Resin composition, cured product, prepreg, metal foil-clad laminate, resin sheet, and printed wiring board

Abstract

Provided are a resin composition that exhibits high heat resistance and low permittivity, a cured product, a prepreg, a metal foil-clad laminate board, a resin sheet, and a printed circuit board. The resin composition includes a compound (A) represented by formula (M1), and a cyanate ester compound (B) having two or more aromatic moieties with at least one cyanate group substituent in each molecule. In formula (M1), A is a 4-6 ring alicyclic group.

Description

Technical Field

[0001] The present invention relates to a resin composition, a cured product, a prepreg, a metal foil-clad laminate, a resin sheet, and a printed wiring board.

Background Art

[0002] In recent years, the high integration and miniaturization of semiconductors used in communication devices, communication machines, personal computers, etc. have been progressing. Along with this, various properties required for printed wiring boards (for example, metal foil-clad laminates, etc.) used in these devices have become increasingly strict. The main required properties include, for example, metal foil peel strength, low water absorption, desmear resistance, flame resistance, low dielectric constant, low dielectric tangent, low coefficient of thermal expansion, heat resistance, etc.

[0003] In order to obtain a printed wiring board with improved properties in each of these aspects, studies have been conducted on resin compositions used as materials for printed wiring boards. For example, Patent Document 1 discloses a resin composition for a printed wiring board containing a bifunctional vinylbenzyl compound (a) containing a predetermined polyphenylene ether skeleton, a predetermined maleimide compound (b), a predetermined cyanate ester resin (c), and a predetermined epoxy resin (d).

[0004] Further, Patent Document 2 discloses a resin composition containing a predetermined cyanate ester compound (A), a predetermined polymaleimide compound (B), and a filler (C) as constituent components. Furthermore, Patent Document 3 discloses a resin composition containing a predetermined polymaleimide compound (A), a modified polyphenylene ether (B) end-modified with a substituent containing a carbon-carbon unsaturated double bond, and a filler (C).

Prior Art Documents

Patent Documents

[0005]

Patent Document 1

Patent Document 2

[0006] As described above, various resin compositions for printed wiring boards have been studied. With recent technological innovations, there has been a demand for a resin composition that is particularly excellent in heat resistance and dielectric properties. An object of the present invention is to solve such problems, and to provide a resin composition having high heat resistance and low dielectric properties, as well as a cured product, prepreg, metal foil-clad laminate, resin sheet, and printed wiring board. In particular, an object is to provide a resin composition suitable for printed wiring board applications. [Means for Solving the Problems]

[0007] As a result of investigations by the present inventors under the above problems, the above problems have been solved by the following means. <1>A resin composition comprising a compound (A) represented by formula (M1) and a cyanate ester compound (B) having two or more aromatic moieties substituted with at least one cyanato group in the molecule. [Chemical Formula] (In formula (M1), R M1 , R M2 , R M3 , and R M4 each independently represent a hydrogen atom or an organic group. R M5 and R M6 each independently represent a hydrogen atom or an alkyl group. Ar M represents a divalent aromatic group. A is a 4- to 6-membered alicyclic group. R M7 and R M8 are each independently an alkyl group. mx is 1 or 2, and lx is 0 or 1. R M9 and RM10 Each independently represents a hydrogen atom or an alkyl group. R M11 , R M12 , R M13 , and R M14 Each independently represents a hydrogen atom or an organic group. nx represents an integer of 1 or more and 20 or less.) <2>The resin composition according to <1>, wherein when the resin solid content in the resin composition is 100 parts by mass, the content of the compound (A) represented by the formula (M1) is 1 to 90 parts by mass. <3>The resin composition according to <1> or <2>, wherein when the resin solid content in the resin composition is 100 parts by mass, the content of the cyanate ester compound (B) having two or more aromatic moieties substituted by the at least one cyanato group in the molecule is 1 to 90 parts by mass. <4>The resin composition according to any one of <1> to <3>, further comprising a filler (D). <5>The resin composition according to <4>, wherein the content of the filler (D) in the resin composition is 50 to 1600 parts by mass with respect to 100 parts by mass of the resin solid content. <6>The resin composition according to any one of <1> to <5>, wherein the cyanate ester compound (B) having two or more aromatic moieties substituted by the at least one cyanato group in the molecule contains at least one selected from the group consisting of a phenol novolac type cyanate ester compound, a naphthol aralkyl type cyanate ester compound, a naphthylene ether type cyanate ester compound, a bisphenol A type cyanate ester compound, a bisphenol M type cyanate ester compound, and a diallylbisphenol A type cyanate ester compound. <7>The resin composition according to any one of <1> to <6>, which is for a printed wiring board. <8>A cured product of the resin composition according to any one of <1> to <7>. <9>A prepreg formed from a base material and the resin composition according to any one of <1> to <7>. <10>A metal foil-clad laminate comprising at least one prepreg according to <9> and a metal foil disposed on one or both sides of the prepreg. <11>A resin sheet including a support and a layer formed from the resin composition according to any one of <1> to <7> disposed on the surface of the support. <12>A printed wiring board including an insulating layer and a conductor layer disposed on the surface of the insulating layer, wherein the insulating layer includes at least one of a layer formed from the resin composition according to any one of <1> to <7> and a layer formed from the prepreg according to <9>.

Effects of the Invention

[0008] According to the present invention, it has become possible to provide a resin composition having high heat resistance and low dielectric properties, as well as a cured product, a prepreg, a metal foil-clad laminate, a resin sheet, and a printed wiring board. In particular, it has become possible to provide a resin composition suitable for printed wiring board applications.

Modes for Carrying Out the Invention

[0009] Hereinafter, modes for carrying out the present invention (hereinafter simply referred to as "the present embodiment") will be described in detail. Note that the following present embodiment is an exemplification for explaining the present invention, and the present invention is not limited to only the present embodiment. In this specification, "~" is used in the sense of including the numerical values described before and after it as a lower limit value and an upper limit value. In this specification, various physical property values and characteristic values are those at 23°C unless otherwise specified. In the notation of groups (atomic groups) in this specification, a notation that does not indicate substitution or non-substitution includes both a group (atomic group) having no substituent and a group (atomic group) having a substituent together with the group having no substituent. For example, the "alkyl group" includes not only an alkyl group having no substituent (unsubstituted alkyl group) but also an alkyl group having a substituent (substituted alkyl group). In this specification, a notation that does not indicate substitution or non-substitution is preferably unsubstituted. Note that "parts by mass" in this specification indicates the relative amount of components, and "mass%" indicates the absolute amount of components.

[0010] In this specification, the resin solid content refers to the components excluding the filler and the solvent, and includes the compound represented by formula (M1), the cyanate ester compound (B) having two or more aromatic moieties substituted by at least one cyanato group in the molecule, and other resin components (C) blended as required, as well as elastomers, silane coupling agents, and other components (such as additives like flame retardants).

[0011] The resin composition of this embodiment is characterized by including the compound (A) represented by formula (M1) and the cyanate ester compound (B) having two or more aromatic moieties substituted by at least one cyanato group in the molecule (which may be referred to as "specific cyanate ester compound" in this specification).

Chemical formula

[0012] By using such a resin composition, a cured product of a resin composition having high heat resistance and excellent low dielectric properties (excellent in low dielectric constant and / or low dielectric tangent) can be obtained. Such a resin composition can be preferably used as a material for printed wiring boards. It is presumed that the reason why the cured product of the resin composition of this embodiment has high heat resistance and low dielectric properties is as follows. That is, in this embodiment, by using a compound having two maleimide groups and having a condensed ring of an alicyclic ring such as an indane ring and an aromatic ring (the compound represented by formula (M1)), it is presumed that a cured product of a resin composition with low dielectric properties can be obtained. Furthermore, by using it in combination with a specific cyanate ester compound (B), it is presumed that a cured product of a resin composition excellent in heat resistance can be obtained. Furthermore, since the distance between the maleimide groups in the molecule of the compound represented by formula (M1) is appropriate, it can be cured appropriately, and it is presumed that a cured product of a resin composition having lower dielectric properties and excellent heat resistance can be obtained.

[0013] <Compound (A) represented by formula (M1)> The resin composition of this embodiment contains the compound (A) represented by formula (M1). Since the compound represented by formula (M1) has two maleimide groups in one molecule, the compounds (A) represented by formula (M1) react with each other, and the compound (A) represented by formula (M1) reacts with a specific cyanate ester compound (B). Furthermore, it reacts with other curable resin components (for example, "other resin component (C)" described later) to form a cured product, and together with the cured product of the specific cyanate ester compound (B) and the like, a cured product is formed. In addition, by adopting the compound (A) represented by formula (M1), the distance between maleimide groups (the distance between crosslinking points) becomes appropriate. Therefore, in the resin composition of this embodiment, the condensed ring structure of an alicyclic ring such as an indane ring contained in the compound (A) represented by formula (M1) exists at an appropriate distance in the cured product, and it is presumed that low dielectric properties and high heat resistance can be achieved. Furthermore, the cured product of the resin composition of this embodiment can maintain good dielectric properties even after moisture absorption by containing the compound (A) represented by formula (M1). Generally, the cured product of this type of resin composition deteriorates in dielectric properties when it absorbs moisture. However, since the A part of the compound (A) represented by formula (M1) has an alicyclic structure, the polarity of the compound is lowered, and it is possible to make it difficult to attract water.

[0014] Hereinafter, the compound represented by formula (M1) will be described.

Chemical formula

[0015] R M1 , R M2 , R M3 , and R M4 each independently represent a hydrogen atom or an organic group. The organic group here is preferably an alkyl group, more preferably an alkyl group having 1 to 12 carbon atoms, still more preferably an alkyl group having 1 to 6 carbon atoms, still more preferably a methyl group, an ethyl group, a propyl group, or a butyl group, and particularly preferably a methyl group. R M1 and R M3 are each independently preferably an alkyl group, and R M2 and R M4 are preferably hydrogen atoms. R M5 and R M6Each independently represents a hydrogen atom or an alkyl group, and the alkyl group is preferred. The alkyl group here is preferably an alkyl group having 1 to 12 carbon atoms, more preferably an alkyl group having 1 to 6 carbon atoms, still more preferably a methyl group, an ethyl group, a propyl group, or a butyl group, and particularly preferably a methyl group. Ar M represents a divalent aromatic group, preferably a phenylene group, a naphthalenediyl group, a phenanthrenediyl group, or an anthracenediyl group, more preferably a phenylene group, and still more preferably an m-phenylene group. Ar M may have a substituent, and as the substituent, an alkyl group is preferred, more preferably an alkyl group having 1 to 12 carbon atoms, still more preferably an alkyl group having 1 to 6 carbon atoms, still more preferably a methyl group, an ethyl group, a propyl group, or a butyl group, and particularly preferably a methyl group. However, Ar M is preferably unsubstituted. A is an alicyclic group having 4 to 6 members, and a 5-membered alicyclic group (preferably a group that forms an indane ring together with a benzene ring) is more preferred. R M7 and R M8 each independently represents an alkyl group, preferably an alkyl group having 1 to 6 carbon atoms, more preferably an alkyl group having 1 to 3 carbon atoms, and particularly preferably a methyl group. mx is 1 or 2, and 2 is preferred. lx is 0 or 1, and 1 is preferred. R M9 and R M10 each independently represents a hydrogen atom or an alkyl group, and the alkyl group is preferred. The alkyl group here is preferably an alkyl group having 1 to 12 carbon atoms, more preferably an alkyl group having 1 to 6 carbon atoms, still more preferably a methyl group, an ethyl group, a propyl group, or a butyl group, and particularly preferably a methyl group. R M11 、R M12 、R M13 、and R M14each independently represents a hydrogen atom or an organic group. The organic group here is preferably an alkyl group, more preferably an alkyl group having 1 to 12 carbon atoms, still more preferably an alkyl group having 1 to 6 carbon atoms, even more preferably a methyl group, an ethyl group, a propyl group, or a butyl group, and particularly preferably a methyl group. R M12 and R M13 each independently preferably represents an alkyl group, and R M11 and R M14 preferably represents a hydrogen atom. nx represents an integer of 1 or more and 20 or less. nx may be an integer of 10 or less. In addition, the resin composition of the present embodiment may contain only one kind of compound (A) represented by the formula (M1) in which at least the value of nx is different, or may contain two or more kinds. When two or more kinds are contained, the average value (average repeating unit number) n of nx in the compound (A) represented by the formula (M1) in the resin composition is preferably 0.95 or more, more preferably 0.98 or more, still more preferably 1.0 or more, even more preferably 1.1 or more, and preferably 10.0 or less, more preferably 8.0 or less, still more preferably 7.0 or less, even more preferably 6.0 or less in order to have a low melting point (low softening point), a low melt viscosity, and excellent handleability. The same applies to the formulas (M2) and (M3) described later.

[0016] The compound represented by the formula (M1) is preferably a compound represented by the following formula (M2).

Chemical formula

[0017] In the formula, R M21 , R M22 , R M23 , and R M24 each independently represents a hydrogen atom or an organic group. The organic group here is preferably an alkyl group, more preferably an alkyl group having 1 to 12 carbon atoms, still more preferably an alkyl group having 1 to 6 carbon atoms, still more preferably a methyl group, an ethyl group, a propyl group, or a butyl group, and particularly preferably a methyl group. R M21 and R M23 are preferably alkyl groups, and R M22 and R M24 are preferably hydrogen atoms. R M25 and R M26 each independently represents a hydrogen atom or an alkyl group, and an alkyl group is preferred. The alkyl group here is preferably an alkyl group having 1 to 12 carbon atoms, more preferably an alkyl group having 1 to 6 carbon atoms, still more preferably a methyl group, an ethyl group, a propyl group, or a butyl group, and particularly preferably a methyl group. R M27 , R M28 , R M29 , and R M30 each independently represents a hydrogen atom or an organic group, and a hydrogen atom is preferred. The organic group here is preferably an alkyl group, more preferably an alkyl group having 1 to 12 carbon atoms, still more preferably an alkyl group having 1 to 6 carbon atoms, still more preferably a methyl group, an ethyl group, a propyl group, or a butyl group, and particularly preferably a methyl group. R M31 and RM32 Each independently represents a hydrogen atom or an alkyl group, and the alkyl group is preferred. The alkyl group herein is preferably an alkyl group having 1 to 12 carbon atoms, more preferably an alkyl group having 1 to 6 carbon atoms, still more preferably a methyl group, an ethyl group, a propyl group, or a butyl group, and particularly preferably a methyl group. R M33 R M34 R M35 and R M36 Each independently represents a hydrogen atom or an organic group. The organic group herein is preferably an alkyl group, more preferably an alkyl group having 1 to 12 carbon atoms, still more preferably an alkyl group having 1 to 6 carbon atoms, still more preferably a methyl group, an ethyl group, a propyl group, or a butyl group, and particularly preferably a methyl group. R M33 and R M36 are preferably hydrogen atoms, and R M34 and R M35 are preferably alkyl groups. R M37 R M38 R M39 Each independently represents a hydrogen atom or an alkyl group, and the alkyl group is preferred. The alkyl group herein is preferably an alkyl group having 1 to 12 carbon atoms, more preferably an alkyl group having 1 to 6 carbon atoms, still more preferably a methyl group, an ethyl group, a propyl group, or a butyl group, and particularly preferably a methyl group. nx represents an integer of 1 or more and 20 or less. nx may be an integer of 10 or less.

[0018] The compound represented by the formula (M2) is preferably a compound of the following formula (M3).

Chemical formula

[0019] The molecular weight of the compound (A) represented by the formula (M1) is preferably 500 or more, more preferably 600 or more, and even more preferably 700 or more. By setting it to be not less than the lower limit value, the dielectric properties (low dielectric constant) and low water absorption of the resulting cured product tend to be further improved. Also, the molecular weight of the compound (A) represented by the formula (M1) is preferably 10,000 or less, more preferably 9,000 or less, even more preferably 7,000 or less, still more preferably 5,000 or less, and even more preferably 4,000 or less. By setting it to be not more than the upper limit value, the heat resistance and handleability of the resulting cured product tend to be further improved.

[0020] In addition, for the compound (A) represented by the formula (M1) used in the present embodiment, it is preferable that the cured product thereof has excellent dielectric properties. For example, for the cured product of the compound (A) represented by the formula (M1) used in the present embodiment, the dielectric constant (Dk) measured according to the cavity resonance perturbation method is preferably 3.0 or less, and more preferably 2.6 or less. Also, the lower limit value of the dielectric constant is, for example, preferably 2.0 or more for practical use. Also, for the cured product of the compound (A) represented by the formula (M1) used in the present embodiment, the dielectric tangent (Df) measured according to the cavity resonance perturbation method is preferably 0.01 or less, and more preferably 0.007 or less. Also, the lower limit value of the dielectric tangent is, for example, preferably 0.0001 or more for practical use.

[0021] In addition, for the compound (A) represented by the formula (M1) used in the present embodiment, it is preferable that the cured product thereof has high heat resistance. For the cured product of the compound (A) represented by the formula (M1) used in the present embodiment, the glass transition temperature measured according to JIS C6481:1996 dynamic viscoelasticity measurement is preferably 180°C or more, more preferably 200°C or more, and even more preferably 230°C or more. By setting it to be not less than the lower limit value, a cured product with more excellent heat resistance can be obtained. Also, the upper limit value of the glass transition temperature is preferably 400°C or less for practical use. As the compound (A) represented by the formula (M1) used in this embodiment, for example, X9-450 and X9-470 manufactured by DIC Corporation can be used.

[0022] When the resin solid content in the resin composition is 100 parts by mass, the content of the compound (A) represented by the formula (M1) in the resin composition of this embodiment is preferably 1 to 90 parts by mass. When the resin solid content in the resin composition is 100 parts by mass, the lower limit value of the content of the compound (A) represented by the formula (M1) is preferably 5 parts by mass or more, more preferably 10 parts by mass or more, further preferably 20 parts by mass or more, still more preferably 30 parts by mass or more, even more preferably 40 parts by mass or more, and may be 45 parts by mass or more. By setting it to be not less than the lower limit value, the chemical resistance and heat resistance of the obtained cured product tend to be further improved. Also, when the resin solid content in the resin composition is 100 parts by mass, the upper limit value of the content of the compound (A) represented by the formula (M1) is preferably 88 parts by mass or less, more preferably 85 parts by mass or less, further preferably 83 parts by mass or less, still more preferably 80 parts by mass or less, and may be 70 parts by mass or less, 60 parts by mass or less, or 55 parts by mass or less. By setting it to be not more than the upper limit value, the low water absorption and heat resistance of the obtained cured product tend to be further improved.

[0023] In addition, in the resin composition of the present embodiment, the content of the compound (A) represented by the formula (M1) is preferably 5% by mass or more, more preferably 10% by mass or more, further preferably 20% by mass or more, still more preferably 30% by mass or more, even more preferably 35% by mass or more, and furthermore, it may be 40% by mass or more or 45% by mass or more. By setting the content to be not less than the lower limit value, the chemical resistance and heat resistance of the obtained cured product tend to be further improved. The upper limit value of the content of the compound (A) represented by the formula (M1) is preferably 95% by mass or less, more preferably 90% by mass or less, further preferably 85% by mass or less, still more preferably 80% by mass or less, even more preferably 75% by mass or less, and furthermore, it may be 70% by mass or less, 60% by mass or less, or 55% by mass or less. By setting the content to be not more than the upper limit value, the low water absorption and heat resistance of the obtained cured product tend to be further improved. The resin composition of the present embodiment may contain only one kind of the compound (A) represented by the formula (M1), or may contain two or more kinds. When two or more kinds are contained, it is preferable that the total amount is within the above range.

[0024] <Specific cyanate ester compound (B)> The resin composition of the present embodiment contains a specific cyanate ester compound (B). In the present embodiment, by using the compound (A) represented by the formula (M1) and the specific cyanate ester compound (B) in combination, compared with the case of using a maleimide compound and the specific cyanate ester compound (B) in combination, which have been conventionally used, better heat resistance and / or low dielectric properties can be achieved.

[0025] As the specific cyanate ester compound (B) used in the present embodiment, a cyanate ester compound having two or more aromatic moieties substituted by at least one cyanato group commonly used in printed wiring boards can be widely used. Specifically, the lower limit of the number of cyanato groups in the specific cyanate ester compound (B) used in this embodiment is preferably 2 or more, more preferably 3 or more. By setting it to be not less than the above lower limit value, the heat resistance of the cured product of the resin composition tends to be further improved. Regarding the upper limit value, although it is not particularly defined, for example, it may be 50 or less. In addition, for the specific cyanate ester compound (B) used in this embodiment, it is preferable that its cured product has excellent dielectric properties. For example, for the cured product of the specific cyanate ester compound (B) used in this embodiment, the dielectric constant (Dk) measured according to the cavity resonance perturbation method is preferably 4.0 or less, more preferably 3.5 or less. Also, the lower limit value of the dielectric constant is, for example, preferably 2.0 or more for practical use. Further, for the cured product of the specific cyanate ester compound (B) used in this embodiment, the dielectric tangent (Df) measured according to the cavity resonance perturbation method is preferably 0.02 or less, more preferably 0.015 or less. Also, the lower limit value of the dielectric tangent is, for example, preferably 0.0001 or more for practical use.

[0026] In addition, for the specific cyanate ester compound (B) used in this embodiment, it is preferable that the heat resistance of its cured product is high. For the cured product of the specific cyanate ester compound (B) used in this embodiment, the glass transition temperature measured according to JIS C6481:1996 dynamic viscoelasticity measurement is preferably 150°C or higher, more preferably 180°C or higher, and even more preferably 200°C or higher. By setting it to be not less than the above lower limit value, a cured product with excellent heat resistance can be obtained.

[0027] The specific cyanate ester compound (B) preferably has a polystyrene-reduced weight average molecular weight of 200 or more, more preferably 300 or more, and even more preferably 400 or more as measured by the GPC method. By setting the lower limit value or higher, the heat resistance of the cured product of the resin composition tends to be further improved. Further, the weight average molecular weight of the specific cyanate ester compound (B) is preferably 1000 or less, more preferably 900 or less, and even more preferably 800 or less. By setting the upper limit value or lower, the moldability and handleability of the resin composition tend to be further improved.

[0028] Examples of the specific cyanate ester compound (B) used in the present embodiment include those represented by the following formula (B1). Formula (B1) [Chemical Formula] (In formula (B1), Ar 1 each independently represents a phenylene group which may have a substituent, a naphthylene group which may have a substituent, or a biphenylene group which may have a substituent. R 6 each independently represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms which may have a substituent, an aryl group having 6 to 12 carbon atoms which may have a substituent, an alkoxy group having 1 to 4 carbon atoms which may have a substituent, an aralkyl group which may have a substituent formed by bonding an alkyl group having 1 to 6 carbon atoms and an aryl group having 6 to 12 carbon atoms, or an alkylaryl group which may have a substituent formed by bonding an alkyl group having 1 to 6 carbon atoms and an aryl group having 6 to 12 carbon atoms, and is selected from any one of them. n 4 represents the number of cyanato groups bonded to Ar 1 and is an integer of 1 to 3. n 5 represents the number of R 1 bonded to Ar 6 and when Ar 1 is a phenylene group, it is 4 - n 4 , when it is a naphthylene group, it is 6 - n 4 , and when it is a biphenylene group, it is 8 - n 4 . n 6represents the average number of repetitions and is an integer from 0 to 50. Specific cyanate ester compounds (B) may be a mixture of compounds with different n 5 and / or n 6 . Z is independently selected from any one of a single bond, a divalent organic group having 1 to 50 carbon atoms (where a hydrogen atom may be substituted with a heteroatom), and a divalent organic group having 1 to 10 nitrogen atoms (-N-R-N, etc.).) The substituent in the above formula (B1) is preferably a nonpolar group.

[0029] The alkyl group in R of formula (B1) 6 may have at least one of a linear structure, a branched structure, and a cyclic structure (such as a cycloalkyl group). Also, the hydrogen atom in the alkyl group in R of formula (B1) 6 and the aryl group in R 6 may be substituted with a halogen atom such as a fluorine atom or a chlorine atom, an alkoxy group such as a methoxy group or a phenoxy group, a cyano group, etc. Specific examples of the alkyl group include a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, a 1-ethylpropyl group, a 2,2-dimethylpropyl group, a cyclopentyl group, a hexyl group, a cyclohexyl group, a trifluoromethyl group, etc. Specific examples of the aryl group include a phenyl group, a xylyl group, a mesityl group, a naphthyl group, a phenoxyphenyl group, an ethylphenyl group, an o-, m- or p-fluorophenyl group, a dichlorophenyl group, a dicyanophenyl group, a trifluorophenyl group, a methoxyphenyl group, an o-, m- or p-tolyl group, etc. Specific examples of the alkoxy group include a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, an n-butoxy group, an isobutoxy group, a tert-butoxy group, etc. Specific examples of the divalent organic group in Z of formula (B1) include a methylene group, an ethylene group, a trimethylene group, a cyclopentylene group, a cyclohexylene group, a trimethylcyclohexylene group, a biphenylylmethylene group, a dimethylmethylene-phenylene-dimethylmethylene group, a fluorenediyl group, a phthalidodiyl group, and the like. The hydrogen atom in the divalent organic group may be substituted with a halogen atom such as a fluorine atom or a chlorine atom, an alkoxy group such as a methoxy group, an aryloxy group such as a phenoxy group, a cyano group, or the like. Examples of the divalent organic group having 1 to 10 nitrogen atoms in Z of formula (B1) include an imino group, a polyimide group, and the like.

[0030] In addition, examples of Z in formula (B1) include those having a structure represented by the following formula (B2) or the following formula (B3). Formula (B2)

Chemical formula

Chemical formula

[0031] Furthermore, examples of Z in the formula (B1) include divalent groups represented by the following formula.

Chemical formula

[0032] Examples of the specific cyanate ester compound (B) include a phenol novolak type cyanate ester compound, a naphthol aralkyl type cyanate ester compound, a biphenyl aralkyl type cyanate ester compound, a naphthylene ether type cyanate ester compound, a xylene resin type cyanate ester compound, an adamantane skeleton type cyanate ester compound, a bisphenol A type cyanate ester compound, a bisphenol M type cyanate ester compound, a diallylbisphenol A type cyanate ester compound, and the like.

[0033] Specific examples of the cyanate ester compound (B) include 1,2-dicyanatobenzene, 1,3-dicyanatobenzene, 1,4-dicyanatobenzene, 1,4-dicyano-2-tert-butylbenzene, 1,4-dicyano-2,4-dimethylbenzene, 1,4-dicyano-2,3,4-trimethylbenzene, 1,3-dicyano-2,4,6-trimethylbenzene, 1,3-dicyano-5-methylbenzene, 2,2'-dicyano-1,1'-binaphthyl, 1,3-, 1,4-, 1,5-, 1,6-, 1,7-, 2,3-, 2,6- or 2,7-dicyanonaphthalene, 2,2'- or 4,4'-dicyanobiphenyl, 4,4'-dicyanooctafluorobiphenyl, 2,4'- or 4,4'-dicyanodiphenylmethane, bis(4-cyano-3,5-dimethylphenyl)methane, 1,1-bis(4-cyanophenyl)ethane, 1,1-bis(4-cyanophenyl)propane, 2,2-bis(4-cyanophenyl)propane, 2,2-bis(3-allyl-4-cyanophenyl)propane, 2,2-bis(4-cyano-3-methylphenyl)propane, 2,2-bis(2-cyano-5-biphenylyl)propane, 2,2-bis(4-cyanophenyl)hexafluoropropane, 2,2-bis(4-cyano-3,5-dimethylphenyl)propane, 1,1-bis(4-cyanophenyl)butane, 1,1-bis(4-cyanophenyl)isobutane, 1,1-bis(4-cyanophenyl)pentane, 1,1-bis(4-cyanophenyl)-3-methylbutane, 1,1-bis(4-cyanophenyl)-2-methylbutane, 1,1-bis(4-cyanophenyl)-2,2-dimethylpropane, 2,2-bis(4-cyanophenyl)butane, 2,2-bis(4-cyanophenyl)pentane, 2,2-bis(4-cyanophenyl)hexane, 2,2-bis(4-cyanophenyl)-3-methylbutane, 2,2-bis(4-cyanophenyl)-4-methylpentane, 2,2-bis(4-cyanophenyl)-3,3-dimethylbutane, 3,3-bis(4-cyanophenyl)hexane, 3,3-bis(4-cyanophenyl)heptane, 3,3-bis(4-cyanophenyl)octane, 3,3-bis(4-cyanophenyl)-2-methylpentane, 3,3-bis(4-cyanatophenyl)-2-methylhexane, 3,3-bis(4-cyanatophenyl)-2,2-dimethylpentane, 4,4-bis(4-cyanatophenyl)-3-methylheptane, 3,3-bis(4-cyanatophenyl)-2-methylheptane, 3,3-bis(4-cyanatophenyl)-2,2-dimethylhexane, 3,3-bis(4-cyanatophenyl)-2,4-dimethylhexane, 3,3-bis(4-cyanatophenyl)-2,2,4-trimethylpentane, 2,2-bis(4-cyanatophenyl)-1,1,1,3,3,3-hexafluoropropane, bis(4-cyanatophenyl)phenylmethane, 1,1-bis(4-cyanatophenyl)-1-phenylethane, bis(4-cyanatophenyl)biphenylmethane, 1,1-bis(4-cyanatophenyl)cyclopentane, 1,1-bis(4-cyanatophenyl)cyclohexane, 2,2-bis(4-cyanato-3-isopropylphenyl)propane, 1,1-bis(3-cyclohexyl-4-cyanatophenyl)cyclohexane, bis(4-cyanatophenyl)diphenylmethane, bis(4-cyanatophenyl)-2,2-dichloroethylene, 1,3-bis[2-(4-cyanatophenyl)-2-propyl]benzene, 1,4-bis[2-(4-cyanatophenyl)-2-propyl]benzene, 1,1-bis(4-cyanatophenyl)-3,3,5-trimethylcyclohexane, 4-[bis(4-cyanatophenyl)methyl]biphenyl, 4,4-dicyanatobenzophenone, 1,3-bis(4-cyanatophenyl)-2-propen-1-one, bis(4-cyanatophenyl)ether, bis(4-cyanatophenyl)sulfide, bis(4-cyanatophenyl)sulfone, 4-cyanatobenzoic acid 4-cyanatophenyl ester (4-cyanatophenyl-4-cyanatobenzoate), bis-(4-cyanatophenyl)carbonate, 1,3-bis(4-cyanatophenyl)adamantane, 1,3-bis(4-cyanatophenyl)-5,7-dimethyladamantane, 3,3-bis(4-cyanatophenyl)isobenzofuran-1(3H)-one (cyanate of phenolphthalein), 3,3-bis(4-cyanato-3-methylphenyl)isobenzofuran-1(3H)-one (cyanate of o-cresolphthalein), 9,9-Bis(4-cyanatophenyl)fluorene, 9,9-bis(4-cyano-3-methylphenyl)fluorene, 9,9-bis(2-cyano-5-biphenylyl)fluorene, tris(4-cyanatophenyl)methane, 1,1,1-tris(4-cyanatophenyl)ethane, 1,1,3-tris(4-cyanatophenyl)propane, α,α,α’-tris(4-cyanatophenyl)-1-ethyl-4-isopropylbenzene, 1,1,2,2-tetrakis(4-cyanatophenyl)ethane, tetrakis(4-cyanatophenyl)methane, 2,4,6-tris(N-methyl-4-cyanoanilino)-1,3,5-triazine, 2,4-bis(N-methyl-4-cyanoanilino)-6-(N-methylanilino)-1,3,5-triazine, bis(N-4-cyano-2-methylphenyl)-4,4’-oxydiphthalimide, bis(N-3-cyano-4-methylphenyl)-4,4’-oxydiphthalimide, bis(N-4-cyanatophenyl)-4,4’-oxydiphthalimide, bis(N-4-cyano-2-methylphenyl)-4,4’-(hexafluoroisopropylidene)diphthalimide, tris(3,5-dimethyl-4-cyanobenzyl)isocyanurate, 2-phenyl-3,3-bis(4-cyanatophenyl)phthalimide, 2-(4-methylphenyl)-3,3-bis(4-cyanatophenyl)phthalimide, 2-phenyl-3,3-bis(4-cyano-3-methylphenyl)phthalimide, 1-methyl-3,3-bis(4-cyanatophenyl)indolin-2-one, 2-phenyl-3,3-bis(4-cyanatophenyl)indolin-2-one, phenol novolak resin and cresol novolak resin (obtained by reacting phenol, alkyl-substituted phenol or halogen-substituted phenol with a formaldehyde compound such as formalin or paraformaldehyde in an acidic solution by a known method), tris-phenol novolak resin (obtained by reacting hydroxybenzaldehyde and phenol in the presence of an acidic catalyst), fluorene novolak resin (obtained by reacting a fluorenone compound and 9,Those obtained by reacting 9-bis(hydroxyaryl)fluorenes in the presence of an acidic catalyst), phenolic aralkyl resins, cresol aralkyl resins, naphthol aralkyl resins, and biphenyl aralkyl resins (by known methods, Ar, 4 -(CH 2 Z’) 2 (Ar 4 is a phenylene group, a naphthylene group or a biphenylene group, which may have substituents.) Those obtained by reacting a bis(halogenomethyl) compound represented by the formula with a phenolic compound in the presence of an acidic catalyst or without a catalyst, Ar 4 -(CH 2 OR) 2 bis(alkoxymethyl) compounds represented by the formula or Ar 4 -(CH 2 OH) 2 Those obtained by reacting a bis(hydroxymethyl) compound represented by the formula with a phenolic compound in the presence of an acidic catalyst, or those obtained by polycondensing an aromatic aldehyde compound, an aralkyl compound, and a phenolic compound), phenolic-modified xylene formaldehyde resins (obtained by reacting xylene formaldehyde resins with phenolic compounds in the presence of an acidic catalyst by known methods), modified naphthalene formaldehyde resins (obtained by reacting naphthalene formaldehyde resins with hydroxy-substituted aromatic compounds in the presence of an acidic catalyst by known methods), phenolic-modified dicyclopentadiene resins, phenolic resins having a polynaphthylene ether structure (obtained by dehydrating and condensing a polyhydric hydroxynaphthalene compound having two or more phenolic hydroxyl groups in one molecule in the presence of a basic catalyst), etc. are cyanated by the same method as described above, and the like can be mentioned, but are not particularly limited. These cyanate ester compounds may be used alone or in combination of two or more.

[0034] Among these, a phenol novolac type cyanate ester compound, a naphthol aralkyl type cyanate ester compound, a naphthylene ether type cyanate ester compound, a bisphenol A type cyanate ester compound, a bisphenol M type cyanate ester compound, and a diallylbisphenol type cyanate ester compound are preferable, a naphthol aralkyl type cyanate ester compound and a bisphenol A type cyanate ester compound are more preferable, and a naphthol aralkyl type cyanate ester compound is particularly preferable because, in addition to the heat resistance and low dielectric properties of the resulting cured product, it is excellent in moldability, low water absorption, and chemical resistance. In particular, by combining a naphthol aralkyl type cyanate ester compound with a compound represented by the formula (M1), the chemical resistance and desmear resistance are effectively improved. This is presumably the result of the synergistic effect of the fact that the naphthol aralkyl type cyanate ester compound is inherently difficult to break because the proportion of aromatic rings in the molecule is relatively high, and the compound represented by the formula (M1) has an alicyclic structure and thus is difficult to absorb moisture.

[0035] In the resin composition of the present embodiment, when the resin solid content in the resin composition is 100 parts by mass, the content of the specific cyanate ester compound (B) is preferably 1 to 90 parts by mass. The lower limit of the content of the specific cyanate ester compound (B) is preferably 5 parts by mass or more, more preferably 10 parts by mass or more, still more preferably 15 parts by mass or more, even more preferably 20 parts by mass or more, even more preferably 25 parts by mass or more, and may be 30 parts by mass or more, 40 parts by mass or more, 45 parts by mass or more when the resin solid content in the resin composition is 100 parts by mass. By setting it to the above lower limit value or more, the heat resistance and low water absorption of the obtained cured product tend to be further improved. Further, the upper limit of the content of the specific cyanate ester compound (B) is preferably 90 parts by mass or less, more preferably 80 parts by mass or less, still more preferably 70 parts by mass or less, even more preferably 65 parts by mass or less, and even more preferably 60 parts by mass or less when the resin solid content in the resin composition is 100 parts by mass. By setting it to the above upper limit value or less, the dielectric properties (low dielectric property) and low water absorption of the obtained cured product tend to be further improved.

[0036] Further, in the resin composition of the present embodiment, the content of the specific cyanate ester compound (B) is preferably 5% by mass or more, more preferably 10% by mass or more, still more preferably 15% by mass or more, even more preferably 20% by mass or more, even more preferably 25% by mass or more, and may be 30% by mass or more, 40% by mass or more, 45% by mass or more of the resin solid content. By setting it to the above lower limit value or more, the heat resistance and low water absorption of the obtained cured product tend to be further improved. Further, the upper limit of the content of the specific cyanate ester compound (B) is preferably 90% by mass or less, more preferably 80% by mass or less, still more preferably 70% by mass or less, even more preferably 65% by mass or less, and even more preferably 60% by mass or less of the resin solid content in the resin composition. By setting it to the above upper limit value or less, the dielectric properties (low dielectric property) and low water absorption of the obtained cured product tend to be further improved. The resin composition of this embodiment may contain only one kind of a specific cyanate ester compound (B), or may contain two or more kinds. When two or more kinds are contained, it is preferable that the total amount is within the above range.

[0037] In the resin composition of this embodiment, it is preferable that the total amount of the compound (A) represented by the formula (M1) and the specific cyanate ester compound (B) is 20% by mass or more of the resin solid content, more preferably 30% by mass or more, still more preferably 40% by mass or more, even more preferably 50% by mass or more, still even more preferably 60% by mass or more, yet even more preferably 70% by mass or more, and it may be 80% by mass or more, 90% by mass or more, 95% by mass or more. By setting it to be not less than the lower limit value, the heat resistance and / or low dielectric property of the obtained cured product tend to be further improved. Also, the upper limit value of the total amount is preferably 100% by mass or less of the resin solid content in the resin composition.

[0038] In the resin composition of this embodiment, the mass ratio of the compound (A) represented by the formula (M1) and the specific cyanate ester compound (B) is preferably from 9:1 to 1:9, more preferably from 5:1 to 1:5, and still more preferably from 3:1 to 1:3. With such a blend ratio, the condensed ring of an alicyclic ring and an aromatic ring such as an indane ring contained in the compound (A) represented by the formula (M1) will exist at an appropriate distance within the cured product, and it becomes possible to effectively achieve high heat resistance and low dielectric property.

[0039] <Other resin solid content (C)> The resin composition of this embodiment may further contain one or more other resin components (C) selected from the group consisting of maleimide compounds, epoxy compounds, phenol compounds, oxetane resins, benzoxazine compounds, and compounds having polymerizable unsaturated groups other than the compound (A) represented by the formula (M1). By containing such components, other desired performances required for printed wiring boards can be more effectively exhibited.

[0040] Each of the above other resin components (C) preferably has a cured product with excellent dielectric properties. For example, each of the other resin components (C) preferably has a relative dielectric constant (Dk) measured according to the cavity resonance perturbation method of the cured product of 4.0 or less, more preferably 3.5 or less. Further, the lower limit of the relative dielectric constant (Dk) is preferably, for example, 2.0 or more for practical use. Also, each of the other resin components (C) preferably has a dielectric tangent (Df) measured according to the cavity resonance perturbation method of the cured product of 0.01 or less, more preferably 0.007 or less. Further, the lower limit of the dielectric tangent (Df) is preferably, for example, 0.0001 or more for practical use.

[0041] In addition, each of the other resin components (C) preferably has a cured product with high heat resistance. For example, each of the other resin components (C) preferably has a glass transition temperature measured according to JIS C6481 dynamic viscoelasticity measurement of the cured product of 150°C or higher, more preferably 180°C or higher, and even more preferably 200°C or higher. By setting it to be the above lower limit value or higher, a cured product with more excellent heat resistance can be obtained. Further, the upper limit of the glass transition temperature is preferably 400°C or lower for practical use.

[0042] Further, the resin composition of the present embodiment may contain an elastomer. Furthermore, the resin composition of the present embodiment may contain a silane coupling agent. Furthermore, the resin composition of the present embodiment may contain an active ester compound. Furthermore, within a range not departing from the gist of the present invention, it may contain additives commonly used in the technical field of the present invention. Hereinafter, details of the other resin component (C), the elastomer, the silane coupling agent, and the active ester will be described.

[0043] <<Maleimide compound other than the compound (A) represented by formula (M1)>> The resin composition of the present embodiment may contain a maleimide compound other than the compound (A) represented by formula (M1) (hereinafter, sometimes simply referred to as "other maleimide compound"). Other maleimide compounds are not particularly limited as long as they have one or more (preferably 2 to 12, more preferably 2 to 6, still more preferably 2 to 4, even more preferably 2 or 3, and even more preferably 2) maleimide groups in one molecule, and compounds commonly used in the field of printed wiring boards can be widely used. Examples of other maleimide compounds include compounds represented by formula (2M) to formula (4M). When these other maleimide compounds are used in materials for printed wiring boards (for example, laminates, metal foil-clad laminates), excellent heat resistance can be imparted.

Chemical formula

Chemical formula

Chemical formula

[0044] Among the compounds represented by the above formulas (2M) to (4M), the compound represented by formula (3M) is more preferable. Other maleimide compounds may be prepared by known methods or commercially available products may be used. Examples of commercially available products include "MIR-3000" manufactured by Nippon Kayaku Co., Ltd. as the compound represented by formula (3M), "BMI-2300" manufactured by Daiwa Kasei Kogyo Co., Ltd. as the compound represented by formula (2M), and "BMI-70" manufactured by K.I. Kasei Co., Ltd. as the compound represented by formula (4M).

[0045] Examples of other maleimide compounds other than the above include oligomers of phenylmethane maleimide, m-phenylene bismaleimide, 2,2-bis(4-(4-maleimidophenoxy)-phenyl)propane, 4-methyl-1,3-phenylene bismaleimide, 1,6-bismaleimide-(2,2,4-trimethyl)hexane, 4,4'-diphenyl ether bismaleimide, 4,4'-diphenyl sulfone bismaleimide, 1,3-bis(3-maleimidophenoxy)benzene, 1,3-bis(4-maleimidophenoxy)benzene, and prepolymers thereof, prepolymers of these maleimides and amines, and the like.

[0046] When the resin composition of the present embodiment contains other maleimide compounds, the lower limit of the content of the other maleimide compounds is preferably 1 part by mass or more, more preferably 10 parts by mass or more, and may be 15 parts by mass or more with respect to 100 parts by mass of the resin solid content in the resin composition. When the content of the other maleimide compounds is 1 part by mass or more, the flame resistance of the resulting cured product tends to improve. Further, when the resin composition of the present embodiment contains other maleimide compounds, the upper limit of the content of the other maleimide compounds is preferably 70 parts by mass or less, more preferably 50 parts by mass or less, further preferably 30 parts by mass or less, and even more preferably 20 parts by mass or less with respect to 100 parts by mass of the resin solid content in the resin composition. When the content of the other maleimide compounds is 70 parts by mass or less, the metal foil peel strength and low water absorption tend to improve. The resin composition in the present embodiment may contain only one kind of other maleimide compound, or may contain two or more kinds. When two or more kinds are contained, it is preferable that the total amount is within the above range. Further, the resin composition in the present embodiment can also be configured to substantially not contain other maleimide compounds. Substantially not containing means that the content of the other maleimide compounds is less than 1 part by mass with respect to 100 parts by mass of the resin solid content in the resin composition.

[0047] <<Epoxy compound>> The resin composition of the present embodiment may contain an epoxy compound. The epoxy compound is not particularly limited as long as it is a compound or resin having 1 or more (preferably 2 to 12, more preferably 2 to 6, further preferably 2 to 4, even more preferably 2 or 3, and even more preferably 2) epoxy groups in one molecule, and compounds commonly used in the field of printed wiring boards can be widely used. Epoxy compounds include, for example, bisphenol A type epoxy resin, bisphenol E type epoxy resin, bisphenol F type epoxy resin, bisphenol S type epoxy resin, phenol novolac type epoxy resin, bisphenol A novolac type epoxy resin, glycidyl ester type epoxy resin, aralkyl novolac type epoxy resin, biphenyl aralkyl type epoxy resin, naphthylene ether type epoxy resin, cresol novolac type epoxy resin, polyfunctional phenol type epoxy resin, naphthalene type epoxy resin, anthracene type epoxy resin, naphthalene skeleton modified novolac type epoxy resin, phenol aralkyl type epoxy resin, naphthol aralkyl type epoxy resin, dicyclopentadiene type epoxy resin, biphenyl type epoxy resin, alicyclic epoxy resin, polyol type epoxy resin, phosphorus-containing epoxy resin, glycidylamine, glycidyl ester, compounds obtained by epoxidizing double bonds such as butadiene, compounds obtained by reacting hydroxyl group-containing silicone resins with epichlorohydrin, and the like. By using these, the moldability and adhesion of the resin composition are improved. Among these, from the viewpoint of further improving flame retardancy and heat resistance, biphenyl aralkyl type epoxy resin, naphthylene ether type epoxy resin, polyfunctional phenol type epoxy resin, and naphthalene type epoxy resin are preferred, and biphenyl aralkyl type epoxy resin is more preferred.

[0048] The resin composition of this embodiment preferably contains an epoxy compound within a range that does not impair the effects of the present invention. When the resin composition of this embodiment contains an epoxy compound, its content is preferably 0.1 part by mass or more, more preferably 1 part by mass or more, and even more preferably 2 parts by mass or more with respect to 100 parts by mass of the resin solid content in the resin composition. When the content of the epoxy compound is 0.1 part by mass or more, the metal foil peel strength and toughness tend to improve. The upper limit of the content of the epoxy compound is preferably 50 parts by mass or less, more preferably 30 parts by mass or less, even more preferably 20 parts by mass or less, still more preferably 10 parts by mass or less, even more preferably 8 parts by mass or less, and even more preferably 5 parts by mass or less with respect to 100 parts by mass of the resin solid content in the resin composition when the resin composition of this embodiment contains an epoxy compound. When the content of the epoxy compound is 50 parts by mass or less, the electrical properties of the resulting cured product tend to improve. The resin composition in this embodiment may contain only one type of epoxy compound or may contain two or more types. When containing two or more types, it is preferable that the total amount is within the above range. Also, the resin composition in this embodiment can be configured to substantially not contain an epoxy compound. Substantially not containing means that the content of the epoxy compound is less than 1 part by mass with respect to 100 parts by mass of the resin solid content in the resin composition.

[0049] <<Phenolic compound>> The resin composition of this embodiment may contain a phenolic compound. The phenolic compound is not particularly limited as long as it is a phenolic compound having one or more (preferably 2 to 12, more preferably 2 to 6, even more preferably 2 to 4, still more preferably 2 or 3, and even more preferably 2) phenolic hydroxyl groups in one molecule, and compounds commonly used in the field of printed wiring boards can be widely used. Phenolic compounds include, for example, bisphenol A type phenolic resin, bisphenol E type phenolic resin, bisphenol F type phenolic resin, bisphenol S type phenolic resin, phenol novolak resin, bisphenol A novolak type phenolic resin, glycidyl ester type phenolic resin, aralkyl novolak phenolic resin, biphenyl aralkyl type phenolic resin, cresol novolak type phenolic resin, polyfunctional phenolic resin, naphthol resin, naphthol novolak resin, polyfunctional naphthol resin, anthracene type phenolic resin, naphthalene skeleton-modified novolak type phenolic resin, phenol aralkyl type phenolic resin, naphthol aralkyl type phenolic resin, dicyclopentadiene type phenolic resin, biphenyl type phenolic resin, alicyclic phenolic resin, polyol type phenolic resin, phosphorus-containing phenolic resin, hydroxyl group-containing silicone resins, and the like. Among these, from the viewpoint of further improving the flame resistance of the resulting cured product, it is preferably at least one selected from the group consisting of biphenyl aralkyl type phenolic resin, naphthol aralkyl type phenolic resin, phosphorus-containing phenolic resin, and hydroxyl group-containing silicone resin.

[0050] The resin composition of the present embodiment preferably contains a phenolic compound within a range that does not impair the effects of the present invention. When the resin composition of the present embodiment contains a phenolic compound, its content is preferably 0.1 part by mass or more and preferably 50 parts by mass or less with respect to 100 parts by mass of the resin solid content in the resin composition. The resin composition in the present embodiment may contain only one type of phenolic compound or may contain two or more types. When containing two or more types, the total amount is preferably within the above range. In addition, the resin composition in the present embodiment can also be configured to substantially not contain a phenolic compound. Substantially not containing means that the content of the phenolic compound is less than 0.1 part by mass with respect to 100 parts by mass of the resin solid content in the resin composition.

[0051] <<Oxetane resin>> The resin composition of this embodiment may contain an oxetane resin. The oxetane resin is not particularly limited as long as it is a compound having one or more (preferably 2 to 12, more preferably 2 to 6, still more preferably 2 to 4, even more preferably 2 or 3, and even more preferably 2) oxetanyl groups, and compounds commonly used in the field of printed wiring boards can be widely used. Examples of the oxetane resin include oxetane, alkyloxetane (e.g., 2-methyloxetane, 2,2-dimethyloxetane, 3-methyloxetane, 3,3-dimethyloxetane, etc.), 3-methyl-3-methoxymethyloxetane, 3,3-bis(trifluoromethyl)oxetane, 2-chloromethyloxetane, 3,3-bis(chloromethyl)oxetane, biphenyl-type oxetane, OXT-101 (manufactured by Toagosei Co., Ltd.), OXT-121 (manufactured by Toagosei Co., Ltd.), and the like.

[0052] The resin composition of this embodiment preferably contains an oxetane resin within a range that does not impair the effects of the present invention. When the resin composition of this embodiment contains an oxetane resin, its content is preferably 0.1 part by mass or more, more preferably 1 part by mass or more, and still more preferably 2 parts by mass or more with respect to 100 parts by mass of the resin solid content in the resin composition. When the content of the oxetane resin is 0.1 part by mass or more, the metal foil peel strength and toughness tend to improve. The upper limit value of the content of the oxetane resin is preferably 50 parts by mass or less, more preferably 30 parts by mass or less, still more preferably 20 parts by mass or less, even more preferably 10 parts by mass or less, and even more preferably 8 parts by mass or less with respect to 100 parts by mass of the resin solid content in the resin composition when the resin composition of this embodiment contains an oxetane resin. When the content of the oxetane resin is 50 parts by mass or less, the electrical properties of the resulting cured product tend to improve. The resin composition in this embodiment may contain only one kind of oxetane resin or two or more kinds of oxetane resins. When two or more kinds are contained, the total amount is preferably within the above range. The resin composition in this embodiment may be configured to be substantially free of oxetane resin. Substantially free means that the content of oxetane resin is less than 0.1 parts by mass per 100 parts by mass of the resin solid content in the resin composition.

[0053] <<Benzoxazine compounds>> The resin composition of the present embodiment may contain a benzoxazine compound. The benzoxazine compound is not particularly limited as long as it has two or more (preferably 2 to 12, more preferably 2 to 6, even more preferably 2 to 4, still more preferably 2 or 3, and even more preferably 2) dihydrobenzoxazine rings in one molecule, and a wide variety of compounds commonly used in the field of printed wiring boards can be used. Examples of the benzoxazine compound include bisphenol A-type benzoxazine BA-BXZ (manufactured by Konishi Chemical Co., Ltd.), bisphenol F-type benzoxazine BF-BXZ (manufactured by Konishi Chemical Co., Ltd.), and bisphenol S-type benzoxazine BS-BXZ (manufactured by Konishi Chemical Co., Ltd.).

[0054] The resin composition of the present embodiment preferably contains a benzoxazine compound in an amount not impairing the effects of the present invention. When the resin composition of the present embodiment contains a benzoxazine compound, the content is preferably 0.1 parts by mass or more and preferably 50 parts by mass or less relative to 100 parts by mass of the resin solid content in the resin composition. The resin composition in the present embodiment may contain only one type of benzoxazine compound, or may contain two or more types. When two or more types are contained, the total amount is preferably in the above range. The resin composition of the present embodiment may be configured to be substantially free of benzoxazine compounds, meaning that the content of the benzoxazine compounds is less than 0.1 parts by mass per 100 parts by mass of the resin solid content in the resin composition.

[0055] <<Compounds having polymerizable unsaturated groups>> The resin composition of this embodiment may contain a compound having a polymerizable unsaturated group. The number of unsaturated groups in the compound is 1 or more per molecule, preferably 2 to 12, more preferably 2 to 6, still more preferably 2 to 4, even more preferably 2 or 3, and even more preferably 2. The compound having a polymerizable unsaturated group is not particularly limited, and compounds commonly used in the field of printed wiring boards can be widely used. Specific examples of the compound having a polymerizable unsaturated group include polyphenylene ether compounds containing two or more carbon-carbon unsaturated double bonds, vinyl compounds (e.g., ethylene, propylene, styrene, divinylbenzene, divinylbiphenyl, etc.), acrylates (e.g., methyl (meth)acrylate, etc.), (meth)acrylates of mono- or polyalcohols (e.g., 2-hydroxypropyl (meth)acrylate, polypropylene glycol di(meth)acrylate, trimethylolpropane di(meth)acrylate, trimethylolpropane tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol hexa(meth)acrylate, etc.), epoxy (meth)acrylates (e.g., bisphenol A type epoxy (meth)acrylate, bisphenol F type epoxy (meth)acrylate, etc.), benzocyclobutene resins, and the like. Details of the polyphenylene ether compound containing two or more carbon-carbon unsaturated double bonds can refer to the descriptions in paragraphs 0026 to 0041 of International Publication No. 2019 / 230661, and this content is incorporated herein.

[0056] The resin composition of this embodiment preferably contains a compound having a polymerizable unsaturated group within a range that does not impair the effects of the present invention. When the resin composition of this embodiment contains a compound having a polymerizable unsaturated group, its content is preferably 0.1 part by mass or more and preferably 50 parts by mass or less based on 100 parts by mass of the resin solid content in the resin composition. The resin composition in this embodiment may contain only one kind of compound having a polymerizable unsaturated group, or may contain two or more kinds. When two or more kinds are contained, it is preferable that the total amount is within the above range. Further, the resin composition in this embodiment can also be configured to substantially not contain a compound having a polymerizable unsaturated group. Substantially not containing means that the content of the compound having a polymerizable unsaturated group is less than 0.1 part by mass with respect to 100 parts by mass of the resin solid content in the resin composition.

[0057] <<Elastomer>> The resin composition of this embodiment may contain an elastomer. In this embodiment, the elastomer is not particularly limited, and examples thereof include at least one selected from the group consisting of polyisoprene, polybutadiene, styrene-butadiene, butyl rubber, ethylene-propylene rubber, styrene-butadiene-ethylene, styrene-butadiene-styrene, styrene-isoprene-styrene, styrene-ethylene-butylene-styrene, styrene-propylene-styrene, styrene-ethylene-propylene-styrene, fluororubber, silicone rubber, their hydrogenated compounds, their alkyl compounds, and their copolymers. Among these, from the viewpoint of excellent electrical properties, at least one selected from the group consisting of styrene-butadiene, styrene-butadiene-ethylene, styrene-butadiene-styrene, styrene-isoprene-styrene, styrene-ethylene-butylene-styrene, styrene-propylene-styrene, styrene-ethylene-propylene-styrene, their hydrogenated compounds, their alkyl compounds, and their copolymers is preferable, and from the viewpoint of being more excellent due to compatibility with a specific cyanate ester compound (B), at least one selected from the group consisting of styrene-butadiene rubber, butadiene rubber, and isoprene rubber is more preferable.

[0058] In this embodiment, from the viewpoint of excellent electrical properties, the elastomer has an SP value of 9 (cal / cm 3 ) 1 / 2The following are preferred. The SP value, also called the solubility parameter, is the square root of the heat of vaporization (cal / cm 3 ) required for 1 cm 3 of a liquid to evaporate. It is calculated from 1 / 2 . Generally, the smaller this value, the lower the polarity, and the closer this value, the higher the affinity between the two components. When the SP value of the elastomer is 9 (cal / cm 3 ) 1 / 2 or less, more suitable electrical properties can be obtained with the resin composition used for printed wiring boards for high-frequency applications.

[0059] In this embodiment, if the elastomer has a polystyrene-reduced weight-average molecular weight of 80,000 or more by the GPC method and is solid at 25°C, it is preferable because the crack resistance is further improved when used for materials for printed wiring boards (e.g., laminates, metal foil-clad laminates). On the other hand, if the polystyrene-reduced weight-average molecular weight by the GPC method is 40,000 or less and it is liquid at 25°C, it is particularly suitable as a build-up material for printed wiring boards because the warp is reduced when the film-coated material is bonded to the substrate.

[0060] The resin composition of this embodiment preferably contains an elastomer within a range that does not impair the effects of the present invention. When the resin composition of this embodiment contains an elastomer, its content is preferably 0.1 part by mass or more, more preferably 1 part by mass or more, and even more preferably 2 parts by mass or more with respect to 100 parts by mass of the resin solid content in the resin composition. The upper limit value of the elastomer content is preferably 50 parts by mass or less, more preferably 30 parts by mass or less, even more preferably 20 parts by mass or less, still more preferably 10 parts by mass or less, and even more preferably 8 parts by mass or less with respect to 100 parts by mass of the resin solid content in the resin composition when the resin composition of this embodiment contains an elastomer. The resin composition in this embodiment may contain only one type of elastomer or two or more types. When two or more types are contained, the total amount is preferably within the above range. Further, the resin composition in the present embodiment can also be configured to substantially not contain an elastomer. Substantially not containing means that the content of the elastomer is less than 0.1 part by mass with respect to 100 parts by mass of the resin solid content in the resin composition.

[0061] <<Silane coupling agent>> The resin composition of the present embodiment may further contain a silane coupling agent. By containing a silane coupling agent, the dispersibility of the filler (D) described later, and the adhesive strength between the resin component, the filler (D), and the base material described later tend to be further improved.

[0062] The silane coupling agent is not particularly limited as long as it is a silane coupling agent generally used for surface treatment of inorganic substances. For example, vinyl silane compounds such as vinyltrimethoxysilane; styryl silane compounds such as p-styryltrimethoxysilane; amino silane compounds such as γ-aminopropyltriethoxysilane and N-β-(aminoethyl)-γ-aminopropyltrimethoxysilane; epoxy silane compounds such as γ-glycidoxypropyltrimethoxysilane; acrylic silane compounds such as γ-acryloxypropyltrimethoxysilane; cationic silane compounds such as N-β-(N-vinylbenzylaminoethyl)-γ-aminopropyltrimethoxysilane hydrochloride; phenyl silane compounds and the like. The silane coupling agent may be used alone or in combination of two or more.

[0063] When the resin composition of the present embodiment contains a silane coupling agent, the lower limit of its content is preferably 0.005 part by mass or more, more preferably 0.01 part by mass or more, and further preferably 0.1 part by mass or more with respect to 100 parts by mass of the resin solid content in the resin composition. Also, the upper limit of the content of the silane coupling agent is preferably 10 parts by mass or less, more preferably 5 parts by mass or less, and further preferably 2 parts by mass or less with respect to 100 parts by mass of the resin solid content in the resin composition. The silane coupling agent can be used alone or in combination of two or more. When two or more are used, the total amount is within the above range.

[0064] <<Active ester compound>> The resin composition of this embodiment may contain an active ester compound. The active ester compound is not particularly limited. For example, compounds having two or more (preferably 2 to 12, more preferably 2 to 6, still more preferably 2 to 4, even more preferably 2 or 3, and even more preferably 2) active ester groups in one molecule can be mentioned. The active ester compound may be a linear, branched or cyclic compound. Among these, from the viewpoint of further improving the heat resistance of the obtained cured product, an active ester compound obtained by reacting a carboxylic acid compound and / or a thiocarboxylic acid compound with a hydroxy compound and / or a thiol compound is preferred, and an active ester compound obtained by reacting a carboxylic acid compound with one or more compounds selected from the group consisting of a phenol compound, a naphthol compound, and a thiol compound is more preferred. An aromatic compound having two or more active ester groups in one molecule obtained by reacting a carboxylic acid compound with an aromatic compound having a phenolic hydroxyl group is still more preferred, and an aromatic compound having two or more active ester groups in one molecule obtained by reacting a compound having at least two or more carboxylic acids in one molecule with an aromatic compound having a phenolic hydroxyl group is particularly preferred. Examples of the above carboxylic acid compound include one or more selected from the group consisting of benzoic acid, acetic acid, succinic acid, maleic acid, itaconic acid, phthalic acid, isophthalic acid, terephthalic acid, and pyromellitic acid. Among these, from the viewpoint of further improving the heat resistance of the obtained cured product, one or more selected from the group consisting of succinic acid, maleic acid, itaconic acid, phthalic acid, isophthalic acid, and terephthalic acid are preferred, and one or more selected from the group consisting of isophthalic acid and terephthalic acid are more preferred. Examples of the above thiocarboxylic acid compound include one or more selected from thioacetic acid and thiobenzoic acid.Examples of the above-mentioned phenol compound or naphthol compound include hydroquinone, resorcinol, bisphenol A, bisphenol F, bisphenol S, phenolphthalein, methylated bisphenol A, methylated bisphenol F, methylated bisphenol S, phenol, o-cresol, m-cresol, p-cresol, catechol, α-naphthol, β-naphthol, 1,5-dihydroxynaphthalene, 1,6-dihydroxynaphthalene, 2,6-dihydroxynaphthalene, dihydroxybenzophenone, trihydroxybenzophenone, tetrahydroxybenzophenone, phloroglucinol, benzenetriol, dicyclopentadienyl diphenol, and phenol novolak. From the perspective of further improving the heat resistance and solvent solubility of the resulting cured product, bisphenol A, bisphenol F, bisphenol S, methylated bisphenol A, methylated bisphenol F, methylated bisphenol S, catechol, α-naphthol, β-naphthol, 1,5-dihydroxynaphthalene, 1,6-dihydroxynaphthalene, 2,6-dihydroxynaphthalene, dihydroxybenzophenone, trihydroxybenzophenone, tetrahydroxybenzophenone, phloroglucinol, benzenetriol, dicyclopentadienyl diphenol, and phenol novolak are preferred. One or more selected from the group consisting of catechol, 1,5-dihydroxynaphthalene, 1,6-dihydroxynaphthalene, 2,6-dihydroxynaphthalene, dihydroxybenzophenone, trihydroxybenzophenone, tetrahydroxybenzophenone, phloroglucinol, benzenetriol, dicyclopentadienyl diphenol, and phenol novolak are more preferred. 1,5-dihydroxynaphthalene, 1,6-dihydroxynaphthalene, 2,One or more selected from the group consisting of 6-dihydroxynaphthalene, dihydroxybenzophenone, trihydroxybenzophenone, tetrahydroxybenzophenone, dicyclopentadienyl diphenol, and phenol novolak are more preferable, and one or more selected from the group consisting of dihydroxybenzophenone, trihydroxybenzophenone, tetrahydroxybenzophenone, dicyclopentadienyl diphenol, and phenol novolak (preferably, one or more selected from the group consisting of dicyclopentadienyl diphenol and phenol novolak, more preferably dicyclopentadienyl diphenol) are particularly preferable., Examples of the thiol compound include one or more selected from the group consisting of benzenedithiol and triazinedithiol. Further, from the viewpoint of further improving the compatibility with the epoxy compound, the active ester compound preferably has at least two or more carboxylic acids in one molecule and is a compound containing an aliphatic chain, and from the viewpoint of further improving the heat resistance, it is preferably a compound having an aromatic ring. More specific examples of the active ester compound include the active ester compounds described in JP-A-2004-277460.,

[0065] Commercially available products may be used for the active ester compound, or it may be prepared by a known method. Examples of commercially available products include compounds containing a dicyclopentadienyl diphenol structure (for example, EXB9451, EXB9460, EXB9460S, HPC-8000-65T (all manufactured by DIC Corporation), etc.), acetylated products of phenol novolak (for example, DC808 (manufactured by Mitsubishi Chemical Corporation)), and benzoylated products of phenol novolak (for example, YLH1026, YLH1030, YLH1048 (all manufactured by Mitsubishi Chemical Corporation)). From the viewpoint of further improving the storage stability of the varnish and the low thermal expansion coefficient of the resin composition when cured (cured product), EXB9460S is preferable.,

[0066] The active ester compound can be prepared by a known method, for example, it can be obtained by a condensation reaction between a carboxylic acid compound and a hydroxy compound. Specific examples include reacting (a) a carboxylic acid compound or its halide, (b) a hydroxy compound, and (c) an aromatic monohydroxy compound in a ratio of 0.05 to 0.75 mol of the phenolic hydroxyl group of (b) and 0.25 to 0.95 mol of (c) per 1 mol of the carboxy group or acid halide group of (a).

[0067] The active ester compound is preferably included within a range that does not impair the effects of the present invention. When the resin composition of the present embodiment contains the active ester compound, it is preferably 1 part by mass or more and preferably 90 parts by mass or less with respect to 100 parts by mass of the resin solid content in the resin composition. The resin composition in the present embodiment may contain only one kind of the active ester compound or may contain two or more kinds. When containing two or more kinds, the total amount is preferably within the above range. Also, the resin composition in the present embodiment can be configured to substantially not contain the active ester compound. Substantially not containing means that the content of the active ester compound is less than 1 part by mass with respect to 100 parts by mass of the resin solid content in the resin composition.

[0068] <(D) Filler> The resin composition of the present embodiment preferably contains a filler (D). By blending the filler (D), the low dielectric constant property, low dielectric tangent property, flame retardancy, and low thermal expansion property of the resin composition can be further improved. In addition, the filler (D) used in this embodiment preferably has excellent dielectric properties. For example, the filler (D) used in this embodiment preferably has a relative permittivity (Dk) measured according to the cavity resonance perturbation method of 8.0 or less, more preferably 6.0 or less. Further, the lower limit of the relative permittivity is, for example, preferably 2.0 or more for practical use. In addition, the filler (D) used in this embodiment preferably has a dissipation factor (Df) measured according to the cavity resonance perturbation method of 0.05 or less, more preferably 0.01 or less. Further, the lower limit of the dissipation factor is, for example, preferably 0.0001 or more for practical use.

[0069] The type of the filler (D) used in this embodiment is not particularly limited, and those generally used in the art can be preferably used. Specifically, silicas such as natural silica, fused silica, synthetic silica, amorphous silica, aerosil, hollow silica, white carbon, titanium white, zinc oxide, magnesium oxide, zirconium oxide, boron nitride, aggregated boron nitride, silicon nitride, aluminum nitride, barium sulfate, aluminum hydroxide, heat-treated aluminum hydroxide (aluminum hydroxide heat-treated to reduce a part of the water of crystallization), boehmite, magnesium hydroxide and other metal hydrates, molybdenum compounds such as molybdenum oxide and zinc molybdate, zinc borate, zinc stannate, alumina, clay, kaolin, talc, fired clay, fired kaolin, fired talc, mica, E-glass, A-glass, NE-glass, C-glass, L-glass, D-glass, S-glass, M-glass G20, glass short fibers (including glass fine powders such as E-glass, T-glass, D-glass, S-glass, Q-glass, etc.), hollow glass, spherical glass and other inorganic fillers, and rubber powders such as styrene type, butadiene type, acrylic type, core-shell type rubber powders, silicone resin powders, silicone rubber powders, silicone composite powders and other organic fillers. Among these, one or more selected from the group consisting of silicas, aluminum hydroxide, boehmite, magnesium oxide, and magnesium hydroxide are preferable. By using these fillers, properties such as the thermal expansion characteristics, dimensional stability, and flame retardancy of the resin composition are improved.

[0070] The content of the filler (D) in the resin composition of this embodiment can be appropriately set according to the desired properties and is not particularly limited. However, relative to 100 parts by mass of the resin solid content in the resin composition, 50 parts by mass or more is preferable, more preferably 75 parts by mass or more. Also, relative to 100 parts by mass of the resin solid content in the resin composition, 1600 parts by mass or less is preferable, more preferably 1200 parts by mass or less, still more preferably 1000 parts by mass or less, even more preferably 750 parts by mass or less, yet even more preferably 500 parts by mass or less, still even more preferably 300 parts by mass or less, and may be 250 parts by mass or less, 200 parts by mass or less. In the resin composition of this embodiment, as an example of a preferred embodiment, an aspect in which the content of the filler (D) is 30% to 80% by mass of the components excluding the solvent is exemplified. The resin composition in this embodiment may contain only one type of the filler (D) or may contain two or more types. When containing two or more types, it is preferable that the total amount is within the above range.

[0071] <Flame retardant> The resin composition of this embodiment may contain a flame retardant. As the flame retardant, known ones can be used. For example, halogen-based flame retardants such as brominated epoxy resin, brominated polycarbonate, brominated polystyrene, brominated styrene, brominated phthalimide, tetrabromobisphenol A, pentabromobenzyl (meth)acrylate, pentabromotoluene, tribromophenol, hexabromobenzene, decabromodiphenyl ether, bis-1,2-pentabromophenyl ethane, chlorinated polystyrene, chlorinated paraffin, etc.; phosphorus-based flame retardants such as red phosphorus, tricresyl phosphate, triphenyl phosphate, cresyldiphenyl phosphate, trixylenyl phosphate, trialkyl phosphate, dialkyl phosphate, tris(chloroethyl) phosphate, phosphazene, 1,3-phenylenebis(2,6-dixylenyl phosphate), 10-(2,5-dihydroxyphenyl)-10H-9-oxa-10-phosphaphenanthrene-10-oxide, etc.; inorganic-based flame retardants such as aluminum hydroxide, magnesium hydroxide, boehmite, bauxite, zinc borate, antimony trioxide, etc.; and silicone-based flame retardants such as silicone rubber, silicone resin, etc. These flame retardants may be used alone or in combination of two or more. Among these, 1,3-phenylenebis(2,6-dixylenyl phosphate) is preferable because it does not impair the low dielectric property.

[0072] When the resin composition of the present embodiment contains a flame retardant, its content is preferably 0.1% by mass or more of the resin composition, and preferably 20% by mass or less, and more preferably 10% by mass or less. The flame retardant can be used alone or in combination of two or more. When two or more are used, the total amount is within the above range.

[0073] <Dispersant> The resin composition of this embodiment may contain a dispersant. As the dispersant, those generally used for paints can be preferably used, and the type thereof is not particularly limited. Preferably, a copolymer-based wetting dispersant is used as the dispersant. Specific examples thereof include DISPERBYK (registered trademark)-110, 111, 161, 180, 2009, 2152, 2155, BYK (registered trademark)-W996, W9010, W903, W940, etc. manufactured by BYK-Chemie Japan Co., Ltd.

[0074] When the resin composition of this embodiment contains a dispersant, the lower limit of its content is preferably 0.01 part by mass or more, more preferably 0.1 part by mass or more, and may be 0.3 part by mass or more with respect to 100 parts by mass of the resin solid content in the resin composition. Also, the upper limit of the content of the dispersant is preferably 10 parts by mass or less, more preferably 5 parts by mass or less, and even more preferably 3 parts by mass or less with respect to 100 parts by mass of the resin solid content in the resin composition. The dispersant can be used alone or in combination of two or more. When two or more are used, the total amount is within the above range.

[0075] <Curing accelerator> The resin composition of this embodiment may further contain a curing accelerator. The curing accelerator is not particularly limited, and examples thereof include imidazoles such as triphenylimidazole; organic peroxides such as benzoyl peroxide, lauroyl peroxide, acetyl peroxide, parachlorobenzoyl peroxide, di-tert-butyl di-perphthalate; azo compounds such as azobisisobutyronitrile; tertiary amines such as N,N-dimethylbenzylamine, N,N-dimethylaniline, N,N-dimethyltoluidine, 2-N-ethylanilinoethanol, tri-n-butylamine, pyridine, quinoline, N-methylmorpholine, triethanolamine, triethylenediamine, tetramethylbutanediamine, N-methylpiperidine; phenols such as phenol, xylenol, cresol, resorcinol, catechol; organic metal salts such as lead naphthenate, lead stearate, zinc naphthenate, zinc octylate, manganese octylate, tin oleate, dibutyltin maleate, manganese naphthenate, cobalt naphthenate, iron acetylacetonate; those obtained by dissolving these organic metal salts in a hydroxyl group-containing compound such as phenol or bisphenol; inorganic metal salts such as tin chloride, zinc chloride, aluminum chloride; organic tin compounds such as dioctyltin oxide, other alkyltins, and alkyltin oxides, etc. Preferred curing accelerators are imidazoles and organic metal salts, and it is more preferable to use both imidazoles and organic metal salts in combination.

[0076] When the resin composition of this embodiment contains a curing accelerator, the lower limit of its content is preferably 0.005 parts by mass or more, more preferably 0.01 parts by mass or more, and even more preferably 0.1 parts by mass or more with respect to 100 parts by mass of the resin solid content in the resin composition. Also, the upper limit of the content of the curing accelerator is preferably 10 parts by mass or less, more preferably 5 parts by mass or less, and even more preferably 2 parts by mass or less with respect to 100 parts by mass of the resin solid content in the resin composition. The curing accelerator can be used alone or in combination of two or more. When two or more are used, the total amount is within the above range.

[0077] <Solvent> The resin composition of this embodiment may contain a solvent, and preferably contains an organic solvent. When containing a solvent, in the resin composition of this embodiment, at least a part, preferably all of the above-mentioned various resin solids are in a form (solution or varnish) dissolved or compatible with the solvent. The solvent is not particularly limited as long as it is a polar organic solvent or a non-polar organic solvent capable of dissolving or being compatible with at least a part, preferably all of the above-mentioned various resin solids. Examples of the polar organic solvent include ketones (such as acetone, methyl ethyl ketone, methyl isobutyl ketone, etc.), cellosolves (such as propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, etc.), esters (such as ethyl lactate, methyl acetate, ethyl acetate, butyl acetate, isoamyl acetate, ethyl lactate, methyl methoxypropionate, methyl hydroxyisobutyrate, etc.), amides (such as dimethoxyacetamide, dimethylformamides, etc.). Examples of the non-polar organic solvent include aromatic hydrocarbons (such as toluene, xylene, etc.). The solvent can be used alone or in combination of two or more. When two or more are used, the total amount is within the above range.

[0078] <Other components> In addition to the above components, the resin composition of this embodiment may contain various polymer compounds such as thermoplastic resins and their oligomers, and various additives. Examples of the additives include ultraviolet absorbers, antioxidants, photoinitiators, fluorescent brighteners, photosensitizers, dyes, pigments, thickeners, flow regulators, lubricants, defoamers, leveling agents, gloss agents, polymerization inhibitors, etc. These additives can be used alone or in combination of two or more.

[0079] <Uses> The resin composition of this embodiment is used as a cured product. Specifically, the resin composition of this embodiment can be suitably used as a low dielectric constant material and / or a low dielectric tangent material, such as an insulating layer of a printed wiring board, a material for a semiconductor package, etc., as a resin composition for electronic materials. The resin composition of this embodiment can be suitably used as a prepreg, a metal foil-clad laminate using the prepreg, a resin sheet, and a material for a printed wiring board. The resin composition of this embodiment is used as a layered (including the meaning of film-like, sheet-like, etc.) material such as an insulating layer of a printed wiring board, a prepreg, a resin sheet, etc. When such a layered material is used, its thickness is preferably 5 μm or more, and more preferably 10 μm or more. As the upper limit value of the thickness, it is preferably 200 μm or less, and more preferably 180 μm or less. Note that the thickness of the above-mentioned layered material means the thickness including the glass cloth, for example, when the resin composition of this embodiment is impregnated into a glass cloth or the like. The material formed from the resin composition of this embodiment may be used for applications where a pattern is formed by exposure and development, or may be used for applications where exposure and development are not performed. In particular, it is suitable for applications where exposure and development are not performed.

[0080] <<Prepreg>> The prepreg of this embodiment is formed from a base material (prepreg base material) and the resin composition of this embodiment. The prepreg of this embodiment can be obtained, for example, by applying (for example, impregnating and / or coating) the resin composition of this embodiment to a base material and then semi-curing it by heating (for example, drying at 120 to 220 °C for 2 to 15 minutes). In this case, the adhesion amount of the resin composition to the base material, that is, the amount of the resin composition (including the filler (D)) with respect to the total amount of the prepreg after semi-curing is preferably in the range of 20 to 99% by mass, and more preferably in the range of 20 to 70% by mass.

[0081] The base material is not particularly limited as long as it is a base material used in various printed wiring board materials. Examples of the material of the base material include glass fibers (e.g., E-glass, D-glass, L-glass, S-glass, T-glass, Q-glass, UN-glass, NE-glass, spherical glass, etc.), inorganic fibers other than glass (e.g., quartz, etc.), and organic fibers (e.g., polyimide, polyamide, polyester, liquid crystal polyester, polytetrafluoroethylene, etc.). The form of the base material is not particularly limited, and examples include woven fabric, non-woven fabric, roving, chopped strand mat, surfacing mat, etc. These base materials may be used alone or in combination of two or more. Among these base materials, from the viewpoint of dimensional stability, a woven fabric subjected to superfine fiber treatment and filling treatment is preferable. From the viewpoints of strength and low water absorption, the base material has a thickness of 200 μm or less and a mass of 250 g / m 2 The following glass woven fabrics are preferable, and from the viewpoint of moisture absorption and heat resistance, a glass woven fabric surface-treated with a silane coupling agent such as epoxy silane treatment or amino silane treatment is preferable. From the viewpoint of electrical characteristics, a low-dielectric glass cloth made of glass fibers exhibiting low dielectric constant and low dielectric tangent, such as L-glass, NE-glass, or Q-glass, is more preferable. Examples of the base material with low dielectric constant include, for example, a base material having a dielectric constant of 5.0 or less (preferably 3.0 to 4.9). Examples of the base material with low dielectric tangent include, for example, a base material having a dielectric tangent of 0.006 or less (preferably 0.001 to 0.005). The dielectric constant and the dielectric tangent are values measured at 10 GHz by a perturbation method cavity resonator.

[0082] <<Metal foil-clad laminate>> The metal foil-clad laminate of the present embodiment includes a layer formed from at least one prepreg of the present embodiment and metal foil disposed on one or both sides of the layer formed from the prepreg. As a method for manufacturing the metal foil-clad laminate of the present embodiment, for example, there is a method of arranging at least one prepreg of the present embodiment (preferably stacking two or more), disposing metal foil on one or both sides thereof, and performing lamination molding. More specifically, it can be manufactured by disposing metal foil such as copper foil or aluminum foil on one or both sides of the prepreg and performing lamination molding. The number of prepregs is preferably 1 to 10, more preferably 2 to 10, and even more preferably 2 to 9. The metal foil is not particularly limited as long as it is used as a material for printed wiring boards, and examples include copper foils such as rolled copper foil and electrolytic copper foil. The thickness of the metal foil (preferably copper foil) is not particularly limited and may be about 1.5 to 70 μm. As the molding method, there are methods usually used when molding printed wiring board laminates and multilayer boards. More specifically, using a multi-stage press, multi-stage vacuum press, continuous molding machine, autoclave molding machine, etc., at a temperature of about 180 to 350 °C, a heating time of about 100 to 300 minutes, and a surface pressure of 20 to 100 kg / cm 2 There is a method of performing lamination molding. Further, a multilayer board can also be obtained by combining the prepreg of the present embodiment and a separately manufactured wiring board for inner layers and performing lamination molding. As a method for manufacturing a multilayer board, for example, copper foil of about 35 μm is disposed on both sides of one prepreg of the present embodiment, lamination is formed by the above molding method, an inner layer circuit is then formed, a blackening treatment is performed on this circuit to form an inner layer circuit board, and then this inner layer circuit board and the prepreg of the present embodiment are alternately arranged one by one, and further copper foil is disposed on the outermost layer, and lamination molding is preferably performed under vacuum under the above conditions to manufacture a multilayer board. The metal foil-clad laminate of the present embodiment can be suitably used as a printed wiring board.

[0083] The metal foil-clad laminate of this embodiment preferably has a low dielectric constant (Dk) measured using laminate A from which the metal foil has been removed by etching. Specifically, the dielectric constant (Dk) of the laminate A is preferably 4.3 or less, more preferably 4.1 or less. There is no particular limitation on the lower limit value of the dielectric constant (Dk), but for example, 3.0 or more is practical. Also, the metal foil-clad laminate of this embodiment preferably has a low dissipation factor (Df) measured using laminate A from which the metal foil has been removed by etching. Specifically, the dissipation factor (Df) is preferably 0.0060 or less, more preferably 0.0050 or less. There is no particular limitation on the lower limit value of the dissipation factor (Df), but for example, 0.0027 or more is practical. The dielectric constant (Dk) and the dissipation factor (Df) are measured according to the methods described in the examples below.

[0084] Also, the metal foil-clad laminate of this embodiment preferably has a high glass transition temperature measured using laminate A from which the metal foil has been removed by etching. Specifically, the glass transition temperature of the laminate A is preferably, for example, 250°C or higher, more preferably 270°C or higher. The upper limit value of the glass transition temperature is, for example, 400°C or lower, which is practical. The glass transition temperature of the metal foil-clad laminate is measured according to the description in the examples below.

[0085] The metal foil-clad laminate of this embodiment preferably has a water absorption rate of 0.35 mass% or less, more preferably 0.25 mass% or less, after being treated at 121°C and 2 atmospheres for 1 hour using a pressure cooker tester in accordance with JIS C6485:2008. The lower limit of the water absorption rate is, for example, 0 mass%. Also, the metal foil-clad laminate of this embodiment preferably has a water absorption rate of 0.35 mass% or less, more preferably 0.25 mass% or less, after being treated at 121°C and 2 atmospheres for 5 hours using a pressure cooker tester in accordance with JIS C6485:2008. The lower limit of the water absorption rate is, for example, 0 mass%.

[0086] As described above, the resin composition for electronic materials obtained by using the resin composition (resin composition composed of a specific component combination) of the present embodiment has excellent heat resistance, low dielectric properties (low dielectric constant, low dielectric tangent), low water absorption, and further excellent chemical resistance and desmear resistance of the cured product.

[0087] <<Printed Wiring Board>> The printed wiring board of the present embodiment is a printed wiring board including an insulating layer and a conductor layer disposed on the surface of the insulating layer, wherein the insulating layer includes at least one of a layer formed from the resin composition of the present embodiment and a layer formed from the prepreg of the present embodiment. Such a printed wiring board can be manufactured according to a conventional method, and its manufacturing method is not particularly limited. Hereinafter, an example of the manufacturing method of the printed wiring board will be shown. First, prepare a metal foil-clad laminate such as the above-described metal foil-clad laminate. Next, perform an etching process on the surface of the metal foil-clad laminate to form an inner layer circuit and produce an inner layer substrate. Perform a surface treatment on the surface of the inner layer circuit of the inner layer substrate as necessary to enhance the adhesion strength, then stack the required number of the above-described prepregs on the surface of the inner layer circuit, and further laminate a metal foil for the outer layer circuit on the outside thereof, and perform heating and pressing to integrally mold. In this way, a multilayer laminate in which an insulating layer composed of a base material and a cured product of the resin composition is formed between the inner layer circuit and the metal foil for the outer layer circuit is manufactured. Next, after performing drilling for through holes and via holes on this multilayer laminate, form a plating metal film for electrically connecting the inner layer circuit and the metal foil for the outer layer circuit on the wall surface of the holes, and further perform an etching process on the metal foil for the outer layer circuit to form the outer layer circuit, thereby manufacturing the printed wiring board.

[0088] The printed wiring board obtained in the above manufacturing example has an insulating layer and a conductor layer formed on the surface of the insulating layer, and the insulating layer has a configuration including the resin composition of the present embodiment described above and / or its cured product. That is, the prepreg of the present embodiment described above (for example, a prepreg formed from a base material and the resin composition of the present embodiment impregnated or coated thereon) and the layer formed from the resin composition of the metal foil-clad laminate of the present embodiment described above become the insulating layer of the present embodiment.

[0089] <<Resin sheet>> The resin sheet of this embodiment includes a support and a layer formed from the resin composition of this embodiment disposed on the surface of the support. The resin sheet can be used as a build-up film or a dry film solder resist. As a method for manufacturing the resin sheet, although not particularly limited, for example, a method of obtaining a resin sheet by applying (coating) a solution in which the above-described resin composition of this embodiment is dissolved in a solvent to a support and drying it can be mentioned.

[0090] Examples of the support used here include polyethylene films, polypropylene films, polycarbonate films, polyethylene terephthalate films, ethylene tetrafluoroethylene copolymer films, and release films obtained by applying a release agent to the surfaces of these films, organic film substrates such as polyimide films, conductor foils such as copper foils and aluminum foils, glass plates, SUS (Steel Use Stainless) plates, and plate-like materials such as FRP (Fiber-Reinforced Plastics), but it is not particularly limited.

[0091] Examples of the coating method (coating process) include a method of applying a solution in which the resin composition of this embodiment is dissolved in a solvent onto a support using a bar coater, die coater, doctor blade, baker applicator, etc. Also, after drying, the support can be peeled off or etched from the resin sheet in which the support and the resin composition are laminated to obtain a single-layer sheet. In addition, a single-layer sheet can be obtained without using a support by supplying a solution in which the above-described resin composition of this embodiment is dissolved in a solvent into a mold having a sheet-shaped cavity, drying it, etc. to form it into a sheet shape.

[0092] In the production of the single-layer sheet or resin sheet of the present embodiment, the drying conditions for removing the solvent are not particularly limited. However, if the temperature is too low, the solvent is likely to remain in the resin composition, and if the temperature is too high, the curing of the resin composition progresses. Therefore, a temperature of 20°C to 200°C for 1 to 90 minutes is preferred. The single-layer sheet or resin sheet can also be used in an uncured state where only the solvent has been dried, or can be used in a semi-cured (B-stage) state as needed. Furthermore, the thickness of the resin layer in the single-layer sheet or resin sheet of the present embodiment can be adjusted according to the concentration and coating thickness of the solution of the resin composition of the present embodiment used for coating (painting), and is not particularly limited. However, generally, as the coating thickness increases, the solvent is more likely to remain during drying, so 0.1 to 500 μm is preferred.

Example

[0093] The present invention will be described more specifically with reference to the following examples. The materials, amounts used, ratios, treatment details, treatment procedures, etc. shown in the following examples can be appropriately changed without departing from the spirit of the present invention. Therefore, the scope of the present invention is not limited to the specific examples shown below. If the measuring instruments and the like used in the examples are difficult to obtain due to being obsolete or the like, measurements can be made using other instruments having equivalent performance.

[0094] <Synthesis Example 1 Synthesis of Naphthol Aralkyl Type Cyanate Ester Compound (SNCN)> 300 g (1.28 mol in terms of OH group) of 1-naphthol aralkyl resin (manufactured by Nippon Steel & Sumikin Chemical Co., Ltd.) and 194.6 g (1.92 mol) (1.5 mol per 1 mol of hydroxy group) of triethylamine were dissolved in 1800 g of dichloromethane to obtain Solution 1. 125.9 g (2.05 mol) of cyanogen chloride (1.6 mol per 1 mol of hydroxy group), 293.8 g of dichloromethane, 194.5 g (1.92 mol) of 36% hydrochloric acid (1.5 mol per 1 mol of hydroxy group), and 1205.9 g of water were stirred while maintaining the liquid temperature at -2 to -0.5 °C, and Solution 1 was poured in over 30 minutes. After the pouring of Solution 1 was completed, the mixture was stirred at the same temperature for 30 minutes, and then a solution (Solution 2) prepared by dissolving 65 g (0.64 mol) of triethylamine (0.5 mol per 1 mol of hydroxy group) in 65 g of dichloromethane was poured in over 10 minutes. After the pouring of Solution 2 was completed, the mixture was stirred at the same temperature for 30 minutes to complete the reaction. Thereafter, the reaction solution was allowed to stand to separate the organic phase and the aqueous phase. The obtained organic phase was washed 5 times with 1300 g of water. The electrical conductivity of the waste water in the fifth water wash was 5 μS / cm, and it was confirmed that the ionic compounds that could be removed were sufficiently removed by washing with water. The organic phase after water washing was concentrated under reduced pressure, and finally concentrated to dryness at 90 °C for 1 hour to obtain 331 g of the target naphthol aralkyl type cyanate ester compound (SNCN) (orange viscous substance). The weight average molecular weight of the obtained SNCN was 600. Also, the IR spectrum of SNCN showed absorption at 2250 cm -1 (cyanate ester group), and no absorption of the hydroxy group was shown.

[0095] Example 1 50 parts by mass of the compound (A) represented by the formula (M1) ("X9-450", manufactured by DIC Corporation, the compound represented by the formula (M1)), 50 parts by mass of the naphthol aralkyl type cyanate ester compound (SNCN) obtained in Synthesis Example 1 (a cyanate ester compound having two or more aromatic moieties substituted by at least one cyanato group in the molecule), 100 parts by mass of fused silica ("SC2050-MNU", average particle diameter 0.5 μm (manufactured by Admatechs Co., Ltd.)), and 0.2 parts by mass of manganese octylate (catalyst) were dissolved in methyl ethyl ketone and mixed to obtain a varnish. The above-mentioned addition amounts each indicate the solid content. This varnish was further diluted with methyl ethyl ketone, impregnated and coated on an E-glass woven fabric (manufactured by Arisawa Manufacturing Co., Ltd., product number: 2116) with a thickness of 0.094 mm, and heated and dried at 150 °C for 5 minutes to obtain a prepreg having a resin composition amount (including the filler) of 60% by mass, an E-glass woven fabric (glass cloth amount) of 40% by mass, and a thickness of 100 μm.

[0096] Eight sheets of the obtained prepreg were stacked, and 12-μm-thick electrolytic copper foils were placed on the top and bottom, and laminated molding was performed at a pressure of 30 kgf / cm 2 and a temperature of 220 °C for 120 minutes to obtain a metal foil-clad laminate with an insulating layer thickness of 0.8 mm. As the 12-μm-thick electrolytic copper foil, 3EC-M3-VLP, manufactured by Mitsui Mining & Smelting Co., Ltd., was used. Using the obtained metal foil-clad laminate, evaluations were performed on moldability (presence or absence of voids), peel strength, glass transition temperature (Tg), dielectric constant (Dk), dissipation factor (Df), water absorption, chemical resistance, and desmear resistance. The evaluation results are shown in Table 1.

[0097] (Measurement methods and evaluation methods) (1) Moldability (presence or absence of voids) The internal appearance (insulating layer) of the metal foil-clad laminate was visually confirmed, and those with voids observed were judged as "void present", and those without voids observed were judged as "void absent". (2) Peel strength The peel strength was measured using the metal foil-clad laminate in accordance with JIS-C6481:1996 to measure the peel strength of the copper foil. The unit was shown as kg / cm. (3) Glass transition temperature (Tg) The glass transition temperature was measured using a dynamic viscoelasticity measuring device (DMA) in accordance with JIS-K7244-4:1999 (Plastics - Test methods for dynamic mechanical properties - Part 4: Tensile vibration - Non-resonant method). The dynamic viscoelasticity of a laminate obtained by removing the copper foil of a metal foil-clad laminate by etching (hereinafter referred to as "laminate A") was measured under a nitrogen atmosphere at a starting temperature of 30°C, an ending temperature of 400°C, a heating rate of 5°C / min, a measurement frequency of 1 Hz. The maximum value of the loss tangent (tanδ) obtained at that time was defined as the glass transition temperature. As the dynamic viscoelasticity measuring device, EXSTAR6000 DMS6100 manufactured by Seiko Instruments Inc. was used. Evaluation was conducted as follows. A: 270°C or higher B: 250°C or higher and less than 270°C C: 230°C or higher and less than 250°C D: Less than 230°C

[0098] (4) Dielectric constant (Dk) and dielectric loss tangent (Df): Using the laminate A, the dielectric constant (Dk) and dielectric loss tangent (Df) at 10 GHz were measured by a perturbation method cavity resonator. As the perturbation method cavity resonator, Agilent8722ES manufactured by Agilent Technologies was used. Evaluation was conducted as follows. <dk> A: Below 4.1 B: Exceeding 4.1 and below 4.3 C: Exceeding 4.3 <df> A: 0.0050 or less B: More than 0.0050 and 0.0060 or less C: More than 0.0060

[0099] Also, using a pressure cooker tester, after standing for 5 hours under the conditions of 121°C and 2 atmospheres, Dk and Df were measured in the same manner as above. Evaluation was carried out as follows. <Dk (after water absorption)> A: 4.2 or less B: More than 4.2 and 4.3 or less C: More than 4.3 <Df (after water absorption)> A: 0.0110 or less B: More than 0.0110 and 0.0120 or less C: More than 0.0120 and 0.0130 or less D: More than 0.0130

[0100] (5) Water absorption rate: Samples obtained by cutting laminate A into 30 mm × 30 mm were used to measure the water absorption rate after treatment at 121°C and 2 atmospheres for 1 hour and 5 hours using a pressure cooker tester in accordance with JIS C6485:2008. In Table 1, "1h" corresponds to the water absorption rate after treatment for 1 hour, and "5h" corresponds to the water absorption rate after treatment for 5 hours. The pressure cooker tester used was the PC-3 model manufactured by Hirayama Seisakusho Co., Ltd. Evaluation was carried out as follows. A: 0.25 mass% or less B: More than 0.25 mass% and 0.35 mass% or less C: More than 0.35 mass%

[0101] (6) Chemical resistance: Samples of laminate A cut into 50 mm × 50 mm were immersed in a hydrochloric acid aqueous solution at 60 °C adjusted to 4 N for 1 hour or 2 hours. The mass reduction rate (mass %) was calculated from the mass of laminate A before and after immersion. The smaller the absolute value, the better the chemical resistance (acid resistance). Also, they were immersed in a sodium hydroxide aqueous solution at 70 °C adjusted to 1 N for 1 hour or 2 hours. The mass reduction rate (mass %) was calculated from the mass of laminate A before and after immersion and shown as an absolute value. The smaller the absolute value, the better the chemical resistance (alkali resistance). Evaluated as follows. A: 0 mass % or more and 0.4 mass % or less B: More than 0.4 mass % and 1.0 mass % or less C: More than 1.0 mass % and 2.0 mass % or less D: More than 2.0 mass %

[0102] (7) Resistance to desmear: For laminate A, the following immersion treatment was carried out. First, laminate A was immersed in a swelling liquid (manufactured by Atotech Japan, Swelling Dip Securigant P) at 80 °C for 10 minutes. Next, the immersed laminate A was immersed in a roughening liquid (manufactured by Atotech Japan, Concentrate Compact CP) at 80 °C for 5 minutes. Next, the immersed laminate A was immersed in a neutralizing liquid (manufactured by Atotech Japan, Reduction Conditioner Securigant P500) at 45 °C for 10 minutes. The mass reduction rate (mass %) of laminate A after performing this series of immersion treatments once, twice, and three times was measured. In Table 1, "1 time" corresponds to "the mass reduction rate (mass %) after performing the immersion treatment once", "2 times" corresponds to "the mass reduction rate (mass %) after performing the immersion treatment twice", and "3 times" corresponds to "the mass reduction rate (mass %) after performing the immersion treatment three times". The numerical values are shown as absolute values. Evaluated as follows. A: 1.0 mass % or less B: More than 1.0 mass % and 2.0 mass % or less C: More than 2.0 mass %

[0103] Example 2 In Example 1, the naphthol aralkyl type cyanate ester compound (SNCN) was changed to the same amount of bisphenol A type cyanate ester compound (manufacturer: Mitsubishi Gas Chemical Company, Inc., product number CYTESTER (registered trademark) TA), and the addition amount of manganese octylate (catalyst) was changed from 0.2 parts by mass to 0.3 parts by mass. Otherwise, it was carried out in the same manner. The results are shown in Table 1.

[0104] Comparative Example 1 In Example 1, the compound (A) represented by the formula (M1) ("X9-450", manufactured by DIC Corporation) was changed to the same amount of the compound having the following structure (manufactured by Kayaku Kasei Co., Ltd., BMI-70 (trade name)), and the addition amount of manganese octylate (catalyst) was changed from 0.2 parts by mass to 0.4 parts by mass. Otherwise, it was carried out in the same manner. The results are shown in Table 1.

Chemical formula

[0105] Comparative Example 2 In Example 1, the compound (A) represented by the formula (M1) ("X9-450", manufactured by DIC Corporation) was changed to the same amount of the maleimide compound having the following structure (manufactured by Daiwa Kasei Kogyo Co., Ltd., BMI-2300 (trade name)), and the addition amount of manganese octylate (catalyst) was changed from 0.2 parts by mass to 0.15 parts by mass. Otherwise, it was carried out in the same manner. The results are shown in Table 1.

Chemical formula

[0106] Comparative Example 3 In Example 1, the compound (A) represented by the formula (M1) ("X9-450", manufactured by DIC Corporation) was changed to the same amount of the maleimide compound having the following structure (manufactured by Nippon Kayaku Co., Ltd., MIR-3000 (trade name)). Otherwise, it was carried out in the same manner. The results are shown in Table 1.

Chemical formula

[0107]

Table 1

Industrial Applicability

[0108] As described above, the resin composition of the present invention can be widely and effectively used in various applications such as electrical and electronic materials, machine tool materials, and aerospace materials. For example, it can be used as electrical insulation materials, semiconductor plastic packages, encapsulating materials, adhesives, laminated materials, resists, build-up laminated board materials, etc. In particular, it can be effectively used as a printed wiring board material for coping with high integration and high density in recent information terminal devices and communication devices. In addition, the metal foil-clad laminate of the present invention has particularly low water absorption, chemical resistance, desmear resistance, and heat resistance, so its industrial practicality is extremely high.< / df> < / dk>

Claims

1. A resin composition comprising a compound (A) represented by formula (M1) and a cyanate ester compound (B) having two or more aromatic moieties substituted with at least one cyanato group in the molecule, wherein the cyanate ester compound (B) having two or more aromatic moieties substituted with at least one cyanato group in the molecule is a naphthol aralkyl type cyanate ester compound, wherein, based on 100 parts by mass of the resin solid content contained in the resin composition, the content of the compound (A) represented by formula (M1) is 1 to 90 parts by mass, and the content of the cyanate ester compound (B) is 1 to 90 parts by mass, A resin composition wherein the total amount of the compound (A) represented by formula (M1) and the cyanate ester compound (B) is 20% by mass or more of the resin solid content. 【Chemical 1】 (In formula (M1), R Ｍ１ , R Ｍ２ , R Ｍ３ , and R Ｍ４ each independently represent a hydrogen atom or an alkyl group having 1 to 12 carbon atoms. R Ｍ５ and R Ｍ６ each independently represent a hydrogen atom or an alkyl group having 1 to 12 carbon atoms. Ar Ｍ represents a divalent aromatic group. A is an alicyclic group having 4 to 6 members. R Ｍ７ and R Ｍ８ are each independently an alkyl group having 1 to 6 carbon atoms. mx is 1 or 2, and lx is 0 or 1. R Ｍ９ and R Ｍ１０ each independently represent a hydrogen atom or an alkyl group having 1 to 12 carbon atoms. R Ｍ１１ , R Ｍ１２ , R Ｍ１３ , and R Ｍ１４ each independently represent a hydrogen atom or an alkyl group having 1 to 12 carbon atoms. nx represents an integer of 1 or more and 20 or less.)

2. The resin composition according to claim 1, further comprising a filler (D).

3. The resin composition according to claim 2, wherein the content of the filler (D) in the resin composition is 50 to 1600 parts by mass based on 100 parts by mass of the resin solid content.

4. The resin composition according to any one of claims 1 to 3, which is for a printed wiring board.

5. A cured product of the resin composition according to any one of claims 1 to 4.

6. A prepreg comprising a base material and the resin composition according to any one of claims 1 to 4 formed thereon.

7. A metal foil-clad laminate comprising at least one prepreg according to claim 6 and a metal foil disposed on one or both sides of the prepreg.

8. A resin sheet comprising a support and a layer formed of the resin composition according to any one of claims 1 to 4 disposed on the surface of the support.

9. A printed wiring board comprising an insulating layer and a conductor layer disposed on the surface of the insulating layer, wherein the insulating layer comprises at least one of a layer formed of the resin composition according to any one of claims 1 to 4 and a layer formed of the prepreg according to claim 6.

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