TW202212417A - resin composition - Google Patents

Abstract

The present invention addresses the problem of providing a resin composition with which it is possible to obtain a cured product having a low arithmetic average roughness (Ra), a low relative dielectric constant (Dk), and a low dielectric loss tangent (Df). The solution of the present invention is a resin composition containing (A) a maleimide compound containing, in one molecule, a divalent group represented by formula (1), a divalent group represented by formula (2) and/or a divalent group represented by formula (3), (B) an epoxy resin, and (C) an inorganic filler, wherein the content of the component (C) is more than 30% by mass when a non-volatile component in the resin composition is taken as 100% by mass (the definition of each symbol is as described in the specification).

Description

resin composition

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

As a manufacturing technique of a printed wiring board, the manufacturing method of the build-up method by alternately stacking insulating layers and conductor layers is known. In the manufacturing method by the build-up method, the insulating layer is generally formed by curing the resin composition.

In recent years, along with the increase in the frequency of signals due to the progress of miniaturization and higher performance of electronic equipment, lower dielectric constant and dielectric tangent of the insulating layer of the multilayer printed wiring board are required. In addition, in order to improve the adhesion with miniaturized and high-density wiring, an insulating layer with a smaller surface roughness is required.

Patent Documents 1 and 2 disclose resin compositions using various maleimide compounds. [Prior Art Literature] [Patent Literature]

[Patent Document 1] International Publication No. 2018/212116 [Patent Document 2] International Publication No. 2020/045489

[The problem to be solved by the invention]

The subject of this invention is providing the resin composition which can obtain the hardened|cured material whose arithmetic mean roughness (Ra) is small, and a specific permittivity (Dk) and a dielectric tangent (Df) are low. [Means of Solving Problems]

In order to achieve the subject of the present invention, as a result of intensive research, the present inventors found that by using a specific maleimide compound as a component of the resin composition, unexpectedly, the arithmetic mean roughness (Ra) is small, In addition, the present invention has been completed as a cured product having a low specific permittivity (Dk) and dielectric tangent (Df).

That is, the present invention includes the following contents. [1]. A resin composition comprising (A) a maleimide compound, (B) an epoxy resin, and (C) an inorganic filler, and wherein the nonvolatile content in the resin composition is 100% by mass When the content of the component (C) exceeds 30 mass %, the maleimide compound contains, in 1 molecule, a divalent group represented by the formula (1) and a divalent group represented by the formula (2) a valent group and/or a divalent group represented by the formula (3),

[wherein, X ¹ represents a single bond, -C(R ¹⁰ ) ₂ -, -O-, -CO-, -S-, -SO-, -SO ₂ -, -CONH-, -NHCO-, -COO -, or -OCO-; R ¹⁰ independently represents a hydrogen atom, an alkyl group, an alkenyl group, an aryl-alkyl group, or an aryl group; R ¹¹ , R ¹² , R ¹³ , R ¹⁴ , R ²¹ , R ²² , R ²³ , and R ²⁴ , at least one of them independently represents an alkyl group, an alkenyl group, an aryl-alkyl group, or an aryl group, and the other represents a hydrogen atom; and * represents a bonding site]

[In the formula, R ³¹ , R ³² , and R ³³ each independently represent a hydrogen atom, an alkyl group, an alkenyl group, an aryl-alkyl group, or an aryl group; and * represents a bonding site]

[In the formula, R ⁴¹ and R ⁴² each independently represent a hydrogen atom, an alkyl group, an alkenyl group, an aryl-alkyl group, or an aryl group; and * represents a bonding site]. [2]. The resin composition according to the above [1], wherein X ¹ is -C(R ¹⁰ ) ₂ -; R ¹¹ , R ¹² , R ²¹ , and R ²² are each independently an alkyl group; and R ¹⁰ , R ¹³ , R ¹⁴ , R ²³ , R ²⁴ , R ³¹ , R ³² , R ³³ , R ⁴¹ , and R ⁴² are hydrogen atoms. [3]. The resin composition according to the above [1] or [2], wherein the (A) component further contains a divalent group represented by the formula (4) in 1 molecule,

[wherein, X ² , X ³ , and X ⁴ independently represent a single bond, -C(R ⁵⁰ ) ₂ -, -O-, -CO-, -S-, -SO-, -SO ₂ -, - CONH-, -NHCO-, -COO-, or -OCO-; R ⁵⁰ , R ⁵¹ , R ⁵² , R ⁵³ , R ⁵⁴ , R ⁶¹ , R ⁶² , R ⁶³ , R ⁶⁴ , R ⁷¹ , R ⁷² , R ⁷³ , R ⁷⁴ , R ⁸¹ , R ⁸² , R ⁸³ , and R ⁸⁴ each independently represent a hydrogen atom, an alkyl group, an alkenyl group, an aryl-alkyl group, or an aryl group; and * represents a bonding site]. [4]. The resin composition according to the above [3], wherein X ² and X ⁴ are -O-; X ³ is -C(R ⁵⁰ ) ₂ -; R ⁵⁰ is each independently an alkyl group; and R ⁵¹ , R ⁵² , R ⁵³ , R ⁵⁴ , R ⁶¹ , R ⁶² , R ⁶³ , R ⁶⁴ , R ⁷¹ , R ⁷² , R ⁷³ , R ⁷⁴ , R ⁸¹ , R ⁸² , R ⁸³ , and R ⁸⁴ are hydrogen atoms. [5]. The resin composition according to any one of the above [1] to [4], wherein the content of the component (A) is 1 mass % when the nonvolatile content in the resin composition is 100 mass % %~40% by mass. [6]. The resin composition according to any one of [1] to [5], further comprising (A') radically polymerizable compounds other than the (A) component. [7]. The resin composition according to any one of the above [1] to [6], wherein the (B) component contains (B-1) an epoxy resin having a condensed ring structure. [8]. The resin composition according to the above [7], wherein the component (B-1) contains a naphthol aralkyl type epoxy resin. [9]. The resin composition according to any one of the above [1] to [8], wherein the content of the component (B) is 1 mass % when the nonvolatile content in the resin composition is 100 mass % %~50% by mass. [10]. The resin composition according to any one of the above [1] to [9], wherein the mass ratio of (A) component to (B) component ((A) component/(B) component) is 0.3~ 3. [11]. The resin composition according to any one of the above [1] to [10], wherein the content of the component (C) is 50 mass % when the non-volatile matter in the resin composition is 100 mass % %above. [12]. The resin composition according to any one of the above [1] to [11], wherein the mass ratio of (A) component to (C) component ((A) component/(C) component) is 0.05~ 0.5. [13]. The resin composition according to any one of the above [1] to [12], further comprising (D) an active ester compound. [14]. The resin composition according to any one of the above [1] to [13], wherein the dielectric tangent of the cured product of the resin composition is 0.005 or less when measured at 5.8 GHz and 23°C. [15]. The resin composition according to any one of the above [1] to [14], wherein the specific permittivity of the cured product of the resin composition is 3.0 or less when measured at 5.8 GHz and 23°C. [16]. A cured product of the resin composition according to any one of the above [1] to [15]. [17]. A sheet-like laminate material comprising the resin composition of any one of the above [1] to [15]. [18]. A resin sheet comprising a support body and a resin composition layer provided on the support body, the resin composition layer being formed of the resin composition of any one of the above [1] to [15]. [19]. A printed wiring board including an insulating layer made of a cured product of the resin composition according to any one of the above [1] to [15]. [20]. A semiconductor device comprising the printed wiring board of the above [19]. [Effect of invention]

According to the resin composition of the present invention, a cured product having a small arithmetic mean roughness (Ra) and a low specific permittivity (Dk) and a low dielectric tangent (Df) can be obtained.

[The best form of implementing the invention]

Hereinafter, the present invention will be described in detail based on this suitable embodiment. However, the present invention is not limited to the following embodiments and examples, and can be modified and implemented arbitrarily without departing from the scope of the claims of the present invention and its equivalents.

<Resin composition> The resin composition of the present invention contains (A) a maleimide compound, (B) an epoxy resin, and (C) an inorganic filler, and when the nonvolatile content in the resin composition is 100% by mass, ( C) The content of the component is more than 30 mass %, wherein the maleimide compound contains a divalent group represented by the formula (1) and a divalent group represented by the formula (2) in one molecule. and/or a divalent group represented by formula (3). By using such a resin composition, it is possible to obtain a cured product having a small arithmetic mean roughness (Ra) and a low specific permittivity (Dk) and a dielectric tangent (Df).

The resin composition of the present invention may contain any components in addition to (A) a maleimide compound, (B) an epoxy resin, and (C) an inorganic filler, wherein the maleimide The amine compound contains, in one molecule, a divalent group represented by formula (1), a divalent group represented by formula (2), and/or a divalent group represented by formula (3). Examples of optional components include (A') other maleimide compounds, (D) active ester compounds, (E) hardening accelerators, (F) other additives, and (G) organic solvents. Hereinafter, each component contained in the resin composition will be described in detail.

<(A) Specific maleimide compound> The resin composition of the present invention contains (A) a maleimide compound (hereinafter also referred to as a "specific maleimide compound"), wherein the maleimide compound contains, in one molecule, the formula (1 ) represented by the bivalent group, and the bivalent group represented by the formula (2) and/or the bivalent group represented by the formula (3). The maleimide compound refers to an organic compound containing at least one maleimide group (2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl) in the molecule. (A) The specific maleimide compound may be used alone or in combination of two or more at an arbitrary ratio.

(A) The specific maleimide compound contains a divalent group represented by the formula (1) in one molecule:

[In the formula, * represents a bond site, and other symbols are as described below].

In formula (1), X ¹ represents a single bond, -C(R ¹⁰ ) ₂ -, -O-, -CO-, -S-, -SO-, -SO ₂ -, -CONH-, -NHCO-, -COO-, or -OCO-. X ¹ is preferably -C(R ¹⁰ ) ₂ -, -O-, -CO-, -S-, -SO-, or -SO ₂ -; more preferably -C(R ¹⁰ ) ₂ -, or - O-; particularly preferably -C(R ¹⁰ ) ₂ -.

In formula (1), R ¹⁰ each independently represents a hydrogen atom, an alkyl group, an alkenyl group, an aryl-alkyl group (an alkyl group substituted with one aryl group at a substitutable position), or an aryl group. R ¹⁰ is preferably each independently a hydrogen atom or an alkyl group; particularly preferably a hydrogen atom.

The term "alkyl (group)" refers to a linear, branched and/or cyclic monovalent aliphatic saturated hydrocarbon group. The alkyl (group) preferably has 1 to 14 carbon atoms, more preferably 1 to 10 carbon atoms, and more preferably 1 to 6 or 4 to 10 carbon atoms. Examples of the alkyl (group) include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, Nonyl, decyl, cyclopentyl, cyclohexyl, methylcyclohexyl, dimethylcyclohexyl, trimethylcyclohexyl, cyclopentylmethyl, cyclohexylmethyl and the like. The alkenyl (group) refers to a linear, branched and/or cyclic monovalent aliphatic unsaturated hydrocarbon group having at least one carbon-carbon double bond. The alkenyl (group) preferably has 2 to 14 carbon atoms, more preferably 2 to 10 carbon atoms, more preferably 2 to 6 or 4 to 10 carbon atoms. As an alkene (group), a vinyl group, a propenyl group, a butenyl group, a pentenyl group, a hexenyl group, a heptenyl group, an octenyl group, a nonenyl group, a decenyl group, a cyclohexenyl group, etc. are mentioned, for example. The aryl (group) refers to a monovalent aromatic hydrocarbon group. The aryl (group) preferably has 6 to 14 carbon atoms. As an aryl group, a phenyl group, a 1-naphthyl group, a 2-naphthyl group, etc. are mentioned, for example.

In formula (1), R ¹¹ , R ¹² , R ¹³ , R ¹⁴ , R ²¹ , R ²² , R ²³ , and R ²⁴ , at least one of them (preferably at least two, and more preferably At least 4) each independently represents an alkyl group, an alkenyl group, an aryl-alkyl group, or an aryl group; and the others represent a hydrogen atom. Preferably at least one (and preferably at least two) of R ¹¹ , R ¹² , R ¹³ , and R ¹⁴ , and at least one (and more preferably at least two) of R ²¹ , R ²² , R ²³ , and R ²⁴ Preferably at least 2) are each independently an alkyl group, an alkenyl group, an aryl-alkyl group, or an aryl group; and the others are hydrogen atoms. It is also preferred that R ¹¹ , R ¹² , R ²¹ , and R ²² are each independently alkyl, alkenyl, aryl-alkyl, or aryl; and R ¹³ , R ¹⁴ , R ²³ , and R ²⁴ are hydrogen atom. Particularly preferably, R ¹¹ , R ¹² , R ²¹ , and R ²² are each independently an alkyl group; and R ¹³ , R ¹⁴ , R ²³ , and R ²⁴ are hydrogen atoms.

The divalent radical represented by the formula (1) is particularly preferably a divalent radical represented by the formula (1'):

[In the formula, * represents a bonding site].

(A) The specific maleimide compound contains, in addition to the divalent group represented by the formula (1), a divalent group represented by the formula (2) in one molecule:

[wherein, * represents a bond site, and other symbols are as described below], and/or a divalent group represented by formula (3):

[In the formula, * represents a bond site, and other symbols are as described below]. It is preferable that (A) specific maleimide compound further contains the divalent group represented by formula (2) in 1 molecule in addition to the divalent group represented by formula (1).

In formula (2), R ³¹ , R ³² , and R ³³ each independently represent a hydrogen atom, an alkyl group, an alkenyl group, an aryl-alkyl group, or an aryl group. R ³¹ , R ³² , and R ³³ are preferably each independently a hydrogen atom or an alkyl group; particularly preferably a hydrogen atom.

In formula (3), R ⁴¹ and R ⁴² each independently represent a hydrogen atom, an alkyl group, an alkenyl group, an aryl-alkyl group, or an aryl group. R ⁴¹ and R ⁴² are preferably each independently a hydrogen atom or an alkyl group; particularly preferably a hydrogen atom.

(A) Specific maleimide compounds other than the divalent group represented by the formula (1), the divalent group represented by the formula (2), and/or the divalent group represented by the formula (3) In addition to the group, it is preferable to further contain a divalent group represented by the formula (4) in one molecule:

[In the formula, * represents a bond site, and other symbols are as described below].

In formula (4), X ² , X ³ , and X ⁴ each independently represent a single bond, -C(R ⁵⁰ ) ₂ -, -O-, -CO-, -S-, -SO-, -SO ₂ - , -CONH-, -NHCO-, -COO-, or -OCO-. Preferably, X ² , X ³ , and X ⁴ are each independently -C(R ⁵⁰ ) ₂ -, -O-, -CO-, -S-, -SO-, or -SO ₂ -. More preferably, X ² , X ³ , and X ⁴ are each independently -C(R ⁵⁰ ) ₂ - or -O-. In particular, X ² and X ⁴ are -O-; and X ³ is -C(R ⁵⁰ ) ₂ -.

In formula (4), R ⁵⁰ each independently represents a hydrogen atom, an alkyl group, an alkenyl group, an aryl-alkyl group, or an aryl group. R ⁵⁰ is preferably each independently a hydrogen atom or an alkyl group; particularly preferably each independently an alkyl group.

In formula (4), R ⁵¹ , R ⁵² , R ⁵³ , R ⁵⁴ , R ⁶¹ , R ⁶² , R ⁶³ , R ⁶⁴ , R ⁷¹ , R ⁷² , R ⁷³ , R ⁷⁴ , R ⁸¹ , R ⁸² , R ⁸³ , and R ⁸⁴ each independently represent a hydrogen atom, an alkyl group, an alkenyl group, an aryl-alkyl group, or an aryl group. R ⁵¹ , R ⁵² , R ⁵³ , R ⁵⁴ , R ⁶¹ , R ⁶² , R ⁶³ , R ⁶⁴ , R ⁷¹ , R ⁷² , R ⁷³ , R ⁷⁴ , R ⁸¹ , R ⁸² , R ⁸³ , and R ⁸⁴ are compared Preferably, they are each independently a hydrogen atom or an alkyl group; particularly preferably, they are a hydrogen atom.

The divalent radical represented by the formula (4) is particularly preferably a divalent radical represented by the formula (4'):

[In the formula, * represents a bonding site].

In one embodiment, the specific maleimide compound (A) preferably contains a divalent group represented by the formula (1) and a divalent group represented by the formula (2) in one molecule. and/or a maleimide-terminated polyimide obtained by a divalent group represented by the formula (3) (hereinafter also referred to as "specific maleimide-terminated polyimide"). The maleimide-terminated polyimide refers to a chain-like polyimide having maleimide groups at both ends (a chain-like polymer including an imide structure in a repeating unit). It is known that a maleimide-terminated polyimide system can be obtained, for example, by subjecting a component containing a diamine compound, maleic anhydride, and tetracarboxylic dianhydride to an imidization reaction.

In one embodiment, (A) the specific maleimide compound is preferably the maleimide compound represented by the formula (A1):

[In the formula, A ¹ each independently represents a carbon atom, an oxygen atom, a nitrogen atom, and a sulfur atom selected from the group consisting of 2 or more (for example, 2 to 3000, 2 to 1000, 2 to 100, and 2 to 50). A divalent organic group composed of skeleton atoms; A ² independently represents a single bond, or is selected from more than 1 (for example, 1~3000, 1~1000, 1~100, 1~50) A divalent organic group composed of skeleton atoms of carbon atom, oxygen atom, nitrogen atom, and sulfur atom; n1 represents an integer of 1 or more; n2 represents an integer of 0 or more; either one of n1' and n2' represents 1 and The other side represents 0; m independently represents 0 or 1; other symbols are the same as those of formula (1)]. In formula (A1) and formulas (A2) to (A5) described below, the order and arrangement of n1 units and n2 units are not particularly limited, and include alternating copolymers, block copolymers, random copolymers, etc. . In formula (A1) and formulae (A2) to (A4) described below, each of the unit systems of n1 unit and n2 unit may be the same or different.

A ¹ is each independently preferably a divalent group represented by the following formula (Y1):

[In the formula, Y ¹¹ independently represents a single bond, an alkylene group or an alkenylene group; Y ¹² independently represents a single bond, an alkylene group, an alkenylene group, -O-, -CO-, -S-, -SO -, -SO ₂ -, -CONH-, -NHCO-, -COO-, or -OCO-; Z ¹ independently represents a non-aromatic ring that may have a substituent or an aromatic ring that may have a substituent; a represents 0 or an integer of 1 or more (preferably 0 or an integer of 1 to 5); * represents a bond site]. Still, each unit of a unit system can be the same, or it can be different.

In the present specification, the "substituent" is not particularly limited, and examples thereof include an alkyl group, an alkenyl group, an aryl group, an aryl-alkyl group, an alkyl-oxy group, an alkenyl-oxy group, an aryl-oxy group, a Alkyl-carbonyl, alkenyl-carbonyl, aryl-carbonyl, alkyl-oxy-carbonyl, alkenyl-oxy-carbonyl, aryl-oxy-carbonyl, alkyl-carbonyl-oxy, alkenyl- Monovalent substituents such as carbonyl-oxy and aryl-carbonyl-oxy may include divalent substituents such as pendant oxygen (=O) if they can be substituted.

The term "alkylene" refers to a linear or branched bivalent aliphatic saturated hydrocarbon group. The alkylene group is preferably an alkylene group having 1 to 14 carbon atoms. Examples of the alkylene group include a methylene group, an ethylidene group, a trimethylene group, a tetramethylene group, a pentamethylene group, a hexamethylene group, a heptamethylene group, an octamethylene group, and an octamethylene group. , nonamethylene, decamethylene and other straight-chain alkylene groups; ethylene (-CH(CH ₃ )-), propylene (-CH(CH ₂ CH ₃ )-), isopropylene (-C(CH ₃ ) ₂ -), ethylmethylmethylene (-C(CH ₃ )(CH ₂ CH ₃ )-), diethylmethylene (-C(CH ₂ CH ₃ ) ₂ -), 2-methyltetramethylene, 2,3-dimethyltetramethylene, 1,3-dimethyltetramethylene, 2-methylpentamethylene, 2,2-dimethylene Methylpentamethylene, 2,4-dimethylpentamethylene, 1,3,5-methylpentamethylene, 2-methylhexamethylene, 2,2-dimethylhexamethylene Methyl, 2,4-dimethylhexamethylene, 1,3,5-trimethylhexamethylene, 2,2,4-trimethylhexamethylene, 2,4,4-trimethylhexamethylene Branched chain alkylene such as methyl hexamethylene and the like. The alkenylene group means a linear or branched divalent aliphatic unsaturated hydrocarbon group having at least one carbon-carbon double bond. The alkenylene group is preferably an alkenylene group having 2 to 14 carbon atoms. The alkenylene group includes, for example, a group obtained by substituting an arbitrary carbon-carbon single bond in the specific example of the alkylene group with a carbon-carbon double bond.

The so-called aromatic ring refers to a ring according to Hückel's rule, and the number of electrons contained in the π electron system on the ring is 4n+2 (n is a natural number), which includes not only monocyclic aromatic rings, and Condensed aromatic rings obtained by condensing two or more monocyclic aromatic rings also include condensed aromatic rings obtained by condensing one or more monocyclic non-aromatic rings on one or more monocyclic aromatic rings ring. Although the aromatic ring can be a carbocyclic ring or a heterocyclic ring, in one embodiment, a carbocyclic ring is preferred. Examples of the aromatic ring include monocyclic aromatic rings (preferably 5- or 6-membered) such as benzene rings and pyridine rings, condensed aromatic rings (preferably 8- to 6-membered rings) such as indenane rings, fluorene rings, and naphthalene rings. 15 members) etc.

The non-aromatic ring means a ring other than an aromatic ring, and includes a monocyclic non-aromatic ring and a condensed non-aromatic ring obtained by condensing two or more monocyclic non-aromatic rings. The non-aromatic ring system can be a carbocycle or a heterocycle, and in one embodiment, a carbocycle is preferred. The non-aromatic ring system may be a saturated ring or an unsaturated ring, and in one embodiment, a saturated ring is preferred. Examples of non-aromatic rings include monocycloalkane rings such as cyclopropane ring, cyclobutane ring, cyclopentane ring, cyclohexane ring, cycloheptane ring, and cyclooctane ring; Monocyclic olefin rings such as hexene rings and cycloheptene rings; monocyclic non-aromatic heterocycles such as pyrrolidine rings, tetrahydrofuran rings, dioxane rings, tetrahydropyran rings, etc. Aromatic rings (preferably 3-10 members); condensed non-aromatic rings (preferably 8- 15 members).

The specific example of the divalent group represented by the formula (Y1) is not particularly limited, and the divalent organic group represented by the following can be mentioned:

[In the formula, * represents a bonding site].

A ² is each independently preferably a divalent group (including a single bond) represented by the formula (Y2):

[wherein, Y ² independently represents a single bond, an alkylene group, an alkenylene group, -O-, -CO-, -S-, -SO-, -SO ₂ -, -CONH-, -NHCO-, - COO-, or -OCO-; Z ² independently represents a non-aromatic ring that may have a substituent, or an aromatic ring that may have a substituent; b represents an integer of 0 or more (preferably an integer of 0 or 1 to 5). ); * indicates the bonding position]. Still, each unit of the b unit system can be the same, or it can be different.

Specific examples of the divalent group represented by the formula (Y2) are not particularly limited, except for -CH ₂ -, -CH(CH ₃ )-, -CH(CH ₂ CH ₃ )-, and -C(CH ₃ ) ) ₂ -, -C(CH ₃ )(CH ₂ CH ₃ )-, -C(CH ₂ CH ₃ ) ₂ -, -O-, -CO-, -S-, -SO-, and -SO ₂ - In addition, divalent organic groups represented by the following are exemplified:

[In the formula, * represents a bonding site].

n1 is preferably an integer representing 1-100, more preferably an integer representing 5-50, more preferably an integer representing 10-35, and particularly preferably an integer representing 15-25. n2 is preferably an integer representing 1-100, preferably an integer representing 5-50, more preferably an integer representing 10-35, and particularly preferably an integer representing 15-25.

In the above embodiment, (A) the specific maleimide compound is preferably the maleimide compound represented by the formula (A2) (the n1 unit and the n2 unit is a bond):

[In the formula, each symbol system is the same as the formula (1), (4) and (A1)], more preferably a maleimide compound represented by the formula (A3) (a bond between the n1 unit and the n2 unit is a bond) key):

[wherein, X ⁵ , X ⁶ , and X ⁷ each independently represent a single bond, -C(R ⁹⁰ ) ₂ -, -O-, -CO-, -S-, -SO-, -SO ₂ -, - CONH-, -NHCO-, -COO-, or -OCO- (preferably: X ⁵ and X ⁷ are -O-, X ⁶ is -C(R ⁹⁰ ) ₂ -); R ⁹⁰ , R ⁹¹ , R ⁹² , R ⁹³ , R ⁹⁴ , R ⁰¹ , R ⁰² , R ⁰³ , and R ⁰⁴ independently represent a hydrogen atom, an alkyl group, an alkenyl group, an aryl-alkyl group, or an aryl group (preferably: R ⁹⁰ is an alkane group) group, the others are hydrogen atoms); the other symbols are the same as those of formulas (1), (4) and (A1)], particularly preferably a maleimide compound (n1 unit and n2 unit) represented by formula (A4) There is a bond between the units):

[In the formula, each symbol system is the same as the formula (4), (A1) and (A3)].

In one embodiment, the weight average molecular weight of the (A) specific maleimide compound is not particularly limited, but is preferably 3,000 or more, more preferably 4,000 or more, and more preferably 5,000 or more. The upper limit of the weight average molecular weight of the specific maleimide compound (A) is not particularly limited, but is preferably 500,000 or less, more preferably 200,000 or less, and more preferably 100,000 or less. The weight average molecular weight of the maleimide compound can be measured in terms of polystyrene by gel permeation chromatography (GPC).

In one embodiment, the functional group equivalent of the maleimide group of the (A) specific maleimide compound is not particularly limited, preferably 1000g/eq.~200000g/eq., and preferably 1500g/eq.~100000g/eq., more preferably 2000g/eq.~50000g/eq.. The functional group equivalent of the maleimide group refers to the mass of the compound per 1 equivalent of the maleimide group.

As a specific example of the specific maleimide compound (A), the maleimide compound represented by the following formula (A5) (a bond between the n1 unit and the n2 unit is a bond):

[In the formula, each symbol system is the same as that of the formula (A1)].

(A) As a commercial item of a specific maleimide compound, "BMI-6100" by Designer Molecules Corporation etc. are mentioned, for example.

The content of the (A) specific maleimide compound in the resin composition is not particularly limited, but when the nonvolatile content in the resin composition is 100% by mass, it is preferably 50% by mass or less, and more Preferably it is 40 mass % or less, More preferably, it is 30 mass % or less, More preferably, it is 20 mass % or less, Especially preferably, it is 15 mass % or less. The lower limit of the content of the (A) specific maleimide compound in the resin composition is not particularly limited, but when the nonvolatile content in the resin composition is 100% by mass, it is preferably 0.1% by mass or more, It is also preferably 1 mass % or more, more preferably 3 mass % or more, still more preferably 5 mass % or more, and particularly preferably 7 mass % or more.

<(A') Other radically polymerizable compounds> The resin composition system of the present invention may further contain (A') radically polymerizable compounds other than the (A) component as optional components. (A') The radically polymerizable compound type may be used alone or in any combination of two or more types.

(A') The radically polymerizable compound may be, for example, a compound having a radically polymerizable unsaturated group. The radically polymerizable unsaturated group is not particularly limited as long as it can radically polymerize, and an ethylenically unsaturated group having a carbon-carbon double bond at the terminal or inside is preferred, and specifically, an allyl group may be used. , unsaturated aliphatic groups such as 3-cyclohexenyl; aromatic groups containing unsaturated aliphatic groups such as p-vinylphenyl, m-vinylphenyl, styryl, etc.; acrylyl, methyl α, β-unsaturated carbonyl groups such as acryloyl group, maleinyl group, fumaric acid group, etc. The radically polymerizable compound (A') preferably has one or more radically polymerizable unsaturated groups, and more preferably has two or more radically polymerizable unsaturated groups.

As the other radical polymerizable compound (A'), well-known radical polymerizable compounds can be widely used, and although not particularly limited, for example, (A'-1) maleimide-based compounds other than (A) component can be mentioned. Radical polymerizable compounds, (A'-2) vinylphenyl radical polymerizable compounds, (A'-3) (meth)acrylic radical polymerizable compounds, and the like.

<(A'-1) Maleimide-based radically polymerizable compound> (A'-1) Maleimide-based radically polymerizable compound compounds other than the component (A) and containing one or more (preferably two or more) maleimide groups in one molecule organic compounds. (A'-1) The maleimide-based radically polymerizable compound may be used alone or in combination of two or more at an arbitrary ratio. (A'-1) The maleimide-based radically polymerizable compound is composed of, for example, (A'-1-1) maleimide-terminated polyimide, (A) other than the component (A) '-1-2) A maleimide compound of at least one of an aromatic maleimide compound and (A'-1-3) an aliphatic maleimide compound is preferable.

<(A'-1-1) Maleimide-terminated polyimide> (A'-1-1) Maleimide-terminated polyimide is not equivalent to the maleimide compound of the component (A), but a chain polyimide having maleimide groups at both ends amine. (A'-1-1) Maleimide-terminated polyimide can be obtained, for example, by subjecting a component containing a diamine compound, maleic anhydride and tetracarboxylic dianhydride to an imidization reaction Element.

In one embodiment, (A'-1-1) maleimide-terminated polyimide is, for example, a maleimide compound represented by the following formula (B):

[In the formula, n represents an integer of 1 or more (preferably an integer of 1 to 100, preferably an integer of 1 to 50, particularly preferably an integer of 1 to 20); other symbols and formula (A1) are same]. Still, each unit of the n-unit system can be the same, or it can be different.

(A'-1-1) The weight-average molecular weight (Mw) of the maleimide-terminated polyimide is preferably 500 to 500,000, and more preferably 1,000 to 200,000. The weight average molecular weight of the maleimide compound can be measured in terms of polystyrene by gel permeation chromatography (GPC).

(A'-1-1) The functional group equivalent of the maleimide group of the maleimide-terminated polyimide group is preferably 300 g/eq.~200000 g/eq., and more preferably 500 g/eq. ~100000g/eq..

As a commercial item of (A'-1-1) maleimide-terminated polyimide, for example, "BMI-1500", "BMI-1700", "BMI-3000J" manufactured by Designer Molecules, etc. .

<(A'-1-2) Aromatic maleimide compound> (A'-1-2) The aromatic maleimide compound represents a maleimide compound not corresponding to the components (A) and (A'-1-1), and contains one or more in one molecule It means a maleimide compound containing an aromatic ring of 2 or more maleimide groups. In one embodiment, the (A'-2) aromatic maleimide compound may be an addition polymerization type aromatic maleimide compound. (A'-2) The aromatic maleimide compound may be N,N'-1,3-phenylene dimaleimide, N,N'-1,4-phenylene dimaleimide Maleimide having one aromatic ring such as lyimide, or polymaleimide having two or more aromatic rings, and maleimide having two or more aromatic rings is better.

In one embodiment, the (A'-1-2) aromatic maleimide compound is, for example, the maleimide compound represented by the formula (C):

[In the formula, R ^c each independently represents a substituent; X ^c each independently represents a single bond, an alkylene group, an alkenylene group, -O-, -CO-, -S-, -SO-, -SO ₂ -, - CONH-, -NHCO-, -COO-, or -OCO- (preferably a single bond or an alkylene group); Z ^c each independently represents a non-aromatic ring that may have a substituent, or an aromatic ring that may have a substituent ( Preferably it is an aromatic ring which may have a substituent, particularly preferably a benzene ring which may have a substituent); s represents an integer of 1 or more (preferably an integer of 1 to 100, preferably an integer of 1 to 50, more preferably an integer from 1 to 20); t independently represents an integer of 0 or more than 1; u independently represents an integer from 0 to 2 (preferably 0)], especially the formula (C1-1)~(C1- 4) Maleimide compound represented:

[In the formula, R ^c1 , R ^c2 and R ^c3 each independently represent an alkyl group; X ^c1 and X ^c2 each independently represent a single bond or an alkylene group; s represents an integer of 1 or more (preferably an integer of 1 to 100, and It is preferably an integer of 1-50, more preferably an integer of 1-20); t' represents an integer of 1-5; u1, u2 and u3 independently represent an integer of 0-2 (preferably 0)]. Still, each respective unit system of s units, t units, t' units, u units, u1 units, u2 units, and u3 units may be the same, or may be different.

(A'-1-2) The weight average molecular weight (Mw) of the aromatic maleimide compound is preferably 150 to 5,000, and more preferably 300 to 2,500.

(A'-1-2) The functional group equivalent of the maleimide group of the aromatic maleimide compound is preferably 50 g/eq. to 2000 g/eq., more preferably 100 g/eq. to 1000 g /eq., more preferably 150g/eq.~500g/eq., particularly preferably 200g/eq.~300g/eq..

As commercial products of the (A'-1-2) aromatic maleimide compound, for example, "MIR-3000-70MT" manufactured by Nippon Kayaku Co., Ltd.; "BMI-50P" manufactured by K·I Chemical Co., Ltd. ; "BMI-1000", "BMI-1000H", "BMI-1100", "BMI-1100H", "BMI-4000", "BMI-5100" manufactured by Yamato Chemical Co., Ltd.; "BMI-5100" manufactured by K･I Chemical Co., Ltd. BMI-4,4'-BPE", "BMI-70", "BMI-80" manufactured by K･I Chemical Co., Ltd., etc.

<(A'-1-3) Aliphatic maleimide compound> The (A'-1-3) aliphatic maleimide compound refers to a non-aromatic hydrocarbon (preferably having 2 to 50 carbon atoms) as a basic skeleton and having 2 or more (preferably 2 to 50 carbon atoms) in one molecule. 2) maleimide-based compounds.

In one embodiment, the (A'-1-3) aliphatic maleimide compound is, for example, a maleimide compound represented by the following formula (D):

[In the formula, X ^d each independently represents a single bond, an alkylene group or an alkenylene group (preferably an alkylene group or an alkenylene group) ^; Aromatic ring (preferably a monocyclic alkane ring or a monocyclic olefin ring which may have a group selected from an alkyl group and an alkenyl group); x represents an integer of 0 or more (preferably an integer of 1 or more, particularly preferably 1 )]. Still, each unit system of x units can be the same, or can be different.

Specific examples of the (A'-1-3) aliphatic maleimide compound include N,N'-ethylidenedimaleimide, N,N'-tetramethylenebis Chain-like aliphatic bismaleimide compounds such as maleimide and N,N'-hexamethylenedimaleimide; 1-maleimide-3-maleimide Aminomethyl-3,5,5-trimethylcyclohexane (IPBM), 1,1'-(cyclohexane-1,3-diylbismethylene)bis(1H-pyrrole-2,5 -dione) (CBM), 1,1'-(4,4'-methylenebis(cyclohexane-4,1-diyl))bis(1H-pyrrole-2,5-dione)( MBCM) and other alicyclic bismaleimide compounds; bismaleimide containing dimer acid skeleton, etc.

The so-called bismaleimide containing a dimer acid backbone represents the substitution of the two terminal carboxyl groups (-COOH) of the dimer acid into a maleimide group or a maleimide methyl group (2,5 - Dihydro-2,5-dioxo-1H-pyrrol-1-ylmethyl) bismaleimide compound. Dimer acids are known compounds obtained by dimerizing unsaturated fatty acids (preferably those with 11 to 22 carbon atoms, particularly preferably those with 18 carbon atoms), and their industrial manufacturing processes are almost the same in the industry. is standardized. Dimer acid-based dimer acids with 36 carbon atoms obtained by dimerizing unsaturated fatty acids with 18 carbon atoms such as oleic acid and linoleic acid, which are particularly inexpensive and easily available, are easily available as the main component . In addition, the dimer acid system may contain arbitrary amounts of monomeric acid, trimer acid, other polymerized fatty acid, etc., depending on the production method, the degree of purification, and the like. In addition, although double bonds remain after the polymerization reaction of the unsaturated fatty acid, in this specification, the hydrogenated product whose degree of unsaturation is reduced by further hydrogenation reaction is also included in the dimer acid.

(A'-1-3) The molecular weight of the aliphatic maleimide compound is preferably 150 to 5000, and more preferably 300 to 1000.

(A'-1-3) The functional group equivalent of the maleimide group of the aliphatic maleimide compound is preferably 50 g/eq. to 2000 g/eq., and more preferably 100 g/eq. to 1000 g /eq., more preferably 200g/eq.~600g/eq., particularly preferably 300g/eq.~400g/eq..

As a commercial item of the (A'-1-3) aliphatic maleimide compound, "BMI-689" manufactured by Designer Molecules, Inc., etc. may be mentioned, for example.

<(A'-2) Vinylphenyl-based radical polymerizable compound> (A'-2) The vinylphenyl-based radically polymerizable compound is a radically polymerizable compound having a vinylphenyl group. The vinylphenyl-based radically polymerizable compound preferably has two or more vinylphenyl groups per molecule.

In one embodiment, the (A'-2) vinylphenyl-based radically polymerizable compound is preferably a vinylbenzyl-modified polyphenylene ether having a vinylbenzyl group and a polyphenylene ether skeleton, and has The repeating unit represented by the formula (E-1) (the number of repeating units is preferably 2 to 300, and preferably 2 to 100) and vinylbenzyl modified polyphenylene ether of vinylbenzyl (especially the polyphenylene ether). Particularly preferred is a vinylbenzyl group-modified polyphenylene ether in which the hydrogen atoms of the hydroxyl groups at both ends of the phenyl ether are substituted with vinylbenzyl groups.

[In the formula, R ^e1 , R ^e2 , R ^e3 and R ^e4 each independently represent a hydrogen atom or a substituent (preferably a hydrogen atom or an alkyl group, particularly preferably a hydrogen atom or a methyl group)].

In another embodiment, the (A'-2) vinylphenyl-based radically polymerizable compound is a compound having a repeating unit represented by the formula (E-2) (the number of repeating units is preferably 2 to 200). Vinylbenzene polymers are preferred.

[In the formula, R ^e5 , R ^e6 and R ^e7 each independently represent a hydrogen atom or a substituent (preferably a hydrogen atom)]. The divinylbenzene polymer system may further be a copolymer having other styrene skeleton units such as styrene units and ethylstyrene units. When there are other styrene skeleton units, the ratio of the repeating unit of formula (E-2) is preferably 5 to 70 mol % relative to all styrene skeleton units.

(A'-2) The number average molecular weight of the vinylphenyl-based radically polymerizable compound is preferably 500 to 100,000, and more preferably 700 to 80,000. (A'-2) The functional group equivalent of the vinyl group of the vinylphenyl-based radically polymerizable compound is preferably 200 g/eq. to 3000 g/eq., and more preferably 200 g/eq. to 2000 g/eq.

As commercially available products of the (A'-2) vinylphenyl radical polymerizable compound, "OPE-2St 1200" and "OPE-2St 2200" (vinylbenzyl modified quality polyphenylene ether); "ODV-XET-X03", "ODV-XET-X04", "ODV-XET-X05" (divinylbenzene polymer) manufactured by Nippon Steel Chemical & Material Co., Ltd.

<(A'-3) (Meth)acrylic radical polymerizable compound> (A'-3) The (meth)acrylic radical polymerizable compound is a radical polymerizable compound having an acryl group and/or a methacryl group. (A'-3) The (meth)acrylic radical polymerizable compound preferably has two or more acryl group and/or methacryl group per molecule. (A'-3) The (meth)acrylic radical polymerizable compound is preferably a (meth)acrylic modified polyphenylene ether having an acryl group and/or a methacryl group and a polyphenylene ether skeleton , with a repeating unit represented by formula (F) (the number of repeating units is preferably 2~300, and preferably 2~100) and acrylyl and/or methacryloyl (meth)acrylic acid modified Quality polyphenylene ether (especially polyphenylene ether modified polyphenylene ether at both ends of the polyphenylene ether by replacing the hydrogen atoms of the hydroxyl groups at both ends with acrylyl and/or methacrylyl groups) is particularly preferred.

[In the formula, R ^f1 , R ^f2 , R ^f3 and R ^f4 each independently represent a hydrogen atom or a substituent (preferably a hydrogen atom or an alkyl group, particularly preferably a hydrogen atom or a methyl group)].

(A'-3) The number average molecular weight of the (meth)acrylic radical polymerizable compound is preferably 500 to 10,000, and more preferably 700 to 5,000. (A'-3) The functional group equivalent of the acryl group and the methacryloyl group of the (meth)acrylic radical polymerizable compound is preferably 200 g/eq. to 3000 g/eq., and more preferably 300 g/ eq.~2000g/eq..

As a commercial item of (A'-3) (meth)acrylic radical polymerizable compound, for example, "SA9000" and "SA9000-111" (methacrylic acid modified polyphenylene ether) manufactured by SABIC Innovative Plastics Co., Ltd. )Wait.

The content of (A') other radically polymerizable compounds in the resin composition is not particularly limited, but when the nonvolatile content in the resin composition is 100% by mass, it is preferably 50% by mass or less, and more Preferably it is 40 mass % or less, More preferably, it is 30 mass % or less, More preferably, it is 20 mass % or less, Especially preferably, it is 10 mass % or less. The lower limit of the content of the other radically polymerizable compound (A') in the resin composition is not particularly limited, but when the nonvolatile content in the resin composition is 100% by mass, for example, it may be 0% by mass or more, 0.1 mass % or more, 1 mass % or more, 2 mass % or more, and the like.

When the total radical polymerizable compound (the total of (A) component and (A') component) in the resin composition is 100% by mass, the (A) specific maleimide compound in the resin composition is The content is preferably 10% by mass or more, more preferably 30% by mass or more, more preferably 40% by mass or more, and particularly preferably 50% by mass or more.

<(B) Epoxy resin> The resin composition of this invention contains (B) an epoxy resin. The (B) epoxy resin means a curable resin having an epoxy group. The epoxy resin (B) is preferably an epoxy resin containing a condensed ring structure (B-1).

<(B-1) Epoxy resin containing condensed ring structure> The epoxy resin containing a condensed ring structure (B-1) means a resin having one or more condensed rings and one or more (preferably two or more) epoxy groups in one molecule. (B-1) The epoxy resin system containing a condensed ring structure may be used individually by 1 type, and may be used in combination of 2 or more types in arbitrary ratios.

(B-1) The condensed ring system contained in the epoxy resin containing a condensed ring structure is preferably a condensed aromatic carbocyclic ring. The condensed aromatic carbocyclic ring system is an aromatic carbocyclic ring with more than two cyclic formulas obtained by condensing two or more benzene rings. The carbon number system is preferably 10-18, preferably 10-14, for example A naphthalene ring, an anthracene ring, a phenanthrene ring, etc., a naphthalene ring is particularly preferred.

(B-1) The epoxy resin system containing a condensed ring structure may be any of a glycidyl ether type, a glycidyl amine type, a glycidyl ester type, and an olefin oxidation (alicyclic type) type, among which the glycidyl ether type is used. is better.

(B-1) The epoxy resin system containing a condensed ring structure may be a monomer type or a repeating structure type. Here, the so-called repeating structure type refers to a polymer structure having an average of 3 or more repeating units including one or two or more condensed rings; Molecular structure of a repeating unit of two or more condensed rings. (B-1) The epoxy resin containing a condensed ring structure is selected from the group consisting of (B-1-1) an epoxy resin containing a monomeric condensed ring structure, and (B-1-2) a condensed epoxy containing a repeating structure The epoxy resin among the epoxy resins of the ring structure preferably contains (B-1-2) an epoxy resin containing a condensed ring structure of a repeating structure type.

(B-1-1) The epoxy resin containing a monomeric condensed ring structure includes, for example, 1,6-bis(glycidoxy)naphthalene, 1,5-bis(glycidoxy) Monomer-containing monomers having one condensed ring in 1 molecule, such as naphthalene, 2,7-bis(glycidoxy)naphthalene, 2,6-bis(glycidoxy)naphthalene, etc. Epoxy resin with condensed ring structure; bis[2-(glycidyloxy)-1-naphthyl]methane, 2,2-bis[2-(glycidyloxy)-1-naphthyl] Propane, bis[2,7-bis(glycidyloxy)-1-naphthyl]methane, 2,2-bis[2,7-bis(glycidyloxy)-1-naphthyl] Propane, [2,7-bis(glycidyloxy)-1-naphthyl][2-(glycidyloxy)-1-naphthyl]methane, 2-[2,7-bis( Glycidoxy)-1-naphthyl]-2-[2-(glycidyloxy)-1-naphthyl]propane, etc., containing monomers having two condensed rings in one molecule The condensed ring structure of epoxy resin.

In one embodiment, (B-1-1) The epoxy resin containing a monomeric condensed ring structure is preferably a bifunctional to tetrafunctional epoxy resin, and a bifunctional or trifunctional epoxy resin is preferred. For further preference, bifunctional epoxy resins are particularly preferred.

(B-1-1) The epoxy equivalent of the epoxy resin containing the monomeric condensed ring structure is not particularly limited, but is preferably 50 g/eq. or more, more preferably 80 g/eq. or more, and more preferably 100 g/eq. or more, more preferably 120 g/eq. or more, particularly preferably 130 g/eq. or more. (B-1-1) The upper limit of the epoxy equivalent of the epoxy resin containing a monomeric condensed ring structure is not particularly limited, but is preferably 1000 g/eq. or less, more preferably 500 g/eq. or less, and more It is preferably 300 g/eq. or less, more preferably 200 g/eq. or less, and particularly preferably 160 g/eq. or less. The epoxy equivalent is the mass of the epoxy group per 1 equivalent of the resin. The epoxy equivalent can be measured according to JIS K7236.

(B-1-1) The molecular weight of the epoxy resin containing a monomeric condensed ring structure is not particularly limited, but is preferably 2,000 or less, more preferably 1,000 or less, more preferably 700 or less, and still more preferably 600 or less, especially 500 or less.

(B-1-1) Commercially available epoxy resins containing a monomeric condensed ring structure include, for example, "HP-4032D" and "HP-4032SS" manufactured by DIC Corporation (with one molecule per molecule). Epoxy resin with naphthalene ring); "EXA-4750", "HP-4770", "HP-4700", "HP-4710" manufactured by DIC Corporation (epoxy resin having two naphthalene rings in one molecule) )Wait.

(B-1-2) As the epoxy resin containing a condensed ring structure of a repeating structure type, for example, a naphthol novolak type epoxy resin, a naphthol-phenol co- novolac type epoxy resin, a naphthol-methyl epoxy resin, Phenol co-acetal type epoxy resins, naphthol aralkyl type epoxy resins, naphthalene glycol aralkyl type epoxy resins, naphthyl ether type epoxy resins, etc. have three or more condensations in one molecule Epoxy resins containing a condensed ring structure of a repeating structure. In one embodiment, it is preferable that (B-1-2) the epoxy resin system containing the condensed ring structure of the repeating structure type contains a naphthol aralkyl type epoxy resin.

(B-1-2) The epoxy equivalent of the epoxy resin containing the condensed ring structure of the repeating structure is not particularly limited, but is preferably 50 g/eq. or more, more preferably 100 g/eq. or more, and more preferably 200 g/eq. or more, more preferably 250 g/eq. or more, particularly preferably 300 g/eq. or more. (B-1-2) The upper limit of the epoxy equivalent of the epoxy resin containing the condensed ring structure of the repeating structure is not particularly limited, but is preferably 2000 g/eq. or less, more preferably 1000 g/eq. or less, and more Preferably it is 500 g/eq. or less, more preferably 400 g/eq. or less.

(B-1-2) Commercially available epoxy resins containing a condensed ring structure of a repeating structure include "ESN-155", "ESN-185V", and "ESN" manufactured by Nippon Steel Chemical & Material Co., Ltd. -175", "ESN-475V", "ESN-485", "TX-1507B" (naphthol aralkyl type epoxy resin); "EXA-7311", "EXA-7311-G3" manufactured by DIC Corporation , "EXA-7311-G4", "EXA-7311-G4S", "HP-6000", "HP-6000-L" (naphthyl ether type epoxy resin); "NC7000L" manufactured by Nippon Kayaku Co., Ltd. (Naphthol novolac epoxy resin) etc.

In one embodiment, the epoxy resin containing a condensed ring structure (B-1) preferably contains a naphthol aralkyl type epoxy resin.

The resin composition may contain (B-2) other epoxy resins in addition to the epoxy resin containing the condensed ring structure (B-1), when the total epoxy resin in the resin composition is 100% by mass , the content of the epoxy resin containing the condensed ring structure (B-1) in the resin composition is preferably 50 mass % or more, 60 mass % or more, from the viewpoint of clearly obtaining the desired effect of the present invention, and It is preferably 70 mass % or more and 80 mass % or more, more preferably 90 mass % or more and 95 mass % or more, still more preferably 98 mass % or more and 99 mass % or more, and particularly preferably 100 mass %.

<(B-2) Other epoxy resins> (B-2) Other epoxy resins include, for example, bixylenol type epoxy resins, bisphenol A type epoxy resins, bisphenol F type epoxy resins, bisphenol S type epoxy resins, and bisphenol AF type epoxy resin, dicyclopentadiene type epoxy resin, trisphenol type epoxy resin, phenol novolac type epoxy resin, tert-butyl-catechol type epoxy resin, glycidylamine type epoxy resin , glycidyl ester type epoxy resin, cresol novolac type epoxy resin, phenol aralkyl type epoxy resin, biphenyl type epoxy resin, linear aliphatic epoxy resin, epoxy resin with butadiene structure Resin, alicyclic epoxy resin, heterocyclic epoxy resin, spiro ring-containing epoxy resin, cyclohexane type epoxy resin, cyclohexane dimethanol type epoxy resin, trimethylolpropane type epoxy resin Resin, tetraphenylethane type epoxy resin, isocyanurate type epoxy resin, phenolphthalimidine type epoxy resin, phenolphthalein type epoxy resin, etc. (B-2) Other epoxy resins may be used alone or in combination of two or more.

It is preferable that the resin composition contains an epoxy resin having two or more epoxy groups in one molecule as the other epoxy resin (B-2). The ratio of the epoxy resin having two or more epoxy groups in 1 molecule is preferably 50 mass % or more, and more preferably 60 mass % relative to 100 mass % of the nonvolatile content of the other epoxy resins (B-2). mass % or more, particularly preferably 70 mass % or more.

The epoxy resin system includes epoxy resins that are liquid at a temperature of 20°C (hereinafter sometimes referred to as "liquid epoxy resins") and epoxy resins that are solid at a temperature of 20°C (hereinafter sometimes referred to as "liquid epoxy resins"). solid epoxy resin”). The resin composition of the present invention may contain only a liquid epoxy resin, only a solid epoxy resin, or a liquid epoxy resin and a solid ring as the other epoxy resin (B-2). Oxygen resin combination.

As a liquid epoxy resin system, the liquid epoxy resin which has two or more epoxy groups in 1 molecule is preferable.

As liquid epoxy resins, bisphenol A type epoxy resin, bisphenol F type epoxy resin, bisphenol AF type epoxy resin, glycidyl ester type epoxy resin, glycidyl amine type epoxy resin, phenol novolac Varnish-type epoxy resins, alicyclic epoxy resins having an ester skeleton, cyclohexane-type epoxy resins, cyclohexanedimethanol-type epoxy resins, and epoxy resins having a butadiene structure are preferable.

Specific examples of liquid epoxy resins include "828US", "828EL", "jER828EL", "825", and "Epikote 828EL" (bisphenol A type epoxy resin) manufactured by Mitsubishi Chemical Co., Ltd.; "jER807" and "1750" (bisphenol F type epoxy resin) manufactured by the company; "jER152" (phenol novolac epoxy resin) manufactured by Mitsubishi Chemical; "630" and "630LSD" manufactured by Mitsubishi Chemical , "604" (glycidylamine-type epoxy resin); "ED-523T" (glycyrrhizol-type epoxy resin) manufactured by ADEKA; "EP-3950L", "EP-3980S" (glycidyl) manufactured by ADEKA Amine type epoxy resin); "EP-4088S" (dicyclopentadiene type epoxy resin) manufactured by ADEKA; "ZX1059" (bisphenol A type epoxy resin and bisphenol F) manufactured by Nippon Steel & Sumitomo Chemical type epoxy resin mixture); "EX-721" (glycidyl ester type epoxy resin) manufactured by Nagasechemtex; "Celloxide 2021P" (alicyclic epoxy resin with an ester skeleton) manufactured by Daicel; Daicel "PB-3600" manufactured by the company, "JP-100", "JP-200" (epoxy resin with a butadiene structure) manufactured by Nippon Soda Co., Ltd.; "ZX1658", " ZX1658GS" (liquid 1,4-glycidyl cyclohexane type epoxy resin) etc. These systems may be used alone or in combination of two or more.

The solid epoxy resin is preferably a solid epoxy resin having three or more epoxy groups in one molecule, and an aromatic solid epoxy resin having three or more epoxy groups in one molecule is preferred. Resin is also preferred.

As solid epoxy resins, bixylenol type epoxy resins, cresol novolac type epoxy resins, dicyclopentadiene type epoxy resins, trisphenol type epoxy resins, biphenyl type epoxy resins, Phenol A type epoxy resin, bisphenol AF type epoxy resin, phenol aralkyl type epoxy resin, tetraphenylethane type epoxy resin, phenolphthalimide type epoxy resin, phenolphthalein type epoxy resin are preferred .

Specific examples of solid epoxy resins include "N-690" (cresol novolak type epoxy resin) manufactured by DIC Corporation; "N-695" (cresol novolak type epoxy resin) manufactured by DIC Corporation resin); "HP-7200", "HP-7200HH", "HP-7200H", "HP-7200L" (dicyclopentadiene epoxy resin) manufactured by DIC Corporation; "EPPN- 502H" (triphenol type epoxy resin); "NC3000H", "NC3000", "NC3000L", "NC3000FH", "NC3100" (biphenyl type epoxy resin) manufactured by Nippon Kayaku Co., Ltd.; manufactured by Mitsubishi Chemical Co., Ltd. "YX4000H", "YX4000", "YX4000HK", "YL7890" (bixylenol type epoxy resin); "YL6121" (biphenyl type epoxy resin) manufactured by Mitsubishi Chemical Corporation; "YX7700" manufactured by Mitsubishi Chemical Corporation "(Phenol aralkyl type epoxy resin); "PG-100", "CG-500" manufactured by Osaka Gas Chemicals; "YL7760" (bisphenol AF type epoxy resin) manufactured by Mitsubishi Chemical Corporation; Mitsubishi chemical "YL7800" (fluorene type epoxy resin) manufactured by the company; "jER1010" (bisphenol A type epoxy resin) manufactured by Mitsubishi Chemical Corporation; "jER1031S" (tetraphenylethane type epoxy resin) manufactured by Mitsubishi Chemical Corporation ; "WHR991S" (phenolphthalimide type epoxy resin) manufactured by Nippon Kayaku Co., Ltd. These systems may be used alone or in combination of two or more.

(B) The epoxy equivalent of the epoxy resin is preferably 50g/eq.~5,000g/eq., more preferably 60g/eq.~2,000g/eq., more preferably 70g/eq.~1,000g/ eq., more preferably 80g/eq.~500g/eq..

The weight average molecular weight (Mw) of the (B) epoxy resin is preferably 100 to 5,000, more preferably 250 to 3,000, and more preferably 400 to 1,500. The weight average molecular weight of the resin can be measured in terms of polystyrene by gel permeation chromatography (GPC).

The content of the (B) epoxy resin in the resin composition is not particularly limited, but when the nonvolatile content in the resin composition is 100% by mass, it is preferably 60% by mass or less, and more preferably 50% by mass Below, 40 mass % or less is more preferable, 30 mass % or less is still more preferable, and 20 mass % or less is especially preferable. The lower limit of the content of the epoxy resin (B) in the resin composition is not particularly limited, but when the nonvolatile content in the resin composition is 100% by mass, it is preferably 0.01% by mass or more, more preferably 0.1% by mass % or more, preferably 1 mass % or more, more preferably 1 mass % or more, still more preferably 5 mass % or more, and particularly preferably 10 mass % or more.

The mass ratio ((A) component/(B) component) of the (A) specific maleimide compound to (B) the epoxy resin in the resin composition is preferably 0.1 or more, and more preferably 0.3 or more, Particularly preferred is 0.5 or more. The upper limit of the mass ratio ((A) component/(B) component) of the (A) specific maleimide compound to (B) epoxy resin in the resin composition is preferably 10 or less, and more preferably 3 Hereinafter, 1 or less is particularly preferred.

<(C) Inorganic fillers> The resin composition of the present invention contains (C) an inorganic filler. (C) The inorganic filler is contained in the resin composition in the form of particles.

(C) An inorganic compound is used as a material of an inorganic filler. As the material of the (C) inorganic filler, for example, silica, alumina, glass, cordierite, silicon oxide, barium sulfate, barium carbonate, talc, clay, mica powder, zinc oxide, hydrotalcite, water Bauxite, aluminum hydroxide, magnesium hydroxide, calcium carbonate, magnesium carbonate, magnesium oxide, boron nitride, aluminum nitride, manganese nitride, aluminum borate, strontium carbonate, strontium titanate, calcium titanate, magnesium titanate, Bismuth titanate, titanium oxide, zirconium oxide, barium titanate, barium titanate zirconate, barium zirconate, calcium zirconate, zirconium phosphate, and zirconium tungsten phosphate, etc. Among these, silica is particularly suitable. As silica, amorphous silica, fused silica, crystalline silica, synthetic silica, hollow silica, etc. are mentioned, for example. Moreover, spherical silica is preferable as a silica system. (C) Inorganic filler system may be used individually by 1 type, and may be used in combination of 2 or more types at arbitrary ratios.

(C) Commercial products of the inorganic filler include "UFP-30" manufactured by Denka Chemical Industries, Ltd.; "SP60-05" and "SP507-05" manufactured by Nippon Steel & SUMIKIN MATERIALS; and "SP507-05" manufactured by Admatechs "YC100C", "YA050C", "YA050C-MJE", "YA010C"; "UFP-30" made by Denca; "ShirufiruNSS-3N", "ShirufiruNSS-4N", "ShirufiruNSS-5N" made by Tokuyama ; "SC2500SQ", "SO-C4", "SO-C2", "SO-C1" made by Admatechs; "DAW-03", "FB-105FD" made by Denca, etc.

The average particle size of the inorganic filler (C) is not particularly limited, but is preferably 10 μm or less, more preferably 5 μm or less, more preferably 2 μm or less, still more preferably 1 μm or less, and particularly preferably 0.7 μm or less. (C) The lower limit of the average particle diameter of the inorganic filler is not particularly limited, but is preferably 0.01 μm or more, more preferably 0.05 μm or more, more preferably 0.1 μm or more, and particularly preferably 0.2 μm or more. (C) The average particle diameter of the inorganic filler can be measured by a laser diffraction/scattering method based on the Mie scattering theory. Specifically, the particle size distribution of the inorganic filler is produced on a volume basis by a laser diffraction scattering particle size distribution measuring device, and the median diameter is measured as the average particle size. The measurement sample can be obtained by weighing 100 mg of the inorganic filler and 10 g of methyl ethyl ketone into a vial, and dispersing it with ultrasonic waves for 10 minutes. Using a laser diffraction particle size distribution measuring device for the measurement sample, and using the light source wavelengths as blue and red, the volume-based particle size distribution of the inorganic filler was measured by a flow cell method, and the obtained particle size The distribution calculates the average particle diameter as the median particle diameter. As a laser diffraction particle size distribution measuring device, "LA-960" manufactured by HORIBA, Ltd., etc. is mentioned, for example.

(C) The specific surface area of the inorganic filler is not particularly limited, but is preferably 0.1 m ² /g or more, more preferably 0.5 m ² /g or more, more preferably 1 m ² /g or more, particularly preferably 3 m ² /g or more. (C) The upper limit of the specific surface area of the inorganic filler is not particularly limited, but is preferably 100 m ² /g or less, more preferably 70 m ² /g or less, more preferably 50 m ² /g or less, particularly preferably 30 m ² /g or less. The specific surface area of the inorganic filler was obtained by adsorbing nitrogen gas on the surface of the sample using a specific surface area measuring device (Macsorb HM-1210, manufactured by Mounttech) according to the BET method, and calculating the specific surface area by the BET multipoint method.

(C) The inorganic filler is preferably surface-treated with an appropriate surface-treating agent. The moisture resistance and dispersibility of the (C) inorganic filler can be improved by surface treatment. Examples of the surface treatment agent include vinyl-based silane coupling agents such as vinyltrimethoxysilane and vinyltriethoxysilane; 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane , 3-glycidoxypropylmethyldimethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropylmethyldiethoxysilane, 3-glycidyl Epoxy-based silane coupling agents such as oxypropyltriethoxysilane; styrene-based silane coupling agents such as p-styryltrimethoxysilane; 3-methacryloyloxypropylmethyldimethyldimethylene oxysilane, 3-methacryloyloxypropyltrimethoxysilane, 3-methacryloyloxypropylmethyldiethoxysilane, 3-methacryloyloxypropyltriethoxysilane Methacrylic silane coupling agents such as methacrylic silane; acrylic silane coupling agents such as 3-acryloyloxypropyltrimethoxysilane; N-2-(aminoethyl)-3-aminopropylmethyl Dimethoxysilane, N-2-(aminoethyl)-3-aminopropyltrimethoxysilane, 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxy Silane, 3-triethoxysilyl-N-(1,3-dimethyl-butylene)propylamine, N-phenyl-3-aminopropyltrimethoxysilane, N-phenyl-8- Amino-based silane coupling agents such as aminooctyltrimethoxysilane, N-(vinylbenzyl)-2-aminoethyl-3-aminopropyltrimethoxysilane, etc.; Trimeric isocyanate-based silane coupling agents such as silylpropyl) trimeric isocyanate; ureido-based silane coupling agents such as 3-ureidopropyl trialkoxysilane and the like; 3-mercaptopropylmethyldimethoxy Mercapto-based silane coupling agents such as silane and 3-mercaptopropyltrimethoxysilane; isocyanate-based silane coupling agents such as 3-isocyanatopropyltriethoxysilane; 3-trimethoxysilylpropyl succinic anhydride, etc. Anhydride-based silane coupling agent; silane coupling agent such as; methyltrimethoxysilane, dimethyldimethoxysilane, phenyltrimethoxysilane, methyltriethoxysilane, dimethyldiethoxysilane Silane, phenyltriethoxysilane, n-propyltriethoxysilane, n-propyltriethoxysilane, hexyltrimethoxysilane, hexyltriethoxysilane, octyltriethoxysilane , decyltrimethoxysilane, 1,6-bis(trimethoxysilyl)hexane, trifluoropropyltrimethoxysilane, etc. non-silane coupling-alkoxysilane compounds, etc. Moreover, a surface treatment agent system may be used individually by 1 type, and may be used in combination of 2 or more types in arbitrary ratios.

Commercially available surface treatment agents include "KBM-1003", "KBE-1003" (vinyl silane coupling agent) manufactured by Shin-Etsu Chemical Co., Ltd.; "KBM-303", "KBM-402", "KBM-403", "KBE-402", "KBE-403" (epoxy silane coupling agent); "KBM-1403" (styrene silane coupling agent); "KBM-502", "KBM-503" ", "KBE-502", "KBE-503" (methacrylic silane coupling agent); "KBM-5103" (acrylic silane coupling agent); "KBM-602", "KBM-603", "KBM" -903", "KBE-903", "KBE-9103P", "KBM-573", "KBM-575" (amine-based silane coupling agent); "KBM-9659" (trimeric isocyanate-based silane coupling agent) ; "KBE-585" (urea-based silane coupling agent); "KBM-802", "KBM-803" (mercapto-based silane coupling agent); "KBE-9007N" (isocyanate-based silane coupling agent); "X- 12-967C" (acid anhydride 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 coupling- alkoxysilane compounds), etc.

From the viewpoint of improving the dispersibility of the inorganic filler, the degree of surface treatment by the surface treatment agent is preferably within a specified range. Specifically, 100% by mass of the inorganic filler is preferably surface-treated with a surface treatment agent of 0.2% by mass to 5% by mass, more preferably 0.2% by mass to 3% by mass, and 0.3% by mass to 3% by mass. It is more preferable to carry out surface treatment in mass % to 2 mass %.

The degree of surface treatment by the surface treatment agent can be evaluated in terms of the amount of carbon 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 of the inorganic filler is preferably 0.02 mg/m ² or more, more preferably 0.1 mg/m ² or more, and 0.2 mg /m ² or more is more preferable. On the other hand, from the viewpoint of preventing the increase of the melt viscosity of the resin composition or the increase of the melt viscosity in the form of a sheet, 1.0 mg/m ² or less is preferable, and 0.8 mg/m ² or less is still more preferable. better, more preferably 0.5 mg/m ² or less.

(C) The carbon content per unit surface area of the inorganic filler can be measured after washing the surface-treated inorganic filler with a solvent (eg, methyl ethyl ketone (MEK)). Specifically, a sufficient amount of MEK as a solvent can be added to the inorganic filler surface-treated with the surface-treating agent, followed by ultrasonic cleaning at 25° C. for 5 minutes. After removing the supernatant and drying the solid content, the amount of carbon per unit surface area of the inorganic filler can be measured using a carbon analyzer. As a carbon analyzer, "EMIA-320V" manufactured by Horiba, Ltd., etc. can be used.

When the nonvolatile content in the resin composition is 100% by mass, the content of the (C) inorganic filler in the resin composition is more than 30% by mass, and from the viewpoint of further suppressing the thermal expansion coefficient, it is preferable to be 40 mass % or more, preferably 45 mass % or more, more preferably 50 mass % or more, and particularly preferably 55 mass % or more. The upper limit of the content of the (C) inorganic filler in the resin composition is not particularly limited, but when the nonvolatile content in the resin composition is 100% by mass, it is preferably 90% by mass or less, and more preferably 90% by mass or less. It is 80 mass % or less, More preferably, it may be 75 mass % or less, Especially preferably, it may be 70 mass % or less.

The mass ratio ((A) component/(C) component) of the (A) specific maleimide compound to (C) the inorganic filler in the resin composition is preferably 0.01 or more, and more preferably 0.05 or more, Particularly preferred is 0.1 or more. The upper limit of the mass ratio ((A) component/(C) component) of the (A) specific maleimide compound to the (C) inorganic filler in the resin composition is preferably 1 or less, and more preferably 0.5 Below, it is especially preferable that it is 0.3 or less.

<(D) Active ester compound> The resin composition of the present invention may contain (D) an active ester compound as an optional component. (D) Active ester compound type may be used individually by 1 type, and may be used in combination of 2 or more types in arbitrary ratios. In one embodiment, the (D) active ester compound may have a function of reacting with the (B) epoxy resin to harden the resin composition.

As the active ester compound (D), it is generally preferable to use phenolic esters, thiophenolic esters, N-hydroxyamine esters, esters of heterocyclic hydroxy compounds, and the like, which have high reactivity in one molecule of two or more. ester-based compounds. The active ester compound is preferably obtained by a condensation reaction of a carboxylic acid compound and/or a thiocarboxylic acid compound with a hydroxy compound and/or a thiol compound. In particular, from the viewpoint of improving heat resistance, an active ester compound obtained from a carboxylic acid compound and a hydroxy compound is preferred, and an active ester compound obtained from a carboxylic acid compound and a phenol compound and/or a naphthol compound is preferred. and better. Examples of the carboxylic acid compound include benzoic acid, acetic acid, succinic acid, maleic acid, itonic acid, phthalic acid, isophthalic acid, terephthalic acid, pyrometic acid, and the like. Examples of the phenol compound or naphthol compound include hydroquinone, resorcinol, bisphenol A, bisphenol F, bisphenol S, reduced phenolphthalein, methylated bisphenol A, methylated bisphenol F, methylated bisphenol S, phenol, o-cresol, m-cresol, p-cresol, catechol, α-naphthol, β-naphthol, 1,5-dihydroxynaphthalene, 1,6-dihydroxyl Naphthalene, 2,6-dihydroxynaphthalene, dihydroxybenzophenone, trihydroxybenzophenone, tetrahydroxybenzophenone, phloroglucinol, phloroglucinol, dicyclopentadiene type diphenol compound, phenol novolac, etc. . Here, the "dicyclopentadiene-type diphenol compound" refers to a diphenol compound obtained by condensing two molecules of phenol and one molecule of dicyclopentadiene.

Specifically, as the component (D), a dicyclopentadiene-type active ester compound, a naphthalene-type active ester compound containing a naphthalene structure, an active ester compound containing an acetylated compound of a phenol novolak, and a benzene-based active ester compound containing a phenol novolak are used. The active ester compound of the formate is preferred, and at least one selected from the group consisting of dicyclopentadiene-type active ester compounds and naphthalene-type active ester compounds is also preferred, and the dicyclopentadiene-type active ester compound is better. As a dicyclopentadiene-type active ester compound, the active ester compound containing a dicyclopentadiene-type diphenol structure is preferable. The "dicyclopentadiene-type diphenol structure" refers to a bivalent structural unit composed of phenylene-dicyclopentene-phenylene.

(D) Commercial products of the active ester compound include "EXB9451", "EXB9460", "EXB9460S", "EXB-8000L", and "EXB" as the active ester compound having a dicyclopentadiene-type diphenol structure. -8000L-65M", "EXB-8000L-65TM", "HPC-8000L-65TM", "HPC-8000", "HPC-8000-65T", "HPC-8000H", "HPC-8000H-65TM", (manufactured by DIC Corporation); Examples of active ester compounds containing a naphthalene structure include "EXB-8100L-65T", "EXB-8150-60T", "EXB-8150-62T", "EXB-9416-70BK", "HPC-8150-60T", "HPC-8150-62T" (manufactured by DIC Corporation); examples of phosphorus-containing active ester compounds include "EXB9401" (manufactured by DIC Corporation); acetylated compounds of phenol novolacs Examples of active ester compounds include "DC808" (manufactured by Mitsubishi Chemical Co., Ltd.); as active ester compounds of benzyl compounds of phenol novolacs, "YLH1026", "YLH1030", and "YLH1048" (Mitsubishi Chemical Co., Ltd.) manufactured by ); "PC1300-02-65MA" (manufactured by AIR WATER) etc. are mentioned as an active ester compound containing a styryl group and a naphthalene structure.

(D) The active ester group equivalent of the active ester compound is preferably 50g/eq.~500g/eq., more preferably 50g/eq.~400g/eq., more preferably 100g/eq.~300g/eq. . The active ester group equivalent means the mass of the active ester compound per 1 equivalent of the active ester group.

The content of the (D) active ester compound in the resin composition is not particularly limited, but when the nonvolatile content in the resin composition is 100% by mass, it is preferably 50% by mass or less, and more preferably 40% by mass Below, 30 mass % or less is more preferable, 20 mass % or less is still more preferable, and 15 mass % or less is especially preferable. The lower limit of the content of the (D) active ester compound in the resin composition is not particularly limited, but when the nonvolatile content in the resin composition is 100% by mass, for example, it may be 0% by mass or more, 0.01% by mass or more, etc. , preferably 0.1 mass % or more, more preferably 1 mass % or more, more preferably 3 mass % or more, still more preferably 5 mass % or more, and particularly preferably 7 mass % or more.

The mass ratio ((A) component/(D) component) of the (A) specific maleimide compound to (D) the active ester compound in the resin composition is preferably 0.1 or more, more preferably 0.5 or more, Particularly preferred is 0.8 or more. The upper limit of the mass ratio ((A) component/(D) component) of the (A) specific maleimide compound to (D) the active ester compound in the resin composition is preferably 10 or less, and more preferably 3 Hereinafter, 1.5 or less is particularly preferable.

<(E) Hardening accelerator> The resin composition system of this invention may contain (E) a hardening accelerator as an arbitrary component.

Examples of the curing accelerator include phosphorus-based curing accelerators, urea-based curing accelerators, guanidine-based curing accelerators, imidazole-based curing accelerators, metal-based curing accelerators, and amine-based curing accelerators. (E) Hardening accelerator system may be used individually by 1 type, and may be used in combination of 2 or more types.

Examples of phosphorus-based curing accelerators include tetrabutylphosphonium bromide, tetrabutylphosphonium chloride, tetrabutylphosphonium acetate, tetrabutylphosphonium decanoate, tetrabutylphosphonium laurate, bis( Tetrabutylphosphonium) pyromellitic acid salt, tetrabutylphosphonium hexahydrophthalate, tetrabutylphosphonium 2,6-bis[(2-hydroxy-5-methylphenyl)methyl] - Aliphatic phosphonium salts such as 4-methylphenate, di-tert-butylmethylphosphonium tetraphenylborate, etc.; methyltriphenylphosphonium bromide, ethyltriphenylphosphonium bromide, propyltriphenyl Phosphonium bromide, butyltriphenylphosphonium bromide, benzyltriphenylphosphonium chloride, tetraphenylphosphonium bromide, p-tolyltriphenylphosphonium tetra-p-tolylborate, tetraphenylphosphonium Tetraphenyl borate, tetraphenyl phosphonium tetra-p-tolyl borate, triphenylethyl phosphonium tetraphenyl borate, gins (3-methylphenyl) ethyl phosphonium tetraphenyl borate, ginseng ( 2-Methoxyphenyl)ethylphosphonium tetraphenylborate, (4-methylphenyl)triphenylthiocyanate, tetraphenylthiocyanate, butyltriphenylthiocyanate Aromatic phosphonium salts such as triphenylphosphine and triphenylborane; Aromatic phosphine and borane complexes such as triphenylphosphine and triphenylborane; Aromatic phosphine and quinone addition reaction products such as triphenylphosphine and p-benzoquinone addition products Reactants; tributylphosphine, tri-tert-butylphosphine, trioctylphosphine, di-tert-butyl(2-butenyl)phosphine, di-tert-butyl(3-methyl-2- aliphatic phosphines such as butenyl) phosphine, tricyclohexyl phosphine, etc.; Phenyl phosphine, diphenylcyclohexyl phosphine, triphenyl phosphine, tri-o-toluene phosphine, tri-m-toluene phosphine, tri-p-toluene phosphine, paras(4-ethylphenyl)phosphine, paras(4-ethylphenyl)phosphine 4-propylphenyl) phosphine, sine (4-isopropylphenyl) phosphine, sine (4-butylphenyl) phosphine, sine (4-tert-butylphenyl) phosphine, sine (2,4) -Dimethylphenyl) phosphine, sine (2,5-dimethylphenyl) phosphine, sine (2,6-dimethylphenyl) phosphine, sine (3,5-dimethylphenyl) phosphine , ginseng (2,4,6-trimethylphenyl) phosphine, ginseng (2,6-dimethyl-4-ethoxyphenyl) phosphine, ginseng (2-methoxyphenyl) phosphine, ginseng (4-Methoxyphenyl)phosphine, Ps(4-ethoxyphenyl)phosphine, Ps(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 , Aromatic phosphines such as 2,2'-bis(diphenylphosphine)diphenyl ether, etc.

Examples of urea-based curing accelerators include 1,1-dimethylurea; 1,1,3-trimethylurea, 3-ethyl-1,1-dimethylurea, 3-cyclohexyl-1 , 1-dimethylurea, 3-cyclooctyl-1,1-dimethylurea and other aliphatic dimethylurea; 3-phenyl-1,1-dimethylurea, 3-(4- Chlorophenyl)-1,1-dimethylurea, 3-(3,4-dichlorophenyl)-1,1-dimethylurea, 3-(3-chloro-4-methylphenyl) -1,1-dimethylurea, 3-(2-methylphenyl)-1,1-dimethylurea, 3-(4-methylphenyl)-1,1-dimethylurea, 3-(3,4-Dimethylphenyl)-1,1-dimethylurea, 3-(4-isopropylphenyl)-1,1-dimethylurea, 3-(4-methylurea Oxyphenyl)-1,1-dimethylurea, 3-(4-nitrophenyl)-1,1-dimethylurea, 3-[4-(4-methoxyphenoxy) Phenyl]-1,1-dimethylurea, 3-[4-(4-chlorophenoxy)phenyl]-1,1-dimethylurea, 3-[3-(trifluoromethyl) Phenyl]-1,1-dimethylurea, N,N-(1,4-phenylene)bis(N',N'-dimethylurea), N,N-(4-methyl- Aromatic dimethylurea such as 1,3-phenylene)bis(N',N'-dimethylurea)[toluenebisdimethylurea], etc.

Examples of guanidine-based curing accelerators include dicyandiamide, 1-methylguanidine, 1-ethylguanidine, 1-cyclohexylguanidine, 1-phenylguanidine, 1-(o-tolyl)guanidine, dicyandiamide Methylguanidine, 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-methyl biguanide, 1-ethyl biguanide, 1-n-butyl biguanide, 1-n-octadecyl biguanide , 1,1-dimethyl biguanide, 1,1-diethyl biguanide, 1-cyclohexyl biguanide, 1-allyl biguanide, 1-phenyl biguanide, 1-(o-tolyl) biguanide, etc.

Examples of imidazole-based curing accelerators include 2-methylimidazole, 2-undecylimidazole, 2-heptadecylimidazole, 1,2-dimethylimidazole, and 2-ethyl-4-methyl Imidazole, 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 trimellitic acid salt, 1-cyanoethyl-2-phenylimidazole trimellitic acid salt, 2,4-diamino-6-[2'-methylimidazolyl-(1')]-ethyl-s-triazine, 2,4-diamino-6-[2'-ten Monoalkylimidazolyl-(1')]-ethyl-s-triazine, 2,4-diamino-6-[2'-ethyl-4'-methylimidazolyl-(1')] -Ethyl-s-triazine, 2,4-diamino-6-[2'-methylimidazolyl-(1')]-ethyl-s-triazine isocyanuric acid adduct, 2-Phenylimidazole isocyanuric acid adduct, 2-phenyl-4,5-dihydroxymethylimidazole, 2-phenyl-4-methyl-5-hydroxymethylimidazole, 2,3- Dihydro-1H-pyrro[1,2-a]benzimidazole, 1-dodecyl-2-methyl-3-benzylimidazolium chloride, 2-methylimidazoline, 2-phenylimidazole imidazole compounds such as linoline and adducts of imidazole compounds and epoxy resins.

Commercially available products can be used as imidazole-based curing accelerators, and examples thereof include "1B2PZ", "2MZA-PW", "2PHZ-PW" manufactured by Shikoku Chemical Co., Ltd., and "P200-H50" manufactured by Mitsubishi Chemical Co., Ltd. .

Examples of the metal-based hardening accelerator include organometallic complexes and organometallic salts of metals such as cobalt, copper, zinc, iron, nickel, manganese, and tin. Specific examples of the organometallic complex include organocobalt complexes such as cobalt (II) acetylacetonate, cobalt (III) acetylacetonate, and the like, and organocopper complexes such as copper (II) acetylacetonate. , Organic zinc complexes such as zinc (II) acetylacetonate, organic iron complexes such as iron (III) acetylacetonate, organic nickel complexes such as nickel (II) acetylacetonate, acetylpyruvic acid Organic manganese complexes such as manganese (II), etc. As an organic metal salt, zinc octylate, tin octylate, zinc naphthenate, cobalt naphthenate, tin stearate, zinc stearate, etc. are mentioned, for example.

Examples of the amine-based curing accelerator include trialkylamines such as triethylamine and tributylamine, 4-dimethylaminopyridine, benzyldimethylamine, 2,4,6,-paraffin ( Dimethylaminomethyl)phenol, 1,8-diazabicyclo(5,4,0)-undecene, etc.

As an amine type hardening accelerator system, a commercial item can be used, for example, "MY-25" by Ajinomoto Fine-Techno Corporation, etc. are mentioned.

The content of the (E) curing accelerator in the resin composition is not particularly limited, but when the nonvolatile content in the resin composition is 100% by mass, it is preferably 15% by mass or less, and more preferably 10% by mass Below, it is more preferable that it is 5 mass % or less, and it is especially preferable that it is 3 mass % or less. The lower limit of the content of the (E) curing accelerator in the resin composition is not particularly limited, but when the nonvolatile content in the resin composition is 100% by mass, for example, it may be 0% by mass or more, 0.001% by mass or more, 0.01 mass % or more, 0.1 mass % or more, 0.5 mass % or more, and the like.

<(F) Other additives> The resin composition system of the present invention may further contain arbitrary additives as nonvolatile components. Examples of such additives include radical polymerization initiators such as peroxide-based radical polymerization initiators and azo-based radical polymerization initiators; phenol-based curing agents, naphthol-based curing agents, and acid anhydrides Epoxy hardeners other than active ester compounds such as hardeners, thiol hardeners, benzoxazine hardeners, cyanate ester hardeners, carbodiimide hardeners, imidazole hardeners, etc.; benzene Thermoplastic resins such as oxygenated resins, polyvinyl acetal resins, polyolefin resins, polysilicon resins, polyether resins, polyphenylene ether resins, polycarbonate resins, polyether ether ketone resins, polyester resins, etc.; rubber particles Organic fillers such as organic fillers; organic metal compounds such as organic copper compounds, organic zinc compounds, organic cobalt compounds, etc.; colorants such as phthalocyanine blue, phthalocyanine green, iodine green, diazo yellow, crystal violet, titanium oxide, carbon black, etc.; Polymerization inhibitors for hydroquinone, catechol, pyrogallol, phenothiazine, etc.; leveling agents for polysiloxane-based leveling agents, acrylic polymer-based leveling agents, etc.; Thickening agent; defoamer for polysiloxane-based defoamer, acrylic-based defoamer, fluorine-based defoamer, vinyl resin-based defoamer, etc.; UV absorber for benzotriazole-based UV absorber; Adhesion enhancers such as urea silanes; adhesion imparting agents such as triazole-based adhesion imparting agents, tetrazole-based adhesion imparting agents, and triazine-based adhesion imparting agents; hindered phenolic antioxidants, hindered Antioxidants such as amine-based antioxidants; fluorescent whitening agents such as stilbene derivatives; surfactants such as fluorine-based surfactants, polysiloxane-based surfactants, etc.; phosphorus-based flame retardants (such as phosphate compounds, Phosphazene compounds, phosphinic acid compounds, red phosphorus), nitrogen-based flame retardants (such as melamine sulfate), halogen-based flame retardants, inorganic flame retardants (such as antimony trioxide) and other flame retardants; Phosphate esters Dispersants such as dispersants, polyoxyalkylene-based dispersants, acetylene-based dispersants, polysiloxane-based dispersants, anionic dispersants, cationic dispersants, etc.; borate-based stabilizers, titanate-based stabilizers stabilizers, aluminate-based stabilizers, zirconate-based stabilizers, isocyanate-based stabilizers, carboxylic acid-based stabilizers, carboxylic acid anhydride-based stabilizers, and the like. (F) Other additive system may be used individually by 1 type, and may be used in combination of 2 or more types by arbitrary ratios. (F) The content of other additives can be appropriately set by the manufacturer.

<(G) Organic solvent> The resin composition of the present invention may further contain an arbitrary organic solvent as a volatile component in addition to the above-mentioned nonvolatile component. As (G) organic solvent system, a well-known thing can be used suitably, and the kind is not specifically limited. As the (G) organic solvent, for example, ketone-based solvents such as acetone, methyl ethyl ketone, methyl isobutyl ketone, and cyclohexanone; methyl acetate, ethyl acetate, butyl acetate, and isobutyl acetate Ester solvents such as esters, isoamyl acetate, methyl propionate, ethyl propionate, γ-butyrolactone, etc.; tetrahydropyran, tetrahydrofuran, 1,4-dioxane, diethyl ether, diiso Ether-based solvents such as propyl ether, dibutyl ether, diphenyl ether, etc.; alcohol-based solvents such as methanol, ethanol, propanol, butanol, ethylene glycol, etc.; 2-ethoxyethyl acetate, propylene glycol monomethyl ether ester-based solvents such as methyl ether acetate, diethylene glycol monoethyl ether acetate, diethylene glycol ethyl acetate, γ-butyrolactone, methyl methoxypropionate, etc.; methyl lactate, Ethyl lactate, methyl 2-hydroxyisobutyrate, etc. ester alcohol solvents; 2-methoxypropanol, 2-methoxyethanol, 2-ethoxyethanol, propylene glycol monomethyl ether, diethyl ether Ether alcohol-based solvents such as glycol monobutyl ether (butyl carbitol); N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrole Amide-based solvents such as pyridone; sulfite-based solvents such as dimethylsulfoxide; nitrile-based solvents such as acetonitrile and propionitrile; aliphatics such as hexane, cyclopentane, cyclohexane, and methylcyclohexane Aromatic hydrocarbon-based solvents; aromatic hydrocarbon-based solvents such as benzene, toluene, xylene, ethylbenzene, trimethylbenzene, etc. (G) An organic solvent system may be used individually by 1 type, and may be used in combination of 2 or more types in arbitrary ratios.

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

<Manufacturing method of resin composition> The resin composition system of the present invention can be produced, for example, by adding (A) a specific maleimide compound, ( B) epoxy resin, (C) inorganic filler, (A') other maleimide compound as needed, (D) active ester compound as needed, (E) hardening accelerator as needed agent, (F) other additives as needed, and (G) organic solvent as needed, and mixed. In addition, in the process of adding and mixing each component, the temperature may be appropriately set, and heating and/or cooling may be performed temporarily or throughout. In addition, during or after the addition and mixing, the resin composition can be uniformly dispersed by stirring or shaking the resin composition using, for example, a stirring device such as a stirrer or a shaking device. In addition, while stirring or shaking, defoaming can also be performed under a low pressure condition such as a vacuum.

<Characteristics of resin composition> When the resin composition of the present invention contains (A) a specific maleimide compound, (B) an epoxy resin, and (C) an inorganic filler, and the nonvolatile content in the resin composition is 100% by mass , (C) The content of component is more than 30 mass %. By using such a resin composition, it is possible to obtain a cured product having a small arithmetic mean roughness (Ra) and a low specific permittivity (Dk) and a dielectric tangent (Df).

The cured product of the resin composition of the present invention may have characteristics such as low dielectric tangent (Df). Therefore, in one embodiment, as in Test Example 1 below, the dielectric tangent (Df) of the cured product of the resin composition when measured at 5.8 GHz and 23° C. is preferably 0.020 or less and 0.010 or less. It is preferably 0.009 or less and 0.008 or less, more preferably 0.007 or less and 0.006 or less, and particularly preferably 0.005 or less and 0.004 or less.

The cured product system of the resin composition of the present invention may have a characteristic that the specific dielectric constant (Dk) is low. Therefore, in one embodiment, as in Test Example 1 below, when measured at 5.8 GHz and 23° C., the specific permittivity (Dk) of the cured product of the resin composition is preferably 5.0 or less, and more preferably It may be 4.0 or less, more preferably 3.5 or less, and particularly preferably 3.0 or less.

In one Embodiment, the hardened|cured material system of the resin composition of this invention may have the characteristic that the arithmetic mean roughness (Ra) of the surface after roughening process is low. Therefore, in one embodiment, the arithmetic mean roughness (Ra) of the surface of the hardened product after roughening treatment as measured in the following test example 2 is preferably 300 nm or less, more preferably 200 nm or less, and more It is preferably 150 nm or less, more preferably 100 nm or less, and particularly preferably 80 nm or less. The lower limit is not particularly limited, but may be, for example, 1 nm or more, 2 nm or more, or the like.

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

<Application of resin composition> The resin composition of the present invention can be suitably used as a resin composition for insulating purposes, especially a resin composition for forming an insulating layer. Specifically, it is suitable as a resin composition for forming the insulating layer (resin composition for forming an insulating layer for forming a conductor layer) for forming a conductor layer (including a rewiring layer) on an insulating layer. thing). Moreover, in the printed wiring board mentioned later, it can be suitably used as a resin composition for forming the insulating layer of a printed wiring board (the resin composition for insulating layer formation of a printed wiring board). The resin composition of the present invention can also be widely used in sheet-like laminate materials such as resin sheets and prepregs, solder resists, underfill materials, die bonding materials, semiconductor sealing materials, hole-filling resins, and parts embedding In applications such as resins that require a resin composition.

In addition, for example, when a semiconductor chip package is manufactured through the following steps (1) to (6), the resin composition of the present invention can also be suitably used as an insulating layer when used to form a rewiring formation layer. Resin composition for rewiring formation layer (resin composition for rewiring formation layer formation), and resin composition for sealing semiconductor wafer (resin composition for semiconductor wafer sealing). When manufacturing a semiconductor chip package, a rewiring layer may be further formed on the sealing layer. (1) The step of laminating a temporary fixing film on the base material, (2) the step of temporarily fixing the semiconductor wafer on the temporary fixing film, (3) the step of forming the sealing layer on the semiconductor wafer, (4) the step of peeling off the base material and the temporary fixing film from the semiconductor wafer, (5) The step of forming a rewiring formation layer as an insulating layer on the surface of the base material of the semiconductor wafer and the surface from which the temporary fixing film has been peeled off, and (6) A step of forming a rewiring layer as a conductor layer on the rewiring formation layer.

In addition, since the resin composition of the present invention can form an insulating layer with good component burying properties, it can also be suitably used when the printed wiring board is a component-embedded circuit board.

<Laminated sheet material> The resin composition of the present invention may be applied and used in a varnish state, but industrially, it is generally suitable to use it in the form of a sheet-like laminate containing the resin composition.

As the sheet-like laminate material, resin sheets and prepregs shown below are preferable.

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

The thickness of the resin composition layer is preferably 50 μm or less from the viewpoint of thinning the printed wiring board and providing a cured product excellent in insulation even if the cured product of the resin composition is a thin film. Also preferably, it is 40 μm or less. The lower limit of the thickness of the resin composition layer is not particularly limited, but it is usually 5 μm or more, 10 μm or more, or the like.

As the support, for example, a film made of a plastic material, a metal foil, or a release paper can be mentioned, and a film and a metal foil made of a plastic material are preferable.

When a film composed of a plastic material is used as the support, the plastic material may, for example, include polyethylene terephthalate (hereinafter abbreviated as "PET"), polyethylene naphthalate (hereinafter abbreviated as "PET"). Polyester such as "PEN"), polycarbonate (hereinafter sometimes abbreviated as "PC"), acrylic acid such as polymethyl methacrylate (PMMA), cyclic polyolefin, triacetyl cellulose (TAC), polyether sulfide (PES), polyether ketone, polyimide, etc. Among them, polyethylene terephthalate and polyethylene naphthalate are preferred, and inexpensive polyethylene terephthalate is particularly preferred.

When using a metal foil as a support body, as a metal foil, a copper foil, an aluminum foil, etc. are mentioned, for example, A copper foil is preferable. As the copper foil system, a foil made of a simple metal of copper can be used, or a foil made of an alloy of copper and other metals (eg, tin, chromium, silver, magnesium, nickel, zirconium, silicon, titanium, etc.) can be used .

Polishing treatment, corona treatment, and antistatic treatment may be applied to the surface of the support to be joined to the resin composition layer.

Moreover, the support body with a mold release layer which has a mold release layer on the surface joined to a resin composition layer can also be used as a support body. As a mold release agent used for the mold release layer of the support body with a mold release layer, for example, a group selected from the group consisting of an alkyd resin, a polyolefin resin, a urethane resin, and a polysiloxane resin can be mentioned. One or more release agents. Commercially available products can be used for the support system with a release layer, and examples include "SK-1" and "AL" manufactured by LINTEC, which are PET films having a release layer containing an alkyd resin-based release agent as a main component. -5", "AL-7", "Lumirror T60" manufactured by Toray Corporation, "PUREX" manufactured by Teijin Corporation, "Unipeel" manufactured by Unitika Corporation, etc.

The thickness of the support body is not particularly limited, but is preferably in the range of 5 μm to 75 μm, and further preferably in the range of 10 μm to 60 μm. Furthermore, when a support with a mold release layer is used, the thickness of the entire support with a mold release layer is preferably within the above range.

In one embodiment, the resin sheet may further include an arbitrary layer as required. As said arbitrary layer, the protective film etc. which are chosen according to a support provided on the surface (that is, the surface opposite to the support) of the resin composition layer which are not joined to a support are mentioned, for example. The thickness of the protective film is not particularly limited, but is, for example, 1 μm to 40 μm. By laminating the protective film, adhesion or damage to the surface of the resin composition layer due to dust or the like can be suppressed.

For example, a resin composition can be formed by directly using a liquid resin composition or preparing a resin varnish in which the resin composition is dissolved in an organic solvent, coating this on a support using a die coater, and drying it to form a resin. The composition layer is used to manufacture a resin sheet.

As an organic solvent, the same thing as the organic solvent demonstrated as a component of a resin composition is mentioned. An organic solvent may be used individually by 1 type, and may be used in combination of 2 or more types.

The drying system can be implemented by known methods such as heating and blowing hot air. The drying conditions are not particularly limited, but the resin composition layer is dried so that the content of the organic solvent in the resin composition layer is 10 mass % or less, preferably 5 mass % or less. The boiling point of the organic solvent in the resin composition or resin varnish varies. For example, when using a resin composition or resin varnish containing an organic solvent in an amount of 30% by mass to 60% by mass, dry it at 50°C to 150°C. From 3 minutes to 10 minutes, a resin composition layer can be formed.

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

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

The sheet-like fiber base material used for the prepreg is not particularly limited, and commonly used ones as the base material for the prepreg, such as glass cloth, aromatic polyamide nonwoven cloth, and liquid crystal polymer nonwoven cloth, can be used. From the viewpoint of reducing the thickness of the printed wiring board, the thickness of the sheet-like fiber base material is preferably 50 μm or less, more preferably 40 μm or less, more preferably 30 μm or less, and particularly preferably 20 μm or less. The lower limit of the thickness of the sheet-like fibrous base material is not particularly limited. Usually 10 μm or more.

The prepreg system can be produced by a well-known method such as a hot melt method and a solvent method.

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

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

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

For example, the printed wiring board system can be manufactured by the method of the following steps (I) and (II) using the above-mentioned resin sheet: (1) the step of laminating resin sheets on the inner substrate in a manner that the resin composition layer of the resin sheet is bonded to the inner substrate; (II) A step of forming an insulating layer by hardening (eg, thermosetting) the resin composition layer.

The "inner layer substrate" used in the step (I) refers to a member that becomes a substrate of a printed wiring board, and examples thereof include glass epoxy substrates, metal substrates, polyester substrates, polyimide substrates, BT resin substrates, thermosetting substrates, etc. type polyphenylene ether substrate, etc. In addition, the substrate may have a conductor layer on one side or both sides, and the conductor layer may be patterned. An inner layer substrate in which a conductor layer (circuit) is formed on one side or both sides of the substrate is sometimes referred to as an "inner layer circuit substrate". Moreover, when manufacturing a printed wiring board, the intermediate product which forms an insulating layer and/or a conductor layer is also included in the so-called "inner-layer board|substrate" of this invention. If the printed wiring board is a circuit board with built-in components, the inner-layer substrate with built-in components can be used.

The lamination system of the inner layer substrate and the resin sheet can be performed, for example, by thermally pressing the resin sheet to the inner layer substrate from the support side. As a member for heat-bonding the resin sheet to the inner layer substrate (hereinafter also referred to as "heat-bonding member"), a heated metal plate (SUS mirror plate, etc.), a metal roll (SUS roll), etc. are mentioned, for example. Furthermore, it is preferable to press the thermocompression member not directly on the resin sheet, but via an elastic material such as heat-resistant rubber, so that the resin sheet sufficiently follows the surface unevenness of the inner layer substrate.

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

The lamination system can be performed by a commercially available vacuum laminating machine. As a commercially available vacuum laminating machine, the vacuum pressurization type|mold lamination machine by Meiki Seisakusho Co., Ltd., the vacuum lamination machine by Nikko-Materials Co., Ltd., a batch type vacuum pressurization lamination machine, etc. are mentioned, for example.

After lamination, under normal pressure (atmospheric pressure), for example, by pressing the thermocompression member from the support side, smoothing treatment of the laminated resin sheet can be performed. The pressing conditions of the smoothing treatment can be set to the same conditions as the heat pressing conditions of the above-mentioned lamination. The smoothing process can be performed by a commercially available laminator. Furthermore, the lamination and smoothing can be continuously performed using the above-mentioned commercially available vacuum laminating machine.

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

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

For example, although the thermal curing conditions of the resin composition layer may vary depending on the type of the resin composition, in one embodiment, the curing temperature is preferably 120°C to 240°C, and more preferably 150°C to 220°C. More preferably, it is 170 degreeC - 210 degreeC. The hardening time is preferably 5 minutes to 120 minutes, more preferably 10 minutes to 100 minutes, and more preferably 15 minutes to 100 minutes.

Before the resin composition layer can be thermally hardened, the resin composition layer can be preheated so as to be lower than the hardening temperature. For example, before thermosetting the resin composition layer, the resin composition layer is heated at a temperature of 50°C to 120°C, preferably 60°C to 115°C, and preferably 70°C to 110°C for 5 minutes or more, preferably Preheating is performed for 5 minutes to 150 minutes, preferably 15 minutes to 120 minutes, and more preferably 15 minutes to 100 minutes.

When manufacturing a printed wiring board, (III) the step of opening a hole in the insulating layer, (IV) the step of roughening the insulating layer, and (V) the step of forming the conductor layer may be further performed. These steps (III) to (V) can be implemented in accordance with various methods known to the industry used for the manufacture of printed wiring boards. Furthermore, if the support is removed after step (II), the removal of the support may be between step (II) and step (III), between step (III) and step (IV), or between step (IV) ) and step (V). In addition, the formation of the insulating layer and the conductor layer in the steps (II) to (V) may be repeated as necessary to form a multilayer wiring board.

In other embodiment, the printed wiring board system of this invention can be manufactured using the above-mentioned prepreg. The manufacturing method is basically the same as the case of using the resin sheet.

Step (III) is a step of opening holes on the insulating layer, whereby holes such as through holes and through holes can be formed on the insulating layer. The step (III) is carried out using, for example, drilling, laser, plasma, etc., depending on the composition and the like of the resin composition used for forming the insulating layer. The size or shape of the holes can be appropriately determined according to the design of the printed wiring board.

Step (IV) is a step of roughening the insulating layer. Usually in this step (IV), smear removal is also carried out. The steps and conditions of the roughening treatment are not particularly limited, and well-known steps and conditions generally used when forming an insulating layer of a printed wiring board can be adopted. For example, a swelling treatment with a swelling liquid, a roughening treatment with an oxidizing agent, and a neutralization treatment with a neutralizing liquid can be sequentially performed to roughen the insulating layer.

The swelling liquid used in the roughening treatment is not particularly limited, and examples thereof include an alkaline solution, a surfactant solution, and the like, and an alkaline solution is preferred. As the alkaline solution, a sodium hydroxide solution and a potassium hydroxide solution are more preferred. good. As a commercially available swelling liquid, "Swelling Dip Securiganth P", "Swelling Dip Securiganth SBU" by Atotech Japan, etc. are mentioned, for example. The swelling treatment by the swelling liquid is not particularly limited, and is performed, for example, by immersing the insulating layer in the swelling liquid at 30° C. to 90° C. for 1 minute to 20 minutes. From the viewpoint of suppressing the swelling of the resin of the insulating layer to an appropriate level, it is preferable to immerse the insulating layer in a swelling liquid of 40° C. to 80° C. for 5 minutes to 15 minutes.

Although it does not specifically limit as an oxidizing agent used for roughening process, For example, the alkaline permanganic acid solution which melt|dissolved potassium permanganate or sodium permanganate in the aqueous solution of sodium hydroxide is mentioned. The roughening treatment by an oxidizing agent such as an alkaline permanganic acid solution is preferably performed by immersing the insulating layer in an oxidizing agent solution heated to 60° C. to 100° C. for 10 minutes to 30 minutes. In addition, the concentration of the permanganate in the alkaline permanganic acid solution is preferably 5% by mass to 10% by mass. Examples of commercially available oxidizing agents include alkaline permanganic acid solutions such as "Concentrate Compact CP" and "Dosing solution Securiganth P" manufactured by Atotech Japan.

Moreover, an acidic aqueous solution is preferable as a neutralization liquid system used for a roughening process, and "Reduction solution Securiganth P" by Atotech Japan is mentioned as a commercial item, for example.

The treatment with the neutralization solution can be performed by immersing the treated surface subjected to the roughening treatment of the oxidizing agent in the neutralization solution at 30° C. to 80° C. for 5 minutes to 30 minutes. From the point of workability etc., the method of immersing the object of the roughening process of an oxidizing agent in the neutralization liquid of 40 degreeC - 70 degreeC for 5 minutes - 20 minutes is preferable.

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

Step (V) is a step of forming a conductor layer, and a conductor layer is formed on the insulating layer. The conductor material used for the conductor layer is not particularly limited. In a suitable embodiment, the conductor layer comprises one selected from the group consisting of gold, platinum, palladium, silver, copper, aluminum, cobalt, chromium, zinc, nickel, titanium, tungsten, iron, tin and indium above metals. The conductor layer may be a simple metal layer or an alloy layer, and the alloy layer may be, for example, an alloy of two or more metals selected from the above group (such as nickel-chromium alloy, copper-nickel alloy, and copper-titanium alloy). ) formed layer. Among them, from the viewpoints of versatility, cost, ease of patterning, etc. of the formation of the conductor layer, a simple metal layer of chromium, nickel, titanium, aluminum, zinc, gold, palladium, silver, or copper, or nickel, The alloy layer of chromium alloy, copper-nickel alloy, and copper-titanium alloy is preferred, and a simple metal layer of chromium, nickel, titanium, aluminum, zinc, gold, palladium, silver or copper, or an alloy layer of nickel-chromium alloy is used. It is still more preferable, and the elemental metal layer of copper is more preferable.

The conductor layer system may have a single-layer structure, or may have a multi-layer structure in which a single metal layer or an alloy layered layer composed of different kinds of metals or alloys is formed of two or more layers. When the conductor layer has a multilayer structure, the layer in contact with the insulating layer is preferably a simple metal layer of chromium, zinc, or titanium, or an alloy layer of a nickel-chromium alloy.

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

In one embodiment, the conductor layer can be formed by plating. For example, the surface of the insulating layer is plated by a conventionally known technique such as a semi-additive method or a full-additive method to form a conductor layer having a desired wiring pattern. It is preferable to form by a semi-additive method. The following shows an example of forming the conductor layer by the semi-additive method.

First, a plating nucleation layer is formed on the surface of the insulating layer by electroless plating. Next, on the formed plating nucleation layer, a mask pattern for exposing a part of the plating nucleation layer is formed in accordance with a desired wiring pattern. On the exposed plating nucleation layer, after forming a metal layer by electrolytic plating, the mask pattern is removed. After that, by removing the unnecessary plating nucleation layer by etching or the like, a conductor layer having a desired wiring pattern can be formed.

In other embodiments, the conductor layer can be formed using metal foil. When a metal foil is used to form the conductor layer, the step (V) is suitably performed between the step (I) and the step (II). For example, after the step (I), the support is removed, and the metal foil is laminated on the surface of the exposed resin composition layer. The lamination of the resin composition layer and the metal foil can be carried out by a vacuum lamination method. The conditions for lamination may be the same as those described for the step (I). Next, step (II) is carried out to form an insulating layer. Then, using the metal foil on the insulating layer, a conductor layer having a desired wiring pattern can be formed by conventional well-known techniques such as an erasing treatment method and an improved semi-additive method.

The metal foil can be produced by known methods such as an electrolytic method and a rolling method, for example. As a commercial item of a metal foil, HLP foil by JX Nippon Mining & Metal Co., Ltd., JXUT-III foil, 3EC-III foil by Mitsui Metal Mining Co., Ltd., TP-III foil, etc. are mentioned, for example.

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

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

Hereinafter, the present invention will be specifically described by way of examples. The present invention is not limited to these embodiments. In addition, the following "parts" and "%" indicating amount, unless otherwise specified, represent "mass parts" and "mass %" respectively. The temperature conditions are room temperature (25°C) unless a special temperature is specified.

<Example 1> Maleimide-terminated polyimide (“BMI-6100” manufactured by Designer Molecules) and 10 parts of naphthol aralkyl type epoxy resin (“ESN-6100” manufactured by Nippon Steel Chemical & Material) were used. 475V”) 18 parts, spherical silica (“SO-C2” manufactured by Admatechs, average particle size 0.5 μm, specific surface area 5.8 m ² /g) 60 parts, active ester compound ("HPC-8150-60T" manufactured by DIC Corporation, toluene solution with a solid content of 60% by mass) 18.3 parts, imidazole-based curing accelerator ("1B2PZ" manufactured by Shikoku Chemical Industry Co., Ltd., 1 -1 part of -benzyl-2-phenylimidazole) was mixed, and it disperse|distributed uniformly with a high-speed rotary stirrer, and prepared the resin composition.

<Example 2> In addition to changing the usage amount of naphthol aralkyl type epoxy resin (“ESN-475V” manufactured by Nippon Steel Chemical & Material Co., Ltd.) from 18 parts to 15 parts, an active ester compound (“HPC-8150-60T manufactured by DIC Corporation”) ”, the amount of toluene solution with a solid content of 60% by mass) was changed from 18.3 parts to 16.7 parts, and an aromatic maleimide (“MIR-3000-70MT” manufactured by Nippon Kayaku Co., Ltd., with a solid content of 70%) was used. A resin composition was prepared in the same manner as in Example 1 except for 5.7 parts of MEK/toluene mixed solution).

<Example 3> A maleimide compound A represented by the following formula (X) (Mw/Mn=1.81, t”= 1.47 (mainly 1, 2 or 3)) of the MEK solution (non-volatile content 70% by mass).

In addition to changing the usage amount of naphthol aralkyl type epoxy resin (“ESN-475V” manufactured by Nippon Steel Chemical & Material Co., Ltd.) from 18 parts to 15 parts, an active ester compound (“HPC-8150-60T manufactured by DIC Corporation”) ”, the amount of toluene solution with a solid content of 60% by mass) was changed from 18.3 parts to 16.7 parts, and further 5.7 parts of aromatic maleimide (maleimide compound A, MEK solution with a solid content of 70%) was used Other than that, the resin composition was prepared in the same manner as in Example 1.

<Example 4> In addition to changing the usage amount of naphthol aralkyl type epoxy resin (“ESN-475V” manufactured by Nippon Steel Chemical & Material Co., Ltd.) from 18 parts to 15 parts, an active ester compound (“HPC-8150-60T manufactured by DIC Corporation”) ”, a toluene solution with a solid content of 60% by mass) was changed from 18.3 parts to 16.7 parts, and a divinylbenzene/styrene copolymer (“ODV-XET-X04” manufactured by Nippon Steel Chemical & Material Co., Ltd.) was used, and the solid A resin composition was prepared in the same manner as in Example 1 except for 6.2 parts of a 65% toluene solution.

<Example 5> In addition to changing the usage amount of naphthol aralkyl type epoxy resin (“ESN-475V” manufactured by Nippon Steel Chemical & Material Co., Ltd.) from 18 parts to 15 parts, an active ester compound (“HPC-8150-60T manufactured by DIC Corporation”) ”, a toluene solution with a solid content of 60% by mass) was changed from 18.3 parts to 16.7 parts, and vinylbenzyl modified polyphenylene ether (“OPE-2St 2200” manufactured by Mitsubishi Gas Chemical Co., Ltd., solid content 65%) was used. Resin composition was prepared in the same manner as in Example 1 except for 6.2 parts of toluene solution.

<Example 6> In addition to changing the usage amount of naphthol aralkyl type epoxy resin (“ESN-475V” manufactured by Nippon Steel Chemical & Material Co., Ltd.) from 18 parts to 15 parts, an active ester compound (“HPC-8150-60T manufactured by DIC Corporation”) ”, a toluene solution with a solid content of 60% by mass) was changed from 18.3 parts to 16.7 parts, and methacrylic acid-modified polyphenylene ether (“SA9000-111” manufactured by Sabic Innovative Plastics Co., Ltd.) was used as a solid content of 50%. A resin composition was prepared in the same manner as in Example 1 except for 8 parts of toluene solution.

<Comparative Example 1> In addition to using 14.3 parts of aromatic maleimide (“MIR-3000-70MT” manufactured by Nippon Kayaku Co., Ltd., a MEK/toluene mixed solution with a solid content of 70%) instead of maleimide-terminated polyimide (Designer A resin composition was prepared in the same manner as in Example 1 except for 10 parts of "BMI-6100" (manufactured by Molecules).

<Comparative Example 2> Instead of using 10 parts of maleimide-terminated polyimide (“BMI-6100” manufactured by Designer Molecules), a naphthol aralkyl type epoxy resin (“ESN-6100” manufactured by Nippon Steel Chemical & Materials Co., Ltd.) was used. 475V") was changed from 18 parts to 23 parts, and the use amount of active ester compound ("HPC-8150-60T" manufactured by DIC Corporation, a toluene solution with a solid content of 60% by mass) was changed from 18.3 parts to 26.7 parts , and the rest were prepared in the same manner as in Example 1 to prepare the resin composition.

<Test example 1: Measurement of specific permittivity (Dk) and dielectric tangent (Df)> As a support, a polyethylene terephthalate film (“AL5” manufactured by LINTEC, thickness 38 μm) provided with a mold release layer was prepared. The resin compositions obtained in Examples and Comparative Examples were uniformly applied on the mold release layer of the support so that the thickness of the resin composition layer after drying was 40 μm. After that, the resin composition was dried at 80° C. to 100° C. (average 90° C.) for 4 minutes to obtain a resin sheet A including a support and a resin composition layer.

The obtained resin sheet A was cured in an oven at 190° C. for 90 minutes. The cured product of the resin composition layer was obtained by peeling off the support body with the resin sheet A taken out from the oven. This cured product was cut into a length of 80 mm and a width of 2 mm as a cured product B for evaluation.

For the hardened product B for evaluation, "HP8362B" manufactured by Agilent Technologies was used, and the value of the dielectric constant (Dk value) and the dielectric value were measured at a measurement frequency of 5.8 GHz and a measurement temperature of 23°C according to the cavity resonance perturbation method. The value of the tangent (Df value). The measurement was performed with two test pieces, and the average was calculated.

<Test Example 2: Measurement of Peel Strength and Arithmetic Average Roughness (Ra)> (1) Preparation of inner layer substrate A glass cloth base epoxy resin double-sided copper-clad laminate (copper foil thickness 18 μm, substrate thickness 0.4 mm, manufactured by Panasonic Corporation) was formed with a microetchant (“CZ8101” manufactured by MEC Corporation) on which inner layer circuits were formed. "R1515A") was etched by 1 μm on both sides to roughen the copper surface.

(2) Lamination of resin sheet A Using a batch-type vacuum pressure laminating machine (manufactured by Nikko-Materials, a two-stage build-up laminating machine "CVP700"), the resin composition layer and the inner layer substrate were brought into contact with each other. The resin sheet A is laminated on both sides of the inner layer substrate. After the lamination system was decompressed for 30 seconds and the air pressure was adjusted to 13 hPa or less, it was carried out by pressing at 120° C. and a pressure of 0.74 MPa for 30 seconds. Next, hot pressing was performed at 100° C. and a pressure of 0.5 MPa for 60 seconds.

(3) Thermosetting of the resin composition layer Then, the inner layer substrate on which the resin sheet A was laminated was put into an oven at 130° C. and heated for 30 minutes, then transferred to an oven at 170° C. for 30 minutes, and the resin composition layer was thermally cured to form an insulating layer . Then, the support body was peeled off, and the cured board|substrate A which has an insulating layer, an inner-layer board|substrate, and an insulating layer in this order was obtained.

(4) Coarsening treatment With respect to the hardened board|substrate A, the desmear process as a roughening process is performed. As the desmear treatment, the following wet desmear treatment was performed.

(Wet degreaser treatment) The cured substrate A was immersed in a swelling solution (“Swelling Dip Securiganth P” manufactured by Atotech Japan, an aqueous solution of diethylene glycol monobutyl ether and sodium hydroxide) at 60° C. for 5 minutes, and then, at 80° C. in an oxidizing agent solution ("Concentrate Compact CP" manufactured by Atotech Japan, an aqueous solution with a potassium permanganate concentration of about 6% and a sodium hydroxide concentration of about 4%) for 20 minutes. Next, it was immersed at 40 degreeC for 5 minutes in a neutralizing liquid ("Reduction solution Securiganth P", sulfuric acid aqueous solution by Atotech Japan company), and it dried at 80 degreeC for 15 minutes.

(5) Measurement of Arithmetic Average Roughness (Ra) of Surface of Insulating Layer After Roughening Treatment The arithmetic mean roughness (Ra) of the surface of the insulating layer of the hardened substrate A after the roughening treatment was measured by using a non-contact surface roughness meter (WYKO NT3300 manufactured by Bruker Corporation) in a VSI mode and a 50-times lens, at 121 μm× Calculated from the value obtained in the 92 μm measurement range. The measurement was performed by obtaining the average value of 10 points respectively.

(6) Formation of Conductor Layer The conductor layer was formed on the roughened surface of the insulating layer of the cured substrate A by the semi-additive method. That is, the roughened substrate was immersed in an electroless plating solution containing PdCl ₂ at 40° C. for 5 minutes, and then immersed in an electroless copper plating solution at 25° C. for 20 minutes. Next, after heating at 150° C. for 30 minutes to perform annealing treatment, an etching resist was formed and patterning was performed by etching. Then, copper sulfate electrolytic plating was performed to form a conductor layer with a thickness of 25 μm, and annealing treatment was performed at 190° C. for 60 minutes. The obtained board|substrate is called "evaluation board|substrate B".

(7) Measurement of peel strength of plated conductor layer The measurement of the peeling strength of an insulating layer and a conductor layer was performed based on Japanese Industrial Standards (JIS C6481). Specifically, for the conductor layer of the evaluation substrate B, a partial opening with a width of 10 mm and a length of 100 mm was cut, and one end was peeled off and clamped with a clipper, and the measurement was carried out at room temperature and at a speed of 50 mm/min and peeled off 35 mm in the vertical direction. The peel strength was obtained by the load (kgf/cm) at the time. The measurement system used a tensile tester (“AC-50C-SL” manufactured by TSE).

The usage-amount of the non-volatile matter of the resin composition of an Example and a comparative example, and the measurement result of a test example are shown in Table 1 below.

According to the above, it can be known that by using a resin composition comprising (A) a maleimide compound, (B) an epoxy resin, and (C) an inorganic filler, and the non-volatile matter in the resin composition is When the component is 100 mass %, the content of the component (C) is more than 30 mass %, wherein the maleimide compound contains a divalent group represented by the formula (1) and the formula ( 2) The bivalent group represented by the formula (3) and/or the bivalent group represented by the formula (3) can obtain a small arithmetic mean roughness (Ra), a specific permittivity (Dk) and a dielectric tangent (Df) ) is low hardening.

Claims (20)

A resin composition comprising (A) a maleimide compound, (B) an epoxy resin, and (C) an inorganic filler, and when the nonvolatile content in the resin composition is 100% by mass, (C) ) component is more than 30% by mass, wherein the maleimide compound contains, in one molecule, a divalent group represented by the formula (1), and a divalent group represented by the formula (2) and /or a divalent group represented by formula (3),

[wherein, X ¹ represents a single bond, -C(R ¹⁰ ) ₂ -, -O-, -CO-, -S-, -SO-, -SO ₂ -, -CONH-, -NHCO-, -COO -, or -OCO-; R ¹⁰ independently represents a hydrogen atom, an alkyl group, an alkenyl group, an aryl-alkyl group, or an aryl group; R ¹¹ , R ¹² , R ¹³ , R ¹⁴ , R ²¹ , R ²² , R ²³ , and R ²⁴ , at least one of them independently represents an alkyl group, an alkenyl group, an aryl-alkyl group, or an aryl group, and the other represents a hydrogen atom; and * represents a bonding site]

[In the formula, R ³¹ , R ³² , and R ³³ each independently represent a hydrogen atom, an alkyl group, an alkenyl group, an aryl-alkyl group, or an aryl group; and * represents a bonding site]

[In the formula, R ⁴¹ and R ⁴² each independently represent a hydrogen atom, an alkyl group, an alkenyl group, an aryl-alkyl group, or an aryl group; and * represents a bonding site]. The resin composition of claim 1, wherein X ¹ is -C(R ¹⁰ ) ₂ -; R ¹¹ , R ¹² , R ²¹ , and R ²² are each independently an alkyl group; and R ¹⁰ , R ¹³ , R ¹⁴ , R ²³ , R ²⁴ , R ³¹ , R ³² , R ³³ , R ⁴¹ , and R ⁴² are hydrogen atoms. The resin composition according to claim 1, wherein the (A) component further contains a divalent group represented by the formula (4) in 1 molecule,

[wherein, X ² , X ³ , and X ⁴ each independently represent a single bond, -C(R ⁵⁰ ) ₂ -, -O-, -CO-, -S-, -SO-, -SO ₂ -, - CONH-, -NHCO-, -COO-, or -OCO-; R ⁵⁰ , R ⁵¹ , R ⁵² , R ⁵³ , R ⁵⁴ , R ⁶¹ , R ⁶² , R ⁶³ , R ⁶⁴ , R ⁷¹ , R ⁷² , R ⁷³ , R ⁷⁴ , R ⁸¹ , R ⁸² , R ⁸³ , and R ⁸⁴ each independently represent a hydrogen atom, an alkyl group, an alkenyl group, an aryl-alkyl group, or an aryl group; and * represents a bonding site]. The resin composition of claim 3, wherein X ² and X ⁴ are -O-; X ³ is -C(R ⁵⁰ ) ₂ -; R ⁵⁰ is each independently an alkyl group; and R ⁵¹ , R ⁵² , R ⁵³ , R ⁵⁴ , R ⁶¹ , R ⁶² , R ⁶³ , R ⁶⁴ , R ⁷¹ , R ⁷² , R ⁷³ , R ⁷⁴ , R ⁸¹ , R ⁸² , R ⁸³ , and R ⁸⁴ are hydrogen atoms. The resin composition according to claim 1, wherein the content of the component (A) is 1 to 40 mass % when the nonvolatile content in the resin composition is 100 mass %. The resin composition according to claim 1, further comprising (A') radically polymerizable compounds other than the (A) component. The resin composition according to claim 1, wherein the (B) component contains (B-1) an epoxy resin having a condensed ring structure. The resin composition according to claim 7, wherein the component (B-1) contains a naphthol aralkyl type epoxy resin. The resin composition according to claim 1, wherein the content of the component (B) is 1 to 50 mass % when the nonvolatile content in the resin composition is 100 mass %. The resin composition of claim 1, wherein the mass ratio of (A) component to (B) component ((A) component/(B) component) is 0.3 to 3. The resin composition according to claim 1, wherein the content of the component (C) is 50 mass % or more when the non-volatile matter in the resin composition is 100 mass %. The resin composition of claim 1, wherein the mass ratio of (A) component to (C) component ((A) component/(C) component) is 0.05 to 0.5. The resin composition according to claim 1, further comprising (D) an active ester compound. The resin composition according to claim 1, wherein, when measured at 5.8 GHz and 23° C., the dielectric tangent of the cured product of the resin composition is 0.005 or less. The resin composition according to claim 1, wherein when measured at 5.8 GHz and 23° C., the specific permittivity of the cured product of the resin composition is 3.0 or less. A hardened product of the resin composition according to any one of claims 1 to 15. A sheet-like laminate material containing the resin composition of any one of claims 1 to 15. A resin sheet having a support body and a resin composition layer provided on the support body, the resin composition layer being formed of the resin composition of any one of claims 1 to 15. A printed wiring board including an insulating layer made of a cured product of the resin composition of any one of claims 1 to 15. A semiconductor device comprising the printed wiring board of claim 19.