TW202330788A - Resin composition, prepreg, metal foil-clad laminate board, resin composite sheet, printed wiring board, and semiconductor device - Google Patents

Abstract

Provided are: a novel resin composition that exhibits an excellent heat resistance after moisture absorption while maintaining an excellent low dielectric loss tangent, and also a prepreg, a metal foil-clad laminate board, a resin composite sheet, a printed wiring board, and a semiconductor device. The resin composition comprises a thermoplastic elastomer (A), a thermoplastic elastomer (B), and a thermosetting resin (C) that is compatible with both (A) and (B). The thermoplastic elastomer (A) is a thermoplastic elastomer comprising a styrene monomer unit and a conjugated diene monomer unit and having a number-average molecular weight of at least 50,000, wherein all of the conjugated diene bonds in the thermoplastic elastomer are hydrogenated. The thermoplastic elastomer (B) is a thermoplastic elastomer comprising a styrene monomer unit and a conjugated diene monomer unit and having a number-average molecular weight of at least 50,000, wherein a portion of the conjugated diene bonds in the thermoplastic elastomer is hydrogenated and/or all are unsaturated bonds.

Description

Resin composition, prepreg, metal foil-clad laminate, resin composite sheet, printed wiring board, and semiconductor device

The present invention relates to a resin composition, a prepreg, a metal foil-clad laminate, a resin composite sheet, a printed wiring board, and a semiconductor device.

In recent years, beginning with portable terminals, semiconductor elements used in electronic equipment, communication equipment, etc. are being rapidly integrated and miniaturized. Along with this, technology capable of mounting semiconductor elements at a high density is required, and improvements are also required for printed wiring boards, which play an important role. On the other hand, the uses of electronic devices and the like continue to be diversified and expanded. In response to this, various properties required for printed wiring boards, metal foil-clad laminates used therein, prepregs, and the like have also become diverse and strict. In order to obtain an improved printed wiring board in consideration of such required characteristics, various materials and processing methods have been proposed. One of them is the improvement and development of the resin material constituting the prepreg.

For example, Patent Document 1 discloses a resin composition comprising a maleimide compound (A), a cyanate compound (B), and a polyphenylene ether compound ( C) and a block copolymer (D) having a styrene skeleton. In addition, Patent Document 2 discloses a resin composition containing a polyfunctional vinyl aromatic polymer (A) and a thermosetting compound (B), and containing no radical polymerization initiator. [Prior Art Literature] [Patent Document]

[Patent Document 1] International Publication No. 2019/230945 [Patent Document 2] International Publication No. 2020/175537

[Problem to be Solved by the Invention]

As mentioned above, the use of electronic equipment and the like continues to diversify and expand, and new materials are also required for resin materials constituting prepregs and the like. In particular, further material development is being sought for resin compositions that are excellent in moisture absorption and heat resistance while maintaining an excellent low dielectric loss tangent. The object of the present invention is to solve the above-mentioned problems. The object is to provide a novel resin composition, a prepreg, a metal foil-clad laminate, and a resin composite that are excellent in moisture absorption and heat resistance while maintaining an excellent low dielectric loss tangent. chips, printed wiring boards, and semiconductor devices. [Means to solve the problem]

Based on the above-mentioned problems, the inventors of the present invention have studied and solved the above-mentioned problems by using a predetermined hydrogenated thermoplastic elastomer together with a predetermined partially hydrogenated or non-hydrogenated thermoplastic elastomer. Specifically, the above-mentioned problems are solved by the following means. <1> A resin composition comprising a thermoplastic elastomer (A), a thermoplastic elastomer (B), and a thermosetting resin compatible with the thermoplastic elastomer (A) and the thermoplastic elastomer (B). Resin (C), the thermoplastic elastomer (A) is a conjugated thermoplastic elastomer in a thermoplastic elastomer containing styrene monomer units and conjugated diene monomer units and having a number average molecular weight of 50,000 or more A thermoplastic elastomer obtained by hydrogenating all diene bonds. The thermoplastic elastomer (B) is a thermoplastic elastomer containing styrene monomer units and conjugated diene monomer units and having a number-average molecular weight of 50,000 or more. A thermoplastic elastomer obtained by hydrogenating part of the conjugated diene bonds of the thermoplastic elastomer, and/or a thermoplastic elastomer with all unsaturated bonds. <2> The resin composition according to <1>, wherein the total content of the thermoplastic elastomer (A) and the thermoplastic elastomer (B) in the resin composition is: 1 to 40 parts by mass. <3> The resin composition according to <1> or <2>, wherein, in the resin composition, the mass ratio of the thermoplastic elastomer (A) to the thermoplastic elastomer (B) is 1:1-10. <4> The resin composition according to any one of <1> to <3>, wherein the compatible thermosetting resin (C) is a thermosetting resin containing an aromatic ring and a vinyl group. <5> The resin composition according to any one of <1> to <4>, wherein the compatible thermosetting resin (C) is selected from polymers having constituent units represented by formula (V) , and one or more of the group consisting of polyphenylene ether compounds having a carbon-carbon unsaturated double bond at the end; [Chemical 1] (In formula (V), Ar represents an aromatic hydrocarbon linking group; * represents a bonding position.) <6> The resin composition according to any one of <1> to <5>, wherein the compatible thermosetting Content of the permanent resin (C) is 10-90 mass parts with respect to 100 mass parts of resin solid content. <7> The resin composition according to any one of <1> to <6>, further comprising 1 selected from the group consisting of cyanate compounds, maleimide compounds, and epoxy compounds. More than one other resin (D). <8> The resin composition according to <7>, wherein the maleimide compound is selected from a compound represented by formula (M0), a compound represented by formula (M1), a compound represented by formula (M2), One or more species in the group consisting of a compound represented by formula (M3), a compound represented by formula (M4), and a compound represented by formula (M5). [Chem 2] (In formula (M0), R ⁵¹ each independently represent a hydrogen atom, an alkyl group with 1 to 8 carbons, or a phenyl group, R ⁵² each independently represent a hydrogen atom or a methyl group, and n ₁ represents an integer of 1 or more. ) [Chem3] (In formula (M1), R ^M1 , R ^M2 , R ^M3 , and R ^M4 are each independently representing a hydrogen atom or an organic group; R ^M5 and R ^M6 are each independently representing a hydrogen atom or an alkyl group; Ar ^M represents 2 Aromatic group of valency; A is the alicyclic group of 4~6 membered ring; R ^M7 and R ^M8 are each independently an alkyl group; mx is 1 or 2, lx is 0 or 1; R ^M9 and R ^M10 are each R ^M11 , R ^M12 , R ^M13 , and R ^M14 each independently represent a hydrogen atom or an organic group; R ^M15 each independently represent an alkyl group with a carbon number of 1 to 10, and a carbon number Alkyloxy group with 1~10 carbon number, alkylthio group with 1~10 carbon number, aryl group with 6~10 carbon number, aryloxy group with 1~10 carbon number, arylthio group with 1~10 carbon number , halogen atom, hydroxyl or mercapto; px represents an integer of 0~3; nx represents an integer of 1~20.) [Chemical 4] (In the formula (M2), R ⁵⁴ each independently represent a hydrogen atom or a methyl group, and n ₄ represents an integer of 1 or more.) [Chem. 5] (In formula (M3), R ⁵⁵ each independently represent a hydrogen atom, an alkyl group with 1 to 8 carbons, or a phenyl group, and n ₅ represents an integer ranging from 1 to 10.) [Chemical 6] (In the formula (M4), R ⁵⁶ each independently represent a hydrogen atom, a methyl group or an ethyl group, and R ⁵⁷ each independently represent a hydrogen atom or a methyl group.) [Chem. 7] (In formula (M5), R ⁵⁸ each independently represent a hydrogen atom, an alkyl group with 1 to 8 carbons, or a phenyl group, R ⁵⁹ each independently represent a hydrogen atom or a methyl group, and n ₆ represents an integer of 1 or more. ) <9> The resin composition according to <7>, wherein the maleimide compound includes a compound represented by formula (M1) and/or a compound represented by formula (M3); [Chem. 8] (In formula (M1), R ^M1 , R ^M2 , R ^M3 , and R ^M4 are each independently representing a hydrogen atom or an organic group; R ^M5 and R ^M6 are each independently representing a hydrogen atom or an alkyl group; Ar ^M represents 2 Aromatic group of valency; A is the alicyclic group of 4~6 membered ring. R ^M7 and R ^M8 are each independently an alkyl group; mx is 1 or 2, lx is 0 or 1; R ^M9 and R ^M10 are each R ^M11 , R ^M12 , R ^M13 , and R ^M14 each independently represent a hydrogen atom or an organic group; R ^M15 each independently represent an alkyl group with a carbon number of 1 to 10, and a carbon number Alkyloxy group with 1~10 carbon number, alkylthio group with 1~10 carbon number, aryl group with 6~10 carbon number, aryloxy group with 1~10 carbon number, arylthio group with 1~10 carbon number , halogen atom, hydroxyl or mercapto; px represents an integer of 0~3; nx represents an integer of 1~20.) [Chemical 9] (In formula (M3), R ⁵⁵ each independently represents a hydrogen atom, an alkyl group with 1 to 8 carbons, or a phenyl group, and n ₅ represents an integer ranging from 1 to 10.) <10> such as <1> to <9 > The resin composition according to any one of the above, which further contains a flame retardant (E). <11> The resin composition according to <10>, wherein the flame retardant (E) contains a phosphorus-based flame retardant. <12> The resin composition according to any one of <1> to <11>, further comprising a filler (F). <13> The resin composition according to <12>, wherein the filler (F) contains a material selected from silicon dioxide, aluminum hydroxide, aluminum nitride, boron nitride, forsterite, titanium oxide , barium titanate, strontium titanate, and calcium titanate at least one of the group. <14> The resin composition according to <12> or <13>, wherein the content of the filler (F) is 10 to 300 parts by mass relative to 100 parts by mass of resin solid content. <15> The resin composition according to any one of <1> to <14>, further comprising a monomer or oligomer having an ethylenically unsaturated group, the monomer or oligomer having an ethylenically unsaturated group The content of is 0.5-30 mass parts with respect to 100 mass parts of resin solid content. <16> The resin composition according to any one of <1> to <15>, wherein the total content of the thermoplastic elastomer (A) and the thermoplastic elastomer (B) in the resin composition is 100 parts by mass of resin solid content is 1~40 parts by mass; In the resin composition, the mass ratio of the thermoplastic elastomer (A) to the thermoplastic elastomer (B) is 1:1~10; The curable resin (C) is a thermosetting resin containing an aromatic ring and a vinyl group; the compatible thermosetting resin (C) includes a polymer selected from a constituent unit represented by formula (V), and One or more of the group consisting of polyphenylene ether compounds having a carbon-carbon unsaturated double bond at the end; [Chem. 10] (In the formula (V), Ar represents an aromatic hydrocarbon linking group; * represents a bonding position.) The content of the compatible thermosetting resin (C) is 10 to 90 parts by mass relative to 100 parts by mass of the resin solid content Parts; The resin composition further contains other resins (D) selected from the group consisting of cyanate compounds, maleimide compounds, and epoxy compounds; the maleimide compound Containing at least one selected from the group consisting of compounds represented by formula (M1), compounds represented by formula (M3), and compounds represented by formula (M5); the resin composition further contains a flame retardant (E ); The flame retardant (E) contains a phosphorus flame retardant; The resin composition further contains a filler (F); The filler (F) contains a material selected from silicon dioxide, aluminum hydroxide, aluminum nitride , boron nitride, forsterite (Forsterite), titanium oxide, barium titanate, strontium titanate, and calcium titanate; the content of the filler (F) relative to the resin solid 100 parts by mass of components is 10~300 parts by mass; the resin composition further contains monomers or oligomers with ethylenically unsaturated groups, and the content of monomers or oligomers with ethylenically unsaturated groups is relatively Based on 100 parts by mass of resin solid content, it is 0.5~30 parts by mass; [Chemical 11] (In formula (M1), R ^M1 , R ^M2 , R ^M3 , and R ^M4 are each independently representing a hydrogen atom or an organic group; R ^M5 and R ^M6 are each independently representing a hydrogen atom or an alkyl group; Ar ^M represents 2 Aromatic group of valency; A is the alicyclic group of 4~6 membered ring; R ^M7 and R ^M8 are each independently an alkyl group; mx is 1 or 2, lx is 0 or 1; R ^M9 and R ^M10 are each R ^M11 , R ^M12 , R ^M13 , and R ^M14 each independently represent a hydrogen atom or an organic group; R ^M15 each independently represent an alkyl group with a carbon number of 1 to 10, and a carbon number Alkyloxy group with 1~10 carbon number, alkylthio group with 1~10 carbon number, aryl group with 6~10 carbon number, aryloxy group with 1~10 carbon number, arylthio group with 1~10 carbon number , halogen atom, hydroxyl or mercapto; px represents an integer of 0~3; nx represents an integer of 1~20.) [Chemical 12] (In formula (M3), R ⁵⁵ each independently represent a hydrogen atom, an alkyl group with 1 to 8 carbons, or a phenyl group, and n ₅ represents an integer ranging from 1 to 10.) [Chem. 13] (In formula (M5), R ⁵⁸ each independently represent a hydrogen atom, an alkyl group with 1 to 8 carbons, or a phenyl group, R ⁵⁹ each independently represent a hydrogen atom or a methyl group, and n ₆ represents an integer of 1 or more. ) <17> A prepreg formed from a base material and a resin composition according to any one of <1> to <16>. <18> A metal foil-clad laminate comprising: at least one layer formed of the prepreg according to <17>, and a metal foil arranged on one or both sides of the layer formed of the prepreg. <19> A resin composite sheet comprising a support, and a layer formed of the resin composition according to any one of <1> to <16> arranged on the surface of the support. <20> A printed wiring board comprising an insulating layer and a conductor layer arranged on the surface of the insulating layer, the insulating layer comprising a layer selected from any one of the resin composition of <1> to <16> and At least one of the layers formed from the prepreg according to <17>. <21> A semiconductor device comprising the printed wiring board as described in <20>. [Effect of Invention]

According to the present invention, it is possible to provide novel resin compositions, prepregs, metal foil-clad laminates, resin composite sheets, printed wiring boards, and semiconductor devices.

Hereinafter, the form for carrying out the present invention (hereinafter also simply referred to as "the present embodiment") will be described in detail. On the other hand, the present embodiment below is an illustration for explaining the present invention, and the present invention is not limited to the present embodiment. In addition, "~" in this specification has the meaning which includes the numerical value described before and after it as a lower limit and an upper limit. In this specification, the values of various physical properties and characteristics are those at 23°C unless otherwise specified. In the description of the group (atomic group) in this specification, the description that does not specify substituted or unsubstituted includes a group (atomic group) without a substituent and a group (atomic group) with a substituent. For example, "alkyl" is not limited to an alkyl group without a substituent (unsubstituted alkyl group), but also includes an alkyl group with a substituent (substituted alkyl group). In this specification, descriptions that do not specify substituted and non-substituted are preferably non-substituted. In this specification, the relative permittivity means the ratio of the permittivity of a substance to the permittivity of vacuum. In addition, in this specification, the relative permittivity may be simply referred to as "permittivity". In this specification, "(meth)acrylic acid" means both of acrylic acid and methacrylic acid, or any one of them. When the standards described in this manual vary depending on the year and the measurement method etc., unless otherwise specified, they are defined as the standards as of January 1, 2021.

In this specification, the resin solid content refers to the components after excluding fillers and solvents, and its gist includes thermoplastic elastomer (A), thermoplastic elastomer (B), and thermoplastic elastomer (A) and thermoplastic elastomer (B). ) Thermosetting resin (C) that is compatible with these two elastomers, and other resins (D), silane coupling agent, and other resin additives (additives such as flame retardants, etc.) that are blended according to requirements.

The resin composition of this embodiment is characterized in that it contains a thermoplastic elastomer (A), a thermoplastic elastomer (B), and is compatible with the thermoplastic elastomer (A) and the thermoplastic elastomer (B). In the thermosetting resin (C), the thermoplastic elastomer (A) is the thermoplastic elastomer among thermoplastic elastomers containing styrene monomer units and conjugated diene monomer units and having a number average molecular weight of 50,000 or more A thermoplastic elastomer obtained by hydrogenating all of the conjugated diene bonds. The thermoplastic elastomer (B) is a thermoplastic elastomer containing styrene monomer units and conjugated diene monomer units with a number-average molecular weight of 50,000 or more. A thermoplastic elastomer obtained by hydrogenating part of the conjugated diene bonds of the thermoplastic elastomer in the body, and/or a thermoplastic elastomer with all unsaturated bonds. By constituting in this way, it is possible to obtain a resin composition excellent in moisture absorption and heat resistance while maintaining an excellent low dielectric loss tangent. In addition, in this embodiment, it is presumed that by blending a thermoplastic elastomer, flexibility can be imparted to the resin composition, and the occurrence of cracks in the obtained cured product can be effectively suppressed. Furthermore, it is presumed that thermal expansion of the cured product can be effectively suppressed by blending a thermoplastic elastomer. In particular, it is presumed that by using the thermoplastic elastomer (A), a resin composition excellent in dielectric properties can be obtained. It is presumed that this is due to the effect of reducing the polarity of the elastomer by hydrogenating the conjugated diene bond. In addition, it is presumed that the thermoplastic elastomer (B) is a large and highly polar resin with a number average molecular weight of 50,000 or more, so it is compatible with the resin component (thermoplastic elastomer (A) and the (A) and (B) The thermosetting resin (C)) has excellent compatibility and improves the moisture absorption and heat resistance of the resin composition.

＜Thermoplastic elastomer (A)＞ The resin composition of this embodiment contains a thermoplastic elastomer (A). The thermoplastic elastomer (A) is a thermoplastic elastomer containing styrene monomer units and conjugated diene monomer units and having a number-average molecular weight of 50,000 or more, in which all conjugated diene bonds of the thermoplastic elastomer are hydrogenated The resulting thermoplastic elastomer (in this specification, it may also be referred to as "hydrogenated styrene-based thermoplastic elastomer"). By containing the thermoplastic elastomer (A), the effect of being excellent in low dielectric loss tangent, crack resistance, and low thermal expansion can be achieved.

The thermoplastic elastomer (A) in this embodiment contains a styrene monomer unit. By containing a styrene monomer unit, it exists in the tendency for the compatibility with a thermosetting resin (C) to be excellent. As the styrene monomer, styrene, α-methylstyrene, p-methylstyrene, divinylbenzene (vinylstyrene), N,N-dimethyl-p-aminoethylbenzene are exemplified Ethylene, N,N-diethyl-p-aminoethylstyrene, etc. Among them, styrene, α-methylstyrene, and p-methylstyrene are preferable from the viewpoint of availability and productivity . Among these, styrene is particularly preferable. The content of styrene monomer units is preferably in the range of 10 to 50% by mass of all monomer units, more preferably in the range of 13 to 45% by mass, and still more preferably in the range of 15 to 40% by mass. When the content of the styrene monomer unit is 50% by mass or less, the adhesiveness and adhesiveness to the substrate and the like will become more favorable. Moreover, if it is 10 mass % or more, since the increase of adhesion can be suppressed, it will become difficult to generate|occur|produce residual adhesive and a trace, and the easy peelability of adhesive surfaces will become favorable, it is preferable. The thermoplastic elastomer (A) may contain only one type of styrene monomer unit, or may contain two or more types. When containing 2 or more types, it is preferable that the total amount is the said range. The method for measuring the content of the styrene monomer unit in the thermoplastic elastomer (A) of this embodiment can refer to the records in International Publication No. 2017/126469, and the content is included in this specification. The same applies to the conjugated diene monomer unit and the like described later.

The thermoplastic elastomer (A) in this embodiment contains a conjugated diene monomer unit. By containing a conjugated diene monomer unit, it tends to be excellent in low dielectric loss tangent, crack resistance, and low thermal expansion. The conjugated diene monomer is not particularly limited when it is a diene having one pair of conjugated double bonds. Conjugated diene monomers, such as 1,3-butadiene, 2-methyl-1,3-butadiene (isoprene), 2,3-dimethyl-1,3-butadiene Diene, 1,3-pentadiene, 2-methyl-1,3-pentadiene, 1,3-hexadiene, and farnesene, preferably 1,3-butadiene, and isoprene, more preferably 1,3-butadiene. The thermoplastic elastomer (A) may contain only 1 type of conjugated diene monomer unit, and may contain 2 or more types.

In the thermoplastic elastomer (A) used in this embodiment, the mass ratio of styrene monomer unit to conjugated diene monomer unit is preferably styrene monomer unit/conjugated diene monomer unit=5/95 The range of ~40/60 is more preferably the range of 7/93~37/63, further preferably the range of 10/90~35/65. When the mass ratio of the above-mentioned styrene monomer unit to the conjugated diene monomer unit is in the range of 5/95 to 40/60, the increase of adhesion can be suppressed and the high adhesive force can be maintained, and the peelability of the adhesive surfaces is good.

The thermoplastic elastomer (A) used in this embodiment is a thermoplastic elastomer in which all of the conjugated diene bonds are hydrogenated. Here, hydrogenation in its entirety means substantially hydrogenating the double bond based on the conjugated diene monomer unit in the thermoplastic elastomer (A), except that the hydrogenation rate (hydrogenation rate) is 100%. , also includes the meaning of more than 80%. The hydrogenation rate in the thermoplastic elastomer (A) used in this embodiment is preferably at least 85%, more preferably at least 90%, and still more preferably at least 95%.

The thermoplastic elastomer (A) used in this embodiment may or may not contain other monomer units other than the styrene monomer unit and the conjugated diene monomer unit. Other monomer units include monomer units derived from aromatic vinyl compounds other than styrene monomers, and the like. In the thermoplastic elastomer (A) used in this embodiment, the total amount of styrene monomer units and conjugated diene monomer units is preferably 90% by mass or more, more preferably 95% by mass or more, of all monomer units. More preferably, it is 97 mass % or more. As mentioned above, a thermoplastic elastomer (A) may contain only 1 type of styrene monomer unit and a conjugated diene monomer unit, respectively, and may contain 2 or more types. When two or more types are contained, the total amount is preferably within the above-mentioned range.

The number average molecular weight of the thermoplastic elastomer (A) used in this embodiment is 50,000 or more. When it is 50,000 or more, crack resistance tends to be excellent. The above number average molecular weight is preferably 60,000 or more, more preferably 70,000 or more, further preferably 80,000 or more, further preferably 90,000 or more, further preferably 100,000 or more, still more preferably 150,000 or more. The upper limit of the number average molecular weight of the thermoplastic elastomer (A) is preferably not more than 400,000, more preferably not more than 350,000, still more preferably not more than 300,000. There exists a tendency for the compatibility with a thermoplastic elastomer (B) and a thermosetting resin (C) to be improved more by being below the said upper limit. When the resin composition of this embodiment contains two or more kinds of thermoplastic elastomers (A), it is preferable that the number average molecular weight of these mixtures falls within the above-mentioned range.

The thermoplastic elastomer (A) used in this embodiment may be a block polymer or a random polymer. As a composition of the thermoplastic elastomer (A) used in this embodiment, SEBS (styrene-ethylene/butylene-styrene copolymer), SEPS (styrene-ethylene/propylene-styrene copolymer), etc. are illustrated.

Examples of commercially available thermoplastic elastomers (A) used in this embodiment include SEPTON (registered trademark) 2104 manufactured by Kuraray Co., Ltd., S.O.E. (registered trademark) S1606, S1613 manufactured by Asahi Kasei Co., Ltd., S1605, DYNARON (registered trademark) 9901P manufactured by JSR Co., Ltd., etc.

The content of the thermoplastic elastomer (A) in the resin composition of this embodiment is preferably at least 0.5 parts by mass, more preferably at least 1 part by mass, and still more preferably at least 2 parts by mass, based on 100 parts by mass of resin solid content. More preferably, it is 3 mass parts or more, More preferably, it is 4 mass parts or more. There exists a tendency for low dielectric loss tangent property, crack resistance, and low thermal expansion property to be further improved by being more than the said lower limit. In addition, the upper limit of the content of the thermoplastic elastomer (A) is preferably not more than 20 parts by mass, more preferably not more than 18 parts by mass, more preferably not more than 15 parts by mass, and still more preferably not more than 15 parts by mass, based on 100 parts by mass of resin solid content. It is 12 mass parts or less, More preferably, it is 10 mass parts or less. There exists a tendency for moisture absorption heat resistance to improve more by being below the said upper limit. The resin composition of this embodiment may contain only 1 type of thermoplastic elastomer (A), and may contain 2 or more types. When two or more kinds are included, the total amount is preferably within the above-mentioned range.

＜Thermoplastic elastomer (B)＞ The resin composition of this embodiment contains a thermoplastic elastomer (B). The thermoplastic elastomer (B) is a thermoplastic elastomer containing a styrene monomer unit and a conjugated diene monomer unit and having a number average molecular weight of 50,000 or more, and a part of the conjugated diene bond of the thermoplastic elastomer The thermoplastic elastomer obtained by hydrogenation, and/or, the thermoplastic elastomer with all unsaturated bonds. By containing the thermoplastic elastomer (B), the compatibility with the thermoplastic elastomer (A) is improved, and the moisture absorption and heat resistance are excellent.

The thermoplastic elastomer (B) in this embodiment contains a styrene monomer unit. By containing a styrene monomer unit, it exists in the tendency for the compatibility with a thermosetting resin (C) to be excellent. Examples of styrene monomers include styrene, α-methylstyrene, p-methylstyrene, divinylbenzene (vinylstyrene), N,N-dimethyl-p-aminoethylstyrene, Among them, N,N-diethyl-p-aminoethylstyrene is preferable from the viewpoint of availability and productivity, styrene, α-methylstyrene, and p-methylstyrene. Among these, styrene is particularly preferred. The content of the styrene monomer unit is preferably in the range of 10 to 50% by mass of all the monomer units, more preferably in the range of 13 to 45% by mass, and still more preferably in the range of 15 to 40% by mass. When the content of the styrene monomer unit is 50% by mass or less, the adhesiveness and adhesiveness to the substrate and the like will become more favorable. Moreover, if it is 10 mass % or more, since the increase of adhesion can be suppressed, adhesive residue and residue trace will not generate|occur|produce easily, and the easy peelability of adhesive surfaces tends to become favorable, it is preferable. The thermoplastic elastomer (B) may contain only one type of styrene monomer unit, or may contain two or more types. When two or more kinds are contained, the total amount is preferably within the above-mentioned range. For the determination method of the content of the styrene monomer unit in the thermoplastic elastomer (B) of this embodiment, reference may be made to the records in International Publication No. 2017/126469, and the contents thereof are incorporated into this specification. The same applies to the conjugated diene monomer unit and the like described later.

The thermoplastic elastomer (B) in this embodiment contains a conjugated diene monomer unit. By containing a conjugated diene monomer unit, it tends to be excellent in low dielectric loss tangent, crack resistance, and low thermal expansion. The conjugated diene monomer is not particularly limited when it is a diene having one pair of conjugated double bonds. Conjugated diene monomers, such as 1,3-butadiene, 2-methyl-1,3-butadiene (isoprene), 2,3-dimethyl-1,3-butadiene Diene, 1,3-pentadiene, 2-methyl-1,3-pentadiene, 1,3-hexadiene, and bacteriochlorene, preferably 1,3-butadiene, and isopentene Diene, more preferably 1,3-butadiene. The thermoplastic elastomer (B) may contain only one type of conjugated diene monomer unit, or may contain two or more types.

In the thermoplastic elastomer (B) used in this embodiment, the mass ratio of styrene monomer unit to conjugated diene monomer unit is preferably styrene monomer unit/conjugated diene monomer unit=5/95 The range of ~40/60 is more preferably the range of 7/93~37/63, further preferably the range of 10/90~35/65. When the mass ratio of the above-mentioned styrene monomer unit to the conjugated diene monomer unit is in the range of 5/95 to 40/60, the increase of adhesion can be suppressed and high adhesive force can be maintained, and the easy peelability of the adhesive surfaces becomes good.

The thermoplastic elastomer (B) used in this embodiment is a thermoplastic elastomer in which conjugated diene bonds are not hydrogenated, or only part of them are hydrogenated. Here, only a part of the hydrogenation means that a part of the double bond of the conjugated diene monomer unit in the thermoplastic elastomer (B) is hydrogenated, and means that the hydrogenation rate (hydrogenation rate) is less than 80%. The hydrogenation rate of the thermoplastic elastomer (B) used in this embodiment is more preferably 60% or less, more preferably 40% or less, still more preferably 20% or less, still more preferably 10% or less, still more preferably Below 5%.

The thermoplastic elastomer (B) used in this embodiment may or may not contain other monomer units other than the styrene monomer unit and the conjugated diene monomer unit. Other monomer units include monomer units derived from aromatic vinyl compounds other than styrene monomers, and the like. The total amount of thermoplastic elastomer (B)-based styrene monomer units and conjugated diene monomer units used in this embodiment is preferably 90% by mass or more, more preferably 95% by mass or more, of all monomer units. More preferably, it is 97% by mass or more, and still more preferably, it is 99% by mass or more. As mentioned above, a thermoplastic elastomer (B) may contain only 1 type of styrene monomer unit and a conjugated diene monomer unit, respectively, and may contain 2 or more types. When two or more types are contained, the total amount is preferably within the above-mentioned range.

The number average molecular weight of the thermoplastic elastomer (B) used in this embodiment is 50,000 or more. When it is 50,000 or more, there exists a tendency for crack resistance and the compatibility with a thermoplastic elastomer (A) to be more excellent. The above number average molecular weight is preferably 60,000 or more, more preferably 70,000 or more, further preferably 80,000 or more, further preferably 100,000 or more, further preferably 120,000 or more, still more preferably 150,000 or more. The upper limit of the number average molecular weight of the thermoplastic elastomer (B) is preferably not more than 400,000, more preferably not more than 350,000, still more preferably not more than 300,000. There exists a tendency for the compatibility with a thermosetting resin (C) to be improved more by being below the said upper limit. When the resin composition of this embodiment contains 2 or more types of thermoplastic elastomers (B), it is preferable that the number average molecular weight of these mixtures falls within the said range.

The thermoplastic elastomer (B) used in this embodiment may be a block polymer or a random polymer. As a composition of the thermoplastic elastomer (B) used in this embodiment, SBS (styrene-butadiene-styrene copolymer) etc. are illustrated.

Examples of commercially available thermoplastic elastomer (B) used in the present embodiment include TR2250 manufactured by JSR Co., Ltd., S.O.E. (registered trademark) S1609 manufactured by Asahi Kasei Co., Ltd., and the like.

The content of the thermoplastic elastomer (B) in the resin composition of this embodiment is preferably at least 0.5 parts by mass, more preferably at least 1 part by mass, and still more preferably at least 2 parts by mass, based on 100 parts by mass of resin solid content. It is still more preferably 3 parts by mass or more, and still more preferably 4 parts by mass or more. There exists a tendency for low dielectric loss tangent property, crack resistance, and low thermal expansion property to be improved more by being more than the said lower limit. In addition, the upper limit of the content of the thermoplastic elastomer (B) is preferably not more than 20 parts by mass, more preferably not more than 18 parts by mass, more preferably not more than 15 parts by mass, and still more preferably not more than 15 parts by mass, based on 100 parts by mass of the solid content of the resin. It is preferably at most 12 parts by mass, more preferably at most 10 parts by mass. There exists a tendency for moisture absorption heat resistance to improve more by being below the said upper limit. The resin composition of this embodiment may contain only 1 type of thermoplastic elastomer (B), and may contain 2 or more types. When two or more types are contained, the total amount is preferably within the above-mentioned range.

In the resin composition of this embodiment, the mass ratio of the thermoplastic elastomer (A) to the thermoplastic elastomer (B) is preferably 1:1-10. When the thermoplastic elastomer (B) is 1 part by mass or more with respect to 1 part by mass of the thermoplastic elastomer (A), the moisture absorption heat resistance tends to be further improved. In addition, when the thermoplastic elastomer (B) is 10 parts by mass or less with respect to 1 part by mass of the thermoplastic elastomer (A), low dielectric loss tangent and crack resistance tend to be further improved. The mass ratio of thermoplastic elastomer (A) to thermoplastic elastomer (B) is more preferably 1:1~9, more preferably 1:1~8, still more preferably 1:1~7, still more preferably 1 : 1~5.

The total content of the thermoplastic elastomer (A) and the thermoplastic elastomer (B) in the resin composition of the present embodiment is preferably 1 to 40 parts by mass based on 100 parts by mass of the resin solid content. There exists a tendency for low dielectric loss tangent property, crack resistance, and low thermal expansion property to be improved more by being more than the said lower limit. Moreover, there exists a tendency for moisture absorption heat resistance to improve more by being below the said upper limit. The above-mentioned total amount is more preferably 3 parts by mass or more, further preferably 5 parts by mass or more, and still more preferably 7 parts by mass or more, based on 100 parts by mass of resin solid content. Furthermore, it is preferably 10 parts by mass or more. In addition, the above-mentioned total amount is preferably 35 parts by mass or less, further preferably 30 parts by mass or less, still more preferably 25 parts by mass or less, and still more preferably 20 parts by mass or less, based on 100 parts by mass of resin solid content.

＜Compatible thermosetting resin (C)＞ The resin composition of this embodiment contains the thermosetting resin (C) compatible with two types of elastomers, a thermoplastic elastomer (A) and a thermoplastic elastomer (B). Improvement of low The effect of dielectric properties and moisture absorption heat resistance. Here, compatibility means that after the thermoplastic elastomer (A) and thermoplastic elastomer (B) are fully mixed with the thermosetting resin (C) and left to stand, there will be no obvious separation. By visual observation. The above-mentioned compatible thermosetting resin (C) is preferably a thermosetting resin containing an aromatic ring and a vinyl group. By using such a resin, affinity with the styrene monomer unit contained in a thermoplastic elastomer (A) and a thermoplastic elastomer (B) tends to be easy, and compatibility tends to be improved more. The molecular weight of the compatible thermosetting resin (C) is preferably at least 300, more preferably at least 500, more preferably at least 1,000, and still more preferably at least 1,500 in terms of the number average molecular weight Mn. The upper limit is preferably not more than 130,000, more preferably not more than 120,000, further preferably not more than 110,000, and still more preferably not more than 100,000. When two or more types of thermosetting resins (C) are contained, the number average molecular weight of the mixture is preferably within the above-mentioned range.

In this embodiment, the above-mentioned compatible thermosetting resin (C) preferably includes a polymer selected from a polymer having a constituent unit represented by formula (V), and a polyphenylene ether having a carbon-carbon unsaturated double bond at the end One or more of the group consisting of compounds. If such a resin is used, the effects of the present invention can be exhibited more effectively. [chemical 14] (In the formula (V), Ar represents an aromatic hydrocarbon linking group. * represents a bonding position.)

Moreover, the said compatible thermosetting resin (C) may contain the structural unit derived from maleic anhydride. For the details of such resins, refer to the records of International Publication No. 2017/209108, the contents of which are incorporated into this specification. Moreover, the said compatible thermosetting resin (C) may contain the structural unit derived from the compound which has an acid group and an acid anhydride group.

In the resin composition of this embodiment, when the resin solid content in the resin composition is 100 parts by mass, the content of the above-mentioned compatible thermosetting resin (C) is preferably 10 to 90 parts by mass. The lower limit of the content of the above-mentioned compatible thermosetting resin (C) is preferably 15 parts by mass or more, more preferably 20 parts by mass or more, when the resin solid content in the resin composition is 100 parts by mass. More preferably, it is 25 mass parts or more. By making the content of the above-mentioned compatible thermosetting resin (C) more than the above-mentioned lower limit, low dielectric properties can be achieved, and particularly low dielectric loss tangent can be effectively achieved. On the other hand, the upper limit of the content of the above-mentioned compatible thermosetting resin (C) is preferably 80 parts by mass or less, more preferably 60 parts by mass when the resin solid content in the resin composition is 100 parts by mass. Parts or less, more preferably 50 parts by mass or less, further preferably 40 parts by mass or less. By being below the said upper limit, the metal foil peeling strength of the hardened|cured material obtained can be improved effectively. The above-mentioned compatible thermosetting resin (C) may be contained in the resin composition only by one type, or may contain two or more types. When two or more types are contained, the total amount is preferably within the above-mentioned range.

<<Polymer having a structural unit represented by formula (V)>> The resin composition of the present embodiment preferably contains a polymer having a structural unit represented by formula (V). By containing the polymer having the structural unit represented by the formula (V), a resin composition having more excellent low dielectric properties (low dielectric coefficient, low dielectric loss tangent) can be obtained. [chemical 15] (In formula (V), Ar represents an aromatic hydrocarbon linking group. * Indicates a bonding position.) The aromatic hydrocarbon linking group may be composed only of aromatic hydrocarbons which may have substituents, or may be composed of The group composed of a combination of an aromatic hydrocarbon which may have a substituent and another linking group is preferably a group composed only of an aromatic hydrocarbon which may also have a substituent. In addition, the substituents that aromatic hydrocarbons may also have include substituent Z (for example, alkyl having 1 to 6 carbons, alkenyl having 2 to 6 carbons, alkynyl having 2 to 6 carbons, alkynyl having 1 to 6 carbons, etc. 6 alkoxy group, hydroxyl group, amino group, carboxyl group, halogen atom, etc.). In addition, the above-mentioned aromatic hydrocarbon preferably has no substituent. An aromatic hydrocarbon linking group is usually a divalent linking group.

Specifically, the aromatic hydrocarbon linking group is preferably phenylene, naphthalenediyl, anthracenediyl, phenanthrene diyl, biphenyldiyl, and fenestyl diyl, which may also have substituents. The base of the phenylene group. The substituents are exemplified by the above-mentioned substituent Z, but the above-mentioned phenylene group and the like are preferably those without a substituent.

The structural unit represented by the formula (V) preferably includes at least one of the structural unit represented by the following formula (V1), the structural unit represented by the following formula (V2), and the structural unit represented by the following formula (V3). In addition, * in the following formula represents a bonding position. In addition, the structural units represented by formulas (V1) to (V3) may be collectively referred to as "structural unit (a)" below

[chemical 16] In the formulas (V1)~(V3), L ¹ is an aromatic hydrocarbon linking group (preferably having 6~22 carbons, more preferably 6~18, further preferably 6~10). Specifically, phenylene groups which may have substituents, naphthalenediyl groups, anthracenediyl groups, phenanthrene diyl groups, biphenylenediyl groups, and fenylenediyl groups may be mentioned, among which phenylene groups which may also have substituents are preferred. The substituents are exemplified by the above-mentioned substituent Z, but the above-mentioned phenylene group and the like are preferably those without a substituent. The compound forming the constituent unit (a) is preferably a divinyl aromatic compound, such as divinylbenzene, bis(1-methylvinyl)benzene, divinylnaphthalene, divinylanthracene, divinyl Biphenyl, divinylphenanthrene, etc. Among them, divinylbenzene is particularly preferred. One type of these divinyl aromatic compounds may be used, or two or more types may be used as required.

The polymer having the structural unit represented by the formula (V) may be a homopolymer of the structural unit (a) as described above, or may be a copolymer with a structural unit derived from another monomer. When the polymer having the constituent units represented by formula (V) is a copolymer, the copolymerization ratio is preferably at least 5 mole % of the constituent unit (a), more preferably at least 10 mole %, further preferably at least 15 mole % %above. The upper limit is preferably not more than 90 mol %, more preferably not more than 85 mol %, further preferably not more than 80 mol %, still more preferably not more than 70 mol %, and still more preferably not more than 60 mol % % or less, more preferably less than 50 mole %, more preferably less than 40 mole %, especially preferably less than 30 mole %, or less than 25 mole %.

As a structural unit derived from another monomer, the structural unit (b) derived from the aromatic compound (monovinyl aromatic compound) which has one vinyl group is illustrated.

The structural unit (b) derived from a monovinyl aromatic compound is preferably a structural unit represented by the following formula (V4).

[chemical 17] In the formula (V4), L ² is an aromatic hydrocarbon linking group, and ideal specific examples include the above-mentioned examples of L ¹ . R ^V1 is a hydrogen atom or a hydrocarbon group with 1 to 12 carbons (preferably an alkyl group). When R ^V1 is a hydrocarbon group, its carbon number is preferably 1-6, more preferably 1-3. R ^V1 and L ² may also have the substituent Z mentioned above.

When the polymer having the structural unit represented by the formula (V) is a copolymer containing the structural unit (b) derived from a monovinyl aromatic compound, examples of the monovinyl aromatic compound include styrene, vinyl naphthalene , Vinyl biphenyl and other vinyl aromatic compounds; o-methylstyrene, m-methylstyrene, p-methylstyrene, o-, p-dimethylstyrene, o-ethylvinylbenzene, m-ethyl Alkyl-substituted vinyl aromatic compounds such as vinylbenzene, p-ethylvinylbenzene, methylvinylbiphenyl, ethylvinylbiphenyl, etc. The monovinyl aromatic compound exemplified here may also have the substituent Z mentioned above as appropriate. In addition, these monovinyl aromatic compounds may be used by 1 type, and may use 2 or more types.

When the polymer having the structural unit represented by the formula (V) is a copolymer containing the structural unit (b), the copolymerization ratio of the structural unit (b) is preferably 10 mol% or more, more preferably 15 mol% or more, Furthermore, it may be 20 mol% or more, 30 mol% or more, 40 mol% or more, 50 mol% or more, 60 mol% or more, 70 mol% or more, or 75 mol% or more. The upper limit is preferably not more than 98 mol%, more preferably not more than 90 mol%, and still more preferably not more than 85 mol%.

The polymer having the structural unit represented by the formula (V) may have other structural units than the structural unit (a) and the structural unit (b). As another structural unit, the structural unit (c) etc. which originate in a cycloolefin compound are mentioned, for example. As a cycloolefin compound, the hydrocarbon which has a double bond in a ring structure is mentioned. Specifically, in addition to monocyclic cyclic olefins such as cyclobutene, cyclopentene, cyclohexene, and cyclooctene, those having a noramphene ring structure such as noramphene and dicyclopentadiene can also be used. Compounds, indene, acenaphthene and other aromatic ring condensed cycloalkene compounds, etc. Examples of norcamphene compounds include those described in paragraphs 0037 to 0043 of JP-A-2018-39995, and these contents are incorporated in this specification. In addition, the cycloolefin compound exemplified here may further have the substituent Z described above.

When the polymer having the structural unit represented by the formula (V) is a copolymer containing the structural unit (c), the copolymerization ratio of the structural unit (c) is preferably 10 mol% or more, more preferably 20 mol% or more , and further preferably more than 30 mol%. The upper limit is preferably 90 mol% or less, more preferably 80 mol% or less, more preferably 70 mol% or less, may be 50 mol% or less, and may be 30 mol% or less.

A polymer having a structural unit represented by formula (V) may further contain a structural unit (d) derived from a different polymerizable compound (hereinafter also referred to as another polymerizable compound). As another polymeric compound (monomer), the compound containing 3 vinyl groups is mentioned, for example. Specifically, 1,3,5-trivinylbenzene, 1,3,5-trivinylnaphthalene, and 1,2,4-trivinylcyclohexane are mentioned. Or, ethylene glycol diacrylate, butadiene, etc. are mentioned. The copolymerization ratio of the structural unit (d) derived from another polymerizable compound is preferably at most 30 mol%, more preferably at most 20 mol%, and still more preferably at most 10 mol%.

As an embodiment of the polymer having the structural unit represented by the formula (V), a polymer in which the structural unit (a) is essential and contains at least one of the structural units (b) to (d) is exemplified. In addition, an aspect in which the total of the structural units (a) to (d) accounts for 95 mol% or more, further 98 mol% or more of all the structural units is exemplified. As another embodiment of the polymer having the structural unit represented by the formula (V), it is preferable that the structural unit (a) is essential and among all the structural units excluding the terminal, the structural unit containing an aromatic ring is 90 mole. mol% or more, more preferably 95 mol% or more, or 100 mol%. In addition, when calculating the mole % with respect to all the structural units, 1 structural unit is defined as being derived from 1 molecule of monomer (for example, diethylene aromatic compounds, monovinyl aromatic compounds, etc.).

The production method of the polymer having the structural unit represented by formula (V) is not particularly limited, and it can be a common method, for example, making a raw material containing a divinyl aromatic compound (according to the presence of a Lewis acid catalyst) demand, the coexistence of monovinyl aromatic compounds, cycloolefin compounds, etc.) polymerization. As the Lewis acid catalyst, metal fluorides such as boron trifluoride or complexes thereof can be used.

The structure of the chain terminal of the polymer having the constituent unit represented by the formula (V) is not particularly limited, and the description of the group derived from the above divinyl aromatic compound includes a structure of the following formula (E1). In addition, L ¹ in the formula (E1) is the same as defined in the above formula (V1). ＊Indicates the bonding position. ＊-CH=CH-L ¹ -CH=CH ₂ (E1)

When a group derived from a monovinyl aromatic compound becomes a chain terminal, a structure adopting the following formula (E2) is exemplified. L ² and R ^V1 in the formula have the same meanings as those defined in the above formula (V4). ＊Indicates the bonding position. ＊-CH=CH-L ² -R ^V1 (E2)

The molecular weight of the polymer having a constituent unit represented by formula (V) is preferably at least 300, more preferably at least 500, further preferably at least 1,000, and more preferably at least 1,500 in terms of the number average molecular weight Mn. The upper limit of the number average molecular weight Mn is preferably 130,000 or less, more preferably 120,000 or less, further preferably 110,000 or less, still more preferably 100,000 or less. The molecular weight of the polymer having a structural unit represented by formula (V) is preferably 1,000 or more, more preferably 2,000 or more, and still more preferably 3,000 or more, in terms of weight average molecular weight Mw. By being more than the above lower limit, the excellent low dielectric properties of the polymer having the structural unit represented by the formula (V), especially the Df and the dielectric properties after moisture absorption, can be effectively exerted in the resin composition. In the hardening of things. The upper limit of the weight average molecular weight Mw is preferably at most 160,000, more preferably at most 150,000, further preferably at most 140,000, and still more preferably at most 130,000. When lamination|stacking a prepreg or a resin sheet on a circuit formation board|substrate by being below the said upper limit, it exists in the tendency for embedding failure not to generate|occur|produce easily. The monodispersity (Mw/Mn) represented by the ratio of the weight average molecular weight Mw to the number average molecular weight Mn is preferably 100 or less, more preferably 50 or less, further preferably 20 or less. The lower limit of the monodispersity is practically 1.1 or more, and 10 or more can satisfy the required performance. The above-mentioned Mw and Mn were measured in accordance with the description of the Examples described later. When the resin composition of this embodiment contains two or more polymers having structural units represented by the formula (V), Mw, Mn, and Mw/Mn of the mixture are preferably within the above-mentioned ranges.

The vinyl equivalent of the polymer having the constituent unit represented by formula (V) is preferably at least 200 g/eq., more preferably at least 230 g/eq., and still more preferably at least 250 g/eq. In addition, the equivalent weight of the above-mentioned vinyl group is preferably 1200 g/eq. or less, more preferably 1000 g/eq. or less, further preferably 800 g/eq. or less, 600 g/eq. the following. By being more than the said lower limit, there exists a tendency for the storage stability of a resin composition to improve and the fluidity of a resin composition to improve. Therefore, it tends to improve formability, prevent voids from being generated during formation of a prepreg, and obtain a more reliable printed wiring board. On the other hand, there exists a tendency for the moisture absorption heat resistance of the hardened|cured material obtained to improve by being below the said upper limit.

In addition, it is preferable that the cured product of the polymer having the structural unit represented by the formula (V) used in this embodiment has excellent dielectric properties. For example, the cured product of the polymer having the constituent units represented by the formula (V) used in this embodiment should preferably have a relative permittivity (Dk) at 10 GHz of 2.80 or less as measured by the cavity resonator perturbation method. It is preferably 2.60 or less, more preferably 2.50 or less, and still more preferably 2.40 or less. In addition, the lower limit of the above-mentioned relative permittivity is, for example, practically 1.80 or more. In addition, the cured product of the polymer having the structural unit represented by the formula (V) used in this embodiment preferably has a dielectric loss tangent (Df) at 10 GHz measured by the cavity resonator perturbation method of 0.0030 or less. It is preferably 0.0020 or less, more preferably 0.0010 or less. In addition, the lower limit value of the above-mentioned dielectric loss tangent is, for example, practically 0.0001 or more. The dielectric loss tangent (Df) was measured according to the method described in the examples described later. The relative permittivity (Dk) is also measured according to the method for measuring Df in the embodiment.

Regarding the polymer having the structural unit represented by the formula (V) in this specification, refer to the compounds described in paragraphs 0029 to 0058 of International Publication No. 2017/115813 and their synthesis reaction conditions, etc., Japanese Patent Application Laid-Open No. 2018-039995 Compounds and synthesis reaction conditions described in paragraphs 0013 to 0058 of the publication, compounds and synthesis reaction conditions thereof described in paragraphs 0008 to 0043 of JP-A No. 2018-168347, JP-A No. 2006-070136 Compounds described in paragraphs 0014 to 0042 and their synthesis reaction conditions, etc., compounds described in paragraphs 0014 to 0061 of JP-A-2006-089683, and their synthesis reaction conditions, etc., paragraph 0008 of JP-A-2008-248001 The compounds described in ~0036 and their synthesis reaction conditions, etc., are incorporated into this specification.

In the case where the resin composition of this embodiment contains a polymer having a structural unit represented by formula (V), when the resin solid content in the resin composition is 100 parts by mass, the amount of polymer having a structural unit represented by formula (V) The content of the polymer is preferably 5-50 parts by mass. The lower limit of the content of the polymer having a constituent unit represented by formula (V) is preferably 10 parts by mass or more, more preferably 15 parts by mass or more, when the resin solid content in the resin composition is 100 parts by mass, It may be 20 mass parts or more, and may be 25 mass parts or more. By setting the content of the polymer having the structural unit represented by the formula (V) to be equal to or greater than the above lower limit, low dielectric properties, especially low dielectric loss tangent can be effectively achieved. On the other hand, the upper limit of the content of the polymer having the structural unit represented by formula (V) is preferably 45 parts by mass or less, more preferably 40 parts by mass, when the resin solid content in the resin composition is 100 parts by mass. It is not more than 35 parts by mass, more preferably not more than 35 parts by mass. Moreover, the metal foil peeling strength of the hardened|cured material obtained can be improved effectively by being below the said upper limit. The polymer having the structural unit represented by the formula (V) may contain only one type, or may contain two or more types in the resin composition. When containing 2 or more types, it is preferable that a total amount shall be the said range.

＜<Polyphenylene ether compound with carbon-carbon unsaturated double bond at the end>> The resin composition of this embodiment may also contain a polyphenylene ether compound having a carbon-carbon unsaturated double bond at the end. The polyphenylene ether compound having a carbon-carbon unsaturated double bond at the end preferably has a group selected from the group consisting of a (meth)acrylic group, a maleimide group, and a vinylbenzyl group at the end. polyphenylene ether compound. In addition, the polyphenylene ether compound having a carbon-carbon unsaturated double bond at the end is preferably a polyphenylene ether compound having two or more carbon-carbon unsaturated double bonds at the end. By using these polyphenylene ether compounds, there exists a tendency for the low dielectric characteristic of a printed wiring board to be improved more effectively. These will be described in detail below.

The polyphenylene ether compound having a carbon-carbon unsaturated double bond at the terminal is an example of a compound having a phenylene ether skeleton represented by the following formula (X1).

[chemical 18] (In formula (X1), R ²⁴ , R ²⁵ , R ²⁶ , and R ²⁷ may be the same or different, and represent an alkyl group, aryl group, halogen atom, or hydrogen atom with 6 or less carbon atoms.)

The polyphenylene ether compound having a carbon-carbon unsaturated double bond at the end may further contain a repeating unit represented by formula (X2): [Chem. 19] (In formula (X2), R ²⁸ , R ²⁹ , R ³⁰ , R ³⁴ , and R ³⁵ may be the same or different, and represent an alkyl or phenyl group with 6 or less carbon atoms. ^{R 31} , R ³² , and R ³³ The system may be the same or different, and is a hydrogen atom, an alkyl group or a phenyl group with a carbon number of 6 or less.), and/or, a repeating unit represented by formula (X3): [Chemical 20] (In formula (X3), R ³⁶ , R ³⁷ , R ³⁸ , R ³⁹ , R ⁴⁰ , R ⁴¹ , R ⁴² , and R ⁴³ may be the same or different, and are hydrogen atoms, alkyl groups with 6 or less carbon atoms, or Phenyl. -A- is a straight-chain, branched or cyclic divalent hydrocarbon group with carbon number less than 20.).

The polyphenylene ether compound having a carbon-carbon unsaturated double bond at the terminal is preferably a modified polyphenylene ether compound obtained by functionalizing part or all of the terminal with an ethylenically unsaturated group (hereinafter sometimes referred to as "Modified polyphenylene ether compound (g)") is more preferably one having two or more terminal groups selected from the group consisting of (meth)acrylic group, maleimide group, and vinylbenzyl group Based modified polyphenylene ether compound. By using such a modified polyphenylene ether compound (g), the dielectric loss tangent (Df) of the cured product of the resin composition can be made smaller. These can be used 1 type or in combination of 2 or more types.

Examples of the modified polyphenylene ether compound (g) include compounds represented by formula (OP-1). [chem 21] (In formula (OP-1), X represents an aromatic group, -(YO)n ₂ - represents a polyphenylene ether structure, R ¹ , R ² , and R ³ each independently represent a hydrogen atom, an alkyl group, an alkenyl group or alkynyl, n ₁ represents an integer of 1 to 6, n ₂ represents an integer of 1 to 100, and n ₃ represents an integer of 1 to 4.) When n ₂ and/or n ₃ are an integer of 2 or more, n ₂ constitute Each of the unit (YO) and/or n _three constituent units may be the same or different. n ₃ is preferably 2 or more, more preferably 2.

The modified polyphenylene ether compound (g) in this embodiment is preferably a compound represented by formula (OP-2). [chem 22] Here, -(OXO)- is preferably formula (OP-3): [Chemical 23] (In formula (OP-3), R ⁴ , R ⁵ , R ⁶ , R ¹⁰ , and R ¹¹ may be the same or different, and are alkyl groups or phenyl groups with 6 or less carbon atoms. ^{R 7} , R ⁸ , and R ⁹ may be the same or different, and are hydrogen atoms, alkyl groups or phenyl groups with a carbon number of 6 or less.) and/or formula (OP-4): [Chemical 24] (In formula (OP-4), R ¹² , R ¹³ , R ¹⁴ , R ¹⁵ , R ¹⁶ , R ¹⁷ , R ¹⁸ , and R ¹⁹ may be the same or different, and are hydrogen atoms and alkyl groups with 6 or less carbon atoms Or phenyl. -A- is a linear, branched or cyclic divalent hydrocarbon group with carbon number less than 20.).

In addition, -(YO)- is preferably formula (OP-5): [Chemical 25] (In the formula (OP-5), R ²⁰ and R ²¹ may be the same or different, and are alkyl groups or phenyl groups with 6 or less carbons. ^{R 22} and R ²³ may be the same or different, and are hydrogen atoms with 6 carbons. The following alkyl or phenyl.). In formula (OP-2), at least one of a and b is not 0, and represents an integer of 0 to 100, preferably an integer of 0 to 50, more preferably an integer of 1 to 30. When a and/or b are an integer of 2 or more, two or more -(YO)-s may be independently arranged in one structure, or two or more structures may be arranged in a block or random manner arrangement.

For -A- in formula (OP-4), for example, methylene, ethylene, 1-methylethylene, 1,1-propylene, 1,4-phenylene bis (1-methylethylene) group, 1,3-phenylenebis(1-methylethylene) group, cyclohexylene, phenylmethylene, naphthylmethylene, 1-phenyl Divalent organic groups such as ethylene, but not limited to these.

Among the above-mentioned modified polyphenylene ether compounds (g), R ⁴ , R ⁵ , R ⁶ , R ¹⁰ , R ¹¹ , R ²⁰ , and R ²¹ are preferably alkyl groups with 3 or less carbon atoms, and R ⁷ , R ⁸ , R ⁹ , R ¹² , R ¹³ , R ¹⁴ , R ¹⁵ , R ¹⁶ , R ¹⁷ , R ¹⁸ , R ¹⁹ , R ²² , and R ²³ are polyphenylene ether compounds that are hydrogen atoms or alkyl groups with 3 or less carbon atoms, Especially suitable for -(OXO)-series formula (OP-9), formula (OP-10), and/or formula (OP-11) represented by formula (OP-3) or formula (OP-4), with -(YO)-series formula (OP-12) or formula (OP-13) represented by formula (OP-5). When a and/or b are an integer of 2 or more, two or more -(YO)- are each independently arranged in two or more structures of formula (OP-12) and/or formula (OP-13), or It can be a block or random arrangement of formula (OP-12) and formula (OP-13).

[chem 26] [chem 27] (In formula (OP-10), R ⁴⁴ , R ⁴⁵ , R ⁴⁶ , and R ⁴⁷ may be the same or different, and are hydrogen atoms or methyl groups. -B- is a straight chain, branched or cyclic chain with 20 or less carbon atoms The divalent hydrocarbon group.) -B- as a specific example is the same thing as the specific example of -A- in formula (OP-4). [chem 28] (In formula (OP-11), -B- is a straight-chain, branched or cyclic divalent hydrocarbon group with carbon number less than 20.) -B- as a specific example can be listed with -A in formula (OP-4) The specific examples of - are the same. [chem 29] [chem 30]

The polyphenylene ether compound having a carbon-carbon unsaturated double bond at the terminal can be produced by a known method, and a commercially available product can also be used. As a commercial item, "SA9000" by SABIC Innovative Plastics is mentioned, for example as a modified polyphenylene ether compound having a methacrylic group terminal. In addition, examples of the modified polyphenylene ether compound having a vinylbenzyl group at the terminal include "OPE-2St1200" and "OPE-2st2200" manufactured by Mitsubishi Gas Chemical. In addition, as a modified polyphenylene ether compound having a vinylbenzyl group terminal, a polyphenylene ether compound having a hydroxyl group terminal such as “SA90” manufactured by SABIC Innovative Plastics Co., Ltd. modified with vinylbenzyl chloride can also be used. Derived from vinylbenzyl.

In addition, for detailed descriptions of polyphenylene ether compounds having a carbon-carbon unsaturated double bond at the end, refer to Japanese Patent Application Publication No. 2006-028111, Japanese Patent Application Publication No. 2018-016709, International Publication No. 2019-138992, International The description of Publication No. 2022-054303 is incorporated into this specification.

The polystyrene-equivalent number average molecular weight (details (following the method described in the examples described later) is preferably more than 500 and less than 3,000. When the number average molecular weight is 500 or more, the resin composition of this embodiment tends to suppress sticking more when it is formed into a coating film. When the number average molecular weight is 3,000 or less, there exists a tendency for the solubility with respect to a solvent to improve more. In addition, the polyphenylene ether compound having a carbon-carbon unsaturated double bond at the end (preferably a modified polyphenylene ether compound (g)) is the polystyrene-equivalent weight average molecular weight obtained by GPC (details are based on the following examples) The method described) is preferably from 800 to 10,000, more preferably from 800 to 5,000. By being more than the above-mentioned lower limit, the relative permittivity (Dk) and dielectric loss tangent (Df) of the cured product of the resin composition tend to be lower, and by being below the above-mentioned upper limit, there are There is a tendency to improve the solubility, low viscosity and formability of the resin composition to solvents when making varnishes and the like. In addition, in the case of the modified polyphenylene ether compound (g), the carbon-carbon unsaturated double bond equivalent at the terminal is 400-5000 g per one carbon-carbon unsaturated double bond, more preferably 400-2500 g. There exists a tendency for the relative permittivity (Dk) and dielectric loss tangent (Df) of the hardened|cured material of a resin composition to become lower by being more than the said lower limit. There exists a tendency for the solubility of the resin composition with respect to a solvent, low viscosity, and moldability to be improved more by being below the said upper limit.

In the case where the resin composition of this embodiment contains a polyphenylene ether compound having a carbon-carbon unsaturated double bond at the end, the lower limit of the content of the polyphenylene ether compound having a carbon-carbon unsaturated double bond at the end is relatively The resin solid content in the resin composition is preferably 1 part by mass or more, more preferably 3 parts by mass or more, further preferably 5 parts by mass or more, and still more preferably 7 parts by mass or more, per 100 parts by mass of the resin solid content. There exists a tendency for the low water absorption and low dielectric characteristics (Dk and/or Df) of the hardened|cured material obtained to be improved more by being more than the said lower limit. In addition, the upper limit of the content of the polyphenylene ether compound having a carbon-carbon unsaturated double bond at the terminal is preferably 70 parts by mass or less, more preferably 60 parts by mass, based on 100 parts by mass of the resin solid content in the resin composition. It is preferably not more than 50 parts by mass, more preferably not more than 40 parts by mass, and may be not more than 30 parts by mass or not more than 25 parts by mass. There exists a tendency for the copper foil peeling strength of the hardened|cured material obtained to be improved more by being below the said upper limit. The resin composition in this embodiment may contain only one type of polyphenylene ether compound having a carbon-carbon unsaturated double bond at the terminal, or may contain two or more types. When two or more types are contained, the total amount is preferably within the above-mentioned range.

＜Other resins (D)＞ The resin composition of this embodiment may further contain other resin (D). As far as other resins (D) are concerned, it is preferable to contain a compound selected from maleimide compounds, cyanate compounds, epoxy compounds, phenolic compounds, alkenyl-substituted nadiimide (nadiimide) compounds, oxygen At least one selected from the group consisting of heterocyclobutane resins and benzodiazepine compounds, preferably selected from the group consisting of cyanate compounds, maleimide compounds, and epoxy compounds One or more of the other resins (D). Such other resins (D) are not essential components to achieve the effects of the present invention, but by blending these components, various physical properties can be imparted to the resin composition or cured product, or the resin composition or cured product can be further improved. Dielectric properties, moisture absorption and heat resistance, etc. These other resins (D) may be used individually by 1 type, and may use 2 or more types together.

＜＜Cyanate compound＞＞ The resin composition of this embodiment may also contain a cyanate compound. As long as the cyanate compound contains more than one cyanate group (cyanooxy group) in one molecule (preferably 2~12, more preferably 2~6, further preferably 2~4, further preferably 2 or 3 , The compound that is more preferably 2) is not particularly limited, and compounds generally used in the field of printed wiring boards can be widely used. In addition, the cyanate compound is preferably a compound in which a cyanate group is directly bonded to an aromatic skeleton (aromatic ring). As the cyanate compound, there may be mentioned, for example, those selected from the group consisting of phenol novolac type cyanate compounds, naphthol aralkyl type cyanate compounds (naphthol aralkyl type cyanate esters), naphthyl ether type cyanate compounds, Ester compound, biphenyl aralkyl type cyanate compound, xylene resin type cyanate compound, trisphenol methane type cyanate compound, adamantane skeleton type cyanate compound, bisphenol M type cyanate compound , a bisphenol A type cyanate compound, and a diallyl bisphenol A type cyanate compound and at least one selected from the group consisting of. Among them, from the viewpoint of improving the low water absorption of the obtained cured product, it is preferable to select from the group consisting of phenol novolak type cyanate ester compound, naphthol aralkyl type cyanate ester compound, naphthyl ether type In the group consisting of cyanate compounds, xylene resin type cyanate compounds, bisphenol M type cyanate compounds, bisphenol A type cyanate compounds, and diallyl bisphenol A type cyanate compounds At least one of them is more preferably a naphthol aralkyl type cyanate compound. These cyanate compounds can be prepared by known methods, and commercially available items can also be used. In addition, cyanate compounds having a naphthol aralkyl skeleton, naphthyl ether skeleton, xylene skeleton, trisphenolmethane skeleton, or adamantane skeleton have relatively large functional group equivalents, and unreacted cyanic acid Since there are few ester groups, cured products using these resin compositions tend to have better low water absorption properties. Moreover, since it has an aromatic frame|skeleton or an adamantane frame|skeleton, there exists a tendency for plating adhesiveness to improve more.

The resin composition of this embodiment preferably contains a cyanate compound within the range that does not impair the effect of the present invention. When the resin composition of this embodiment contains a cyanate compound, the lower limit of the content is preferably 0.1 parts by mass or more, more preferably 2 parts by mass or more, relative to 100 parts by mass of the resin solid content in the resin composition. , It can also be more than 5 parts by mass. When the content of the cyanate compound is 0.1 parts by mass or more, the heat resistance, combustion resistance, chemical resistance, low relative permittivity, low dielectric loss tangent, and insulation of the obtained cured product tend to be improved. The upper limit of the content of the cyanate compound is preferably 70 parts by mass or less, more preferably It is 50 mass parts or less, More preferably, it is 40 mass parts or less, More preferably, it is 30 mass parts or less, More preferably, it is 20 mass parts or less. The resin composition in this embodiment may contain only one type of cyanate ester compound, or may contain two or more types. When two or more types are contained, the total amount is preferably within the above-mentioned range.

<<maleimide compound>> The resin composition of this embodiment may contain a maleimide compound. The resin composition of this embodiment, as long as it has one or more (preferably 2 to 12, more preferably 2 to 6, more preferably 2 to 4, still more preferably 2 or 3, still more preferably 2) The maleimide-based compound is not particularly limited, and can be widely used as a compound generally used in the field of printed wiring boards. In this embodiment, the maleimide compound preferably comprises a compound selected from the compounds represented by the formula (M0), the compound represented by the formula (M1), the compound represented by the formula (M2), the compound represented by the formula (M3), the compound represented by the formula The compound represented by (M4) and the group consisting of the compound represented by formula (M5) are more preferably one or more selected from the group consisting of the compound represented by formula (M0), the compound represented by formula (M1), the compound represented by formula One or more of the compound represented by the formula (M3), the compound represented by the formula (M4), and the compound represented by the formula (M5) are selected from the group consisting of the compound represented by the formula (M1), the compound represented by the formula The compound represented by (M3) and the compound represented by the formula (M5) are preferably one or more of the group consisting of the compound represented by the formula (M1) and/or the compound represented by the formula (M3). When these maleimide compounds are used in materials for printed wiring boards (for example, metal-clad laminates), excellent heat resistance can be imparted. [chem 31] (In formula (M0), R ⁵¹ each independently represent a hydrogen atom, an alkyl group with 1 to 8 carbons, or a phenyl group, R ⁵² each independently represent a hydrogen atom or a methyl group, and n ₁ represents an integer of 1 or more. ) R ⁵¹ is preferably each independently selected from the group consisting of a hydrogen atom, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, and phenyl One of the group, more preferably a hydrogen atom and/or a methyl group, more preferably a hydrogen atom. R ⁵² is preferably methyl. n ₁ is preferably an integer of 1 to 10, more preferably an integer of 1 to 5, more preferably an integer of 1 to 3, still more preferably 1 or 2, still more preferably 1. Specifically, the following compounds can be cited as preferred examples of the formula (M0). [chem 32] In the above formula, R ⁸ each independently represent a hydrogen atom, a methyl group or an ethyl group, preferably a methyl group.

The compound represented by the formula (M0) may be a mixture of two or more types other than only one type. Examples of mixtures include mixtures of compounds with different n ₁ , mixtures of compounds with different types of substituents for R ⁵¹ and/or R ⁵² , the bond between the maleimide group of the benzene ring and the oxygen atom Mixtures of compounds having different knot positions (meta, para, ortho), and mixtures of compounds combining two or more of the above differences, etc. Hereinafter, the same applies to formulas (M1) to (M5). [chem 33] (In formula (M1), R ^M1 , R ^M2 , R ^M3 , and R ^M4 are each independently representing a hydrogen atom or an organic group; R ^M5 and R ^M6 are each independently representing a hydrogen atom or an alkyl group; Ar ^M represents 2 Aromatic group of valency; A is the alicyclic group of 4~6 membered ring; R ^M7 and R ^M8 are each independently an alkyl group; mx is 1 or 2, lx is 0 or 1; R ^M9 and R ^M10 are each R ^M11 , R ^M12 , R ^M13 , and R ^M14 each independently represent a hydrogen atom or an organic group; R ^M15 each independently represent an alkyl group with a carbon number of 1 to 10, and a carbon number Alkyloxy group with 1~10 carbon number, alkylthio group with 1~10 carbon number, aryl group with 6~10 carbon number, aryloxy group with 1~10 carbon number, arylthio group with 1~10 carbon number , halogen atom, hydroxyl or mercapto; px represents an integer of 0~3; nx represents an integer of 1~20)

R ^M1 , R ^M2 , R ^M3 , and R ^M4 in the formula each independently represent a hydrogen atom or an organic group. The organic group here is preferably an alkyl group, more preferably an alkyl group with 1 to 12 carbons, further preferably an alkyl group with 1 to 6 carbons, and further preferably a methyl group, an ethyl group, a propyl group, or a butyl group, wherein Especially preferred is methyl. R ^M1 and R ^M3 are each independently preferably an alkyl group, and R ^M2 and R ^M4 are preferably a hydrogen atom. R ^M5 and R ^M6 each independently represent a hydrogen atom or an alkyl group, preferably an alkyl group. 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, further 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 naphthalene diyl group, a phenanthrene diyl group, and an anthracene diyl group, more preferably a phenylene group, and even more preferably a m-phenylene group. Ar ^M may also have a substituent, and the substituent is preferably an alkyl group, more preferably an alkyl group having 1 to 12 carbon atoms, further preferably an alkyl group having 1 to 6 carbon atoms, and even more preferably a methyl group or an ethyl group. , propyl, butyl, especially methyl. However, Ar ^M is preferably unsubstituted. A is an alicyclic group with 4 to 6 members, more preferably a 5-membered alicyclic group (preferably a group that combines a benzene ring to form an indan ring). R ^M7 and R ^M8 are each independently 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 especially preferably a methyl group. mx is 1 or 2, preferably 2. lx is 0 or 1, preferably 1. R ^M9 and R ^M10 each independently represent a hydrogen atom or an alkyl group, more preferably an alkyl group. 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, further 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 ^M14 each independently represent a hydrogen atom or an organic group. The organic group here is preferably an alkyl group, more preferably an alkyl group with 1 to 12 carbons, further preferably an alkyl group with 1 to 6 carbons, and further preferably a methyl group, an ethyl group, a propyl group, or a butyl group, wherein Especially preferred is methyl. R ^M12 and R ^M13 are each independently preferably an alkyl group, and R ^M11 and R ^M14 are preferably a hydrogen atom. R ^M15 each independently represents an alkyl group with 1 to 10 carbons, an alkyloxy group with 1 to 10 carbons, an alkylthio group with 1 to 10 carbons, an aryl group with 6 to 10 carbons, and an alkyl group with 1 to 10 carbons. An aryloxy group with ~10 carbons, an arylthio group with 1 to 10 carbons, a halogen atom, a hydroxyl group or a mercapto group, preferably an alkyl group with 1 to 4 carbons, a cycloalkyl group with 3 to 6 carbons, or a carbon number Aryl group of 6~10. px represents an integer of 0 to 3, preferably an integer of 0 to 2, more preferably 0 or 1, and more preferably 0. nx represents an integer from 1 to 20. nx may also be an integer of 10 or less. Moreover, the resin composition of this embodiment may contain the compound represented by formula (M1), and may contain at least 1 type of compound which differs in the value of nx, and may contain 2 or more types. When two or more types are contained, the average value (average number of repeating units) n of nx in the compound represented by the formula (M1) in the resin composition is to have a low melting point (low softening point), low melt viscosity, and excellent workability It is preferably at least 0.92, more preferably at least 0.95, still more preferably at least 1.0, and still more preferably at least 1.1. In addition, n is preferably 10.0 or less, more preferably 8.0 or less, further preferably 7.0 or less, still more preferably 6.0 or less, and may be 5.0 or less. The same applies to the following formula (M1-1) and the like.

The compound represented by the formula (M1) is preferably a compound represented by the following formula (M1-1). [chem 34] (In formula (M1-1), R ^M21 , R ^M22 , R ^M23 , and R ^M24 are each independently representing a hydrogen atom or an organic group. R ^M25 and R ^M26 are each independently representing a hydrogen atom or an alkyl group. ^{R M27} , R ^M28 , R ^M29 , and R ^M30 each independently represent a hydrogen atom or an organic group. ^{R M31} and R ^M32 each independently represent a hydrogen atom or an alkyl group. R ^M33 , R ^M34 , R ^M35 , and R ^M36 are Each independently represents a hydrogen atom or an organic group. R ^M37 , R ^M38 , and R ^M39 each independently represent a hydrogen atom or an alkyl group. nx represents an integer of 1 to 20.)

In the formula, R ^M21 , R ^M22 , R ^M23 , and R ^M24 each independently represent a hydrogen atom or an organic group. The organic group here is preferably an alkyl group, more preferably an alkyl group with 1 to 12 carbons, more preferably an alkyl group with 1 to 6 carbons, more preferably methyl, ethyl, propyl, butyl, especially Preferably it is methyl. 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 represent a hydrogen atom or an alkyl group, preferably an alkyl group. The alkyl group here is preferably an alkyl group with 1 to 12 carbon atoms, more preferably an alkyl group with 1 to 6 carbon atoms, further 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 represent a hydrogen atom or an organic group, preferably a hydrogen atom. The organic group here is preferably an alkyl group, more preferably an alkyl group with 1 to 12 carbon atoms, further preferably an alkyl group with 1 to 6 carbon atoms, further preferably a methyl group, an ethyl group, a propyl group, a butyl group, especially Preferably it is methyl. R ^M31 and R ^M32 each independently represent a hydrogen atom or an alkyl group, preferably an alkyl group. 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, further 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 represent a hydrogen atom or an organic group. The organic group here is preferably an alkyl group, more preferably an alkyl group with 1 to 12 carbon atoms, further preferably an alkyl group with 1 to 6 carbon atoms, further preferably a methyl group, an ethyl group, a propyl group, a butyl group, especially Preferably it is methyl. R ^M33 and R ^M36 are preferably hydrogen atoms, and R ^M34 and R ^M35 are preferably alkyl groups. R ^M37 , R ^M38 , and R ^M39 each independently represent a hydrogen atom or an alkyl group, preferably an alkyl group. 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, further preferably a methyl group, an ethyl group, a propyl group, or a butyl group, and particularly preferably a methyl group. nx represents an integer ranging from 1 to 20. nx may also be an integer of 10 or less.

The compound represented by the formula (M1-1) is preferably a compound represented by the following formula (M1-2). [chem 35] (In formula (M1-2), R ^M21 , R ^M22 , R ^M23 , and R ^M24 each independently represent a hydrogen atom or an organic group. ^{R M25} and R ^M26 each independently represent a hydrogen atom or an alkyl group. ^{R M27} , R ^M28 , R ^M29 , and R ^M30 are each independently representing a hydrogen atom or an organic group. ^{R M31} and R ^M32 are each independently representing a hydrogen atom or an alkyl group. R ^M33 , R ^M34 , R ^M35 , and R ^M36 are each independently independently represent a hydrogen atom or an organic group. ^{R M37} , R ^M38 , and R ^M39 each independently represent a hydrogen atom or an alkyl group. nx represents an integer of 1 to 20.)

In formula (M1-2), ^RM21 , ^RM22 , ^RM23 , ^RM24 , ^RM25 , RM26, ^RM27 , ^RM28 , ^RM29 , ^{RM30 , RM31} , ^RM32 , ^RM33 , ^RM34 , R ^M35 , R ^M36 , R ^M37 , R ^M38 , R ^M39 , and nx are respectively R ^M21 , R ^M22 , R M23 , R ^M24 , R ^M25 , ^{R M26 ,} R ^M27 , R ^M28 , R ^M29 , R ^M30 , R ^M31 , R ^M32 , R ^M33 , R ^{M34 , R M35 , R M36 , R M37} , R ^M38 , R ^M39 , and nx are synonymous, and preferred ranges are also the same.

The compound represented by the formula (M1-1) is preferably a compound represented by the following formula (M1-3), more preferably a compound represented by the following formula (M1-4). [chem 36] (In the formula (M1-3), nx represents an integer of 1 to 20.) nx may be an integer of 10 or less. [chem 37] (In the formula (M1-4), nx represents an integer of 1 to 20.) nx may be an integer of 10 or less.

The molecular weight of the compound represented by the formula (M1) is preferably 500 or more, more preferably 600 or more, and still more preferably 700 or more. There exists a tendency for the low dielectric characteristic and low water absorption of the obtained hardened|cured material to improve more by being more than the said lower limit. In addition, the molecular weight of the compound represented by formula (M1) is preferably 10,000 or less, more preferably 9,000 or less, more preferably 7,000 or less, more preferably 5,000 or less, more preferably 4,000 or less. There exists a tendency for the heat resistance and handleability of the hardened|cured material obtained to be improved more by being below the said upper limit.

[chem 38] (In the formula (M2), R ⁵⁴ each independently represent a hydrogen atom or a methyl group, and n ₄ represents an integer of 1 or more.) n ₄ is preferably an integer of 1 to 10, more preferably an integer of 1 to 5, and further preferably It is an integer of 1 to 3, more preferably 1 or 2, and may be 1. The compound represented by the formula (M2) may also be a mixture of compounds with different n ₄ , preferably a mixture. In addition, it may also be a mixture of compounds different in other parts as described in the part of the compound represented by formula (M0). [chem 39] (In formula (M3), R ⁵⁵ each independently represent a hydrogen atom, an alkyl group with 1 to 8 carbons, or a phenyl group, and n ₅ represents an integer ranging from 1 to 10.) R ⁵⁵ is preferably each independently selected from Hydrogen atom, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, and phenyl group, preferably hydrogen atom and/or a methyl group, more preferably a hydrogen atom. n ₅ is preferably an integer of 1 to 5, more preferably an integer of 1 to 3, further preferably 1 or 2. The compound represented by formula (M3) may also be a mixture of compounds with different n ₅ , preferably a mixture. In addition, it may also be a mixture of compounds different in other parts as described in the part of the compound represented by formula (M0). [chemical 40] (In formula (M4), R ⁵⁶ are each independently representing a hydrogen atom, methyl or ethyl, and R ⁵⁷ are each independently representing a hydrogen atom or methyl.) R ⁵⁶ is preferably each independently a methyl or ethyl , more preferably a methyl group and an ethyl group in each of the two benzene rings, and R ⁵⁷ is preferably a methyl group.

[chem 41] (In formula (M5), R ⁵⁸ each independently represent a hydrogen atom, an alkyl group with 1 to 8 carbons, or a phenyl group, R ⁵⁹ each independently represent a hydrogen atom or a methyl group, and n ₆ represents an integer of 1 or more. ) R ⁵⁸ is preferably each independently selected from the group consisting of a hydrogen atom, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, and phenyl One of the group of is more preferably a hydrogen atom and/or a methyl group, and is still more preferably a hydrogen atom. R ⁵⁹ is preferably methyl. n ₆ is preferably an integer of 1 to 10, more preferably an integer of 1 to 5, more preferably an integer of 1 to 3, still more preferably 1 or 2, and may be 1. The compound represented by the formula (M5) may also be a mixture of compounds with different n ₆ , preferably a mixture. In addition, it may also be a mixture of compounds different in other parts as described in the part of the compound represented by formula (M0).

A maleimide compound can be manufactured by a well-known method, and a commercial item can also be used. Commercially available products include, for example, "BMI-80" manufactured by K･I Chemical Industry Co., Ltd. as a compound represented by formula (M0), and "BMI-80" manufactured by DIC Corporation as a compound represented by formula (M1). "NE-X-9470S", the compound represented by the formula (M2) includes "BMI-2300" manufactured by Daiwa Chemical Industry Co., Ltd., and the compound represented by the formula (M3) includes "MIR" manufactured by Nippon Kayaku Co., Ltd. -3000-70MT", the compound represented by the formula (M4) includes "BMI-70" manufactured by K･I Chemical Industry Co., Ltd., and the compound represented by the formula (M5) includes the Nippon Kayaku Co., Ltd. "MIR-5000".

In addition, examples of maleimide compounds other than the above-mentioned ones include N-phenylmaleimide, oligomers of phenylmethane maleimide, metaphenylbismaleimide, 4-methyl-1,3-phenylene bismaleimide, 1,6-bismaleimide-(2,2,4-trimethyl)hexane, 4,4'-bismaleimide Phenyl ether bismaleimide, 4,4'-diphenyl bismaleimide, 1,3-bis(3-maleimidephenoxy)benzene, 1,3-bis (4-Maleimidephenoxy)benzene, prepolymers thereof, prepolymers of maleimide and amines, etc.

In the case where the resin composition of this embodiment contains a maleimide compound, the lower limit of the content is preferably 1 part by mass or more, more preferably 5 parts by mass, relative to 100 parts by mass of the resin solid content in the resin composition. It is more preferably at least 10 parts by mass, more preferably at least 20 parts by mass. When the content of the maleimide compound is 1 part by mass or more, the low dielectric properties and flame resistance of the cured product obtained tend to be improved. In addition, the upper limit of the maleimide compound content is preferably not more than 70 parts by mass, more preferably not more than 60 parts by mass, and still more preferably 50 parts by mass relative to 100 parts by mass of resin solid content in the resin composition. Below, 40 mass parts or less may be sufficient. When the content of the maleimide compound is 70 parts by mass or less, metal foil peel strength and low water absorption tend to be improved. The resin composition of this embodiment may contain only 1 type of maleimide compound, and may contain 2 or more types. When two or more types are contained, the total amount is preferably within the above-mentioned range.

＜＜Epoxy compound＞＞ The resin composition of this embodiment may also contain an epoxy compound. As long as the epoxy compound has one or more (preferably 2 to 12, more preferably 2 to 6, further preferably 2 to 4, further preferably 2 or 3, further preferably 2) epoxy groups in one molecule The compound or resin used is not particularly limited, and compounds generally used in the field of printed wiring boards can be widely used. Epoxy compounds, such as bisphenol A type epoxy resin, bisphenol E type epoxy resin, bisphenol F type epoxy resin, bisphenol S type epoxy resin, phenol novolak type epoxy resin, bisphenol A Novolac-type epoxy resin, glycidyl ester-type epoxy resin, aralkyl novolak-type epoxy resin, biphenyl aralkyl-type epoxy resin, naphthyl ether-type epoxy resin, cresol novolac Type epoxy resin, multifunctional 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 Type epoxy resin, dicyclopentadiene type epoxy resin, biphenyl type epoxy resin, alicyclic epoxy resin, polyol type epoxy resin, phosphorus epoxy resin, glycidylamine, epoxy Propyl esters, compounds obtained by epoxidizing the double bond of butadiene, etc., compounds obtained by reacting hydroxyl-containing polysiloxane resins with epichlorohydrin, etc. By using these, the formability and adhesiveness of a resin composition will be improved. Among them, in view of improving flame retardancy and heat resistance, biphenyl aralkyl epoxy resins, naphthyl ether epoxy resins, polyfunctional phenol epoxy resins, and naphthalene epoxy resins are suitable. The resin is more preferably a biphenyl aralkyl type epoxy resin.

The resin composition of this embodiment preferably contains an epoxy compound within the range that does not impair the effects of the present invention. When the resin composition of this embodiment contains an epoxy compound, the content thereof is preferably 0.1 part by mass or more, more preferably 1 part by mass or more, and still more preferably 100 parts by mass of the resin solid content in the resin composition. 2 parts by mass or more. When content of an epoxy compound is 0.1 mass part or more, there exists a tendency for metal foil peeling strength and toughness 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, relative to 100 parts by mass of the resin solid content in the resin composition when the resin composition of the present embodiment contains an epoxy compound. It is not more than 20 parts by mass, more preferably not more than 20 parts by mass, still more preferably not more than 10 parts by mass, still more preferably not more than 8 parts by mass, still more preferably not more than 5 parts by mass. When content of an epoxy compound is 50 mass parts or less, there exists a tendency for the electric characteristic of the hardened|cured material obtained to improve. The resin composition in this embodiment may contain only 1 type of epoxy compound, and may contain 2 or more types. When containing 2 or more types, it is preferable that a total amount shall be the said range. In addition, the resin composition in this embodiment may be a structure which does not contain an epoxy compound substantially. Substantially not containing means that the content of the epoxy compound is less than 1 part by mass, preferably less than 0.1 part by mass, more preferably less than 0.01 part by mass, based on 100 parts by mass of resin solid content in the resin composition.

In addition to the above, for other resins (D), reference may be made to the descriptions in paragraphs 0037-0123 and 0133-0145 of JP-A-2020-117714, and these contents are incorporated in this specification.

Regarding the total amount of other resins (D), when other resins (D) are contained, the total content thereof is preferably 5 parts by mass or more, more preferably 10 parts by mass or more, based on 100 parts by mass of resin solid content, More preferably, it is 20 mass parts or more, Still more preferably, it is 30 mass parts or more. There exists a tendency for a glass transition temperature and heat resistance to be improved more by being more than the said lower limit. In addition, the upper limit of the total content of the above-mentioned other resins (D) is preferably not more than 70 parts by mass, more preferably not more than 60 parts by mass, and still more preferably not more than 50 parts by mass, based on 100 parts by mass of resin solid content. It is 40 mass parts or less. There exists a tendency for low dielectric loss tangent to be improved more by being below the said upper limit.

＜Flame retardant (E)＞ The resin composition of this embodiment may contain a flame retardant (E). Examples of the flame retardant (E) include phosphorus-based flame retardants, halogen-based flame retardants, inorganic-based flame retardants, and polysiloxane-based flame retardants, and phosphorus-based flame retardants are preferred. As the flame retardant (E), known ones can be used, such as brominated epoxy resin, brominated polycarbonate, brominated polystyrene, brominated styrene, brominated phthalimide, tetrabromo Bisphenol A, pentabromobenzyl (meth)acrylate, pentabromotoluene, tribromophenol, hexabromobenzene, decabromodiphenyl ether, bis-1,2-pentabromophenylethane, chlorinated poly Styrene, chlorinated paraffin and other halogen flame retardants, red phosphorus, tricresyl phosphate, triphenyl phosphate, cresol diphenyl phosphate, trixylyl phosphate, trialkyl phosphate, di Alkyl phosphate, ginseng (chloroethyl) phosphate, phosphazene, 1,3-phenylene bis(2,6-xylyl phosphate), 10-(2,5-dihydroxyphenyl)- Phosphorous flame retardants such as 10H-9-oxa-10-phosphaphenanthrene-10-oxide, aluminum hydroxide, magnesium hydroxide, some boehmite, boehmite, zinc borate, antimony trioxide and other inorganic It is a flame retardant, polysiloxane rubber, polysiloxane resin and other polysiloxane flame retardants. In this embodiment, among these, 1,3-phenylene bis(2,6-xylyl phosphate) is preferable in consideration of not impairing low dielectric properties.

When the resin composition of this embodiment contains the flame retardant (E), the content thereof is preferably 1 part by mass or more, more preferably 5 parts by mass or more, based on 100 parts by mass of resin solid content in the resin composition. In addition, the upper limit of the content of the flame retardant is preferably not more than 25 parts by mass, more preferably not more than 20 parts by mass. The flame retardant (E) may be used alone or in combination of two or more. When using 2 or more types, the total amount shall be the said range.

＜Filler (F)＞ The resin composition of this embodiment preferably contains a filler (F). By containing the filler (F), the dielectric properties (low dielectric constant, low dielectric loss tangent, etc.), flame resistance, and physical properties such as low thermal expansion of the resin composition and its cured product can be further improved. In addition, the filler (F) used in this embodiment is preferably excellent in low dielectric properties. For example, the filler (F) used in this embodiment preferably has a relative permittivity (Dk) of 8.0 or less, more preferably 6.0 or less, and still more preferably 4.0 or less, as measured by the cavity resonator perturbation method. In addition, the lower limit of the above-mentioned relative permittivity is, for example, practically 2.0 or more. In addition, the filler (F) used in this embodiment preferably has a dielectric loss tangent (Df) of 0.05 or less, more preferably 0.01 or less, as measured by the cavity resonator perturbation method. In addition, the lower limit value of the above-mentioned dielectric loss tangent is, for example, practically 0.0001 or more.

The kind of filler (F) used in this embodiment is not particularly limited, and general users in the industry can be used appropriately. Specifically, natural silica, fused silica, synthetic silica, amorphous silica, Aerosil, silica such as hollow silica, alumina, white carbon, titanium dioxide, titanium oxide, etc. , zinc oxide, magnesium oxide, zirconia and other metal oxides, zinc borate, zinc stannate, forsterite, barium titanate, strontium titanate, calcium titanate and other composite oxides, boron nitride, condensed nitrogen Boron nitride, silicon nitride, aluminum nitride and other nitrides, aluminum hydroxide, aluminum hydroxide heat-treated products (aluminum hydroxide is heat-treated to remove part of the crystal water), boehmite, magnesium hydroxide and other metal hydroxides (including hydrate), molybdenum compounds such as molybdenum oxide or zinc molybdate, barium sulfate, clay, kaolin, talc, calcined clay, calcined kaolin, calcined talc, mica, E-glass, A-glass, NE-glass, C- Glass, L-glass, D-glass, S-glass, M-glass G20, glass short fiber (including E glass, T glass, D glass, S glass, Q glass and other glass powders.), hollow glass, ball Inorganic fillers such as glass, styrene type, butadiene type, acrylic type rubber powder, core shell type rubber powder, silicone resin powder, polysiloxane rubber Powder, polysiloxane composite powder and other organic fillers, etc. In this embodiment, the filler (F) preferably contains an inorganic filler, and more preferably contains an inorganic filler selected from the group consisting of silicon dioxide, aluminum hydroxide, aluminum nitride, boron nitride, forsterite, titanium oxide, and barium titanate. , strontium titanate, and calcium titanate, and in consideration of low dielectric properties, it is more preferable to contain one selected from the group consisting of silicon dioxide and aluminum hydroxide. more than one species, and further preferably contains silicon dioxide. By using these fillers, the heat resistance, dielectric properties, thermal expansion properties, dimensional stability, flame retardancy and other properties of the hardened resin composition will be further improved.

The content of the filler (F) in the resin composition of this embodiment can be appropriately set according to the desired characteristics. Although there is no particular limitation, it is preferably 10 parts by mass relative to 100 parts by mass of the resin solid content in the resin composition. It is more preferably 20 parts by mass or more, further preferably 40 parts by mass or more, further preferably 60 parts by mass or more, and still more preferably 80 parts by mass or more. There exists a tendency for low thermal expansion property and low dielectric loss tangent property to be further improved by being more than the said lower limit. In addition, the upper limit of the content of the filler is preferably not more than 300 parts by mass, more preferably not more than 250 parts by mass, further preferably not more than 200 parts by mass, and still more preferably not more than 150 parts by mass, based on 100 parts by mass of the solid content of the resin. Parts or less, more preferably 120 parts by mass or less. Formability tends to be improved more by being below the said upper limit. In the resin composition of the present embodiment, as an example of a preferable embodiment, an aspect in which the content of the filler (F) is 30% by mass to 80% by mass of the components excluding the solvent is exemplified. The resin composition of this embodiment may contain only 1 type of filler (F), and may contain 2 or more types. When containing 2 or more types, it is preferable that a total amount shall be the said range.

In the resin composition of this embodiment, when using a filler (F), especially an inorganic filler, you may contain a silane coupling agent further. By containing the silane coupling agent, the dispersibility of the filler (F) and the adhesive strength between the resin component and the filler (F) and the base material described below tend to be further improved. The silane coupling agent is not particularly limited, and examples include silane coupling agents generally used in the surface treatment of inorganic substances, such as aminosilane compounds (such as γ-aminopropyltriethoxysilane, N-β- (Aminoethyl)-γ-aminopropyl trimethoxysilane, etc.), epoxy silane compounds (such as γ-glycidoxypropyl trimethoxysilane, etc.), vinyl silane compounds (such as Vinyltrimethoxysilane, etc.), styrylsilane compounds (such as styryltrimethoxysilane, etc.), acrylic silane compounds (such as γ-acrylpropyltrimethoxysilane, etc.), cationic silanes Compounds (such as N-β-(N-vinylbenzylaminoethyl)-γ-aminopropyltrimethoxysilane hydrochloride, etc.), phenylsilane-based compounds, and the like. A silane coupling agent can be used individually by 1 type, or in combination of 2 or more types. In particular, by using at least one selected from the group consisting of vinyl silane compounds, acrylic silane compounds, and styryl silane compounds as a silane coupling agent, and using a silane coupling agent containing an aromatic ring and a vinyl group A thermosetting resin (especially, a polymer having a constituent unit represented by formula (V)) as the above-mentioned compatible thermosetting resin (C) can obtain a resin that maintains excellent dielectric properties and has excellent moisture absorption and heat resistance Composition. The content of the silane coupling agent is not particularly limited, and may be 0.1 to 5.0 parts by mass relative to 100 parts by mass of resin solids.

＜Monomers or oligomers with ethylenically unsaturated groups＞ In the resin composition of this embodiment, in order to improve thermosetting properties and curability due to active energy rays (such as photocurability due to ultraviolet rays, etc.), monomers or oligomers having ethylenically unsaturated groups can also be used in combination. things. The oligomer or monomer having an ethylenically unsaturated group used in this embodiment is not particularly limited as long as it is an oligomer or monomer having one or more ethylenically unsaturated groups in one molecule. Examples thereof include monomers or oligomers having (meth)acryl groups, vinyl groups, and the like. In addition, in this specification, a compound corresponding to a monomer or an oligomer having an ethylenically unsaturated group, and a compound corresponding to a polyphenylene ether compound having a carbon-carbon unsaturated double bond at the terminal is regarded as It is a polyphenylene ether compound with a carbon-carbon unsaturated double bond at the end.

More specifically, as a monomer having an ethylenically unsaturated group, a compound (F1) having a molecular weight of less than 1000 and containing one organic group containing an ethylenically unsaturated bond in the molecule (compound (F1) ). It is presumed that by using the compound (F1), the ethylenically unsaturated bond of the compound (F1) reacts with the above-mentioned compatible thermosetting resin (C) to improve the moisture absorption and heat resistance of the cured product obtained. The ethylenically unsaturated bond constituting the above-mentioned ethylenically unsaturated bond-containing organic group does not include the meaning of containing an ethylenically unsaturated bond as a part of an aromatic ring. On the other hand, it includes the meaning of containing an ethylenically unsaturated bond as part of a non-aromatic ring. As an example containing an ethylenically unsaturated bond as a part of a non-aromatic ring, a cyclohexenyl group in a molecule, etc. are mentioned. Moreover, it also includes the part other than the terminal of the organic group of a linear or branched chain, that is, the meaning which contains an ethylenically unsaturated bond in a linear or branched chain. The above-mentioned organic group containing an ethylenically unsaturated bond is more preferably one selected from the group consisting of vinyl, allyl, acrylic, and methacrylic, more preferably vinyl. In addition, in this specification, the compound which corresponds to the monomer or oligomer which has an ethylenically unsaturated group and also corresponds to this compound which is a silane coupling agent is regarded as a silane coupling agent.

The compound (F1) used in this embodiment is preferably composed of only atoms selected from carbon atoms, hydrogen atoms, oxygen atoms and silicon atoms, more preferably composed of only atoms selected from carbon atoms, hydrogen atoms, and oxygen atoms. Atoms make up. In addition, the compound (F1) used in this embodiment may have a polar group or may not have a polar group. The compound (F1) used in this embodiment preferably does not have a polar group. As the polar group, an amino group, a carboxyl group, a hydroxyl group, and a nitro group are exemplified.

In this embodiment, the molecular weight of the compound (F1) is preferably 70 or more, more preferably 80 or more, and still more preferably 90 or more. There exists a tendency for compound (F1) to be suppressed from volatilizing from the resin composition of this embodiment, its hardened|cured material, etc. by being more than the said lower limit. The upper limit of the molecular weight of the compound (F1) is preferably 500 or less, more preferably 400 or less, further preferably 300 or less, still more preferably 200 or less, and may be 150 or less. There exists a tendency for the effect of raising the reactivity of the thermosetting resin (C) compatible with the said upper limit to be more improved by being below the said upper limit. In the case where the resin composition of this embodiment contains two or more compounds (F1), the average molecular weight of the compound (F1) is preferably within the above-mentioned range, and more preferably the molecular weight of each compound is within the above-mentioned preferred range. In the range.

In this embodiment, the compound (F1) preferably has a boiling point of 110°C or higher, more preferably 115°C or higher, and still more preferably 120°C or higher. By being more than the said lower limit, volatilization of the compound (F1) at the time of thermosetting a resin composition can be suppressed, and a thermosetting resin (C) can be made to react with a compound (F1). The boiling point of the above-mentioned compound (F1) is preferably not higher than 300°C, more preferably not higher than 250°C, still more preferably not higher than 200°C. By being below the said upper limit, it becomes difficult to remain in hardened|cured material as a residual solvent. When the resin composition of this embodiment contains 2 or more types of compounds (F1), it is sufficient that the average boiling point falls within the said range, and it is preferable that the boiling point of each compound falls within the said preferable range.

As the compound (F1), there are exemplified (meth)acrylate compounds, aromatic vinyl compounds (preferably styrene compounds), saturated fatty acid vinyl compounds, cyanide vinyl compounds, ethylenically unsaturated carboxylic acids, ethylenically unsaturated carboxylic acids, ethylenically Unsaturated carboxylic acid anhydride, ethylenically unsaturated dicarboxylic acid monoalkyl ester, ethylenically unsaturated carboxylic acid amide, etc., preferably selected from (meth)acrylate compounds, aromatic vinyl compounds, and saturated fatty acids At least one of the group consisting of vinyl compounds is more preferably an aromatic vinyl compound. Specific examples of the compound (F1) include methylstyrene and ethylvinylbenzene.

On the other hand, the resin composition of this embodiment preferably contains styrene oligomer (F2) for the purpose of improving low dielectric constant and low dielectric loss tangent. The styrene oligomer (F2) of this embodiment is obtained by polymerizing at least one selected from the group consisting of styrene, the above-mentioned styrene derivatives, and vinyltoluene, and its number average molecular weight is 178~1600, the average number of aromatic rings is 2~14, the total amount of 2~14 aromatic rings is more than 50% by mass, and the boiling point is 300°C or more without branching structure.

Examples of the styrene oligomer (F2) used in this embodiment include styrene polymers, vinyltoluene polymers, α-methylstyrene polymers, and vinyltoluene-α-methylstyrene polymers. substances, styrene-α-styrene polymers, etc. Commercially available products can also be used as the styrene polymer, for example, Piccolastic A5 (manufactured by Eastman Chemical Company), Piccolastic A-75 (manufactured by Eastman Chemical Company), Piccotex 75 (manufactured by Eastman Chemical Company), FTR-8100 (manufactured by Mitsui Chemicals Co., Ltd.), FTR-8120 (manufactured by Mitsui Chemicals Co., Ltd.). Moreover, Piccotex LC (manufactured by Eastman Chemical Company.) can be mentioned as a vinyltoluene-α-methylstyrene polymer. In addition, examples of α-methylstyrene polymers include Kristalex 3070 (manufactured by Eastman Chemical Company), Kristalex 3085 (manufactured by Eastman Chemical Company), Kristalex (3100), Kristalex 5140 (manufactured by Eastman Chemical Company), FMR -0100 (manufactured by Mitsui Chemicals Co., Ltd.), FMR-0150 (manufactured by Mitsui Chemicals Co., Ltd.). Moreover, as a styrene-α-styrene polymer, FTR-2120 (made by Mitsui Chemicals Co., Ltd.) is mentioned. These styrene oligomers may be used alone or in combination of two or more. In the resin composition of this embodiment, the α-methylstyrene oligomer is thermally cured well, has good embedding properties of fine wiring, and is excellent in solder heat resistance, low relative permittivity, and low dielectric loss tangent. So better.

In addition, the details of monomers or oligomers with ethylenically unsaturated groups can refer to the records in paragraphs 0069-0087 of International Publication No. 2017/135168, and paragraphs 0065-0067 of International Publication No. 2019/230945. etc. are included in this manual.

By using a monomer or oligomer having an ethylenically unsaturated group, and as the above-mentioned compatible thermosetting resin (C), a thermosetting resin containing an aromatic ring and a vinyl group (especially, having the formula (V ) represents the constituent unit of the polymer) to obtain a resin composition excellent in moisture absorption and heat resistance while maintaining excellent dielectric properties.

When the resin composition of this embodiment contains a monomer or oligomer having an ethylenically unsaturated group, the content thereof is preferably 0.5 parts by mass or more, more preferably 1 part by mass, based on 100 parts by mass of the solid content of the resin. Above, more preferably 2 mass parts or more, still more preferably 3 mass parts or more, may be 5 mass parts or more. There exists a tendency for a low dielectric characteristic to improve more by being more than the said lower limit. In addition, the upper limit of the content of the above-mentioned monomer or oligomer having an ethylenically unsaturated group is preferably 30 parts by mass or less, more preferably 25 parts by mass or less, and further preferably 100 parts by mass of resin solids. 20 parts by mass or less, more preferably 15 parts by mass or less, further preferably 10 parts by mass or less. There exists a tendency for heat resistance to be improved more by being below the said upper limit. In addition, there is a tendency to further improve low dielectric constant, low dielectric loss tangent and chemical resistance. The resin composition of this embodiment may contain only one type of monomer or oligomer having an ethylenically unsaturated group, or may contain two or more types. When two or more types are contained, the total amount is preferably within the above-mentioned range.

＜Active ester compound＞ The resin composition of this embodiment may also contain an active ester compound. The active ester compound is not particularly limited, and for example, there are two or more (preferably 2 to 12, more preferably 2 to 6, further preferably 2 to 4, further preferably 2 or 3, further preferably It is the active ester compound of 2). The active ester compound can also be a linear or branched or cyclic compound. Among these, active esters obtained by reacting carboxylic acid compounds and/or thiocarboxylic acid compounds with hydroxyl compounds and/or thiol compounds are preferable from the viewpoint of further improving the heat resistance of the obtained cured product. The compound is more preferably an active ester compound obtained by reacting a carboxylic acid compound with one or more compounds selected from the group consisting of phenol compounds, naphthol compounds, and thiol compounds, and is further preferably 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, especially a compound having two or more carboxylic acids in one molecule . An aromatic compound having two or more active ester groups in one molecule obtained by reacting with an aromatic compound having a phenolic hydroxyl group. Examples of the above-mentioned carboxylic acid compound include those 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. One or more of the group. Among them, it is preferably selected from the group consisting of succinic acid, maleic acid, itaconic acid, phthalic acid, and isophthalic acid in view of improving the heat resistance of the obtained cured product. One or more species selected from the group consisting of dicarboxylic acid and terephthalic acid, more preferably one or more species selected from the group consisting of isophthalic acid and terephthalic acid. As said thiocarboxylic acid compound, one or more types selected from thioacetic acid and thiobenzoic acid are mentioned, for example. Examples of the above-mentioned phenol compound or naphthol compound include those selected from hydroquinone, resorcinol, bisphenol A, bisphenol F, bisphenol S, reduced phenolphthalein, methylated bisphenol A, Methylated bisphenol F, methylated bisphenol S, phenol, o-cresol, m-cresol, p-cresol, catechol, α-naphthol, β-naphthol, 1,5-dihydroxynaphthalene , 1,6-dihydroxynaphthalene, 2,6-dihydroxynaphthalene, dihydroxybenzophenone, trihydroxybenzophenone, tetrahydroxybenzophenone, pyroglucinol, benzenetriol, dicyclopenta One or more of the group consisting of dienyl diphenol and phenol novolak, bisphenol A, bisphenol F, and bisphenol S are preferable from the viewpoint of improving the heat resistance and solvent solubility of the cured product obtained. , methylated bisphenol A, methylated bisphenol F, methylated bisphenol S, catechol, α-naphthol, β-naphthol, 1,5-dihydroxynaphthalene, 1,6-di Hydroxynaphthalene, 2,6-dihydroxynaphthalene, dihydroxybenzophenone, trihydroxybenzophenone, tetrahydroxybenzophenone, pyroglucinol, pyroglucinol, dicyclopentadienyl diphenol, Phenol novolac, preferably selected from catechol, 1,5-dihydroxynaphthalene, 1,6-dihydroxynaphthalene, 2,6-dihydroxynaphthalene, dihydroxybenzophenone, trihydroxydihydroxy At least one selected from the group consisting of benzophenone, tetrahydroxybenzophenone, pyroglucinol, pyroglucinol, dicyclopentadienyl diphenol, and phenol novolac, and is further preferably selected from the group consisting of 1,5-Dihydroxynaphthalene, 1,6-Dihydroxynaphthalene, 2,6-Dihydroxynaphthalene, Dihydroxybenzophenone, Trihydroxybenzophenone, Tetrahydroxybenzophenone, Dicyclopentadiene One or more of the group consisting of diphenol and phenol novolac, especially preferably selected from the group consisting of dihydroxybenzophenone, trihydroxybenzophenone, tetrahydroxybenzophenone, dicyclopentadiene One or more species selected from the group consisting of alkenyl diphenol and phenol novolac (preferably one or more species selected from the group consisting of dicyclopentadienyl diphenol and phenol novolac, more preferably dicyclopentadienyldiphenol). As the above-mentioned thiol compound, one or more kinds selected from the group consisting of benzenedithiol and trithioldithiol can be mentioned. In addition, the active ester compound is preferably a compound having two or more carboxylic acids and an aliphatic chain in one molecule from the viewpoint of improving compatibility with epoxy compounds, and is preferably a compound having an aliphatic chain from the viewpoint of improving heat resistance. Compounds with aromatic rings. As a more specific active ester compound, the active ester compound described in Unexamined-Japanese-Patent No. 2004-277460 is mentioned.

The active ester compound can use a commercial item, and can also prepare it by a well-known method. Examples of commercially available products include compounds containing a dicyclopentadienyl diphenol structure (such as EXB9451, EXB9460, EXB9460S, HPC-8000-65T (all manufactured by DIC Corporation), etc.), acetylated phenol novolac ( For example, DC808 (manufactured by Mitsubishi Chemical Corporation)), and benzoyl compounds of phenol novolac (such as YLH1026, YLH1030, YLH1048 (all manufactured by Mitsubishi Chemical Corporation)), consider improving the storage stability of the varnish and making the resin composition From the viewpoint of low thermal expansion when hardened (cured product), EXB9460S is preferable.

The active ester compound can be prepared by a known method, for example, it can be obtained by condensation reaction of a carboxylic acid compound and a hydroxyl compound. As a specific example, (a) carboxylic acid compound or its halide, (b) hydroxy compound, (c) aromatic monohydroxy compound, with respect to (a) carboxyl or acyl halide 1 mole, ( The method in which the phenolic hydroxyl group of b) is 0.05-0.75 mol and (c) 0.25-0.95 mol are reacted.

It is preferable to contain an active ester compound within the range not impairing the effects of the present invention. When the resin composition of this embodiment contains an active ester compound, it is preferably 1 part by mass or more and 90 parts by mass or less with respect to 100 parts by mass of resin solid content in the resin composition. The resin composition in this embodiment may contain only one type of active ester compound, or may contain two or more types. When two or more types are contained, the total amount is preferably within the above range. In addition, the resin composition in this embodiment may be a structure not containing an active ester compound substantially. Substantially not containing means that the content of the active ester compound is less than 1 part by mass relative to 100 parts by mass of the resin solid content in the resin composition, preferably less than 0.1 part by mass, more preferably less than 0.01 part by mass .

＜Dispersant＞ The resin composition of this embodiment may also contain a dispersant. As the dispersant, those used for general coatings can be suitably used, and the type is not particularly limited. The dispersant is preferably a wetting and dispersing agent with a copolymer base. As a specific example, DISPERBYK (registered trademark)-110, 111, 161, 180, 2009, 2152, 2155, BYK (registered trademark) manufactured by BYK JAPAN KK. -W996, W9010, W903, W940, etc.

In the case where the resin composition of this embodiment contains a dispersant, the lower limit of the content is preferably 0.01 parts by mass or more, more preferably 0.1 parts by mass or more, relative to 100 parts by mass of resin solids in the resin composition, It may be 0.3 parts by mass or more. In addition, the upper limit of the content of the dispersant is preferably not more than 10 parts by mass, more preferably not more than 5 parts by mass, and still more preferably not more than 3 parts by mass relative to 100 parts by mass of resin solid content in the resin composition. A dispersant can be used individually by 1 type, or in combination of 2 or more types. When using 2 or more types, a total amount will be in the said range.

＜Hardening Accelerator＞ The resin composition of this embodiment may further contain a hardening accelerator. The hardening accelerator is not particularly limited, and examples include imidazoles such as 2-ethyl-4-methylimidazole and triphenylimidazole; benzoyl peroxide, lauryl peroxide, acetyl peroxide, peroxide p-Chlorobenzoyl, di-tert-butyl diperoxyphthalate, α,α'-bis(tert-butyl peroxide) diisopropylbenzene, 2,5-dimethyl-2,5 -Organic peroxides such as bis(tert-butylperoxy)hexane, 2,5-dimethyl-2,5-bis(tert-butylperoxy)hexyne-3; azodinitrile (e.g. Azo compounds such as azobisisobutyronitrile); N,N-dimethylbenzylamine, N,N-dimethylaniline, N,N-dimethyltoluidine, 2-N-ethylaniline ethanol , tri-n-butylamine, pyridine, quinoline, N-methyl 𠰌line, triethanolamine, triethylenediamine, tetramethylbutanediamine, N-methylpiperidine, etc. Phenols such as cresol, cresol, resorcinol, and catechol; pyrolysis-type free radical generators such as 2,3-dimethyl-2,3-diphenylbutane; lead naphthenate, Lead stearate, zinc naphthenate, zinc octoate, manganese octoate, tin oleate, dibutyltin malate, manganese naphthenate, cobalt naphthenate, iron acetylacetonate and other organic metal salts; Dissolved in hydroxyl-containing compounds such as phenol and bisphenol; tin chloride, zinc chloride, aluminum chloride and other inorganic metal salts; dioctyl tin oxide, other alkyl tin, alkyl tin oxide and other organic tin compounds wait. The ideal hardening accelerators are imidazoles and organic metal salts, more preferably a combination of imidazoles and organic metal salts. Moreover, in this embodiment, the structure which does not contain a polymerization initiator, such as an organic peroxide and an azo compound substantially, may be sufficient. Substantially not containing means that the content of the polymerization initiator is less than 0.1 parts by mass with respect to 100 parts by mass of the resin solid content in the resin composition.

When the resin composition of this embodiment contains a curing accelerator, the lower limit of the content is preferably 0.005 parts by mass or more, more preferably 0.01 parts by mass or more, relative to 100 parts by mass of the resin solid content in the resin composition. , and more preferably 0.1 parts by mass or more. In addition, the upper limit of the content of the hardening accelerator is preferably 10 parts by mass or less, more preferably 5 parts by mass or less, and still more preferably 2 parts by mass or less, based on 100 parts by mass of resin solid content in the resin composition. A hardening accelerator can be used individually by 1 type, or in combination of 2 or more types. When using 2 or more types, a total amount will be in the said range.

<Solvent> The resin composition of this embodiment may contain a solvent, preferably an organic solvent. In the case of containing a solvent, the resin composition of this embodiment is at least a part of the solid content of the above-mentioned various resins, and is preferably in a form (solution or varnish) that is completely dissolved or compatible with the solvent. As the solvent, as long as it is a polar organic solvent or a non-polar organic solvent that can dissolve or dissolve at least a part of the above-mentioned various resin solid components, it is preferably a polar organic solvent or a non-polar organic solvent that can dissolve or compatible all of the above-mentioned various resin solid components. The solvent is not particularly limited. As a polar organic solvent, for example, ketones (such as acetone, methyl ethyl ketone, methyl isobutyl ketone, etc.), cellosulfones (such as propylene glycol monomethyl ether, propylene glycol monomethyl ether, etc.) Acetate, etc.), esters (such as ethyl lactate, methyl acetate, ethyl acetate, butyl acetate, isopentyl acetate, ethyl lactate, methyl methoxypropionate, methyl hydroxyisobutyrate, etc. ), amides (eg, dimethoxyacetamide, dimethylformamide, etc.), and examples of nonpolar organic solvents include aromatic hydrocarbons (eg, toluene, xylene, etc.). A solvent can be used individually by 1 type or in combination of 2 or more types. When using 2 or more types, a total amount will be the said range.

＜Other ingredients＞ The resin composition of this embodiment may contain various polymer compounds such as thermoplastic resins and oligomers thereof, and various additives in addition to the above-mentioned components. Examples of additives include ultraviolet absorbers, antioxidants, photopolymerization initiators, fluorescent brighteners, photosensitizers, dyes, pigments, thickeners, flow regulators, lubricants, defoamers, coating agent, gloss agent, polymerization inhibitor, etc. These additives may be used alone or in combination of two or more.

＜Use＞ The resin composition of this embodiment is used as a cured product. Specifically, the resin composition of this embodiment can be used as a low relative permittivity material and/or a low dielectric loss tangent material, and can be suitably used as a resin for electronic materials such as an insulating layer of a printed wiring board and a semiconductor packaging material. Composition. The resin composition of this embodiment can be suitably used as a material for a prepreg, a metal foil-clad laminate using a prepreg, a resin composite sheet, and a printed wiring board. The resin composition of this embodiment is used as a layered material (including the meaning of a film shape, a sheet shape, etc.) such as a prepreg or a resin composite sheet that becomes an insulating layer of a printed wiring board, and it is made into such a layered material. , the thickness is preferably not less than 5 μm, more preferably not less than 10 μm. The upper limit of the thickness is preferably 200 μm or less, more preferably 180 μm or less. In addition, the thickness of the above-mentioned layered material includes the thickness of the glass cloth, for example, when impregnating the resin composition of the present embodiment into glass cloth or the like. The material formed from the resin composition of the present embodiment can be used in applications where exposure and development are performed to form a pattern, and can also be used in applications where exposure and development are not performed. In particular, it is suitable for use in applications where exposure and development are not performed.

＜＜Prepreg＞＞ The prepreg system of this embodiment is formed from a base material (prepreg base material) and the resin composition of this embodiment. The prepreg of the present embodiment, for example, is dried by heating (for example, at 120~220° C. Minute method, etc.) to make it semi-hardened. In this case, the adhesion amount of the resin composition to the substrate, that is, the amount of the resin composition (including the filler (F)) relative to the total amount of the semi-cured prepreg is preferably in the range of 20 to 99% by mass, more preferably It is preferably in the range of 20 to 80% by mass.

It will not specifically limit as a base material, if it is a base material used for various printed wiring board materials. As the material of the substrate, for example, glass fiber (such as E-glass, D-glass, L-glass, S-glass, T-glass, Q-glass, UN-glass, NE-glass, spherical glass, etc.) , Inorganic fibers other than glass (such as quartz, etc.), organic fibers (such as polyimide, polyamide, polyester, liquid crystal polyester, polytetrafluoroethylene, etc.). The form of the substrate is not particularly limited, and examples thereof include woven fabrics, nonwoven fabrics, rovings, chopped strand mats, and surface mats. These base materials may be used individually, and may use 2 or more types together. Among these substrates, in consideration of dimensional stability, it is preferable to be a woven fabric treated with ultra-fiber opening and hole filling; in consideration of strength and low water absorption, the thickness of the substrate is preferably less than 200 μm, and the mass The glass fabric ^below 250g/m2 is suitable for surface treatment with silane coupling agents such as epoxy silane and amino silane in consideration of moisture absorption and heat resistance. From the viewpoint of electrical characteristics, it is more suitable to be a low-dielectric glass cloth made of glass fibers such as L-glass, NE-glass, and Q-glass that exhibit low relative permittivity and low dielectric loss tangent. The substrate with low relative permittivity is, for example, a substrate with a relative permittivity of 5.0 or less (preferably 3.0 to 4.9). The substrate with low dielectric loss tangent is, for example, a substrate with a dielectric loss tangent of 0.006 or less (preferably 0.001 to 0.005). Relative permittivity and dielectric loss tangent are values measured at 10GHz by perturbation method cavity resonator.

<<Metal Foil Clad Laminate>> The metal foil clad laminate of this embodiment includes at least one layer formed of the prepreg of this embodiment, and one side of the layer formed of the prepreg is arranged Or metal foil on both sides. In terms of the manufacturing method of the metal foil-clad laminate of this embodiment, for example, arrange at least one prepreg of this embodiment (preferably overlapping two or more sheets), and arrange metal foil on one or both sides of the prepreg And carry out the method of laminated forming. More specifically, it can be produced by arranging metal foils such as copper and aluminum on one or both sides of a prepreg and performing lamination molding. The number of sheets of prepreg is preferably 1 to 10 sheets, more preferably 2 to 10 sheets, and further preferably 2 to 9 sheets. As metal foil, it will not specifically limit if it is used for the material for printed wiring boards, For example, copper foils, such as rolled copper foil and electrolytic copper foil, are mentioned. The thickness of the metal foil (preferably copper foil) is not particularly limited, and may be about 1.5-70 μm. As for the molding method, there are listed methods commonly used for molding laminated boards and multilayer boards for printed wiring boards. More specifically, multilayer presses, multilayer vacuum presses, continuous molding machines, and autoclave molding are used. Machine, etc., the method of lamination forming at a temperature of about 180~350°C, a heating time of about 100~300 minutes, and a surface pressure of about 20~100kg/cm ² . In addition, a multilayer board can also be produced by combining the prepreg of this embodiment with a wiring board for an inner layer that is produced separately and performing lamination molding. In the method of manufacturing a multilayer board, for example, copper foils of about 35 μm are placed on both sides of a prepreg of this embodiment, laminated and formed by the above-mentioned forming method, an inner layer circuit is formed, and the circuit is implemented. The inner layer circuit board is formed by blackening treatment, and then the inner layer circuit board and the prepreg of this embodiment are alternately arranged one by one, and copper foil is arranged on the outermost layer. Lamination forming under vacuum can produce multi-layer boards. The metal foil-clad laminate of this embodiment can be suitably used as a printed wiring board.

In addition, the metal foil-clad laminate of this embodiment preferably has a low dielectric loss tangent (Df) as measured by using a laminate in which the metal foil is removed by etching. Specifically, the dielectric loss tangent (Df) at 10 GHz measured by the cavity resonator perturbation method is preferably less than 0.0040, more preferably less than 0.0030, further preferably less than 0.0025, and still more preferably less than 0.0025. There is no particular limitation on the lower limit of the dielectric loss tangent (Df), for example, it is 0.0001 or more in practice. The measurement of the dielectric loss tangent follows the description of the examples described later. In addition, the metal foil-clad laminate of this embodiment preferably has a low coefficient of thermal expansion (CTE) as measured by using a laminate in which the metal foil is removed by etching. Specifically, the above-mentioned CTE is preferably 10 ppm/°C or less. The lower limit is ideally 0, and practically 0.001 ppm/°C or more. The measurement of CTE follows the description of the Examples described later.

As described above, the resin composition for electronic materials obtained by using the resin composition of this embodiment (resin composition composed of a combination of specific components) can have a cured product having dielectric properties (low dielectric loss tangent), Good properties of moisture absorption and heat resistance, crack resistance, appearance of hardened products, and low thermal expansion.

＜＜Printed Wiring Board＞＞ The printed wiring board of this embodiment is a printed wiring board including an insulating layer and a conductor layer arranged on the surface of the insulating layer, and the insulating layer includes a layer formed of the resin composition of this embodiment and a prepreg of this embodiment At least one of the layers formed. Such a printed wiring board can be manufactured according to a common method, and the manufacturing method is not specifically limited. An example of the manufacturing method of a printed wiring board is shown below. First, a metal foil-clad laminate such as the above-mentioned copper-clad laminate is prepared. Then, an etching process is performed on the surface of the metal foil-clad laminate to form an inner layer circuit to make an inner layer substrate. According to the requirement, carry out surface treatment to improve the bonding strength on the surface of the inner layer circuit of the inner layer substrate, then stack the required number of the above-mentioned prepregs on the surface of the inner layer circuit, and further laminate the outer layer circuit on the outside The metal foil is formed into one by heating and pressing. In this way, a multi-layer laminate in which a base material and an insulating layer made of a hardened resin composition are formed between the metal foils for the inner layer circuit and the outer layer circuit is produced. Next, after the through hole or via hole is applied to the multi-layer laminated board, the metal foil for the inner layer circuit and the outer layer circuit is formed on the wall surface of the hole. The metal film is plated, and the metal foil for the outer circuit is further etched to form an outer circuit to manufacture a printed wiring board.

The printed wiring board obtained in the above production example has an insulating layer and a conductive layer formed on the surface of the insulating layer, and the insulating layer is composed of the above-mentioned resin composition and/or cured product of the present embodiment. That is, the above-mentioned prepreg of this embodiment (for example, a prepreg formed of a base material and the resin composition of this embodiment impregnated or coated on the base material), the metal foil-clad laminate of this embodiment above The layer formed of the resin composition of the board becomes the insulating layer of this embodiment. In addition, the present embodiment also relates to a semiconductor device including the above-mentioned printed wiring board. For details of the semiconductor device, refer to paragraphs 0200 to 0202 of JP-A-2021-021027, and these contents are incorporated into this specification.

＜＜Resin Composite Sheet＞＞ The resin composite sheet of this embodiment contains a support body, and the layer which consists of the resin composition of this embodiment arrange|positioned on the surface of this support body. Resin composite sheets can be used as stack-up films or dry film solder masks. The method for producing the resin composite sheet is not particularly limited, and for example, a solution obtained by dissolving the above-mentioned resin composition of the present embodiment in a solvent is applied (coated) on a support and dried, And obtain the method of resin composite sheet.

As the support used here, for example, polyethylene film, polypropylene film, polycarbonate film, polyethylene terephthalate film, ethylene tetrafluoroethylene copolymer film, and the Release film coated with a release agent on the surface, organic film substrates such as polyimide film, conductive foil such as copper foil and aluminum foil, glass plate, SUS (Steel Use Stainless) plate, FRP (Fiber-Reinforced Plastics (Fiber-Reinforced Plastics)) and other plate-shaped objects are not particularly limited.

As for the coating method (coating method), for example, a solution obtained by dissolving the resin composition of the present embodiment in a solvent can be applied on the methods on the support body. In addition, a single-layer sheet can also be obtained by peeling or etching the support from the resin composite sheet obtained by laminating the support and the resin composition after drying. In addition, by supplying the solution obtained by dissolving the resin composition of the above-mentioned embodiment in a solvent into a mold having a sheet-shaped cavity, drying, etc., and forming it into a sheet shape, it is also possible to form a sheet without using a support. A single layer tablet is obtained.

In addition, in the production of the single-layer sheet or the resin composite sheet of this embodiment, the drying conditions when removing the solvent are not particularly limited, considering that if it is low temperature, the solvent will easily remain in the resin composition, and if it is high temperature, the resin composition will be damaged. The material will harden, so it is advisable to use it at a temperature of 20°C~200°C for 1~90 minutes. In addition, in a single-layer sheet or a resin composite sheet, the resin composition can be used in an uncured state obtained by drying only the solvent, or in a semi-cured (B-staged) state as required. In addition, the thickness of the resin layer in the single-layer sheet or resin composite sheet of this embodiment can be adjusted by the concentration of the solution of the resin composition of this embodiment and the coating thickness during coating (coating), and there is no special limitation. , considering that generally, when the coating thickness becomes thicker, the solvent tends to remain during drying, it is preferably 0.1 to 500 μm. [Example]

Examples are given below to describe the present invention more specifically. Materials, usage amounts, ratios, processing contents, processing procedures, and the like shown in the following examples can be appropriately changed without departing from the gist of the present invention. Therefore, the scope of the present invention is not limited to the specific examples shown below. In the event that the measuring instruments used in the examples are difficult to obtain due to production discontinuation, etc., other instruments with equivalent performance can be used for measurement.

<Synthesis Example 1 Synthesis of Modified Polyphenylene Ether Compound><<Synthesis of Bifunctional Phenyl Ether Oligomer>> CuBr was added to a 12L vertical reactor equipped with a stirring device, a thermometer, an air inlet tube, and a partition ₂ 9.36g (42.1mmol), 1.81g (10.5mmol) of N,N'-di-tert-butylethylenediamine, 67.77g (671.0mmol) of n-butyldimethylamine, 2,600g toluene, at a reaction temperature of 40 ℃, 129.32g (0.48mol) of 2,2',3,3',5,5'-hexamethyl-(1,1'-biphenol)-4,4'-diol, 878.4g (7.2mol) of 2,6-dimethylphenol, 1.22g (7.2mmol) of N,N'-di-tert-butylethylenediamine, and 26.35g (260.9mmol) of n-butyldimethylamine were dissolved in A mixed solution of 2,300 g of methanol was added dropwise and stirred over 230 minutes in a state where nitrogen and air were mixed and adjusted to an oxygen concentration of 8 vol% and the mixed gas was bubbling at a flow rate of 5.2 L/min. After completion of the dropwise addition, 1,500 g of water in which 48.06 g (126.4 mmol) of tetrasodium ethylenediaminetetraacetate was dissolved was added to stop the reaction. The aqueous layer and the organic layer were liquid-separated, and the organic layer was washed with 1N aqueous hydrochloric acid solution and then with pure water. The obtained solution was concentrated to 50% by mass by an evaporator to obtain 1981 g of a toluene solution of a bifunctional phenylene ether oligomer (resin "A"). Resin "A" had a polystyrene-equivalent number average molecular weight of 1975 by GPC method, a polystyrene-equivalent weight average molecular weight of 3514 by GPC method, and a hydroxyl equivalent of 990.

＜＜Synthesis of Modified Polyphenylene Ether Compound＞＞ Into a reactor equipped with a stirring device, a thermometer, and a reflux tube, 833.4 g of a toluene solution of resin "A", 76.7 g of vinylbenzyl chloride (manufactured by AGC SEIMI CHEMICAL CO., LTD., "CMS-P"), 1,600 g of dichloromethane, 6.2 g of benzyldimethylamine, 199.5 g of pure water, and 83.6 g of a 30.5% by mass NaOH aqueous solution were stirred at a reaction temperature of 40°C. After stirring for 24 hours, the organic layer was washed with 1N aqueous hydrochloric acid solution and then with pure water. The obtained solution was concentrated with an evaporator, dropped into methanol to solidify, and the solid was collected by filtration and vacuum-dried to obtain 450.1 g of a modified polyphenylene ether compound. The number average molecular weight in terms of polystyrene by GPC method of the modified polyphenylene ether compound was 2250, the weight average molecular weight in terms of polystyrene by GPC method was 3920, and the vinyl equivalent was 1189 g/vinyl.

<Synthesis Example 2 Synthesis of naphthol aralkyl type cyanate compound (SNCN)> Make α-naphthol aralkyl resin (SN495V, OH group equivalent: 236g/eq., manufactured by Nippon Steel Chemical Co., Ltd.: The number of repeating units including a naphthol aralkyl group is 1 to 5.) 0.47 mol (OH group conversion) was dissolved in 500 mL of chloroform, and 0.7 mol of triethylamine was added to the solution to prepare a solution 1. With the temperature maintained at -10°C, solution 1 was added dropwise over 1.5 hours to 300 g of a 0.93 mole cyanogen chloride solution in chloroform added to the reactor, and stirred for 30 minutes after the addition was complete. Thereafter, a mixed solution of 0.1 mol of triethylamine and 30 g of chloroform was dropped into the reactor, and stirred for 30 minutes to complete the reaction. After the hydrochloride of triethylamine produced as a by-product was separated by filtration from the reaction solution, the obtained filtrate was washed with 500 mL of 0.1N hydrochloric acid, and then washed with 500 mL of water was repeated 4 times. After drying it over sodium sulfate, evaporate it at 75°C, and degas it under reduced pressure at 90°C to obtain the α-naphthol aralkyl type cyanate compound represented by formula (S1) as a brown solid (where R ^C1 ~ R ^C4 are all hydrogen atoms, n ^c is a mixture of 1 ~ 5.). The obtained α-naphthol aralkyl type cyanate compound was analyzed by infrared absorption spectrum, and it was confirmed that there was cyanate group absorption around 2264 cm ^-1 . [chem 42]

<Synthesis Example 3 Synthesis of Polymer (va) Having a Structural Unit Represented by Formula (V)> Put into the reactor 2.25 moles (292.9g) of divinylbenzene, 1.32 moles (172.0g) of ethyl vinylbenzene, 11.43 moles (1190.3g) of styrene, 15.0 moles (1532.0g) of n-propyl acetate ), adding 600 millimoles of boron trifluoride diethyl ether complex at 70° C., and allowing it to react for 4 hours. After stopping the polymerization reaction with aqueous sodium bicarbonate solution, the oil layer was washed 3 times with pure water, and devolatilized under reduced pressure at 60° C. to recover polymer (va) having a constituent unit represented by formula (V). The obtained polymer (va) having the structural unit represented by the formula (V) was weighed, and it was confirmed that 860.8 g of the polymer (va) having the structural unit represented by the formula (V) was obtained.

The obtained polymer (va) having a constituent unit represented by formula (V) had a number average molecular weight Mn of 2,060, a weight average molecular weight Mw of 30,700, and a monodispersity Mw/Mn of 14.9. By conducting ¹³ C-NMR and ¹ H-NMR analysis, in the polymer (va) having a structural unit represented by formula (V), resonance lines derived from each monomer unit used as a raw material were observed. Based on the NMR measurement results and GC analysis results, the ratio of each monomer unit (constituent unit derived from each raw material) in the polymer (va) having a structural unit represented by formula (V) was calculated as follows. Constituent units derived from divinylbenzene: 20.9 mol % (24.3 mass %) Constituent units derived from ethylvinylbenzene: 9.1 mol % (10.7 mass %) Constituent units derived from styrene: 70.0 mol % (65.0 % by mass) In addition, the structural unit having a residual vinyl group derived from divinylbenzene was 16.7 mol% (18.5% by mass).

<Determination of weight average molecular weight and number average molecular weight> Weight average molecular weight (Mw) and number average molecular weight (Mn) are determined by gel permeation chromatography (GPC) method. A liquid delivery pump (manufactured by Shimadzu Corporation, LC-20AD), a differential refractive index detector (manufactured by Shimadzu Corporation, RID-10A), a GPC column (manufactured by Showa Denko Corporation, GPC KF-801, 802, 803, 804), tetrahydrofuran was used as the solvent, the flow rate was 1.0mL/min, the column temperature was 40°C, and the calibration curve caused by monodisperse polystyrene was used.

Example 1 Mix 30 parts by mass of the modified polyphenylene ether compound obtained in Synthesis Example 1 above, and a maleimide compound (manufactured by Nippon Kayaku Co., Ltd., MIR-3000-70MT, equivalent to the compound represented by formula (M3)) 30 Parts by mass, 5 parts by mass of the naphthol aralkyl type cyanate compound (SNCN) obtained in Synthesis Example 2 above, α-methylstyrene oligomer (KA3085 (trade name), weight average molecular weight: 664, Eastman Chemical Company) 5 parts by mass, phosphorus-based flame retardant (PX-200, Daihachi Chemical Industry Co., Ltd.) 15 parts by mass, hydrogenated styrene-based thermoplastic elastomer (SEBS, SEPTON2104, Mn83000, Kuraray Co., Ltd. 7.5 parts by mass, non-hydrogenated styrene-based thermoplastic elastomer (SBS, TR2250, Mn115000, manufactured by JSR Co., Ltd.) 7.5 parts by mass, silicon dioxide (manufactured by Admatechs Company Limited, SC2050-MNU) 100 parts by mass, using methyl ethyl ketone The varnish was obtained by diluting to 65% by mass in terms of solid content. In addition, the compounding quantity of each component shows the solid content quantity.

This varnish was dip-coated on NE glass fabric with a thickness of 0.1 mm (manufactured by Nitto Industries Co., Ltd., 2013 S101S), and heated and dried at 165° C. for 5 minutes to obtain a prepreg with a resin composition content of 60% by mass (thickness 0.1mm). In addition, the characteristics of the NE glass woven fabric used are as follows. Types corresponding to IPC: 2013 Longitudinal density (root/25mm): 46 Transverse density (root/25mm): 44.1 Thickness (mm): 0.070 Mass (g/m ² ): 80.7 The prepreg to be obtained is 1 piece or stacked 8 pieces , arrange 12μm-thick electrolytic copper foil (3EC-M3-VLP, manufactured by Mitsui Metal Mining Co., Ltd.) on both sides, and vacuum press at a pressure of 30kgf/cm ² and a temperature of 220°C for 120 minutes to obtain an insulating layer with a thickness of 0.1mm or 0.8 mm copper clad laminates as metal clad laminates.

For the obtained copper clad laminates, the physical properties (dielectric loss tangent (Df), moisture absorption heat resistance, crack resistance, appearance after curing, coefficient of thermal expansion (CTE)) were evaluated according to the method described later.

＜Dielectric loss tangent＞ For the obtained copper-clad laminated board, the test piece (30mm×150mm×0.8mm) produced by etching and removing the copper foil was used to measure the dielectric loss tangent (Df ). The measurement temperature was set at 23°C. The cavity resonator of the perturbation method used Agilent Technologies, Ltd. product, Agilent8722ES. Evaluation was performed as follows. A: Less than 0.0025 B: 0.0025 or more

＜Moisture absorption and heat resistance＞ With respect to the obtained copper-clad laminate, all the copper foil on one side was removed by etching, and half of the copper foil on the other side was removed by etching to prepare a test piece (50 mm×50 mm×0.8 mm). The test piece was left to stand in the presence of saturated water vapor at 121°C and 2 atmospheres for 3 hours using a pressure cooking tester, and then immersed in a solder bath at 260°C for 30 seconds to observe whether it peeled off. The pressure cooking tester is PC-3 manufactured by Hirayama Seisakusho Co., Ltd. A: No abnormality B: with peeling

＜Crack resistance (MIT test)＞ For the obtained copper-clad laminate, according to JIS C5016:1994, a test piece (15mm×130mm×0.1mm) with a wiring pattern of a wiring width of 1mm was formed on the copper foil, and the terminal part of the conductor pattern of the test piece was installed. Set the wire covered with insulation, fix the upper end of the test piece to the plunger, set a load of 1kgf on the lower end, and start bending in two directions at an angle of 135° and a speed of 175cpm in the energized state, and measure until the wire breaks The number of back and forth bending so far. Evaluation was performed as follows. S: more than 81 times A: More than 71 times and less than 80 times B: More than 40 times and less than 70 times C: Less than 39 times

＜Appearance after hardening＞ The copper foil of the obtained copper-clad laminate was removed by etching to obtain a test piece (330 mm×330 mm×0.1 mm) for external appearance observation after hardening. The surface was observed to confirm the separation state of the thermoplastic elastomer (A) and/or thermoplastic elastomer (B) and the thermosetting resin (C), and the presence or absence of abnormal appearance was evaluated by the following evaluation criteria. Evaluation was performed as follows. The evaluation was conducted by a majority vote of 5 experts. A: No abnormality B: Poor appearance

＜Coefficient of thermal expansion (CTE: Coefficient of linear Thermal Expansion)＞ For the test piece (4.5mm×10mm×0.1mm) obtained by etching and removing the copper foil of the obtained copper-clad laminate, the TMA method (thermomechanical analysis: Thermo- Mechanical Analysis), measure the thermal expansion coefficient of the test piece, and obtain its value. Specifically, the copper foil on both sides of the copper-clad laminate obtained above was removed by etching and the size was reduced, and then the temperature was raised from 30°C to 340°C at 10°C per minute in a thermomechanical analysis device (manufactured by TA Instruments). , Measure the linear coefficient of thermal expansion (CTE(X)) (unit: ppm/°C) from 30°C to 300°C in the plane direction. The measurement direction is to measure the longitudinal direction (Warp) of the glass cloth of the laminate. ppm is the volume ratio. For other details, the above-mentioned JIS C 6481 5.19 is followed. Evaluation was performed as follows. A: Below 10ppm/℃ B: more than 10ppm/℃

Example 2 In Example 1, the hydrogenated styrene-based thermoplastic elastomer (SEPTON2104) was changed to the same amount of hydrogenated styrene-based thermoplastic elastomer (SEBS, S.O.E. (registered trademark) S1605, Mn250000, manufactured by Asahi Kasei Co., Ltd.), except Otherwise, proceed in the same manner.

Example 3 In Example 2, a partially hydrogenated styrene-based thermoplastic elastomer (SBBS, S.O.E. (registered trademark) S1609, Mn228000, manufactured by Asahi Kasei Co., Ltd.) was mixed with an equivalent amount to replace the non-hydrogenated styrene-based thermoplastic elastomer (SBS, Except for TR2250 and Mn115000, manufactured by Asahi Kasei Co., Ltd.), it carried out in the same manner.

Example 4 In Example 3, the blending amount of the modified polyphenylene ether compound obtained in the above Synthesis Example 1 was changed to 15 parts by mass, and 15 parts by mass of the polymer (va) obtained in the above Synthesis Example 3 was further blended. , proceed in the same way.

Example 5 In Example 4, the blending amount of the hydrogenated styrene-based thermoplastic elastomer (SEBS, S.O.E. (registered trademark) S1605, Mn250000, manufactured by Asahi Kasei Co., Ltd.) was changed to 2 parts by mass, and the partially hydrogenated styrene-based thermoplastic elastomer It carried out in the same manner except having changed the compounding quantity of the elastomer (SBBS, S.O.E. (registered trademark) S1609, Mn228000, manufactured by Asahi Kasei Co., Ltd.) to 13 parts by mass.

Comparative example 1 In Example 1, hydrogenated styrene-based thermoplastic elastomer (SEPTON2104) and non-hydrogenated styrene-based thermoplastic elastomer (TR2250) were not blended, and a blend of maleimide compound (MIR-3000-70MT) Except having changed the quantity into 45 mass parts, it carried out in the same manner.

Comparative example 2 In Example 1, no hydrogenated styrene-based thermoplastic elastomer (SEPTON2104) and non-hydrogenated styrene-based thermoplastic elastomer (TR2250) were blended, and 15 parts by mass of hydrogenated styrene-based thermoplastic elastomer (S1605) was blended, except Otherwise, proceed in the same manner.

Comparative example 3 In Example 1, it carried out similarly except having mixed the hydrogenated styrene-type thermoplastic elastomer (S1605) of the same amount instead of the non-hydrogenated styrene-type thermoplastic elastomer (TR2250).

Comparative example 4 In Example 1, the modified polyphenylene ether compound obtained in Synthesis Example 1 above was not blended, and the blending amount of the maleimide compound (MIR-3000-70MT) was changed to 60 parts by mass. Proceed in the same way.

Comparative Example 5 In Comparative Example 4, the hydrogenated styrene-based thermoplastic elastomer (SEPTON 2104) was blended with the same amount of hydrogenated styrene-based thermoplastic elastomer (S1605), and it was carried out in the same manner.

[Table 1] Example 1 Example 2 Example 3 Example 4 Example 5 Dielectric loss tangent A A A A A Moisture absorption and heat resistance A A A A A Crack resistance A S S A S Appearance after hardening A A A A A CTE(X) A A A A A

[Table 2] Comparative example 1 Comparative example 2 Comparative example 3 Comparative example 4 Comparative Example 5 Dielectric loss tangent B A A B B Moisture absorption and heat resistance A B B B B Crack resistance C S S A S Appearance after hardening A A A B B CTE(X) B A A A A

Claims (21)

A resin composition comprising a thermoplastic elastomer (A), a thermoplastic elastomer (B), and a thermosetting resin (C) compatible with both the thermoplastic elastomer (A) and the thermoplastic elastomer (B), The thermoplastic elastomer (A) is a thermoplastic elastomer containing a styrene monomer unit and a conjugated diene monomer unit and having a number average molecular weight of 50,000 or more, in which all conjugated diene bonds of the thermoplastic elastomer are removed Thermoplastic elastomers obtained by hydrogenation, The thermoplastic elastomer (B) is a part of the conjugated diene bond of the thermoplastic elastomer in the thermoplastic elastomer containing styrene monomer units and conjugated diene monomer units and having a number average molecular weight of 50,000 or more A thermoplastic elastomer obtained by hydrogenation, and/or a thermoplastic elastomer with all unsaturated bonds. The resin composition according to claim 1, wherein, in the resin composition, the total content of the thermoplastic elastomer (A) and the thermoplastic elastomer (B) is 1 to 40 parts by mass relative to 100 parts by mass of the resin solid content parts by mass. The resin composition according to claim 1 or 2, wherein, in the resin composition, the mass ratio of the thermoplastic elastomer (A) to the thermoplastic elastomer (B) is 1:1~10. The resin composition according to claim 1 or 2, wherein the compatible thermosetting resin (C) is a thermosetting resin containing an aromatic ring and a vinyl group. The resin composition according to claim 1 or 2, wherein the compatible thermosetting resin (C) comprises a polymer selected from a constituent unit represented by formula (V), and a polymer having a carbon-carbon One or more of the group consisting of polyphenylene ether compounds with saturated double bonds; In formula (V), Ar represents an aromatic hydrocarbon linking group; * represents a bonding position. The resin composition according to claim 1 or 2, wherein the content of the compatible thermosetting resin (C) is 10 to 90 parts by mass relative to 100 parts by mass of resin solid content. The resin composition according to claim 1 or 2, further comprising at least one other resin (D) selected from the group consisting of cyanate compounds, maleimide compounds, and epoxy compounds. The resin composition as claimed in item 7, wherein the maleimide compound is selected from the group consisting of compounds represented by formula (M0), compounds represented by formula (M1), compounds represented by formula (M2), compounds represented by formula (M3 ) compound, compound represented by formula (M4), and compound represented by formula (M5) constituted by one or more species; In formula (M0), R ⁵¹ each independently represent a hydrogen atom, an alkyl group with 1 to 8 carbons, or a phenyl group, R ⁵² each independently represent a hydrogen atom or a methyl group, and n ₁ represents an integer of 1 or more; 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 an alicyclic group of 4~6 member ring; R ^M7 and R ^M8 are each independently an alkyl group; mx is 1 or 2, lx is 0 or 1; R ^M9 and R ^M10 are independently R ^M11 , R ^M12 , R ^M13 , and R ^M14 each independently represent a hydrogen atom or an organic group; R ^M15 each independently represent an alkyl group with a carbon number of 1 to 10, and a carbon number of 1 Alkyloxy with ~10 carbons, alkylthio with 1 to 10 carbons, aryl with 6 to 10 carbons, aryloxy with 1 to 10 carbons, arylthio with 1 to 10 carbons, Halogen atom, hydroxyl or mercapto; px represents an integer from 0 to 3; nx represents an integer from 1 to 20; In formula (M2), R ⁵⁴ each independently represent a hydrogen atom or a methyl group, n ₄ represents an integer of 1 or more; In the formula (M3), ^R55 each independently represent a hydrogen atom, an alkyl group with 1 to 8 carbons, or a phenyl group, and _n5 represents an integer ranging from 1 to 10; In formula (M4), R ⁵⁶ each independently represent a hydrogen atom, methyl or ethyl, and R ⁵⁷ each independently represent a hydrogen atom or methyl; In formula (M5), R ⁵⁸ each independently represent a hydrogen atom, an alkyl group having 1 to 8 carbons, or a phenyl group, R ⁵⁹ each independently represent a hydrogen atom or a methyl group, and n ₆ represents an integer of 1 or more. The resin composition according to claim 7, wherein the maleimide compound comprises a compound represented by formula (M1) and/or a compound represented by formula (M3); 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 an alicyclic group of 4~6 member ring; R ^M7 and R ^M8 are each independently an alkyl group; mx is 1 or 2, lx is 0 or 1; R ^M9 and R ^M10 are independently R ^M11 , R ^M12 , R ^M13 , and R ^M14 each independently represent a hydrogen atom or an organic group; R ^M15 each independently represent an alkyl group with a carbon number of 1 to 10, and a carbon number of 1 Alkyloxy with ~10 carbons, alkylthio with 1 to 10 carbons, aryl with 6 to 10 carbons, aryloxy with 1 to 10 carbons, arylthio with 1 to 10 carbons, Halogen atom, hydroxyl or mercapto; px represents an integer from 0 to 3; nx represents an integer from 1 to 20; In the formula (M3), R ⁵⁵ each independently represent a hydrogen atom, an alkyl group having 1 to 8 carbons, or a phenyl group, and n ₅ represents an integer of 1 to 10. The resin composition according to claim 1 or 2 further contains a flame retardant (E). The resin composition according to claim 10, wherein the flame retardant (E) includes a phosphorus-based flame retardant. The resin composition according to claim 1 or 2 further contains a filler (F). The resin composition according to claim 12, wherein the filler (F) comprises silicon dioxide, aluminum hydroxide, aluminum nitride, boron nitride, forsterite, titanium oxide, titanic acid One or more species selected from the group consisting of barium, strontium titanate, and calcium titanate. The resin composition according to claim 12, wherein the content of the filler (F) is 10 to 300 parts by mass relative to 100 parts by mass of the solid content of the resin. If the resin composition of Claim 1 or 2 further contains monomers or oligomers with ethylenically unsaturated groups, the content of monomers or oligomers with ethylenically unsaturated groups is 100% relative to the solid content of the resin. Parts by mass are 0.5 to 30 parts by mass. The resin composition according to claim 1, wherein, in the resin composition, the total content of the thermoplastic elastomer (A) and the thermoplastic elastomer (B) is 1 to 40 parts by mass relative to 100 parts by mass of the resin solid content Parts by mass; In the resin composition, the mass ratio of the thermoplastic elastomer (A) to the thermoplastic elastomer (B) is 1:1~10; the compatible thermosetting resin (C) contains aromatic rings and Vinyl thermosetting resin; The compatible thermosetting resin (C) comprises a polymer selected from the constituent units represented by formula (V), and a polymer having a carbon-carbon unsaturated double bond at the end. One or more of the group consisting of phenyl ether compounds; In the formula (V), Ar represents an aromatic hydrocarbon linking group; * represents a bonding position; the content of the compatible thermosetting resin (C) is 10 to 90 parts by mass relative to 100 parts by mass of the solid content of the resin; The resin composition further contains at least one other resin (D) selected from the group consisting of cyanate compounds, maleimide compounds, and epoxy compounds; the maleimide compound includes selected At least one selected from the group consisting of compounds represented by formula (M1), compounds represented by formula (M3), and compounds represented by formula (M5); the resin composition further contains a flame retardant (E); The flame retardant (E) contains a phosphorus-based flame retardant; the resin composition further contains a filler (F); the filler (F) contains a material selected from silicon dioxide, aluminum hydroxide, aluminum nitride, nitrogen One or more of the group consisting of boron oxide, forsterite, titanium oxide, barium titanate, strontium titanate, and calcium titanate; the content of the filler (F) is 100% relative to the solid content of the resin Parts by mass, 10 to 300 parts by mass; The resin composition further contains monomers or oligomers with ethylenically unsaturated groups, the content of monomers or oligomers with ethylenically unsaturated groups, relative to the resin 100 parts by mass of solid content is 0.5 to 30 parts by mass; 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 an alicyclic group of 4~6 member ring; R ^M7 and R ^M8 are each independently an alkyl group; mx is 1 or 2, lx is 0 or 1; R ^M9 and R ^M10 are independently R ^M11 , R ^M12 , R ^M13 , and R ^M14 each independently represent a hydrogen atom or an organic group; R ^M15 each independently represent an alkyl group with a carbon number of 1 to 10, and a carbon number of 1 Alkyloxy with ~10 carbons, alkylthio with 1 to 10 carbons, aryl with 6 to 10 carbons, aryloxy with 1 to 10 carbons, arylthio with 1 to 10 carbons, Halogen atom, hydroxyl or mercapto; px represents an integer from 0 to 3; nx represents an integer from 1 to 20; In the formula (M3), ^R55 each independently represent a hydrogen atom, an alkyl group with 1 to 8 carbons, or a phenyl group, and _n5 represents an integer ranging from 1 to 10; In formula (M5), R ⁵⁸ each independently represent a hydrogen atom, an alkyl group having 1 to 8 carbons, or a phenyl group, R ⁵⁹ each independently represent a hydrogen atom or a methyl group, and n ₆ represents an integer of 1 or more. A prepreg is formed from a base material and the resin composition according to any one of claims 1 to 16. A metal foil-clad laminate comprising: at least one layer formed of the prepreg according to claim 17, and metal foils arranged on one or both sides of the layer formed of the prepreg. A resin composite sheet comprising a support and a layer formed of the resin composition according to any one of claims 1 to 16 arranged on the surface of the support. A printed wiring board comprising an insulating layer and a conductor layer arranged on the surface of the insulating layer, the insulating layer including a layer formed of the resin composition according to any one of claims 1 to 16. A semiconductor device comprising the printed wiring board according to claim 20.