resin composition

Abstract

This invention provides a resin composition that yields a cured product with low specific capacitance (Dk) and dielectric tangent (Df), and excellent peel strength of the electroplated conductor layer. The resin composition comprises (A) an amine compound having a biphenyl backbone, (B) a maleimine compound having an aliphatic chain with 7 or more carbon atoms, and (C) a maleimine compound without an aliphatic chain with 7 or more carbon atoms.

Description

Technical Field

[0001] This invention relates to resin compositions containing maleimide. Furthermore, it relates to cured products, sheet-like laminates, resin films, printed circuit boards, and semiconductor devices obtained using these resin compositions. Prior Technology

[0002] As a manufacturing technology for printed circuit boards, a build-up method, in which insulating and conductor layers are alternately deposited, is known. In build-up methods, the insulating layer is generally formed by curing a resin composition. In recent years, there has been a demand for further improvements in the dielectric constant and dielectric tangent of the insulating layer, as well as the peel strength of the electroplated conductor layer.

[0003] To date, various maleimide compounds are known (Patent Documents 1-3). [Previous Technical Documents] [Patent Literature]

[0004] [Patent Document 1] Japanese Patent Application Publication No. 2019-203122 [Patent Document 2] International Publication No. 2018 / 212116 [Patent Document 3] International Publication No. 2020 / 045489 Summary of the Invention

[0005] [The problem that the invention aims to solve]

[0006] The objective of this invention is to provide a resin composition that yields a hardened material with low specific capacitance (Dk) and dielectric tangent (Df) and excellent peel strength of the electroplated conductor layer. [Methods used to solve problems]

[0007] In order to achieve the objectives of this invention, the inventors carefully examined the materials and unexpectedly discovered that by using a resin composition comprising (A) an amine compound having a biphenyl skeleton, (B) a maleimine compound having an aliphatic chain having 7 or more carbon atoms, and (C) a maleimine compound not having an aliphatic chain having 7 or more carbon atoms, they could obtain a hardened material with low specific capacitance (Dk) and dielectric tangent (Df) and excellent peel strength of the electroplated conductor layer, thus completing this invention.

[0008] That is, the present invention includes the following contents. [1] A resin composition comprising (A) an amine compound having a biphenyl skeleton, (B) Maleimine compounds having aliphatic chains with 7 or more carbon atoms, and (C) Maleimine compounds that do not have aliphatic chains with 7 or more carbon atoms. [2] As described in [1] above, component (B) has maleimine groups directly bonded to carbon atoms that do not form an aromatic ring. [3] The resin composition as described in [1] or [2] above, wherein component (C) has maleimide groups directly bonded to the carbon atoms constituting the aromatic ring. [4] The resin composition of any one of [1] to [3] above, wherein component (A) has a primary amine group. [5] The resin composition of any one of [1] to [4] above, wherein component (A) has an amine group directly bonded to the carbon atom constituting the aromatic ring. [6] A resin composition as described in any of [1] to [5] above, wherein component (A) comprises having formula (A1):

[0009]

[0010] [In the formula, V and W independently represent -C(R')2-, -O-, and -O-, respectively.] -CO-, -S-, -SO-, -SO2-, -CONH-, or -NHCO-, R each independently represents a substituent, R' each independently represents a hydrogen atom or substituent, h, i, and j each independently represent an amine compound represented by an integer from 0 to 2. [7] For any of the resin compositions in [1] to [6] above, when the non-volatile component in the resin composition is set to 100% by mass, the content of component (A) is 3% to 40% by mass. [8] For any of the resin compositions in [1] to [7] above, when the non-volatile component in the resin composition is set to 100% by mass, the content of component (B) is 3% to 40% by mass. [9] For any of the resin compositions in [1] to [8] above, when the non-volatile component in the resin composition is set to 100% by mass, the content of component (C) is 3% to 40% by mass.

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

[11] The resin composition of any of the above [1] to

[10] has a mass ratio of component (A) to the total of components (B) and (C) (component (A) / total of components (B) and (C)) of 0.1 to 0.5.

[12] The resin composition of any of the above [1] to

[11] further includes (D) free radical polymeric compound other than component (B) and component (C).

[13] The resin composition of any of the above [1] to

[12] further includes (E) inorganic filler.

[14] As in the resin composition described in

[13] above, when the non-volatile component in the resin composition is set to 100% by mass, the content of component (E) is 25% by mass or more.

[15] The resin composition of any one of [1] to

[14] above, wherein the dielectric tangent of the cured resin composition is less than 0.004 when measured at 5.8 GHz and 23 °C.

[16] The resin composition of any one of [1] to

[15] above, wherein the specific capacitance of the cured resin composition is 2.9 or less when measured at 5.8 GHz and 23 °C.

[17] A hardened material, which is a hardened material of the resin composition of any one of [1] to

[16] above.

[18] A sheet-like laminated material comprising a resin composition as described in any one of [1] to

[16] above.

[19] A resin sheet having a support and a resin composition layer formed on the support by any of the resin compositions described in [1] to

[16] above.

[20] A printed wiring board having an insulating layer made of a hardened resin composition of any one of [1] to

[16] above.

[21] A semiconductor device comprising the printed wiring board of

[20] described above. [Invention Effects]

[0011] When the resin composition according to the present invention is obtained, a hardened material with low specific capacitance (Dk) and dielectric tangent (Df) and excellent peel strength of the electroplated conductor layer can be obtained. [Forms of Invention Implementation]

[0012] The present invention will now be described in detail based on preferred embodiments. However, the present invention is not limited to the embodiments and examples described below, and may be modified in any way without departing from the scope of the claims of the present invention and their equivalents.

[0013] <Resin Composition> The resin composition of this invention comprises (A) an amine compound having a biphenyl backbone, (B) a maleimine compound having aliphatic chains with 7 or more carbon atoms, and (C) a maleimine compound without aliphatic chains with 7 or more carbon atoms. By using this resin composition, a cured product with low specific capacitance (Dk) and dielectric tangent (Df) and excellent peel strength of the electroplated conductor layer can be obtained.

[0014] In addition to (A) an amine compound having a biphenyl skeleton, (B) a maleimine compound having a fatty chain with 7 or more carbon atoms, and (C) a maleimine compound without a fatty chain having 7 or more carbon atoms, the resin composition of the present invention may further contain any other components. Examples of such components include (D) any free radical polymerizable compound, (E) inorganic filler, (F) curing accelerator, (G) other additives, and (H) organic solvent. The components contained in the resin composition will be described in detail below.

[0015] <(A) Amine compounds with a biphenyl skeleton> The resin composition of this invention contains (A) an amine compound having a biphenyl skeleton. Component (A) can be used alone or in combination of two or more. In one embodiment, the amino groups contained in component (A) can undergo addition reactions with components (B) and (C) (and component (D) when included). In one embodiment, component (A) preferably has two or more amino groups per molecule, more preferably three or more amino groups. Component (A) can have any one of a primary, secondary, or tertiary amino group; in one embodiment, it preferably has a primary amino group. In one embodiment, component (A) preferably has an amino group (aromatic amino group) directly bonded to a carbon atom constituting an aromatic ring as an amino group, more preferably a primary aromatic amino group, and most preferably, the amino groups contained in component (A) are only primary aromatic amino groups.

[0016] In one embodiment, component (A) preferably includes formula (A1):

[0017]

[0018] [In the formula, V and W independently represent -C(R')2-, -O-, and -O-, respectively.] -CO-, -S-, -SO-, -SO2-, -CONH-, or -NHCO- (preferably) -C(R')2 -), R each independently represents a substituent, R' each independently represents a hydrogen atom or a substituent (preferably a hydrogen atom), h, i, and j each independently represent an integer from 0 to 2 (preferably 0) representing a repeating unit of an amine compound. Furthermore, the h, i, and j units may be the same or different.

[0019] In this specification, there is no particular limitation on the substituents. Examples of monovalent substituents include alkyl, alkenyl, aryl, alkyl-aryl (aryl group substituted with one or more alkyl groups), aryl-aryl (aryl group substituted with one or more aryl groups), aryl-alkyl (alkyl group substituted with one or more aryl groups), alkyl-oxy, alkenyl-oxy, aryl-oxy, alkyl-carbonyl, alkenyl-carbonyl, aryl-carbonyl, alkyl-oxy-carbonyl, alkenyl-oxy-carbonyl, aryl-oxy-carbonyl, alkyl-carbonyl-oxy, alkenyl-carbonyl-oxy, aryl-carbonyl-oxy, alkyl-carbonyl-oxy, alkenyl-carbonyl-oxy, aryl-carbonyl-oxy, etc. When substitution is possible, divalent substituents such as side oxygen (=O) may also be included.

[0020] Alkyl groups refer to monovalent saturated hydrocarbon groups that are straight-chain, branched, and / or cyclic. There is no particular limitation on the number of carbon atoms, but it is preferred to have 1 to 14 carbon atoms, more preferably 1 to 10 carbon atoms, and even more preferably 1 to 6 or 4 to 10 carbon atoms. Examples of alkyl groups include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, cyclopentyl, cyclohexyl, methylcyclohexyl, dimethylcyclohexyl, trimethylcyclohexyl, cyclopentylmethyl, and cyclohexylmethyl. Alkenyl groups refer to monovalent aliphatic unsaturated hydrocarbon groups that have at least one carbon-carbon double bond and are straight-chain, branched, and / or cyclic. The alkenyl group is not particularly limited, but it is preferably composed of 2 to 14 carbon atoms, more preferably 2 to 10 carbon atoms, and even more preferably 2 to 6 or 4 to 10 carbon atoms. Examples of alkenyl groups include vinyl, propenyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, and cyclohexenyl. The aryl group refers to a monovalent aromatic hydrocarbon group. The aryl group is preferably composed of 6 to 14 carbon atoms. Examples of aryl groups include phenyl, 1-naphthyl, and 2-naphthyl.

[0021] (A) The weight-average molecular weight (Mw) of the component is preferably 300 to 4000, more preferably 300 to 3000, and even more preferably 300 to 2000. (A) The weight-average molecular weight of the component can be determined by gel permeation chromatography (GPC) using a polystyrene equivalent.

[0022] The functional group equivalent of the amino group in component (A) is preferably 100 g / eq. to 1000 g / eq., more preferably 100 g / eq. to 500 g / eq. The functional group equivalent of the amino group in component (A) is the mass of component (A) equal to 1 amino group.

[0023] (A) Specific examples of the components can be listed, for example, those with formula (A2):

[0024]

[0025] Amine compounds represented by repeating units.

[0026] (A) Commercially available products containing this ingredient include, for example, "BAN" (an amine compound of formula (A2) above) manufactured by Nippon Kayaku Co., Ltd.

[0027] The content of component (A) in the resin composition is not particularly limited. When the non-volatile component in the resin composition is set to 100% by mass, it is preferably 60% by mass or less, more preferably 50% by mass or less, even more preferably 40% by mass or less, even more preferably 30% by mass or less, and most preferably 25% by mass or less. The lower limit of the content of component (A) in the resin composition is not particularly limited. When the non-volatile component in the resin composition is set to 100% by mass, it is preferably 0.1% by mass or more, more preferably 1% by mass or more, even more preferably 3% by mass or more, even more preferably 5% by mass or more, and most preferably 7% by mass or more.

[0028] <(B) Maleimine compounds with aliphatic chains having 7 or more carbon atoms> The resin composition of this invention contains (B) a maleimine compound having an aliphatic chain with 7 or more carbon atoms. Component (B) can be used alone or in combination of two or more. A maleimine compound refers to an organic compound containing at least one (preferably two or more) maleimine group (2,5-dihydro-2,5-dioxo-1H-pyrrole-1-yl) in one molecule. In one embodiment, component (B) is preferably a maleimine group directly bonded to carbon atoms that do not form an aromatic ring, and the maleimine group contained in component (B) is particularly preferably a maleimine group directly bonded only to carbon atoms that do not form an aromatic ring.

[0029] Aliphatic chains refer to aliphatic chains in which the skeletal atoms are linked by single, double, or triple bonds, preferably aliphatic chains in which the skeletal atoms are linked by single or double bonds, and particularly preferably aliphatic chains in which the skeletal atoms are linked only by single bonds. Furthermore, aliphatic chains may have branches, but do not form part or all of a ring structure.

[0030] The aliphatic chain can be an aliphatic carbon chain with only carbon atoms as the backbone atoms (e.g., alkyl chains, alkenyl chains, etc.). Besides carbon atoms, it can also be aliphatic chains containing heteroatoms, such as oxygen, nitrogen, and sulfur atoms, as the backbone atoms (e.g., polyepoxide chains, polyalkylimide chains, etc.). In one embodiment, an aliphatic carbon chain with only carbon atoms as the backbone atoms is preferred. There is no particular limit to the upper limit of the number of carbon atoms in the backbone of this aliphatic chain; for example, it can be less than 3000, less than 1000, less than 100, less than 50, etc. For aliphatic chains with 7 or more carbon atoms, it is preferable that the main chain of the aliphatic chain has 7 or more carbon atoms.

[0031] In one embodiment, the maleic anhydride compound of component (B) is preferably of formula (B1):

[0032]

[0033] [In the formula, A1 independently represents a divalent organic group with an aliphatic chain having 7 or more carbon atoms, A2 independently represents a divalent organic group without an aliphatic chain having 7 or more carbon atoms, B1 independently represents a tetravalent organic group with an aromatic ring and / or a non-aromatic ring, n1 and n2 represent integers of 0 or more (preferably integers from 0 or 1 to 100), m1 and m2 represent either one being 1 and the others being 0, and the sum of n1 and m1 is 1 or more.] This refers to maleimide compounds. Furthermore, the order and arrangement of the n1 and n2 units are arbitrary, including cross-linked copolymers, block copolymers, random copolymers, etc. Also, the n1 and n2 units can be the same or different.

[0034] Aromatic rings refer to rings that conform to Hückel's rule, which states that the number of electrons in the π-electron system of the ring is 4n+2 (where n is a natural number). Aromatic rings can be carbon rings with carbon atoms as the ring constituent atoms, or heterocycles containing oxygen, nitrogen, sulfur, or other heteroatoms besides carbon atoms as ring constituent atoms. In most embodiments, carbon rings are preferred. Aromatic rings include not only monocyclic aromatic rings and condensed rings formed by the condensation of two or more monocyclic aromatic rings, but also condensed rings formed by the condensation of one or more monocyclic non-aromatic rings on one or more monocyclic aromatic rings. Specific examples of aromatic rings include benzene rings, naphthalene rings, anthracene rings, indene rings, fumonisin rings, and tetrahydronaphthalene rings.

[0035] Non-aromatic rings refer to rings other than aromatic rings. Non-aromatic rings can be carbon rings or heterocyclic rings; in one embodiment, a carbon ring is preferred. Non-aromatic rings can be saturated or unsaturated; in one embodiment, a saturated ring is preferred. Non-aromatic rings include monocyclic non-aromatic rings such as cycloalkanes and cycloalkenes, and condensed non-aromatic rings formed by the condensation of two or more monocyclic non-aromatic rings such as cross-linked hydrocarbon rings. Cycloalkanes are monocyclic aliphatic saturated hydrocarbon rings, such as cyclobutane, cyclopentane, cyclohexane, cycloheptane, and cyclooctane rings with 3 to 8 carbon atoms. Cycloalkenes are monocyclic aliphatic unsaturated hydrocarbon rings having at least one carbon-carbon double bond, such as cyclobutene, cyclopentene, cyclohexene, cycloheptene, cyclooctene, cyclopentadiene, and cyclohexadiene rings with 4 to 8 carbon atoms. Cross-linked hydrocarbon rings are non-aromatic rings composed of two or more rings with two or more atoms in total. Examples include norbornene rings, decahydronaphthalene rings, adamantane rings, and tetrahydrodicyclopentadiene rings, which are cross-linked hydrocarbon rings with 8 to 15 carbon atoms.

[0036] 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, even more preferably 1.5 or less, and especially preferably 1.2 or less.

[0037] A1 represents a divalent organic group with an aliphatic chain having 7 or more carbon atoms. The skeleton atoms of the "divalent organic group" represented by A1 can be selected from carbon atoms, oxygen atoms, nitrogen atoms, and sulfur atoms. There is no particular limitation on the number of skeleton atoms, such as less than 3000, less than 1000, less than 100, less than 50, etc.

[0038] In one embodiment, each divalent group is preferably obtained by removing two amino groups from a dimer diamine. A dimer diamine refers to a compound in which two terminal carboxyl groups (-COOH) of a dimer acid are replaced with amino groups or aminomethyl groups, and it has an aliphatic carbon chain with 7 or more carbon atoms. The dimer acid is, for example, a dimer of an unsaturated fatty acid (preferably an unsaturated fatty acid with 11 to 22 carbon atoms, particularly an unsaturated fatty acid with 18 carbon atoms such as oleic acid and linolenic acid) or its hydrogenation.

[0039] In other embodiments, A1 is preferably a non-aromatic hydrocarbon group with a divalent aliphatic carbon chain having 7 or more carbon atoms, and more preferably is formula (b1):

[0040]

[0041] [In the formula, Y1 independently represents a straight-chain or branched (preferably straight-chain) alkyl group with 7 or more atoms (preferably the number of atoms in the alkyl main chain), or a straight-chain or branched (preferably straight-chain) alkyl group with 7 or more atoms (preferably the number of atoms in the alkenyl main chain) (preferably straight-chain); cyclo(Zy1) represents a cycloalkane ring that may have a group selected from alkyl and alkenyl groups, or a cycloalkenyl ring that may have a group selected from alkyl and alkenyl groups (preferably a cyclohexane ring that may have an alkyl group); d represents 0 or 1 (preferably 1); * represents the bonding site] The 2-valent base is represented.

[0042] Alkenyl groups refer to divalent saturated hydrocarbon groups, and are straight-chain or branched alkenyl groups with 7 or more carbon atoms, for example, 7 to 200, preferably 7 to 100, and more preferably 7 to 50. Alkenyl groups refer to divalent aliphatic unsaturated hydrocarbon groups having at least one carbon-carbon double bond, and are straight-chain or branched alkenyl groups with 7 or more carbon atoms, for example, 7 to 200, preferably 7 to 100, and more preferably 7 to 50.

[0043] Specific examples of the divalent base represented by equation (b1) can be listed below:

[0044]

[0045] [In the formula, * indicates the bonding location].

[0046] A2 independently represents a divalent organic group that does not have an aliphatic chain with 7 or more carbon atoms (that is, when it has an aliphatic chain, the most carbon-containing aliphatic chain in that aliphatic group has 6 or fewer carbon atoms). The skeleton atoms of the "divalent organic group" represented by A2 can be selected from carbon, oxygen, nitrogen, and sulfur atoms, and the number of skeleton atoms is not particularly limited, for example, it can be 5~3000, 5~1000, 5~100, 5~50, etc. A2 can be, for example, a divalent group obtained by removing two amino groups from a diamine compound that does not have an aliphatic chain with 7 or more carbon atoms, which is commonly used as a raw material for polyimide, but there is no particular limitation.

[0047] A2 is preferably independent of each other and does not have an aliphatic chain with 7 or more carbon atoms, and has an aromatic ring and / or a non-aromatic ring divalent organogroup (that is, when it has an aliphatic chain, the aliphatic chain with the most carbon atoms has 6 or less carbon atoms, and has an aromatic ring and / or a non-aromatic ring divalent organogroup), more preferably formula (b2):

[0048]

[0049] [In the formula, Y21 independently represents a single bond, or -C(Rx)2- (preferably -C(Rx)2-); Y22 independently represents a single bond, -C(Ry)2-, -O-, -CO-, -S-, -SO-, -SO2-, -CONH-, or -NHCO- (preferably -C(Ry)2- or -O-); Rx and Ry each independently represent a hydrogen atom, methyl, ethyl, or phenyl (preferably a hydrogen atom); each of the rings Zy2 independently represents a non-aromatic ring having an alkyl or phenyl group selected from 1 to 6 carbon atoms, or an aromatic ring having an alkyl or phenyl group selected from 1 to 6 carbon atoms; e represents an integer of 0 or more (preferably an integer of 0 or 1 to 5); * represents a divalent group representing a bonding site. Furthermore, the units of e can be the same or different.

[0050] Specific examples of the divalent base represented by equation (b2) can be listed below:

[0051]

[0052] [In the formula, * indicates the bonding location].

[0053] B1 independently represents a tetravalent organic group having an aromatic ring and / or a non-aromatic ring. The skeletal atoms of the "tetravalent organic group" represented by B1 are, for example, selected from carbon, oxygen, nitrogen, and sulfur atoms. The number of skeletal atoms is not particularly limited, and can be, for example, 5~3000, 5~1000, 5~100, 5~50, etc. B1 can be, for example, a tetravalent group obtained by removing two anhydride groups (-CO-O-CO-) from a tetracarboxylic anhydride having an aromatic ring and / or a non-aromatic ring, which is commonly used as a raw material for polyimide, but there is no particular limitation.

[0054] B1 is preferably independent of each other and does not have an aliphatic chain with 7 or more carbon atoms, and has an aromatic ring and / or a tetravalent organogroup of non-aromatic ring (that is, when it has an aliphatic chain, the aliphatic chain with the most carbon atoms has 6 or less carbon atoms, and has an aromatic ring and / or a tetravalent organogroup of non-aromatic ring), more preferably formula (b3):

[0055]

[0056] In the formula, R1 independently represents an alkyl or phenyl group with 1 to 6 carbon atoms; X1 independently represents a single bond, -C(Rz)2-, -O-, -CO-, -S-, -SO-, -SO2-, -CONH-, or -NHCO- (preferably -C(Rz)2- or -O-); Rz each independently represents a hydrogen atom, methyl, ethyl, or phenyl (preferably a hydrogen atom); ring Zx1 each independently represents a non-aromatic ring selected from alkyl and phenyl groups having 1 to 6 carbon atoms, or an aromatic ring selected from alkyl and phenyl groups having 1 to 6 carbon atoms; a each independently represents an integer from 0 to 2 (preferably 0); b represents 0 or 1; c represents an integer greater than 0 or 1 (preferably an integer from 0 or 1 to 5); * indicates a bonding site] The four-valent base is represented. Also, the a-unit and c-unit can be the same or different.

[0057] Specific examples of the four-valent base represented by equation (b3) can be listed below:

[0058]

[0059] [In the formula, * indicates the bonding location].

[0060] In one embodiment, the maleic anhydride compound of component (B) is preferably of formula (B2):

[0061]

[0062] [In the formula, the symbols are the same as those in formulas (B1), (b1), (b2), and (b3)] The compound represented (where the n1 unit and the n2 unit are bonded) is more preferably represented by formula (B3):

[0063]

[0064] [In the formula, the symbols are the same as those in formulas (B1), (b2), and (b3)] The compound is represented by a bond between the n1 unit and the n2 unit.

[0065] (B) Specific examples of the components can be listed as follows: (B4-1) to (B4-5):

[0066]

[0067] [In the formula, n1' and n2' each independently represent an integer from 1 to 20 (preferably an integer from 1 to 10)] The term refers to maleimine compounds. Furthermore, the order and arrangement of the n1' and n2' units are arbitrary, including cross-linked copolymers, block copolymers, random copolymers, etc.

[0068] (B) The weight-average molecular weight (Mw) of the component is not particularly limited, but is preferably 200 to 50,000, more preferably 300 to 40,000, and even more preferably 400 to 20,000. (B) The weight-average molecular weight of the component can be determined by gel permeation chromatography (GPC) using a value converted from polystyrene.

[0069] (B) Commercially available products containing these ingredients include, for example, "BMI-689", "BMI-1500", "BMI-1700", "BMI-3000J", and "BMI-2500" manufactured by Designer Molecules.

[0070] The content of component (B) in the resin composition is not particularly limited. When the non-volatile component in the resin composition is set to 100% by mass, it is preferably 50% by mass or less, more preferably 40% by mass or less, even more preferably 30% by mass or less, even more preferably 25% by mass or less, and most preferably 20% by mass or less. The lower limit of the content of component (B) in the resin composition is not particularly limited. When the non-volatile component in the resin composition is set to 100% by mass, it is preferably 1% by mass or more, more preferably 3% by mass or more, even more preferably 5% by mass or more, even more preferably 10% by mass or more, and most preferably 15% by mass or more.

[0071] <(C) Maleimine compounds that do not have aliphatic chains with 7 or more carbon atoms> The resin composition of this invention contains (C) a maleimine compound other than (B) that does not have a fatty chain with 7 or more carbon atoms. That is, when component (C) has a fatty chain, the fatty chain with the most carbon atoms has 6 or fewer carbon atoms. Component (C) can be used alone or in any combination of two or more types.

[0072] In one embodiment, component (C) is preferably a maleimide group that is directly bonded to the carbon atom constituting the aromatic ring, and the maleimide group contained in component (C) is particularly preferably a maleimide group that is directly bonded to the carbon atom constituting the aromatic ring.

[0073] In one embodiment, the maleic anhydride compound of component (C) is preferably of formula (C1-1) or (C1-2):

[0074]

[0075] [In the formula, B2 represents a tetravalent organic group that does not have a fatty chain with 7 or more carbon atoms; n represents an integer of 1 or more (preferably an integer from 1 to 100); A3 represents a divalent organic group that does not have a fatty chain with 7 or more carbon atoms; R3 represents an alkyl or phenyl group with 1 to 6 carbon atoms; s represents an integer of 1 or more (preferably an integer of 1 or 1 to 100, more preferably an integer of 1 or 1 to 50, and even more preferably an integer of 1 or 1 to 20); t represents an integer of 0 to 2 (preferably 0); the other symbols are the same as in formula (B1)] This refers to maleimine compounds. Also, the units n, s, and t can be the same or different.

[0076] B2 independently represents a tetravalent organic group that does not have an aliphatic chain with 7 or more carbon atoms (that is, when it has an aliphatic chain, the tetravalent organic group whose most carbon-containing aliphatic chain has 6 or fewer carbon atoms). The skeleton atoms of the "tetravalent organic group" represented by B2 are, for example, selected from carbon atoms, oxygen atoms, nitrogen atoms, and sulfur atoms. The number of skeleton atoms is not particularly limited, and can be, for example, 5~3000, 5~1000, 5~100, 5~50, etc. B2 can be, for example, a tetravalent group obtained by removing two anhydride groups (-CO-O-CO-) from a tetracarboxylic anhydride that does not have an aliphatic chain with 7 or more carbon atoms, which is commonly used as a raw material for polyimide, but there is no particular limitation.

[0077] B2 is preferably an organic group that does not have an aliphatic chain with 7 or more carbon atoms and has an aromatic ring and / or a non-aromatic ring tetravalent organic group (that is, when it has an aliphatic chain, the aliphatic chain with the most carbon atoms has 6 or less carbon atoms and has an aromatic ring and / or a non-aromatic ring tetravalent organic group), and more preferably a tetravalent group represented by the above formula (b3).

[0078] A3 represents a divalent organic group that does not have an aliphatic chain with 7 or more carbon atoms. The skeleton atoms of the "divalent organic group" represented by A3 can be selected from carbon atoms, oxygen atoms, nitrogen atoms, and sulfur atoms. The number of skeleton atoms is not particularly limited, and can be, for example, 1~3000, 1~1000, 1~100, 1~50, etc.

[0079] The maleimide compound represented by formula (C1-1) is preferably of formula (C2-1):

[0080]

[0081] [In the formula, the symbols are the same as those in formulas (C1-1), (b2), and (b3)] The expressed maleimine compound is preferably represented by formula (C3-1):

[0082]

[0083] [In the formula, R2 independently represents alkyl or phenyl groups with 1 to 6 carbon atoms; f independently represents integers from 0 to 2; the other symbols are the same as in formulas (C1-1), (b2), and (b3).] This refers to maleimide compounds. Also, the f-units can be the same or different.

[0084] The maleimide compound represented by formula (C1-2) is preferably of formula (C2-2):

[0085]

[0086] [In the formula, X3 independently represents single bonds, -C(Ra)2-, -O-, -CO-, -S-, -SO-, -SO2-, -CONH-, or -NHCO-; Ra each independently represents a hydrogen atom, methyl, ethyl, or phenyl; ring Zx3 represents a non-aromatic ring that may have alkyl or phenyl groups selected from 1 to 6 carbon atoms, or an aromatic ring that may have alkyl or phenyl groups selected from 1 to 6 carbon atoms; u each independently represents an integer of 0 or more (preferably an integer from 0 or 1 to 50); other symbols are the same as in formula (C1-2)] The expressed maleimine compound is preferably of formula (C3-2):

[0087]

[0088] [In the formula, X4 independently represents a single bond, -C(Rb)(Rc)-, -O-, -CO-, -S-, -SO-, -SO2-, -CONH-, or -NHCO-; R4 and Rb independently represent a hydrogen atom, a methyl group, or a phenyl group; R5 independently represents a hydrogen atom, an alkyl group with 1 to 6 carbon atoms, or a phenyl group; Rc represents a hydrogen atom, a methyl group, or a phenyl group; or R5 and Rc are bonded together to form a ring (e.g., an inden ring) that may have a group selected from alkyl and alkenyl groups; R6 independently represents a hydrogen atom, an alkyl group with 1 to 6 carbon atoms, or a phenyl group; v represents an integer of 0 or more (preferably an integer of 0 or 1 to 10); other symbols are the same as in formula (C1-2)] This refers to maleimine compounds. Also, the u and v units can be the same or different.

[0089] (C) Specific examples of the components can be listed as formulas (C4-1) to (C4-4):

[0090]

[0091] [In the formula, n' and n” each independently represent an integer from 1 to 20 (preferably an integer from 1 to 10); s' represents an integer from 1 to 100 (preferably an integer from 1 to 50, more preferably an integer from 1 to 20); v' each independently represents an integer from 1 to 10 (preferably an integer from 1 to 5)] This refers to maleimide compounds. Furthermore, the order and configuration of the n' and n" units are arbitrary, including cross-linked copolymers, block copolymers, random copolymers, etc.

[0092] (C) The weight-average molecular weight (Mw) of the component is not particularly limited, but is preferably 200~50000, more preferably 300~40000, and even more preferably 400~20000. The weight-average molecular weight of the component can be determined by gel permeation chromatography (GPC) using a polystyrene equivalent.

[0093] (C) Commercially available products containing this ingredient include, for example, "BMI-6100" manufactured by Designer Molecules and "MIR-3000-70MT" manufactured by Nippon Kayaku Co., Ltd.

[0094] The content of component (C) in the resin composition is not particularly limited. When the non-volatile component in the resin composition is set to 100% by mass, it is preferably 50% by mass or less, more preferably 40% by mass or less, even more preferably 30% by mass or less, even more preferably 25% by mass or less, and most preferably 20% by mass or less. The lower limit of the content of component (C) in the resin composition is not particularly limited. When the non-volatile component in the resin composition is set to 100% by mass, it is preferably 1% by mass or more, more preferably 3% by mass or more, even more preferably 5% by mass or more, even more preferably 10% by mass or more, and most preferably 15% by mass or more.

[0095] In the resin composition, the mass ratio of component (C) to component (B) (component (C) / (B)) is not particularly limited, but preferably 0.01 or more, more preferably 0.1 or more, even more preferably 0.5 or more, and particularly preferably 0.8 or more. The upper limit of the mass ratio of component (C) to component (B) (component (C) / (B)) is not particularly limited, but preferably 50 or less, more preferably 40 or less, even more preferably 20 or less, and particularly preferably 5 or less.

[0096] In the resin composition, the mass ratio of component (A) to the total of components (B) and (C) (component (A) / total of components (B) and (C)) is not particularly limited, but preferably 0.01 or more, more preferably 0.05 or more, even more preferably 0.1 or more, and particularly preferably 0.2 or more. The upper limit of the mass ratio of component (A) to the total of components (B) and (C) (component (A) / total of components (B) and (C)) is not particularly limited, but preferably 5 or less, more preferably 1 or less, even more preferably 0.5 or less, and particularly preferably 0.3 or less.

[0097] <(D) Arbitrary free radical polymeric compounds> The resin composition of the present invention includes a free radical polymerizable compound (D) other than component (B) and component (C), which are optional components. Component (D) can be used alone or in any combination of two or more types.

[0098] (D) Component, for example, may be a compound having a free radical polymerizable unsaturated group. The free radical polymerizable unsaturated group is not particularly limited during free radical polymerization, but is preferably an vinyl unsaturated group with a carbon-carbon double bond at the end or inside. Specifically, it may be an unsaturated aliphatic group such as allyl or 3-cyclohexenyl; an aromatic group containing an unsaturated aliphatic group such as p-vinylphenyl, m-vinylphenyl, or styryl; or an α,β-unsaturated carbonyl group such as acrylonitrile, methacryl, maleic anhydride, or trans-butenidyl. Component (D) is preferably having one or more free radical polymerizable unsaturated groups, more preferably two or more.

[0099] As component (D), well-known free radical polymerizable compounds can be widely used without particular limitation. Examples include (D-1) vinylphenyl free radical polymerizable compounds and (D-2) (meth)acrylic acid free radical polymerizable compounds.

[0100] <(D-1) Vinylphenyl free radical polymeric compounds> (D-1) Vinylphenyl radical polymerizable compounds are free radical polymerizable compounds containing vinylphenyl groups. Preferably, each vinylphenyl radical polymerizable compound contains two or more vinylphenyl groups.

[0101] In one embodiment, (D-1) a vinylphenyl-based free radical polymerizable compound is preferably a vinylbenzyl-modified polyphenylene ether having a vinylbenzyl and polyphenylene ether backbone, and particularly preferably having the formula (D1):

[0102]

[0103] [In the formula, R11, R12, R13 and R14 each independently represent a hydrogen atom or a substituent (preferably a hydrogen atom or an alkyl group, especially a hydrogen atom or a methyl group)] The repeated unit (number of repeated units, preferably 2 to 300, more preferably 2 to 100) and the vinyl benzyl modified polyphenylene ether having a vinyl benzyl group (especially the polyphenylene ether in which the hydrogen atoms of the two terminal hydroxyl groups are replaced by the two terminal vinyl benzyl modified polyphenylene ethers of the vinyl benzyl group).

[0104] In other embodiments, (D-1) vinylphenyl-based free radical polymerizable compounds are preferably those having formula (D2):

[0105]

[0106] [In the formula, R15, R16, and R17 each independently represent a hydrogen atom or a substituent (preferably a hydrogen atom)] The divinylbenzene polymer represents the repeating units (number of repeating units, preferably 2 to 200). This divinylbenzene polymer can be a copolymer containing other styrene backbone units such as styrene units and ethylstyrene units. When other styrene backbone units are present, the ratio of repeating units in formula (D2) to all styrene backbone units is preferably 5 to 70 moles.

[0107] (D-1) The number average molecular weight of the vinylphenyl free radical polymerizable compound is not particularly limited, but preferably 500~100000, more preferably 700~80000. (D) The number average molecular weight of the component can be determined by gel permeation chromatography (GPC) using a polystyrene equivalent. (D-1) The functional group equivalent of the vinyl group in the vinylphenyl free radical polymerizable compound is not particularly limited, but preferably 200 g / eq.~3000 g / eq., more preferably 200 g / eq.~2000 g / eq.

[0108] (D-1) Commercially available vinylphenyl free radical polymerizable compounds include, for example, “OPE-2St 1200” and “OPE-2St 2200” (vinylbenzene modified polyphenylene ether) manufactured by Mitsubishi Gas Chemical Co., Ltd.; and “ODV-XET-X03”, “ODV-XET-X04”, and “ODV-XET-X05” (divinylbenzene polymer) manufactured by NIPPON STEEL Chemical & Material Co., Ltd.

[0109] <(D-2)(meth)acrylic acid-based free radical polymers> (D-2)(meth)acrylic acid-based free radical polymerizable compounds are free radical polymerizable compounds having acrylonitrile and / or methacrylonitrile. Preferably, each molecule of the (D-2)(meth)acrylic acid-based free radical polymerizable compound has two or more acrylonitrile and / or methacrylonitrile groups. More preferably, the (D-2)(meth)acrylic acid-based free radical polymerizable compound is a (meth)acrylic acid-modified polyphenylene ether having an acrylonitrile and / or methacrylonitrile group and a polyphenylene ether backbone, particularly preferably having formula (D3):

[0110]

[0111] [In the formula, R21, R22, R23 and R24 each independently represent a hydrogen atom or a substituent (preferably a hydrogen atom or an alkyl group, especially a hydrogen atom or a methyl group)] The repeated units (number of repeated units, preferably 2 to 300, more preferably 2 to 100) and acrylonitrile and / or methacrylic (meth)acrylic modified polyphenylene ethers (especially polyphenylene ethers in which the hydrogen atoms of the two terminal hydroxyl groups are replaced by acrylonitrile and / or methacrylic (meth)acrylic modified polyphenylene ethers).

[0112] The number-average molecular weight of the (D-2)(meth)acrylic acid free radical polymerizable compound is not particularly limited, but is preferably 500-10000, more preferably 700-5000. The functional equivalents of the acrylonitrile and methacrylonitrile groups in the (D-2)(meth)acrylic acid free radical polymerizable compound are not particularly limited, but are preferably 200 g / eq.-3000 g / eq., more preferably 300 g / eq.-2000 g / eq.

[0113] Commercially available (D-2) (meth)acrylic acid is a free radical polymerizable compound, such as "SA9000" and "SA9000-111" (methacrylic acid modified polyphenylene ether) manufactured by SABIC Innovative Plastics.

[0114] The content of component (D) in the resin composition is not particularly limited. When the non-volatile component in the resin composition is set to 100% by mass, it is preferably 60% by mass or less, more preferably 50% by mass or less, even more preferably 40% by mass or less, even more preferably 30% by mass or less, and most preferably 20% by mass or less. The lower limit of the content of component (D) in the resin composition is not particularly limited. When the non-volatile component in the resin composition is set to 100% by mass, it can be, for example, 0% by mass or more, 0.1% by mass or more, 1% by mass or more, 3% by mass or more, 5% by mass or more, 7% by mass or more, etc.

[0115] <(E) Inorganic filler> The resin composition of the present invention contains (E) inorganic filler as an arbitrary component. The (E) inorganic filler is contained in the resin composition in a particle state.

[0116] (E) Inorganic filler materials, using inorganic compounds. Examples of inorganic filler materials include, for example, silicon dioxide, alumina, glass, lapis lazuli, barium sulfate, barium carbonate, talc, clay, mica powder, zinc oxide, hydrotalcite, gibbsite, aluminum hydroxide, magnesium hydroxide, calcium carbonate, magnesium carbonate, magnesium oxide, boron nitride, aluminum nitride, manganese nitride, aluminum borate, strontium carbonate, strontium titanate, calcium titanate, magnesium titanate, bismuth titanate, titanium oxide, zirconium oxide, barium titanate, barium zirconate titanate, barium zirconate, calcium zirconate, zirconium phosphate, zirconium phosphotungstenate, granular iron, iron-based alloys, etc. Among these, silicon dioxide is particularly preferred. Examples of silicon dioxide include, for example, amorphous silicon dioxide, fused silicon dioxide, crystalline silicon dioxide, synthetic silicon dioxide, hollow silicon dioxide, etc. Furthermore, silicon dioxide, preferably spherical silicon dioxide. (E) Inorganic fillers may be used alone or in combination of two or more in any ratio.

[0117] (E) Commercially available inorganic fillers include, for example, "UFP-30" manufactured by Denka Chemical Industry Co., Ltd.; "SP60-05" and "SP507-05" manufactured by NIPPON STEEL & SUMIKIN MATERIALS Co., Ltd.; "YC100C", "YA050C", "YA050C-MJE", and "YA010C" manufactured by Admatechs Co., Ltd.; "UFP-30" manufactured by Denka Co., Ltd.; "SilFileNSS-3N", "SilFileNSS-4N", and "SilFileNSS-5N" manufactured by Tokuyama Co., Ltd.; "SC2500SQ", "SO-C4", "SO-C2", and "SO-C1" manufactured by Admatechs Co., Ltd.; and "DAW-03" and "FB-105FD" manufactured by Denka Co., Ltd.

[0118] (E) The average particle size of the inorganic filler is not particularly limited, but preferably 10 μm or less, more preferably 5 μm or less, even more preferably 2 μm or less, still more preferably 1 μm or less, and 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 preferably 0.01 μm or more, more preferably 0.05 μm or more, even more preferably 0.1 μm or more, and particularly preferably 0.2 μm or more. (E) The average particle size of the inorganic filler can be determined by laser diffraction and scattering based on Mie scattering theory. Specifically, by using a laser diffraction and scattering particle size distribution measuring device, the particle size distribution of the inorganic filler is prepared on a volume basis, and the median particle size can be used as the average particle size for measurement. The sample for measurement can be prepared by weighing 100 mg of inorganic filler and 10 g of methyl ethyl ketone in a small glass bottle and dispersing it ultrasonically for 10 minutes. A laser diffraction particle size distribution measuring device is used, employing blue and red light source wavelengths, to determine the volumetric particle size distribution of the inorganic filler sample using a flow cell method. The average particle size is then calculated from the obtained particle size distribution using the median particle size. Examples of laser diffraction particle size distribution measuring devices include the "LA-960" manufactured by Horiba Manufacturing Co., Ltd.

[0119] (E) The specific surface area of ​​the inorganic filler is not particularly limited, but preferably 0.1 m² / g or more, more preferably 0.5 m² / g or more, even more preferably 1 m² / g or more, and particularly preferably 3 m² / g or more. (E) The upper limit of the specific surface area of ​​the inorganic filler is not particularly limited, but preferably 100 m² / g or less, more preferably 70 m² / g or less, even more preferably 50 m² / g or less, and particularly preferably 40 m² / g or less. The specific surface area of ​​the inorganic filler is obtained according to the BET method, using a specific surface area measuring device (Macsorb HM-1210 manufactured by MOUNTECH), by adsorbing nitrogen gas onto the surface of the sample, and calculating the specific surface area using the BET multi-point method.

[0120] (E) The inorganic filler is preferably surface-treated with a suitable surface treatment agent. Surface treatment improves the moisture resistance and dispersibility of the (E) inorganic filler. Examples of surface treatment agents include vinyl silane coupling agents such as vinyltrimethoxysilane and vinyltriethoxysilane; epoxy silane coupling agents such as 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, 3-epoxypropoxypropylmethyldimethoxysilane, 3-epoxypropoxypropyltrimethoxysilane, 3-epoxypropoxypropylmethyldiethoxysilane, and 3-epoxypropoxypropyltriethoxysilane; styrene silane coupling agents such as p-styrenetrimethoxysilane; and 3-methacryloxypropylmethyldimethoxysilane and 3-methacryloxypropyltriethoxysilane. Methacrylic silane coupling agents such as acetylacetyltrimethoxysilane, 3-methacrylic acetylacetylmethyldiethoxysilane, and 3-methacrylic acetylacetyltriethoxysilane; acrylic silane coupling agents such as 3-acetylacetyltrimethoxysilane; N-2-(aminoethyl)-3-aminopropylmethyldiethoxysilane, N-2-(aminoethyl)-3-aminopropyltrimethoxysilane, 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, and 3-triethoxysilyl-N-(1,3-dimethyl-butylene)propylamine. Amine-based silane coupling agents such as N-phenyl-3-aminopropyltrimethoxysilane, N-phenyl-8-aminooctyltrimethoxysilane, and N-(vinylbenzyl)-2-aminoethyl-3-aminopropyltrimethoxysilane; isocyanurate-based silane coupling agents such as tri-(trimethoxysilylpropyl)isocyanurate; urea-based silane coupling agents such as 3-ureopropyltrialkoxysilane; mercapto-based silane coupling agents such as 3-mercaptopropylmethyldimethoxysilane and 3-mercaptopropyltrimethoxysilane; and isocyanate-based silanes such as 3-isocyanatepropyltriethoxysilane. Coupling agents; anhydride-based silane coupling agents such as 3-trimethoxysilylpropylsuccinic anhydride; silane coupling agents such as methyltrimethoxysilane, dimethyldimethoxysilane, phenyltrimethoxysilane, methyltriethoxysilane, dimethyldiethoxysilane, phenyltriethoxysilane, n-propyltrimethoxysilane, n-propyltriethoxysilane, hexyltrimethoxysilane, hexyltriethoxysilane, octyltriethoxysilane, decyltrimethoxysilane, 1,6-bis(trimethoxysilyl)hexane, trifluoropropyltrimethoxysilane, etc. Furthermore, surface treatment agents can be used alone or in combination of two or more in any ratio.

[0121] Commercially available surface treatment agents include, for example, Shin-Etsu Chemical Co., Ltd.'s "KBM-1003" and "KBE-1003" (vinyl silane coupling agents); "KBM-303," "KBM-402," "KBM-403," "KBE-402," and "KBE-403" (epoxy silane coupling agents); "KBM-1403" (styrene-based silane coupling agent); and "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-903", "KBE-9103P", "KBM-573", "KBM-575" (amine) Silane coupling agents (based on hydroxyl groups); "KBM-9659" (isocyanurate-based silane coupling agent); "KBE-585" (urea-based silane coupling agent); "KBM-802", "KBM-803" (mercapto-based silane coupling agents); "KBE-9007N" (isocyanate-based silane coupling agent); "X-12-967C" (anhydride-based silane coupling agent); "KBM-13", "KBM-22" "KBM-103", "KBE-13", "KBE-22", "KBE-103", "KBM-3033", "KBE-3033", "KBM-3063", "KBE-3063", "KBE-3083", "KBM-3103C", "KBM-3066", "KBM-7103" (non-silane coupled-alkoxysilane compound), etc.

[0122] From the perspective of improving the dispersibility of inorganic fillers by adjusting the degree of surface treatment with the surface treatment agent, it is preferable to apply the treatment within a specific range. Specifically, it is preferable to apply 0.2% to 5% by mass of the surface treatment agent to 100% by mass of the inorganic filler, more preferably 0.2% to 3% by mass, and even more preferably 0.3% to 2% by mass.

[0123] The degree of surface treatment by the surface treatment agent can be evaluated by the carbon content per unit surface area of ​​the inorganic filler. From the viewpoint of improving the dispersibility of the inorganic filler, the carbon content per unit surface area is preferably 0.02 mg / m² or more, more preferably 0.1 mg / m² or more, and even more preferably 0.2 mg / m² or more. Furthermore, from the viewpoint of preventing an increase in the melt viscosity of the resin composition or the melt viscosity of the flake form, it is preferably 1.0 mg / m² or less, more preferably 0.8 mg / m² or less, and even more preferably 0.5 mg / m² or less.

[0124] The carbon content per unit surface area of ​​an inorganic filler can be determined after cleaning it with a solvent (e.g., methyl ethyl ketone (MEK)). Specifically, a sufficient amount of MEK is added to the inorganic filler, which has been surface-treated with a surface-treatment agent, and the mixture is ultrasonically cleaned at 25°C for 5 minutes. After removing the supernatant and drying the solid components, the carbon content per unit surface area of ​​the inorganic filler can be determined using a carbon analyzer. A carbon analyzer such as the "EMIA-320V" manufactured by Horiba Corporation can be used.

[0125] The content of inorganic filler (E) in the resin composition is not particularly limited. When the non-volatile component in the resin composition is set to 100% by mass, it is preferably 90% by mass or less, more preferably 80% by mass or less, even more preferably 75% by mass or less, and particularly preferably 70% by mass or less. The lower limit of the content of inorganic filler (E) in the resin composition is not particularly limited. When the non-volatile component in the resin composition is set to 100% by mass, it can be, for example, 0% by mass or more, 1% by mass or more, 5% by mass or more, 10% by mass or more, etc., preferably 20% by mass or more, more preferably 25% by mass or more, even more preferably 35% by mass or more, and particularly preferably 40% by mass or more.

[0126] <(F) Hardening Accelerator> The resin composition of the present invention may include a curing accelerator (F) as an arbitrary component. In one embodiment, the curing accelerator (F) may function as a catalyst for promoting the addition reaction of component (A) with components (B) and (C) (and component (D) when component (D) is included).

[0127] (F) Curing accelerators, such as (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, are preferred. In one embodiment, (F) the curing accelerator preferably includes (F-1) an imidazole-based curing accelerator. (F) the curing accelerator can be used alone or in combination of two or more.

[0128] (F-1) Imidazole-based hardening accelerators, such as 2-methylimidazole, 2-undecylimidazole, 2-heptadecylimidazole, 1,2-dimethylimidazole, 2-ethyl-4-methylimidazole, 1,2-dimethylimidazole, 2-ethyl-4-methylimidazole, 2-phenylimidazole, 2-phenyl-4-methylimidazole, 1-benzyl-2-methylimidazole, 1-benzyl-2-phenylimidazole, 1-cyanoethyl-2-methylimidazole, 1-cyanoethyl-2-undecylimidazole, 1-cyanoethyl-2-ethyl-4-methylimidazole, 1-cyanoethyl-2-phenylimidazole, 1-cyanoethyl-2-undecylimidazole ontium trimellitate, 1-cyanoethyl-2-phenylimidazole ontium trimellitate, 2,4-diamino-6-[2'-methylimidazole-(1')] Imidazole compounds such as 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-phenylimidazolyl isocyanuric acid adduct, 2-phenyl-4,5-dihydroxymethylimidazolium, 2-phenyl-4-methyl-5-hydroxymethylimidazolium, 2,3-dihydro-1H-pyrrolo[1,2-a]benzimidazole, 1-dodecyl-2-methyl-3-benzylimidazolium chloride, 2-methylimidazoline, 2-phenylimidazoline, etc., and adducts of imidazole compounds with epoxy resins.

[0129] (F-1) Imidazole hardening accelerators can be commercially available, such as "1B2PZ", "2MZA-PW", "2PHZ-PW" manufactured by Shikoku Chemical Co., Ltd., and "P200-H50" manufactured by Mitsubishi Chemical Co., Ltd.

[0130] (F-2) Phosphorus-based hardening accelerators, such as tetrabutylphosphonium bromide, tetrabutylphosphine chloride, tetrabutylphosphonium acetate, tetrabutylphosphonium decanoate, tetrabutylphosphonium laurate, bis(tetrabutylphosphonium)pyromellitic ester, tetrabutylphosphonium hydrogen hexahydrophthalate, tetrabutylphosphonium 2,6-bis[(2-hydroxy-5-methylphenyl)methyl]-4-methylphenolate (Phenolate), di-tert-butylmethylphosphonium tetraphenylborate, etc., aliphatic phosphonium salts; methyltriphenylphosphonium bromide, ethyltriphenylphosphonium bromide, propyltriphenylphosphonium bromide, butyltriphenylphosphonium bromide, benzyltriphenylphosphonium chloride, tetraphenylphosphonium bromide, p-tolyl Aromatic phosphonium salts of triphenylphosphonium tetra-p-tolylborate, tetraphenylphosphonium tetraphenylborate, tetraphenylphosphonium tetrap-tolylborate, triphenylethylphosphonium tetraphenylborate, tri(3-methylphenyl)ethylphosphonium tetraphenylborate, tri(2-methoxyphenyl)ethylphosphonium tetraphenylborate, (4-methylphenyl)triphenylphosphonium thiocyanate, tetraphenylphosphonium thiocyanate, butyltriphenylphosphonium thiocyanate, etc.; aromatic phosphine-borane complexes of triphenylphosphine-triphenylborane, etc.; aromatic phosphine-quinone addition reactants of triphenylphosphine-p-benzoquinone, etc.; tributylphosphine, tri-tert-butylphosphine, trioctylphosphine, di-tert-butylphosphine, etc. Aliphatic phosphines such as rt-butyl(2-butenyl)phosphine, di-tert-butyl(3-methyl-2-butenyl)phosphine, and tricyclohexylphosphine; dibutylphenylphosphine, di-tert-butylphenylphosphine, methyldiphenylphosphine, ethyldiphenylphosphine, butyldiphenylphosphine, diphenylcyclohexylphosphine, triphenylphosphine, tri-o-tolylphosphine, tri-m-tolylphosphine, tri-p-tolylphosphine, tri(4-ethylphenyl)phosphine, tri(4-propylphenyl)phosphine, tri(4-isopropylphenyl)phosphine, tri(4-butylphenyl)phosphine, tri(4-tert-butylphenyl)phosphine, tri(2,4-dimethylphenyl)phosphine, and tri(2,5-dimethylphenyl)phosphine. Aromatic phosphines such as tris(2,6-dimethylphenyl)phosphine, tris(3,5-dimethylphenyl)phosphine, tris(2,4,6-trimethylphenyl)phosphine, tris(2,6-dimethyl-4-ethoxyphenyl)phosphine, tris(2-methoxyphenyl)phosphine, tris(4-methoxyphenyl)phosphine, tris(4-ethoxyphenyl)phosphine, tris(4-tert-butoxyphenyl)phosphine, diphenyl-2-pyridylphosphine, 1,2-bis(diphenylphosphino)ethane, 1,3-bis(diphenylphosphino)propane, 1,4-bis(diphenylphosphino)butane, 1,2-bis(diphenylphosphino)acetylene, and 2,2'-bis(diphenylphosphino)diphenyl ether.

[0131] (F-3) Urea-based hardening accelerators, examples of which include aliphatic dimethylureas such as 1,1-dimethylurea; 1,1,3-trimethylurea, 3-ethyl-1,1-dimethylurea, 3-cyclohexyl-1,1-dimethylurea, and 3-cyclooctyl-1,1-dimethylurea; 3-phenyl-1,1-dimethylurea, 3-(4-chlorophenyl)-1,1-dimethylurea, 3-(3,4-dichlorophenyl)-1,1-dimethylurea, 3-(3-chloro-4-methylphenyl)-1,1-dimethylurea, 3-(2-methylphenyl)-1,1-dimethylurea, 3-(4-methylphenyl)-1,1-dimethylurea, and 3-(3,4-dimethylphenyl)-1 Aromatic dimethylureas such as 1-dimethylurea, 3-(4-isopropylphenyl)-1,1-dimethylurea, 3-(4-methoxyphenyl)-1,1-dimethylurea, 3-(4-nitrophenyl)-1,1-dimethylurea, 3-[4-(4-methoxyphenoxy)phenyl]-1,1-dimethylurea, 3-[4-(4-chlorophenoxy)phenyl]-1,1-dimethylurea, 3-[3-(trifluoromethyl)phenyl]-1,1-dimethylurea, N,N-(1,4-epenylphenyl)bis(N',N'-dimethylurea), N,N-(4-methyl-1,3-epenylphenyl)bis(N',N'-dimethylurea)[toluenebisdimethylurea], etc.

[0132] (F-4) Guanidine-based hardening accelerators include, for example, dicyandiamide, 1-methylguanidine, 1-ethylguanidine, 1-cyclohexylguanidine, 1-phenylguanidine, 1-(o-tolyl)guanidine, dimethylguanidine, diphenylguanidine, trimethylguanidine, tetramethylguanidine, pentamethylguanidine, 1,5,7-triazabicyclo[4.4.0]dec-5-ene, 7-methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene, 1-methylbiguanidine, 1-ethylbiguanidine, 1-n-butylbiguanidine, 1-n-octadecylbiguanidine, 1,1-dimethylbiguanidine, 1,1-diethylbiguanidine, 1-cyclohexylbiguanidine, 1-allylbiguanidine, 1-phenylbiguanidine, 1-(o-tolyl)biguanidine, etc.

[0133] (F-5) Metal-based hardening accelerators, such as organometallic complexes or organometallic salts of metals like cobalt, copper, zinc, iron, nickel, manganese, and tin. Specific examples of organometallic complexes include organocobalt complexes such as cobalt(II) and cobalt(III) acetoacetone, organocopper complexes such as copper(II) acetoacetone, organozinc complexes such as zinc(II) acetoacetone, organoiron complexes such as iron(III) acetoacetone, organonickel complexes such as nickel(II) acetoacetone, and organomanganese complexes such as manganese(II) acetoacetone. Examples of organometallic salts include zinc octoate, tin octoate, zinc naphthenate, cobalt naphthenate, tin stearate, and zinc stearate.

[0134] (F-6) Amine-based hardening accelerators, such as trialkylamines like triethylamine and tributylamine, 4-dimethylaminopyridine, benzyldimethylamine, 2,4,6-tris(dimethylaminomethyl)phenol, and 1,8-diazabicyclo(5,4,0)-undecene, etc.

[0135] (F-6) Amine-based hardening accelerators, commercially available products can be used, such as "MY-25" manufactured by ajinomoto-fine-techno.

[0136] The content of (F) curing accelerator in the resin composition is not particularly limited. When the non-volatile component in the resin composition is set to 100% by mass, it is preferably 10% by mass or less, more preferably 5% by mass or less, even more preferably 3% by mass or less, and most preferably 1% by mass or less. The lower limit of the content of (F) curing accelerator in the resin composition is not particularly limited. When the non-volatile component in the resin composition is set to 100% by mass, it can be, for example, 0% by mass or more, 0.001% by mass or more, 0.01% by mass or more, 0.1% by mass or more, 0.5% by mass or more, etc.

[0137] <(G) Other Additives> The resin composition of the present invention may also contain any additives as non-volatile components. Examples of such additives include, for instance, curing agents other than component (A) such as phenolic curing agents and thiol curing agents; thermosetting resins such as epoxy resins, epoxy acrylate resins, urethane acrylate resins, urethane resins, cyanate ester resins, benzoxazine resins, unsaturated polyester resins, phenolic resins, melamine resins, polysiloxane resins, and phenoxy resins; free radical polymerization initiators such as peroxide-based free radical polymerization initiators and azo-based free radical polymerization initiators; and polyvinyl alcohol acetal resins, polyolefin resins, and polyurethane resins. Thermoplastic resins such as esters, polyether resins, polyphenylene ether resins, polycarbonate resins, polyetheretherketone resins, and polyester resins; organic fillers such as rubber particles; organometallic compounds such as organocopper compounds, organozinc compounds, and organocobalt compounds; colorants such as phthalocyanine blue, phthalocyanine green, iodine green, diazo yellow, crystal violet, titanium dioxide, and carbon black; polymerization inhibitors such as hydroquinone, catechol, pyrogallol, and phenothiazine; leveling agents such as polysiloxane-based leveling agents and acrylic polymer-based leveling agents; and tackifiers such as Benton and microcrystalline kaolinite. Defoamers including polysiloxane-based, acrylic-based, fluorinated, and vinyl resin-based defoamers; ultraviolet absorbers including benzotriazole-based ultraviolet absorbers; adhesion enhancers including ureasilanes; adhesion promoters including triazole-based, tetraazole-based, and triazine-based adhesion promoters; antioxidants including hindered phenol-based and hindered amine-based antioxidants; fluorescent whitening agents including piracetam derivatives; surfactants including fluorinated and polysiloxane-based surfactants; and phosphorus-based flame retardants (e.g., phosphoric acid). Flame retardants including ester compounds, phosphazene compounds, phosphonic acid compounds, red phosphorus, nitrogen-based flame retardants (e.g., melamine sulfate), halogen-based flame retardants, and inorganic flame retardants (e.g., antimony trioxide); dispersants including phosphate ester dispersants, polyoxyethylene dispersants, acetylene dispersants, polysiloxane dispersants, anionic dispersants, and cationic dispersants; stabilizers including borate stabilizers, titanate stabilizers, aluminate stabilizers, zirconate stabilizers, isocyanate stabilizers, carboxylic acid stabilizers, and carboxylic anhydride stabilizers. (G) Other additives may be used alone or in combination of two or more in any ratio. (G) The content of other additives can be appropriately set by someone skilled in the art.

[0138] <(H) Organic solvents> In addition to the non-volatile components mentioned above, the resin composition of this invention may contain any organic solvent as a volatile component. (H) The organic solvent may be any known type, and there is no particular limitation on its type. Examples of organic solvents 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; and methyl methoxypropionate, propylene glycol monomethyl ether acetate, diethylene glycol monoethyl ether acetate, ethyl diethylene glycol acetate, γ-butyrolactone, and methyl methoxypropionate. Ether-ester solvents; 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); acetylamine solvents such as N,N-dimethylformamide, N,N-dimethylacetylamine, and N-methyl-2-pyrrolidone; urethane 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) Organic solvents can be used alone or in combination of two or more in any ratio.

[0139] In one embodiment, the content of (H) organic solvent is not particularly limited. When the total component in the resin composition is set to 100% by mass, it can be, for example, 60% or less by mass, 40% or less by mass, 30% or less by mass, 20% or less by mass, 15% or less by mass, 10% or less by mass, etc.

[0140] <Manufacturing Method of Resin Composition> The resin composition of the present invention is manufactured, for example, by adding and mixing (A) an amine compound having a biphenyl skeleton, (B) a maleimide compound having an aliphatic chain with 7 or more carbon atoms, (C) a maleimide compound without an aliphatic chain with 7 or more carbon atoms, (D) any free radical polymerizable compound if necessary, (E) an inorganic filler if necessary, (F) a curing accelerator if necessary, (G) other additives if necessary, and (H) an organic solvent if necessary, in any order and / or partially or entirely simultaneously. Furthermore, the mixing process of adding each component can be appropriately temperature-controlled, and heating and / or cooling can be performed temporarily or continuously. Also, during or after the mixing process, the resin composition can be stirred or agitated using, for example, a mixer or other stirring or oscillating device to achieve uniform dispersion. Furthermore, degassing can also be performed simultaneously under low-pressure conditions such as vacuum while stirring or agitating.

[0141] Properties of Resin Compositions The resin composition of this invention comprises (A) an amine compound having a biphenyl backbone, (B) a maleimine compound having an aliphatic chain with 7 or more carbon atoms, and (C) a maleimine compound without an aliphatic chain having 7 or more carbon atoms. By using this resin composition, a cured product with low specific capacitance (Dk) and dielectric tangent (Df) and excellent peel strength of the electroplated conductor layer can be obtained.

[0142] The cured resin composition of the present invention can have a low dielectric tangent (Df). Therefore, in one embodiment, as in Test Example 1 below, the dielectric tangent (Df) of the cured resin composition measured at 5.8 GHz and 23°C is preferably 0.020 or less, 0.010 or less, more preferably 0.008 or less, 0.007 or less, even more preferably 0.006 or less, 0.005 or less, and particularly preferably 0.004 or less, 0.003 or less.

[0143] The cured resin composition of the present invention may have a low specific capacitance (Dk). Therefore, in one embodiment, as in Test Example 1 below, the specific capacitance (Dk) of the cured resin composition measured at 5.8 GHz and 23°C is preferably 5.0 or less, more preferably 4.0 or less, even more preferably 3.5 or less, still more preferably 3.0 or less, and particularly preferably 2.9 or less.

[0144] The cured resin composition of the present invention exhibits excellent peel strength of the electroplated conductor layer. Therefore, in one embodiment, as in Test Example 2 below, the cured material forms a copper-plated conductor layer. In the vertical direction, the copper plating peel strength, calculated from the load during peeling of the copper-plated conductor layer, is preferably 0.2 kgf / cm or more, more preferably 0.3 kgf / cm or more, even more preferably 0.35 kgf / cm or more, and particularly preferably 0.4 kgf / cm or more. There is no particular upper limit; for example, it can be 10 kgf / cm or less.

[0145] In one embodiment, the cured resin composition of the present invention may have a low arithmetic mean roughness (Ra) of the surface after roughening treatment. Therefore, in one embodiment, as in Test Example 2 below, the arithmetic mean roughness (Ra) of the surface of the cured material after roughening treatment is preferably 300 nm or less, more preferably 200 nm or less, even more preferably 150 nm or less, even more preferably 120 nm or less, and most preferably 100 nm or less. The lower limit is not particularly limited; for example, it may be 1 nm or more, 2 nm or more, etc.

[0146] <Uses of Resin Compositions> The resin composition of this invention is suitable for use as a resin composition for insulating purposes, particularly for forming insulating layers. Specifically, it is suitable for use as a resin composition for forming an insulating layer for forming a conductor layer (including a rewiring layer) formed on an insulating layer (resin composition for forming an insulating layer for forming a conductor layer). Furthermore, it is suitable for use as a resin composition for forming an insulating layer in printed circuit boards (printed circuit board insulating layer forming resin composition) as described later. The resin composition of this invention can be widely used in applications requiring resin compositions, such as sheet-like laminates like resin sheets and prepregs, solder resists, underfill materials, die bond materials, semiconductor packaging materials, buried via resins, and component embedding resins.

[0147] Furthermore, for example, when manufacturing a semiconductor wafer package via steps (1) to (6) below, the resin composition of the present invention can be used as a resin composition for forming a rewiring layer of an insulating layer for forming a rewiring layer (resin composition for forming a rewiring layer), and as a resin composition for semiconductor wafer packaging (resin composition for semiconductor wafer packaging). When manufacturing a semiconductor wafer package, a rewiring layer can be further formed on the sealing layer. (1) Step of temporarily fixing the film on the substrate. (2) The step of temporarily fixing the semiconductor wafer onto the temporary fixing film. (3) The step of forming a sealing layer on a semiconductor wafer. (4) The step of peeling the substrate and the temporary fixing film from the semiconductor wafer. (5) The step of forming a redistribution layer as an insulating layer on the surface of the substrate and the temporarily fixed thin film after the semiconductor wafer has been stripped, and (6) Step of forming a rewiring layer as a conductor layer on the rewiring forming layer.

[0148] Furthermore, the resin composition of the present invention provides an insulating layer with good component embedding properties, making it suitable for use in printed wiring boards where components are embedded in the circuit board.

[0149] <Thin laminated materials> The resin composition of the present invention can also be applied in a varnish state. Industrially, it is generally suitable for use in the form of a sheet-like laminate containing the resin composition.

[0150] The sheet-like laminated material is preferably a resin sheet or prepreg as shown below.

[0151] In one embodiment, the resin sheet comprises a support and a resin composition layer disposed on the support, wherein the resin composition layer is formed from the resin composition of the present invention.

[0152] The thickness of the resin composition layer, from the viewpoint of providing a curing material with excellent insulation even when the printed circuit board is made thin and the cured resin composition is a thin film, is preferably 50 μm or less, and more preferably 40 μm or less. There is no particular limitation on the lower limit of the resin composition layer thickness; it is generally 5 μm or more, 10 μm or more, etc.

[0153] Examples of supports include films made of plastic materials, metal foils, and release paper, with films and metal foils made of plastic materials being more preferred.

[0154] When using a film made of plastic material as a support, examples of plastic materials include polyesters such as polyethylene terephthalate (hereinafter sometimes abbreviated as "PET") and polyethylene naphthalate (hereinafter sometimes abbreviated as "PEN"), acrylics such as polycarbonate (hereinafter sometimes abbreviated as "PC") and polymethyl methacrylate (PMMA), cyclic polyolefins, triacetyl cellulose (TAC), polyether sulfide (PES), polyether ketone, and polyimide. Among these, polyethylene terephthalate and polyethylene naphthalate are preferred, and inexpensive polyethylene terephthalate is particularly preferred.

[0155] When using metal foil as a support, examples of metal foils include copper foil and aluminum foil, with copper foil being preferred. Copper foil can be made of copper alone or as an alloy of copper with other metals (e.g., tin, chromium, silver, magnesium, nickel, zirconium, silicon, titanium, etc.).

[0156] The surfaces where the support and the resin composition layers meet can be treated with matte finish or corona treatment.

[0157] Furthermore, as a support, a support with a release layer can also be used, the surface of which bonds with the resin composition layer has a release layer. The release agent used in the release layer of the support with the release layer can be, for example, one or more release agents selected from the group consisting of alkyd resins, polyolefin resins, urethane resins, and polysiloxane resins. Commercially available products can be used as the support with the release layer, for example, PET films having a release layer with an alkyd resin-based release agent as the main component, such as Lintec's "SK-1", "AL-5", and "AL-7"; Toray's "Lumirror T60"; Teijin's "Purex"; and Unitika's "Unipeel", etc.

[0158] The thickness of the support is not particularly limited, but is preferably in the range of 5μm to 75μm, and more preferably in the range of 10μm to 60μm. Furthermore, when using a support with an attached release layer, the overall thickness of the support with the release layer is preferably within the above-mentioned range.

[0159] In one embodiment, the resin sheet may further contain any arbitrary layer if necessary. This arbitrary layer may include, for example, a protective film disposed on the surface of the resin composition layer that is not bonded to the support (i.e., the surface opposite to the support), depending on the support. The thickness of the protective film is not particularly limited, and may be, for example, 1 μm to 40 μm. By laminating the protective film, the adhesion or scratches of dirt or other contaminants to the surface of the resin composition layer can be suppressed.

[0160] Resin sheets, such as liquid resin compositions, can be directly or by preparing a resin varnish in which the resin composition is dissolved in an organic solvent. This varnish is then applied to a support using a die coater or similar device and dried to form a resin composition layer.

[0161] Organic solvents may be listed as those that are the same as those listed in the composition description of the resin. One organic solvent may be used alone, or two or more may be used in combination.

[0162] Drying can be carried out using conventional methods such as heating or blowing hot air. There are no particular limitations on drying conditions; the organic solvent content in the resin composition layer should be dried to below 10% by mass, preferably below 5% by mass. This also varies depending on the boiling point of the organic solvent in the resin composition or resin varnish. For example, when using a resin composition or resin varnish containing 30% to 60% by mass of organic solvent, a resin composition layer can be formed by drying at 50°C to 150°C for 3 to 10 minutes.

[0163] Resin sheets can be rolled into rolls for storage. If the resin sheet has a protective film, the protective film can be peeled off for later use.

[0164] In one embodiment, the prepreg system is formed by impregnating the resin composition of the present invention into a sheet-like fiber substrate.

[0165] The sheet-like fiber substrate used in the prepreg is not particularly limited and can be commonly used as a substrate for prepregs such as glass cloth, aromatic polyamide nonwoven fabric, and liquid crystal polymer nonwoven fabric. From the viewpoint of thinning printed circuit boards, the thickness of the sheet-like fiber substrate is preferably 50 μm or less, more preferably 40 μm or less, even more preferably 30 μm or less, and particularly preferably 20 μm or less. There is no particular limitation on the lower limit of the thickness of the sheet-like fiber substrate. It is usually 10 μm or more.

[0166] Prepregs can be manufactured using conventional methods such as hot-melt methods and solvent methods.

[0167] The thickness of the prepreg can be the same as that of the resin composition layer in the aforementioned resin sheet.

[0168] The sheet-like laminated material of the present invention is suitable for use in forming the insulating layer of a printed wiring board (for use in the insulating layer of a printed wiring board), and is suitable for use in forming the interlayer insulating layer of a printed wiring board (for use in the interlayer insulating layer of a printed wiring board).

[0169] Printed Wiring Board The printed wiring board of the present invention includes an insulating layer composed of a hardened material obtained by curing the resin composition of the present invention.

[0170] Printed wiring boards, for example using the aforementioned resin film, can be manufactured by a method comprising the steps (I) and (II) below. (I) A step of laminating resin sheets by bonding a resin composition layer of a resin sheet to the inner substrate. (II) Step of curing the resin composition layer (e.g., thermosetting) to form an insulating layer

[0171] The "inner layer substrate" used in step (I) refers to the component that becomes the substrate of the printed wiring board, such as glass epoxy board, metal substrate, polyester substrate, polyimide substrate, BT resin substrate, thermosetting polyphenylene ether substrate, etc. Furthermore, one or both sides of the substrate may have a conductor layer, which can be patterned. An inner layer substrate with conductor layers (circuit) formed on one or both sides of the substrate is sometimes called an "inner layer circuit board". Furthermore, in the manufacture of the printed wiring board, intermediate manufactured materials with insulating layers and / or conductor layers are also included in the "inner layer substrate" of this invention. When the printed wiring board is a component-embedded circuit board, an inner layer substrate with embedded components can be used.

[0172] The lamination of the inner layer substrate and the resin sheet can be performed, for example, by heating and pressing the resin sheet onto the inner layer substrate from the support side. The component for heating and pressing the resin sheet onto the inner layer substrate (hereinafter referred to as the "heat-pressing component") can be, for example, a heated metal plate (SUS mirror plate, etc.) or a metal roller (SUS roller). Furthermore, it is preferable not to directly press the resin sheet onto the heat-pressing component, but rather to press the resin sheet by using an elastic material such as heat-resistant rubber, which allows the resin sheet to fully follow the surface irregularities of the inner layer substrate.

[0173] The lamination of the inner substrate and the resin sheet can be performed using a vacuum lamination method. In the vacuum lamination method, the heating and pressing temperature is preferably in the range of 60°C to 160°C, more preferably in the range of 80°C to 140°C; the heating and pressing pressure is preferably in the range of 0.098 MPa to 1.77 MPa, more preferably in the range of 0.29 MPa to 1.47 MPa; and the heating and pressing time is preferably in the range of 20 seconds to 400 seconds, more preferably in the range of 30 seconds to 300 seconds. Lamination is preferably performed under reduced pressure conditions below 26.7 hPa.

[0174] Lamination can be performed using commercially available vacuum laminators. Examples of commercially available vacuum laminators include the vacuum pressure laminator manufactured by Meiki Manufacturing Co., Ltd., the vacuum coating machine manufactured by Nikko-Materials Co., Ltd., and the batch vacuum pressure laminator.

[0175] After lamination, the resin sheet can be smoothed under normal pressure (atmospheric pressure), for example, by pressing a heated pressing member from the support side. The pressing conditions for smoothing can be the same as the heating and pressing conditions for lamination described above. Smoothing can be performed using a commercially available laminator. Furthermore, lamination and smoothing can be performed continuously using the aforementioned commercially available vacuum laminator.

[0176] The support can be removed between step (I) and step (II), or after step (II).

[0177] In step (II), the resin composition layer is cured (e.g., thermosetting) to form an insulating layer composed of the cured resin composition. The curing conditions for the resin composition layer are not particularly limited; commonly used conditions can be used when forming the insulating layer of the printed wiring board.

[0178] For example, the thermosetting conditions of the resin composition layer vary depending on the type of resin composition, etc. In one embodiment, the curing temperature is preferably 120°C to 240°C, more preferably 150°C to 220°C, and even more preferably 170°C to 210°C. The curing time is preferably 5 minutes to 120 minutes, more preferably 10 minutes to 100 minutes, and even more preferably 15 minutes to 100 minutes.

[0179] Before heat curing the resin composition layer, the resin composition layer can be preheated at a temperature lower than the curing temperature. For example, before heat curing the resin composition layer, the resin composition layer can be preheated at a temperature of 50°C to 120°C, preferably 60°C to 115°C, more preferably 70°C to 110°C, for at least 5 minutes, preferably 5 minutes to 150 minutes, more preferably 15 minutes to 120 minutes, and even more preferably 15 minutes to 100 minutes.

[0180] When manufacturing a printed wiring board, steps (III) of creating openings in the insulating layer, (IV) of roughening the insulating layer, and (V) of forming the conductor layer can be further performed. These steps (III) to (V) can be performed by those skilled in the art of manufacturing printed wiring boards using various known methods. Furthermore, when removing the support after step (II), the removal of the support can be performed between steps (II) and (III), between steps (III) and (IV), or between steps (IV) and (V). Also, if necessary, the formation of the insulating and conductor layers in steps (II) to (V) can be repeated to form a multilayer wiring board.

[0181] In other embodiments, the printed wiring board of the present invention can be manufactured using the prepreg described above. The manufacturing method is basically the same as that used in the case of resin sheets.

[0182] Step (III) is the step of creating holes in the insulating layer, thereby forming vias, through holes, etc. Step (III) is carried out using tools such as drills, lasers, or plasma, depending on the composition of the resin used to form the insulating layer. The size or shape of the holes can be appropriately determined according to the design of the printed circuit board.

[0183] Step (IV) is a roughening process for the insulating layer. Typically, in this step (IV), adhesive residue is removed. The order and conditions of the roughening process are not particularly limited; commonly used and known sequences and conditions can be employed when forming the insulating layer of a printed circuit board. For example, the insulating layer can be roughened by performing a swelling treatment with a swelling solution, a roughening treatment using an oxidizing agent, and a neutralization treatment using a neutralizing solution in this sequence.

[0184] The swelling solution that can be used in the roughening step is not particularly limited, and examples include alkaline solutions and surfactant solutions, with alkaline solutions being preferred, and sodium hydroxide solutions and potassium hydroxide solutions being even more preferred. Commercially available swelling solutions include, for example, "Swelling Dip Securiganth P" and "Swelling Dip Securiganth SBU" manufactured by Atotec Japan. The swelling treatment using the swelling solution is not particularly limited; for example, the insulating layer can be immersed in a swelling solution at 30°C to 90°C for 1 to 20 minutes. From the viewpoint of achieving an appropriate level of resin swelling in the insulating layer, it is preferable to immerse the insulating layer in a swelling solution at 40°C to 80°C for 5 to 15 minutes.

[0185] The oxidant used for roughening is not particularly limited, but examples include alkaline permanganate solutions containing potassium permanganate or sodium permanganate dissolved in an aqueous solution of sodium hydroxide. For roughening treatment with oxidants such as alkaline permanganate solutions, it is preferable to immerse the insulating layer in an oxidant solution heated to 60°C to 100°C for 10 to 30 minutes. Furthermore, the concentration of permanganate in the alkaline permanganate solution is preferably 5% to 10% by mass. Commercially available oxidants include alkaline permanganate solutions such as "Concentrate Compact CP" and "Dosing Solution Securiganth P" manufactured by Atotech Japan.

[0186] Furthermore, the neutralizing solution used in the roughening process is preferably an acidic aqueous solution. Commercially available products include, for example, "Reduction solution Securiganth P" manufactured by Atotech Japan.

[0187] The treatment using a neutralizing solution involves immersing the surface roughened by the oxidant in a neutralizing solution at 30°C to 80°C for 5 to 30 minutes. From a workability point of view, it is preferable to immerse the roughened surface by the oxidant in a neutralizing solution at 40°C to 70°C for 5 to 20 minutes.

[0188] In one embodiment, the root mean square roughness (Rq) of the surface of the roughened insulating layer is preferably below 500 nm, more preferably below 400 nm, and even more preferably below 300 nm. The lower limit is not particularly limited; for example, it can be above 1 nm, above 2 nm, etc. The root mean square roughness (Rq) can be measured using a non-contact surface roughness meter.

[0189] Step (V) is the step of forming a conductor layer, which 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 can be a single metal layer or an alloy layer. Examples of alloy layers include layers formed from two or more metal alloys selected from the above group (e.g., nickel-chromium alloy, copper-nickel alloy, and copper-titanium alloy). From the viewpoint of versatility, cost, and ease of patterning in conductor layer formation, a single metal layer of chromium, nickel, titanium, aluminum, zinc, gold, palladium, silver, or copper, or an alloy layer of nickel-chromium alloy, copper-nickel alloy, or copper-titanium alloy, is preferred. More preferably, a single metal layer of chromium, nickel, titanium, aluminum, zinc, gold, palladium, silver, or copper, or an alloy layer of nickel-chromium alloy, is even more preferred. A single metal layer of copper is also preferred.

[0190] The conductor layer can be a single-layer structure, or a multi-layer structure consisting of two or more single-metal layers or alloy layers of different types of metals or alloys. When the conductor layer is a multi-layer structure, the layer in contact with the insulating layer is preferably a single-metal layer of chromium, zinc, or titanium, or an alloy layer of nickel-chromium alloy.

[0191] The thickness of the conductor layer depends on the desired design of the printed circuit board, and is generally 3μm~35μm, preferably 5μm~30μm.

[0192] In one embodiment, the conductor layer can be formed by plating. For example, by plating the surface of the insulating layer using conventional techniques such as semi-additive and fully additive methods, a conductor layer with the desired wiring pattern can be formed. From the viewpoint of ease of manufacturing, it is preferable to form it by the semi-additive method. The following shows an example of forming a conductor layer by the semi-additive method.

[0193] First, an electroplated seed layer is formed on the surface of the insulating layer using electroless plating. Next, a masking pattern corresponding to the desired wiring pattern is formed on the formed electroplated seed layer, exposing a portion of the seed layer. A metal layer is then formed on the exposed seed layer by electroplating, and the masking pattern is removed. Finally, the unwanted portion of the seed layer is removed by etching or other methods, thus forming a conductor layer with the desired wiring pattern.

[0194] In other embodiments, the conductor layer can be formed using metal foil. When forming the conductor layer using metal foil, step (V) is preferably performed between steps (I) and (II). For example, after step (I), the support is removed, and metal foil is deposited on the surface of the exposed resin composition layer. The deposition of the resin composition layer and the metal foil can be performed by vacuum deposition. The deposition conditions can be the same as those described in step (I). Next, step (II) is performed to form an insulating layer. Then, using the metal foil on the insulating layer, a conductor layer with the desired wiring pattern can be formed by conventional techniques such as subtractive processes or simulated semi-additive processes.

[0195] Metal foils can be manufactured using conventional methods such as electrolysis and rolling. Commercially available metal foils include, for example, HLP foil and JXUT-III foil manufactured by JX Minerals & Metals Corporation, and 3EC-III foil and TP-III foil manufactured by Mitsui Mining & Metals Corporation.

[0196] Semiconductor Devices 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.

[0197] Semiconductor devices can be categorized into various semiconductor devices supplied to electrical products (e.g., computers, mobile phones, digital cameras, and televisions) and vehicles (e.g., motorcycles, automobiles, trams, ships, and aircraft). Implementation

[0198] [Example]

[0199] The present invention will be described in more detail below with reference to the embodiments. The present invention is not limited to these embodiments. Furthermore, the terms "parts" and "%" used to indicate quantities will, unless otherwise specified, indicate "parts by mass" and "% by mass," respectively. In particular, the temperature condition when no temperature is specified is room temperature (25°C).

[0200] <Example 1> Ten parts of an amine compound containing a biphenyl skeleton ("BAN" manufactured by Nippon Kayaku Co., Ltd.), 20 parts of an aliphatic maleimide compound ("BMI-689" manufactured by Designer Molecules Co., Ltd.), 28.6 parts of an aromatic maleimide compound ("MIR-3000-70MT" manufactured by Nippon Kayaku Co., Ltd., a 70% solid MEK / toluene mixed solution), 1 part of an imidazole-based curing accelerator ("1B2PZ" manufactured by Shikoku Kasei Co., Ltd., 1-benzyl-2-phenylimidazolium), and 60 parts of spherical silica ("SO-C2" manufactured by Admatechs Co., Ltd., with an average particle size of 0.5 μm and a specific surface area of ​​5.8 m² / g) surface-treated with a silane coupling agent ("KBM-573" manufactured by Shin-Etsu Chemical Co., Ltd., N-phenyl-3-aminopropyltrimethoxysilane) were mixed and uniformly dispersed using a high-speed rotary mixer to prepare a resin composition.

[0201] <Example 2> Except for using 20 parts of aliphatic maleimide compound (Designer Molecules "BMI-1500") instead of 20 parts of aliphatic maleimide compound (Designer Molecules "BMI-689"), the resin composition was prepared in the same manner as in Example 1.

[0202] <Example 3> Except for using 20 parts of an aliphatic maleimide compound (Designer Molecules, "BMI-2500") instead of 20 parts of an aliphatic maleimide compound (Designer Molecules, "BMI-689"), the resin composition was prepared in the same manner as in Example 1.

[0203] <Example 4> Except for using 20 parts of an aliphatic maleimide compound (Designer Molecules "BMI-3000J") instead of 20 parts of an aliphatic maleimide compound (Designer Molecules "BMI-689"), the resin composition was prepared in the same manner as in Example 1.

[0204] <Example 5> Except for using 20 parts of aromatic maleimide compound (Designer Molecules "BMI-6100") to replace 28.6 parts of aromatic maleimide compound (MIR-3000-70MT, Nippon Kayaku Co., Ltd., a 70% solid MEK / toluene mixed solution), the resin composition was prepared in the same way in Example 2.

[0205] <Example 6> Except for using 20 parts of aromatic maleimide compound (Designer Molecules "BMI-6100") to replace 28.6 parts of aromatic maleimide compound (MIR-3000-70MT, Nippon Kayaku Co., Ltd., a 70% solid MEK / toluene mixed solution), the resin composition was prepared in the same way in Example 3.

[0206] <Example 7> Except for changing the amount of aromatic maleimide compound (MIR-3000-70MT manufactured by Nippon Kayaku Co., Ltd., a 70% solid MEK / toluene mixed solution) from 28.6 parts to 14.3 parts, and further using 10 parts of aromatic maleimide compound (BMI-6100 manufactured by Designer Molecules Co., Ltd.), the resin composition was prepared in the same manner as in Example 2.

[0207] <Example 8> A MEK solution (70% by mass) of maleicimine compound A (Mw / Mn=1.81, v”=1.47 (mainly 1, 2 or 3)) represented by the following formula (X) was prepared to be synthesized by the method described in Synthesis Example 1 of Patent Application Publication No. 2020-500211 of the China Invention Association.

[0208]

[0209] Except for replacing 28.6 parts of aromatic maleimide compound (maleimide compound A represented by formula (X), a MEK solution with 70% by mass of solid content) with 28.6 parts of aromatic maleimide compound (MIR-3000-70MT manufactured by Nippon Kayaku Co., Ltd., a MEK / toluene mixed solution with 70% by mass of solid content), the resin composition was prepared in the same manner as in Example 2.

[0210] <Example 9> Except for changing the amount of spherical silica (Admatechs' SO-C2) surface-treated with silane coupling agent (Shin-Etsu Chemical Co., Ltd. "KBM-573", N-phenyl-3-aminopropyltrimethoxysilane) from 60 parts to 70 parts, and further using 15.4 parts of vinyl benzyl modified polyphenylene ether (Mitsubishi Gas Chemical Co., Ltd. "OPE-2St 2200", toluene solution with 65% solids content), the resin composition was prepared in the same manner as in Example 2.

[0211] <Example 10> Except for changing the amount of spherical silica (Admatechs' SO-C2) surface-treated with silane coupling agent (Shin-Etsu Chemical Co., Ltd.'s "KBM-573" and N-phenyl-3-aminopropyltrimethoxysilane) from 60 parts to 70 parts, and further using 20 parts of methacrylic acid modified polyphenylene ether (a toluene solution with SABIC Innovative Plastics' "SA9000-111" as 50% solid component), the resin composition was prepared in the same manner as in Example 2.

[0212] <Example 11> Except for changing the amount of spherical silica (Admatechs' SO-C2) surface-treated with silane coupling agent (Shin-Etsu Chemical Co., Ltd.'s "KBM-573", N-phenyl-3-aminopropyltrimethoxysilane) from 60 parts to 70 parts, and further using 15.4 parts of divinylbenzene / styrene copolymer (NIPPON STEEL Chemical & Material Co., Ltd.'s "ODV-XET-X04", a toluene solution with 65% solids content), the resin composition was prepared in the same manner as in Example 2.

[0213] <Comparative Example 1> Except for the absence of 20 parts of the aliphatic maleimide compound (Designer Molecules' "BMI-689"), and the change in the amount of the aromatic maleimide compound (Nippon Kayaku Co.'s "MIR-3000-70MT", a 70% solid MEK / toluene mixed solution) from 28.6 parts to 57.1 parts, the resin composition was prepared in the same manner as in Example 1.

[0214] <Comparative Example 2> Except for changing the amount of aliphatic maleimide compound (Designer Molecules, "BMI-689") from 20 parts to 10 parts, and using 10 parts of an amine compound without a biphenyl skeleton (Nippon Kayaku Co., Ltd., "AA") instead of 10 parts of an amine compound containing a biphenyl skeleton (Nippon Kayaku Co., Ltd., "BAN"), the resin composition was prepared in the same manner as in Example 1.

[0215] <Experimental Example 1: Determination of specific capacitance (Dk) and dielectric tangent (Df)> A polyethylene terephthalate film (Lintec Corporation "AL5", thickness 38 μm) with a release layer was prepared as a support. The resin composition obtained in the examples and comparative examples was uniformly coated onto the release layer of this support, so that the thickness of the dried resin composition layer was 40 μm. Then, the resin composition was dried at 80°C to 100°C (average 90°C) for 4 minutes to obtain a resin sheet A comprising the support and the resin composition layer.

[0216] The obtained resin sheet A was cured in an oven at 190°C for 90 minutes. After removing the resin sheet A from the oven, the support was peeled off to obtain a cured resin composition layer. The cured material was cut into pieces with a length of 80 mm and a width of 2 mm, which were used as evaluation cured material B.

[0217] For the evaluation of hardened material B, the dielectric constant (Dk value) and dielectric tangent (Df value) were measured using the cavity perturbation method (HP8362B) manufactured by Agilent Technologies at a measurement frequency of 5.8 GHz and a measurement temperature of 23 °C. Measurements were performed on two test pieces, and the average values ​​were calculated.

[0218] <Experimental Example 2: Determination of Peel Strength and Arithmetic Mean Roughness (Ra)> (1) Preparation of inner layer substrate The inner circuit support glass cloth substrate epoxy resin double-sided copper multilayer board (copper foil thickness 18μm, substrate thickness 0.4mm, Panasonic "R1515A") is formed by etching 1μm on both sides with micro etchant (MEC "CZ8101") to roughen the copper surface.

[0219] (2) Lamination of resin sheet A Using a batch vacuum pressure laminator (Nikko-Materials, 2-stage CVP700), the resin sheet A obtained in Example 1 was laminated onto both sides of the inner layer substrate by contacting the resin composition layer with the inner layer substrate. The lamination was performed by depressurizing for 30 seconds, adjusting the pressure to below 13 hPa, and then pressing at 120°C and 0.74 MPa for 30 seconds. Next, it was hot-pressed at 100°C and 0.5 MPa for 60 seconds.

[0220] (3) Thermal curing of resin composition layers Then, the inner layer substrate with resin sheet A is placed in an oven at 130°C and heated for 30 minutes. Next, it is transferred to an oven at 190°C and heated for 30 minutes to thermally harden the resin composition layer and form an insulating layer. Then, the support is peeled off to obtain a hardened substrate A having an insulating layer, an inner layer substrate, and an insulating layer in sequence.

[0221] (4) Roughening treatment The hardened substrate A undergoes a roughening process to remove adhesive residue. The following wet adhesive residue removal process is performed as the adhesive residue removal treatment.

[0222] (Wet degumming treatment) The hardened substrate A was immersed in a swelling solution (an aqueous solution of Swelling Dip Securiganth P manufactured by Atotech Japan, diethylene glycol monobutyl ether, and sodium hydroxide) at 60°C for 5 minutes. Then, it was immersed in an oxidizing agent solution (an aqueous solution of Concentrate Compact CP manufactured by Atotech Japan, approximately 6% potassium permanganate, and approximately 4% sodium hydroxide) at 80°C for 20 minutes. Next, it was immersed in a neutralizing solution (a aqueous solution of Reduction Solution Securiganth P manufactured by Atotech Japan and sulfuric acid) at 40°C for 5 minutes, and then dried at 80°C for 15 minutes.

[0223] (5) Determination of the arithmetic mean roughness (Ra) of the surface of the insulation layer after roughening treatment Using a non-contact surface roughness meter (Bruker WYKO NT3300), in VSI mode with a 50x lens, and a measurement range of 121μm × 92μm, the arithmetic mean roughness (Ra) of the insulating layer surface of the hardened substrate A after roughening treatment was obtained. The average value of 10 points was calculated for each measurement.

[0224] (6) Formation of the conductor layer According to the semi-additive method, a conductor layer is formed on the roughened surface of the insulating layer of the hardened substrate A. Specifically, the roughened substrate is immersed in an electroless plating solution containing PdCl2 at 40°C for 5 minutes, followed by immersion in an electroless copper plating solution at 25°C for 20 minutes. Next, it is annealed at 150°C for 30 minutes to form an etch resist, and a pattern is formed by etching. Then, copper sulfate electroplating is performed to form a conductor layer with a thickness of 25 μm, followed by annealing at 190°C for 60 minutes. The resulting substrate is referred to as "evaluation substrate B".

[0225] (7) Determination of peel strength of electroplated conductor layer The peel strength between the insulation layer and the conductor layer was measured according to Japanese Industrial Standard (JIS C6481). Specifically, on the conductor layer of the evaluation substrate B, a section 10 mm wide and 100 mm long was cut, and this end was peeled off. The peel was held in place with a gripper, and at room temperature, the load (kgf / cm) at which a 35 mm vertical peel was pulled was measured at a speed of 50 mm / min. The peel strength was then determined using a tensile testing machine (TSE Corporation "AC-50C-SL").

[0226] The amount of non-volatile components used in the resin composition of the examples and comparative examples, and the test results of the test examples are shown in Table 1 below.

[0227]

[0228] The above describes how, by using a resin composition comprising (A) an amine compound having a biphenyl skeleton, (B) a maleimide compound having an aliphatic chain with 7 or more carbon atoms, and (C) a maleimide compound without an aliphatic chain with 7 or more carbon atoms, a hardened material with low specific capacitance (Dk) and dielectric tangent (Df) and excellent peel strength of the electroplated conductor layer can be obtained.

Claims

1. A resin composition comprising (A) an amine compound having a biphenyl backbone, (B) a maleimide compound having a fatty chain having 7 or more carbon atoms, (C) a maleimide compound not having a fatty chain having 7 or more carbon atoms, and (E) an inorganic filler; wherein component (A) comprises having the formula (A1):

1. [In the formula, V and W each independently represent -C(R')2-, R each independently represents a substituent, R' each independently represents a hydrogen atom or substituent, and h, i, and j each independently represent an integer from 0 to 2] represents an amine compound with repeating units, wherein component (B) is an inclusion formula (B1):

1. [In the formula, A1 independently represents a divalent organic group having an aliphatic chain with 7 or more carbon atoms, A2 independently represents a divalent organic group not having an aliphatic chain with 7 or more carbon atoms, B1 independently represents a tetravalent organic group having an aromatic ring and / or a non-aromatic ring, n1 and n2 represent integers of 0 or more, m1 and m2 represent either 1 or the others as 0, and the sum of n1 and m1 is 1 or more] represents a maleimine compound, wherein component (C) is an inclusion formula (C1-1) or (C1-2):

1. [In the formula, B2 independently represents a tetravalent organic group without a fatty chain having 7 or more carbon atoms; n represents an integer of 1 or more; A3 independently represents a divalent organic group without a fatty chain having 7 or more carbon atoms; R3 independently represents an alkyl or phenyl group with 1 to 6 carbon atoms; s represents an integer of 1 or more; t independently represents an integer of 0 to 2; other symbols are the same as in formula (B1)] represents a maleimine compound, wherein when the non-volatile component in the resin composition is set to 100% by mass, the content of component (A) is 5% by mass or more, wherein the mass ratio of component (A) to the total of components (B) and (C) ((A) component / (B) component and (C) total)) is 0.1 to 0.

3.

2. As in the resin composition of claim 1, where the non-volatile component in the resin composition is set to 100% by mass, the content of component (B) is 3% to 40% by mass.

3. As in the resin composition of claim 1, where the non-volatile component in the resin composition is set to 100% by mass, the content of component (C) is 3% to 40% by mass.

4. The resin composition as claimed in claim 1, wherein the mass ratio of component (C) to component (B) (component (C) / component (B)) is 0.5 to 20.

5. The resin composition of claim 1 further comprises (D) a free radical polymerizable compound other than components (B) and (C).

6. In the resin composition of claim 1, where the non-volatile component in the resin composition is set to 100% by mass, the content of component (E) is 25% by mass or more.

7. The resin composition of claim 1, wherein the dielectric tangent of the cured resin composition is less than 0.004 when measured at 5.8 GHz and 23 °C.

8. The resin composition of claim 1, wherein the specific capacitance of the cured resin composition is 2.9 or less when measured at 5.8 GHz and 23 °C.

9. A cured material, which is a cured material of the resin composition of any one of claims 1 to 8.

10. A sheet-like laminated material comprising a resin composition as claimed in any one of claims 1 to 8.

11. A resin sheet having a support and a resin composition layer formed of any one of the resin compositions of claims 1 to 8 disposed on the support.

12. A printed wiring board having an insulating layer made of a cured resin composition of any one of claims 1 to 8.

13. A semiconductor device comprising the printed wiring board of claim 12.