Resin composition

Abstract

To provide a novel resin composition capable of giving a cured product exhibiting good adhesion with a plated conductor when forming a wiring pattern by a semi-additive method, and exhibiting good adhesion with a substrate conductor when exposed to a high temperature and high humidity environment even when adopting a composition which contributes good dielectric characteristics.SOLUTION: A resin composition includes : (A) a compound represented by the following formula (1); (B) an epoxy resin; and (C) a curing agent. R1 is independently a substituted or unsubstituted univalent hydrocarbon group, or a substituted or unsubstituted univalent heteroatom-containing hydrocarbon group; R2 is a hydrogen atom, a substituted or unsubstituted univalent hydrocarbon group, or a substituted or unsubstituted univalent heteroatom-containing hydrocarbon group; R3 is a substituted or unsubstituted bivalent hydrocarbon group; R4 is a hydrogen atom, a substituted or unsubstituted univalent hydrocarbon group, a substituted or unsubstituted univalent heteroatom-containing hydrocarbon group, or a substituted or unsubstituted amino group; m is a number of 0-4; and n is 0 or 1.SELECTED DRAWING: None

Description

Technical Field

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

Background Art

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

[0003] On the other hand, with the recent high-speedization of communication, insulating materials for circuit boards are required to have excellent dielectric properties (low dielectric constant, low dielectric tangent) in order to reduce transmission loss when operating in a high-frequency environment. As insulating materials with excellent dielectric properties, specific curing agents such as active ester-based curing agents that can reduce and suppress the generation of polar groups such as secondary hydroxyl groups in the curing reaction of epoxy resins are used, or a specific composition is adopted such as high blending of inorganic fillers (for example, Patent Documents 1 to 3).

Prior Art Documents

Patent Documents

[0004]

Patent Document 1

Patent Document 2

Patent Document 3

Summary of the Invention

Problems to be Solved by the Invention

[0005] As a manufacturing technique for a circuit board, a manufacturing method by a build-up method in which an insulating layer and a conductor layer (circuit layer) are alternately laminated is known. In the manufacturing method by the build-up method, generally, a resin composition layer is laminated on a substrate using a resin sheet or the like, and the resin composition layer is cured to form an insulating layer. Thereafter, the insulating layer is roughened and subjected to a plating process to provide a conductor layer and form a wiring pattern. Here, as a method for forming a wiring pattern, generally, a semi-additive method is used from the viewpoint of easily forming fine wirings.

[0006] When the present inventors formed a wiring pattern by the semi-additive method and formed an insulating layer using a conventional resin composition that contributes to good dielectric properties, they found that the adhesion between the obtained insulating layer and the plated conductor was sometimes not sufficiently obtained. Although such adhesion to the plated conductor can be improved by using a certain amount of dimethylaminopyridine (DMAP) as a curing accelerator, when DMAP is used in an amount that provides good adhesion to the plated conductor, the adhesion to the underlying conductor, particularly after exposure to a high-temperature and high-humidity environment, tends to deteriorate.

[0007] An object of the present invention is to provide a novel resin composition that exhibits good adhesion to a plated conductor when forming a wiring pattern by the semi-additive method even when adopting a composition that contributes to good dielectric properties, and exhibits good adhesion to an underlying conductor when exposed to a high-temperature and high-humidity environment, and can provide a cured product.

Means for Solving the Problems

[0008] As a result of intensive studies, the present inventors have found that the above problems can be solved by a resin composition having the following configuration, and have completed the present invention.

[0009] That is, the present invention includes the following contents. [1] A resin composition containing (A) a compound represented by the following formula (1), (B) an epoxy resin, and (C) a curing agent.

Chemical formula

[10] The resin composition according to any one of [1] to [9], wherein the content of the component (A) is 0.1% by mass or more and 10% by mass or less when the resin components in the resin composition are 100% by mass.

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

[10] , wherein the value of the dielectric tangent of the cured product is 0.004 or less.

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

[11] , which is for an insulating layer of a circuit board.

[13] A resin sheet including a support and a layer of the resin composition according to any one of [1] to

[12] provided on the support.

[14] The resin sheet according to

[13] , wherein the support is a thermoplastic resin film or a metal foil.

[15] A cured product of the resin composition according to any one of [1] to

[12] .

[16] A circuit board including an insulating layer made of a cured product of the resin composition according to any one of [1] to

[12] .

[17] A semiconductor device including the circuit board according to

[16] .

Advantages of the Invention

[0010] According to the present invention, even when a composition contributing to good dielectric properties is adopted, a cured product can be provided that exhibits good adhesion to a plating conductor when a wiring pattern is formed by the semi-additive method and exhibits good adhesion to an underlying conductor when exposed to a high-temperature and high-humidity environment, and a novel resin composition can be provided.

Embodiments for Carrying Out the Invention

[0011] <Explanation of Terms> In this specification, the term "hydrocarbon group" refers to a group obtained by removing one or more hydrogen atoms from a hydrocarbon compound. Specifically, a monovalent hydrocarbon group refers to a group obtained by removing one hydrogen atom from a hydrocarbon compound, and a divalent hydrocarbon group refers to a group obtained by removing two hydrogen atoms from a hydrocarbon compound. Here, the hydrocarbon group may be any saturated or unsaturated hydrocarbon group and may have a cyclic structure. Examples of the monovalent hydrocarbon group include an alkyl group, an alkenyl group, an alkynyl group, an alkapolyenyl group, and a monovalent carbocyclic group. Examples of the divalent hydrocarbon group include an alkylene group, an alkenylene group, an alkynylene group, an alkapolyenylene group, and a divalent carbocyclic group. In this specification, unless otherwise specified, the number of carbon atoms in the hydrocarbon group is preferably 1 or more, more preferably 2 or more, still more preferably 3 or more, 4 or more, 5 or more, or 6 or more, and preferably 50 or less, more preferably 40 or less, still more preferably 30 or less, 20 or less, 18 or less, 16 or less, 14 or less, or 12 or less. The number of carbon atoms of the substituents described later is not included in the number of carbon atoms.

[0012] In the present specification, the term "heteroatom-containing hydrocarbon group" refers to a group obtained by removing one or more hydrogen atoms from a hydrocarbon compound containing a heteroatom. Specifically, a monovalent heteroatom-containing hydrocarbon group refers to a group obtained by removing one hydrogen atom from a hydrocarbon compound containing a heteroatom, and a divalent heteroatom-containing hydrocarbon group refers to a group obtained by removing two hydrogen atoms from a hydrocarbon compound containing a heteroatom. In the "heteroatom-containing hydrocarbon group" in the present specification, the heteroatom may be bonded to any of the carbon atoms constituting the group. For example, (i) it may be interposed between carbon-carbon bonds, or (ii) it may be bonded to a terminal carbon. Further, in the "heteroatom-containing hydrocarbon group" in the present specification, the bond may extend from a carbon atom or from a heteroatom. The heteroatom-containing hydrocarbon group may be either a saturated or unsaturated heteroatom-containing hydrocarbon group, and may have a cyclic structure. In the present specification, the term "heteroatom" refers to an atom other than a carbon atom and a hydrogen atom, and examples thereof include an oxygen atom, a nitrogen atom, a sulfur atom, a silicon atom, and the like. Examples of the monovalent heteroatom-containing hydrocarbon group include a heteroalkyl group, a heteroalkenyl group, a heteroalkynyl group, a heteroalkapolyenyl group, and a monovalent heterocyclic group. The monovalent heteroatom-containing hydrocarbon group also includes a monovalent group formed by bonding a divalent group selected from the group consisting of -O-, -S-, -C(=O)-, -S(=O)-, -S(=O)2-, -N(R)-, -Si(R)2-, and combinations thereof to the bond of a monovalent carbocyclic group or a monovalent heterocyclic group (wherein R represents a hydrogen atom or a substituent described later. The same applies hereinafter). In the present specification, unless otherwise specified, the number of heteroatoms in the heteroatom-containing hydrocarbon group is preferably 1 or more, 2 or more, or 3 or more, and is preferably 10 or less, 8 or less, or 6 or less. Further, the number of carbon atoms thereof is preferably 1 or more, more preferably 2 or more, still more preferably 3 or more, 4 or more, 5 or more, or 6 or more, and is preferably 50 or less, more preferably 40 or less, still more preferably 30 or less, 20 or less, 18 or less, 16 or less, 14 or less, or 12 or less. The number of heteroatoms and carbon atoms of the substituents described later are not included in the number of heteroatoms and carbon atoms of the heteroatom-containing hydrocarbon group.

[0013] As used herein, the term "alkyl group" refers to a monovalent saturated hydrocarbon group, which may be either linear or branched. The number of carbon atoms in the alkyl group is as described for the "hydrocarbon group", but is preferably 1 or more and 12 or less, more preferably 1 or more and 10 or less, still more preferably 1 or more and 8 or less, or 1 or more and 6 or less. Examples of the alkyl group include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a tert-pentyl group, a neopentyl group, a 2-pentyl group, a 3-pentyl group, an n-hexyl group, and a 2-hexyl group.

[0014] As used herein, the term "alkenyl group" refers to a monovalent unsaturated hydrocarbon group having one carbon-carbon double bond, which may be either linear or branched. The number of carbon atoms in the alkenyl group is as described for the "hydrocarbon group", but is preferably 2 or more and 12 or less, more preferably 2 or more and 10 or less, still more preferably 2 or more and 8 or less, or 2 or more and 6 or less. Examples of the alkenyl group include a vinyl group, an allyl group, a propenyl group, a butenyl group, a pentenyl group, a hexenyl group, a heptenyl group, an octenyl group, a nonenyl group, a decenyl group, and their respective isomers.

[0015] As used herein, the term "alkynyl group" refers to a monovalent unsaturated hydrocarbon group having one carbon-carbon triple bond, which may be either linear or branched. The number of carbon atoms in the alkynyl group is as described for the "hydrocarbon group", but is preferably 2 or more and 12 or less, more preferably 2 or more and 10 or less, still more preferably 2 or more and 8 or less, or 2 or more and 6 or less. Examples of the alkynyl group include an ethynyl group, a propynyl group, a butynyl group, a pentynyl group, a hexynyl group, a heptynyl group, an octynyl group, a nonynyl group, a decynyl group, and their respective isomers.

[0016] As used herein, the term "alkapolyenyl group" refers to a monovalent unsaturated hydrocarbon group having two or more carbon-carbon double bonds, which may be linear or branched. The number of carbon-carbon double bonds in the alkapolyenyl group is preferably 2 or more and 6 or less, more preferably 2 or more and 4 or less, or 2 or 3. The number of carbon atoms in the alkapolyenyl group is as described for the "hydrocarbon group", but is preferably 3 or more and 12 or less, more preferably 3 or more and 10 or less, still more preferably 3 or more and 8 or less, or 3 or more and 6 or less. In addition, the lower limit of the number of carbon atoms is preferably 4 or more. Examples of the alkapolyenyl group include a butadienyl group, a hexatrienyl group, and their respective isomers.

[0017] As used herein, the term "monovalent carbocyclic group" refers to a group obtained by removing one hydrogen atom on the carbocyclic ring from a cyclic hydrocarbon. Here, the carbocyclic ring may be either a saturated carbocyclic ring or an unsaturated carbocyclic ring, and may be any of a monocyclic carbocyclic ring, a condensed polycyclic carbocyclic ring formed by condensation of two or more monocyclic carbocyclic rings, or a spirocyclic carbocyclic ring formed by spiro-bonding of two or more monocyclic carbocyclic rings. The number of carbon atoms of the monovalent carbocyclic group is as described for the "hydrocarbon group", but is preferably 3 or more and 20 or less, more preferably 3 or more and 15 or less, still more preferably 3 or more and 14 or less, 3 or more and 12 or less, 3 or more and 10 or less, 3 or more and 7 or less, or 3 or more and 6 or less. Examples of the monovalent carbocyclic group include, as a monovalent saturated carbocyclic group, a cycloalkyl group; and, as a monovalent unsaturated carbocyclic group, a cycloalkenyl group, a cycloalkynyl group, and a cycloalkapolyenyl group. Among the cycloalkapolyenyl groups, those that exhibit aromaticity in accordance with Hückel's rule where the number of electrons contained in the π-electron system on the ring is 4p + 2 (p is a natural number) are also referred to as "aryl groups". Examples of the cycloalkyl group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, dicyclopentanyl group, perhydropentalenyl group, perhydroazulenyl group, perhydroindenyl group, perhydronaphthyl group, spiro[4.4]nonyl group, spiro[4.5]decanyl group, spiro[5.5]undecanyl group, bicyclo[2.2.1]heptyl group, bicyclo[3.1.1]heptyl group, bicyclo[2.2.2]octyl group, adamantyl group, and noradamantyl group. Examples of the cycloalkenyl group include a cyclopropenyl group, a cyclobutenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, dicyclopentenyl group, bicyclo[2.2.1]hepta-2-enyl group, bicyclo[3.1.1]hepta-2-enyl group, and bicyclo[2.2.2]octa-2-enyl group. Examples of the cycloalkynyl group include a cyclopropynyl group, a cyclobutinyl group, a cyclopentynyl group, a cyclohexynyl group, and a cycloheptynyl group.As the cycloalkapolyenyl group, those having 2 to 10 (preferably 2 to 8, more preferably 2 to 7, or 2 to 6) carbon-carbon double bonds are suitable. For example, (a) cyclohexadienyl group, cycloheptadienyl group, pentalenyl group, biphenylenyl group, as-indacenyl group, s-indacenyl group; (b) cyclopentadienyl group, phenyl group, azulienyl group, indenyl group, indanyl group, naphthyl group, dihydronaphthyl group, tetrahydronaphthyl group, fluorenyl group, phenanthrenyl group, anthracenyl group. Among them, as the aryl group exhibiting aromaticity, those listed in the latter group (b) etc. can be mentioned.

[0018] In this specification, the term "alkylene group" refers to a divalent saturated hydrocarbon group, which may be either linear or branched. The number of carbon atoms of the alkylene group is as described for the "hydrocarbon group", and its preferred range is the same as that of the above "alkyl group". Examples of the alkylene group include divalent groups obtained by further removing one hydrogen atom from the above "alkyl group". The term "alkenylene group" refers to a divalent unsaturated hydrocarbon group having one carbon-carbon double bond, which may be either linear or branched. The number of carbon atoms of the alkenylene group is as described for the "hydrocarbon group", and its preferred range is the same as that of the above "alkenyl group". Examples of the alkenylene group include divalent groups obtained by further removing one hydrogen atom from the above "alkenyl group". The term "alkynylene group" refers to a divalent unsaturated hydrocarbon group having one carbon-carbon triple bond, which may be either linear or branched. The number of carbon atoms of the alkynylene group is as described for the "hydrocarbon group", and its preferred range is the same as that of the above "alkynyl group". Examples of the alkynylene group include divalent groups obtained by further removing one hydrogen atom from the above "alkynyl group". The term "alkapolyenylene group" refers to a divalent unsaturated hydrocarbon group having two or more carbon-carbon double bonds, which may be either linear or branched. The preferred ranges of the number of carbon-carbon double bonds in the alkapolyenylene group and the number of carbon atoms in the alkapolyenylene group are the same as those of the above-mentioned "alkapolyenyl group". Examples of the alkapolyenylene group include divalent groups obtained by further removing one hydrogen atom from the above-mentioned "alkapolyenyl group". The term "divalent carbocyclic group" refers to a group obtained by removing two hydrogen atoms on the carbocyclic ring from a cyclic hydrocarbon. The number of carbon atoms in the divalent carbocyclic group is as described for the "hydrocarbon group", and its preferred range is the same as that of the above-mentioned "monovalent carbocyclic group". Examples of the divalent carbocyclic group include, for example, a cycloalkylene group as a divalent saturated carbocyclic group; a cycloalkenylene group, a cycloalkynylene group, and a cycloalkapolyenylene group as divalent unsaturated carbocyclic groups, and among the cycloalkapolyenylene groups, those having aromaticity are also referred to as "arylene groups". Examples of the divalent carbocyclic group include divalent groups obtained by further removing one hydrogen atom from the above-mentioned "monovalent carbocyclic group".

[0019] As used herein, the term "heteroalkyl group" refers to a monovalent saturated hydrocarbon group containing a heteroatom, which may be either linear or branched. The number of heteroatoms and carbon atoms in the heteroalkyl group is as described for the "heteroatom-containing hydrocarbon group", but the number of heteroatoms is preferably 1 or more and 6 or less, more preferably 1 or more and 4 or less, or 1 or 2, and the number of carbon atoms is preferably 1 or more and 12 or less, more preferably 1 or more and 10 or less, still more preferably 1 or more and 8 or less, or 1 or more and 6 or less. In the heteroalkyl group, the heteroatom is preferably at least one selected from the group consisting of an oxygen atom, a nitrogen atom, a sulfur atom, and a silicon atom. For example, it may be present as a heteroatom such as -O- or -S-, or may be present as a heteroatom-containing group such as -C(=O)-, -S(=O)-, -S(=O)2-, -N(R)-, -Si(R)2-, or a combination thereof, or a combination of these with -O- or -S-. When the heteroalkyl group contains two or more heteroatoms, they may be the same or different from each other. As described above, the heteroatom may be interposed between carbon-carbon bonds or may be bonded to a terminal carbon.Examples of the heteroalkyl group include, for example, those in which the heteroatom is bonded to the terminal carbon: (i) an alkyloxy group (alkoxy group), an alkylthio group, an alkylsulfonyl group, an alkylsulfinyl group, an alkylcarbonyl group, an alkylamino group, an alkylsilyl group, an alkyloxycarbonyl group, an alkylcarbonyloxy group, an alkylamide group, an alkylimide group, an alkylureido group, an alkylsulfonylamino group, an alkyloxycarbonylamino group, and an alkylsilyloxy group, etc. (in the above, the mode in which a bond extends from the heteroatom or heteroatom-containing group), and also (ii) a hydroxyalkyl group, a mercaptoalkyl group, a sulfoalkyl group, an aminoalkyl group, a silylalkyl group, a carboxyalkyl group, an amidoalkyl group, an imidoalkyl group, and a ureidoalkyl group, etc. (in the above, the mode in which a bond extends from a carbon atom); those in which the heteroatom is interposed between carbon-carbon bonds include monovalent saturated hydrocarbon groups segmented by one or more divalent groups selected from the group consisting of -O-, -S-, -C(=O)-, -S(=O)-, -S(=O)2-, -N(R)-, -Si(R)2-, and combinations thereof. When the heteroalkyl group is an alkoxy group, specific examples thereof include a methyloxy group, an ethyloxy group, an n-propyloxy group, an isopropyloxy group, an n-butyloxy group, a sec-butyloxy group, an isobutyloxy group, a tert-butyloxy group, an n-pentyloxy group, an isopentyloxy group, a tert-pentyloxy group, a neopentyloxy group, a 2-pentyloxy group, a 3-pentyloxy group, an n-hexyloxy group, and a 2-hexyloxy group. Specific examples of the alkylthio group may be obtained by substituting "thio group" for "oxy group" in the above, and the same substitution and application may be made for specific examples of other groups such as the alkylsulfonyl group.

[0020] As used herein, the term "heteroalkenyl group" refers to a monovalent unsaturated hydrocarbon group containing a heteroatom and having one carbon-carbon double bond, which may be either linear or branched. The number of heteroatoms and carbon atoms in the heteroalkenyl group is as described for the "heteroatom-containing hydrocarbon group", but the number of heteroatoms is preferably 1 or more and 6 or less, more preferably 1 or more and 4 or less, or 1 or 2, and the number of carbon atoms is preferably 2 or more and 12 or less, more preferably 2 or more and 10 or less, still more preferably 2 or more and 8 or less, or 2 or more and 6 or less. Regarding the preferred types of heteroatoms and their positions of existence in the group, it is as described for the above "heteroalkyl group". Preferred examples of the heteroalkenyl group can be obtained by replacing "alkyl" with "alkenyl" and "monovalent saturated hydrocarbon group" with "monovalent unsaturated hydrocarbon group having one carbon-carbon double bond" in the groups exemplified for the above "heteroalkyl group". For example, as a mode in which a heteroatom is bonded to a terminal carbon and a bond extends from the heteroatom or a heteroatom-containing group, alkenyloxy group, alkenylthio group, alkenylsulfonyl group, alkenylsulfinyl group, alkenylcarbonyl group, alkenylamino group, alkenylsilyl group, alkenyloxycarbonyl group, alkenylcarbonyloxy group, alkenylamide group, alkenylimide group, alkenylureido group, alkenylsulfonylamino group, alkenyloxycarbonylamino group, and alkenylsilyloxy group, etc. can be mentioned. When the heteroalkenyl group is an alkenyloxy group, specific examples thereof include vinyloxy group, allyloxy group, propenyloxy group, butenyloxy group, pentyloxy group, hexyloxy group, heptyloxy group, octenyloxy group, nonenyloxy group, decenyloxy group, and their respective isomers. Specific examples of the alkenylthio group can be obtained by replacing "oxy group" with "thio group" in the above, and the same applies to specific examples of other groups such as the alkenylsulfonyl group.

[0021] As used herein, the term "heteroalkynyl group" refers to a monovalent unsaturated hydrocarbon group that contains a heteroatom and has one carbon-carbon triple bond, and may be either linear or branched. The number of heteroatoms and carbon atoms in the heteroalkynyl group is as described for the "heteroatom-containing hydrocarbon group", but the number of heteroatoms is preferably 1 or more and 6 or less, more preferably 1 or more and 4 or less, or 1 or 2, and the number of carbon atoms is preferably 2 or more and 12 or less, more preferably 2 or more and 10 or less, still more preferably 2 or more and 8 or less, or 2 or more and 6 or less. Regarding the preferred types of heteroatoms and their positions of existence in the group, it is as described for the above "heteroalkyl group". Preferred examples of the heteroalkynyl group may be obtained by respectively substituting "alkyl" with "alkynyl" and "monovalent saturated hydrocarbon group" with "monovalent unsaturated hydrocarbon group having one carbon-carbon triple bond" in the groups exemplified for the above "heteroalkyl group". For example, as a mode in which a heteroatom is bonded to a terminal carbon and a bond extends from the heteroatom or a heteroatom-containing group, there may be mentioned an alkynyloxy group, an alkynylthio group, an alkynylsulfonyl group, an alkynylsulfinyl group, an alkynylcarbonyl group, an alkynylamino group, an alkynylsilyl group, an alkynyloxycarbonyl group, an alkynylcarbonyloxy group, an alkynylamide group, an alkynylimide group, an alkynylureido group, an alkynylsulfonylamino group, an alkynyloxycarbonylamino group, and an alkynylsilyloxy group, etc. When the heteroalkynyl group is an alkynyloxy group, specific examples thereof include an ethynyloxy group, a propynyloxy group, a butynyloxy group, a pentynyloxy group, a hexynyloxy group, a heptynyloxy group, an octynyloxy group, a nonynyloxy group, a decynyloxy group, and their respective isomers. Specific examples of the alkynylthio group may be obtained by substituting "oxy group" with "thio group" as described above, and the same applies to specific examples of other groups such as the alkynylsulfonyl group.

[0022] As used herein, the term "heteroalkapolyenyl group" refers to a monovalent unsaturated hydrocarbon group that contains a heteroatom and has two or more carbon-carbon double bonds, and may be either linear or branched. The number of heteroatoms and carbon atoms in the heteroalkapolyenyl group is as described for the "heteroatom-containing hydrocarbon group", but the number of heteroatoms is preferably 1 or more and 6 or less, more preferably 1 or more and 4 or less, or 1 or 2, and the number of carbon atoms is preferably 3 or more and 12 or less, more preferably 3 or more and 10 or less, still more preferably 3 or more and 8 or less, or 3 or more and 6 or less. Preferred examples of the heteroalkapolyenyl group may be obtained by respectively replacing "alkyl" with "alkapolyenyl" and "monovalent saturated hydrocarbon group" with "monovalent unsaturated hydrocarbon group having two or more carbon-carbon double bonds" in the groups exemplified for the above "heteroalkyl group". For example, as a mode in which a heteroatom is bonded to a terminal carbon and a bond extends from the heteroatom or heteroatom-containing group, an alkapolyenyloxy group, an alkapolyenylthio group, an alkapolyenylsulfonyl group, an alkapolyenylsulfinyl group, an alkapolyenylcarbonyl group, an alkapolyenylamino group, an alkapolyenylsilyl group, an alkapolyenyloxycarbonyl group, an alkapolyenylcarbonyloxy group, an alkapolyenylamide group, an alkapolyenylimide group, an alkapolyenylureido group, an alkapolyenylsulfonylamino group, an alkapolyenyloxycarbonylamino group, and an alkapolyenylsilyloxy group, etc. may be mentioned. When the heteroalkapolyenyl group is an alkapolyenyloxy group, specific examples thereof include a butadienyloxy group, a hexatrienyloxy group, and their respective isomers. Specific examples of the alkapolyenylthio group may be obtained by replacing "oxy group" with "thio group" in the above, and the same applies to specific examples of other groups such as the alkapolyenylsulfonyl group.

[0023] In this specification, the term "monovalent heterocyclic group" refers to a group obtained by removing one hydrogen atom on the heterocycle from a heterocyclic compound. Here, the heterocycle may be either a saturated heterocycle or an unsaturated heterocycle, and may be any of a monocyclic heterocycle, a condensed polycyclic heterocycle, or a spirocyclic heterocycle. The number of heteroatoms and carbon atoms in the monovalent heterocyclic group is as described for the "heteroatom-containing hydrocarbon group", but the number of heteroatoms is preferably 1 or more and 10 or less, more preferably 1 or more and 8 or less, still more preferably 1 or more and 6 or less, or 1 or more and 4 or less. The number of ring members of the monovalent heterocyclic group is preferably 5 or more and 20 or less, more preferably 5 or more and 15 or less, still more preferably 5 or more and 12 or less, or 5 or more and 10 or less. In the monovalent heterocyclic group, the heteroatom is preferably one or more selected from the group consisting of an oxygen atom, a nitrogen atom, and a sulfur atom. Examples of the monovalent heterocyclic group include pyrrole, imidazole, triazole, tetrazole, pyrazole, pyridine, pyrazine, triazine, pyrimidine, pyridazine, azepine, diazepine, furan, pyran, oxepine, thiophene, thiopyran, thiepine, oxazole, isoxazole, thiazole, isothiazole, furazan, oxadiazole, oxazine, oxadiazine, oxazepine, oxadiazepine, thiadiazole, thiazine, thiadiazine, thiazepine, thiadiazepine, indole, isoindole, indolizine, benzofuran, isobenzofuran, benzothiophene, isobenzothiophene, dithianaphthalene, indazole, quinoline, isoquinoline, quinolidine, purine, phthalazine, pteridine, naphthyridine, quinoxaline, quinazoline, cinnoline, benzoxazole, benzothiazole, benzimidazole, chromene, benzoxepine, benzoxazepine, benzoxadiazepine, benzothiepine, benzothiazepine, benzothiadiazepine, benzoazepine, benzodiazepine, benzofurazan, benzothiadiazole, benzotriazole, carbazole, β-carboline, acridine, phenazine, dibenzofuran, xanthene, dibenzothiophene, phenothiazine, phenoxazine, phenoxathiin, thianthrene, phenanthridine, phenanthroline, pyrroline, pyrrolidine, imidazoline, imidazolidine,Triazoline, triazolidine, tetrazoline, tetrazolidine, pyrazoline, pyrazolidine, dihydropyridine, tetrahydropyridine, piperidine, dihydropyrazine, tetrahydropyrazine, piperazine, dihydropyrimidine, tetrahydropyrimidine, perhydropyrimidine, dihydropyridazine, tetrahydropyridazine, perhydropyridazine, dihydroazepine, tetrahydroazepine, perhydroazepine, dihydrodiazepine, tetrahydrodiazepine, perhydrodiazepine, dihydrofuran, tetrahydrofuran, dihydropyran, tetrahydropyran, dihydrooxepine, tetrahydrooxepine, perhydrooxepine, dihydrothiophene, tetrahydrothiophene, dihydrothiopyran, tetrahydrothiopyran, dihydrothiepine, tetrahydrothiepine, perhydrothiepine, dihydrooxazole, tetrahydrooxazole (oxazolidine), dihydroisoxazole, tetrahydroisoxazole (isoxazolidine), dihydrothiazole, tetrahydrothiazole (thiazolidine), dihydroisothiazole, tetrahydroisothiazole (isothiazolidine), dihydrofurazan, tetrahydrofurazan, dihydrooxadiazole, tetrahydrooxadiazole (oxadiazolidine), dihydrooxazine, tetrahydrooxazine, dihydrooxadiazine, tetrahydrooxadiazine, dihydrooxazepine, tetrahydrooxazepine, perhydrooxazepine, dihydrooxadiazepine, tetrahydrooxadiazepine, perhydrooxadiazepine, dihydrothiadiazole, tetrahydrothiadiazole (thiadiazolidine), dihydrothiazine, tetrahydrothiazine, dihydrothiadiazine, tetrahydrothiadiazine, dihydrothiazepine, tetrahydrothiazepine, perhydrothiazepine, dihydrothiadiazepine, tetrahydrothiadiazepine, perhydrothiadiazepine, morpholine, thiomorpholine, oxathiane, indoline, isoindoline, dihydrobenzofuran, perhydrobenzofuran, dihydroisobenzofuran, perhydroisobenzofuran, dihydrobenzothiophene, perhydrobenzothiophene, dihydroisobenzothiophene, perhydroisobenzothiophene, dihydroindazole,Monovalent groups formed by removing one hydrogen atom from heterocyclic rings such as perhydroindazole, dihydroquinoline, tetrahydroquinoline, perhydroquinoline, dihydroisoquinoline, tetrahydroisoquinoline, perhydroisoquinoline, dihydrophthalazine, tetrahydrophthalazine, perhydrophthalazine, dihydronaphthyridine, tetrahydronaphthyridine, perhydronaphthyridine, dihydroquinoxaline, tetrahydroquinoxaline, perhydroquinoxaline, dihydroquinazoline, tetrahydroquinazoline, perhydroquinazoline, dihydrosinnoline, tetrahydrosinnoline, perhydrosinnoline, benzoxathiane, dihydrobenzoxazine, dihydrobenzothiazine, pyrazinomorpholine, dihydrobenzoxazole, perhydrobenzoxazole, dihydrobenzothiazole, perhydrobenzothiazole, dihydrobenzimidazole, perhydrobenzimidazole, dihydrobenzazepine, tetrahydrobenzazepine, dihydrobenzodiazepine, tetrahydrobenzodiazepine, benzodioxepane, dihydrobenzoxazepine, tetrahydrobenzoxazepine, dihydrocarbazole, tetrahydrocarbazole, perhydrocarbazole, dihydroacridine, tetrahydroacridine, perhydroacridine, dihydrodibenzofuran, dihydrodibenzothiophene, tetrahydrodibenzofuran, tetrahydrodibenzothiophene, perhydrodibenzofuran, perhydrodibenzothiophene, dioxolane, dioxane, dithiolane, dithiane, dioxaindane, benzodioxane, chroman, benzodithiolane, and benzodithiane. Among the monovalent heterocyclic groups, those having aromaticity are also referred to as "heteroaryl groups". For example, heteroaryl groups formed by removing one hydrogen atom from monocyclic aromatic heterocycles such as pyridine, pyridazine, pyrimidine, pyrazine, furan, thiophene, pyrrole, pyrazole, imidazole, triazole, tetrazole, oxazole, isoxazole, thiazole, isothiazole, oxadiazole, and thiadiazole; benzofuran, benzothiophene, indole, isoindole, benzoxazole, benzothiazole, benzimidazole, indazole, benzisoxazole, benzisothiazole,Examples of the heteroaryl group include those formed by removing one hydrogen atom from a polycyclic aromatic heterocyclic ring such as benzoxadiazole, benzothiadiazole, purine, quinoline, isoquinoline, cinnoline, phthalazine, quinazoline, quinoxaline, pteridine, imidazoxazole, imidazolethiazole, imidazoleimidazole, and furopyridine.

[0024] As described above, the "hydrocarbon group containing a heteroatom" in the present specification includes a monovalent group formed by bonding a divalent group selected from the group consisting of -O-, -S-, -C(=O)-, -S(=O)-, -S(=O)2-, -N(R)-, -Si(R)2-, and combinations thereof to the bond of a monovalent carbocyclic group (hereinafter, also referred to as "monovalent group A" for convenience). Here, the monovalent carbocyclic group is as described above including its type and the number of carbon atoms. Examples of the monovalent group A include, for example, those containing a monovalent saturated carbocyclic group such as a cycloalkyloxy group, a cycloalkylthio group, a cycloalkylsulfonyl group, a cycloalkylsulfinyl group, a cycloalkylcarbonyl group, a cycloalkylamino group, a cycloalkylsilyl group, a cycloalkyloxycarbonyl group, a cycloalkylcarbonyloxy group, a cycloalkylamide group, a cycloalkylimide group, a cycloalkylureido group, a cycloalkylsulfonylamino group, a cycloalkyloxycarbonylamino group, and a cycloalkylsilyloxy group. Examples of the monovalent group A also include, for example, those containing an aryl group as a monovalent unsaturated carbocyclic group such as an aryloxy group, an arylcarbonyl group, an arylamino group, an arylsilyl group, an aryloxycarbonyl group, an arylcarbonyloxy group, an arylamide group, an arylimide group, an arylureido group, an arylsulfonylamino group, an aryloxycarbonylamino group, and an arylsilyloxy group. For those containing other unsaturated carbocyclic groups such as a cycloalkenyl group as a monovalent unsaturated carbocyclic group, the above "aryl" may be read as "cycloalkenyl" etc. and applied accordingly.

[0025] As described above, the "heteroatom-containing hydrocarbon group" in this specification includes a monovalent group formed by bonding a divalent group selected from the group consisting of -O-, -S-, -C(=O)-, -S(=O)-, -S(=O)2-, -N(R)-, -Si(R)2-, and combinations thereof to the bond of a monovalent heterocyclic group (hereinafter, also referred to as "monovalent group B" for convenience). Here, the monovalent heterocyclic group is as described above, including its type, the number of heteroatoms, and the number of carbon atoms. Examples of the monovalent group B include a heterocyclic oxy group, a heterocyclic thio group, a heterocyclic sulfonyl group, a heterocyclic sulfinyl group, a heterocyclic carbonyl group, a heterocyclic amino group, a heterocyclic silyl group, a heterocyclic oxycarbonyl group, a heterocyclic carbonyloxy group, a heterocyclic amide group, a heterocyclic imide group, a heterocyclic ureido group, a heterocyclic sulfonylamino group, a heterocyclic oxycarbonylamino group, and a heterocyclic silyloxy group. When the heterocyclic ring exhibits aromaticity, examples of the monovalent group B may be obtained by reading "heterocyclic ring" as "heteroaryl" in the above and applying it.

[0026] In this specification, the term "halogen atom" refers to an atom selected from a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. A monovalent group having a bond extending from the halogen atom is also referred to as a "halogeno group", and examples include a fluoro group, a chloro group, a bromo group, and an iodo group.

[0027] In this specification, "C p ~C q " (p and q are positive integers and satisfy p < q) represents that the number of carbon atoms of the organic group described immediately after this term is p to q. For example, "C1~C 12 alkyl group" indicates an alkyl group having 1 to 12 carbon atoms, and "C6~C 10 aryl-C1~C6 alkyl group" indicates an arylalkyl group having 6 to 10 carbon atoms in the aryl part and 1 to 6 carbon atoms in the alkyl part.

[0028] As used herein, the term "optionally substituted" with respect to a compound or a group means both the case where a hydrogen atom of the compound or the group is not substituted with a substituent and the case where some or all of the hydrogen atoms of the compound or the group are substituted with a substituent.

[0029] As used herein, the term "substituent" means, unless otherwise specified, a halogeno group, an alkyl group, an alkenyl group, an alkynyl group, an alkapolyenyl group, a cycloalkyl group, a cycloalkenyl group, a cycloalkynyl group, an alkoxy group, an alkylthio group, an alkylsulfonyl group, an alkylsulfinyl group, an alkyloxycarbonyl group, an alkylsulfonylamino group, an alkyloxycarbonylamino group, a cycloalkyloxy group, an aryl group, an aryloxy group, an arylthio group, an arylsulfonyl group, an arylsulfinyl group, an aryloxycarbonyl group, an arylsulfonylamino group, an aryloxycarbonylamino group, an arylalkyl group, an arylalkoxy group, a monovalent heterocyclic group, a monovalent heterocyclic oxy group, a monovalent heterocyclic sulfonylamino group, an alkylidene group, an amino group, a silyl group, an acyl group, an acyloxy group, a carboxy group, a sulfo group, a cyano group, a nitro group, a hydroxy group, a mercapto group, a carbamoyl group, a sulfamoyl group, and an oxo group.

[0030] The halogeno group, alkyl group, alkenyl group, alkynyl group, and alkapolyenyl group used as substituents are as described above, including their preferred embodiments.

[0031] The cycloalkyl group, cycloalkenyl group, and cycloalkynyl group used as substituents are as described for the above-mentioned "monovalent carbocyclic group", but the number of carbon atoms thereof is preferably 3 to 12, more preferably 3 to 6.

[0032] The alkoxy group, alkylthio group, alkylsulfonyl group, alkylsulfinyl group, alkyloxycarbonyl group, alkylsulfonylamino group, and alkyloxycarbonylamino group used as substituents are as described for the above-mentioned "heteroalkyl group", and the number of carbon atoms thereof is preferably 1 to 12, more preferably 1 to 6.

[0033] The cycloalkyloxy group used as a substituent is a monovalent group (the "monovalent group A") belonging to the above-mentioned "hydrocarbon group containing a heteroatom", and the number of carbon atoms thereof is as described above, but is preferably 3 to 12, more preferably 3 to 6. Examples of the cycloalkyloxy group include a cyclopropyloxy group, a cyclobutyloxy group, a cyclopentyloxy group, and a cyclohexyloxy group.

[0034] The aryl group used as a substituent is as described for the above-mentioned "monovalent carbocyclic group", and the number of carbon atoms thereof is preferably 6 to 14, more preferably 6 to 10.

[0035] The aryloxy group, arylthio group, arylsulfonyl group, arylsulfinyl group, aryloxycarbonyl group, arylsulfonylamino group, and aryloxycarbonylamino group used as substituents are monovalent groups (the "monovalent group A") belonging to the above-mentioned "hydrocarbon group containing a heteroatom", and the number of carbon atoms thereof is as described above, but is preferably 6 to 14, more preferably 6 to 10. Examples of the aryloxy group used as a substituent include a phenoxy group, a 1-naphthyloxy group, and a 2-naphthyloxy group.

[0036] The number of carbon atoms of the arylalkyl group used as a substituent is preferably 7 to 25, more preferably 7 to 19, still more preferably 7 to 15, and even more preferably 7 to 11. Examples of the arylalkyl group include phenyl-C1-C 12 alkyl group, naphthyl-C1-C 12 alkyl group, and anthracenyl-C1-C 12An alkyl group may be mentioned.

[0037] The number of carbon atoms of the arylalkoxy group used as a substituent is preferably 7 to 25, more preferably 7 to 19, still more preferably 7 to 15, and even more preferably 7 to 11. Examples of the arylalkoxy group include phenyl-C1~C 12 alkoxy group, and naphthyl-C1~C 12 alkoxy group may be mentioned.

[0038] The monovalent heterocyclic group used as a substituent is as described above for the "monovalent heterocyclic group". Among them, a 3- to 15-membered monovalent heterocyclic group having 1 to 5 heteroatoms selected from the group consisting of an oxygen atom, a nitrogen atom, and a sulfur atom (a heteroaryl group when exhibiting aromaticity) is preferable.

[0039] The monovalent heterocyclic oxy group and the monovalent heterocyclic sulfonylamino group used as substituents are monovalent groups belonging to the above-mentioned "heteroatom-containing hydrocarbon group" ("monovalent group B"), and the number of heteroatoms and carbon atoms thereof is as described above. Among them, a monovalent heterocyclic oxy group containing a 3- to 15-membered heterocyclic ring having 1 to 5 heteroatoms selected from the group consisting of an oxygen atom, a nitrogen atom, and a sulfur atom (a heteroaryloxy group when exhibiting aromaticity) and a monovalent heterocyclic sulfonylamino group (a heteroarylsulfonylamino group when exhibiting aromaticity) are preferable.

[0040] The alkylidene group used as a substituent refers to a group in which two hydrogen atoms are removed from the same carbon atom of an alkane. The number of carbon atoms of the alkylidene group is preferably 1 to 20, more preferably 1 to 14, still more preferably 1 to 12, even more preferably 1 to 6, and particularly preferably 1 to 3. Examples of the alkylidene group include methylidene group, ethylidene group, propylidene group, isopropylidene group, butylidene group, sec-butylidene group, isobutylidene group, tert-butylidene group, pentylidene group, hexylidene group, heptylidene group, octylidene group, nonylidene group, and decylidene group.

[0041] The acyl group used as a substituent refers to a group represented by the formula: -C(=O)-R' (wherein R' represents a hydrogen atom, an alkyl group, an alkenyl group, a cycloalkyl group or an aryl group. The same applies hereinafter). The alkyl group, cycloalkyl group and aryl group represented by R' are as described above. The number of carbon atoms of the acyl group is preferably 2 to 13, more preferably 2 to 7. Examples of the acyl group include an acetyl group, a propionyl group, a butyryl group, an isobutyryl group, a valeryl group, an isovaleryl group, a pivaloyl group, a hexanoyl group, an acryloyl group, a methacryloyl group, a crotonoyl group, an isocrotonoyl group, a benzoyl group, and a naphthoyl group.

[0042] The acyloxy group used as a substituent refers to a group represented by the formula: -O-C(=O)-R'. The number of carbon atoms of the acyloxy group is preferably 2 to 13, more preferably 2 to 7. Examples of the acyloxy group include an acetoxy group, a propionyloxy group, a butyryloxy group, an isobutyryloxy group, a valeryloxy group, an isovaleryloxy group, a pivaloyloxy group, a hexanoyloxy group, an acryloyloxy group, a methacryloyloxy group, a crotonoyloxy group, an isocrotonoyloxy group, a benzoyloxy group, and a naphthoyloxy group.

[0043] The above substituents may further have substituents (hereinafter sometimes referred to as "secondary substituents"). Unless otherwise specified, the same substituents as those described above may be used as the secondary substituents. Examples of the substituents having secondary substituents include a halogenoalkyl group (an alkyl group having a halogeno group as a secondary substituent), an arylalkylthio group (an alkylthio group having an aryl group as a secondary substituent), a heteroarylalkoxy group (an alkoxy group having a heteroaryl group as a secondary substituent), a heteroarylalkylthio group (an alkylthio group having a heteroaryl group as a secondary substituent), a halogenoalkoxy group (an alkoxy group having a halogeno group as a secondary substituent), a halogenoalkylthio group (an alkylthio group having a halogeno group as a secondary substituent), a hydroxyalkoxy group (an alkoxy group having a hydroxy group as a secondary substituent), an alkoxyalkoxy group (an alkoxy group having an alkoxy group as a secondary substituent), a mono- or dialkylamino group (an amino group having one (monosubstituted) or two (disubstituted) alkyl groups as secondary substituents), a mono- or dialkylcarbamoyl group (a carbamoyl group having one (monosubstituted) or two (disubstituted) alkyl groups as secondary substituents), a mono- or dialkylsulfamoyl group (a sulfamoyl group having one (monosubstituted) or two (disubstituted) alkyl groups as secondary substituents), and a mono- or diacylamino group (an amino group having one (monosubstituted) or two (disubstituted) acyl groups as secondary substituents).

[0044] Hereinafter, the present invention will be described in detail with reference to its preferred embodiments. However, the present invention is not limited to the following embodiments and exemplifications, and can be arbitrarily modified and implemented without departing from the scope of the claims of the present invention and its equivalent scope.

[0045] [Resin Composition] The resin composition of the present invention contains (A) a compound represented by the following formula (1), (B) an epoxy resin, and (C) a curing agent. [Chemical formula] (In the formula, R 1each independently represents a monovalent hydrocarbon group which may have a substituent, or a monovalent heteroatom-containing hydrocarbon group which may have a substituent; R 2 represents a hydrogen atom, a monovalent hydrocarbon group which may have a substituent, or a monovalent heteroatom-containing hydrocarbon group which may have a substituent; R 3 represents a divalent hydrocarbon group which may have a substituent; R 4 represents a hydrogen atom, a monovalent hydrocarbon group which may have a substituent, a monovalent heteroatom-containing hydrocarbon group which may have a substituent, or an amino group which may have a substituent; m represents a number from 0 to 4; n represents 0 or 1.)

[0046] As described above, when forming a wiring pattern by the semi-additive method, when an insulating layer is formed using a conventional resin composition that contributes to good dielectric properties (for example, a resin composition adopting a specific composition such as using a specific curing agent such as an active ester-based curing agent that can reduce and suppress the generation of polar groups such as secondary hydroxyl groups in the curing reaction of an epoxy resin, or highly compounding an inorganic filler), it has been found that the adhesion between the obtained insulating layer and the plated conductor may not be sufficiently obtained. Although such adhesion to the plated conductor can be improved by using a certain amount of dimethylaminopyridine (DMAP) as a curing accelerator, it has been found that when DMAP is used in an amount that results in good adhesion to the plated conductor, the adhesion to the underlying conductor, particularly after exposure to a high-temperature and high-humidity environment, tends to deteriorate. Further, it has been confirmed that the deterioration of the adhesion to the underlying conductor after exposure to a high-temperature and high-humidity environment becomes prominent when highly compounding a specific curing agent such as an active ester-based curing agent or further highly compounding an inorganic filler in order to bring about better dielectric properties.

[0047] Furthermore, when using DMAP in an amount that provides good adhesion to the plating conductor in the case of adopting a specific composition that contributes to good dielectric properties, it has been confirmed that depending on the surface circuit pattern of the substrate that is the base, when the obtained insulating layer is roughened, cracks may occur in the insulating layer on the pattern.

[0048] In contrast, according to the present invention that uses a specific modified aminopyridine compound represented by the above formula (1) in a resin composition containing an epoxy resin and a curing agent, even when adopting a specific composition that contributes to good dielectric properties, when forming a wiring pattern by the semi-additive method, it exhibits good adhesion to the plating conductor and can provide a cured product that exhibits good adhesion to the underlying conductor when exposed to a high-temperature and high-humidity environment. Furthermore, it has been confirmed that while exhibiting adhesion to the plating conductor that is as good as when using a certain amount of DMAP when forming a wiring pattern by the semi-additive method, it can significantly reduce and suppress the occurrence of cracks on the pattern regardless of the surface circuit pattern of the substrate that is the base.

[0049] <Compound represented by formula (1)> The resin composition of the present invention contains, as component (A), a compound represented by the following formula (1). Thereby, the resin composition of the present invention can achieve the intended effect.

[0050] [Chemical formula] (In the formula, R 1 each independently represents a monovalent hydrocarbon group that may have a substituent, or a monovalent heteroatom-containing hydrocarbon group that may have a substituent, R 2 represents a hydrogen atom, a monovalent hydrocarbon group that may have a substituent, or a monovalent heteroatom-containing hydrocarbon group that may have a substituent, R 3 represents a divalent hydrocarbon group that may have a substituent, R 4represents a hydrogen atom, a monovalent hydrocarbon group which may have a substituent, a monovalent heteroatom-containing hydrocarbon group which may have a substituent, or an amino group which may have a substituent, m represents a number from 0 to 4, n represents 0 or 1.)

[0051] In formula (1), R 1 each independently represents a monovalent hydrocarbon group which may have a substituent, or a monovalent heteroatom-containing hydrocarbon group which may have a substituent.

[0052] R 1 For the monovalent hydrocarbon group and the monovalent heteroatom-containing hydrocarbon group in R, as described above, from the viewpoint of being able to enjoy the effects of the present invention more, the number of carbon atoms thereof is preferably 12 or less, more preferably 10 or less, still more preferably 8 or less or 6 or less, and the lower limit thereof is preferably 1 or more or 2 or more.

[0053] Among them, even when adopting a specific composition contributing to good dielectric characteristics, when forming a wiring pattern by the semi-additive method, it exhibits better adhesion to the plating conductor and can realize a cured product that exhibits better adhesion to the underlying conductor when exposed to a high-temperature and high-humidity environment. From this viewpoint, the monovalent hydrocarbon group in R 1 is preferably a C1-C 12 alkyl group, a C2-C 12 alkenyl group, or a C2-C 12 alkynyl group, and more preferably a C1-C8 alkyl group, a C2-C8 alkenyl group, or a C2-C8 alkynyl group.

[0054] From the same viewpoint, the monovalent heteroatom-containing hydrocarbon group in R 1 is a C1-C 12 heteroalkyl group, a C2-C 12 heteroalkenyl group, or a C2-C 12Preferably, it is a heteroalkynyl group, more preferably a C1-C8 heteroalkyl group, a C2-C8 heteroalkenyl group, or a C2-C8 heteroalkynyl group. The heteroatom contained in the monovalent group is as described above. Among them, it preferably contains one or more heteroatoms selected from an oxygen atom and a nitrogen atom. The number of heteroatoms in the monovalent group is preferably 1 or more, and the upper limit is preferably 5 or less, 4 or less, or 3 or less. In a preferred embodiment, R 1 The monovalent heteroatom-containing hydrocarbon group in is a monovalent group with a bond extending from a heteroatom. More preferably, it is a C1-C8 alkoxy group, a C2-C8 alkenyloxy group, or a C2-C8 alkynyloxy group.

[0055] R 1 The substituent that the monovalent group in may have is as described above. However, from the viewpoint of being able to more enjoy the effects of the present invention, it is preferably one or more selected from the group consisting of an alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group, a cycloalkenyl group, a cycloalkynyl group, an alkoxy group, a cycloalkyloxy group, an aryl group, and a monovalent heterocyclic group. The preferred range of the number of carbon atoms and the like of each substituent is as described above.

[0056] In formula (1), m represents a number from 0 to 4. Among them, from the viewpoint of being able to more enjoy the effects of the present invention, m is preferably from 0 to 3, more preferably from 0 to 2, and even more preferably 0 or 1. When m is 2 or more and a plurality of R 1 exist, the plurality of R 1 may be determined independently of each other, and they may be the same or different from each other.

[0057] In formula (1), when m is 1 or more, it is preferable that R 1 is bonded to one or more carbon atoms at the 2-position and 3-position of the pyridine ring.

[0058] In formula (1), R 2represents a hydrogen atom, a monovalent hydrocarbon group which may have a substituent, or a monovalent heteroatom-containing hydrocarbon group which may have a substituent.

[0059] R 2 The monovalent hydrocarbon group and the monovalent heteroatom-containing hydrocarbon group in R are as described above. From the viewpoint of more enjoying the effects of the present invention, the number of carbon atoms thereof is preferably 12 or less, more preferably 10 or less, still more preferably 8 or less, 6 or less, or 4 or less, and the lower limit thereof is preferably 1 or more or 2 or more.

[0060] Among them, even when adopting a specific composition that contributes to good dielectric properties, when forming a wiring pattern by the semi-additive method, it exhibits better adhesion to the plating conductor and realizes a cured product that exhibits better adhesion to the underlying conductor when exposed to a high-temperature and high-humidity environment. From this viewpoint, the monovalent hydrocarbon group in R 2 is preferably a C1-C 12 alkyl group, a C2-C 12 alkenyl group, or a C2-C 12 alkynyl group, more preferably a C1-C8 alkyl group, a C2-C8 alkenyl group, or a C2-C8 alkynyl group, and still more preferably a C1-C4 alkyl group, a C2-C4 alkenyl group, or a C2-C4 alkynyl group.

[0061] From the same viewpoint, the monovalent heteroatom-containing hydrocarbon group in R 2 is a C1-C 12 heteroalkyl group, a C2-C 12 heteroalkenyl group, or a C2-C 12It is preferably a heteroalkynyl group, more preferably a C1-C8 heteroalkyl group, a C2-C8 heteroalkenyl group, or a C2-C8 heteroalkynyl group, and even more preferably a C1-C4 heteroalkyl group, a C2-C4 heteroalkenyl group, or a C2-C4 heteroalkynyl group. The heteroatom contained in the monovalent group is as described above. Among them, it preferably contains one or more heteroatoms selected from an oxygen atom and a nitrogen atom. The number of heteroatoms in the monovalent group is preferably 1 or more, and the upper limit thereof is preferably 5 or less, 4 or less, or 3 or less. In a preferred embodiment, R 2 The monovalent heteroatom-containing hydrocarbon group in is a monovalent group with a bond extending from the heteroatom. More preferably, it is a C1-C8 alkoxy group, a C2-C8 alkenyloxy group, or a C2-C8 alkynyloxy group.

[0062] R 2 The substituent that the monovalent group in may have is as described above. From the viewpoint of being able to enjoy the effects of the present invention more, it is preferably one or more selected from the group consisting of an alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group, a cycloalkenyl group, a cycloalkynyl group, an alkoxy group, a cycloalkyloxy group, an aryl group, and a monovalent heterocyclic group. The preferred range of the number of carbon atoms and the like of each substituent is as described above.

[0063] (Component (A) is characterized in that the amino group bonded to the 4-position of the pyridine ring is substituted with a monovalent group represented by the formula: -C(=O)-(R 3 ) n -R 4 Here, n represents 0 or 1. When n is 0, the amino group bonded to the 4-position of the pyridine ring is substituted with a monovalent group represented by the formula: -C(=O)-R 4 When n is 1, the amino group bonded to the 4-position of the pyridine ring is substituted with a monovalent group represented by the formula: -C(=O)-R 3 -R 4

[0064] In formula (1), R 3represents a divalent hydrocarbon group which may have a substituent.

[0065] R 3 Regarding the divalent hydrocarbon group in R, as described above, from the viewpoint of more enjoying the effects of the present invention, the number of carbon atoms thereof is preferably 12 or less, more preferably 10 or less, still more preferably 8 or less, 6 or less, or 4 or less, and the lower limit thereof is preferably 1 or more or 2 or more.

[0066] Among them, even when adopting a specific composition contributing to good dielectric properties, when forming a wiring pattern by the semi-additive method, it exhibits better adhesion to the plating conductor and realizes a cured product that exhibits better adhesion to the underlying conductor when exposed to a high-temperature and high-humidity environment. From this viewpoint, the divalent hydrocarbon group in R 3 is preferably a C1-C 12 alkylene group, a C2-C 12 alkenylene group, or a C2-C 12 alkynylene group, more preferably a C1-C8 alkylene group, a C2-C8 alkenylene group, or a C2-C8 alkynylene group, and still more preferably a C1-C4 alkylene group, a C2-C4 alkenylene group, or a C2-C4 alkynylene group.

[0067] R 3 The substituent that the divalent hydrocarbon group in R may have is as described above. From the viewpoint of more enjoying the effects of the present invention, it is preferably one or more selected from the group consisting of an alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group, a cycloalkenyl group, a cycloalkynyl group, an alkoxy group, a cycloalkyloxy group, an aryl group, and a monovalent heterocyclic group. The preferred range of the number of carbon atoms and the like of each substituent is as described above.

[0068] In formula (1), R 4 represents a hydrogen atom, a monovalent hydrocarbon group which may have a substituent, a monovalent heteroatom-containing hydrocarbon group which may have a substituent, or an amino group which may have a substituent.

[0069] R 4 The monovalent hydrocarbon group or monovalent heteroatom-containing hydrocarbon group in R is as described above. From the viewpoint of more enjoying the effects of the present invention, the number of carbon atoms is preferably 12 or less, more preferably 10 or less, still more preferably 8 or less or 6 or less, and the lower limit is preferably 1 or more or 2 or more.

[0070] Among them, even when adopting a specific composition contributing to good dielectric properties, when forming a wiring pattern by the semi-additive method, it exhibits better adhesion to the plating conductor and can realize a cured product that exhibits better adhesion to the underlying conductor when exposed to a high-temperature and high-humidity environment. From this viewpoint, the monovalent hydrocarbon group in R 4 is preferably a C1-C 12 alkyl group, C2-C 12 alkenyl group, C2-C 12 alkynyl group, C3-C 12 cycloalkyl group, or a C6-C 10 aryl group, more preferably a C1-C8 alkyl group, C2-C8 alkenyl group, C2-C8 alkynyl group, C4-C 10 cycloalkyl group, or a C6 aryl group.

[0071] From the same viewpoint, the monovalent heteroatom-containing hydrocarbon group in R 4 is preferably a C1-C 12 heteroalkyl group, C2-C 12 heteroalkenyl group, C2-C 12 heteroalkynyl group, or a monovalent C1-C 12 heterocyclic group, more preferably a C1-C8 heteroalkyl group, C2-C8 heteroalkenyl group, C2-C8 heteroalkynyl group, or a monovalent C1-C9 heterocyclic group. The heteroatoms contained in the monovalent group are as described above. Among them, it preferably contains one or more heteroatoms selected from an oxygen atom, a nitrogen atom, and a sulfur atom, the number of heteroatoms in the monovalent group is preferably 1 or more, and the upper limit is preferably 5 or less, 4 or less, or 3 or less. R 4When the monovalent heteroatom-containing hydrocarbon group in is a monovalent C1-C 12 When it is a heterocyclic group, from the viewpoint of being able to more enjoy the effects of the present invention, C1-C 12 It is preferably a heteroaryl group, more preferably a C1-C9 heteroaryl group, and even more preferably a 5- to 10-membered C1-C9 heteroaryl group containing 1 to 5 heteroatoms selected from oxygen atoms, nitrogen atoms, and sulfur atoms, and the heteroaryl group is preferably monocyclic or bicyclic. R 4 The monovalent heteroatom-containing hydrocarbon group in is also preferably a C3-C 12 carbocyclic oxy group, more preferably a C3-C 12 cycloalkyloxy group, and even more preferably a C4-C 10 cycloalkyloxy group. In a preferred embodiment, R 4 The monovalent heteroatom-containing hydrocarbon group in is a monovalent group with a bond extending from a heteroatom or a monovalent heterocyclic group, and more preferably a C1-C8 alkoxy group, a C2-C8 alkenyloxy group, a C2-C8 alkynyloxy group, a C4-C 10 cycloalkyloxy group, or a C1-C9 heteroaryl group.

[0072] Particularly from the viewpoint of being able to more enjoy the effects of the present invention, R 4 represents an alkyl group which may have a substituent, an alkenyl group which may have a substituent, an alkynyl group which may have a substituent, a cycloalkyl group which may have a substituent, an aryl group which may have a substituent, an alkoxy group which may have a substituent, an alkenyloxy group which may have a substituent, an alkynyloxy group which may have a substituent, a cycloalkyloxy group which may have a substituent, a heteroaryl group which may have a substituent, or an amino group which may have a substituent. In these, the preferred ranges such as the number of carbon atoms are as described above.

[0073] R 4The monovalent hydrocarbon group, monovalent heteroatom-containing hydrocarbon group, and substituent that may be contained in the amino group are as described above. However, from the viewpoint of more enjoying the effects of the present invention, an alkyl group, alkenyl group, alkynyl group, cycloalkyl group, cycloalkenyl group, cycloalkynyl group, alkoxy group, cycloalkyloxy group, aryl group, monovalent heterocyclic group, and amino group It is preferably at least one selected from the group consisting of. The preferred range of the number of carbon atoms and the like of each substituent is as described above.

[0074] Even when a specific composition that contributes to good dielectric properties is adopted, when a wiring pattern is formed by the semi-additive method, it exhibits particularly good adhesion to the plating conductor and is exposed to a high-temperature and high-humidity environment. Examples of compounds represented by formula (1) that are particularly suitable from the viewpoint of realizing a cured product that exhibits particularly good adhesion to the underlying conductor are shown below.

[0075] In a preferred embodiment, in formula (1), R 1 represents a C1-C8 alkyl group that may have a substituent, or a C2-C8 alkenyl group that may have a substituent, R 2 represents a C1-C4 alkyl group that may have a substituent, R 3 represents a C1-C4 alkylene group that may have a substituent, R 4 represents a C1-C8 alkyl group that may have a substituent, a C2-C8 alkenyl group that may have a substituent, a C1-C8 heteroalkyl group that may have a substituent (the heteroatom is one or more selected from oxygen atoms and nitrogen atoms and the number of heteroatoms is 1 or more and 3 or less), or a monovalent C1-C9 heterocyclic group that may have a substituent (the heteroatom is one or more selected from oxygen atoms, nitrogen atoms, and sulfur atoms and the number of heteroatoms is 1 or more and 5 or less), m and n are each independently 0 or 1. Here, the substituent is as described above including its preferred embodiment.

[0076] In a more preferred embodiment, in formula (1), R 1 represents a C1-C8 alkyl group which may have a substituent, or a C2-C8 alkenyl group which may have a substituent, R 2 represents a C1-C4 alkyl group which may have a substituent, R 3 represents a C1-C4 alkylene group which may have a substituent, R 4 represents a C1-C4 alkyl group which may have a substituent, a C2-C4 alkenyl group which may have a substituent, a C1-C4 alkoxy group which may have a substituent, or a C1-C9 heteroaryl group (the heteroatom is one or more selected from an oxygen atom, a nitrogen atom and a sulfur atom and the number of heteroatoms is 1 or more and 5 or less, and it is a monocyclic or bicyclic ring of 5 members or more and 10 members or less), m and n are each independently 0 or 1. Here, the substituent is as described above including its preferred embodiments.

[0077] Hereinafter, an example of the synthesis procedure of component (A) will be shown.

[0078] In one embodiment, component (A) is (a1) a 4-aminopyridine compound which may have a substituent, and (a2) an organic acid halide compound and, if necessary (when m in formula (1) is 1 or more), (a3) an organic boronic acid or its derivative are reacted to synthesize.

[0079] -(a1) 4-aminopyridine compound which may have a substituent- Component (a1) is a 4-aminopyridine compound which may have a substituent, and is represented by the following formula (a1).

[0080]

Chemical formula

[0081] As the component (a1), depending on the structure of the target component (A) (the value of m in formula (1) and the bonding position of R 1 , the type of R 2 ), an optional 4-aminopyridine compound which may have a substituent may be used. Suitable values of m in formula (1), the bonding position of R 1 , and suitable examples of R 2 are as described above for formula (1). For example, when the target component (A) is such that in formula (1) m = 0 and R 2 = a C1-C4 alkyl group, 4-(C1-C4 alkylamino)pyridine may be used as the component (a1). When the target component (A) is such that in formula (1) m = 1, the bonding position of R 1 is the 2-position of the pyridine ring, and R 2 = a C1-C4 alkyl group, 2-bromo-N-C1-C4 alkylpyridin-4-amine may be used as the component (a1).

[0082] -(a2) Organic acid halide compound- The component (a2) is an organic acid halide compound and is represented by the following formula (a2).

Chemical formula

[0083] As the component (a2), depending on the structure of the target component (A) (the value of n in formula (1) and the types of R 3 , R 4 ), an optional organic acid halide compound may be used. Suitable values of n in formula (1) and suitable examples of R 3 , R 4 are as described above for formula (1). For example, when the target component (A) is such that in formula (1) n = 0 and R 4When it is a C1 alkyl group (methyl group), acetyl chloride may be used as the component (a2). When the target component (A) has n = 0 in the formula (1), R 4 When it is a C2 alkenyl group, acrylic acid chloride may be used as the component (a2). When the target component (A) has n = 0 in the formula (1), R 4 When it is a C6 aryl group (phenyl group), benzoyl chloride may be used as the component (a2). When the target component (A) has n = 0 in the formula (1), R 4 When it is a C1 alkoxy group, methyl chloroformate may be used as the component (a2). When the target component (A) has n = 0 in the formula (1), R 4 When it is an amino group substituted with a methyl group and a phenyl group, methylphenylcarbamic acid chloride may be used as the component (a2). When the target component (A) has n = 1 in the formula (1), R 3 When it is a C1 alkylene group, R 4 When it is a C3 heteroaryl group having two amino groups (the heteroatom is a nitrogen atom and the number of heteroatoms is 3; that is, a triazinyl group), first, 2-cyanoacetyl chloride may be reacted with the component (a1), and the resulting compound may be reacted with dicyandiamide for cyclization.

[0084] (a1) component and (a2) component condensation reaction may proceed in a solvent-free system without using a solvent, or may proceed in an organic solvent system using an organic solvent. The organic solvent used in the condensation reaction is not particularly limited as long as the reaction proceeds smoothly. For example, halogenated hydrocarbon solvents such as dichloromethane, 1,2-dichloroethane, 1,4-dichlorobutane, chlorobenzene, o-dichlorobenzene; ketone solvents such as acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone; acetic acid ester solvents such as ethyl acetate, butyl acetate, cellosolve acetate, propylene glycol monomethyl ether acetate, carbitol acetate; carbitol solvents such as cellosolve, butyl carbitol; aromatic hydrocarbon solvents such as toluene, xylene; amide solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone. The organic solvent may be used alone or in combination of two or more.

[0085] In the condensation reaction, a base may be used. Examples of the base include alkali metal hydroxides such as sodium hydroxide (caustic soda) and potassium hydroxide; tertiary amines such as triethylamine, pyridine, N,N-diisopropylethylamine, N,N-dimethyl-4-aminopyridine (DMAP). The base may be used alone or in combination of two or more.

[0086] In the condensation reaction, a condensing agent or an interlayer transfer catalyst may also be used. These may be any conventionally known ones that can be used in the amidation reaction.

[0087] The reaction temperature in the condensation reaction is not particularly limited as long as the condensation reaction proceeds. For example, it may be in the range of 0 to 80 °C. Also, the reaction time in the condensation reaction is not particularly limited as long as the structure of the target (A) component is achieved. For example, it may be in the range of 30 minutes to 48 hours.

[0088] After the condensation reaction, the condensation product may be purified. For example, after the condensation reaction, purification steps such as washing with water or microfiltration may be performed to remove by-product salts and excess starting materials from the system. Specifically, after the condensation reaction, an amount of aqueous solvent necessary to dissolve the by-product salts is added, and the mixture is allowed to stand and separated by liquid-liquid extraction, and the aqueous layer is discarded or subjected to extraction treatment with an organic solvent. Further, if necessary, an acid is added for neutralization and washing with water is repeated. Thereafter, after passing through a dehydration step by a chemical agent or azeotropy and performing microfiltration to remove impurities and purifying, if necessary, the organic solvent is removed by distillation to obtain a condensation product of the (a1) component and the (a2) component. When the target (A) component has m = 0 in the formula (1), that is, does not have R 1 the condensation product of the (a1) component and the (a2) component may be used as the (A) component.

[0089] -(a3) Organic boronic acid or its derivative- (a3) component is an organic boronic acid or its derivative (also simply referred to as "organic boronic acid compound") and is represented by the following formula (a3).

Chemical formula

[0090] When the target (A) component has m of 1 or more in the formula (1), that is, has R 1 the (a3) component may be reacted (cross-coupled) with the condensation product of the (a1) component and the (a2) component to synthesize the (A) component.

[0091] (As the (a3) component, any organic boronic acid compound may be used according to the structure of the target (A) component (the type of R 1 in the formula (1)). R in the formula (1) 1A preferred example is as described above for formula (1). For example, when the target component (A) has R 1 = a C8 alkenyl group in formula (1), octen-1-ylboronic acid or a derivative thereof may be used as the component (a3). When the target component (A) has R 1 = a C3 alkenyl group (methyl group) in formula (1), propen-1-ylboronic acid or a derivative thereof may be used as the component (a3).

[0092] (The reaction of the condensation product of the component (a1) and the component (a2) with the above component (a3) may be carried out under any conditions as long as the reaction proceeds smoothly. For example, in a solvent that does not adversely affect this reaction, such as 1,4-dioxane, toluene, butanol, etc., in the presence of a catalyst such as [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium, tris(dibenzylideneacetone)dipalladium, tetrakis(triphenylphosphine)palladium, etc., the condensation product of the component (a1) and the component (a2) may be reacted with the above component (a3). At this time, a co-solvent such as water may be used, and the reaction may also be carried out in the presence of a base such as sodium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, tripotassium phosphate, etc., or 2,4,6-triisopropyl-2'-(dicyclohexylphosphino)biphenyl, etc. After the reaction, the reaction product may be purified. The purification may be carried out by the same method as above.)

[0093] In addition, in formula (a1), a substituted 4-aminopyridine compound in which X is R 1 may also be used. For example, when the target component (A) has m = 1, R 1 = a C1 alkyl group (methyl group), and R 2 = a C1 alkyl group (methyl group) in formula (1), (A) may be synthesized by subjecting N,2-dimethylpyridin-4-amine or N,3-dimethylpyridin-4-amine to a condensation reaction with the component (a2).

[0094] Even when adopting a specific composition that contributes to good dielectric properties, from the perspective of realizing a cured product that exhibits excellent adhesion to an electroplated conductor when forming a wiring pattern by the semi-additive method and also exhibits excellent adhesion to an underlying conductor when exposed to a high-temperature and high-humidity environment, the content of component (A) in the resin composition, when the resin component in the resin composition is 100% by mass, is preferably 0.1% by mass or more, more preferably 0.2% by mass or more, 0.4% by mass or more, 0.6% by mass or more, or 0.8% by mass or more, still more preferably 1% by mass or more, 1.2% by mass or more, 1.4% by mass or more, or 1.5% by mass or more. The upper limit of the content, from the perspective of reducing and suppressing the occurrence of cracks on the pattern regardless of the surface circuit pattern of the substrate as the base while exhibiting good adhesion to the electroplated conductor when forming a wiring pattern by the semi-additive method, is preferably 10% by mass or less, more preferably 8% by mass or less, 7% by mass or less, or 6% by mass or less, still more preferably 5% by mass or less. In the present invention, the "resin component" referred to in the resin composition means the component excluding the (D) inorganic filler described later among the non-volatile components constituting the resin composition.

[0095] <(B) Epoxy resin> The resin composition of the present invention contains an epoxy resin as component (B).

[0096] Examples of the epoxy resin include bisphenol type epoxy resin, dicyclopentadiene type epoxy resin, trisphenol type epoxy resin, naphthol novolak type epoxy resin, phenol novolak type epoxy resin, tert-butyl-catechol type epoxy resin, naphthalene type epoxy resin, naphthol type epoxy resin, anthracene type epoxy resin, glycidylamine type epoxy resin, glycidyl ester type epoxy resin, cresol novolak type epoxy resin, biphenyl type epoxy resin, linear aliphatic epoxy resin, epoxy resin having a butadiene structure, alicyclic epoxy resin, heterocyclic epoxy resin, spiro ring-containing epoxy resin, cyclohexane type epoxy resin, cyclohexanedimethanol type epoxy resin, naphthylene ether type epoxy resin, trimethylol type epoxy resin, and tetraphenylethane type epoxy resin. The bisphenol type epoxy resin refers to an epoxy resin having a bisphenol structure, and examples thereof include bisphenol A type epoxy resin, bisphenol F type epoxy resin, bisphenol S type epoxy resin, and bisphenol AF type epoxy resin. The biphenyl type epoxy resin refers to an epoxy resin having a biphenyl structure, and the biphenyl structure may have substituents such as an alkyl group, an alkoxy group, and an aryl group. Therefore, the bixylenol type epoxy resin and the biphenyl aralkyl type epoxy resin are also included in the biphenyl type epoxy resin. The epoxy resin may be used alone or in combination of two or more.

[0097] As the epoxy resin, an aromatic epoxy resin is preferred. Here, the aromatic epoxy resin means an epoxy resin having an aromatic ring in its molecule.

[0098] The epoxy resin preferably has two or more epoxy groups in one molecule. When the non-volatile component of the epoxy resin is 100% by mass, the proportion of the epoxy resin having two or more epoxy groups in one molecule is preferably 50% by mass or more, more preferably 60% by mass or more, and still more preferably 70% by mass or more.

[0099] Epoxy resins include liquid epoxy resins (hereinafter referred to as "liquid epoxy resins") that are liquid at a temperature of 20°C and solid epoxy resins (hereinafter referred to as "solid epoxy resins") that are solid at a temperature of 20°C.

[0100] As the liquid epoxy resin, a liquid epoxy resin having two or more epoxy groups in one molecule is preferred.

[0101] As the liquid epoxy resin, bisphenol A type epoxy resin, bisphenol F type epoxy resin, bisphenol AF type epoxy resin, naphthalene type epoxy resin, glycidyl ester type epoxy resin, glycidyl amine type epoxy resin, phenol novolac type epoxy resin, alicyclic epoxy resins such as alicyclic epoxy resins having an ester skeleton, cyclohexane type epoxy resin, cyclohexanedimethanol type epoxy resin, and epoxy resins having a butadiene structure are preferred.

[0102] Specific examples of the liquid epoxy resin include "HP-4032", "HP-4032D", "HP-4032SS" (naphthalene type epoxy resin) manufactured by DIC Corporation; "828US", "jER828EL", "825", "Epicoat 828EL" (bisphenol A type epoxy resin) manufactured by Mitsubishi Chemical Corporation; "jER807", "1750" (bisphenol F type epoxy resin) manufactured by Mitsubishi Chemical Corporation; "jER152" (phenol novolac type epoxy resin) manufactured by Mitsubishi Chemical Corporation; "630", "630LSD" (glycidyl amine type epoxy resin) manufactured by Mitsubishi Chemical Corporation; "ZX1059" (a mixture of bisphenol A type epoxy resin and bisphenol F type epoxy resin) manufactured by Nippon Steel Chemical & Material Co., Ltd.; "EX-721" (glycidyl ester type epoxy resin) manufactured by Nagase ChemteX Corporation; "Celloxide 2021P" (alicyclic epoxy resin having an ester skeleton) manufactured by Daicel Corporation; "PB-3600" (epoxy resin having a butadiene structure) manufactured by Daicel Corporation; "ZX1658", "ZX1658GS" (liquid 1,4-glycidylcyclohexane type epoxy resin) manufactured by Nippon Steel Chemical & Material Co., Ltd., and the like.

[0103] As the solid epoxy resin, a solid epoxy resin having three or more epoxy groups in one molecule is preferable, and an aromatic solid epoxy resin having three or more epoxy groups in one molecule is more preferable.

[0104] As the solid epoxy resin, a bixylenol type epoxy resin, a naphthalene type epoxy resin, a naphthalene type tetrafunctional epoxy resin, a cresol novolak type epoxy resin, a dicyclopentadiene type epoxy resin, a tris-phenol type epoxy resin, a naphthol type epoxy resin, a biphenyl type epoxy resin, a naphthylene ether type epoxy resin, an anthracene type epoxy resin, a bisphenol A type epoxy resin, a bisphenol AF type epoxy resin, a tetraphenylethane type epoxy resin are preferable.

[0105] Specific examples of the solid epoxy resin include "HP-4032H" (naphthalene-type epoxy resin) manufactured by DIC Corporation; "HP-4700", "HP-4710" (naphthalene-type tetrafunctional epoxy resin) manufactured by DIC Corporation; "N-690" (cresol novolak-type epoxy resin) manufactured by DIC Corporation; "N-695" (cresol novolak-type epoxy resin) manufactured by DIC Corporation; "HP-7200HH", "HP-7200H", "HP-7200" (dicyclopentadiene-type epoxy resin) manufactured by DIC Corporation; "EXA-7311", "EXA-7311-G3", "EXA-7311-G4", "EXA-7311-G4S", "HP6000" (naphthylene ether-type epoxy resin) manufactured by DIC Corporation; "EPPN-502H" (trisphenol-type epoxy resin) manufactured by Nippon Kayaku Co., Ltd.; "NC7000L" (naphthol novolak-type epoxy resin) manufactured by Nippon Kayaku Co., Ltd.; "NC3000H", "NC3000", "NC3000L", "NC3100" (biphenyl-type epoxy resin) manufactured by Nippon Kayaku Co., Ltd.; "ESN475V" (naphthol-type epoxy resin) manufactured by Nippon Steel Chemical & Material Co., Ltd.; "ESN485" (naphthol novolak-type epoxy resin) manufactured by Nippon Steel Chemical & Material Co., Ltd.; "YX4000H", "YX4000", "YL6121" (biphenyl-type epoxy resin) manufactured by Mitsubishi Chemical Corporation; "YX4000HK" (bixylenol-type epoxy resin) manufactured by Mitsubishi Chemical Corporation; "YX8800" (anthracene-type epoxy resin) manufactured by Mitsubishi Chemical Corporation; "PG-100", "CG-500" manufactured by Osaka Gas Chemical Co., Ltd.; "YL7760" (bisphenol AF-type epoxy resin) manufactured by Mitsubishi Chemical Corporation; "YL7800" (fluorene-type epoxy resin) manufactured by Mitsubishi Chemical Corporation; "jER1010" (solid bisphenol A-type epoxy resin) manufactured by Mitsubishi Chemical Corporation; "jER1031S" (tetraphenylethane-type epoxy resin) manufactured by Mitsubishi Chemical Corporation, and the like.

[0106] The resin composition of the present invention may contain only a liquid epoxy resin, only a solid epoxy resin, or a combination of a liquid epoxy resin and a solid epoxy resin as the epoxy resin. When a liquid epoxy resin and a solid epoxy resin are used in combination, their quantitative ratio (liquid epoxy resin: solid epoxy resin) is preferably 1:0.01 to 1:50, more preferably 1:0.05 to 1:20, still more preferably 1:0.1 to 1:10, by mass ratio.

[0107] The epoxy equivalent of the epoxy resin is preferably 50 g / eq. to 5000 g / eq., more preferably 50 g / eq. to 3000 g / eq., still more preferably 80 g / eq. to 2000 g / eq., and even more preferably 110 g / eq. to 1000 g / eq. The epoxy equivalent is the mass of the epoxy resin containing 1 equivalent of epoxy groups. This epoxy equivalent can be measured according to JIS K7236.

[0108] The weight average molecular weight (Mw) of the epoxy resin is preferably 100 to 5000, more preferably 250 to 3000, still more preferably 400 to 1500. The Mw of the epoxy resin can be measured as a value in terms of polystyrene by gel permeation chromatography (GPC) method.

[0109] In combination with the above-mentioned component (A) and component (C) described later, from the viewpoint of realizing a cured product that exhibits excellent adhesion to a plating conductor when forming a wiring pattern by the semi-additive method and excellent adhesion to an underlying conductor when exposed to a high-temperature and high-humidity environment, the content of component (B) in the resin composition is preferably 5% by mass or more, more preferably 10% by mass or more, still more preferably 12% by mass or more, 14% by mass or more, or 15% by mass or more, when the resin components in the resin composition are 100% by mass. The upper limit of the content is not particularly limited and may be determined according to the properties required for the resin composition. For example, it may be 60% by mass or less, 55% by mass or less, or 50% by mass or less.

[0110] <(C) Curing agent> The resin composition of the present invention contains a curing agent as component (C).

[0111] Examples of component (C) include active ester-based curing agents, cyanate ester-based curing agents, carbodiimide-based curing agents, phenol-based curing agents, naphthol-based curing agents, acid anhydride-based curing agents, amine-based curing agents, etc. Component (C) may be used alone or in combination of two or more.

[0112] By using a specific curing agent that can reduce and suppress the generation of polar groups such as secondary hydroxyl groups in the curing reaction of epoxy resins, a resin composition with good dielectric properties can be achieved. Examples of curing agents that contribute to such good dielectric properties include active ester-based curing agents, cyanate ester-based curing agents, and carbodiimide-based curing agents.

[0113] As described above, when forming a wiring pattern by the semi-additive method, it has been found that in some cases, sufficient adhesion between the obtained insulating layer and the plated conductor cannot be obtained even when an insulating layer is formed by adopting a specific composition that contributes to good dielectric properties. Although the adhesion to such a plated conductor can be improved by using a certain amount of DMAP as a curing accelerator, it has been found that when DMAP is used in an amount sufficient to improve the adhesion to the plated conductor, the adhesion to the underlying conductor tends to deteriorate after exposure to a high-temperature and high-humidity environment. In addition, it has been confirmed that the deterioration of the adhesion to the underlying conductor after exposure to a high-temperature and high-humidity environment becomes prominent when a specific curing agent such as an active ester-based curing agent is highly formulated in order to provide even better dielectric properties.

[0114] On the other hand, according to the present invention using the above component (A), even when a specific composition that contributes to good dielectric properties is adopted, a cured product can be obtained that exhibits good adhesion to a plated conductor when forming a wiring pattern by the semi-additive method and also exhibits good adhesion to the underlying conductor when exposed to a high-temperature and high-humidity environment.

[0115] Therefore, in one embodiment, the component (C) includes at least one curing agent selected from the group consisting of (C-1) active ester-based curing agents, cyanate ester-based curing agents, and carbodiimide-based curing agents. According to the resin composition of the present invention, while enjoying the excellent effects (contributing to good dielectric properties) originally exhibited by such component (C-1), when a wiring pattern is formed by the semi-additive method, it exhibits good adhesion to the plating conductor and can provide a cured product that exhibits good adhesion to the underlying conductor when exposed to a high-temperature and high-humidity environment, which is advantageous.

[0116] - Active ester-based curing agent - As the active ester curing agent, a compound having one or more active ester groups in one molecule can be used. Among them, as the active ester curing agent, a compound having two or more highly reactive ester groups in one molecule, such as phenolic esters, thiophenolic esters, N-hydroxyamine esters, and esters of heterocyclic hydroxy compounds, is preferable. The active ester curing agent is preferably obtained by a condensation reaction of a carboxylic acid compound and / or a thiocarboxylic acid compound with a hydroxy compound and / or a thiol compound. In particular, from the viewpoint of improving heat resistance, an active ester curing agent derived from a carboxylic acid compound is preferable, an active ester curing agent obtained from a carboxylic acid compound and a hydroxy compound is more preferable, and an active ester curing agent obtained from a carboxylic acid compound and a phenol compound and / or a naphthol compound is even more preferable.

[0117] Examples of the carboxylic acid compound include benzoic acid, acetic acid, succinic acid, maleic acid, itaconic acid, phthalic acid, isophthalic acid, terephthalic acid, pyromellitic acid, and the like.

[0118] Examples of the phenolic compound or naphthol compound 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-dihydroxynaphthalene, 1,6-dihydroxynaphthalene, 2,6-dihydroxynaphthalene, dihydroxybenzophenone, trihydroxybenzophenone, tetrahydroxybenzophenone, phloroglucin, benzenetriol, dicyclopentadiene-type diphenol compounds, phenol novolac, and the like. Herein, the "dicyclopentadiene-type diphenol compound" refers to a diphenol compound obtained by condensing two molecules of phenol with one molecule of dicyclopentadiene.

[0119] Preferable specific examples of the active ester curing agent include an active ester curing agent containing a naphthalene structure (also referred to as a "naphthalene-type active ester curing agent"), an active ester curing agent containing a dicyclopentadiene-type diphenol structure (also referred to as a "dicyclopentadiene-type active ester curing agent"), an active ester curing agent containing an acetylated product of phenol novolac, and an active ester curing agent containing a benzoylated product of phenol novolac. The "dicyclopentadiene-type diphenol structure" represents a divalent structural unit composed of phenylene-dicyclopentylene-phenylene.

[0120] Among them, from the viewpoint of being able to provide good dielectric properties in the combination of the component (A) and the component (B), the naphthalene-type active ester curing agent and the dicyclopentadiene-type active ester curing agent are more preferable.

[0121] Examples of commercially available active ester curing agents include, as dicyclopentadiene-type active ester curing agents, for example, "EXB9451", "EXB9460", "EXB9460S", "EXB-8000L", "EXB-8000L-65M", "EXB-8000L-65TM", "HPC-8000L-65TM", "HPC-8000", "HPC-8000-65T", "HPC-8000H", "HPC-8000H-65TM" (manufactured by DIC Corporation); as naphthalene-type active ester curing agents, for example, "EXB-8100L-65T", "EXB-8150-60T", "EXB-8150-62T", "EXB-9416-70BK", "HPC-8150-60T", "HPC-8150-62T" (manufactured by DIC Corporation), "PC1300-02-65MA" (manufactured by Air Water, Inc.); as active ester compounds that are acetylated products of phenol novolac, for example, "DC808" (manufactured by Mitsubishi Chemical Corporation); as active ester compounds that are benzoylated products of phenol novolac, for example, "YLH1026", "YLH1030", "YLH1048" (manufactured by Mitsubishi Chemical Corporation); as phosphorus-containing active ester compounds, for example, "EXB9401" (manufactured by DIC Corporation), and the like.

[0122] - Cyanate Ester-Based Curing Agents - Examples of cyanate ester-based curing agents include, for example, bifunctional cyanate resins such as bisphenol A dicyanate, polyphenol cyanate, oligo(3-methylene-1,5-phenylene cyanate), 4,4'-methylenebis(2,6-dimethylphenyl cyanate), 4,4'-ethylidenediphenyl dicyanate, hexafluorobisphenol A dicyanate, 2,2-bis(4-cyanate)phenylpropane, 1,1-bis(4-cyanatephenylmethane), bis(4-cyanate-3,5-dimethylphenyl)methane, 1,3-bis(4-cyanatephenyl-1-(methylethylidene))benzene, bis(4-cyanatephenyl)thioether, and bis(4-cyanatephenyl)ether; polyfunctional cyanate resins derived from phenol novolac and cresol novolac, etc.; prepolymers in which some of these cyanate resins are triazine-modified; and the like.

[0123] Specific examples of the cyanate ester-based curing agent include "PT30" and "PT60" (phenol novolak type polyfunctional cyanate ester resin), "ULL-950S" (polyfunctional cyanate ester resin), "BA230", "BA230S75" (prepolymer in which part or all of bisphenol A dicyanate is triazine-formed into a trimer), etc. manufactured by Lonza Japan Co., Ltd.

[0124] - Carbodiimide-based curing agent - The carbodiimide-based curing agent is a compound having one or more, preferably two or more carbodiimide groups (-N = C = N-) in one molecule. Specific examples of the carbodiimide-based curing agent include Carbodilite (registered trademark) V-03 (carbodiimide group equivalent: 216 g / eq.), V-05 (carbodiimide group equivalent: 262 g / eq.), V-07 (carbodiimide group equivalent: 200 g / eq.); V-09 (carbodiimide group equivalent: 200 g / eq.) manufactured by Nisshinbo Chemical Co., Ltd.; and Stabaxol (registered trademark) P (carbodiimide group equivalent: 302 g / eq.) manufactured by Rhein Chemie.

[0125] In the resin composition of the present invention, the component (C) may contain a curing agent other than the component (C-1). For example, the component (C) may contain one or more curing agents selected from the group consisting of (C-2) phenol-based curing agents, naphthol-based curing agents, acid anhydride-based curing agents, and amine-based curing agents.

[0126] - Phenol-based curing agent and naphthol-based curing agent - As phenolic curing agents and naphtholic curing agents, those having a novolak structure are preferred from the viewpoints of heat resistance and water resistance. Further, from the viewpoint of adhesion to the conductor layer, nitrogen-containing phenolic curing agents and nitrogen-containing naphtholic curing agents are preferred, and phenolic curing agents containing a triazine skeleton and naphtholic curing agents containing a triazine skeleton are more preferred. From the viewpoint of realizing an insulating layer that is good in all of heat resistance, water resistance, and adhesion to the conductor layer, phenolic curing agents and naphtholic curing agents having both a triazine skeleton and a novolak structure are particularly suitable.

[0127] Specific examples of the phenolic curing agent and the naphtholic curing agent include, for example, "MEH-7700", "MEH-7810", "MEH-7851", "MEH-8000H" manufactured by Meiwa Kasei Co., Ltd.; "NHN", "CBN", "GPH" manufactured by Nippon Kayaku Co., Ltd.; "SN-170", "SN-180", "SN-190", "SN-475", "SN-485", "SN-495", "SN-495V", "SN-375", "SN-395" manufactured by Nippon Steel Chemical & Material Co., Ltd.; "TD-2090", "TD-2090-60M", "LA-7052", "LA-7054", "LA-1356", "LA-3018", "LA-3018-50P", "EXB-9500", "HPC-9500", "KA-1160", "KA-1163", "KA-1165" manufactured by DIC Corporation; "GDP-6115L", "GDP-6115H", "ELPC75", etc. manufactured by Gunei Chemical Industry Co., Ltd.

[0128] - Acid anhydride-based curing agent - Examples of the acid anhydride-based curing agent include curing agents having one or more acid anhydride groups in one molecule. Specific examples of the acid anhydride-based curing agent include phthalic anhydride, tetrahydrophthalic anhydride, hexahydrophthalic anhydride, methyltetrahydrophthalic anhydride, methylhexahydrophthalic anhydride, methyl nadic anhydride, hydrogenated methyl nadic anhydride, trialkyltetrahydrophthalic anhydride, dodecenyl succinic anhydride, 5-(2,5-dioxotetrahydro-3-furanyl)-3-methyl-3-cyclohexene-1,2-dicarboxylic anhydride, trimellitic anhydride, pyromellitic anhydride, benzophenone tetracarboxylic dianhydride, biphenyltetracarboxylic dianhydride, 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(anhydrotrimellitate), and polymer-type acid anhydrides such as a styrene-maleic acid resin obtained by copolymerizing styrene and maleic acid. Commercially available products of the acid anhydride-based curing agent include "MH-700" manufactured by Shin Nippon Rika Co., Ltd.

[0129] - Amine-based curing agent - Examples of amine curing agents include curing agents having one or more amino groups in one molecule, such as aliphatic amines, polyether amines, alicyclic amines, aromatic amines, etc. Specific examples of amine curing agents include 4,4'-methylenebis(2,6-dimethylaniline), diphenyldiaminosulfone, 4,4'-diaminodiphenylmethane, 4,4'-diaminodiphenylsulfone, 3,3'-diaminodiphenylsulfone, m-phenylenediamine, m-xylylenediamine, diethyltoluenediamine, 4,4'-diaminodiphenyl ether, 3,3'-dimethyl-4,4'-diaminobiphenyl, 2,2'-dimethyl-4,4'-diaminobiphenyl, 3,3'-dihydroxybenzidine, 2,2-bis(3-amino-4-hydroxyphenyl)propane, 3,3-dimethyl-5,5-diethyl-4,4-diphenylmethanediamine, 2,2-bis(4-aminophenyl)propane, 2,2-bis(4-(4-aminophenoxy)phenyl)propane, 1,3-bis(3-aminophenoxy)benzene, 1,3-bis(4-aminophenoxy)benzene, 1,4-bis(4-aminophenoxy)benzene, 4,4'-bis(4-aminophenoxy)biphenyl, bis(4-(4-aminophenoxy)phenyl)sulfone, bis(4-(3-aminophenoxy)phenyl)sulfone, etc. The amine curing agent may be a commercially available product, for example, "KAYABOND C-200S", "KAYABOND C-100", "KAYAHARD A-A", "KAYAHARD A-B", "KAYAHARD A-S" manufactured by Nippon Kayaku Co., Ltd., "EPICURE W" manufactured by Mitsubishi Chemical Corporation, etc.

[0130] (A) In combination with the component and the (B) component, from the viewpoint of easily realizing a resin composition having good dielectric properties, when the resin component in the resin composition is 100% by mass, the content of the (C) component in the resin composition is preferably 10% by mass or more, more preferably 20% by mass or more, still more preferably 30% by mass or more, 35% by mass or more, or 40% by mass or more. The upper limit of the content is not particularly limited and may be determined according to the properties required for the resin composition. For example, it may be 80% by mass or less, 75% by mass or less, or 70% by mass or less.

[0131] (In combination with component (A) and component (B), from the viewpoint of realizing a resin composition having good dielectric properties, the content of component (C-1) in component (C) is preferably 70% by mass or more, more preferably 80% by mass or more, still more preferably 85% by mass or more, 90% by mass or more, or 95% by mass or more when the non-volatile component of component (C) is 100% by mass. The upper limit of the content is not particularly limited and may be 100% by mass, but may be, for example, 99.5% by mass or less, 99% by mass or less, etc.)

[0132] In the resin composition of the present invention, the mass ratio of component (C-1) to component (B) ((C-1) component / (B) component) is preferably 1 or more, more preferably 1.1 or more, still more preferably 1.2 or more, 1.4 or more, from the viewpoint of providing a cured product having excellent dielectric properties. As described above, according to the resin composition of the present invention using component (A), even when component (C-1) is contained to such an extent that excellent dielectric properties can be realized, when a wiring pattern is formed by the semi-additive method, it exhibits good adhesion to the plating conductor and can provide a cured product that exhibits good adhesion to the underlying conductor when exposed to a high-temperature and high-humidity environment. For example, in the resin composition of the present invention, the mass ratio of component (C-1) to component (B) may be increased to 1.5 or more, 1.6 or more, or 1.7 or more. The upper limit of the mass ratio ((B) component / (A) component) may be, for example, 2 or less, 1.9 or less, 1.8 or less, etc.)

[0133] <(D) Inorganic filler> The resin composition of the present invention may further contain an inorganic filler as component (D). By containing component (D), the linear thermal expansion coefficient and the dielectric tangent can be further reduced.)

[0134] Examples of the material for the component (D) include silica, alumina, glass, cordierite, silicon oxide, barium sulfate, barium carbonate, talc, clay, mica powder, zinc oxide, hydrotalcite, boehmite, aluminum silicate, aluminum hydroxide, magnesium hydroxide, calcium carbonate, magnesium carbonate, magnesium oxide, boron nitride, aluminum nitride, manganese nitride, aluminum borate, strontium carbonate, strontium titanate, calcium titanate, magnesium titanate, bismuth titanate, titanium oxide, zirconium oxide, barium titanate, barium zirconate titanate, barium zirconate, calcium zirconate, zirconium phosphate, and zirconium tungstate phosphate. Among these, silica is particularly preferred. Examples of silica include amorphous silica, fused silica, crystalline silica, synthetic silica, and hollow silica. Also, spherical silica is preferred as the silica. The component (D) may be used alone or in combination of two or more.

[0135] Examples of the commercially available products of the component (D) include "SP60-05", "SP507-05" manufactured by Nippon Steel Chemical & Material Co., Ltd.; "SC2500SQ", "SO-C4", "SO-C2", "SO-C1", "YC100C", "YA050C", "YA050C-MJE", "YA010C" manufactured by Admatechs Co., Ltd.; "UFP-30", "DAW-03", "FB-105FD" manufactured by Denka Co., Ltd.; "Silfill NSS-3N", "Silfill NSS-4N", "Silfill NSS-5N" manufactured by Tokuyama Corporation; "Celfiers" manufactured by Pacific Cement Co., Ltd. 」 na and the like can be mentioned.

[0136] (D) component's average particle size is not particularly limited, but preferably 10 μm or less, more preferably 5 μm or less, still more preferably 3 μm or less, 2 μm or less, 1 μm or less, or 0.7 μm or less. The lower limit of the average particle size is not particularly limited, but preferably 0.01 μm or more, more preferably 0.05 μm or more, still more preferably 0.07 μm or more, 0.1 μm or more, or 0.2 μm or more. (D) component's average particle size can be measured by the laser diffraction / scattering method based on the Mie scattering theory. Specifically, it can be measured by creating the particle size distribution of the inorganic filler on a volume basis with a laser diffraction / scattering type particle size distribution measuring device and taking its median diameter as the average particle size. As the measurement sample, 100 mg of the inorganic filler and 10 g of methyl ethyl ketone can be weighed into a vial and dispersed by ultrasonic waves for 10 minutes. The measurement sample can be used to measure the volume-based particle size distribution of the inorganic filler in a flow cell method using a laser diffraction type particle size distribution measuring device with the light source wavelengths of blue and red, and the average particle size can be calculated as the median diameter from the obtained particle size distribution. Examples of the laser diffraction type particle size distribution measuring device include "LA-960" manufactured by Horiba, Ltd.

[0137] (D) component's specific surface area is not particularly limited, but preferably 0.1 m 2 / g or more, more preferably 0.5 m 2 / g or more, still more preferably 1 m 2 / g or more, 3 m 2 / g or more, or 5 m 2 / g or more. The upper limit of the specific surface area is not particularly limited, but preferably 100 m 2 / g or less, more preferably 80 m 2 / g or less, still more preferably 60 m 2 / g or less, 50 m 2 / g or less, or 40 m 2 / g or less. (D) component's specific surface area can be obtained by adsorbing nitrogen gas on the sample surface using a specific surface area measuring device (Macsorb HM-1210 manufactured by Mountech Co., Ltd.) according to the BET method and calculating the specific surface area using the BET multi-point method.

[0138] The component (D) may be a non-hollow inorganic filler with a porosity of 0% by volume (preferably non-hollow silica), a hollow inorganic filler with a porosity exceeding 0% by volume (preferably hollow silica), or may contain both. The component (D) may contain only a non-hollow inorganic filler (preferably non-hollow silica), only a hollow inorganic filler (preferably hollow silica), or may contain a combination of a non-hollow inorganic filler (preferably non-hollow silica) and a hollow inorganic filler (preferably hollow silica). When the component (D) contains a hollow inorganic filler, it is suitable because it is easy to realize a resin composition that provides a cured product having even better dielectric properties with a lower dielectric constant suppressed. The porosity of the hollow inorganic filler is preferably 10% by volume or more, more preferably 15% by volume or more, still more preferably 20% by volume or more, and the upper limit thereof is preferably 90% by volume or less, more preferably 85% by volume or less, still more preferably 80% by volume or less, 75% by volume or less, 70% by volume or less, 65% by volume or less, 60% by volume or less, 55% by volume or less, or 50% by volume or less. The porosity P (% by volume) of the inorganic filler is defined as the volume-based ratio (total volume of pores / volume of particles) of the total volume of pores present in one or more inside the particles to the volume of the whole particles based on the outer surface of the particles. For example, the measured value D M (g / cm 3 ) and the theoretical value D T (g / cm 3 ) of the material density of the material forming the inorganic filler are used to calculate by the following formula (1).

[0139]

Equation

[0140] The actual density of the inorganic filler can be measured, for example, using a true density measuring device. Examples of the true density measuring device include ULTRAPYCNOMETER 1000 manufactured by QUANTACHROME. As the measurement gas, for example, nitrogen is used.

[0141] Component (D) is preferably surface-treated with an appropriate surface treatment agent. By being surface-treated, the moisture resistance and dispersibility of component (D) can be enhanced. Examples of the surface treatment agent include silane coupling agents such as vinyl-based silane coupling agents, epoxy-based silane coupling agents, styryl-based silane coupling agents, (meth)acrylic-based silane coupling agents, amino-based silane coupling agents, isocyanurate-based silane coupling agents, ureido-based silane coupling agents, mercapto-based silane coupling agents, isocyanate-based silane coupling agents, and acid anhydride-based silane coupling agents; non-silane coupling - alkoxysilane compounds such as methyltrimethoxysilane and phenyltrimethoxysilane; and silazane compounds. The surface treatment agent may be used alone or in combination of two or more.

[0142] Examples of commercially available surface treatment agents include "KBM403" (3-glycidoxypropyltrimethoxysilane) manufactured by Shin-Etsu Chemical Co., Ltd., "KBM803" (3-mercaptopropyltrimethoxysilane) manufactured by Shin-Etsu Chemical Co., Ltd., "KBE903" (3-aminopropyltriethoxysilane) manufactured by Shin-Etsu Chemical Co., Ltd., "KBM573" (N-phenyl-3-aminopropyltrimethoxysilane) manufactured by Shin-Etsu Chemical Co., Ltd., "SZ-31" (hexamethyldisilazane) manufactured by Shin-Etsu Chemical Co., Ltd., and the like.

[0143] From the viewpoint of improving the dispersibility of the inorganic filler, the degree of surface treatment with the surface treatment agent preferably falls within a predetermined range. Specifically, 100% by mass of the inorganic filler is preferably surface-treated with 0.2 to 5% by mass of the surface treatment agent.

[0144] The degree of surface treatment with the surface treatment agent can be evaluated by the amount of carbon per unit surface area of the inorganic filler. The amount of carbon per unit surface area of the inorganic filler is preferably 0.02 mg / m 2 or more from the viewpoint of improving the dispersibility of the inorganic filler, more preferably 0.1 mg / m 2 or more, and still more preferably 0.2 mg / m 2The above is more preferable. On the other hand, from the viewpoint of preventing an increase in the melt viscosity of the resin composition and the melt viscosity in the sheet form, 1.0 mg / m 2 or less is preferable, 0.8 mg / m 2 or less is more preferable, and 0.5 mg / m 2 or less is even more preferable. The amount of carbon per unit surface area of the component (D) can be measured after washing the surface-treated inorganic filler with a solvent (for example, methyl ethyl ketone (MEK)). Specifically, a sufficient amount of MEK as a solvent is added to the inorganic filler surface-treated with a surface treatment agent, and ultrasonic cleaning is performed at 25 °C for 5 minutes. After removing the supernatant and drying the solid content, the amount of carbon per unit surface area of the inorganic filler can be measured using a carbon analyzer. As the carbon analyzer, "EMIA-320V" manufactured by Horiba, Ltd. can be used.

[0145] When the resin composition of the present invention contains the component (D), the content of the component (D) in the resin composition is, from the viewpoint of easily realizing a resin composition that provides even better dielectric properties in combination with the components (A) to (C), when the non-volatile components in the resin composition are 100% by mass, for example, 40% by mass or more, preferably 50% by mass or more. As described above, according to the present invention using the component (A), even when adopting a specific composition that contributes to good dielectric properties, when forming a wiring pattern by the semi-additive method, it exhibits good adhesion to a plating conductor and can provide a cured product that exhibits good adhesion to an underlying conductor when exposed to a high-temperature and high-humidity environment. For example, in the resin composition of the present invention, the content of the component (D) may be increased to 60% by mass or more, 65% by mass or more, 70% by mass or more, 72% by mass or more, or 74% by mass or more. The upper limit of the content of the component (D) is not particularly limited, but can be, for example, 90% by mass or less, 85% by mass or less, etc.

[0146] From the same perspective, when the content of component (D) in the resin composition is based on 100% by volume of the non-volatile components in the resin composition, for example, it is 30% by volume or more, preferably 40% by volume or more. As described above, according to the present invention using component (A), the content of component (D) can be further increased. For example, in the resin composition of the present invention, the content of component (D) may be increased to 45% by volume or more, 50% by volume or more, 55% by volume or more, 56% by volume or more, 58% by volume or more, or 60% by volume or more. The upper limit of the content of component (D) is not particularly limited, but may be, for example, 75% by volume or less, 70% by volume or less, etc.

[0147] Therefore, in a preferred embodiment, the content of component (D) in the resin composition is 60% by mass or more when the non-volatile components in the resin composition are 100% by mass, or 45% by volume or more when the non-volatile components in the resin composition are 100% by volume.

[0148] <(E) Thermoplastic resin> The resin composition of the present invention may contain a thermoplastic resin as component (E).

[0149] Examples of the thermoplastic resin include phenoxy resin, polyvinyl acetal resin, polyolefin resin, polybutadiene resin, polyimide resin, polyamideimide resin, polyetherimide resin, polysulfone resin, polyethersulfone resin, polyphenylene ether resin, polycarbonate resin, polyetheretherketone resin, and polyester resin. The thermoplastic resin may be used alone or in combination of two or more.

[0150] The weight average molecular weight of the thermoplastic resin in terms of polystyrene is preferably in the range of 8,000 to 70,000, more preferably in the range of 10,000 to 60,000, and even more preferably in the range of 20,000 to 60,000. The weight average molecular weight of the thermoplastic resin in terms of polystyrene is measured by the gel permeation chromatography (GPC) method. Specifically, the weight average molecular weight of the thermoplastic resin in terms of polystyrene is measured at a column temperature of 40 °C using LC-9A / RID-6A manufactured by Shimadzu Corporation as the measuring device, Shodex K-800P / K-804L / K-804L manufactured by Showa Denko K.K. as the column, and chloroform or the like as the mobile phase, and can be calculated using the calibration curve of standard polystyrene.

[0151] Examples of the phenoxy resin include phenoxy resins having one or more skeletons selected from the group consisting of bisphenol A skeleton, bisphenol F skeleton, bisphenol S skeleton, bisphenol acetophenone skeleton, novolak skeleton, biphenyl skeleton, fluorene skeleton, dicyclopentadiene skeleton, norbornene skeleton, naphthalene skeleton, anthracene skeleton, adamantane skeleton, terpene skeleton, and trimethylcyclohexane skeleton. The terminal of the phenoxy resin may be any functional group such as a phenolic hydroxyl group or an epoxy group. The phenoxy resin may be used alone or in combination of two or more. Specific examples of the phenoxy resin include "1256" and "4250" (both are bisphenol A skeleton-containing phenoxy resins), "YX8100" (bisphenol S skeleton-containing phenoxy resin), and "YX6954" (bisphenol acetophenone skeleton-containing phenoxy resin) manufactured by Mitsubishi Chemical Corporation, and in addition, "FX280" and "FX293" manufactured by Nippon Steel Chemical & Material Co., Ltd., "YX7553", "YL6794", "YL7213", "YL7290", and "YL7482" manufactured by Mitsubishi Chemical Corporation, etc.

[0152] Examples of the polyvinyl acetal resin include, for example, polyvinyl formal resin and polyvinyl butyral resin, and polyvinyl butyral resin is preferred. Specific examples of the polyvinyl acetal resin include, for example, "Denka Butyral 4000-2", "Denka Butyral 5000-A", "Denka Butyral 6000-C", "Denka Butyral 6000-EP" manufactured by Denka Co., Ltd., and the Esrec BH series, BX series, KS series, BL series, BM series, etc. manufactured by Sekisui Chemical Co., Ltd.

[0153] Specific examples of the polyimide resin include "Ricacote SN20" and "Ricacote PN20" manufactured by Shin Nippon Rika Co., Ltd. Specific examples of the polyimide resin also include modified polyimides such as linear polyimide obtained by reacting bifunctional hydroxyl group-terminated polybutadiene, diisocyanate compound and tetracarboxylic dianhydride (described in JP-A-2006-37083), and polyimide containing polysiloxane skeleton (described in JP-A-2002-12667 and JP-A-2000-319386, etc.).

[0154] Specific examples of the polyamideimide resin include "Vylon Max HR11NN" and "Vylon Max HR16NN" manufactured by Toyobo Co., Ltd. Specific examples of the polyamideimide resin also include modified polyamideimides such as polysiloxane skeleton-containing polyamideimide "KS9100", "KS9300", etc. manufactured by Hitachi Chemical Co., Ltd.

[0155] Specific examples of the polyethersulfone resin include "PES5003P" manufactured by Sumitomo Chemical Co., Ltd.

[0156] Specific examples of the polysulfone resin include polysulfone "P1700", "P3500", etc. manufactured by Solvay Advanced Polymers, LLC.

[0157] When the resin composition of the present invention contains the component (E), the content of the component (E) in the resin composition may be determined according to the properties required for the resin composition. However, when the resin component in the resin composition is 100% by mass, for example, it is 0.1% by mass or more, preferably 0.3% by mass or more, more preferably 0.5% by mass or more, 0.6% by mass or more, or 0.8% by mass or more. The upper limit of the content of the component (E) is not particularly limited, but may be, for example, 10% by mass or less, 8% by mass or less, 6% by mass or less, etc.

[0158] <(F) Radical polymerizable resin> The resin composition of the present invention may contain a radical polymerizable resin as the component (F).

[0159] The type of the radical polymerizable resin is not particularly limited as long as it has one or more (preferably two or more) radical polymerizable unsaturated groups in one molecule. Examples of the radical polymerizable resin include resins having one or more selected from maleimide groups, vinyl groups, allyl groups, styryl groups, vinylphenyl groups, acryloyl groups, methacryloyl groups, fumaroyl groups, and maleoyl groups as radical polymerizable unsaturated groups. Among them, from the viewpoint of providing a cured product having good dielectric properties, the radical polymerizable resin is preferably one or more selected from maleimide resins, (meth)acrylic resins, and styryl resins.

[0160] As the maleimide resin, as long as it has one or more (preferably two or more) maleimide groups (2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl groups) in one molecule, its type is not particularly limited. Examples of the maleimide resin include (1) maleimide resins containing an aliphatic skeleton (preferably an aliphatic skeleton with 36 carbon atoms derived from dimer diamine), such as "BMI-3000J", "BMI-5000", "BMI-1400", "BMI-1500", "BMI-1700", "BMI-689" (all manufactured by Dicnae Moleculars), "SLK6895-T90" (manufactured by Shin-Etsu Chemical Co., Ltd.); (2) maleimide resins containing an indane skeleton described in Invention Association Public Technical Report Publication No. 2020-500211; (3) maleimide resins containing an aromatic ring skeleton directly bonded to the nitrogen atom of the maleimide group, such as "MIR-3000-70MT" (manufactured by Nippon Kayaku Co., Ltd.), "BMI-4000" (manufactured by Daiwa Kasei Co., Ltd.), "BMI-80" (manufactured by KAI Chemical Co., Ltd.).

[0161] (Meta)acrylic resin, as long as it has one or more (preferably two or more) (meta)acryloyl groups in one molecule, its type is not particularly limited and it may be a monomer or an oligomer. Here, the term "(meta)acryloyl group" is a general term for acryloyl group and methacryloyl group. Examples of the methacrylic resin include, in addition to (meta)acrylate monomers, (meta)acrylic resins such as "A-DOG" (manufactured by Shin-Nakamura Chemical Co., Ltd.), "DCP-A" (manufactured by Kyoeisha Chemical Co., Ltd.), "NPDGA", "FM-400", "R-687", "THE-330", "PET-30", "DPHA" (all manufactured by Nippon Kayaku Co., Ltd.).

[0162] As the styryl resin, as long as it has one or more (preferably two or more) styryl groups or vinylphenyl groups in one molecule, its type is not particularly limited and it may be a monomer or an oligomer. Examples of the styryl resin include, in addition to styrene monomer, styryl resins such as "OPE-2St", "OPE-2St 1200", "OPE-2St 2200" (all manufactured by Mitsubishi Gas Chemical Co., Ltd.).

[0163] When the resin composition of the present invention contains the component (F), the content of the component (F) in the resin composition may be determined according to the properties required for the resin composition. However, when the resin component in the resin composition is 100% by mass, for example, it is 0.1% by mass or more, preferably 0.3% by mass or more, more preferably 0.5% by mass or more or 0.6% by mass or more. The upper limit of the content of the component (F) is not particularly limited, but may be, for example, 10% by mass or less, 8% by mass or less, 6% by mass or less, etc.

[0164] <(G) Curing accelerator> The resin composition of the present invention may contain a curing accelerator other than the component (A) as the component (G).

[0165] Examples of the component (G) include phosphorus-based curing accelerators, amine-based curing accelerators, imidazole-based curing accelerators, guanidine-based curing accelerators, metal-based curing accelerators, peroxide-based curing accelerators, etc. The curing accelerator may be used alone or in combination of two or more.

[0166] When the resin composition of the present invention contains the component (G), the content of the component (G) in the resin composition, when the resin component in the resin composition is 100% by mass, is preferably 0.001% by mass or more, more preferably 0.005% by mass or more, still more preferably 0.01% by mass or more, and preferably 1% by mass or less, more preferably 0.8% by mass or less, 0.7% by mass or less or 0.6% by mass or less.

[0167] <Optional additive> The resin composition of the present invention may further contain an optional additive. Examples of such additives include radical polymerization initiators such as peroxide-based radical polymerization initiators and azo-based radical polymerization initiators; organometallic compounds such as organic copper compounds, organic zinc compounds, and organic cobalt compounds; colorants such as phthalocyanine blue, phthalocyanine green, iodine green, diazo yellow, crystal violet, titanium oxide, and carbon black; polymerization inhibitors such as hydroquinone, catechol, pyrogallol, and phenothiazine; leveling agents such as silicone-based leveling agents and acrylic polymer-based leveling agents; thickeners such as benton and montmorillonite; antifoaming agents such as silicone-based antifoaming agents, acrylic-based antifoaming agents, fluorine-based antifoaming agents, and vinyl resin-based antifoaming agents; ultraviolet absorbers such as benzotriazole-based ultraviolet absorbers; adhesion improvers such as urea silane; adhesion imparting agents such as triazole-based adhesion imparting agents, tetrazole-based adhesion imparting agents, and triazine-based adhesion imparting agents; antioxidants such as hindered phenol-based antioxidants; fluorescent brighteners such as stilbene derivatives; surfactants such as fluorine-based surfactants and silicone-based surfactants; flame retardants such as phosphorus-based flame retardants (e.g., phosphate ester compounds, phosphazene compounds, phosphinic acid compounds, red phosphorus), nitrogen-based flame retardants (e.g., melamine sulfate), halogen-based flame retardants, and inorganic flame retardants (e.g., antimony trioxide); dispersants such as phosphate ester-based dispersants, polyoxyalkylene-based dispersants, acetylene-based dispersants, silicone-based dispersants, anionic dispersants, and cationic dispersants; stabilizers such as borate-based stabilizers, titanate-based stabilizers, aluminate-based stabilizers, zirconate-based stabilizers, isocyanate-based stabilizers, carboxylic acid-based stabilizers, and carboxylic anhydride-based stabilizers. The content of such additives may be determined according to the properties required for the resin composition.

[0168] <Organic solvent> The resin composition of the present invention may further contain an organic solvent as a volatile component. Examples of the organic solvent include ketone solvents such as acetone, methyl ethyl ketone, methyl isobutyl ketone, and cyclohexanone; ester solvents such as methyl acetate, ethyl acetate, butyl acetate, isobutyl acetate, isoamyl acetate, methyl propionate, ethyl propionate, and γ-butyrolactone; ether solvents such as tetrahydropyran, tetrahydrofuran, 1,4-dioxane, diethyl ether, diisopropyl ether, dibutyl ether, and diphenyl ether; alcohol solvents such as methanol, ethanol, propanol, butanol, and ethylene glycol; ether ester solvents such as 2-ethoxyethyl acetate, propylene glycol monomethyl ether acetate, diethylene glycol monoethyl ether acetate, ethyl diglycol acetate, γ-butyrolactone, and methyl methoxypropionate; ester alcohol solvents such as methyl lactate, ethyl lactate, and methyl 2-hydroxyisobutyrate; ether alcohol solvents such as 2-methoxypropanol, 2-methoxyethanol, 2-ethoxyethanol, propylene glycol monomethyl ether, and diethylene glycol monobutyl ether (butyl carbitol); amide solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, and N-methyl-2-pyrrolidone; sulfoxide solvents such as dimethyl sulfoxide; nitrile solvents such as acetonitrile and propionitrile; aliphatic hydrocarbon solvents such as hexane, cyclopentane, cyclohexane, and methylcyclohexane; aromatic hydrocarbon solvents such as benzene, toluene, xylene, ethylbenzene, and trimethylbenzene. The organic solvent may be used alone or in combination of two or more.

[0169] The resin composition of the present invention can be produced, for example, by adding components (A), (B), (C), and, if necessary, components (D), (E), (F), (G), other additives, and organic solvents to an arbitrary preparation container in an arbitrary order and / or partially or entirely simultaneously and mixing them. Further, during the process of adding and mixing each component, the temperature can be appropriately set, and heating and / or cooling can be performed temporarily or throughout the process. Further, during or after the process of adding and mixing, the resin composition may be stirred or shaken using a stirring device or a shaking device such as a mixer to be uniformly dispersed. Further, defoaming may be performed under low-pressure conditions such as under vacuum simultaneously with stirring or shaking.

[0170] As described above, the resin composition of the present invention containing component (A) exhibits good adhesion to a plating conductor when forming a wiring pattern by the semi-additive method, even when adopting a specific composition that contributes to good dielectric properties, and can provide a cured product that exhibits good adhesion to an underlying conductor when exposed to a high-temperature and high-humidity environment. Furthermore, while exhibiting good adhesion to a plating conductor comparable to the case where a certain amount of DMAP is used when forming a wiring pattern by the semi-additive method, it can significantly reduce and suppress the occurrence of cracks on the pattern regardless of the surface circuit pattern of the underlying substrate.

[0171] In one embodiment, the cured product of the resin composition of the present invention is characterized by having a low dielectric tangent (Df). For example, when measured at 5.8 GHz and 23 °C as described in [Test Example 1: Measurement of Dielectric Tangent] to be described later, the dielectric tangent (Df) of the cured product of the resin composition of the present invention can preferably be 0.004 or less, 0.0038 or less, 0.0036 or less, 0.0034 or less, or 0.0032 or less.

[0172] In one embodiment, the cured product of the resin composition of the present invention exhibits high adhesion to the underlying conductor. For example, when exposed to high temperature and high humidity conditions of 130°C and 85% RH for 100 hours as described in the [Test Example 3: Measurement of Adhesion Strength to Copper Foil after High Temperature and High Humidity Environment Test] section to be described later, the adhesion strength to the conductor foil after exposure to the high temperature and high humidity conditions is preferably 0.35 kgf / cm or more, 0.4 kgf / cm or more, 0.45 kgf / cm or more, 0.46 kgf / cm or more, 0.48 kgf / cm or more, 0.5 kgf / cm or more.

[0173] In one embodiment, the cured product of the resin composition of the present invention exhibits high adhesion to the plated conductor. For example, when a plated conductor is formed as described in the [Test Example 4: Measurement of Adhesion Strength to Plated Copper] section to be described later, the adhesion strength to the plated conductor is preferably 0.45 kgf / cm or more, 0.5 kgf / cm or more, 0.52 kgf / cm or more, 0.54 kgf / cm or more, 0.55 kgf / cm or more.

[0174] As described above, even when the resin composition of the present invention adopts a specific composition that contributes to good dielectric properties, it exhibits good adhesion to a plating conductor when a wiring pattern is formed by the semi-additive method, and can provide a cured product that exhibits good adhesion to an underlying conductor when exposed to a high-temperature and high-humidity environment. Furthermore, when a certain amount of DMAP is used when forming a wiring pattern by the semi-additive method, it exhibits good adhesion to a plating conductor comparable to that in the case of using a certain amount of DMAP, and can significantly reduce and suppress the occurrence of cracks on the pattern regardless of the surface circuit pattern of the underlying substrate. Therefore, the resin composition of the present invention can be suitably used as a resin composition for forming an insulating layer of a printed wiring board (resin composition for insulating layer of a printed wiring board), and can be more suitably used as a resin composition for forming an interlayer insulating layer of a printed wiring board (resin composition for interlayer insulating layer of a printed wiring board). The resin composition of the present invention can also be suitably used when the printed wiring board is a circuit board with built-in components. The resin composition of the present invention can also be suitably used as a resin composition for forming an insulating layer of a redistribution substrate of a semiconductor package (resin composition for insulating layer of a redistribution substrate). In the present invention, a printed wiring board and a redistribution substrate are collectively referred to as a "circuit board". Therefore, the resin composition of the present invention can be suitably used for an insulating layer of a circuit board. By forming an insulating layer using the resin composition of the present invention, a circuit board having a fine circuit with a minimum L / S ratio of preferably 5 / 5 μm or less, more preferably 4 / 4 μm or less, still more preferably 3 / 3 μm or less, or 2 / 2 μm or less can be manufactured while realizing good adhesion to a plating conductor and an underlying conductor, which is beneficial.

[0175] The resin composition of the present invention can be further widely used in applications where a resin composition is required, such as resin sheets, sheet-like laminated materials such as prepregs, solder resists, underfill materials, die bonding materials, hole filling resins, component embedding resins, and the like.

[0176] [Sheet-like laminated material (resin sheet, prepreg)] The resin composition of the present invention can be used as it is, or it may be used in the form of a sheet-like laminated material containing the resin composition.

[0177] As the sheet-like laminated material, the resin sheets and prepregs shown below are preferable.

[0178] In one embodiment, the resin sheet includes a support and a layer of the resin composition provided on the support (hereinafter simply referred to as "resin composition layer"), and the resin composition layer is formed from the resin composition of the present invention.

[0179] The thickness of the resin composition layer varies depending on the application, and may be appropriately determined according to the application. For example, from the viewpoint of thinning printed wiring boards and semiconductor packages, the thickness of the resin composition layer is preferably 100 μm or less, 80 μm or less, 60 μm or less, 50 μm or less, 40 μm or less, or 30 μm or less. The lower limit of the thickness of the resin composition layer is not particularly limited, but may usually be 1 μm or more, 5 μm or more, etc.

[0180] Examples of the support include thermoplastic resin films, metal foils, and release papers, and thermoplastic resin films and metal foils are preferable. Therefore, in a preferred embodiment, the support is a thermoplastic resin film or a metal foil.

[0181] When a thermoplastic resin film is used as the support, examples of the thermoplastic resin include polyesters such as polyethylene terephthalate (PET) and polyethylene naphthalate (PEN), acrylics such as polycarbonate (PC) and polymethyl methacrylate (PMMA), cyclic polyolefins, triacetyl cellulose (TAC), polyethersulfide (PES), polyether ketone, polyimide, etc. Among them, polyethylene terephthalate and polyethylene naphthalate are preferable, and inexpensive polyethylene terephthalate is particularly preferable.

[0182] When using a metal foil as the support, examples of the metal foil include, for example, copper foil, aluminum foil, etc., and copper foil is preferred. As the copper foil, a foil made of single metal copper may be used, or a foil made of an alloy of copper and other metals (for example, tin, chromium, silver, magnesium, nickel, zirconium, silicon, titanium, etc.) may be used.

[0183] The support may be subjected to matting treatment, corona treatment, or antistatic treatment on the surface that joins the resin composition layer. Further, as the support, a support with a release layer having a release layer on the surface that joins the resin composition layer may be used. Examples of the release agent used for the release layer of the support with a release layer include one or more release agents selected from the group consisting of alkyd resins, polyolefin resins, urethane resins, and silicone resins. As the support with a release layer, a commercially available product may be used. For example, "SK-1", "AL-5", "AL-7" manufactured by Lintec Corporation, which are PET films having a release layer mainly composed of an alkyd resin-based release agent, "Lumirror T60" manufactured by Toray Industries, Inc., "Purex" manufactured by Teijin Limited, "Unipile" manufactured by Unitika Ltd., etc.

[0184] The thickness of the support is not particularly limited, but a range of 5 μm to 75 μm is preferred, and a range of 10 μm to 60 μm is more preferred. When using a support with a release layer, it is preferred that the total thickness of the support with a release layer is within the above range.

[0185] When using a metal foil as the support, a metal foil with a support substrate in which a support substrate that can be peeled off is laminated on a thin metal foil may be used. In one embodiment, the metal foil with a support substrate includes a support substrate, a release layer provided on the support substrate, and a metal foil provided on the release layer. When using a metal foil with a support substrate as the support, the resin composition layer is provided on the metal foil.

[0186] In the metal foil with a support substrate, the material of the support substrate is not particularly limited, and examples thereof include copper foil, aluminum foil, stainless steel foil, titanium foil, copper alloy foil, etc. When using copper foil as the support substrate, it may be an electrolytic copper foil or a rolled copper foil. Further, the release layer is not particularly limited as long as the metal foil can be peeled from the support substrate, and examples thereof include an alloy layer of an element selected from the group consisting of Cr, Ni, Co, Fe, Mo, Ti, W, and P; an organic film, etc.

[0187] In the metal foil with a support substrate, as the material of the metal foil, for example, copper foil and copper alloy foil are preferable.

[0188] In the metal foil with a support substrate, the thickness of the support substrate is not particularly limited, but the range of 10 μm to 150 μm is preferable, and the range of 10 μm to 100 μm is more preferable. Further, the thickness of the metal foil may be, for example, in the range of 0.1 μm to 10 μm.

[0189] In one embodiment, the resin sheet may further include any layer as necessary. Examples of such an arbitrary layer include a protective film, etc. provided on the surface of the resin composition layer that is not joined to the support (that is, the surface opposite to the support). The thickness of the protective film is not particularly limited, but is, for example, 1 μm to 40 μm. By laminating the protective film, adhesion of dust, etc. and scratches to the surface of the resin composition layer can be suppressed.

[0190] The resin sheet can be manufactured, for example, by directly using a liquid resin composition or preparing a resin varnish in which the resin composition is dissolved in an organic solvent, applying this on a support using a die coater or the like, and further drying to form a resin composition layer.

[0191] Examples of the organic solvent include the same ones as the organic solvents described as components of the resin composition. The organic solvent may be used alone or in combination of two or more.

[0192] Drying may be carried out by known methods such as heating and hot air blowing. The drying conditions are not particularly limited, but the drying is carried out so that the content of the organic solvent in the resin composition layer is 10% by mass or less, preferably 5% by mass or less. Although it also varies depending on the boiling point of the organic solvent in the resin composition or resin varnish, for example, when using a resin composition or resin varnish containing 30% by mass to 60% by mass of the organic solvent, the resin composition layer can be formed by drying at 50°C to 150°C for 3 minutes to 10 minutes.

[0193] The resin sheet can be wound up and stored in a roll shape. When the resin sheet has a protective film, it can be used by peeling off the protective film.

[0194] In one embodiment, the prepreg is formed by impregnating a sheet-shaped fiber base material with the resin composition of the present invention.

[0195] The sheet-shaped fiber base material used for the prepreg is not particularly limited, and those commonly used as prepreg base materials such as glass cloth, aramid nonwoven fabric, and liquid crystal polymer nonwoven fabric can be used. From the viewpoint of thinning printed wiring boards and semiconductor chip packages, the thickness of the sheet-shaped fiber base material is preferably 50 μm or less, more preferably 40 μm or less, still more preferably 30 μm or less, and particularly preferably 20 μm or less. The lower limit of the thickness of the sheet-shaped fiber base material is not particularly limited. Usually, it is 10 μm or more.

[0196] The prepreg can be manufactured by known methods such as the hot melt method and the solvent method.

[0197] The thickness of the prepreg can be in the same range as the resin composition layer in the above-mentioned resin sheet.

[0198] The sheet-like laminated material of the present invention can be suitably used for forming an insulating layer of a printed wiring board (for the insulating layer of a printed wiring board), and can be more suitably used for forming an interlayer insulating layer of a printed wiring board (for the interlayer insulating layer of a printed wiring board). The sheet-like laminated material of the present invention can also be suitably used for forming an insulating layer of a redistribution substrate of a semiconductor package (for the insulating layer of a redistribution substrate). That is, the sheet-like laminated material of the present invention can be suitably used as an insulating layer for a circuit board.

[0199] [Circuit board] An insulating layer of a circuit board can be formed using the resin composition of the present invention. The present invention also provides such a circuit board, that is, a circuit board including an insulating layer made of a cured product of the resin composition of the present invention.

[0200] <Printed wiring board> In one embodiment, the circuit board of the present invention is a printed wiring board.

[0201] The printed wiring board can be manufactured, for example, by a method including the following steps (I) and (II) using the above resin sheet. (I) A step of laminating a resin sheet on an inner layer substrate so that the resin composition layer of the resin sheet is joined to the inner layer substrate (II) A step of curing (for example, thermally curing) the resin composition layer to form an insulating layer

[0202] The "inner layer substrate" used in Process (I) is a member that serves as the substrate of a printed wiring board. Examples thereof include glass epoxy substrates, metal substrates, polyester substrates, polyimide substrates, BT resin substrates, thermosetting polyphenylene ether substrates, and the like. Further, the substrate may have conductor layers on one or both sides thereof, and these conductor layers may be pattern-processed. An inner layer substrate having conductor layers (circuits) formed on one or both sides of the substrate is sometimes referred to as an "inner layer circuit board". Also, in the production of a printed wiring board, an intermediate product on which an insulating layer and / or a conductor layer is to be further formed is also included in the "inner layer substrate" as referred to in the present invention. When the printed wiring board is a component-embedded circuit board, an inner layer substrate incorporating components may be used.

[0203] The lamination of the inner layer substrate and the resin sheet can be performed, for example, by thermocompression bonding the resin sheet to the inner layer substrate from the support side. Examples of the member for thermocompression bonding the resin sheet to the inner layer substrate (hereinafter, also referred to as "thermocompression bonding member") include a heated metal plate (such as a SUS mirror plate) or a metal roll (such as a SUS roll). Note that the thermocompression bonding member may be pressed directly against the resin sheet, or may be pressed via an elastic material such as a heat-resistant rubber so that the resin sheet sufficiently follows the surface unevenness of the inner layer substrate.

[0204] The lamination of the inner layer substrate and the resin sheet may be carried out by a vacuum lamination method. In the vacuum lamination method, the thermocompression bonding temperature is preferably in the range of 60°C to 160°C, more preferably in the range of 80°C to 140°C, the thermocompression bonding pressure is preferably in the range of 0.098 MPa to 1.77 MPa, more preferably in the range of 0.29 MPa to 1.47 MPa, and the thermocompression bonding time is preferably in the range of 20 seconds to 400 seconds, more preferably in the range of 30 seconds to 300 seconds. The lamination can preferably be carried out under a reduced pressure condition of a pressure of 26.7 hPa or less.

[0205] The lamination can be carried out using a commercially available vacuum laminator. Examples of the commercially available vacuum laminator include a vacuum pressure type laminator manufactured by Meiki Seisakusho Co., Ltd., a vacuum applicator manufactured by Nichco Materials Co., Ltd., a batch type vacuum pressure laminator, and the like.

[0206] After lamination, under normal pressure (atmospheric pressure), for example, by pressing a heat-bonding member from the support side, a smoothing process of the laminated resin sheet may be performed. The pressing conditions for the smoothing process can be the same as those for the heat-bonding conditions of the above lamination. The smoothing process can be performed by a commercially available laminator. Note that the lamination and the smoothing process may be continuously performed using the above-mentioned commercially available vacuum laminator.

[0207] The support may be removed between step (I) and step (II), or may be removed after step (II). Note that when a metal foil is used as the support, a conductor layer may be formed using the metal foil without peeling the support. Further, when a metal foil with a support substrate is used as the support, the support substrate (and the release layer) may be peeled off. And a conductor layer can be formed using the metal foil.

[0208] In step (II), the resin composition layer is cured (for example, thermally cured) to form an insulating layer made of a cured product of the resin composition. The curing conditions of the resin composition layer are not particularly limited, and conditions usually employed when forming an insulating layer of a printed wiring board may be used.

[0209] For example, the thermal curing conditions of the resin composition layer vary depending on the type of the resin composition and the like. In one embodiment, the curing temperature is preferably 140°C to 250°C, more preferably 150°C to 240°C, and still more preferably 180°C to 230°C. The curing time can be preferably 5 minutes to 240 minutes, more preferably 10 minutes to 150 minutes, and still more preferably 15 minutes to 120 minutes.

[0210] Before thermally curing the resin composition layer, the resin composition layer may be preheated at a temperature lower than the curing temperature. For example, prior to thermally curing the resin composition layer, the resin composition layer may be preheated at a temperature of 50°C to 140°C, preferably 60°C to 135°C, more preferably 70°C to 130°C for 5 minutes or more, preferably 5 minutes to 150 minutes, more preferably 15 minutes to 120 minutes, and still more preferably 15 minutes to 100 minutes.

[0211] When manufacturing a printed wiring board, the steps of (III) drilling holes in the insulating layer, (IV) roughening the insulating layer, and (V) forming a conductor layer may be further carried out. These steps (III) to (V) may be carried out according to various methods known to those skilled in the art used for manufacturing printed wiring boards. When removing the support after step (II), the removal of the support may be carried out between step (II) and step (III), between step (III) and step (IV), or between step (IV) and step (V). Further, if necessary, the formation of the insulating layer and the conductor layer in steps (I) to (V) may be repeated to form a multilayer wiring board.

[0212] In another embodiment, the printed wiring board of the present invention can be manufactured using the above-described prepreg. The manufacturing method is basically the same as the case of using a resin sheet.

[0213] Step (III) is a step of drilling holes in the insulating layer, whereby holes such as via holes and through holes can be formed in the insulating layer. Step (III) may be carried out using, for example, a drill, a laser, a plasma, etc., according to the composition of the resin composition used for forming the insulating layer. The dimensions and shapes of the holes may be appropriately determined according to the design of the printed wiring board.

[0214] Step (IV) is a step of roughening the insulating layer. Usually, in this step (IV), removal of smear (desmear) is also carried out. The procedures and conditions for the roughening treatment are not particularly limited, and known procedures and conditions usually used when forming the insulating layer of a printed wiring board can be adopted. For example, the insulating layer can be roughened by carrying out swelling treatment with a swelling liquid, roughening treatment with an oxidizing agent, and neutralization treatment with a neutralizing liquid in this order.

[0215] The swelling liquid used for the roughening treatment is not particularly limited, and examples thereof include an alkaline solution and a surfactant solution. Preferably, it is an alkaline solution, and as the alkaline solution, a sodium hydroxide solution and a potassium hydroxide solution are more preferable. Examples of commercially available swelling liquids include "Swelling Dip Security P" and "Swelling Dip Security SBU" manufactured by Atotech Japan Co., Ltd. The swelling treatment with the swelling liquid is not particularly limited, but for example, it can be carried out by immersing the insulating layer in the swelling liquid at 30°C to 90°C for 1 minute to 20 minutes. From the viewpoint of suppressing the swelling of the resin of the insulating layer to an appropriate level, it is preferable to immerse the insulating layer in the swelling liquid at 40°C to 80°C for 5 minutes to 15 minutes.

[0216] The oxidizing agent used for the roughening treatment is not particularly limited, and examples thereof include an alkaline permanganate solution in which potassium permanganate or sodium permanganate is dissolved in an aqueous solution of sodium hydroxide. The roughening treatment with an oxidizing agent such as an alkaline permanganate solution is preferably carried out by immersing the insulating layer in the oxidizing agent solution heated to 60°C to 100°C for 10 minutes to 30 minutes. Further, the concentration of the permanganate in the alkaline permanganate solution is preferably 5% by mass to 10% by mass. Examples of commercially available oxidizing agents include alkaline permanganate solutions such as "Concentrate Compact CP" and "Dosing Solution Security P" manufactured by Atotech Japan Co., Ltd.

[0217] Further, as the neutralizing liquid used for the roughening treatment, an acidic aqueous solution is preferable, and examples of commercially available products include "Reduction Solution Security P" manufactured by Atotech Japan Co., Ltd.

[0218] The treatment with the neutralizing liquid can be carried out by immersing the treated surface, which has been roughened with the oxidizing agent, in the neutralizing liquid at 30°C to 80°C for 5 minutes to 30 minutes. From the viewpoint of workability and the like, a method of immersing the object roughened with the oxidizing agent in the neutralizing liquid at 40°C to 70°C for 5 minutes to 20 minutes is preferable.

[0219] Step (V) is a step of forming a conductor layer, and the conductor layer is formed on an insulating layer. The conductor material used for the conductor layer is not particularly limited. In a preferred embodiment, the conductor layer contains one or more metals selected from the group consisting of gold, platinum, palladium, silver, copper, aluminum, cobalt, chromium, zinc, nickel, titanium, tungsten, iron, tin, and indium. The conductor layer may be a single-metal layer or an alloy layer. Examples of the alloy layer include layers formed from alloys of two or more metals selected from the above group (for example, nickel-chromium alloy, copper-nickel alloy, and copper-titanium alloy). Among them, from the viewpoints of versatility, cost, ease of patterning, etc. of conductor layer formation, a single-metal layer of chromium, nickel, titanium, aluminum, zinc, gold, palladium, silver, or copper, or an alloy layer of nickel-chromium alloy, copper-nickel alloy, or copper-titanium alloy is preferred, a single-metal layer of chromium, nickel, titanium, aluminum, zinc, gold, palladium, silver, or copper, or an alloy layer of nickel-chromium alloy is more preferred, and a single-metal layer of copper is even more preferred.

[0220] The conductor layer may have a single-layer structure or a multilayer structure in which two or more single-metal layers or alloy layers made of different types of metals or alloys are laminated. When the conductor layer has a multilayer structure, the layer in contact with the insulating layer is preferably a single-metal layer of chromium, zinc, or titanium, or an alloy layer of nickel-chromium alloy.

[0221] The thickness of the conductor layer depends on the design of the desired printed wiring board, but is generally 3 μm to 35 μm, preferably 5 μm to 30 μm.

[0222] In one embodiment, the conductor layer may be formed by plating. From the viewpoint of easily forming fine wiring, it is preferably formed by a semi-additive method. Hereinafter, an example of forming the conductor layer by the semi-additive method is shown.

[0223] First, a plating seed layer is formed on the surface of the insulating layer by electroless plating. Next, a mask pattern is formed on the formed plating seed layer to expose a part of the plating seed layer corresponding to a desired wiring pattern. After forming a metal layer by electrolytic plating on the exposed plating seed layer, the mask pattern is removed. Thereafter, an unnecessary plating seed layer is removed by etching or the like to form a conductor layer having a desired wiring pattern.

[0224] In another embodiment, the conductor layer may be formed using a metal foil. When forming the conductor layer using a metal foil, step (V) is preferably carried out between step (I) and step (II). For example, after step (I), the support is removed, and a metal foil is laminated on the surface of the exposed resin composition layer. The lamination of the resin composition layer and the metal foil may be carried out by a vacuum lamination method. The lamination conditions may be the same as those described for step (I). Next, step (II) is carried out to form an insulating layer. Thereafter, using the metal foil on the insulating layer, a conductor layer having a desired wiring pattern can be formed by a conventionally known technique such as the modified semi-additive method.

[0225] The metal foil can be manufactured by a known method such as an electrolytic method or a rolling method. Examples of commercially available metal foils include HLP foil, JXUT-III foil manufactured by JX Nippon Mining & Metals Corporation, 3EC-III foil, TP-III foil manufactured by Mitsui Mining & Smelting Co., Ltd., and the like.

[0226] Alternatively, as described above, when a metal foil or a metal foil with a support substrate is used as the support of the resin sheet, the conductor layer may be formed using the metal foil.

[0227] <Redistribution Substrate of Semiconductor Package> In one embodiment, the circuit board of the present invention is a redistribution substrate (redistribution layer) of a semiconductor package. Hereinafter, it will be described in accordance with the manufacturing method of the semiconductor package.

[0228] The semiconductor package includes an insulating layer made of a cured product of the resin composition of the present invention as an insulating layer of the redistribution substrate. Note that the semiconductor package may include a sealing layer made of a cured product of the resin composition of the present invention.

[0229] The semiconductor package can be manufactured, for example, by a method including the following steps (1) to (6) using the resin composition and resin sheet of the present invention. In order to form the redistribution formation layer (insulating layer for forming the redistribution substrate) in step (5) or the sealing layer in step (3), the resin composition and resin sheet of the present invention may be used. Hereinafter, an example of forming the redistribution formation layer and the sealing layer using the resin composition and resin sheet is shown. However, the technology for forming the redistribution formation layer and the sealing layer of the semiconductor package is known, and those skilled in the art can manufacture the semiconductor package according to the known technology using the resin composition and resin sheet of the present invention. (1) Step of laminating a temporary fixing film on a base material (2) Step of temporarily fixing a semiconductor chip on the temporary fixing film (3) Step of forming a sealing layer on the semiconductor chip (4) Step of peeling the base material and the temporary fixing film from the semiconductor chip (5) Step of forming a redistribution formation layer as an insulating layer on the surface of the base material and the temporary fixing film of the semiconductor chip from which they are peeled, and (6) Step of forming a redistribution layer as a conductor layer on the redistribution formation layer

[0230] - Step (1) - The material used for the base material is not particularly limited. Examples of the base material include semiconductor wafers such as silicon wafers; glass wafers; glass substrates; metal substrates such as copper, titanium, stainless steel, and cold-rolled steel sheets (SPCC); substrates impregnated with epoxy resins or the like in glass fibers and subjected to thermosetting treatment (for example, FR-4 substrates); substrates made of bismaleimide triazine resins (BT resins), and the like.

[0231] The temporary fixing film can be peeled off from the semiconductor chip in step (4), and the material is not particularly limited as long as it can temporarily fix the semiconductor chip. A commercially available product can be used as the temporary fixing film. Examples of commercially available products include Rivar Alpha manufactured by Nitto Denko Corporation.

[0232] - Step (2)- The temporary fixing of the semiconductor chip can be performed using a known device such as a flip chip bonder or a die bonder. The layout and the number of arrangements of the semiconductor chips can be appropriately set according to the shape and size of the temporary fixing film, the number of semiconductor packages to be produced, etc. For example, they can be temporarily fixed in a matrix arrangement with multiple rows and multiple columns.

[0233] - Step (3)- The resin composition layer of the resin sheet of the present invention is laminated on the semiconductor chip, or the resin composition of the present invention is applied on the semiconductor chip and cured (for example, thermally cured) to form a sealing layer.

[0234] For example, the lamination of the semiconductor chip and the resin sheet can be performed by removing the protective film of the resin sheet and then thermocompression bonding the resin sheet to the semiconductor chip from the support side. Examples of the member for thermocompression bonding the resin sheet to the semiconductor chip (hereinafter also referred to as "thermocompression bonding member") include a heated metal plate (such as a SUS mirror plate) or a metal roll (such as a SUS roll). It is preferable to press through an elastic material such as a heat-resistant rubber so that the resin sheet sufficiently follows the surface unevenness of the semiconductor chip instead of pressing the thermocompression bonding member directly against the resin sheet. The lamination of the semiconductor chip and the resin sheet may be carried out by the vacuum lamination method, and the lamination conditions are the same as the lamination conditions described in relation to the manufacturing method of the printed wiring board, and the preferable range is also the same.

[0235] After the lamination, the resin composition is thermally cured to form a sealing layer. The thermal curing conditions are the same as the thermal curing conditions described in relation to the manufacturing method of the printed wiring board.

[0236] The support of the resin sheet may be peeled off after laminating and thermosetting the resin sheet on the semiconductor chip, or the support may be peeled off before laminating the resin sheet on the semiconductor chip.

[0237] When forming the sealing layer by applying the resin composition of the present invention, the coating conditions are the same as those for forming the resin composition layer described in relation to the resin sheet of the present invention, and the preferred ranges are also the same.

[0238] - Step (4)- The method of peeling the base material and the temporary fixing film can be appropriately changed according to the material of the temporary fixing film, etc. For example, methods of peeling by heating and foaming (or expanding) the temporary fixing film, and methods of irradiating ultraviolet rays from the base material side to reduce the adhesive force of the temporary fixing film and peeling it, etc. can be mentioned.

[0239] In the method of peeling by heating and foaming (or expanding) the temporary fixing film, the heating conditions are usually 100 to 250 ° C for 1 to 90 seconds or 5 to 15 minutes. Also, in the method of irradiating ultraviolet rays from the base material side to reduce the adhesive force of the temporary fixing film and peeling it, the irradiation amount of ultraviolet rays is usually 10 mJ / cm 2 ~1000 mJ / cm 2 is.

[0240] - Step (5)- The resin composition and resin sheet of the present invention are used to form a redistribution formation layer (insulating layer of the redistribution substrate).

[0241] After forming the redistribution formation layer, in order to layer-connect the semiconductor chip and the conductor layer described later, via holes may be formed in the redistribution formation layer. The via holes may be formed by a known method according to the material of the redistribution formation layer.

[0242] - Step (6)- The formation of the conductor layer on the rewiring formation layer may be carried out in the same manner as in step (V) described in relation to the method for manufacturing a printed wiring board. Note that steps (5) and (6) may be repeated to alternately stack (build up) the conductor layer (rewiring layer) and the rewiring formation layer (insulating layer).

[0243] In manufacturing a semiconductor package, steps of (7) forming a solder resist layer on the conductor layer (rewiring layer), (8) forming bumps, and (9) dicing and singulating a plurality of semiconductor packages into individual semiconductor packages may further be carried out. These steps may be carried out according to various methods known to those skilled in the art and used in the manufacture of semiconductor packages.

[0244] The resin composition and resin sheet of the present invention can provide a cured product that exhibits excellent dielectric properties, exhibits good adhesion to a plating conductor when a wiring pattern is formed by a semi-additive method, and exhibits good adhesion to an underlying conductor when exposed to a high-temperature and high-humidity environment. By forming a rewiring formation layer (insulating layer) using the resin composition and resin sheet of the present invention, a semiconductor package with extremely low transmission loss can be realized regardless of whether it is a fan-in type package or a fan-out type package, without concern about a decrease in conductor adhesion. In one embodiment, the semiconductor package of the present invention is a fan-out type package. The resin composition and resin sheet of the present invention are applicable regardless of whether they are a fan-out panel level package (FOPLP) or a fan-out wafer level package (FOWLP). In one embodiment, the semiconductor package of the present invention is a fan-out panel level package (FOPLP) or a fan-out wafer level package (FOWLP).

[0245] [Semiconductor Device] The semiconductor device of the present invention includes a layer made of a cured product of the resin composition layer of the present invention. The semiconductor device of the present invention can be manufactured using the circuit board of the present invention.

[0246] Examples of semiconductor devices include various semiconductor devices used in electrical products (e.g., computers, mobile phones, digital cameras, televisions, etc.) and vehicles (e.g., motorcycles, automobiles, trains, ships, airplanes, etc.).

Example

[0247] Hereinafter, the present invention will be specifically described by way of examples. The present invention is not limited to these examples. In the following, "parts" and "%" representing amounts mean "parts by mass" and "mass %", respectively, unless otherwise specified.

[0248] [Synthesis Example 1] Dichloromethane (25 mL) was added to 4-(methylamino)pyridine (540 mg, 5.0 mmol), acetyl chloride (390 μL, 5.5 mmol), and triethylamine (1.0 mL, 7.5 mmol), and the mixture was stirred overnight at room temperature. A saturated aqueous sodium hydrogen carbonate solution was added to the reaction solution, and the mixture was extracted twice with dichloromethane. The organic layer was dried over magnesium sulfate. After filtering off the desiccant, the residue obtained by concentration under reduced pressure was purified by silica gel column chromatography (dichloromethane / methanol) to obtain a compound represented by the following chemical formula.

[0249]

Chemical formula

[0250] [Synthesis Example 2] Using acryloyl chloride (440 μL, 5.5 mmol) instead of acetyl chloride, a compound represented by the following chemical formula was obtained in the same manner as in Synthesis Example 1.

[0251]

Chemical formula

[0252] [Synthesis Example 3] Using benzoyl chloride (630 μL, 5.5 mmol) instead of acetyl chloride, the compound represented by the following chemical formula was obtained in the same manner as in Synthesis Example 1.

[0253] [Chemical formula]

[0254] [Synthesis Example 4] Using methyl chloroformate (420 μL, 5.5 mmol) instead of acetyl chloride, the compound represented by the following chemical formula was obtained in the same manner as in Synthesis Example 1.

[0255] [Chemical formula]

[0256] [Synthesis Example 5] Using methyl phenylcarbamate chloride (790 μL, 5.5 mmol) instead of acetyl chloride, the compound represented by the following chemical formula was obtained in the same manner as in Synthesis Example 1.

[0257] [Chemical formula]

[0258] [Synthesis Example 6] Using 2-cyanoacetyl chloride (570 mg, 5.5 mmol) instead of acetyl chloride, the same operation as in Synthesis Example 1 was carried out. To the obtained compound, dicyandiamide (420 mg, 5.0 mmol), potassium hydroxide (11 mg, 0.2 mmol) and 2-methoxyethanol (20 mL) were added, and the mixture was stirred at 130 °C overnight. After the reaction solution was returned to room temperature, water was added, and the precipitated solid was collected by filtration to obtain the compound represented by the following chemical formula.

[0259] [Chemical formula]

[0260] [Synthesis Example 7] Using N-ethylpyridin-4-amine (590 μL, 5.0 mmol) instead of 4-(methylamino)pyridine, a compound represented by the following chemical formula was obtained in the same manner as in Synthesis Example 1.

[0261] [Chemical Formula]

[0262] [Synthesis Example 8] Using 2-bromo-N-methylpyridin-4-amine (940 mg, 5.0 mmol) instead of 4-(methylamino)pyridine, the same operation as in Synthesis Example 1 was performed. To the obtained compound, (E)-1-octen-1-ylboronic acid (1.2 g, 5.0 mmol) and 1,1'-bis(diphenylphosphino)ferrocenedichloropalladium(II) (180 mg, 0.25 mmol) were added, and 1,4-dioxane (7.5 mL) and 2 mol / L aqueous sodium carbonate solution (2.5 mL) were added, followed by stirring at 90 °C overnight. The insoluble matter in the reaction solution was filtered off with celite using ethyl acetate, the filtrate was added to water and extracted twice with ethyl acetate, and the organic layer was dried over magnesium sulfate. After filtering off the drying agent, the residue obtained by concentration under reduced pressure was purified by silica gel column chromatography (dichloromethane / methanol) to obtain a compound represented by the following chemical formula.

[0263] [Chemical Formula]

[0264] [Synthesis Example 9] Using 3-bromo-N-methylpyridin-4-amine (940 mg, 5.0 mmol) instead of 2-bromo-N-methylpyridin-4-amine and trans-1-propen-1-ylboronic acid (430 mg, 5.0 mmol) instead of (E)-1-octen-1-ylboronic acid, a compound represented by the following chemical formula was obtained in the same manner as in Synthesis Example 8.

[0265] [Chemical]

[0266] [Synthesis Example 10] Using N,2-dimethylpyridin-4-amine (611 mg, 5.0 mmol) instead of 4-(methylamino)pyridine, the same procedure as in Synthesis Example 1 was carried out to obtain a compound represented by the following chemical formula.

[0267] [Chemical]

[0268] [Synthesis Example 11] Using N,3-dimethylpyridin-4-amine (611 mg, 5.0 mmol) instead of 4-(methylamino)pyridine, the same procedure as in Synthesis Example 1 was carried out to obtain a compound represented by the following chemical formula.

[0269] [Chemical]

[0270] [Example 1] (1) Preparation of Resin Composition 20 parts of a biphenyl-type epoxy resin (manufactured by Nippon Kayaku Co., Ltd., "NC-3000", epoxy equivalent weight of about 275 g / eq.) were heated and dissolved in 30 parts of MEK with stirring to obtain a dissolved composition. This was cooled to room temperature, and to this dissolved composition were added 50 parts of an active ester compound (a toluene solution of "HPC-8150-62T" manufactured by DIC, active ester group equivalent weight of about 229 g / eq., non-volatile component ratio of 62%), 170 parts of spherical silica (manufactured by Admatechs Co., Ltd., "SO-C2", average particle size of 0.5 μm) surface-treated with a silane coupling agent (manufactured by Shin-Etsu Chemical Co., Ltd., "KBM-573"), 2 parts of a triazine skeleton-containing phenolic curing agent (manufactured by DIC, "LA-3018-50P", active group equivalent weight of about 151 g / eq., 2-methoxypropanol solution with a non-volatile component ratio of 50%), 10 parts of a carbodiimide-based curing agent (manufactured by Nisshinbo Chemical Inc., "V-03", toluene solution with an active group equivalent weight of about 216 g / eq., non-volatile component ratio of 50%), 2 parts of a phenoxy resin (manufactured by Mitsubishi Chemical Corporation, "YX7553BH30", 1:1 solution of MEK and cyclohexanone with a non-volatile component ratio of 30%), and 1 part of the compound obtained in Synthesis Example 1 as a curing accelerator were mixed and uniformly dispersed with a high-speed rotary mixer to prepare a resin composition (resin varnish).

[0271] (2) Production of resin sheet As a support, a polyethylene terephthalate film (manufactured by Toray Industries, Inc., "Lumirror R80"; thickness 38 μm, softening point 130 °C) having a release treatment on the surface with an alkyd resin-based release agent (manufactured by Lintec Corporation, "AL-5") was prepared. On this support, the resin composition was uniformly applied so that the thickness of the resin composition layer after drying would be 40 μm, and it was dried at 90 °C for 3 minutes. Next, a polyethylene terephthalate film similar to the support was laminated as a protective film on the exposed surface of the resin composition layer (the surface not joined to the support) to obtain a resin sheet having a layer structure of support / resin composition layer / protective film.

[0272] [Example 2] The compound obtained in Synthesis Example 2 was used as the curing accelerator. Except for the above matters, a resin composition (resin varnish) was prepared and a resin sheet was obtained in the same manner as in Example 1.

[0273] [Example 3] The compound obtained in Synthesis Example 3 was used as a curing accelerator. Except for the above matters, a resin composition (resin varnish) was prepared in the same manner as in Example 1 to obtain a resin sheet.

[0274] [Example 4] The compound obtained in Synthesis Example 4 was used as a curing accelerator. Except for the above matters, a resin composition (resin varnish) was prepared in the same manner as in Example 1 to obtain a resin sheet.

[0275] [Example 5] The compound obtained in Synthesis Example 5 was used as a curing accelerator. Except for the above matters, a resin composition (resin varnish) was prepared in the same manner as in Example 1 to obtain a resin sheet.

[0276] [Example 6] The compound obtained in Synthesis Example 6 was used as a curing accelerator. Except for the above matters, a resin composition (resin varnish) was prepared in the same manner as in Example 1 to obtain a resin sheet.

[0277] [Example 7] The compound obtained in Synthesis Example 7 was used as a curing accelerator. Except for the above matters, a resin composition (resin varnish) was prepared in the same manner as in Example 1 to obtain a resin sheet.

[0278] [Example 8] The compound obtained in Synthesis Example 8 was used as a curing accelerator. Except for the above matters, a resin composition (resin varnish) was prepared in the same manner as in Example 1 to obtain a resin sheet.

[0279] [Example 9] The compound obtained in Synthesis Example 9 was used as a curing accelerator. Except for the above matters, a resin composition (resin varnish) was prepared in the same manner as in Example 1 to obtain a resin sheet.

[0280] [Example 10] The compound obtained in Synthesis Example 10 was used as a curing accelerator. Except for the above matters, a resin composition (resin varnish) was prepared in the same manner as in Example 1 to obtain a resin sheet.

[0281] [Example 11] The compound obtained in Synthesis Example 11 was used as a curing accelerator. Except for the above matters, a resin composition (resin varnish) was prepared in the same manner as in Example 1 to obtain a resin sheet.

[0282] [Example 12] The amount of the compound obtained in Synthesis Example 1 was increased to 2.5 parts as a curing accelerator. Except for the above matters, a resin composition (resin varnish) was prepared in the same manner as in Example 1 to obtain a resin sheet.

[0283] [Example 13] The amount of the compound obtained in Synthesis Example 1 was reduced to 0.1 part as a curing accelerator. Except for the above matters, a resin composition (resin varnish) was prepared in the same manner as in Example 1 to obtain a resin sheet.

[0284] [Example 14] The amount of spherical silica ("SO-C2" manufactured by Admatechs Co., Ltd.) was reduced to 100 parts. Further, 15 parts of hollow aluminosilicate particles ("MGH-005" manufactured by Pacific Cement Co., Ltd., average particle size 1.6 μm, porosity 80% by volume) surface-treated with a silane coupling agent ("KBM-573" manufactured by Shin-Etsu Chemical Co., Ltd.) were added to the resin composition. Except for the above matters, a resin composition (resin varnish) was prepared in the same manner as in Example 1 to obtain a resin sheet.

[0286] [Example 16] Except for using 46 parts of an active ester compound ("HPC-8000-65T" manufactured by DIC Corporation, toluene solution with an active ester group equivalent of about 223 g / eq. and a non-volatile component ratio of 65%) instead of 50 parts of the active ester compound ("HPC-8150-62T" manufactured by DIC Corporation), a resin composition (resin varnish) was prepared in the same manner as in Example 1 to obtain a resin sheet.

[0287] [Example 17] Instead of 20 parts of a biphenyl-type epoxy resin (manufactured by Nippon Kayaku Co., Ltd., "NC-3000", epoxy equivalent of about 275 g / eq.), 20 parts of a naphthalene-type epoxy resin (manufactured by DIC Corporation, "HP-4032-SS", epoxy equivalent of about 145 g / eq.) was used. Otherwise, in the same manner as in Example 1, a resin composition (resin varnish) was prepared to obtain a resin sheet.

[0288] [Example 18] Instead of 2 parts of a phenolic curing agent containing a triazine skeleton (manufactured by DIC Corporation, "LA-3018-50P"), 1 part of a naphthalene-type phenolic curing agent (manufactured by Nippon Steel Chemical & Material Co., Ltd., "SN-485", phenolic equivalent of about 215 g / eq.) was used. Otherwise, in the same manner as in Example 1, a resin composition (resin varnish) was prepared to obtain a resin sheet.

[0289] [Example 19] Instead of 20 parts of a biphenyl-type epoxy resin (manufactured by Nippon Kayaku Co., Ltd., "NC-3000", epoxy equivalent of about 275 g / eq.), 20 parts of a naphthol aralkyl-type epoxy resin (manufactured by Nippon Steel Chemical & Material Co., Ltd., "ESN-475V", epoxy equivalent of about 332 g / eq.) was used. The amount of the active ester compound (manufactured by DIC Corporation, "HPC-8150-62T") was reduced to 25 parts, and 9 parts of a petroleum naphtha (fraction with a boiling point of 180°C to 217°C) solution of a phenol novolac-type polyfunctional cyanate ester resin (manufactured by Lonza Japan Co., Ltd., "PT30", cyanate equivalent of about 124) with a non-volatile content of 85% by mass and 10 parts of a prepolymer of bisphenol A dicyanate (manufactured by Lonza Japan Co., Ltd., "BA230S75", cyanate equivalent of about 232, methyl ethyl ketone (MEK) varnish with a non-volatile content of 75%) were added. In addition, 0.1 part of cobalt(II) acetylacetonate (hereinafter abbreviated as Co(II)acac) (manufactured by Tokyo Chemical Industry Co., Ltd.) was added as a curing accelerator. Otherwise, in the same manner as in Example 1, a resin composition (resin varnish) was prepared to obtain a resin sheet.

[0290] [Example 20] Instead of 2 parts of a phenoxy resin (「YX7553BH30」manufactured by Mitsubishi Chemical Corporation, a 1:1 solution of MEK and cyclohexanone with a non-volatile content of 30% by mass), 2 parts of a maleimide resin containing a cyclohexane ring (「SLK-6895-T90」manufactured by Shin-Etsu Chemical Co., Ltd., a toluene solution with a non-volatile content of 90% by mass) were used. Except for the above matters, a resin composition (resin varnish) was prepared and a resin sheet was obtained in the same manner as in Example 1.

[0291] [Comparative Example 1] Instead of 1 part of the compound obtained in Synthesis Example 1, 1 part of 4-dimethylaminopyridine was used as a curing accelerator. Except for the above matters, a resin composition (resin varnish) was prepared and a resin sheet was obtained in the same manner as in Example 20 and a resin sheet was obtained.

[0292] [Comparative Example 2] The amount of 4-dimethylaminopyridine was increased to 2.5 parts. Except for the above matters, a resin composition (resin varnish) was prepared and a resin sheet was obtained in the same manner as in Comparative Example 1.

[0293] [Comparative Example 3] The amount of 4-dimethylaminopyridine was reduced to 0.1 part. Except for the above matters, a resin composition (resin varnish) was prepared and a resin sheet was obtained in the same manner as in Comparative Example 1.

[0294] [Comparative Example 4] Instead of 1 part of the compound obtained in Synthesis Example 1, 1 part of an imidazole-based curing accelerator (「1B2PZ」manufactured by Shikoku Kasei Kogyo Co., Ltd., 1-benzyl-2-phenylimidazole) was used. Except for the above matters, a resin composition (resin varnish) was prepared and a resin sheet was obtained in the same manner as in Example 1.

[0295] [Reference Example 1] The amount of spherical silica (「SO-C2」manufactured by Admatechs Co., Ltd., average particle size 0.5 μm) surface-treated with a silane coupling agent (「KBM-573」manufactured by Shin-Etsu Chemical Co., Ltd.) was reduced to 89 parts. Except for the above matters, a resin composition (resin varnish) was adjusted and a resin sheet was obtained in the same manner as in Example 20 and a resin sheet was obtained.

[0296] [Reference Example 2] The amount of the active ester compound (“HPC-8150-62T” manufactured by DIC Corporation) was reduced to 27 parts. , reduce the amount of spherical silica (manufactured by Admatechs Co., Ltd. "SO-C2", average particle size 0.5 μm) surface-treated with a silane coupling agent (manufactured by Shin-Etsu Chemical Co., Ltd. "KBM-573") to 135 parts Except for the above matters, a resin composition (resin varnish) was adjusted in the same manner as in the 20 Example to obtain a resin sheet.

[0297] [Various Evaluation Tests] [Test Example 1: Measurement of Dielectric Loss Tangent] The protective film was peeled off from the resin sheets prepared in the Examples and Comparative Examples, heated at 200 °C for 90 minutes to thermally cure the resin composition layer, and then the support was peeled off to obtain a cured film formed of the cured product of the resin composition. The cured film was cut into pieces with a width of 2 mm and a length of 80 mm to obtain Cured Product A for evaluation.

[0298] For the obtained Cured Product A for evaluation, using “HP8362B” manufactured by Agilent Technologies, the value of the dielectric loss tangent (Df value) was measured at a measurement frequency of 5.8 GHz and a measurement temperature of 23 °C by the cavity resonance perturbation method. Measurements were performed on three test pieces, and the average value was calculated.

[0299] [Test Example 2: Crack Evaluation Test] (1) Lamination of Resin Sheets An inner layer substrate (manufactured by Hitachi Chemical Co., Ltd., “MCL-E700G”, conductor layer thickness 35 μm, total thickness 0.4 mm, residual copper ratio 40%) having circuit conductors (copper) formed with a line / space ratio (L / S) of 8 μm / 8 μm on both sides was prepared. The protective film was peeled off from the resin sheet, and the resin sheet was laminated on both sides of the inner layer substrate so that the resin composition layer was in contact with the inner layer substrate. Such lamination was performed using a batch-type vacuum pressure laminator (two-stage build-up laminator “CVP700” manufactured by Nichco Materials Co., Ltd.). After vacuum suction at 120 °C for 30 seconds, it was pressed for 30 seconds from above the support through a heat-resistant rubber under the conditions of a temperature of 120 °C and a pressure of 0.7 MPa. Next, under atmospheric pressure, pressing was performed for 60 seconds using a SUS mirror plate under the conditions of a temperature of 120 °C and a pressure of 0.55 MPa.

[0300] (2) Thermal curing of the resin composition layer The support was peeled off from the laminated resin sheet. It was placed in an oven at 130 °C and heated for 30 minutes, then transferred to an oven at 170 °C and heated for 30 minutes to thermally cure the resin composition layer and form an insulating layer. Thus, a sample substrate having a layer structure of inner layer substrate / insulating layer was obtained. Next, the sample substrate was left to stand and cooled to room temperature (25 °C).

[0301] (3) Roughening treatment The sample substrate was immersed in Swelling Dip Securigant P manufactured by Atotech Japan Co., Ltd., which is a swelling liquid, at 60 °C for 10 minutes. Next, it was immersed in Concentrate Compact P manufactured by Atotech Japan Co., Ltd., which is a roughening liquid (aqueous solution of KMnO4: 60 g / L, NaOH: 40 g / L), at 80 °C for 20 minutes. Finally, it was immersed in Reduction Solution Securigant P manufactured by Atotech Japan Co., Ltd., which is a neutralizing liquid, at 40 °C for 5 minutes. Thereafter, the sample substrate was dried at 80 °C for 30 minutes.

[0302] (4) Evaluation of cracks Among the surfaces of the insulating layer of the sample substrate after desmear treatment, the area on the L / S pattern of the inner layer substrate was observed. In 100 portions on the pattern of the inner layer substrate, it was confirmed whether cracks occurred on the surface along the pattern shape, and the number of portions on the pattern where no cracks occurred was counted. Among the 100 portions, the ratio of the portions where no cracks occurred was calculated as the "yield". A higher yield is more preferable. Therefore, the calculated yield was scored according to the following criteria. 1 point: 0% or more and less than 20%. 2 points: 20% or more and less than 40%. 3 points: 40% or more and less than 60%. 4 points: 60% or more and less than 80%. 5 points: 80% or more. A score of 3 points or more was judged as a crack evaluation "○". Also, a score of 2 points or less was judged as a crack evaluation "×".

[0303] [Test Example 3: Measurement of adhesion strength with copper foil after high-temperature and high-humidity environment test] (1) Pretreatment of copper foil The shiny surface of an electrolytic copper foil (manufactured by Mitsui Mining & Smelting Co., Ltd., "3EC-III", thickness 35 μm) was immersed in a micro-etching agent (manufactured by Meck Co., Ltd., "CZ-8101") to roughen the copper surface (Ra value = 1 μm), and then a rust preventive treatment was performed using a rust preventive solution (manufactured by Meck Co., Ltd., "CL8300"). The obtained copper foil is referred to as CZ copper foil. Further, it was heat-treated in an oven at 130 °C for 30 minutes.

[0304] (2) Preparation of samples As an inner layer substrate, a glass cloth-based epoxy resin double-sided copper-clad laminate (copper foil thickness 18 μm, substrate thickness 0.4 mm, manufactured by Panasonic Corporation, "R1515A") was prepared. Next, the resin sheets obtained in the examples and comparative examples were laminated on both sides of the inner layer circuit board using a batch-type vacuum pressure laminator (manufactured by Nichco Materials Co., Ltd., 2-stage build-up laminator "CVP700") so that the resin composition layer was joined to the inner layer substrate. The lamination was carried out by reducing the pressure for 30 seconds to make the atmospheric pressure 13 hPa or less, and then crimping at 100 °C and a pressure of 0.74 MPa for 30 seconds. After lamination, the support was peeled off. The treated surface of the CZ copper foil was laminated on the exposed resin composition layer under the same conditions as above. Then, the resin composition layer was cured under the curing conditions of 190 °C for 90 minutes to form an insulating layer, thereby preparing a sample having a structure of CZ copper foil / insulating layer / inner layer circuit board / insulating layer / CZ copper foil.

[0305] (3) Measurement of copper foil adhesion after high temperature and high humidity environment test The prepared sample was cut into small pieces of 150 × 30 mm. A cut was made in the copper foil portion of the small piece with a cutter to a width of 10 mm and a length of 150 mm, and a high-temperature and high-humidity environment test was carried out for 100 hours under the conditions of 130 °C and 85% RH using a highly accelerated life test device (manufactured by Kusumoto Chemicals, Ltd., "PM422"). Then, one end in the length direction of the copper foil was peeled off, this peeled-off end was grasped with a gripping tool (manufactured by T.S.E. Co., Ltd., auto-comb type tester AC-50C-SL), and at room temperature (25 °C), the load (kgf / cm) when it was peeled off vertically by 100 mm at a speed of 50 mm / min was measured.

[0306] [Test Example 4: Measurement of adhesion strength with plated copper] (1) Preparation of Inner Layer Substrate As the inner layer substrate, a glass cloth base epoxy resin double-sided copper-clad laminate having copper foil on the surface (copper foil thickness 18 μm, substrate thickness 0.8 mm, "R1515A" manufactured by Panasonic) was prepared. The copper foil on the surface of this inner layer substrate was etched with a micro-etching agent ("CZ8101" manufactured by Meck) at a copper etching amount of 1 μm to perform roughening treatment. Thereafter, drying was performed at 190 °C for 30 minutes.

[0307] (2) Lamination of Resin Sheet The resin sheets obtained in the above-described examples and comparative examples were laminated on both sides of the inner layer substrate using a batch-type vacuum pressure laminator (two-stage build-up laminator "CVP700" manufactured by Nichco Materials) so that the resin composition layer was joined to the inner layer substrate. This lamination was performed by reducing the pressure for 30 seconds to make the atmospheric pressure 13 hPa or less, and then crimping at a temperature of 100 °C and a pressure of 0.74 MPa for 30 seconds.

[0308] (3) Thermal Curing of Resin Composition Layer Next, the laminated resin sheet was thermally pressed at 100 °C and a pressure of 0.5 MPa for 60 seconds under atmospheric pressure to be smoothed. Further, this was put into an oven at 130 °C and heated for 30 minutes, and then transferred to an oven at 170 °C and heated for 30 minutes to thermally cure the resin composition layer to form an insulating layer. Thereafter, the support was peeled off to obtain a cured substrate having a structure of insulating layer / inner layer substrate / insulating layer.

[0309] (4) Roughening Treatment The obtained cured substrate was immersed in a swelling liquid ("Swelling Dip·Security Gun P" manufactured by Atotech Japan) at 60 °C for 10 minutes, then immersed in a roughening liquid ("Concentrate·Compact P" manufactured by Atotech Japan, aqueous solution of KMnO4: 60 g / L, NaOH: 40 g / L) at 80 °C for 20 minutes, and finally immersed in a neutralizing liquid ("Reduction Solution·Security Gun P" manufactured by Atotech Japan) at 40 °C for 5 minutes. The obtained substrate is referred to as a roughened substrate.

[0310] (5) Formation of the conductor layer The roughened substrate was immersed in an electroless plating solution containing PdCl2 at 40°C for 5 minutes, and then immersed in an electroless copper plating solution at 25°C for 20 minutes. After annealing by heating at 150°C for 30 minutes, an etching resist was formed. After pattern formation by etching, copper sulfate electrolytic plating was performed to form a conductor layer with a thickness of 30 μm. Next, annealing treatment was performed at 200°C for 60 minutes to obtain Evaluation Substrate A.

[0311] (6) Measurement of the adhesion strength (peel strength) of the plated conductor layer A cut with a width of 10 mm and a length of 150 mm was made in a portion of the conductor layer of Evaluation Substrate A that did not contain via holes. One end of this was peeled off and grasped with a gripping tool (manufactured by T.S.E. Co., Ltd., Auto Com type testing machine AC-50C-SL), and the load (kgf / cm) when peeled off vertically by 100 mm at a speed of 50 mm / min at room temperature (25°C) was measured.

[0312] The results of Examples 1 to 20, Comparative Examples 1 to 4, and Reference Examples 1 and 2 are shown in Table 1.

[0313]

Table 1

Claims

1. A resin composition comprising (A) a compound represented by the following formula (1), (B) an epoxy resin, and (C) a curing agent, wherein the content of component (A) is 0.1% by mass or more and 10% by mass or less when the resin components in the resin composition are 100% by mass, the content of component (B) is 15% by mass or more when the resin components in the resin composition are 100% by mass, and the content of component (C) is 30% by mass or more when the resin components in the resin composition are 100% by mass. 【Chemical Formula 1】 (In the formula, R １ each independently represents a monovalent hydrocarbon group which may have a substituent, or a monovalent heteroatom-containing hydrocarbon group which may have a substituent, R ２ represents a monovalent hydrocarbon group which may have a substituent, or a monovalent heteroatom-containing hydrocarbon group which may have a substituent, R ３ represents a divalent hydrocarbon group which may have a substituent, R ４ represents a monovalent hydrocarbon group which may have a substituent, a monovalent heteroatom-containing hydrocarbon group which may have a substituent, or an amino group which may have a substituent. The monovalent hydrocarbon group which may have a substituent as R4 is an alkyl group which may have a substituent, an alkenyl group which may have a substituent, an alkynyl group which may have a substituent, a cycloalkyl group which may have a substituent, or an aryl group which may have a substituent. The monovalent heteroatom-containing hydrocarbon group which may have a substituent as R4 is an alkoxy group which may have a substituent, an alkenyloxy group which may have a substituent, an alkynyloxy group which may have a substituent, a cycloalkyloxy group which may have a substituent, or a heteroaryl group which may have a substituent. m represents a number from 0 to 4, and n represents 0 or 1. )

2. R １ 、R ２ and R ４ The resin composition according to claim 1, wherein the monovalent hydrocarbon group or monovalent heteroatom-containing hydrocarbon group in has 1 to 12 carbon atoms.

3. R ３ The resin composition according to claim 1, wherein the divalent hydrocarbon group in has 1 to 12 carbon atoms.

4. R ４ represents an alkyl group which may have a substituent, an alkenyl group which may have a substituent, an alkynyl group which may have a substituent, a cycloalkyl group which may have a substituent, an aryl group which may have a substituent, an alkoxy group, an alkenyloxy group which may have a substituent, an alkynyloxy group which may have a substituent, a cycloalkyloxy group which may have a substituent, a heteroaryl group which may have a substituent, or an amino group which may have a substituent, The resin composition according to claim 1.

5. The resin composition according to claim 1, wherein the component (C) contains one or more curing agents selected from the group consisting of (C-1) active ester-based curing agents, cyanate ester-based curing agents, and carbodiimide-based curing agents.

6. The resin composition according to claim 5, wherein the mass ratio of the component (C-1) to the component (B) ((C-1) component / (B) component) is 1 or more.

7. The resin composition according to claim 1, further comprising (D) an inorganic filler.

8. The content of the component (D) is 60% by mass or more when the non-volatile components in the resin composition are 100% by mass, or 45% by volume or more when the non-volatile components in the resin composition are 100% by volume, The resin composition according to claim 7.

9. The resin composition according to claim 1, wherein the value of the dielectric tangent of the cured product is 0.004 or less.

10. The resin composition according to claim 1, which is for an insulating layer of a circuit board.

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

12. The resin sheet according to claim 11, wherein the support is a thermoplastic resin film or a metal foil.

13. The cured product of the resin composition according to any one of claims 1 to 10.

14. A circuit board comprising an insulating layer made of the cured product of the resin composition according to any one of claims 1 to 10.

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

Images