 12 is the same as

[0058] R 24 each independently represents a divalent hydrocarbon group which may have a substituent, and R in formula (B-1a) 14 is the same as

[0059] n2 represents an integer of 0 or more and is the same as n1 in formula (B-1a).

[0060] The active ester compound represented by formula (B-1a) is preferably an active ester compound represented by formula (B-1c). [ka] In the formula, R 31 each independently represents a monovalent aromatic group which may have a substituent, R 32 each independently represents a divalent aromatic group which may have a substituent, and n3 represents an integer of 0 or greater.

[0061] R 31 each independently represents a monovalent aromatic group which may have a substituent, and R in formula (B-1a) 11 is the same as

[0062] R 32 each independently represents a divalent aromatic group which may have a substituent, and R in formula (B-1a) 12 is the same as

[0063] n3 represents an integer of 0 or more and is the same as n1 in formula (B-1a).

[0064] Specific examples of the component (B-1) include the compound represented by the following formula (1): However, the component (B-1) is not limited to these specific examples: In the formula, n represents an integer of 0 or greater. [ka]

[0065] The component (B-1) may be synthesized by a known method. The component (B-1) can be synthesized, for example, by the method described in WO 2018 / 235424 or WO 2018 / 235425.

[0066] The weight average molecular weight of the component (B-1) is preferably 150 or more, more preferably 200 or more, and even more preferably 250 or more, and is preferably 5000 or less, more preferably 3000 or less, and even more preferably 2000 or less. The weight average molecular weight of the component (A) can be measured by gel permeation chromatography (GPC) (polystyrene equivalent).

[0067] The active ester equivalent of component (B-1) is preferably 150 g / eq or more, more preferably 200 g / eq or more, even more preferably 250 g / eq or more, and is preferably 1,000 g / eq or less, more preferably 800 g / eq or less, even more preferably 600 g / eq or less. The active ester equivalent represents the mass of resin per equivalent of active ester group.

[0068] The quantitative ratio of component (A) to component (B-1), expressed as the ratio of [total number of active ester groups in component (B-1)] / [total number of epoxy groups in epoxy resin (A)], is preferably 0.01 or more, more preferably 0.1 or more, and even more preferably 0.3 or more, and is preferably 5 or less, more preferably 3 or less, and even more preferably 2 or less. Here, the "number of epoxy groups in epoxy resin (A)" refers to the sum of all values ​​obtained by dividing the mass of the non-volatile components of epoxy resin (A) present in the resin composition by the epoxy equivalent. Furthermore, the "number of active ester groups in component (B-1)" refers to the sum of all values ​​obtained by dividing the mass of the non-volatile components of component (B-1) present in the resin composition by the active ester group equivalent. By maintaining the quantitative ratio of component (A) to component (B-1) within this range, the effects of the present invention can be significantly achieved.

[0069] The content of the (B-1) component is preferably 1% by mass or more, more preferably 3% by mass or more, and even more preferably 5% by mass or more, and is preferably 20% by mass or less, more preferably 15% by mass or less, and even more preferably 10% by mass or less, when the non-volatile components in the resin composition are taken as 100% by mass.

[0070] The content of the (B-1) component is preferably 15% by mass or more, more preferably 20% by mass or more, and even more preferably 25% by mass or more, and is preferably 50% by mass or less, more preferably 45% by mass or less, and even more preferably 40% by mass or less, when the resin component in the resin composition is taken as 100% by mass.

[0071] The content of the (B-1) component, when the entire (B) component is taken as 100% by mass, is preferably 20% by mass or more, more preferably 25% by mass or more, even more preferably 30% by mass or more, 35% by mass or more, 40% by mass or more, 45% by mass or more, or 50% by mass or more, and is preferably 90% by mass or less, even more preferably 85% by mass or less, and even more preferably 80% by mass or less.

[0072] When the content of component (A) when the nonvolatile components in the resin composition are taken as 100% by mass is defined as a, and the content of component (B-1) when the nonvolatile components in the resin composition are taken as 100% by mass is defined as b1, a / b1 is preferably 0.1 or more, more preferably 0.3 or more, even more preferably 0.5 or more, and is preferably 2.5 or less, more preferably 2 or less, even more preferably 1.5 or less. By adjusting the content so that a / b1 falls within this range, the effects of the present invention can be significantly achieved.

[0073] -(B-2) Active ester compound other than component (B-1)- The component (B) contains, as the component (B-2), an active ester compound other than the components (B-1). The component (B-2) may be used alone or in combination of two or more.

[0074] The component (B-2) has an active ester moiety. The number of active ester moieties contained in one molecule of the component (B-2) is usually one or more, and preferably two or more.

[0075] The component (B-2) is preferably an activated ester compound (B-2-i) containing a carbon-carbon double bond. Here, the carbon-carbon double bond refers to a carbon-carbon double bond moiety (C=C) that can be polymerized with each other by radicals or the like, and does not include reactively inert carbon-carbon double bonds that constitute aromatic groups such as benzene rings.

[0076] Examples of the component (B-2-i) include (B-2-a) a compound containing a substituent containing a carbon-carbon double bond and an active ester moiety, and (B-2-b) a compound having a skeleton containing a carbon-carbon double bond and an active ester moiety.

[0077] The terminal of component (B-2-a) is preferably a monovalent aromatic group. Examples of the monovalent aromatic group include aryl groups, and the aryl groups are as described above. Among these, a phenyl group is preferred as the monovalent aromatic group at the terminal of component (B-2-a).

[0078] The component (B-2-a) may have, in addition to a substituent containing a carbon-carbon double bond and an active ester moiety, an aromatic group, an aliphatic group, an oxygen atom, or a group consisting of a combination thereof.

[0079] The aromatic group that may be contained in component (B-2-a) is preferably a divalent aromatic group, more preferably an arylene group or an aralkylene group, and even more preferably an arylene group. The arylene group is as described above. As the aralkylene group, an aralkylene group having 7 to 30 carbon atoms is preferred, an aralkylene group having 7 to 20 carbon atoms is more preferred, and an aralkylene group having 7 to 15 carbon atoms is even more preferred. Of these, a phenylene group is preferred.

[0080] The aliphatic group that may be contained in component (B-2-a) is preferably a divalent aliphatic group, more preferably a divalent saturated aliphatic group, and even more preferably an alkylene group or a cycloalkylene group. As the alkylene group, an alkylene group having 1 to 10 carbon atoms is preferred, an alkylene group having 1 to 6 carbon atoms is more preferred, and an alkylene group having 1 to 3 carbon atoms is even more preferred. Examples of the alkylene group include a methylene group, an ethylene group, a propylene group, a 1-methylmethylene group, a 1,1-dimethylmethylene group, a 1-methylethylene group, a 1,1-dimethylethylene group, a 1,2-dimethylethylene group, a butylene group, a 1-methylpropylene group, a 2-methylpropylene group, a 1,1-dimethyl-3-methylpropylene group, a pentylene group, and a hexylene group, with a 1,1-dimethylmethylene group being preferred.

[0081] The cycloalkylene group is preferably a cycloalkylene group having 3 to 20 carbon atoms, more preferably a cycloalkylene group having 3 to 15 carbon atoms, and even more preferably a cycloalkylene group having 5 to 10 carbon atoms. The cycloalkylene group may have a monocyclic structure or a polycyclic structure. Examples of the cycloalkylene group include a cyclopropylene group, a cyclobutylene group, a cyclopentylene group, a cyclohexylene group, a cyclopentylene group, a cycloheptylene group, and cycloalkylene groups represented by the following formulas (a) to (d). In formulas (a) to (d), "*" represents a bond. [ka]

[0082] The group consisting of these combinations is preferably a divalent group, and examples thereof include a group consisting of a combination of an aliphatic group and an aromatic group, a group consisting of a combination of an aromatic group, an aliphatic group and an aromatic group, etc. One embodiment of the group consisting of these combinations is a group consisting of a combination of arylene-alkylene-arylene, and a group consisting of a combination of phenylene-1,1-dimethylmethylene-phenylene is preferred.

[0083] The aromatic group and aliphatic group that may be contained in the component (B-2-a) may further have a substituent, which is the same as the substituent that may be contained in the aromatic ester skeleton.

[0084] In the component (B-2-a), examples of the substituent containing a carbon-carbon double bond include vinyl groups, propenyl groups (allyl groups, 1-propenyl groups, isopropenyl groups), butenyl groups (1-butenyl groups, crotyl groups, methallyl groups, isocrotyl groups, etc.), pentenyl groups (1-pentenyl groups, etc.), hexenyl groups (1-hexenyl groups, etc.), heptenyl groups (1-heptenyl groups, etc.), octenyl groups (1-octenyl groups, etc.), cyclopentenyl groups (2-cyclopentenyl groups, etc.), and cyclohexenyl groups (3-cyclohexenyl groups, etc.), with allyl groups being preferred.

[0085] The component (B-2-a) contains a substituent containing a carbon-carbon double bond. The number of substituents containing a carbon-carbon double bond per molecule of the component (B-2-a) is preferably 1 or more, more preferably 2 or more, and is preferably 10 or less, more preferably 8 or less, and even more preferably 5 or less.

[0086] The carbon-carbon double bond-containing substituent contained in component (B-2-a) may be present as a substituent on a terminal monovalent aromatic group, or as a substituent on an aromatic group or an aliphatic group. When component (B-2-a) contains a carbon-carbon double bond-containing substituent as a substituent on a terminal monovalent aromatic group, component (B-2-a) preferably contains a carbon-carbon double bond-containing substituent as a substituent on both terminal aromatic groups.

[0087] The component (B-2-a) preferably contains either an active ester compound represented by the following general formula (Bi) or an active ester compound represented by the following general formula (B-ii), and more preferably contains an active ester compound represented by the general formula (Bi). [ka] In formula (Bi), Ar11 each independently represents a monovalent aromatic group which may have a substituent, Ar 12 each independently represents a divalent aromatic group which may have a substituent, Ar 13 each independently represents a divalent aromatic group which may have a substituent, a divalent aliphatic group which may have a substituent, an oxygen atom, a sulfur atom, or a divalent group consisting of a combination thereof. mi and ni each independently represent an integer of 0 or more. However, Ar 11 , Ar 12 , and Ar 13 At least one of has a substituent containing a carbon-carbon double bond. In formula (B-ii), Ar 11 each independently represents a monovalent aromatic group which may have a substituent, Ar 12 each independently represents a divalent aromatic group which may have a substituent, Ar 13 each independently represents a divalent aromatic group which may have a substituent, a divalent aliphatic group which may have a substituent, an oxygen atom, a sulfur atom, or a divalent group consisting of a combination thereof. mii and nii each independently represent an integer of 0 or more. However, Ar 11 , Ar 12 , and Ar 13 At least one of has a substituent containing a carbon-carbon double bond.

[0088] In formula (Bi) and formula (B-ii), Ar 11 Each of R in formula (B-1) represents a monovalent aromatic group which may have a substituent. 11 It is the same as the monovalent aromatic group represented by Ar 11 is preferably a phenyl group or a naphthyl group, more preferably a phenyl group, a 1-naphthyl group or a 2-naphthyl group, and even more preferably a 1-naphthyl group.

[0089] Ar 11 The monovalent aromatic group represented by may have a substituent. The substituent is the same as the substituent that the aromatic ester skeleton may have. Among them, Ar 11When has a substituent, the substituent is preferably a substituent containing a carbon-carbon double bond.

[0090] In formula (Bi) and formula (B-ii), Ar 12 Each of R in formula (B-1) represents a divalent aromatic group which may have a substituent. 12 It is the same as the divalent aromatic group represented by Ar 12 is preferably a phenylene group, more preferably a 1,3-phenylene group.

[0091] Ar 12 The divalent aromatic group represented by may have a substituent. The substituent is the same as the substituent that the aromatic ester skeleton may have. Among them, Ar in formula (Bi) 12 has preferably an aralkyl group as a substituent, and more preferably a benzyl group as a substituent.

[0092] In the general formula (Bi) and the formula (B-ii), Ar 13 each independently represents a divalent aromatic group which may have a substituent, a divalent aliphatic group which may have a substituent, an oxygen atom, a sulfur atom, or a divalent group consisting of a combination thereof, and a divalent group consisting of a combination thereof is preferred. 12 The same applies to the divalent aromatic group represented by the formula:

[0093] The divalent aliphatic group is preferably a divalent saturated aliphatic group, more preferably an alkylene group or a cycloalkylene group, and more preferably a cycloalkylene group, as described above.

[0094] Divalent groups formed by these combinations are preferably divalent groups formed by combining an optionally substituted divalent aromatic group and an optionally substituted divalent aliphatic group, and more preferably divalent groups formed by alternating multiple optionally substituted divalent aromatic groups and multiple optionally substituted divalent aliphatic groups. Specific examples of the divalent groups include the following divalent groups (B1) to (B13), of which either (B10) or (B11) is preferred. In the formula, a1 to a9 represent integers of 0 to 10, preferably integers of 0 to 6, and more preferably integers of 0 to 5. "*" represents a bond, and the wavy line represents a structure obtained by reaction of an aromatic compound, an acid halide of an aromatic compound, or an ester of an aromatic compound used in synthesizing component (B-2). [ka] [ka]

[0095] Ar 13 The divalent aromatic group and the divalent aliphatic group represented by may have a substituent. The substituent is the same as the substituent that the aromatic ester skeleton may have.

[0096] In general formula (Bi), mi represents an integer of 0 or more, preferably an integer of 0 to 10, more preferably an integer of 0 to 8, even more preferably an integer of 0 to 6, and particularly preferably 0.

[0097] In general formula (Bi), ni represents an integer of 0 or more, preferably an integer of 0-30, more preferably an integer of 3-30, and even more preferably an integer of 6-30.

[0098] In general formula (B-ii), mii and nii each independently represent an integer of 0 or greater, preferably an integer of 0 to 20, more preferably an integer of 0 to 15, and even more preferably an integer of 0 to 10 or an integer of 0 to 6.

[0099] The active ester compound represented by general formula (Bi) is preferably a compound represented by the following general formula (Bia): [ka] In the formula (Bia), Ar 21 each independently represents a monovalent aromatic group which may have a substituent, Ar 22 each independently represents a divalent aromatic group which may have a substituent, Ar 23 each independently represents a divalent aromatic group which may have a substituent, a divalent aliphatic group which may have a substituent, an oxygen atom, a sulfur atom, or a divalent group consisting of a combination thereof. mi1 and ni1 each independently represent an integer of 0 or greater.

[0100] Ar 21 each independently represents a monovalent aromatic group which may have a substituent, and Ar in formula (Bi) 11 is the same as

[0101] Ar 22 each independently represents a divalent aromatic group which may have a substituent, and Ar in formula (Bi) 12 is the same as

[0102] Ar 23 each independently represents a divalent aromatic group which may have a substituent, a divalent aliphatic group which may have a substituent, an oxygen atom, a sulfur atom, or a divalent group consisting of a combination thereof, and Ar 13 is the same as

[0103] mi1 represents an integer of 0 or more and is the same as mi in formula (Bi). Also, ni1 represents an integer of 0 or more and is the same as ni in formula (Bi).

[0104] Specific examples of the component (B-2-a) include the following compounds (Bi) to (Biv). Specific examples of the component (B-2-a) include the compounds described in paragraphs 0068 to 0071 of WO 2018 / 235424 and paragraphs 0113 to 0115 of WO 2018 / 235425. However, the component (B-2-a) is not limited to these specific examples. In the formula, a represents an integer of 0 to 6, s represents 0 or 1 or more, and r represents an integer of 1 to 10. n and m are integers of 0 or more. [ka]

[0105] The component (B-2-a) may be synthesized by a known method. The component (B-2a) can be synthesized, for example, by the method described in WO 2018 / 235424 or WO 2018 / 235425.

[0106] In the component (B-2-b), an example of a skeleton containing a carbon-carbon double bond is a butadiene skeleton. The butadiene skeleton refers to a carbon skeleton contained in a butenediyl group. Here, the butenediyl group includes a 2-butene-1,4-diyl group and a 3-butene-1,2-diyl group (i.e., a vinylethylene group). The 2-butene-1,4-diyl group may be either a cis or trans isomer. Hereinafter, a structure containing a butadiene skeleton may be referred to as a "butadiene structure" as appropriate. This butadiene structure includes the 2-butene-1,4-diyl group and the 3-butene-1,2-diyl group, as well as groups in which the hydrogen atoms contained in these groups are substituted with substituents. Examples of the substituent include halogen atoms; saturated aliphatic hydrocarbon groups such as alkyl groups and cycloalkyl groups; aromatic hydrocarbon groups such as aryl groups; and hydrocarbon oxy groups such as alkoxy groups, cycloalkyloxy groups, and aryloxy groups.

[0107] Preferred examples of the butadiene structure include structures represented by the following formulae (B14) and (B15). [ka] In formula (B14) and formula (B15), R b are each independently a hydrogen atom, a halogen atom, or an alkyl group having 1 to 6 carbon atoms, preferably a hydrogen atom or a halogen atom, more preferably a hydrogen atom. Also, * represents a bonding site.

[0108] The butadiene structure is preferably a structure represented by formula (B14). Therefore, the component (B-2-b) preferably contains a butadiene structure represented by formula (B14) as a structure having a butadiene skeleton, and may contain only a butadiene structure represented by formula (B14).

[0109] The number of butadiene structures contained in one molecule of component (B-2-b) is usually at least 1, and preferably at least 2. In particular, component (B-2-b) more preferably contains a polybutadiene structure in which two or more butadiene structures are bonded to one another.

[0110] The component (B-2-b) is preferably an active ester compound represented by the following formula (B-iii): [ka] In formula (B-iii), Ar 1 each independently represents a monovalent aromatic group which may have a substituent, Ar 2 each independently represents a divalent aromatic group which may have a substituent, and R 1 each independently represents a divalent aliphatic group which may have a substituent, and R 2 each independently represents a butadiene structure, and m and n each independently represent an integer of 0 or greater.

[0111] Ar 1 each independently represents a monovalent aromatic group which may have a substituent, and Ar in formula (Bi) 11 It is the same as the monovalent aromatic group represented by Ar 1 is preferably a 1-methylphenyl group.

[0112] Ar 12 each independently represents a divalent aromatic group which may have a substituent, and Ar in formula (Bi) 12 is the same as the divalent aromatic group represented by

[0113] R 1 each independently represents a divalent aliphatic group which may have a substituent, and R in formula (B-1a) 14 is the same as the divalent aliphatic group represented by

[0114] R 2 each independently represents a butadiene structure, and the butadiene structure is as described above.

[0115] The symbol m represents an integer of 0 or greater, and is preferably an integer of 0 to 10, more preferably an integer of 0 to 8, and even more preferably an integer of 0 to 6. Each symbol n independently represents an integer of 0 or greater, and is preferably an integer of 1 or greater, more preferably an integer of 3 or greater, and even more preferably an integer of 6 or greater. The upper limit is preferably an integer of 50 or less, more preferably an integer of 40 or less, and even more preferably an integer of 30 or less.

[0116] Ar 1 A monovalent aromatic group substituent represented by Ar 12 and R 1 The divalent aliphatic group represented by may have a substituent. The substituent is the same as the substituent that the aromatic ester skeleton may have.

[0117] Specific examples of the component (B-2-b) include the compounds represented by the following formula (B-iv): However, the component (B-2-b) is not limited to these specific examples. 1 , m and n each independently represent Ar 1 , m and n. [ka]

[0118] The component (B-2-i) preferably contains either the component (B-2-a) or the component (B-2-b). Therefore, the component (B-2-i) preferably contains either the active ester compound represented by formula (Bi), the active ester compound represented by formula (B-ii), or the active ester compound represented by formula (B-iii), more preferably the active ester compound represented by formula (Bi) or the active ester compound represented by formula (B-iii), and even more preferably the active ester compound represented by formula (Bi).

[0119] The weight-average molecular weight of component (B-2-i) is preferably at least 150, more preferably at least 200, and even more preferably at least 250, and is preferably at most 3000, more preferably at most 2000, and even more preferably at most 1500. The weight-average molecular weight of component (B-2-i) is the weight-average molecular weight in terms of polystyrene measured by gel permeation chromatography (GPC).

[0120] The active ester equivalent of component (B-2-i) is preferably 50 g / eq or more, more preferably 100 g / eq or more, even more preferably 150 g / eq, and is preferably 2000 g / eq or less, more preferably 1000 g / eq or less, even more preferably 500 g / eq or less. The active ester equivalent represents the mass of resin per equivalent of active ester group.

[0121] The quantitative ratio of component (A) to component (B-2-i), expressed as the ratio of [total number of active ester groups in component (B-2-i)] / [total number of epoxy groups in epoxy resin (A)], is preferably 0.01 or more, more preferably 0.02 or more, even more preferably 0.03 or more, and is preferably 5 or less, more preferably 4 or less, and even more preferably 3 or less. Here, the "number of active ester groups in component (B-2-i)" refers to the total value obtained by dividing the mass of the non-volatile components of component (B-2-i) present in the resin composition by the active ester group equivalent. By keeping the quantitative ratio of component (A) to component (B-2-i) within this range, the effects of the present invention can be significantly achieved.

[0122] The quantitative ratio of component (A) to component (B-1) and (B-2-i), expressed as the ratio of [total number of active groups in component (B-1) and (B-2-i)] / [total number of epoxy groups in epoxy resin (A)], is preferably 0.01 or more, more preferably 0.3 or more, even more preferably 0.5 or more, and preferably 5 or less, more preferably 4 or less, even more preferably 3 or less. Here, the "number of active groups in component (B-1) and (B-2-i)" refers to the total value obtained by dividing the mass of the non-volatile components of component (B-1) and (B-2-i) present in the resin composition by the active ester group equivalent. By setting the quantitative ratio of component (A) to component (B-1) and (B-2-i) within this range, the effects of the present invention can be significantly achieved.

[0123] The content of component (B-2-i) is preferably 1% by mass or more, more preferably 2% by mass or more, and even more preferably 2.5% by mass or more, and is preferably 15% by mass or less, more preferably 10% by mass or less, and even more preferably 8% by mass or less, when the non-volatile components of the resin composition are taken as 100% by mass.

[0124] The content of the (B-2-i) component is preferably 1% by mass or more, more preferably 5% by mass or more, even more preferably 8% by mass or more, or 15% by mass or more, and is preferably 35% by mass or less, more preferably 30% by mass or less, and even more preferably 25% by mass or less, when the resin component of the resin composition is taken as 100% by mass.

[0125] The content of component (B-2-i), when the entire component (B) is taken as 100% by mass, is preferably 60% by mass or less, more preferably 55% by mass or less, and even more preferably 50% by mass or less, and is preferably 10% by mass or more, more preferably 15% by mass or more, and even more preferably 20% by mass or more.

[0126] When the content of component (A) when the nonvolatile components in the resin composition are taken as 100% by mass is defined as a, and the content of component (B-2-i) when the nonvolatile components in the resin composition are taken as 100% by mass is defined as b2, a / b2 is preferably 0.5 or more, more preferably 1 or more, even more preferably 1.5 or more, and is preferably 5 or less, more preferably 4 or less, and even more preferably 3.5 or less. By adjusting the content so that a / b2 falls within this range, the effects of the present invention can be significantly achieved.

[0127] When the content of component (A) is defined as a when the nonvolatile components in the resin composition are taken as 100% by mass, and the total content of components (B-1) and (B-2-i) when the nonvolatile components in the resin composition are taken as 100% by mass is defined as b, a / b is preferably 0.1 or more, more preferably 0.3 or more, even more preferably 0.5 or more, and is preferably 3 or less, more preferably 1.5 or less, and even more preferably 1 or less. By adjusting the content so that a / b1 falls within this range, the effects of the present invention can be significantly achieved.

[0128] When the content of component (B-1) when the nonvolatile components in the resin composition are taken as 100% by mass is taken as b1, and the content of component (B-2-i) when the nonvolatile components in the resin composition are taken as 100% by mass is taken as b2, b1 / b2 is preferably at least 0.3, more preferably at least 0.5, even more preferably at least 1, and preferably at most 10, more preferably at most 8, and even more preferably at most 5. By adjusting the content so that b1 / b2 falls within this range, the effects of the present invention can be significantly achieved.

[0129] The component (B-2) may contain, in addition to the component (B-2-i) which is an active ester compound containing a carbon-carbon double bond, an active ester compound (B-2-ii) which does not contain a carbon-carbon double bond. The component (B-2-ii) may be used alone or in combination of two or more.

[0130] As the component (B-2-ii), compounds having two or more highly reactive ester groups per molecule, such as phenol esters, thiophenol esters, N-hydroxyamine esters, and esters of heterocyclic hydroxy compounds, are preferred.

[0131] The component (B-2-ii) is preferably one obtained by a condensation reaction between a carboxylic acid compound and / or a thiocarboxylic acid compound and a hydroxy compound and / or a thiol compound. From the viewpoint of improving heat resistance in particular, an active ester resin obtained from a carboxylic acid compound and a hydroxy compound is preferred, and an active ester resin obtained from a carboxylic acid compound and a phenol compound and / or a naphthol compound is more preferred. Examples of the carboxylic acid compound include benzoic acid, acetic acid, succinic acid, maleic acid, itaconic acid, phthalic acid, isophthalic acid, terephthalic acid, and pyromellitic acid. Examples of phenol compounds or naphthol compounds include hydroquinone, resorcinol, bisphenol A, bisphenol F, bisphenol S, phenolphthalene, methylated bisphenol A, methylated bisphenol F, methylated bisphenol S, phenol, o-cresol, m-cresol, p-cresol, catechol, α-naphthol, β-naphthol, 1,5-dihydroxynaphthalene, 1,6-dihydroxynaphthalene, 2,6-dihydroxynaphthalene, dihydroxybenzophenone, trihydroxybenzophenone, tetrahydroxybenzophenone, phloroglucin, benzenetriol, dicyclopentadiene-type diphenol compounds, and phenol novolak. Here, "dicyclopentadiene-type diphenol compounds" refers to diphenol compounds obtained by condensing one dicyclopentadiene molecule with two phenol molecules.

[0132] Specifically, the component (B-2-ii) is preferably a dicyclopentadiene-type active ester resin, a naphthalene-type active ester resin containing a naphthalene structure, an active ester resin containing an acetylated product of phenol novolac, or an active ester resin containing a benzoylated product of phenol novolac, and among these, a naphthalene-type active ester resin is more preferred. As the dicyclopentadiene-type active ester resin, an active ester resin containing a dicyclopentadiene-type diphenol structure is preferred.

[0133] Commercially available products of the component (B-2-ii) include, for example, activated ester resins containing a dicyclopentadiene-type diphenol structure, such as "EXB9451," "EXB9460," "EXB9460S," "EXB-8000L," "EXB-8000L-65M," "EXB-8000L-65TM," "HPC-8000L-65TM," "HPC-8000," "HPC-8000-65T," "HPC-8000H," "HPC-8000H-65TM," and "NE-V-1100-70T" (manufactured by DIC Corporation); and activated ester resins containing a naphthalene structure, such as "HP-B-8151-62T," "EXB-8100L-65T," "EXB-8150-60T," and "E Examples of activated ester resins that contain phenol novolac include "XB-8150-62T," "EXB-9416-70BK," "HPC-8150-60T," "HPC-8150-62T," and "HPC-8151-62T" (manufactured by DIC Corporation); "EXB9401" (manufactured by DIC Corporation) as a phosphorus-containing activated ester resin; "DC808" (manufactured by Mitsubishi Chemical Corporation) as an activated ester resin that is an acetylated product of phenol novolac; "YLH1026," "YLH1030," and "YLH1048" (manufactured by Mitsubishi Chemical Corporation) as an activated ester resin that is a benzoylated product of phenol novolac; and "PC1300-02-65MA" (manufactured by Air Water Inc.) as an activated ester resin containing a styryl group and a naphthalene structure.

[0134] The active ester group equivalent range of component (B-2-ii) is preferably 50 g / eq or more, more preferably 100 g / eq or more, and preferably 3,000 g / eq or less, more preferably 1,000 g / eq or less, even more preferably 500 g / eq or less, and particularly preferably 300 g / eq or less. The active ester group equivalent is the mass of an active ester compound containing one equivalent of an active ester group.

[0135] The quantitative ratio of component (A) to component (B-2-ii), expressed as the ratio of [total number of active ester groups in component (B-2-ii)] / [total number of epoxy groups in epoxy resin (A)], is preferably at least 0.01, more preferably at least 0.03, even more preferably at least 0.05, 0.1, 0.15, or 0.2, and is preferably at most 5, more preferably at most 4, and even more preferably at most 3. Here, the "number of active ester groups in component (B-2-ii)" refers to the total value obtained by dividing the mass of the non-volatile components of component (B-2-ii) present in the resin composition by the active ester group equivalent.

[0136] The content of component (B-2-ii) is preferably 0.5% by mass or more, more preferably 1% by mass or more, and even more preferably 2% by mass or more, and is preferably 5% by mass or less, more preferably 4% by mass or less, and even more preferably 3% by mass or less, when the non-volatile components in the resin composition are taken as 100% by mass.

[0137] The content of the (B-2-ii) component is preferably 1% by mass or more, more preferably 1.5% by mass or more, and even more preferably 2% by mass or more, and is preferably 20% by mass or less, more preferably 15% by mass or less, and even more preferably 10% by mass or less, when the resin component in the resin composition is taken as 100% by mass.

[0138] The content of the (B-2-ii) component, when the total amount of the (B) component is taken as 100% by mass, is preferably 60% by mass or less, more preferably 55% by mass or less, and even more preferably 50% by mass or less, and is preferably 10% by mass or more, more preferably 15% by mass or more, and even more preferably 20% by mass or more.

[0139] The content of component (B-2) is preferably 1% by mass or more, more preferably 2% by mass or more, and even more preferably 2.5% by mass or more, and is preferably 15% by mass or less, more preferably 10% by mass or less, and even more preferably 8% by mass or less, when the non-volatile components of the resin composition are taken as 100% by mass.

[0140] The content of the (B-2) component is preferably 1% by mass or more, more preferably 5% by mass or more, even more preferably 8% by mass or more, or 15% by mass or more, and is preferably 35% by mass or less, more preferably 30% by mass or less, and even more preferably 25% by mass or less, when the resin component of the resin composition is taken as 100% by mass.

[0141] The content of the (B-2) component, when the entire (B) component is taken as 100% by mass, is preferably 60% by mass or less, more preferably 55% by mass or less, and even more preferably 50% by mass or less, and is preferably 10% by mass or more, more preferably 15% by mass or more, and even more preferably 20% by mass or more.

[0142] The quantitative ratio of component (A) to component (B), expressed as the ratio of [total number of active groups in component (B)] / [total number of epoxy groups in epoxy resin (A)], is preferably 0.01 or more, more preferably 0.3 or more, and even more preferably 0.5 or more, and is preferably 5 or less, more preferably 4 or less, and even more preferably 3 or less. Here, the "number of active groups in component (B)" refers to the total value obtained by dividing the mass of the non-volatile components of component (B) present in the resin composition by the active ester group equivalent. By keeping the quantitative ratio of component (A) to component (B) within this range, it becomes possible to achieve significant effects of the present invention.

[0143] The content of component (B) is preferably 1% by mass or more, more preferably 3% by mass or more, and even more preferably 5% by mass or more, and is preferably 25% by mass or less, more preferably 20% by mass or less, and even more preferably 15% by mass or less, when the non-volatile components in the resin composition are taken as 100% by mass.

[0144] The content of component (B) is preferably 30% by mass or more, more preferably 35% by mass or more, and even more preferably 40% by mass or more, and is preferably 65% ​​by mass or less, more preferably 60% by mass or less, and even more preferably 55% by mass or less, when the resin component in the resin composition is taken as 100% by mass.

[0145] <(C) Inorganic filler> The resin composition contains an inorganic filler (C) as component (C). By including the inorganic filler (C) in the resin composition, a cured product having a low dielectric loss tangent and a low linear thermal expansion coefficient can be obtained. The inorganic filler (C) is usually contained in the resin composition in the form of particles. The component (C) may be used alone or in combination of two or more.

[0146] (C) Inorganic fillers are inorganic compounds. Examples of (C) inorganic filler materials include silica, alumina, glass, cordierite, silicon oxide, barium sulfate, barium carbonate, talc, clay, mica powder, zinc oxide, hydrotalcite, boehmite, aluminum hydroxide, magnesium hydroxide, calcium carbonate, magnesium carbonate, magnesium oxide, boron nitride, aluminum nitride, manganese nitride, aluminum borate, strontium carbonate, strontium titanate, calcium titanate, magnesium titanate, bismuth titanate, titanium oxide, zirconium oxide, barium titanate, barium titanate zirconate, barium zirconate, calcium zirconate, zirconium phosphate, and zirconium tungstate phosphate. Among these, silica is particularly preferred. Examples of silica include amorphous silica, fused silica, crystalline silica, synthetic silica, and hollow silica. Spherical silica is preferred.

[0147] (C) Examples of commercially available inorganic fillers include "SP60-05" and "SP507-05" manufactured by Nippon Steel Chemical & Material Co., Ltd.; "YC100C," "YA050C," "YA050C-MJE," "YA010C," "SC2500SQ," "SO-C4," "SO-C2," and "SO-C1" manufactured by Admatechs Co., Ltd.; "UFP-30," "DAW-03," and "FB-105FD" manufactured by Denka Company, Limited; "Silfil NSS-3N," "Silfil NSS-4N," and "Silfil NSS-5N" manufactured by Tokuyama Corporation; and "CellSpheres MGH-005" manufactured by Taiheiyo Cement Corporation.

[0148] The average particle size of the (C) inorganic filler is preferably 0.01 μm or more, more preferably 0.1 μm or more, even more preferably 0.3 μm or more, 0.4 μm or more, or 0.5 μm or more, and is preferably 10 μm or less, more preferably 5 μm or less, and even more preferably 3 μm or less.

[0149] (C) The average particle size of an inorganic filler can be measured by a laser diffraction / scattering method based on Mie scattering theory. Specifically, a volumetric particle size distribution of the inorganic filler is created using a laser diffraction / scattering particle size distribution analyzer, and the median diameter is used as the average particle size. A measurement sample can be prepared by weighing 100 mg of inorganic filler and 10 g of methyl ethyl ketone into a vial and dispersing the mixture ultrasonically for 10 minutes. The volumetric particle size distribution of the inorganic filler is measured using a laser diffraction particle size distribution analyzer with blue and red light source wavelengths using a flow cell system, and the average particle size can be calculated as the median diameter from the particle size distribution obtained. Examples of laser diffraction particle size distribution analyzers include the LA-960 manufactured by Horiba, Ltd.

[0150] (C) The BET specific surface area of ​​the inorganic filler is preferably 0.1 m 2 / g or more, more preferably 0.5m 2 / g or more, more preferably 1m 2 / g or more, preferably 100m 2 / g or less, more preferably 70m2 / g or less, more preferably 40m 2 / g or less.

[0151] (C) The specific surface area of ​​the inorganic filler can be measured according to the BET method by adsorbing nitrogen gas onto the sample surface using a specific surface area measuring device (Macsorb HM-1210 manufactured by Mountech Co., Ltd.) and calculating the specific surface area using the BET multipoint method.

[0152] The (C) inorganic filler is preferably treated with a surface treatment agent from the viewpoint of improving moisture resistance and dispersibility. Examples of the surface treatment agent include a fluorine-containing silane coupling agent, an aminosilane coupling agent, an epoxysilane coupling agent, a mercaptosilane coupling agent, a silane coupling agent, an alkoxysilane, an organosilazane compound, and a titanate coupling agent. One type of surface treatment agent may be used alone, or two or more types may be used in any combination.

[0153] Examples of commercially available surface treatment agents include Shin-Etsu Chemical Co., Ltd.'s "KBM403" (3-glycidoxypropyltrimethoxysilane), Shin-Etsu Chemical Co., Ltd.'s "KBM803" (3-mercaptopropyltrimethoxysilane), Shin-Etsu Chemical Co., Ltd.'s "KBE903" (3-aminopropyltriethoxysilane), Shin-Etsu Chemical Co., Ltd.'s "KBM573" (N-phenyl-3-aminopropyltrimethoxysilane), Shin-Etsu Chemical Co., Ltd.'s "SZ-31" (hexamethyldisilazane), Shin-Etsu Chemical Co., Ltd.'s "KBM103" (phenyltrimethoxysilane), Shin-Etsu Chemical Co., Ltd.'s "KBM-4803" (long-chain epoxy-type silane coupling agent), and Shin-Etsu Chemical Co., Ltd.'s "KBM-7103" (3,3,3-trifluoropropyltrimethoxysilane).

[0154] The degree of surface treatment with the surface treatment agent preferably falls within a specific range from the viewpoint of improving the dispersibility of the inorganic filler. Specifically, 100% by mass of the inorganic filler is preferably surface-treated with 0.2% to 5% by mass of the surface treatment agent, more preferably with 0.2% to 3% by mass of the surface treatment agent, and even more preferably with 0.3% to 2% by mass of the surface treatment agent.

[0155] The degree of surface treatment with the surface treatment agent can be evaluated by the amount of carbon per unit surface area of ​​the inorganic filler. From the viewpoint of improving the dispersibility of the inorganic filler, the amount of carbon per unit surface area of ​​the inorganic filler is set to 0.02 mg / m 2 More than 0.1 mg / m is preferable. 2 More preferably, 0.2 mg / m or more 2 On the other hand, from the viewpoint of preventing an increase in the melt viscosity of the resin composition, it is more preferable that the content be 1.0 mg / m 2 Preferably less than 0.8 mg / m 2 Less than 0.5 mg / m is more preferable. 2 The following is even more preferred:

[0156] (C) The amount of carbon per unit surface area of ​​the inorganic filler can be measured after the surface-treated inorganic filler is washed with a solvent (e.g., methyl ethyl ketone (MEK)). Specifically, a sufficient amount of MEK as a solvent is added to the inorganic filler that has been surface-treated with a surface treatment agent, and ultrasonic cleaning is performed at 25°C for 5 minutes. After removing the supernatant and drying the solid content, the amount of carbon per unit surface area of ​​the inorganic filler can be measured using a carbon analyzer. An "EMIA-320V" manufactured by Horiba, Ltd., or the like can be used as the carbon analyzer.

[0157] The degree of surface treatment with a surface treatment agent can be evaluated by the amount of carbon per unit mass of the inorganic filler. The amount of carbon per unit mass of the inorganic filler is preferably 0.01% by mass or more, more preferably 0.05% by mass or more, and even more preferably 0.1% by mass or more, and is preferably 1.0% by mass or less, more preferably 0.8% by mass or less, and even more preferably 0.5% by mass or less. The amount of carbon per unit mass of (C) inorganic filler can be measured using a carbon analyzer, just like the amount of carbon per unit surface area of ​​(C) inorganic filler.

[0158] The content of (C) inorganic filler is preferably 50% by mass or more, more preferably 55% by mass or more, even more preferably 60% by mass or more, 65% by mass or more, or 70% by mass or more, and is preferably 90% by mass or less, more preferably 85% by mass or less, and even more preferably 80% by mass or less, assuming that the non-volatile components in the resin composition are 100% by mass.

[0159] <(D) Radical Polymerizable Compound> The resin composition may contain a radically polymerizable compound (D) as component (D). This radically polymerizable compound (D) as component (D) excludes those corresponding to components (A) to (C). The component (D) may be used alone or in combination of two or more.

[0160] The (D) radical polymerizable compound may contain an ethylenically unsaturated bond. Therefore, the (D) radical polymerizable compound may have a radical polymerizable group containing an ethylenically unsaturated bond. Examples of the radical polymerizable group include unsaturated hydrocarbon groups such as vinyl, allyl, 1-propenyl, 3-cyclohexenyl, 3-cyclopentenyl, 2-vinylphenyl, 3-vinylphenyl, and 4-vinylphenyl; and α,β-unsaturated carbonyl groups such as acryloyl, methacryloyl, and maleimide groups (2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl). The (D) radical polymerizable compound preferably has two or more radical polymerizable groups.

[0161] Examples of the (D) radical polymerizable compound include a (meth)acrylic radical polymerizable compound, a styrene radical polymerizable compound, an allyl radical polymerizable compound, a maleimide radical polymerizable compound, etc. The (D) component preferably contains any one of a styrene radical polymerizable compound, an allyl radical polymerizable compound, and a maleimide radical polymerizable compound, more preferably any one of an allyl radical polymerizable compound and a maleimide radical polymerizable compound, and even more preferably contains a maleimide radical polymerizable compound.

[0162] The (meth)acrylic radical polymerizable compound is, for example, a compound having one or more, preferably two or more, acryloyl groups and / or methacryloyl groups. Examples of the (meth)acrylic radical polymerizable compound include cyclohexane-1,4-dimethanol di(meth)acrylate, cyclohexane-1,3-dimethanol di(meth)acrylate, tricyclodecane dimethanol di(meth)acrylate, neopentyl glycol di(meth)acrylate, 1,4-butanediol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, 1,8-octanediol di(meth)acrylate, 1,9-nonanediol di(meth)acrylate, and the like. Low molecular weight (molecular weight less than 1000) aliphatic (meth)acrylic acid ester compounds such as dioxane glycol di(meth)acrylate, 3,6-dioxa-1,8-octanediol di(meth)acrylate, 1,10-decanediol di(meth)acrylate, trimethylolpropane tri(meth)acrylate, trimethylolethane tri(meth)acrylate, glycerin tri(meth)acrylate, and pentaerythritol tetra(meth)acrylate; low molecular weight (molecular weight less than 1000) ether-containing (meth)acrylic acid ester compounds such as tris(3-hydroxypropyl)isocyanurate tri(meth)acrylate, tris(2-hydroxyethyl)isocyanurate tri(meth)acrylate, and ethoxylated isocyanuric acid tri(meth)acrylate; and high molecular weight (molecular weight 1000 or more) acrylic acid ester compounds such as (meth)acrylic-modified polyphenylene ether resins.Examples of commercially available (meth)acrylic radically polymerizable compounds include "A-DOG" (dioxane glycol diacrylate) manufactured by Shin-Nakamura Chemical Co., Ltd., "DCP-A" (tricyclodecane dimethanol diacrylate) and "DCP" (tricyclodecane dimethanol dimethacrylate) manufactured by Kyoeisha Chemical Co., Ltd., "KAYARAD R-684" (tricyclodecane dimethanol diacrylate) and "KAYARAD R-604" (dioxane glycol diacrylate) manufactured by Nippon Kayaku Co., Ltd., and "SA9000" and "SA9000-111" (methacrylic-modified polyphenylene ether) manufactured by SABIC.

[0163] The styrene-based radical polymerizable compound is, for example, a compound having one or more, preferably two or more, vinyl groups directly bonded to an aromatic carbon atom. Examples of the styrene-based radical polymerizable compound 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; and high-molecular-weight (molecular-weight 1000 or more) styrene-based compounds such as styrene-modified polyphenylene ether resin and styrene-divinylbenzene copolymer. Commercially available styrene-based radical polymerizable compounds include, for example, "ODV-XET(X03)", "ODV-XET(X04)", and "ODV-XET(X05)" (styrene-divinylbenzene copolymers) manufactured by Nippon Steel Chemical & Material Co., Ltd., and "OPE-2St 1200" and "OPE-2St 2200" (styrene-modified polyphenylene ether resins) manufactured by Mitsubishi Gas Chemical Company, Inc. Further, examples of the styrene-based radical polymerizable compound include Copolymer A described in WO 2017 / 115813.

[0164] The allyl radical polymerizable compound is, for example, a compound having one or more, preferably two or more, allyl groups. Examples of allyl radical polymerizable compounds include aromatic carboxylic acid allyl ester compounds such as diallyl diphenate, triallyl trimellitate, diallyl phthalate, diallyl isophthalate, diallyl terephthalate, diallyl 2,6-naphthalenedicarboxylate, and diallyl 2,3-naphthalenecarboxylate; isocyanuric acid allyl ester compounds such as 1,3,5-triallyl isocyanurate and 1,3-diallyl-5-glycidyl isocyanurate; epoxy-containing aromatic allyl compounds such as 2,2-bis[3-allyl-4-(glycidyloxy)phenyl]propane; benzoxazine-containing aromatic allyl compounds such as bis[3-allyl-4-(3,4-dihydro-2H-1,3-benzoxazin-3-yl)phenyl]methane; ether-containing aromatic allyl compounds such as 1,3,5-triallyl ether benzene; and allyl silane compounds such as diallyldiphenylsilane. Commercially available allyl radical polymerizable compounds include "TAIC" (1,3,5-triallyl isocyanurate) manufactured by Nippon Kasei Chemical Industry Co., Ltd., "DAD" (diallyl diphenate) manufactured by Nisshoku Techno Fine Chemical Co., Ltd., "TRIAM-705" (triallyl trimellitate) manufactured by Fujifilm Wako Pure Chemical Industries, Ltd., "DAND" (2,3-naphthalene carboxylic acid diallyl) manufactured by Nisshoku Techno Fine Chemical Co., Ltd., "ALP-d" (bis[3-allyl-4-(3,4-dihydro-2H-1,3-benzoxazin-3-yl)phenyl]methane) manufactured by Shikoku Chemical Industry Co., Ltd., "RE-810NM" (2,2-bis[3-allyl-4-(glycidyloxy)phenyl]propane) manufactured by Nippon Kayaku Co., Ltd., and "DA-MGIC" (1,3-diallyl-5-glycidyl isocyanurate) manufactured by Shikoku Chemical Industry Co., Ltd.

[0165] The maleimide radical polymerizable compound is, for example, a compound having one or more, preferably two or more, maleimide groups. The maleimide radical polymerizable compound may be an aliphatic maleimide compound containing an aliphatic amine skeleton, or an aromatic maleimide compound containing an aromatic amine skeleton. Commercially available maleimide radical polymerizable compounds include, for example, "SLK-2600" manufactured by Shin-Etsu Chemical Co., Ltd., "BMI-1500," "BMI-1700," "BMI-3000J," "BMI-689," and "BMI-2500" (dimer diamine structure-containing maleimide compounds) manufactured by DesiCner Molecules, Inc., "BMI-6100" (aromatic maleimide compound) manufactured by DesiCner Molecules, Inc., "MIR-5000-60T" and "MIR-3000-70MT" (biphenylaralkyl maleimide compounds) manufactured by Nippon Kayaku Co., Ltd., "BMI-70" and "BMI-80" manufactured by K.I. Chemical Industry Co., Ltd., and "BMI-2300" and "BMI-TMH" manufactured by Daiwa Kasei Kogyo Co., Ltd. Furthermore, as the maleimide-based radical polymerizable compound, a maleimide resin (maleimide compound containing an indane ring skeleton) disclosed in Technical Disclosure No. 2020-500211 of the Japan Institute of Invention and Innovation may be used.

[0166] The ethylenically unsaturated bond equivalent of the (D) radically polymerizable compound is preferably 20 g / eq. to 3,000 g / eq., more preferably 50 g / eq. to 2,500 g / eq., even more preferably 70 g / eq. to 2,000 g / eq., and particularly preferably 90 g / eq. to 1,500 g / eq. The ethylenically unsaturated bond equivalent represents the mass of the radically polymerizable compound per equivalent of the ethylenically unsaturated bond.

[0167] The weight-average molecular weight (Mw) of the (D) radically polymerizable compound is preferably 40,000 or less, more preferably 10,000 or less, even more preferably 5,000 or less, and particularly preferably 3,000 or less. The lower limit is not particularly limited, but may be, for example, 150 or more. The weight-average molecular weight can be measured as a polystyrene-equivalent value by gel permeation chromatography (GPC).

[0168] The content of component (D) is preferably 0.1% by mass or more, more preferably 0.5% by mass or more, and even more preferably 1% by mass or more, and is preferably 10% by mass or less, more preferably 5% by mass or less, and even more preferably 3% by mass or less, when the non-volatile components in the resin composition are taken as 100% by mass.

[0169] The content of component (D) is preferably 1% by mass or more, more preferably 5% by mass or more, and even more preferably 8% by mass or more, and is preferably 20% by mass or less, more preferably 15% by mass or less, and even more preferably 12% by mass or less, when the resin component in the resin composition is taken as 100% by mass.

[0170] <(E) Optional Hardener> The resin composition may contain, as component (E), an optional curing agent (E) other than component (B). The optional curing agent (E) as component (E) refers to a resin that can react with the epoxy resin (A) to cure the resin composition. The optional curing agent (E) does not include those that fall under the aforementioned components (A) to (D). For example, although a maleimide resin may react with the epoxy resin (A) under an appropriate catalyst, the maleimide resin is not classified as an optional curing agent (E). The optional curing agents (E) may be used singly or in combination of two or more.

[0171] Preferred examples of the optional curing agent (E) include phenolic resins, benzoxazine resins, cyanate ester resins, carbodiimide resins, acid anhydride resins, and amine resins.

[0172] As the phenolic resin, a resin having one or more, preferably two or more, hydroxyl groups (phenolic hydroxyl groups) bonded to an aromatic ring such as a benzene ring or a naphthalene ring per molecule can be used. From the viewpoint of heat resistance and water resistance, a phenolic resin having a novolac structure is preferred. From the viewpoint of adhesion, a nitrogen-containing phenolic resin is preferred, and a triazine skeleton-containing phenolic resin is more preferred. Among these, a triazine skeleton-containing phenolic novolac resin is preferred from the viewpoint of highly satisfying heat resistance, water resistance, and adhesion.

[0173] Specific examples of phenolic resins include "MEH-7700," "MEH-7810," "MEH-7851," and "MEH-8000H" manufactured by Meiwa Kasei Co., Ltd.; "NHN," "CBN," and "GPH" manufactured by Nippon Kayaku Co., Ltd.; and "SN-170," "SN-180," "SN-190," "SN-475," "SN-485," "SN-495," "SN-495V," and "SN-3" manufactured by Nippon Steel Chemical & Material Co., Ltd. 75" and "SN-395" manufactured by DIC Corporation; "TD-2090", "TD-2090-60M", "LA-7052", "LA-7054", "LA-1356", "LA-3018", "LA-3018-50P", "LA-1356", "TD2090", and "TD-2090-60M" manufactured by Gun-ei Chemical Co., Ltd.; and "GDP-6115L", "GDP-6115H", and "ELPC75" manufactured by Gun-ei Chemical Co., Ltd. The benzoxazine resin may be a resin having one or more, preferably two or more, benzoxazine rings in one molecule. Specific examples of the benzoxazine resin include "JBZ-OP100D" and "ODA-BOZ" manufactured by JFE Chemical Corporation, "HFB2006M" manufactured by Showa Polymer Co., Ltd., and "Pd", "Fa", and "ALP-d" manufactured by Shikoku Chemicals Corporation.

[0174] As the cyanate ester resin, a resin having one or more, preferably two or more, cyanate groups in one molecule can be used. Examples of cyanate ester resins include bifunctional cyanate ester resins such as bisphenol A dicyanate, polyphenol cyanate, oligo(3-methylene-1,5-phenylene cyanate), 4,4'-methylenebis(2,6-dimethylphenyl cyanate), 4,4'-ethylidene diphenyl dicyanate, hexafluorobisphenol A dicyanate, 2,2-bis(4-cyanate)phenylpropane, 1,1-bis(4-cyanatephenylmethane), bis(4-cyanate-3,5-dimethylphenyl)methane, 1,3-bis(4-cyanatephenyl-1-(methylethylidene))benzene, bis(4-cyanatephenyl)thioether, and bis(4-cyanatephenyl)ether; multifunctional cyanate ester resins derived from phenol novolac, cresol novolac, and the like; and prepolymers in which these cyanate ester resins are partially triazine converted. Specific examples of cyanate ester resins include "PT30" and "PT60" (phenol novolac type multifunctional cyanate ester resins) manufactured by Arxada, "BA230" and "BA230S75" (prepolymers in which part or all of bisphenol A dicyanate has been triazine converted to a trimer).

[0175] As the carbodiimide resin, a resin having one or more, preferably two or more, carbodiimide structures in one molecule can be used. Specific examples of the carbodiimide resin include aliphatic biscarbodiimides such as tetramethylene-bis(t-butylcarbodiimide) and cyclohexanebis(methylene-t-butylcarbodiimide); aromatic biscarbodiimides such as phenylene-bis(xylylcarbodiimide); aliphatic polycarbodiimides such as polyhexamethylenecarbodiimide, polytrimethylhexamethylenecarbodiimide, polycyclohexylenecarbodiimide, poly(methylenebiscyclohexylenecarbodiimide), and poly(isophoronecarbodiimide); poly(phenylenecarbodiimide), poly(naphthalenecarbodiimide); Examples of polycarbodiimides include aromatic polycarbodiimides such as poly(methylenediphenylenecarbodiimide), poly(tolylenecarbodiimide), poly(methyldiisopropylphenylenecarbodiimide), poly(triethylphenylenecarbodiimide), poly(diethylphenylenecarbodiimide), poly(triisopropylphenylenecarbodiimide), poly(diisopropylphenylenecarbodiimide), poly(xylylenecarbodiimide), poly(tetramethylxylylenecarbodiimide), poly(methylenediphenylenecarbodiimide), and poly[methylenebis(methylphenylene)carbodiimide]. Commercially available carbodiimide resins include, for example, "Carbodilite V-02B," "Carbodilite V-03," "Carbodilite V-04K," "Carbodilite V-05," "Carbodilite V-07," and "Carbodilite V-09" manufactured by Nisshinbo Chemical Inc.; and "Stavaxol P," "Stavaxol P400," and "Hykasil 510" manufactured by Lanxess AG.

[0176] As the acid anhydride resin, a resin having one or more, preferably two or more, acid anhydride groups in one molecule can be used. Specific examples of the acid anhydride resin include phthalic anhydride, tetrahydrophthalic anhydride, hexahydrophthalic anhydride, methyltetrahydrophthalic anhydride, methylhexahydrophthalic anhydride, methylnadic anhydride, hydrogenated methylnadic anhydride, trialkyltetrahydrophthalic anhydride, dodecenyl succinic anhydride, 5-(2,5-dioxotetrahydro-3-furanyl)-3-methyl-3-cyclohexene-1,2-dicarboxylic anhydride, trimellitic anhydride, pyromellitic anhydride, and benzophenonetetracarboxylic anhydride. Examples of suitable anhydrides include hydrates, biphenyltetracarboxylic dianhydride, naphthalenetetracarboxylic dianhydride, oxydiphthalic dianhydride, 3,3'-4,4'-diphenylsulfonetetracarboxylic dianhydride, 1,3,3a,4,5,9b-hexahydro-5-(tetrahydro-2,5-dioxo-3-furanyl)-naphtho[1,2-C]furan-1,3-dione, ethylene glycol bis(anhydrotrimellitate), and polymeric anhydrides such as styrene-maleic acid resin, which is a copolymer of styrene and maleic acid. Commercially available acid anhydride resins include, for example, "HNA-100," "MH-700," "MTA-15," "DDSA," and "OSA" manufactured by New Japan Chemical Co., Ltd.; "YH-306" and "YH-307" manufactured by Mitsubishi Chemical Corporation; "HN-2200" manufactured by Resonac Corporation; and "EF-30," "EF-40," "EF-60," and "EF-80" manufactured by Cray Valley Chemical Industries, Ltd.

[0177] The amine resin may be a resin having one or more, preferably two or more, amino groups in one molecule. Examples of the amine resin include aliphatic amines, polyether amines, alicyclic amines, and aromatic amines, with aromatic amines being preferred. The amine resin is preferably a primary amine or secondary amine, with primary amines being more preferred. Specific examples of the amine resin include 4,4'-methylenebis(2,6-dimethylaniline), 4,4'-diaminodiphenylmethane, 4,4'-diaminodiphenyl sulfone, 3,3'-diaminodiphenyl sulfone, m-phenylenediamine, m-xylylenediamine, diethyltoluenediamine, 4,4'-diaminodiphenyl ether, 3,3'-dimethyl-4,4'-diaminobiphenyl, 2,2'-dimethyl-4,4'-diaminobiphenyl, 3,3'-dihydroxybenzidine, and 2,2-bis(3-amino-4-hydroxyphenyl)propanol. Examples of suitable bis(4-aminophenoxy)benzene include bis(4-aminophenyl)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, and bis(4-(3-aminophenoxy)phenyl)sulfone. Commercially available amine resins include, for example, "SEIKACURE-S" manufactured by Seika Corporation; "KAYABOND C-200S," "KAYABOND C-100," "KAYAHARD AA," "KAYAHARD AB," and "KAYAHARD AS" manufactured by Nippon Kayaku Co., Ltd.; "Epicure W" manufactured by Mitsubishi Chemical Corporation; and "DTDA" manufactured by Sumitomo Seika Chemicals Co., Ltd.

[0178] The active group equivalent of component (E) is preferably 50 g / eq. to 3,000 g / eq., more preferably 100 g / eq. to 1,000 g / eq., even more preferably 100 g / eq. to 500 g / eq., and particularly preferably 100 g / eq. to 300 g / eq. The active group equivalent represents the mass of resin per equivalent of active group.

[0179] The quantitative ratio of component (A) to component (E), expressed as the ratio of [total number of active groups in component (E)] / [total number of epoxy groups in epoxy resin (A)], is preferably 0.01 or more, more preferably 0.05 or more, even more preferably 0.1 or more, 0.15 or more, 0.2 or more, or 0.25 or more, and is preferably 5 or less, more preferably 4 or less, and even more preferably 3 or less, 2 or less, or 1 or less. Here, the "number of active groups in component (E)" refers to the total value obtained by dividing the mass of the non-volatile components of component (E) present in the resin composition by the active group equivalent.

[0180] The quantitative ratio of component (A) to components (B) and (E), expressed as the ratio of [total number of active ester groups in component (B) and active groups in component (E)] / [total number of epoxy groups in epoxy resin (A)], is preferably 0.01 or more, more preferably 0.3 or more, even more preferably 0.5 or more, 0.7 or more, 0.9 or more, 1 or more, 1.1 or more, or 1.2 or more, and is preferably 5 or less, more preferably 4 or less, and even more preferably 3 or less. Here, "the number of active groups in components (B) and (E)" refers to the total value obtained by dividing the mass of the non-volatile components of components (B) and (E) present in the resin composition by the active group equivalent.

[0181] The content of component (E) is preferably 0.5% by mass or more, more preferably 1% by mass or more, and even more preferably 1.5% by mass or more, and is preferably 5% by mass or less, more preferably 4% by mass or less, and even more preferably 3% by mass or less, assuming that the non-volatile components in the resin composition are 100% by mass.

[0182] The content of component (E) is preferably 0.1% by mass or more, more preferably 0.5% by mass or more, even more preferably 1% by mass or more, 2% by mass or more, 4% by mass or more, or 6% by mass or more, based on 100% by mass of the resin components in the resin composition. The upper limit is preferably 20% by mass or less, more preferably 15% by mass or less, and even more preferably 10% by mass or less.

[0183] <(F)Organic filler> The resin composition according to this embodiment may contain an organic filler (F) as an optional component. The organic filler (F) as component (F) does not include those corresponding to the above-mentioned components (A) to (E). The organic filler (F) is usually incompatible with resin components other than the organic filler (F), is contained in the resin composition in the form of particles, and is contained in the cured product while maintaining this particle state. Furthermore, one type of organic filler (F) may be used alone, or two or more types may be used in combination.

[0184] The (F) organic filler may be particles of an organic material. A rubber component is preferred as the organic material contained in the (F) organic filler. Examples of rubber components include silicone-based elastomers such as polydimethylsiloxane; olefin-based thermoplastic elastomers such as polybutadiene, polyisoprene, polychlorobutadiene, ethylene-vinyl acetate copolymer, styrene-butadiene copolymer, styrene-isoprene copolymer, styrene-isobutylene copolymer, acrylonitrile-butadiene copolymer, isoprene-isobutylene copolymer, isobutylene-butadiene copolymer, ethylene-propylene-diene terpolymer, and ethylene-propylene-butene terpolymer; and thermoplastic elastomers such as acrylic thermoplastic elastomers such as polypropyl(meth)acrylate, polybutyl(meth)acrylate, polycyclohexyl(meth)acrylate, and polyoctyl(meth)acrylate. Furthermore, silicone-based rubbers such as polyorganosiloxane rubber may be mixed into the rubber component. The rubber component contained in the rubber particles has a glass transition temperature of, for example, 0°C or lower, preferably -10°C or lower, more preferably -20°C or lower, and even more preferably -30°C or lower.

[0185] The (F) organic filler may be a core-shell type rubber particle consisting of a core particle containing the above-mentioned 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 term "core-shell type" does not necessarily refer only to those in which the core particle and the shell portion are clearly distinguishable, but also includes those in which the boundary between the core particle and the shell portion is unclear, and the core particle does not necessarily have to be completely covered with the shell portion.

[0186] Specific examples of (F) organic fillers include "CHT" manufactured by Samsung SDI; "B602" manufactured by Techno UMG; "Paraloid EXL-2602", "Paraloid EXL-2603", "Paraloid EXL-2655", "Paraloid EXL-2311", "Paraloid-EXL2313", "Paraloid EXL-2315", "Paraloid KM-330", "Paraloid KM-336P", and "Paraloid KCZ-201" manufactured by Dow; and "Metabrene C-223A" and "Metabrene E- 901," "Metabrene S-2001," "Metabrene W-450A," "Metabrene SRK-200," "Kane Ace M-511," "Kane Ace M-600," "Kane Ace M-400," "Kane Ace M-580," and "Kane Ace MR-01" manufactured by Kaneka Corporation, and "Staphyloid AC3355," "Staphyloid AC3816," "Staphyloid AC3816N," "Staphyloid AC3832," "Staphyloid AC4030," and "Staphyloid AC3364" manufactured by Aica Kogyo Co., Ltd.

[0187] The content of the (F) organic filler is preferably 0.01% by mass or more, more preferably 0.1% by mass or more, even more preferably 0.3% by mass or more, relative to 100% by mass of the nonvolatile components in the resin composition, and is preferably 3% by mass or less, more preferably 2% by mass or less, even more preferably 1% by mass or less.

[0188] The content of the (F) organic filler, relative to 100% by mass of the resin component in the resin composition, is preferably 0.1% by mass or more, more preferably 0.5% by mass or more, even more preferably 1% by mass or more, and is preferably 10% by mass or less, more preferably 8% by mass or less, 6% by mass or less, or 5% by mass or less, more preferably 4% by mass or less, or 3% by mass or less, even more preferably 2% by mass or less.

[0189] <(G) Curing accelerator> The resin composition may contain a (G) curing accelerator as an optional component. The (G) curing accelerator as component (G) does not include those corresponding to the above-mentioned components (A) to (F). The (G) curing accelerator acts as a catalyst for the reaction of the (A) epoxy resin, thereby accelerating the curing of the resin composition.

[0190] Examples of the (G) curing accelerator include phosphorus-based curing accelerators, urea-based curing accelerators, guanidine-based curing accelerators, imidazole-based curing accelerators, metal-based curing accelerators, amine-based curing accelerators, etc. One type of (G) curing accelerator may be used alone, or two or more types may be used in combination.

[0191] Examples of the phosphorus-based curing accelerator include aliphatic phosphonium salts such as tetrabutylphosphonium bromide, tetrabutylphosphonium chloride, tetrabutylphosphonium acetate, tetrabutylphosphonium decanoate, tetrabutylphosphonium laurate, bis(tetrabutylphosphonium)pyromellitate, tetrabutylphosphonium hydrogenhexahydrophthalate, tetrabutylphosphonium 2,6-bis[(2-hydroxy-5-methylphenyl)methyl]-4-methylphenolate, and di-tert-butyldimethylphosphonium tetraphenylborate; methyltriphenylphosphonium bromide, ethyltriphenylphosphonium bromide, propyltriphenylphosphonium bromide, butyltriphenylphosphonium bromide, benzyltriphenylphosphonium chloride, tetraphenylphosphonium bromide, p-tolyltriphenylphosphonium tetra-p-tolylborate, and tetraphenylphosphonium tetra-p-tolylborate. aromatic phosphonium salts such as tetraphenylborate, tetraphenylphosphonium tetra-p-tolylborate, triphenylethylphosphonium tetraphenylborate, tris(3-methylphenyl)ethylphosphonium tetraphenylborate, tris(2-methoxyphenyl)ethylphosphonium tetraphenylborate, (4-methylphenyl)triphenylphosphonium thiocyanate, tetraphenylphosphonium thiocyanate, and butyltriphenylphosphonium thiocyanate; aromatic phosphine-borane complexes such as triphenylphosphine-triphenylborane; aromatic phosphine-quinone adducts such as triphenylphosphine-p-benzoquinone adduct; aliphatic phosphines such as tributylphosphine, tri-tert-butylphosphine, trioctylphosphine, di-tert-butyl(2-butenyl)phosphine, di-tert-butyl(3-methyl-2-butenyl)phosphine, and tricyclohexylphosphine;Dibutylphenylphosphine, di-tert-butylphenylphosphine, methyldiphenylphosphine, ethyldiphenylphosphine, butyldiphenylphosphine, diphenylcyclohexylphosphine, triphenylphosphine, tri-o-tolylphosphine, tri-m-tolylphosphine, tri-p-tolylphosphine, tris(4-ethylphenyl)phosphine, tris(4-propylphenyl)phosphine, tris(4-isopropylphenyl)phosphine, tris(4-butylphenyl)phosphine, tris(4-tert-butylphenyl)phosphine, tris(2,4-dimethylphenyl)phosphine, tris(2,5-dimethylphenyl)phosphine, tris(2,6-dimethylphenyl)phosphine aromatic phosphines such as benzene, tris(3,5-dimethylphenyl)phosphine, tris(2,4,6-trimethylphenyl)phosphine, tris(2,6-dimethyl-4-ethoxyphenyl)phosphine, tris(2-methoxyphenyl)phosphine, tris(4-methoxyphenyl)phosphine, tris(4-ethoxyphenyl)phosphine, tris(4-tert-butoxyphenyl)phosphine, diphenyl-2-pyridylphosphine, 1,2-bis(diphenylphosphino)ethane, 1,3-bis(diphenylphosphino)propane, 1,4-bis(diphenylphosphino)butane, 1,2-bis(diphenylphosphino)acetylene, and 2,2'-bis(diphenylphosphino)diphenyl ether;

[0192] Examples of the urea-based curing accelerator include 1,1-dimethylurea; aliphatic dimethylureas such as 1,1,3-trimethylurea, 3-ethyl-1,1-dimethylurea, 3-cyclohexyl-1,1-dimethylurea, and 3-cyclooctyl-1,1-dimethylurea; 3-phenyl-1,1-dimethylurea, 3-(4-chlorophenyl)-1,1-dimethylurea, 3-(3,4-dichlorophenyl)-1,1-dimethylurea, 3-(3-chloro-4-methylphenyl)-1,1-dimethylurea, 3-(2-methylphenyl)-1,1-dimethylurea, 3-(4-methylphenyl)-1,1-dimethylurea, and 3-(3,4-dimethylphenyl)-1,1-dimethylurea. aromatic dimethylureas such as toluene bis(dimethylurea), 3-(4-isopropylphenyl)-1,1-dimethylurea, 3-(4-methoxyphenyl)-1,1-dimethylurea, 3-(4-nitrophenyl)-1,1-dimethylurea, 3-[4-(4-methoxyphenoxy)phenyl]-1,1-dimethylurea, 3-[4-(4-chlorophenoxy)phenyl]-1,1-dimethylurea, 3-[3-(trifluoromethyl)phenyl]-1,1-dimethylurea, N,N-(1,4-phenylene)bis(N',N'-dimethylurea), and N,N-(4-methyl-1,3-phenylene)bis(N',N'-dimethylurea) [toluene bisdimethylurea].

[0193] Examples of guanidine curing accelerators include dicyandiamide, 1-methylguanidine, 1-ethylguanidine, 1-cyclohexylguanidine, 1-phenylguanidine, 1-(o-tolyl)guanidine, dimethylguanidine, diphenylguanidine, trimethylguanidine, tetramethylguanidine, pentamethylguanidine, 1,5,7-triazabicyclo[4.4.0]dec-5-ene, 7-methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene, 1-methylbiguanide, 1-ethylbiguanide, 1-n-butylbiguanide, 1-n-octadecylbiguanide, 1,1-dimethylbiguanide, 1,1-diethylbiguanide, 1-cyclohexylbiguanide, 1-allylbiguanide, 1-phenylbiguanide, and 1-(o-tolyl)biguanide.

[0194] Examples of the imidazole curing accelerator include 2-methylimidazole, 2-undecylimidazole, 2-heptadecylimidazole, 1,2-dimethylimidazole, 2-ethyl-4-methylimidazole, 1,2-dimethylimidazole, 2-ethyl-4-methylimidazole, 2-phenylimidazole, 2-phenyl-4-methylimidazole, 1-benzyl-2-methylimidazole, and 1-benzyl-2-methylimidazole. Phenylimidazole, 1-cyanoethyl-2-methylimidazole, 1-cyanoethyl-2-undecylimidazole, 1-cyanoethyl-2-ethyl-4-methylimidazole, 1-cyanoethyl-2-phenylimidazole, 1-cyanoethyl-2-undecylimidazole, 1-cyanoethyl-2-phenylimidazolium trimellitate, 1-cyanoethyl-2-phenylimidazolium trimellitate, 2,4-diamino-6-[2'-methylimidazolyl -(1')]-ethyl-s-triazine, 2,4-diamino-6-[2'-undecylimidazolyl-(1')]-ethyl-s-triazine, 2,4-diamino-6-[2'-ethyl-4'-methylimidazolyl-(1')]-ethyl-s-triazine, 2,4-diamino-6-[2'-methylimidazolyl-(1')]-ethyl-s-triazine isocyanuric acid adduct, 2-phenylimidazole isocyanuric acid adduct Examples of imidazole compounds include 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, and 2-phenylimidazoline, as well as adducts of imidazole compounds with epoxy resins. Commercially available imidazole curing accelerators include "1B2PZ," "2E4MZ," "2MZA-PW," "2MZ-OK," "2MA-OK," "2MA-OK-PW," "2PHZ," "2PHZ-PW," "Cl1Z," "Cl1Z-CN," "Cl1Z-CNS," and "C11Z-A" manufactured by Shikoku Chemicals Corporation; and "P200-H50" manufactured by Mitsubishi Chemical Corporation.

[0195] Examples of metal-based curing accelerators include organometallic complexes or organometallic salts of metals such as cobalt, copper, zinc, iron, nickel, manganese, and tin. Specific examples of organometallic complexes include organic cobalt complexes such as cobalt(II) acetylacetonate and cobalt(III) acetylacetonate, organic copper complexes such as copper(II) acetylacetonate, organic zinc complexes such as zinc(II) acetylacetonate, organic iron complexes such as iron(III) acetylacetonate, organic nickel complexes such as nickel(II) acetylacetonate, and organic manganese complexes such as manganese(II) acetylacetonate. Examples of organometallic salts include zinc octoate, tin octoate, zinc naphthenate, cobalt naphthenate, tin stearate, and zinc stearate.

[0196] Examples of the amine curing accelerator include trialkylamines such as triethylamine and tributylamine, 4-dimethylaminopyridine, benzyldimethylamine, 2,4,6-tris(dimethylaminomethyl)phenol, 1,8-diazabicyclo(5,4,0)-undecene, etc. Commercially available amine curing accelerators may be used, such as "MY-25" manufactured by Ajinomoto Fine-Techno Co., Inc.

[0197] The content of the (G) curing accelerator is preferably 0.01% by mass or more, more preferably 0.1% by mass or more, even more preferably 0.2% by mass or more, relative to 100% by mass of the non-volatile components in the resin composition, and is preferably 5% by mass or less, more preferably 2% by mass or less, even more preferably 1% by mass or less.

[0198] The content of the (G) curing accelerator is preferably 0.01% by mass or more, more preferably 0.1% by mass or more, and even more preferably 1% by mass or more, relative to 100% by mass of the resin component in the resin composition, and is preferably 10% by mass or less, more preferably 6% by mass or less, and even more preferably 3% by mass or less.

[0199] <(H) Optional Additives> The resin composition may further contain (H) an optional additive as an optional component. The optional additive (H) as component (H) does not include those corresponding to the above-mentioned components (A) to (G). Examples of the optional additive (H) include thermoplastic resins; organometallic compounds such as organocopper compounds, organozinc compounds, and organocobalt compounds; colorants such as phthalocyanine blue, phthalocyanine green, iodine green, diazo yellow, crystal violet, titanium oxide, and carbon black; polymerization inhibitors such as hydroquinone, catechol, pyrogallol, and phenothiazine; leveling agents such as silicone-based leveling agents and acrylic polymer-based leveling agents; thickeners such as bentone and montmorillonite; antifoaming agents such as silicone-based antifoaming agents, acrylic-based antifoaming agents, fluorine-based antifoaming agents, and vinyl resin-based antifoaming agents; ultraviolet absorbers such as benzotriazole-based ultraviolet absorbers; adhesion improvers such as urea silanes; triazole-based adhesion promoters, tetrazole-based adhesion promoters, and triazine-based adhesion promoters. Examples of the additives include adhesion promoters such as viscosity-imparting agents; antioxidants such as hindered phenol antioxidants; fluorescent brighteners such as stilbene derivatives; surfactants such as fluorine-based surfactants and silicone-based surfactants; flame retardants such as phosphorus-based flame retardants (e.g., phosphate ester compounds, phosphazene compounds, phosphinic acid compounds, and 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; and stabilizers such as borate-based stabilizers, titanate-based stabilizers, aluminate-based stabilizers, zirconate-based stabilizers, isocyanate-based stabilizers, carboxylic acid-based stabilizers, and carboxylic anhydride-based stabilizers. (H) Optional additives may be used singly or in combination of two or more.

[0200] <(I) Solvent> The resin composition may further contain (I) a solvent as an optional volatile component in addition to the nonvolatile components (A) to (H) described above. The (I) solvent is typically an organic solvent. Examples of organic solvents include ketone-based solvents such as acetone, methyl ethyl ketone (MEK), methyl isobutyl ketone, and cyclohexanone; ester-based solvents such as methyl acetate, ethyl acetate, butyl acetate, isobutyl acetate, isoamyl acetate, methyl propionate, ethyl propionate, and γ-butyrolactone; ether-based solvents such as tetrahydropyran, tetrahydrofuran, 1,4-dioxane, diethyl ether, diisopropyl ether, dibutyl ether, diphenyl ether, and anisole; alcohol-based solvents such as methanol, ethanol, propanol, butanol, and ethylene glycol; 2-ethoxyethyl acetate, propylene glycol monomethyl ether acetate, diethylene glycol monoethyl ether acetate, ethyl diglycol acetate, γ-butyrolactone, and methoxypropion. Examples of suitable solvents include ether ester solvents such as methyl lactate; ester alcohol solvents such as methyl lactate, ethyl lactate, and methyl 2-hydroxyisobutyrate; ether alcohol solvents such as 2-methoxypropanol, 2-methoxyethanol, 2-ethoxyethanol, propylene glycol monomethyl ether, and diethylene glycol monobutyl ether (butyl carbitol); amide solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, and N-methyl-2-pyrrolidone; sulfoxide solvents such as dimethyl sulfoxide; nitrile solvents such as acetonitrile and propionitrile; aliphatic hydrocarbon solvents such as hexane, cyclopentane, cyclohexane, and methylcyclohexane; and aromatic hydrocarbon solvents such as benzene, toluene, xylene, ethylbenzene, and trimethylbenzene. (I) The solvents may be used singly or in combination of two or more.

[0201] The amount of (I) solvent, relative to 100% by mass of all components in the resin composition, can be, for example, 60% by mass or less, 40% by mass or less, 30% by mass or less, 20% by mass or less, 15% by mass or less, or 10% by mass or less, or may be 0% by mass.

[0202] <Method of manufacturing resin composition> The resin composition can be produced, for example, by mixing components that can be contained in the resin composition. The above-mentioned components may be mixed in part or all at the same time, or may be mixed sequentially. In the process of mixing each component, the temperature may be appropriately set, and thus heating and / or cooling may be performed temporarily or throughout. Furthermore, stirring or shaking may be performed in the process of mixing each component.

[0203] <Physical properties and applications of resin compositions> The resin composition contains a combination of component (A), components (B-1) and (B-2) as components (B), and component (C), and therefore can provide a cured product with low dielectric properties and a low coefficient of linear thermal expansion, as well as high adhesion before and after the HAST test and a high glass transition temperature. Furthermore, the cured product can usually also have excellent smear removal properties.

[0204] A cured product obtained by thermally curing the resin composition at 190°C for 90 minutes exhibits the characteristic of a low dielectric constant. Therefore, the cured product provides an insulating layer with a low dielectric constant. The dielectric loss tangent is preferably 4 or less, more preferably 3.5 or less, and even more preferably 3.4 or less. There is no particular lower limit, but it can be 0.001 or more. The dielectric constant can be measured according to the method described in the examples below.

[0205] A cured product obtained by thermally curing the resin composition at 190°C for 90 minutes exhibits the characteristic of a low dielectric loss tangent. Therefore, the cured product provides an insulating layer with a low dielectric loss tangent. The dielectric loss tangent is preferably 0.003 or less, more preferably 0.0029 or less, and even more preferably 0.0028 or less. There is no particular lower limit, but it can be 0.00001 or more. The dielectric loss tangent can be measured according to the method described in the examples below.

[0206] A cured product obtained by thermally curing a resin composition at 100°C for 30 minutes and then at 170°C for 30 minutes exhibits excellent adhesion to copper foil before HAST testing. Therefore, the cured product provides an insulating layer that exhibits excellent adhesion (peel strength) to copper foil before HAST testing. The peel strength is preferably 0.4 kgf / cm or more, more preferably 0.5 kgf / cm or more, and even more preferably 0.6 kgf / cm or more. The upper limit of the peel strength may be 10 kgf / cm or less. The peel strength can be measured according to the method described in the Examples below.

[0207] A cured product obtained by thermally curing a resin composition at 100°C for 30 minutes and then at 170°C for 30 minutes exhibits excellent adhesion to copper foil after accelerated environmental testing (HAST). Therefore, the cured product provides an insulating layer that exhibits excellent adhesion (peel strength) to copper foil after HAST testing. The peel strength after HAST testing is preferably 0.2 kgf / cm or more, more preferably 0.3 kgf / cm or more, and even more preferably 0.35 kgf / cm or more. The upper limit of the peel strength after HAST testing may be 10 kgf / cm or less. The peel strength can be measured according to the method described in the Examples below.

[0208] A cured product obtained by thermally curing a resin composition at 190°C for 90 minutes exhibits the characteristic of a high glass transition temperature (Tg). Therefore, the cured product provides an insulating layer with a high glass transition temperature. The glass transition temperature is preferably 155°C or higher, more preferably 160°C or higher, and even more preferably 165°C or higher. There is no particular upper limit, but it can be 500°C or lower, for example. The glass transition temperature can be measured according to the method described in the examples below.

[0209] A cured product obtained by thermally curing the resin composition at 190°C for 90 minutes exhibits the characteristic of a low coefficient of linear thermal expansion (CTE). Thus, the cured product provides an insulating layer with a low coefficient of linear thermal expansion. The coefficient of linear thermal expansion is preferably 25 ppm / °C or less, more preferably 20 ppm / °C or less, and even more preferably 18 ppm / °C or less. There is no particular lower limit, but it can be 1 ppm / °C or more. The coefficient of linear thermal expansion can be measured according to the method described in the examples below.

[0210] A cured product obtained by thermally curing a resin composition at 130°C for 30 minutes and then at 170°C for 30 minutes can usually have excellent smear removability. For example, when an insulating layer is formed from the cured product by the method described in <Test 3. Evaluation test of smear removability> in the Examples below and the smear removability is evaluated, the maximum smear length can be reduced to less than 5 µm.

[0211] <Applications of resin composition> The resin composition according to this embodiment can be used to form an insulating layer, and is particularly preferably used to form an insulating layer for a circuit board. The resin composition may also be used to manufacture a resin sheet. Typically, an insulating layer is formed using this resin sheet. The resin composition may also be used for other purposes, such as solder resist, underfill material, die bonding material, hole filling resin, sealing resin, and component embedding resin.

[0212] [Resin sheet] The resin sheet of the present invention includes a support and a resin composition layer formed on the support from the resin composition of the present invention. The resin composition layer includes the above-described resin composition, and preferably includes only the above-described resin composition.

[0213] From the viewpoint of thinning, the thickness of the resin composition layer provided in the resin sheet is preferably 200 μm or less, more preferably 150 μm or less, and even more preferably 100 μm or less. The lower limit of the thickness of the resin composition layer can be, for example, 1 μm or more, 3 μm or more, 5 μm or more, etc.

[0214] Examples of the support include plastic film, metal foil, and release paper, with plastic film and metal foil being preferred.

[0215] When a film of a plastic material is used as the support, examples of the plastic material include polyesters such as polyethylene terephthalate (hereinafter sometimes abbreviated as "PET") and polyethylene naphthalate (hereinafter sometimes abbreviated as "PEN"), polycarbonate (hereinafter sometimes abbreviated as "PC"), acrylics such as polymethyl methacrylate (PMMA), cyclic polyolefins, triacetyl cellulose (TAC), polyether sulfide (PES), polyether ketone, polyimide, etc. Among these, polyethylene terephthalate and polyethylene naphthalate are preferred, with inexpensive polyethylene terephthalate being particularly preferred.

[0216] When a metal foil is used as the support, examples of the metal foil include copper foil and aluminum foil, with copper foil being preferred. The copper foil may be a foil made of a single metal, copper, or an alloy of copper and another metal (e.g., tin, chromium, silver, magnesium, nickel, zirconium, silicon, titanium, etc.).

[0217] The surface of the support that is to be bonded to the resin composition layer may be subjected to a surface treatment such as matte treatment, corona treatment, or antistatic treatment.

[0218] The support may be a support with a release layer, which has a release layer on the surface that bonds with the resin composition layer. Examples of the release agent used in the release layer of the support with a release layer include one or more release agents selected from the group consisting of alkyd-based release agents, polyolefin-based release agents, urethane-based release agents, and silicone-based release agents. Commercially available products may be used as the support with a release layer, including PET films having a release layer primarily composed of a silicone-based release agent or an alkyd resin-based release agent, such as "PET501010," "SK-1," "AL-5," and "AL-7" manufactured by Lintec Corporation; "Lumirror T60" manufactured by Toray Industries, Inc.; "Purex" manufactured by Teijin Limited; and "Uni-Peel" manufactured by Unitika Limited.

[0219] The thickness of the support is not particularly limited, but is preferably 1 μm or more, more preferably 5 μm or more, even more preferably 10 μm or more, and is preferably 75 μm or less, more preferably 60 μm or less, even more preferably 50 μm or less. When a support with a release layer is used, it is preferable that the thickness of the entire support with a release layer is within the above range.

[0220] The resin sheet may include any optional member as needed. For example, the resin sheet may include a protective film for protecting the resin composition layer. The protective film is usually provided on the surface of the resin composition layer that is not bonded to the support (i.e., the surface opposite to the support). The thickness of the protective film is not particularly limited, but is, for example, 1 μm to 40 μm. When the protective film is provided, adhesion of dust and scratches to the surface of the resin composition layer can be suppressed.

[0221] The resin sheet can be produced, for example, by a method including forming a resin composition layer on a support. Specifically, the resin sheet can be produced by applying a liquid (varnish-like) resin composition directly or by mixing a solvent and the resin composition to prepare a liquid (varnish-like) resin composition, applying the liquid (varnish-like) resin composition to a support, and then drying it as necessary to form a resin composition layer. The solvent may be the same as the (I) solvent described as a component of the resin composition.

[0222] The resin composition can be applied using a coating device such as a die coater. Drying can be performed by a drying method such as heating or hot air blowing. The drying conditions are not particularly limited, but drying is typically performed so that the solvent content in the resin composition layer is 10% by mass or less, preferably 5% by mass or less. Although this may vary depending on the boiling point of the solvent, for example, when a resin composition containing 30% by mass to 60% by mass of solvent is used, a resin composition layer can be formed by drying at 50°C to 150°C for 3 to 10 minutes.

[0223] The produced resin sheet can be stored by being wound up in a roll. When the resin sheet has a protective film, the resin sheet can usually be used by peeling off the protective film.

[0224] [Circuit board] A circuit board according to one embodiment of the present invention includes an insulating layer formed from the cured product of the resin composition described above. The insulating layer may include only the cured product of the resin composition. The thickness of the insulating layer is not particularly limited and may be, for example, in the same range as the thickness of the resin composition layer provided in the resin sheet. Furthermore, the insulating layer can usually have properties similar to those of the cured product of the resin composition described above.

[0225] Preferably, the circuit board includes an inner layer substrate and the insulating layer is provided on the inner layer substrate. The circuit board may also include a conductor layer. For example, the conductor layer may be provided on an insulating layer. An example of a preferred method for manufacturing a circuit board will be described below.

[0226] A preferred example of a method for manufacturing a circuit board includes the steps of: Step (I) of forming a resin composition layer on an inner layer substrate; a step (II) of curing the resin composition layer; Includes.

[0227] An "inner layer substrate" is a member that serves as the base material of a circuit board, and examples thereof include glass epoxy substrates, metal substrates, polyester substrates, polyimide substrates, BT resin substrates, and thermosetting polyphenylene ether substrates. The inner layer substrate may have a conductor layer on one or both sides. The conductor layer of the inner layer substrate may be patterned. An inner layer substrate having a conductor layer (circuit) formed on one or both sides of the substrate is sometimes called an "inner layer circuit board." The term "inner layer substrate" also includes intermediate products on which insulating layers and / or conductor layers are to be further formed during the production of a circuit board. In addition, inner layer substrates with built-in components may also be used.

[0228] The resin composition layer may be formed on the inner layer substrate by, for example, a method including applying a resin composition to the inner layer substrate and drying it as necessary, but is preferably formed using a resin sheet. The method for forming a resin composition layer using a resin sheet typically includes laminating the resin sheet and the inner layer substrate. The resin sheet and the inner layer substrate are laminated so that the resin composition layer of the resin sheet and the inner layer substrate are bonded. This lamination may be performed, for example, by thermocompression bonding the resin sheet to the inner layer substrate from the support side. Examples of a member for thermocompression bonding the resin sheet to the inner layer substrate (hereinafter also referred to as a "thermocompression bonding member") include a heated metal plate (such as a SUS panel) or a metal roll (such as a SUS roll). It is preferable to press the thermocompression bonding member not directly against the resin sheet but through an elastic material such as heat-resistant rubber so that the resin sheet can sufficiently conform to the surface irregularities of the inner layer substrate.

[0229] The lamination of the inner layer substrate and the resin sheet may be carried out by a vacuum lamination method. In the vacuum lamination method, the thermocompression temperature is preferably in the range of 60°C to 160°C, more preferably 80°C to 140°C, the thermocompression pressure is preferably in the range of 0.098MPa to 1.77MPa, more preferably 0.29MPa to 1.47MPa, and the thermocompression time is preferably in the range of 20 seconds to 400 seconds, more preferably 30 seconds to 300 seconds. The lamination is preferably carried out under reduced pressure conditions of 26.7hPa or less.

[0230] The lamination may be performed using a commercially available vacuum laminator, such as a vacuum pressure laminator manufactured by Meiki Seisakusho Co., Ltd., a vacuum applicator manufactured by Nikko Materials Co., Ltd., or a batch-type vacuum pressure laminator.

[0231] The method for manufacturing a circuit board may include smoothing the resin sheet after lamination under normal pressure (atmospheric pressure), for example, by pressing the resin sheet from the support side with a thermocompression member. The pressing conditions for the smoothing may be the same as those for the thermocompression bonding of the lamination. The smoothing may be performed using a commercially available laminator. The lamination and smoothing may be performed consecutively using the commercially available vacuum laminator.

[0232] The method for producing a circuit board according to this example includes a step (II) of curing the resin composition layer after the step (I). By curing the resin composition layer in the step (II), an insulating layer containing a cured product of the resin composition can be formed.

[0233] The resin composition layer is usually cured by thermal curing. The thermal curing conditions for the resin composition layer may vary depending on the type of resin composition. For example, the curing temperature is preferably 120°C to 240°C, more preferably 150°C to 220°C, and even more preferably 170°C to 210°C. The curing time is preferably 5 minutes to 120 minutes, more preferably 10 minutes to 100 minutes, and even more preferably 15 minutes to 100 minutes.

[0234] The method for producing a circuit board may include preheating the resin composition layer at a temperature lower than the curing temperature before thermally curing the resin composition layer. For example, prior to thermally curing the resin composition layer, the resin composition layer may be preheated for typically 5 minutes or more, preferably 5 minutes to 150 minutes, more preferably 15 minutes to 120 minutes, and even more preferably 15 minutes to 100 minutes, at a temperature of typically 50°C to 150°C, preferably 60°C to 140°C, and more preferably 70°C to 130°C. Preheating is typically carried out after step (I). Furthermore, when a smoothing treatment is carried out after laminating the inner layer substrate and the resin sheet, preheating can typically be carried out after the smoothing treatment.

[0235] When a resin sheet is used, the method for producing a circuit board may include a step of peeling off the support of the resin sheet after laminating the inner layer substrate and the resin sheet. The peeling off of the support may be performed between steps (I) and (II), or after step (II). Furthermore, when the method for producing a circuit board includes step (III) of forming holes in the insulating layer, step (IV) of roughening the insulating layer, and step (V) of forming a conductor layer, as described below, the peeling off of the support may be performed between steps (II) and (III), between steps (III) and (IV), or between steps (IV) and (V).

[0236] The method for producing a circuit board may include, after step (II), step (III) of forming holes such as via holes or through holes in the insulating layer. The method for forming the holes may be selected depending on factors such as the composition of the resin composition used to form the insulating layer. For example, holes may be formed by processing methods such as drilling, laser processing, and plasma processing, with laser processing being preferred. For example, holes may be formed by irradiating the insulating layer with laser light after peeling off the support, or by irradiating the insulating layer with laser light through the support. The dimensions and shape of the holes may be determined appropriately depending on the design of the circuit board.

[0237] The method for manufacturing a circuit board may include a step (IV) of roughening the insulating layer. The roughening treatment can roughen the surface of the insulating layer. The roughening treatment can also remove smears (resin residues) from the insulating layer. Therefore, this roughening treatment is sometimes called a "desmear treatment." For example, when holes are formed in step (III), smears may form in the holes. Therefore, it is preferable to perform the roughening treatment of step (IV) after step (III) to remove the smears.

[0238] The procedure and conditions for the roughening treatment are not particularly limited, and known procedures and conditions that are commonly used when forming an insulating layer for a circuit board can be adopted. For example, the roughening treatment may be performed by subjecting the insulating layer to a swelling treatment using a swelling liquid, an oxidation treatment using an oxidizing agent, and a neutralization treatment using a neutralizing liquid in this order.

[0239] Examples of swelling liquids used in the roughening treatment include alkaline solutions and surfactant solutions, with alkaline solutions being preferred. Sodium hydroxide solutions and potassium hydroxide solutions are more preferred as alkaline solutions. Commercially available swelling liquids include "Swelling Dip Securiganth P" and "Swelling Dip Securiganth SBU" manufactured by Atotech Japan. Swelling treatment using a swelling liquid can be performed, for example, by immersing the insulating layer in a swelling liquid at 30°C to 90°C for 1 to 20 minutes. To keep the swelling of the resin in the insulating layer to an appropriate level, it is preferable to immerse the insulating layer in a swelling liquid at 40°C to 80°C for 5 to 15 minutes.

[0240] Examples of oxidizing agents used in the roughening treatment include alkaline permanganate solutions prepared by dissolving potassium permanganate or sodium permanganate in an aqueous solution of sodium hydroxide. Oxidation treatment using an oxidizing agent such as alkaline permanganate solution is preferably carried out by immersing the insulating layer in an oxidizing agent solution heated to 60°C to 100°C for 10 to 30 minutes. The concentration of permanganate in the alkaline permanganate solution is preferably 5% by mass to 10% by mass. Commercially available oxidizing agents include alkaline permanganate solutions such as "Concentrate Compact CP" and "Dosing Solution Securigance P" manufactured by Atotech Japan.

[0241] The neutralizing solution used in the roughening treatment is preferably an acidic aqueous solution, and a commercially available product such as "Reduction Solution Securigant P" manufactured by Atotech Japan can be cited as an example. Neutralization treatment using a neutralizing solution can be carried out by immersing the surface that has been oxidized with an oxidizing agent in a neutralizing solution at 30°C to 80°C for 5 to 30 minutes. From the standpoint of workability, a preferred method is to immerse the object that has been oxidized with an oxidizing agent in a neutralizing solution at 40°C to 70°C for 5 to 20 minutes.

[0242] The method for producing a circuit board may include step (V) of forming a conductor layer on the insulating layer. When the method for producing a circuit board includes step (III) or (IV), step (V) of forming a conductor layer is usually preferably carried out after steps (III) and (IV).

[0243] The conductive material used for the conductor layer is not particularly limited. In a preferred embodiment, the conductor layer contains one or more metals selected from the group consisting of gold, platinum, palladium, silver, copper, aluminum, cobalt, chromium, zinc, nickel, titanium, tungsten, iron, tin, and indium. The conductor layer may be a single metal layer or an alloy layer. Examples of alloy layers include layers formed from an alloy of two or more metals selected from the above group (e.g., nickel-chromium alloy, copper-nickel alloy, and copper-titanium alloy). Among these, from the viewpoints of versatility in forming the conductor layer, cost, ease of patterning, etc., single metal layers of chromium, nickel, titanium, aluminum, zinc, gold, palladium, silver, or copper, or alloy layers of nickel-chromium alloy, copper-nickel alloy, or copper-titanium alloy are preferred. Single metal layers of chromium, nickel, titanium, aluminum, zinc, gold, palladium, silver, or copper, or alloy layers of nickel-chromium alloy are more preferred, and single metal layers of copper are even more preferred.

[0244] The conductor layer may have a single layer structure or a multi-layer structure including two or more single metal or alloy layers made of different types of metals or alloys. When the conductor layer has a multi-layer structure, the layer in contact with the insulating layer is preferably a single metal layer of chromium, zinc, or titanium, or an alloy layer of a nickel-chromium alloy.

[0245] The thickness of the conductor layer depends on the design of the circuit board, but is preferably 3 μm to 35 μm, and more preferably 5 μm to 30 μm.

[0246] The conductor layer may be formed by plating. For example, a conductor layer having a desired wiring pattern can be formed by plating the surface of the insulating layer using a conventionally known technique such as a semi-additive method or a full-additive method. From the viewpoint of ease of production, the semi-additive method is preferred. An example of forming a conductor layer by a semi-additive method will be described below.

[0247] First, an electroless plated layer (plating seed layer) is formed on the surface of the insulating layer by electroless plating. Next, a mask pattern is formed on the formed electroless plated layer, exposing a portion of the electroless plated layer corresponding to the desired wiring pattern. After forming an electroless plated layer on the exposed electroless plated layer by electrolytic plating, the mask pattern is removed. Thereafter, unnecessary electroless plated layer is removed by etching, thereby forming a conductor layer having the desired wiring pattern.

[0248] As another example, the conductor layer may be formed using a metal foil. When a metal foil is used to form the conductor layer, step (V) is preferably performed between steps (I) and (II). For example, after step (I), the support is removed, and a metal foil is laminated on the exposed surface of the resin composition layer. The lamination of the resin composition layer and the metal foil may be performed by a vacuum lamination method. The lamination conditions may be the same as those described for step (I). Next, step (II) is performed to form an insulating layer. Thereafter, a conductor layer having a desired wiring pattern can be formed using the metal foil on the insulating layer by a known technique such as a subtractive method or a modified semi-additive method. The metal foil can be manufactured by a known method such as an electrolytic method or a rolling method. Commercially available metal foils include, for example, HLP foil and JXUT-III foil manufactured by JX Nippon Mining & Smelting Co., Ltd., and 3EC-III foil and TP-III foil manufactured by Mitsui Mining & Smelting Co., Ltd.

[0249] When a conductor layer is formed on an insulating layer, the method for manufacturing a circuit board may include performing an annealing treatment after the formation of the conductor layer. The annealing treatment can improve the adhesion between the insulating layer and the conductor layer. The annealing treatment can be performed, for example, by heating at 150°C to 210°C for 20 to 180 minutes.

[0250] In the method for manufacturing a circuit board, each of the above steps may be performed only once or may be repeated two or more times. For example, steps (I) to (V) may be performed repeatedly to form a circuit board having a multilayer structure, such as a multilayer printed wiring board having a plurality of insulating layers and conductor layers.

[0251] The method for manufacturing a circuit board may include any additional steps in addition to the steps described above. For example, the method for manufacturing a circuit board may include a step of providing a semiconductor chip so that the semiconductor chip is bonded to the conductor layer. Specifically, when manufacturing a circuit board for a semiconductor chip package including a semiconductor chip, the method for manufacturing a circuit board may include a step of providing the semiconductor chip. The semiconductor chip may be bonded under appropriate conditions that allow conductive connection between the terminal electrodes of the semiconductor chip and the conductor layer formed on the insulating layer. For example, conditions used in flip-chip mounting may be used. The semiconductor chip may be bonded via an insulating adhesive or by reflow bonding. If necessary, the provided semiconductor chip may be filled with a mold underfill material. The method for manufacturing a circuit board may also include, for example, a step of forming a sealing layer, a step of forming a solder resist layer, and a step of dicing the manufactured circuit board into individual pieces.

[0252] Examples of circuit boards include printed wiring boards and semiconductor chip packages. Examples of semiconductor chip packages include FC-CSP, MIS-BGA package, ETS-BGA package, fan-out type WLP (Wafer Level Package), fan-in type WLP, fan-out type PLP (Panel Level Package), and fan-in type PLP. In these semiconductor chip packages, it is preferable to form a rewiring formation layer as an insulating layer using a cured product obtained by curing the above-mentioned resin composition. However, the circuit board is not limited to those exemplified here.

[0253] [Semiconductor Devices] The circuit board can be used to manufacture a semiconductor device. The semiconductor device includes the circuit board described above. Examples of the semiconductor device include various semiconductor devices used in electrical appliances (e.g., computers, mobile phones, smartphones, tablet devices, wearable devices, digital cameras, medical equipment, and televisions) and vehicles (e.g., motorcycles, automobiles, trains, ships, and aircraft). [Example]

[0254] The present invention will be specifically described below with reference to examples. However, the present invention is not limited to these examples. In the following description, "parts" and "%" representing amounts mean "parts by mass" and "% by mass", respectively, unless otherwise specified. Furthermore, unless otherwise specified, the temperature and pressure conditions were room temperature (23°C) and atmospheric pressure (1 atm). In the following description, "Mw" represents weight-average molecular weight, and "Mn" represents number-average molecular weight, unless otherwise specified.

[0255] <Synthesis Example 1: Synthesis of Active Ester Resin 1> A flask equipped with a thermometer, dropping funnel, condenser, distillation column, and stirrer was charged with 320 g (2.0 mol) of 2,7-dihydroxynaphthalene, 184 g (1.7 mol) of benzyl alcohol, and 5.0 g of paratoluenesulfonic acid monohydrate. The mixture was stirred at room temperature while blowing in nitrogen. The temperature was then raised to 150 °C and the mixture was stirred for 4 hours while distilling off the resulting water. After the reaction was complete, 900 g of methyl isobutyl ketone and 5.4 g of 20% aqueous sodium hydroxide solution were added to neutralize the mixture. The aqueous layer was then removed by separation, washed three times with 280 g of water, and the methyl isobutyl ketone was removed under reduced pressure to obtain 460 g of benzyl-modified naphthalene compound (A'). The resulting benzyl-modified naphthalene compound (A') was a black solid with a hydroxyl equivalent of 180 g / eq.

[0256] A flask equipped with a thermometer, dropping funnel, condenser, distillation column, and stirrer was charged with 203.0 g of isophthalic acid chloride (molar number of acid chloride groups: 2.0 mol) and 1,400 g of toluene. The system was then purged with nitrogen under reduced pressure and dissolved. Next, 72.4 g (0.67 mol) of orthocresol and 240 g of benzyl-modified naphthalene compound (A') (molar number of phenolic hydroxyl groups: 1.33 mol) were charged and the system was then purged with nitrogen under reduced pressure and dissolved. Next, 0.70 g of tetrabutylammonium bromide was dissolved. While purging with nitrogen gas, the system was maintained at 60°C or below, and 400 g of 20% aqueous sodium hydroxide solution was added dropwise over 3 hours. The reaction was then allowed to proceed under these conditions with stirring for 1 hour.

[0257] After the reaction was completed, the mixture was allowed to stand for liquid separation and the aqueous layer was removed. Furthermore, water was added to the toluene layer in which the reactant was dissolved, and the mixture was stirred and mixed for 15 minutes, after which the mixture was allowed to stand for liquid separation and the aqueous layer was removed. This procedure was repeated until the pH of the aqueous layer reached 7. The water was then removed by decanting, yielding active ester resin 1 in the form of a toluene solution with a non-volatile content of 65% by mass. The active ester group equivalent of the obtained active ester resin 1 was 238 g / eq.

[0258] <Synthesis Example 2: Synthesis of Active Ester Resin 2> A flask equipped with a thermometer, dropping funnel, condenser, distillation column, and stirrer was charged with 165 g of a polyaddition resin (hydroxyl equivalent: 165 g / eq., softening point: 85°C) of dicyclopentadiene and phenol, 134 g (1.0 mol) of ortho-allylphenol, and 1200 g of toluene. The system was then purged with nitrogen under reduced pressure. Next, 203 g (1.0 mol) of isophthalic acid chloride was added, and the system was purged with nitrogen under reduced pressure. 0.6 g of tetrabutylammonium bromide was added, and while purging with nitrogen gas, the system was maintained at 60°C or below. 412 g of 20% aqueous sodium hydroxide solution was added dropwise over 3 hours. After the addition, the mixture was stirred for 1.0 hour. After the reaction was complete, the aqueous layer was removed by static separation. Water was added to the resulting toluene layer and stirred for 15 minutes. The aqueous layer was then removed by static separation. This procedure was repeated until the pH of the aqueous layer reached 7. The nonvolatile components were then adjusted to 70% by mass by heat drying to obtain active ester resin 2 represented by the following formula (mainly composed of compounds where S = an integer of 0 to 6 and r = an integer of 0 to 6). The active ester group equivalent of the obtained active ester resin 2 was 214 g / eq. [ka]

[0259] <Synthesis Example 3: Synthesis of Maleimide Resin D> According to Synthesis Example 1 in Japan Institute of Invention and Innovation Disclosure Technical Bulletin No. 2020-500211, an MEK solution (62% by mass of non-volatile components) of maleimide resin D represented by the following formula (1) was prepared. The Mw / Mn of this maleimide resin D was 1.81, and t'' in formula (1) was 1.47 (mainly 1, 2, or 3). [ka]

[0260] <Synthesis Example 4: Synthesis of vinyl resin D-1> According to Example 1 of WO 2017 / 115813, 3.0 moles (390.6 g) of divinylbenzene, 1.8 moles (229.4 g) of ethylvinylbenzene, 10.2 moles (1066.3 g) of styrene, and 15.0 moles (1532.0 g) of n-propyl acetate were charged into a 5.0 L reactor, and 600 mmol of boron trifluoride diethyl ether complex was added at 70 °C. The reaction was allowed to proceed for 4 hours. The polymerization solution was terminated with aqueous sodium bicarbonate solution. The oil layer was then washed three times with pure water, and the polymer was recovered by devolatilization under reduced pressure at 60 °C. The resulting polymer was weighed, and it was confirmed that 896.7 g of vinyl resin D-1 was obtained as the polymer. The weight-average molecular weight Mw of vinyl resin D-1 was 41,300.

[0261] <Examples 1 to 12 and Comparative Examples 1 to 3> (1) Preparation of resin composition: Each component was weighed and mixed according to the formulation shown in the table below, and then 10 parts of MEK and 10 parts of cyclohexanone were added and uniformly dispersed using a high-speed rotary mixer to obtain a resin composition (resin varnish). Note that the formulation shown in the table below indicates the amount (parts by mass) of nonvolatile components. [Table 1]

[0262] Details of each component listed in the table are as follows: (A) Epoxy resin: HP-4032-SS: Epoxy equivalent weight 144g / eq., manufactured by DIC, naphthalene-type epoxy resin. NC-3000L: Epoxy equivalent 270g / eq., manufactured by Nippon Kayaku Co., Ltd., biphenyl type epoxy resin. (B-1) Ingredients: Active ester resin 5: A toluene solution of a compound represented by the following formula (mainly consisting of compounds where n is an integer of 0 to 6), active ester group equivalent weight 250 g / eq., and nonvolatile content 62 mass %. [ka] (B-2-i) Ingredients: Active ester resin 2: an active ester resin having an active ester group equivalent of 214 g / eq., synthesized in Synthesis Example 2, and a toluene solution containing 70% by mass of nonvolatile components. Active ester resin 3: Active ester group equivalent weight 248 g / eq., compound represented by the following formula (mainly consisting of compounds where n is an integer from 0 to 6 and m is an integer from 0 to 6). Toluene solution with non-volatile content of 70 mass%. [ka] Active ester resin 4: Active ester group equivalent weight 1002 g / eq., manufactured by DIC Corporation, active ester resin represented by the following formula (mainly composed of compounds where m is an integer between 0 and 6, and n is an integer between 6 and 30). [ka] Component (B-2-ii): HPC-8000L-65MT: Active ester group equivalent weight 223 g / eq., toluene / MEK solution with 65% non-volatile content by mass, manufactured by DIC Corporation, active ester resin containing dicyclopentadiene-type diphenol structure. Active ester resin 1: Active ester group equivalent weight 238 g / eq., active ester resin synthesized in Synthesis Example 1. (C) Ingredients: SO-C2: Spherical silica surface-treated with an amino-silane coupling agent (Shin-Etsu Chemical Co., Ltd. "KBM573"), average particle size 0.5 μm, specific surface area 5.8 m 2 / g, manufactured by Admatechs Co., Ltd. (D) Ingredients: Maleimide resin D: Maleimide resin D synthesized in Synthesis Example 3. MIR-3000-70MT: Toluene-MEK solution with 70% by mass of non-volatile components, manufactured by Nippon Kayaku Co., Ltd., maleimide resin with the structure shown in the following formula (mainly consisting of compounds where n = 1 to 6). [ka] · SLK-6895: Aliphatic maleimide resin manufactured by Shin-Etsu Chemical Co., Ltd. SLK-1500: Aliphatic maleimide resin manufactured by Shin-Etsu Chemical Co., Ltd. OPE-2St-1200: Toluene solution with 65% non-volatile content, manufactured by Mitsubishi Gas Chemical Co., Ltd., a styrene-based radical polymerizable resin with a polyphenylene ether skeleton. Vinyl resin D-1: Vinyl resin D-1 synthesized in Synthesis Example 4. (E) Ingredients: LA-3018-50P: 1-methoxy-2-propanol solution with a phenolic hydroxyl group equivalent of 151 g / eq. and 50% non-volatile content by mass, manufactured by DIC Corporation, phenolic resin. (F) Ingredients: EXL-2655: Organic filler containing rubber components, manufactured by Dow. (G) Ingredients: 1B2PZ: Imidazole-based curing accelerator manufactured by Shikoku Chemicals Corporation.

[0263] (2) Production of resin sheet A: A polyethylene terephthalate film ("AL5" manufactured by Lintec Corporation, thickness 38 μm) with a release layer was prepared as a support. The obtained resin composition was uniformly applied onto the release layer of this support so that the thickness of the resin composition layer after drying would be 40 μm. The resin composition was then dried at 80°C to 100°C (average 90°C) for 4 minutes to obtain a resin sheet A having a layer structure of resin composition layer / support.

[0264] <Test 1. Measurement test of dielectric constant and dielectric loss tangent> Resin sheet A was heated in an oven at 190°C for 90 minutes to cure the resin composition layer. The support was then peeled off to obtain a cured resin composition layer. The cured product was cut into a length of 30 mm and a width of 40 mm to obtain a cured product sample for measuring dielectric properties.

[0265] The dielectric constant and dielectric loss tangent of the cured sample were measured by the split cylinder method using a measuring device (Agilent Technologies, "HP8362B") at a measurement frequency of 10 GHz and a measurement temperature of 90°C. Measurements were performed on two test pieces, and the average was calculated.

[0266] <Test 2. Measurement test of glass transition temperature (Tg) and coefficient of linear thermal expansion (CTE)> Resin sheet A was cured in an oven at 190°C for 90 minutes, and the support was then peeled off to obtain a cured film. This cured film was cut into a 20 mm long, 6 mm wide piece to obtain a cured sample for measuring the linear thermal expansion coefficient. The Tg and CTE of this cured sample were measured using a TMA device (thermomechanical analyzer, manufactured by Rigaku Corporation). Specifically, the cured sample was loaded into the device and subjected to two consecutive measurements under the following conditions: a load of 1 g and a heating rate of 5°C / min (the first measurement was performed by raising the temperature from 25°C to 220°C, and the second measurement was performed by raising the temperature from 25°C to 250°C). The second value was recorded.

[0267] <Test 3. Evaluation test of smear removal ability> (1) Preparation of inner layer board: Both sides of a glass cloth-based epoxy resin double-sided copper-clad laminate (copper foil thickness 18 μm, substrate thickness 0.4 mm, Panasonic "R1515A") with an inner layer circuit formed thereon were etched by 1 μm with a microetching agent (MEC "CZ8101") to roughen the copper surface, thereby obtaining an inner layer substrate.

[0268] (2) Lamination of resin sheet A: Using a batch-type vacuum pressure laminator (Nikko Materials Co., Ltd., two-stage build-up laminator "CVP700"), resin sheet A was laminated on both sides of the inner layer substrate so that the resin composition layer was in contact with the inner layer substrate. Lamination was performed by reducing the pressure for 30 seconds to adjust the air pressure to 13 hPa or less, followed by pressure bonding at 120°C and a pressure of 0.74 MPa for 30 seconds. The resin composition layer was then smoothed by heat pressing at 100°C and a pressure of 0.5 MPa for 60 seconds.

[0269] (3) Thermal curing of the resin composition layer: The inner layer substrate laminated with resin sheet A was then placed in an oven at 130°C and heated for 30 minutes, and then transferred to an oven at 170°C and heated for 30 minutes to thermally cure the resin composition layer and form an insulating layer. The support was then peeled off to obtain a cured substrate having a structure of insulating layer / inner layer substrate / insulating layer.

[0270] (4) Formation of via holes: The insulating layer of the obtained cured substrate was drilled using a CO2 laser processing machine ("LK-2K212 / 2C" manufactured by Via Mechanics) under the conditions of a frequency of 2000 Hz, a pulse width of 3 μs, an output of 0.95 W, and a shot count of 3 to form via holes. The opening diameter (diameter, top diameter) of the formed via hole on the surface of the insulating layer was 50 μm, and the diameter (bottom diameter) at the bottom of the insulating layer was 50 μm.

[0271] (5) Roughening treatment: The insulating layer of the cured substrate having the via holes formed therein was subjected to a desmear treatment as a roughening treatment, which was the following wet desmear treatment.

[0272] (wet desmear treatment) The cured substrate was immersed in a swelling solution (Atotech Japan's "Swelling Dip Securigant P," an aqueous solution of diethylene glycol monobutyl ether and sodium hydroxide) at 60°C for 10 minutes. The cured substrate was then immersed in an oxidizing solution (Atotech Japan's "Concentrate Compact P," an aqueous solution of approximately 6% potassium permanganate and 4% sodium hydroxide) at 80°C for 25 minutes. Finally, the cured substrate was immersed in a neutralizing solution (Atotech Japan's "Reduction Solution Securigant P," an aqueous sulfuric acid solution) at 40°C for 5 minutes. The cured substrate was then dried at 80°C for 15 minutes. The cured substrate after this desmearing process is hereinafter referred to as "Evaluation Substrate A."

[0273] (6) Evaluation of smear removal: The periphery of the bottom of the via hole of evaluation substrate A was observed with a scanning electron microscope (SEM). From the obtained image, the length of the longest smear (resin residue) extending from the wall surface of the bottom of the via hole (maximum smear length) was measured and evaluated according to the following criteria. ○: Maximum smear length is less than 5 μm. ×: Maximum smear length is 5 μm or more.

[0274] <Test Example 4: Measurement of adhesion between conductor layer before and after high temperature and high humidity environmental test (HAST)> (1) Laminating resin sheet A onto the inner layer substrate A glass cloth-based epoxy resin double-sided copper-clad laminate (copper foil thickness 18 μm, substrate thickness 0.8 mm, Panasonic "R1515A") was prepared as an inner layer substrate. The copper foil on this surface was roughened by etching using a microetching agent (MEC "CZ8101") to remove 1 μm of copper.

[0275] The resin sheet A obtained above was laminated onto both sides of the inner layer substrate using a batch-type vacuum pressure laminator (a two-stage build-up laminator "CVP700" manufactured by Nikko Materials Co., Ltd.) so that the resin composition layer of the resin sheet A was in contact with the inner layer substrate. The lamination was performed by reducing the pressure for 30 seconds to 13 hPa or less, and then pressing at a temperature of 100°C and a pressure of 0.74 MPa for 30 seconds.

[0276] The laminated resin sheet A was then heat-pressed at atmospheric pressure at 100°C under a pressure of 0.5 MPa for 60 seconds to smooth the surface. The support was then peeled off to obtain an "intermediate multilayer body I" comprising a resin composition layer / inner layer substrate / resin composition layer in this order.

[0277] (2) Copper foil lamination A copper foil (thickness: 35 μm, manufactured by Mitsui Mining & Smelting Co., Ltd., "3EC-III") having a shiny surface was prepared. The shiny surface of this copper foil was roughened by etching with a microetching agent (manufactured by MEC Co., Ltd., "CZ8101") to an etching amount of 1 μm. The copper foil obtained in this manner is referred to as "roughened copper foil."

[0278] This roughened copper foil was laminated on both sides of intermediate multilayer body I so that the roughened surface of the roughened copper foil was bonded to the resin composition layer of intermediate multilayer body I. This lamination was carried out under the same conditions as for laminating resin sheet A to the inner layer substrate described above. In this way, an "intermediate multilayer body II" containing roughened copper foil / resin composition layer / inner layer substrate / resin composition layer / roughened copper foil in this order was obtained.

[0279] (3) Thermal curing of the resin composition layer The obtained intermediate laminate II was placed in a 100 ° C. oven and heated for 30 minutes, then transferred to a 170 ° C. oven and heated for 30 minutes. Next, the intermediate laminate II was removed from the oven under room temperature atmosphere, and then placed in a 190 ° C. oven and heated for an additional 90 minutes. This resulted in thermal curing of the resin composition layer, and an "evaluation substrate C" was obtained, which included, in this order: roughened copper foil / insulating layer as a cured product of the resin composition layer / inner layer substrate / insulating layer as a cured product of the resin composition layer / roughened copper foil. In this evaluation substrate C, the roughened copper foil corresponds to the conductor layer.

[0280] (4) Measurement of adhesion strength with the conductor layer The peel strength between the roughened copper foil and the insulating layer was measured using the obtained evaluation substrate C. This peel strength measurement was performed in accordance with JIS C6481. Specifically, the peel strength measurement was performed by the following procedure.

[0281] A slit was made in the roughened copper foil of evaluation substrate C, surrounding a rectangular area 10 mm wide and 100 mm long. One end of this rectangular area was peeled off and gripped with a gripping tool (TSE Autocom type testing machine "AC-50C-SL"). A 35 mm long area of ​​this rectangular area was peeled off vertically, and the load (kgf / cm) at the time of peeling was measured as the peel strength. The peeling was performed at room temperature at a rate of 50 mm / min.

[0282] Furthermore, an environmental test (HAST test) was carried out for 100 hours under conditions of 130°C and 85% RH, and then the peel strength was measured in the same manner as above.

[0283] [Table 2]

Claims

1. (A) an epoxy resin, (B) an active ester compound, and (C) an inorganic filler, A resin composition in which the component (B) comprises (B-1) an active ester compound represented by the following formula (B-1a), and (B-2) an active ester compound other than the component (B-1): 【Chemistry 1】 In the formula, R １１ each independently represents a monovalent aromatic group which may have a substituent, R １２ each independently represents a divalent aromatic group which may have a substituent, R １３ each independently represents a divalent aromatic group having a fused ring structure, which may have a substituent; R １４ each independently represents a divalent hydrocarbon group which may have a substituent, and n1 represents an integer of 0 or greater.

2. 2. The resin composition according to claim 1, wherein the component (B-2) includes (B-2-i) an active ester compound containing a carbon-carbon double bond.

3. The resin composition according to claim 1, wherein the component (B-2-i) contains any one of an active ester compound represented by formula (B-i), an active ester compound represented by formula (B-ii), and an active ester compound represented by formula (B-iii). 【Chemistry 2】 In formula (B-i), Ar １１ each independently represents a monovalent aromatic group which may have a substituent, Ar １２ each independently represents a divalent aromatic group which may have a substituent, Ar １３ each independently represents a divalent aromatic group which may have a substituent, a divalent aliphatic group which may have a substituent, an oxygen atom, a sulfur atom, or a divalent group consisting of a combination thereof. mi and ni each independently represent an integer of 0 or more. １１ , Ar １２ , and Ar １３ At least one of has a substituent containing a carbon-carbon double bond. In formula (B-ii), Ar １１ each independently represents a monovalent aromatic group which may have a substituent, Ar １２ each independently represents a divalent aromatic group which may have a substituent, Ar １３ each independently represents a divalent aromatic group which may have a substituent, a divalent aliphatic group which may have a substituent, an oxygen atom, a sulfur atom, or a divalent group consisting of a combination thereof. mii and nii each independently represent an integer of 0 or more. １１ , Ar １２ , and Ar １３ At least one of has a substituent containing a carbon-carbon double bond. In formula (B-iii), Ar １ each independently represents a monovalent aromatic group which may have a substituent, Ar ２ each independently represents a divalent aromatic group which may have a substituent, R １ each independently represents a divalent aliphatic group which may have a substituent, R ２ each independently represents a butadiene structure, m and n each independently represent an integer greater than 0.

4. The resin composition according to claim 1, wherein the component (B-2) includes (B-2-ii) an active ester compound that does not contain a carbon-carbon double bond.

5. The resin composition according to claim 1 , further comprising (D) a radically polymerizable compound.

6. The resin composition according to claim 5 , wherein the component (D) comprises a maleimide resin.

7. The resin composition according to claim 1 , further comprising (E) another curing agent.

8. 2. The resin composition according to claim 1, wherein the content of the component (B-1) is 20% by mass or more and 90% by mass or less, when the entire component (B) is taken as 100% by mass.

9. In formula (B-1a), R １４ The resin composition according to claim 1 , wherein represents a divalent group formed by combining a divalent aromatic group and a divalent aliphatic group.

10. A resin sheet comprising a support and a resin composition layer provided on the support, the resin composition comprising the resin composition according to any one of claims 1 to 9.

11. A circuit board comprising an insulating layer formed from a cured product of the resin composition according to any one of claims 1 to 9.

12. A semiconductor device comprising the circuit board according to claim 11.

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