Resin compositions, prepregs, metal foil laminates, resin composites, printed wiring boards, and semiconductor devices.

Abstract

The present invention provides novel resin compositions that maintain excellent low dielectric loss tangent while exhibiting excellent moisture absorption and heat resistance, as well as prepregs, metal foil laminates, resin composites, printed wiring boards, and semiconductor devices. This invention provides a resin composition comprising a thermoplastic elastomer (A), a thermoplastic elastomer (B), and a thermosetting resin (C) compatible with both elastomers (A) and (B). The thermoplastic elastomer (A) is obtained by hydrogenating all the conjugated diene bonds of a thermoplastic elastomer containing styrene monomer units and conjugated diene monomer units with a number average molecular weight of 50,000 or more. The thermoplastic elastomer (B) is obtained by hydrogenating a portion of the conjugated diene bonds of a thermoplastic elastomer containing styrene monomer units and conjugated diene monomer units with a number average molecular weight of 50,000 or more, and / or is a thermoplastic elastomer with all bonds being unsaturated.

Description

Technical Field

[0001] This invention relates to resin compositions, prepregs, metal foil laminates, resin composites, printed wiring boards, and semiconductor devices. Prior Technology

[0002] In recent years, starting with portable devices, semiconductor components used in electronic and communication equipment have been rapidly becoming more integrated and miniaturized. This has led to a demand for technologies capable of high-density mounting of semiconductor components, requiring improvements to the crucial printed circuit boards (PCBs). On the other hand, the applications of electronic devices and the like continue to diversify and expand. Consequently, the various characteristics required for printed circuit boards, the metal-clad laminates used in them, and prepregs have become more diverse and stringent. To obtain improved printed circuit boards that take into account these required characteristics, various materials and processing methods have been proposed. One example is the improved development of resin materials constituting the prepreg.

[0003] For example, Patent Document 1 discloses a resin composition containing a maleicimine compound (A), a cyanate compound (B), a polyphenylene ether compound (C) with an average molecular weight of 1,000 or more to 7,000 as indicated in a predetermined formula, and a block copolymer (D) having a styrene backbone. In addition, Patent Document 2 discloses a resin composition containing a polyfunctional vinyl aromatic polymer (A) and a thermosetting compound (B), and without a free radical polymerization initiator. [Previous Technical Documents] [Patent Literature]

[0004] [Patent Document 1] International Publication No. 2019 / 230945 [Patent Document 2] International Publication No. 2020 / 175537 Summary of the Invention

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

[0006] As mentioned above, the applications of electronic devices and the like continue to diversify and expand, requiring new materials for the resins that constitute prepregs. In particular, there is a growing demand for resin compositions that maintain excellent low dielectric loss tangent while exhibiting good moisture absorption and heat resistance. The purpose of this invention is to solve the above-mentioned problems and to provide novel resin compositions, as well as prepregs, metal foil laminates, resin composites, printed wiring boards, and semiconductor devices that maintain excellent low dielectric loss tangent while exhibiting excellent moisture absorption and heat resistance. [Methods for solving problems]

[0007] Based on the aforementioned issues, the inventors, after investigation, solved these issues by using a predetermined hydrogenated thermoplastic elastomer with a predetermined partially hydrogenated or non-hydrogenated thermoplastic elastomer. Specifically, the aforementioned issues were solved by the following means. <1> 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 obtained by hydrogenating all the conjugated diene bonds in a thermoplastic elastomer containing styrene monomer units and conjugated diene monomer units with a number average molecular weight of 50,000 or more. The thermoplastic elastomer (B) is a thermoplastic elastomer obtained by hydrogenating a portion of the conjugated diene bonds in a thermoplastic elastomer containing styrene monomer units and conjugated diene monomer units with a number average molecular weight of 50,000 or more, and / or a thermoplastic elastomer with all bonds being unsaturated. <2> like <1> The resin composition 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 relative to 100 parts by mass of the resin solids. <3> like <1> or <2> The resin composition wherein the mass ratio of the thermoplastic elastomer (A) to the thermoplastic elastomer (B) in the resin composition is 1:1 to 10. <4> like <1> ~ <3> The resin composition of any one of the following, wherein the compatible thermosetting resin (C) is a thermosetting resin containing an aromatic ring and a vinyl group. <5> like <1> ~ <4> The resin composition of any one of the following, wherein the compatible thermosetting resin (C) comprises one or more selected from the group consisting of polymers having constituent units represented by formula (V) and polyphenylene ether compounds having carbon-carbon unsaturated double bonds at the ends; [Chemistry 1] (In formula (V), Ar represents an aromatic hydrocarbon linker; * indicates the bond position.) <6> like <1> ~ <5> The resin composition of any one of the following, wherein the content of the compatible thermosetting resin (C) is 10 to 90 parts by mass relative to 100 parts by mass of the resin solids. <7> like <1> ~ <6> The resin composition of any one of the following, wherein it further contains one or more other resins selected from the group consisting of cyanate compounds, maleimide compounds and epoxy compounds (D). <8> like <7> The resin composition, wherein the maleimine compound comprises one or more compounds 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), compounds represented by formula (M4), and compounds represented by formula (M5). [Chemistry 2] (In formula (M0), R51 each independently represents a hydrogen atom, an alkyl group with 1 to 8 carbon atoms, or a phenyl group; R52 each independently represents a hydrogen atom or a methyl group; and n1 represents an integer greater than 1.) [Chemistry 3] In formula (M1), RM1, RM2, RM3, and RM4 each independently represent a hydrogen atom or an organic group; RM5 and RM6 each independently represent a hydrogen atom or an alkyl group; ArM represents a divalent aromatic group; A represents a 4-6 membered alicyclic group; RM7 and RM8 each independently represent an alkyl group; mx represents 1 or 2, lx represents 0 or 1; RM9 and RM10 each independently represent a hydrogen atom or an alkyl group; RM11, RM12, RM13, and RM14 each independently represent a hydrogen atom or an organic group; R The M15 series independently represents alkyl, alkyloxy, alkylthio, aryl, aryloxy, arylthio, halogen, hydroxyl, or mercapto groups having 1 to 10 carbon atoms; px represents an integer from 0 to 3; nx represents an integer from 1 to 20. [Chemistry 4] (In formula (M2), R 54 each independently represents a hydrogen atom or a methyl group, and n 4 represents an integer greater than or equal to 1.) [Chemistry 5] (In formula (M3), R 55 each independently represents a hydrogen atom, an alkyl group with 1 to 8 carbon atoms, or a phenyl group, and n 5 represents an integer between 1 and 10.) [Chemistry 6] (In formula (M4), R56 series each independently represents a hydrogen atom, a methyl group, or an ethyl group, and R57 series each independently represents a hydrogen atom or a methyl group.) [Chemistry 7] (In formula (M5), R 58 each independently represents a hydrogen atom, an alkyl group with 1 to 8 carbon atoms, or a phenyl group; R 59 each independently represents a hydrogen atom or a methyl group; and n 6 represents an integer greater than 1.) <9> like <7> The resin composition, wherein the maleimide compound comprises a compound represented by formula (M1) and / or a compound represented by formula (M3); [Chemistry 8] In formula (M1), RM1, RM2, RM3, and RM4 each independently represent a hydrogen atom or an organic group; RM5 and RM6 each independently represent a hydrogen atom or an alkyl group; ArM represents a divalent aromatic group; A represents a 4-6 member alicyclic group. RM7 and RM8 each independently represent an alkyl group; mx represents 1 or 2, lx represents 0 or 1; RM9 and RM10 each independently represent a hydrogen atom or an alkyl group; RM11, RM12, RM13, and RM14 each independently represent a hydrogen atom or an organic group; R The M15 series independently represents alkyl, alkyloxy, alkylthio, aryl, aryloxy, arylthio, halogen, hydroxyl, or mercapto groups having 1 to 10 carbon atoms; px represents an integer from 0 to 3; nx represents an integer from 1 to 20. [Chemistry 9] (In formula (M3), R 55 each independently represents a hydrogen atom, an alkyl group with 1 to 8 carbon atoms, or a phenyl group, and n 5 represents an integer between 1 and 10.) <10> like <1> ~ <9> The resin composition of any one of them also contains a flame retardant (E). <11> like <10> The resin composition, wherein the flame retardant (E) comprises a phosphorus-based flame retardant. <12> like <1> ~ <11> The resin composition of any one of them further contains filler (F). <13> like <12> The resin composition, wherein the filler (F) comprises one or more selected from the group consisting of silicon dioxide, aluminum hydroxide, aluminum nitride, boron nitride, forsterite, titanium dioxide, barium titanate, strontium titanate, and calcium titanate. <14> like <12> or <13> The resin composition, wherein the content of the filler (F) is 10 to 300 parts by mass relative to 100 parts by mass of the resin solids. <15> like <1> ~ <14> The resin composition of any one of the above contains a monomer or oligomer having an ethylene unsaturated group, and the content of the monomer or oligomer having an ethylene unsaturated group is 0.5 to 30 parts by mass relative to 100 parts by mass of the resin solids. <16> like <1> ~ <15> The resin composition of any one of the following, 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 relative to 100 parts by mass of the resin solids; In this resin composition, the mass ratio of the thermoplastic elastomer (A) to the thermoplastic elastomer (B) is 1:1 to 10; The compatible thermosetting resin (C) is a thermosetting resin containing aromatic rings and vinyl groups; The compatible thermosetting resin (C) comprises one or more selected from the group consisting of polymers having constituent units represented by formula (V) and polyphenylene ether compounds having carbon-carbon unsaturated double bonds at the ends; [Chemistry 10] (In formula (V), Ar represents an aromatic hydrocarbon linker; * indicates the bond 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 solids; The resin composition further contains one or more other resins selected from the group consisting of cyanate compounds, maleimide compounds, and epoxy compounds (D); The maleimine compound comprises one or more compounds 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 also contains flame retardant (E); The flame retardant (E) contains phosphorus-based flame retardants; The resin composition also contains filler (F); The filler (F) comprises one or more of the following: silicon dioxide, aluminum hydroxide, aluminum nitride, boron nitride, forsterite, titanium dioxide, barium titanate, strontium titanate, and calcium titanate. The content of this filler (F) is 10 to 300 parts by weight relative to 100 parts by weight of the resin solids; The resin composition further contains monomers or oligomers with vinyl unsaturated groups, and the content of the monomers or oligomers with vinyl unsaturated groups is 0.5 to 30 parts by weight per 100 parts by weight of the resin solids. [Chemistry 11] In formula (M1), RM1, RM2, RM3, and RM4 each independently represent a hydrogen atom or an organic group; RM5 and RM6 each independently represent a hydrogen atom or an alkyl group; ArM represents a divalent aromatic group; A represents a 4-6 membered alicyclic group; RM7 and RM8 each independently represent an alkyl group; mx represents 1 or 2, lx represents 0 or 1; RM9 and RM10 each independently represent a hydrogen atom or an alkyl group; RM11, RM12, RM13, and RM14 each independently represent a hydrogen atom or an organic group; R The M15 series independently represents alkyl, alkyloxy, alkylthio, aryl, aryloxy, arylthio, halogen, hydroxyl, or mercapto groups having 1 to 10 carbon atoms; px represents an integer from 0 to 3; nx represents an integer from 1 to 20. [Chemistry 12] (In formula (M3), R 55 each independently represents a hydrogen atom, an alkyl group with 1 to 8 carbon atoms, or a phenyl group, and n 5 represents an integer between 1 and 10.) [Chemistry 13] (In formula (M5), R 58 each independently represents a hydrogen atom, an alkyl group with 1 to 8 carbon atoms, or a phenyl group; R 59 each independently represents a hydrogen atom or a methyl group; and n 6 represents an integer greater than 1.) <17> A prepreg, comprising a substrate and, as shown in the figure, a prepreg. <1> ~ <16> The resin composition of any one of the above is formed. <18> A metal foil-coated laminate, comprising: as shown in... <17> A layer formed of at least one layer of a prepreg and a metal foil disposed on one or both sides of the layer formed of the prepreg. <19> A resin composite sheet includes a support and a surface disposed on the support, as shown in the figure. <1> ~ <16> A layer formed from any of the resin compositions mentioned above. <20> A printed wiring board includes an insulating layer and a conductor layer disposed on the surface of the insulating layer, the insulating layer comprising, for example, a conductor layer selected from, <1> ~ <16> The layer formed by any of the resin compositions and the layer formed by such <17> At least one of the layers in which the prepreg is formed. <21> A semiconductor device, comprising such <20> Printed wiring board. [Effects of the Invention]

[0008] This invention provides novel resin compositions, as well as prepregs, metal foil laminates, resin composites, printed wiring boards, and semiconductor devices that maintain excellent low dielectric loss tangent while exhibiting excellent moisture absorption and heat resistance. Implementation

[0009] The following describes in detail the embodiments used to implement the present invention (hereinafter also referred to as "the embodiments"). However, the embodiments described below are illustrative of the present invention, and the present invention is not limited to the embodiments. Furthermore, the "~" in this specification means that the values ​​before and after it are the lower and upper limits. Unless otherwise specified, all physical properties and characteristic values ​​in this specification are based on values ​​at 23°C. In this specification, the use of radicals (atomic groups) without specifying whether they are substituted or unsubstituted includes both unsubstituted and substituted radicals (atomic groups). For example, "alkyl" is not limited to unsubstituted alkyl groups (unsubstituted alkyl groups), but also includes substituted alkyl groups (substituted alkyl groups). In this specification, the use of radicals without specifying whether they are substituted or unsubstituted should be interpreted as unsubstituted. In this specification, relative permittivity refers to the ratio of the dielectric constant of a material to the dielectric constant of vacuum. Furthermore, in this specification, relative permittivity is sometimes simply referred to as "dielectric constant". In this specification, "(meth)acrylic acid" means either or both of acrylic acid and methacrylic acid. In cases where the standards described in this manual vary depending on the year and the measurement methods, unless otherwise specified, they are defined as standards as of January 1, 2021.

[0010] In this specification, the solid resin components refer to the components excluding fillers and solvents. They mainly include thermoplastic elastomer (A), thermoplastic elastomer (B), thermosetting resin (C) compatible with both thermoplastic elastomer (A) and thermoplastic elastomer (B), other resins (D) to be blended as needed, silane coupling agents, and other resin additives (flame retardants and other additives).

[0011] The resin composition of this embodiment is characterized by containing a thermoplastic elastomer (A), a thermoplastic elastomer (B), and a thermosetting resin (C) compatible with both thermoplastic elastomers (A and B). The thermoplastic elastomer (A) is obtained by hydrogenating all the conjugated diene bonds of a thermoplastic elastomer containing styrene monomer units and conjugated diene monomer units with a number average molecular weight of 50,000 or more. The thermoplastic elastomer (B) is obtained by hydrogenating a portion of the conjugated diene bonds of a thermoplastic elastomer containing styrene monomer units and conjugated diene monomer units with a number average molecular weight of 50,000 or more, and / or, is a thermoplastic elastomer with all bonds being unsaturated. By constructing it in this way, a resin composition with excellent moisture absorption and heat resistance can be obtained while maintaining excellent low dielectric loss tangent. Furthermore, in this embodiment, it is speculated that by incorporating thermoplastic elastomers, the resin composition can be given flexibility, effectively suppressing the formation of cracks in the obtained cured product. Further, it is speculated that by incorporating thermoplastic elastomers, the thermal expansion of the cured product can be effectively suppressed. In particular, it is speculated that by using thermoplastic elastomer (A), a resin composition with excellent dielectric properties can be obtained. This is speculated to be due to the decrease in the polarity of the elastomer caused by hydrogenation of the conjugated diene bonds. Furthermore, it is speculated that since thermoplastic elastomer (B) is a resin with a large and highly polar number average molecular weight of 50,000 or more, it has excellent compatibility with the resin components (thermoplastic elastomer (A) and thermosetting resin (C) compatible with (A) and (B)), thereby improving the moisture absorption and heat resistance of the resin composition.

[0012] <Thermoplastic Elastomers (A)> The resin composition of this embodiment contains a thermoplastic elastomer (A). The thermoplastic elastomer (A) is obtained by hydrogenating all the conjugated diene bonds in a thermoplastic elastomer containing styrene monomer units and conjugated diene monomer units with a number average molecular weight of 50,000 or more (in this specification, it is sometimes also referred to as "hydrogenated styrene-based thermoplastic elastomer"). By containing the thermoplastic elastomer (A), excellent effects of low dielectric loss tangent, crack resistance, and low thermal expansion are achieved.

[0013] The thermoplastic elastomer (A) in this embodiment contains styrene monomer units. By containing styrene monomer units, it tends to have excellent compatibility with the thermosetting resin (C). Examples of styrene monomers include styrene, α-methylstyrene, p-methylstyrene, divinylbenzene (vinylstyrene), N,N-dimethyl-p-aminoethylstyrene, and N,N-diethyl-p-aminoethylstyrene. Among these, considering availability and manufacturability, styrene, α-methylstyrene, and p-methylstyrene are preferable. Styrene is particularly preferable among these. The content of styrene monomer units should preferably be in the range of 10-50% by mass of all monomer units, more preferably in the range of 13-45% by mass, and even more preferably in the range of 15-40% by mass. If the content of styrene monomer units is less than 50% by mass, the adhesion and bonding with substrates become better. In addition, if it is 10% by mass or more, it tends to suppress the increase of adhesion, reduce the generation of residues and marks, and improve the ease of peeling between adhesive surfaces, which is therefore more ideal. Thermoplastic elastomer (A) may contain only one type of styrene monomer unit, or it may contain two or more types. In the case of containing two or more types, the total amount should preferably be within the range described above. The method for determining the content of styrene monomer units in the thermoplastic elastomer (A) of this embodiment can be referred to International Publication No. 2017 / 126469, the contents of which are incorporated herein by reference. The same applies to the conjugated diene monomer units, etc., described later.

[0014] The thermoplastic elastomer (A) in this embodiment contains conjugated diene monomer units. By containing conjugated diene monomer units, it tends to exhibit excellent low dielectric loss tangent, crack resistance, and low thermal expansion. There are no particular limitations on the conjugated diene monomer, provided it is a diene having one pair of conjugated double bonds. Examples of conjugated diene monomers include 1,3-butadiene, 2-methyl-1,3-butadiene (isoprene), 2,3-dimethyl-1,3-butadiene, 1,3-pentadiene, 2-methyl-1,3-pentadiene, 1,3-hexadiene, and farnesene; 1,3-butadiene and isoprene are preferred, and 1,3-butadiene is more preferred. Thermoplastic elastomer (A) may contain only one type of conjugated diene monomer unit or more than two types.

[0015] In the thermoplastic elastomer (A) used in this embodiment, the mass ratio of styrene monomer units to conjugated diene monomer units is preferably in the range of 5 / 95 to 40 / 60, more preferably in the range of 7 / 93 to 37 / 63, and even more preferably in the range of 10 / 90 to 35 / 65. If the above-mentioned mass ratio of styrene monomer units to conjugated diene monomer units is in the range of 5 / 95 to 40 / 60, the increase in adhesion can be suppressed and high adhesion can be maintained, and the adhesive surfaces can be easily peeled off.

[0016] The thermoplastic elastomer (A) used in this embodiment is a thermoplastic elastomer in which all conjugated diene bonds are hydrogenated. Here, "all hydrogenated" means, in essence, that the double bonds in the conjugated diene monomer units of the thermoplastic elastomer (A) are hydrogenated, including not only those with a hydrogenation rate (hydrogenation rate) of 100%, but also those with a rate of 80% or higher. The hydrogenation rate in the thermoplastic elastomer (A) used in this embodiment is preferably 85% or higher, more preferably 90% or higher, and even more preferably 95% or higher.

[0017] The thermoplastic elastomer (A) used in this embodiment may contain other monomer units besides styrene monomer units and conjugated diene monomer units, or it may not contain other monomer units. Examples of other monomer units include monomer units derived from aromatic vinyl compounds other than styrene monomers. In this embodiment, the thermoplastic elastomer (A) is preferably composed of styrene monomer units and conjugated diene monomer units at a mass percentage of 90% or more of all monomer units, more preferably 95% or more, and even more preferably 97% or more. As described above, thermoplastic elastomer (A) may contain only one type of styrene monomer unit and one type of conjugated diene monomer unit, or it may contain two or more types. When it contains two or more types, the total amount should preferably be within the range described above.

[0018] The number-average molecular weight of the thermoplastic elastomer (A) used in this embodiment is 50,000 or more. A number-average molecular weight of 50,000 or more tends to provide excellent crack resistance. The aforementioned 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, and further preferably 150,000 or more. The upper limit of the number-average molecular weight of the aforementioned thermoplastic elastomer (A) is preferably 400,000 or less, more preferably 350,000 or less, and further preferably 300,000 or less. A number-average molecular weight below the aforementioned upper limit tends to further improve compatibility with the thermoplastic elastomer (B) and the thermosetting resin (C). When the resin composition of this embodiment contains two or more thermoplastic elastomers (A), the number average molecular weight of such mixtures should conform to the above range.

[0019] The thermoplastic elastomer (A) used in this embodiment can be a block polymer or a random polymer. Examples of components of the thermoplastic elastomer (A) used in this embodiment include SEBS (styrene-ethylene / butene-styrene copolymer) and SEPS (styrene-ethylene / propylene-styrene copolymer).

[0020] Examples of commercially available thermoplastic elastomers (A) used in this embodiment include SEPTON (registered trademark) 2104 manufactured by Kuraray Co., Ltd., SOE (registered trademark) S1606, S1613, S1605 manufactured by Asahi Kasei Co., Ltd., and DYNARON (registered trademark) 9901P manufactured by JSR Co., Ltd.

[0021] The content of thermoplastic elastomer (A) in the resin composition of this embodiment is preferably 0.5 parts by mass or more, more preferably 1 part by mass or more, further preferably 2 parts by mass or more, further preferably 3 parts by mass or more, and further preferably 4 parts by mass or more, relative to 100 parts by mass of the resin solids. By reaching or exceeding the above-mentioned lower limit, there is a tendency to further improve low dielectric loss tangent, crack resistance, and low thermal expansion. Furthermore, the upper limit of the content of the above-mentioned thermoplastic elastomer (A) is preferably 20 parts by mass or less, more preferably 18 parts by mass or less, further preferably 15 parts by mass or less, further preferably 12 parts by mass or less, and further preferably 10 parts by mass or less, relative to 100 parts by mass of the resin solids. By reaching or below the above-mentioned upper limit, there is a tendency to further improve moisture absorption and heat resistance. The resin composition of this embodiment may contain only one thermoplastic elastomer (A), or it may contain two or more. In the case of containing two or more, the total amount should preferably be within the range described above.

[0022] <Thermoplastic Elastomers (B)> The resin composition of this embodiment contains a thermoplastic elastomer (B). The thermoplastic elastomer (B) is a thermoplastic elastomer obtained by hydrogenating a portion of the conjugated diene bonds in a thermoplastic elastomer containing styrene monomer units and conjugated diene monomer units with a number average molecular weight of 50,000 or more, and / or a thermoplastic elastomer with entirely unsaturated bonds. By containing thermoplastic elastomer (B), compatibility with thermoplastic elastomer (A) is improved, and excellent moisture absorption and heat resistance are achieved.

[0023] The thermoplastic elastomer (B) in this embodiment contains styrene monomer units. By containing styrene monomer units, it tends to have excellent compatibility with the thermosetting resin (C). Examples of styrene monomers include styrene, α-methylstyrene, p-methylstyrene, divinylbenzene (vinylstyrene), N,N-dimethyl-p-aminoethylstyrene, and N,N-diethyl-p-aminoethylstyrene. Among these, considering availability and manufacturability, styrene, α-methylstyrene, and p-methylstyrene are preferable. Styrene is particularly preferable among these. The content of styrene monomer units should preferably be in the range of 10-50% by mass of all monomer units, more preferably in the range of 13-45% by mass, and even more preferably in the range of 15-40% by mass. If the content of styrene monomer units is less than 50% by mass, the adhesion and bonding with substrates become better. In addition, if it is 10% by mass or more, it can suppress the increase of adhesion, make it less likely to produce residues or marks, and tend to have good peelability between adhesive surfaces, which is more ideal. Thermoplastic elastomer (B) may contain only one type of styrene monomer unit, or it may contain two or more types. In the case of containing two or more types, the total amount should preferably be within the range mentioned above. The method for determining the content of styrene monomer units in the thermoplastic elastomer (B) of this embodiment can be found in International Publication No. 2017 / 126469, the contents of which are incorporated herein by reference. The same applies to the conjugated diene monomer units, etc., described later.

[0024] The thermoplastic elastomer (B) in this embodiment contains conjugated diene monomer units. By containing conjugated diene monomer units, it tends to exhibit excellent low dielectric loss tangent, crack resistance, and low thermal expansion. There are no particular limitations on the conjugated diene monomer, provided it is a diene having one pair of conjugated double bonds. Examples of conjugated diene monomers include 1,3-butadiene, 2-methyl-1,3-butadiene (isoprene), 2,3-dimethyl-1,3-butadiene, 1,3-pentadiene, 2-methyl-1,3-pentadiene, 1,3-hexadiene, and chlorophenene; 1,3-butadiene and isoprene are preferred, and 1,3-butadiene is more preferred. Thermoplastic elastomer (B) may contain only one type of conjugated diene monomer unit, or it may contain two or more types.

[0025] In the thermoplastic elastomer (B) used in this embodiment, the mass ratio of styrene monomer units to conjugated diene monomer units is preferably in the range of 5 / 95 to 40 / 60, more preferably in the range of 7 / 93 to 37 / 63, and even more preferably in the range of 10 / 90 to 35 / 65. If the above-mentioned mass ratio of styrene monomer units to conjugated diene monomer units is in the range of 5 / 95 to 40 / 60, the increase in adhesion can be suppressed and high adhesion can be maintained, and the ease of peeling between the adhesive surfaces becomes better.

[0026] The thermoplastic elastomer (B) used in this embodiment is a thermoplastic elastomer whose conjugated diene bonds are not hydrogenated, or only partially hydrogenated. Here, "only partially hydrogenated" means that only a portion of the double bonds of the conjugated diene monomer units in the thermoplastic elastomer (B) are hydrogenated, indicating that the hydrogenation rate (hydrogenation rate) is less than 80%. The hydrogenation rate of the thermoplastic elastomer (B) used in this embodiment is preferably 60% or less, more preferably 40% or less, more preferably 20% or less, more preferably 10% or less, and more preferably 5% or less.

[0027] The thermoplastic elastomer (B) used in this embodiment may or may not contain other monomer units besides styrene monomer units and conjugated diene monomer units. Examples of other monomer units include monomer units derived from aromatic vinyl compounds other than styrene monomers. In this embodiment, the total mass of the thermoplastic elastomer (B) system styrene monomer units and conjugated diene monomer units is preferably 90% or more by mass of all monomer units, more preferably 95% or more by mass, further preferably 97% or more by mass, and even more preferably 99% or more by mass. As described above, thermoplastic elastomer (B) may contain only one type of styrene monomer unit and one type of conjugated diene monomer unit, or it may contain two or more types. When it contains two or more types, the total amount should preferably be within the range described above.

[0028] The number average molecular weight of the thermoplastic elastomer (B) used in this embodiment is 50,000 or more. A number average molecular weight of 50,000 or more tends to result in better crack resistance and compatibility with the thermoplastic elastomer (A). The aforementioned 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, and further preferably 150,000 or more. The upper limit of the number average molecular weight of the aforementioned thermoplastic elastomer (B) is preferably 400,000 or less, more preferably 350,000 or less, and further preferably 300,000 or less. A number average molecular weight below the aforementioned upper limit tends to further improve compatibility with the thermosetting resin (C). In the case where the resin composition of this embodiment contains two or more thermoplastic elastomers (B), the number average molecular weight of such mixtures should conform to the above-mentioned range.

[0029] The thermoplastic elastomer (B) used in this embodiment can be a block polymer or a random polymer. Examples of components of the thermoplastic elastomer (B) used in this embodiment include SBS (styrene-butadiene-styrene copolymer).

[0030] Examples of commercially available thermoplastic elastomers (B) used in this embodiment include TR2250 manufactured by JSR Corporation and SOE (registered trademark) S1609 manufactured by Asahi Kasei Corporation.

[0031] The content of thermoplastic elastomer (B) in the resin composition of this embodiment is preferably 0.5 parts by mass or more, more preferably 1 part by mass or more, further preferably 2 parts by mass or more, even more preferably 3 parts by mass or more, and even more preferably 4 parts by mass or more, relative to 100 parts by mass of the resin solids. Reaching the lower limit or above tends to improve low dielectric loss tangent, crack resistance, and low thermal expansion. Furthermore, the upper limit of the content of thermoplastic elastomer (B) is preferably 20 parts by mass or less, more preferably 18 parts by mass or less, further preferably 15 parts by mass or less, even more preferably 12 parts by mass or less, and even more preferably 10 parts by mass or less, relative to 100 parts by mass of the resin solids. Reaching the upper limit or below tends to improve moisture absorption and heat resistance. The resin composition of this embodiment may contain only one type of thermoplastic elastomer (B), or it may contain two or more types. When it contains two or more types, the total amount should preferably be within the range described above.

[0032] In the resin composition of this embodiment, the mass ratio of thermoplastic elastomer (A) to thermoplastic elastomer (B) is preferably 1:1 to 10. When the mass ratio of thermoplastic elastomer (B) to thermoplastic elastomer (A) is 1 part by mass or more, there is a tendency to improve moisture absorption and heat resistance. Furthermore, when the mass ratio of thermoplastic elastomer (B) to thermoplastic elastomer (A) is 10 parts by mass or less, there is a tendency to improve low dielectric loss tangent and crack resistance. The mass ratio of thermoplastic elastomer (A) to thermoplastic elastomer (B) is more preferably 1:1 to 9, further preferably 1:1 to 8, even further preferably 1:1 to 7, and even further preferably 1:1 to 5.

[0033] In this embodiment, the combined content of thermoplastic elastomer (A) and thermoplastic elastomer (B) in the resin composition is ideally 1 to 40 parts by mass relative to 100 parts by mass of the resin solids. Reaching or exceeding the lower limit of this value tends to further improve low dielectric loss tangent, crack resistance, and low thermal expansion. Furthermore, reaching or falling below the upper limit of this value tends to further improve moisture absorption and heat resistance. The above-mentioned total amount, relative to 100 parts by weight of the resin solids, is preferably 3 parts by weight or more, more preferably 5 parts by weight or more, and even more preferably 7 parts by weight or more. It is even more preferably 10 parts by weight or more. Furthermore, the above-mentioned total amount, relative to 100 parts by weight of the resin solids, is preferably 35 parts by weight or less, more preferably 30 parts by weight or less, even more preferably 25 parts by weight or less, and even more preferably 20 parts by weight or less.

[0034] <Compatible thermosetting resin (C)> The resin composition of this embodiment contains a thermosetting resin (C) compatible with both thermoplastic elastomer (A) and thermoplastic elastomer (B). By containing a compatible thermosetting resin (C) (hereinafter also referred to as "compatible thermosetting resin (C)" or "thermosetting resin (C)" in this specification), the effects of improving low dielectric properties and moisture absorption and heat resistance are achieved. Here, compatibility means that when thermoplastic elastomer (A) and thermoplastic elastomer (B) are thoroughly mixed with thermosetting resin (C) and left to stand, no obvious separation occurs, which can usually be observed visually. The aforementioned compatible thermosetting resin (C) is preferably a thermosetting resin containing aromatic rings and vinyl groups. By using such a resin, there is a tendency for it to readily accept the styrene monomer units contained in the thermoplastic elastomer (A) and thermoplastic elastomer (B), thus further improving compatibility. The molecular weight of the aforementioned compatible thermosetting resin (C), in terms of number average molecular weight Mn, is preferably 300 or more, more preferably 500 or more, more preferably 1,000 or more, and even more preferably 1,500 or more. The upper limit is preferably 130,000 or less, more preferably 120,000 or less, even more preferably 110,000 or less, and even more preferably 100,000 or less. When the mixture contains two or more thermosetting resins (C), the number average molecular weight of the mixture should preferably fall within the aforementioned range.

[0035] In this embodiment, the aforementioned compatible thermosetting resin (C) preferably comprises one or more compounds selected from the group consisting of polymers having constituent units represented by formula (V) and polyphenylene ether compounds having carbon-carbon unsaturated double bonds at the ends. Using such a resin will more effectively realize the effects of the present invention. [Chemistry 14] (In formula (V), Ar represents an aromatic hydrocarbon linker. * indicates the bond position.)

[0036] Furthermore, the aforementioned compatible thermosetting resin (C) may also contain constituent units derived from maleic anhydride. For details regarding such resins, please refer to International Publication No. 2017 / 209108, the contents of which are incorporated herein by reference. In addition, the aforementioned compatible thermosetting resin (C) may also contain constituent units from compounds having acid groups and anhydride groups.

[0037] In this embodiment of the resin composition, when the resin solids content in the resin composition is set to 100 parts by mass, the content of the aforementioned compatible thermosetting resin (C) is preferably 10 to 90 parts by mass. The lower limit of the content of the aforementioned compatible thermosetting resin (C), when the resin solids content in the resin composition is set to 100 parts by mass, is preferably 15 parts by mass or more, more preferably 20 parts by mass or more, and even more preferably 25 parts by mass or more. By setting the content of the aforementioned compatible thermosetting resin (C) to the aforementioned lower limit or above, low dielectric properties can be achieved, and in particular, low dielectric loss tangent can be effectively achieved. On the other hand, the upper limit of the content of the aforementioned compatible thermosetting resin (C), when the resin solids content in the resin composition is 100 parts by mass, is preferably 80 parts by mass or less, more preferably 60 parts by mass or less, even more preferably 50 parts by mass or less, and even more preferably 40 parts by mass or less. By setting the value below the aforementioned upper limit, the peel strength of the obtained hardened metal foil can be effectively improved. The aforementioned compatible thermosetting resin (C) may contain only one type or two or more types in the resin composition. When it contains two or more types, the total amount should preferably be within the range described above.

[0038] <<Polymers with constituent units represented by formula (V)>> The resin composition of this embodiment preferably contains a polymer having a constituent unit represented by formula (V). By containing a polymer having a constituent unit represented by formula (V), a resin composition with better low dielectric properties (low dielectric constant, low dielectric loss tangent) can be obtained. [Chemistry 15] (In formula (V), Ar represents an aromatic hydrocarbon linker. * indicates the bond position.) The aromatic hydrocarbon linking group can be a group consisting solely of an aromatic hydrocarbon that may also have substituents, or it can be a group consisting of an aromatic hydrocarbon that may also have substituents combined with other linking groups. It is preferable that it is a group consisting solely of an aromatic hydrocarbon that may also have substituents. Furthermore, aromatic hydrocarbons may also have substituents, including substituents Z (e.g., alkyl groups with 1 to 6 carbon atoms, alkenyl groups with 2 to 6 carbon atoms, alkoxy groups with 2 to 6 carbon atoms, hydroxyl groups, amino groups, carboxyl groups, halogen atoms, etc.). In addition, the aforementioned aromatic hydrocarbons are preferably unsubstituented. Aromatic hydrocarbon linkages are usually divalent linkages.

[0039] The aromatic hydrocarbon linking group, specifically, is preferably a phenyl group, naphthyl group, anthracene diyl group, phenanthrene diyl group, biphenyl diyl group, or fenandiyl group, which may also have substituents, and preferably a phenyl group, which may also have substituents. The substituent is exemplified by the substituent Z above, but the aforementioned phenyl groups are preferably unsubstituents.

[0040] The constituent unit represented by equation (V) should preferably include at least one of the constituent units represented by equation (V1), equation (V2), and equation (V3). Furthermore, * in the following equations indicates a bond position. Additionally, the constituent units represented by equations (V1) to (V3) are sometimes collectively referred to as "constituent unit (a)".

[0041] [Chemistry 16] In formulas (V1) to (V3), L1 represents an aromatic hydrocarbon linking group (preferably with 6 to 22 carbon atoms, more preferably 6 to 18, and even more preferably 6 to 10). Specifically, examples that may have substituents include phenyl, naphthyl, anthracenediyl, phenanthrenediyl, biphenyldiyl, and fenandrolyl, among which phenyl may also have substituents. The substituents are those exemplified by substituent Z above, but the aforementioned phenyl groups are preferably unsubstituented. The compound forming the constituent unit (a) is preferably a divinyl aromatic compound, such as divinylbenzene, bis(1-methylvinyl)benzene, divinylnaphthalene, divinylanthracene, divinylbiphenyl, divinylphenanthrene, etc. Divinylbenzene is particularly preferred. One such divinyl aromatic compound may be used, or two or more may be used as required.

[0042] A polymer having a constituent unit represented by formula (V) can be a homopolymer of constituent unit (a) or a copolymer of constituent units from other monomers, as described above. When the polymer having constituent units represented by formula (V) is a copolymer, its copolymerization ratio is preferably 5 mol% or more, more preferably 10 mol% or more, and even more preferably 15 mol% or more. As for the upper limit, it is preferably 90 mol% or less, more preferably 85 mol% or less, even more preferably 80 mol% or less, even more preferably 70 mol% or less, even more preferably 60 mol% or less, even more preferably 50 mol% or less, even more preferably 40 mol% or less, especially preferably 30 mol% or less, and may also be 25 mol% or less.

[0043] Regarding constituent units derived from other monomers, an example is a constituent unit (b) derived from an aromatic compound having one vinyl group (monovinyl aromatic compound).

[0044] The constituent unit (b) of the monovinyl aromatic compound shall preferably be a constituent unit represented by the following formula (V4).

[0045] [Chemistry 17] In formula (V4), L2 is an aromatic hydrocarbon linker, and in ideal concrete example, the example of L1 mentioned above can be cited. RV1 is a hydrogen atom or a hydrocarbon group with 1 to 12 carbon atoms (preferably an alkyl group). When RV1 is a hydrocarbon group, it is preferably 1 to 6 carbon atoms, and more preferably 1 to 3 carbon atoms. RV1 and L2 may also have the aforementioned substituent Z.

[0046] When a polymer having a constituent unit represented by formula (V) is a copolymer containing a constituent unit (b) from a monovinyl aromatic compound, examples of monovinyl aromatic compounds include vinyl aromatic compounds such as styrene, vinylnaphthalene, and vinyl biphenyl; and alkyl-substituted vinyl aromatic compounds such as o-methylstyrene, m-methylstyrene, p-methylstyrene, o, p-dimethylstyrene, o-ethylvinylbenzene, m-ethylvinylbenzene, p-ethylvinylbenzene, methylvinylbiphenyl, and ethylvinylbiphenyl. The monovinyl aromatic compounds exemplified here may also suitably have the aforementioned substituent Z. Furthermore, one or more of these monovinyl aromatic compounds may be used.

[0047] When the polymer having the constituent unit represented by formula (V) is a copolymer containing constituent unit (b), the copolymerization ratio of constituent unit (b) is preferably 10 mol% or more, more preferably 15 mol% or more, and may further 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. As an upper limit, it is preferably 98 mol% or less, more preferably 90 mol% or less, and further preferably 85 mol% or less.

[0048] Polymers having the constituent units represented by formula (V) may also have other constituent units besides constituent units (a) and (b). Examples of other constituent units include constituent units (c) from cyclic olefin compounds. Cyclic olefin compounds include hydrocarbons having double bonds within their ring structures. Specifically, in addition to monocyclic cyclic olefins such as cyclobutene, cyclopentene, cyclohexene, and cyclooctene, examples include compounds with a norunten ring structure such as norcamphene and dicyclopentadiene, and cyclic olefin compounds formed by the condensation of aromatic rings such as indene and acenaphthene. Examples of norunten compounds include those described in paragraphs 0037 to 0043 of Japanese Patent Application Publication No. 2018-39995, the contents of which are incorporated herein by reference. Furthermore, the cyclic olefin compounds illustrated herein may also have the aforementioned substituent Z.

[0049] When the polymer having the constituent unit represented by formula (V) is a copolymer containing the constituent unit (c), the copolymerization ratio of the constituent unit (c) is preferably 10 mol% or more, more preferably 20 mol% or more, and even more preferably 30 mol% or more. As an upper limit, it is preferably 90 mol% or less, more preferably 80 mol% or less, more preferably 70 mol% or less, and may be 50 mol% or less, or may be 30 mol% or less.

[0050] Polymers having constituent units represented by formula (V) may further incorporate constituent units (d) from different polymeric compounds (hereinafter also referred to as other polymeric compounds). Examples of other polymeric compounds (monomers) include compounds containing three vinyl groups. Specifically, examples include 1,3,5-trivinylbenzene, 1,3,5-trivinylnaphthalene, and 1,2,4-trivinylcyclohexane. Alternatively, examples include ethylene glycol diacrylate and butadiene. The copolymerization ratio of constituent units (d) from other polymeric compounds is preferably 30 mol% or less, more preferably 20 mol% or less, and further preferably 10 mol% or less.

[0051] As one embodiment of a polymer having constituent units represented by formula (V), an example is a polymer in which constituent unit (a) is necessary and contains at least one of constituent units (b) to (d). Furthermore, an example is a polymer in which the total of constituent units (a) to (d) accounts for 95 mol% or more, and more specifically 98 mol% or more of all constituent units. As another embodiment of the polymer having a constituent unit represented by formula (V), it is preferable that the constituent unit (a) is necessary and that, among all constituent units excluding the end units, the constituent units containing aromatic rings are 90 mol% or more, more preferably 95 mol% or more, or even 100 mol%. Furthermore, when calculating moles of all constituent units, one constituent unit is defined as a monomer (e.g., divinyl aromatic compounds, monovinyl aromatic compounds, etc.) that is used in the manufacture of a polymer having constituent units represented by formula (V).

[0052] The manufacturing method of polymers having constituent units represented by formula (V) is not particularly limited and can be any general method. For example, polymerizing raw materials containing divinyl aromatic compounds (monovinyl aromatic compounds, cycloolefin compounds, etc., may coexist depending on the requirements) in the presence of a Lewis acid catalyst. As for the Lewis acid catalyst, metal fluorides such as boron trifluoride or their complexes can be used.

[0053] There is no particular limitation on the structure of the chain ends of polymers having constituent units represented by formula (V). For the example of the base of the aforementioned divinyl aromatic compound, a structure adopting the following formula (E1) can be cited. Furthermore, L1 in formula (E1) is the same as that specified in formula (V1) above. * indicates the bond position. *-CH=CH-L 1-CH=CH 2(E1)

[0054] When the group from a monovinyl aromatic compound becomes the chain terminus, it can be represented by the structure of the following formula (E2). In this formula, L2 and RV1 have the same meaning as those defined in formula (V4) above. * indicates the bond position. *-CH=CH-L 2-R V1(E2)

[0055] The molecular weight of the polymer having the constituent units represented by formula (V), in terms of the number average molecular weight Mn, is preferably 300 or more, more preferably 500 or more, further preferably 1,000 or more, and more preferably 1,500 or more. 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, and even more preferably 100,000 or less. The molecular weight of the polymer having the constituent unit represented by formula (V), in terms of weight average molecular weight Mw, is preferably 1,000 or more, more preferably 2,000 or more, and even more preferably 3,000 or more. By reaching the lower limit value above the above, the excellent low dielectric properties of the polymer having the constituent unit represented by formula (V), especially the dielectric properties after moisture absorption, can be effectively utilized in the cured resin composition. The upper limit value of the weight average molecular weight Mw is preferably 160,000 or less, more preferably 150,000 or less, even more preferably 140,000 or less, and even more preferably 130,000 or less. By reaching the upper limit value above the above, when the prepreg or resin sheet is laminated on the circuit forming substrate, there is a tendency to be less prone to poor filling. The monodispersity (Mw / Mn), expressed as the ratio of weight-average molecular weight Mw to number-average molecular weight Mn, should preferably be 100 or less, more preferably 50 or less, and even more preferably 20 or less. In practical terms, a lower limit for monodispersity of 1.1 or more is also acceptable for the required performance. The above Mw and Mn were determined according to the description of the examples described later. When the resin composition of this embodiment contains two or more polymers having constituent units represented by formula (V), the Mw, Mn, and Mw / Mn of the mixture should conform to the above range.

[0056] The vinyl equivalent of the polymer having the constituent unit represented by formula (V) is preferably 200 g / eq. or more, more preferably 230 g / eq. or more, and even more preferably 250 g / eq. or more. Furthermore, the vinyl equivalent is preferably 1200 g / eq. or less, more preferably 1000 g / eq. or less, and even more preferably 800 g / eq. or less, 600 g / eq. or less, 400 g / eq. or less, or 300 g / eq. or less. By reaching the lower limit or above, there is a tendency to improve the storage stability of the resin composition and improve the flowability of the resin composition. Therefore, there is a tendency to improve moldability, reduce the likelihood of voids during the formation of prepregs, and obtain printed circuit boards with higher reliability. On the other hand, by reaching the upper limit or below, there is a tendency to improve the moisture absorption and heat resistance of the obtained cured material.

[0057] Furthermore, the polymer with constituent units represented by formula (V) used in this embodiment exhibits desirable dielectric properties in its cured form. For example, the relative permittivity (Dk) at 10 GHz, measured by the cavity resonator perturbation method, is preferably 2.80 or less, more preferably 2.60 or less, further preferably 2.50 or less, and even more preferably 2.40 or less. Moreover, the lower limit of the aforementioned relative permittivity is, for example, 1.80 or more in practical terms. Furthermore, the dielectric loss tangent (Df) at 10 GHz, measured by the cavity resonator perturbation method, is preferably 0.0030 or less, more preferably 0.0020 or less, and even more preferably 0.0010 or less. Moreover, the lower limit of the aforementioned dielectric loss tangent is, for example, 0.0001 or more in practical terms. The dielectric loss tangent (Df) was measured according to the method described in the following examples. The relative permittivity (Dk) was also measured according to the method for measuring Df in the examples.

[0058] Regarding polymers having constituent units represented by formula (V) in this specification, reference can be made to the compounds and their synthesis reaction conditions described in paragraphs 0029 to 0058 of International Patent Application Publication No. 2017 / 115813, the compounds and their synthesis reaction conditions described in paragraphs 0013 to 0058 of Japanese Patent Application Publication No. 2018-039995, and the compounds and their synthesis reaction conditions described in paragraphs 0008 to 0043 of Japanese Patent Application Publication No. 2018-168347. The following contents are included in this specification: reaction conditions, compounds and their synthesis reaction conditions described in paragraphs 0014 to 0042 of Japanese Patent Application Publication No. 2006-070136, compounds and their synthesis reaction conditions described in paragraphs 0014 to 0061 of Japanese Patent Application Publication No. 2006-089683, and compounds and their synthesis reaction conditions described in paragraphs 0008 to 0036 of Japanese Patent Application Publication No. 2008-248001.

[0059] In the case where the resin composition of this embodiment contains a polymer having constituent units represented by formula (V), when the resin solids content in the resin composition is set to 100 parts by mass, the content of the polymer having constituent units represented by formula (V) should preferably be 5 to 50 parts by mass. The lower limit of the content of the polymer having constituent units represented by formula (V), when the resin solids content in the resin composition is 100 parts by mass, should preferably be 10 parts by mass or more, more preferably 15 parts by mass or more, and may be 20 parts by mass or more, or may be 25 parts by mass or more. By setting the content of the polymer having constituent units represented by formula (V) to the above-mentioned lower limit or above, low dielectric properties can be effectively achieved, especially low dielectric loss tangent. On the other hand, the upper limit of the content of the polymer having constituent units represented by formula (V), when the resin solids content in the resin composition is 100 parts by mass, should preferably be 45 parts by mass or less, more preferably 40 parts by mass or less, and further preferably 35 parts by mass or less. Furthermore, by setting the value below the aforementioned upper limit, the peel strength of the obtained hardened material can be effectively improved. A polymer having a constituent unit represented by formula (V) may contain only one type or more types in a resin composition. In the case of containing more than two types, the total amount should preferably be within the range described above.

[0060] <<Polyphenylene ether compounds with carbon-carbon unsaturated double bonds at the ends>> The resin composition of this embodiment may also contain polyphenylene ether compounds with carbon-carbon unsaturated double bonds at the ends. Polyphenylene ether compounds having carbon-carbon unsaturated double bonds at the ends are preferably polyphenylene ether compounds having a group selected from the group consisting of (meth)acrylate, maleimide, and vinylbenzyl groups at the ends. Furthermore, polyphenylene ether compounds having carbon-carbon unsaturated double bonds at the ends are preferably polyphenylene ether compounds having two or more carbon-carbon unsaturated double bonds at the ends. By using such polyphenylene ether compounds, there is a tendency to more effectively improve the low dielectric properties of printed circuit boards. The following will explain these in detail.

[0061] Polyphenylene ether compounds having carbon-carbon unsaturated double bonds at the ends are exemplified by compounds having a polyphenylene ether skeleton represented by the following formula (X1).

[0062] [Chemistry 18] (In formula (X1), R24, R25, R26, and R27 may be the same or different, representing alkyl, aryl, halogen, or hydrogen atoms with 6 or fewer carbon atoms.)

[0063] Polystyrene ether compounds with carbon-carbon unsaturated double bonds at the ends may also contain repeating units represented by formula (X2): [Chemistry 19] (In formula (X2), R28, R29, R30, R34, and R35 may be the same or different, representing alkyl or phenyl groups with 6 or fewer carbon atoms. R31, R32, and R33 may be the same or different, representing hydrogen atoms and alkyl or phenyl groups with 6 or fewer carbon atoms.) 、 and / or 、repeating units represented by formula (X3): [Chemistry 20] (In formula (X3), R36, R37, R38, R39, R40, R41, R42, and R43 may be the same or different, and are hydrogen atoms, alkyl groups or phenyl groups with 6 or fewer carbon atoms. -A- are straight-chain, branched or cyclic divalent hydrocarbon groups with 20 or fewer carbon atoms.)

[0064] Polyphenylene ether compounds having carbon-carbon unsaturated double bonds at the ends are preferably modified polyphenylene ether compounds (hereinafter sometimes referred to as "modified polyphenylene ether compound (g)") obtained by functionalizing one or all of the ends with vinyl unsaturated groups, and more preferably modified polyphenylene ether compounds having two or more groups selected from the group consisting of (meth)acrylate, maleimide, and vinylbenzyl groups at the ends. By using such modified polyphenylene ether compounds (g), the dielectric loss tangent (Df) of the cured resin composition can be reduced. One or more of these compounds can be used.

[0065] For modified polyphenylene ether compounds (g), compounds represented by formula (OP-1) can be listed. [Chemistry 21] (In formula (OP-1), X represents an aromatic group, -(YO)n 2- represents a polyphenylene ether structure, R1, R2, and R3 each independently represent a hydrogen atom, alkyl, alkenyl, or alkynyl group, n1 represents an integer from 1 to 6, n2 represents an integer from 1 to 100, and n3 represents an integer from 1 to 4.) When n2 and / or n3 are integers greater than 2, the n2 constituent units (YO) and / or n3 constituent units may be the same or different. n3 should preferably be greater than 2, and more preferably 2.

[0066] The modified polyphenylene ether compound (g) in this embodiment is preferably a compound represented by formula (OP-2). [Chemistry 22] Here, -(OXO)- should be represented by formula (OP-3): [Chemistry 23] (In formula (OP-3), R4, R5, R6, R10, and R11 may be the same or different, and are alkyl or phenyl groups with 6 or fewer carbon atoms. R7, R8, and R9 may be the same or different, and are hydrogen atoms, alkyl or phenyl groups with 6 or fewer carbon atoms.) AND / or (OP-4): [Chemistry 24] (In formula (OP-4), R12, R13, R14, R15, R16, R17, R18, and R19 may be the same or different, and are hydrogen atoms, alkyl groups with 6 or fewer carbon atoms, or phenyl groups. -A- are straight-chain, branched, or cyclic divalent hydrocarbon groups with 20 or fewer carbon atoms.)

[0067] Furthermore, -(YO)- should be in the form (OP-5): [Chemistry 25] (In formula (OP-5), R20 and R21 may be the same or different, and are alkyl or phenyl groups with 6 or fewer carbon atoms. R22 and R23 may be the same or different, and are hydrogen atoms, alkyl or phenyl groups with 6 or fewer carbon atoms.) In formula (OP-2), at least one of a and b is not 0, and represents an integer from 0 to 100, preferably an integer from 0 to 50, and more preferably an integer from 1 to 30. When a and / or b are integers of 2 or more, the two or more -(YO)- can each be obtained by an independent arrangement of one type of structure, or they can be arranged in two or more types of structures in a block or random arrangement.

[0068] Regarding the -A- in formula (OP-4), examples of divalent organic groups include methylene, ethylene, 1-methylethylene, 1,1-propylene, 1,4-epoxyphenylbis(1-methylethylene), 1,3-epoxyphenylbis(1-methylethylene), cyclohexylene, phenylmethylene, naphthylmethylene, and 1-phenylethylene, but it is not limited to these.

[0069] Among the modified polyphenylene ether compounds (g) mentioned above, it is preferable that R4, R5, R6, R10, R11, R20, and R21 are alkyl groups with 3 or fewer carbon atoms, and R7, R8, R9, R12, R13, R14, R15, R16, R17, R18, R19, R22, and R23 are polyphenylene ether compounds with hydrogen atoms or alkyl groups with 3 or fewer carbon atoms. In particular, it is preferable that the -(OXO)- series (OP-9), (OP-10), and / or (OP-11) represented by formula (OP-3) or formula (OP-4) are preferred, and the -(YO)- series (OP-12) or (OP-13) represented by formula (OP-5) are preferred. When a and / or b are integers of 2 or more, the two or more -(YO)- groups can each independently form a structure of two or more arrangements of formula (OP-12) and / or formula (OP-13), or they can also form a structure of formula (OP-12) and formula (OP-13) arranged in segments or randomly.

[0070] [Chemistry 26] [Chemistry 27] (In formula (OP-10), R44, R45, R46, and R47 may be the same or different, and are either hydrogen atoms or methyl groups. -B- is a straight-chain, branched, or cyclic divalent hydrocarbon group with 20 or fewer carbon atoms.) -B- can be listed as a specific example that is the same as the specific example of -A- in equation (OP-4). [Chemistry 28] (In formula (OP-11), -B- is a straight-chain, branched, or cyclic divalent hydrocarbon group with 20 or fewer carbon atoms.) -B- can be listed as a specific example that is the same as the specific example of -A- in equation (OP-4). [Chemistry 29] [Chemistry 30]

[0071] Polyphenylene ether compounds with carbon-carbon unsaturated double bonds at their ends can be manufactured by known methods or commercially available products can be used. For example, SABIC Innovative Plastics' "SA9000" is a commercially available product for modified polyphenylene ether compounds with methacrylate groups at their ends. Mitsubishi Gas Chemical's "OPE-2St1200" and "OPE-2St2200" are examples of modified polyphenylene ether compounds with vinyl benzyl groups at their ends. Furthermore, modified polyphenylene ether compounds with vinyl benzyl groups at their ends can also be obtained by modifying hydroxyl-terminated polyphenylene ether compounds such as SABIC Innovative Plastics' "SA90" to vinyl benzyl groups using vinyl benzyl chloride or similar substances.

[0072] Furthermore, for detailed descriptions of polyphenylene ether compounds having carbon-carbon unsaturated double bonds at the ends, please refer to Japanese Patent Application Publication No. 2006-028111, Japanese Patent Application Publication No. 2018-016709, International Publication No. 2019-138992, and International Publication No. 2022-054303, the contents of which are incorporated herein by reference.

[0073] The number average molecular weight (MAM) of polystyrene converted by GPC (gel permeation chromatography) of polyphenylene ether compounds (preferably modified polyphenylene ether compounds (g)) having carbon-carbon unsaturated double bonds at the ends (details follow the method described in the examples below) is preferably 500 to 3,000. With a MAM of 500 or higher, there is a tendency to further suppress adhesion when the resin composition of this embodiment is formed into a coating. With a MAM of 3,000 or lower, there is a tendency to further improve solubility in solvents. Furthermore, the weight-average molecular weight (based on the method described in the later examples) of the polyphenylene ether compound (preferably a modified polyphenylene ether compound (g)) having carbon-carbon unsaturated double bonds at the ends of the polyphenylene ether compound is preferably 800 to 10,000, and more preferably 800 to 5,000. By reaching the lower limit value above, there is a tendency for the relative permittivity (Dk) and dielectric loss tangent (Df) of the cured resin composition to become lower, and by reaching the upper limit value below, there is a tendency for the solubility, low viscosity, and formability of the resin composition in solvents to be further improved when making varnishes, etc., as described later. Furthermore, when modifying the polyphenylene ether compound (g), the equivalent amount of terminal carbon-carbon unsaturated double bonds is 400~5000g per carbon-carbon unsaturated double bond, more preferably 400~2500g. By exceeding the aforementioned lower limit, the relative permittivity (Dk) and dielectric loss tangent (Df) of the cured resin composition tend to become lower. By falling below the aforementioned upper limit, the solubility, low viscosity, and formability of the resin composition in solvents tend to be further improved.

[0074] In this embodiment, when the resin composition contains a polyphenylene ether compound with carbon-carbon unsaturated double bonds at the ends, the lower limit of the content of the polyphenylene ether compound with carbon-carbon unsaturated double bonds at the ends 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 further preferably 7 parts by mass or more, relative to 100 parts by mass of the resin solids in the resin composition. By reaching the above-mentioned lower limit or above, there is a tendency to further improve the low water absorption and low dielectric properties (Dk and / or Df) of the obtained cured product. Furthermore, the upper limit of the content of the polyphenylene ether compound with carbon-carbon unsaturated double bonds at the ends is preferably 70 parts by mass or less, more preferably 60 parts by mass or less, further preferably 50 parts by mass or less, further preferably 40 parts by mass or less, and may also be 30 parts by mass or less, or 25 parts by mass or less, relative to 100 parts by mass of the resin solids in the resin composition. By reaching the above-mentioned upper limit or below, there is a tendency to further improve the copper foil peel strength of the obtained cured product. The resin composition in this embodiment may contain only one type of polyphenylene ether compound with a carbon-carbon unsaturated double bond at the end, or it may contain two or more types. When it contains two or more types, the total amount should preferably be within the range described above.

[0075] <Other Resins (D)> The resin composition of this embodiment may further contain other resins (D). Regarding other resins (D), it is preferable to contain at least one selected from the group consisting of maleimide compounds, cyanate compounds, epoxy compounds, phenolic compounds, alkenyl-substituted nadiimide compounds, oxacyclobutane resins, and benzo[a]pyrene compounds, and more preferably, to contain one or more other resins (D) selected from the group consisting of cyanate compounds, maleimide compounds, and epoxy compounds. While such other resins (D) are not essential components for achieving the effects of this invention, by incorporating these components, various physical properties can be imparted to the resin composition or cured material, or the dielectric properties, moisture absorption, and heat resistance of the resin composition or cured material can be further improved. These other resins (D) may be used alone or in combination of two or more.

[0076] <<Cyanate Compounds>> The resin composition of this embodiment may also contain cyanate ester compounds. There are no particular limitations on cyanate ester compounds as long as they contain one or more cyanate groups (cyanoxy groups) per molecule (preferably 2 to 12, more preferably 2 to 6, further preferably 2 to 4, further preferably 2 or 3, further preferably 2), and they can be widely used in the field of printed circuit boards. In addition, cyanate ester compounds are preferably compounds in which the cyanate groups are directly bonded to the aromatic skeleton (aromatic ring). Examples of cyanate compounds include at least one selected from the group consisting of phenolic varnish-type cyanate compounds, naphthol aralkyl-type cyanate compounds (naphthol aralkyl-type cyanate), naphthyl ether-type cyanate compounds, biphenyl aralkyl-type cyanate compounds, xylene resin-type cyanate compounds, triphenol methane-type cyanate compounds, adamantane skeleton-type cyanate compounds, bisphenol M-type cyanate compounds, bisphenol A-type cyanate compounds, and diallyl bisphenol A-type cyanate compounds. Among these, considering the viewpoint of further improving the low water absorption of the obtained cured product, it is preferable to select at least one selected from the group consisting of phenolic varnish-type cyanate compounds, naphthol aralkyl-type cyanate compounds, naphthyl ether-type cyanate compounds, xylene resin-type cyanate compounds, bisphenol M-type cyanate compounds, bisphenol A-type cyanate compounds, and diallyl bisphenol A-type cyanate compounds, and more preferably naphthol aralkyl-type cyanate compounds. These cyanate compounds can be prepared by known methods or commercially available products can be used. Furthermore, cyanate compounds having a naphthol aralkyl skeleton, naphthyl ether skeleton, xylene skeleton, pyromethane skeleton, or adamantane skeleton have a larger functional group equivalent number and fewer unreacted cyanate groups compared to other compounds, thus resin compositions using these compounds tend to have better low water absorption properties when cured. In addition, due to the presence of an aromatic skeleton or adamantane skeleton, there is a tendency for improved plating adhesion.

[0077] The resin composition of this embodiment preferably contains a cyanate ester compound without impairing the effects of the present invention. When the resin composition of this embodiment contains a cyanate ester compound, the lower limit of its content is preferably 0.1 parts by mass or more, more preferably 2 parts by mass or more, and may be 5 parts by mass or more, relative to 100 parts by mass of the resin solids in the resin composition. By having a cyanate ester compound content of 0.1 parts by mass or more, there is a tendency to improve the heat resistance, flame resistance, chemical resistance, low relative permittivity, low dielectric loss tangent, and insulation properties of the obtained cured product. The upper limit of the cyanate ester compound content, when the resin composition of this embodiment contains a cyanate ester compound, is preferably 70 parts by mass or less, more preferably 50 parts by mass or less, further preferably 40 parts by mass or less, further preferably 30 parts by mass or less, and further preferably 20 parts by mass or less, relative to 100 parts by mass of the resin solids in the resin composition. The resin composition in this embodiment may contain only one cyanate ester compound, or it may contain two or more. When it contains two or more compounds, the total amount should preferably be within the range described above.

[0078] <<Malayin Compounds>> The resin composition of this embodiment may also contain maleimide compounds. There are no particular limitations on the resin composition of this embodiment, as long as it is a compound having one or more maleimide groups per molecule (preferably 2-12, more preferably 2-6, further preferably 2-4, even more preferably 2 or 3, even more preferably 2), and it can be widely used in compounds commonly used in the field of printed circuit boards. In this embodiment, the maleimine compound preferably includes one or more compounds selected from the group consisting of compounds represented by formula (M0), formula (M1), formula (M2), formula (M3), formula (M4), and formula (M5), more preferably including one or more compounds selected from the group consisting of compounds represented by formula (M0), formula (M1), formula (M3), formula (M4), and formula (M5), more preferably including one or more compounds selected from the group consisting of compounds represented by formula (M1), formula (M3), and formula (M5), and further preferably including compounds represented by formula (M1) and / or formula (M3). If these maleimide compounds are used in materials for printed wiring boards (such as metal foil laminates), they can impart excellent heat resistance. [Chemistry 31] (In formula (M0), R51 each independently represents a hydrogen atom, an alkyl group with 1 to 8 carbon atoms, or a phenyl group; R52 each independently represents a hydrogen atom or a methyl group; and n1 represents an integer greater than 1.) R 51 is preferably selected independently from one of the group consisting of hydrogen atom, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tributyl, n-pentyl and phenyl, more preferably hydrogen atom and / or methyl, more preferably hydrogen atom. R 52 should preferably be methyl. n 1 should ideally be an integer from 1 to 10, more preferably an integer from 1 to 5, further preferably an integer from 1 to 3, even further preferably 1 or 2, and even further preferably 1. Specifically, the following compounds can be cited as preferred examples of formula (M0). [Chemistry 32] In the above formula, each of the R 8 series independently represents a hydrogen atom, a methyl group, or an ethyl group, and it is preferable to use a methyl group.

[0079] The compound represented by formula (M0) can be a single compound or a mixture of two or more compounds. Examples of mixtures include mixtures of compounds with different n1, mixtures of compounds with different types of substituents R51 and / or R52, mixtures of compounds with different bonding positions (meta, para, or ortho) of the maleimine group and oxygen atom on the benzene ring, and mixtures of compounds combining two or more of the above-mentioned dissimilar compounds. The same applies to formulas (M1) to (M5) below. [Chemistry 33] In formula (M1), RM1, RM2, RM3, and RM4 each independently represent a hydrogen atom or an organic group; RM5 and RM6 each independently represent a hydrogen atom or an alkyl group; ArM represents a divalent aromatic group; A represents a 4-6 membered alicyclic group; RM7 and RM8 each independently represent an alkyl group; mx represents 1 or 2, lx represents 0 or 1; RM9 and RM10 each independently represent a hydrogen atom or an alkyl group; RM11, RM12, RM13, and RM14 each independently represent a hydrogen atom or an organic group; R The M15 series independently represents alkyl, alkyloxy, alkylthio, aryl, aryloxy, arylthio, halogen, hydroxyl, or mercapto groups with 1 to 10 carbon atoms; px represents an integer from 0 to 3; nx represents an integer from 1 to 20.

[0080] In the formula, RM1, RM2, RM3, and RM4 each independently represent a hydrogen atom or an organic group. The organic group here is preferably an alkyl group, more preferably an alkyl group having 1 to 12 carbon atoms, further preferably an alkyl group having 1 to 6 carbon atoms, and even more preferably methyl, ethyl, propyl, or butyl, with methyl being particularly preferred. RM1 and RM3 are each preferably an alkyl group, and RM2 and RM4 are preferably hydrogen atoms. RM5 and RM6 each independently represent a hydrogen atom or an alkyl group, and should preferably be alkyl. The alkyl group here should preferably be an alkyl group with 1 to 12 carbon atoms, more preferably an alkyl group with 1 to 6 carbon atoms, and even more preferably methyl, ethyl, propyl, or butyl, with methyl being particularly preferred. Ar M represents a divalent aromatic group, preferably anthracene, naphthyl, phenanthrene, or anthracene, more preferably anthracene, and even more preferably m-anthracene. Ar M may also have substituents, preferably alkyl, more preferably alkyl with 1 to 12 carbon atoms, even more preferably alkyl with 1 to 6 carbon atoms, and even more preferably methyl, ethyl, propyl, or butyl, especially methyl. However, Ar M is preferably unsubstituted. The A series consists of 4-6 member alicyclic groups, preferably 5-membered alicyclic groups (preferably groups that combine with a benzene ring to form an indane ring). The RM7 and RM8 series are each independently alkyl groups, preferably alkyl groups with 1-6 carbons, more preferably alkyl groups with 1-3 carbons, and especially preferably methyl groups. mx series 1 or 2, preferably 2. lx is either 0 or 1, and should ideally be 1. RM9 and RM10 each independently represent a hydrogen atom or an alkyl group, with alkyl being more preferred. 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, and further preferably methyl, ethyl, propyl, or butyl, with methyl being particularly preferred. RM11, RM12, RM13, and RM14 each independently represent a hydrogen atom or an organic group. The organic group here is preferably an alkyl group, more preferably an alkyl group having 1 to 12 carbon atoms, further preferably an alkyl group having 1 to 6 carbon atoms, and even more preferably methyl, ethyl, propyl, or butyl, with methyl being particularly preferred. RM12 and RM13 are each preferably alkyl groups, and RM11 and RM14 are preferably hydrogen atoms. The RM15 series can be independently represented by alkyl, alkyloxy, alkylthio, aryl, aryloxy, arylthio, halogen atom, hydroxyl or mercapto groups having 1 to 10 carbon atoms, preferably alkyl with 1 to 4 carbon atoms, cycloalkyl with 3 to 6 carbon atoms, or aryl with 6 to 10 carbon atoms. px represents an integer from 0 to 3, preferably an integer from 0 to 2, even more preferably 0 or 1, and even more preferably 0. nx represents an integer from 1 to 20. nx can also be an integer less than 10. Furthermore, the resin composition of this embodiment may contain a compound represented by formula (M1) and at least one compound with a different value of nx, or it may contain two or more compounds. When it contains two or more compounds, the average value (average number of repeating units) n of nx in the compound represented by formula (M1) in the resin composition, in order to have a low melting point (low softening point), low melt viscosity, and good workability, is preferably 0.92 or higher, more preferably 0.95 or higher, further preferably 1.0 or higher, and even more preferably 1.1 or higher. In addition, n is preferably 10.0 or less, more preferably 8.0 or less, further preferably 7.0 or less, further preferably 6.0 or less, and may also be 5.0 or less. The same applies to formulas (M1-1) and the like described later.

[0081] The compound represented by formula (M1) should preferably be represented by the following formula (M1-1). [Chemistry 34] (In formula (M1-1), RM21, RM22, RM23, and RM24 each independently represent a hydrogen atom or an organic group. RM25 and RM26 each independently represent a hydrogen atom or an alkyl group. RM27, RM28, RM29, and RM30 each independently represent a hydrogen atom or an organic group. RM31 and RM32 each independently represent a hydrogen atom or an alkyl group. RM33, RM34, RM35, and RM36 each independently represent a hydrogen atom or an organic group. RM37, RM38, and RM39 each independently represent a hydrogen atom or an alkyl group. nx represents an integer from 1 to 20.)

[0082] In the formula, RM21, RM22, RM23, and RM24 each independently represent a hydrogen atom or an organic group. The organic group here is preferably an alkyl group, more preferably an alkyl group having 1 to 12 carbon atoms, more preferably an alkyl group having 1 to 6 carbon atoms, and more preferably methyl, ethyl, propyl, or butyl, especially methyl. RM21 and RM23 are preferably alkyl groups, and RM22 and RM24 are preferably hydrogen atoms. RM25 and RM26 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, and further preferably methyl, ethyl, propyl, or butyl, with methyl being particularly preferred. RM27, RM28, RM29, and RM30 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 having 1 to 12 carbon atoms, further preferably an alkyl group having 1 to 6 carbon atoms, and even more preferably methyl, ethyl, propyl, or butyl, especially methyl. RM31 and RM32 each independently represent a hydrogen atom or an alkyl group, and should preferably be alkyl. The alkyl group here should preferably be an alkyl group with 1 to 12 carbon atoms, more preferably an alkyl group with 1 to 6 carbon atoms, and even more preferably methyl, ethyl, propyl, or butyl, with methyl being particularly preferred. RM33, RM34, RM35, and RM36 each independently represent a hydrogen atom or an organic group. The organic group here is preferably an alkyl group, more preferably an alkyl group having 1 to 12 carbon atoms, further preferably an alkyl group having 1 to 6 carbon atoms, and even more preferably methyl, ethyl, propyl, or butyl, especially methyl. RM33 and RM36 should preferably be hydrogen atoms, and RM34 and RM35 should preferably be alkyl groups. RM37, RM38, and RM39 each independently represent a hydrogen atom or an alkyl group, and should preferably be an alkyl group. The alkyl group here should preferably be an alkyl group having 1 to 12 carbon atoms, more preferably an alkyl group having 1 to 6 carbon atoms, and even more preferably methyl, ethyl, propyl, or butyl, with methyl being particularly preferred. nx represents an integer greater than 1 and less than 20. nx can also be an integer less than 10.

[0083] The compound represented by formula (M1-1) should preferably be a compound represented by formula (M1-2). [Chemistry 35] (In formula (M1-2), RM21, RM22, RM23, and RM24 each independently represent a hydrogen atom or an organic group. RM25 and RM26 each independently represent a hydrogen atom or an alkyl group. RM27, RM28, RM29, and RM30 each independently represent a hydrogen atom or an organic group. RM31 and RM32 each independently represent a hydrogen atom or an alkyl group. RM33, RM34, RM35, and RM36 each independently represent a hydrogen atom or an organic group. RM37, RM38, and RM39 each independently represent a hydrogen atom or an alkyl group. nx represents an integer from 1 to 20.)

[0084] In formula (M1-2), RM21, RM22, RM23, RM24, RM25, RM26, RM27, RM28, RM29, RM30, RM31, RM32, RM33, RM34, RM35, RM36, RM37, RM38, RM39, and nx are respectively synonyms of RM21, RM22, RM23, RM24, RM25, RM26, RM27, RM28, RM29, RM30, RM31, RM32, RM33, RM34, RM35, RM36, RM37, RM38, RM39, and nx in formula (M1-1), and their preferred ranges are also the same.

[0085] The compound represented by formula (M1-1) is preferably represented by formula (M1-3), and more preferably by formula (M1-4). [Chemistry 36] (In formula (M1-3), nx represents an integer between 1 and 20.) nx can also be an integer less than 10. [Chemistry 37] (In formula (M1-4), nx represents an integer between 1 and 20.) nx can also be an integer less than 10.

[0086] The molecular weight of the compound represented by formula (M1) is preferably 500 or higher, more preferably 600 or higher, and even more preferably 700 or higher. By achieving the lower limit or higher of the above, the low dielectric properties and low water absorption of the obtained cured material tend to be further improved. Furthermore, the molecular weight of the compound represented by formula (M1) is preferably 10,000 or lower, more preferably 9,000 or lower, more preferably 7,000 or lower, more preferably 5,000 or lower, and more preferably 4,000 or lower. By achieving the upper limit or lower of the above, the heat resistance and workability of the obtained cured material tend to be further improved.

[0087] [Chemistry 38] (In formula (M2), R 54 each independently represents a hydrogen atom or a methyl group, and n 4 represents an integer greater than or equal to 1.) n 4 should ideally be an integer from 1 to 10, more preferably an integer from 1 to 5, further preferably an integer from 1 to 3, and even further preferably 1 or 2, or 1. The compound represented by formula (M2) may also be a mixture of n-4 different compounds, preferably a mixture. In addition, it may also be a mixture of other compounds that are different from those described in part of the compound represented by formula (M0). [Chemistry 39] (In formula (M3), R 55 independently represents a hydrogen atom, an alkyl group with 1 to 8 carbon atoms, or a phenyl group, and n 5 represents an integer between 1 and 10.) R 55 is preferably selected independently from one of the group consisting of hydrogen atom, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tributyl, n-pentyl and phenyl, more preferably hydrogen atom and / or methyl, and even more preferably hydrogen atom. n 5 should preferably be an integer between 1 and 5, more preferably an integer between 1 and 3, and even more preferably 1 or 2. The compound represented by formula (M3) may also be a mixture of n-5 different compounds, preferably a mixture. In addition, it may also be a mixture of other compounds that are different from those represented by formula (M0). [Chemistry 40] (In formula (M4), R56 series each independently represents a hydrogen atom, a methyl group, or an ethyl group, and R57 series each independently represents a hydrogen atom or a methyl group.) R 56 is preferably methyl or ethyl, each independently, and more preferably methyl and ethyl in each of the two separate benzene rings; R 57 is preferably methyl.

[0088] [Chemistry 41] (In formula (M5), R 58 each independently represents a hydrogen atom, an alkyl group with 1 to 8 carbon atoms, or a phenyl group; R 59 each independently represents a hydrogen atom or a methyl group; and n 6 represents an integer greater than 1.) R 58 is preferably selected independently from one of the group consisting of hydrogen atom, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tributyl, n-pentyl and phenyl, more preferably hydrogen atom and / or methyl, and even more preferably hydrogen atom. R 59 should preferably be methyl. n 6 should ideally be an integer from 1 to 10, more preferably an integer from 1 to 5, further preferably an integer from 1 to 3, and even further preferably 1 or 2, or 1. The compound represented by formula (M5) may also be a mixture of n-6 different compounds, preferably a mixture. In addition, it may also be a mixture of other compounds that are different from those described in part of the compound represented by formula (M0).

[0089] Maleimine compounds can be manufactured using known methods or commercially available products can be used. For example, compounds represented by formula (M0) include "BMI-80" manufactured by K.I Chemical Industry Co., Ltd.; compounds represented by formula (M1) include "NE-X-9470S" manufactured by DIC Corporation; compounds represented by formula (M2) include "BMI-2300" manufactured by Yamato Chemical Industry Co., Ltd.; compounds represented by formula (M3) include "MIR-3000-70MT" manufactured by Nippon Kayaku Co., Ltd.; compounds represented by formula (M4) include "BMI-70" manufactured by K.I Chemical Industry Co., Ltd.; and compounds represented by formula (M5) include "MIR-5000" manufactured by Nippon Kayaku Co., Ltd.

[0090] In addition to the above, examples of maleimide compounds include, for example, oligomers of N-phenylmaleimide, phenylmethanemaleimide, m-phenylbismaleimide, 4-methyl-1,3-phenylbismaleimide, 1,6-bismaleimide-(2,2,4-trimethyl)hexane, 4,4'-diphenyl ether bismaleimide, 4,4'-diphenyl monazine bismaleimide, 1,3-bis(3-maleimide phenoxy)benzene, 1,3-bis(4-maleimide phenoxy)benzene, and prepolymers of these, as well as prepolymers of these maleimides and amines.

[0091] In the case where the resin composition of this embodiment contains a maleimide compound, the lower limit of its content, relative to 100 parts by mass of the resin solids in the resin composition, is preferably 1 part by mass or more, more preferably 5 parts by mass or more, further preferably 10 parts by mass or more, and further preferably 20 parts by mass or more. By having a maleimide compound content of 1 part by mass or more, there is a tendency to improve the low dielectric properties and flame retardancy of the obtained cured product. Furthermore, the upper limit of the maleimide compound content, relative to 100 parts by mass of the resin solids in the resin composition, is preferably 70 parts by mass or less, more preferably 60 parts by mass or less, further preferably 50 parts by mass or less, and may also be 40 parts by mass or less. By having a maleimide compound content of 70 parts by mass or less, there is a tendency to improve the peel strength and low water absorption of the metal foil. The resin composition of this embodiment may contain only one maleic anhydride compound, or it may contain two or more. When it contains two or more, the total amount should preferably be within the range described above.

[0092] <<Epoxy Compounds>> The resin composition of this embodiment may also contain epoxy compounds. There are no particular limitations on epoxy compounds or resins that have one or more epoxy groups in one molecule (preferably 2 to 12, more preferably 2 to 6, further preferably 2 to 4, further preferably 2 or 3, and even more preferably 2). They are commonly used in the field of printed wiring boards. Epoxy compounds, for example, include bisphenol A type epoxy resin, bisphenol E type epoxy resin, bisphenol F type epoxy resin, bisphenol S type epoxy resin, phenolic varnish type epoxy resin, bisphenol A phenolic varnish type epoxy resin, glycidyl ester type epoxy resin, aralkylphenolic varnish type epoxy resin, biphenyl aralkyl type epoxy resin, naphthyl ether type epoxy resin, cresol phenolic varnish type epoxy resin, polyfunctional phenol type epoxy resin, naphthalene type epoxy resin, and anthracene. This includes various epoxy resins such as naphthalene-based modified phenolic varnish epoxy resins, phenolic aralkyl epoxy resins, naphthol aralkyl epoxy resins, dicyclopentadiene epoxy resins, biphenyl epoxy resins, alicyclic epoxy resins, polyol epoxy resins, phosphorus-containing epoxy resins, glycidylamine, glycidyl ester, compounds obtained by epoxidizing the double bonds of butadiene, and compounds obtained by reacting hydroxyl-containing polysiloxane with epichlorohydrin. Using these improves the moldability and adhesion of the resin composition. Among these, considering further improvements in flame retardancy and heat resistance, biphenyl aralkyl epoxy resins, naphthyl ether epoxy resins, polyfunctional phenolic epoxy resins, and naphthalene-based epoxy resins are preferred, with biphenyl aralkyl epoxy resins being particularly suitable.

[0093] The resin composition of this embodiment preferably contains an epoxy compound within a range that does not impair the effects of the present invention. When the resin composition of this embodiment contains an epoxy compound, its content, relative to 100 parts by mass of the resin solids in the resin composition, is preferably 0.1 parts by mass or more, more preferably 1 part by mass or more, and further preferably 2 parts by mass or more. By having an epoxy compound content of 0.1 parts by mass or more, there is a tendency to improve the peel strength and toughness of the metal foil. The upper limit of the epoxy compound content, when the resin composition of this embodiment contains an epoxy compound, relative to 100 parts by mass of the resin solids in the resin composition, is preferably 50 parts by mass or less, more preferably 30 parts by mass or less, further preferably 20 parts by mass or less, further preferably 10 parts by mass or less, further preferably 8 parts by mass or less, and further preferably 5 parts by mass or less. By having an epoxy compound content of 50 parts by mass or less, there is a tendency to improve the electrical properties of the obtained cured product. The resin composition in this embodiment may contain only one epoxy compound, or it may contain two or more. When it contains two or more, the total amount should preferably fall within the range described above. Furthermore, the resin composition in this embodiment may also be substantially free of epoxy compounds. "Substantially free" means that, relative to 100 parts by mass of the solid resin component in the resin composition, the content of epoxy compounds is less than 1 part by mass, preferably less than 0.1 parts by mass, and more preferably less than 0.01 parts by mass.

[0094] In addition to the above, for other resins (D), please refer to paragraphs 0037-0123 and 0133-0145 of Japanese Patent Application Publication No. 2020-117714, which are incorporated herein by reference.

[0095] Regarding the total amount of other resins (D), when other resins (D) are present, their total content relative to 100 parts by mass of the resin solids should preferably be 5 parts by mass or more, more preferably 10 parts by mass or more, further preferably 20 parts by mass or more, and even more preferably 30 parts by mass or more. Reaching the lower limit or above tends to further improve glass transition temperature and heat resistance. Furthermore, the upper limit of the total content of the aforementioned other resins (D), relative to 100 parts by mass of the resin solids, should preferably be 70 parts by mass or less, more preferably 60 parts by mass or less, further preferably 50 parts by mass or less, and may also be 40 parts by mass or less. Reaching the upper limit or below tends to further improve low dielectric loss tangent.

[0096] <Flame retardant (E)> The resin composition of this embodiment may also contain a flame retardant (E). Examples of flame retardants (E) include phosphorus-based flame retardants, halogen-based flame retardants, inorganic flame retardants, and polysiloxane-based flame retardants, with phosphorus-based flame retardants being preferable. As flame retardants (E), known alternatives can be used, such as brominated epoxy resins, brominated polycarbonates, brominated polystyrene, brominated styrene, brominated dimethylimide, tetrabromobisphenol A, pentabromobenzyl (meth)acrylate, pentabromotoluene, tribromophenol, hexabromobenzene, decabromodiphenyl ether, bis-1,2-pentabromophenyl ethane, chlorinated polystyrene, chlorinated paraffin and other halogenated flame retardants, red phosphorus, trimethylbenzene phosphate, triphenyl phosphate, cresol diphenyl phosphate, trimethylbenzene, etc. Phosphorus-based flame retardants include phenyl phosphate esters, trialkyl phosphate esters, dialkyl phosphate esters, trichloroethyl phosphate esters, phosphazenes, 1,3-phenylbis(2,6-dimethylyl phosphate ester), 10-(2,5-dihydroxyphenyl)-10H-9-oxa-10-phosphaphenanthrene-10-oxide, aluminum hydroxide, magnesium hydroxide, some gibbsite, zinc borate, antimony trioxide, etc., and polysiloxane-based flame retardants such as polysiloxane rubber and polysiloxane resin. In this embodiment, among these, considering that the low dielectric properties are not compromised, 1,3-epoxyphenylbis(2,6-dimethylphosphophosphate) is preferable.

[0097] In the case where the resin composition of this embodiment contains a flame retardant (E), its content, relative to 100 parts by mass of the resin solids in the resin composition, should preferably be 1 part by mass or more, and more preferably 5 parts by mass or more. Furthermore, the upper limit of the content of the aforementioned flame retardant should preferably be 25 parts by mass or less, and more preferably 20 parts by mass or less. Flame retardant (E) can be used alone or in combination of two or more. When using two or more, the total dosage shall be within the range described above.

[0098] <Fill Material (F)> The resin composition of this embodiment preferably contains filler (F). By containing filler (F), the dielectric properties (low dielectric constant, low dielectric loss tangent, etc.), flame retardancy, and low thermal expansion of the resin composition and its cured product can be further improved. Furthermore, the filler material (F) used in this embodiment should preferably have excellent low dielectric properties. For example, the filler material (F) used in this embodiment should preferably have a relative permittivity (Dk) of 8.0 or less, more preferably 6.0 or less, and even more preferably 4.0 or less, as measured by the cavity resonator perturbation method. Moreover, the lower limit of the aforementioned relative permittivity is, for example, 2.0 or more in practical terms. Furthermore, the filler material (F) used in this embodiment should preferably have a dielectric loss tangent (Df) of 0.05 or less, more preferably 0.01 or less, as measured by the cavity resonator perturbation method. Moreover, the lower limit of the aforementioned dielectric loss tangent is, for example, 0.0001 or more in practical terms.

[0099] The type of filler (F) used in this embodiment is not particularly limited and can be appropriately used by general users in the industry. Specifically, examples include natural silica, fused silica, synthetic silica, amorphous silica, aerosil, hollow silica, and other silica-based materials; alumina, white carbon, titanium dioxide, titanium dioxide, zinc oxide, magnesium oxide, zirconium oxide, and other metal oxides; zinc borate, zinc stannate, forsterite, barium titanate, strontium titanate, calcium titanate, and other composite oxides; boron nitride, condensed boron nitride, silicon nitride, aluminum nitride, and other nitrides; aluminum hydroxide; heat-treated aluminum hydroxide (aluminum hydroxide that has undergone heat treatment to remove some of its water of crystallization); boehmite; and hydroxides. Inorganic fillers include magnesium hydroxide and other metal hydroxides (including hydrates), 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 fibers (including E-glass, T-glass, D-glass, S-glass, Q-glass, and other glass micropowders), insulated glass, and spherical glass. Additionally, organic fillers include styrene-type, butadiene-type, and acrylic-type rubber powders, core-shell rubber powders, polysiloxane resin powders, polysiloxane rubber powders, and polysiloxane composite powders. In this embodiment, the filler (F) preferably contains an inorganic filler, and more preferably contains one or more selected from the group consisting of silicon dioxide, aluminum hydroxide, aluminum nitride, boron nitride, magnesium olivine, titanium oxide, barium titanate, strontium titanate, and calcium titanate. Considering the low dielectric properties, it is even more preferable to contain one or more selected from the group consisting of silicon dioxide and aluminum hydroxide, and further preferably to contain silicon dioxide. By using such fillers, the heat resistance, dielectric properties, thermal expansion properties, dimensional stability, and flame retardancy of the cured resin composition will be further improved.

[0100] The content of filler (F) in the resin composition of this embodiment can be appropriately set according to the desired characteristics. Although there is no particular limitation, relative to 100 parts by mass of the resin solids in the resin composition, it is preferably 10 parts by mass or more, 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 even more preferably 80 parts by mass or more. By reaching the lower limit value above the above, there is a tendency to further improve low thermal expansion and low dielectric loss tangent. In addition, the upper limit value of the filler content relative to 100 parts by mass of the resin solids is preferably 300 parts by mass or less, more preferably 250 parts by mass or less, further preferably 200 parts by mass or less, even more preferably 150 parts by mass or less, and even more preferably 120 parts by mass or less. By reaching the upper limit value below the above, there is a tendency to further improve moldability. In the resin composition of this embodiment, as one example of a preferred embodiment, a sample is shown in which the content of filler (F) is 30% to 80% by mass of the component excluding solvent. The resin composition of this embodiment may contain only one type of filler (F), or it may contain two or more types. In the case of containing two or more types, the total amount should preferably be within the range described above.

[0101] In the resin composition of this embodiment, when using filler (F), especially inorganic filler, a silane coupling agent may be further included. By including a silane coupling agent, there is a tendency to further improve the dispersibility of filler (F) and the adhesion strength between the resin composition and filler (F) and the substrate described later. Silane coupling agents are not particularly limited, but can be listed as those commonly used in the surface treatment of inorganic materials, such as aminosilane compounds (e.g., γ-aminopropyltriethoxysilane, N-β-(aminoethyl)-γ-aminopropyltrimethoxysilane, etc.), epoxysilane compounds (e.g., γ-epoxypropoxypropyltrimethoxysilane, etc.), vinylsilane compounds (e.g., vinyltrimethoxysilane, etc.), styrylsilane compounds (e.g., styryltrimethoxysilane, etc.), acrylic silane compounds (e.g., γ-acrylpropyltrimethoxysilane, etc.), cationic silane compounds (e.g., N-β-(N-vinylbenzylaminoethyl)-γ-aminopropyltrimethoxysilane hydrochloride, etc.), and phenylsilane compounds, etc. Silane coupling agents can be used alone or in combination of two or more. In particular, by using at least one of the groups consisting of vinyl silane compounds, acrylic silane compounds, and styrene silane compounds as a silane coupling agent, and using a thermosetting resin containing aromatic rings and vinyl groups (especially a polymer having the constituent units represented by formula (V)) as the above-mentioned compatible thermosetting resin (C), a resin composition that maintains excellent dielectric properties and has excellent moisture absorption and heat resistance can be obtained. There is no particular limit to the content of the silane coupling agent; it can be 0.1 to 5.0 parts by weight relative to 100 parts by weight of the resin solids.

[0102] <Monomers or oligomers containing vinyl unsaturated groups> In the resin composition of this embodiment, in order to improve thermosetting properties and curing properties caused by active energy rays (such as photocuring properties caused by ultraviolet light), monomers or oligomers having vinyl unsaturated groups can also be used. The oligomers or monomers having vinyl unsaturated groups used in this embodiment are not particularly limited as long as they have one or more vinyl unsaturated groups per molecule; examples include monomers or oligomers having (meth)acrylic groups, vinyl groups, etc. Furthermore, in this specification, compounds that are equivalent to monomers or oligomers having vinyl unsaturated groups, and also equivalent to polyphenylene ether compounds having carbon-carbon unsaturated double bonds at the ends, are considered as polyphenylene ether compounds having carbon-carbon unsaturated double bonds at the ends.

[0103] More specifically, as monomers containing ethylene unsaturated groups, compounds (F1) with a molecular weight of less than 1000 and containing one organic group with an ethylene unsaturated bond (Compound (F1)) can be listed. It is speculated that by using Compound (F1), the ethylene unsaturated bond of Compound (F1) will react with the aforementioned compatible thermosetting resin (C), thereby improving the moisture absorption and heat resistance of the obtained cured product. The vinyl unsaturated bonds constituting the aforementioned organic groups containing vinyl unsaturated bonds do not include the meaning of vinyl unsaturated bonds being part of an aromatic ring. On the other hand, they do include the meaning of vinyl unsaturated bonds being part of a non-aromatic ring. Examples of vinyl unsaturated bonds being part of a non-aromatic ring include cyclohexenyl groups in a molecule. Furthermore, it also includes the portion other than the end of the organic group in a straight or branched chain, that is, the meaning of vinyl unsaturated bonds being present in the straight or branched chain. The organic groups containing vinyl unsaturated bonds are preferably selected from one of the groups consisting of vinyl, allyl, acrylic, and methacrylic groups, and are more preferably vinyl. Furthermore, in this specification, a compound that is equivalent to a monomer or oligomer having an ethylene unsaturated group and is also equivalent to a silane coupling agent is considered a silane coupling agent.

[0104] The compound (F1) used in this embodiment is preferably composed only of atoms selected from carbon, hydrogen, oxygen and silicon atoms, and more preferably only of atoms selected from carbon, hydrogen and oxygen atoms. Furthermore, the compound (F1) used in this embodiment may or may not have a polar group. The compound (F1) used in this embodiment is preferably non-polar. Examples of polar groups include amino, carboxyl, hydroxyl, and nitro groups.

[0105] In this embodiment, the molecular weight of compound (F1) is preferably 70 or higher, more preferably 80 or higher, and even more preferably 90 or higher. By reaching the lower limit value mentioned above, there is a tendency to suppress the volatilization of compound (F1) from the resin composition or its cured form in this embodiment. The upper limit value of the molecular weight of compound (F1) is preferably 500 or lower, more preferably 400 or lower, even more preferably 300 or lower, and even more preferably 200 or lower, or may be 150 or lower. By reaching the upper limit value mentioned above, there is a tendency to further improve the reactivity with the aforementioned compatible thermosetting resin (C). In the case where the resin composition of this embodiment contains two or more compounds (F1), the average molecular weight of the compounds (F1) should preferably be within the range mentioned above, and more preferably the molecular weight of each compound should be within the preferred range mentioned above.

[0106] In this embodiment, the compound (F1) preferably has a boiling point of 110°C or higher, more preferably 115°C or higher, and even more preferably 120°C or higher. By achieving the lower limit value mentioned above, the volatilization of the compound (F1) during the thermosetting of the resin composition can be suppressed, thereby allowing the thermosetting resin (C) to react with the compound (F1). The boiling point of the compound (F1) is preferably 300°C or lower, more preferably 250°C or lower, and even more preferably 200°C or lower. By achieving the upper limit value mentioned above, it is less likely to remain as a residual solvent in the cured product. In the case where the resin composition of this embodiment contains two or more compounds (F1), the average boiling point should fall within the above-mentioned range, and preferably the boiling point of each compound should be included in the above-mentioned preferred range.

[0107] Examples of compounds (F1) include (meth)acrylate compounds, aromatic vinyl compounds (preferably styrene compounds), saturated fatty acid vinyl compounds, cyanide vinyl compounds, vinyl unsaturated carboxylic acids, vinyl unsaturated carboxylic anhydrides, vinyl unsaturated dicarboxylic acid monoalkyl esters, vinyl unsaturated carboxylamines, etc., preferably selected from at least one of the groups consisting of (meth)acrylate compounds, aromatic vinyl compounds, and saturated fatty acid vinyl compounds, and more preferably aromatic vinyl compounds. Specific examples of compounds (F1) include methylstyrene and ethyl vinylbenzene.

[0108] On the other hand, the resin composition of this embodiment also preferably contains styrene oligomer (F2) to improve the low dielectric constant and low dielectric loss tangent. The styrene oligomer (F2) of this embodiment is a compound with an unbranched structure that is polymerized from at least one of the group consisting of styrene, the above-mentioned styrene derivatives, and vinyltoluene.

[0109] Examples of styrene oligomers (F2) used in this embodiment include styrene polymers, vinyltoluene polymers, α-methylstyrene polymers, vinyltoluene-α-methylstyrene polymers, and styrene-α-styrene polymers. Commercially available styrene polymers may also be used, such as 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), and FTR-8120 (manufactured by Mitsui Chemicals). Furthermore, Piccotex LC (manufactured by Eastman Chemical Company) is an example of 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.), and FMR-0150 (manufactured by Mitsui Chemicals Co., Ltd.). Furthermore, examples of styrene-α-styrene polymers include FTR-2120 (manufactured by Mitsui Chemicals Co., Ltd.). These styrene oligomers can be used alone or in combination of two or more. In the resin composition of this embodiment, the α-methylstyrene oligomer exhibits good thermosetting properties, excellent embedding properties for fine wiring, and superior solder heat resistance, low relative permittivity, and low dielectric loss tangent, thus making it superior.

[0110] Furthermore, details of monomers or oligomers having vinyl unsaturated groups can be found in paragraphs 0069 to 0087 of International Publication No. 2017 / 135168 and paragraphs 0065 to 0067 of International Publication No. 2019 / 230945, which are incorporated herein by reference.

[0111] By using monomers or oligomers having vinyl unsaturated groups and as the above-mentioned compatible thermosetting resin (C), and using thermosetting resins containing aromatic rings and vinyl groups (especially polymers having constituent units represented by formula (V), a resin composition with excellent moisture absorption and heat resistance can be obtained while maintaining excellent dielectric properties.

[0112] In the case where the resin composition of this embodiment contains monomers or oligomers having vinyl unsaturated groups, the content of such monomers or oligomers relative to 100 parts by mass of the resin solids is preferably 0.5 parts by mass or more, more preferably 1 part by mass or more, further preferably 2 parts by mass or more, further preferably 3 parts by mass or more, and may also be 5 parts by mass or more. Reaching the aforementioned lower limit or above tends to further improve the low dielectric properties. Furthermore, the upper limit of the content of the aforementioned monomers or oligomers having vinyl unsaturated groups relative to 100 parts by mass of the resin solids is preferably 30 parts by mass or less, more preferably 25 parts by mass or less, further preferably 20 parts by mass or less, further preferably 15 parts by mass or less, and further preferably 10 parts by mass or less. Reaching the aforementioned upper limit or below tends to further improve heat resistance. Furthermore, it tends to further improve low dielectric constant, low dielectric loss tangent, and chemical resistance. The resin composition of this embodiment may contain only one monomer or oligomer with an ethylene unsaturated group, or it may contain two or more. When it contains two or more, the total amount should preferably be within the range described above.

[0113] <Active Ester Compounds> The resin composition of this embodiment may also contain active ester compounds. As an active ester compound, there are no particular limitations. Examples include compounds having two or more (preferably 2 to 12, more preferably 2 to 6, further preferably 2 to 4, further preferably 2 or 3, further preferably 2) active ester groups in one molecule. The active ester compound can also be a straight-chain, branched, or cyclic compound. Among these, considering the viewpoint of further improving the heat resistance of the obtained cured product, it is preferable to obtain an active ester compound by reacting a carboxylic acid compound and / or a thiocarboxylic acid compound with a hydroxyl compound and / or a thiol compound; more preferably, it is preferable to obtain an active ester compound by reacting a carboxylic acid compound with one or more compounds selected from the group consisting of phenolic compounds, naphthol compounds, and thiol compounds; further preferably, it is preferable to obtain an aromatic compound having two or more active ester groups in one molecule by reacting a carboxylic acid compound with an aromatic compound having phenolic hydroxyl groups; and especially preferably, it is preferable to obtain an aromatic compound having two or more active ester groups in one molecule by reacting a compound having two or more carboxylic acids in one molecule with an aromatic compound having phenolic hydroxyl groups. As the aforementioned carboxylic acid compound, one or more may be selected from the group consisting of benzoic acid, acetic acid, succinic acid, maleic acid, itaconic acid, phthalic acid, isophthalic acid, terephthalic acid, and pyromellitic acid. Among these, considering the viewpoint of further improving the heat resistance of the obtained cured product, it is preferable to select one or more from the group consisting of succinic acid, maleic acid, itaconic acid, phthalic acid, isophthalic acid, and terephthalic acid, and more preferably to select one or more from the group consisting of isophthalic acid and terephthalic acid. Examples of the above-mentioned thiocarboxylic acid compounds include one or more selected from thioacetic acid and thiobenzoic acid. Examples of the aforementioned phenolic or naphthol compounds include hydroquinone, resorcinol, bisphenol A, bisphenol F, bisphenol S, reduced phenolphthalein, methylated bisphenol A, methylated bisphenol F, methylated bisphenol S, phenol, o-cresol, m-cresol, p-cresol, catechol, α-naphthol, β-naphthol, 1,5-dihydroxynaphthol, 1,6-dihydroxynaphthol, 2,6-dihydroxynaphthol, dihydroxybenzophenone, trihydroxybenzophenone, and tetrahydroxybenzophenone. One or more of the following groups constitute methyl ketone, pyrogallol, phenylglycerol, dicyclopentadienyl diphenol, and phenolic varnish, and considering the viewpoint of further improving the heat resistance and solvent solubility of the obtained cured product, are preferably bisphenol A, bisphenol F, bisphenol S, methylated bisphenol A, methylated bisphenol F, methylated bisphenol S, catechol, α-naphthol, β-naphthol, 1,5-dihydroxynaphthol, 1,6-dihydroxynaphthol, 2,6-dihydroxynaphthol, dihydroxybenzophenone, trihydroxybenzophenone, or tetrahydroxybenzophenone. Methyl ketone, pyrogallol, benzotriol, dicyclopentadienyl diphenol, and phenolic varnish are preferably selected from one or more of the group consisting of catechol, 1,5-dihydroxynaphthalene, 1,6-dihydroxynaphthalene, 2,6-dihydroxynaphthalene, dihydroxybenzophenone, trihydroxybenzophenone, tetrahydroxybenzophenone, pyrogallol, benzotriol, dicyclopentadienyl diphenol, and phenolic varnish, and more preferably selected from the group consisting of 1,5-dihydroxynaphthalene, 1,6-dihydroxynaphthalene, 2,6-dihydroxynaphthalene, dihydroxybenzophenone, trihydroxybenzophenone, tetrahydroxybenzophenone, pyrogallol, benzotriol, dicyclopentadienyl diphenol, and phenolic varnish. One or more of the group consisting of naphthalene, dihydroxybenzophenone, trihydroxybenzophenone, tetrahydroxybenzophenone, dicyclopentadienyldiphenol, and phenolic varnish, especially preferably selected from one or more of the group consisting of dihydroxybenzophenone, trihydroxybenzophenone, tetrahydroxybenzophenone, dicyclopentadienyldiphenol, and phenolic varnish (preferably selected from one or more of the group consisting of dicyclopentadienyldiphenol and phenolic varnish, more preferably dicyclopentadienyldiphenol). The aforementioned thiol compounds may be selected from one or more compounds in the group consisting of benzenedithiol and tridithiol. Furthermore, considering the need to further improve compatibility with epoxides, reactive ester compounds are preferably compounds containing two or more carboxylic acids and aliphatic chains per molecule; considering the need to further improve heat resistance, compounds containing aromatic rings are preferable. More specific examples of reactive ester compounds can be found in Japanese Patent Application Publication No. 2004-277460.

[0114] The active ester compounds can be commercially available or prepared by known methods. Examples of commercially available compounds include those containing a dicyclopentadienyldiphenol structure (e.g., EXB9451, EXB9460, EXB9460S, HPC-8000-65T (all manufactured by DIC), acetylated derivatives of phenolic varnishes (e.g., DC808 (manufactured by Mitsubishi Chemical), and benzoyl derivatives of phenolic varnishes (e.g., YLH1026, YLH1030, YLH1048 (all manufactured by Mitsubishi Chemical)). Considering the need for improved storage stability of the varnish and lower thermal expansion during resin curing (of the cured product), EXB9460S is preferable.

[0115] Active ester compounds can be prepared by known methods, such as by the condensation reaction of a carboxylic acid compound with a hydroxyl compound. As a specific example, a method can be described in which (a) a carboxylic acid compound or its halide, (b) a hydroxyl compound, and (c) an aromatic monohydroxyl compound are reacted in a ratio of 1 mole relative to the carboxyl or acetohalo group of (a), 0.05 to 0.75 moles relative to the phenolic hydroxyl group of (b), and 0.25 to 0.95 moles relative to (c).

[0116] The resin composition of this embodiment preferably contains an active ester compound within a range that does not impair the effects of the present invention. When the resin composition of this embodiment contains an active ester compound, the amount should preferably be 1 part by weight or more, and further preferably 90 parts by weight or less, relative to 100 parts by weight of the resin solids in the resin composition. The resin composition in this embodiment may contain only one type of active ester compound, or it may contain two or more types. When it contains two or more types, the total amount should preferably be within the range described above. Furthermore, the resin composition in this embodiment may also be substantially free of active ester compounds. "Substantially free" means that the content of the active ester compound relative to 100 parts by mass of the resin solids in the resin composition is less than 1 part by mass, preferably less than 0.1 parts by mass, and more preferably less than 0.01 parts by mass.

[0117] <Dispersant> The resin composition of this embodiment may also contain a dispersant. As a dispersant, any commonly used dispersant in coatings may be suitable, and there is no particular limitation on its type. A copolymer-based wetting dispersant is preferred; specific examples include BYK JAPAN KK's DISPERBYK (registered trademark) 110, 111, 161, 180, 2009, 2152, 2155, BYK (registered trademark) W996, W9010, W903, W940, etc.

[0118] In the case where the resin composition of this embodiment contains a dispersant, the lower limit of its content, relative to 100 parts by mass of the resin solids in the resin composition, is preferably 0.01 parts by mass or more, more preferably 0.1 parts by mass or more, and may also be 0.3 parts by mass or more. Furthermore, the upper limit of the above-mentioned dispersant content, relative to 100 parts by mass of the resin solids in the resin composition, is preferably 10 parts by mass or less, more preferably 5 parts by mass or less, and further preferably 3 parts by mass or less. A single dispersant may be used alone, or in combination of two or more. When using two or more dispersants, the total dosage shall fall within the range described above.

[0119] Hardening accelerator The resin composition of this embodiment may further contain a curing accelerator. There are no particular limitations on the curing accelerator, but examples include imidazoles such as 2-ethyl-4-methylimidazolium and triphenylimidazolium; organic peroxides such as benzoyl peroxide, lauryl peroxide, acetyl peroxide, p-chlorobenzoyl peroxide, ditert-tert-butyl peroxide phthalate, α,α'-di(tert-butyl peroxide)diisopropylbenzene, 2,5-dimethyl-2,5-di(tert-butyl peroxide)hexane, and 2,5-dimethyl-2,5-bis(tert-butyl peroxide)hexyn-3; azo compounds such as azodicarbonamide (e.g., azobisisobutyronitrile); N,N-dimethylbenzylamine, N,N-dimethylaniline, N,N-dimethyltoluidine, 2-N-ethylaniline ethanol, and tri-N-ethylbenzylamine. Tertiary amines such as butylamine, pyridine, quinoline, N-methylpyridine, triethanolamine, triethylenediamine, tetramethylbutanediamine, and N-methylpiperidine; phenols such as phenol, xylenol, cresol, resorcinol, and catechol; high-temperature decomposition free radical generators such as 2,3-dimethyl-2,3-diphenylbutane; organometallic salts such as lead naphthenate, lead stearate, zinc naphthenate, zinc octanoate, manganese octanoate, tin oleate, dibutyltin malate, manganese naphthenate, cobalt naphthenate, and iron acetoacetone; compounds formed by dissolving these organometallic salts in phenol, bisphenol, and other hydroxyl-containing compounds; inorganic metal salts such as tin chloride, zinc chloride, and aluminum chloride; organotin compounds such as dioctyltin oxide, other alkyltin, and alkyltin oxide. Ideal hardening accelerators are imidazoles and organometallic salts, and it is even more advisable to use a combination of imidazoles and organometallic salts. Furthermore, in this embodiment, the composition may also substantially not contain polymerization initiators such as organic peroxides and azo compounds. "Substantially not containing" means that the content of the polymerization initiator is less than 0.1 parts by mass relative to 100 parts by mass of the resin solids in the resin composition.

[0120] In this embodiment, when the resin composition contains a curing accelerator, the lower limit of its content is preferably 0.005 parts by mass or more, more preferably 0.01 parts by mass or more, and even more preferably 0.1 parts by mass or more, relative to 100 parts by mass of the resin solids in the resin composition. Furthermore, the upper limit of the curing accelerator content is preferably 10 parts by mass or less, more preferably 5 parts by mass or less, and even more preferably 2 parts by mass or less, relative to 100 parts by mass of the resin solids in the resin composition. One type of hardening accelerator may be used alone, or in combination of two or more. When two or more are used, the total dosage shall be within the range described above.

[0121] Solvent The resin composition of this embodiment may contain solvents, preferably organic solvents. When solvents are present, the resin composition of this embodiment comprises at least a portion of the aforementioned solid resin components, and is preferably in a form that is completely dissolved or miscible with the solvent (solution or varnish). As a solvent, any polar or non-polar organic solvent that can dissolve or be miscible with at least a portion of the aforementioned resin solid components is acceptable. Preferably, any polar or non-polar organic solvent that can dissolve or be miscible with all of the aforementioned resin solid components is acceptable. Examples of polar organic solvents include ketones (e.g., acetone, methyl ethyl ketone, methyl isobutyl ketone, etc.), ceroxysulfates (e.g., propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, etc.), esters (e.g., ethyl lactate, methyl acetate, ethyl acetate, butyl acetate, isoamyl acetate, ethyl lactate, methyl methoxypropionate, methyl hydroxyisobutyrate, etc.), and acetamides (e.g., dimethoxyacetamide, dimethylmethoxyacetamide, etc.). Examples of non-polar organic solvents include aromatic hydrocarbons (e.g., toluene, xylene, etc.). One solvent may be used alone, or two or more solvents may be used in combination. When two or more solvents are used, the total amount shall be within the range described above.

[0122] <Other Ingredients> In addition to the components mentioned above, the resin composition of this embodiment may also contain thermoplastic resins, oligomers, and other polymeric compounds, as well as various additives. Examples of additives include ultraviolet absorbers, antioxidants, photopolymerization initiators, fluorescent whitening agents, photosensitizers, dyes, pigments, tackifiers, flow modifiers, lubricants, defoamers, leveling agents, gloss agents, and polymerization inhibitors. These additives may be used individually or in combination of two or more.

[0123] <Applications> The resin composition of this embodiment is used as a curing agent. Specifically, the resin composition of this embodiment is a material with a low relative permittivity and / or a low dielectric loss tangent, and is suitable for use as a resin composition for electronic materials such as insulating layers for printed circuit boards and semiconductor packaging materials. The resin composition of this embodiment is suitable for use as a prepreg, a metal-clad laminate using a prepreg, a resin composite sheet, and a material for printed circuit boards. The resin composition of this embodiment is used as a layered material (including thin film, sheet, etc.) such as a prepreg or resin composite sheet for use as an insulating layer in a printed wiring board. When such a layered material is manufactured, its thickness is preferably 5 μm or more, and more preferably 10 μm or more. As an upper limit for the thickness, it is preferably 200 μm or less, and more preferably 180 μm or less. Furthermore, the thickness of the aforementioned layered material, for example, when the resin composition of this embodiment is impregnated with glass cloth, includes the thickness of the glass cloth. The material formed from the resin composition of this embodiment can be used for applications involving exposure and development to form patterns, as well as for applications without exposure and development. In particular, it is suitable for applications without exposure and development.

[0124] <<Prepreg>> The prepreg system of this embodiment is formed from a substrate (prepreg substrate) and the resin composition of this embodiment. The prepreg of this embodiment is obtained, for example, by applying the resin composition of this embodiment to a substrate (e.g., impregnation and / or coating), and then semi-curing it by heating (e.g., drying at 120-220°C for 2-15 minutes). In this case, the amount of resin composition adhering to the substrate, that is, the amount of resin composition (including filler (F)) relative to the total amount of the semi-cured prepreg, is preferably in the range of 20-99% by mass, and more preferably in the range of 20-80% by mass.

[0125] There are no particular limitations on the substrate material used in various printed circuit board materials. Examples of substrate materials include glass fibers (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), and organic fibers (such as polyimide, polyamide, polyester, liquid crystal polyester, polytetrafluoroethylene, etc.). Regarding the form of the substrate, there are no particular limitations; examples include woven fabrics, non-woven fabrics, rovings, chopped strand mats, and surfacing mats. These substrates can be used alone or in combination of two or more types. Among these substrates, considering dimensional stability, fabrics treated with super-opened fibers and pore-filling are preferable. Considering strength and low water absorption, glass fabrics with a thickness of less than 200 μm and a mass of less than 250 g / m² are preferable. Considering moisture absorption and heat resistance, glass fabrics surface-treated with silane coupling agents such as epoxy silanes and amino silanes are preferable. Considering electrical properties, low-dielectric glass cloths composed of glass fibers exhibiting low relative permittivity and low dielectric loss tangent, such as L-glass, NE-glass, and Q-glass, are even more suitable. Examples of substrates with low relative permittivity include those with a relative permittivity of 5.0 or less (preferably 3.0 to 4.9). Examples of substrates with low dielectric loss tangent include those with a dielectric loss tangent of 0.006 or less (preferably 0.001 to 0.005). The relative permittivity and dielectric loss tangent were measured at 10 GHz using a perturbation method cavity resonator.

[0126] <<Metal Foil-Clad Laminates>> The metal-clad laminate of this embodiment comprises at least one layer formed from the prepreg of this embodiment, and metal foil disposed on one or both sides of the prepreg layer. Regarding the manufacturing method of the metal-clad laminate of this embodiment, for example, a method can be used to arrange at least one piece of the prepreg (preferably overlapping two or more pieces), arrange metal foil on one or both sides of it, and then laminate it. More specifically, it can be manufactured by arranging copper, aluminum, or other metal foils on one or both sides of the prepreg and then laminating them. The number of prepreg pieces is preferably 1 to 10, more preferably 2 to 10, and even more preferably 2 to 9. As for the metal foil, there is no particular limitation as long as it is a material used for printed circuit boards, such as rolled copper foil, electrolytic copper foil, etc. The thickness of the metal foil (preferably copper foil) is not particularly limited and can be approximately 1.5 to 70 μm. Regarding the forming method, methods commonly used in forming multilayer boards and laminates for printed circuit boards can be listed. More specifically, methods using multilayer laminators, multilayer vacuum laminators, continuous forming machines, and autoclave forming machines, with temperatures of approximately 180-350°C, heating times of approximately 100-300 minutes, and surface pressures of approximately 20-100 kg / cm², can be employed for lamination forming. Furthermore, multilayer boards can also be manufactured by combining the prepreg of this embodiment with a separately manufactured inner layer circuit board and performing lamination forming. Regarding the manufacturing method of multilayer boards, for example, copper foil of approximately 35 μm is placed on both sides of a prepreg of this embodiment. After lamination and formation using the above forming method, an inner layer circuit is formed. This circuit is then blackened to form an inner layer circuit board. Subsequently, one inner layer circuit board and one prepreg of this embodiment are alternately placed one on each side, and copper foil is placed on the outermost layer. Under the above conditions, lamination forming can be performed under vacuum, thus enabling the manufacture of multilayer boards. The metal foil laminate of this embodiment is suitable for use as a printed wiring board.

[0127] Furthermore, the metal-clad laminate of this embodiment should preferably have a low dielectric loss tangent (Df) as measured by using a laminate with the metal foil removed by etching. Specifically, the dielectric loss tangent (Df) at 10 GHz, measured using the cavity resonator perturbation method, should preferably be 0.0040 or less, more preferably 0.0030 or less, further preferably 0.0025 or less, and even more preferably less than 0.0025. There is no particular limitation on the lower limit of the above dielectric loss tangent (Df), for example, practically it is 0.0001 or more. The dielectric loss tangent was determined in accordance with the description of the examples described later. Furthermore, the metal-clad laminate of this embodiment should preferably have a low coefficient of thermal expansion (CTE) as measured by using a laminate with the metal foil removed by etching. Specifically, the CTE should preferably be 10 ppm / ℃ or less. Ideally, the lower limit should be 0, and practically it should be 0.001 ppm / ℃ or more. The determination of CTE was performed in accordance with the description of the examples described later.

[0128] As described above, the resin composition for electronic materials obtained by using the resin composition of this embodiment (a resin composition composed of a combination of specific components) can have excellent properties in its cured form, such as dielectric properties (low dielectric loss tangent), moisture absorption and heat resistance, as well as excellent crack resistance, appearance of the cured form, and low thermal expansion.

[0129] Printed Wiring Boards The printed circuit board of this embodiment comprises an insulating layer and a conductor layer disposed on the surface of the insulating layer. The insulating layer comprises at least one of a layer formed of a resin composition of this embodiment and a layer formed of a prepreg of this embodiment. Such a printed circuit board can be manufactured by conventional methods, and the manufacturing method is not particularly limited. An example of a manufacturing method for a printed circuit board is shown below. First, a metal-clad laminate, such as the copper-clad laminate, is prepared. Next, an etching process is performed on the surface of the metal-clad laminate to form inner layer circuits to create an inner layer substrate. As required, a surface treatment is performed on the surface of the inner layer circuits of the inner layer substrate to improve the adhesion strength. Then, the required number of prepregs are stacked on the surface of the inner layer circuits, and metal foils for outer layer circuits are further stacked on the outside. The substrate is then heated and pressed to form a single unit. In this manner, a multilayer laminate is manufactured in which a substrate and an insulating layer composed of a hardened resin composition are formed between the metal foils for the inner and outer layer circuits. Next, through holes or via holes are made in the multilayer board, and a plated metal film is formed on the wall of the hole to conduct the metal foil used for the inner layer circuit and the outer layer circuit. The outer layer circuit is then formed by etching the metal foil used for the outer layer circuit to manufacture the printed wiring board.

[0130] The printed wiring board obtained by the above manufacturing example will have an insulating layer and a conductor layer formed on the surface of the insulating layer. The insulating layer contains the resin composition of the present embodiment and / or its cured form. That is, the prepreg of the present embodiment (e.g., a prepreg formed from a substrate and the resin composition of the present embodiment impregnated or coated on the substrate) and the layer formed from the resin composition of the metal foil laminate of the present embodiment become the insulating layer of the present embodiment. Furthermore, this embodiment also relates to a semiconductor device containing the aforementioned printed wiring board. For details of the semiconductor device, please refer to paragraphs 0200 to 0202 of Japanese Patent Application Publication No. 2021-021027, which are incorporated herein by reference.

[0131] <<Resin Composite Sheet>> The resin composite sheet of this embodiment includes a support and a layer formed of the resin composition of this embodiment disposed on the surface of the support. The resin composite sheet can be used as a stacking film or a dry film solder resist. There are no particular limitations on the manufacturing method of the resin composite sheet; for example, a method can be used to obtain the resin composite sheet by coating a solution obtained by dissolving the resin composition of this embodiment in a solvent onto a support and then drying it.

[0132] Regarding the support used here, examples include polyethylene film, polypropylene film, polycarbonate film, polyethylene terephthalate film, ethylene tetrafluoroethylene copolymer film, and release films obtained by coating the surface of such films with a release agent, organic film substrates such as polyimide film, conductor foils such as copper foil and aluminum foil, glass plates, SUS (Steel Use Stainless) plates, FRP (Fiber-Reinforced Plastics) and other sheet-like materials, without particular limitation.

[0133] Regarding the coating method, examples include applying a solution obtained by dissolving the resin composition of this embodiment in a solvent onto a support using a coating rod, a die coater, a doctor blade, or a BAKER-type coating applicator. Alternatively, a single-layer sheet can be obtained by peeling or etching the support from the resin composite sheet obtained by laminating the support and the resin composition after drying. Furthermore, a single-layer sheet can be obtained without using a support by supplying a solution obtained by dissolving the resin composition of this embodiment in a solvent into a mold having a sheet-like mold groove, and then drying it to form a sheet.

[0134] Furthermore, in the fabrication of the single-layer sheet or resin composite sheet of this embodiment, there are no particular limitations on the drying conditions when removing the solvent. Considering that if the temperature is too low, solvent residue may easily remain in the resin composition, and if the temperature is too high, the resin composition will harden, it is advisable to use a temperature of 20°C to 200°C for 1 to 90 minutes. In addition, in the single-layer sheet or resin composite sheet, the resin composition can be used in an uncured state after only drying the solvent, or it can be used in a semi-cured (B-stage) state as required. Furthermore, 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 resin composition solution and the coating thickness during coating (coating), and there are no particular limitations. Considering that generally, if the coating thickness is too thick, solvent residue is more likely to remain during drying, it is advisable to use a thickness of 0.1 to 500 μm. [Example]

[0135] The following examples illustrate the present invention in more detail. The materials, amounts, proportions, processing contents, and processing order shown in the following examples can be appropriately modified without departing from the spirit of the present invention. Therefore, the scope of the present invention is not limited to the specific examples shown below. In cases where the measuring instruments used in the embodiments are difficult to obtain due to production stoppages or other reasons, other instruments with equivalent performance can be used for measurement.

[0136] <Synthesis Example 1: Synthesis of Modified Polyphenylene Ether Compounds> <<Synthesis of 2-functionalized phenyl ether oligomers>> In a 12L vertical reactor equipped with a stirrer, thermometer, air inlet pipe, and baffle, 29.36g (42.1mmol) of CuBr, 1.81g (10.5mmol) of N,N'-di-tert-butylethylenediamine, 67.77g (671.0mmol) of n-butyldimethylamine, and 2,600g of toluene were added. The mixture was stirred at a reaction temperature of 40°C. 129.32g (0.48mol) of 2,2',3,3',5,5'-hexamethyl-(1,1'-biphenol)-4,4'-diol, 2,6'-diol, and other pre-mixed components were added. A mixture of 878.4 g (7.2 mol) of dimethylphenol, 1.22 g (7.2 mmol) of N,N'-di-tert-butylethylenediamine, and 26.35 g (260.9 mmol) of n-butyldimethylamine was dissolved in 2,300 g of methanol. The mixture was added dropwise over 230 minutes with stirring, using a nitrogen and air mixture adjusted to an oxygen concentration of 8% by volume at a flow rate of 5.2 L / min. After the addition was complete, 1,500 g of water containing 48.06 g (126.4 mmol) of tetrasodium ethylenediaminetetraacetate was added to stop the reaction. The aqueous and organic layers were separated. The organic layer was washed with a 1N hydrochloric acid solution and then with pure water. The resulting solution was concentrated to 50% by mass using an evaporator to obtain 1981 g of a toluene solution of a difunctional phenyl ether oligomer (resin "A"). The GPC-converted number average molecular weight of polystyrene from resin "A" is 1975, the GPC-converted weight average molecular weight of polystyrene is 3514, and the hydroxyl equivalent is 990.

[0137] Synthesis of Modified Polyphenylene Ether Compounds In a reactor equipped with a stirrer, thermometer, and reflux pipe, 833.4 g of a toluene solution of resin "A", 76.7 g of vinyl benzyl chloride (manufactured by AGC SEIMI CHEMICAL CO., LTD., "CMS-P"), 1,600 g of dichloromethane, 6.2 g of benzyl dimethylamine, 199.5 g of pure water, and 83.6 g of a 30.5% (w / w) NaOH aqueous solution were added. The reaction was carried out at a reaction temperature of 40°C with stirring. After stirring for 24 hours, the organic layer was washed with a 1N hydrochloric acid aqueous solution and then washed with pure water. The obtained solution was concentrated using an evaporator, added dropwise to methanol for solidification, and the solid was recovered by filtration and vacuum dried to obtain 450.1 g of modified polyphenylene ether compound. The GPC-converted number average molecular weight of the modified polyphenylene ether compound is 2250, the GPC-converted weight average molecular weight of the polystyrene is 3920, and the vinyl equivalent is 1189 g / vinyl.

[0138] <Synthetic Example 2: Synthesis of Naphthol Arylalkyl Cyanate Compound (SNCN)> 0.47 mol (OH group conversion) of α-naphthol aralkyl resin (SN495V, OH group equivalent: 236 g / eq., manufactured by Nippon Steel Chemical Co., Ltd.: containing 1 to 5 repeating units of naphthol aralkyl group) was dissolved in 500 mL of chloroform. 0.7 mol of triethylamine was added to this solution to prepare solution 1. While maintaining the temperature at -10°C, solution 1 was added dropwise over 1.5 hours to a chloroform solution containing 0.93 mol of cyanogen chloride. After the addition was complete, the mixture was stirred for 30 minutes. Then, a mixture of 0.1 mol of triethylamine and 30 g of chloroform was added dropwise to the reactor, and the reaction was stopped by stirring for 30 minutes. The byproduct triethylamine hydrochloride was separated from the reaction solution by filtration. The filtrate was washed four times with 500 mL of 0.1 N hydrochloric acid, followed by washing with 500 mL of water. After drying with sodium sulfate, the mixture was evaporated at 75°C and then degassed under reduced pressure at 90°C to obtain a brown solid α-naphthol aralkyl cyanate compound represented by formula (S1) (where RC1 to RC4 are all hydrogen atoms, and nc is a mixture of 1 to 5). The obtained α-naphthol aralkyl cyanate compound was analyzed by infrared absorption spectroscopy, confirming absorption of the cyanate group near 2264 cm-1. [Chemistry 42]

[0139] <Synthetic Example 3: Synthesis of a polymer (va) having constituent units represented by formula (V)> 2.25 mol (292.9 g) of divinylbenzene, 1.32 mol (172.0 g) of ethylvinylbenzene, 11.43 mol (1190.3 g) of styrene, and 15.0 mol (1532.0 g) of n-propyl acetate were added to a reactor. 600 mmol of a boron trifluoride diethyl ether complex was added at 70°C, and the reaction was allowed to proceed for 4 hours. After stopping the polymerization reaction with an aqueous sodium bicarbonate solution, the oil layer was washed three times with pure water, and the mixture was subjected to vacuum volatilization at 60°C to recover the polymer (va) containing the constituent units represented by formula (V). The obtained polymer (va) containing the constituent units represented by formula (V) was weighed, confirming that 860.8 g of polymer (va) containing the constituent units represented by formula (V) was obtained.

[0140] The obtained polymer (va) with constituent units represented by formula (V) has 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. Resonance lines from each monomer unit used as a raw material were observed in the polymer (va) with constituent units represented by formula (V) by 13C-NMR and 1H-NMR analysis. Based on the NMR and GC analysis results, the proportions of each monomer unit (from each raw material) in the polymer (va) with constituent units represented by formula (V) were calculated as follows. Constituents from divinylbenzene: 20.9 moles (24.3% by mass) Constituents from ethyl vinylbenzene: 9.1 moles (10.7% by mass) Constituents from styrene: 70.0 moles (65.0% by mass) In addition, the constituent units of residual vinyl groups from divinylbenzene are 16.7 moles (18.5% by mass).

[0141] <Determination of weight-average molecular weight and number-average molecular weight> Weight-average molecular weight (Mw) and number-average molecular weight (Mn) were determined by gel permeation chromatography (GPC). A delivery pump (Shimadzu Corporation, LC-20AD), a differential refractive index detector (Shimadzu Corporation, RID-10A), and GPC columns (Showa Denko Corporation, GPC KF-801, 802, 803, 804) were used. Tetrahydrofuran was used as the solvent at a flow rate of 1.0 mL / min and a column temperature of 40 °C. A calibration curve was obtained using monodisperse polystyrene.

[0142] Example 1 The mixture comprises 30 parts by mass of the modified polyphenylene ether compound obtained in Synthesis Example 1, 30 parts by mass of the maleimide compound (manufactured by Nippon Kayaku Co., Ltd., MIR-3000-70MT, equivalent to the compound represented by formula (M3)), 5 parts by mass of the naphthol aralkyl cyanate compound (SNCN) obtained in Synthesis Example 2, 5 parts by mass of the α-methylstyrene oligomer (KA3085 (trade name), weight average molecular weight: 664, manufactured by Eastman Chemical Company), 15 parts by mass of the phosphorus-based flame retardant (PX-200, Daihachi Chemical Industry Co., Ltd.), 7.5 parts by mass of the hydrogenated styrene thermoplastic elastomer (SEBS, SEPTON2104, Mn83000, manufactured by Kuraray Co., Ltd.), 7.5 parts by mass of the non-hydrogenated styrene thermoplastic elastomer (SBS, TR2250, Mn115000, manufactured by JSR Co., Ltd.), and silicon dioxide (Admatechs Company). Limited production, SC2050-MNU) 100 parts by weight, diluted with methyl ethyl ketone to obtain a solid content of 65% by weight to obtain a varnish. In addition, the blending amount of each component indicates the amount of solid content.

[0143] The varnish was impregnated onto a 0.1 mm thick NE glass fabric (manufactured by Nitto Bosek Corporation, 2013 S101S), and dried at 165°C for 5 minutes to obtain a prepreg (0.1 mm thick) with a resin composition content of 60% by mass. Furthermore, the characteristics of the NE glass fabric used are as described below. IPC corresponding categories: 2013 Longitudinal density (roots / 25mm): 46 Lateral density (roots / 25mm): 44.1 Thickness (mm): 0.070 Mass (g / m²): 80.7 One or eight prepregs are stacked together, and 12μm thick electrolytic copper foil (3EC-M3-VLP, manufactured by Mitsui Metal Mining Co., Ltd.) is placed on both sides. The prepregs are then vacuum pressed at a pressure of 30kgf / cm2 and a temperature of 220℃ for 120 minutes to obtain a copper-clad laminate with an insulation layer thickness of 0.1mm or 0.8mm as a metal-clad laminate.

[0144] For the obtained copper-clad laminate, the physical properties (dielectric loss tangent (Df), moisture absorption and heat resistance, crack resistance, appearance after curing, and coefficient of thermal expansion (CTE)) were evaluated according to the methods described below.

[0145] <Dielectric loss tangent> For the obtained copper-clad laminate, a test piece (30mm×150mm×0.8mm) was made by etching away the copper foil. The dielectric loss tangent (Df) at 10GHz was measured using a perturbation method cavity resonator. The measurement temperature was set to 23℃. The perturbation method cavity resonator uses Agilent Technologies, Ltd. products, Agilent 8722ES. Evaluate as follows. A: Not reached 0.0025 B: 0.0025 or higher

[0146] <Moisture absorption and heat resistance> For the obtained copper-clad laminate, a test piece (50mm × 50mm × 0.8mm) was prepared by etching away all the copper foil on one side and etching away half of the copper foil on the other side. This test piece was then subjected to a pressure cooking test chamber at 121°C and 2 atmospheres of saturated steam for 3 hours, followed by immersion in a solder bath at 260°C for 30 seconds to observe for any peeling. The pressure cooking test chamber used was a PC-3 model manufactured by Hirayama Manufacturing Co., Ltd. A: No abnormalities B: There is peeling

[0147] Crack resistance (MIT test) For the obtained copper-clad laminate, in accordance with JIS C5016:1994, a test piece (15mm×130mm×0.1mm) with a wiring pattern of 1mm width was made on the copper foil. Insulated wires were installed at the terminals of the conductor pattern on the test piece. The upper end of the test piece was fixed to a plunger, and a load of 1kgf was applied to the lower end. Under the condition of power-on, the test piece was bent in both directions at an angle of 135° and a speed of 175cpm. The number of back-and-forth bends until the wire broke was measured. Evaluate as follows. S: 81 times or more A: 71 to 80 times B: 40 to 70 times C: Less than 39 times

[0148] <Appearance after hardening> The copper foil of the obtained copper-clad laminate was removed by etching to obtain a test piece (330mm×330mm×0.1mm) for appearance observation after curing. The surface was observed to confirm the separation state of thermoplastic elastomer (A) and / or thermoplastic elastomer (B) from thermosetting resin (C), and the presence of any appearance abnormalities was evaluated according to the following evaluation criteria. The evaluation will be conducted as follows. The evaluation will be carried out by a majority vote of 5 experts. A: No abnormalities B: There are cosmetic defects.

[0149] Coefficient of linear thermal expansion (CTE) For the test piece (4.5mm × 10mm × 0.1mm) obtained by etching away the copper foil of the copper-clad laminate, the coefficient of thermal expansion of the test piece was determined using the TMA (Thermo-Mechanical Analysis) method specified in JIS C 6481 5.19. Specifically, after etching away the copper foil on both sides of the obtained copper-clad laminate and reducing its size, the linear coefficient of thermal expansion (CTE(X)) (unit: ppm / ℃) in the planar direction was measured using a thermo-mechanical analysis apparatus (manufactured by TA Instruments) at a temperature increase of 10℃ per minute from 30℃ to 340℃. The measurement direction was the longitudinal direction (warp) of the glass cloth of the laminate. ppm is a volume ratio. For other details, please refer to JIS C 6481 5.19. Evaluate as follows. A: Below 10ppm / ℃ B: Exceeding 10ppm / ℃

[0150] Example 2 In Example 1, the hydrogenated styrene thermoplastic elastomer (SEPTON2104) was replaced with an equal amount of hydrogenated styrene thermoplastic elastomer (SEBS, SOE (registered trademark) S1605, Mn250000, manufactured by Asahi Kasei Corporation), and otherwise the same method was used.

[0151] Example 3 In Example 2, an equal amount of partially hydrogenated styrene-based thermoplastic elastomers (SBBS, SOE (registered trademark) S1609, Mn228000, manufactured by Asahi Kasei Corporation) were added to replace non-hydrogenated styrene-based thermoplastic elastomers (SBS, TR2250, Mn115000, manufactured by Asahi Kasei Corporation), and otherwise the process was carried out in the same manner.

[0152] Example 4 In Example 3, the amount of the modified polyphenylene ether compound obtained in Synthesis Example 1 was changed to 15 parts by mass, and 15 parts by mass of the polymer (va) obtained in Synthesis Example 3 were also added. Otherwise, the process was carried out in the same manner.

[0153] Example 5 In Example 4, the amount of hydrogenated styrene-based thermoplastic elastomers (SEBS, SOE (registered trademark) S1605, Mn250000, manufactured by Asahi Kasei Corporation) was changed to 2 parts by mass, and the amount of some hydrogenated styrene-based thermoplastic elastomers (SBBS, SOE (registered trademark) S1609, Mn228000, manufactured by Asahi Kasei Corporation) was changed to 13 parts by mass. Otherwise, the process was carried out in the same manner.

[0154] Comparative Example 1 In Example 1, neither hydrogenated styrene-based thermoplastic elastomer (SEPTON2104) nor non-hydrogenated styrene-based thermoplastic elastomer (TR2250) were incorporated, and the amount of maleimide compound (MIR-3000-70MT) was changed to 45 parts by mass. Otherwise, the process was carried out in the same manner.

[0155] Comparative Example 2 In Example 1, neither hydrogenated styrene-based thermoplastic elastomer (SEPTON2104) nor non-hydrogenated styrene-based thermoplastic elastomer (TR2250) were incorporated, but 15 parts by weight of hydrogenated styrene-based thermoplastic elastomer (S1605) were incorporated. Otherwise, the process was carried out in the same manner.

[0156] Comparative Example 3 In Example 1, an equal amount of hydrogenated styrene-based thermoplastic elastomer (S1605) was added to replace the non-hydrogenated styrene-based thermoplastic elastomer (TR2250), otherwise the process was carried out in the same manner.

[0157] Comparative Example 4 In Example 1, the modified polyphenylene ether compound obtained in Synthesis Example 1 was not incorporated, and the amount of maleimide compound (MIR-3000-70MT) was changed to 60 parts by mass. Otherwise, the process was carried out in the same manner.

[0158] Comparative Example 5 In Comparative Example 4, an equal amount of hydrogenated styrene-based thermoplastic elastomer (S1605) was added to replace the hydrogenated styrene-based thermoplastic elastomer (SEPTON2104), and otherwise the same procedure was followed.

[0159] [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

[0160] [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

1. 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), wherein the thermoplastic elastomer (A) is obtained by hydrogenating all the conjugated diene bonds of the thermoplastic elastomer containing styrene monomer units and conjugated diene monomer units and having a number average molecular weight of 50,000 or more; and the thermoplastic elastomer (B) is obtained by hydrogenating a portion of the conjugated diene bonds of the thermoplastic elastomer containing styrene monomer units and conjugated diene monomer units and having a number average molecular weight of 50,000 or more, and / or is a thermoplastic elastomer with all bonds being unsaturated. The compatible thermosetting resin (C) comprises one or more polymers selected from the group consisting of polymers having constituent units represented by formula (V) and polyphenylene ether compounds having carbon-carbon unsaturated double bonds at the ends; the content of the thermoplastic elastomer (A) is 0.5 parts by mass or more and 20 parts by mass or less per 100 parts by mass of the resin solids; the content of the thermoplastic elastomer (B) is 0.5 parts by mass or more and 20 parts by mass or less per 100 parts by mass of the resin solids; and the content of the compatible thermosetting resin (C) is 10 to 90 parts by mass or less per 100 parts by mass of the resin solids; in formula (V), Ar represents an aromatic hydrocarbon linker; * represents a bond position.

2. The resin composition as claimed in 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 solids.

3. The resin composition as claimed in 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 to 10.

4. A resin composition comprising a thermoplastic elastomer (A), a thermoplastic elastomer (B), a thermosetting resin (C) compatible with both the thermoplastic elastomer (A) and the thermoplastic elastomer (B), and one or more other resins (D) selected from the group consisting of cyanate compounds, maleimide compounds, and epoxy compounds, wherein the thermoplastic elastomer (A) is a thermoplastic elastomer obtained by hydrogenating all the conjugated diene bonds of a thermoplastic elastomer containing styrene monomer units and conjugated diene monomer units and having a number average molecular weight of 50,000 or more. The thermoplastic elastomer (B) is a thermoplastic elastomer obtained by hydrogenating a portion of the conjugated diene bonds in a thermoplastic elastomer containing styrene monomer units and conjugated diene monomer units with a number average molecular weight of 50,000 or more, and / or a thermoplastic elastomer with all bonds being unsaturated. The content of the thermoplastic elastomer (A) is 0.5 parts by mass or more and 20 parts by mass or less per 100 parts by mass of resin solids. The content of the thermoplastic elastomer (B) is 0.5 parts by mass or more and 20 parts by mass or less per 100 parts by mass of resin solids. The content of the compatible thermosetting resin (C) is 10 to 90 parts by mass or less per 100 parts by mass of resin solids.

5. The resin composition as claimed in claim 4, wherein, The maleimine compound comprises one or more compounds 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), compounds represented by formula (M4), and compounds represented by formula (M5); in formula (M0), R51 each independently represents a hydrogen atom, an alkyl or phenyl group having 1 to 8 carbon atoms, R52 each independently represents a hydrogen atom or a methyl group, and n1 represents an integer of 1 or more; In formula (M1), RM1, RM2, RM3, and RM4 each independently represent a hydrogen atom or an organic group; RM5 and RM6 each independently represent a hydrogen atom or an alkyl group; ArM represents a divalent aromatic group; A represents an alicyclic group with 4 to 6 members; RM7 and RM8 each independently represent an alkyl group; mx represents 1 or 2, lx represents 0 or 1; RM9 and RM10 each independently represent a hydrogen atom or an alkyl group; RM11, RM12, RM13, and RM14 each independently represent a hydrogen atom or an organic group; RM15 each independently represents an alkyl group with 1 to 10 carbon atoms, an alkyloxy group with 1 to 10 carbon atoms, an alkylthio group with 1 to 10 carbon atoms, an aryl group with 6 to 10 carbon atoms, an aryloxy group with 1 to 10 carbon atoms, an arylthio group with 1 to 10 carbon atoms, a halogen atom, a hydroxyl group, or a mercapto group; px represents an integer from 0 to 3; nx represents an integer from 1 to 20. In formula (M2), R54 each independently represents a hydrogen atom or a methyl group, and n4 represents an integer greater than or equal to 1; In formula (M3), R55 each independently represents a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or a phenyl group, and n5 represents an integer greater than or equal to 10; In formula (M4), R56 each independently represents a hydrogen atom, a methyl group, or an ethyl group, and R57 each independently represents a hydrogen atom or a methyl group; In formula (M5), R58 each independently represents a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or a phenyl group, and R59 each independently represents a hydrogen atom or a methyl group, and n6 represents an integer greater than or equal to 1.

6. The resin composition as claimed in claim 4, wherein, The maleimine compound includes compounds represented by formula (M1) and / or compounds represented by formula (M3); In formula (M1), RM1, RM2, RM3, and RM4 each independently represent a hydrogen atom or an organic group; RM5 and RM6 each independently represent a hydrogen atom or an alkyl group; ArM represents a divalent aromatic group; A represents an alicyclic group with 4 to 6 members; RM7 and RM8 each independently represent an alkyl group; mx represents 1 or 2, lx represents 0 or 1; RM9 and RM10 each independently represent a hydrogen atom or an alkyl group; RM11, RM12, RM13, and RM14 each independently represent a hydrogen atom or an organic group; RM15 each independently represents an alkyl group with 1 to 10 carbon atoms, an alkyloxy group with 1 to 10 carbon atoms, an alkylthio group with 1 to 10 carbon atoms, an aryl group with 6 to 10 carbon atoms, an aryloxy group with 1 to 10 carbon atoms, an arylthio group with 1 to 10 carbon atoms, a halogen atom, a hydroxyl group, or a mercapto group; px represents an integer from 0 to 3; nx represents an integer from 1 to 20. In formula (M3), R55 each independently represents a hydrogen atom, an alkyl group with 1 to 8 carbon atoms, or a phenyl group, and n5 represents an integer between 1 and 10.

7. The resin composition of claim 1 or 4 further contains a flame retardant (E).

8. The resin composition as claimed in claim 7, wherein, The flame retardant (E) contains phosphorus-based flame retardants.

9. The resin composition of claim 1 or 4 further contains filler (F).

10. The resin composition as claimed in claim 9, wherein, The filler (F) comprises one or more of the following: silicon dioxide, aluminum hydroxide, aluminum nitride, boron nitride, forsterite, titanium dioxide, barium titanate, strontium titanate, and calcium titanate.

11. The resin composition as claimed in claim 9, wherein, The content of the filler (F) is 10 to 300 parts by mass relative to 100 parts by mass of the resin solids.

12. The resin composition of claim 1 or 4 further contains monomers or oligomers having vinyl unsaturated groups, wherein the content of the monomers or oligomers having vinyl unsaturated groups is 0.5 to 30 parts by weight relative to 100 parts by weight of the resin solids.

13. The resin composition as claimed in claim 1, wherein, In this 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 solids; the mass ratio of the thermoplastic elastomer (A) to the thermoplastic elastomer (B) in this resin composition is 1:1 to 10; the compatible thermosetting resin (C) is a thermosetting resin containing an aromatic ring and a vinyl group; the compatible thermosetting resin (C) includes one or more compounds selected from the group consisting of polymers having a constituent unit represented by formula (V) and polyphenylene ether compounds having a carbon-carbon unsaturated double bond at the end; in formula (V), Ar represents an aromatic hydrocarbon linker; * represents a bond 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 solids. The resin composition further contains one or more other resins (D) selected from the group consisting of cyanate compounds, maleimide compounds, and epoxy compounds; the maleimide compounds include one or more 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) includes a phosphorus-based flame retardant; the resin composition further contains a filler (F); the filler (F) includes one or more selected from the group consisting of silicon dioxide, aluminum hydroxide, aluminum nitride, boron nitride, forsterite, titanium dioxide, barium titanate, strontium titanate, and calcium titanate; the content of the filler (F) is 10 to 300 parts by weight relative to 100 parts by weight of the resin solids. The resin composition further contains monomers or oligomers with vinyl unsaturated groups, and the content of the monomers or oligomers with vinyl unsaturated groups is 0.100 parts by weight of the resin solids.5-30 parts by mass; In formula (M1), RM1, RM2, RM3, and RM4 each independently represent a hydrogen atom or an organic group; RM5 and RM6 each independently represent a hydrogen atom or an alkyl group; ArM represents a divalent aromatic group; A represents a 4-6 member alicyclic group; RM7 and RM8 each independently represent an alkyl group; mx represents 1 or 2, lx represents 0 or 1; RM9 and RM10 each independently represent a hydrogen atom or an alkyl group; RM11, RM12, RM13, and RM14 each independently represent a hydrogen atom or an organic group; RM15 each independently represents an alkyl group with 1-10 carbon atoms, an alkyloxy group with 1-10 carbon atoms, an alkylthio group with 1-10 carbon atoms, an aryl group with 6-10 carbon atoms, an aryloxy group with 1-10 carbon atoms, an arylthio group with 1-10 carbon atoms, a halogen atom, a hydroxyl group, or a mercapto group; px represents an integer from 0 to 3; nx represents an integer from 1 to 20; In formula (M3), R55 each independently represents a hydrogen atom, an alkyl group or phenyl group having 1 to 8 carbon atoms, and n5 represents an integer from 1 to 10; In formula (M5), R58 each independently represents a hydrogen atom, an alkyl group or phenyl group having 1 to 8 carbon atoms, R59 each independently represents a hydrogen atom or a methyl group, and n6 represents an integer from 1 to 1.

14. A prepreg formed from a substrate and a resin composition as claimed in any one of claims 1 to 13.

15. A metal foil laminate comprising: a layer formed of at least one layer of a prepreg as claimed in claim 14, and metal foil disposed on one or both sides of the layer formed of the prepreg.

16. A resin composite sheet comprising a support and a layer disposed on the surface of the support, formed of a resin composition of any one of claims 1 to 13.

17. A printed wiring board comprising an insulating layer and a conductor layer disposed on the surface of the insulating layer, the insulating layer comprising a layer formed of a resin composition as claimed in any one of claims 1 to 13.

18. A semiconductor device comprising a printed wiring board as claimed in claim 17.

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