CN113717523A

CN113717523A - Resin composition

Info

Publication number: CN113717523A
Application number: CN202110566375.4A
Authority: CN
Inventors: 川合贤司
Original assignee: Ajinomoto Co Inc
Current assignee: Ajinomoto Co Inc
Priority date: 2020-05-26
Filing date: 2021-05-24
Publication date: 2021-11-30
Also published as: JP7400627B2; JP2021187893A; KR20210146230A; TW202208475A

Abstract

The invention provides a resin composition which can obtain a cured product with low relative dielectric constant (Dk) and dielectric loss tangent (Df) and excellent stripping strength of a plated conductor layer. The solution of the present invention is a resin composition comprising: (A) an amine compound having a biphenyl skeleton, (B) a maleimide compound having an aliphatic chain having 7 or more carbon atoms, and (C) a maleimide compound having no aliphatic chain having 7 or more carbon atoms.

Description

Resin composition

Technical Field

The present invention relates to a resin composition containing maleimide. The present invention also relates to a cured product, a sheet-like laminate, a resin sheet, a printed wiring board, and a semiconductor device obtained using the resin composition.

Background

As a technique for manufacturing a printed wiring board, a manufacturing method using a stack (build) method in which insulating layers and conductor layers are alternately stacked is known. In the manufacturing method using the stack method, generally, the insulating layer is formed by curing a resin composition. In recent years, further improvement in dielectric properties such as dielectric constant and dielectric loss tangent of the insulating layer and further improvement in peel strength of the plated conductor layer have been desired.

Heretofore, various maleimide compounds have been known (patent documents 1 to 3).

Documents of the prior art

Patent document

Patent document 1: japanese patent laid-open publication No. 2019-203122

Patent document 2: international publication No. 2018/212116

Patent document 3: international publication No. 2020/045489.

Disclosure of Invention

Technical problem to be solved by the invention

The present invention addresses the problem of providing a resin composition that can give a cured product that has a low relative dielectric constant (Dk) and a low dielectric loss tangent (Df), and that has excellent peel strength of a plated conductor layer.

Technical scheme for solving technical problem

As a result of earnest studies to solve the problems of the present invention, the present inventors have found that a cured product having a low relative permittivity (Dk) and a low dielectric loss tangent (Df) and excellent peel strength of a plated conductor layer can be obtained unexpectedly by using a resin composition containing (a) an amine compound having a biphenyl skeleton, (B) a maleimide compound having an aliphatic chain having 7 or more carbon atoms, and (C) a maleimide compound having no aliphatic chain having 7 or more carbon atoms, and have completed the present invention.

Namely, the present invention includes the following;

[1] a resin composition comprising:

(A) amine compound having biphenyl skeleton,

(B) A maleimide compound having an aliphatic chain having 7 or more carbon atoms, and

(C) a maleimide compound having no aliphatic chain having 7 or more carbon atoms;

[2] the resin composition according to the above [1], wherein the component (B) has: a maleimide group directly bonded (directly bonded) to a carbon atom not constituting an aromatic ring;

[3] the resin composition according to the above [1] or [2], wherein the component (C) has: a maleimide group directly bonded to a carbon atom constituting an aromatic ring;

[4] the resin composition according to any one of the above [1] to [3], wherein the component (A) has a primary amino group;

[5] the resin composition according to any one of the above [1] to [4], wherein the component (A) has: an amino group directly bonded to a carbon atom constituting an aromatic ring.

[6] The resin composition according to any one of the above [1] to [5], wherein,

(A) the components comprise: an amine compound having a repeating unit represented by the formula (A1),

[ chemical formula 1]

Wherein V and W each independently represent-C (R')₂-、-O-、-CO-、-S-、-SO-、-SO₂-, -CONH-, or-NHCO-, R independently represents a substituent, R' independently represents a hydrogen atom or a substituent, and h, i, and j independently represent an integer of 0 to 2.

[7] The resin composition according to any one of the above [1] to [6], wherein the content of the component (A) is 3 to 40% by mass, based on 100% by mass of nonvolatile components in the resin composition;

[8] the resin composition according to any one of the above [1] to [7], wherein the content of the component (B) is 3 to 40% by mass, based on 100% by mass of nonvolatile components in the resin composition;

[9] the resin composition according to any one of the above [1] to [8], wherein the content of the component (C) is 3 to 40% by mass, based on 100% by mass of nonvolatile components in the resin composition;

[10] the resin composition according to any one of the above [1] to [9], wherein the mass ratio of the component (C) to the component (B), (component (C)/component (B)), is 0.5 to 20;

[11] the resin composition according to any one of the above [1] to [10], wherein the mass ratio of the component (A) to the total of the components (B) and (C), (the total of component (A)/component (B) and component (C)), is 0.1 to 0.5;

[12] the resin composition according to any one of the above [1] to [11], further comprising (D) a radical polymerizable compound other than the components (B) and (C);

[13] the resin composition according to any one of the above [1] to [12], further comprising (E) an inorganic filler;

[14] the resin composition according to the above [13], wherein the content of the component (E) is 25% by mass or more, assuming that the nonvolatile content in the resin composition is 100% by mass;

[15] the resin composition according to any one of the above [1] to [14], wherein a dielectric loss tangent of a cured product of the resin composition is 0.004 or less when measured at 5.8GHz and 23 ℃;

[16] the resin composition according to any one of the above [1] to [15], wherein a cured product of the resin composition has a relative dielectric constant of 2.9 or less as measured at 5.8GHz and 23 ℃;

[17] a cured product of the resin composition according to any one of the above [1] to [16 ];

[18] a sheet-like laminate comprising the resin composition according to any one of the above [1] to [16 ];

[19] a resin sheet, comprising: a support and a resin composition layer formed of the resin composition according to any one of the above [1] to [16] provided on the support;

[20] a printed wiring board comprising an insulating layer formed of a cured product of the resin composition according to any one of [1] to [16 ];

[21] a semiconductor device comprising the printed wiring board according to [20 ].

ADVANTAGEOUS EFFECTS OF INVENTION

The resin composition of the present invention can provide a cured product having a low relative dielectric constant (Dk) and dielectric loss tangent (Df) and an excellent peel strength of a plated conductor layer.

Detailed Description

The present invention will be described in detail below with reference to preferred embodiments thereof. However, the present invention is not limited to the embodiments and examples described below, and may be modified and implemented without departing from the scope of the claims and their equivalents.

< resin composition >

The resin composition of the present invention comprises (a) an amine compound having a biphenyl skeleton, (B) a maleimide compound having an aliphatic chain having 7 or more carbon atoms, and (C) a maleimide compound having no aliphatic chain having 7 or more carbon atoms. By using such a resin composition, a cured product having a low relative dielectric constant (Dk) and dielectric loss tangent (Df) and excellent peel strength of the plated conductor layer can be obtained.

The resin composition of the present invention may further contain an optional component in addition to (a) the amine compound having a biphenyl skeleton, (B) the maleimide compound having an aliphatic chain having 7 or more carbon atoms, and (C) the maleimide compound having no aliphatic chain having 7 or more carbon atoms. Examples of the optional component include (D) an optional radical polymerizable compound, (E) an inorganic filler, (F) a curing accelerator, (G) other additives, and (H) an organic solvent. Hereinafter, each component contained in the resin composition will be described in detail.

< (A) an amine compound having a biphenyl skeleton

The resin composition of the present invention contains (a) an amine compound having a biphenyl skeleton. (A) The components can be used alone in 1 kind, also can be used in 2 or more arbitrary combinations. In one embodiment, the amino group contained in the component (a) may undergo an addition reaction with the components (B) and (C) (and the component (D) in the case where the component (D) is contained), or the like. In one embodiment, the component (A) preferably has 2 or more amino groups in 1 molecule, more preferably 3 or more amino groups in 1 molecule. (A) Among the components, the amino group may have any of a primary amino group, a secondary amino group and a tertiary amino group, and in one embodiment, the amino group is preferably a primary amino group. In one embodiment, the amino group in the component (a) is preferably an amino group directly bonded to a carbon atom constituting an aromatic ring (aromatic amino group), more preferably an aromatic primary amino group, and particularly preferably the amino group contained in the component (a) is only an aromatic primary amino group.

In one embodiment, the component (a) preferably contains: an amine compound having a repeating unit represented by the formula (A1).

[ chemical formula 2]

[ wherein V and W each independently represent-C (R')₂-、-O-、-CO-、-S-、-SO-、-SO₂-, -CONH-, or-NHCO- (preferably-C (R')₂-, R independently represent a substituent, R' independently represents a hydrogen atom or a substituent (preferably a hydrogen atom), and h, i and j independently represent an integer of 0 to 2 (preferably 0)]。

The h cell, the i cell, and the j cell may be the same or different.

In the present specification, the substituent is not particularly limited, and examples thereof include an alkyl group, an alkenyl group, an aryl group, an alkyl-aryl group (an aryl group substituted with 1 or more alkyl groups), an aryl-aryl group (an aryl group substituted with 1 or more aryl groups), an aryl-alkyl group (an alkyl group substituted with 1 or more aryl groups), an alkyl-oxy group, an alkenyl-oxy group, an aryl-oxy group, monovalent substituents such as alkyl-carbonyl, alkenyl-carbonyl, aryl-carbonyl, alkyl-oxy-carbonyl, alkenyl-oxy-carbonyl, aryl-oxy-carbonyl, alkyl-carbonyl-oxy, alkenyl-carbonyl-oxy, and aryl-carbonyl-oxy may further include divalent substituents such as an oxo group (═ O), as long as the substituents are substitutable.

"alkyl" refers to a straight, branched, and/or cyclic monovalent saturated hydrocarbon group. The alkyl group is not particularly limited, and is preferably an alkyl group having 1 to 14 carbon atoms, more preferably an alkyl group having 1 to 10 carbon atoms, and still more preferably an alkyl group having 1 to 6 or 4 to 10 carbon atoms. Examples of the alkyl group include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, a decyl group, a cyclopentyl group, a cyclohexyl group, a methylcyclohexyl group, a dimethylcyclohexyl group, a trimethylcyclohexyl group, a cyclopentylmethyl group, and a cyclopentylmethyl group. Alkenyl refers to a straight, branched, and/or cyclic monovalent aliphatic unsaturated hydrocarbon group having at least 1 carbon-carbon double bond. The alkenyl group is not particularly limited, but is preferably an alkenyl group having 2 to 14 carbon atoms, more preferably an alkenyl group having 2 to 10 carbon atoms, and still more preferably an alkenyl group having 2 to 6 or 4 to 10 carbon atoms. Examples of the alkenyl group include a vinyl 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 a cyclohexenyl group. Aryl means a monovalent aromatic hydrocarbon group. The aryl group is preferably an aryl group having 6 to 14 carbon atoms. Examples of the aryl group include a phenyl group, a 1-naphthyl group, and a 2-naphthyl group.

(A) The weight average molecular weight (Mw) of the component (B) is preferably 300 to 4000, more preferably 300 to 3000, further preferably 300 to 2000. (A) The weight average molecular weight of the component (d) can be measured as a value in terms of polystyrene by a Gel Permeation Chromatography (GPC) method.

(A) The equivalent of the amino functional group of the component (A) is preferably 100 to 1000g/eq, more preferably 100 to 500g/eq. (A) The functional group equivalent of the amino group of the component (a) is the mass of the component (a) per 1 equivalent of the amino group.

Specific examples of the component (a) include amine compounds having a repeating unit represented by the formula (a 2).

[ chemical formula 3]

Examples of commercially available products of component (A) include "BAN" (amine compound of formula (A2) described above) manufactured by Nippon Kagaku K.K.

The content of the component (a) in the resin composition is not particularly limited, and is preferably 60% by mass or less, more preferably 50% by mass or less, further preferably 40% by mass or less, further more preferably 30% by mass or less, particularly preferably 25% by mass or less, with respect to 100% by mass of nonvolatile components in the resin composition. The lower limit of the content of the component (A) in the resin composition is not particularly limited, but is preferably 0.1% by mass or more, more preferably 1% by mass or more, further preferably 3% by mass or more, further preferably 5% by mass or more, particularly preferably 7% by mass or more, when the nonvolatile content in the resin composition is 100% by mass.

< (B) a maleimide compound having an aliphatic chain of 7 or more carbon atoms

The resin composition of the present invention contains (B) a maleimide compound having an aliphatic chain having 7 or more carbon atoms. (B) The components can be used alone in 1 kind, also can be used in 2 or more arbitrary combinations. The maleimide compound is an organic compound containing at least 1, preferably 2 or more, maleimide group (2, 5-dihydro-2, 5-dioxo-1H-pyrrol-1-yl) in 1 molecule. In one embodiment, the component (B) preferably has a maleimide group directly bonded to a carbon atom not constituting an aromatic ring, and particularly preferably the maleimide group contained in the component (B) is only a maleimide group directly bonded to a carbon atom not constituting an aromatic ring.

The aliphatic chain means an aliphatic chain in which the skeleton atoms are bonded via a single bond, a double bond or a triple bond, preferably an aliphatic chain in which the skeleton atoms are bonded via a single bond or a double bond, particularly preferably an aliphatic chain in which the skeleton atoms are bonded via only a single bond. Further, the aliphatic chain may have a branched chain, but does not constitute a part or all of the ring structure.

The aliphatic chain may be an aliphatic carbon chain having only carbon atoms as skeleton atoms (for example, an alkylene chain, an alkenylene chain, etc.), or may be a heteroatom-containing aliphatic chain having, as skeleton atoms, heteroatoms selected from oxygen atoms, nitrogen atoms, and sulfur atoms in addition to carbon atoms (for example, a polyalkylene oxide (polyalkylene oxide) chain, a polyalkylene imine chain, etc.), and in one embodiment, an aliphatic carbon chain having only carbon atoms as skeleton atoms is preferable. The upper limit of the number of carbon atoms in the backbone atoms of the aliphatic chain is not particularly limited, and may be, for example, 3000 or less, 1000 or less, 100 or less, 50 or less, or the like. The aliphatic chain having 7 or more carbon atoms is preferably one having 7 or more carbon atoms in the main chain.

In one embodiment, the maleimide compound of component (B) preferably includes a maleimide compound represented by formula (B1).

[ chemical formula 4]

[ in the formula, A¹Each independently represents a divalent organic group having an aliphatic chain of 7 or more carbon atoms, A²Each independently represents a divalent organic group having no aliphatic chain having 7 or more carbon atoms, B¹Each independently represents a tetravalent organic group having an aromatic ring and/or a non-aromatic ring, n1 and n2 represent 0 or an integer of 1 or more (preferably 0 or an integer of 1 to 100), either one of m1 and m2 represents 1 and the other represents 0, and the total of n1 and m1 is 1 or more]. The order and arrangement of the n1 units and the n2 units are arbitrary, and include alternating copolymers, block copolymers, random copolymers, and the like. In addition, each of the n1 cells and the n2 cells may be the same or different.

An aromatic ring is a ring which follows the Huckel's rule and has 4n +2 electrons per pi-electron system on the ring (n is a natural number). The aromatic ring may be a carbocyclic ring having a carbon atom as a ring-forming atom or a heterocyclic ring having a hetero atom such as an oxygen atom, a nitrogen atom, a sulfur atom and the like as a ring-forming atom, and in one embodiment, the carbocyclic ring is preferable. The aromatic ring includes not only a monocyclic aromatic ring and a fused ring in which 2 or more monocyclic aromatic rings are fused, but also a fused ring in which 1 or more monocyclic non-aromatic rings are fused to 1 or more monocyclic aromatic rings. Specific examples of the aromatic ring include a benzene ring, a naphthalene ring, an anthracene ring, an indane ring, a fluorene ring, a tetralin ring, and the like.

Non-aromatic refers to rings other than aromatic rings. The non-aromatic ring may be carbocyclic or heterocyclic, and in one embodiment is preferably carbocyclic. The non-aromatic ring may be a saturated ring or an unsaturated ring, and in one embodiment, a saturated ring is preferred. The non-aromatic ring includes a fused non-aromatic ring obtained by fusing a monocyclic non-aromatic ring such as a cycloalkane ring or a cycloalkene ring and 2 or more monocyclic non-aromatic rings such as a bridged hydrocarbon ring. The cycloalkane ring is a monocyclic aliphatic saturated hydrocarbon ring, and examples thereof include cycloalkane rings having 3 to 8 carbon atoms such as a cyclobutane ring, a cyclopentane ring, a cyclohexane ring, a cycloheptane ring, and a cyclooctane ring. The cycloolefin ring is a monocyclic aliphatic unsaturated hydrocarbon ring having at least 1 carbon-carbon double bond, and examples thereof include a cycloolefin ring having 4 to 8 carbon atoms such as a cyclobutene ring, a cyclopentene ring, a cyclohexene ring, a cycloheptene ring, a cyclooctene ring, a cyclopentadiene ring, and a cyclohexadiene ring. The bridging hydrocarbon ring is a non-aromatic ring formed of 2 or more rings having 2 or more atoms in total, and examples thereof include a bridging hydrocarbon ring having 8 to 15 carbon atoms such as a norbornane ring, a decalin ring, an adamantane ring, and a tetrahydrodicyclopentadiene ring.

When n1 is 1 or more, the ratio of n1 to n2 (n2/n1) is preferably 5.0 or less, more preferably 2.0 or less, still more preferably 1.5 or less, particularly preferably 1.2 or less.

A¹Each independently represents a divalent organic group having an aliphatic chain having 7 or more carbon atoms. With A¹The skeleton atom of the "divalent organic group" is, for example, selected from the group consisting of carbon atom, oxygen atom, nitrogen atom and sulfur atom, and the number of skeleton atoms is not particularly limitedThe amount of the surfactant may be, for example, 3000 or less, 1000 or less, 100 or less, 50 or less, or the like.

In one embodiment, A¹Each independently is preferably a divalent group obtained by removing 2 amino groups from dimer diamine. Dimer diamine is a compound obtained by replacing 2 terminal carboxyl groups (-COOH) of dimer acid with amino groups or aminomethyl groups, and has an aliphatic carbon chain having 7 or more carbon atoms. The dimer acid is, for example, a dimer of an unsaturated fatty acid (preferably an unsaturated fatty acid having 11 to 22 carbon atoms, particularly preferably an unsaturated fatty acid having 18 carbon atoms such as oleic acid and linoleic acid) or a hydrogenated product thereof.

In another embodiment, A¹Each independently preferably a divalent non-aromatic hydrocarbon group having an aliphatic carbon chain of 7 or more carbon atoms.

A¹Each independently preferably a divalent group represented by the formula (b1),

[ chemical formula 5]

[ in the formula, Y¹Each independently represents a linear or branched (preferably linear) alkylene group having 7 or more atoms (preferably the number of atoms in the alkylene main chain), or a linear or branched (preferably linear) alkenylene group having 7 or more atoms (preferably the number of atoms in the alkenylene main chain), preferably a linear or branched (preferably linear) alkylene group having 7 or more carbon atoms, and the ring Z^y1Denotes a cycloalkane ring which may have a group selected from alkyl and alkenyl groups, or a cycloalkene ring which may have a group selected from alkyl and alkenyl groups, preferably a cyclohexane ring which may have an alkyl group, d denotes 0 or 1 (preferably 1); denotes a bonding site]。

The alkylene group is a divalent saturated hydrocarbon group, and the number of carbon atoms of a linear or branched alkylene group having 7 or more carbon atoms is, for example, 7 to 200, preferably 7 to 100, more preferably 7 to 50. The alkenylene group is a divalent aliphatic unsaturated hydrocarbon group having at least 1 carbon-carbon double bond, and the number of carbon atoms of a straight-chain or branched alkenylene group having 7 or more carbon atoms is, for example, 7 to 200, preferably 7 to 100, more preferably 7 to 50.

Specific examples of the divalent group represented by the formula (b1) include divalent groups represented by the following formula.

[ chemical formula 6]

[ in the formula, a symbol represents a binding site ].

A²Each independently represents a divalent organic group having no aliphatic chain having 7 or more carbon atoms (that is, in the case of having an aliphatic chain, the divalent organic group having 6 or less carbon atoms of the aliphatic chain having the largest carbon number in these aliphatic chains). With A²The number of the skeleton atoms of the "divalent organic group" is not particularly limited, and may be, for example, 5 to 3000, 5 to 1000, 5 to 100, 5 to 50, and the like. A. the²For example, the divalent group is a divalent group obtained by removing 2 amino groups from a diamine compound having no aliphatic chain having 7 or more carbon atoms, which is generally used as a raw material of polyimide, and is not particularly limited.

A²Each independently preferably is a divalent organic group having an aromatic ring and/or a non-aromatic ring, which does not have an aliphatic chain having 7 or more carbon atoms (i.e., in the case of having an aliphatic chain, the aliphatic chain having the largest number of carbon atoms in these aliphatic chains has 6 or less carbon atoms and has an aromatic ring and/or a non-aromatic ring), and more preferably is a divalent group represented by formula (b 2).

[ chemical formula 7]

[ in the formula, Y²¹Each independently represents a single bond, or-C (R)^x)₂- (preferably-C (R)^x)₂-)，Y²²Each independently represents a single bond, -C (R)^y)₂-、-O-、-CO-、-S-、-SO-、-SO₂-, -CONH-, or-NHCO- (preferably-C (R))^y)₂-or-O-), R^xAnd R^yEach independently represents a hydrogen atom, a methyl group, an ethyl group or a phenyl group (preferably a hydrogen atom), and the ring Z^y2Each independently represents a non-aromatic ring which may have a group selected from an alkyl group having 1 to 6 carbon atoms and a phenyl group, or an aromatic ring which may have a group selected from an alkyl group having 1 to 6 carbon atoms and a phenyl group, e represents an integer of 0 or 1 or more (preferably an integer of 0 or 1 to 5), and represents a binding site]. The unit e may be the same or different from one another.

Specific examples of the divalent group represented by the formula (b2) include divalent groups represented by the following formula.

[ chemical formula 8]

[ in the formula, a symbol represents a binding site ].

B¹Each independently represents a tetravalent organic group having an aromatic ring and/or a non-aromatic ring. With B¹The skeleton atom of the "tetravalent organic group" is, for example, selected from carbon atom, oxygen atom, nitrogen atom and sulfur atom, and the number of skeleton atoms is not particularly limited, and may be, for example, 5 to 3000, 5 to 1000, 5 to 100, 5 to 50, and the like. B is¹For example, the quaternary group is a tetravalent group obtained by removing 2 anhydride groups (-CO-O-CO-) from a tetracarboxylic anhydride having an aromatic ring and/or a non-aromatic ring, which is generally used as a raw material of polyimide, and is not particularly limited.

B¹Each independently preferably is a tetravalent organic group having an aromatic ring and/or a non-aromatic ring, which does not have an aliphatic chain having 7 or more carbon atoms (i.e., a tetravalent organic group having an aromatic ring and/or a non-aromatic ring, which has 6 or less carbon atoms, of the aliphatic chain having the largest number of carbon atoms in these aliphatic chains), more preferably a tetravalent group represented by formula (b 3).

[ chemical formula 9]

[ in the formula, R¹Each independently represents an alkyl group having 1 to 6 carbon atoms or a phenyl group, X¹Each independently represents a single bond, -C (R)^z)₂-、-O-、-CO-、-S-、-SO-、-SO₂-, -CONH-, or-NHCO- (preferably-C (R)^z)₂-or-O-), R^zEach independently represents a hydrogen atom, a methyl group, an ethyl group or a phenyl group (preferably a hydrogen atom), and the ring Z^x1Independently represent a non-aromatic ring which may have a group selected from an alkyl group having 1 to 6 carbon atoms and a phenyl group, or an aromatic ring which may have a group selected from an alkyl group having 1 to 6 carbon atoms and a phenyl group, a independently represents an integer of 0 to 2 (preferably 0), b represents 0 or 1, c represents an integer of 0 or 1 or more (preferably 0 or an integer of 1 to 5), and a represents a bonding site]. The units a and c may be the same or different from each other.

Specific examples of the tetravalent group represented by formula (b3) include tetravalent groups represented by the following formulae.

[ chemical formula 10]

[ in the formula, a symbol represents a binding site ].

In one embodiment, the maleimide compound of component (B) is more preferably a compound represented by formula (B2) (the bond between the n1 unit and the n2 unit is preferably a bond).

[ chemical formula 11]

[ in the formula, the symbols are the same as those in formulae (B1), (B1), (B2) and (B3) ].

(B) The maleimide compound of the component (B) is more preferably a compound represented by the formula (B3) (wherein the bond between the n1 unit and the n2 unit is a bond),

[ chemical formula 12]

[ in the formula, the symbols are the same as those in formulae (B1), (B2) and (B3) ].

Specific examples of the component (B) include maleimide compounds represented by the formulae (B4-1) to (B4-5).

[ chemical formula 13]

[ in the formula, n1 'and n2' each independently represent an integer of 1 to 20, preferably an integer of 1 to 10 ]. The order and arrangement of the n1 'unit and the n2' unit are arbitrary, and include an alternating copolymer, a block copolymer, a random copolymer, and the like.

(B) The weight average molecular weight (Mw) of the component (B) is not particularly limited, but is preferably 200 to 50000, more preferably 300 to 40000, still more preferably 400 to 20000. (B) The weight average molecular weight of the component (d) can be measured as a value in terms of polystyrene by a Gel Permeation Chromatography (GPC) method.

Examples of the commercially available products of component (B) include "BMI-689", "BMI-1500", "BMI-1700", "BMI-3000J" and "BMI-2500" manufactured by Designer Molecules, Inc.

The content of the component (B) in the resin composition is not particularly limited, and is preferably 50% by mass or less, more preferably 40% by mass or less, further preferably 30% by mass or less, further more preferably 25% by mass or less, particularly preferably 20% by mass or less, with respect to 100% by mass of nonvolatile components in the resin composition. The lower limit of the content of the component (B) in the resin composition is not particularly limited, but is preferably 1% by mass or more, more preferably 3% by mass or more, further preferably 5% by mass or more, further more preferably 10% by mass or more, particularly preferably 15% by mass or more, with respect to 100% by mass of the nonvolatile component in the resin composition.

< (C) Maleimide Compound having no aliphatic chain having 7 or more carbon atoms

The resin composition of the present invention contains (C) a maleimide compound having no aliphatic chain having 7 or more carbon atoms as a component other than (B). That is, when component (C) has an aliphatic chain, the aliphatic chain having the largest number of carbon atoms in the aliphatic chain has 6 or less carbon atoms. (C) The components can be used alone in 1 kind, also can be used in 2 or more arbitrary combinations.

In one embodiment, the component (C) preferably has a maleimide group directly bonded to a carbon atom constituting an aromatic ring, and particularly preferably the maleimide group contained in the component (C) is only a maleimide group directly bonded to a carbon atom constituting an aromatic ring.

In one embodiment, the maleimide compound of component (C) preferably includes a maleimide compound represented by formula (C1-1) or (C1-2).

[ chemical formula 14]

[ in the formula, B²Independently represent a tetravalent organic group having no aliphatic chain having 7 or more carbon atoms, n represents an integer of 1 or more (preferably an integer of 1 to 100), A³Each independently represents a divalent organic group having no aliphatic chain having 7 or more carbon atoms, R³Each independently represents an alkyl group having 1 to 6 carbon atoms or a phenyl group, s represents an integer of 1 or more (preferably 1 or an integer of 1 to 100, more preferably 1 or an integer of 1 to 50, further more preferably 1 or an integer of 1 to 20), t independently represents an integer of 0 to 2 (preferably 0), and the other symbols are the same as those in the formula (B1)]. The n unit, the s unit, and the t unit may be the same or different from each other.

B²Each independently represents a tetravalent organic group having no aliphatic chain having 7 or more carbon atoms (i.e., having an aliphatic chain in which the number of carbon atoms in the aliphatic chain is the largestA tetravalent organic group having 6 or less carbon atoms in the aliphatic chain). With B²The skeleton atom of the "tetravalent organic group" is, for example, selected from carbon atom, oxygen atom, nitrogen atom and sulfur atom, and the number of skeleton atoms is not particularly limited, and may be, for example, 5 to 3000, 5 to 1000, 5 to 100, 5 to 50, and the like. B is²For example, the quaternary group is a tetravalent group obtained by removing 2 anhydride groups (-CO-O-CO-) from a tetracarboxylic anhydride having no aliphatic chain having 7 or more carbon atoms, which is generally used as a raw material of polyimide, and is not particularly limited.

B²Each independently preferably is a tetravalent organic group having an aromatic ring and/or a non-aromatic ring, which does not have an aliphatic chain having 7 or more carbon atoms (i.e., a tetravalent organic group having an aromatic ring and/or a non-aromatic ring, which has 6 or less carbon atoms, of the aliphatic chain having the largest number of carbon atoms in these aliphatic chains), more preferably a tetravalent group represented by the above formula (b 3).

A³Each independently represents a divalent organic group having no aliphatic chain having 7 or more carbon atoms. With A³The skeleton atom of the "divalent organic group" is selected from, for example, a carbon atom, an oxygen atom, a nitrogen atom and a sulfur atom, and the number of skeleton atoms is not particularly limited, and may be, for example, 1 to 3000, 1 to 1000, 1 to 100, 1 to 50, and the like.

The maleimide compound represented by the formula (C1-1) is preferably a maleimide compound represented by the formula (C2-1).

[ chemical formula 15]

[ in the formula, the symbols are the same as those in formulae (C1-1), (b2) and (b3) ].

The maleimide compound represented by the formula (C1-1) is more preferably a maleimide compound represented by the formula (C3-1),

[ chemical formula 16]

[ in the formula, R²Each independently represents an alkyl group having 1 to 6 carbon atoms or a phenyl group, each f independently represents an integer of 0 to 2, and the other symbols are the same as those in the formulae (C1-1), (b2) and (b3)]. The f units may be the same or different from one another.

The maleimide compound represented by the formula (C1-2) is preferably a maleimide compound represented by the formula (C2-2).

[ chemical formula 17]

[ in the formula, X³Each independently represents a single bond, -C (R)^a)₂-、-O-、-CO-、-S-、-SO-、-SO₂-, -CONH-, or-NHCO-, R^aEach independently represents a hydrogen atom, a methyl group, an ethyl group or a phenyl group, ring Z^x3Represents a non-aromatic ring which may have a group selected from an alkyl group having 1 to 6 carbon atoms and a phenyl group, or an aromatic ring which may have a group selected from an alkyl group having 1 to 6 carbon atoms and a phenyl group, u independently represents an integer of 0 or 1 or more (preferably 0 or an integer of 1 to 50), and the other symbols are the same as those in the formula (C1-2)]。

The maleimide compound represented by the formula (C1-2) is more preferably a maleimide compound represented by the formula (C3-2),

[ chemical formula 18]

[ in the formula, X⁴Each independently represents a single bond, -C (R)^b)(R^c)-、-O-、-CO-、-S-、-SO-、-SO₂-, -CONH-, or-NHCO-, R⁴And R^bEach independently represents a hydrogen atom, a methyl group or a phenyl group, R⁵Each independently represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms or a phenyl group, R^cRepresents a hydrogen atom, a methyl group or a phenyl group, or R⁵And R^cAre combined with each other to formA ring having a group selected from alkyl and alkenyl (e.g., indane ring), R⁶Each independently represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms or a phenyl group, v represents an integer of 0 or 1 or more (preferably 0 or an integer of 1 to 10), and the other symbols are the same as those in the formula (C1-2)]. The u unit and the v unit may be the same or different from each other.

Specific examples of the component (C) include maleimide compounds represented by the formulae (C4-1) to (C4-4).

[ chemical formula 19]

[ in the formula, n 'or n' each independently represents an integer of 1 to 20 (preferably an integer of 1 to 10), s 'represents an integer of 1 to 100 (preferably an integer of 1 to 50, more preferably an integer of 1 to 20), and v' each independently represents an integer of 1 to 10 (preferably an integer of 1 to 5) ]. The order and arrangement of the n' units and the n "units are arbitrary, and include alternating copolymers, block copolymers, random copolymers, and the like.

(C) The weight average molecular weight (Mw) of the component (B) is not particularly limited, but is preferably 200 to 50000, more preferably 300 to 40000, still more preferably 400 to 20000. (C) The weight average molecular weight of the component (d) can be measured as a value in terms of polystyrene by a Gel Permeation Chromatography (GPC) method.

Examples of the commercially available product of component (C) include "BMI-6100" manufactured by Designer polymers, and "MIR-3000-70 MT" manufactured by Nippon chemical Co., Ltd.

The content of the component (C) in the resin composition is not particularly limited, and is preferably 50% by mass or less, more preferably 40% by mass or less, further preferably 30% by mass or less, further more preferably 25% by mass or less, particularly preferably 20% by mass or less, with respect to 100% by mass of nonvolatile components in the resin composition. The lower limit of the content of the component (C) in the resin composition is not particularly limited, and is preferably 1 mass% or more, more preferably 3 mass% or more, further preferably 5 mass% or more, further more preferably 10 mass% or more, particularly preferably 15 mass% or more, when the nonvolatile content in the resin composition is 100 mass%.

The mass ratio of the component (C) to the component (B) (component (C)/component (B)) in the resin composition is not particularly limited, but is preferably 0.01 or more, more preferably 0.1 or more, further preferably 0.5 or more, particularly preferably 0.8 or more. (C) The upper limit of the mass ratio of the component (B) to the component (C) is not particularly limited, but is preferably 50 or less, more preferably 40 or less, further preferably 20 or less, particularly preferably 5 or less.

The mass ratio of the "(a) component" to the total of the "(B) component and (C)" component (total of (a) component/(B) component and (C)) in the resin composition is not particularly limited, but is preferably 0.01 or more, more preferably 0.05 or more, further preferably 0.1 or more, particularly preferably 0.2 or more. (A) The upper limit of the mass ratio of the component (A) to the total of the components (B) and (C), i.e., the upper limit of the mass ratio of the component (A) to the total of the components (B) and (C), is not particularly limited, but is preferably 5 or less, more preferably 1 or less, still more preferably 0.5 or less, and particularly preferably 0.3 or less.

< (D) an optional radically polymerizable compound

The resin composition of the present invention may contain, as an optional component, (D) a radical polymerizable compound other than the components (B) and (C). (D) The components can be used alone in 1 kind, also can be used in 2 or more arbitrary combinations.

(D) The component (C) may be, for example, a compound having a radical polymerizable unsaturated group. The radical polymerizable unsaturated group is not particularly limited as long as it is radical polymerizable, and is preferably an ethylenically unsaturated group having a carbon-carbon double bond at the terminal or inside, and specifically may be an unsaturated aliphatic group such as allyl group or 3-cyclohexenyl group; aromatic groups containing unsaturated aliphatic groups such as p-vinylphenyl group, m-vinylphenyl group, and styryl group; and α, β -unsaturated carbonyl groups such as acryloyl, methacryloyl, maleoyl, and fumaroyl groups. (D) The component (B) preferably has 1 or more radical polymerizable unsaturated groups, more preferably 2 or more radical polymerizable unsaturated groups.

As the component (D), known radically polymerizable compounds can be widely used, and examples thereof include, but are not particularly limited to, (D-1) vinyl-phenyl radically polymerizable compounds, (D-2) (meth) acrylic radically polymerizable compounds, and the like.

< D-1) vinyl-phenyl radical polymerizable Compound

(D-1) the vinylphenyl radical polymerizable compound is a radical polymerizable compound having a vinylphenyl group. The (D-1) vinylphenyl radical polymerizable compound preferably has 2 or more vinylphenyl groups per 1 molecule on average.

In one embodiment, (D-1) the vinylbenzyl radical polymerizable compound is preferably a vinylbenzyl-modified polyphenylene ether having a vinylbenzyl group and a polyphenylene ether skeleton, and particularly preferably a vinylbenzyl-modified polyphenylene ether having a repeating unit represented by the formula (D1) (the number of the repeating unit is preferably 2 to 300, more preferably 2 to 100) and a vinylbenzyl group (particularly, a both-terminal vinylbenzyl-modified polyphenylene ether in which hydrogen atoms of both terminal hydroxyl groups of the polyphenylene ether are replaced with vinylbenzyl groups).

[ chemical formula 20]

[ in the formula, R¹¹、R¹²、R¹³And R¹⁴Each independently represents a hydrogen atom or a substituent, preferably a hydrogen atom or an alkyl group, particularly preferably a hydrogen atom or a methyl group]。

In another embodiment, the (D-1) vinylphenyl radical polymerizable compound is preferably a divinylbenzene polymer having a repeating unit represented by the formula (D2) (the number of repeating units is preferably 2 to 200).

[ chemical formula 21]

[ in the formula, R¹⁵、R¹⁶And R¹⁷Each independently represents a hydrogen atom or a substituent, preferably a hydrogen atom]. The divinylbenzene polymer may be a copolymer further having other styrene skeleton units such as a styrene unit and an ethylstyrene unit. When other styrene skeleton units are present, the proportion of the repeating unit of formula (D2) is preferably 5 to 70 mol% based on the total styrene skeleton units.

The number average molecular weight of the (D-1) vinylphenyl radical polymerizable compound is not particularly limited, but is preferably 500 to 100000, more preferably 700 to 80000. (D) The number average molecular weight of the component (d) can be measured as a value in terms of polystyrene by a Gel Permeation Chromatography (GPC) method. (D-1) the functional group equivalent of the vinyl group in the vinyl-phenyl radical polymerizable compound is not particularly limited, but is preferably 200g/eq to 3000g/eq, more preferably 200g/eq to 2000g/eq.

Examples of commercially available products of the (D-1) vinylphenyl radical polymerizable compound include "OPE-2 St 1200" and "OPE-2 St 2200" manufactured by Mitsubishi gas chemical corporation (vinylbenzyl-modified polyphenylene ether); "ODV-XET-X03", "ODV-XET-X04" and "ODV-XET-X05" (divinylbenzene polymer) manufactured by Nikko Tekken chemical Co., Ltd.

< (D-2) (meth) acrylic radically polymerizable compound

The (D-2) (meth) acrylic radical polymerizable compound is a radical polymerizable compound having an acryloyl group and/or a methacryloyl group. The (D-2) (meth) acrylic radical polymerizable compound preferably has 2 or more acryloyl groups and/or methacryloyl groups in an average of 1 molecule. The (D-2) (meth) acrylic radical polymerizable compound is preferably a (meth) acrylic-modified polyphenylene ether having "acryloyl group and/or methacryloyl group" and a "polyphenylene ether skeleton", and particularly preferably a (meth) acrylic-modified polyphenylene ether having a repeating unit represented by the formula (D3) (the number of repeating units is preferably 2 to 300, more preferably 2 to 100) and an acryloyl group and/or a methacryloyl group (particularly, a both-terminal (meth) acrylic-modified polyphenylene ether in which hydrogen atoms of both terminal hydroxyl groups of the polyphenylene ether are replaced with acryloyl group and/or methacryloyl group).

[ chemical formula 22]

[ in the formula, R²¹、R²²、R²³And R²⁴Each independently represents a hydrogen atom or a substituent, preferably a hydrogen atom or an alkyl group, particularly preferably a hydrogen atom or a methyl group]。

The number average molecular weight of the (D-2) (meth) acrylic radical polymerizable compound is not particularly limited, but is preferably 500 to 10000, more preferably 700 to 5000. The equivalent weight of the functional groups of the acryloyl group and the methacryloyl group in the (D-2) (meth) acrylic radical polymerizable compound is not particularly limited, but is preferably 200g/eq to 3000g/eq, more preferably 300g/eq to 2000g/eq.

Examples of commercially available products of the (D-2) (meth) acrylic radically polymerizable compound include "SA 9000" and "SA 9000-111" (methacrylic-modified polyphenylene ether) manufactured by Sabic Innovative Plastics, Inc. (SABIC Innovative Plastics).

The content of the component (D) in the resin composition is not particularly limited, and is preferably 60% by mass or less, more preferably 50% by mass or less, further preferably 40% by mass or less, further more preferably 30% by mass or less, particularly preferably 20% by mass or less, with respect to 100% by mass of nonvolatile components in the resin composition. The lower limit of the content of the component (D) in the resin composition is not particularly limited, and may be, for example, 0 mass%, 0.1 mass% or more, 1 mass% or more, 3 mass% or more, 5 mass% or more, 7 mass% or more, or the like, assuming that the nonvolatile component in the resin composition is 100 mass%.

(E) inorganic filler

The resin composition of the present invention may contain (E) an inorganic filler as an optional component. (E) The inorganic filler is contained in the resin composition in the form of particles.

As the material of the inorganic filler (E), an inorganic compound is used. Examples of the material of the inorganic filler (E) include silica, alumina, glass, cordierite, silicon oxide, barium sulfate, barium carbonate, talc, clay, mica powder, zinc oxide, hydrotalcite, boehmite, aluminum hydroxide, magnesium hydroxide, calcium carbonate, magnesium 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 zirconate, barium zirconate, calcium zirconate, zirconium phosphate tungstate, ferrite, and iron-based alloys. Among them, silica is particularly preferable. Examples of the silica include amorphous silica, fused silica, crystalline silica, synthetic silica, hollow silica and the like. Further, as the silica, spherical silica is preferable. (E) The inorganic filler may be used alone in 1 kind, or 2 or more kinds may be used in combination at an arbitrary ratio.

Examples of commercially available products of the (E) inorganic filler include "UFP-30" manufactured by electrochemical industries, Ltd "," SP60-05 "and" SP507-05 "manufactured by Nippon iron and Steel materials, YC 100C" and "YA 050C" and "YA 050C-MJE" and "YA 010C" manufactured by Denka, "UFP-30" manufactured by Denka, SILFIL NSS-3N "and" SILFIL NSS-4N "and" SILFIL NSS-5N "manufactured by Denka, SC2500 SQ" and "SO-C4" and "SO-C2" and "SO-C1" manufactured by Denka, and "DAW-03" and "FB-105 FD" manufactured by Denka.

(E) The average particle size of the inorganic filler is not particularly limited, but is preferably 10 μm or less, more preferably 5 μm or less, further preferably 2 μm or less, further preferably 1 μm or less, particularly preferably 0.7 μm or less. (E) The lower limit of the average particle size of the inorganic filler is not particularly limited, but is preferably 0.01 μm or more, more preferably 0.05 μm or more, still more preferably 0.1 μm or more, particularly preferably 0.2 μm or more. (E) The average particle diameter of the inorganic filler can be measured by a laser diffraction scattering method based on Mie scattering theory. Specifically, the particle size distribution of the inorganic filler can be measured on a volume basis by a laser diffraction scattering particle size distribution measuring apparatus, and the median particle size is measured as an average particle size. As the measurement sample, a sample obtained by weighing 100mg of the inorganic filler and 10g of methyl ethyl ketone in a vial and dispersing them by ultrasonic waves for 10 minutes can be used. For the measurement sample, the volume-based particle size distribution of the inorganic filler was measured by a flow cell (flowcell) system using a laser diffraction type particle size distribution measuring apparatus with the wavelengths of the light source used being blue and red, and the average particle size was calculated from the obtained particle size distribution as the median particle size. Examples of the laser diffraction type particle size distribution measuring apparatus include "LA-960" manufactured by horiba, Ltd.

(E) The specific surface area of the inorganic filler is not particularly limited, but is preferably 0.1m²More than g, preferably 0.5m²More preferably 1m or more per gram²More than g, particularly preferably 3m²More than g. (E) The upper limit of the specific surface area of the inorganic filler is not particularly limited, but is preferably 100m²A ratio of less than g, preferably 70m²A total of 50m or less²A specific ratio of the total amount of the components is 40m or less²The ratio of the carbon atoms to the carbon atoms is less than g. The specific surface area of the inorganic filler can be obtained by adsorbing nitrogen gas onto the surface of a sample by the BET method using a specific surface area measuring apparatus (MacsorbHM-1210, manufactured by Mountech corporation) and calculating the specific surface area by the BET multipoint method.

(E) The inorganic filler is preferably surface-treated with a suitable surface treatment agent. By performing the surface treatment, the moisture resistance and dispersibility of the inorganic filler (E) can be improved. Examples of the surface treatment agent include: vinyl silane coupling agents such as vinyltrimethoxysilane and vinyltriethoxysilane; epoxy silane coupling agents such as 2- (3, 4-epoxycyclohexyl) ethyltrimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropylmethyldiethoxysilane and 3-glycidoxypropyltriethoxysilane; styrene-based silane coupling agents such as p-styryltrimethoxysilane; methacrylic silane coupling agents such as 3-methacryloxypropylmethyldimethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3-methacryloxypropylmethyldiethoxysilane and 3-methacryloxypropyltriethoxysilane; acrylic silane coupling agents such as 3-acryloxypropyltrimethoxysilane; amino silane coupling agents such as N-2- (aminoethyl) -3-aminopropylmethyldimethoxysilane, N-2- (aminoethyl) -3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, 3-triethoxysilyl-N- (1, 3-dimethyl-butylene) propylamine, N-phenyl-3-aminopropyltrimethoxysilane, N-phenyl-8-aminooctyltrimethoxysilane, and N- (vinylbenzyl) -2-aminoethyl-3-aminopropyltrimethoxysilane; isocyanurate-based silane coupling agents such as tris (trimethoxysilylpropyl) isocyanurate; ureido-type silane coupling agents such as 3-ureidopropyltrialkoxysilane; mercapto silane coupling agents such as 3-mercaptopropylmethyldimethoxysilane and 3-mercaptopropyltrimethoxysilane; isocyanate-based silane coupling agents such as 3-isocyanatopropyltriethoxysilane; acid anhydride silane coupling agents such as 3-trimethoxysilylpropyl succinic anhydride; and the like; and non-silane-coupled alkoxysilane compounds such as methyltrimethoxysilane, dimethyldimethoxysilane, phenyltrimethoxysilane, methyltriethoxysilane, dimethyldiethoxysilane, phenyltriethoxysilane, n-propyltrimethoxysilane, n-propyltriethoxysilane, hexyltrimethoxysilane, hexyltriethoxysilane, octyltriethoxysilane, decyltrimethoxysilane, 1, 6-bis (trimethoxysilyl) hexane, and trifluoropropyltrimethoxysilane. The surface treatment agent may be used alone or in combination of two or more kinds at an arbitrary ratio.

Examples of commercially available surface treatment agents include: "KBM-1003", "KBE-1003" (vinyl-based silane coupling agent), "KBM-303", "KBM-402", "KBM-403", "KBE-402", "KBE-403" (epoxy-based silane coupling agent), "KBM-1403" (styrene-based silane coupling agent), "KBM-502", "KBM-503", "KBE-502", "KBE-503" (methacrylic silane coupling agent), "KBM-5103" (acrylic silane coupling agent), "KBM-602", "KBM-603", "KBM-903", "KBE-9103P", "KBM-573", "KBM-575" (amino-based silane coupling agent), "KBM-9659" (isocyanurate-based silane coupling agent), "KBE-585" (ureido silane coupling agent), "KBM-802", "KBM-803" (mercapto silane coupling agent), "KBE-9007N" (isocyanate silane coupling agent), "X-12-967C" (anhydride silane coupling agent), "KBM-13", "KBM-22", "KBM-103", "KBE-13", "KBE-22", "KBE-103", "KBM-3033", "KBE-3033", "KBM-3063", "KBE-3083", "KBM-3103C", "KBM-3063066", "KBM-7103" (non-silane coupling alkoxysilane compound), and the like.

From the viewpoint of improving the dispersibility of the inorganic filler, the degree of surface treatment by the surface treatment agent is preferably controlled within a predetermined range. Specifically, it is preferable that 100% by mass of the inorganic filler is surface-treated with 0.2 to 5% by mass of the surface treatment agent, more preferably 100% by mass of the inorganic filler is surface-treated with 0.2 to 3% by mass of the surface treatment agent, and still more preferably 100% by mass of the inorganic filler is surface-treated with 0.3 to 2% by mass of the surface treatment agent.

The degree of surface treatment by the surface treatment agent can be evaluated by the amount of carbon per unit surface area of the inorganic filler. From the viewpoint of improving the dispersibility of the inorganic filler, the amount of carbon per unit surface area of the inorganic filler is preferably 0.02mg/m²Above, preferably 0.1mg/m²The above, more preferably 0.2mg/m²The above. On the other hand, from the viewpoint of preventing the melt viscosity of the resin composition and the increase in melt viscosity in the form of a sheet, it is preferably 1.0mg/m²The concentration is preferably 0.8mg/m or less²More preferably 0.5mg/m or less²The following.

(E) The amount of carbon per unit surface area of the inorganic filler material can be measured after subjecting the surface-treated inorganic filler material to a cleaning treatment with a solvent such as Methyl Ethyl Ketone (MEK). Specifically, to the inorganic filler surface-treated with the surface treatment agent, a sufficient amount of MEK was added as a solvent, and ultrasonic cleaning was performed at 25 ℃ for 5 minutes. After removing the supernatant liquid and drying the solid components, 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.

The content of the inorganic filler (E) in the resin composition is not particularly limited, and when the nonvolatile content in the resin composition is 100% by mass, it is preferably 90% by mass or less, more preferably 80% by mass or less, further more preferably 75% by mass or less, particularly preferably 70% by mass or less. The lower limit of the content of the inorganic filler (E) in the resin composition is not particularly limited, and when the nonvolatile content in the resin composition is set to 100 mass%, it may be, for example, 0 mass% or more, 1 mass% or more, 5 mass% or more, 10 mass% or more, or the like, preferably 20 mass% or more, more preferably 25 mass% or more, still more preferably 35 mass% or more, particularly preferably 40 mass% or more.

(F) curing Accelerator

The resin composition of the present invention may contain (F) a curing accelerator as an optional component. In one embodiment, the (F) curing accelerator may function as a catalyst for accelerating an addition reaction of the component (a) with the components (B) and (C) (and the component (D) in the case where the component (D) is contained).

Examples of the curing accelerator (F) include (F-1) imidazole-based curing accelerators, (F-2) phosphorus-based curing accelerators, (F-3) urea-based curing accelerators, (F-4) guanidine-based curing accelerators, (F-5) metal-based curing accelerators, and (F-6) amine-based curing accelerators. In one embodiment, (F) the curing accelerator preferably includes (F-1) an imidazole-based curing accelerator. (F) The curing accelerator may be used alone in 1 kind, or 2 or more kinds may be used in combination.

Examples of the imidazole-based curing accelerator (F-1) include: 2-methylimidazole, 2-undecylimidazole, 2-heptadecylimidazole, 1, 2-dimethylimidazole, 2-ethyl-4-methylimidazole, 2-phenylimidazole, 2-phenyl-4-methylimidazole, 1-benzyl-2-phenylimidazole, 1-cyanoethyl-2-methylimidazole, 1-cyanoethyl-2-undecylimidazole, 1-cyanoethyl-2-ethyl-4-methylimidazole, 1-cyanoethyl-2-phenylimidazole, 1-cyanoethyl-2-undecylimidazolium trimellitate, salts thereof with a group selected from the group consisting of, 1-cyanoethyl-2-phenylimidazolium trimellitate, 2, 4-diamino-6- [2' -methylimidazolyl- (1') ] -ethyl-s-triazine, 2, 4-diamino-6- [2' -undecylimidazolyl- (1') ] -ethyl-s-triazine, 2, 4-diamino-6- [2' -ethyl-4 ' -methylimidazolyl- (1') ] -ethyl-s-triazine, 2, 4-diamino-6- [2' -methylimidazolyl- (1') ] -ethyl-s-triazine isocyanuric acid adduct, 2-phenylimidazole isocyanuric acid adduct, 2-phenyl-4, imidazole compounds such as 5-dihydroxymethylimidazole, 2-phenyl-4-methyl-5-hydroxymethylimidazole, 2, 3-dihydro-1H-pyrrolo [1,2-a ] benzimidazole, 1-dodecyl-2-methyl-3-benzylimidazolium chloride, 2-methylimidazoline and 2-phenylimidazoline, and adducts of imidazole compounds with epoxy resins.

As the imidazole-based curing accelerator (F-1), commercially available products can be used, and examples thereof include "1B 2 PZ", "2 MZA-PW" and "2 PHZ-PW" manufactured by Sizhou chemical Co., Ltd, "P200-H50" manufactured by Mitsubishi chemical Co., Ltd.

Examples of the phosphorus-based curing accelerator (F-2) include: aliphatic phosphonium salts such as tetrabutylphosphonium bromide, tetrabutylphosphonium chloride, tetrabutylphosphonium acetate, tetrabutylphosphonium decanoate, tetrabutylphosphonium laurate, bis (tetrabutylphosphonium) pyromellitate, tetrabutylphosphonium hexahydrophthalate, tetrabutylphosphonium 2, 6-bis [ (2-hydroxy-5-methylphenyl) methyl ] -4-methylphenolate, di-t-butylmethylphosphonium tetraphenylborate and the like; aromatic phosphonium salts such as methyltriphenylphosphonium bromide, ethyltriphenylphosphonium bromide, propyltriphenylphosphonium bromide, butyltriphenylphosphonium bromide, benzyltriphenylphosphonium chloride, tetraphenylphosphonium bromide, p-tolyltriphenylphosphonium tetra-p-tolylborate, tetraphenylphosphonium tetraphenylborate, tetraphenylphosphonium tetra-p-tolylborate, triphenylethylphosphonium tetraphenylborate, tris (3-methylphenyl) ethylphosphonium tetraphenylborate, tris (2-methoxyphenyl) ethylphosphonium tetraphenylborate, (4-methylphenyl) triphenylphosphonium thiocyanate, tetraphenylphosphonium thiocyanate, butyltriphenylphosphonium thiocyanate and the like; aromatic phosphine-borane complexes such as triphenylphosphine-triphenylborane; an aromatic phosphine-quinone addition reaction product such as a triphenylphosphine-p-benzoquinone addition reaction product; aliphatic phosphines such as tributylphosphine, tri-tert-butylphosphine, trioctylphosphine, di-tert-butyl (2-butenyl) phosphine, di-tert-butyl (3-methyl-2-butenyl) phosphine, and tricyclohexylphosphine; dibutylphenylphosphine, di-t-butylphenyl phosphine, methyldiphenylphosphine, ethyldiphenylphosphine, butyldiphenylphosphine, diphenylcyclohexylphosphine, triphenylphosphine, tri-o-tolylphosphine, tri-m-tolylphosphine, tri-p-tolylphosphine, tri (4-ethylphenyl) phosphine, tri (4-propylphenyl) phosphine, tri (4-isopropylphenyl) phosphine, tri (4-butylphenyl) phosphine, tri (4-t-butylphenyl) phosphine, tri (2, 4-dimethylphenyl) phosphine, tri (2, 5-dimethylphenyl) phosphine, tri (2, 6-dimethylphenyl) phosphine, tri (3, 5-dimethylphenyl) phosphine, tri (2,4, 6-trimethylphenyl) phosphine, tri (2, 6-dimethyl-4-ethoxyphenyl) phosphine, tri (2-methoxyphenyl) phosphine, triphenylphosphine, tri (4-t-butylphenyl) phosphine, tri (4-methylphenyl) phosphine, tri (4-methoxyphenyl) phosphine, tri (4-methylphenyl) phosphine, tri (4-phenyl) phosphine, tri (4-methylphenyl) phosphine, tri (4-butyl-phenyl) phosphine, tri (4-phenyl) phosphine, tri (2-phenyl) phosphine, tri (4, tri (2-phenyl) phosphine, tri (4, tri (2-butyl-phenyl) phosphine, tri (2-butyl, tri (4, tri (2-phenyl) phosphine, tri (4, tri-phenyl) phosphine, tri (2-butyl, tri (4, tri-phenyl) phosphine, tri (2-phenyl) phosphine, tri (, And aromatic phosphines such as tris (4-methoxyphenyl) phosphine, tris (4-ethoxyphenyl) phosphine, tris (4-tert-butoxyphenyl) phosphine, diphenyl-2-pyridylphosphine, 1, 2-bis (diphenylphosphino) ethane, 1, 3-bis (diphenylphosphino) propane, 1, 4-bis (diphenylphosphino) butane, 1, 2-bis (diphenylphosphino) acetylene, and 2, 2' -bis (diphenylphosphino) diphenyl ether.

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

Examples of the guanidine-based curing accelerator (F-4) include: dicyandiamide, 1-methylguanidine, 1-ethylguanidine, 1-cyclohexylguanidine, 1-phenylguanidine, 1- (o-tolyl) guanidine, dimethylguanidine, diphenylguanidine, trimethylguanidine, tetramethylguanidine, pentamethylguanidine, 1,5, 7-triazabicyclo [4.4.0] dec-5-ene, 7-methyl-1, 5, 7-triazabicyclo [4.4.0] dec-5-ene, 1-methylbiguanide, 1-ethylbiguanide, 1-n-butylbiguanide, 1-n-octadecyl biguanide, 1-dimethylbiguanide, 1-diethylbiguanide, 1-cyclohexylbiguanide, 1-allylbiguanide, 1-phenylbiguanide, 1- (o-tolyl) biguanide and the like.

Examples of the metal-based curing accelerator (F-5) include organometallic complexes or organometallic salts of metals such as cobalt, copper, zinc, iron, nickel, manganese, and tin. Specific examples of the organometallic complex include: organic cobalt complexes such as cobalt (II) acetylacetonate and cobalt (III) acetylacetonate, organic copper complexes such as copper (II) acetylacetonate, organic zinc complexes such as zinc (II) acetylacetonate, organic iron complexes such as iron (III) acetylacetonate, organic nickel complexes such as nickel (II) acetylacetonate, and organic manganese complexes such as manganese (II) acetylacetonate. Examples of the organic metal salt include zinc octylate, tin octylate, zinc naphthenate, cobalt naphthenate, tin stearate, and zinc stearate.

Examples of the (F-6) amine-based curing accelerator include trialkylamines such as triethylamine and tributylamine, 4-dimethylaminopyridine, benzyldimethylamine, 2,4, 6-tris (dimethylaminomethyl) phenol, and 1, 8-diazabicyclo [5.4.0] undecene.

As the (F-6) amine-based curing accelerator, commercially available products can be used, and examples thereof include "MY-25" manufactured by Ajinomoto Fine-Technino, Inc.

The content of the curing accelerator (F) in the resin composition is not particularly limited, and is preferably 10% by mass or less, more preferably 5% by mass or less, further more preferably 3% by mass or less, particularly preferably 1% by mass or less, when the nonvolatile content in the resin composition is 100% by mass. The lower limit of the content of the (F) curing accelerator in the resin composition is not particularly limited, and may be, for example, 0 mass% or more, 0.001 mass% or more, 0.01 mass% or more, 0.1 mass% or more, 0.5 mass% or more, or the like, assuming that the nonvolatile content in the resin composition is 100 mass%.

< (G) other additives

The resin composition of the present invention may further contain an optional additive as a nonvolatile component. Examples of such additives include: curing agents other than the component (A), such as phenol curing agents and thiol curing agents; thermosetting resins such as epoxy resins, epoxy acrylate resins, urethane acrylate resins, polyurethane resins, cyanate ester resins, benzoxazine resins, unsaturated polyester resins, phenol resins, melamine resins, silicone resins, and epoxy resins; radical polymerization initiators such as peroxide radical polymerization initiators and azo radical polymerization initiators; thermoplastic resins such as polyvinyl acetal resin, polyolefin resin, polysulfone resin, polyethersulfone resin, polyphenylene ether resin, polycarbonate resin, polyetheretherketone resin, and polyester resin; organic fillers such as rubber particles, organic metal compounds such as organic copper compounds, organic zinc compounds, and organic cobalt compounds; colorants such as phthalocyanine blue, phthalocyanine green, olive green, diazo yellow, crystal violet, titanium oxide, and carbon black; polymerization inhibitors such as hydroquinone, catechol, pyrogallol, and phenothiazine; leveling agents such as silicone leveling agents and acrylic polymer leveling agents; thickeners such as bentonite (Benton) and montmorillonite; defoaming agents such as silicone defoaming agents, acrylic defoaming agents, fluorine defoaming agents, vinyl resin defoaming agents and the like; ultraviolet absorbers such as benzotriazole-based ultraviolet absorbers; adhesion improving agents 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 antioxidants and hindered amine antioxidants; fluorescent whitening agents such as stilbene derivatives; surfactants such as fluorine-based surfactants and silicone-based surfactants; flame retardants such as phosphorus flame retardants (e.g., phosphate ester compounds, phosphazene compounds, phosphinic acid compounds, red phosphorus), nitrogen flame retardants (e.g., melamine sulfate), halogen flame retardants, inorganic flame retardants (e.g., antimony trioxide), and the like; dispersants such as phosphate dispersants, polyoxyalkylene dispersants, acetylene dispersants, silicone dispersants, anionic dispersants, and cationic dispersants; and stabilizers such as borate stabilizers, titanate stabilizers, aluminate stabilizers, zirconate stabilizers, isocyanate stabilizers, carboxylic acid stabilizers, and carboxylic anhydride stabilizers. (G) The other additives may be used alone in 1 kind, or 2 or more kinds may be used in combination in an arbitrary ratio. The content of (G) other additives can be appropriately set if it is a person skilled in the art.

(H) organic solvent

The resin composition of the present invention may contain an arbitrary organic solvent as a volatile component in addition to the nonvolatile component. As the organic solvent (H), known organic solvents can be suitably used, and the kind thereof is not particularly limited. Examples of the organic solvent (H) 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, carbitol acetate, gamma-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-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. (H) The organic solvent can be used alone in 1 kind, can also be used in 2 or more kinds in any ratio combination.

In one embodiment, the content of the (H) organic solvent is not particularly limited, and may be, for example, 60 mass% or less, 40 mass% or less, 30 mass% or less, 20 mass% or less, 15 mass% or less, 10 mass% or less, or the like, when the total components in the resin composition are 100 mass%.

< method for producing resin composition >

The resin composition of the present invention can be produced, for example, by: in an arbitrary preparation vessel, (a) an amine compound having a biphenyl skeleton, (B) a maleimide compound having an aliphatic chain having 7 or more carbon atoms, (C) a maleimide compound having no aliphatic chain having 7 or more carbon atoms, (D) an arbitrary radical polymerizable compound to be used if necessary, (E) an inorganic filler to be used if necessary, (F) a curing accelerator to be used if necessary, (G) other additives to be used if necessary, and (H) an organic solvent to be used if necessary are added and mixed in an arbitrary order and/or partially or all at the same time. In addition, the temperature may be appropriately set during the addition and mixing of the components, and heating and/or cooling may be performed temporarily or continuously. In addition, during or after the addition and mixing, the resin composition may be uniformly dispersed by stirring or shaking the resin composition using a stirring device or a shaking device such as a mixer. Further, defoaming can be performed under low pressure conditions such as vacuum while stirring or shaking.

< Property of resin composition >

The cured product of the resin composition of the present invention can have a low dielectric loss tangent (Df). Therefore, in one embodiment, as shown in test example 1 below, the dielectric loss tangent (Df) of a cured product of the resin composition measured under the conditions of 5.8GHz and 23 ℃ is preferably 0.020 or less, 0.010 or less, more preferably 0.008 or less, 0.007 or less, still more preferably 0.006 or less, 0.005 or less, particularly preferably 0.004 or less, and 0.003 or less.

The cured product of the resin composition of the present invention can have a low relative dielectric constant (Dk). Therefore, in one embodiment, as shown in test example 1 below, the relative dielectric constant (Dk) of the cured product of the resin composition measured under the conditions of 5.8GHz and 23 ℃ is preferably 5.0 or less, more preferably 4.0 or less, still more preferably 3.5 or less, still more preferably 3.0 or less, and particularly preferably 2.9 or less.

The cured product of the resin composition of the present invention can have excellent peel strength of the plated conductor layer. Therefore, in one embodiment, as shown in test example 2 below, the peel strength of the copper plating layer calculated from the load when the copper-plated conductor layer is peeled off in the vertical direction by forming the copper-plated conductor layer on the cured product is preferably 0.2kgf/cm or more, more preferably 0.3kgf/cm or more, still more preferably 0.35kgf/cm or more, and particularly preferably 0.4kgf/cm or more. The upper limit is not particularly limited, and may be, for example, 10kgf/cm or less.

In one embodiment, a cured product of the resin composition of the present invention may have a feature of low arithmetic average roughness (Ra) of a surface after roughening treatment. Therefore, in one embodiment, the arithmetic average roughness (Ra) of the surface of the cured product after the roughening treatment, which is measured as shown in test example 2 described below, is preferably 300nm or less, more preferably 200nm or less, still more preferably 150nm or less, still more preferably 120nm or less, and particularly preferably 100nm or less. The lower limit is not particularly limited, and may be 1nm or more, 2nm or more, or the like.

< use of resin composition >

The resin composition of the present invention can be suitably used as a resin composition for insulation applications, particularly a resin composition for forming an insulation layer. Specifically, it can be suitably used as: a resin composition for forming an insulating layer (a resin composition for forming an insulating layer for forming a conductor layer) for forming a conductor layer (including a rewiring layer) formed on the insulating layer. In addition, in a printed wiring board described later, it can be suitably used as: a resin composition for forming an insulating layer of a printed wiring board (resin composition for forming an insulating layer of a printed wiring board). The resin composition of the present invention can be used in a wide range of applications requiring a resin composition, such as a resin sheet, a sheet-like laminate material such as a prepreg, a solder resist, an underfill material, a die bonding material, a semiconductor sealing material, a filling resin (a hole-filling resin), a component-embedding resin, and the like.

Further, for example, when a semiconductor chip package is manufactured through the following steps (1) to (6), the resin composition of the present invention can be suitably used as: a resin composition for forming a rewiring layer as an insulating layer for forming a rewiring layer (a resin composition for forming a rewiring layer), and a resin composition for sealing a semiconductor chip (a resin composition for sealing a semiconductor chip). In manufacturing the semiconductor chip package, a rewiring layer may be further formed on the sealing layer;

(1) a step of laminating a temporary fixing film on the base material,

(2) a step of temporarily fixing the semiconductor chip on the temporary fixing film,

(3) a step of forming a sealing layer on the semiconductor chip,

(4) a step of peeling the base material and the temporary fixing film from the semiconductor chip,

(5) a step of forming a rewiring formation layer as an insulating layer on the surface of the semiconductor chip from which the base material and the temporary fixing film are peeled, and

(6) and forming a rewiring layer as a conductor layer on the rewiring-forming layer.

The resin composition of the present invention can be suitably used also in the case where the printed wiring board is a component-embedded circuit board, because it provides an insulating layer having good component embeddability.

< sheet-like laminated Material >

The resin composition of the present invention can be used by coating in the form of varnish, but in general, it is industrially preferable to use the resin composition in the form of a sheet-like laminate containing the resin composition.

As the sheet-like laminate, a resin sheet or a prepreg described below is preferred.

In one embodiment, the resin sheet includes a support and a resin composition layer provided on the support, and the resin composition layer is formed of the resin composition of the present invention.

The thickness of the resin composition layer is preferably 50 μm or less, more preferably 40 μm or less, from the viewpoint of making the printed wiring board thinner and providing a cured product of the resin composition having excellent insulation even when the cured product is a thin film. The lower limit of the thickness of the resin composition layer is not particularly limited, and may be usually 5 μm or more and 10 μm or more.

Examples of the support include a film made of a plastic material, a metal foil, and a release paper, and a film made of a plastic material and a metal foil are preferable.

When a film made of a plastic material is used as the support, examples of the plastic material include: polyester such as polyethylene terephthalate (hereinafter sometimes abbreviated as "PET") and polyethylene naphthalate (hereinafter sometimes abbreviated as "PEN"), acrylic polymer such as polycarbonate (hereinafter sometimes abbreviated as "PC") and polymethyl methacrylate (PMMA), cyclic polyolefin, triacetyl cellulose (TAC), polyether sulfide (PES), polyether ketone, polyimide, and the like. Among them, polyethylene terephthalate and polyethylene naphthalate are preferable, and particularly, inexpensive polyethylene terephthalate is preferable.

When a metal foil is used as the support, examples of the metal foil include copper foil and aluminum foil, and copper foil is preferred. As the copper foil, a foil formed of a single metal of copper may be used, and a foil formed of an alloy of copper and another metal (for example, tin, chromium, silver, magnesium, nickel, zirconium, silicon, titanium, or the like) may also be used.

The surface of the support to be bonded to the resin composition layer may be subjected to matting treatment, corona treatment, or antistatic treatment.

Further, as the support, a support with a release layer having a release layer on a surface to be bonded to the resin composition layer can be used. Examples of the release agent used for the release layer of the support with a release layer include at least one selected from alkyd resins, polyolefin resins, polyurethane resins, and silicone resins. As the support having a release layer, commercially available products can be used, and examples thereof include "SK-1", "AL-5" and "AL-7" available from Leideke corporation, as a PET film having a release layer containing an alkyd resin-based release agent as a main component, "LumirrorT 60" available from Toyo corporation, "Purex" available from Diitenko corporation, and "Unipel" available from Unitika corporation.

The thickness of the support is not particularly limited, but is preferably in the range of 5 μm to 75 μm, more preferably 10 μm to 60 μm. When a support with a release layer is used, the thickness of the entire support with a release layer is preferably within the above range.

In one embodiment, the resin sheet may further include an arbitrary layer, as necessary. Examples of the optional layer include a protective film provided on a surface of the resin composition layer not bonded to the support (i.e., a surface opposite to the support) and selected for the support. The thickness of the protective film is not particularly limited, and is, for example, 1 μm to 40 μm. By laminating the protective film, it is possible to suppress adhesion of dust or the like to the surface of the resin composition layer or generation of damage on the surface of the resin composition layer.

The resin sheet can be produced, for example, by: the resin composition layer is formed by directly applying a liquid resin composition onto a support using a die coater or the like, or by preparing a resin varnish in which a resin composition is dissolved in an organic solvent, applying the resin varnish onto a support using a die coater or the like, and drying the resin varnish.

Examples of the organic solvent include the same organic solvents as those described as components of the resin composition. The organic solvent may be used alone in 1 kind, or 2 or more kinds may be used in combination.

The drying can be carried out by a known method such as heating or blowing hot air. The drying conditions are not particularly limited, but drying is performed so that the content of the organic solvent in the resin composition layer is 10 mass% or less, preferably 5 mass% or less. The drying conditions vary depending on the boiling point of the organic solvent in the resin composition or the resin varnish, and for example, when a resin composition or a resin varnish containing 30 to 60 mass% of the organic solvent is used, the resin composition layer can be formed by drying at 50 to 150 ℃ for 3 to 10 minutes.

The resin sheet may be wound into a roll and stored. When the resin sheet has a protective film, the protective film can be peeled off and used.

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

The sheet-like fibrous base material used in the prepreg is not particularly limited, and materials commonly used as a base material for the prepreg, such as glass cloth, aramid nonwoven fabric, and liquid crystal polymer nonwoven fabric, can be used. From the viewpoint of thinning of the printed wiring board, the thickness of the fibrous base material in sheet form is preferably 50 μm or less, more preferably 40 μm or less, further preferably 30 μm or less, particularly preferably 20 μm or less. The lower limit of the thickness of the sheet-like fibrous base material is not particularly limited. Usually 10 μm or more.

The prepreg can be produced by a known method such as a hot melt method or a solvent method.

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

The sheet-like laminate of the present invention can be suitably used for forming an insulating layer of a printed wiring board (for an insulating layer of a printed wiring board), and more suitably used for forming an interlayer insulating layer of a printed wiring board (for an interlayer insulating layer of a printed wiring board).

< printed wiring board >

The printed wiring board of the present invention includes an insulating layer formed of a cured product obtained by curing the resin composition of the present invention.

The printed wiring board can be produced, for example, by a method including the steps (I) and (II) below using the above-described resin sheet;

(I) a step of laminating the resin sheet on the inner substrate so that the resin composition layer of the resin sheet is bonded to the inner substrate, and (II) a step of curing (for example, thermosetting) the resin composition layer to form an insulating layer.

The "inner layer substrate" used in the step (I) is a member to be a substrate of a printed wiring board, and examples thereof include a glass epoxy substrate, a metal substrate, a polyester substrate, a polyimide substrate, a BT resin substrate, a thermosetting polyphenylene ether substrate, and the like. In addition, the substrate may have a conductor layer on one or both surfaces thereof, and the conductor layer may be subjected to patterning. An inner layer substrate having a conductor layer (circuit) formed on one surface or both surfaces of a substrate is sometimes referred to as an "inner layer circuit substrate". In addition, an intermediate manufactured article in which an insulating layer and/or a conductor layer is to be further formed when manufacturing a printed wiring board is also included in the so-called "inner layer substrate" in the present invention. When the printed wiring board is a component-embedded circuit board, an inner layer substrate in which components are embedded may be used.

The lamination of the inner layer substrate and the resin sheet can be performed, for example, by heating and pressure-bonding the resin sheet to the inner layer substrate from the support side. Examples of the member for heat-pressure bonding the resin sheet to the inner layer substrate (hereinafter also referred to as "heat-pressure bonding member") include a heated metal plate (SUS end plate or the like) and a metal roll (SUS roll). It is preferable that the heating and pressure-bonding member is not directly pressed against the resin sheet, but is pressed via an elastic material such as heat-resistant rubber so that the resin sheet sufficiently follows the surface irregularities of the inner layer substrate.

The lamination of the inner substrate and the resin sheet may be performed by a vacuum lamination method. In the vacuum lamination method, the heating and press-bonding temperature is preferably in the range of 60 to 160 ℃, more preferably 80 to 140 ℃, the heating and press-bonding pressure is preferably in the range of 0.098 to 1.77MPa, more preferably 0.29 to 1.47MPa, and the heating and press-bonding time is preferably in the range of 20 to 400 seconds, more preferably 30 to 300 seconds. The lamination is preferably performed under reduced pressure of 26.7hPa or less.

The lamination can be carried out by means of a commercially available vacuum laminator. Examples of commercially available vacuum laminators include a vacuum pressure laminator manufactured by Nikko-Materials, vacuum applicators (vacuum applicators) manufactured by Nikko-Materials, and batch vacuum pressure laminators.

After the lamination, the thermocompression bonding member is pressed at normal pressure (atmospheric pressure), for example, from the support side, whereby the smoothing treatment of the laminated resin sheets can be performed. The pressing conditions for the smoothing treatment may be set to the same conditions as the above-described conditions for the heat and pressure bonding of the laminate. The smoothing treatment may be performed by a commercially available laminator. The lamination and smoothing treatment can be continuously performed using a commercially available vacuum laminator as described above.

The support may be removed between the steps (I) and (II), or may be removed after the step (II).

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

For example, the heat curing conditions of the resin composition layer vary depending on the kind of the resin composition, and in one embodiment, the curing temperature is preferably 120 to 240 ℃, more preferably 150 to 220 ℃, and further preferably 170 to 210 ℃. The curing time may be preferably from 5 minutes to 120 minutes, more preferably from 10 minutes to 100 minutes, and still more preferably from 15 minutes to 100 minutes.

The resin composition layer may be preheated at a temperature lower than the curing temperature before the resin composition layer is thermally cured. For example, before the resin composition layer is thermally cured, the resin composition layer is preheated at a temperature of 50 to 120 ℃, preferably 60 to 115 ℃, more preferably 70 to 110 ℃ for 5 minutes or more, preferably 5 to 150 minutes, more preferably 15 to 120 minutes, further preferably 15 to 100 minutes.

In the production of the printed wiring board, (III) a step of forming a hole in the insulating layer, (IV) a step of roughening the insulating layer, and (V) a step of forming a conductor layer may be further performed. These steps (III) to (V) can be carried out by various methods known to those skilled in the art, which can be used for manufacturing a printed wiring board. When the support is removed after step (II), the support may be removed between step (II) and step (III), between step (III) and step (IV), or between step (IV) and step (V). If necessary, the insulating layer and the conductor layer may be formed by repeating the steps (II) to (V) to form a multilayer wiring board.

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

In the step (III), a hole such as a via hole or a through hole can be formed in the insulating layer by forming the hole in the insulating layer. The step (III) can be performed using, for example, a drill, a laser, plasma, or the like, depending on the composition of the resin composition used for forming the insulating layer. The size and shape of the hole may be determined as appropriate according to the design of the printed wiring board.

The step (IV) is a step of roughening the insulating layer. In general, in this step (IV), stain (smear) is also removed. The step and conditions of the roughening treatment are not particularly limited, and known steps and conditions generally used for forming an insulating layer of a printed wiring board can be used. For example, the roughening treatment may be performed on the insulating layer by sequentially performing a swelling treatment with a swelling liquid, a roughening treatment with an oxidizing agent, and a neutralizing treatment with a neutralizing liquid.

The swelling solution used in the roughening treatment is not particularly limited, and examples thereof include an alkali solution and a surfactant solution, and an alkali solution is preferred, and a sodium hydroxide solution and a potassium hydroxide solution are more preferred. Examples of commercially available Swelling liquids include "spinning Dip securigant P" and "spinning Dip securigant SBU" manufactured by atmott JAPAN (ato ech JAPAN). The swelling treatment with the swelling solution is not particularly limited, and may be performed, for example, by immersing the insulating layer in the swelling solution at 30 to 90 ℃ for 1 to 20 minutes. From the viewpoint of suppressing swelling of the resin of the insulating layer to an appropriate level, it is preferable to immerse the insulating layer in a swelling solution at 40 to 80 ℃ for 5 to 15 minutes.

The oxidizing agent used in the roughening treatment is not particularly limited, and examples thereof include an alkaline permanganic acid solution obtained by dissolving potassium permanganate or sodium permanganate in an aqueous solution of sodium hydroxide. The roughening treatment with an oxidizing agent such as an alkaline permanganate solution is preferably performed by immersing the insulating layer in an oxidizing agent solution heated to 60 to 100 ℃ for 10 to 30 minutes. The concentration of permanganate in the alkaline permanganate solution is preferably 5 to 10% by mass. Examples of commercially available oxidizing agents include alkaline permanganic acid solutions such as "Concentrate Compact CP" and "Dosing Solution securigant P" manufactured by anmant japan.

The neutralizing Solution used for the roughening treatment is preferably an acidic aqueous Solution, and examples of commercially available products include "Reduction Solution securigant P" manufactured by anmant japan co.

The treatment with the neutralizing solution may be performed by immersing the treated surface on which the roughening treatment with the oxidizing agent is performed in the neutralizing solution at 30 to 80 ℃ for 5 to 30 minutes. From the viewpoint of handling and the like, it is preferable to immerse the object subjected to the roughening treatment with the oxidizing agent in a neutralizing solution at 40 to 70 ℃ for 5 to 20 minutes.

In one embodiment, the root mean square roughness (Rq) of the surface of the insulating layer after the roughening treatment is preferably 500nm or less, more preferably 400nm or less, and further more preferably 300nm or less. The lower limit is not particularly limited, and may be, for example, 1nm or more, 2nm or more, or the like. Root mean square roughness (Rq) can be measured using a non-contact surface roughness meter.

Step (V) is a step of forming a conductor layer, and the conductor layer is formed on the insulating layer. The conductor material used in 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, and examples of the alloy layer include layers formed of an alloy of two or more metals selected from the above-mentioned metals (for example, a nickel-chromium alloy, a copper-nickel alloy, and a copper-titanium alloy). Among them, from the viewpoint of versatility of forming a conductor layer, cost, ease of patterning, and the like, a single metal layer of chromium, nickel, titanium, aluminum, zinc, gold, palladium, silver, or copper, or an alloy layer of a nickel-chromium alloy, a copper-nickel alloy, or a copper-titanium alloy is preferable, a single metal layer of chromium, nickel, titanium, aluminum, zinc, gold, palladium, silver, or copper, or an alloy layer of a nickel-chromium alloy is more preferable, and a single metal layer of copper is even more preferable.

The conductor layer may have a single-layer structure, or may have a multilayer structure in which 2 or more layers of single metal layers or alloy layers made of different metals or alloys are stacked. 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 a nickel-chromium alloy.

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

In one embodiment, the conductor layer may be formed by plating. For example, a conductor layer having a desired wiring pattern can be formed by plating the surface of the insulating layer by a conventionally known technique such as a semi-additive method or a full-additive method, and is preferably formed by the semi-additive method from the viewpoint of ease of manufacturing. An example of forming a conductor layer by a semi-additive method is shown below.

First, a plating seed layer is formed on the surface of the insulating layer by electroless plating. Next, a mask pattern for exposing a part of the plating seed layer is formed on the formed plating seed layer in accordance with a desired wiring pattern. On the exposed plating seed layer, a metal layer is formed by electrolytic plating, and then the mask pattern is removed. Then, the unnecessary plating seed layer is removed by etching or the like, and a conductor layer having a desired wiring pattern can be formed.

In other embodiments, the conductor layer may be formed using a metal foil. When the conductor layer is formed using a metal foil, the step (V) is preferably performed between the steps (I) and (II). For example, after the 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 performed by a vacuum lamination method. The conditions for lamination may be the same as those described for the step (I). Next, step (II) is performed to form an insulating layer. Then, a conductor layer having a desired wiring pattern can be formed by a conventionally known technique such as a subtractive (reactive) method or a modified semi-additive method using a metal foil on an insulating layer.

The metal foil can be produced by a known method such as an electrolytic method or a rolling method. As the commercially available products of the metal foil, for example, HLP foil manufactured by JXNissan Metal Co., Ltd, JXUT-III foil, 3EC-III foil manufactured by Mitsui Metal mining Co., Ltd, TP-III foil, and the like can be cited.

< semiconductor device >

The semiconductor device of the present invention includes the printed wiring board of the present invention. The semiconductor device of the present invention can be manufactured using the printed wiring board of the present invention.

Examples of the semiconductor device include various semiconductor devices used in electric products (for example, a computer, a mobile phone, a digital camera, a television, and the like), vehicles (for example, a motorcycle, an automobile, a train, a ship, an aircraft, and the like), and the like.

Examples

The present invention will be described in detail with reference to examples. The present invention is not limited by these examples. In the following, unless otherwise explicitly stated, "parts" and "%" representing amounts mean "parts by mass" and "% by mass", respectively. The temperature condition in the case where the temperature is not particularly specified is room temperature (25 ℃).

< example 1 >

10 parts of an amine compound having a biphenyl skeleton (BAN, manufactured by Nippon Kagaku K.K.), 20 parts of an aliphatic maleimide compound (BMI-689, manufactured by Designer Molecules Co., Ltd.), 28.6 parts of an aromatic maleimide compound (MIR-3000-70 MT, manufactured by Nippon Kagaku K.K., a MEK/toluene mixed solution having a solid content of 70%), 1 part of an imidazole-based curing accelerator ("1B 2 PZ" manufactured by mitsui chemical industry co., ltd., 1-benzyl-2-phenylimidazole), 60 parts of a spherical silica (SO-C2 "manufactured by yokohama chemical industry co., ltd., average particle diameter of 0.5 μm, specific surface area of 5.8 m) surface-treated with a silane coupling agent (" KBM-573 ", N-phenyl-3-aminopropyltrimethoxysilane).²And/g) and uniformly dispersed by a high-speed rotary mixer to prepare a resin composition.

< example 2 >

A resin composition was prepared in the same manner as in example 1, except that 20 parts of an aliphatic maleimide compound ("BMI-1500" manufactured by Designer polymers) was used in place of 20 parts of the aliphatic maleimide compound ("BMI-689" manufactured by Designer polymers).

< example 3 >

A resin composition was prepared in the same manner as in example 1, except that 20 parts of an aliphatic maleimide compound ("BMI-2500" manufactured by Designer polymers) was used in place of 20 parts of the aliphatic maleimide compound ("BMI-689" manufactured by Designer polymers).

< example 4 >

A resin composition was prepared in the same manner as in example 1 except that 20 parts of an aliphatic maleimide compound ("BMI-3000J" manufactured by Designer polymers) was used in place of 20 parts of the aliphatic maleimide compound ("BMI-689" manufactured by Designer polymers).

< example 5 >

A resin composition was prepared in the same manner as in example 2, except that 20 parts of an aromatic maleimide compound ("BMI-6100" manufactured by Designer Molecules) was used in place of 28.6 parts of the aromatic maleimide compound ("MIR-3000-70 MT" manufactured by Nippon Kagaku K.K.).

< example 6 >

A resin composition was prepared in the same manner as in example 3, except that 20 parts of an aromatic maleimide compound ("BMI-6100" manufactured by Designer Molecules) was used in place of 28.6 parts of the aromatic maleimide compound ("MIR-3000-70 MT" manufactured by Nippon Kagaku K.K.).

< example 7 >

A resin composition was prepared in the same manner as in example 2, except that the amount of the aromatic maleimide compound (MIR-3000-70 MT manufactured by Nippon chemical Co., Ltd., "MEK/toluene mixed solution having a solid content of 70%) was changed from 28.6 parts to 14.3 parts, and 10 parts of the aromatic maleimide compound (BMI-6100 manufactured by Designer Molecules) was used.

< example 8 >

An MEK solution (70 mass% of nonvolatile content) of a maleimide compound a (Mw/Mn ═ 1.81, v ″ -1.47 (mainly 1,2, or 3)) represented by the following formula (X) synthesized by the method described in synthesis example 1 of japanese patent application publication No. 2020-500211 was prepared.

[ chemical formula 23]

A resin composition was prepared in the same manner as in example 2, except that 28.6 parts of an aromatic maleimide compound (maleimide compound A represented by formula (X), MEK solution with a solid content of 70% by mass) was used in place of 28.6 parts of the aromatic maleimide compound (MEK/toluene mixed solution with a solid content of 70% "MIR-3000-70 MT", manufactured by Nippon Kabushiki Kaisha).

< example 9 >

A resin composition was prepared in the same manner as in example 2, except that the amount of spherical silica (SO-C2, manufactured by Yadmax, K.K.) surface-treated with a silane coupling agent ("KBM-573", N-phenyl-3-aminopropyltrimethoxysilane) was changed from 60 parts to 70 parts, and 15.4 parts of vinylbenzyl-modified polyphenylene ether (OPE-2 St2200, manufactured by Mitsubishi gas chemical, 65% solids in toluene) was used.

< example 10 >

A resin composition was prepared in the same manner as in example 2, except that the amount of spherical silica (SO-C2, manufactured by Yttrium corporation) surface-treated with a silane coupling agent ("KBM-573", N-phenyl-3-aminopropyltrimethoxysilane) was changed from 60 parts to 70 parts, and 20 parts of methacrylic acid-modified polyphenylene ether (obtained by dissolving SA9000-111, manufactured by Sabourne Seikaga Innovative plastics Co., Ltd., in a toluene solution having a solid content of 50%) was used.

< example 11 >

A resin composition was prepared in the same manner as in example 2, except that the amount of spherical silica (SO-C2, manufactured by Yttrium corporation) surface-treated with a silane coupling agent ("KBM-573", N-phenyl-3-aminopropyltrimethoxysilane) was changed from 60 parts to 70 parts, and 15.4 parts of a divinylbenzene/styrene copolymer (ODV-XET-X04, manufactured by Nikko chemical Co., Ltd., 65% in solid content in toluene) was used.

< comparative example 1 >

A resin composition was prepared in the same manner as in example 1, except that 20 parts of an aliphatic maleimide compound ("BMI-689" manufactured by Designer Molecies) was not used, and the amount of the aromatic maleimide compound ("MIR-3000-70 MT" manufactured by Nippon Kabushiki Kaisha, MEK/toluene mixed solution having a solid content of 70%) was changed from 28.6 parts to 57.1 parts.

< comparative example 2 >

A resin composition was prepared in the same manner as in example 1, except that the amount of the aliphatic maleimide compound ("BMI-689" manufactured by Designer Molecies) was changed from 20 parts to 10 parts, and 10 parts of an amine compound having no biphenyl skeleton ("A-A" manufactured by Nippon Kasei corporation) was used instead of 10 parts of an amine compound having a biphenyl skeleton ("BAN" manufactured by Nippon Kasei corporation).

< test example 1: measurement of relative dielectric constant (Dk) and dielectric loss tangent (Df) >

As the support, a polyethylene terephthalate film (AL 5, manufactured by Linekeko Co., Ltd., thickness: 38 μm) provided with a release layer was prepared. The resin compositions obtained in examples and comparative examples were uniformly applied to the release layer of the support so that the thickness of the resin composition layer after drying became 40 μm. Then, the resin composition was dried at 80 to 100 ℃ (average 90 ℃) for 4 minutes to obtain a resin sheet a including a support and a resin composition layer.

The resulting resin sheet A was cured in an oven at 190 ℃ for 90 minutes. The resin sheet a was taken out of the oven, and the support was peeled off from the resin sheet a, whereby a cured product of the resin composition layer was obtained. The cured product was cut into a length of 80mm and a width of 2mm to obtain a cured product B for evaluation.

The evaluation of cured product B, using Agilent Technologies "HP 8362B", by resonant cavity perturbation method to determine the frequency of 5.8GHz, measurement temperature 23 ℃ under the conditions of dielectric constant value (Dk value) and dielectric loss tangent value (Df value). The measurement was performed on 2 test pieces, and the average value was calculated.

< test example 2: measurement of peeling Strength and arithmetic average roughness (Ra) >

(1) Preparation of inner layer substrate

Both surfaces of a glass cloth substrate epoxy resin double-sided copper-clad laminate (copper foil 18 μm thick, substrate 0.4mm thick, "R1515A" manufactured by songhua corporation) on which an inner layer circuit was formed were subjected to roughening treatment of the copper surface by etching 1 μm with a microetching agent ("CZ 8101" manufactured by Mege (MEC) corporation).

(2) Lamination of resin sheet A

The resin sheet a obtained in test example 1 was laminated on both surfaces of the inner substrate using a batch vacuum press Laminator (2-Stage build up Laminator (CVP 700), manufactured by Nikko Materials co., ltd.) so that the resin composition layer was in contact with the inner substrate. The lamination was carried out by: the pressure was reduced for 30 seconds to 13hPa or less, and then the pressure was bonded at 120 ℃ and 0.74MPa for 30 seconds. Next, hot pressing was performed at 100 ℃ for 60 seconds under a pressure of 0.5 MPa.

(3) Thermal curing of resin composition layers

Then, the inner substrate laminated with the resin sheet a was put into an oven at 130 ℃ and heated for 30 minutes, and then, was moved to an oven at 190 ℃ and heated for 30 minutes, whereby the resin composition layer was thermally cured to form an insulating layer. Then, the support was peeled off to obtain a cured substrate a having the insulating layer, the interlayer substrate, and the insulating layer in this order.

(4) Roughening treatment

For the cured substrate a, desmear treatment as roughening treatment was performed. As the desmear treatment, the following wet desmear treatment was performed.

(Wet desmutting treatment)

The cured substrate a was immersed in a Swelling solution ("spinning Dip SecuriganthP" manufactured by anmet japan corporation, an aqueous solution of diethylene glycol monobutyl ether and sodium hydroxide) at 60 ℃ for 5 minutes, and then immersed in an oxidizing agent solution ("concentration Compact CP" manufactured by anmet japan corporation, an aqueous solution having a potassium permanganate concentration of about 6% and a sodium hydroxide concentration of about 4%) at 80 ℃ for 20 minutes. Next, the plate was immersed in a neutralizing Solution ("Reduction Solution Securigint P" manufactured by Anmet Japan K.K., aqueous sulfuric acid Solution) at 40 ℃ for 5 minutes, and then dried at 80 ℃ for 15 minutes.

(5) Measurement of arithmetic average roughness (Ra) of roughened insulating layer surface

The arithmetic mean roughness (Ra) of the insulating layer surface of the cured substrate A after the roughening treatment was determined from the value obtained by using a non-contact surface roughness meter (WYKO NT3300 manufactured by Bruker Co., Ltd.) and a measurement range of 121 μm × 92 μm using a VSI mode and a 50-fold lens. The average value of 10 points was obtained for each measurement.

(6) Formation of conductor layer

A conductor layer was formed on the roughened surface of the insulating layer of the cured substrate A by a semi-additive method. That is, the roughened substrate is made to contain PdCl₂The electroless copper plating solution of (3) was immersed at 40 ℃ for 5 minutes, and then immersed at 25 ℃ for 20 minutes in an electroless copper plating solution. Subsequently, the substrate was heated at 150 ℃ for 30 minutes, annealed, and then formed into a resist layer, and patterned by etching. Then, copper sulfate electrolytic plating was performed to form a conductor layer having a thickness of 25 μm, and annealing treatment was performed at 190 ℃ for 60 minutes. The resulting substrate was referred to as "evaluation substrate B".

(7) Measurement of peel Strength of plated conductor layer

The peel strength between the insulating layer and the conductive layer was measured in accordance with japanese industrial standards (JISC 6481). Specifically, a part of the conductor layer of the evaluation substrate B having a width of 10mm and a length of 100mm was cut to form a cut, one end of the cut was peeled off and clamped by a jig, and the load (kgf/cm) at which the test substrate was peeled off at a speed of 50 mm/min in the vertical direction by 35mm was measured at room temperature to determine the peel strength. A tensile tester ("AC-50C-SL" manufactured by TSE Co., Ltd.) was used for the measurement.

The amounts of nonvolatile components used in the resin compositions of examples and comparative examples and the results of the test examples are shown in table 1 below.

[ Table 1]

As is clear from the above, by using a resin composition containing (a) an amine compound having a biphenyl skeleton, (B) a maleimide compound having an aliphatic chain having 7 or more carbon atoms, and (C) a maleimide compound having no aliphatic chain having 7 or more carbon atoms, a cured product having a low relative permittivity (Dk) and a low dielectric loss tangent (Df) and excellent peel strength of a plated conductor layer can be obtained.

Claims

1. A resin composition comprising:

(A) amine compound having biphenyl skeleton,

(B) Maleimide compound having aliphatic chain having 7 or more carbon atoms, and

(C) a maleimide compound having no aliphatic chain having 7 or more carbon atoms.

2. The resin composition according to claim 1, wherein the component (B) has: a maleimide group directly bonded to a carbon atom not constituting an aromatic ring.

3. The resin composition according to claim 1, wherein the (C) component has: a maleimide group directly bonded to a carbon atom constituting the aromatic ring.

4. The resin composition according to claim 1, wherein the component (A) has a primary amino group.

5. The resin composition according to claim 1, wherein the (a) component has: an amino group directly bonded to a carbon atom constituting an aromatic ring.

6. The resin composition according to claim 1, wherein,

7. The resin composition according to claim 1, wherein the content of the component (A) is 3 to 40% by mass, based on 100% by mass of nonvolatile components in the resin composition.

8. The resin composition according to claim 1, wherein the content of the component (B) is 3 to 40% by mass, based on 100% by mass of nonvolatile components in the resin composition.

9. The resin composition according to claim 1, wherein the content of the component (C) is 3 to 40% by mass, based on 100% by mass of nonvolatile components in the resin composition.

10. The resin composition according to claim 1, wherein the mass ratio of component (C) to component (B), (component (C)/component (B)), is 0.5 to 20.

11. The resin composition according to claim 1, wherein the mass ratio of component (A) to the total of components (B) and (C), (the total of component (A)/component (B) and component (C)), is 0.1 to 0.5.

12. The resin composition according to claim 1, further comprising (D) a radically polymerizable compound other than the components (B) and (C).

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

14. The resin composition according to claim 13, wherein the content of the component (E) is 25% by mass or more, assuming that the nonvolatile content in the resin composition is 100% by mass.

15. The resin composition according to claim 1, wherein a cured product of the resin composition has a dielectric loss tangent of 0.004 or less as measured at 5.8GHz and 23 ℃.

16. The resin composition according to claim 1, wherein a cured product of the resin composition has a relative dielectric constant of 2.9 or less, as measured at 5.8GHz and 23 ℃.

17. A cured product of the resin composition according to any one of claims 1 to 16.

18. A sheet-like laminate comprising the resin composition according to any one of claims 1 to 16.

19. A resin sheet having:

support body, and

a resin composition layer formed of the resin composition according to any one of claims 1 to 16, provided on the support.

20. A printed wiring board comprising an insulating layer formed from a cured product of the resin composition according to any one of claims 1 to 16.

21. A semiconductor device comprising the printed wiring board of claim 20.