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

Abstract

Provided are a resin composition and a cured product, a prepreg, a metal-foil-clad laminate, a resin composite sheet, a printed circuit board, and a semiconductor device. The resin composition contains a resin (A) having a terminal group represented by formula (T1) and an indane skeleton and a maleimide compound (B), and a cured product of the maleimide compound (B) has a relative permittivity of 2.0-2.8 at a frequency of 10 GHz measured according to the cavity resonator perturbation method. In formula (T1), Ma each independently represent a C1-12 hydrocarbon group optionally substituted with a halogen atom, and x represents an integer of 0-4. * represents a bonding position with another site.

Description

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

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

[0002] In recent years, the integration and miniaturization of semiconductor elements used in mobile terminals, electronic devices, communication devices, and other devices has accelerated. This has led to a demand for technologies that enable high-density packaging of semiconductor elements, and improvements are also being sought in printed wiring boards, which play an important role in this process. Meanwhile, the applications of electronic devices and other devices have continued to diversify and expand. Accordingly, the properties required of printed wiring boards and the metal foil-clad laminates and prepregs used therein have become more diverse and stricter. Taking these required properties into account, various materials and processing methods have been proposed to obtain improved printed wiring boards. One example is the development of improved resin materials that make up prepregs and resin composite sheets.

[0003] Patent Document 1 discloses a resin having an isopropenylphenyl group at its terminal and an indane skeleton as a material suitable for semiconductor encapsulation and printed wiring boards.

[0004] Japanese Patent Application Laid-Open No. 2021-143333

[0005] However, when the resin having an indane skeleton described in Patent Document 1 is used as is, it does not cure sufficiently, resulting in problems with the moldability of the cured product. Therefore, it is desirable to incorporate another thermosetting compound. When a resin composition containing such a resin having an indane skeleton and another thermosetting compound is used in an insulating layer of a printed wiring board, the cured product is required to have excellent low dielectric properties (Dk and / or Df). Furthermore, depending on the application, excellent heat resistance is also required. The present invention aims to solve these problems and provides a resin composition capable of providing a cured product having excellent low dielectric properties and excellent heat resistance, as well as a cured product, a prepreg, a metal foil-clad laminate, a resin composite sheet, a printed wiring board, and a semiconductor device.

[0006] In light of the above-mentioned problems, the above-mentioned problems have been solved by blending a maleimide compound having a low relative dielectric constant with a resin having a specific indane skeleton. Specifically, the above-mentioned problems have been solved by the following means: <1> A resin composition comprising: a resin (A) having a terminal group represented by formula (T1) and an indane skeleton; and a maleimide compound (B), wherein a cured product of the maleimide compound (B) has a relative dielectric constant of 2.0 to 2.8 at a frequency of 10 GHz as measured according to a cavity resonator perturbation method. (In formula (T1), Ma each independently represents a hydrocarbon group having 1 to 12 carbon atoms which may be substituted with a halogen atom, x represents an integer of 0 to 4, and * represents a bonding position to another moiety.) <2> The resin composition according to <1>, wherein the resin (A) includes a resin represented by formula (T1-1). (In formula (T1-1), R represents a group containing a structural unit represented by formula (Tx). Each Ma independently represents a hydrocarbon group having 1 to 12 carbon atoms which may be substituted with a halogen atom. x represents an integer of 0 to 4.) (In formula (Tx), n, o, and p represent the average number of repeating units, n represents a number greater than 0 and equal to or less than 20, o and p each independently represent a number from 0 to 20, and 1.0≦n+o+p≦20.0. Each Ma independently represents a hydrocarbon group having 1 to 12 carbon atoms which may be substituted with a halogen atom. x represents an integer from 0 to 4. The structural units (a), (b), and (c) are each bonded to the structural units (a), (b), and (c) or to other groups at *, and the respective structural units may be bonded randomly.) <3> The resin composition according to <1> or <2>, wherein, in the structural unit represented by formula (Tx), 1.1≦n+o+p≦20.0. <4> The resin composition according to any one of <1> to <3>, wherein the parameter α calculated from formula (α) in the resin (A) is 0.55 or more and 1.00 or less, and the parameter β calculated from formula (β) is 0.20 or more and 3.00 or less. (The brackets in formula (α) and formula (β) are １The integral between corresponding chemical shift values ​​in H-NMR is shown.) <5> The resin composition according to any one of <1> to <4>, wherein the resin (A) contains a resin represented by formula (T1-1), and the parameter α calculated from formula (α) in the resin (A) is 0.55 or more and 1.00 or less, and the parameter β calculated from formula (β) is 0.20 or more and 3.00 or less. (The brackets in formula (α) and formula (β) are １ The integral between the corresponding chemical shift values ​​in H-NMR is shown.) (In formula (T1-1), R represents a group containing a structural unit represented by formula (Tx). Each Ma independently represents a hydrocarbon group having 1 to 12 carbon atoms which may be substituted with a halogen atom. x represents an integer of 0 to 4.) (In formula (Tx), n, o, and p represent the average number of repeating units, n is a number greater than 0 and equal to or less than 20, o and p each independently represent a number from 0 to 20, and 1.0≦n+o+p≦20.0. Each Ma independently represents a hydrocarbon group having 1 to 12 carbon atoms which may be substituted with a halogen atom. x represents an integer from 0 to 4. The structural units (a), (b), and (c) are each bonded to the structural units (a), (b), and (c) or to other groups via *, and the structural units may be bonded randomly.) <6> The resin composition according to any one of <1> to <5>, wherein the number average molecular weight of the resin (A) is 400 to 3,000, and the weight average molecular weight of the resin (A) is 500 to 6,000. <7> The resin composition according to any one of <1> to <6>, wherein Mw / Mn, which is the ratio of the weight-average molecular weight of the resin (A) to the number-average molecular weight of the resin (A), is 1.1 to 3.0. <8> The resin composition according to any one of <1> to <7>, wherein the content of the resin (A) is 5 to 90 parts by mass relative to 100 parts by mass of the resin solid content in the resin composition. <9> The resin composition according to any one of <1> to <8>, wherein the content of the maleimide compound (B) is 5 to 90 parts by mass relative to 100 parts by mass of the resin solid content in the resin composition. <10> The resin composition according to any one of <1> to <9>, wherein the maleimide compound (B) includes one or more selected from the group consisting of a compound represented by formula (M0), a compound represented by formula (M1), a compound represented by formula (M3), a compound represented by formula (M5), and a compound represented by formula (M7). (In formula (M0), R ５１ each independently represents a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or a phenyl group; R ５２ each independently represents a hydrogen atom or a methyl group; n １ represents an integer of 1 or more.) (In formula (M1), R Ｍ１ , R Ｍ２ , R Ｍ３ , and R Ｍ４ R each independently represents a hydrogen atom or an organic group. Ｍ５ and R Ｍ６ each independently represents a hydrogen atom or an alkyl group. Ｍrepresents a divalent aromatic group. A is a 4- to 6-membered alicyclic group. R Ｍ７ and R Ｍ８ are each independently an alkyl group. mx is 1 or 2, and lx is 0 or 1. R Ｍ９ and R Ｍ１０ R each independently represents a hydrogen atom or an alkyl group. Ｍ１１ , R Ｍ１２ , R Ｍ１３ , and R Ｍ１４ R each independently represents a hydrogen atom or an organic group. Ｍ１５ each independently represents an alkyl group having 1 to 10 carbon atoms, an alkyloxy group having 1 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, an aryloxy group having 6 to 10 carbon atoms, an arylthio group having 6 to 10 carbon atoms, a halogen atom, a hydroxyl group, or a mercapto group. px represents an integer of 0 to 3. nx represents an integer of 1 to 20. (In formula (M3), R ５５ each independently represents a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or a phenyl group; n ５ represents an integer of 1 or more and 10 or less.) (In formula (M5), R ５８ each independently represents a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or a phenyl group; R ５９ each independently represents a hydrogen atom or a methyl group; n ６ represents an integer of 1 or more.) (In the above formula (M7), R １ each independently represents an alkyl group having 1 to 10 carbon atoms; R ２ each independently represents an alkyl group, alkoxy group, or alkylthio group having 1 to 10 carbon atoms; an aryl group, aryloxy group, or arylthio group having 6 to 10 carbon atoms; a cycloalkyl group having 3 to 10 carbon atoms; a halogen atom; a hydroxyl group; or a mercapto group; ３ , R ４ , R ５ and R ６ each independently represents a hydrogen atom or a methyl group, and R ３ and R ４one of which is a hydrogen atom and the other is a methyl group, and R ５ and R ６ one of which is a hydrogen atom and the other is a methyl group, １ is the following formula (x): (In formula (x), R ７ and R ８ each independently represents a hydrogen atom or a methyl group, and R ７ and R ８ one of which is a hydrogen atom and the other is a methyl group, and R ９ each independently represents an alkyl group, alkoxy group, or alkylthio group having 1 to 10 carbon atoms; an aryl group, aryloxy group, or arylthio group having 6 to 10 carbon atoms; a cycloalkyl group having 3 to 10 carbon atoms; a halogen atom; a hydroxyl group; or a mercapto group, and t represents an integer of 0 to 4. １ X per benzene ring to which １ is the average number of substitutions and represents a number from 0 to 4, p represents an integer from 1 to 3, q ​​represents an integer from 0 to 4, and k represents an integer from 1 to 100.) <11> The resin composition according to any one of <1> to <10>, further comprising a compound having two or more polymerizable carbon-carbon unsaturated double bonds. <12> The resin composition according to <11>, wherein the compound having two or more polymerizable carbon-carbon unsaturated double bonds comprises at least one selected from the group consisting of a vinyl aryl compound, a (meth)acrylate compound, and a (meth)allyl compound. <13> The resin composition according to <12>, wherein the compound having two or more polymerizable carbon-carbon unsaturated double bonds comprises at least one selected from the group consisting of a polyphenylene ether compound containing two or more terminal carbon-carbon unsaturated double bonds, and a polymer having a structural unit represented by formula (V). (In formula (V), Ar represents an aromatic hydrocarbon linking group. * represents a bonding position.) <14> The resin (A) contains a resin represented by formula (T1-1), and in the structural unit represented by formula (Tx), 1.1≦n+o+p≦20.0, the parameter α calculated from formula (α) in the resin (A) is 0.55 or more and 1.00 or less, and the parameter β calculated from formula (β) is 0.20 or more and 3.00 or less, the number average molecular weight of the resin (A) is 400 to 3000 and the weight average molecular weight of the resin (A) is 500 to 6000, Mw / Mn is the ratio of the weight average molecular weight of the resin (A) to the number average molecular weight of the resin (A), and the content of the resin (A) is 5 to 90 parts by mass per 100 parts by mass of resin solids in the resin composition, The resin composition according to any one of <1> to <13>, wherein the content of the maleimide compound (B) is 5 to 90 parts by mass relative to 100 parts by mass of a resin solid content in the resin composition, and the maleimide compound (B) includes one or more compounds selected from the group consisting of a compound represented by formula (M0), a compound represented by formula (M1), a compound represented by formula (M3), a compound represented by formula (M5), and a compound represented by formula (M7). (The brackets in formula (α) and formula (β) are １ The integral between the corresponding chemical shift values ​​in H-NMR is shown.) (In formula (T1-1), R represents a group containing a structural unit represented by formula (Tx). Each Ma independently represents a hydrocarbon group having 1 to 12 carbon atoms which may be substituted with a halogen atom. x represents an integer of 0 to 4.) (In formula (Tx), n, o, and p represent the average number of repeating units, n is a number greater than 0 and equal to or less than 20, o and p each independently represent a number from 0 to 20, and 1.0≦n+o+p≦20.0. Each Ma independently represents a hydrocarbon group having 1 to 12 carbon atoms which may be substituted with a halogen atom. x represents an integer from 0 to 4. The structural units (a), (b), and (c) are each bonded to the structural units (a), (b), and (c) or to other groups at *, and the respective structural units may be bonded randomly.) (In formula (M0), R ５１each independently represents a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or a phenyl group; R ５２ each independently represents a hydrogen atom or a methyl group; n １ represents an integer of 1 or more.) (In formula (M1), R Ｍ１ , R Ｍ２ , R Ｍ３ , and R Ｍ４ R each independently represents a hydrogen atom or an organic group. Ｍ５ and R Ｍ６ each independently represents a hydrogen atom or an alkyl group. Ｍ represents a divalent aromatic group. A is a 4- to 6-membered alicyclic group. R Ｍ７ and R Ｍ８ are each independently an alkyl group. mx is 1 or 2, and lx is 0 or 1. R Ｍ９ and R Ｍ１０ R each independently represents a hydrogen atom or an alkyl group. Ｍ１１ , R Ｍ１２ , R Ｍ１３ , and R Ｍ１４ R each independently represents a hydrogen atom or an organic group. Ｍ１５ each independently represents an alkyl group having 1 to 10 carbon atoms, an alkyloxy group having 1 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, an aryloxy group having 6 to 10 carbon atoms, an arylthio group having 6 to 10 carbon atoms, a halogen atom, a hydroxyl group, or a mercapto group. px represents an integer of 0 to 3. nx represents an integer of 1 to 20. (In formula (M3), R ５５ each independently represents a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or a phenyl group; n ５ represents an integer of 1 or more and 10 or less.) (In formula (M5), R ５８ each independently represents a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or a phenyl group; R ５９ each independently represents a hydrogen atom or a methyl group; n ６ represents an integer of 1 or more.) (In the above formula (M7), R １each independently represents an alkyl group having 1 to 10 carbon atoms; R ２ each independently represents an alkyl group, alkoxy group, or alkylthio group having 1 to 10 carbon atoms; an aryl group, aryloxy group, or arylthio group having 6 to 10 carbon atoms; a cycloalkyl group having 3 to 10 carbon atoms; a halogen atom; a hydroxyl group; or a mercapto group; ３ , R ４ , R ５ and R ６ each independently represents a hydrogen atom or a methyl group, and R ３ and R ４ one of which is a hydrogen atom and the other is a methyl group, and R ５ and R ６ one of which is a hydrogen atom and the other is a methyl group, １ is the following formula (x): (In formula (x), R ７ and R ８ each independently represents a hydrogen atom or a methyl group, and R ７ and R ８ one of which is a hydrogen atom and the other is a methyl group, and R ９ each independently represents an alkyl group, alkoxy group, or alkylthio group having 1 to 10 carbon atoms; an aryl group, aryloxy group, or arylthio group having 6 to 10 carbon atoms; a cycloalkyl group having 3 to 10 carbon atoms; a halogen atom; a hydroxyl group; or a mercapto group, and t represents an integer of 0 to 4. １ X per benzene ring to which １is the average number of substitutions and represents a number from 0 to 4, p represents an integer from 1 to 3, q ​​represents an integer from 0 to 4, and k represents an integer from 1 to 100.) <15> The resin composition according to <14>, further comprising a compound having two or more polymerizable carbon-carbon unsaturated double bonds. <16> The resin composition according to <15>, wherein the compound having two or more polymerizable carbon-carbon unsaturated double bonds comprises at least one selected from the group consisting of a vinyl aryl compound, a (meth)acrylate compound, and a (meth)allyl compound. <17> The resin composition according to <16>, wherein the vinyl aryl compound comprises at least one selected from the group consisting of a polyphenylene ether compound containing two or more terminal carbon-carbon unsaturated double bonds, and a polymer having a structural unit represented by formula (V). (In formula (V), Ar represents an aromatic hydrocarbon linking group. * represents a bonding position.) <18> The resin composition according to any one of <1> to <17>, further comprising a filler. <19> The resin composition according to <18>, wherein the filler comprises one or more selected from the group consisting of silica, aluminum hydroxide, talc, aluminum nitride, boron nitride, forsterite, titanium oxide, barium titanate, strontium titanate, and calcium titanate. <20> The resin composition according to <18> or <19>, wherein the content of the filler in the resin composition is 1 to 1,600 parts by mass per 100 parts by mass of resin solids in the resin composition. <21> The resin composition according to any one of <18> to <20>, wherein the filler comprises silica slurry. <22> The resin composition according to any one of <18> to <21>, further comprising a compound having two or more polymerizable carbon-carbon unsaturated double bonds, wherein the mass ratio of the compound having two or more polymerizable carbon-carbon unsaturated double bonds to the filler is 1:1 to 50. <23> The resin composition according to any one of <18> to <22>, further comprising a compound having two or more polymerizable carbon-carbon unsaturated double bonds, wherein the compound having two or more polymerizable carbon-carbon unsaturated double bonds comprises a polyphenylene ether compound represented by formula (OP): (In formula (OP), X represents an aromatic group, and —(Y—O)ｎ１ - represents a polyphenylene ether structure, n1 represents an integer of 1 to 100, and n2 represents an integer of 1 to 4. Rx is a group represented by formula (Rx-1) or formula (Rx-2). (In formula (Rx-1) and formula (Rx-2), R １ , R ２ , and R ３ each independently represent a hydrogen atom, an alkyl group, an alkenyl group, or an alkynyl group. * represents a bonding site with an oxygen atom. Each Mc independently represents a hydrocarbon group having 1 to 12 carbon atoms. z represents an integer of 0 to 4. r represents an integer of 0 to 6.) <24> The resin composition according to any one of <18> to <23>, wherein the filler contains a silica slurry and powdered silica, and further contains a compound having two or more polymerizable carbon-carbon unsaturated double bonds, and the compound having two or more polymerizable carbon-carbon unsaturated double bonds contains a polyphenylene ether compound represented by formula (OP). (In formula (OP), X represents an aromatic group, and —(Y—O) ｎ１ - represents a polyphenylene ether structure, n1 represents an integer of 1 to 100, and n2 represents an integer of 1 to 4. Rx is a group represented by formula (Rx-1) or formula (Rx-2). (In formula (Rx-1) and formula (Rx-2), R １ , R ２ , and R ３each independently represent a hydrogen atom, an alkyl group, an alkenyl group, or an alkynyl group. * represents a bonding site with an oxygen atom. Each Mc independently represents a hydrocarbon group having 1 to 12 carbon atoms. z represents an integer of 0 to 4. r represents an integer of 0 to 6.) <25> The resin composition according to any one of <1> to <24>, which is for use in a printed wiring board. <26> A cured product of the resin composition according to any one of <1> to <25>. <27> A prepreg formed from a substrate and the resin composition according to any one of <1> to <25>. <28> A metal foil-clad laminate comprising at least one prepreg according to <27> and a metal foil disposed on one or both sides of the prepreg. <29> A resin composite sheet comprising a support and a layer formed from the resin composition according to any one of <1> to <25>, which is disposed on a surface of the support. <30> A printed wiring board comprising an insulating layer and a conductor layer disposed on a surface of the insulating layer, wherein the insulating layer comprises a layer formed from the resin composition according to any one of <1> to <25>. <31> A semiconductor device comprising the printed wiring board according to <30>.

[0007] The present invention makes it possible to provide a resin composition capable of providing a cured product having excellent low dielectric properties and excellent heat resistance, as well as a cured product, a prepreg, a metal foil-clad laminate, a resin composite sheet, a printed wiring board, and a semiconductor device.

[0008] The resin obtained in Synthesis Example 1 １ The H-NMR chart is shown below.

[0009] Hereinafter, a detailed description will be given of an embodiment of the present invention (hereinafter simply referred to as "the present embodiment"). Note that the following present embodiment is an example for explaining the present invention, and the present invention is not limited to this embodiment. In this specification, the term "to" is used to mean that the numerical values ​​before and after it are included as lower and upper limits. In this specification, various physical property values ​​and characteristic values ​​are those at 23°C unless otherwise specified. In the description of a group (atomic group), a notation that does not indicate substituted or unsubstituted encompasses both a group (atomic group) that has no substituent and a group (atomic group) that has a substituent. For example, the term "alkyl group" encompasses not only an alkyl group that has no substituent (unsubstituted alkyl group) but also an alkyl group that has a substituent (substituted alkyl group). In this specification, when a notation that does not indicate substituted or unsubstituted is used, unsubstituted is preferred. In this specification, the term "(meth)allyl group" refers to either or both of allyl and methallyl, "(meth)acrylate" refers to either or both of acrylate and methacrylate, "(meth)acrylic" refers to either or both of acrylic and methacrylic, and "(meth)acryloyl" refers to either or both of acryloyl and methacryloyl. In this specification, the term "process" refers not only to an independent process, but also to a process that cannot be clearly distinguished from other processes, as long as the intended effect of the process is achieved. If the measurement methods, etc. described in the standards shown in this specification vary from year to year, they shall be based on the standards as of January 1, 2023, unless otherwise specified.

[0010] In this specification, the resin solids content refers to components excluding fillers and solvents, and is intended to include the resin (A), the maleimide compound (B), and other components that are blended as necessary, compounds having two or more polymerizable carbon-carbon unsaturated double bonds, and resin additive components (additives such as curing accelerators and flame retardants). In this specification, the terms relative permittivity and dielectric constant are used interchangeably.

[0011] The resin composition of the present embodiment is characterized in that it contains a resin (A) (sometimes simply referred to as "resin (A)" in this specification) having a terminal group represented by formula (T1) and an indane skeleton, and a maleimide compound (B), and that a cured product of the maleimide compound (B) has a relative dielectric constant of 2.0 to 2.8 at a frequency of 10 GHz measured according to a cavity resonator perturbation method. (In formula (T1), each Ma independently represents a hydrocarbon group having 1 to 12 carbon atoms which may be substituted with a halogen atom, x represents an integer of 0 to 4, and * represents the bonding position to another moiety.)

[0012] By adopting such a configuration, a resin composition can be obtained that can provide a cured product with excellent low dielectric properties (Dk and Df) and excellent heat resistance. The inventors have discovered that a resin (A) having an indane skeleton can provide a cured product with excellent low dielectric properties (Dk and / or Df), but have also discovered that a resin (A) having an indane skeleton alone does not cure sufficiently. In this embodiment, by incorporating a maleimide compound (B), the curing of a resin composition containing a resin (A) having an indane skeleton and a maleimide compound (B) can be effectively promoted, and a resin composition can be obtained that can provide a cured product with excellent low dielectric properties (Dk and / or Df) and heat resistance. Furthermore, by using a maleimide compound (B) whose cured product has a relative dielectric constant of 2.0 to 2.8, a resin composition can be obtained that can provide a cured product with even more excellent low dielectric properties (Dk and / or Df). In particular, although the maleimide compound (B) tends to have a low glass transition temperature, it is presumed that in this embodiment, the resin composition was sufficiently cured, making it possible to provide a cured product with excellent heat resistance. Hereinafter, the details of this embodiment will be described.

[0013] <Resin (A) Having a Terminal Group Represented by Formula (T1) and an Indane Skeleton> The resin composition of the present embodiment includes a resin (A) having a terminal group represented by Formula (T1) and an indane skeleton. (In formula (T1), each Ma independently represents a hydrocarbon group having 1 to 12 carbon atoms which may be substituted with a halogen atom, x represents an integer of 0 to 4, and * represents the bonding position to another moiety.)

[0014] In formula (T1), each Ma is preferably a hydrocarbon group having 1 to 10 carbon atoms which may be substituted with a halogen atom, more preferably a hydrocarbon group having 1 to 5 carbon atoms which may be substituted with a halogen atom, and even more preferably a hydrocarbon group having 1 to 3 carbon atoms which may be substituted with a halogen atom. Examples of halogen atoms include a fluorine atom, a chlorine atom, and a bromine atom, and a fluorine atom or a chlorine atom is preferred. Each Ma is preferably a hydrocarbon group having 1 to 12 carbon atoms which is not substituted with a halogen atom. The hydrocarbon group is preferably an alkyl group, and more preferably a linear alkyl group. A methyl group or an ethyl group is particularly preferred as Ma.

[0015] x is preferably an integer of 0 to 3, more preferably an integer of 0 to 2, even more preferably 0 or 1, and even more preferably 0.

[0016] The resin (A) may have terminal groups represented by formula (T1) at all or only some of the terminals of each resin molecule. The number of terminal groups represented by formula (T1) in the resin molecule of resin (A) is preferably two.

[0017] Resin (A) has an indane skeleton. There are no particular limitations on the number of indane skeletons contained in resin molecules of resin (A), as long as at least one molecule contains at least one indane skeleton. However, the number of indane skeletons in the resin molecule of resin (A) is preferably 1 or more, and more preferably 1 to 20, per molecule. By adopting such a configuration, the effects of the present invention tend to be more effectively exhibited.

[0018] The resin (A) preferably contains a structural unit represented by formula (Txn). (In formula (Txn), n represents the average number of repeating units and is a number greater than 0 and equal to or less than 20. Each Ma independently represents a hydrocarbon group having 1 to 12 carbon atoms which may be substituted with a halogen atom. x represents an integer of 0 to 4.)

[0019] In formula (Txn), each Ma is preferably a hydrocarbon group having 1 to 10 carbon atoms which may be substituted with a halogen atom, more preferably a hydrocarbon group having 1 to 5 carbon atoms which may be substituted with a halogen atom, and even more preferably a hydrocarbon group having 1 to 3 carbon atoms which may be substituted with a halogen atom. Examples of halogen atoms include a fluorine atom, a chlorine atom, and a bromine atom, and a fluorine atom or a chlorine atom is preferred. Each Ma is preferably a hydrocarbon group having 1 to 12 carbon atoms which is not substituted with a halogen atom. The hydrocarbon group is preferably an alkyl group, and more preferably a linear alkyl group. A methyl group or an ethyl group is particularly preferred as Ma.

[0020] x is preferably an integer of 0 to 3, more preferably an integer of 0 to 2, even more preferably 0 or 1, and even more preferably 0.

[0021] The resin (A) more preferably contains a resin represented by formula (T1-1), and even more preferably contains a resin represented by formula (T1-1-2). (In formula (T1-1), R represents a group containing a structural unit represented by formula (Tx). Ma each independently represents a hydrocarbon group having 1 to 12 carbon atoms which may be substituted with a halogen atom. x is an integer of 0 to 4.) In formula (T1-1), Ma and x have the same meanings as Ma and x in formula (T1), and the preferred ranges are also the same. (In formula (T1-1-2), R is a group containing a structural unit represented by formula (Tx).) (In formula (Tx), n, o, and p represent the average number of repeating units, n is a number greater than 0 and equal to or less than 20, o and p each independently represent a number from 0 to 20, and 1.0≦n+o+p≦20.0. Each Ma independently represents a hydrocarbon group having 1 to 12 carbon atoms which may be substituted with a halogen atom. x represents an integer from 0 to 4. The structural units (a), (b), and (c) are each bonded to the structural units (a), (b), and (c) or to other groups at *, and the respective structural units may be bonded randomly.)

[0022] In formula (Tx), n, o, and p each represent the average number of repeating units in all molecules in the resin. In formula (Tx), the sum of n, o, and p is preferably 1.1≦n+o+p, more preferably 1.2≦n+o+p, even more preferably 1.5≦n+o+p, even more preferably 2.0≦n+o+p, even more preferably 2.5≦n+o+p, even more preferably 3.0≦n+o+p, and particularly preferably 3.3≦n+o+p. In addition, in formula (Tx), the sum of n, o, and p is preferably n+o+p≦20.0, more preferably n+o+p≦10.0, even more preferably n+o+p≦8.0, even more preferably n+o+p≦7.0, and even more preferably n+o+p≦6.4. The sum of n, o, and p can be calculated using the method described in the Examples below. In formula (Tx), Ma and x have the same meanings as Ma and x in formula (Txn), respectively, and the preferred ranges are also the same.

[0023] The resin represented by formula (T1-1) (preferably the resin represented by formula (T1-1-2)) preferably has a parameter α calculated from formula (α) of 0.55 or more and 1.00 or less. The resin represented by formula (T1-1) (preferably the resin represented by formula (T1-1-2)) preferably has a parameter β calculated from formula (β) of 0.20 or more and 3.00 or less. By setting parameters α and β within the above ranges, the obtained cured product tends to have low dielectric properties (Dk and / or Df) and excellent heat resistance. (The brackets in formula (α) and formula (β) are １ The integral between the corresponding chemical shift values ​​in H-NMR is shown.)

[0024] Here, α indicates the ratio of the structural unit having an indane skeleton (structural unit (a) in formula (Tx)) in the resin represented by formula (T1-1) (preferably, the resin represented by formula (T1-1-2)). More specifically, it is presumed that by adjusting the structural unit having an indane skeleton so as to satisfy the range of the parameter α, the rigidity of the resulting resin molecules will be high and the glass transition temperature will be high. Furthermore, it is presumed that molecules with high rigidity have lower mobility than molecules with low rigidity, and therefore the relaxation time during dielectric relaxation will be longer and Df will be lower. When synthesizing the resin represented by formula (T1-1), α can be increased by conditions such as diluting the concentration of raw materials, using a highly polar solvent, increasing the amount of catalyst, and raising the reaction temperature. Meanwhile, β defines the terminal double bond ratio in the resin represented by formula (T1-1) (preferably, the resin represented by formula (T1-1-2)). More specifically, by adjusting the structural unit having an indane skeleton so that the parameter β falls within the above range, it is presumed that, for example, the number of crosslinking points with the functional group of the maleimide compound (B) described below increases, making it easier to form a network upon thermal curing, and resulting in a cured product with a high glass transition temperature and a low Df. β can be increased by reducing the amount of catalyst, lowering the reaction temperature, using a low-polarity solvent, or other conditions when synthesizing the resin represented by formula (T1-1).

[0025] More specifically, for the resin of Synthesis Example 1 described below, the 2.55 ppm to 2.31 ppm corresponds to the peak derived from the structural unit (a), the 6.24 ppm to 5.91 ppm corresponds to the peak derived from the structural unit (b), the 2.98 ppm to 2.55 ppm corresponds to the peak derived from the structural unit (c), the 5.49 ppm to 4.89 ppm corresponds to the peak derived from the isopropenyl group and the structural unit (c), the 4.89 ppm to 4.45 ppm corresponds to the peak derived from the structural unit (c), and the 2.31 ppm to 1.96 ppm corresponds to the peak derived from the isopropenyl group and the structural unit (a). More specifically, H used in calculating the parameters α and β is shown in the following structural formula: Used to calculate the above parameters α and β １ The H-NMR peaks can be assigned as follows using the Hs described above: 2.55 ppm to 2.31 ppm: H ａ１ ・6.24ppm to 5.91ppm:H ｂ１ ・2.98ppm~2.55ppm:H ｃ１ ・5.49ppm~4.89ppm:H ｉ２ and H ｉ３ and H ｃ２ ・4.89ppm~4.45ppm:H ｃ３ ・2.31ppm~1.96ppm:H ａ２ and H ｉ１

[0026] From the above, the formula for parameters α and β is written by the amount of each hydrogen atom as shown below. ａ１ The larger the amount of H in the isopropenyl group, i.e., the more five-membered rings there are in the structural unit (a), the larger the parameter β. ｉ１ The quantity of H ｉ２ and H ｉ３ The formula is shown so that the numerator is 1.5 times the total amount of (H ｉ２ and H ｉ３ 1.5 times the total amount of H ｉ１ The total amount of

[0027] When synthesizing a resin represented by formula (T1-1) (preferably a resin represented by formula (T1-1-2)), the parameters α and β of the resin represented by formula (T1-1) (preferably a resin represented by formula (T1-1-2)) can be adjusted using the method for increasing the parameters α and β described above. Of course, the parameters α and β may also be adjusted by a method other than those described above.

[0028] The parameter α is preferably 0.57 or more, more preferably 0.59 or more, even more preferably 0.60 or more, even more preferably 0.62 or more, and may be 0.65 or more, 0.70 or more, 0.75 or more, or 0.80 or more. By setting the parameter α at or above the lower limit, the heat resistance of the resulting cured product tends to be further improved. Since the low dielectric properties (Dk and / or Df) and heat resistance of the resulting cured product tend to be excellent, the larger the parameter α, the better, but it may be 1.00 or less, 0.95 or less, 0.90 or less, 0.85 or less, 0.82 or less, 0.80 or less, 0.77 or less, 0.75 or less, or 0.74 or less. The parameter β is preferably 0.25 or more, more preferably 0.30 or more, even more preferably 0.35 or more, even more preferably 0.40 or more, even more preferably 0.43 or more, even more preferably 0.50 or more, and may be 0.60 or more, 0.65 or more, 0.70 or more, 0.77 or more, 0.80 or more, 0.90 or more, or 0.95 or more. By setting the parameter β to be equal to or greater than the lower limit, the heat resistance of the obtained cured product tends to be improved and the Df tends to be lower. The parameter β is preferably 3.00 or less, more preferably 2.50 or less, even more preferably 2.00 or less, even more preferably 1.50 or less, even more preferably 1.30 or less, even more preferably 1.20 or less, particularly preferably 1.10 or less, or may be 1.00 or less, 0.95 or less, 0.90 or less, 0.85 or less, 0.83 or less, or 0.80 or less. By setting the parameter β to the above upper limit or less, the heat resistance of the obtained cured product tends to be improved and Df tends to be lower.

[0029] The polystyrene-equivalent number average molecular weight (Mn) of resin (A) measured by GPC (gel permeation chromatography) (details follow the method described in the Examples below) is preferably 400 or more, more preferably 500 or more, even more preferably 550 or more, even more preferably 600 or more, and even more preferably 650 or more. By setting the number average molecular weight to the above lower limit or higher, the heat resistance of the obtained cured product tends to be improved and the Df tends to be lower. Furthermore, the upper limit of the polystyrene-equivalent number average molecular weight (Mn) of resin (A) measured by GPC (gel permeation chromatography) is preferably 3000 or less, more preferably 2500 or less, even more preferably 2000 or less, even more preferably 1500 or less, even more preferably 1250 or less, and may be 1000 or less or 800 or less depending on the application, etc. By setting the number average molecular weight to the above upper limit or less, the heat resistance of the resulting cured product tends to be improved, and the dielectric constant (Dk) and dielectric loss tangent (Df) tend to be lower. Furthermore, the polystyrene-equivalent weight average molecular weight (Mw) of the resin (A) measured by GPC (details follow the method described in the Examples below) is preferably 500 or more, more preferably 800 or more, even more preferably 900 or more, and even more preferably 1000 or more. By setting the weight average molecular weight to the above lower limit or more, the heat resistance of the resulting cured product tends to be improved, and the Df tends to be lower. The upper limit of the polystyrene-equivalent weight average molecular weight (Mw) of the resin (A) measured by GPC (details follow the method described in the Examples below) is preferably 6000 or less, more preferably 5000 or less, even more preferably 4000 or less, even more preferably 3000 or less, and even more preferably 2800 or less. It may be 2500 or less, 2000 or less, or 1500 or less depending on the application. By adjusting the weight average molecular weight to the above upper limit or less, the heat resistance of the obtained cured product tends to be improved, and the relative dielectric constant (Dk) and dielectric loss tangent (Df) tend to be lower.

[0030] The resin (A) preferably has a Mw / Mn ratio, which is the ratio of weight average molecular weight to number average molecular weight, of 1.1 to 3.0. The Mw / Mn of the resin (A) is more preferably 1.2 or more, even more preferably 1.3 or more, even more preferably 1.4 or more, even more preferably 1.5 or more, and even more preferably 1.6 or more. The Mw / Mn of the resin (A) is more preferably 2.5 or less, even more preferably 2.4 or less, and may be 2.3 or less, 2.0 or less, or 1.8 or less. The weight average molecular weight and number average molecular weight are measured according to the methods described in the Examples below.

[0031] In this embodiment, the functional group equivalent (isopropenyl group equivalent) of the resin (A) is preferably 100 g / eq. or more, more preferably 150 g / eq. or more, even more preferably 200 g / eq. or more, still more preferably 250 g / eq. or more, even more preferably 275 g / eq. or more, still more preferably 300 g / eq. or more, and is preferably 7500 eq. or less, more preferably 5000 eq. or less, even more preferably 4000 eq. or less, still more preferably 3000 g / eq. or less, still more preferably 2000 g / eq. or less, still more preferably 1500 g / eq. or less, particularly still more preferably 1000 g / eq. or less, or may even be 800 g / eq. or less, 750 g / eq. or less, 700 g / eq. or less, or 500 g / eq. or less. By setting the functional group equivalent weight of resin (A) to the above lower limit or more, the resulting cured product tends to have better low dielectric properties (Dk and / or Df, particularly Df) and better peel strength. Furthermore, by setting the functional group equivalent weight of resin (A) to the above upper limit or less, the resulting cured product tends to have better low dielectric properties (Dk and / or Df, particularly Df) and better heat resistance (particularly glass transition temperature). The functional group equivalent weight (isopropenyl group equivalent weight) of resin (A) is determined according to the method described in the Examples below.

[0032] The content of resin (A) in the resin composition of this embodiment is preferably 5 parts by mass or more, more preferably 8 parts by mass or more, per 100 parts by mass of the resin solid content in the resin composition. Depending on the application, it may be 10 parts by mass or more, 14 parts by mass or more, or 18 parts by mass or more. By setting the content of resin (A) at or above the lower limit, the dielectric loss tangent (Df) of the resulting cured product can be reduced, and heat resistance tends to be improved. Furthermore, the upper limit of the content of resin (A) is preferably 90 parts by mass or less, more preferably 70 parts by mass or less, even more preferably 55 parts by mass or less, even more preferably 50 parts by mass or less, even more preferably 45 parts by mass or less, even more preferably 40 parts by mass or less, particularly preferably 35 parts by mass or less, and may be 30 parts by mass or less, 25 parts by mass or less, or 22 parts by mass or less, depending on the application, etc. By setting the content of resin (A) to the above upper limit or less, the moldability of the resin composition, the heat resistance (glass transition temperature) of the obtained cured product, and the moisture absorption heat resistance tend to be improved. The resin composition of this embodiment may contain only one type of resin (A), or may contain two or more types. When two or more types are contained, it is preferable that the total amount is in the above range.

[0033] The method for producing the resin (A) in this embodiment is not particularly limited, and resins obtained by known production methods can be used. Furthermore, the raw materials, reaction temperature, catalyst type, catalyst amount, reaction solvent, raw material concentration, etc., used in synthesizing the resin (A) are not particularly limited, and can be appropriately selected or controlled depending on the desired physical properties described above.

[0034] In this embodiment, examples of raw materials that can be used when synthesizing resin (A) include m-bis(α-hydroxyisopropyl)benzene, p-bis(α-hydroxyisopropyl)benzene, 1,3-diisopropenylbenzene, and 1,4-diisopropenylbenzene.

[0035] <Maleimide Compound (B)> The resin composition of this embodiment contains a maleimide compound (B), and the cured product of the maleimide compound (B) has a dielectric constant of 2.0 to 2.8 at a frequency of 10 GHz, as measured by a cavity resonator perturbation method. The dielectric constant of the cured product of the maleimide compound (B) is preferably 2.7 or less, more preferably 2.6 or less. Furthermore, a practical lower limit of the dielectric constant is, for example, 2.0 or more. The dielectric constant of the cured product of the maleimide compound (B) is measured according to the method described in the Examples below. The glass transition temperature of the cured product of the maleimide compound (B) is typically 150°C or higher, and may be 170°C or higher, 180°C or higher, or 200°C or higher, and is typically 350°C or lower. The glass transition temperature of the maleimide compound (B) is measured according to the description in the Examples below. The resin composition of this embodiment is advantageous in that it can achieve high heat resistance even when the cured product of the maleimide compound (B) has a relatively low glass transition temperature. Furthermore, high heat resistance can be achieved even when the maleimide compound (B) used has a glass transition temperature of 280°C or lower, 260°C or lower, 250°C or lower, 240°C or lower, or 230°C or lower.

[0036] In this embodiment, the maleimide compound (B) is preferably a compound having one or more (preferably two or more, more preferably 2 to 12, even more preferably 2 to 6, still more preferably 2 to 4, still more preferably 2 or 3, and still more preferably 2) maleimide groups per molecule. More specifically, the maleimide compound (B) preferably includes one or more selected from the group consisting of a compound represented by formula (M0), a compound represented by formula (M1), a compound represented by formula (M3), a compound represented by formula (M5), and a compound represented by formula (M7), and more preferably includes a compound represented by formula (M7).

[0037] (In formula (M0), R ５１ each independently represents a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or a phenyl group; R ５２ each independently represents a hydrogen atom or a methyl group; n １represents an integer of 1 or more.) R ５１ are each independently preferably a hydrogen atom, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a t-butyl group, an n-pentyl group, or a phenyl group, more preferably one of a hydrogen atom and a methyl group, and even more preferably a hydrogen atom. ５２ is preferably a methyl group. １ is preferably an integer of 1 to 10, more preferably an integer of 1 to 5, even more preferably an integer of 1 to 3, even more preferably 1 or 2, and even more preferably 1. The compound represented by formula (M0) may be a single type or a mixture of two or more types. Examples of the mixture include compounds represented by formula (M0) such as １ a mixture of compounds with different R ５１ and / or R ５２ a mixture of compounds having different types of substituents, a mixture of compounds having different bonding positions (meta, para, or ortho positions) of the maleimide group and the oxygen atom relative to the benzene ring, and a mixture of compounds having a combination of two or more of the above differences. The same applies to the compound represented by formula (M1) below.

[0038] (In formula (M1), R Ｍ１ , R Ｍ２ , R Ｍ３ , and R Ｍ４ R each independently represents a hydrogen atom or an organic group. Ｍ５ and R Ｍ６ each independently represents a hydrogen atom or an alkyl group. Ｍ represents a divalent aromatic group. A is a 4- to 6-membered alicyclic group. R Ｍ７ and R Ｍ８ are each independently an alkyl group. mx is 1 or 2, and lx is 0 or 1. R Ｍ９ and R Ｍ１０ R each independently represents a hydrogen atom or an alkyl group. Ｍ１１ , R Ｍ１２ , R Ｍ１３ , and R Ｍ１４ R each independently represents a hydrogen atom or an organic group. Ｍ１５each independently represents an alkyl group having 1 to 10 carbon atoms, an alkyloxy group having 1 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, an aryloxy group having 6 to 10 carbon atoms, an arylthio group having 6 to 10 carbon atoms, a halogen atom, a hydroxyl group, or a mercapto group. px represents an integer of 0 to 3. nx represents an integer of 1 to 20.

[0039] R in the formula Ｍ１ , R Ｍ２ , R Ｍ３ , and R Ｍ４ R each independently represents a hydrogen atom or an organic group. The organic group here is preferably an alkyl group, more preferably an alkyl group having 1 to 12 carbon atoms, even more preferably an alkyl group having 1 to 6 carbon atoms, and even more preferably a methyl group, an ethyl group, a propyl group, or a butyl group, with a methyl group being particularly preferred. Ｍ１ and R Ｍ３ are each independently preferably an alkyl group, and R Ｍ２ and R Ｍ４ is preferably a hydrogen atom. Ｍ５ and R Ｍ６ Each of Ar independently represents a hydrogen atom or an alkyl group, and an alkyl group is preferable. The alkyl group here is preferably an alkyl group having 1 to 12 carbon atoms, more preferably an alkyl group having 1 to 6 carbon atoms, further preferably a methyl group, an ethyl group, a propyl group, or a butyl group, and among these, a methyl group is particularly preferable. Ｍ represents a divalent aromatic group, preferably a phenylene group, a naphthalenediyl group, a phenanthrenediyl group, or an anthracenediyl group, more preferably a phenylene group, and even more preferably an m-phenylene group. Ｍ may have a substituent, and the substituent is preferably an alkyl group, more preferably an alkyl group having 1 to 12 carbon atoms, even more preferably an alkyl group having 1 to 6 carbon atoms, still more preferably a methyl group, an ethyl group, a propyl group, or a butyl group, and particularly preferably a methyl group. Ｍ A is preferably a 4- to 6-membered alicyclic group, more preferably a 5-membered alicyclic group (preferably a group that forms an indane ring when combined with a benzene ring).Ｍ７ and R Ｍ８ are each independently an alkyl group, preferably an alkyl group having 1 to 6 carbon atoms, more preferably an alkyl group having 1 to 3 carbon atoms, and particularly preferably a methyl group. mx is 1 or 2, preferably 2. lx is 0 or 1, preferably 1. R Ｍ９ and R Ｍ１０ R each independently represents a hydrogen atom or an alkyl group, with an alkyl group being more preferred. The alkyl group here is preferably an alkyl group having 1 to 12 carbon atoms, more preferably an alkyl group having 1 to 6 carbon atoms, further preferably a methyl group, an ethyl group, a propyl group, or a butyl group, with a methyl group being particularly preferred. Ｍ１１ , R Ｍ１２ , R Ｍ１３ , and R Ｍ１４ R each independently represents a hydrogen atom or an organic group. The organic group here is preferably an alkyl group, more preferably an alkyl group having 1 to 12 carbon atoms, even more preferably an alkyl group having 1 to 6 carbon atoms, and even more preferably a methyl group, an ethyl group, a propyl group, or a butyl group, with a methyl group being particularly preferred. Ｍ１２ and R Ｍ１３ are each independently preferably an alkyl group, and R Ｍ１１ and R Ｍ１４ is preferably a hydrogen atom. Ｍ１５each independently represent an alkyl group having 1 to 10 carbon atoms, an alkyloxy group having 1 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, an aryloxy group having 6 to 10 carbon atoms, an arylthio group having 6 to 10 carbon atoms, a halogen atom, a hydroxyl group, or a mercapto group, and is preferably an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, or an aryl group having 6 to 10 carbon atoms. px represents an integer of 0 to 3, preferably an integer of 0 to 2, more preferably 0 or 1, and even more preferably 0. nx represents an integer of 1 to 20. nx may be an integer of 10 or less. The resin composition of this embodiment may contain only one or more compounds represented by formula (M1) having at least different values ​​of nx. When two or more types are contained, the average value of nx (average number of repeating units) n in the compound represented by formula (M1) in the resin composition is preferably 0.92 or more, more preferably 0.95 or more, even more preferably 1.0 or more, and even more preferably 1.1 or more, in order to have a low melting point (low softening point), low melt viscosity, and excellent handleability. Furthermore, n is preferably 10.0 or less, more preferably 8.0 or less, even more preferably 7.0 or less, even more preferably 6.0 or less, and may be 5.0 or less. The same applies to formula (M1-1) described later.

[0040] The compound represented by formula (M1) is preferably a compound represented by the following formula (M1-1): (In formula (M1-1), R Ｍ２１ , R Ｍ２２ , R Ｍ２３ , and R Ｍ２４ R each independently represents a hydrogen atom or an organic group. Ｍ２５ and R Ｍ２６ R each independently represents a hydrogen atom or an alkyl group. Ｍ２７ , R Ｍ２８ , R Ｍ２９ , and R Ｍ３０ R each independently represents a hydrogen atom or an organic group. Ｍ３１ and R Ｍ３２R each independently represents a hydrogen atom or an alkyl group. Ｍ３３ , R Ｍ３４ , R Ｍ３５ , and R Ｍ３６ R each independently represents a hydrogen atom or an organic group. Ｍ３７ , R Ｍ３８ , and R Ｍ３９ each independently represents a hydrogen atom or an alkyl group; and nx represents an integer of 1 or more and 20 or less.

[0041] R in the formula Ｍ２１ , R Ｍ２２ , R Ｍ２３ , and R Ｍ２４ R each independently represents a hydrogen atom or an organic group. The organic group here is preferably an alkyl group, more preferably an alkyl group having 1 to 12 carbon atoms, even more preferably an alkyl group having 1 to 6 carbon atoms, still more preferably a methyl group, an ethyl group, a propyl group, or a butyl group, and particularly preferably a methyl group. Ｍ２１ and R Ｍ２３ is preferably an alkyl group, and R Ｍ２２ and R Ｍ２４ is preferably a hydrogen atom. Ｍ２５ and R Ｍ２６ R each independently represents a hydrogen atom or an alkyl group, preferably an alkyl group. The alkyl group here is preferably an alkyl group having 1 to 12 carbon atoms, more preferably an alkyl group having 1 to 6 carbon atoms, further preferably a methyl group, an ethyl group, a propyl group, or a butyl group, and among these, a methyl group is particularly preferred. Ｍ２７ , R Ｍ２８ , R Ｍ２９ , and R Ｍ３０ R each independently represents 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, even more preferably an alkyl group having 1 to 6 carbon atoms, still more preferably a methyl group, an ethyl group, a propyl group, or a butyl group, and particularly preferably a methyl group. Ｍ３１ and R Ｍ３２R each independently represents a hydrogen atom or an alkyl group, preferably an alkyl group. The alkyl group here is preferably an alkyl group having 1 to 12 carbon atoms, more preferably an alkyl group having 1 to 6 carbon atoms, further preferably a methyl group, an ethyl group, a propyl group, or a butyl group, and among these, a methyl group is particularly preferred. Ｍ３３ , R Ｍ３４ , R Ｍ３５ , and R Ｍ３６ R each independently represents a hydrogen atom or an organic group. The organic group here is preferably an alkyl group, more preferably an alkyl group having 1 to 12 carbon atoms, even more preferably an alkyl group having 1 to 6 carbon atoms, still more preferably a methyl group, an ethyl group, a propyl group, or a butyl group, and particularly preferably a methyl group. Ｍ３３ and R Ｍ３６ is preferably a hydrogen atom, and R Ｍ３４ and R Ｍ３５ is preferably an alkyl group. Ｍ３７ , R Ｍ３８ , and R Ｍ３９ each independently represents a hydrogen atom or an alkyl group, with an alkyl group being preferred. The alkyl group here is preferably an alkyl group having 1 to 12 carbon atoms, more preferably an alkyl group having 1 to 6 carbon atoms, further preferably a methyl group, an ethyl group, a propyl group, or a butyl group, with a methyl group being particularly preferred. nx represents an integer of 1 to 20. nx may also be an integer of 10 or less.

[0042] The compound represented by formula (M1-1) is preferably a compound represented by the following formula (M1-2): (In formula (M1-2), R Ｍ２１ , R Ｍ２２ , R Ｍ２３ , and R Ｍ２４ R each independently represents a hydrogen atom or an organic group. Ｍ２５ and R Ｍ２６ R each independently represents a hydrogen atom or an alkyl group. Ｍ２７ , R Ｍ２８ , R Ｍ２９ , and R Ｍ３０ R each independently represents a hydrogen atom or an organic group. Ｍ３１ and R Ｍ３２R each independently represents a hydrogen atom or an alkyl group. Ｍ３３ , R Ｍ３４ , R Ｍ３５ , and R Ｍ３６ R each independently represents a hydrogen atom or an organic group. Ｍ３７ , R Ｍ３８ , and R Ｍ３９ each independently represents a hydrogen atom or an alkyl group; and nx represents an integer of 1 or more and 20 or less.

[0043] In formula (M1-2), R Ｍ２１ , R Ｍ２２ , R Ｍ２３ , R Ｍ２４ , R Ｍ２５ , R Ｍ２６ , R Ｍ２７ , R Ｍ２８ , R Ｍ２９ , R Ｍ３０ , R Ｍ３１ , R Ｍ３２ , R Ｍ３３ , R Ｍ３４ , R Ｍ３５ , R Ｍ３６ , R Ｍ３７ , R Ｍ３８ , R Ｍ３９ , and nx are R in formula (M1-1), respectively. Ｍ２１ , R Ｍ２２ , R Ｍ２３ , R Ｍ２４ , R Ｍ２５ , R Ｍ２６ , R Ｍ２７ , R Ｍ２８ , R Ｍ２９ , R Ｍ３０ , R Ｍ３１ , R Ｍ３２ , R Ｍ３３ , R Ｍ３４ , R Ｍ３５ , R Ｍ３６ , R Ｍ３７ , R Ｍ３８ , R Ｍ３９ , and nx, and the preferred ranges are also the same.

[0044] The compound represented by formula (M1-1) is preferably a compound represented by the following formula (M1-3), and more preferably a compound represented by the following formula (M1-4). (In formula (M1-3), nx represents an integer of 1 or more and 20 or less.) nx may be an integer of 10 or less. (In formula (M1-4), nx represents an integer of 1 or more and 20 or less.)

[0045] The molecular weight of the compound represented by formula (M1) is preferably 500 or more, more preferably 600 or more, and even more preferably 700 or more. By making the molecular weight equal to or greater than the lower limit, the low dielectric properties and low water absorption of the resulting cured product tend to be further improved. Furthermore, the molecular weight of the compound represented by formula (M1) is preferably 10,000 or less, more preferably 9,000 or less, even more preferably 7,000 or less, even more preferably 5,000 or less, and even more preferably 4,000 or less. By making the molecular weight equal to or less than the upper limit, the heat resistance and handleability of the resulting cured product tend to be further improved.

[0046] (In formula (M3), R ５５ each independently represents a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or a phenyl group; n ５ represents an integer of 1 or more and 10 or less.) R ５５ are each independently preferably a hydrogen atom, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a t-butyl group, an n-pentyl group, or a phenyl group, more preferably one of a hydrogen atom and a methyl group, and even more preferably a hydrogen atom. ５ is preferably an integer of 1 or more and 5 or less, more preferably an integer of 1 to 3, and even more preferably 1 or 2. The compound represented by formula (M3) may be a mixture of compounds where n5 is different, and a mixture is preferred. Furthermore, as described in the section on the compound represented by formula (M0), it may also be a mixture of compounds where the other moieties are different.

[0047] (In formula (M5), R ５８ each independently represents a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or a phenyl group; R ５９ each independently represents a hydrogen atom or a methyl group; n６ represents an integer of 1 or more.) R ５８ are each independently preferably a hydrogen atom, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a t-butyl group, an n-pentyl group, or a phenyl group, more preferably one of a hydrogen atom and a methyl group, and even more preferably a hydrogen atom. ５９ is preferably a methyl group. ６ is preferably an integer of 1 to 10, more preferably an integer of 1 to 5, even more preferably an integer of 1 to 3, still more preferably 1 or 2, and may be 1. In the compound represented by formula (M5), n ６ The compound represented by formula (M0) may be a mixture of compounds having different moieties, and is preferably a mixture. As described in the compound represented by formula (M0), the compound may be a mixture of compounds having different moieties.

[0048] (In the above formula (M7), R １ each independently represents an alkyl group having 1 to 10 carbon atoms; R ２ each independently represents an alkyl group, alkoxy group, or alkylthio group having 1 to 10 carbon atoms; an aryl group, aryloxy group, or arylthio group having 6 to 10 carbon atoms; a cycloalkyl group having 3 to 10 carbon atoms; a halogen atom; a hydroxyl group; or a mercapto group; ３ , R ４ , R ５ and R ６ each independently represents a hydrogen atom or a methyl group, and R ３ and R ４ one of which is a hydrogen atom and the other is a methyl group, and R ５ and R ６ one of which is a hydrogen atom and the other is a methyl group, １ is the following formula (x): (In formula (x), R ７ and R ８ each independently represents a hydrogen atom or a methyl group, and R ７ and R ８ one of which is a hydrogen atom and the other is a methyl group, and R ９each independently represents an alkyl group, alkoxy group, or alkylthio group having 1 to 10 carbon atoms; an aryl group, aryloxy group, or arylthio group having 6 to 10 carbon atoms; a cycloalkyl group having 3 to 10 carbon atoms; a halogen atom; a hydroxyl group; or a mercapto group, and t represents an integer of 0 to 4. １ X per benzene ring to which １ is the average number of substitutions, and represents a number from 0 to 4, p represents an integer from 1 to 3, q ​​represents an integer from 0 to 4, and k represents an integer from 1 to 100.

[0049] For details of the maleimide compound (M7) used in this embodiment, please refer to the description in Japanese Patent No. 7160151, the contents of which are incorporated herein by reference.

[0050] The maleimide compound (B) may be produced by a known method, or a commercially available product may be used. Examples of commercially available products include "BMI-80" manufactured by K.I. Chemical Industry Co., Ltd. as the compound represented by formula (M0), "NE-X-9470S" and "NE-X-9480S" manufactured by DIC Corporation as the compound represented by formula (M1), "MIR-3000-70MT" manufactured by Nippon Kayaku Co., Ltd. as the compound represented by formula (M3), "MIR-5000" manufactured by Nippon Kayaku Co., Ltd. as the compound represented by formula (M5), and "NE-X-9500" manufactured by DIC Corporation as the compound represented by formula (M7).

[0051] In addition to the above, examples of the maleimide compound (B) include compounds described in paragraphs 0061 to 0066 of WO 2020 / 262577 and Japanese Patent No. 7160151, which have a relative dielectric constant of 2.0 to 2.8 at a frequency of 10 GHz measured according to a cavity resonator perturbation method of the cured product, and the like, and the contents of which are incorporated herein by reference.

[0052] Furthermore, examples of the maleimide compound (B) other than those mentioned above include compounds having two or more maleimide groups, and specific examples thereof include m-phenylene bismaleimide, 2,2-bis(4-(4-maleimidophenoxy)-phenyl)propane, 4-methyl-1,3-phenylene bismaleimide, 1,6-bismaleimide-(2,2,4-trimethyl)hexane, prepolymers thereof, and prepolymers of these maleimides and amines.

[0053] The maleimide group equivalent of the maleimide compound (B) is preferably 130 g / eq. or more, more preferably 150 g / eq. or more, even more preferably 170 g / eq. or more, even more preferably 180 g / eq. or more, and even more preferably 200 g / eq. or more, and is preferably 1000 g / eq. or less, more preferably 800 g / eq. or less, even more preferably 700 g / eq. or less, even more preferably 600 g / eq. or less, and even more preferably 500 g / eq. or less. By setting it to the above lower limit or more, the low dielectric properties (Dk and / or Df, especially Df) of the obtained cured product tend to be more excellent. Furthermore, by setting it to the above upper limit or less, the effect of excellent moisture absorption and heat resistance tends to be further improved. The maleimide group equivalent can be measured according to the method described below.

[0054] The lower limit of the content of the maleimide compound (B) in the resin composition of this embodiment is preferably 5 parts by mass or more, more preferably 7 parts by mass or more, even more preferably 10 parts by mass or more, even more preferably 15 parts by mass or more, even more preferably 20 parts by mass or more, even more preferably 25 parts by mass or more, particularly preferably 30 parts by mass or more, and may even be 35 parts by mass or more, 40 parts by mass or more, depending on the application, etc. When the content of the maleimide compound (B) is equal to or greater than the above lower limit, the heat resistance and moisture absorption heat resistance of the obtained cured product tend to be improved. Furthermore, the upper limit of the content of the maleimide compound (B) is preferably 90 parts by mass or less, more preferably 80 parts by mass or less, even more preferably 70 parts by mass or less, even more preferably 60 parts by mass or less, even more preferably 55 parts by mass or less, and even more preferably 50 parts by mass or less, relative to 100 parts by mass of the resin solid content in the resin composition. When the content of the maleimide compound (B) (B) is equal to or less than the above upper limit, the resulting cured product tends to have improved low dielectric properties, peel strength, and low water absorption. The resin composition in this embodiment may contain only one type of maleimide compound (B), or may contain two or more types. When two or more types are contained, it is preferable that the total amount is in the above range.

[0055] <Compound Having Two or More Polymerizable Carbon-Carbon Unsaturated Double Bonds> The resin composition of this embodiment may further contain a compound having two or more polymerizable carbon-carbon unsaturated double bonds. The inclusion of such a compound increases the curability of the resin composition, and tends to further improve the moisture absorption heat resistance of the resulting cured product. Specifically, the upper limit of the number of carbon-carbon unsaturated double bonds contained in the compound having two or more carbon-carbon unsaturated double bonds used in this embodiment is preferably 2,000 or less, may be 10 or less, or may even be 5 or less, and may particularly be 2.

[0056] The polymerizable carbon-carbon unsaturated double bond possessed by the compound having two or more polymerizable carbon-carbon unsaturated double bonds means a carbon-carbon unsaturated double bond that can react with the carbon-carbon unsaturated double bond possessed by the resin (A) upon curing, and is a compound having a terminal carbon-carbon unsaturated double bond. Note that a compound having a polymerizable carbon-carbon unsaturated double bond that also falls under the category of maleimide compound (B) is classified as maleimide compound (B).

[0057] In the compound having two or more polymerizable carbon-carbon unsaturated double bonds, the polymerizable carbon-carbon unsaturated double bond is preferably at least one selected from the group consisting of a vinyl group, a (meth)allyl group, a (meth)acryloyl group, and a vinylene group, more preferably contains at least one selected from the group consisting of a vinyl group, a (meth)allyl group, and a (meth)acryloyl group, and even more preferably contains a vinyl group.

[0058] Specifically, the compound having two or more polymerizable carbon-carbon unsaturated double bonds preferably includes at least one selected from the group consisting of vinyl aryl compounds, (meth)acrylate compounds, and (meth)allyl compounds. An example of a vinyl aryl compound is a polyphenylene ether compound having two or more terminal carbon-carbon unsaturated double bonds, the terminal group of which is a vinylbenzyl group, and a polymer having a structural unit represented by formula (V). Specific examples of the compound having two or more polymerizable carbon-carbon unsaturated double bonds preferably include at least one selected from the group consisting of polyphenylene ether compounds having two or more terminal carbon-carbon unsaturated double bonds and polymers having a structural unit represented by formula (V). (In formula (V), Ar represents an aromatic hydrocarbon linking group. * represents a bonding position.)

[0059] The content of the compound having two or more polymerizable carbon-carbon unsaturated double bonds in the resin composition of this embodiment is preferably 5 parts by mass or more, more preferably 10 parts by mass or more, even more preferably 20 parts by mass or more, even more preferably 30 parts by mass or more, even more preferably 40 parts by mass or more, and preferably 90 parts by mass or less, more preferably 80 parts by mass or less, and even more preferably 75 parts by mass or less, per 100 parts by mass of the resin solids in the resin composition. By setting the content at or above the lower limit, the peel strength and heat resistance tend to be better. Furthermore, by setting the content at or below the upper limit, the low dielectric properties (Dk and / or Df) of the resulting cured product tend to be better. The resin composition of this embodiment may contain only one type of compound having two or more polymerizable carbon-carbon unsaturated double bonds, or may contain two or more types. When two or more types are included, the total amount preferably falls within the above range.

[0060] <<Polyphenylene Ether Compound Having a Terminal Carbon-Carbon Unsaturated Double Bond>> The resin composition of this embodiment may contain a polyphenylene ether compound having a terminal carbon-carbon unsaturated double bond. The polyphenylene ether compound having a terminal carbon-carbon unsaturated double bond is preferably a polyphenylene ether compound having two or more terminal carbon-carbon unsaturated double bonds. In this embodiment, the polyphenylene ether compound preferably contains, as the carbon-carbon unsaturated double bond, one or more groups selected from the group consisting of a (meth)acryloyl group and a vinylbenzyl group. Use of a polyphenylene ether compound containing these groups tends to more effectively improve the dielectric properties and low water absorption of printed wiring boards and the like. In this embodiment, it is also preferable to contain both a polyphenylene ether compound having a group represented by formula (Rx-1) described below and a polyphenylene ether compound having a group represented by formula (Rx-2). By using such a composition, the low dielectric properties (Dk and / or Df, particularly Df) of the obtained cured product are more excellent, and the heat resistance over time (low dielectric properties (Dk and / or Df, particularly Df) after heating) of the obtained cured product can be more effectively maintained. These are described in detail below.

[0061] Examples of polyphenylene ether compounds having a terminal carbon-carbon unsaturated double bond include compounds having a phenylene ether skeleton represented by the following formula (X1).

[0062] (In formula (X1), R ２４ , R ２５ , R ２６ , and R ２７ may be the same or different and represent an alkyl group having 6 or less carbon atoms, an aryl group, a halogen atom, or a hydrogen atom.

[0063] The polyphenylene ether compound having a terminal carbon-carbon unsaturated double bond is represented by the formula (X2): (In formula (X2), R ２８ , R ２９ , R ３０ , R ３４, and R ３５ may be the same or different and represent an alkyl group having 6 or less carbon atoms or a phenyl group. ３１ , R ３２ , and R ３３ may be the same or different and are a hydrogen atom, an alkyl group having 6 or less carbon atoms, or a phenyl group.) and / or a repeating unit represented by formula (X3): (In formula (X3), R ３６ , R ３７ , R ３８ , R ３９ , R ４０ , R ４１ , R ４２ , and R ４３ may be the same or different and are a hydrogen atom, an alkyl group having 6 or less carbon atoms, or a phenyl group. -A- is a linear, branched, or cyclic divalent hydrocarbon group having 20 or less carbon atoms.

[0064] The polyphenylene ether compound having a terminal carbon-carbon unsaturated double bond is preferably a modified polyphenylene ether compound in which some or all of the terminals are functionalized with ethylenically unsaturated groups (hereinafter, sometimes referred to as "modified polyphenylene ether compound (g)"), and more preferably a modified polyphenylene ether compound having two or more groups selected from the group consisting of (meth)acryloyl groups and vinylbenzyl groups at the terminals. By using such a modified polyphenylene ether compound (g), it is possible to further reduce the dielectric dissipation factor (Df) of the cured product of the resin composition, and to improve its low water absorption and metal foil peel strength. These modified polyphenylene ether compounds (g) may be used alone or in combination of two or more.

[0065] The modified polyphenylene ether compound (g) may be a polyphenylene ether compound represented by formula (OP). (In formula (OP), X represents an aromatic group, and —(Y—O) ｎ１- represents a polyphenylene ether structure, n1 represents an integer of 1 to 100, and n2 represents an integer of 2 to 4. Rx is a group represented by formula (Rx-1) or formula (Rx-2). (In formula (Rx-1) and formula (Rx-2), R １ , R ２ , and R ３ each independently represents a hydrogen atom, an alkyl group, an alkenyl group, or an alkynyl group. * represents a bonding site with an oxygen atom. Each Mc independently represents a hydrocarbon group having 1 to 12 carbon atoms. z represents an integer of 0 to 4. r represents an integer of 0 to 6.

[0066] The aromatic group represented by X may or may not have a substituent on the benzene ring, but preferably has one. When the aromatic group has a substituent, examples thereof include the above-mentioned substituent Z, and the substituent is preferably at least one selected from the group consisting of an alkyl group having 6 or less carbon atoms, an aryl group, and a halogen atom, more preferably an alkyl group having 3 or less carbon atoms, and even more preferably a methyl group. In addition, the -(Y-O)n １ The polyphenylene ether structure represented by - may or may not have a substituent on the benzene ring, but preferably has one. When it has a substituent, examples of the substituent Z include the above-mentioned substituent Z, but it is preferably an alkyl group having 6 or less carbon atoms or a phenyl group, more preferably an alkyl group having 3 or less carbon atoms, and even more preferably a methyl group. １ and / or n ２ When n is an integer of 2 or more, １ n structural units (Y-O) and / or n ２ The n constitutional units may be the same or different. ２ is preferably 22 or more, more preferably 2.

[0067] In formula (Rx-1) and formula (Rx-2), R １ , R ２ , and R ３ R each independently represents a hydrogen atom, an alkyl group, an alkenyl group, or an alkynyl group. １is preferably a hydrogen atom or an alkyl group, more preferably a hydrogen atom or a methyl group, and even more preferably a hydrogen atom. ２ and R ３ are each independently preferably a hydrogen atom or an alkyl group, more preferably a hydrogen atom or a methyl group, and even more preferably a hydrogen atom. １ , R ２ , and R ３ The number of carbon atoms in each of the alkyl group, alkenyl group, and alkynyl group is preferably 5 or less, and more preferably 3 or less.

[0068] In formula (Rx-1), r represents an integer of 0 to 6, and may be an integer of 1 or more, and is preferably an integer of 5 or less, more preferably an integer of 4 or less, even more preferably an integer of 3 or less, still more preferably 1 or 2, and even more preferably 1.

[0069] In formula (Rx-1), each Mc independently represents a hydrocarbon group having 1 to 12 carbon atoms, preferably a hydrocarbon group having 1 to 10 carbon atoms, more preferably a linear or branched alkyl group having 1 to 10 carbon atoms, still more preferably a methyl group, ethyl group, isopropyl group, isobutyl group, t-butyl group, pentyl group, octyl group, or nonyl group, and even more preferably a methyl group, ethyl group, isopropyl group, isobutyl group, or t-butyl group. In formula (Rx-1), z represents an integer of 0 to 4, preferably an integer of 0 to 3, more preferably an integer of 0 to 2, still more preferably 0 or 1, and still more preferably 0.

[0070] A specific example of the group represented by formula (Rx-1) is a vinylbenzyl group, and a specific example of the group represented by formula (Rx-2) is a (meth)acryloyl group.

[0071] The resin composition of the present embodiment preferably contains, as the polyphenylene ether compound having a terminal carbon-carbon unsaturated double bond, a compound represented by formula (OP), which contains both a polyphenylene ether compound having a group represented by formula (Rx-1) and a compound having a polyphenylene ether group having a group represented by formula (Rx-2).

[0072] The modified polyphenylene ether compound (g) includes a compound represented by formula (OP-1). (In formula (OP-1), X represents an aromatic group, and —(Y—O)n ２ - represents a polyphenylene ether structure, and R １ , R ２ , and R ３ each independently represents a hydrogen atom, an alkyl group, an alkenyl group, or an alkynyl group; n １ represents an integer of 0 to 6, and n ２ represents an integer from 1 to 100, and n ３ represents an integer of 2 to 4.) The aromatic group represented by X may or may not have a substituent on the benzene ring, but preferably has one. When the aromatic group has a substituent, examples thereof include the above-mentioned substituent Z, but it is preferably at least one selected from the group consisting of an alkyl group having 6 or less carbon atoms, an aryl group, and a halogen atom, more preferably an alkyl group having 3 or less carbon atoms, and even more preferably a methyl group. In addition, the -(Y-O)n ２ The polyphenylene ether structure represented by - may or may not have a substituent on the benzene ring, but preferably has one. When it has a substituent, examples of the substituent Z include the above-mentioned substituent Z, but it is preferably an alkyl group having 6 or less carbon atoms or a phenyl group, more preferably an alkyl group having 3 or less carbon atoms, and even more preferably a methyl group. ２ and / or n ３ When n is an integer of 2 or more, ２ n structural units (Y-O) and / or n ３ The n constitutional units may be the same or different. ３is preferably 2 or more, more preferably 2.

[0073] The modified polyphenylene ether compound (g) in this embodiment is preferably a compound represented by formula (OP-2). Here, -(O-X-O)- represents the formula (OP-3): (In formula (OP-3), R ４ , R ５ , R ６ , R ９ , R １０ , and R １１ may be the same or different and are alkyl groups or phenyl groups having 6 or less carbon atoms. ７ and R ８ may be the same or different and are a hydrogen atom, an alkyl group having 6 or less carbon atoms, or a phenyl group.) and / or a group represented by formula (OP-4): (In formula (OP-4), R １２ , R １３ , R １４ , R １５ , R １６ , R １７ , R １８ , and R １９ may be the same or different and are a hydrogen atom, an alkyl group having 6 or less carbon atoms, or a phenyl group. -A- is a linear, branched, or cyclic divalent hydrocarbon group having 20 or less carbon atoms.

[0074] In addition, -(Y-O)- represents a group represented by formula (OP-5): (In formula (OP-5), R ２０ , R ２１ may be the same or different and are alkyl groups or phenyl groups having 6 or less carbon atoms. ２２ , R ２３ may be the same or different and are a hydrogen atom, an alkyl group having 6 or less carbon atoms, or a phenyl group. ２０ and R ２１are each independently a group having one or more methyl groups and / or cyclohexyl groups, the rigidity of the resulting resin molecules is increased, and since highly rigid molecules have lower mobility than less rigid molecules, the relaxation time during dielectric relaxation is longer, resulting in excellent low dielectric properties (Dk and / or Df, particularly Dk), which is preferable. An example of formula (OP-5) is the following structure. For the polyphenylene ether compound having the above structure, the description in JP 2019-194312 A can be referred to, the contents of which are incorporated herein by reference.

[0075] In formula (OP-2), a and b each independently represent an integer of 0 to 100, and at least one of a and b is an integer of 1 to 100. a and b each independently represent an integer of 0 to 50, more preferably an integer of 1 to 30, and preferably an integer of 1 to 10. When a and / or b is an integer of 2 or greater, two or more -(Y-O)- groups may each independently represent an arrangement of one type of structure, or two or more types of structures may be arranged in blocks or randomly. Furthermore, when a compound represented by formula (OP-2) is contained, the average value of a preferably satisfies 1<a<10, and the average value of b preferably satisfies 1<b<10.

[0076] Examples of -A- in formula (OP-4) include divalent organic groups such as a methylene group, an ethylidene group, a 1-methylethylidene group, a 1,1-propylidene group, a 1,4-phenylenebis(1-methylethylidene) group, a 1,3-phenylenebis(1-methylethylidene) group, a cyclohexylidene group, a phenylmethylene group, a naphthylmethylene group, and a 1-phenylethylidene group, but are not limited to these.

[0077] Among the compounds represented by the above formula (OP-2), R ４ , R ５ , R ６ , R ９ , R １０ , R １１ , R ２０ , and R ２１ is an alkyl group having 3 or less carbon atoms, and R ７, R ８ , R １４ , R １５ , R １６ , R １７ , R ２２ , and R ２３ is a hydrogen atom or an alkyl group having 3 or less carbon atoms, and it is particularly preferred that -(O-X-O)- represented by formula (OP-3) or formula (OP-4) is formula (OP-9), formula (OP-10), and / or formula (OP-11), and that -(Y-O)- represented by formula (OP-5) is formula (OP-12) or formula (OP-13). When a and / or b are integers of 2 or more, the two or more -(Y-O)- may each independently be a structure in which two or more of formula (OP-12) and / or formula (OP-13) are arranged, or a structure in which formula (OP-12) and formula (OP-13) are arranged in blocks or randomly.

[0078] (In formula (OP-10), R ４４ , R ４５ , R ４６ , and R ４７ may be the same or different and are a hydrogen atom or a methyl group. -B- is a linear, branched or cyclic divalent hydrocarbon group having 20 or less carbon atoms. Specific examples of -B- include the same as the specific examples of -A- in formula (OP-4). (In formula (OP-11), -B- represents a linear, branched, or cyclic divalent hydrocarbon group having 20 or less carbon atoms.) Specific examples of -B- include the same as the specific examples of -A- in formula (OP-4).

[0079] The modified polyphenylene ether compound (g) is more preferably a compound represented by formula (OP-14) and / or a compound represented by formula (OP-15), and even more preferably a compound represented by formula (OP-15). (In formula (OP-14), a and b each independently represent an integer of 0 to 100, and at least one of a and b is an integer of 1 to 100.) a and b in formula (OP-14) each independently have the same meanings as a and b in formula (OP-2), and the preferred ranges are also the same. (In formula (OP-15), a and b each independently represent an integer of 0 to 100, and at least one of a and b is an integer of 1 to 100.) a and b in formula (OP-15) each independently have the same meanings as a and b in formula (OP-2), and the preferred ranges are also the same.

[0080] The polyphenylene ether compound having a terminal carbon-carbon unsaturated double bond may be produced by a known method, or a commercially available product may be used. Examples of commercially available products include "SA9000" manufactured by SABIC Innovative Plastics, which is a modified polyphenylene ether compound having a terminal methacryloyl group. Examples of modified polyphenylene ether compounds having a terminal vinylbenzyl group include "OPE-2St1200" and "OPE-2st2200" manufactured by Mitsubishi Gas Chemical Company. Examples of modified polyphenylene ether compounds having a terminal hydroxyl group, such as "SA90" manufactured by SABIC Innovative Plastics, which have been modified to a vinylbenzyl group using vinylbenzyl chloride or the like, may also be used as modified polyphenylene ether compounds having a terminal hydroxyl group.

[0081] In addition, for details of polyphenylene ether compounds having terminal carbon-carbon unsaturated double bonds, see JP 2006-028111 A, JP 2018-131519 A, WO 2019-138992, and WO 2022-054303. The contents of these publications are incorporated herein by reference.

[0082] The polyphenylene ether compound having a terminal carbon-carbon unsaturated double bond (preferably a modified polyphenylene ether compound (g)) preferably has a polystyrene-equivalent number average molecular weight (details follow the method described in the Examples below) measured by GPC (gel permeation chromatography) of 500 or more and 3,000 or less. A number average molecular weight of 500 or more tends to further suppress stickiness when the resin composition of the present embodiment is formed into a coating film. Furthermore, a number average molecular weight of 3,000 or less tends to further improve solubility in solvents. Furthermore, the polyphenylene ether compound having a terminal carbon-carbon unsaturated double bond (preferably a modified polyphenylene ether compound (g)) preferably has a polystyrene-equivalent weight average molecular weight (details follow the method described in the Examples below) measured by GPC of 800 or more and 10,000 or less, more preferably 800 or more and 5,000 or less. When the weight-average molecular weight is equal to or greater than the lower limit, the dielectric constant (Dk) and dielectric dissipation factor (Df) of the cured product of the resin composition tend to be lower, and when the weight-average molecular weight is equal to or less than the upper limit, the solubility, low viscosity, and moldability of the resin composition in solvents when preparing varnishes, etc., as described below, tend to be further improved. Furthermore, the terminal carbon-carbon unsaturated double bond equivalent of the polyphenylene ether compound (preferably, the modified polyphenylene ether compound (g)) having a terminal carbon-carbon unsaturated double bond is preferably 400 to 5,000 g, more preferably 400 to 2,500 g, per carbon-carbon unsaturated double bond. When the terminal carbon-carbon unsaturated double bond equivalent is equal to or greater than the lower limit, the dielectric constant (Dk) and dielectric dissipation factor (Df) of the cured product of the resin composition tend to be lower, and when the weight-average molecular weight is equal to or less than the upper limit, the solubility, low viscosity, and moldability of the resin composition in solvents tend to be further improved.

[0083] The functional group equivalent (equivalent of carbon-carbon unsaturated double bond) in a polyphenylene ether compound having a terminal carbon-carbon unsaturated double bond is calculated from the reciprocal of the amount of double bonds determined from the results of measurement using an infrared spectrometer. The double bond equivalent [g / eq.] was determined as follows: A powder of the polyphenylene ether compound is weighed and the weight is recorded. This powder is placed in a measuring flask and then diluted to a predetermined amount with carbon disulfide to prepare a measurement sample. This sample liquid is placed in a measurement cell and set in an infrared spectrophotometer (FT / IR-4600, manufactured by JASCO Corporation). Subsequently, infrared spectroscopy of the sample liquid is performed. In the case of a vinyl group in a polyphenylene ether compound, the IR spectrum of 905 cm is －１ When the carbon-carbon unsaturated double bond is a methacrylic group, the peak area of ​​the spectrum around 1640 cm is recorded. －１ The peak area of ​​the spectrum near the peak is recorded. From this area value and the calibration curve, the double bond concentration [mol / L] is determined as a measured value. Next, the double bond equivalent is calculated using the following formula: Double bond equivalent [g / eq.] = Powder weight in measurement sample [g] / Double bond concentration [mol / L] × Measurement sample liquid volume [L]. The maleimide group equivalent of the maleimide compound (B) and the functional group equivalent of other thermosetting compounds other than the polyphenylene ether compound having a terminal carbon-carbon unsaturated double bond can also be measured using the same method. When two or more other thermosetting compounds are contained, the functional group equivalent of the other thermosetting compounds is the sum (weighted average) of the values ​​obtained by multiplying the functional group equivalent of each thermosetting compound by its mass fraction. The same applies to when two or more maleimide compounds (B) are contained, or when two or more maleimide compounds (B) and two or more other thermosetting compounds are contained.

[0084] When the resin composition of this embodiment contains a polyphenylene ether compound having a terminal carbon-carbon unsaturated double bond, the lower limit of the content is preferably 1 part by mass or more, more preferably 2 parts by mass or more, even more preferably 3 parts by mass or more, even more preferably 4 parts by mass or more, and even more preferably 5 parts by mass or more, per 100 parts by mass of the resin solids in the resin composition. By setting the content at or above the lower limit, the moldability of the resin composition and the heat resistance, low water absorption, and low dielectric properties (Dk and / or Df) of the resulting cured product tend to be further improved. Furthermore, the upper limit of the content of the polyphenylene ether compound having a terminal carbon-carbon unsaturated double bond is preferably 90 parts by mass or less, more preferably 70 parts by mass or less, per 100 parts by mass of the resin solids in the resin composition. Furthermore, depending on the application, it may be 60 parts by mass or less, 40 parts by mass or less, 20 parts by mass or less, 10 parts by mass or less, or 8 parts by mass or less. By adjusting the content to be equal to or less than the upper limit, the low dielectric properties (Dk and / or Df) and chemical resistance of the obtained cured product tend to be improved. The resin composition in this embodiment may contain only one type of polyphenylene ether compound having a terminal carbon-carbon unsaturated double bond, or may contain two or more types. When two or more types are contained, it is preferable that the total amount be in the above range.

[0085] <<Polymer Having a Structural Unit Represented by Formula (V)>> The resin composition of the present embodiment may contain a polymer having a structural unit represented by formula (V). By containing a polymer having a structural unit represented by formula (V), a resin composition with excellent low dielectric properties (low dielectric constant, low dielectric loss tangent) can be obtained. (In formula (V), Ar represents an aromatic hydrocarbon linking group. * represents a bonding position.) The aromatic hydrocarbon linking group may be a group consisting only of aromatic hydrocarbons which may have a substituent, or a group consisting of a combination of aromatic hydrocarbons which may have a substituent and other linking groups. The aromatic hydrocarbon linking group is preferably a group consisting only of aromatic hydrocarbons which may have a substituent. Examples of the substituent that the aromatic hydrocarbon may have include the substituent Z (e.g., an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an alkynyl group having 2 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a hydroxy group, an amino group, a carboxy group, a halogen atom, etc.). It is also preferable that the aromatic hydrocarbon does not have a substituent. The aromatic hydrocarbon linking group is usually a divalent linking group.

[0086] Specific examples of the aromatic hydrocarbon linking group include a phenylene group, a naphthalenediyl group, an anthracenediyl group, a phenanthrenediyl group, a biphenyldiyl group, and a fluorenediyl group, each of which may have a substituent, and among these, a phenylene group which may have a substituent is preferred. Examples of the substituent include the above-mentioned substituent Z, but it is preferable that the above-mentioned phenylene group and other groups do not have a substituent.

[0087] It is more preferable that the polymer having a structural unit represented by formula (V) contains at least one of a structural unit represented by formula (V1) below, a structural unit represented by formula (V2) below, and a structural unit represented by formula (V3) below. In the formulas below, * represents a bonding position. Furthermore, hereinafter, the structural units represented by formulas (V1) to (V3) may be collectively referred to as "structural unit (a)."

[0088] In formulas (V1) to (V3), L １is an aromatic hydrocarbon linking group (preferably having 6 to 22 carbon atoms, more preferably 6 to 18, and even more preferably 6 to 10 carbon atoms). Specific examples include phenylene groups, naphthalenediyl groups, anthracenediyl groups, phenanthrenediyl groups, biphenyldiyl groups, and fluorenediyl groups, each of which may have a substituent. Of these, phenylene groups, which may have a substituent, are preferred. Examples of the substituent include the aforementioned substituent Z, but it is preferable that the aforementioned groups, such as the phenylene group, be unsubstituted. The compound forming the structural unit (a) is preferably a divinyl aromatic compound. That is, a polymer having a structural unit represented by formula (V) preferably contains a structural unit (a) derived from a divinyl aromatic compound. Examples of divinyl aromatic compounds include divinylbenzene, bis(1-methylvinyl)benzene, divinylnaphthalene, divinylanthracene, divinylbiphenyl, and divinylphenanthrene. Of these, divinylbenzene is particularly preferred. These divinyl aromatic compounds may be used alone, or two or more types may be used as needed.

[0089] As mentioned above, the polymer having the structural unit represented by formula (V) may be a homopolymer of the structural unit (a), but may also be a copolymer with a structural unit derived from another monomer.When the polymer having the structural unit represented by formula (V) is a copolymer, its copolymerization ratio is preferably 3 mol% or more of the structural unit (a), more preferably 5 mol% or more, even more preferably 10 mol% or more, and may even be 15 mol% or more.The upper limit 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, particularly more preferably 30 mol% or less, and may even be 25 mol% or less, 20 mol% or less.

[0090] An example of a structural unit derived from another monomer is a structural unit (b) derived from an aromatic compound having one vinyl group (monovinyl aromatic compound).

[0091] The structural unit (b) derived from a monovinyl aromatic compound preferably includes a structural unit represented by the following formula (V4).

[0092] In formula (V4), L ２ is an aromatic hydrocarbon linking group, and preferred examples thereof include the above L １ Examples include the following. * indicates the bonding position. R Ｖ１ is a hydrogen atom or a hydrocarbon group having 1 to 12 carbon atoms (preferably an alkyl group). Ｖ１ When R is a hydrocarbon group, it preferably has 1 to 6 carbon atoms, more preferably 1 to 3 carbon atoms. Ｖ１ and L ２ may have the above-mentioned substituent Z.

[0093] When the polymer having a structural unit represented by formula (V) is a copolymer containing a structural unit (b) derived from a monovinyl aromatic compound, examples of the monovinyl aromatic compound include vinyl aromatic compounds such as styrene, vinylnaphthalene, and vinylbiphenyl; and nuclear 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 optionally have the aforementioned substituent Z. Furthermore, these monovinyl aromatic compounds may be used alone or in combination with two or more. Among these, the structural unit (b) preferably contains a structural unit derived from at least one selected from the group consisting of o-ethylvinylbenzene, m-ethylvinylbenzene, and p-ethylvinylbenzene. It is more preferable that the structural unit (b) further contains a structural unit derived from styrene in addition to a structural unit derived from at least one selected from the group consisting of o-ethylvinylbenzene, m-ethylvinylbenzene, and p-ethylvinylbenzene.

[0094] When the polymer having the structural unit represented by formula (V) is a copolymer containing the structural unit (b), the copolymerization ratio of the structural unit (b) is preferably 10 mol% or more, more preferably 15 mol% or more, 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. The upper limit is preferably 98 mol% or less, more preferably 90 mol% or less, and even more preferably 85 mol% or less.

[0095] A polymer having a structural unit represented by formula (V) may have structural units other than the structural unit (a) and the structural unit (b). Examples of such structural units include structural unit (c) derived from a cycloolefin compound. Examples of cycloolefin compounds include hydrocarbons having a double bond within the ring structure. Specific examples include monocyclic olefins such as cyclobutene, cyclopentene, cyclohexene, and cyclooctene, as well as compounds having a norbornene ring structure such as norbornene and dicyclopentadiene, and cycloolefin compounds having condensed aromatic rings such as indene and acenaphthylene. Examples of norbornene compounds include those described in paragraphs 0037 to 0043 of JP 2018-039995 A, the contents of which are incorporated herein by reference. The cycloolefin compounds exemplified here may further have the aforementioned substituent Z.

[0096] When the polymer having the structural unit represented by formula (V) is a copolymer containing the structural unit (c), the copolymerization ratio of the structural unit (c) is preferably 10 mol% or more, more preferably 20 mol% or more, and even more preferably 30 mol% or more. The upper limit is preferably 90 mol% or less, more preferably 80 mol% or less, and even more preferably 70 mol% or less, and may be 50 mol% or less, or may be 30 mol% or less.

[0097] A polymer having a structural unit represented by formula (V) may further incorporate a structural unit (d) derived from a different polymerizable compound (hereinafter also referred to as "other polymerizable compound"). Examples of other polymerizable compounds (monomers) include compounds containing three vinyl groups. Specific examples include 1,3,5-trivinylbenzene, 1,3,5-trivinylnaphthalene, and 1,2,4-trivinylcyclohexane. Alternatively, examples include ethylene glycol diacrylate, 1,3-butadiene, and isoprene. The copolymerization ratio (d) of the structural unit (d) derived from the other polymerizable compound is preferably 30 mol% or less, more preferably 20 mol% or less, and even more preferably 10 mol% or less.

[0098] An example of an embodiment of a polymer having a structural unit represented by formula (V) is a polymer that essentially contains the structural unit (a) and contains at least one of the structural units (b) to (d). Further examples include polymers in which the total of the structural units (a) to (d) accounts for 95 mol% or more, and even 98 mol% or more, of all structural units. Another embodiment of a polymer having a structural unit represented by formula (V) is a polymer that essentially contains the structural unit (a), and in which, of all structural units excluding the terminals, structural units containing aromatic rings account for preferably 90 mol% or more, more preferably 95 mol% or more, and even 100 mol%. Note that, when calculating the mol% per total structural units, one structural unit is considered to be derived from one molecule of a monomer (e.g., a divinyl aromatic compound, a monovinyl aromatic compound, etc.) used in the production of a polymer having a structural unit represented by formula (V).

[0099] The method for producing a polymer having a structural unit represented by formula (V) is not particularly limited and may be a conventional method, but examples thereof include polymerizing a raw material containing a divinyl aromatic compound (optionally in the presence of a monovinyl aromatic compound, a cycloolefin compound, etc.) in the presence of a Lewis acid catalyst. The Lewis acid catalyst may be a metal fluoride such as boron trifluoride or a complex thereof.

[0100] The structure of the chain end of the polymer having the structural unit represented by formula (V) is not particularly limited, but in terms of the group derived from the divinyl aromatic compound, it may have a structure represented by the following formula (E1). １ is the same as defined in the above formula (V1). * represents the bonding position. *-CH=CH-L １ -CH=CH ２ (E1)

[0101] When a group derived from a monovinyl aromatic compound is at the chain end, the structure may be that of the following formula (E2): ２ and R Ｖ１ are the same as defined in the formula (V4). * represents a bonding position. *-CH=CH-L ２ -R Ｖ１ (E2)

[0102] The molecular weight of the polymer having the structural unit represented by formula (V) is preferably 400 or more, more preferably 500 or more, even more preferably 1,000 or more, and even more preferably 1,500 or more, in terms of number average molecular weight Mn. The upper limit of the number average molecular weight Mn is preferably 130,000 or less, more preferably 120,000 or less, even more preferably 110,000 or less, even more preferably 100,000 or less, and may be 30,000 or less, 10,000 or less, or 5,000 or less. The molecular weight of the polymer having the structural unit represented by formula (V) is preferably 3,000 or more, more preferably 5,000 or more, even more preferably 10,000 or more, in terms of weight average molecular weight Mw. By setting the weight average molecular weight Mw at or above the lower limit, the excellent low dielectric properties of the polymer having the structural unit represented by formula (V), particularly Df and dielectric properties after moisture absorption, can be effectively exhibited in the cured product of the resin composition. The upper limit of the weight-average molecular weight Mw is preferably 130,000 or less, more preferably 100,000 or less, even more preferably 80,000 or less, and even more preferably 50,000 or less. By keeping the weight-average molecular weight Mw below the upper limit, poor embedding tends to be less likely when the prepreg or resin sheet is laminated on a circuit-forming substrate. The monodispersity (Mw / Mn), expressed as the ratio of the weight-average molecular weight Mw to the number-average molecular weight Mn, is preferably 100 or less, more preferably 50 or less, even more preferably 20 or less, and may be 15 or less, or even 12 or less. As for the lower limit, a practical value is 1.1 or more, preferably 2.0 or more, more preferably 4 or more, even more preferably 5 or more, even more preferably 7 or more, and even more preferably 8 or more. The Mw and Mn are measured according to the description in the Examples below. When the resin composition of the present embodiment contains two or more polymers having a structural unit represented by formula (V), it is preferable that the Mw, Mn and Mw / Mn of the mixture satisfy the above ranges.

[0103] The vinyl group equivalent of the polymer having a structural unit represented by formula (V) is preferably 200 g / eq. or more, more preferably 230 g / eq. or more, even more preferably 250 g / eq. or more, and may be 300 g / eq. or more, or 350 g / eq. or more. The vinyl group equivalent is preferably 1200 g / eq. or less, more preferably 1000 g / eq. or less, and may further be 800 g / eq. or less, 600 g / eq. or less, 500 g / eq. or less, 400 g / eq. or less, or 350 g / eq. or less. When the vinyl group equivalent is equal to or greater than the lower limit, the storage stability of the resin composition tends to be improved, and the flowability of the resin composition tends to be improved. Therefore, moldability is improved, voids are less likely to occur during the formation of prepregs, etc., and a more reliable printed wiring board tends to be obtained. On the other hand, when the vinyl group equivalent is equal to or less than the upper limit, the heat resistance of the resulting cured product tends to be improved. The glass transition temperature of the polymer having a structural unit represented by formula (V) is preferably 170°C or higher, more preferably 180°C or higher, even more preferably 190°C or higher, and even more preferably 200°C or higher. The upper limit of the glass transition temperature is preferably 350°C or lower, and may be 300°C or lower. The glass transition temperature here can be determined using a dynamic viscoelasticity measuring device in accordance with JIS-K7244-4:1999 (Plastics - Test methods for dynamic mechanical properties - Part 4: Non-resonance method), by measuring the dynamic viscoelasticity of a measurement sample at a starting temperature of 30°C, an ending temperature of 400°C, a heating rate of 5°C / min, a measurement frequency of 1 Hz, and under a nitrogen atmosphere, and the maximum value of the loss tangent (tan σ) obtained at this time can be determined as the glass transition temperature. As the dynamic viscoelasticity measuring device, an EXSTAR6000 DMS6100 manufactured by Seiko Instruments Inc. can be used.

[0104] The cured product of a polymer having a structural unit represented by formula (V) preferably has excellent low dielectric properties. For example, the cured product of the polymer having the structural unit represented by formula (V) used in this embodiment preferably has a relative dielectric constant (Dk) of 2.80 or less, more preferably 2.60 or less, even more preferably 2.50 or less, and even more preferably 2.40 or less, at 10 GHz, measured according to a cavity resonator perturbation method. Furthermore, a practical lower limit of the relative dielectric constant is, for example, 1.80 or more. Furthermore, the cured product of the polymer having the structural unit represented by formula (V) preferably has a dielectric loss tangent (Df) of 0.0030 or less, more preferably 0.0020 or less, and even more preferably 0.0010 or less, at 10 GHz, measured according to a cavity resonator perturbation method. Furthermore, a practical lower limit of the dielectric loss tangent is, for example, 0.0001 or more. The relative dielectric constant (Dk) and dielectric loss tangent (Df) are measured by the following method.

[0105] The solvent of the polymer having a structural unit represented by formula (V) was evaporated to dryness to obtain a powder of a polymer having a structural unit represented by formula (V). Using the obtained powder of the polymer having a structural unit represented by formula (V), a cured plate was prepared as follows. The powder was filled into a mold having a side length of 100 mm and a thickness of 1.6 mm, and 12 μm copper foil (3EC-M3-VLP, manufactured by Mitsui Mining & Smelting Co., Ltd.) was placed on both sides. The mold was vacuum pressed at a pressure of 30 kg / cm and a temperature of 220°C for 120 minutes to obtain a cured plate having a side length of 100 mm and a thickness of 1.6 mm. The copper foil on both sides of the obtained cured plate was then removed by etching, and the relative permittivity (Dk) and dielectric loss tangent (Df) were measured after drying for 60 minutes at 120°C at a frequency of 10 GHz using a cavity resonator perturbation method in accordance with JIS C218:2007. The cavity resonator used was manufactured by EM Lab, and the network analyzer used was P5005A manufactured by Keysight Technologies.

[0106] For polymers having a structural unit represented by formula (V) in this specification, the compounds described in paragraphs 0029 to 0058 of WO 2017 / 115813 and their synthesis reaction conditions, etc., the compounds described in paragraphs 0013 to 0058 of JP-A 2018-039995 and their synthesis reaction conditions, etc., the compounds described in paragraphs 0008 to 0043 of JP-A 2018-168347 and their synthesis reaction conditions, etc., the compounds described in paragraphs 0014 to 0042 of JP-A 2006-070136 and their synthesis reaction conditions, etc., the compounds described in paragraphs 0014 to 0061 of JP-A 2006-089683 and their synthesis reaction conditions, etc., the compounds described in paragraphs 0008 to 0036 of JP-A 2008-248001 and their synthesis reaction conditions, etc. can be referenced, and are incorporated herein.

[0107] When the resin composition of this embodiment contains a polymer having a structural unit represented by formula (V), the content thereof is preferably 1 part by mass or more, more preferably 5 parts by mass or more, even more preferably 8 parts by mass or more, even more preferably 10 parts by mass or more, and even more preferably 12 parts by mass or more, relative to 100 parts by mass of the resin solid content, and is preferably 90 parts by mass or less, more preferably 70 parts by mass or less, even more preferably 50 parts by mass or less, even more preferably 40 parts by mass or less, and even more preferably 35 parts by mass or less. The resin composition of this embodiment may contain only one type of polymer having a structural unit represented by formula (V), or may contain two or more types. When the resin composition of this embodiment contains two or more types of polymers having a structural unit represented by formula (V), it is preferable that the total amount be in the above range.

[0108] <<(Meth)acrylate Compound>> The resin composition of the present embodiment may contain a (meth)acrylate compound (hereinafter, may be referred to as a “polyfunctional (meth)acrylate compound”). However, a (meth)acrylate compound that also falls under the category of a polyphenylene ether compound having a terminal carbon-carbon unsaturated double bond is considered to be classified as a polyphenylene ether compound having a terminal carbon-carbon unsaturated double bond.

[0109] The (meth)acrylate compound used in this embodiment is usually a compound containing two or more (meth)acryloyloxy groups in one molecule, and preferably three or more (meth)acryloyloxy groups in one molecule. The polyfunctional (meth)acrylate compound is preferably a compound having three to five (meth)acryloyloxy groups, more preferably a compound having three or four (meth)acryloyloxy groups, and even more preferably a compound having three (meth)acryloyloxy groups. The (meth)acrylate compound is preferably a compound having a methacryloyloxy group. The polyfunctional (meth)acrylate compound has a large number of (meth)acrylate groups that serve as crosslinking points, so it is firmly cured with the resin (A) and the maleimide compound (B), resulting in a cured product with low dielectric properties (Dk and / or Df) and excellent heat resistance. The polyfunctional (meth)acrylate compound is preferably a compound represented by formula (MA). Formula (MA) (In formula (MA), R １ represents a hydrogen atom or a substituent, R ２ each independently represents a hydrogen atom or a methyl group.

[0110] In formula (MA), R １ represents a hydrogen atom or a substituent, and is more preferably a substituent having a formula weight of 15 to 500, more preferably a substituent having a formula weight of 15 to 300, even more preferably a substituent having a formula weight of 15 to 100, and even more preferably a substituent having a formula weight of 15 to 50.

[0111] R １is preferably a hydrocarbon group or a (meth)acryloyloxy group, more preferably a hydrocarbon group having 22 or fewer carbon atoms, and even more preferably an alkyl group having 1 to 22 carbon atoms or an alkenyl group having 2 to 22 carbon atoms. By using a compound having an alkyl group having 1 to 22 carbon atoms or an alkenyl group having 2 to 22 carbon atoms, a resin composition can be provided that is excellent in crosslinkability and can yield a cured product with high toughness. This can prevent cracking during etching or other processes, even when the resin composition does not contain a substrate such as glass cloth. From the viewpoint of improving handleability, the number of carbon atoms in the alkyl group and / or alkenyl group is preferably 2 or more, and may be 8 or more, or even 12 or more and 18 or less. This is thought to improve the resin flow properties of the resin composition, resulting in improved circuit filling properties when using the resin composition of this embodiment to fabricate a multilayer circuit board or the like.

[0112] In this embodiment, the (meth)acrylic group equivalent of the compound represented by formula (MA) is preferably 1000 g / eq. or less. If the equivalent is 1000 g / eq. or less, a high Tg tends to be more reliably obtained. The lower limit of the (meth)acrylic group equivalent is, for example, 99 g / eq. or more.

[0113] The alkyl group having 1 to 22 carbon atoms is preferably a linear alkyl group having 1 to 22 carbon atoms or a branched alkyl group having 3 to 22 carbon atoms, such as a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, a decyl group, a dodecyl group, a tetradecyl group, a hexadecyl group, an octadecyl group, an eicosyl group, a docosyl group, etc. The alkenyl group having 2 to 22 carbon atoms is preferably an alkenyl group having 2 to 15 carbon atoms, such as an allyl group, a decenyl group, etc.

[0114] Specific examples of the compound represented by formula (MA) include trimethylolpropane trimethacrylate, trimethylolpropane triacrylate, pentaerythritol tetra(meth)acrylate, etc. These may be used alone or in combination of two or more, or may be used as a prepolymer.

[0115] The compound represented by formula (MA) may also be commercially available. Although there is no particular limitation on the commercially available product, an example of the commercially available product is trimethylolpropane trimethacrylate, such as "NK Ester TMPT" manufactured by Shin-Nakamura Chemical Co., Ltd.

[0116] The molecular weight of the polyfunctional (meth)acrylate compound is preferably 200 or more, more preferably 300 or more, and may be 330 or more, 400 or more, or 500 or more. By setting the molecular weight to the above-mentioned lower limit or more, the low dielectric properties (Dk and / or Df) and heat resistance of the obtained cured product tend to be further improved. Furthermore, the molecular weight of the (meth)acrylate compound (preferably a compound represented by formula (MA)) is preferably 3000 or less, more preferably 2000 or less, even more preferably 1000 or less, and even more preferably 800 or less. By setting the molecular weight to the above-mentioned upper limit or less, the low thermal expansion properties of the obtained cured product tend to be further improved.

[0117] In addition to the above, the (meth)acrylate compound may also be a resin having a (meth)acrylic group described in WO 2022 / 210095 (for example, the compounds described in Synthesis Examples 5 and 21 of the same publication) and a resin having a (meth)acrylic group described in Japanese Patent No. 6962507 (for example, the compounds described in Examples 1 to 9), or a compound described in paragraph 0049 of JP-A 2019-194312, the contents of which are incorporated herein by reference.

[0118] When the resin composition of this embodiment contains a (meth)acrylate compound, the content thereof is preferably 1 part by mass or more, more preferably 3 parts by mass or more, even more preferably 5 parts by mass or more, and may be 10 parts by mass or more, per 100 parts by mass of the resin solid content in the resin composition. By setting the content of the polyfunctional (meth)acrylate compound at or above the above-mentioned lower limit, the resin composition tends to have excellent moldability, and the heat resistance and low thermal expansion properties of the obtained cured product tend to be further improved. Furthermore, the upper limit of the content of the (meth)acrylate compound is preferably 40 parts by mass or less, more preferably 30 parts by mass or less, and may be 20 parts by mass or less, per 100 parts by mass of the resin solid content in the resin composition. By setting the content of the (meth)acrylate compound at or below the above-mentioned upper limit, the heat resistance and low dielectric properties (Dk and / or Df) of the obtained cured product tend to be further improved. The resin composition of this embodiment may contain only one type of (meth)acrylate compound, or may contain two or more types. When two or more types are contained, it is preferable that the total amount is within the above-mentioned range.

[0119] <<(Meth)allyl Compound>> The resin composition of this embodiment may contain a (meth)allyl compound. The (meth)allyl compound preferably contains an allyl compound. The (meth)allyl compound is preferably a compound containing two or more (meth)allyl groups, more preferably a compound containing two or more allyl groups. The (meth)allyl compound preferably contains at least one selected from the group consisting of a (meth)allyl isocyanurate compound, a tri(meth)allyl cyanurate compound, a (meth)allyl group-substituted nadimide compound, a (meth)allyl compound having a glycoluril structure, and a diallyl phthalate. More preferably, the (meth)allyl compound contains at least one selected from the group consisting of a (meth)allyl isocyanurate compound, a (meth)allyl group-substituted nadimide compound, and a (meth)allyl compound having a glycoluril structure. Still more preferably, the (meth)allyl isocyanurate compound and / or a (meth)allyl group-substituted nadimide compound is further preferred. Still more preferably, the (meth)allyl group-substituted nadimide compound is further preferred.

[0120] Examples of the tri(meth)allyl cyanurate compound include tri(meth)allyl cyanurate compounds (for example, triallyl cyanurate having the structure shown below). Examples of the (meth)allyl compound include resins having an allyl group described in WO 2022 / 210095 (for example, compounds described in Synthesis Examples 3, 4, 6, 20, and 22 of the same publication), the contents of which are incorporated herein by reference.

[0121] When the resin composition of this embodiment contains a (meth)allyl compound, its molecular weight is preferably 195 or more, more preferably 300 or more, and may be 400 or more, or even 500 or more. By making it equal to or greater than the lower limit, low dielectric properties and heat resistance tend to be further improved. The molecular weight of the (meth)allyl compound is also preferably 3000 or less, more preferably 2000 or less, even more preferably 1000 or less, and even more preferably 800 or less. By making it equal to or less than the upper limit, low thermal expansion tends to be further improved.

[0122] When the resin composition of this embodiment contains a (meth)allyl compound, the content thereof is preferably 1 part by mass or more, more preferably 3 parts by mass or more, even more preferably 5 parts by mass or more, and may even be 10 parts by mass or more, per 100 parts by mass of the resin solid content in the resin composition. By setting the content of the (meth)allyl compound to be equal to or greater than the above-mentioned lower limit, excellent moldability and heat resistance tend to be further improved. Furthermore, the upper limit of the content of the (meth)allyl compound is preferably 40 parts by mass or less, more preferably 30 parts by mass or less, and even more preferably 20 parts by mass or less, per 100 parts by mass of the resin solid content in the resin composition. By setting the content of the (meth)allyl compound to be equal to or less than the above-mentioned upper limit, low thermal expansion tends to be further improved. The resin composition of this embodiment may contain only one type of (meth)allyl compound, or may contain two or more types. When two or more types are contained, the total amount preferably falls within the above-mentioned range.

[0123] <<<(Meth)allyl isocyanurate compound>>> The (meth)allyl isocyanurate compound is not particularly limited as long as it is a compound having two or more (meth)allyl groups and an isocyanurate ring (an isocyanurate skeleton). Because the (meth)allyl isocyanurate compound has a large number of (meth)allyl groups that serve as crosslinking points, it tends to be firmly cured with the resin (A) and the maleimide compound (B), and to produce a cured product with low dielectric properties (Dk and / or Df) and excellent heat resistance. As the (meth)allyl isocyanurate compound, a compound represented by formula (TA) is preferred. Formula (TA) (In formula (TA), R Ａ represents a substituent).

[0124] In formula (TA), R Ａ represents a substituent, and is more preferably a substituent having a formula weight of 15 to 500.

[0125] R Ａ A first example is an alkyl group having 1 to 22 carbon atoms or an alkenyl group having 2 to 22 carbon atoms. By using an allyl compound having an alkyl group having 1 to 22 carbon atoms or an alkenyl group having 2 to 22 carbon atoms, a resin composition can be provided that is excellent in crosslinkability and can yield a cured product with high toughness. This can prevent cracking during etching or other processes, even when the resin composition does not contain a substrate such as glass cloth. From the viewpoint of improving handleability, the number of carbon atoms in the alkyl group and / or alkenyl group is preferably 3 or more, more preferably 8 or more, and may even be 12 or more or 18 or less. This improves the resin flow properties of the resin composition, which is believed to result in improved circuit filling properties when using the resin composition of this embodiment to fabricate a multilayer circuit board or the like.

[0126] R Ａ A second example of R is a group containing an allyl isocyanurate group. Ａ When the compound represented by formula (TA) contains an allyl isocyanurate group, the compound represented by formula (TA) is preferably a compound represented by formula (TA-1). (In formula (TA-1), RＡ２ is a divalent linking group.

[0127] In formula (TA-1), R Ａ２ is preferably a divalent linking group having a formula weight of 54 to 250, more preferably a divalent linking group having a formula weight of 54 to 250 and both ends of which are carbon atoms, and even more preferably an aliphatic hydrocarbon group having 2 to 20 carbon atoms (however, the aliphatic hydrocarbon group may contain an ether group or may have a hydroxyl group). More specifically, R Ａ２ is preferably a group represented by any one of the following formulas (i) to (iii): (In formulas (i) to (iii), p ｃ１ represents the number of repeating methylene units and is an integer of 2 to 18. ｃ２ represents the number of repeating units of the oxyethylene group, and is 0 or 1. * represents a bonding site. ｃ１ is preferably an integer of 2 to 10, more preferably an integer of 3 to 8, and even more preferably an integer of 3 to 5. ｃ２ may be 0 or 1, but is preferably 1.

[0128] R Ａ A third example is a phosphorus-based substituent.

[0129] R Ａ２ is preferably the first example.

[0130] In this embodiment, it is preferable that the reactive group (allyl group) equivalent of the compound represented by formula (TA) is 1000 g / eq. or less. If the equivalent is 1000 g / eq. or less, it is believed that a high Tg can be obtained more reliably.

[0131] Examples of the alkyl group having 1 to 22 carbon atoms include linear or branched alkyl groups, such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, dodecyl, tetradecyl, hexadecyl, octadecyl, eicosyl, and docosyl groups. Examples of the alkenyl group having 2 to 22 carbon atoms include allyl and decenyl groups.

[0132] Specific examples of the compound represented by formula (TA) include triallyl isocyanurate, 5-octyl-1,3-diallyl isocyanurate, 5-dodecyl-1,3-diallyl isocyanurate, 5-tetradecyl-1,3-diallyl isocyanurate, 5-hexadecyl-1,3-diallyl isocyanurate, 5-octadecyl-1,3-diallyl isocyanurate, 5-eicosyl-1,3-diallyl isocyanurate, 5-docosyl-1,3-diallyl isocyanurate, and 5-decenyl-1,3-diallyl isocyanurate. These may be used alone or in combination of two or more, or may be used as a prepolymer.

[0133] The method for producing the compound represented by formula (TA) is not particularly limited, but for example, the compound can be obtained by reacting diallyl isocyanurate with an alkyl halide in an aprotic polar solvent such as N,N'-dimethylformamide, in the presence of a basic substance such as sodium hydroxide, potassium carbonate, or triethylamine, at a temperature of about 60°C to 150°C.

[0134] Furthermore, commercially available compounds represented by formula (TA) can also be used. Commercially available compounds include, but are not limited to, L-DAIC manufactured by Shikoku Chemical Industries Ltd., and P-DAIC having a phosphorus-based substituent manufactured by Shikoku Chemical Industries Ltd. An example of triallyl isocyanurate is TAIC manufactured by Shinryo Corporation. An example of a compound represented by formula (TA-1) is DD-1 manufactured by Shikoku Chemical Industries Ltd.

[0135] The molecular weight of the (meth)allyl isocyanurate compound (preferably a compound represented by formula (TA)) is preferably 200 or more, more preferably 300 or more, and may be 400 or more, or even 500 or more. By setting the molecular weight to be equal to or greater than the above-mentioned lower limit, the low dielectric properties (Dk and / or Df) and heat resistance of the obtained cured product tend to be further improved. Furthermore, the molecular weight of the (meth)allyl isocyanurate compound (preferably a compound represented by formula (TA)) is preferably 3000 or less, more preferably 2000 or less, even more preferably 1000 or less, and even more preferably 800 or less. By setting the molecular weight to be equal to or less than the above-mentioned upper limit, the low thermal expansion properties of the obtained cured product tend to be further improved.

[0136] When the resin composition of this embodiment contains a (meth)allyl isocyanurate compound, the content thereof is preferably 1 part by mass or more, more preferably 3 parts by mass or more, even more preferably 5 parts by mass or more, and may even be 10 parts by mass or more, per 100 parts by mass of the resin solid content in the resin composition. By setting the content of the (meth)allyl isocyanurate compound at or above the above-mentioned lower limit, the resin composition tends to have excellent moldability, and the heat resistance and low thermal expansion properties of the obtained cured product tend to be further improved. Furthermore, the upper limit of the content of the (meth)allyl isocyanurate compound is preferably 40 parts by mass or less, more preferably 30 parts by mass or less, and may even be 20 parts by mass or less, per 100 parts by mass of the resin solid content in the resin composition. By setting the content of the (meth)allyl isocyanurate compound at or below the above-mentioned upper limit, the heat resistance and low dielectric properties (Dk and / or Df) of the obtained cured product tend to be further improved. The resin composition of this embodiment may contain only one type of (meth)allyl isocyanurate compound, or may contain two or more types of (meth)allyl isocyanurate compounds. When two or more types are contained, the total amount is preferably within the above range.

[0137] <<<<(Meth)allyl Group-Substituted Nadimide Compound>>> The (meth)allyl group-substituted nadimide compound is not particularly limited as long as it is a compound having two or more (meth)allyl group-substituted nadimide groups in the molecule. Specific examples include compounds represented by the following formula (AN-1): (In formula (AN-1), R １ each independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms; R ２ represents an alkylene group having 1 to 6 carbon atoms, a phenylene group, a biphenylene group, a naphthylene group, or a group represented by formula (AN-2) or (AN-3). (In formula (AN-2), R ３ represents a methylene group, an isopropylidene group, —C(═O)—, —O—, —S—, or —S(═O) ２ represents a group represented by the formula: (In formula (AN-3), R ４ each independently represents an alkylene group having 1 to 4 carbon atoms or a cycloalkylene group having 5 to 8 carbon atoms.

[0138] Furthermore, commercially available compounds represented by formula (AN-1) can also be used. Examples of commercially available compounds include, but are not limited to, the compound represented by formula (AN-4) (BANI-M (manufactured by Maruzen Petrochemical Co., Ltd.)) and the compound represented by formula (AN-5) (BANI-X (manufactured by Maruzen Petrochemical Co., Ltd.)). These compounds may be used alone or in combination of two or more. Formula (AN-4)

[0139] The molecular weight of the (meth)allyl group-substituted nadimide compound (preferably a compound represented by formula (AN)) is preferably 400 or more, more preferably 500 or more, and may be 550 or more. By setting the molecular weight of the (meth)allyl group-substituted nadimide compound to the above-mentioned lower limit or more, low dielectric properties, low thermal expansion properties, and heat resistance tend to be further improved. The molecular weight of the (meth)allyl group-substituted nadimide compound (preferably a compound represented by formula (AN)) is also preferably 1500 or less, more preferably 1000 or less, even more preferably 800 or less, and may be 700 or less, or 600 or less. By setting the molecular weight of the (meth)allyl group-substituted nadimide compound to the above-mentioned upper limit or less, moldability and peel strength tend to be further improved.

[0140] When the resin composition of the present embodiment contains a (meth)allyl group-substituted nadimide compound (preferably a compound represented by formula (AN)), the content thereof is preferably 1 part by mass or more, more preferably 3 parts by mass or more, even more preferably 5 parts by mass or more, and may even be 10 parts by mass or more, per 100 parts by mass of the resin solid content in the resin composition. By setting the content of the (meth)allyl group-substituted nadimide compound to be equal to or greater than the above-mentioned lower limit, excellent moldability and further improved low dielectric properties, low thermal expansion, and heat resistance tend to be achieved. Furthermore, the upper limit of the content of the (meth)allyl group-substituted nadimide compound (preferably a compound represented by formula (AN)) is preferably 40 parts by mass or less, more preferably 30 parts by mass or less, even more preferably 25 parts by mass or less, and may even be 20 parts by mass or less, per 100 parts by mass of the resin solid content in the resin composition. By setting the content of the (meth)allyl group-substituted nadimide compound to be equal to or less than the above-mentioned upper limit, moldability and peel strength tend to be further improved. The resin composition of the present embodiment may contain only one (meth)allyl group-substituted nadimide compound, or may contain two or more (meth)allyl group-substituted nadimide compounds. When two or more (meth)allyl group-substituted nadimide compounds are contained, the total amount is preferably in the above range.

[0141] <<<<(Meth)allyl Compound Having a Glycoluril Structure>>> The (meth)allyl compound having a glycoluril structure is not particularly limited as long as it is a compound containing a glycoluril structure and two or more (meth)allyl groups. When a (meth)allyl compound having a glycoluril structure is blended into a resin composition, the number of (meth)allyl groups can be increased, that is, the number of crosslinking points can be increased. Therefore, similar to the (meth)allyl isocyanurate compound, it tends to be firmly cured with the resin (A) and the maleimide compound (B), and a cured product with low dielectric properties (Dk and / or Df) and excellent heat resistance can be obtained. In this embodiment, the (meth)allyl compound having a glycoluril structure is preferably a compound represented by formula (GU). Formula (GU) (In formula (GU), R １ are each independently a hydrogen atom or a substituent, and R １ At least two of R are groups containing a (meth)allyl group. ２ each independently represents a hydrogen atom, an alkyl group, or an aryl group. １ are each independently preferably a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, or an alkenyl group having 2 to 5 carbon atoms, more preferably an alkenyl group having 2 to 5 carbon atoms, more preferably a (meth)allyl group, and even more preferably an allyl group. １ In formula (GU), it is preferable that three or four of R are groups containing a (meth)allyl group, and it is more preferable that four of R are groups containing a (meth)allyl group. ２ are each independently preferably a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or a phenyl group, and more preferably a hydrogen atom or a methyl group.

[0142] A specific example of the compound represented by formula (GU) is 1,3,4,6-tetraallylglycoluril (a compound in which all R's in formula (GU) are allyl groups).

[0143] The (meth)allyl compound having a glycoluril structure may be commercially available, and examples thereof include, but are not limited to, TA-G manufactured by Shikoku Chemicals Corporation.

[0144] The molecular weight of the (meth)allyl compound having a glycoluril structure (preferably a compound represented by formula (GU)) is preferably 195 or more, more preferably 220 or more, even more preferably 250 or more, and may be 300 or more, or 400 or more. By setting the molecular weight of the (meth)allyl compound having a glycoluril structure to the above-mentioned lower limit or more, the heat resistance and low thermal expansion of the obtained cured product tend to be further improved. The molecular weight of the (meth)allyl compound having a glycoluril structure (preferably a compound represented by formula (GU)) is also preferably 1500 or less, more preferably 1000 or less, even more preferably 800 or less, and may be 700 or less, or 600 or less. By setting the molecular weight of the (meth)allyl compound having a glycoluril structure to the above-mentioned upper limit or less, the low dielectric properties (Dk and / or Df) and heat resistance of the obtained cured product tend to be further improved.

[0145] When the resin composition of the present embodiment contains a (meth)allyl compound having a glycoluril structure (preferably a compound represented by formula (GU)), the content thereof is preferably 1 part by mass or more, more preferably 3 parts by mass or more, even more preferably 5 parts by mass or more, and may even be 10 parts by mass or more, per 100 parts by mass of the resin solid content in the resin composition. By setting the content of the (meth)allyl compound having a glycoluril structure to be equal to or greater than the above-mentioned lower limit, the resin composition tends to have excellent moldability, and the heat resistance and low thermal expansion of the obtained cured product tend to be further improved. Furthermore, the upper limit of the content of the (meth)allyl compound having a glycoluril structure (preferably a compound represented by formula (GU)) is preferably 40 parts by mass or less, more preferably 30 parts by mass or less, even more preferably 25 parts by mass or less, and may even be 20 parts by mass or less, per 100 parts by mass of the resin solid content in the resin composition. By setting the content of the (meth)allyl compound having a glycoluril structure to be equal to or less than the above-mentioned upper limit, the low dielectric properties (Dk and / or Df) of the obtained cured product tend to be further improved. The resin composition of the present embodiment may contain only one (meth)allyl compound having a glycoluril structure, or may contain two or more (meth)allyl compounds. When two or more compounds are contained, the total amount is preferably in the above range.

[0146] <<Other Compounds Having Two or More Polymerizable Carbon-Carbon Unsaturated Double Bonds>> In addition to the above, examples of compounds having two or more polymerizable carbon-carbon unsaturated double bonds that can be used in the present embodiment include compounds having an indane skeleton with a carbon-carbon unsaturated double bond at its terminal other than the resin (A).

[0147] <Other Thermosetting Compounds> The resin composition of this embodiment may contain other thermosetting compounds in addition to the resin (A), the maleimide compound (B), and the compound having two or more polymerizable carbon-carbon unsaturated double bonds. Examples of such other thermosetting compounds include epoxy compounds, phenolic compounds, oxetane compounds, benzoxazine compounds, arylcyclobutene resins, polyamide compounds, polyimide compounds, cyanate ester compounds, and compounds having a vinylene group. Preferably, the resin composition contains at least one compound selected from the group consisting of a monofunctional vinyl aryl compound, a monofunctional (meth)acrylate compound, and a monofunctional (meth)allyl compound. More preferably, the resin composition contains at least one compound selected from the group consisting of an epoxy compound, a phenolic compound, an oxetane compound, a benzoxazine compound, a cyanate ester compound, and a compound having a vinylene group. It is also preferable to contain at least one compound selected from the group consisting of a monofunctional vinyl aryl compound, a monofunctional (meth)acrylate compound, and a monofunctional (meth)allyl compound.

[0148] The content of these other thermosetting compounds is preferably less than 50 parts by mass, more preferably less than 30 parts by mass, even more preferably less than 10 parts by mass, even more preferably less than 5 parts by mass, and even more preferably less than 3 parts by mass, relative to 100 parts by mass of the resin solid content in the resin composition. It may be less than 1 part by mass, or it may be 0.5 parts by mass or more. The resin composition of this embodiment may contain only one type of other thermosetting compound, or may contain two or more types. When two or more types are contained, it is preferable that the total amount is within the above range.

[0149] <<Epoxy Compound>> The resin composition of this embodiment may contain an epoxy compound. The epoxy compound is not particularly limited as long as it is a compound or resin having one or more epoxy groups (preferably 2 to 12, more preferably 2 to 6, even more preferably 2 to 4, still more preferably 2 or 3, and still more preferably 2) per molecule, and a wide variety of compounds commonly used in the field of printed wiring boards can be used. Examples of the epoxy compound include phenol novolac epoxy resins, bisphenol A novolac epoxy resins, glycidyl ester epoxy resins, aralkyl novolac epoxy resins, biphenyl aralkyl epoxy resins, naphthylene ether epoxy resins, cresol novolac epoxy resins, multifunctional phenol epoxy resins, naphthalene epoxy resins, anthracene epoxy resins, naphthalene skeleton-modified novolac epoxy resins, phenol aralkyl epoxy resins, naphthol aralkyl epoxy resins, dicyclopentadiene epoxy resins, biphenyl epoxy resins, alicyclic epoxy resins, polyol epoxy resins, phosphorus-containing epoxy resins, glycidyl amines, glycidyl esters, compounds in which the double bonds of butadiene or the like have been epoxidized, and compounds obtained by reacting hydroxyl group-containing silicone resins with epichlorohydrin. Use of these compounds improves the moldability and adhesion of the resin composition. Among these, from the viewpoint of further improving flame retardancy and heat resistance, the epoxy compound is preferably one or more selected from the group consisting of biphenylaralkyl epoxy resins, naphthylene ether epoxy resins, polyfunctional phenolic epoxy resins, and naphthalene epoxy resins, and more preferably a biphenylaralkyl epoxy resin.

[0150] When the resin composition of this embodiment contains an epoxy compound, the content thereof is preferably 0.1 parts by mass or more, more preferably 1 part by mass or more, and even more preferably 2 parts by mass or more, relative to 100 parts by mass of the resin solid content in the resin composition. When the epoxy compound content is 0.1 parts by mass or more, the metal foil peel strength and toughness tend to be improved. The upper limit of the epoxy compound content is preferably 50 parts by mass or less, more preferably 30 parts by mass or less, even more preferably 20 parts by mass or less, and even more preferably 10 parts by mass or less, and may be 8 parts by mass or less, or 5 parts by mass or less, relative to 100 parts by mass of the resin solid content in the resin composition. When the epoxy compound content is 50 parts by mass or less, the electrical properties of the resulting cured product tend to be improved. The resin composition of this embodiment may contain only one type of epoxy compound, or may contain two or more types. When two or more types are contained, the total amount is preferably within the above range. The resin composition of this embodiment may also be configured to be substantially free of epoxy compounds. "Substantially free" means that the content of the epoxy compound is less than 0.1 parts by mass, preferably less than 0.01 parts by mass, and may even be less than 0.001 parts by mass, per 100 parts by mass of the resin solid content in the resin composition.

[0151] <<Phenol Compound>> The resin composition of this embodiment may contain a phenolic compound. The phenolic compound is not particularly limited as long as it has one or more phenolic hydroxyl groups (preferably 2 to 12, more preferably 2 to 6, even more preferably 2 to 4, even more preferably 2 or 3, and even more preferably 2) per molecule. A wide variety of compounds commonly used in the field of printed wiring boards can be used. Examples of the phenolic compound include phenol novolac resins, bisphenol A novolac phenolic resins, glycidyl ester phenolic resins, aralkyl novolac phenolic resins, biphenyl aralkyl phenolic resins, cresol novolac phenolic resins, multifunctional phenolic resins, naphthol resins, naphthol novolac resins, multifunctional naphthol resins, anthracene phenolic resins, naphthalene skeleton-modified novolac phenolic resins, phenol aralkyl phenolic resins, naphthol aralkyl phenolic resins, dicyclopentadiene phenolic resins, biphenyl phenolic resins, alicyclic phenolic resins, polyol phenolic resins, phosphorus-containing phenolic resins, and hydroxyl group-containing silicone resins. Among these, from the viewpoint of further improving the flame resistance of the resulting cured product, it is preferable to select at least one selected from the group consisting of biphenyl aralkyl phenolic resins, naphthol aralkyl phenolic resins, phosphorus-containing phenolic resins, and hydroxyl group-containing silicone resins.

[0152] When the resin composition of this embodiment contains a phenolic compound, the content thereof is preferably 0.1 parts by mass or more, more preferably 1 part by mass or more, and even more preferably 2 parts by mass or more, per 100 parts by mass of the resin solid content in the resin composition. The content is preferably 50 parts by mass or less, more preferably 30 parts by mass or less, even more preferably 20 parts by mass or less, still more preferably 10 parts by mass or less, and may even be 5 parts by mass or less. The resin composition of this embodiment may contain only one type of phenolic compound, or may contain two or more types. When two or more types are contained, the total amount is preferably within the above range. The resin composition of this embodiment may also be configured to be substantially free of phenolic compounds. "Substantially free" means that the content of phenolic compounds is less than 0.1 parts by mass per 100 parts by mass of the resin solid content in the resin composition.

[0153] <<Oxetane Compound>> The resin composition of this embodiment may contain an oxetane compound. The oxetane compound is not particularly limited as long as it is a compound having one or more oxetanyl groups (preferably 2 to 12, more preferably 2 to 6, even more preferably 2 to 4, even more preferably 2 or 3, and even more preferably 2), and a wide variety of compounds commonly used in the field of printed wiring boards can be used. Examples of the oxetane compound include oxetane, alkyloxetane (e.g., 2-methyloxetane, 2,2-dimethyloxetane, 3-methyloxetane, 3,3-dimethyloxetane, etc.), 3-methyl-3-methoxymethyloxetane, 3,3-di(trifluoromethyl)oxetane, 2-chloromethyloxetane, 3,3-bis(chloromethyl)oxetane, biphenyl oxetane, OXT-101 (manufactured by Toagosei Co., Ltd.), and OXT-121 (manufactured by Toagosei Co., Ltd.).

[0154] The resin composition of this embodiment preferably contains an oxetane compound to a degree that does not impair the effects of the present invention. When the resin composition of this embodiment contains an oxetane compound, the content thereof is preferably 0.1 parts by mass or more, more preferably 1 part by mass or more, and even more preferably 2 parts by mass or more, per 100 parts by mass of the resin solid content in the resin composition. When the content of the oxetane compound is 0.1 parts by mass or more, the metal foil peel strength and toughness of the resulting cured product tend to be improved. When the resin composition of this embodiment contains an oxetane compound, the upper limit of the content of the oxetane compound is preferably 50 parts by mass or less, more preferably 30 parts by mass or less, even more preferably 20 parts by mass or less, even more preferably 10 parts by mass or less, and even more preferably 8 parts by mass or less, per 100 parts by mass of the resin solid content in the resin composition. When the content of the oxetane compound is 50 parts by mass or less, the electrical properties of the resulting cured product tend to be improved. The resin composition of this embodiment may contain only one oxetane compound, or may contain two or more oxetane compounds. When two or more types are contained, the total amount is preferably in the above range. Furthermore, the resin composition in this embodiment may be configured to be substantially free of oxetane compounds. "Substantially free" means that the content of the oxetane compounds is less than 0.1 parts by mass per 100 parts by mass of the resin solid content in the resin composition.

[0155] <<Benzoxazine Compound>> The resin composition of this embodiment may contain a benzoxazine compound. The benzoxazine compound is not particularly limited as long as it is a compound having two or more (preferably 2 to 12, more preferably 2 to 6, even more preferably 2 to 4, even more preferably 2 or 3, and even more preferably 2) dihydrobenzoxazine rings per molecule, and a wide variety of compounds commonly used in the field of printed wiring boards can be used. Examples of benzoxazine compounds include bisphenol A-type benzoxazine BA-BXZ (manufactured by Konishi Chemical Co., Ltd.), bisphenol F-type benzoxazine BF-BXZ (manufactured by Konishi Chemical Co., Ltd.), and bisphenol S-type benzoxazine BS-BXZ (manufactured by Konishi Chemical Co., Ltd.).

[0156] The resin composition of this embodiment preferably contains a benzoxazine compound to the extent that the effects of the present invention are not impaired. When the resin composition of this embodiment contains a benzoxazine compound, the content thereof is preferably 0.1 parts by mass or more and preferably 50 parts by mass or less per 100 parts by mass of the resin solid content in the resin composition. The resin composition of this embodiment may contain only one type of benzoxazine compound, or may contain two or more types. When two or more types are contained, it is preferable that the total amount is in the above range. Furthermore, the resin composition of this embodiment may be configured to be substantially free of a benzoxazine compound. "Substantially free" means that the content of the benzoxazine compound is less than 0.1 parts by mass per 100 parts by mass of the resin solid content in the resin composition.

[0157] <<Cyanate Ester Compound>> The cyanate ester compound that can be used in the resin composition of this embodiment is not particularly limited as long as it contains one or more (preferably two or more, more preferably 2 to 12, even more preferably 2 to 6, still more preferably 2 to 4, even more preferably 2 or 3, and still more preferably 2) cyanate groups (cyanato groups) in one molecule, and a wide variety of compounds commonly used in the field of printed wiring boards can be used. Furthermore, the cyanate ester compound is preferably a compound in which the cyanate group is directly bonded to an aromatic skeleton (aromatic ring). Examples of the cyanate ester compound include at least one selected from the group consisting of phenol novolac-type cyanate ester compounds, naphthol aralkyl-type cyanate ester compounds (naphthol aralkyl-type cyanates), naphthylene ether-type cyanate ester compounds, biphenyl aralkyl-type cyanate ester compounds, xylene resin-type cyanate ester compounds, trisphenolmethane-type cyanate ester compounds, adamantane skeleton-type cyanate ester compounds, bisphenol M-type cyanate ester compounds, bisphenol A-type cyanate ester compounds, and diallyl bisphenol A-type cyanate ester compounds. Among these, from the viewpoint of further improving the low water absorption of the obtained cured product, at least one selected from the group consisting of phenol novolac cyanate ester compounds, naphthol aralkyl cyanate ester compounds, naphthylene ether cyanate ester compounds, xylene resin cyanate ester compounds, bisphenol M cyanate ester compounds, bisphenol A cyanate ester compounds, and diallyl bisphenol A cyanate ester compounds is preferred, at least one selected from the group consisting of phenol novolac cyanate ester compounds and naphthol aralkyl cyanate ester compounds is more preferred, and naphthol aralkyl cyanate ester compounds are even more preferred. These cyanate ester compounds may be prepared by known methods, or commercially available products may be used.In addition, cyanate ester compounds having a naphthol aralkyl skeleton, a naphthylene ether skeleton, a xylene skeleton, a trisphenolmethane skeleton, or an adamantane skeleton have a relatively large functional group equivalent weight and a small number of unreacted cyanate ester groups, so that cured products of resin compositions using these compounds tend to have even more excellent low water absorption. Furthermore, mainly due to the presence of an aromatic skeleton or an adamantane skeleton, plating adhesion tends to be even more improved.

[0158] As the naphthol aralkyl cyanate ester compound, a compound represented by the following formula (1) is more preferred. (In formula (1), R 3 each independently represents a hydrogen atom or a methyl group, and n3 represents an integer of 1 or greater.

[0159] In formula (1), R 3 each independently represents a hydrogen atom or a methyl group, and among these, a hydrogen atom is preferred. In formula (1), n3 represents an integer of 1 or more, preferably an integer of 1 to 20, more preferably an integer of 1 to 10, and even more preferably an integer of 1 to 6.

[0160] The novolac-type cyanate ester compound is not particularly limited, but is preferably, for example, a compound represented by the following formula (VII). (In formula (VII), R ６ each independently represents a hydrogen atom or a methyl group, and n7 represents an integer of 1 or greater.

[0161] In formula (VII), R ６ each independently represents a hydrogen atom or a methyl group, and among these, a hydrogen atom is preferable. In formula (VII), n7 represents an integer of 1 or more, preferably an integer of 1 to 20, more preferably an integer of 1 to 10, and even more preferably an integer of 1 to 6.

[0162] As the bisphenol A type cyanate ester compound, one or more compounds selected from the group consisting of 2,2-bis(4-cyanatophenyl)propane and prepolymers of 2,2-bis(4-cyanatophenyl)propane may be used.

[0163] The resin composition of this embodiment preferably contains a cyanate ester compound to a degree that does not impair the effects of the present invention. When the resin composition of this embodiment contains a cyanate ester compound, the lower limit of the cyanate ester compound content is preferably 0.1 parts by mass or more, more preferably 2 parts by mass or more, more preferably 5 parts by mass or more, and even more preferably 8 parts by mass or more, per 100 parts by mass of the resin solid content in the resin composition. When the cyanate ester compound content is 0.1 parts by mass or more, the heat resistance, flame resistance, chemical resistance, low dielectric properties (low relative dielectric constant, low dielectric dissipation factor), and insulating properties of the resulting cured product tend to be improved. When the resin composition of this embodiment contains a cyanate ester compound, the upper limit of the cyanate ester compound content is preferably 70 parts by mass or less, more preferably 50 parts by mass or less, even more preferably 40 parts by mass or less, even more preferably 30 parts by mass or less, and even more preferably 20 parts by mass or less, per 100 parts by mass of the resin solid content in the resin composition. The resin composition of this embodiment may contain only one type of cyanate ester compound, or may contain two or more types of cyanate ester compounds. When two or more types are contained, the total amount is preferably within the above range.

[0164] <<Compound Having a Vinylene Group>> The resin composition of this embodiment may contain a compound having a vinylene group. Examples of compounds having a vinylene group include compounds containing one or more -CH=CH- groups in the molecule, and compounds containing one -CH=CH- group in the molecule are preferred. Furthermore, compounds having a vinylene group that also qualify as the maleimide compound (B) are referred to as maleimide compounds. Specific examples of compounds having a vinylene group include acenaphthylene and pyracylene, with acenaphthylene being more preferred. In this specification, compounds that also qualify as compounds having a vinylene group but are explicitly listed as components other than compounds having a vinylene group (e.g., curing accelerators), such as the imidazole compounds described below, are not considered to be compounds having a vinylene group.

[0165] <Filler> The resin composition of this embodiment preferably contains a filler. By including a filler, the dielectric properties (low dielectric constant, low dielectric loss tangent, etc.), flame resistance, low thermal expansion, and other physical properties of the resin composition and its cured product can be further improved. Furthermore, the filler used in this embodiment more preferably has excellent low dielectric properties (Dk and / or Df). For example, the filler used in this embodiment preferably has a relative dielectric constant (Dk) of 8.0 or less, more preferably 6.0 or less, and even more preferably 4.0 or less at a frequency of 10 GHz, as measured according to a cavity resonator perturbation method. Furthermore, a practical lower limit of the relative dielectric constant is, for example, 2.0 or more. Furthermore, the filler used in this embodiment preferably has a dielectric loss tangent (Df) of 0.05 or less, more preferably 0.01 or less at a frequency of 10 GHz, as measured according to a cavity resonator perturbation method. Furthermore, a practical lower limit of the dielectric loss tangent is, for example, 0.0001 or more.

[0166] The filler used in this embodiment is not particularly limited in type, and can suitably be used as the one generally used in this industry.Specifically, silica such as natural silica, fused silica, synthetic silica, amorphous silica, aerosil, hollow silica, alumina, white carbon, titanium white, titanium oxide, zinc oxide, magnesium oxide, zirconium oxide, etc. metal oxide, zinc borate, zinc stannate, forsterite, barium titanate, strontium titanate, calcium titanate, etc. composite oxide, boron nitride, aggregated boron nitride, silicon nitride, aluminum nitride, etc. nitride, aluminum hydroxide, aluminum hydroxide heat treatment product (aluminum hydroxide is heat treated, and part of crystal water is reduced), boehmite, magnesium hydroxide, etc. metal hydroxide (including hydrate), acid Examples of fillers include molybdenum compounds such as molybdenum chloride and zinc molybdate, barium sulfate, clay, kaolin, talc, calcined clay, calcined kaolin, calcined talc, mica, E-glass, A-glass, NE-glass, NER-glass, C-glass, L-glass, D-glass, S-glass, M-glass G20, short glass fibers (including fine glass powders such as E-glass, T-glass, D-glass, S-glass, and Q-glass), hollow glass, and spherical glass, as well as organic fillers such as styrene-type, butadiene-type, and acrylic-type rubber powders, core-shell-type rubber powders, silicone resin powders, silicone rubber powders, and silicone composite powders. In this embodiment, inorganic fillers are preferred, and more preferably contain one or more selected from the group consisting of silica, aluminum hydroxide, talc, aluminum nitride, boron nitride, forsterite, titanium oxide, barium titanate, strontium titanate, and calcium titanate. From the viewpoint of low dielectric properties (Dk and / or Df), more preferably contain one or more selected from the group consisting of silica and aluminum hydroxide, and even more preferably contain silica. The use of these inorganic fillers further improves the properties of the cured product of the resin composition, such as heat resistance, dielectric properties, thermal expansion properties, dimensional stability, and flame retardancy.

[0167] The filler used in the resin composition of this embodiment is preferably an inorganic filler. The inorganic filler used in this embodiment may be treated with a surface treatment agent. The surface treatment agent is preferably a surface treatment agent having at least one selected from the group consisting of an epoxy group, an amino group, and an organic group containing a carbon-carbon unsaturated bond, and CH ２ A surface treatment agent having an organic group containing ═C(X)— (X is a hydrogen atom or a methyl group) is more preferred, a surface treatment agent containing at least one selected from the group consisting of a vinyl group, an allyl group, and a (meth)acryloyl group is even more preferred, and a surface treatment agent containing a vinylsilyl group is even more preferred.

[0168] The surface treatment agent preferably contains a silane coupling agent. By containing a silane coupling agent, the dispersibility of the inorganic filler, the adhesive strength between the resin solid content and the inorganic filler, and the adhesive strength between the inorganic filler and a substrate, which will be described later, tend to be further improved. The silane coupling agent is not particularly limited, and examples include silane coupling agents generally used for the surface treatment of inorganic substances, with silane coupling agents having a carbon-carbon unsaturated bond being more preferred. That is, in this embodiment, an inorganic filler that has been surface-treated with a silane coupling agent having a carbon-carbon unsaturated bond is preferred. More specifically, examples of the silane coupling agent include aminosilane compounds (e.g., γ-aminopropyltriethoxysilane, N-β-(aminoethyl)-γ-aminopropyltrimethoxysilane, etc.), epoxysilane compounds (e.g., γ-glycidoxypropyltrimethoxysilane, etc.), vinylsilane compounds (e.g., vinyltrimethoxysilane, vinyltriethoxysilane, tetravinylsilane, triethylvinylsilane, 1,3-vinyltetramethylsiloxane, etc.), styrylsilane compounds (e.g., 4-vinylphenyltrimethoxysilane, etc.), acrylicsilane compounds (e.g., γ-acryloxypropyltrimethoxysilane, etc.), cationic silane compounds (e.g., N-β-(N-vinylbenzylaminoethyl)-γ-aminopropyltrimethoxysilane hydrochloride, etc.), and phenylsilane compounds. The silane coupling agent preferably contains at least one selected from the group consisting of vinylsilane compounds, styrylsilane compounds, and acrylicsilane compounds, and more preferably a vinylsilane compound. The silane coupling agent may be used alone or in combination of two or more. The content of the compound (c1) (preferably the silane coupling agent) is not particularly limited, but is, for example, 0.1 to 5.0 parts by mass per 100 parts by mass of the resin solid content.

[0169] Usually, the surface treatment agent reacts with the functional group (preferably hydroxyl group) on the surface of the inorganic filler to bond and integrate. Furthermore, when the surface treatment agent and the inorganic filler are reacted in a liquid phase slurry, a part of the surface treatment agent may not be integrated and may exist in the slurry as a free compound. The content of the inorganic filler in the resin composition of this embodiment is the amount including the slurry. The particle diameter (D ５０ ) is preferably 0.1 to 3.0 μm.

[0170] The filler used in this embodiment is preferably blended into the resin composition in any one of the following forms 1 to 4. By using such a configuration, a cured product with superior heat resistance can be obtained.

[0171] In the first embodiment, the filler contains a silica slurry. By using the silica slurry, the silica can be uniformly dispersed in the resin composition, and the silica can also be uniformly dispersed in the resulting cured product.

[0172] In mode 2, the resin composition comprises a compound having two or more polymerizable carbon-carbon unsaturated double bonds and a filler (preferably an inorganic filler), and the mass ratio of the compound having two or more polymerizable carbon-carbon unsaturated double bonds to the filler is 1:1 to 50. By adopting the configuration of mode 2, silica can be uniformly dispersed in the resin composition, and moldability tends to be further improved by increasing the viscosity of the varnish. In mode 2, the mass ratio of the compound having two or more polymerizable carbon-carbon unsaturated double bonds to the filler is preferably 1 or more, more preferably 2 or more, even more preferably 3 or more, even more preferably 4 or more, and even more preferably 5 or more, when the compound having two or more polymerizable carbon-carbon unsaturated double bonds is taken as 1, and may also be 40 or less, more preferably 30 or less, even more preferably 20 or less, even more preferably 10 or less, or even 8 or less.

[0173] In embodiment 3, the resin composition comprises a compound having two or more polymerizable carbon-carbon unsaturated double bonds, the compound having two or more polymerizable carbon-carbon unsaturated double bonds comprises a polyphenylene ether compound represented by formula (OP), and the filler comprises powdered silica. In embodiment 3, by using a compound having two or more polymerizable carbon-carbon unsaturated double bonds, particularly a polyphenylene ether compound represented by formula (OP), it is possible to more easily disperse silica in the resin composition even when powdered silica is used as the filler. (In formula (OP), X represents an aromatic group, and —(Y—O) ｎ１ - represents a polyphenylene ether structure, n1 represents an integer of 1 to 100, and n2 represents an integer of 1 to 4. Rx is a group represented by formula (Rx-1) or formula (Rx-2). (In formula (Rx-1) and formula (Rx-2), R １ , R ２ , and R ３ each independently represents a hydrogen atom, an alkyl group, an alkenyl group, or an alkynyl group. * represents a bonding site with an oxygen atom. Each Mc independently represents a hydrocarbon group having 1 to 12 carbon atoms. z represents an integer of 0 to 4. r represents an integer of 0 to 6.

[0174] In embodiment 4, the resin composition contains a silica slurry and powdered silica as fillers, and further contains a compound having two or more polymerizable carbon-carbon unsaturated double bonds, wherein the compound having two or more polymerizable carbon-carbon unsaturated double bonds contains a polyphenylene ether compound represented by formula (OP). By adopting the configuration of embodiment 4, it is possible to uniformly disperse silica in the resin composition, and by increasing the viscosity of the varnish, moldability tends to be further improved. (In formula (OP), X represents an aromatic group, and —(Y—O) ｎ１ - represents a polyphenylene ether structure, n1 represents an integer of 1 to 100, and n2 represents an integer of 1 to 4. Rx is a group represented by formula (Rx-1) or formula (Rx-2). (In formula (Rx-1) and formula (Rx-2), R １ , R ２, and R ３ each independently represents a hydrogen atom, an alkyl group, an alkenyl group, or an alkynyl group. * represents a bonding site with an oxygen atom. Each Mc independently represents a hydrocarbon group having 1 to 12 carbon atoms. z represents an integer of 0 to 4. r represents an integer of 0 to 6.

[0175] The filler content in the resin composition of this embodiment can be appropriately set depending on the desired properties and is not particularly limited. However, it is preferably 10 parts by mass or more, more preferably 20 parts by mass or more, even more preferably 25 parts by mass or more, even more preferably 30 parts by mass or more, and even more preferably 35 parts by mass or more, relative to 100 parts by mass of the resin solid content in the resin composition. By setting the filler content at or above the lower limit, the resulting cured product tends to have better low thermal expansion and low dielectric loss tangent. Furthermore, the upper limit of the filler content is preferably 1600 parts by mass or less, more preferably 1000 parts by mass or less, even more preferably 500 parts by mass or less, even more preferably 100 parts by mass or less, even more preferably 80 parts by mass or less, and may be 60 parts by mass or less, 50 parts by mass or less, or 40 parts by mass or less, relative to 100 parts by mass of the resin solid content. Setting the filler content at or below the upper limit tends to further improve the moldability of the resin composition. In the resin composition of this embodiment, as an example of a preferred embodiment, the content of the filler is 1 to 95% by mass of the components excluding the solvent, and preferably 30 to 80% by mass. The resin composition of this embodiment may contain only one type of filler, or may contain two or more types. When two or more types are contained, it is preferable that the total amount is in the above range.

[0176] <Elastomer> The resin composition of this embodiment may contain an elastomer. The elastomer may be thermoplastic, thermosetting, or neither thermoplastic nor thermosetting, but is preferably thermoplastic. The elastomer of this embodiment is not particularly limited, and examples thereof include at least one selected from the group consisting of polyisoprene, polybutadiene, styrene butadiene, butyl rubber, ethylene propylene rubber, styrene butadiene ethylene, styrene butadiene styrene, styrene isoprene styrene, styrene ethylene butylene styrene, styrene propylene styrene, styrene ethylene propylene styrene, fluororubber, silicone rubber, hydrogenated compounds thereof, alkyl compounds thereof, and copolymers thereof. Examples of elastomers include oligomers or polymers having a curable vinyl functional group and polybutadiene resins described in paragraphs 0044 and 0045 of JP 2019-194312 A, the contents of which are incorporated herein by reference.

[0177] The number-average molecular weight of the elastomer (preferably a thermoplastic elastomer) used in this embodiment is preferably 1,000 or more. By setting the number-average molecular weight to 1,000 or more, the resulting cured product tends to have better low dielectric properties (Dk and / or Df, particularly low dielectric loss tangent). The number-average molecular weight is preferably 1,500 or more, more preferably 2,000 or more, and may be 600,000 or more, 700,000 or more, or 800,000 or more depending on the application. The upper limit of the number-average molecular weight of the elastomer is preferably 400,000 or less, more preferably 350,000 or less, and even more preferably 300,000 or less. Setting the number-average molecular weight below the upper limit tends to improve the solubility of the elastomer component in the resin composition. When the resin composition of this embodiment contains two or more elastomers, it is preferable that the number-average molecular weight of the mixture thereof falls within the above range.

[0178] The elastomer used in this embodiment may be a resin containing a polybutadiene structure. The polybutadiene structure may be partially or completely hydrogenated. Specific examples include B-1000, B-2000, B-3000, BI-2000, and BI-3000 manufactured by Nippon Soda Co., Ltd., and Ricon 100, Ricon 130, Ricon 131, Ricon 142, Ricon 150, Ricon 181, and Ricon 184 manufactured by CRAY VALLEY.

[0179] The elastomer used in this embodiment may be a resin having a poly(meth)acrylate structure, such as Teisan Resin manufactured by Nagase ChemteX Corporation, and ME-2000, W-197C, KG-15, and KG-3000 manufactured by Negami Chemical Industrial Co., Ltd.

[0180] The elastomer used in this embodiment may be a resin having a polycarbonate structure. Resins having a polycarbonate structure are sometimes referred to as "polycarbonate resins." Examples of such resins include carbonate resins without reactive groups, hydroxyl group-containing carbonate resins, phenolic hydroxyl group-containing carbonate resins, carboxyl group-containing carbonate resins, acid anhydride group-containing carbonate resins, isocyanate group-containing carbonate resins, urethane group-containing carbonate resins, and epoxy group-containing carbonate resins. Here, the term "reactive group" refers to a functional group capable of reacting with other components, such as a hydroxyl group, a phenolic hydroxyl group, a carboxyl group, an acid anhydride group, an isocyanate group, a urethane group, or an epoxy group. Specific examples of polycarbonate resins include FPC0220 and FPC2136 manufactured by Mitsubishi Gas Chemical Company, Inc., and T6002 and T6001 (polycarbonate diol) manufactured by Asahi Kasei Corporation.

[0181] The elastomer used in this embodiment is a resin having a polysiloxane structure, such as SMP-2006, SMP-2003PGMEA, SMP-5005PGMEA, KR-510, and SMP-7014-3S manufactured by Shin-Etsu Silicones Co., Ltd.

[0182] The elastomer used in this embodiment may be a resin having a polyalkylene structure and / or a polyalkyleneoxy structure. The polyalkyleneoxy structure is preferably a polyalkyleneoxy structure having 2 to 15 carbon atoms, more preferably a polyalkyleneoxy structure having 3 to 10 carbon atoms, and particularly preferably a polyalkyleneoxy structure having 5 to 6 carbon atoms. Specific examples of resins having a polyalkylene structure and / or a polyalkyleneoxy structure include PTXG-1000 and PTXG-1800 manufactured by Asahi Kasei Fibers Corporation.

[0183] The elastomer used in this embodiment is a resin having a polyisoprene structure, such as KL-610 and KL613 manufactured by Kuraray Co., Ltd.

[0184] The elastomer used in this embodiment is a resin having a polyisobutylene structure, such as SIBSTAR-073T (styrene-isobutylene-styrene triblock copolymer) and SIBSTAR-042D (styrene-isobutylene diblock copolymer), both manufactured by Kaneka Corporation.

[0185] In this embodiment, the elastomer is preferably an elastomer containing styrene monomer units and conjugated diene monomer units (hereinafter referred to as "elastomer (e)"). By using such elastomer (e), the low dielectric properties (Dk and / or Df, particularly low dielectric loss tangent) of the resulting cured product are more excellent.

[0186] The elastomer (e) contains a styrene monomer unit. The inclusion of the styrene monomer unit improves the solubility of the elastomer (e) in the resin composition. 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, styrene, α-methylstyrene, and p-methylstyrene are preferred from the standpoints of availability and productivity. Of these, styrene is particularly preferred. The content of the styrene monomer unit in the elastomer (e) is preferably 10% by mass or more, more preferably 13% by mass or more, and even more preferably 15% by mass or more, of the total monomer units, and is preferably 50% by mass or less, more preferably 45% by mass or less, and even more preferably 40% by mass or less. By ensuring that the content of the styrene monomer unit is equal to or less than the above upper limit, adhesion and tackiness to substrates and the like are improved. Furthermore, when the content of the styrene monomer unit is equal to or greater than the lower limit, the adhesion can be suppressed, adhesive residue and stop marks are less likely to occur, and the adhesive surfaces tend to be easily peeled from each other, which is preferable. The elastomer (e) may contain only one type of styrene monomer unit, or may contain two or more types. When two or more types are contained, it is preferable that the total amount is within the above range. The method for measuring the content of the styrene monomer unit in the elastomer (e) 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 and the like described below.

[0187] The elastomer (e) contains a conjugated diene monomer unit. The inclusion of the conjugated diene monomer unit improves the solubility of the elastomer (e) in a resin composition. The conjugated diene monomer is not particularly limited as long as it is a diolefin having one pair of conjugated double bonds. Examples of the conjugated diene monomer 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. The elastomer (e) may contain only one type of conjugated diene monomer unit, or may contain two or more types.

[0188] In the elastomer (e), the mass ratio of the styrene monomer units to the conjugated diene monomer units (styrene monomer units / conjugated diene monomer units) is preferably in the range of 5 / 95 to 80 / 20, more preferably 7 / 93 to 77 / 23, and even more preferably 10 / 90 to 70 / 30. When the mass ratio of the styrene polymer units to the conjugated diene monomer units is in the range of 5 / 95 to 80 / 20, it is possible to suppress the increase in adhesion, maintain high adhesive strength, and improve the ease of peeling between adhesive surfaces.

[0189] The conjugated diene bonds of the elastomer (e) may be entirely hydrogenated, partially hydrogenated, or not hydrogenated at all.

[0190] The elastomer (e) may or may not contain other monomer units in addition to the styrene monomer units and the conjugated diene monomer units. Examples of other monomer units include aromatic vinyl compound units other than styrene monomer units. The total of the styrene monomer units and the conjugated diene monomer units in the elastomer (e) is preferably 90% by mass or more, more preferably 95% by mass or more, even more preferably 97% by mass or more, and even more preferably 99% by mass or more, of the total monomer units. As described above, the elastomer (e) may contain only one type of styrene monomer unit and one type of conjugated diene monomer unit, or two or more types. When two or more types are contained, the total amount is preferably within the above range.

[0191] The elastomer (e) used in this embodiment may be a block polymer or a random polymer. It may be a hydrogenated elastomer in which the conjugated diene monomer units are hydrogenated, an unhydrogenated elastomer in which no hydrogenation is performed, or a partially hydrogenated elastomer in which only a portion of the conjugated diene monomer units are hydrogenated. An unhydrogenated elastomer or a partially hydrogenated elastomer is preferred. In one embodiment of this embodiment, the elastomer (e) is a hydrogenated elastomer. Here, the term "hydrogenated elastomer" refers to an elastomer in which the double bonds based on the conjugated diene monomer units in the elastomer are hydrogenated, and includes elastomers with a hydrogenation rate (hydrogenation rate) of 80% or more as well as elastomers with a hydrogenation rate (hydrogenation rate) of 100%. The hydrogenation rate of the hydrogenated elastomer is preferably 85% or more, more preferably 90% or more, and even more preferably 95% or more. In this embodiment, the hydrogenation rate is 1It is calculated from the results of H-NMR spectrum measurement. In one embodiment of this embodiment, the elastomer (e) is an unhydrogenated elastomer. Here, the unhydrogenated elastomer refers to an elastomer in which the proportion of hydrogenated double bonds based on conjugated diene monomer units in the elastomer, i.e., the hydrogenation rate (hydrogenation rate) is 20% or less. The hydrogenation rate is preferably 15% or less, more preferably 10% or less, and even more preferably 5% or less. On the other hand, a partially hydrogenated elastomer refers to an elastomer in which some of the double bonds based on conjugated diene monomer units in the elastomer are hydrogenated, and typically refers to an elastomer in which the hydrogenation rate (hydrogenation rate) is less than 80% but more than 20%.

[0192] Examples of commercially available elastomers (e) used in this embodiment include SEPTON (registered trademark) 2104, V9461, and S8104 manufactured by Kuraray Co., Ltd., S.O.E. (registered trademark) S1606, S1613, S1609, and S1605 manufactured by Asahi Kasei Corporation, Tuftec (registered trademark) H1041, H1043, P2000, and MP10 manufactured by Asahi Kasei Corporation, and DYNARON (registered trademark) 9901P and TR2250 manufactured by JSR Corporation.

[0193] The elastomer used in this embodiment may also be a liquid diene. Liquid diene refers to a liquid elastomer containing a conjugated diene monomer unit. 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. Examples of liquid dienes used in this embodiment include liquid polybutadiene, liquid polyisoprene, modified liquid polybutadiene, modified liquid polyisoprene, liquid acrylonitrile-butadiene copolymer, and liquid styrene-butadiene copolymer. The number average molecular weight of the liquid diene is not particularly limited as long as it is liquid at 20°C, but is preferably 500 or more and 10,000 or less.

[0194] When the resin composition of this embodiment contains an elastomer (preferably, elastomer (e)), the content thereof is preferably 1 part by mass or more, more preferably 5 parts by mass or more, and even more preferably 8 parts by mass or more, per 100 parts by mass of the resin solid content in the resin composition. Depending on the application, the content may be 10 parts by mass or more, or 12 parts by mass or more. By setting the content at or above the lower limit, the dielectric properties (low dielectric tangent) tend to be further improved. Furthermore, the upper limit of the elastomer content is preferably 45 parts by mass or less, more preferably 40 parts by mass or less, even more preferably 35 parts by mass or less, even more preferably 32 parts by mass or less, and even more preferably 28 parts by mass or less, per 100 parts by mass of the resin solid content in the resin composition. By setting the content at or below the upper limit, the heat resistance tends to be further improved. The resin composition of this embodiment may contain only one type of elastomer, or may contain two or more types. When two or more types of elastomers are contained, the total amount is preferably within the above range. Furthermore, the resin composition of this embodiment may be configured to be substantially free of elastomer. "Substantially free" means that the content of elastomer is less than 1 part by mass, preferably less than 0.1 part by mass, and more preferably less than 0.01 part by mass, per 100 parts by mass of the resin solid content in the resin composition.

[0195] <Curing Accelerator> The resin composition of the present embodiment may further contain a curing accelerator. The curing accelerator is not particularly limited, and examples thereof include imidazoles such as 2-ethyl-4-methylimidazole and triphenylimidazole; organic peroxides such as benzoyl peroxide, lauroyl peroxide, acetyl peroxide, parachlorobenzoyl peroxide, di-tert-butyl-di-perphthalate, α,α'-di(t-butylperoxy)diisopropylbenzene, 2,5-dimethyl-2,5-di(t-butylperoxy)hexane, and 2,5-dimethyl-2,5-bis(t-butylperoxy)hexyne-3; azo compounds such as azobisnitrile; N,N-dimethylbenzylamine, N,N-dimethylaniline, N,N-dimethyltoluidine, 2-N-ethylanilinoethanol, tri-n-butylamine, pyridine, quinoline, and N-methylmorpholine. tertiary amines such as triethanolamine, triethylenediamine, tetramethylbutanediamine, and N-methylpiperidine; phenols such as phenol, xylenol, cresol, resorcinol, and catechol; high-temperature decomposition type radical generators such as 2,3-dimethyl-2,3-diphenylbutane; organic metal salts such as lead naphthenate, lead stearate, zinc naphthenate, zinc octylate, manganese octylate, tin oleate, dibutyltin maleate, manganese naphthenate, cobalt naphthenate, and iron acetylacetonate; compounds obtained by dissolving these organic metal salts in hydroxyl group-containing compounds such as phenol and bisphenol; inorganic metal salts such as tin chloride, zinc chloride, and aluminum chloride; and organic tin compounds such as dioctyltin oxide, other alkyl tins, and alkyl tin oxides. Among these, preferred curing accelerators are imidazoles, organic metal salts, and organic peroxides, with imidazoles and organic peroxides being more preferred.

[0196] When the resin composition of this embodiment contains a curing accelerator, the lower limit of its content is preferably 0.005 parts by mass or more, more preferably 0.01 parts by mass or more, and even more preferably 0.1 parts by mass or more, per 100 parts by mass of the resin solid content in the resin composition. The upper limit of the curing accelerator content is preferably 10 parts by mass or less, more preferably 5 parts by mass or less, even more preferably 3 parts by mass or less, even more preferably 2 parts by mass or less, even more preferably 1.5 parts by mass or less, even more preferably 1.0 parts by mass or less, even more preferably 0.8 parts by mass or less, and even more preferably 0.7 parts by mass or less, per 100 parts by mass of the resin solid content in the resin composition. The resin composition of this embodiment is preferable because the resin composition can be sufficiently cured even when the content of the curing accelerator is 0.8 parts by mass or less. The curing accelerators can be used alone or in combination of two or more. When two or more types are used, the total amount falls within the above range.

[0197] <Flame Retardant> The resin composition of this embodiment may contain a flame retardant. Examples of flame retardants include phosphorus-based flame retardants, halogen-based flame retardants, inorganic flame retardants, and silicone-based flame retardants, with phosphorus-based flame retardants being preferred. Known flame retardants can be used, including, for example, halogen-based flame retardants such as brominated epoxy resin, brominated polycarbonate, brominated polystyrene, brominated styrene, brominated phthalimide, tetrabromobisphenol A, pentabromobenzyl (meth)acrylate, pentabromotoluene, tribromophenol, hexabromobenzene, decabromodiphenyl ether, bis-1,2-pentabromophenylethane, chlorinated polystyrene, and chlorinated paraffin; red phosphorus; tricresyl phosphate; triphenyl phosphate; and cresyl diphenyl phosphate. Examples of suitable flame retardants include phosphorus-based flame retardants such as phosphate, trixylenyl phosphate, trialkyl phosphate, dialkyl phosphate, tris(chloroethyl)phosphate, phosphazene, 1,3-phenylenebis(2,6-dixylenyl phosphate), and 10-(2,5-dihydroxyphenyl)-10H-9-oxa-10-phosphaphenanthrene-10-oxide; inorganic flame retardants such as aluminum hydroxide, magnesium hydroxide, partial boehmite, boehmite, zinc borate, and antimony trioxide; and silicone-based flame retardants such as silicone rubber and silicone resin. In this embodiment, of these, 1,3-phenylenebis(2,6-dixylenyl phosphate) is preferred because it does not impair the low dielectric properties (Dk and / or Df).

[0198] When the resin composition of this embodiment contains a flame retardant, the content thereof is preferably 1 part by mass or more, more preferably 2 parts by mass or more, and even more preferably 3 parts by mass or more, per 100 parts by mass of the resin solid content in the resin composition. The lower limit of the content of the flame retardant is preferably 30 parts by mass or less, more preferably 20 parts by mass or less, and even more preferably 10 parts by mass or less, per 100 parts by mass of the resin solid content in the resin composition. The flame retardants can be used alone or in combination of two or more. When two or more types are used, the total amount falls within the above range.

[0199] <Active ester compound> The resin composition of the present embodiment may contain an active ester compound within a range that does not impair the effects of the present invention. The active ester compound is not particularly limited, and for example, the description in paragraphs 0064 to 0066 of WO 2021 / 172317 can be referred to, the contents of which are incorporated herein by reference.

[0200] When the resin composition of this embodiment contains an active ester compound, the amount is preferably 1 part by mass or more and preferably 50 parts by mass or less per 100 parts by mass of the resin solid content in the resin composition. The resin composition of this embodiment may contain only one type of active ester compound, or may contain two or more types. When two or more types are contained, it is preferable that the total amount is in the above range. Furthermore, the resin composition of this embodiment may be configured to be substantially free of an active ester compound. "Substantially free" means that the content of the active ester compound 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 per 100 parts by mass of the resin solid content in the resin composition.

[0201] <Aromatic Oligomer> The resin composition of this embodiment may contain an aromatic oligomer. The aromatic oligomer is an oligomer having a structural unit derived from an aromatic vinyl compound, and typically refers to a compound having a weight-average molecular weight of less than 3,000. The aromatic oligomer is also typically a thermoplastic oligomer. Note that the aromatic oligomer in this embodiment does not include compounds explicitly listed in any of the above items, such as polymers having a structural unit represented by formula (V) or thermoplastic elastomers. Examples of the aromatic vinyl compounds include styrene, α-methylstyrene, 2-methylstyrene, 3-methylstyrene, 4-methylstyrene, 4-propylstyrene, 4-t-butylstyrene, 4-cyclohexylstyrene, 4-dodecylstyrene, 2,4-dimethylstyrene, 2,4-diisopropylstyrene, 2,4,6-trimethylstyrene, 2-ethyl-4-benzylstyrene, 4-(phenylbutyl)styrene, 1-vinylnaphthalene, 2-vinylnaphthalene, vinylanthracene, N,N-diethyl-4-aminoethylstyrene, vinylpyridine, 4-methoxystyrene, monochlorostyrene, dichlorostyrene, and divinylbenzene. These aromatic vinyl compounds may be used alone or in combination of two or more. Among these, styrene, α-methylstyrene, and 4-methylstyrene are preferred, and α-methylstyrene is more preferred.

[0202] The aromatic oligomer may contain a constituent unit derived from a monomer other than an aromatic vinyl compound, such as (meth)acrylic acid, a (meth)acrylic acid derivative, (meth)acrylamide, a (meth)acrylamide derivative, (meth)acrylonitrile, isoprene, 1,3-butadiene, ethylene, vinyl acetate, vinyl chloride, vinylidene chloride, N-vinylindole, N-vinylphthalimide, N-vinylpyrrolidone, N-vinylcarbazole, or N-vinylcaprolactam.

[0203] The content of structural units derived from aromatic vinyl compounds in the aromatic oligomer is preferably 60% by mass or more, more preferably 70% by mass or more, even more preferably 80% by mass or more, still more preferably 90% by mass or more, and even more preferably 95% by mass or more.

[0204] The weight average molecular weight (Mw) of the aromatic oligomer is preferably 300 or more, more preferably 500 or more, and even more preferably 1,000 or more, and is usually less than 3,000, preferably 2,800 or less, more preferably 2,500 or less, and may be 2,000 or less. The weight average molecular weight (Mw) of the aromatic oligomer is a value determined by gel permeation chromatography in terms of standard polystyrene.

[0205] Examples of aromatic oligomers include polystyrene, poly-α-methylstyrene, poly-4-methylstyrene, styrene / α-methylstyrene copolymer, styrene / 4-methylstyrene copolymer, α-methylstyrene / 4-methylstyrene copolymer, and styrene / α-methylstyrene / 4-methylstyrene copolymer. One type of aromatic oligomer may be used alone, or two or more types may be used in combination.

[0206] Commercially available aromatic oligomers may be used. Examples of commercially available aromatic oligomers include Picolastic A5 (polystyrene, softening point 5°C, Mw 350), Picolastic A-75 (polystyrene, softening point 74°C, Mw 1300), Picotex 75 (α-methylstyrene / 4-methylstyrene copolymer, softening point 75°C, Mw 1100), Picotex LC (α-methylstyrene / 4-methylstyrene copolymer, softening point 91°C, Mw 1350), and Crystalle EASTMAN aromatic polymers such as KRYSTALEX 3070 (styrene / α-methylstyrene copolymer, softening point 70°C, Mw 950), KRYSTALEX 3085 (styrene / α-methylstyrene copolymer, softening point 85°C, Mw 1150), and KRYSTALEX 3100 (styrene / α-methylstyrene copolymer, softening point 100°C, Mw 1500); YS RESIN SX-100 (polystyrene, softening point 100°C, Mw 2500); FMR-0150 (styrene / aromatic hydrocarbon copolymer, softening point 145°C, Mw 2040; manufactured by Mitsui Chemicals), FTR-6100 (styrene / aliphatic hydrocarbon copolymer, softening point 95°C, Mw 1210; manufactured by Mitsui Chemicals), FTR-6110 (styrene / aliphatic hydrocarbon copolymer, softening point 110°C, Mw 1570; manufactured by Mitsui Chemicals), FTR-6125 (styrene / aliphatic hydrocarbon copolymer, softening point 110°C, Mw 1570; manufactured by Mitsui Chemicals), Examples of suitable aromatic oligomers include FTR-7100 (styrene / α-methylstyrene / aliphatic hydrocarbon copolymer, softening point 100°C, Mw 1440; manufactured by Mitsui Chemicals), FTR-0100 (poly-α-methylstyrene, softening point 100°C, Mw 1960; manufactured by Mitsui Chemicals), and FTR-2120 (styrene / α-methylstyrene copolymer, softening point 120°C, Mw 2630; manufactured by Mitsui Chemicals). In addition to the above, examples of suitable aromatic oligomers include those described in paragraphs 0069 to 0087 of WO 2017 / 135168, which correspond to the aromatic oligomers. The contents of these paragraphs are incorporated herein by reference.

[0207] When the resin composition of this embodiment contains an aromatic oligomer, the content thereof is preferably 1 part by mass or more, more preferably 2 parts by mass or more, even more preferably 3 parts by mass or more, and may even be 4 parts by mass or more, per 100 parts by mass of the resin solid content. By setting the content at or above the lower limit, the relative dielectric constant and dielectric loss tangent tend to be further reduced. Furthermore, the upper limit of the aromatic oligomer content is preferably 45 parts by mass or less, more preferably 30 parts by mass or less, even more preferably 15 parts by mass or less, even more preferably 10 parts by mass or less, and may even be 8 parts by mass or less, per 100 parts by mass of the resin solid content. By setting the content at or below the upper limit, chemical resistance tends to be further improved. The resin composition of this embodiment may contain only one type of aromatic oligomer, or may contain two or more types. When two or more types are contained, the total amount preferably falls within the above range.

[0208] <Dispersant> The resin composition of this embodiment may contain a dispersant. As the dispersant, those generally used for paints can be suitably used, and the type is not particularly limited. As the dispersant, a copolymer-based wetting dispersant is preferably used, and specific examples thereof include DISPERBYK (registered trademark)-110, 111, 161, 180, 2009, 2152, 2155, BYK (registered trademark)-W996, W9010, W903, and W940, manufactured by BYK Japan K.K.

[0209] When the resin composition of this embodiment contains a dispersant, the lower limit of the content is preferably 0.01 parts by mass or more, more preferably 0.1 parts by mass or more, and may be 0.3 parts by mass or more, per 100 parts by mass of the resin solid content in the resin composition. The upper limit of the dispersant content is preferably 10 parts by mass or less, more preferably 5 parts by mass or less, and may be 3 parts by mass or less, per 100 parts by mass of the resin solid content in the resin composition. The dispersants can be used alone or in combination of two or more. When two or more types are used, the total amount falls within the above range.

[0210] <Solvent> The resin composition of this embodiment may contain a solvent, and preferably contains an organic solvent. When a solvent is contained, the resin composition of this embodiment is in a form (solution or varnish) in which at least a portion, preferably all, of the various resin solid components described above are dissolved or compatible in the solvent. The solvent is not particularly limited as long as it is a polar organic solvent or a non-polar organic solvent that can dissolve or compatible at least a portion, preferably all, of the various resin solid components described above. Examples of polar organic solvents include ketones (e.g., acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, etc.), cellosolves (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 amides (e.g., dimethoxyacetamide, dimethylformamide, etc.). Examples of non-polar organic solvents include aromatic hydrocarbons (e.g., toluene, xylene, etc.). The solvents may be used alone or in combination of two or more. When two or more solvents are used, the total amount falls within the above range.

[0211] <Other Components> In addition to the above components, the resin composition of this embodiment may contain various polymeric compounds such as thermoplastic resins and their oligomers, petroleum resins, and various additives. Examples of additives include ultraviolet absorbers, antioxidants, photopolymerization initiators, fluorescent brighteners, photosensitizers, dyes, pigments, thickeners, flow modifiers, lubricants, antifoaming agents, leveling agents, gloss agents, and polymerization inhibitors. These additives can be used alone or in combination of two or more. In one example of this embodiment, the resin (A), the maleimide compound (B), and the polymer having a structural unit represented by formula (V), the flame retardant, and the polyphenylene ether compound represented by formula (OP), which are blended as needed, account for 90% by mass or more of the total resin solids, more preferably 95% by mass or more, and even more preferably 98% by mass or more.

[0212] <Applications> The resin composition of this embodiment is used as a cured product. Specifically, the resin composition of this embodiment can be suitably used as a low-dielectric-constant material and / or a low-dielectric-tangent material, such as an insulating layer for a printed wiring board, a semiconductor package material, or other electronic material resin composition. The resin composition of this embodiment can be suitably used as a material for a prepreg, a metal foil-clad laminate using a prepreg, a resin composite sheet, and a printed wiring board.

[0213] The resin composition of this embodiment preferably has a low dielectric constant (Dk) and dielectric loss tangent (Df) when cured. Specifically, when molded into a 1.0 mm thick cured plate, the dielectric constant (Dk) at a frequency of 10 GHz measured according to the cavity resonator perturbation method is preferably 2.85 or less. The lower limit of the dielectric constant (Dk) is not particularly specified, but a practical value is, for example, 0.01 or more. Furthermore, when molded into a 1.0 mm thick cured plate, the dielectric loss tangent (Df) at a frequency of 10 GHz measured according to the cavity resonator perturbation method is preferably 0.0022 or less. The lower limit of the dielectric loss tangent (Df) is not particularly specified, but a practical value is, for example, 0.0001 or more. More specifically, the dielectric constant (Dk) and dielectric loss tangent (Df) of the cured plate are measured by the method described in the Examples below. The resin composition of this embodiment preferably has a high glass transition temperature when cured. Specifically, the glass transition temperature of the cured product of the resin composition of the present embodiment is preferably 233°C or higher, more preferably 240°C or higher, even more preferably 245°C or higher, and even more preferably 250°C or higher, and practically 300°C or lower.

[0214] The resin composition of this embodiment is used as a layered material (including film and sheet forms) such as a prepreg or resin composite sheet that serves as an insulating layer for a printed wiring board. When used as such a layered material, the thickness is preferably 5 μm or more, more preferably 10 μm or more. The upper limit of the thickness is preferably 200 μm or less, more preferably 180 μm or less. Note that the thickness of the layered material refers to the thickness including the glass cloth, for example, when the resin composition of this embodiment is impregnated into glass cloth or the like. Materials formed from the resin composition of this embodiment may be used in applications where a pattern is formed by exposure and development, or in applications where exposure and development are not required. They are particularly suitable for applications where exposure and development are not required.

[0215] <<Prepreg>> The prepreg of this embodiment is formed from a substrate (prepreg substrate) and the resin composition of this embodiment. The prepreg of this embodiment can be obtained, for example, by applying the resin composition of this embodiment to the substrate (e.g., by impregnation and / or coating) and then semi-curing by heating (e.g., by drying at 120 to 220°C for 2 to 15 minutes). In this case, the amount of resin composition attached to the substrate, i.e., the amount of resin composition (including filler) relative to the total amount of semi-cured prepreg, is preferably in the range of 20 to 99% by mass, and more preferably in the range of 20 to 80% by mass.

[0216] The substrate is not particularly limited as long as it is a substrate used in various printed wiring board materials. Examples of the substrate material include glass fibers (e.g., E-glass, D-glass, L-glass, S-glass, T-glass, Q-glass, UN-glass, NE-glass, NER-glass, spherical glass, etc.), inorganic fibers other than glass (e.g., quartz, etc.), and organic fibers (e.g., polyimide, polyamide, polyester, liquid crystal polyester, polytetrafluoroethylene, etc.). The form of the substrate is not particularly limited, and examples include woven fabric, nonwoven fabric, roving, chopped strand mat, surfacing mat, etc. These substrates may be used alone or in combination of two or more. Among these substrates, from the viewpoint of dimensional stability, woven fabrics that have been subjected to an ultra-opening treatment and a clogging treatment are preferred. From the viewpoint of strength and low water absorption, the substrate should have a thickness of 200 μm or less and a mass of 250 g / m ２ The following glass woven fabrics are preferred, and from the viewpoint of moisture absorption and heat resistance, glass woven fabrics that have been surface-treated with a silane coupling agent such as epoxy silane or amino silane are preferred. From the viewpoint of electrical properties, low-dielectric glass cloths made of glass fibers exhibiting a low relative dielectric constant and low dielectric dissipation factor, such as L-glass, NE-glass, NER-glass, and Q-glass, are more preferred. Examples of substrates with a low relative dielectric constant include substrates with a relative dielectric constant of 5.0 or less (preferably 3.0 to 4.9). Examples of substrates with a low dielectric dissipation factor include substrates with a dielectric dissipation factor of 0.006 or less (preferably 0.001 to 0.005). The relative dielectric constant and dielectric dissipation factor are values ​​measured at a frequency of 10 GHz using a perturbation method cavity resonator.

[0217] <<Metal Foil-Clad Laminate>> The metal foil-clad laminate of this embodiment includes at least one layer formed from the prepreg of this embodiment and a metal foil disposed on one or both sides of the layer formed from the prepreg. Examples of methods for producing the metal foil-clad laminate of this embodiment include a method in which at least one prepreg of this embodiment (preferably two or more prepregs) is disposed, and a metal foil is disposed on one or both sides of the prepreg, followed by laminate molding. More specifically, the laminate can be produced by disposing a metal foil, such as copper or aluminum, on one or both sides of the prepreg and then laminating the prepreg. The number of prepregs is preferably 1 to 10, more preferably 2 to 10, and even more preferably 2 to 9. The metal foil may be any foil suitable for use in printed wiring boards, including, but not limited to, copper foils such as rolled copper foil and electrolytic copper foil. The thickness of the metal foil (preferably, copper foil) is not particularly limited and may be approximately 1.5 to 70 μm. Furthermore, when copper foil is used as the metal foil, the copper foil preferably has a surface roughness Rz of 0.2 to 4.0 μm, as measured in accordance with JIS B0601:2013. By adjusting the surface roughness Rz to 0.2 μm or more, the copper foil surface roughness becomes appropriate, and the copper foil peel strength tends to be further improved. On the other hand, by adjusting the surface roughness Rz to 4.0 μm or less, the copper foil surface roughness becomes appropriate, and the dielectric loss tangent characteristics of the resulting cured product tend to be further improved. From the viewpoint of reducing the dielectric loss tangent, the surface roughness Rz of the copper foil is more preferably 0.5 μm or more, even more preferably 0.6 μm or more, particularly preferably 0.7 μm or more, and more preferably 3.5 μm or less, even more preferably 3.0 μm or less, and particularly preferably 2.0 μm or less.

[0218] Examples of laminate molding methods include those commonly used when molding printed wiring board laminates and multilayer boards. More specifically, examples include methods using a multi-stage press, multi-stage vacuum press, continuous molding machine, autoclave molding machine, or the like, at a temperature of about 180 to 350°C, a heating time of about 100 to 300 minutes, and a surface pressure of about 1 to 10 MPa. A multilayer board can also be produced by combining the prepreg of this embodiment with a separately prepared inner layer wiring board for laminate molding. A multilayer board can be produced, for example, by placing copper foil of about 35 μm on both sides of a single prepreg of this embodiment, laminating using the molding method described above, forming an inner layer circuit, and blackening this circuit to form an inner layer circuit board. Then, this inner layer circuit board and the prepreg of this embodiment are alternately arranged one by one, and copper foil is placed on the outermost layer. This laminate molding can be carried out under the above conditions, preferably under vacuum, to produce a multilayer board. The metal foil-clad laminate of this embodiment can be suitably used as a printed wiring board.

[0219] The metal foil-clad laminate of this embodiment preferably has a peel strength of 0.28 kN / m or more, more preferably 0.38 kN / m or more, and even more preferably 0.50 kN / m or more, measured in accordance with the provisions of 5.7 "Peel Strength" of JIS C6481. There is no particular upper limit to the peel strength, but even if it is 2.00 kN / m or less, the required performance is sufficiently met.

[0220] As described above, the resin composition for electronic materials obtained using the resin composition of the present embodiment (a resin composition including a combination of specific components) can provide a cured product that has low dielectric properties (low dielectric constant, low dielectric dissipation factor, particularly low dielectric constant), moisture absorption heat resistance, peel strength against metal foil, as well as excellent properties such as heat resistance, desmear resistance, crack resistance, cured product appearance, and low thermal expansion.

[0221] <<Printed Wiring Board>> The printed wiring board of this embodiment includes an insulating layer and a conductor layer disposed on the surface of the insulating layer, wherein the insulating layer includes at least one of a layer formed from the resin composition of this embodiment and a layer formed from the prepreg of this embodiment. Such a printed wiring board can be manufactured using conventional methods, and the manufacturing method is not particularly limited. An example of a method for manufacturing a printed wiring board is described below. First, a metal foil-clad laminate, such as the copper foil-clad laminate described above, is prepared. Next, the surface of the metal foil-clad laminate is etched to form an inner layer circuit, thereby producing an inner layer substrate. If necessary, the surface of the inner layer circuit of this inner layer substrate is subjected to a surface treatment to increase adhesive strength. Next, a required number of the prepregs described above are stacked on the surface of the inner layer circuit, and metal foil for an outer layer circuit is further laminated on the outside, followed by heating and pressurizing to form an integral mold. In this way, a multilayer laminate is manufactured, in which an insulating layer composed of a substrate and a cured product of the resin composition is formed between the inner layer circuit and the metal foil for the outer layer circuit. Next, this multilayer laminate is subjected to drilling processing for through holes and via holes, and then a plated metal film is formed on the wall surface of the hole to provide electrical continuity between the inner layer circuit and the metal foil for the outer layer circuit.The metal foil for the outer layer circuit is then etched to form the outer layer circuit, thereby producing a printed wiring board.

[0222] The printed wiring board obtained in the above manufacturing example has an insulating layer and a conductor layer formed on the surface of this insulating layer, and the insulating layer contains the resin composition of the present embodiment described above and / or its cured product. That is, the prepreg of the present embodiment described above (for example, a prepreg formed from a base material and the resin composition of the present embodiment impregnated or applied thereto), or the layer formed from the resin composition of the metal foil-clad laminate of the present embodiment described above, serves as the insulating layer of the present embodiment. This embodiment also relates to a semiconductor device including the printed wiring board. For details of the semiconductor device, please refer to paragraphs 0200 to 0202 of JP 2021-021027 A, the contents of which are incorporated herein by reference.

[0223] Furthermore, it is preferable that the insulating layer formed from the cured product of the resin composition of this embodiment has a small surface roughness after roughening treatment. Specifically, the arithmetic mean roughness Ra of the surface of the insulating layer after roughening treatment is preferably 200 nm or less, more preferably 150 nm or less, and particularly preferably 100 nm or less. The lower limit of the arithmetic mean roughness Ra is not particularly limited, but may be, for example, 10 nm or more. The arithmetic mean roughness Ra of the surface of the insulating layer is measured using a non-contact surface roughness meter in VSI mode with a 50x magnification lens. The non-contact surface roughness meter used is a WYKONT3300 manufactured by Veeco Instruments.

[0224] <<Resin Composite Sheet>> The resin composite sheet of this embodiment includes a support and a layer formed from the resin composition of this embodiment and disposed on the surface of the support. The resin composite sheet can be used as a build-up film or a dry film solder resist. There are no particular limitations on the method for producing the resin composite sheet, but examples include a method of obtaining a resin composite sheet by applying (coating) a solution obtained by dissolving the resin composition of this embodiment in a solvent to a support and drying the applied solution.

[0225] Examples of the support used here include, but are not limited to, polyethylene film, polypropylene film, polycarbonate film, polyethylene terephthalate film, ethylene tetrafluoroethylene copolymer film, and release films obtained by applying a release agent to the surface of these films, organic film substrates such as polyimide film, conductive foils such as copper foil and aluminum foil, glass plates, SUS (Steel Use Stainless) plates, FRP (Fiber-Reinforced Plastics), and other plate-shaped materials.

[0226] Examples of application methods (coating methods) include methods in which a solution of the resin composition of this embodiment dissolved in a solvent is applied to a support using a bar coater, die coater, doctor blade, baker applicator, or the like. Furthermore, after drying, a single-layer sheet can be obtained by peeling or etching the support from a resin composite sheet in which the support and the resin composition are laminated. It should be noted that a single-layer sheet can also be obtained without using a support by supplying a solution of the resin composition of this embodiment dissolved in a solvent into a mold having a sheet-shaped cavity and drying it to form it into a sheet.

[0227] In the production of the monolayer sheet or resin composite sheet of this embodiment, the drying conditions for removing the solvent are not particularly limited. However, because low temperatures tend to leave the solvent in the resin composition, and high temperatures accelerate curing of the resin composition, drying conditions of 20°C to 200°C for 1 to 90 minutes are preferred. The monolayer sheet or resin composite sheet can be used in an uncured state after the solvent has been dried, or it can be used in a semi-cured (B-staged) state as needed. Furthermore, the thickness of the resin layer in the monolayer sheet or resin composite sheet of this embodiment can be adjusted by the concentration and coating thickness of the solution of the resin composition of this embodiment used for coating (coating). While not particularly limited, a thickness of 0.1 to 500 μm is preferred because a thicker coating thickness generally leads to more solvent remaining during drying.

[0228] The present invention will be explained in more detail below with reference to examples. The materials, amounts used, ratios, treatment contents, treatment procedures, etc. shown in the following examples can be changed as appropriate without departing from the spirit of the present invention. Therefore, the scope of the present invention is not limited to the specific examples shown below. If the measuring instruments used in the examples are difficult to obtain due to discontinuation or the like, measurements can be made using other instruments with equivalent performance.

[0229] <Measurement of Weight-Average Molecular Weight and Number-Average Molecular Weight> The weight-average molecular weight (Mw) and number-average molecular weight (Mn) of compounds (including resins) were measured by gel permeation chromatography (GPC) using a liquid pump (Shimadzu Corporation, LC-20AD), a differential refractive index detector (Shimadzu Corporation, RID-20A), and GPC columns (Showa Denko K.K., GPC KF-801, 802, 803, 804), with tetrahydrofuran as the solvent, a flow rate of 1.0 mL / min, a column temperature of 40°C, and a calibration curve based on monodisperse polystyrene.

[0230] <Measurement of parameters α and β> The parameters α and β in the resin (A) are determined by the following methods: １ The calculated values ​​were calculated by H-NMR measurement. The synthesized resin was dissolved in a mixed solvent of heptane and methanol, and the procedure of drying and solidifying was repeated to remove the residual solvent contained in the recovered solid. Then, the recovered solid was dissolved in CDCl ３ (containing 0.03% by volume of TMS (tetramethylsilane)), １ H-NMR measurement was carried out. １ In H-NMR, the parameters α and β of each resin were calculated using the following formula. The peak position of TMS (tetramethylsilane) was set to 0 ppm. The instrument used was an NMR AVANCE NEO500 manufactured by Bruker. (The brackets in formula (α) and formula (β) are １ The integral between the corresponding chemical shift values ​​in H-NMR is shown.)

[0231] Synthesis Example 1 Synthesis of Resin (A) Having a Terminal Group Represented by Formula (T1) and an Indane Skeleton 520 g of toluene, 0.75 g of activated clay, 150 g of 1,3-diisopropenylbenzene (Tokyo Chemical Industry Co., Ltd.), and a stirrer were placed in a flask equipped with a thermometer and a condenser, and heated to an internal temperature of 50°C while stirring. The mixture was then gradually heated to an internal temperature of 70°C over 5 hours, and reacted at the internal temperature of 70°C for an additional hour. After allowing to cool, the activated clay was removed by filtration, and the solvent was distilled off under heating and reduced pressure, yielding 129 g of a solid resin. １The H-NMR chart is shown in Figure 1. The Mw of the obtained resin (A) was 1193, the Mn was 693, and the Mw / Mn was 1.7. In formula (Tx), the parameter α was 0.63, the parameter β was 1.07, and n + o + p was 3.4. The structures in parentheses represented by (a), (b), and (c) in formula (Tx) all have the same molecular weight, and n + o + p was calculated assuming that the Mn of the synthesized resin was the average molecular weight. Furthermore, GPC analysis confirmed that the residual monomer was 1% by mass or less. The functional group equivalent (isopropenyl group equivalent) of the obtained resin (A) was 324 g / eq. The functional group equivalent (g / eq.) of resin (A) was calculated from (number average molecular weight (Mn) ÷ 2) ÷ β.

[0232] Synthesis Example 2: Synthesis of polyphenylene ether compound (B1) having a terminal carbon-carbon unsaturated double bond Synthesis of bifunctional phenylene ether oligomer A vertical reactor equipped with a stirrer, a thermometer, an air inlet tube, and a baffle plate was charged with CuBr. ２ 0.33 g (1.5 mmol) of copper bromide, 0.63 g (3.7 mmol) of N,N'-di-t-butylethylenediamine, 6.95 g (69 mmol), 670 g of toluene, and 320 g of methanol were charged and dissolved by stirring at a reaction temperature of 40°C. Separately, in advance, in a separate vessel, 46.2 g (171 mmol) of 2,2',3,3',5,5'-hexamethyl-(1,1'-biphenyl)-4,4'-diol, 129.5 g (1,060 mmol) of 2,6-dimethylphenol, and CuBr ２0.33 g (1.5 mmol) of copper bromide, 0.63 g (3.7 mmol) of N,N'-di-t-butylethylenediamine, 6.95 g (69 mmol) of n-butyldimethylamine, 440 g of toluene, and 170 g of methanol were charged and dissolved with stirring at a reaction temperature of 40°C. Subsequently, while bubbling a mixed gas adjusted to an oxygen concentration of 8% by mixing nitrogen and air into the mixed solution in the polymerization tank, the mixed solution in the dropping tank was added dropwise over 280 minutes and stirred. After completion of the dropwise addition, 700 g of water in which 7.1 g (16 mmol) of tetrasodium ethylenediaminetetraacetate had been dissolved was added to terminate the reaction. The aqueous layer and the organic layer were separated, and the organic layer was washed with a 1 M aqueous hydrochloric acid solution and then with pure water. The resulting solution was concentrated to 50% by mass using an evaporator, yielding 340 g of phenylene ether resin toluene solution A. The number average molecular weight as calculated on a polystyrene basis by the GPC method was 985, the weight average molecular weight as calculated on a polystyrene basis by the GPC method was 1090, and the hydroxyl equivalent was 478 g / eq.

[0233] <<Synthesis of Modified Polyphenylene Ether Compound>> A reactor equipped with a stirrer, a thermometer, and a reflux condenser was charged with 300 g of the toluene solution A of the phenylene ether resin obtained above, 57.5 g (0.38 mol) of vinylbenzyl chloride (manufactured by AGC Seimi Chemical Co., Ltd., "CMS-P"), 1,200 g of methylene chloride, 5 g (0.037 mol) of benzyldimethylamine, 70 g of pure water, and 63 g of a 30.5 mass% aqueous NaOH solution, and the mixture was stirred at a reaction temperature of 40°C. After stirring for 24 hours, the organic layer was washed with a 1 M aqueous hydrochloric acid solution and then with pure water. The resulting solution was concentrated and added dropwise to methanol to solidify. The solid was collected by filtration and dried in vacuo to obtain 178 g of a polyphenylene ether compound (B1) mainly composed of a compound represented by formula (OP-15). The number average molecular weight (GPC) was 1,200 in terms of polystyrene, the weight average molecular weight (GPC) was 1,840 in terms of polystyrene, the vinyl double bond equivalent was 620 g / eq., and the hydroxyl equivalent was 48,500 g / eq.

[0234] Synthesis Example 3: Synthesis of polymer (va) having structural units represented by formula (V) 2.25 moles (292.9 g) of divinylbenzene, 1.32 moles (172.0 g) of ethylvinylbenzene, 11.43 moles (1190.3 g) of styrene, and 15.0 moles (1532.0 g) of n-propyl acetate were charged into a reactor, and 600 mmol of a boron trifluoride diethyl ether complex was added at 70°C, followed by a reaction for 4 hours. The polymerization reaction was terminated with an aqueous sodium bicarbonate solution, and the oil layer was washed three times with pure water. The mixture was then subjected to reduced pressure devolatilization at 60°C, and polymer (va) having structural units represented by formula (V) was recovered. The obtained polymer (va) having structural units represented by formula (V) was weighed, and it was confirmed that 860.8 g of polymer (va) having structural units represented by formula (V) was obtained.

[0235] The resulting polymer (va) having a structural unit represented by formula (V) had a number average molecular weight Mn of 2,060, a weight average molecular weight Mw of 30,700, and a monodispersity index Mw / Mn of 14.9. １３ C-NMR and １ By performing H-NMR analysis, resonance lines derived from each monomer unit used as a raw material were observed in polymer (va) having a structural unit represented by formula (V). Based on the NMR measurement results and GC analysis results, the proportions of each monomer unit (structural unit derived from each raw material) in polymer (va) having a structural unit represented by formula (V) were calculated as follows: structural units derived from divinylbenzene: 20.9 mol% (24.3 mass%), structural units derived from ethylvinylbenzene: 9.1 mol% (10.7 mass%), structural units derived from styrene: 70.0 mol% (65.0 mass%), and the proportion of structural units having residual vinyl groups derived from divinylbenzene was 16.7 mol% (18.5 mass%). The vinyl group equivalent was 241 g / eq.

[0236] <Method for Measuring the Relative Permittivity of a Cured Product of Maleimide Compound (B) at a Frequency of 10 GHz, Measured by a Cavity Resonator Perturbation Method> The relative permittivity of a cured product of maleimide compound (B) at a frequency of 10 GHz, measured by a cavity resonator perturbation method, was measured as follows. The solvent in the maleimide compound (B) was evaporated to dryness, yielding a powder of maleimide compound (B). Using the obtained powder of maleimide compound (B), a cured plate was produced as follows. The powder was filled into a mold measuring 100 mm on a side and 1.6 mm in thickness, and 12 μm copper foil (3EC-M3-VLP, manufactured by Mitsui Mining & Smelting Co., Ltd.) was placed on both sides. The mixture was vacuum-pressed at a pressure of 30 kg / cm and a temperature of 220°C for 120 minutes to obtain a cured plate measuring 100 mm on a side and 1.6 mm in thickness. The copper foil on both sides of the obtained cured plate was removed by etching, and then the dielectric constant (Dk) and dielectric loss tangent (Df) were measured after drying for 60 minutes at 120°C at a frequency of 10 GHz using a cavity resonator perturbation method in accordance with JIS C218:2007. The cavity resonator used was manufactured by EM Lab, and the network analyzer used was a P5005A manufactured by Keysight Technologies. If the maleimide compound alone did not cure under the following conditions, an imidazole catalyst (TPIZ, 2E4MZ) was used as a curing accelerator in a ratio of 0.5 parts by mass per 100 parts by mass of the maleimide compound (B) and cured. Furthermore, if the composition did not cure even with the imidazole catalyst, Perbutyl P (manufactured by NOF Corporation) was used in a ratio of 0.5 parts by mass per 100 parts by mass of the maleimide compound (B) and cured.

[0237] The maleimide compound (ma1) (manufactured by DIC Corporation, NE-X-9500, corresponding to the maleimide compound having the structural unit represented by the above formula (M7)) had a relative dielectric constant of 2.5 as measured according to the above method. The glass transition temperature, measured according to the following method, was 227°C.

[0238] The maleimide compound (ma2) (manufactured by DIC Corporation, NE-X-9470S, corresponding to the maleimide compound having the structural unit represented by formula (M1) above) had a dielectric constant of 2.4 as measured according to the above-mentioned method. The glass transition temperature, measured according to the following method, was 265°C.

[0239] <Method for Measuring Glass Transition Temperature of Maleimide Compound (B)> The glass transition temperature of the maleimide compound (B) was measured according to the following method. A powder of the maleimide compound (B) was obtained by evaporating the solvent of the maleimide compound (B) to dryness. A cured plate was produced in the same manner as described above using the obtained powder of maleimide compound (B). The glass transition temperature was measured using a dynamic viscoelasticity analyzer (DMA) in accordance with JIS-K7244-5:1999 (Plastics - Test methods for dynamic mechanical properties - Part 5: Bending vibration - Non-resonance method) under conditions of a starting temperature of 30°C, an ending temperature of 350°C, a heating rate of 10°C / min, and a measurement frequency of 10 Hz. The copper foil on both sides of the obtained cured plate was removed by etching, and the sample was cut (downsized) to 12.7 mm x 30 mm x 1.6 mm, and the dynamic viscoelasticity was measured. The maximum value of the dynamic elastic modulus (Loss Modulus) obtained was taken as the glass transition temperature. The dynamic viscoelasticity measuring device used was a DMA Q-800 manufactured by TA Instruments.

[0240] Example 1 A mixture of 51 parts by mass of the resin (A) obtained in Synthesis Example 1 above, 45 parts by mass of a maleimide compound (ma1) (NE-X-9500 manufactured by DIC Corporation, corresponding to a maleimide compound having a structural unit represented by the above formula (M7)), 4.0 parts by mass of a phosphorus-based flame retardant (PX-200 manufactured by Daihachi Chemical Industry Co., Ltd., 1,3-phenylenebis(2,6-dixylenyl phosphate)), 0.8 parts by mass of DISPERBYK-2009 (manufactured by BYK Japan KK) and 0.6 parts by mass of DISPERBYK-161 (manufactured by BYK Japan KK) as dispersants, and silica (vinyl silane slurry silica, manufactured by Admatechs Co., Ltd., SC2050-MNU, average particle diameter (D ５０ 40 parts by mass of a 0.5 μm curing agent and 0.50 parts by mass of a curing accelerator (Perbutyl P, manufactured by NOF Corporation) were mixed and diluted with methyl ethyl ketone to a solid content of 65% by mass to obtain a varnish. The blending amounts of each component described above are expressed as solid content values.

[0241] <Production of Metal Foil-Clad Laminate> The varnish obtained above was impregnated and coated onto a 0.1 mm thick NE glass woven fabric (N856D S101SC, manufactured by Nitto Boseki Co., Ltd.), and then heated and dried at 155°C for 5 minutes to obtain a prepreg (thickness 0.135 mm) with a resin composition content of 76 mass%. The properties of the NE glass woven fabric used are as follows: IPC applicable grade: 1078 Density (counts / 25 mm) warp: 53 Density (counts / 25 mm) weft: 53 Thickness (mm): 0.044 Mass (g / m ２ ) : 43.5 One or six of the obtained prepregs were stacked, and 12 μm thick electrolytic copper foil (3EC-M3-VLP, manufactured by Mitsui Mining & Smelting Co., Ltd.) was placed on both sides, and a pressure of 30 kgf / cm was applied. ２ The laminate was then vacuum pressed at 220° C. for 120 minutes to obtain a copper foil-clad laminate having an insulating layer thickness of 0.135 mm or 0.8 mm as a metal foil-clad laminate.

[0242] <Measurement and Evaluation Methods> (1) Dielectric Properties After the copper foil on both sides of the copper foil-clad laminate obtained as described above was removed by etching, it was cut (downsized) to 1.0 mm x 100 mm x 0.8 mm. The dielectric constant (Dk) and dielectric loss tangent (Df) were measured at a frequency of 10 GHz after drying at 120°C for 60 minutes using a cavity resonator perturbation method in accordance with JIS C218:2007. The cavity resonator used was manufactured by EM Lab, and the network analyzer used was a P5005A manufactured by Keysight Technologies. The measurement temperature was 23°C. The properties were evaluated as follows: A: Dk is 2.85 or less and Df is 0.0022 or less; B: Dk is greater than 2.85 and / or Df is greater than 0.0022.

[0243] (2) Glass transition temperature (Tg) The glass transition temperature was measured using a dynamic viscoelasticity measuring apparatus (DMA) in accordance with JIS-K7244-5:1999 (Plastics - Test methods for dynamic mechanical properties - Part 5: Bending vibration - Non-resonance method), starting temperature 30 ° C., ending temperature 350 ° C., heating rate 10 ° C. / min, measurement frequency 10 Hz, under the conditions of a laminate obtained by removing the copper foil on both sides of the copper foil-clad laminate obtained above by etching (hereinafter referred to as "Laminate A"), after cutting (downsizing) to 12.7 mm × 30 mm × 0.8 mm, dynamic viscoelasticity was measured, and the maximum value of the dynamic elastic modulus (Loss Modulus) obtained at that time was taken as the glass transition temperature. The dynamic viscoelasticity measuring apparatus used was a DMA Q-800 manufactured by TA Instruments.

[0244] (3) Coefficient of thermal expansion (CTE: Coefficient of linear Thermal Expansion) For the laminate A obtained as described above, the thermal expansion coefficient of the test piece was measured by the TMA method (Thermo-Mechanical Analysis) specified in JIS C 6481 5.19, and the value was determined. Specifically, the copper foil on both sides of the copper foil-clad laminate obtained above was removed by etching, and the laminate was cut (downsized) to 4.5 mm x 10 mm x 0.135 mm. After that, the temperature was raised from 30 ° C. to 320 ° C. at a rate of 10 ° C. per minute using a thermomechanical analyzer (TA Instruments, TMA Q-400), and the linear thermal expansion coefficient (CTE (X)) (unit: ppm / ° C.) in the plane direction from 30 ° C. to 300 ° C. was measured. The measurement direction was the longitudinal direction (Warp) of the glass cloth of the laminate. The ppm is a volume ratio. Other details are in accordance with the above-mentioned JIS C 6481 5.19.

[0245] (4) Moisture absorption heat resistance (moisture absorption treatment using a pressure cooker tester) The copper foil-clad laminate obtained as described above was cut (downsized) to 50 mm x 50 mm x 0.8 mm, and all of the copper foil on one side was removed by etching. On the other side, half of the copper foil was removed by etching to obtain a sample for measuring moisture absorption heat resistance. The obtained sample was left to stand for 5 hours in the presence of saturated steam at 121 ° C and 2 atmospheres using a pressure cooker tester, and then immersed (dipped) in a solder bath at 260 ° C for 30 seconds, and the presence or absence of abnormalities in appearance was visually observed. The pressure cooker tester used was a PC-3 model manufactured by Hirayama Seisakusho Co., Ltd. Each measurement was performed on three sheets, and the three sheets were evaluated as follows: A: 0 sheets with abnormalities in appearance B: 1 to 2 sheets with abnormalities in appearance C: 3 sheets with abnormalities in appearance The appearance was observed by five experts and decided by majority vote.

[0246] Example 2 6.0 parts by mass of the polyphenylene ether compound (B1) having a terminal carbon-carbon unsaturated double bond obtained in Synthesis Example 2 above, spherical silica (powder silica, average particle diameter (D ５０ ) 1.1 μm, SC-4500SQ, Admatechs Co., Ltd.) 15 parts by mass, spherical silica (powdered silica, average particle diameter (D ５０ ) 0.7 μm, SFP-130MC) 15 parts by mass, a silane coupling agent (KMB-1003, Shin-Etsu Chemical Co., Ltd.) 0.75 parts by mass, and a wetting and dispersing agent (DISPERBYK-161, BYK Japan K.K.) 0.30 parts by mass were mixed to produce a master batch. Next, 15 parts by mass of the resin (A) obtained in Synthesis Example 1, 45 parts by mass of a maleimide compound (ma1) (NE-X-9500 manufactured by DIC Corporation, corresponding to a maleimide compound having a structural unit represented by the above formula (M7)), 30 parts by mass of the polymer (va) obtained in Synthesis Example 3 above having a structural unit represented by the formula (V), 4.0 parts by mass of a phosphorus-based flame retardant (PX-200 manufactured by Daihachi Chemical Industry Co., Ltd., 1,3-phenylenebis(2,6-dixylenyl phosphate)), and silica (vinyl silane slurry silica, SC2050-MNU manufactured by Admatechs Co., Ltd., average particle size (D ５０) 0.5 μm) 10 parts by mass, 0.20 parts by mass of DISPERBYK-2009 (manufactured by BYK Japan Co., Ltd.) and 0.30 parts by mass of DISPERBYK-161 (manufactured by BYK Japan Co., Ltd.) as dispersants, and 0.50 parts by mass of a curing accelerator (Perbutyl P, manufactured by NOF Corporation) were mixed and diluted with methyl ethyl ketone to a solid content of 65% by mass to obtain a mixture. The masterbatch obtained above was blended into the obtained mixture and stirred to obtain a varnish. The blending amounts of each component described above indicate values ​​in terms of solid content. A metal foil-clad laminate was produced using the obtained varnish in the same manner as in Example 1 and evaluated.

[0247] Example 3 The same procedure was performed as in Example 2, except that the content of the resin (A) obtained in Synthesis Example 1 above was changed to 23 parts by mass, the content of the maleimide compound (ma1) was changed to 44 parts by mass, and the content of the polymer (va) having a structural unit represented by formula (V) obtained in Synthesis Example 3 above was changed to 23 parts by mass.

[0248] Example 4 The same procedure was performed as in Example 2, except that the content of the resin (A) obtained in Synthesis Example 1 above was changed to 30 parts by mass, and the content of the polymer (va) having a structural unit represented by Formula (V) obtained in Synthesis Example 3 above was changed to 15 parts by mass.

[0249] Example 5 The same procedures were carried out as in Example 1, except that 45 parts by mass of the maleimide compound (ma1) was not added, 52 parts by mass of the maleimide compound (ma2) (NE-X-9470S, manufactured by DIC Corporation, corresponding to the maleimide compound having the structural unit represented by the above formula (M1)) was added, and the content of the resin (A) obtained in the above Synthesis Example 1 was changed to 44 parts by mass.

[0250] Example 6 In Example 2, spherical silica (powder silica, average particle diameter (D ５０ ) 1.1 μm, SC-4500SQ, Admatechs Co., Ltd.) 15 parts by mass and spherical silica (powdered silica, average particle diameter (D ５０A masterbatch was produced by not blending 15 parts by mass of SFP-130MC (0.7 μm) and 21 parts by mass of hollow silica (porosity 32%, average particle size (D50) 4.0 μm), and by blending 0.38 parts by mass of silane coupling agent (KMB-1003, Shin-Etsu Chemical Co., Ltd.).

[0251] Comparative Example 1 The same procedure was carried out as in Example 2, except that the resin (A) obtained in Synthesis Example 1 above was not blended, the content of the maleimide compound (ma1) was 46 parts by mass, and the content of the polymer (va) having a structural unit represented by formula (V) obtained in Synthesis Example 3 above was 44 parts by mass.

[0252] Comparative Example 2 The same procedure was carried out in Example 2, except that the content of the resin (A) obtained in Synthesis Example 1 above was changed to 49 parts by mass, the maleimide compound (ma1) was not blended, and the content of the polymer (va) having a structural unit represented by formula (V) obtained in Synthesis Example 3 above was changed to 41 parts by mass.

[0253]

Claims

1. A resin composition comprising: a resin (A) having a terminal group represented by formula (T1) and an indane skeleton; and a maleimide compound (B), wherein a cured product of the maleimide compound (B) has a relative dielectric constant of 2.0 to 2.8 at a frequency of 10 GHz as measured according to a cavity resonator perturbation method. (In formula (T1), Ma each independently represents a hydrocarbon group having 1 to 12 carbon atoms which may be substituted with a halogen atom, x represents an integer of 0 to 4, and * represents a bonding position to another moiety.) 2. The resin composition according to claim 1, wherein the resin (A) comprises a resin represented by formula (T1-1). (In formula (T1-1), R is a group containing a structural unit represented by formula (Tx). Each Ma independently represents a hydrocarbon group having 1 to 12 carbon atoms which may be substituted with a halogen atom. x is an integer of 0 to 4.) (In formula (Tx), n, o, and p represent the average number of repeating units, n represents a number greater than 0 and equal to or less than 20, o and p each independently represent a number from 0 to 20, and 1.0≦n+o+p≦20.

0. Each Ma independently represents a hydrocarbon group having 1 to 12 carbon atoms which may be substituted with a halogen atom. x represents an integer from 0 to 4. The structural units (a), (b), and (c) are each bonded to the structural units (a), (b), and (c) or to other groups at *, and each structural unit may be bonded randomly.) 3. The resin composition according to claim 1, wherein in the structural unit represented by formula (Tx), 1.1≦n+o+p≦20.

0.

4. The resin composition according to claim 1, wherein the parameter α calculated from formula (α) in the resin (A) is 0.55 or more and 1.00 or less, and the parameter β calculated from formula (β) is 0.20 or more and 3.00 or less. (The numbers in the parentheses in formula (α) and formula (β) are １ The integral between the corresponding chemical shift values ​​in H-NMR is shown.) 5. The resin composition according to claim 1, wherein the resin (A) contains a resin represented by formula (T1-1), and the parameter α calculated from formula (α) in the resin (A) is 0.55 or more and 1.00 or less, and the parameter β calculated from formula (β) is 0.20 or more and 3.00 or less. (The numbers in the parentheses in formula (α) and formula (β) are １ The integral between the corresponding chemical shift values ​​in H-NMR is shown.) (In formula (T1-1), R is a group containing a structural unit represented by formula (Tx). Each Ma independently represents a hydrocarbon group having 1 to 12 carbon atoms which may be substituted with a halogen atom. x is an integer of 0 to 4.) (In formula (Tx), n, o, and p represent the average number of repeating units, n represents a number greater than 0 and equal to or less than 20, o and p each independently represent a number from 0 to 20, and 1.0≦n+o+p≦20.

0. Each Ma independently represents a hydrocarbon group having 1 to 12 carbon atoms which may be substituted with a halogen atom. x represents an integer from 0 to 4. The structural units (a), (b), and (c) are each bonded to the structural units (a), (b), and (c) or to other groups at *, and each structural unit may be bonded randomly.) 6. The resin composition according to claim 1 or 5, wherein the number average molecular weight of the resin (A) is 400 to 3,000, and the weight average molecular weight of the resin (A) is 500 to 6,000.

7. The resin composition according to claim 1 or 5, wherein the ratio of the weight average molecular weight of said resin (A) to the number average molecular weight of said resin (A), Mw / Mn, is 1.1 to 3.

0.

8. The resin composition according to claim 1 or 5, wherein the content of said resin (A) is 5 to 90 parts by mass based on 100 parts by mass of resin solids in said resin composition.

9. The resin composition according to claim 1 or 5, wherein the content of the maleimide compound (B) is 5 to 90 parts by mass based on 100 parts by mass of resin solids in the resin composition.

10. A resin composition according to claim 1 or 5, wherein the maleimide compound (B) comprises one or more selected from the group consisting of a compound represented by formula (M0), a compound represented by formula (M1), a compound represented by formula (M3), a compound represented by formula (M5), and a compound represented by formula (M7). (In formula (M0), R ５１ each independently represents a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or a phenyl group; R ５２ each independently represents a hydrogen atom or a methyl group; n １ represents an integer of 1 or more.) (In formula (M1), R Ｍ１ , R Ｍ２ , R Ｍ３ , and R Ｍ４ R each independently represents a hydrogen atom or an organic group. Ｍ５ and R Ｍ６ Each independently represents a hydrogen atom or an alkyl group. Ｍ represents a divalent aromatic group. A is a 4- to 6-membered alicyclic group. R Ｍ７ and R Ｍ８ are each independently an alkyl group. mx is 1 or 2, and lx is 0 or 1. R Ｍ９ and R Ｍ１０ Each of R independently represents a hydrogen atom or an alkyl group. Ｍ１１ , R Ｍ１２ , R Ｍ１３ , and R Ｍ１４ R each independently represents a hydrogen atom or an organic group. Ｍ１５ each independently represents an alkyl group having 1 to 10 carbon atoms, an alkyloxy group having 1 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, an aryloxy group having 6 to 10 carbon atoms, an arylthio group having 6 to 10 carbon atoms, a halogen atom, a hydroxyl group, or a mercapto group. px represents an integer of 0 to 3. nx represents an integer of 1 to 20.) (In formula (M3), R ５５ each independently represents a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or a phenyl group; ５ represents an integer of 1 or more and 10 or less.) (In formula (M5), R ５８ each independently represents a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or a phenyl group; R ５９ each independently represents a hydrogen atom or a methyl group; n ６ represents an integer of 1 or more.) (In the above formula (M7), R １ each independently represents an alkyl group having 1 to 10 carbon atoms; R ２ each independently represents an alkyl group, an alkoxy group, or an alkylthio group having 1 to 10 carbon atoms; an aryl group, an aryloxy group, or an arylthio group having 6 to 10 carbon atoms; a cycloalkyl group having 3 to 10 carbon atoms; a halogen atom; a hydroxyl group; or a mercapto group; ３ , R ４ , R ５ and R ６ each independently represents a hydrogen atom or a methyl group, and R ３ and R ４ one of which is a hydrogen atom and the other is a methyl group; R ５ and R ６ One of X is a hydrogen atom and the other is a methyl group; １ is represented by the following formula (x): (In formula (x), R ７ and R ８ each independently represents a hydrogen atom or a methyl group, and R ７ and R ８ one of which is a hydrogen atom and the other is a methyl group; R ９ each independently represents an alkyl group, an alkoxy group, or an alkylthio group having 1 to 10 carbon atoms; an aryl group, an aryloxy group, or an arylthio group having 6 to 10 carbon atoms; a cycloalkyl group having 3 to 10 carbon atoms; a halogen atom; a hydroxyl group; or a mercapto group; and t represents an integer of 0 to 4. １ X per benzene ring to which １ is the average number of substitutions, and represents a number from 0 to 4, p represents an integer from 1 to 3, q ​​represents an integer from 0 to 4, and k represents an integer from 1 to 100.

11. The resin composition according to claim 1 or 5, further comprising a compound having two or more polymerizable carbon-carbon unsaturated double bonds.

12. The resin composition according to claim 11, wherein the compound having two or more polymerizable carbon-carbon unsaturated double bonds includes at least one selected from the group consisting of vinyl aryl compounds, (meth)acrylate compounds, and (meth)allyl compounds.

13. The resin composition according to claim 12, wherein the compound having two or more polymerizable carbon-carbon unsaturated double bonds comprises at least one member selected from the group consisting of a polyphenylene ether compound containing two or more terminal carbon-carbon unsaturated double bonds, and a polymer having a structural unit represented by formula (V). (In formula (V), Ar represents an aromatic hydrocarbon linking group. * represents a bonding position.) 14. The resin (A) contains a resin represented by formula (T1-1), and in the structural unit represented by formula (Tx), 1.1≦n+o+p≦20.0; the parameter α calculated from formula (α) in the resin (A) is 0.55 or more and 1.00 or less, and the parameter β calculated from formula (β) is 0.20 or more and 3.00 or less; the number average molecular weight of the resin (A) is 400 to 3000 and the weight average molecular weight of the resin (A) is 500 to 6000; Mw / Mn, which is the ratio of the weight average molecular weight of the resin (A) to the number average molecular weight of the resin (A), is 1.1 to 3.0; the content of the resin (A) is 5 to 90 parts by mass relative to 100 parts by mass of resin solid content in the resin composition; and the content of the maleimide compound (B) is 5 to 90 parts by mass relative to 100 parts by mass of resin solid content in the resin composition; 2. The resin composition according to claim 1, wherein the maleimide compound (B) comprises one or more selected from the group consisting of a compound represented by formula (M0), a compound represented by formula (M1), a compound represented by formula (M3), a compound represented by formula (M5), and a compound represented by formula (M7). (The numbers in the parentheses in formula (α) and formula (β) are １ The integral between the corresponding chemical shift values ​​in H-NMR is shown.) (In formula (T1-1), R is a group containing a structural unit represented by formula (Tx). Each Ma independently represents a hydrocarbon group having 1 to 12 carbon atoms which may be substituted with a halogen atom. x is an integer of 0 to 4.) (In formula (Tx), n, o, and p represent the average number of repeating units, n represents a number greater than 0 and equal to or less than 20, o and p each independently represent a number from 0 to 20, and 1.0≦n+o+p≦20.

0. Each Ma independently represents a hydrocarbon group having 1 to 12 carbon atoms which may be substituted with a halogen atom. x represents an integer from 0 to 4. The structural units (a), (b), and (c) are each bonded to the structural units (a), (b), and (c) or to other groups at *, and each structural unit may be bonded randomly.) (In formula (M0), R ５１ each independently represents a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or a phenyl group; R ５２ each independently represents a hydrogen atom or a methyl group; n １ represents an integer of 1 or more.) (In formula (M1), R Ｍ１ , R Ｍ２ , R Ｍ３ , and R Ｍ４ R each independently represents a hydrogen atom or an organic group. Ｍ５ and R Ｍ６ Each independently represents a hydrogen atom or an alkyl group. Ｍ represents a divalent aromatic group. A is a 4- to 6-membered alicyclic group. R Ｍ７ and R Ｍ８ are each independently an alkyl group. mx is 1 or 2, and lx is 0 or 1. R Ｍ９ and R Ｍ１０ Each of R independently represents a hydrogen atom or an alkyl group. Ｍ１１ , R Ｍ１２ , R Ｍ１３ , and R Ｍ１４ R each independently represents a hydrogen atom or an organic group. Ｍ１５ each independently represents an alkyl group having 1 to 10 carbon atoms, an alkyloxy group having 1 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, an aryloxy group having 6 to 10 carbon atoms, an arylthio group having 6 to 10 carbon atoms, a halogen atom, a hydroxyl group, or a mercapto group. px represents an integer of 0 to 3. nx represents an integer of 1 to 20.) (In formula (M3), R ５５ each independently represents a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or a phenyl group; n ５ represents an integer of 1 or more and 10 or less.) (In formula (M5), R ５８ each independently represents a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or a phenyl group; R ５９ each independently represents a hydrogen atom or a methyl group; n ６ represents an integer of 1 or more.) (In the above formula (M7), R １ each independently represents an alkyl group having 1 to 10 carbon atoms; R ２ each independently represents an alkyl group, an alkoxy group, or an alkylthio group having 1 to 10 carbon atoms; an aryl group, an aryloxy group, or an arylthio group having 6 to 10 carbon atoms; a cycloalkyl group having 3 to 10 carbon atoms; a halogen atom; a hydroxyl group; or a mercapto group; ３ , R ４ , R ５ and R ６ each independently represents a hydrogen atom or a methyl group, and R ３ and R ４ one of which is a hydrogen atom and the other is a methyl group; R ５ and R ６ One of X is a hydrogen atom and the other is a methyl group; １ is represented by the following formula (x): (In formula (x), R ７ and R ８ each independently represents a hydrogen atom or a methyl group, and R ７ and R ８ one of which is a hydrogen atom and the other is a methyl group; R ９ each independently represents an alkyl group, an alkoxy group, or an alkylthio group having 1 to 10 carbon atoms; an aryl group, an aryloxy group, or an arylthio group having 6 to 10 carbon atoms; a cycloalkyl group having 3 to 10 carbon atoms; a halogen atom; a hydroxyl group; or a mercapto group; and t represents an integer of 0 to 4. １ X per benzene ring to which １ is the average number of substitutions, and represents a number from 0 to 4, p represents an integer from 1 to 3, q ​​represents an integer from 0 to 4, and k represents an integer from 1 to 100.

15. The resin composition according to claim 14, further comprising a compound having two or more polymerizable carbon-carbon unsaturated double bonds.

16. The resin composition according to claim 15, wherein the compound having two or more polymerizable carbon-carbon unsaturated double bonds includes at least one selected from the group consisting of vinyl aryl compounds, (meth)acrylate compounds, and (meth)allyl compounds.

17. The resin composition according to claim 16, wherein the vinyl aryl compound comprises at least one member selected from the group consisting of polyphenylene ether compounds containing two or more terminal carbon-carbon unsaturated double bonds and polymers having a structural unit represented by formula (V). (In formula (V), Ar represents an aromatic hydrocarbon linking group. * represents a bonding position.) 18. The resin composition according to any one of claims 1 to 5 and 14 to 17, further comprising a filler.

19. The resin composition according to claim 18, wherein the filler comprises one or more selected from the group consisting of silica, aluminum hydroxide, talc, aluminum nitride, boron nitride, forsterite, titanium oxide, barium titanate, strontium titanate, and calcium titanate.

20. The resin composition according to claim 18, wherein the content of the filler in the resin composition is 1 to 1,600 parts by mass per 100 parts by mass of resin solids in the resin composition.

21. The resin composition of claim 18, wherein the filler comprises a silica slurry.

22. The resin composition according to claim 18, further comprising a compound having two or more polymerizable carbon-carbon unsaturated double bonds, and a mass ratio of the compound having two or more polymerizable carbon-carbon unsaturated double bonds to the filler is 1:1 to 1:

50.

23. The resin composition according to claim 18, further comprising a compound having two or more polymerizable carbon-carbon unsaturated double bonds, the compound having two or more polymerizable carbon-carbon unsaturated double bonds comprising a polyphenylene ether compound represented by formula (OP), and the filler comprising powdered silica. (In formula (OP), X represents an aromatic group, -(Y-O) ｎ１ - represents a polyphenylene ether structure, n1 represents an integer of 1 to 100, and n2 represents an integer of 1 to 4. Rx is a group represented by formula (Rx-1) or formula (Rx-2). (In formula (Rx-1) and formula (Rx-2), R １ , R ２ , and R ３ each independently represents a hydrogen atom, an alkyl group, an alkenyl group, or an alkynyl group. * is a bonding site with an oxygen atom. Each Mc independently represents a hydrocarbon group having 1 to 12 carbon atoms. z represents an integer of 0 to 4. r represents an integer of 0 to 6.

24. The resin composition according to claim 18, wherein the filler comprises a silica slurry and powdered silica, and further comprises a compound having two or more polymerizable carbon-carbon unsaturated double bonds, and the compound having two or more polymerizable carbon-carbon unsaturated double bonds comprises a polyphenylene ether compound represented by formula (OP). (In formula (OP), X represents an aromatic group, -(Y-O) ｎ１ - represents a polyphenylene ether structure, n1 represents an integer of 1 to 100, and n2 represents an integer of 1 to 4. Rx is a group represented by formula (Rx-1) or formula (Rx-2). (In formula (Rx-1) and formula (Rx-2), R １ , R ２ , and R ３ each independently represents a hydrogen atom, an alkyl group, an alkenyl group, or an alkynyl group. * is a bonding site with an oxygen atom. Each Mc independently represents a hydrocarbon group having 1 to 12 carbon atoms. z represents an integer of 0 to 4. r represents an integer of 0 to 6.

25. The resin composition according to any one of claims 1 to 5 and 14 to 17, which is for use in a printed wiring board.

26. A cured product of the resin composition according to any one of claims 1 to 5 and 14 to 17.

27. A prepreg formed from a substrate and the resin composition according to any one of claims 1 to 5 and 14 to 17.

28. A metal foil clad laminate comprising at least one prepreg according to claim 27 and a metal foil disposed on one or both sides of the prepreg.

29. A resin composite sheet comprising a support and a layer formed from the resin composition according to any one of claims 1 to 5 and 14 to 17, which is disposed on the surface of the support.

30. A printed wiring board comprising an insulating layer and a conductor layer disposed on a surface of the insulating layer, wherein the insulating layer comprises a layer formed from a resin composition according to any one of claims 1 to 5 and 14 to 17.

31. A semiconductor device comprising the printed wiring board according to claim 30.

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