Resin composition

Abstract

The present invention addresses the problem of providing a resin composition and the like capable of forming a cured product having low dielectric properties and linear thermal expansion coefficient, and also having high adhesion and glass transition temperature before and after a HAST test. [Solution] A resin composition containing (A) an epoxy resin, (B) an active ester compound, and (C) an inorganic filler, the component (B) containing (B-1) an active ester compound represented by formula (B-1a) and (B-2) an active ester compound other than the component (B-1).

Description

Technical Field

[0001] This invention relates to resin compositions, resin sheets, circuit boards, and semiconductor devices. Background Technology

[0002] Printed wiring boards and other circuit boards are widely used in various electronic devices. As a method for manufacturing circuit boards, a method is known in which insulating layers and conductor layers are alternately stacked on an inner layer substrate. The insulating layer is, for example, formed from a cured resin composition (Patent Documents 1 and 2). Specifically, by forming a resin composition layer containing a resin composition and then curing that resin composition layer, an insulating layer containing a cured resin composition is formed.

[0003] Existing technical documents Patent documents Patent Document 1: Japanese Patent Application Publication No. 2022-100697 Patent Document 2: Japanese Patent Application Publication No. 2023-037522 Summary of the Invention

[0004] The technical problem to be solved by the invention In recent years, there have been increasing demands on resin compositions that can form insulating layers with low relative permittivity and dielectric loss tangent, excellent adhesion to the conductor layer before and after HAST (High Accelerated Stress Test) testing, high glass transition temperature (Tg), and low coefficient of linear thermal expansion (CTE). Sometimes, relative permittivity and dielectric loss tangent are collectively referred to as dielectric properties.

[0005] The present invention was made in view of the above-mentioned problems, and its object is to provide: a resin composition capable of forming a cured product with low dielectric properties and low coefficient of linear thermal expansion, and high adhesion and glass transition temperature before and after HAST test; 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 containing the circuit board.

[0006] Methods for solving technical problems The inventors conducted in-depth research on the above-mentioned problems and found that by including (A) epoxy resin, (B) active ester compound and (C) inorganic filler material, and including the active ester compound shown in formula (B-1a) and other active ester compounds as component (B), the above-mentioned problems can be solved, and the present invention is thus completed.

[0007] That is, the present invention includes the following contents. [1] A resin composition comprising: (A) Epoxy resin, (B) Active ester compounds, and (C) Inorganic filler materials (B) The ingredient comprises: (B-1) an active ester compound represented by formula (B-1a) below, and (B-2) an active ester compound other than the ingredient (B-1). [Chemical Formula 1] In the formula, R 11 Each of these can be independently represented as a monovalent aromatic group with optional substituents. R 12 Each of the following can be independently represented as a divalent aromatic group with optional substituents: R 13 Each of these can be independently represented as a divalent aromatic group with a fused ring structure, optionally having a substituent. R 14 Each can be independently represented as a divalent hydrocarbon group with optional substituents. n1 represents an integer greater than or equal to 0. [2] The resin composition according to [1], wherein the (B-2) component comprises (B-2-i) an active ester compound containing a carbon-carbon double bond. [3] The resin composition according to [1] or [2], wherein the (B-2-i) component comprises any one of the active ester compound of formula (Bi), the active ester compound of formula (B-ii), and the active ester compound of formula (B-iii). [Chemical Formula 2] In formula (Bi), Ar 11 Each of these can be independently represented as a monovalent aromatic group with optional substituents. Ar 12 Each of the following can be independently represented as a divalent aromatic group with optional substituents: Ar 13 Each of these can be independently represented as an optional divalent aromatic group with substituents, an optional divalent aliphatic group with substituents, an oxygen atom, a sulfur atom, or a divalent group composed of combinations thereof. mi and ni represent integers greater than 0 independently. Among them, Ar 11 Ar 12 and Ar 13 At least one of them has a substituent containing a carbon-carbon double bond; In equation (B-ii), Ar 11 Each of these can be independently represented as a monovalent aromatic group with optional substituents. Ar 12 Each of the following can be independently represented as a divalent aromatic group with optional substituents: Ar 13 Each of these can be independently represented as an optional divalent aromatic group with substituents, an optional divalent aliphatic group with substituents, an oxygen atom, a sulfur atom, or a divalent group composed of combinations thereof. mii and nii independently represent integers greater than 0. Among them, Ar 11 Ar 12 and Ar 13 At least one of them has a substituent containing a carbon-carbon double bond; In equation (B-iii), Ar 1 Each of these can be independently represented as a monovalent aromatic group with optional substituents. Ar 2 Each of the following can be independently represented as a divalent aromatic group with optional substituents: R 1 Each of these can be independently represented as a divalent aliphatic group with optional substituents. R 2 The butadiene structure is represented independently. m and n each represent an integer greater than 0 independently. [4] The resin composition according to any one of [1] to [3], wherein the (B-2) component comprises (B-2-ii) an active ester compound that does not contain carbon-carbon double bonds. [5] The resin composition according to any one of [1] to [4], wherein it further comprises (D) a free radical polymerizable compound. [6] The resin composition according to [5], wherein component (D) comprises maleimide resin. [7] The resin composition according to any one of [1] to [6], wherein it further comprises (E) other curing agents. [8] The resin composition according to any one of [1] to [7], wherein when the total content of component (B) is 100% by mass, the content of component (B-1) is 20% by mass or more and 90% by mass or less. [9] The resin composition according to any one of [1] to [8], wherein, in formula (B-1a), R 14 This indicates 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 comprising any one of the resin compositions described in [1] to [9] disposed on the support.

[11] A circuit board comprising an insulating layer formed by curing a resin composition according to any one of [1] to [9].

[12] A semiconductor device comprising the circuit board described in

[11] . Invention Effects

[0008] According to the present invention, the following can be provided: a resin composition capable of forming a cured product with low dielectric properties and low coefficient of linear thermal expansion, and high adhesion and glass transition temperature before and after HAST testing; a resin sheet comprising the resin composition; a cured product of the resin composition; a circuit board comprising the cured product of the resin composition; and a semiconductor device comprising the circuit board. Detailed Implementation

[0009] Hereinafter, the present invention will be described using preferred embodiments. However, the present invention is not limited to the embodiments and examples shown below, and can be implemented in any way without departing from the scope of the claims and their equivalents.

[0010] [Resin Composition] The resin composition comprises (A) an epoxy resin, (B) an active ester compound, and (C) an inorganic filler. Component (B) comprises an active ester compound with the structure shown in formula (B-1a) (B-1) and an active ester compound other than component (B-1) (B-2). In this invention, by combining component (A), components (B-1) and (B-2) as component (B), and component (C), a cured product with low dielectric properties and coefficient of linear thermal expansion, and high adhesion and glass transition temperature before and after HAST testing can be obtained. Furthermore, cured products with excellent stain removal properties can generally be obtained as well.

[0011] The resin composition may be further combined with components (A) to (C) to include any other components. Examples of such components include (D) a free radical polymerizable compound, (E) a curing agent (except for substances belonging to (B) reactive ester compounds), (F) a curing accelerator, (G) a thermoplastic resin, (H) other additives, and (I) a solvent. The components contained in the resin composition will be described in detail below.

[0012] <(A) Epoxy Resin> The resin composition contains (A) epoxy resin as component (A). Epoxy resin (A) can be a curable resin having epoxy groups. By containing epoxy resin (A) in the resin composition, a cured product exhibiting good mechanical strength and insulation reliability can be obtained. Epoxy resin (A) can be used alone or in combination with two or more types.

[0013] Examples of epoxy resins (A) include xylenol-type epoxy resins, bisphenol A-type epoxy resins, bisphenol F-type epoxy resins, bisphenol S-type epoxy resins, bisphenol AF-type epoxy resins, dicyclopentadiene-type epoxy resins, triphenol-type epoxy resins, naphthol phenolic varnish-type epoxy resins, phenol phenolic varnish-type epoxy resins, tert-butyl-catechol-type epoxy resins, naphthalene-type epoxy resins, naphthol-type epoxy resins, anthracene-type epoxy resins, glycidylamine-type epoxy resins, glycidyl ester-type epoxy resins, and glycidylcyclohexane-type epoxy resins. Resins, including alkyl diglycidyl ether type epoxy resin, cresol phenolic varnish type epoxy resin, biphenyl type epoxy resin, linear aliphatic epoxy resin, epoxy resin with butadiene structure, alicyclic epoxy resin, heterocyclic epoxy resin, epoxy resin containing spirocyclic ring, cyclohexane type epoxy resin, cyclohexane-diethanol type epoxy resin, naphthyl ether type epoxy resin, tris(hydroxymethyl) type epoxy resin, tetraphenylethane type epoxy resin, phenol benzopyrrolidone type epoxy resin, etc.

[0014] The resin composition preferably includes an epoxy resin having two or more epoxy groups per molecule as component (A). From the viewpoint of significantly obtaining the desired effect of the present invention, the proportion of epoxy resin having two or more epoxy groups per molecule relative to 100% by mass of 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] The epoxy resin includes an epoxy resin that is liquid at 20°C (hereinafter sometimes referred to as "liquid epoxy resin") and an epoxy resin that is solid at 20°C (hereinafter sometimes referred to as "solid epoxy resin"). In the resin composition, component (A) may contain only liquid epoxy resin or only solid epoxy resin; a combination of both is preferred.

[0016] As a liquid epoxy resin, a liquid epoxy resin having two or more epoxy groups in one molecule is preferred.

[0017] As liquid epoxy resins, preferred types include bisphenol A epoxy resin, bisphenol F epoxy resin, bisphenol AF epoxy resin, naphthalene epoxy resin, glycidyl ester epoxy resin, glycidylamine epoxy resin, phenolic varnish epoxy resin, alicyclic epoxy resin with an ester skeleton, cyclohexane epoxy resin, cyclohexanediol epoxy resin, glycidylamine epoxy resin, and epoxy resin with a butadiene structure, glycidylcyclohexane epoxy resin, phenol benzopyrrolidone epoxy resin, and alkyl diglycidyl ether epoxy resin, with naphthalene epoxy resin being more preferred.

[0018] Specific examples of liquid epoxy resins include: DIC's "HP4032", "HP4032D", and "HP4032SS" (naphthalene-type epoxy resin); Mitsubishi Chemical's "828US", "jER828EL", "825", and "EPIKOTE828EL" (bisphenol A type epoxy resin); Mitsubishi Chemical's "jER807" and "1750" (bisphenol F type epoxy resin); Mitsubishi Chemical's "jER152" (phenolic varnish type epoxy resin); Mitsubishi Chemical's "630" and "630LSD" (glycidyl amine type epoxy resin); Nippon Steel Chemical Materials Co., Ltd.'s "ZX1059" (a mixture of bisphenol A and bisphenol F type epoxy resins); Nagase ChemteX's "EX-721" (glycidyl ester type epoxy resin); and Daicel's "CELLOXID". 2021P (alicyclic epoxy resin with an ester skeleton); Daicel's "PB-3600" (an epoxy resin with a butadiene structure); Nippon Steel Chemical Materials Co., Ltd.'s "ZX1658" and "ZX1658GS" (liquid 1,4-glycidylcyclohexane type epoxy resin); Mitsubishi Chemical Co., Ltd.'s "YED216D" (alkyl diglycidyl ether type epoxy resin), etc. These can be used individually or in combination of two or more.

[0019] As a 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] As solid epoxy resins, preferred types include xylenol-type epoxy resins, naphthalene-type epoxy resins, naphthalene-type tetrafunctional epoxy resins, cresol-phenolic varnish-type epoxy resins, dicyclopentadiene-type epoxy resins, triphenol-type epoxy resins, naphthol-type epoxy resins, biphenyl-type epoxy resins, naphthalene ether-type epoxy resins, anthracene-type epoxy resins, bisphenol A-type epoxy resins, bisphenol AF-type epoxy resins, and tetraphenylethane-type epoxy resins, with biphenyl-type epoxy resins being more preferred.

[0021] Specific examples of solid epoxy resins include: DIC's "HP4032H" (naphthalene-type epoxy resin), "HP-4700", "HP-4710" (naphthalene-type tetrafunctional epoxy resin), "N-690" (cresol phenolic varnish type epoxy resin), "N-695" (cresol phenolic varnish 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", and "HP6000L" (naphthyl ether type epoxy resin); and Nippon Kayaku Co., Ltd.'s "EPPN-502H" (triphenol type epoxy resin), "NC7000L" (naphthalene phenolic varnish type epoxy resin), "NC3000H", and "NC3" (naphthalene phenolic varnish type epoxy resin). 000, NC3000L, NC3100 (biphenyl type epoxy resin); Nippon Steel Chemical Materials Co., Ltd.'s "ESN475V" (naphthalene type epoxy resin) and "ESN485" (naphthalene phenolic varnish type epoxy resin); Mitsubishi Chemical Co., Ltd.'s "YX4000H", "YL6121" (biphenyl type epoxy resin), "YX4000HK" (bixylenol type epoxy resin), and "YX8800" (anthracite type epoxy resin) Epoxy resins include: "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 Co., Ltd.; and "WHR-991S" (phenol benzopyrrolidone type epoxy resin) manufactured by Nippon Kayaku Co., Ltd. These can be used individually or in combination of two or more.

[0022] When liquid epoxy resin and solid epoxy resin are used in combination as component (A), their mass ratio (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] (A) 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. Epoxy equivalent is the mass of epoxy resin containing 1 equivalent of epoxy groups. This epoxy equivalent can be determined according to JIS K 7236.

[0024] (A) The weight-average molecular weight (Mw) of 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 the weight-average molecular weight converted from polystyrene by gel permeation chromatography (GPC).

[0025] When the non-volatile component in the resin composition is set to 100% by mass, 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. 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] When the resin component in the resin composition is set to 100% by mass, 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. 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] It should be noted that, in this invention, unless otherwise explicitly stated, the content of each component in the resin composition is the value when the non-volatile component in the resin composition is set to 100% by mass. The non-volatile component refers to the entirety of the non-volatile component in the resin composition excluding the solvent. Furthermore, the resin composition of the resin composition indicates the composition after removing (C) the inorganic filler material from the non-volatile component of the resin composition.

[0028] <(B) Active Ester Compounds> The resin composition contains an active ester compound (B) as component (B). This active ester compound (B) does not contain any substances belonging to component (A) mentioned above. In the resin composition, as component (B), an active ester compound (B-1) represented by formula (B-1a) and an active ester compound (B-2) other than component (B-1) are combined and contained in the resin composition. As a result, a cured product with low dielectric properties and coefficient of linear thermal expansion, good adhesion before and after HAST testing, and a high glass transition temperature can be obtained. Furthermore, a cured product with excellent stain removal properties is generally also obtained. Component (B) can be used alone or in any combination of two or more components.

[0029] Component (B) contains an active ester site in one molecule. The active ester site in component (B) is preferably an aromatic ester skeleton. An aromatic ester skeleton refers to a skeleton having an ester bond and an aromatic ring bonded to one or both ends of the ester bond. Preferably, the aromatic ester skeleton has aromatic rings at both ends of the ester bond. Examples of groups having such a skeleton include: arylcarbonyloxy, aryloxycarbonyl, aryloxycarbonyloxy, aryloxycarbonyl, arylcarbonyloxyaryl, aryloxycarbonylaryl, aryloxycarbonylaryl, aryloxycarbonylaryl, aryloxycarbonylaryl, heteroarylcarbonyloxy, heteroaryloxycarbonyl, heteroarylcarbonyloxy, heteroaryloxycarbonyl, heteroarylcarbonyloxyaryl, heteroaryloxycarbonylaryl, heteroaryloxycarbonylaryl, heteroaryloxycarbonylaryl, heteroaryloxycarbonylaryl, heteroaryloxycarbonylaryl, heteroaryloxycarbonylaryl, heteroaryloxycarbonylaryl, heteroaryloxycarbonylaryl, heteroaryloxycarbonylaryl, heteroaryloxycarbonylaryl, heteroaryloxycarbonylaryl, heteroaryloxycarbonylaryl, heteroaryloxycarbonylaryl, heteroaryloxycarbonylaryl, heteroaryloxycarbonylaryl, arylcarbonyloxycarbonylaryl, aryloxycarbonylaryl, aryloxycarbonylaryl, aryloxycarbonylaryl, etc. Furthermore, the number of carbon atoms in the groups having such a skeleton is preferably 7 to 20, more preferably 7 to 15, and even more preferably 7 to 11.

[0030] As an aryl group, aryl groups with 6 to 30 carbon atoms are preferred, aryl groups with 6 to 20 carbon atoms are more preferred, and aryl groups with 6 to 10 carbon atoms are even more preferred. Examples of such aryl groups include phenyl, 1-methylphenyl, naphthyl, and anthracene. Here, naphthyl is a concept that includes 1-naphthyl and 2-naphthyl groups.

[0031] A heteroaryl group is a monovalent group formed by removing one hydrogen atom from an aromatic heterocycle. The aromatic heterocycle, as a cyclizing atom, contains not only carbon atoms but also heteroatoms such as oxygen, nitrogen, and sulfur atoms. Preferably, heteroaryl groups have 3 to 30 carbon atoms; more preferably, they have 4 to 20 carbon atoms; and even more preferably, they have 6 to 10 carbon atoms. Examples of such heteroaryl groups include furanyl, thiophene, pyrrole, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, imidazole, pyridinyl, pyridazinyl, pyrazinyl, and triazinyl (e.g., 1,3,5-triazin-2-yl).

[0032] As the arylene group, an arylene group having 6 to 30 carbon atoms is preferred, an arylene group having 6 to 20 carbon atoms is more preferred, and an arylene group having 6 to 10 carbon atoms is further preferred. Examples of such arylene groups include a phenylene group, a naphthylene group, an anthrylene group, a biphenylene group (-C6H4-C6H4-), etc. Here, the phenylene group is a concept including 1,2-phenylene, 1,3-phenylene, and 1,4-phenylene, and the naphthylene group is a concept including 1,2-naphthylene, 1,3-naphthylene, 1,4-naphthylene, 1,5-naphthylene, 1,6-naphthylene, 1,7-naphthylene, and 1,8-naphthylene.

[0033] The heteroarylene group refers to a divalent group formed by removing two hydrogen atoms from an aromatic heterocyclic ring, and in the aromatic heterocyclic ring, as ring-forming atoms, in addition to carbon atoms, there are also heteroatoms such as oxygen atoms, nitrogen atoms, sulfur atoms, etc. As the heteroarylene group, a heteroarylene group having 3 to 30 carbon atoms is preferred, a heteroarylene group having 4 to 20 carbon atoms is more preferred, and a heteroarylene group having 6 to 10 carbon atoms is further preferred. 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 an aryl group, an arylene group, a heteroaryl group, and a heteroarylene group may optionally have substituents. There is no particular limitation on the substituents, and examples thereof include a halogen atom, -OH, -O-C 1-6 alkyl, -N(C 1-10 alkyl)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, -COOH, -C(O)H, -NO2, a substituent containing a carbon-carbon double bond, etc. Here, the term "C p-q "(p and q are positive integers, satisfying p < q.) such a term means 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" means an alkyl group having 1 to ١٠ carbon atoms. These substituents may combine with each other to form a ring, and the ring structure also includes a spiro ring or a fused ring. The details of the substituent containing a carbon-carbon double bond are described below.

[0035] The term "aromatic group" refers to a group formed by removing one or more hydrogen atoms from the aromatic ring of an aromatic compound. The term "aromatic ring" refers to a ring that follows Hückel's rule, containing 4n+2 electrons (n ​​being a natural number) in its π-electron system. This includes monocyclic aromatic rings and fused polycyclic aromatic rings formed by the condensation of two or more monocyclic aromatic rings. Aromatic rings can be carbon rings or heterocycles containing heteroatoms such as oxygen, nitrogen, and sulfur atoms.

[0036] -The compound represented by formula (B-1a)- In the resin composition, component (B) contains a compound of formula (B-1a) as component (B-1). Component (B-1) can be used alone or in combination of two or more. [Chemical Formula 3] In the formula, R 11 Each of the following independently represents a monovalent aromatic group optionally having a substituent, R 12 Each of the following independently represents a divalent aromatic group optionally having a substituent, R 13 Each of the following independently represents a divalent aromatic group with a fused ring structure, optionally having substituents; R 14 Each of these groups independently represents a divalent hydrocarbon group with a substituent. n1 represents an integer greater than or equal to 0.

[0037] R 11 Each of these terms independently represents a monovalent aromatic group optionally having a substituent. A monovalent aromatic group is a group obtained by removing one hydrogen atom from the aromatic ring of an aromatic compound. The monovalent aromatic group preferably has 6 to 30 carbon atoms, more preferably 6 to 20, and even more preferably 6 to 10. This number of carbon atoms does not include the number of carbon atoms of the substituent. Examples of monovalent aromatic groups include aryl and heteroaryl groups, with aryl being preferred.

[0038] Regarding aryl and heteroaryl groups, as described above. Wherein, R... 11 Naphthyl is preferred, 1-naphthyl and 2-naphthyl are more preferred, and 1-naphthyl is even more preferred.

[0039] R 11 The monovalent aromatic group may optionally have substituents. These substituents are the same as those optionally present on the aromatic ester skeleton.

[0040] R 12Each of these terms independently represents a divalent aromatic group optionally having a substituent. A divalent aromatic group is a group obtained by removing two hydrogen atoms from the aromatic ring of an aromatic compound. Examples of divalent aromatic groups include arylene and heteroarylene, with arylene being preferred. The number of carbon atoms in the divalent aromatic group is preferably 6 to 24, more preferably 6 to 18, and even more preferably 6 to 14.

[0041] Regarding aryl and heteroaryl groups, as described above. Wherein, R 12 Phenylidene is preferred, and 1,3-phenylene is more preferred.

[0042] R 12 The divalent aromatic group may optionally have substituents. These substituents are the same as those optionally present on the aromatic ester skeleton.

[0043] R 13 Each of these terms independently represents a divalent aromatic group having a fused ring structure, optionally with substituents. Examples of divalent aromatic groups having a fused ring structure include arylene groups and heteroarylene groups, with arylene groups 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, further preferably 8 or more, preferably 24 or less, more preferably 18 or less, and even more preferably 14 or less.

[0044] Examples of aryl groups having a fused ring structure include 1,2-naphthylene, 1,3-naphthylene, 1,4-naphthylene, 1,5-naphthylene, 1,6-naphthylene, 1,7-naphthylene, 1,8-naphthylene, etc.; anthraceneylene; phenanthrenediyl, etc., with naphthylene being preferred, and 1,5-phenylene being more preferred.

[0045] Examples of heteroaryl groups with fused ring structures include carbazolediyl, quinolinediyl, and isoquinolinediyl.

[0046] R 13 The divalent aromatic group representing the fused ring structure may optionally have substituents. These substituents are the same as those optionally present on the aromatic ester skeleton.

[0047] R 14 Each of these can be independently represented as a divalent hydrocarbon group, optionally with substituents. Examples of divalent hydrocarbon groups include divalent aromatic groups, divalent aliphatic groups, or combinations thereof. A divalent hydrocarbon group is a group obtained by removing two hydrogen atoms from a hydrocarbon compound, while a divalent aliphatic group is a group obtained by removing two hydrogen atoms bonded to an aliphatic carbon atom in an aliphatic compound. Wherein, R... 14 Preferably, it represents a divalent aromatic group.

[0048] R14 The divalent aromatic group represented by R 12 The divalent aromatic groups are the same.

[0049] R 14 The divalent aliphatic group can be any of straight-chain, 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. This number of carbon atoms does not include the number of carbon atoms in the substituents. Examples of divalent aliphatic groups include alkylene groups and alkenyl groups, with alkylene groups being preferred.

[0050] The alkylene group can be linear, branched, or cyclic. Examples of alkylene groups include methylene, ethylene, propylene, 2-propylene, 1,1-dimethyl-3-methylpropylene, butylene, pentylene, hexylene, cyclopropylene, cyclobutylene, cyclopentylene, cyclohexylene, decahydronaphthylene, norcamphenene, bicyclopentylene, adamantylene, 1-methylmethylene, 1,1-dimethylmethylene, 1-methylethylene, 1,1-dimethylethylene, 1,2-dimethylethylene, butylene, 1-methylpropylene, and 2-methylpropylene. Among these, methylene is preferred as an alkylene group.

[0051] The alkenyl group can be linear, branched, or cyclic. Examples of alkenyl groups include vinylene, propenylene, butenylene, pentenylene, hexenylene, cyclopropenylene, cyclobutenylene, cyclopentenylene, cyclohexenylene, and norbornylene.

[0052] Examples of divalent groups formed by combining a divalent aromatic group and a divalent aliphatic group include alkylene-arylene, alkylene-arylene-alkylene, etc., with alkylene-arylene-alkylene being preferred, methylene-phenylene-methylene being more preferred, and methylene-1,4-phenylene-methylene being even more preferred.

[0053] R 14 The divalent hydrocarbon group, divalent aromatic group, and divalent aliphatic group may optionally have substituents. These substituents are the same as those optionally present in the aromatic ester skeleton.

[0054] n1 represents an integer greater than or equal to 0, preferably an integer greater than or equal to 1, more preferably an integer greater than or equal to 2, preferably an integer less than or equal to 15, more preferably an integer less than or equal to 10, and even more preferably an integer less than or equal to 8.

[0055] The active ester compound represented by formula (B-1a) is preferably the active ester compound represented by formula (B-1b). [Chemical Formula 4] In the formula, R 21 Each of the following independently represents a monovalent aromatic group optionally having a substituent, R 22 Each of the following independently represents a divalent aromatic group optionally having a substituent, R 24 Each of these groups independently represents a divalent hydrocarbon group with an optional substituent. n2 represents an integer greater than or equal to 0.

[0056] R 21 Each of these independently represents a monovalent aromatic group optionally having a substituent, and R in formula (B-1a) 11 same.

[0057] R 22 Each of these independently represents a divalent aromatic group with optional substituents, and R in formula (B-1a) 12 same.

[0058] R 24 The distribution independently represents a divalent hydrocarbon group with optional substituents, and R in formula (B-1a). 14 same.

[0059] n2 represents an integer greater than or equal to 0, which is the same as n1 in equation (B-1a).

[0060] The active ester compound represented by formula (B-1a) is preferably the active ester compound represented by formula (B-1c). [Chemical Formula 5] In the formula, R 31 Each of the following independently represents a monovalent aromatic group optionally having a substituent, R 32 Each of these groups independently represents a divalent aromatic group with a substituent. n3 represents an integer greater than or equal to 0.

[0061] R 31 Each of these independently represents a monovalent aromatic group optionally having a substituent, and R in formula (B-1a) 11 same.

[0062] R 32 Each of these independently represents a divalent aromatic group with optional substituents, and R in formula (B-1a) 12 same.

[0063] n3 represents an integer greater than or equal to 0, which is the same as n1 in equation (B-1a).

[0064] As a specific example of component (B-1), the compound shown in (1) below can be cited. However, component (B-1) is not limited to these specific examples. In the formula, n represents an integer greater than 0. [Chemical Formula 6]

[0065] (B-1) The component can be a compound synthesized by known methods. The synthesis of (B-1) can be carried out, for example, by the methods described in International Publication No. 2018 / 235424 or International Publication No. 2018 / 235425.

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

[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, preferably 1000 g / eq. or less, more preferably 800 g / eq. or less, and even more preferably 600 g / eq. or less. The active ester equivalent indicates the mass of resin per 1 equivalent of active ester groups.

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

[0069] When the non-volatile component in the resin composition is set to 100% by mass, the content of component (B-1) is preferably 1% by mass or more, more preferably 3% by mass or more, even more preferably 5% by mass or more, preferably 20% by mass or less, more preferably 15% by mass or less, and even more preferably 10% by mass or less.

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

[0071] When component (B) is set to 100% by mass, the content of component (B-1) 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, 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) in the resin composition is set to 100% by mass, and the content of component (B-1) in the resin composition is set to 100% by mass, and the ratio of a / b1 is preferably 0.1 or more, more preferably 0.3 or more, even more preferably 0.5 or more, preferably 2.5 or less, more preferably 2 or less, and even more preferably 1.5 or less, the effects of the present invention can be significantly obtained by adjusting the content so that a / b1 is within such a range.

[0073] -(B-2) Active ester compounds other than (B-1) (B) contains (B-2) active ester compounds other than (B-1) as component (B-2). Component (B-2) can be used alone or in combination with two or more.

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

[0075] The (B-2) component is preferably an active ester compound containing a (B-2-i) carbon-carbon double bond. Here, the carbon-carbon double bond refers to the carbon-carbon double bond site (C=C) that can polymerize with each other through free radicals, etc., and does not include reactive carbon-carbon double bonds that form aromatic groups such as benzene rings.

[0076] Examples of (B-2-i) components include (B-2-a) compounds having substituents containing carbon-carbon double bonds and active ester sites, and (B-2-b) compounds having a skeleton containing carbon-carbon double bonds and active ester sites.

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

[0078] In addition to having substituents containing carbon-carbon double bonds and active ester sites, the (B-2-a) component may also have any of the following: aromatic groups, aliphatic groups, oxygen atoms, and groups formed by combinations thereof.

[0079] As for the aromatic groups that can be present in the (B-2-a) component, divalent aromatic groups are preferred, more preferably arylene or arylenealkyl groups, and even more preferably arylene. Regarding arylene, as described above. As for arylenealkyl groups, arylenealkyl groups with 7 to 30 carbon atoms are preferred, more preferably arylenealkyl groups with 7 to 20 carbon atoms, and even more preferably arylenealkyl groups with 7 to 15 carbon atoms. Among these, phenylene is preferred.

[0080] As aliphatic groups that can be present in the (B-2-a) component, divalent aliphatic groups are preferred, divalent saturated aliphatic groups are more preferred, and alkylene or cycloalkylene groups are even more preferred. As alkylene groups, alkylene groups with 1 to 10 carbon atoms are preferred, alkylene groups with 1 to 6 carbon atoms are more preferred, and alkylene groups with 1 to 3 carbon atoms are even more preferred. Examples of alkylene groups include methylene, ethylene, propylene, 1-methylmethylene, 1,1-dimethylmethylene, 1-methylethylene, 1,1-dimethylethylene, 1,2-dimethylethylene, butylene, 1-methylpropylene, 2-methylpropylene, 1,1-dimethyl-3-methylpropylene, pentylene, hexylene, etc., with 1,1-dimethylmethylene being the most preferred.

[0081] As a cycloalkylene group, a cycloalkylene group with 3 to 20 carbon atoms is preferred, a cycloalkylene group with 3 to 15 carbon atoms is more preferred, and a cycloalkylene group with 5 to 10 carbon atoms is even more preferred. The cycloalkylene group can be a monocyclic or polycyclic structure. Examples of cycloalkylene groups include cyclopropylene, cyclobutylene, cyclopentylene, cyclohexylene, cyclopentylene, cycloheptylene, and cycloalkylene groups shown in formulas (a) to (d) below. In formulas (a) to (d), "*" indicates a bonding bond. [Chemical Formula 7]

[0082] As a group formed by combining these groups, a divalent group is preferred, and examples include groups formed by combining aliphatic and aromatic groups; groups formed by combining aromatic, aliphatic, and aromatic groups, etc. As one embodiment of a group formed by combining these groups, it is a group formed by a combination of arylene-alkylene-arylene, preferably a group formed by a combination of phenylene-1,1-dimethylmethylene-phenylene.

[0083] The (B-2-a) component may have aromatic and aliphatic groups, and optionally substituents. These substituents are the same as those optionally present in the aromatic ester skeleton.

[0084] In component (B-2-a), examples of substituents containing carbon-carbon double bonds include vinyl, propenyl (allyl, 1-propenyl, isopropenyl), butenyl (1-butenyl, crotonyl, methallyl, isocrotonyl, etc.), pentenyl (1-pentenyl, etc.), hexenyl (1-hexenyl, etc.), heptenyl (1-heptenyl, etc.), octenyl (1-cyclooctenyl, etc.), cyclopentenyl (2-cyclopentenyl, etc.), cyclohexenyl (3-cyclohexenyl, etc.), etc., with allyl being preferred.

[0085] The (B-2-a) component has substituents containing carbon-carbon double bonds. The number of substituents containing carbon-carbon double bonds in each molecule of (B-2-a) component is preferably 1 or more, more preferably 2 or more, more preferably 10 or less, more preferably 8 or less, and even more preferably 5 or less.

[0086] The carbon-carbon double bond substituent in component (B-2-a) can be a substituent for a terminal monovalent aromatic group, or it can be a substituent for an aromatic group or an aliphatic group. When component (B-2-a) has a carbon-carbon double bond substituent as a substituent for a terminal monovalent aromatic group, component (B-2-a) preferably has a carbon-carbon double bond substituent as a substituent for both terminal aromatic groups.

[0087] The (B-2-a) component preferably comprises any one of the active ester compounds represented by the following general formula (Bi) and the active ester compounds represented by the following general formula (B-ii), and more preferably comprises the active ester compound represented by the general formula (Bi). [Chemical Formula 8] In formula (Bi), Ar 11 Each of the following independently represents a monovalent aromatic group optionally having a substituent, Ar 12Each of the following independently represents a divalent aromatic group optionally having a substituent, Ar 13 Each of these groups independently represents a divalent aromatic group with optional substituents, a divalent aliphatic group with optional substituents, an oxygen atom, a sulfur atom, or a divalent group formed by combinations thereof. mi and ni independently represent integers greater than 0. Where Ar... 11 Ar 12 and Ar 13 At least one of them has a substituent containing a carbon-carbon double bond. In equation (B-ii), Ar 11 Each of the following independently represents a monovalent aromatic group optionally having a substituent, Ar 12 Each of the following independently represents a divalent aromatic group optionally having a substituent, Ar 13 Each of these groups independently represents a divalent aromatic group with optional substituents, a divalent aliphatic group with optional substituents, an oxygen atom, a sulfur atom, or a divalent group formed by combinations thereof. mii and nii independently represent integers greater than 0. Where Ar... 11 Ar 12 and Ar 13 At least one of them has a substituent containing a carbon-carbon double bond.

[0088] In equations (Bi) and (B-ii), Ar 11 Each of these groups independently represents a monovalent aromatic group optionally having a substituent. As a monovalent aromatic group, it is related to R in formula (B-1a). 11 The aromatic groups with the same monovalent valence are represented. Among them, Ar... 11 Phenyl or naphthyl are preferred, phenyl, 1-naphthyl or 2-naphthyl are more preferred, and 1-naphthyl is even more preferred.

[0089] Ar 11 The monovalent aromatic group may optionally have substituents. These substituents are the same as those optionally present in the aromatic ester skeleton. Wherein, Ar 11 When substituents are present, the substituents are preferably substituents containing carbon-carbon double bonds.

[0090] In equations (Bi) and (B-ii), Ar 12 Each of these independently represents a divalent aromatic group optionally having a substituent. As a divalent aromatic group, it is related to R in formula (B-1a). 12 The divalent aromatic groups are the same. Among them, Ar... 12 Phenylidene is preferred, and 1,3-phenylene is more preferred.

[0091] Ar 12The divalent aromatic group represented may optionally have substituents. These substituents are the same as those optionally present in the aromatic ester skeleton. Specifically, Ar in formula (Bi) 12 Preferably, it has an aralkyl group as a substituent, and more preferably, it has a benzyl group as a substituent.

[0092] In general formulas (Bi) and (B-ii), Ar 13 Each of these can be independently represented as a divalent aromatic group optionally having a substituent, a divalent aliphatic group optionally having a substituent, an oxygen atom, a sulfur atom, or a divalent group formed by combinations thereof, preferably a divalent group formed by combinations thereof. As a divalent aromatic group, it is associated with Ar... 12 The divalent aromatic groups are the same.

[0093] As a divalent aliphatic group, a divalent saturated aliphatic group is more preferred, and alkylene or cycloalkylene groups are more preferred, with cycloalkylene groups being even more preferred. The terms alkylene and cycloalkylene are as described above.

[0094] The divalent group formed by combining these groups is preferably a divalent group formed by combining a divalent aromatic group optionally having a substituent and a divalent aliphatic group optionally having a substituent, and more preferably a divalent group formed by alternating combinations of multiple divalent aromatic groups optionally having a substituent and multiple divalent aliphatic groups optionally having a substituent. Specific examples of the divalent groups described above include the following divalent groups (B1) to (B13), with (B10) and (B11) being preferred. In the formula, a1 to a9 represent integers from 0 to 10, preferably integers from 0 to 6, and more preferably integers from 0 to 5. "*" indicates a bonding bond, and the wavy line indicates a structure obtained by reacting an aromatic compound, an acyl halide of an aromatic compound, or an ester of an aromatic compound used in the synthesis of component (B-2). [Chemical Formula 9] [Chemical Formula 10]

[0095] Ar 13 The divalent aromatic group and divalent aliphatic group may optionally have substituents. These substituents are the same as those optionally present on the aromatic ester skeleton.

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

[0097] In the general formula (Bi), ni represents an integer greater than or equal to 0, preferably an integer from 0 to 30, more preferably an integer from 3 to 30, and even more preferably an integer from 6 to 30.

[0098] In the general formula (B-ii), mii and nii independently represent integers greater than or equal to 0, preferably integers from 0 to 20, more preferably integers from 0 to 15, and even more preferably integers from 0 to 10 or integers from 0 to 6.

[0099] The active ester compound represented by the general formula (Bi) is preferably a compound represented by the following general formula (Bia). [Chemical Formula 11] In formula (Bia), Ar 21 Each of the following independently represents a monovalent aromatic group optionally having a substituent, Ar 22 Each of the following independently represents a divalent aromatic group optionally having a substituent, Ar 23 Each of these can independently represent a divalent aromatic group with substituents, a divalent aliphatic group with substituents, an oxygen atom, a sulfur atom, or a divalent group formed by combinations thereof. mi1 and ni1 can independently represent integers greater than 0.

[0100] Ar 21 Each of these independently represents a monovalent aromatic group optionally having a substituent, and is associated with Ar in formula (Bi). 11 same.

[0101] Ar 22 Each of these independently represents a divalent aromatic group optionally having a substituent, and is related to Ar in formula (Bi). 12 same.

[0102] Ar 23 Each of these independently represents a divalent aromatic group optionally having a substituent, a divalent aliphatic group optionally having a substituent, an oxygen atom, a sulfur atom, or a divalent group composed of combinations thereof, and is related to Ar in formula (Bi). 13 same.

[0103] mi1 represents an integer greater than or equal to 0, which is the same as mi in equation (Bi). Additionally, ni1 represents an integer greater than or equal to 0, which is the same as ni in equation (Bi).

[0104] Specific examples of (B-2-a) components include compounds (Bi) to (Biv). Additionally, specific examples of (B-2-a) components include compounds described in paragraphs 0068 to 0071 of International Publication No. 2018 / 235424 and paragraphs 0113 to 0115 of International Publication No. 2018 / 235425. However, (B-2-a) components are not limited to these specific examples. In the formula, a represents an integer from 0 to 6, s represents 0 or more, and r represents an integer from 1 to 10. n and m are integers greater than or equal to 0. [Chemical Formula 12]

[0105] (B-2-a) can be a compound synthesized by known methods. The synthesis of (B-2a) can be carried out, for example, by the methods described in International Publication No. 2018 / 235424 or International Publication No. 2018 / 235425.

[0106] In the (B-2-b) component, the butadiene skeleton can be cited as an example of a carbon-carbon double bond-containing skeleton. The butadiene skeleton refers to the carbon skeleton contained in butenediyl. Here, butenediyl includes 2-buten-1,4-diyl and 3-buten-1,2-diyl (i.e., vinylethylene). The aforementioned 2-buten-1,4-diyl can be either cis or trans. Hereinafter, the structure containing the butadiene skeleton is sometimes appropriately referred to as a "butadiene structure." This butadiene structure includes the aforementioned 2-buten-1,4-diyl and 3-buten-1,2-diyl, and groups in which the hydrogen atoms contained in these groups are replaced by substituents. Examples of substituents include: halogen atoms; saturated aliphatic hydrocarbon groups such as alkyl and cycloalkyl groups; aromatic hydrocarbon groups such as aryl groups; alkoxy, cycloalkyloxy, aryloxy, and other alkyloxy groups; etc.

[0107] As a preferred example of a butadiene structure, the structures shown in formulas (B14) to (B15) below can be cited. [Chemical Formula 13] In equations (B14) and (B15), R b Each of the following can be independently represented: 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. Additionally, * indicates a bonding site.

[0108] As for the butadiene structure, the structure shown in formula (B14) is preferred. Therefore, for the (B-2-b) component, as a structure having a butadiene skeleton, it is preferable to include the butadiene structure shown in formula (B14), or it may only include the butadiene structure shown in formula (B14).

[0109] The (B-2-b) component typically contains one or more butadiene structures per molecule, preferably two or more. More preferably, the (B-2-b) component comprises a polybutadiene structure formed by the combination of two or more butadiene structures.

[0110] The (B-2-b) component is preferably an active ester compound represented by the following formula (B-iii). [Chemical Formula 14] In equation (B-iii), Ar 1 Each of the following independently represents a monovalent aromatic group optionally having a substituent, Ar 2 Each of the following independently represents a divalent aromatic group optionally having a substituent, R 1 Each independently represents a divalent aliphatic group optionally having substituents, R 2 Each of these characters independently represents the butadiene structure. m and n independently represent integers greater than or equal to 0.

[0111] Ar 1 Each of these independently represents a monovalent aromatic group optionally having a substituent, and is associated with Ar in formula (Bi). 11 The aromatic groups with the same monovalent valence are represented. Among them, Ar... 1 1-Methylphenyl is preferred.

[0112] Ar 12 Each of these independently represents a divalent aromatic group optionally having a substituent, and is related to Ar in formula (Bi). 12 The divalent aromatic groups are the same.

[0113] R 1 Each of these independently represents a divalent aliphatic group optionally having a substituent, and R in formula (B-1a) 14 The divalent aliphatic groups are the same.

[0114] R 2 The butadiene structure is represented independently, as described above.

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

[0116] Ar 1The 1-valent aromatic group, Ar 12 The divalent aromatic group and R represent 1 The divalent aliphatic group may optionally have substituents. These substituents are the same as those optionally present on the aromatic ester skeleton.

[0117] Specific examples of the (B-2-b) component include the compounds shown in (B-iv) below. However, the (B-2-b) component is not limited to these specific examples. In the formula, Ar... 1 m and n are independently related to Ar in equation (B-iii) 1 m and n are the same. [Chemical Formula 15]

[0118] The (B-2-i) component preferably comprises any one of the (B-2-a) and (B-2-b) components. Therefore, the (B-2-i) component preferably comprises any one of the active ester compound shown in formula (Bi), the active ester compound shown in formula (B-ii), and the active ester compound shown in formula (B-iii), more preferably comprises any one of the active ester compound shown in formula (Bi) and the active ester compound shown in formula (B-iii), and even more preferably comprises the active ester compound shown in formula (Bi).

[0119] The weight-average molecular weight of the (B-2-i) component is preferably 150 or more, more preferably 200 or more, even more preferably 250 or more, preferably 3000 or less, more preferably 2000 or less, and even more preferably 1500 or less. The weight-average molecular weight of the (B-2-i) component is the weight-average molecular weight converted from polystyrene as determined by gel permeation chromatography (GPC).

[0120] The active ester equivalent of the (B-2-i) component is preferably 50 g / eq or more, more preferably 100 g / eq or more, even more preferably 150 g / eq or more, preferably 2000 g / eq or less, more preferably 1000 g / eq or less, and even more preferably 500 g / eq or less. The active ester equivalent indicates the mass of resin per 1 equivalent of active ester groups.

[0121] The ratio of component (A) to component (B-2-i), measured as the ratio of [total number of active ester groups in component (B-2-i)] to [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, preferably 5 or less, more preferably 4 or less, and even more preferably 3 or less. Here, "number of active ester groups in component (B-2-i)" refers to the sum of all values ​​obtained by dividing the mass of the non-volatile component of component (B-2-i) present in the resin composition by the equivalent amount of active ester groups. By ensuring that the ratio of component (A) to component (B-2-i) is within the aforementioned range, the effects of the present invention can be significantly obtained.

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

[0123] When the non-volatile component of the resin composition is set to 100% by mass, the content of the (B-2-i) component is preferably 1% by mass or more, more preferably 2% by mass or more, even more preferably 2.5% by mass or more, preferably 15% by mass or less, more preferably 10% by mass or less, and even more preferably 8% by mass or less.

[0124] When the resin component of the resin composition is set to 100% by mass, 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, 15% by mass or more, preferably 35% by mass or less, more preferably 30% by mass or less, and even more preferably 25% by mass or less.

[0125] When component (B) is set to 100% by mass, the content of component (B-2-i) is preferably 60% by mass or less, more preferably 55% by mass or less, even more preferably 50% by mass or less, 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) in the resin composition is set to 100% by mass, and the content of component (B-2-i) in the resin composition is set to 100% by mass, and the ratio of non-volatile components in the resin composition is set to b2, a / b2 is preferably 0.5 or more, more preferably 1 or more, further preferably 1.5 or more, preferably 5 or less, more preferably 4 or less, and further preferably 3.5 or less. By adjusting the content so that a / b2 is within the aforementioned range, the effects of the present invention can be significantly obtained.

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

[0128] When the content of component (B-1) when the non-volatile component in the resin composition is set to 100% by mass is set as b1, and the content of component (B-2-i) when the non-volatile component in the resin composition is set to 100% by mass is set as b2, the ratio of b1 to b2 is preferably 0.3 or more, more preferably 0.5 or more, even more preferably 1 or more, preferably 10 or less, more preferably 8 or less, and even more preferably 5 or less. By adjusting the content so that b1 / b2 is within the aforementioned range, the effects of the present invention can be significantly obtained.

[0129] As component (B-2), in addition to the active ester compound containing a carbon-carbon double bond as component (B-2-i), it may further include an active ester compound without a carbon-carbon double bond (B-2-ii). Component (B-2-ii) may be used alone or in combination of two or more.

[0130] As the (B-2-ii) component, compounds having two or more highly reactive ester groups in one molecule, such as phenolic esters, thiophenolic esters, N-hydroxylamine esters, and heterocyclic hydroxyl compounds, are preferred.

[0131] The (B-2-ii) component is preferably a substance obtained by the condensation reaction of a carboxylic acid compound and / or a thiocarboxylic acid compound with a hydroxyl compound and / or a thiol compound. Particularly from the viewpoint of improving heat resistance, an active ester resin obtained from a carboxylic acid compound and a hydroxyl compound is preferred, and an active ester resin obtained from a carboxylic acid compound and a phenolic compound and / or a naphthol compound is more preferred. Examples of carboxylic acid compounds include, for instance, benzoic acid, acetic acid, succinic acid, maleic acid, itaconic acid, phthalic acid, isophthalic acid, terephthalic acid, and pyromellitic acid. Examples of phenolic or naphthol compounds include hydroquinone, resorcinol, bisphenol A, bisphenol F, bisphenol S, phenolphthalein, methylated bisphenol A, methylated bisphenol F, methylated bisphenol S, phenol, o-cresol, m-cresol, p-cresol, catechol, α-naphthol, β-naphthol, 1,5-dihydroxynaphthol, 1,6-dihydroxynaphthol, 2,6-dihydroxynaphthol, dihydroxybenzophenone, trihydroxybenzophenone, tetrahydroxybenzophenone, phloroglucinol, pyroglucinol, dicyclopentadiene-type diphenol compounds, and linear phenolic resins. Here, "dicyclopentadiene-type diphenol compounds" refers to diphenol compounds obtained by condensing two molecules of phenol into one molecule of dicyclopentadiene.

[0132] Specifically, as the (B-2-ii) component, preferred active ester resins include dicyclopentadiene-type resins, naphthoid-type active ester resins containing a naphthalene structure, active ester resins containing acetylated linear phenolic resins, and active ester resins containing benzoylated linear phenolic resins, with naphthoid-type active ester resins being more preferred. As the dicyclopentadiene-type active ester resin, an active ester resin containing a dicyclopentadiene-type diphenol structure is preferred.

[0133] Regarding commercially available products containing the (B-2-ii) component, examples of reactive ester resins containing a dicyclopentadiene-type diphenol structure include "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); examples of reactive ester resins containing a naphthalene structure include "HP-B-8151-62T", "EXB-8100L-65T", and "EXB- Examples of active ester resins include “8150-60T”, “EXB-8150-62T”, “EXB-9416-70BK”, “HPC-8150-60T”, “HPC-8150-62T”, and “HPC-8151-62T” (manufactured by DIC Corporation); “EXB9401” (manufactured by DIC Corporation) is an example of an active ester resin containing phosphorus; “DC808” (manufactured by Mitsubishi Chemical Corporation) is an example of an active ester resin containing an acetylated linear phenolic resin; “YLH1026”, “YLH1030”, and “YLH1048” (manufactured by Mitsubishi Chemical Corporation) are examples of active ester resins containing styrene and naphthalene structures; and “PC1300-02-65MA” (manufactured by Air Water Corporation) is an example of an active ester resin containing styrene and naphthalene structures.

[0134] The active ester equivalent of the (B-2-ii) component is preferably 50 g / eq. or more, more preferably 100 g / eq. or more, more preferably 3000 g / eq. or less, more preferably 1000 g / eq. or less, further preferably 500 g / eq. or less, and particularly preferably 300 g / eq. or less. The active ester equivalent is the mass of an active ester compound containing 1 equivalent of an active ester group.

[0135] The ratio of component (A) to component (B-2-ii), measured as the ratio of [total number of active ester groups in component (B-2-ii)] to [total number of epoxy groups in epoxy resin (A)], is preferably 0.01 or more, more preferably 0.03 or more, even more preferably 0.05 or more, 0.1 or more, 0.15 or more, or 0.2 or more, preferably 5 or less, more preferably 4 or less, and even more preferably 3 or less. Here, "number of active ester groups in component (B-2-ii)" refers to the sum of all values ​​obtained by dividing the mass of the non-volatile component of component (B-2-ii) present in the resin composition by the equivalent amount of active ester groups.

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

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

[0138] When component (B) is set to 100% by mass, the content of component (B-2-ii) is preferably 60% by mass or less, more preferably 55% by mass or less, even more preferably 50% by mass or less, preferably 10% by mass or more, more preferably 15% by mass or more, and even more preferably 20% by mass or more.

[0139] When the non-volatile component of the resin composition is set to 100% by mass, the content of component (B-2) is preferably 1% by mass or more, more preferably 2% by mass or more, even more preferably 2.5% by mass or more, preferably 15% by mass or less, more preferably 10% by mass or less, and even more preferably 8% by mass or less.

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

[0141] When component (B) is set to 100% by mass, the content of component (B-2) is preferably 60% by mass or less, more preferably 55% by mass or less, even more preferably 50% by mass or less, preferably 10% by mass or more, more preferably 15% by mass or more, and even more preferably 20% by mass or more.

[0142] The ratio of component (A) to component (B), expressed as the ratio of [total number of active groups in component (B)] to [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, preferably 5 or less, more preferably 4 or less, and even more preferably 3 or less. Here, "number of active groups in component (B)" refers to the sum of all values ​​obtained by dividing the mass of the non-volatile component of component (B) present in the resin composition by the equivalent amount of active ester groups. By keeping the ratio of component (A) to component (B) within the aforementioned range, the effects of the present invention can be significantly obtained.

[0143] When the non-volatile component in the resin composition is set to 100% by mass, the content of component (B) is preferably 1% by mass or more, more preferably 3% by mass or more, even more preferably 5% by mass or more, preferably 25% by mass or less, even more preferably 20% by mass or less, and even more preferably 15% by mass or less.

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

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

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

[0147] Commercially available products as (C) inorganic filler materials include, for example, “SP60-05” and “SP507-05” manufactured by Nippon Steel Chemical Materials Co., Ltd.; “YC100C”, “YA050C”, “YA050C-MJE”, “YA010C”, “SC2500SQ”, “SO-C4”, “SO-C2”, and “SO-C1” manufactured by Yatoma Co., Ltd.; “UFP-30”, “DAW-03”, and “FB-105FD” manufactured by Denka Co., Ltd.; “Silfil NSS-3N”, “Silfil NSS-4N”, and “Silfil NSS-5N” manufactured by Tokuyama Co., Ltd.; and “CellSpheres” and “MGH-005” manufactured by Pacific Cement Co., Ltd.

[0148] (C) The average particle size of the inorganic filler material 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, 0.5 μm or more, 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 inorganic filler materials can be determined by laser diffraction scattering based on the Mie scattering theory. Specifically, a laser diffraction scattering particle size distribution measuring device can be used to prepare a particle size distribution on a volume basis, and the median particle size can be used as the average particle size for measurement. The sample for testing can be obtained by weighing 100 mg of inorganic filler material and 10 g of methyl ethyl ketone into a tube and dispersing it ultrasonically for 10 minutes. For the sample to be tested, a laser diffraction particle size distribution measuring device can be used, using blue and red light source wavelengths, to measure the volume-based particle size distribution of the inorganic filler material in a flow cell manner, and the average particle size can be calculated based on the obtained particle size distribution as the median particle size. Examples of laser diffraction particle size distribution measuring devices include the "LA-960" manufactured by Horiba Manufacturing Co., Ltd.

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

[0151] (C) The specific surface area of ​​inorganic filler materials can be determined by the BET method. Nitrogen gas is adsorbed on the sample surface using a specific surface area measuring device (Macsorb HM-1210 manufactured by Mountech), and the specific surface area is calculated using the BET multi-point method.

[0152] From the viewpoint of improving moisture resistance and dispersibility, (C) inorganic filler materials are preferably treated with surface treatment agents. Examples of surface treatment agents include fluorinated silane coupling agents, aminosilane coupling agents, epoxysilane coupling agents, mercaptosilane coupling agents, silane coupling agents, alkoxysilanes, organosilazane compounds, titanate coupling agents, etc. A single surface treatment agent can be used, or two or more can be used in combination.

[0153] Commercially available surface treatment agents include, for example, "KBM403" (3-epoxypropoxypropyltrimethoxysilane) manufactured by Shin-Etsu Chemical Industry Co., Ltd., "KBM803" (3-mercaptopropyltrimethoxysilane) manufactured by Shin-Etsu Chemical Industry Co., Ltd., "KBE903" (3-aminopropyltriethoxysilane) manufactured by Shin-Etsu Chemical Industry Co., Ltd., "KBM573" (N-phenyl-3-aminopropyltrimethoxysilane) manufactured by Shin-Etsu Chemical Industry Co., Ltd., "SZ-31" (hexamethyldisilazane) manufactured by Shin-Etsu Chemical Industry Co., Ltd., "KBM103" (phenyltrimethoxysilane) manufactured by Shin-Etsu Chemical Industry Co., Ltd., "KBM-4803" (long-chain epoxy silane coupling agent) manufactured by Shin-Etsu Chemical Industry Co., Ltd., and "KBM-7103" (3,3,3-trifluoropropyltrimethoxysilane) manufactured by Shin-Etsu Chemical Industry Co., Ltd.

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

[0155] The degree of surface treatment using surface treatment agents can be evaluated by the carbon content per unit surface area of ​​the inorganic filler material. From the viewpoint of improving the dispersibility of the inorganic filler material, the carbon content per unit surface area of ​​the inorganic filler material is preferably 0.02 mg / m². 2 The above, more preferably 0.1 mg / m 2 The above is further preferred to be 0.2 mg / m³. 2 That's all. On the other hand, from the viewpoint of preventing an increase in the melt viscosity of the resin composition, 1.0 mg / m³ is preferred. 2 The following is more preferably 0.8 mg / m³ 2The following is a further preferred value: 0.5 mg / m³ 2 the following.

[0156] (C) The carbon content per unit surface area of ​​the inorganic filler material can be determined after cleaning the surface-treated inorganic filler material with a solvent (e.g., methyl ethyl ketone (MEK)). Specifically, a sufficient amount of MEK is added as a solvent to the surface-treated inorganic filler material, and ultrasonic cleaning is performed at 25°C for 5 minutes. After removing the supernatant and drying the solid components, the carbon content per unit surface area of ​​the inorganic filler material can be determined using a carbon analyzer. A carbon analyzer such as the "EMIA-320V" manufactured by Horiba Corporation can be used.

[0157] Furthermore, the degree of surface treatment using the surface treatment agent can be evaluated by the carbon content per unit mass of the inorganic filler material. The carbon content per unit mass of the inorganic filler material is preferably 0.01% by mass or more, more preferably 0.05% by mass or more, even more preferably 0.1% by mass or more, and 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 carbon content per unit mass of (C) inorganic filler material, like the carbon content per unit surface area of ​​(C) inorganic filler material, can also be determined using a carbon analyzer.

[0158] When the non-volatile component in the resin composition is set to 100% by mass, the content of (C) inorganic filler material 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, 70% by mass or more, preferably 90% by mass or less, more preferably 85% by mass or less, and even more preferably 80% by mass or less.

[0159] <(D) Free radical polymerizable compounds> The resin composition may contain a (D) radical polymerizable compound as component (D). The (D) radical polymerizable compound as component (D) does not include substances belonging to components (A) through (C). Component (D) may be used alone or in combination of two or more.

[0160] (D) Radical polymerizable compounds may contain olefinically unsaturated bonds. Therefore, (D) radical polymerizable compounds may have radical polymerizable groups containing olefinically unsaturated bonds. Examples of radical polymerizable groups 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 (2,5-dihydro-2,5-dioxo-1H-pyrrole-1-yl). (D) Radical polymerizable compounds preferably have two or more radical polymerizable groups.

[0161] Examples of (D) radical polymerizable compounds include (meth)acrylic acid-based radical polymerizable compounds, styrene-based radical polymerizable compounds, allyl-based radical polymerizable compounds, and maleimide-based radical polymerizable compounds. As component (D), it is preferable to include any one of styrene-based radical polymerizable compounds, allyl-based radical polymerizable compounds, and maleimide-based radical polymerizable compounds; more preferably, it includes any one of allyl-based radical polymerizable compounds and maleimide-based radical polymerizable compounds; and even more preferably, it includes maleimide-based radical polymerizable compounds.

[0162] (Meth)acrylic acid-based free radical polymerizable compounds, for example, compounds having one or more, preferably two or more, acryloyl and / or methacryloyl groups. Examples of low molecular weight (molecular weight less than 1000) aliphatic (meth)acrylate compounds, such as cyclohexane-1,4-diethanol di(meth)acrylate, cyclohexane-1,3-diethanol di(meth)acrylate, tricyclodecane-diethanol di(meth)acrylate, neopentyl glycol di(meth)acrylate, 1,4-butanediol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, 1,8-octanediol di(meth)acrylate, 1,9-nonanediol di(meth)acrylate, 1,10-decanediol di(meth)acrylate, trimethylolpropane tri(meth)acrylate, trimethylolethane tri(meth)acrylate, glycerol tri(meth)acrylate, and pentaerythritol tetra(meth)acrylate; and dioxanediol di(meth)acrylate, 3,6-dioxane-1,8-octanediol di(meth)acrylate, etc. Low molecular weight (molecular weight less than 1000) ether-containing (meth)acrylate compounds such as diol di(meth)acrylate, 3,6,9-trioxaundecane-1,11-diol di(meth)acrylate, polyethylene glycol di(meth)acrylate, polypropylene glycol di(meth)acrylate, 9,9-bis[4-(2-acryloyloxyethoxy)phenyl]fluorene, ethoxylated bisphenol A di(meth)acrylate, propoxylated bisphenol A di(meth)acrylate, etc.; low molecular weight (molecular weight less than 1000) isocyanurate-containing (meth)acrylate compounds such as tri(3-hydroxypropyl)isocyanurate tri(meth)acrylate, tri(2-hydroxyethyl)isocyanurate tri(meth)acrylate, ethoxylated isocyanurate tri(meth)acrylate, etc.; high molecular weight (molecular weight greater than 1000) acrylate compounds such as (meth)acrylate-modified polyphenylene ether resin, etc. Commercially available (meth)acrylic acid-based free radical polymerizable compounds include, for example, "A-DOG" (dioxanediol diacrylate) manufactured by Shin-Nakamura Chemical Industry Co., Ltd., "DCP-A" (tricyclodecanediethanol diacrylate) and "DCP" (tricyclodecanediethanol dimethacrylate) manufactured by Kyoeisha Chemical Co., Ltd., "KAYARAD R-684" (tricyclodecanediethanol diacrylate) and "KAYARAD R-604" (dioxanediol diacrylate) manufactured by Nippon Kayaku Co., Ltd., and "SA9000" and "SA9000-111" (methacrylic acid modified polyphenylene ether) manufactured by SABIC.

[0163] Styrene-based free radical polymerizable compounds can be, for example, compounds having one or more, preferably two or more, vinyl groups directly bonded to aromatic carbon atoms. Examples of styrene-based free radical polymerizable compounds include low molecular weight (molecular weight less than 1000) styrene-based compounds such as divinylbenzene, 2,4-divinyltoluene, 2,6-divinylnaphthalene, 1,4-divinylnaphthalene, 4,4'-divinylbiphenyl, 1,2-bis(4-vinylphenyl)ethane, 2,2-bis(4-vinylphenyl)propane, and bis(4-vinylphenyl) ether; 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 free radical polymerizable compounds include, for example, "ODV-XET(X03)", "ODV-XET(X04)", and "ODV-XET(X05)" (styrene-divinylbenzene copolymer) manufactured by Nippon Steel Chemical Materials Co., Ltd., and "OPE-2St 1200" and "OPE-2St2200" (styrene-modified polyphenylene ether resin) manufactured by Mitsubishi Gas Chemical Co., Ltd. Other styrene-based free radical polymerizable compounds include, for example, copolymer A described in International Publication No. 2017 / 115813.

[0164] Allyl-based free radical polymerizable compounds are, for example, compounds having one or more, preferably two or more, allyl groups. Examples of allyl-based free radical polymerizable compounds include aromatic carboxylic acid allyl ester compounds such as diallyl diphenyl ester, triallyl trimellitate, diallyl phthalate, diallyl isophthalate, diallyl terephthalate, diallyl 2,6-naphthalenedicarboxylate, and diallyl 2,3-naphthalenedicarboxylate; 1,3,5-triallyl isocyanurate, and 1,3-diallyl-5-glycidyl isocyanurate. Allyl isocyanurate compounds such as esters; aromatic allyl compounds containing epoxy groups such as 2,2-bis[3-allyl-4-(glycidoxy)phenyl]propane; aromatic allyl compounds containing benzoxazine such as bis[3-allyl-4-(3,4-dihydro-2H-1,3-benzoxazine-3-yl)phenyl]methane; aromatic allyl compounds containing ethers such as 1,3,5-triallyl ether benzene; and allylsilane compounds such as diallyl diphenylsilane. Commercially available allyl-based free radical polymerizable compounds include: TAIC (1,3,5-triallyl isocyanurate) manufactured by Nippon Chemical Co., Ltd.; DAD (dallyl biphenyl dicarboxylate) manufactured by Nisshoku Techno Fine Chemical Co., Ltd.; TRIAM-705 (triallyl trimellitate) manufactured by Fujifilm and Hikari Pure Chemical Industries Co., Ltd.; and Nisshoku Techno Fine Chemical Co., Ltd. Products manufactured under the trade name "DAND" (2,3-naphthoic acid diallyl ester) by Chemical Co., Ltd., "ALP-d" (bis[3-allyl-4-(3,4-dihydro-2H-1,3-benzoxazin-3-yl)phenyl]methane) by Shikoku Chemical Co., Ltd., "RE-810NM" (2,2-bis[3-allyl-4-(glycidoxy)phenyl]propane) by Nippon Kayaku Co., Ltd., and "DA-MGIC" (1,3-diallyl-5-glycidyl isocyanurate) by Shikoku Chemical Co., Ltd., etc.

[0165] Maleimide-based free radical polymerizable compounds may be, for example, compounds having one or more, preferably two or more, maleimide groups. Maleimide-based free radical polymerizable compounds may be aliphatic maleimide compounds containing an aliphatic amine skeleton, or aromatic maleimide compounds containing an aromatic amine skeleton. Commercially available maleimide-based free radical polymerizable compounds include, for example, Shin-Etsu Chemical Co., Ltd.'s "SLK-2600", Designer Molecules Inc.'s "BMI-1500", "BMI-1700", "BMI-3000J", "BMI-689", "BMI-2500" (maleimide compounds containing a dimeric diamine structure), Designer Molecules Inc.'s "BMI-6100" (aromatic maleimide compounds), Nippon Kayaku Co., Ltd.'s "MIR-5000-60T" and "MIR-3000-70MT" (biphenyl aryl maleimide compounds), KI Chemical Co., Ltd.'s "BMI-70" and "BMI-80", and Daiwa Chemical Industry Co., Ltd.'s "BMI-2300" and "BMI-TMH". Alternatively, the maleimide resin (a maleimide compound containing an indane ring skeleton) disclosed in Japanese Invention Association Publication No. 2020-500211 can also be used as a maleimide-based free radical polymerizable compound.

[0166] (D) The olefinic unsaturated bond equivalent of the free radical 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 olefinic unsaturated bond equivalent represents the mass of the free radical polymerizable compound per 1 olefinic unsaturated bond.

[0167] (D) The weight-average molecular weight (Mw) of the free radical 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, and for example, it can be 150 or more. The weight-average molecular weight can be determined by gel permeation chromatography (GPC) as a value converted from polystyrene.

[0168] When the non-volatile component in the resin composition is set to 100% by mass, the content of component (D) is preferably 0.1% by mass or more, more preferably 0.5% by mass or more, even more preferably 1% by mass or more, preferably 10% by mass or less, more preferably 5% by mass or less, and even more preferably 3% by mass or less.

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

[0170] [(E) Any curing agent] The resin composition may include any curing agent (E) other than component (B) as component (E). Any curing agent (E) as component (E) refers to a resin capable of reacting with epoxy resin (A) to cure the resin composition. The curing agent (E) does not include substances belonging to components (A) to (D) above. For example, maleimide resin can react with epoxy resin (A) under a suitable catalyst, but maleimide resin is not classified as any curing agent (E). Any curing agent (E) may be used alone or in combination of two or more.

[0171] Preferred examples of any curing agent in (E) include phenolic resins, benzoxazine resins, cyanate ester resins, carbodiimide resins, acid anhydride resins, amine resins, etc.

[0172] As phenolic resins, resins having one or more, preferably two or more, hydroxyl groups (phenolic hydroxyl groups) bonded to aromatic rings such as benzene rings or naphthalene rings in one molecule can be used. From the viewpoint of heat resistance and water resistance, phenolic resins with a phenolic structure are preferred. Furthermore, from the viewpoint of adhesion, nitrogen-containing phenolic resins are preferred, and phenolic resins containing a triazine skeleton are more preferred. Among these, linear phenolic resins containing a triazine skeleton are 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 Chemical Co., Ltd.; "NHN", "CBN", and "GPH" manufactured by Nippon Kayaku Co., Ltd.; "SN-170", "SN-180", "SN-190", "SN-475", "SN-485", "SN-495", "SN-495V", "SN-375", and "SN-395" manufactured by Nippon Steel Chemical Materials Co., Ltd.; "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 DIC Co., Ltd.; and "GDP-6115L", "GDP-6115H", and "ELPC" manufactured by Gunei Chemical Co., Ltd. 75” etc. As benzoxazine resins, resins having one or more, preferably two or more, benzoxazine rings within one molecule can be used. Specific examples of benzoxazine resins include "JBZ-OP100D" and "ODA-BOZ" manufactured by JFE Chemical Co., Ltd.; "HFB2006M" manufactured by Showa Polymer Co., Ltd.; and "Pd", "Fa", and "ALP-d" manufactured by Shikoku Chemical Industry Co., Ltd.

[0174] As a cyanate ester resin, a resin having one or more, preferably two or more, cyanate ester groups in one molecule can be used. Examples of difunctional cyanate resins include: bisphenol A dicyanate, polyphenol cyanate, oligomeric (3-methylene-1,5-phenylene cyanate), 4,4'-methylenebis(2,6-dimethylphenyl cyanate), 4,4'-ethylene diphenyl dicyanate, hexafluorobisphenol A dicyanate, 2,2-bis(4-cyanoesteryl)phenylpropane, 1,1-bis(4-cyanoesterylphenylmethane), bis(4-cyanoesteryl-3,5-dimethylphenyl)methane, 1,3-bis(4-cyanoesterylphenyl-1-(methylethylene))benzene, bis(4-cyanoesterylphenyl) sulfide, and bis(4-cyanoesterylphenyl) ether; polyfunctional cyanate resins derived from linear phenolic resins and cresol phenolic resins; prepolymers obtained by triazineizing a portion of these cyanate resins; etc. Specific examples of cyanate ester resins include "PT30" and "PT60" (linear phenolic polyfunctional cyanate ester resins), "BA230" and "BA230S75" (prepolymers in which some or all of the bisphenol A dicyanate is triazineized to form a trimer), manufactured by Arxada Corporation.

[0175] As a carbodiimide resin, resins having one or more, preferably two or more, carbodiimide structures within one molecule can be used. Specific examples of carbodiimide resins include: aliphatic bis(tert-butylcarbodiimide), cyclohexanebis(methylene-tert-butylcarbodiimide), and other aliphatic biscarbodiimides; aromatic biscarbodiimides such as phenylene-bis(xylylcarbodiimide); aliphatic polycarbodiimides such as polyhexamethylenecarbodiimide, polytrimethylhexamethylenecarbodiimide, polycyclohexylcarbodiimide, poly(methylene biscyclohexylcarbodiimide), and poly(isophoronecarbodiimide); poly(phenylenecarbodiimide), poly(… Aromatic polycarbodiimides such as naphthylcarbodiimide, poly(tolylcarbodiimide), poly(methyldiisopropylphenylcarbodiimide), poly(triethylphenylcarbodiimide), poly(diethylphenylcarbodiimide), poly(triisopropylphenylcarbodiimide), poly(diisopropylphenylcarbodiimide), poly(xylylcarbodiimide), poly(tetramethylxylylcarbodiimide), poly(methylenediphenylcarbodiimide), and poly[methylenebis(methylphenyl)carbodiimide] are also included. 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 Co., Ltd.; and "Stabaxol P", "Stabaxol P400" and "Hycasyl 510" manufactured by Lanxess Co., Ltd.

[0176] As an anhydride resin, resins having one or more, preferably two or more, anhydride groups in one molecule can be used. Specific examples of anhydride resins include: phthalic anhydride, tetrahydrophthalic anhydride, hexahydrophthalic anhydride, methyltetrahydrophthalic anhydride, methylhexahydrophthalic anhydride, methylnadic anhydride, hydrogenated methylnadic anhydride, trialkyltetrahydrophthalic anhydride, dodecenylsuccinic anhydride, 5-(2,5-dioxotetrahydro-3-furanyl)-3-methyl-3-cyclohexene-1,2-dicarboxylic anhydride, trimellitic anhydride, and pyromellitic anhydride. Benzophenone tetracarboxylic dianhydride, biphenyl tetracarboxylic dianhydride, naphthalene tetracarboxylic dianhydride, oxydiphthalic dianhydride, 3,3'-4,4'-diphenylsulfone tetracarboxylic dianhydride, 1,3,3a,4,5,9b-hexahydro-5-(tetrahydro-2,5-dioxo-3-furanyl)-naphtho[1,2-C]furan-1,3-dione, ethylene glycol bis(triphenyl) ester, styrene-maleic acid resin obtained by copolymerization of styrene and maleic acid, and other polymeric anhydrides. Commercially available anhydride resins include, for example, “HNA-100”, “MH-700”, “MTA-15”, “DDSA”, and “OSA” manufactured by Shin Nippon Rika Co., Ltd.; “YH-306” and “YH-307” manufactured by Mitsubishi Chemical Co., Ltd.; “HN-2200” manufactured by Resonac Co., Ltd.; and “EF-30”, “EF-40”, “EF-60”, and “EF-80” manufactured by Cray Valley Co., Ltd.

[0177] As an amine resin, a resin having one or more, preferably two or more, amino groups within one molecule can be used. Examples of amine resins include aliphatic amines, polyether amines, alicyclic amines, and aromatic amines, with aromatic amines being preferred. The amine resin is preferably a primary or secondary amine, more preferably a primary amine. Specific examples of amine resins include 4,4'-methylenebis(2,6-dimethylaniline), 4,4'-diaminodiphenylmethane, 4,4'-diaminodiphenyl sulfone, 3,3'-diaminodiphenyl sulfone, m-phenylenediamine, m-xylenediamine, diethyltoluenediamine, 4,4'-diaminodiphenyl ether, 3,3'-dimethyl-4,4'-diaminobiphenyl, 2,2'-dimethyl-4,4'-diaminobiphenyl, 3,3'-dihydroxybiphenylamine, and 2,2-bis(3-amino-4-hydroxy) 2,2-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, bis(4-(3-aminophenoxy)phenyl)sulfone, etc. 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 Co., Ltd.; and "DTDA" manufactured by Sumitomo Seika Co., Ltd.

[0178] (E) The active group equivalent of component (E) is preferably 50 g / eq. to 3000 g / eq., more preferably 100 g / eq. to 1000 g / eq., even more preferably 100 g / eq. to 500 g / eq., and particularly preferably 100 g / eq. to 300 g / eq. The active group equivalent indicates the mass of resin per 1 equivalent of active groups.

[0179] The ratio of component (A) to component (E), expressed as the ratio of [total number of active groups in component (E)] to [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, preferably 5 or less, more preferably 4 or less, even more preferably 3 or less, 2 or less, or 1 or less. Here, "number of active groups in component (E)" refers to the sum of all values ​​obtained by dividing the mass of the non-volatile component of component (E) present in the resin composition by the equivalent amount of active groups.

[0180] The ratio of component (A) to components (B) and (E), expressed as the ratio of [the total number of active ester groups in component (B) and active groups in component (E)] to [the 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, 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 sum of all values ​​obtained by dividing the mass of the non-volatile components of components (B) and (E) present in the resin composition by the equivalent amount of active groups.

[0181] When the non-volatile component in the resin composition is set to 100% by mass, the content of component (E) is preferably 0.5% by mass or more, more preferably 1% by mass or more, more preferably 1.5% by mass or more, preferably 5% by mass or less, more preferably 4% by mass or less, and more preferably 3% by mass or less.

[0182] When the resin component in the resin composition is set to 100% by mass, 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. 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 materials> The resin composition according to this embodiment may also include (F) organic filler as an optional component. The (F) organic filler, as component (F), does not contain substances belonging to components (A) to (E) described above. The (F) organic filler is typically included in the resin composition as particles incompatible with the resin components other than the (F) organic filler, and is included in the cured product while maintaining this particle state. Furthermore, one type of (F) organic filler may be used alone, or two or more may be used in combination.

[0184] As the (F) organic filler material, particles of organic material can be used. As the organic material contained in the (F) organic filler material, a rubber component is preferred. Examples of rubber components include: silicone elastomers such as polydimethylsiloxane; olefin-based thermoplastic elastomers such as polybutadiene, polyisoprene, polychloroprene, 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 acrylic thermoplastic elastomers such as poly(meth)acrylate, poly(meth)acrylate, poly(meth)acrylate, poly(cyclohexyl methacrylate), and poly(octyl methacrylate). Furthermore, silicone rubbers such as polysiloxane rubber can be mixed into the rubber component. The glass transition temperature of the rubber component contained in the rubber particles is, for example, below 0°C, preferably below -10°C, more preferably below -20°C, and even more preferably below -30°C.

[0185] (F) Organic filler materials can be core-shell type rubber particles formed by graft copolymerization of core particles containing the rubber components listed above and a shell composed of monomer components that can copolymerize with the rubber components contained in the core particles. The term "core-shell type" here does not necessarily refer only to the type in which the core particles and the shell can be clearly distinguished, but also includes the type in which the boundary between the core particles and the shell is not clear, and the core particles may not be completely covered by the shell.

[0186] Specific examples of (F) organic filler materials include: Samsung SDI's "CHT"; TechnoUMG's "B602"; Dow's "PARALOID EXL-2602", "PARALOID EXL-2603", "PARALOID EXL-2655", "PARALOID EXL-2311", "PARALOID EXL2313", "PARALOID EXL-2315", "PARALOID KM-330", "PARALOID KM-336P", "PARALOID KCZ-201"; Mitsubishi Rayon's "Metablen C-223A", "Metablen E-901", "Metablen S-2001", "Metablen W-450A", "Metablen SRK-200"; and KANEKA's "Kaneace M-511", "Kaneace M-600", "Kaneace M-511", "Kaneace M-600", "Kaneace M-511", "Kaneace M-600", "Kaneace M-223A", "Metablen E-901", "Metablen S-2001", "Metablen W-450A", "Metablen SRK-200"; and KANEKA's "Kaneace M-511", "Kaneace M-600", "Kaneace M-223A", "Metablen E-901", "Metablen S-2001", "Metablen W-450A", "Metablen SRK-200". "M-400", "Kaneace M-580", "Kaneace MR-01", and AICA Industrial Corporation's "STAPHYLOID AC3355", "STAPHYLOID AC3816", "STAPHYLOID AC3816N", "STAPHYLOID AC3832", "STAPHYLOID AC4030", "STAPHYLOID AC3364", etc.

[0187] The content of (F) organic filler material relative to 100% by mass of non-volatile components in the resin composition 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, preferably 3% by mass or less, more preferably 2% by mass or less, and even more preferably 1% by mass or less.

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

[0189] <(G) Curing Accelerator> The resin composition may also contain (G) a curing accelerator as an optional component. The (G) curing accelerator, as component (G), does not contain substances belonging to components (A) to (F) above. The (G) curing accelerator can act as a catalyst on the reaction of the (A) epoxy resin to promote the curing of the resin composition.

[0190] Examples of (G) curing accelerators include phosphorus-based curing accelerators, urea-based curing accelerators, guanidine-based curing accelerators, imidazole-based curing accelerators, metal-based curing accelerators, and amine-based curing accelerators. A single (G) curing accelerator can be used alone, or two or more can be used in combination.

[0191] Examples of phosphorus-based curing accelerators include: tetrabutylphosphonium bromide, tetrabutylphosphonium chloride, tetrabutylphosphonium acetate, tetrabutylphosphonium decanoate, tetrabutylphosphonium laurate, bis(tetrabutylphosphonium)pyromellitictetrate, tetrabutylphosphonium hexahydrophthalate, tetrabutylphosphonium 2,6-bis[(2-hydroxy-5-methylphenyl)methyl]-4-methylphenolate, di-tert-butylmethylphosphonium tetraphenylborate, and other aliphatic phosphonium salts; methyltriphenylphosphonium bromide, ethyltriphenylphosphonium bromide, propyltriphenylphosphonium bromide, butyltriphenylphosphonium bromide, benzyltriphenylphosphonium chloride, tetraphenylphosphonium bromide, and p-tolyltriphenylphosphonium tetraphosphonium bromide. Aromatic phosphonium salts such as p-tolylborate, tetraphenylphosphonium tetraphenylborate, tetraphenylphosphonium tetrap-tolylborate, triphenylethylphosphonium tetraphenylborate, tri(3-methylphenyl)ethylphosphonium tetraphenylborate, tri(2-methoxyphenyl)ethylphosphonium tetraphenylborate, (4-methylphenyl)triphenylphosphonium thiocyanate, tetraphenylphosphonium thiocyanate, and butyltriphenylphosphonium thiocyanate; aromatic phosphine-borane complexes such as triphenylphosphine-triphenylborane; aromatic phosphine-quinone addition reactants such as triphenylphosphine-p-benzoquinone addition reactants; tributylphosphine, tri-tert-butylphosphine, trioctylphosphine, and di-tert-butyl(2-butylphosphine) Aliphatic phosphines such as tricyclohexylphosphine, di-tert-butyl(3-methyl-2-butenyl)phosphine, and tricyclohexylphosphine; and tributylphenylphosphine, tri-tert-butylphenylphosphine, methyldiphenylphosphine, ethyldiphenylphosphine, butyldiphenylphosphine, diphenylcyclohexylphosphine, triphenylphosphine, tri-o-tolylphosphine, tri-m-tolylphosphine, tri-p-tolylphosphine, tri(4-ethylphenyl)phosphine, tri(4-propylphenyl)phosphine, tri(4-isopropylphenyl)phosphine, tri(4-butylphenyl)phosphine, tri(4-tert-butylphenyl)phosphine, tri(2,4-dimethylphenyl)phosphine, tri(2,5-dimethylphenyl)phosphine, and tri(2,6-dimethylphenyl)phosphine. Aromatic phosphines include 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 urea-based curing accelerators 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 include 1-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)[toluenebisdimethylurea], etc.

[0193] Examples of guanidine-based 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-methylbiguanidine, 1-ethylbiguanidine, 1-n-butylbiguanidine, 1-n-octadecylbiguanidine, 1,1-dimethylbiguanidine, 1,1-diethylbiguanidine, 1-cyclohexylbiguanidine, 1-allylbiguanidine, 1-phenylbiguanidine, 1-(o-tolyl)biguanidine, etc.

[0194] Examples of imidazole-based curing accelerators include: 2-methylimidazolium, 2-undecylimidazolium, 2-heptadecylimidazolium, 1,2-dimethylimidazolium, 2-ethyl-4-methylimidazolium, 1,2-dimethylimidazolium, 2-ethyl-4-methylimidazolium, 2-phenylimidazolium, 2-phenyl-4-methylimidazolium, 1-benzyl-2-methylimidazolium, 1-benzyl-2-phenylimidazolium, 1-cyanoethyl-2-methylimidazolium, 1-cyanoethyl-2-undecylimidazolium, 1-cyanoethyl-2-ethyl-4-methylimidazolium, 1-cyanoethyl-2-phenylimidazolium, 1-cyanoethyl-2-undecylimidazolium trimellitate, 1-cyanoethyl-2-phenylimidazolium trimellitate, 2,4-diamino-6-[2'-methylimidazolium-(1')] Imidazole compounds such as 2,4-diamino-6-[2'-undecylimidazolyl-(1')]-ethyl-triazine, 2,4-diamino-6-[2'-ethyl-4'-methylimidazolyl-(1')]-ethyl-triazine, 2,4-diamino-6-[2'-methylimidazolyl-(1')]-ethyl-triazine isocyanuric acid adduct, 2-phenylimidazolyl isocyanuric acid adduct, 2-phenyl-4,5-dihydroxymethylimidazolium, 2-phenyl-4-methyl-5-hydroxymethylimidazolium, 2,3-dihydro-1H-pyrrolo[1,2-a]benzimidazole, 1-dodecyl-2-methyl-3-benzyl chloride imidazolyl, 2-methylimidazoline, 2-phenylimidazoline, etc., as well as adducts of imidazolium compounds with epoxy resins. Commercially available imidazole-based curing accelerators include, for example, those manufactured by Shikoku Chemical Industry Co., Ltd. such as "1B2PZ", "2E4MZ", "2MZA-PW", "2MZ-OK", "2MA-OK", "2MA-OK-PW", "2PHZ", "2PHZ-PW", "Cl1Z", "Cl1Z-CN", "Cl1Z-CNS", and "C11Z-A"; and "P200-H50" manufactured by Mitsubishi Chemical Co., Ltd.

[0195] Examples of organometallic 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 organocobalt complexes such as cobalt(II) and cobalt(III) acetylacetone; organocopper complexes such as copper(II) acetylacetone; organozinc complexes such as zinc(II) acetylacetone; organoiron complexes such as iron(III) acetylacetone; organonickel complexes such as nickel(II) acetylacetone; and organomanganese complexes such as manganese(II) acetylacetone. Examples of organometallic salts include zinc octoate, tin octoate, zinc naphthenate, cobalt naphthenate, tin stearate, and zinc stearate.

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

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

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

[0199] <(H) Any additives> The resin composition may further include any additive (H) as an optional component. The optional additive (H) as component (H) does not contain substances belonging to components (A) to (G) above. Examples of optional additives (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 dioxide, 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 Bentonite and montmorillonite; defoamers such as silicone-based defoamers, acrylic defoamers, fluorinated defoamers, and vinyl resin-based defoamers; ultraviolet absorbers such as benzotriazole-based ultraviolet absorbers; adhesion enhancers such as ureasilanes; and adhesion promoters such as triazole-based, tetraazole-based, and triazine-based adhesion promoters. Properties-enhancing agents; hindered phenolic antioxidants and other antioxidants; fluorescent whitening agents such as zirconia derivatives; surfactants such as fluorinated surfactants and organosilicon surfactants; flame retardants such as phosphorus-based (e.g., phosphate ester compounds, phosphazene compounds, phosphonic acid compounds, red phosphorus), nitrogen-based (e.g., melamine sulfate), halogen-based, and inorganic flame retardants such as antimony trioxide; dispersants such as phosphate ester-based, polyoxyethylene-based, acetylene-based, organosilicon-based, anionic, and cationic dispersants; stabilizers such as borate ester-based, titanate ester-based, aluminate ester-based, zirconate ester-zirconic acid-based, isocyanate-based, carboxylic acid-based, and carboxylic anhydride-based stabilizers, etc. (H) Any additive may be used alone or in combination of two or more.

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

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

[0202] <Method for manufacturing resin composition> A resin composition can be manufactured, for example, by mixing components that may be included in the resin composition. These components may be mixed partially or entirely simultaneously, or sequentially. During the mixing of the components, a suitable temperature can be set, allowing for temporary or continuous heating and / or cooling. Additionally, stirring or agitation may be performed during the mixing of the components.

[0203] <Properties and Uses of Resin Compositions> Since the resin composition comprises component (A), components (B-1) and (B-2) as component (B), and component (C), a cured product with low dielectric properties and coefficient of linear thermal expansion, and high adhesion and glass transition temperature before and after HAST testing can be obtained. In addition, a cured product with excellent stain removal properties can usually be obtained.

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

[0205] The cured product obtained by heat curing the resin composition at 190°C for 90 minutes exhibits 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 limitation on the lower limit, but it can be 0.00001 or more, etc. The dielectric loss tangent can be measured according to the method described in the examples below.

[0206] The cured product obtained by heat curing the resin composition at 100°C for 30 minutes, followed by heat curing at 170°C for 30 minutes, exhibits excellent adhesion to the copper foil before accelerated environmental testing (HAST). Therefore, the cured product provides an insulating layer with excellent adhesion (peel strength) to the copper foil before the HAST test. 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 can be 10 kgf / cm or less, etc. The peel strength can be measured according to the method described in the examples below.

[0207] The cured product obtained by heat curing the resin composition at 100°C for 30 minutes, followed by heat curing at 170°C for 30 minutes, exhibits excellent adhesion to the copper foil after accelerated environmental testing (HAST). Therefore, the cured product provides an insulating layer with excellent adhesion (peel strength) to the 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 can be 10 kgf / cm or less, etc. The peel strength can be measured according to the method described in the examples below.

[0208] The cured product obtained by heat curing the resin composition at 190°C for 90 minutes exhibits 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, and it can be 500°C or lower, etc. The glass transition temperature can be determined according to the method described in the examples below.

[0209] The cured product obtained by heat curing the resin composition at 190°C for 90 minutes exhibits a low coefficient of linear thermal expansion (CTE). Therefore, the cured product provides an insulating layer with a low CTE. The CTE 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 limitation on the lower limit, and it can be 1 ppm / °C or more, etc. The CTE can be determined according to the method described in the examples below.

[0210] Cured products obtained by heat curing the resin composition at 130°C for 30 minutes, followed by heat curing at 170°C for 30 minutes, typically exhibit excellent stain removal properties. For example, in the method described in <Test 3. Evaluation Test of Stain Removability> of the examples described later, when the cured product is used to form an insulating layer and its stain removal properties are evaluated, the maximum stain length can be less than 5 μm.

[0211] <Uses of Resin Compositions> The resin composition described in this embodiment can be used for forming insulating layers, and is particularly preferred for forming insulating layers on circuit boards. Additionally, the resin composition can also be used for manufacturing resin sheets. Typically, these resin sheets are used to form insulating layers. Furthermore, the resin composition can also be used for other applications, such as solder resists, underfill materials, chip bonding materials, via-filling resins, sealing resins, and component embedding resins.

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

[0213] From the viewpoint of thinness, the thickness of the resin composition layer 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 supports include films made of plastic materials, metal foils, and release paper, with films made of plastic materials and metal foils being preferred.

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

[0216] When metal foil is used as a support, examples of metal foil include copper foil and aluminum foil. Copper foil is preferred. As copper foil, foil formed from copper as a single metal can be used, or foil formed from an alloy of copper with other metals (e.g., tin, chromium, silver, magnesium, nickel, zirconium, silicon, titanium, etc.) can be used.

[0217] For the support, surface treatments such as matte treatment, corona treatment, and antistatic treatment can be applied to the surface that bonds with the resin composition layer.

[0218] As a support, a support with a release layer can be used on the surface that bonds to the resin composition layer. Examples of release agents used in the release layer of the support with a release layer include, for example, one or more release agents selected from alkyd-based release agents, polyolefin-based release agents, polyurethane-based release agents, and silicone-based release agents. Commercially available products can be used as the support with the release layer, such as PET films having a release layer primarily composed of silicone-based or alkyd resin-based release agents, such as Lintec's "PET501010", "SK-1", "AL-5", and "AL-7"; Toray's "Lumirror T60"; Teijin's "Purex"; and Unitika's "Unipeel".

[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, preferably 75 μm or less, more preferably 60 μm or less, and even more preferably 50 μm or less. When using a support with a release layer, the overall thickness of the support with the release layer is preferably within the above range.

[0220] The resin sheet can also incorporate any components as needed. For example, the resin sheet can have a protective film that protects the resin composition layer. The protective film is typically applied to the side of the resin composition layer that is not bonded to the support (i.e., the side opposite to the support). The thickness of the protective film is not particularly limited, for example, from 1 μm to 40 μm. With the protective film, it is possible to prevent debris from adhering to the surface of the resin composition layer or to prevent damage.

[0221] Resin sheets can be manufactured, for example, by forming a resin composition layer on a support. Specifically, a liquid (varnish-like) resin composition can be prepared directly or by mixing a solvent with the resin composition, applied to a support, and then dried as needed to form a resin composition layer, thereby manufacturing a resin sheet. As a solvent, the same solvent as described in (I) as a component of the resin composition can be used.

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

[0223] The resulting resin sheets can be wound into rolls for storage. When the resin sheets have a protective film, they can usually be used by peeling off the protective film.

[0224] [Circuit board] One embodiment of the present invention relates to a circuit board comprising an insulating layer formed from a cured product of the aforementioned resin composition. The insulating layer may consist solely of the cured product of the resin composition. The thickness of the insulating layer is not particularly limited, and may, for example, be within the same range as the thickness of the resin composition layer contained in the resin sheet. Furthermore, the insulating layer may generally have the same properties as the cured product of the aforementioned resin composition.

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

[0226] The preferred example involves a method for manufacturing a circuit board that includes: The process of forming a resin composition layer on the inner substrate (I), and Step (II) for curing the resin composition layer.

[0227] "Inner layer substrate" refers to the component that forms the substrate of a circuit board, such as glass epoxy resin substrate, metal substrate, polyester substrate, polyimide substrate, BT resin substrate, and thermosetting polyphenylene ether substrate. Furthermore, the inner layer substrate may have conductive layers on one or both sides. The conductive layers of the inner layer substrate can also be patterned. An inner layer substrate with conductive layers (circuit) formed on one or both sides of the substrate is sometimes called an "inner circuit board." Additionally, intermediate components to be further formed with insulating layers and / or conductive layers during the manufacture of a circuit board are also included in the term "inner layer substrate." Furthermore, inner layer substrates with built-in components can also be used.

[0228] Regarding the formation of the resin composition layer on the inner layer substrate, it can be carried out, for example, by a formation method that includes coating the resin composition on the inner layer substrate and drying it as needed, but it is preferable to use a resin sheet. The method for forming the resin composition layer using a resin sheet generally includes a step of laminating the resin sheet to the inner layer substrate. The lamination of the resin sheet to the inner layer substrate is performed in a manner that the resin composition layer of the resin sheet is bonded to the inner layer substrate. This lamination can be performed, for example, by heating and pressing the resin sheet onto the inner layer substrate from the support side. Examples of components for heating and pressing the resin sheet onto the inner layer substrate (hereinafter also referred to as "heat-pressing component") include, for example, heated metal plates (SUS end plates, etc.) or metal rollers (SUS rollers, etc.). It should be noted that it is preferable not to directly press the heat-pressing component onto the resin sheet, but rather to press it using an elastic material such as heat-resistant rubber so that the resin sheet fully follows the surface irregularities of the inner layer substrate.

[0229] The lamination of the inner substrate and the resin sheet can be performed using vacuum lamination. In vacuum lamination, the heating and pressing temperature is preferably in the range of 60°C to 160°C, more preferably in the range of 80°C to 140°C; the heating and pressing pressure is preferably in the range of 0.098 MPa to 1.77 MPa, more preferably in the range of 0.29 MPa to 1.47 MPa; and the heating and pressing time is preferably in the range of 20 seconds to 400 seconds, more preferably in the range of 30 seconds to 300 seconds. Lamination is preferably performed under reduced pressure conditions of 26.7 hPa or less.

[0230] Lamination can be performed using commercially available vacuum laminators. Examples of commercially available vacuum laminators include the vacuum pressure laminator manufactured by Meiki Manufacturing Co., Ltd., the vacuum dressing machine manufactured by Nikko-Materials Co., Ltd., and batch vacuum pressure laminators.

[0231] The manufacturing method of the circuit board may include, after lamination, pressing the heated bonding member under normal pressure (atmospheric pressure), for example from the support side, thereby performing a smoothing treatment on the resin sheet. The pressing conditions for the smoothing treatment can be the same as the conditions for the heated bonding of the lamination described above. The smoothing treatment can be performed using a commercially available laminator. Lamination and smoothing treatment can be performed continuously using the aforementioned commercially available vacuum laminator.

[0232] The circuit board manufacturing method described in this example includes a step (II) after step (I) in which a resin composition layer is cured. By curing the resin composition layer in step (II), an insulating layer comprising a cured resin composition can be formed.

[0233] The curing of the resin composition layer is usually carried out by heat curing. The heat curing conditions of the resin composition layer can 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. In addition, 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 manufacturing a circuit board may include preheating the resin composition layer at a temperature below the curing temperature before thermal curing. For example, before thermal curing the resin composition layer, it can typically be preheated at a temperature of 50°C to 150°C, preferably 60°C to 140°C, more preferably 70°C to 130°C, for at least 5 minutes, preferably 5 minutes to 150 minutes, more preferably 15 minutes to 120 minutes, and even more preferably 15 minutes to 100 minutes. Preheating is usually performed after step (I). Furthermore, if a smoothing treatment is performed after laminating the inner layer substrate and the resin sheet, preheating can typically be performed after that smoothing treatment.

[0235] When using resin sheets, the circuit board manufacturing method may include a step of peeling off the support of the resin sheet after the inner substrate and the resin sheet are laminated. The peeling off of the support can be performed between steps (I) and (II), or after step (II). Furthermore, if the circuit board manufacturing method, as described below, includes a step (III) of forming holes in the insulating layer, a step (IV) of roughening the insulating layer, and a step (V) of forming a conductor layer, the peeling off of the support can be performed between steps (II) and (III), between steps (III) and (IV), or between steps (IV) and (V).

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

[0237] The method for manufacturing a circuit board may include a step (IV) of roughening the insulating layer. This roughening process roughens the surface of the insulating layer. Furthermore, it removes contaminants (resin residue) from the insulating layer. Therefore, this roughening process is sometimes referred to as a "decontamination process." For example, if a hole is formed in step (III), contaminants may form within the hole; therefore, it is preferable to perform the roughening process (IV) after step (III) to remove the aforementioned contaminants.

[0238] There are no particular limitations on the steps and conditions of the roughening treatment; known steps and conditions commonly used in forming the insulating layer of a circuit board can be adopted. For example, the roughening treatment can be performed by sequentially performing a swelling treatment using a swelling liquid, an oxidation treatment using an oxidizing agent, and a neutralization treatment using a neutralizing liquid on the insulating layer.

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

[0240] Examples of oxidants used in roughening treatments include alkaline permanganate solutions, such as potassium permanganate or sodium permanganate dissolved in an aqueous solution of sodium hydroxide. For roughening treatment using oxidants such as alkaline permanganate solutions, it is preferable to immerse the insulating layer in an oxidant solution heated to 60°C to 100°C for 10 to 30 minutes. Furthermore, the concentration of permanganate in the alkaline permanganate solution is preferably 5% to 10% by mass. Commercially available oxidants include, for example, alkaline permanganate solutions such as "Concentrate Compact CP" and "Dosing Solution Securiganth P" manufactured by Ammet Japan Co., Ltd.

[0241] The neutralizing solution used in the roughening process is preferably an acidic aqueous solution, and a commercially available example is "Reduction Solution Securiganth P" manufactured by Ammet Japan Co., Ltd. The neutralization process using the neutralizing solution can be performed by immersing the surface treated with the oxidizing agent in a neutralizing solution at 30°C to 80°C for 5 to 30 minutes. From an operational point of view, it is preferable to immerse the object treated with the oxidizing agent in a neutralizing solution at 40°C to 70°C for 5 to 20 minutes.

[0242] The method for manufacturing a circuit board may include a step (V) of forming a conductor layer on an insulating layer. In the case where the method for manufacturing a circuit board includes step (III) or (IV), the step (V) of forming the conductor layer is generally preferably performed after steps (III) and (IV).

[0243] The conductor material used in the conductor layer is not particularly limited. In a preferred embodiment, the conductor layer comprises one or more metals selected from gold, platinum, palladium, silver, copper, aluminum, cobalt, chromium, zinc, nickel, titanium, tungsten, iron, tin, and indium. The conductor layer can be a single metal layer or an alloy layer. Examples of alloy layers include layers formed from alloys of two or more metals selected from the above-mentioned metals (e.g., nickel-chromium alloys, copper-nickel alloys, and copper-titanium alloys). From the viewpoints of versatility in conductor layer formation, cost, and ease of pattern formation, a single metal layer of chromium, nickel, titanium, aluminum, zinc, gold, palladium, silver, or copper, or an alloy layer of nickel-chromium alloy, copper-nickel alloy, or copper-titanium alloy, is preferred. A single metal layer of chromium, nickel, titanium, aluminum, zinc, gold, palladium, silver, or copper, or an alloy layer of nickel-chromium alloy, is even more preferred. A single metal layer of copper is even more preferred.

[0244] The conductor layer can have a single-layer structure or a multi-layer structure comprising two or more single-metal layers 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 nickel-chromium alloy.

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

[0246] The conductor layer can be formed by plating. For example, a conductor layer with a desired wiring pattern can be formed by plating the surface of the insulating layer using conventional techniques such as semi-additive and fully additive methods. From the viewpoint of ease of manufacturing, the semi-additive method is preferred. An example of forming a conductor layer by the semi-additive method is shown below.

[0247] First, an electroless plating 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 plating layer, corresponding to the desired wiring pattern, exposing a portion of the electroless plating layer. After forming an electrolytic plating layer on the exposed electroless plating layer by electrolytic plating, the mask pattern is removed. Then, the unwanted electroless plating layer is removed by etching, forming a conductor layer with the desired wiring pattern.

[0248] As another example, the conductor layer can be formed using metal foil. When forming the conductor layer using metal foil, it is preferable to perform step (V) between step (I) and step (II). For example, after step (I), the support is removed, and metal foil is laminated onto the surface of the exposed resin composition layer. The lamination of the resin composition layer and the metal foil can be performed by vacuum lamination. The lamination conditions can be the same as those described for step (I). Next, step (II) is performed to form an insulating layer. Then, using the metal foil on the insulating layer, a conductor layer with a desired wiring pattern can be formed by known techniques such as subtractive processing or modified semi-additive processing. Metal foil can be manufactured, for example, by known methods such as electrolysis or rolling. Commercially available metal foils include, for example, HLP foil and JXUT-III foil manufactured by JX Metals Corporation, and 3EC-III foil and TP-III foil manufactured by Mitsui Mining & Metals Corporation.

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

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

[0251] The method for manufacturing a circuit board can be combined with the aforementioned steps to further include any additional steps. For example, the method may include a step of placing a semiconductor chip in a manner that bonds it to a conductive layer. Specifically, in the case of manufacturing a circuit board for a semiconductor chip package containing a semiconductor chip, the method may include a step of placing the semiconductor chip. For the semiconductor chip, appropriate conditions can be used that allow for conductive connection between the terminal electrodes of the semiconductor chip and the conductive layer formed on the insulating layer. For example, conditions used in flip-chip mounting can be used. Furthermore, the semiconductor chip can be bonded using an insulating adhesive or by reflow soldering. Furthermore, if necessary, the placed semiconductor chip can be filled with a molding underfill material. Additionally, the method may include, for example, a step of forming a sealing layer, a step of forming a solder resist layer, and a step of cutting the manufactured circuit board for monolithic assembly.

[0252] Examples of circuit boards include printed wiring boards and semiconductor chip packages. Examples of semiconductor chip packages include FC-CSP, MIS-BGA packages, ETS-BGA packages, 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 use a cured product formed by curing the aforementioned resin composition to form a rewiring layer as an insulating layer. However, the circuit board is not limited to the circuit board in this example.

[0253] [Semiconductor Devices] The circuit board described above can be used in the manufacture of semiconductor devices. Semiconductor devices include the circuit board described above. Examples of semiconductor devices include various semiconductor devices used in electrical products (e.g., computers, mobile phones, smartphones, tablets, wearable devices, digital cameras, medical devices, and televisions) and vehicles (e.g., motorcycles, automobiles, trams, ships, and airplanes). Example

[0254] The following examples illustrate the invention in detail. However, the invention is not limited to these examples. In the following description, "parts" and "%" refer to "parts by mass" and "% by mass," respectively, unless otherwise specified. Additionally, the temperature and pressure conditions, unless otherwise specified, are room temperature (23°C) and atmospheric pressure (1 atm). In the following description, unless otherwise specified, "Mw" represents weight-average molecular weight, and "Mn" represents number-average molecular weight.

[0255] <Synthesis Example 1: Synthesis of Active Ester Resin 1> 320 g (2.0 mol) of 2,7-dihydroxynaphthalene, 184 g (1.7 mol) of benzyl alcohol, and 5.0 g of p-toluenesulfonic acid monohydrate were added to a flask equipped with a thermometer, dropping funnel, condenser, fractionating tube, and stirrer. The mixture was stirred while being purged with nitrogen at room temperature. The temperature was then raised to 150 °C, and the generated water was distilled off to remove it from the system while stirring for 4 hours. After the reaction was complete, 900 g of methyl isobutyl ketone and 5.4 g of 20% sodium hydroxide aqueous solution were added for neutralization. The aqueous layer was then removed by separation, followed by three washes with 280 g of water. Methyl isobutyl ketone was removed under reduced pressure to obtain 460 g of benzyl-modified naphthalene compound (A'). The obtained benzyl-modified naphthalene compound (A') was a black solid with a hydroxyl equivalent of 180 g / eq.

[0256] In a flask equipped with a thermometer, dropping funnel, condenser, fractionating tube, and stirrer, 203.0 g of isophthaloyl chloride (2.0 mol of acyl chloride group) and 1400 g of toluene were added. The system was purged with nitrogen under reduced pressure and dissolved. Next, 72.4 g (0.67 mol) of o-cresol and 240 g of benzyl-modified naphthalene compound (A') (1.33 mol of phenolic hydroxyl group) were added, and the system was purged with nitrogen under reduced pressure and dissolved. Then, 0.70 g of tetrabutylammonium bromide was dissolved, and while purging with nitrogen and maintaining the system temperature below 60°C, 400 g of 20% sodium hydroxide aqueous solution was added dropwise over 3 hours. The reaction was then continued under these conditions with stirring for 1 hour.

[0257] After the reaction was completed, the mixture was allowed to stand and separated, and the aqueous layer was removed. Then, water was added to the toluene layer containing the reactants and stirred for 15 minutes. The mixture was allowed to stand and separated, and the aqueous layer was removed. This process was repeated until the pH of the aqueous layer reached 7. The water was then removed by decantering to obtain active ester resin 1 in a toluene solution containing 65% by mass of non-volatile components. The active ester equivalent of the obtained active ester resin 1 was 238 g / eq.

[0258] <Synthesis Example 2: Synthesis of Active Ester Resin 2> In a flask equipped with a thermometer, dropping funnel, condenser, fractionating tube, and stirrer, add 165 g of a dicyclopentadiene and phenol addition polymerization resin (hydroxyl equivalent: 165 g / eq., softening point 85 °C), 134 g (1.0 mol) of o-allylphenol, and 1200 g of toluene. The system is then purged with nitrogen under reduced pressure. Next, add 203 g (1.0 mol) of isophthaloyl chloride, and purge with nitrogen under reduced pressure. Then, add 0.6 g of tetrabutylammonium bromide, and while purging with nitrogen and maintaining the system temperature below 60 °C, add 412 g of a 20% sodium hydroxide aqueous solution dropwise over 3 hours. After the addition is complete, stir for 1 hour. After the reaction is complete, remove the aqueous layer by standing and separating the layers. Add water to the resulting toluene layer, stir for 15 minutes, and remove the aqueous layer by standing and separating the layers. Repeat this process until the pH of the aqueous layer reaches 7. Then, the non-volatile components were adjusted to 70% by mass by heating and drying to obtain active ester resin 2 as shown in the following formula (mainly composed of compounds with integers S = 0 to 6 and r = 0 to 6). The active ester equivalent of the obtained active ester resin 2 is 214 g / eq. [Chemical Formula 16]

[0259] <Synthesis Example 3: Synthesis of Maleimide Resin D> According to Synthesis Example 1 published by the Japan Invention Association under Patent No. 2020-500211, a MEK solution of maleimide resin D (62% by mass of non-volatile component) as shown in formula (1) was prepared. The Mw / Mn ratio of the maleimide resin D is 1.81, and t” in formula (1) is 1.47 (mainly 1, 2 or 3). [Chemical Formula 17]

[0260] <Synthesis Example 4: Synthesis of Vinyl Resin D-1> According to Example 1 of International Publication No. 2017 / 115813, 3.0 mol (390.6 g) of divinylbenzene, 1.8 mol (229.4 g) of ethylvinylbenzene, 10.2 mol (1066.3 g) of styrene, and 15.0 mol (1532.0 g) of n-propyl acetate were added to a 5.0 L reactor. 600 mmol of a boron trifluoride diethyl ether complex was added at 70 °C, and the reaction was carried out for 4 hours. The polymerization solution was stopped with an aqueous sodium bicarbonate solution. The oil layer was then washed three times with pure water, and the polymer was recovered by vacuum devolatilization at 60 °C. The obtained polymer was weighed, confirming that 896.7 g of vinyl resin D-1 was obtained. The weight-average molecular weight (Mw) of vinyl resin D-1 was 41300.

[0261] <Examples 1-12 and Comparative Examples 1-3> (1) Preparation of resin composition: Weigh and mix the components according to the formulation listed in the table below, then mix 10 parts MEK and 10 parts cyclohexanone, and disperse evenly using a high-speed rotary mixer to obtain a resin composition (resin varnish). It should be noted that the formulation listed in the table below represents the amount (parts by mass) of non-volatile components. [Table 1]

[0262] The details of each component listed in the table are as follows. (A) Epoxy resin: HP-4032-SS: Epoxy equivalent 144 g / 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 containing the following compound (mainly composed of compounds with n as an integer from 0 to 6), an active ester equivalent of 250 g / eq., and 62% by mass of non-volatile components. [Chemical Formula 18] (B-2-i) components: • Active ester resin 2: 214 g / eq. of active ester group equivalent, active ester resin synthesized in Synthesis Example 2, and a toluene solution containing 70% by mass of non-volatile components. • Active ester resin 3: Active ester equivalent 248 g / eq., a compound shown in the following formula (mainly composed of compounds where n is an integer from 0 to 6 and m is an integer from 0 to 6). A toluene solution containing 70% by mass of non-volatile components. [Chemical Formula 19] • Active ester resin 4: Active ester equivalent 1002 g / eq., manufactured by DIC, active ester resin as shown in the following formula (mainly composed of compounds in which m is an integer from 0 to 6 and n is an integer from 6 to 30). [Chemical Formula 20] (B-2-ii) Ingredients: HPC-8000L-65MT: An active ester resin containing a dicyclopentadiene-type diphenol structure, with an active ester equivalent of 223 g / eq. and 65% by mass of non-volatile components in a toluene / MEK solution. Manufactured by DIC Corporation. • Active ester resin 1: Active ester group equivalent 238 g / eq., the active ester resin synthesized in Synthesis Example 1. (C) Ingredients: • SO-C2: Spherical silica surface-treated with an amino-based silane coupling agent (Shin-Etsu Chemical Industry Co., Ltd. "KBM573"), with an average particle size of 0.5 μm and a specific surface area of ​​5.8 m². 2 / g, made by Yaduma Company. (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 having the structure shown in the following formula (mainly composed of compounds with n=1 to 6). [Chemical Formula 21] ·SLK-6895: Aliphatic maleimide resin manufactured by Shin-Etsu Chemical Industry Co., Ltd. SLK-1500: Aliphatic maleimide resin manufactured by Shin-Etsu Chemical Industry Co., Ltd. •OPE-2St-1200: A styrene-based free radical polymerizable resin with a polyphenylene ether backbone, consisting of a toluene solution containing 65% by mass of non-volatile components and manufactured by Mitsubishi Gas Chemical Co., Ltd. • Vinyl resin D-1: Vinyl resin D-1 synthesized in Synthesis Example 4. (E) Components: LA-3018-50P: Phenolic hydroxyl equivalent 151 g / eq., 50% by mass of non-volatile component in 1-methoxy-2-propanol solution, manufactured by DIC, phenolic resin. (F)Ingredients: EXL-2655: An organic filler material containing rubber components manufactured by Dow Chemical Company. (G) Ingredients: ·1B2PZ: Imidazole-based curing accelerator manufactured by Shikoku Chemical Industry Co., Ltd.

[0263] (2) Manufacturing of resin sheet A: As a support, a polyethylene terephthalate film (Lintec "AL5", 38 μm thick) with a release layer was prepared. The obtained resin composition was uniformly coated onto the release layer of this support, with a dried resin composition layer thickness of 40 μm. The resin composition was then dried at 80°C–100°C (average 90°C) for 4 minutes to obtain a resin sheet A with a resin composition layer / support layer structure.

[0264] <Experiment 1. Determination 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. Then, the support was peeled off to obtain the cured resin composition layer. This cured layer was cut into samples with a length of 30 mm and a width of 40 mm to obtain cured samples for dielectric property testing.

[0265] For the solidified samples, the dielectric constant and dielectric loss tangent were determined using a measuring apparatus (Agilent Technologies, "HP8362B") via the split cylinder method at a measurement frequency of 10 GHz and a measurement temperature of 90 °C. Measurements were performed on two samples, and the average values ​​were calculated.

[0266] <Experiment 2. Determination 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 then the support was peeled off to obtain a cured film. The cured film was cut into 20 mm long and 6 mm wide pieces to obtain a cured sample for measuring the coefficient of linear thermal expansion. For this cured sample, Tg and CTE were measured using a TMA apparatus (Thermomechanical Analysis Apparatus, manufactured by Rigaku Corporation). Specifically, after mounting the cured sample on the apparatus described above, two consecutive measurements were performed under the conditions of a load of 1 g and a heating rate of 5°C / min (the first measurement was performed by heating from 25°C to 220°C, and the second measurement was performed by heating from 25°C to 250°C), and the values ​​of the second measurement were recorded.

[0267] <Experiment 3. Evaluation Test of Stain Removability> (1) Preparation of the inner layer substrate: The inner layer substrate is obtained by etching 1 μm on both sides of a glass cloth substrate epoxy resin double-sided copper-clad laminate (copper foil thickness 18 μm, substrate thickness 0.4 mm, Panasonic "R1515A") with inner layer circuitry formed by the substrate using a micro-etching agent (MEC "CZ8101") to roughen the copper surface.

[0268] (2) Lamination of resin sheet A: Using a batch vacuum pressure laminator (Nikko-materials, 2-stage stacking laminator "CVP700"), resin sheet A was laminated onto both sides of the inner layer substrate in such a manner that the resin composition layer was in contact with the inner layer substrate. The lamination was performed by adjusting the pressure to below 13 hPa after a 30-second depressurization, followed by pressing at 120°C and 0.74 MPa for 30 seconds. Next, a hot press was performed at 100°C and 0.5 MPa for 60 seconds to smooth the resin composition layer.

[0269] (3) Thermosetting of the resin composition layer: Then, the inner substrate with resin sheet A stacked on it is placed in an oven at 130°C and heated for 30 minutes, followed by heating in an oven at 170°C for 30 minutes to thermally cure the resin composition layer and form an insulating layer. Then, the support is peeled off to obtain a cured substrate with an insulating layer / inner substrate / insulating layer structure.

[0270] (4) Formation of through holes: The insulating layer of the resulting cured substrate was processed using a CO2 laser processing machine (Via Machinery Co., Ltd. "LK-2K212 / 2C") at a frequency of 2000 Hz, a pulse width of 3 microseconds, an output power of 0.95 W, and a shot count of 3 to create through-holes. The opening diameter (top diameter) of the insulating layer surface of the formed through-hole is 50 μm, and the diameter (bottom diameter) of the insulating layer bottom surface is also 50 μm.

[0271] (5) Roughening treatment: The insulating layer of the cured substrate with through-holes is subjected to a decontamination treatment as a roughening process. As a decontamination treatment, the following wet decontamination treatment is performed.

[0272] (Wet stain removal treatment) The cured substrate was immersed in a swelling solution (Swelling Dip Securiganth P manufactured by Amtec Japan, an aqueous solution of diethylene glycol monobutyl ether and sodium hydroxide) at 60°C for 10 minutes. Next, the cured substrate was immersed in an oxidizing agent solution (Concentrate Compact P manufactured by Amtec Japan, an aqueous solution of approximately 6% potassium permanganate and approximately 4% sodium hydroxide) at 80°C for 25 minutes. Finally, the cured substrate was immersed in a neutralization solution (Reduction Solution Securiganth P manufactured by Amtec Japan, an aqueous solution of sulfuric acid) at 40°C for 5 minutes. Then, the cured substrate was dried at 80°C for 15 minutes. This decontamination-treated cured substrate is sometimes referred to below as "Evaluation Substrate A".

[0273] (6) Evaluation of stain removal performance: For the evaluation substrate A, the area around the bottom of the via was observed using a scanning electron microscope (SEM). The length of the longest contaminant (maximum contaminant length) extending from the wall surface at the bottom of the via was determined from the obtained image, and the evaluation was performed according to the following criteria. 〇: Maximum contamination length is less than 5μm. ×: The maximum contamination length is 5μm or more.

[0274] <Example 3: Determination of the seal between the conductor layer and the high-temperature and high-humidity environment (HAST) test> (1) Resin sheet A is laminated on the inner substrate. As the inner layer substrate, a glass cloth substrate epoxy resin double-sided copper-clad laminate with copper foil on the surface was prepared (copper foil thickness 18μm, substrate thickness 0.8mm, Panasonic "R1515A"). The copper foil on the surface was etched with a copper etching agent (Mec "CZ8101") at a copper etching amount of 1μm to roughen the surface.

[0275] The resin sheet A obtained above was laminated onto both sides of the inner substrate using a batch vacuum pressure laminator (Nikko-materials CVP700, a two-stage stacking laminator). The resin composition layer of the resin sheet A was in contact with the inner substrate. The lamination was performed by depressurizing the pressure for 30 seconds to bring it below 13 hPa, and then pressing it at 100°C and 0.74 MPa for 30 seconds.

[0276] Next, the laminated resin sheet A is hot-pressed for 60 seconds at 100°C and 0.5 MPa under atmospheric pressure to smooth it. Then, the support is peeled off to obtain "intermediate multilayer I" which sequentially comprises a resin composition layer / inner substrate / resin composition layer.

[0277] (2) Layering of copper foil A copper foil with a glossy surface (35 μm thick, manufactured by Mitsui Metals & Mining Co., Ltd., "3EC-III") was prepared. The glossy surface of the copper foil was roughened by etching with a copper etching amount of 1 μm using a micro-etching agent (manufactured by Mec Corporation, "CZ8101"). The resulting copper foil is referred to as "roughened copper foil".

[0278] The roughened copper foil is laminated on both sides of the intermediate multilayer body I in such a way that the roughened surface of the copper foil is bonded to the resin composition layer of the intermediate multilayer body I. This lamination is performed under the same conditions as the lamination of the resin sheet A on the inner substrate. Thus, an "intermediate multilayer body II" is obtained, which sequentially comprises roughened copper foil / resin composition layer / inner substrate / resin composition layer / roughened copper foil.

[0279] (3) Thermosetting of the resin composition layer The obtained intermediate multilayer II was placed in an oven at 100°C and heated for 30 minutes, then transferred to an oven at 170°C and heated for another 30 minutes. Next, the intermediate multilayer II was removed from the oven and allowed to cool to room temperature, then placed in an oven at 190°C and heated for an additional 90 minutes. This process of thermosetting the resin composition layer resulted in an "evaluation substrate C" sequentially comprising a roughened copper foil, an insulating layer as a cured resin composition layer, an inner substrate, an insulating layer as a cured resin composition layer, and a roughened copper foil. In this evaluation substrate C, the roughened copper foil serves as a conductor layer.

[0280] (4) Determination of the adhesion strength with the conductor layer Using the obtained evaluation substrate C, the peel strength between the roughened copper foil and the insulating layer was measured. This peel strength measurement was performed according to JIS C6481. Specifically, the peel strength was measured through the following procedures.

[0281] A rectangular section, 10 mm wide and 100 mm long, was cut into the roughened copper foil of the evaluation substrate C. One end of this rectangular section was peeled off and clamped in a jig (TSE Auto Com type testing machine "AC-50C-SL"). A 35 mm long section of this rectangular section was peeled off vertically, and the peel load (kgf / cm) was measured as the peel strength. The peeling was performed at a speed of 50 mm / min at room temperature.

[0282] Subsequently, after conducting a 100-hour environmental test (HAST test) at 130°C and 85% RH, the same operation as above was performed to determine the peel strength.

[0283] [Table 2]

Claims

1. A resin composition comprising: (A) Epoxy resin, (B) Active ester compounds, and (C) Inorganic filler materials (B) The ingredient comprises: (B-1) an active ester compound represented by formula (B-1a) below, and (B-2) an active ester compound other than the ingredient (B-1). In the formula, R 11 Each of these can be independently represented as a monovalent aromatic group with optional substituents. R 12 Each of the following can be independently represented as a divalent aromatic group with optional substituents: R 13 Each of these can be independently represented as a divalent aromatic group with a fused ring structure, optionally having a substituent. R 14 Each can be independently represented as a divalent hydrocarbon group with optional substituents. n1 represents an integer greater than or equal to 0.

2. The resin composition according to claim 1, wherein, The (B-2) component contains (B-2-i) active ester compounds with carbon-carbon double bonds.

3. The resin composition according to claim 1, wherein, The (B-2-i) component comprises any one of the active ester compound represented by formula (Bi), the active ester compound represented by formula (B-ii), and the active ester compound represented by formula (B-iii). In formula (Bi), Ar 11 Each of these can be independently represented as a monovalent aromatic group with optional substituents. Ar 12 Each of the following can be independently represented as a divalent aromatic group with optional substituents: Ar 13 Each of these can be independently represented as an optional divalent aromatic group with substituents, an optional divalent aliphatic group with substituents, an oxygen atom, a sulfur atom, or a divalent group composed of combinations thereof. mi and ni represent integers greater than 0 independently. Among them, Ar 11 Ar 12 and Ar 13 At least one of them has a substituent containing a carbon-carbon double bond; In equation (B-ii), Ar 11 Each of these can be independently represented as a monovalent aromatic group with optional substituents. Ar 12 Each of the following can be independently represented as a divalent aromatic group with optional substituents: Ar 13 Each of these can be independently represented as an optional divalent aromatic group with substituents, an optional divalent aliphatic group with substituents, an oxygen atom, a sulfur atom, or a divalent group composed of combinations thereof. mii and nii independently represent integers greater than 0. Among them, Ar 11 Ar 12 and Ar 13 At least one of them has a substituent containing a carbon-carbon double bond; In equation (B-iii), Ar 1 Each of these can be independently represented as a monovalent aromatic group with optional substituents. Ar 2 Each of the following can be independently represented as a divalent aromatic group with optional substituents: R 1 Each of these can be independently represented as a divalent aliphatic group with optional substituents. R 2 The butadiene structure is represented independently. m and n each represent an integer greater than 0 independently.

4. The resin composition according to claim 1, wherein, The (B-2) component contains (B-2-ii) active ester compounds that do not contain carbon-carbon double bonds.

5. The resin composition according to claim 1, wherein, Further includes (D) radical polymerizable compounds.

6. The resin composition according to claim 5, wherein, (D) Component contains maleimide resin.

7. The resin composition according to claim 1, wherein, It further includes (E) other curing agents.

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

9. The resin composition according to claim 1, wherein, In equation (B-1a), R 14 This indicates 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 comprising the resin composition of any one of claims 1 to 9 disposed on the support.

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

12. A semiconductor device comprising the circuit board of claim 11.

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