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

Abstract

Provided is a resin composition comprising: a resin (A) having a terminal group represented by formula (T1) and having an indane backbone structure; a thermoplastic elastomer (B); and at least one thermosetting compound (C) selected from the group consisting of a compound that is different from the resin (A) and has a polymerizable carbon-carbon unsaturated double bond at a terminal, a maleimide compound, and a cyanate ester compound. The thermoplastic elastomer (B) contains a hydrogenated butadiene monomer unit and / or a hydrogenated isoprene monomer unit. In formula (T1), Ma's each independently represent a C1-12 hydrocarbon group which may be substituted by a halogen atom, x represents an integer of 0-4, and * indicates a bonding position to other moiety. Also provided are a cured article, a prepreg, a metal-foil-clad laminate board, a resin composite sheet, a printed circuit board, and a semiconductor device, in each of which the resin composition is used.

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 a 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 other thermosetting compounds. When a resin composition containing such a resin having an indane skeleton and other thermosetting compounds is used in an insulating layer of a printed wiring board, low dielectric properties (Dk and / or Df) are required. Furthermore, depending on the application, long-term heat resistance is also required. Under these circumstances, the present invention aims to provide a resin composition containing such a resin having an indane skeleton and other thermosetting compounds, which has excellent moldability and can provide a cured product having excellent low dielectric properties (Dk and / or Df) and excellent long-term 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 present inventors have conducted research and found that the above-mentioned problems can be solved by blending a hydrogenated thermoplastic elastomer into a resin composition containing a resin having an indane skeleton and another thermosetting compound. Specifically, the above-mentioned problems have been solved by the following means. <1> A resin composition comprising: a resin (A) having an indane skeleton and a terminal group represented by formula (T1); a thermoplastic elastomer (B); and at least one thermosetting compound (C) selected from the group consisting of a compound having a polymerizable carbon-carbon unsaturated double bond at the terminal other than the resin (A), a maleimide compound, and a cyanate ester compound, wherein the thermoplastic elastomer (B) contains hydrogenated butadiene monomer units and / or hydrogenated isoprene monomer units. (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 hydrogenation rate of the thermoplastic elastomer (B) is 70% or more. <3> The resin composition according to <1> or <2>, wherein the thermoplastic elastomer (B) contains styrene monomer units, and hydrogenated butadiene monomer units and / or hydrogenated isoprene monomer units. <4> The resin composition according to any one of <1> to <3>, wherein the thermoplastic elastomer (B) has a number average molecular weight of 2,000 or more. <5> The resin composition according to any one of <1> to <4>, wherein the thermoplastic elastomer (B) is contained in an amount of 2.5 to 50 parts by mass per 100 parts by mass of resin solids in the resin composition. <6> The resin composition according to any one of <1> to <5>, 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. 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 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 respective structural units may be bonded randomly.) <7> The resin composition according to any one of <1> to <6>, containing the resin (A) in an amount of 1 to 90 parts by mass per 100 parts by mass of the resin solid content in the resin composition. <8> The resin composition according to any one of <1> to <7>, wherein the thermosetting compound (C) includes at least one selected from the group consisting of a maleimide compound, a polymer having a structural unit represented by formula (V), a polyphenylene ether compound having a terminal carbon-carbon unsaturated double bond, a (meth)allyl compound, a (meth)acrylate compound, a compound other than the resin (A) having an indane skeleton having a terminal carbon-carbon unsaturated double bond, and a cyanate ester compound. (In formula (V), Ar represents an aromatic hydrocarbon linking group. * represents a bonding position.) <9> The resin composition according to any one of <1> to <8>, wherein the thermosetting compound (C) includes at least one 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 (M4), a compound represented by formula (M5), a polymer having a structural unit represented by formula (V), and a compound represented by formula (OP). (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 RＭ６ 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 (M4), R ５６ each independently represents a hydrogen atom, a methyl group, or an ethyl group; R ５７ each independently represents a hydrogen atom or a methyl group. (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 formula (V), Ar represents an aromatic hydrocarbon linking group. * represents a bonding position.) (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.) <10> The resin composition according to any one of <1> to <9>, comprising 5 to 90 parts by mass of the thermosetting compound (C) per 100 parts by mass of resin solid content in the resin composition. <11> The hydrogenation rate of the thermoplastic elastomer (B) is 70% or more, the thermoplastic elastomer (B) contains styrene monomer units and hydrogenated butadiene monomer units and / or hydrogenated isoprene monomer units, the number average molecular weight of the thermoplastic elastomer (B) is 2,000 or more, the thermoplastic elastomer (B) is contained in a proportion of 2.5 to 50 parts by mass relative to 100 parts by mass of resin solid content in the resin composition, the resin (A) contains a resin represented by formula (T1-1), and the resin (A) is contained in a proportion of 1 to 90 parts by mass relative to 100 parts by mass of resin solid content in the resin composition, The resin composition according to any one of <1> to <10>, wherein the thermosetting compound (C) includes at least one selected from the group consisting of a maleimide compound, a polymer having a structural unit represented by formula (V), a polyphenylene ether compound having a terminal carbon-carbon unsaturated double bond, a (meth)allyl compound, a (meth)acrylate compound, a compound other than the resin (A) having an indane skeleton having a terminal carbon-carbon unsaturated double bond, and a cyanate ester compound; and the resin composition contains 5 to 90 parts by mass of the thermosetting compound (C) per 100 parts by mass of a resin solid content in the resin composition. (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 (V), Ar represents an aromatic hydrocarbon linking group. * represents a bonding position.) <12> The resin composition according to <11>, wherein the thermosetting compound (C) includes at least one 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 (M4), a compound represented by formula (M5), a polymer having a structural unit represented by formula (V), and a compound represented by formula (OP). (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 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 (M4), R ５６ each independently represents a hydrogen atom, a methyl group, or an ethyl group; R ５７ each independently represents a hydrogen atom or a methyl group. (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 formula (V), Ar represents an aromatic hydrocarbon linking group. * represents a bonding position.) (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 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.) <13> The resin composition according to any one of <1> to <12>, further comprising a flame retardant. <14> The resin composition according to any one of <1> to <13>, further comprising a filler. <15> The resin composition according to <14>, wherein the content of the filler is 10 to 1600 parts by mass per 100 parts by mass of resin solids in the resin composition. <16> The resin composition according to any one of <1> to <15>, further comprising a curing accelerator. <17> The resin composition according to <16>, wherein the content of the curing accelerator is 0.1 to 0.8 parts by mass per 100 parts by mass of resin solids in the resin composition. <18> A cured product of the resin composition according to any one of <1> to <17>. <19> A prepreg formed from a substrate and the resin composition according to any one of <1> to <17>. <20> A metal foil-clad laminate comprising at least one layer formed from the prepreg according to <19> and metal foil disposed on one or both sides of the layer formed from the prepreg. <21> A resin composite sheet comprising a support and a layer formed from the resin composition according to any one of <1> to <17> and disposed on the surface of the support. <22> A printed wiring board comprising an insulating layer and a conductor layer disposed on the surface of the insulating layer, wherein the insulating layer comprises a layer formed from the resin composition according to any one of <1> to <17>. <23> A semiconductor device comprising the printed wiring board according to <22>.

[0007] The present invention makes it possible to provide a resin composition that is excellent in moldability and can provide a cured product that has excellent low dielectric properties (Dk and / or Df) and excellent long-term 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] 1 shows an NMR chart of the resin obtained in Synthesis Example 1.

[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 solid content refers to components excluding fillers and solvents, and is intended to include the resin (A), the thermoplastic elastomer (B), the thermosetting compound (C), as well as other components that are blended as necessary, 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 comprises a resin (A) (sometimes simply referred to herein as "resin (A)") having a terminal group represented by formula (T1) and having an indane skeleton, a thermoplastic elastomer (B), and at least one thermosetting compound (C) (sometimes simply referred to herein as "thermosetting compound (C)") selected from the group consisting of a compound having a polymerizable carbon-carbon unsaturated double bond at an end other than that of the resin (A), a maleimide compound, and a cyanate ester compound, wherein the thermoplastic elastomer (B) contains a hydrogenated butadiene monomer unit and / or a hydrogenated isoprene monomer unit. (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] This configuration makes it possible to provide a resin composition that is excellent in moldability, has excellent low dielectric properties (Dk and / or Df), and can provide a cured product with excellent long-term heat resistance. The inventors have previously discovered that the resin (A) having an indane skeleton can provide a cured product with excellent low dielectric properties (Dk and / or Df), but also discovered that the resin (A) having an indane skeleton alone does not cure sufficiently. In this embodiment, by incorporating a thermosetting compound (C), the curing of the resin composition containing the resin (A) having an indane skeleton and the thermosetting compound (C) can be effectively promoted, thereby successfully improving moldability. However, even if the resin composition containing the resin (A) having an indane skeleton and the thermosetting compound (C) can be cured, a cured product with excellent low dielectric properties (Dk and / or Df) is still required. In order to achieve such low dielectric properties (Dk and / or Df), the present embodiment incorporates a thermoplastic elastomer (B). Because the thermoplastic elastomer contains soft components with high thermal mobility, the collision probability of functional groups (isopropenyl groups, maleimide groups, polymerizable carbon-carbon unsaturated double bonds) remaining in the later stages of the curing reaction increases, reducing the number of functional groups remaining in the final product (cured material), presumably improving the low dielectric properties. Furthermore, because the thermoplastic elastomer (B) has good compatibility with the resin (A) having an indane skeleton and the thermosetting compound (C), the thermoplastic elastomer (B) penetrates into the network structure of the cured product of the resin (A) having an indane skeleton and the thermosetting compound (C), forming a so-called semi-IPN structure (semi-interpenetrating polymer network). Furthermore, in this embodiment, it was found that long-term heat resistance can be achieved by using a thermoplastic elastomer (B) that is at least partially hydrogenated. Specifically, excellent low dielectric properties (Dk and / or Df, especially Df) were maintained even after prolonged heating.The reason for this is presumably that the addition of the elastomer reduces the amount of functional groups remaining in the final product (cured product), and that the use of a hydrogenated elastomer further reduces the amount of functional groups remaining in the final product (cured product).

[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 is 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 (A) may also contain a structural unit represented by formula (Ty).

[0024] In addition to the above, resin (A) includes the resins described in paragraphs 0011 to 0025 of WO 2023 / 176766, the resins described in paragraphs 0012 to 0033 of WO 2023 / 176763, and the resins described in paragraphs 0026 to 0043 of WO 2023 / 176765. The compounds described in JP-A-2023-104785 and the compositions described in JP-A-2024-007493 can be taken into consideration, the contents of which are incorporated herein by reference.

[0025] 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 0.30 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.)

[0026] 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, for example, it is presumed that the number of crosslinking points with the functional group of the thermosetting compound (C) described below increases, making it easier to form a network upon thermal curing, 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). When synthesizing the resin represented by formula (T1-1) (preferably the resin represented by formula (T1-1-2)), the parameters α and β of the resin represented by formula (T1-1) (preferably the 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 methods other than those described above.

[0027] The parameter α is preferably 0.35 or more, more preferably 0.40 or more, even more preferably 0.45 or more, even more preferably 0.50 or more, and even more preferably 0.55 or more, and may be 0.57 or more, 0.59 or more, 0.60 or more, 0.62 or more, 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 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 2.50 or less, 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, even more 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.

[0028] 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.

[0029] 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.

[0030] 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 low dielectric properties (Dk and / or Df, particularly Df) of the obtained cured product tend to be better, and the long-term heat resistance (low dielectric properties (Dk and / or Df, particularly Df) after long-term heating) of the obtained cured product tend to be further improved. Furthermore, by setting the functional group equivalent weight of resin (A) to the above upper limit or less, the low dielectric properties (Dk and / or Df, particularly Df) of the obtained cured product tend to be better, and the heat resistance (particularly the glass transition temperature) tends to be better. The functional group equivalent weight (isopropenyl group equivalent weight) of resin (A) is determined according to the method described in the examples below.

[0031] The content of resin (A) in the resin composition of this embodiment 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, 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 Df of the resulting cured product tends to be lower. 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, and particularly preferably 35 parts by mass or less, depending on the application, it may be 30 parts by mass or less, 25 parts by mass or less, or 22 parts by mass or less. Setting the content of resin (A) at or below the upper limit tends to improve the moldability of the resin composition and the heat resistance of the resulting cured product. The resin composition of the present embodiment may contain only one type of resin (A), or may contain two or more types. When two or more types are contained, the total amount is preferably in the above range.

[0032] 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.

[0033] 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.

[0034] <Thermoplastic Elastomer (B)> The resin composition of this embodiment contains a thermoplastic elastomer (B) containing hydrogenated butadiene monomer units and / or hydrogenated isoprene monomer units. By containing such a thermoplastic elastomer (B), the resulting cured product has excellent low dielectric properties (Dk and / or Df) and long-term heat resistance (low dielectric properties (Dk and / or Df, particularly Df) after long-term heating). When the thermoplastic elastomer (B) used in this embodiment is a copolymer, it may be a random copolymer, a block copolymer, or a block copolymer having random blocks.

[0035] More specifically, the thermoplastic elastomer (B) used in this embodiment is preferably an elastomer containing styrene monomer units and hydrogenated butadiene monomer units and / or hydrogenated isoprene monomer units.

[0036] As described above, the thermoplastic elastomer (B) in this embodiment preferably contains a styrene monomer unit. By containing a styrene monomer unit, compatibility with the thermosetting compound (C) tends to be excellent. Examples of styrene monomers include styrene, α-methylstyrene, p-methylstyrene, divinylbenzene (vinylstyrene), N,N-dimethyl-p-aminoethylstyrene, and N,N-diethyl-p-aminoethylstyrene. Of these, styrene, α-methylstyrene, and p-methylstyrene are preferred from the viewpoints of availability and productivity. Of these, styrene is particularly preferred.

[0037] In this embodiment, the content of styrene monomer units in the thermoplastic elastomer (B) is preferably 0% by mass or more, more preferably 10% by mass or more, and even more preferably 20% by mass or more, of the total monomer units in the thermoplastic elastomer (B). It is also preferably 90% by mass or less, more preferably 80% by mass or less, and even more preferably 70% by mass or less. By setting the content of styrene monomer units to the above upper limit or less, the adhesion and tackiness to substrates and the like are improved. Furthermore, a content of styrene monomer units equal to or greater than the above lower limit is more preferable because it can suppress increased tack, reduces the occurrence of adhesive residue and stop marks, and tends to improve the ease of peeling between adhesive surfaces. The thermoplastic elastomer (B) may contain only one type of styrene monomer unit, or two or more types. When two or more types are contained, the total amount is preferably within the above range. The method for measuring the content of styrene monomer units in the thermoplastic elastomer (B) used in 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 butadiene monomer units and the like, which will be described later.

[0038] The thermoplastic elastomer (B) used in this embodiment preferably has a hydrogenation rate (hydrogenation ratio) of 70% or more, more preferably 80% or more, even more preferably 85% or more, even more preferably 90% or more, and still more preferably 95% or more. By using a thermoplastic elastomer with a high hydrogenation rate, the resulting cured product tends to have better low dielectric properties (Dk and / or Df).

[0039] The thermoplastic elastomer (B) used in this embodiment preferably also has a random copolymer block (hereinafter sometimes simply referred to as a "random copolymer block") containing styrene monomer units and at least one selected from the group consisting of hydrogenated butadiene monomer units and / or hydrogenated isoprene monomer units. It is believed that the random arrangement of such monomer units reduces the self-cohesion force of the styrene monomer units in the molecular chain of the thermoplastic elastomer (B), thereby improving the flexibility of the thermoplastic elastomer (B). "Random copolymerization" refers to a disordered arrangement of the monomer units. The random copolymer block is preferably formed by randomly polymerizing styrene monomer units and hydrogenated butadiene monomer units and / or hydrogenated isoprene monomer units.

[0040] The thermoplastic elastomer (B) used in this embodiment may have, in addition to a random copolymer block of styrene monomer units and at least one monomer selected from the group consisting of hydrogenated butadiene monomer units and / or hydrogenated isoprene monomer units, at least one of a polymer block mainly composed of styrene monomer units and a polymer block mainly composed of at least one monomer selected from the group consisting of hydrogenated butadiene monomer units and / or hydrogenated isoprene monomer units. Here, "mainly composed of" means, in the case of a polymer block mainly composed of styrene monomer units, that the proportion of styrene monomer units in the polymer block is 60% by mass or more, preferably 70% by mass or more, more preferably 80% by mass or more, even more preferably 90% by mass or more, and even more preferably 95% by mass or more. The same applies to a polymer block mainly composed of at least one monomer selected from the group consisting of hydrogenated butadiene monomer units and / or hydrogenated isoprene monomer units.

[0041] In the thermoplastic elastomer (B) used in this embodiment, the total of styrene monomer units, butadiene monomer units, isoprene monomer units, hydrogenated butadiene monomer units, and hydrogenated isoprene monomer units is preferably 90% by mass or more, more preferably 95% by mass or more, even more preferably 97% by mass or more, and still more preferably 99% by mass or more of the total monomer units. Here, the butadiene monomer units, isoprene monomer units, hydrogenated butadiene monomer units, and hydrogenated isoprene monomer units may contain at least one of hydrogenated butadiene monomer units and hydrogenated isoprene monomer units, and it is not essential that all of these be contained. In the present embodiment, the total amount of styrene monomer units, butadiene monomer units, isoprene monomer units, hydrogenated butadiene monomer units, and hydrogenated isoprene monomer units is 90 mass% or more of the total monomer units, and a thermoplastic elastomer essentially containing styrene monomer units, hydrogenated butadiene monomer units, and / or hydrogenated isoprene monomer units is more preferred.

[0042] A first specific example of the thermoplastic elastomer (B) used in this embodiment is an elastomer in which styrene monomer units and hydrogenated butadiene monomer units and / or hydrogenated isoprene monomer units account for 90 mass% or more of the total monomer units. A second specific example of the thermoplastic elastomer (B) used in this embodiment is an elastomer in which styrene monomer units and hydrogenated butadiene monomer units and / or hydrogenated isoprene monomer units account for 70 mass% or more of the total monomer units and which contains butadiene monomer units and / or isoprene monomer units.

[0043] The number average molecular weight of the thermoplastic elastomer (B) used in this embodiment is preferably 2,000 or more, preferably 2,500 or more, more preferably 3,000 or more, even more preferably 5,000 or more, still more preferably 10,000 or more, and still more preferably 20,000 or more, and is preferably 600,000 or less, more preferably 500,000 or less, even more preferably 400,000 or less, even more preferably 300,000 or less, and still more preferably 250,000 or less. By setting the number average molecular weight to be equal to or greater than the above-mentioned lower limit, the low dielectric properties (Dk and / or Df) of the obtained cured product will be more excellent, and the long-term heat resistance (low dielectric properties (Dk and / or Df, particularly Df) after long-term heating) of the obtained cured product will tend to be further improved. On the other hand, by setting the number average molecular weight to be equal to or less than the above-mentioned upper limit, moldability will tend to be further improved. When the resin composition of the present embodiment contains two or more types of thermoplastic elastomer (B), it is preferable that the number average molecular weight of the mixture thereof falls within the above range.

[0044] The thermoplastic elastomer (B) used in this embodiment preferably has a glass transition temperature (Tan δ) measured in accordance with JIS K 7244-1:1996 of -20°C to 30°C. By setting the temperature at or above the lower limit, the heat resistance of the resin composition and the resulting cured product tends to be further improved. On the other hand, by setting the temperature at or below the upper limit, the flexibility, low dielectric tangent, and crack resistance of the resin composition and the resulting cured product tend to be further improved. The glass transition temperature is preferably -15°C or higher, more preferably -12°C or higher, and may even be -5°C or higher, 0°C or higher, or 5°C or higher. The upper limit of the glass transition temperature is preferably 27°C or lower, more preferably 25°C or lower, and even more preferably 23°C or lower. When the resin composition of this embodiment contains two or more thermoplastic elastomers (B), the glass transition temperature of the thermoplastic elastomer (B) is the sum of the values ​​obtained by multiplying the glass transition temperature of each thermoplastic elastomer (B) by its mass fraction (wherein the glass transition temperature of each thermoplastic elastomer (B) is within the range of -20°C to 30°C). For example, when 30% by mass of a thermoplastic elastomer (B) having a glass transition temperature of 0°C is blended with 70% by mass of a thermoplastic elastomer (B) having a glass transition temperature of 10°C, the glass transition temperature is 0 x 0.3 + 10 x 0.7 = 7°C.

[0045] Examples of the composition of the thermoplastic elastomer (B) used in this embodiment include SBS (S: styrene, B: butadiene), SIS (I: isoprene), and hydrogenated versions thereof such as SEBS (E: ethylene, B: butylene) and SEPS (E: ethylene, P: propylene). At least one selected from the group consisting of SEBS and SEPS is preferred, with SEPS and SEBS being more preferred. Here, SEPS and SEBS also include partially hydrogenated versions.

[0046] Examples of commercially available products of the thermoplastic elastomer (B) used in this embodiment include S.O.E. (registered trademark) S1605, S1606, S1609, S1613, and Tuftec H1043 manufactured by Asahi Kasei Corporation, SEPTON (registered trademark) 2104 manufactured by Kuraray Co., Ltd., and DYNARON (registered trademark) 9901P manufactured by JSR Corporation.

[0047] The elastomer used in this embodiment may be a resin containing a polybutadiene structure. The polybutadiene structure may be partially or entirely hydrogenated. Specific examples include BI-2000 and BI-3000 manufactured by Nippon Soda Co., Ltd.

[0048] The content of the thermoplastic elastomer (B) in the resin composition of this embodiment is preferably 2.5 parts by mass or more, more preferably 5 parts by mass or more, even more preferably 7.5 parts by mass or more, even more preferably 10 parts by mass or more, even more preferably 12.5 parts by mass or more, even more preferably 15 parts by mass or more, per 100 parts by mass of resin solids. Depending on the intended use, it may even be 20 parts by mass or more, or 25 parts by mass or more. By setting the content at or above the lower limit, low dielectric tangent, crack resistance, and low thermal expansion, particularly low thermal expansion, tend to be further improved. The upper limit of the content of the thermoplastic elastomer (B) is preferably 50 parts by mass or less, more preferably 40 parts by mass or less, per 100 parts by mass of resin solids. Depending on the intended use, it may even be 30 parts by mass or less, 25 parts by mass or less, 21 parts by mass or less, 18 parts by mass or less, or 15 parts by mass or less. Setting the content at or below the upper limit tends to further improve crack resistance. The resin composition of the present embodiment may contain only one type of thermoplastic elastomer (B), or may contain two or more types. When two or more types are contained, the total amount is preferably in the above range.

[0049] <At least one thermosetting compound (C) selected from the group consisting of a compound having a polymerizable carbon-carbon unsaturated double bond at a terminal other than the resin (A), a maleimide compound, and a cyanate ester compound> The resin composition of this embodiment contains at least one thermosetting compound (C) selected from the group consisting of a compound having a polymerizable carbon-carbon unsaturated double bond at a terminal other than the resin (A) (compound (XC)), a maleimide compound, and a cyanate ester compound. The type of thermosetting compound (C) is not particularly limited, but a compound containing two or more thermosetting groups (functional groups capable of undergoing a polymerization reaction triggered by heat) is preferred. The polymerization reaction here is intended to include a reaction in which the molecule bonds with the same and / or different molecules to increase the molecular weight of the molecule. The thermosetting compound (C) preferably contains at least one selected from the group consisting of a maleimide compound, a polymer having a structural unit represented by formula (V), a polyphenylene ether compound having a terminal carbon-carbon unsaturated double bond, a (meth)allyl compound, a (meth)acrylate compound, a compound other than the resin (A) having an indane skeleton having a terminal carbon-carbon unsaturated double bond, and a cyanate ester compound; more preferably contains at least one selected from the group consisting of a maleimide compound, a polymer having a structural unit represented by formula (V), and a polyphenylene ether compound having a terminal carbon-carbon unsaturated double bond; and even more preferably contains at least one 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 (M4), a compound represented by formula (M5), a polymer having a structural unit represented by formula (V), and a compound represented by formula (OP), which will be described in detail later. (In formula (V), Ar represents an aromatic hydrocarbon linking group. * represents a bonding position.)

[0050] The content of the thermosetting compound (C) 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 45 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 solid content in the resin composition. By setting the content at or above the lower limit, the low dielectric properties (Dk and / or Df) of the obtained cured product tend to be more excellent. Furthermore, by setting the content at or below the upper limit, the long-term heat resistance (low dielectric properties (Dk and / or Df, particularly Df) after long-term heating) of the obtained cured product tends to be more excellent. The resin composition of this embodiment may contain only one type of thermosetting compound (C), or may contain two or more types. When two or more types are contained, the total amount is preferably within the above range.

[0051] <<Compound (XC) Having a Polymerizable Carbon-Carbon Unsaturated Double Bond at an End Other Than Resin (A)>> The resin composition of this embodiment may contain a compound (compound (XC)) having a polymerizable carbon-carbon unsaturated double bond at an end other than resin (A). An example of compound (XC) is a low-molecular-weight aromatic vinyl compound. Examples of aromatic vinyl compounds include methylstyrene (e.g., 4-methylstyrene), ethylvinylbenzene, diethyl 4-vinylbenzylphosphonate, 4-vinylbenzyl glycidyl ether, α-methylstyrene, 4-tert-butylstyrene, divinylbenzene, 1,2-bis(4-vinylphenyl)ethane (BVPE), vinylbenzyl ether, 1,3-diisopropenylbenzene, and 1,4-diisopropenylbenzene. Of these, 4-methylstyrene, 4-tert-butylstyrene, divinylbenzene, and 1,2-bis(4-vinylphenyl)ethane are preferred. Further, examples include resins having an isopropenyl group described in WO 2022 / 210095 (for example, compounds described in Synthesis Examples 1, 2, 7, and 8 of the same publication), the contents of which are incorporated herein by reference.

[0052] Another example of a compound (compound (XC)) having a polymerizable carbon-carbon unsaturated double bond at its terminal other than the resin (A) is vinylbenzyl ether. Examples of vinylbenzyl ether include reaction products produced by reacting 4,4'-isopropylidenebis(2,6-dimethylphenol) (tetramethylbisphenol A), hexamethylbiphenol (2,2',3,3',5,5'-hexamethyl-(1,1'-biphenyl)-4,4'-diol), 2,6-dihydroxynaphthalene, or the like with vinylbenzyl chloride and / or vinylbenzyl bromide. Further, resorcinol, catechol, hydroquinone, 2,7-dihydroxynaphthalene, 2-(diphenylphosphoryl)hydroquinone, bis(2,6-dimethylphenol), 2,2'-biphenol, 4,4-biphenol, 2,2',6,6'-tetramethylbiphenol, 3,3',5,5'-tetrabromo-2,2',6,6'-tetramethylbiphenol, 3,3'-dibromo-2,2',6,6'-tetramethylbiphenol, 4,4'-isopropylidenebis(2,6-dibromophenol) (tetrabromobisphenol A), 4,4'-isopropylidenebis(2,6-dimethylphenol) (tetramethylbisphenol A), 4,4'-isopropylidenebis(2-methylphenol), 4,4'-isopropylidenebis(2-allylphenol), 4 ,4'(1,3-phenylenediisopropylidene)bisphenol (bisphenol M), 4,4'-isopropylidenebis(3-phenylphenol), 4,4'-(1,4-phenylenediisopropylidene)bisphenol (bisphenol P), 4,4'-ethylidenediphenol (bisphenol E), 4,4'-oxydiphenol, 4,4'-thiodiphenol, 4,4'-thiobis(2,6-dimethylphenol), 4,4'-sulfonyldiphenol, 4,4'-sulfonylbis(2,6-dimethylphenol), 4,4'-sulfinyldiphenol, 4,4'-hexafluoroisopropylidene)bisphenol (bisphenol AF), 4,4'(1-phenylethylidene)bisphenol (bisphenol AP), bis(4-hydroxyphenyl)-2,2-Dichloroethylene (bisphenol C), bis(4-hydroxyphenyl)methane (bisphenol-F), bis(2,6-dimethyl-4-hydroxyphenyl)methane, 4,4'-(cyclopentylidene)diphenol, 4,4'-(cyclohexylidene)diphenol (bisphenol Z), 4,4'-(cyclododecylidene)diphenol, 4,4'-(bicyclo[2.2.1]heptylidene)diphenol, 4,4'-(9H-fluorene -9,9-diyl)diphenol, 3,3-bis(4-hydroxyphenyl)isobenzofuran-1(3H)-one, 1-(4-hydroxyphenyl)-3,3-dimethyl-2,3-dihydro-1H-inden-5-ol, 1-(4-hydroxy-3,5-dimethylphenyl)-1,3,3,4,6-pentamethyl-2,3-dihydro-1H-inden-5-ol, 3,3,3',3'-tetramethyl-2,2',3,3'-tetrahydro-1,1 Examples of vinylbenzyl ethers include those produced by reacting 5,6'-spirobi[indene]-5,6'-diol (spirobiindane), dihydroxybenzophenone (bisphenol K), tris(4-hydroxyphenyl)methane, tris(4-hydroxyphenyl)ethane, tris(4-hydroxyphenyl)propane, tris(4-hydroxyphenyl)butane, tris(3-methyl-4-hydroxyphenyl)methane, tris(3,5-dimethyl-4-hydroxyphenyl)methane, tetrakis(4-hydroxyphenyl)ethane, tetrakis(3,5-dimethyl-4-hydroxyphenyl)ethane, bis(4-hydroxyphenyl)phenylphosphine oxide, dicyclopentadienylbis(2,6-dimethylphenol), dicyclopentadienylbis(o-cresol), dicyclopentadienylbisphenol, or the like with vinylbenzyl chloride or vinylbenzyl bromide. In addition to the above, the vinylbenzyl compound also includes the vinylbenzyl ether compounds described in paragraph 0041 of JP 2019-194312 A, the contents of which are incorporated herein by reference.

[0053] In addition to the above, compounds having vinylphenyl at the terminal described in WO 2022 / 210095 (for example, compounds described in Synthesis Examples 12 to 16 of the same publication), paragraphs 0029 to 0039 of JP 2022-85610 A, vinyl benzyl ether resins described in paragraph 0041 of JP 2019-194312 A, copolymerized oligomers described in paragraphs 0013 to 0027 of WO 2022 / 014599, copolymers described in JP 2024-007493 A, compounds described in WO 2021 / 100658 A, compounds described in JP 2024-086554 A can also be used, the contents of which are incorporated herein by reference.

[0054] <<Maleimide Compound>> The resin composition of this embodiment may contain a maleimide compound. In this embodiment, the maleimide compound is preferably a compound having one or more (preferably two or more, more preferably 2 to 12, even more preferably 2 to 6, even more preferably 2 to 4, still more preferably 2 or 3, and even more preferably 2) maleimide groups per molecule. More specifically, the maleimide compound preferably includes one or more selected from the group consisting of compounds represented by formulas (M0) to (M7), more preferably includes one or more selected from the group consisting of compounds represented by formulas (M0), (M1), (M3), (M4), and (M5), more preferably includes one or more selected from the group consisting of compounds represented by formulas (M0), (M1), (M3), and (M5), and even more preferably includes a compound represented by formula (M1). (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. ５１are 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 compounds represented by formulas (M1) to (M7) below. (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.

[0055] 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.

[0056] 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.

[0057] 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.

[0058] 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.

[0059] 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.

[0060] 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.)

[0061] 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. (In formula (M2), R ５４ each independently represents a hydrogen atom or a methyl group; n ４ represents an integer of 1 or more. ４ 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 (M2), n ４ It may be, and is preferably, a mixture of compounds in which the other moieties are different. Furthermore, as described in the compound represented by formula (M0), it may be a mixture of compounds in which the other moieties are different. (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. ５is 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. (In formula (M4), R ５６ each independently represents a hydrogen atom, a methyl group, or an ethyl group; R ５７ each independently represents a hydrogen atom or a methyl group.

[0062] (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. 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.

[0063] The maleimide compound (M6) is a compound having a structural unit represented by formula (M6) and maleimide groups at both ends of the molecular chain. (In formula (M6), R ６１ represents a linear or branched alkylene group having 1 to 16 carbon atoms, or a linear or branched alkenylene group having 2 to 16 carbon atoms. ６２represents a linear or branched alkylene group having 1 to 16 carbon atoms, or a linear or branched alkenylene group having 2 to 16 carbon atoms. ６３ Each independently represents a linear or branched alkyl group having 1 to 16 carbon atoms, or a linear or branched alkenyl group having 2 to 16 carbon atoms. Each n independently represents an integer of 0 to 10.) For details of the maleimide compound (M6) and a production method thereof, please refer to paragraphs 0061 to 0066 of WO 2020 / 262577, the contents of which are incorporated herein by reference.

[0064] The maleimide compound (M7) is a maleimide compound obtained by reacting raw materials (1) with an aromatic amine compound (a1) having one to three alkyl groups on an aromatic ring, an aromatic divinyl compound (a2) having two ethenyl groups, and maleic anhydride. The maleimide compound (M7) is preferably a compound represented by formula (M7). (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.

[0065] 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.

[0066] The maleimide compound 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), "BMI-2300" manufactured by Daiwa Kasei Kogyo Co., Ltd. as the compound represented by formula (M2), "MIR-3000-70MT" manufactured by Nippon Kayaku Co., Ltd. as the compound represented by formula (M3), "BMI-70" manufactured by K.I. Chemical Industry Co., Ltd. as the compound represented by formula (M4), "MIR-5000" manufactured by Nippon Kayaku Co., Ltd. as the compound represented by formula (M5), "MIZ-001" manufactured by Nippon Kayaku Co., Ltd. as the maleimide compound (M6), and "NE-X-9500" manufactured by DIC Corporation as the maleimide compound (M7).

[0067] In addition to the above, examples of maleimide compounds include compounds described in paragraphs 0061 to 0066 of WO 2020 / 262577 and Japanese Patent No. 7160151, the contents of which are incorporated herein by reference.

[0068] Furthermore, examples of maleimide compounds other than those mentioned above include compounds having two or more maleimide groups, and specific examples 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, 4,4'-diphenylether bismaleimide, 4,4'-diphenylsulfone bismaleimide, 1,3-bis(3-maleimidophenoxy)benzene, 1,3-bis(4-maleimidophenoxy)benzene, prepolymers of these, and prepolymers of these maleimides and amines.

[0069] The maleimide group equivalent of the maleimide compound 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, particularly Df) of the obtained cured product tend to be more excellent. On the other hand, by setting it to the above upper limit or less, the long-term heat resistance (low dielectric properties (Dk and / or Df, particularly Df) after long-term heating) of the obtained cured product tends to be more improved, and the moldability tends to be more excellent.

[0070] The lower limit of the content of the maleimide compound in the resin composition of this embodiment is preferably 1 part by mass or more, more preferably 5 parts by mass or more, even more preferably 10 parts by mass or more, even more preferably 15 parts by mass or more, and even more preferably 18 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 40 parts by mass or more, 45 parts by mass or more, 50 parts by mass or more, or 52 parts by mass or more. When the content of the maleimide compound is 1 part by mass or more, the flame resistance and long-term heat resistance of the resulting cured product tend to be improved. Furthermore, the upper limit of the content of the maleimide compound is preferably 90 parts by mass or less, more preferably 85 parts by mass or less, even 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 solid content in the resin composition. When the content of the maleimide compound is 90 parts by mass or less, the peel strength and low water absorbency tend to be improved. The resin composition of this embodiment may contain only one type of maleimide compound, or may contain two or more types of maleimide compounds. When two or more types are contained, the total amount is preferably within the above range.

[0071] <<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.

[0072] 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.

[0073] 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)."

[0074] 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.

[0075] 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.

[0076] 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).

[0077] The structural unit (b) derived from a monovinyl aromatic compound preferably includes a structural unit represented by the following formula (V4).

[0078] 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.

[0079] 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.

[0080] 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.

[0081] 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.

[0082] 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.

[0083] 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.

[0084] 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).

[0085] 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.

[0086] 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)

[0087] 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)

[0088] 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.

[0089] 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 can be determined by measuring the dynamic viscoelasticity of a measurement sample 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) 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 during the measurement is taken as the glass transition temperature. An EXSTAR6000 DMS6100 manufactured by Seiko Instruments Inc. can be used as the dynamic viscoelasticity measuring device.

[0090] 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. 4.5 g of resin powder was spread in a stainless steel mold 100 mm x 30 mm x 1.0 mm high frame, placed in a vacuum press (Kitagawa Seiki Co., Ltd.), and held at 200 ° C, 220 ° C, and 240 ° C for 1.5 hours, pressing at a surface pressure of 1.9 MPa to produce a cured plate. The cured plate was downsized to a width of 1.0 mm, dried at 120 ° C for 60 minutes, and then measured for the relative permittivity (Dk) and dielectric loss tangent (Df) after drying at 10 GHz using a perturbation cavity resonator. The measurement temperature was 23 ° C. The perturbation cavity resonator used was a P5005A manufactured by Keysight Technologies.

[0091] 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.

[0092] The content of the polymer having a structural unit represented by formula (V) in the resin composition of this embodiment is preferably 1 part by mass or more, more preferably 5 parts by mass or more, even more preferably 10 parts by mass or more, even more preferably 20 parts by mass or more, even more preferably 25 parts by mass or more, and preferably 90 parts by mass or less, more preferably 70 parts by mass or less, even more preferably 60 parts by mass or less, even more preferably 50 parts by mass or less, and even more preferably 40 parts by mass or less, per 100 parts by mass of the resin solid content. 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.

[0093] <<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 terminal group represented by formula (Rx-1) and a terminal group represented by formula (Rx-2), which will be described later. By using such a composition, the low dielectric properties (Dk and / or Df, particularly Df) of the obtained cured product tend to be more excellent, and the long-term heat resistance (low dielectric properties (Dk and / or Df, particularly Df) after long-term heating) of the obtained cured product tends to be further improved. These are described in detail below.

[0094] 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).

[0095] (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.

[0096] 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 , R３４ , 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.

[0097] 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 the low water absorption and peel strength. These modified polyphenylene ether compounds (g) may be used alone or in combination of two or more.

[0098] 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 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.

[0099] 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 2 or more, more preferably 2.

[0100] 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.

[0101] 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.

[0102] 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.

[0103] 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.

[0104] 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).

[0105] 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 1 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.

[0106] 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 １０ , and R １１ may be the same or different and are alkyl groups or phenyl groups having 6 or less carbon atoms. ７ , R ８ , and R ９ 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.

[0107] 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.

[0108] 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.

[0109] 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.

[0110] Among the compounds represented by the above formula (OP-2), R ４ , R ５ , R ６ , 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 ９ , R １２ , R １３ , R １４ , R １５ , R １６ , R １７ , R １８ , R １９ , 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.

[0111] (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).

[0112] 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.

[0113] 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, Inc. Examples of modified polyphenylene ether compounds having a terminal vinylbenzyl group include polyphenylene ether compounds having a terminal hydroxyl group, such as "SA90" manufactured by SABIC Innovative Plastics, which are modified to a vinylbenzyl group using vinylbenzyl chloride or the like.

[0114] 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.

[0115] 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.

[0116] 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. The double bond concentration [mol / L] is calculated from this area value and the calibration curve. The double bond equivalent is then 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 functional group equivalent of other thermosetting compounds (C) can also be measured using the same method. However, for compounds (monomers) that can be expressed by a single molecular weight, the value calculated by (theoretical molecular weight ÷ number of functional groups) is used as the functional group equivalent. When two or more thermosetting compounds (C) are contained, the functional group equivalent of the thermosetting compound (C) is the sum (weighted average) of the values ​​obtained by multiplying the functional group equivalent of each thermosetting compound (C) by its mass fraction.

[0117] 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 5 parts by mass or more, even more preferably 10 parts by mass or more, even more preferably 20 parts by mass or more, and even more preferably 25 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 80 parts by mass or less, per 100 parts by mass of the resin solids in the resin composition. It may also be 70 parts by mass or less, 60 parts by mass or less, 50 parts by mass or less, 40 parts by mass or less, or 35 parts by mass or less, depending on the application. By setting the content to be equal to or less than the upper limit, the low dielectric properties (particularly low dielectric tangent) 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.

[0118] <<(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.

[0119] 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.

[0120] 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 the molecular weight 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 the molecular weight equal to or less than the upper limit, low thermal expansion tends to be further improved.

[0121] 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.

[0122] <<<(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 (nurate 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 thermosetting compound (C), 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).

[0123] In formula (TA), R Ａ represents a substituent, and is more preferably a substituent having a formula weight of 15 to 500.

[0124] R ＡA 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.

[0125] 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), R Ａ２ is a divalent linking group.

[0126] 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. ｃ１is 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.

[0127] R Ａ A third example is a phosphorus-based substituent.

[0128] R Ａ２ is preferably the first example.

[0129] 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.

[0130] 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.

[0131] 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.

[0132] 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.

[0133] 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.

[0134] 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.

[0135] 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.

[0136] <<<<(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 thereof include compounds represented by the following formula (AN-1): 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 is a methylene group, an isopropylidene group, —C(═O)—, —O—, —S—, or —S(═O) ２ represents a group represented by formula (AN-3). (In formula (AN-3), R ４each independently represents an alkylene group having 1 to 4 carbon atoms or a cycloalkylene group having 5 to 8 carbon atoms.

[0137] 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) Formula (AN-5)

[0138] The molecular weight of the (meth)allyl group-substituted nadimide compound (preferably a compound represented by formula (AN-1)) 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 be equal to or greater than the above-mentioned lower limit, low dielectric properties, low thermal expansion, 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-1)) is also preferably 1500 or less, more preferably 1000 or less, and 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 be equal to or less than the above-mentioned upper limit, moldability and peel strength tend to be further improved.

[0139] When the resin composition of the present embodiment contains a (meth)allyl group-substituted nadimide compound (preferably a compound represented by formula (AN-1)), 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-1)) 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.

[0140] <<<<(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 thermosetting compound (C), 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 １At 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.

[0141] 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).

[0142] In addition, commercially available (meth)allyl compounds having a glycoluril structure can also be used. Examples of commercially available compounds include, but are not limited to, TA-G manufactured by Shikoku Chemicals Corporation.

[0143] 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.

[0144] 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.

[0145] <<(Meth)acrylate Compound>> The resin composition of the present embodiment may contain a (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.

[0146] The (meth)acrylate compound may include either or both of a monofunctional (meth)acrylate compound and a polyfunctional (meth)acrylate compound. Examples of the monofunctional (meth)acrylate compound include an unsaturated epoxy (meth)acrylate compound having a (meth)acryloyl group, a urethane (meth)acrylate compound, a polyether (meth)acrylate compound, a polyalcohol (meth)acrylate compound, an alkyd (meth)acrylate compound, a polyester (meth)acrylate compound, a spiroacetal (meth)acrylate compound, and a silane coupling agent having a (meth)acryloyloxy group (e.g., 3-acryloxypropyltrimethoxysilane).

[0147] On the other hand, the term "polyfunctional (meth)acrylate compound" refers to a compound containing two or more (meth)acryloyloxy groups in one molecule, and preferably contains 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. Since the polyfunctional (meth)acrylate compound has a large number of (meth)acrylate groups that serve as crosslinking points, it is firmly cured with the resin (A) and the thermosetting compound (C), and a cured product having low dielectric properties (Dk and / or Df) and excellent heat resistance is obtained. 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.

[0148] In formula (MA), R １represents 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.

[0149] R １ is 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.

[0150] 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.

[0151] 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.

[0152] 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.

[0153] 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.

[0154] 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.

[0155] In addition to the above, (meth)acrylate compounds include resins having a (meth)acrylic group described in WO 2022 / 210095 (for example, compounds described in Synthesis Examples 5 and 21 of the same publication) and Japanese Patent No. 6,962,507 (for example, compounds described in Examples 1 to 9), compounds described in paragraph 0049 of JP-A-2019-194312, resins having a methacrylic group described in WO 2023 / 089976, and resins having a methacrylic group described in WO 2022 / 234455. The contents of this specification are incorporated herein by reference.

[0156] 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.

[0157] <<Compound Having an Indane Skeleton with a Carbon-Carbon Unsaturated Double Bond at a Terminal Other Than Resin (A)>> The resin composition of the present embodiment may contain a compound having an indane skeleton with a carbon-carbon unsaturated double bond at a terminal other than Resin (A). An example of the compound having an indane skeleton with a carbon-carbon unsaturated double bond at a terminal other than Resin (A) is a resin represented by Formula (T-St). (In formula (T-St), R is a group containing a structural unit represented by formula (Tx-St). Each Arm is independently a benzene ring, a naphthalene ring, or an anthracene ring. Each Ma is independently a hydrocarbon group having 1 to 12 carbon atoms which may be substituted with a halogen atom. Each Mb is independently a hydroxyl group, a halogen atom, or a hydrocarbon group having 1 to 20 carbon atoms which may be substituted with a hydroxyl group or a halogen atom. Each Mc is independently a hydrocarbon group having 1 to 12 carbon atoms. Each x, y, and z are independently an integer of 0 to 4. r1 is an integer of 1 to 6. R １ , R ２ , and R ３ each independently represents a hydrogen atom, an alkyl group, an alkenyl group, or an alkynyl group. (In formula (Tx-St), 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. They are bonded to the structural units (a), (b), and (c), or to other groups, and the structural units may be bonded randomly.)

[0158] In formula (T-St), R is a group containing a structural unit represented by formula (Tx-St). In formula (Tx-St), n, o, and p each represent the average number of repeating units in all molecules in the resin. In formula (Tx-St), 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, particularly even more preferably 3.3≦n+o+p, and furthermore, more preferably 3.5≦n+o+p, 3.7≦n+o+p, 4.0≦n+o+p, 4.2≦n+o+p in that order. In formula (Tx-St), 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, even more preferably n + o + p ≦ 6.5, and even more preferably n + o + p ≦ 6.4. The sum of n, o, and p can be calculated by the method described in the Examples below. In addition, the sum of n, o, and p in formula (Tx-St) is usually the same as the sum of n, o, and p in formula (Tx).

[0159] In formula (Tx-St), Ma and x have the same meanings as Ma and x in formula (Tx) described above, and the preferred ranges are also the same.

[0160] In formula (T-St), each Arm independently represents a benzene ring, a naphthalene ring, or an anthracene ring, preferably a benzene ring or a naphthalene ring, and more preferably a benzene ring. When Arm is a benzene ring and y is an integer of 1 to 4, it is preferred that the OH group bonded to Arm and Mb are bonded at one or two of the ortho and para positions (preferably at least one or two of the ortho positions). In formula (T-St), each Ma independently represents a hydrocarbon group having 1 to 12 carbon atoms which may be substituted with a halogen atom, and has the same meaning as Ma in formula (Tx) described above, and the preferred range is also the same. In formula (T-St), each Mb independently represents a hydroxyl group, a halogen atom, or a hydrocarbon group having 1 to 20 carbon atoms which may be substituted with a hydroxyl group or a halogen atom. A hydroxyl group, a halogen atom, or a hydrocarbon group having 1 to 20 carbon atoms which may be substituted with a halogen atom is preferred, and a hydroxyl group, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a linear or branched alkyl group having 1 to 10 carbon atoms, an alicyclic alkyl group having 4 to 8 carbon atoms, a cumyl group, a phenyl group, or a benzyl group is more preferred. Preferred halogen atoms include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom, with a fluorine atom or a chlorine atom being more preferred. Preferred linear or branched alkyl groups having 1 to 10 carbon atoms include a methyl group, an ethyl group, an isopropyl group, an isobutyl group, a t-butyl group, a pentyl group, an octyl group, and a nonyl group. Preferred alicyclic alkyl groups having 4 to 8 carbon atoms include a cyclohexyl group. In this embodiment, Mb is more preferably a hydroxyl group, a linear or branched alkyl group having 1 to 10 carbon atoms, or a benzyl group, and more preferably a hydroxyl group, a methyl group, an ethyl group, an isopropyl group, an isobutyl group, a t-butyl group, or a benzyl group.

[0161] In formula (T-St), 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 still more preferably a methyl group, ethyl group, isopropyl group, isobutyl group, or t-butyl group.

[0162] In formula (T-St), x has the same meaning as x in formula (Tx) described above, and the preferred range is also the same. In formula (T-St), each y independently represents an integer of 0 to 4, preferably an integer of 0 to 3, and more preferably an integer of 0 to 2. In formula (T-St), each z independently 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 even more preferably 0. In formula (T-St), r1 represents an integer of 1 to 6, preferably an integer of 1 to 5, more preferably an integer of 1 to 4, still more preferably an integer of 1 to 3, still more preferably 1 or 2, and even more preferably 1. In formula (T-St), R １ , R ２ , and R ３ R each independently represents a hydrogen atom, an alkyl group, an alkenyl group, or an alkynyl group, 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.

[0163] In this embodiment, the formula (T-St) is preferably represented by the formula (T-St2). (In formula (T-St2), R is a group containing a structural unit represented by formula (Tx-St). Each Ma independently represents a hydrocarbon group having 1 to 12 carbon atoms which may be substituted with a halogen atom. Each Mb independently represents a hydroxyl group, a halogen atom, or a hydrocarbon group having 1 to 20 carbon atoms which may be substituted with a hydroxyl group or a halogen atom. Each Mc independently represents a hydrocarbon group having 1 to 12 carbon atoms. Each x, y, and z independently represent an integer of 0 to 4. r1 represents an integer of 1 to 6. R １ , R ２ , and R ３ each independently represents a hydrogen atom, an alkyl group, an alkenyl group, or an alkynyl group. (In formula (Tx-St), 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. They are bonded to the structural units (a), (b), and (c), or to other groups, and the structural units may be bonded randomly.)

[0164] In the formula (T-St2), R, Ma, Mb, Mc, x, y, z, r1, R １ , R ２ , and R ３ respectively represent R, Ma, Mb, Mc, x, y, z, r1, and R in formula (T-St). １ , R ２ , and R ３ The same applies to the preferred range.

[0165] Furthermore, the resin represented by formula (T-St) preferably has a parameter α calculated from formula (α) of 0.55 or more and 1.00 or less. (The brackets in formula (α) are: １It represents the integral between the corresponding chemical shift values ​​in H-NMR.) Here, α represents the ratio of the structural unit having an indane skeleton (structural unit (a) in formula (Tx-St)). More specifically, it is presumed that by adjusting the ratio of the structural unit having an indane skeleton so as to satisfy the range of the parameter α, the rigidity of the resulting resin molecules can be increased, and the glass transition temperature of the cured product can be increased.

[0166] The parameter α in the resin represented by formula (T-St) 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 making the parameter α equal to or greater than the lower limit, the low dielectric properties (low relative dielectric constant and / or low dielectric dissipation factor) and heat resistance of the resulting cured product tend to be further improved. Since the low dielectric properties and heat resistance of the resulting cured product tend to be excellent, the parameter α is essentially preferably large, but may be 0.95 or less, 0.94 or less, 0.93 or less, or 0.92 or less.

[0167] Other examples of compounds having an indane skeleton with a terminal carbon-carbon unsaturated double bond other than resin (A) include resins having a structural unit derived from a compound represented by formula (DIP) as the main component and having a structure represented by formula (In-1) and / or formula (In-2) ​​(hereinafter, sometimes referred to as "resin (IP1)"). (In formula (DIP), each Ma independently represents a hydrocarbon group having 1 to 12 carbon atoms which may be substituted with a halogen atom, and x represents an integer of 0 to 4.) (In formula (In-1), each Mb independently represents a hydroxyl group, a halogen atom, or a hydrocarbon group having 1 to 20 carbon atoms which may be substituted with a hydroxyl group or a halogen atom. y represents an integer of 0 to 3. R ｘ is a group containing a carbon-carbon unsaturated double bond. * is a bonding site to other moieties. (In formula (In-2), 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 3; each Mb independently represents a hydroxyl group, a halogen atom, or a hydrocarbon group having 1 to 20 carbon atoms which may be substituted with a hydroxyl group or a halogen atom; y represents an integer of 0 to 4; R ｘ is a group containing a carbon-carbon unsaturated double bond. xp is the number of bonds coming out of the benzene ring and is an integer of 1 or 2. * is a bonding site to another site.) Here, "other site" means a site other than the structure represented by formula (In-1) and / or formula (In-2) ​​contained in resin (IP1). The same applies to other sites in the section on resin (IP1) below.

[0168] The resin (IP1) contains a group (R ｘ) and a structural unit derived from the compound represented by formula (DIP) (particularly, a structural unit derived from the compound represented by formula (DIP) having an indane skeleton (preferably a trimethylindane structure (the same applies hereinafter to the preferred range of the indane skeleton))) via an oxygen atom and / or a low-molecular-weight structural unit such as a phenyleneoxy group which may have a substituent. This is presumably why the content of the structural unit derived from the compound represented by formula (DIP) (particularly the indane skeleton) in the cured product of the resin composition containing resin (IP1) is high, thereby enabling a low Df (dielectric loss tangent). In particular, it is presumed that a low Df can be achieved even at a high curing temperature. Furthermore, resin (IP1) can have excellent heat resistance. Resin (IP1) can also have a low Dk (dielectric constant). It goes without saying that the structural unit derived from the compound represented by formula (DIP) may be synthesized from the compound represented by formula (DIP), or may be synthesized from other raw materials which provide the structural unit derived from the compound represented by formula (DIP). Examples of the compound represented by formula (DIP) include 1,3-diisopropenylbenzene and 1,4-diisopropenylbenzene. Other raw materials that provide structural units derived from the compound represented by formula (DIP) include, for example, α,α'-dihydroxy-1,3-diisopropylbenzene, α,α'-dihydroxy-1,4-diisopropylbenzene, α,α'-dihalogeno-1,3-diisopropylbenzene (e.g., α,α'-dichloro-1,3-diisopropylbenzene), α,α'-dihalogeno-1,4-diisopropylbenzene (e.g., α,α'-dichloro-1,4-diisopropylbenzene), α,α'-dialkoxy-1,3-diisopropylbenzene (e.g., α,α'-dimethoxy-1,3-diisopropylbenzene), α,α'-dialkoxy-1,4-diisopropylbenzene (e.g., α,α'-dimethoxy-1,4-diisopropylbenzene), and equivalents of the compound represented by formula (DIP) that provide the compound represented by formula (DIP) by a unit operation such as heating. In this embodiment, among the above, 1,3-diisopropenylbenzene and α,α'-dihydroxy-1,3-diisopropylbenzene are preferred. The above compounds may be used alone or in combination of two or more.

[0169] First, the formula (DIP) will be explained. (In formula (DIP), each Ma independently represents a hydrocarbon group having 1 to 12 carbon atoms which may be substituted with a halogen atom, and x represents an integer of 0 to 4.) Note that resin (IP1) may contain a plurality of structural units derived from the compound represented by formula (DIP), and in this case, each Ma and x may be the same or different.

[0170] In formula (DIP), Ma each independently represents a hydrocarbon group having 1 to 12 carbon atoms which may be substituted with a halogen atom, and has the same meaning as Ma in formula (T1) above, and the preferred range is also the same.

[0171] In formula (DIP), x represents an integer of 0 to 4, 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.

[0172] Resin (IP1) is primarily composed of structural units derived from the compound represented by formula (DIP). "Mainly composed" means that, of all structural units constituting resin (IP1), structural units derived from the compound represented by formula (DIP) account for the largest proportion. More specifically, the content of structural units derived from the compound represented by formula (DIP) in resin (IP1) is preferably 50 mol% or more of all structural units, more preferably 60 mol% or more, even more preferably 70 mol% or more, even more preferably 80 mol% or more, even more preferably 82 mol% or more, even more preferably 83 mol% or more, and particularly preferably 85 mol% or more. Here, "total structural units" refers to the total amount of structural units derived from all monomer molecules used as raw materials for resin (IP1).

[0173] Resin (IP1) further has a structure represented by formula (In-1) and / or formula (In-2). These groups are usually present as terminal groups. When Resin (IP1) has a structure represented by formula (In-1) and / or formula (In-2), the structural unit derived from the compound represented by formula (DIP) has a group (R ｘ ) via an oxygen atom and / or a low-molecular-weight structural unit such as a phenyleneoxy group which may have a substituent, and it is presumed that this has enabled a low Df (dielectric loss tangent) as described above, and that a low Df can be achieved even at a high curing temperature. Furthermore, as long as the resin (IP1) has a structure represented by formula (In-1) and / or formula (In-2), it may also have terminal groups of other structures. (In formula (In-1), each Mb independently represents a hydroxyl group, a halogen atom, or a hydrocarbon group having 1 to 20 carbon atoms which may be substituted with a hydroxyl group or a halogen atom. y represents an integer of 0 to 3. R ｘ is a group containing a carbon-carbon unsaturated double bond. * is a bonding site to other moieties. (In formula (In-2), 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 3; each Mb independently represents a hydroxyl group, a halogen atom, or a hydrocarbon group having 1 to 20 carbon atoms which may be substituted with a hydroxyl group or a halogen atom; y represents an integer of 0 to 4; R ｘ is a group containing a carbon-carbon unsaturated double bond. xp is the number of bonds coming out of the benzene ring and is an integer of 1 or 2. * is the bonding site to other moieties.

[0174] In formula (In-1), each Mb independently represents a hydroxyl group, a halogen atom, or a hydrocarbon group having 1 to 20 carbon atoms which may be substituted with a hydroxyl group or a halogen atom, and has the same definition as Mb in formula (T-St) described above, and the preferred range is also the same.

[0175] In formula (In-1), y represents an integer of 0 to 3, preferably an integer of 0 to 2, more preferably 0 or 2, and may be 0. Furthermore, y is preferably 2 from the viewpoint of dielectric properties. Furthermore, when y is 1 or more, Mb is preferably R ｘ It is preferably bonded at the adjacent position (ortho position) to the carbon atom to which the O group is bonded.

[0176] In formula (In-1), R ｘ is a group containing a carbon-carbon unsaturated double bond, and more preferably a group having a formula weight of 27 to 120. ｘ Specifically, each of Rx-11 and Rx-2 is preferably a group represented by formula (Rx-11) or a group represented by formula (Rx-2), more preferably a vinylbenzyl group or a (meth)acryloyl group, and even more preferably a vinylbenzyl group. (In formula (Rx-11) 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. r1 represents an integer of 1 to 6.

[0177] Formula (Rx-11) and Formula (Rx-2) have the same meanings and preferred ranges as Formula (Rx-1) and Formula (Rx-2) described in the section on polyphenylene ether compounds above, except for r1. r1 in Formula (Rx-11) 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.

[0178] In formula (In-2), each Ma independently represents a hydrocarbon group having 1 to 12 carbon atoms which may be substituted with a halogen atom, and has the same meaning as Ma in formula (T1), and the preferred range is also the same.

[0179] In formula (In-2), x represents an integer of 0 to 3, preferably an integer of 0 to 2, more preferably 0 or 1, and may be 0.

[0180] In formula (In-2), Mb and R ｘ respectively represent Mb and R in formula (In-1). ｘ The same applies to the preferred range.

[0181] In formula (In-2), y represents an integer of 0 to 4, preferably an integer of 0 to 3, more preferably an integer of 0 to 2, and even more preferably 0 or 2, and may be 0. Furthermore, y is preferably 2 from the viewpoint of dielectric properties. Furthermore, when y is 1 or more, Mb is preferably R ｘ It is preferably bonded at the adjacent position (ortho position) to the carbon atom to which the O group is bonded.

[0182] In formula (In-2), xp is the number of bonds coming out of the benzene ring and is an integer of 1 or 2. When xp is 2, for example, as shown below, two groups coming out of the benzene ring may be bonded to form a ring.

[0183] In the above formula, * is a bonding site with other sites, and R ｘ , Ma, x, Mb and y are R in formula (In-2). ｘ , Ma, x, Mb and y have the same meanings and preferred ranges.

[0184] In formula (In-1) and formula (In-2), R ｘ It is more preferable that the formula weight of each of the (groups containing a carbon-carbon unsaturated double bond) is independently 27 to 120.

[0185] In this embodiment, R ｘ The number of R in one molecule of the resin (IP1) is preferably 2.5 or more, more preferably more than 2.5, even more preferably 2.6 or more, even more preferably 2.7 or more, and still more preferably 2.8 or more. ｘThe number of R in one molecule of resin (IP1) is preferably 8.0 or less, more preferably 7.0 or less, even more preferably 6.5 or less, and even more preferably 6.0 or less, and may be 5.5 or less. ｘ By setting the number of in the above range, the low dielectric properties (low relative dielectric constant and / or low dielectric dissipation factor) and heat resistance of the obtained cured product tend to be further improved.

[0186] In this embodiment, the resin (IP1) preferably contains both a structure represented by formula (In-1) and a structure represented by formula (In-2).

[0187] Resin (IP1) typically contains an indane skeleton in addition to the structures represented by formula (In-1) and / or formula (In-2). Such indane skeletons other than the structures represented by formula (In-1) and / or formula (In-2) ​​are typically formed by a cyclization reaction of a compound represented by formula (DIP). That is, in Resin (IP1) of this embodiment, at least a portion of the structural units derived from the compound represented by formula (DIP) preferably contain an indane skeleton, and more preferably contain a structure represented by formula (In-0). (In formula (In-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 of 0 to 3. xq represents the number of bonds extending from the benzene ring and is an integer of 1 or 2. * represents a bonding site to another moiety. ** represents a bonding site to another moiety or a methyl group bonded to the cyclopentane ring. At least one of the two ** represents a bonding site to another moiety.)

[0188] In formula (In-0), Ma has the same meaning as Ma in formula (DIP), and the preferred range is also the same.

[0189] In formula (In-0), x represents an integer of 0 to 3, preferably an integer of 0 to 2, more preferably 0 or 1, and may be 0.

[0190] In formula (In-0), xq is the number of bonds coming out of the benzene ring and is an integer of 1 or 2. When xq is 2, as shown above, two groups coming out of the benzene ring may be bonded to form a ring.

[0191] The content of the indane skeleton in the resin (IP1) is not particularly limited, but when expressed by the above-mentioned parameter α, α is preferably 0.35 or more and 1.00 or less.

[0192] Specific examples of the structural unit derived from the compound represented by formula (DIP) in resin (IP1) include the structure represented by formula (In-0) above, as well as the following structural units (a) to (c) (hereinafter, sometimes referred to as formula (Tx)): In formula (Tx), * represents a bonding site with structural units (a) to (c), the structure represented by formula (In-1), the structure represented by formula (In-2), the structure represented by formula (In-0), the partial structures exemplified below, etc. In the structural units (a) to (c), Ma and x each independently have the same meaning as Ma and x in formula (DIP), and the preferred ranges are also the same. Specific examples of the structure in resin (IP1) containing a structural unit derived from the compound represented by formula (DIP) include the partial structures exemplified below. It goes without saying that the structural units in resin (IP1) derived from the compound represented by formula (DIP) and the structures containing a structural unit derived from the compound represented by formula (DIP) are not limited to these. Ma and x in the following formulas each independently have the same meaning as Ma and x in formula (DIP), and the preferred ranges are also the same.

[0193] In the above formula, * represents a bonding site to another site.

[0194] Another example of a compound having an indane skeleton with a terminal carbon-carbon unsaturated double bond other than the resin (A) is a resin represented by formula (D) (resin (IP2)). Such a resin (IP2) contains a group (R ｘIt is presumed that the bonding of the structural unit having an indane skeleton, etc., via an oxygen atom and / or a low-molecular-weight structural unit such as a phenyleneoxy group which may have a substituent increases the content of the indane skeleton (preferably a trimethylindane structure) in the cured product of the composition containing resin (IP2), thereby enabling a low Df (dielectric loss tangent). In particular, it is presumed that a low Df can be achieved even at a high curing temperature. Furthermore, the resin of this embodiment can have excellent heat resistance. Furthermore, resin (IP2) can also have a low Dk (dielectric constant). Resin (IP2) may be the same resin as resin (IP1). (In formula (D), R is a group containing a structural unit represented by formula (Tx). R ｘ is a group containing a carbon-carbon unsaturated double bond. ｙ represents a hydrogen atom, a group containing an —O-carbon-carbon unsaturated double bond, or another group. y1 represents an integer of 1 to 4. Mb's each independently represent a hydroxyl group, a halogen atom, or a hydrocarbon group having 1 to 20 carbon atoms which may be substituted with a hydroxyl group or a halogen atom. y 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.)

[0195] In formula (D), R is a group containing a structural unit represented by formula (Tx). That is, in resin (IP2), R contains at least the structural unit (a) in part and may further contain structural units (b) and / or (c). It may also contain structural units other than the structural units (a), (b), and (c) (hereinafter, sometimes referred to as "other structural units") or other groups. That is, the structural units (a), (b), and (c) may each be bonded by * to any of the structural units (a) to (c), other structural units other than the structural units (a) to (c), other groups, and groups bonded to R in formula (D). Furthermore, in resin (IP2), R does not necessarily have to be linear and may be bonded two-dimensionally or three-dimensionally. In this embodiment, resin (IP2) (particularly the group containing the structural unit represented by formula (Tx)) is preferably linear. Linear bonding of the structural units constituting resin (IP2) tends to improve low dielectric properties, which is preferred. Examples of other structural units include structural units derived from the compound represented by formula (DIP) that are bonded to any of structural units (a), (b), and (c). It goes without saying that the structural units derived from the compound represented by formula (DIP) may be synthesized from the compound represented by formula (DIP), or may be synthesized from other raw materials that provide structural units derived from the compound represented by formula (DIP). Examples of other raw materials that provide structural units derived from the compound represented by formula (DIP) include α,α'-dihydroxy-1,3-diisopropylbenzene, α,α'-dihalogeno-1,3-diisopropylbenzene, α,α'-dialkoxy-1,3-diisopropylbenzene, and equivalents of the compound represented by formula (DIP) that provide the compound represented by formula (DIP) through unit operations such as heating.

[0196] (In formula (DIP), each Ma independently represents a hydrocarbon group having 1 to 12 carbon atoms which may be substituted with a halogen atom, and x represents an integer of 0 to 4.) The details of formula (DIP) are the same as those described above in the section on resin (IP1), and the preferred ranges are also the same.

[0197] Furthermore, when resin (IP2) contains other structural units, resin (IP2) may have a branched structure. Furthermore, in resin (IP2), the double bond of structural units (b) and / or (c) may react with a structural unit derived from the compound represented by formula (DIP) to form a ring, thereby constituting a structural unit having an indane skeleton. An example of such a structure is shown below. In the above structure, Ma and x each independently have the same definition as Ma and x in formula (Tx) described above, and the preferred ranges are also the same. In the above structure, * is preferably bonded to any of the terminal groups bonded to R in formula (D) or to any of the structural units (a) to (c). Furthermore, a terminal group may be bonded to the structural unit (a), (b), or (c). Furthermore, resin (IP2) may contain the following compound. In the above compound, Ma and x have the same meanings as Ma and x in the above formula (Tx), respectively, and the preferred ranges are also the same. Furthermore, Mb and y each independently have the same meanings as Mb and y in the above formula (D), and the preferred ranges are also the same. ｘ is a group containing a carbon-carbon unsaturated double bond.

[0198] The formula (Tx) has the same meaning as (Tx) described in the section on resin (A), and the preferred range is also the same.

[0199] In formula (D), R ｘ is a group containing a carbon-carbon unsaturated double bond, and more preferably a group having a formula weight of 27 to 120. ｘ Specifically, each of Rx-11 and Rx-2 is preferably a group represented by formula (Rx-11) or a group represented by formula (Rx-2), more preferably a vinylbenzyl group or a (meth)acryloyl group, and even more preferably a vinylbenzyl group. (In formula (Rx-11) and formula (Rx-2), R １ , R ２ , and R ３each 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. r1 represents an integer of 1 to 6.

[0200] Formula (Rx-11) and Formula (Rx-2) have the same meanings and preferred ranges as Formula (Rx-1) and Formula (Rx-2) described in the section on polyphenylene ether compounds above, except for r1. r1 in Formula (Rx-11) 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.

[0201] In formula (D), R ｙ is a hydrogen atom, a group containing an —O-carbon-carbon unsaturated double bond, or other group. ｙ is bonded to R at any position, but may be bonded to any of the structural units (a), (b), and (c) contained in R, and the other structural units described above. An example of a mode of bonding to R is a mode of bonding to a benzene ring possessed by the structural unit (a), (b), or (c). Yet another example of a mode of bonding to R is a mode of bonding to a structural unit other than the structural units (a), (b), and (c) contained in R. The resin of this embodiment preferably has a structure in which R ｙ At least one of the following is bonded to a benzene ring of the structural unit (a), (b) or (c), and more preferably R ｙ At least one of the following is bonded to a benzene ring of the structural unit (a).

[0202] R ｙ is a group containing an —O-carbon-carbon unsaturated double bond, the group containing a carbon-carbon unsaturated double bond is ｘ The same definition and preferred range are also true. ｙAmong these, the number of groups containing a carbon-carbon unsaturated double bond is preferably 0.2 or more, more preferably 0.3 or more, even more preferably 0.4 or more, still more preferably 0.5 or more, and even more preferably 0.8 or more, and may be 1.0 or more, on the average of all molecules in the resin (IP2). ｙ The number of groups containing a carbon-carbon unsaturated double bond in the resin is, on average for all molecules in the resin, preferably 7 or less, more preferably 6 or less, even more preferably 5 or less, still more preferably 4 or less, and even more preferably 3 or less, and may further be 2.5 or less, 1.5 or less, less than 1.5, 1.4 or less, or 1.2 or less.

[0203] R ｙ When has another group, examples of the other group include an organic group, a hydroxyl group, or a halogen atom. The organic group is preferably a hydrocarbon group having 1 to 20 carbon atoms which may be substituted with a hydroxyl group or a halogen atom, more preferably a hydrocarbon group having 1 to 5 carbon atoms which may be substituted with a hydroxyl group or a halogen atom, even more preferably a saturated hydrocarbon group having 1 to 5 carbon atoms, still more preferably a saturated hydrocarbon group having 1 to 3 carbon atoms, and even more preferably a propyl group or an isopropyl group.

[0204] In formula (D), y1 is an integer of 1 to 4, preferably 1 or more, and more preferably 3 or less, more preferably 2 or less, and even more preferably 1.

[0205] R per molecule of resin (IP2) ｘ and / or R ｙ The total number of groups containing a carbon-carbon unsaturated double bond contained in R is preferably 2.5 or less, more preferably less than 2.5, even more preferably 2.4 or less, and may be 2.2 or less, on the average of all molecules in the resin (IP2). ｘ and / or R ｙThe total number of groups containing a carbon-carbon unsaturated double bond contained in is preferably 0.8 or more, more preferably 1.2 or more, even more preferably 1.3 or more, even more preferably 1.4 or more, still more preferably 1.5 or more, still more preferably 1.8 or more, and may be 2.0 or more. By setting the total number of groups containing a carbon-carbon unsaturated double bond within the above range, the cured product tends to have excellent low dielectric properties.

[0206] In formula (D), each Mb independently represents a hydroxyl group, a halogen atom, or a hydrocarbon group having 1 to 20 carbon atoms which may be substituted with a hydroxyl group or a halogen atom, and has the same definition as Mb in formula (T-St) above, and the preferred range is also the same.

[0207] In formula (D), y represents an integer of 0 to 4, preferably an integer of 0 to 3, more preferably an integer of 0 to 2, and even more preferably 0 or 2, and may be 0. Furthermore, y is preferably 2 from the viewpoint of dielectric properties. Furthermore, when y is 1 or more, Mb is preferably R ｘ It is preferably bonded at the adjacent position (ortho position) to the carbon atom to which the O group is bonded.

[0208] In the resin (IP2) of this embodiment, the formula (D) is preferably represented by the formula (D-1). (In formula (D-1), R is a group containing a structural unit represented by formula (Tx). ｘ are each independently a group containing a carbon-carbon unsaturated double bond. Mb's are each independently a hydroxyl group, a halogen atom, or a hydrocarbon group having 1 to 20 carbon atoms which may be substituted with a hydroxyl group or a halogen atom. y is an integer of 0 to 4.

[0209] Furthermore, formula (D-1) is preferably represented by formula (D-1-2). (In formula (D-1-2), R is a group containing a structural unit represented by formula (Tx). ｘare each independently a group containing a carbon-carbon unsaturated double bond. Mb's are each independently a hydroxyl group, a halogen atom, or a hydrocarbon group having 1 to 20 carbon atoms which may be substituted with a hydroxyl group or a halogen atom. y is an integer of 0 to 4.

[0210] In addition, in the resin (IP2) of this embodiment, the formula (D) is preferably represented by the formula (D-2). (In formula (D-2), R' is a group that, together with the group having an indane skeleton adjacent to the left side, becomes a group containing a structural unit represented by formula (Tx), and R ｘ are each independently a group containing a carbon-carbon unsaturated double bond. Mb's are each independently a hydroxyl group, a halogen atom, or a hydrocarbon group having 1 to 20 carbon atoms which may be substituted with a hydroxyl group or a halogen atom. y is an integer of 0 to 4.

[0211] Furthermore, formula (D-2) is preferably represented by formula (D-2-1). (In formula (D-2-1), R' is a group that, together with the group having an indane skeleton adjacent to the left side, becomes a group containing a structural unit represented by formula (Tx), and R ｘ are each independently a group containing a carbon-carbon unsaturated double bond. Mb's are each independently a hydroxyl group, a halogen atom, or a hydrocarbon group having 1 to 20 carbon atoms which may be substituted with a hydroxyl group or a halogen atom. y is an integer of 0 to 4.

[0212] In formula (D-1), formula (D-1-2), formula (D-2), and formula (D-2-1), R ｘ are each independently R in formula (D). ｘ In formula (D-1) and formula (D-1-2), R each independently has the same meaning as R in formula (D), and the same preferred range applies. In formula (D-2) and formula (D-2-1), R' is a group that, together with the group having an indane skeleton adjacent to it on the left, becomes a group containing a structural unit represented by formula (Tx). That is, in formula (D), R ｙis a group containing an —O-carbon-carbon unsaturated double bond, and the oxygen atom is essentially bonded to the benzene ring of the structural unit (a) in formula (Tx). Specifically, for example, in formula (D-2), the circled portion below corresponds to R in formula (D):

[0213] In formula (D-1), formula (D-1-2), formula (D-2) and formula (D-2-1), Mb and y each independently have the same meaning as Mb and y in formula (D), and the preferred ranges are also the same.

[0214] In this embodiment, the resin (IP1) and / or the resin (IP2) preferably have a parameter α calculated by the formula (α) of 0.35 or more and 1.00 or less. (The brackets in formula (α) are: １ represents the integral between the corresponding chemical shift values ​​in H-NMR.) Here, α represents the ratio of the structural units having an indane skeleton in resin (IP1) and / or resin (IP2) (mainly the structural unit (a) in formula (Tx)). More specifically, by adjusting the ratio of the structural units having an indane skeleton in resin (IP1) and / or resin (IP2) so as to satisfy the range of the parameter α, the rigidity of the resulting resin molecules is increased, and since highly rigid molecules have lower mobility than less rigid molecules, it is presumed that the relaxation time during dielectric relaxation is longer and the dielectric loss tangent (Df) can be lowered. Furthermore, since the rigidity of the resin molecules is increased, it is presumed that the glass transition temperature of the cured product can be increased and the heat resistance is excellent. In this embodiment, it is presumed that R in formula (D) (a group containing a structural unit represented by formula (Tx)) is a group containing a carbon-carbon unsaturated double bond (R ｘ ) via an oxygen atom and / or a low-molecular-weight structural unit such as a phenyleneoxy group which may have a substituent, the content of the indane skeleton in the resin (IP1) and / or the resin (IP2) can be increased.

[0215] The parameter α in resin (IP1) and / or resin (IP2) is more preferably 0.36 or more, even more preferably 0.40 or more, even more preferably 0.45 or more, even more preferably 0.50 or more, and may be 0.55 or more, 0.60 or more, 0.65 or more, or 0.70 or more. By setting the parameter α to the above-mentioned lower limit or more, the low dielectric properties (low relative dielectric constant and / or low dielectric dissipation factor) and heat resistance of the obtained cured product tend to be further improved. Since the parameter α tends to be substantially excellent in low dielectric properties and heat resistance, the parameter α is preferably large, but may be 0.98 or less, 0.95 or less, 0.90 or less, 0.85 or less, 0.84 or less, or 0.82 or less.

[0216] The number-average molecular weight of resin (IP1) and / or resin (IP2) is preferably 8,000 or less, more preferably 4,000 or less. By setting the number-average molecular weight to the above-mentioned lower limit or more, the low dielectric properties (particularly low dielectric tangent) of the resulting cured product tend to be further improved. This is thought to be because increasing the molecular weight increases the proportion of indane skeletons (e.g., structural unit (a) in formula (Tx)) contained in the molecule. Furthermore, by setting the number-average molecular weight to the above-mentioned upper limit or less, the moldability and solvent solubility of the resin tend to be further improved. The lower limit of the number average molecular weight of Resin (IP1) and / or Resin (IP2) is more preferably 500 or more, even more preferably 600 or more, still more preferably 700 or more, and even more preferably 800 or more, and may be 850 or more, 900 or more, 1000 or more, 1100 or more, 1200 or more, 1300 or more, 1400 or more, 1500 or more, 1600 or more, 1700 or more, 1800 or more, 1900 or more, 2000 or more, 2200 or more, 2300 or more, 2400 or more, 2500 or more, or 2600 or more. The upper limit of the number average molecular weight of Resin (IP1) and / or Resin (IP2) is more preferably 7,000 or less, even more preferably 6,000 or less, still more preferably 5,000 or less, and still more preferably 4,000 or less, and may be 3,800 or less, 3,500 or less, 3,200 or less, or 3,000 or less, or may even be 2,800 or less, 2,600 or less, 2,400 or less, 2,200 or less, 2,000 or less, 1,900 or less, 1,800 or less, 1,700 or less, 1,600 or less, or 1,500 or less.

[0217] The method for producing the resin represented by formula (IP1) and / or (IP2) is not particularly limited. For example, they can be produced using a hydroxy resin represented by formula (D) above, in which the RxO and Ry moieties are hydroxyl groups. A first embodiment of the method for producing resin (IP1) and / or resin (IP2) includes reacting a mixture containing a compound represented by formula (DIP) and a compound represented by formula (P1) to synthesize a resin having hydroxyl groups (hereinafter, sometimes referred to as a "hydroxy resin"), and then reacting the hydroxy resin with a compound having a group containing a carbon-carbon unsaturated double bond and a group that reacts with and leaves the hydroxyl group of the hydroxy resin. Furthermore, the hydroxy resin may be synthesized by reacting a compound represented by formula (DIP) with a compound represented by formula (P1), which will be described later, and then further reacting the compound represented by formula (DIP). (In formula (P1), Mb's each independently represent a hydroxyl group, a halogen atom, or a hydrocarbon group having 1 to 20 carbon atoms which may be substituted with a hydroxyl group or a halogen atom; and y represents an integer of 0 to 4.) Mb and y in formula (P1) above have the same meanings as Mb and y in formula (D), and the preferred ranges are also the same.

[0218] A compound having a group containing a carbon-carbon unsaturated double bond and a group that reacts with a hydroxyl group of a hydroxyl resin and is cleaved will be described. The group containing a carbon-carbon unsaturated double bond is preferably a group represented by the above formula (Rx-1) or a group represented by formula (Rx-2), more preferably a vinylbenzyl group or a (meth)acryloyl group, and even more preferably a vinylbenzyl group. On the other hand, examples of the group that reacts with a hydroxyl group of a hydroxyl resin and is cleaved include a halogen atom, a hydroxyl group, an alkoxy group, and a (meth)acryloyl group, with a halogen atom being preferred. Examples of the halogen atom include a chlorine atom, a bromine atom, and an iodine atom, with a chlorine atom or a bromine atom being preferred.

[0219] In a first embodiment of the method for producing resin (IP1) and / or resin (IP2), a polymer (oligomer) mainly composed of structural units derived from the compound represented by formula (DIP) is synthesized from the compound represented by formula (DIP), and then the polymer is reacted with a compound represented by formula (P1) to synthesize a hydroxy resin. The resulting hydroxy resin is then reacted with a compound having a group containing a carbon-carbon unsaturated double bond and a group that reacts with the hydroxyl group of the hydroxy resin to leave, thereby producing resin (IP1) and / or resin (IP2).

[0220] When the resin composition of this embodiment contains a compound having an indane skeleton with a terminal carbon-carbon unsaturated double bond other than the resin (A), the content thereof 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 compound having an indane skeleton with a terminal carbon-carbon unsaturated double bond other than the resin (A), or may contain two or more compounds. When two or more compounds are contained, it is preferable that the total amount is within the above range. Furthermore, the resin composition of this embodiment may be configured to be substantially free of compounds having an indane skeleton with a terminal carbon-carbon unsaturated double bond other than the resin (A). "Substantially free" means that the content of compounds having an indane skeleton with a terminal carbon-carbon unsaturated double bond other than the resin (A) 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.

[0221] <<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, bisphenol E-type cyanate ester compounds, diallyl bisphenol A-type cyanate ester compounds, and indancyanate 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.

[0222] 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.

[0223] 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.

[0224] 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.

[0225] 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.

[0226] 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.

[0227] Examples of the indancyanate compound include compounds represented by the following formula (a): (In formula (a), n is the average number of repetitions and is a number of 3.0 to 15.0.)

[0228] In addition to the above, the cyanate ester compounds that can be used include the compounds described in paragraphs 0035 to 0061 of Japanese Patent Application No. 2024-110099, the contents of which are incorporated herein by reference.

[0229] 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.

[0230] <Curable Compound Other Than Resin (A) and Curable Compound (C)> The resin composition of this embodiment may contain resin (A) and at least one thermosetting compound other than the thermosetting compound (C) selected from the group consisting of a compound having a terminal polymerizable carbon-carbon unsaturated double bond other than the resin (A), a maleimide compound, and a cyanate ester compound. Here, the compound having a terminal polymerizable carbon-carbon unsaturated double bond includes a compound having a structure shown below at the terminal. In the above, * denotes a binding site to another site, and R Ｄ１ is a hydrogen atom, a substituent, or a bonding site with another moiety. Examples of such other thermosetting compounds include perfluorovinyl ether resins, epoxy compounds, phenolic compounds, oxetane compounds, benzoxazine compounds, arylcyclobutene resins, polyamide compounds, polyimide compounds, and compounds having a vinylene group. 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, per 100 parts by mass of the resin solids 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.

[0231] <<Perfluorovinyl ether resin>> The resin composition of this embodiment may contain a perfluorovinyl ether resin. Examples of perfluorovinyl ether resins include perfluorovinyl benzyl ether resins. For details, see the perfluorovinyl ether resins described in paragraph 0043 of JP 2019-194312 A, the contents of which are incorporated herein by reference.

[0232] <<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.

[0233] 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 content of the epoxy compound is 0.1 parts by mass or more, peel strength and toughness tend to be improved. The upper limit of the content of the epoxy compound is preferably 50 parts by mass or less, more preferably 30 parts by mass or less, even more preferably 20 parts by mass or less, 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 content of the epoxy compound is 50 parts by mass or less, the electrical properties of the obtained 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.

[0234] <<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.

[0235] Another example of a phenol compound that can be used in this embodiment is a resin having a hydroxyl group obtained by reacting a mixture containing a compound represented by formula (DIP) and a compound represented by formula (P1). (In formula (DIP), each Ma independently represents a hydrocarbon group having 1 to 12 carbon atoms which may be substituted with a halogen atom, and x represents an integer of 0 to 4.) (In formula (P1), each Mb independently represents a hydroxyl group, a halogen atom, or a hydrocarbon group having 1 to 20 carbon atoms which may be substituted with a hydroxyl group or a halogen atom; and y represents an integer of 0 to 4.)

[0236] Formula (DIP) has the same meaning as Formula (DIP) described in the section on Resin (IP1), and the preferred range is also the same. In Formula (P1), Mb and y each independently have the same meaning as Mb and y in the above-mentioned Formula (T-St), and the preferred range is also the same. For details of the resin having a hydroxyl group obtained by reacting a mixture containing a compound represented by Formula (DIP) and a compound represented by Formula (P1), please refer to the description of Japanese Patent Application No. 2022-180443, the contents of which are incorporated herein by reference.

[0237] Another example of the phenol compound that can be used in this embodiment is a hydroxy resin represented by the formula (T-OH). (In formula (T-OH), R is a group containing a structural unit represented by formula (Tx). R ｔｐ represents a hydrogen atom, a hydroxyl group, an isopropenyl group, or another group. Each Mb independently represents a hydroxyl group, a halogen atom, or a hydrocarbon group having 1 to 20 carbon atoms which may be substituted with a hydroxyl group or a halogen atom. y 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.)

[0238] Formula (T-OH) is preferably represented by formula (T-OH2), and more preferably represented by formula (T-OH3). (In formula (T-OH2), R' is a group that, together with the group having an indane skeleton adjacent to the left side, becomes a group containing a structural unit represented by formula (Tx), and R ｔｐ represents a hydrogen atom, a hydroxyl group, an isopropenyl group, or another group. Each Mb independently represents a hydroxyl group, a halogen atom, or a hydrocarbon group having 1 to 20 carbon atoms which may be substituted with a hydroxyl group or a halogen atom. y represents an integer of 0 to 4. (In formula (T-OH3), R' is a group that, together with the group having an indane skeleton adjacent to the left side, becomes a group containing a structural unit represented by formula (Tx), and R ｔｐ２ represents a hydroxyl group or an isopropenyl group. Each Mb independently represents a hydroxyl group, a halogen atom, or a hydrocarbon group having 1 to 20 carbon atoms which may be substituted with a hydroxyl group or a halogen atom. y represents an integer of 0 to 4.

[0239] In formula (T-OH), R has the same definition as R in formula (T1-1) above, and the preferred range is also the same. Mb and y each independently have the same definition as Mb and y in formula (T-St) above, and the preferred range is also the same. R ｔｐ is preferably a hydroxyl group or an isopropenyl group, more preferably a hydroxyl group.

[0240] In formula (T-OH2) and formula (T-OH3), R' has the same definition as R in formula (T1-1) above, and the preferred range is also the same. Mb and y each independently have the same definition as Mb and y in formula (T-St) above, and the preferred range is also the same. In formula (T-OH2), R ｔｐ is preferably a hydroxyl group or an isopropenyl group, and more preferably a hydroxyl group. ｔｐ２ is preferably a hydroxyl group.

[0241] For details of the hydroxy resins represented by formulas (T-OH1) to (T-OH3), please refer to the description in Japanese Patent Application No. 2022-180444, the contents of which are incorporated herein by reference.

[0242] Another example of the phenol compound that can be used in this embodiment is a hydroxy resin represented by formula (T-OH4). (In formula (T-OH4), R represents a group containing a structural unit represented by formula (Tx). Each Ma independently represents a hydrocarbon group of 1 to 12 carbon atoms which may be substituted with a halogen atom. Each Mb independently represents a hydroxyl group, a halogen atom, or a hydrocarbon group of 1 to 20 carbon atoms which may be substituted with a hydroxyl group or a halogen atom. Each x and y independently represent 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.)

[0243] In formula (T-OH4), Ma and x each independently have the same meaning as Ma and x in formula (T1), and the preferred range is also the same. In formula (T-OH4), Mb and y each independently have the same meaning as Mb and y in formula (T-St) described above, and the preferred range is also the same. In formula (T-OH4), R has the same meaning as R in formula (T-OH), and the preferred range is also the same.

[0244] For details of the hydroxy resin represented by formula (T-OH4), please refer to paragraphs 0018 to 0019 of PCT / JP2023 / 009587, the contents of which are incorporated herein by reference.

[0245] 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.

[0246] <<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.).

[0247] 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, relative to 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 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, still more preferably 10 parts by mass or less, and even more preferably 8 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 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.

[0248] <<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.).

[0249] 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.

[0250] <<Arylcyclobutene Resin>> The resin composition of this embodiment may contain an arylcyclobutene resin. For details, examples include the arylcyclobutene resins described in paragraph 0042 of JP 2019-194312 A, the contents of which are incorporated herein by reference.

[0251] The resin composition of this embodiment preferably contains an arylcyclobutene resin to the extent that the effects of the present invention are not impaired. When the resin composition of this embodiment contains an arylcyclobutene resin, 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 arylcyclobutene resin, 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 arylcyclobutene resin. "Substantially free" means that the content of arylcyclobutene resin is less than 0.1 parts by mass per 100 parts by mass of the resin solid content in the resin composition.

[0252] <<Polyamide Compound>> The resin composition of the present embodiment may contain a polyamide compound or a thermosetting polyamide compound. For details, see the polyamides and the like described in paragraph 0063 of Japanese Patent No. 6951829, the contents of which are incorporated herein by reference.

[0253] The resin composition of this embodiment preferably contains a polyamide compound within a range that does not impair the effects of the present invention. When the resin composition of this embodiment contains a polyamide 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 polyamide 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 polyamide compound. "Substantially free" means that the content of the polyamide compound is less than 0.1 parts by mass per 100 parts by mass of the resin solid content in the resin composition.

[0254] <<Polyimide Compound>> The resin composition of the present embodiment may contain a polyimide compound or a thermosetting polyimide compound. For details, see the polyimides and the like described in paragraph 0064 of Japanese Patent No. 6,951,829, the contents of which are incorporated herein by reference.

[0255] The resin composition of this embodiment preferably contains a polyimide compound to the extent that the effects of the present invention are not impaired. When the resin composition of this embodiment contains a polyimide 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 polyimide 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 polyimide compound. "Substantially free" means that the content of the polyimide compound is less than 0.1 parts by mass per 100 parts by mass of the resin solid content in the resin composition.

[0256] <<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 maleimide compounds are referred to as maleimide compounds. Specific examples of compounds having a vinylene group include preferred acenaphthylene and pyracylene, and more preferred is acenaphthylene. 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 imidazole compounds described below, are not considered to be compounds having a vinylene group.

[0257] <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.

[0258] The filler used in this embodiment is not particularly limited in type, and can be suitably used in the 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, zinc borate, zinc stannate, forsterite, barium titanate, strontium titanate, calcium titanate, composite oxides such as boron nitride, aggregated boron nitride, silicon nitride, aluminum nitride, nitrides such as aluminum hydroxide, aluminum hydroxide heat treatment product (aluminum hydroxide is heat treated and part of the crystal water is reduced), boehmite, magnesium hydroxide, metal hydroxide (including hydrate), molybdenum oxide, Examples of fillers include inorganic fillers such as molybdenum compounds such as arsenic and zinc molybdate, barium sulfate, clay, kaolin, talc, calcined clay, calcined kaolin, calcined talc, mica, E-glass, A-glass, NE-glass, NER-glass, NEZ-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.

[0259] 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 40 parts by mass or more, even more preferably 60 parts by mass or more, and even more preferably 80 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 300 parts by mass or less, even more preferably 250 parts by mass or less, and may be 200 parts by mass or less, or 120 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.

[0260] When a filler, particularly an inorganic filler, is used in the resin composition of this embodiment, a silane coupling agent may be further contained. The inclusion of a silane coupling agent tends to further improve the dispersibility of the filler and the adhesive strength between the resin component and the filler and the substrate described below. The silane coupling agent is not particularly limited, and examples thereof include silane coupling agents generally used for the surface treatment of inorganic substances, such as 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. Among these, it is preferable to include at least one selected from the group consisting of vinylsilane compounds, styrylsilane compounds, and acrylicsilane compounds, and vinylsilane compounds are more preferable. The silane coupling agent may be used alone or in combination of two or more. The content of the silane coupling agent is not particularly limited, but may be 0.1 to 5.0 parts by mass per 100 parts by mass of the resin solid content.

[0261] <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, 2-phenyl-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, Examples of suitable curing accelerators include tertiary amines such as N-methylmorpholine, triethanolamine, triethylenediamine, tetramethylbutanediamine, and N-methylpiperidine; phenols such as phenol, xylenol, cresol, resorcinol, and catechol; high-temperature decomposition 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 prepared by dissolving these organic metal salts in hydroxyl-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.

[0262] 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.

[0263] <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).

[0264] When the resin composition of this embodiment contains a flame retardant, the content thereof is preferably 1 part by mass or more, more preferably 5 parts by mass or more, even more preferably 10 parts by mass or more, and may even be 15 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 25 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.

[0265] <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.

[0266] 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.

[0267] <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.

[0268] 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.

[0269] <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.

[0270] <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, 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. The content of other components (various polymeric compounds such as thermoplastic resins and their oligomers, various additives, etc.) other than the above components in the resin composition of this embodiment is preferably 0 parts by mass or more but less than 10 parts by mass, more preferably 0 parts by mass or more but less than 5 parts by mass, even more preferably 0 parts by mass or more but less than 3 parts by mass, and may be 0 parts by mass or more but less than 1 part by mass, relative to 100 parts by mass of the resin solid content. The content (total amount) of the additives is preferably 0 parts by mass or more and less than 5 parts by mass, more preferably 0 parts by mass or more and less than 3 parts by mass, even more preferably 0 parts by mass or more and less than 1 part by mass, and may be 0 parts by mass or more and less than 0.5 parts by mass, relative to 100 parts by mass of the resin solid content.

[0271] Examples of the polymerization inhibitor include quinone, phenolic, nitroso, hydroxyamine, organic boric acid compounds, and compounds having a phenolic hydroxyl group. Specific examples include 2-nitrophenol, 4-methoxyphenol, 4-tert-butylpyrocatechol, pyrogallol, 4,4'-butylidenebis(6-tert-butyl-m-cresol), tert-butylhydroquinone, 1,4-benzoquinone, 2-hydroxybenzophenone, cuprous chloride, phenothiazine, chloranil, naphthylamine, β-naphthol, 2,6-di-t-butyl-4-cresol, 2,2'-methylenebis(4-methyl- 6-t-butylphenol), pyridine, nitrobenzene, dinitrobenzene, picric acid, 4-toluidine, methylene blue, copper reactants with organic chelating agents, methyl salicylate, dibutylhydroxytoluene, 1,1-diphenyl-2-picrylhydrazyl free radical, hydroquinone, hydroquinone monomethyl ether, mequinol, N-nitroso-N-phenylhydroxylamine aluminum, triethyl borate, tributyl borate, triisopropyl borate, 2,3-dihydroxynaphthalene, 4-methoxy-1-naphthol, methylhydroquinone, etc. The polymerization inhibitor to be used is not limited to the above.

[0272] When the resin composition of this embodiment contains a polymerization inhibitor, the content thereof is preferably 0.001 parts by mass or more, more preferably 0.01 parts by mass or more, even more preferably 0.02 parts by mass or more, and even more preferably 0.04 parts by mass or more, relative to 100 parts by mass of the resin solids. It is also preferably 10 parts by mass or less, more preferably 3 parts by mass or less, even more preferably 1 part by mass or less, even more preferably 0.5 parts by mass or less, and even more preferably 0.2 parts by mass or less. By setting the content at or above the lower limit, the low dielectric properties (Dk and / or Df, particularly Df) of the resulting cured product after long-term heating tend to be further improved. Furthermore, by setting the content at or below the upper limit, the low dielectric properties (Dk and / or Df) and heat resistance of the resulting cured product tend to be excellent. The resin composition of this embodiment may contain only one type of polymerization inhibitor, or two or more types. When two or more types are contained, the total amount is preferably within the above range.

[0273] <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.

[0274] The resin composition of this embodiment preferably has a low dielectric constant (Dk) and dielectric loss tangent (Df) of the cured product. Specifically, the dielectric constant (Dk) at a frequency of 10 GHz measured according to the cavity resonator perturbation method when molded into a 1.0 mm thick cured plate (without metal foil) is preferably less than 2.4. The lower limit of the dielectric constant (Dk) is not particularly specified, but a practical value is, for example, 0.01 or more. Furthermore, the dielectric loss tangent (Df) at a frequency of 10 GHz measured according to the cavity resonator perturbation method when molded into a 1.0 mm thick cured plate (without metal foil) is preferably 0.0020 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. The resin composition of this embodiment preferably satisfies the above Dk of less than 2.40 and Df of 0.0020 or less. Furthermore, after forming the cured sheet into a 1.0 mm thick (without metal foil) and heating it at 130°C for 500 hours, the increase in dielectric loss tangent (Df) at a frequency of 10 GHz measured according to the cavity resonator perturbation method is preferably 0.0040 or less, more preferably 0.0030 or less, even more preferably 0.0020 or less, and even more preferably 0.0010 or less. The lower limit is preferably 0, and may be 0.0001 or more. The relative dielectric constant (Dk) and dielectric loss tangent (Df) of the cured sheet are more specifically measured by the method described in the Examples below.

[0275] 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.

[0276] <<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.

[0277] 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, NEZ-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, NEZ-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.

[0278] <<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.

[0279] 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.

[0280] 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.

[0281] 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.

[0282] <<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.

[0283] 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.

[0284] 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.

[0285] <<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.

[0286] 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.

[0287] 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.

[0288] 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.

[0289] 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.

[0290] <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.

[0291] <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.)

[0292] 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 the mixture was 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 allowed to react for an additional hour at this internal temperature. After allowing to cool, the activated clay was removed by filtration, and the solvent was distilled off under reduced pressure with heating to obtain 129 g of a solid resin. The NMR chart of the resulting resin is shown in Figure 1. The Mw of the resulting 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 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 by (number average molecular weight (Mn) ÷ 2) ÷ β.

[0293] Synthesis Example 2 Polyphenylene Ether Compound (B1) Having Terminal Carbon-Carbon Unsaturated Double Bonds Synthesis of Bifunctional Phenylene Ether Oligomer A 12-L vertical reactor equipped with a stirrer, a thermometer, an air inlet tube, and a baffle plate was charged with CuBr. ２9.36 g (42 mmol) of (copper bromide), 1.81 g (11 mmol) of N,N'-di-t-butylethylenediamine, 67.8 g (670 mmol) of n-butyldimethylamine, and 2600 g of toluene were charged and stirred at an internal temperature of 40°C. To this mixture, a mixed solution of 129.3 g (0.48 mol) of 2,2',3,3',5,5'-hexamethyl-(1,1'-biphenyl)-4,4'-diol, 878 g (7.2 mol) of 2,6-dimethylphenol, 1.22 g (7.2 mmol) of N,N'-di-t-butylethylenediamine, and 26.4 g (261 mmol) of n-butyldimethylamine, which had been dissolved in advance in 2300 g of methanol, was added dropwise over 230 minutes while bubbling a mixed gas prepared by mixing nitrogen and air to an oxygen concentration of 8% at a flow rate of 5.2 L / min, and the mixture was stirred at a reaction temperature of 40°C. After completion of the dropwise addition, 1500 g of water in which 48.1 g (130 mmol) of tetrasodium ethylenediaminetetraacetate had been dissolved was added to quench the reaction. The aqueous and organic layers 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 to obtain 1980 g of a toluene solution A1 of a phenylene ether resin. The number average molecular weight (as converted into polystyrene) measured by the GPC method was 1975, the weight average molecular weight (as converted into polystyrene) measured by the GPC method was 3514, and the hydroxyl equivalent was 990 g / eq.

[0294] <<Synthesis of Modified Polyphenylene Ether Compound>> A reactor equipped with a stirrer, thermometer, and reflux condenser was charged with 833 g of the toluene solution A1 of the phenylene ether resin obtained above, 76.7 g (0.50 mol) of vinylbenzyl chloride (manufactured by AGC Seimi Chemical Co., Ltd., "CMS-P"), 1,600 g of methylene chloride, 6.20 g (0.046 mol) of benzyldimethylamine, 200 g of pure water, and 84 g of a 30.5% by 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 450 g of a polyphenylene ether compound (B1) mainly composed of a compound represented by formula (OP-15). The number average molecular weight (GPC) was 2,250 in terms of polystyrene, the weight average molecular weight (GPC) was 3,920 in terms of polystyrene, the vinyl double bond equivalent was 1,189 g / eq., and the hydroxyl equivalent was 56,250 g / eq.

[0295] 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.

[0296] 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 １By 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.

[0297] Synthesis Example 4 Polyphenylene Ether Compound (B2) Having Terminal Carbon-Carbon Unsaturated Double Bonds 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 (copper bromide) 　 0.33 g (1.5 mmol), N,N'-di-t-butylethylenediamine 0.63 g (3.7 mmol), n-butyldimethylamine 6.95 g (69 mmol), toluene 670 g, and methanol 320 g were charged and dissolved by stirring at an internal temperature of 40°C. To this, 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), and CuBr were added in a separate container (dropping tank) in advance. ２ (copper bromide) 　0.33 g (1.5 mmol), N,N'-di-t-butylethylenediamine 0.63 g (3.7 mmol), n-butyldimethylamine 6.95 g (69 mmol), toluene 440 g, and methanol 170 g were charged and dissolved with stirring at an internal 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 stirring was continued at a reaction temperature of 40 °C. 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 a phenylene ether resin toluene solution A2. 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.

[0298] <<Synthesis of Modified Polyphenylene Ether Compound>> A reactor equipped with a stirrer, thermometer, and reflux condenser was charged with 300 g of the toluene solution A2 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% by 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 (B2) composed primarily 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.

[0299] Example 1 20 parts by mass of the resin (A) obtained in Synthesis Example 1 above, 70 parts by mass of a maleimide compound (ma) shown in the structure below (NE-X-9470S, manufactured by DIC Corporation; functional group equivalent (maleimide group equivalent) was 450 g / eq.), and 10 parts by mass of a hydrogenated styrene-based thermoplastic elastomer (SEPS, SEPTON 2104, Mn 83000, manufactured by Kuraray Co., Ltd.) were dissolved in methyl ethyl ketone and toluene and mixed to obtain a varnish. The contents of each of the above components indicate values ​​based on the solid content.

[0300] Maleimide compound (ma)

[0301] <Production of 1.0 mm Thick Cured Plate Test Pieces> The solvent was evaporated and removed from the resulting varnish to obtain a resin composition powder. Using the resulting resin composition powder, a cured plate was produced as follows. 4.5 g of the resin composition powder was placed in a stainless steel mold frame measuring 100 mm x 30 mm x 1.0 mm high, placed in a vacuum press (manufactured by Kitagawa Seiki Co., Ltd.), and held at 200°C for 1.5 hours, pressing at a surface pressure of 1.9 MPa. Using the resulting cured plate, evaluations of moldability, relative dielectric constant (Dk), dielectric loss tangent (Df), and Df after heat treatment were performed. The evaluation results are shown in Tables 1, 2, and 3.

[0302] <Measurement and Evaluation Methods> (1) Moldability Moldability was evaluated as follows. The cured plate obtained as described above was downsized to a width of 1.0 mm and then dried at 120°C for 60 minutes. A: Moldable and not deformed even under drying conditions of 120°C for 60 minutes. B: Moldable, but deformed under drying conditions of 120°C for 60 minutes, making it impossible to evaluate the properties. C: Unable to mold due to cracking.

[0303] (2) Dielectric Properties Among the samples that underwent the moldability evaluation, samples that received an A rating were used as they were to measure the relative permittivity (Dk) and dielectric loss tangent (Df) at a frequency of 10 GHz using a perturbation method cavity resonator. The measurement temperature was 23°C. The evaluation was as follows: A: Dk is less than 2.40 and Df is 0.0020 or less; B: Dk is less than 2.40 and Df is more than 0.0020, or Dk is 2.40 or more and Df is 0.0020 or less; C: Dk is 2.40 or more and Df is more than 0.0020.

[0304] Furthermore, the samples after the dielectric property measurements were heated at 130°C for 500 hours, and then the dielectric loss tangent (Df) at a frequency of 10 GHz was measured, and the difference from the dielectric loss tangent before heating (Df increase (after 500 hours)) was calculated. Evaluation was performed as follows. Df increase (after 500 hours) = Df (after 500 hours) - Df (before heating) SS: 0.0010 or less S: More than 0.0010 and 0.0020 or less A: More than 0.0020 and 0.0030 or less B: More than 0.0030 and 0.0040 or less C: More than 0.0040 and 0.0050 or less D: More than 0.0050

[0305] The perturbation method cavity resonator used was P5005A manufactured by Keysight Technologies.

[0306] Example 2 The same procedure as in Example 1 was carried out, except that the content of the resin (A) obtained in Synthesis Example 1 above was changed to 20 parts by mass, the content of the maleimide compound (ma) was changed to 60 parts by mass, and the content of the hydrogenated styrene-based thermoplastic elastomer (SEPTON 2104) was changed to 20 parts by mass.

[0307] Example 3 The same procedure as in Example 1 was carried out, except that the content of the resin (A) obtained in Synthesis Example 1 above was changed to 15 parts by mass, the content of the maleimide compound (ma) was changed to 55 parts by mass, and the content of the hydrogenated styrene-based thermoplastic elastomer (SEPTON 2104) was changed to 30 parts by mass.

[0308] Example 4 The same procedures as in Example 1 were carried out, except that the content of the resin (A) obtained in Synthesis Example 1 above was changed to 20 parts by mass, the content of the maleimide compound (ma) was changed to 60 parts by mass, and the hydrogenated styrene-based thermoplastic elastomer (SEPTON 2104) was changed to 20 parts by mass of a hydrogenated styrene-based thermoplastic elastomer (SEBS, Tuftec (registered trademark) H1043, Mn 39000, manufactured by Asahi Kasei Corporation).

[0309] Example 5 The same procedures as in Example 1 were carried out, except that the content of the resin (A) obtained in Synthesis Example 1 above was changed to 20 parts by mass, the content of the maleimide compound (ma) was changed to 60 parts by mass, and the hydrogenated styrene-based thermoplastic elastomer (SEPTON 2104) was changed to 20 parts by mass of a partially hydrogenated styrene-based thermoplastic elastomer (SEBS, S.O.E. (registered trademark) S1609, Mn 228000, manufactured by Asahi Kasei Corporation).

[0310] Example 6 The same procedures as in Example 1 were carried out, except that the content of the resin (A) obtained in Synthesis Example 1 above was changed to 20 parts by mass, no maleimide compound (ma) was added, the content of the polyphenylene ether compound (B1) having a terminal carbon-carbon unsaturated double bond obtained in Synthesis Example 2 was changed to 50 parts by mass, and the content of the hydrogenated styrene-based thermoplastic elastomer (SEPTON2104) was changed to 30 parts by mass.

[0311] Example 7 The same procedures as in Example 1 were carried out, except that the content of the resin (A) obtained in Synthesis Example 1 above was changed to 20 parts by mass, no maleimide compound (ma) was added, the content of the polymer (va) having a structural unit represented by formula (V) obtained in Synthesis Example 3 was changed to 50 parts by mass, and the content of the hydrogenated styrene-based thermoplastic elastomer (SEPTON 2104) was changed to 30 parts by mass.

[0312] Example 8 The same procedures as in Example 1 were carried out, except that the content of the resin (A) obtained in Synthesis Example 1 above was changed to 25 parts by mass, the content of the maleimide compound (ma) was changed to 25 parts by mass, the content of the polyphenylene ether compound (B2) having a terminal carbon-carbon unsaturated double bond obtained in Synthesis Example 4 was changed to 37.5 parts by mass, and the content of the hydrogenated styrene-based thermoplastic elastomer (SEPTON2104) was changed to 12.5 parts by mass.

[0313] Example 9 The same procedure as in Example 1 was carried out, except that the content of the resin (A) obtained in Synthesis Example 1 above was changed to 20 parts by mass, the content of the maleimide compound (ma) was changed to 25 parts by mass, the content of the polymer (va) having a structural unit represented by formula (V) obtained in Synthesis Example 3 above was changed to 25 parts by mass, and the content of the hydrogenated styrene-based thermoplastic elastomer (SEPTON 2104) was changed to 30 parts by mass.

[0314] Example 10 The same procedures as in Example 1 were performed except that the content of the resin (A) obtained in Synthesis Example 1 above was changed to 20 parts by mass, no maleimide compound (ma) was blended, the content of the polyphenylene ether compound (B1) having a terminal carbon-carbon unsaturated double bond obtained in Synthesis Example 2 was changed to 50 parts by mass, and the hydrogenated styrene-based thermoplastic elastomer (SEPTON2104) was changed to 30 parts by mass of a hydrogenated styrene-based thermoplastic elastomer (H1043, Mn39000).

[0315] Example 11 The same procedures as in Example 1 were performed, except that the content of the resin (A) obtained in Synthesis Example 1 above was changed to 20 parts by mass, no maleimide compound (ma) was blended, the content of the polyphenylene ether compound (B1) having a terminal carbon-carbon unsaturated double bond obtained in Synthesis Example 2 was changed to 50 parts by mass, and the hydrogenated styrene-based thermoplastic elastomer (SEPTON2104) was changed to 30 parts by mass of a partially hydrogenated styrene-based thermoplastic elastomer (S1609).

[0316] Example 12 The same procedures as in Example 1 were carried out, except that the content of the resin (A) obtained in Synthesis Example 1 above was 18 parts by mass, no maleimide compound (ma) was added, the content of the polyphenylene ether compound (B1) having a terminal carbon-carbon unsaturated double bond obtained in Synthesis Example 2 was 37 parts by mass, no hydrogenated styrene-based thermoplastic elastomer (SEPTON 2104) was added, the content of the hydrogenated styrene-based thermoplastic elastomer (SEBS, S.O.E. (registered trademark) S1605, manufactured by Asahi Kasei Corporation) was 10 parts by mass, and further, the content of the modified polyphenylene ether compound having a terminal methacrylic group (manufactured by SABIC Innovative Plastics, SA9000, functional group equivalent (vinyl group double bond equivalent) of 1011 g / eq.) was 35 parts by mass.

[0317] Example 13 The same procedures as in Example 1 were performed, except that the content of the resin (A) obtained in Synthesis Example 1 above was changed to 54 parts by mass, the maleimide compound (ma) was not blended, the content of the maleimide compound (compound represented by formula (M3), MIR-3000-70MT, manufactured by Nippon Kayaku Co., Ltd.) was changed to 7 parts by mass, the content of the polyphenylene ether compound (B1) having a terminal carbon-carbon unsaturated double bond obtained in Synthesis Example 2 was changed to 29 parts by mass, the hydrogenated styrene-based thermoplastic elastomer (SEPTON2104) was not blended, and the content of the hydrogenated styrene-based thermoplastic elastomer (SEBS, S.O.E. (registered trademark) S1605, manufactured by Asahi Kasei Corporation) was changed to 10 parts by mass.

[0318] Example 14 In Example 1, the content of the resin (A) obtained in Synthesis Example 1 above was changed to 31 parts by mass, the maleimide compound (ma) was not blended, the content of the maleimide compound (compound represented by formula (M4), manufactured by K.I. Chemical Industry Co., Ltd., BMI-70, functional group equivalent (maleimide group equivalent) was 221 g / eq.) was changed to 12 parts by mass, the hydrogenated styrene-based thermoplastic elastomer (SEPTON2104) was not blended, and the hydrogenated styrene-based thermoplastic elastomer (SEPTON2104) was not blended. The same procedure was repeated except that the content of the methacrylic acid copolymer (SEBS, S.O.E. (registered trademark) S1605, manufactured by Asahi Kasei Corporation) was 10 parts by mass, the content of the methacrylic-terminated modified polyphenylene ether compound (SABIC Innovative Plastics, SA9000, functional group equivalent (vinyl group double bond equivalent) was 1011 g / eq.) was 19 parts by mass, the content of 1,2-bis(4-vinylphenyl)ethane (BVPE, manufactured by Angene International) was 28 parts by mass, and the content of Perbutyl P (α,α'-di(t-butylperoxy)diisopropylbenzene, manufactured by NOF Corporation) was 0.5 parts by mass.

[0319] Example 15 In Example 1, the content of resin (A) obtained in Synthesis Example 1 above was changed to 37 parts by mass, the maleimide compound (ma) was not blended, the content of the maleimide compound (compound represented by formula (M3), MIR-3000-70MT manufactured by Nippon Kayaku Co., Ltd.) was changed to 17 parts by mass, the hydrogenated styrene-based thermoplastic elastomer (SEPTON2104) was not blended, the content of the hydrogenated styrene-based thermoplastic elastomer (SEBS, S.O.E. (registered trademark) S1605, manufactured by Asahi Kasei Corporation) was changed to 10 parts by mass, and further, The same procedure was repeated except that the content of the modified polyphenylene ether compound (SABIC Innovative Plastics, SA9000, functional group equivalent (vinyl group double bond equivalent) was 1011 g / eq.) in which (A) is a methacrylic group was changed to 9 parts by mass, the content of triallyl isocyanurate (Nippon Chemical Industry Co., Ltd., molecular weight 249.7, number of terminal double bonds 3) was changed to 27 parts by mass, and the content of Perbutyl P (α,α'-di(t-butylperoxy)diisopropylbenzene, NOF Corporation) was changed to 1.0 part by mass.

[0320] Example 16 In Example 1, the content of the resin (A) obtained in Synthesis Example 1 above was changed to 20 parts by mass, the maleimide compound (ma) was not blended, the content of the maleimide compound (compound represented by formula (M3), MIR-3000-70MT manufactured by Nippon Kayaku Co., Ltd.) was changed to 32 parts by mass, the hydrogenated styrene-based thermoplastic elastomer (SEPTON2104) was not blended, the content of the hydrogenated styrene-based thermoplastic elastomer (H1043, Mn39000) was changed to 20 parts by mass, and further, The same procedure was repeated except that the content of the modified polyphenylene ether compound (SABIC Innovative Plastics, SA9000, functional group equivalent (vinyl group double bond equivalent) was 1011 g / eq.) was 9 parts by mass, the content of triallyl isocyanurate (Nippon Kasei Chemical Co., Ltd., molecular weight 249.7, number of terminal double bonds 3) was 19 parts by mass, and the content of Perbutyl P (α,α'-di(t-butylperoxy)diisopropylbenzene, NOF Corporation) was 1.0 part by mass.

[0321] Comparative Example 1 The same procedure as in Example 1 was carried out, except that the resin (A) and maleimide compound (ma) obtained in Synthesis Example 1 above were not blended, 80 parts by mass of the polymer (va) having a structural unit represented by formula (V) obtained in Synthesis Example 3 above was blended, and the content of the hydrogenated styrene-based thermoplastic elastomer (SEPTON 2104) was changed to 20 parts by mass.

[0322] Comparative Example 2 The same procedures as in Example 1 were carried out, except that the content of the resin (A) obtained in Synthesis Example 1 above was changed to 30 parts by mass, the maleimide compound (ma) and the hydrogenated styrene-based thermoplastic elastomer (SEPTON 2104) were not blended, and 70 parts by mass of the polymer (va) having a structural unit represented by formula (V) obtained in Synthesis Example 3 above was blended.

[0323] Comparative Example 3 The same procedure as in Example 1 was carried out, except that the content of the resin (A) obtained in Synthesis Example 1 above was changed to 70 parts by mass, the maleimide compound (ma) was not blended, and the content of the hydrogenated styrene-based thermoplastic elastomer (SEPTON 2104) was changed to 30 parts by mass.

[0324] Comparative Example 4 The same procedure as in Example 1 was carried out except that the content of the resin (A) obtained in Synthesis Example 1 above was changed to 30 parts by mass, the content of the maleimide compound (ma) was changed to 70 parts by mass, and the hydrogenated styrene-based thermoplastic elastomer (SEPTON 2104) was not blended.

[0325] Comparative Example 5 The same procedure as in Example 1 was carried out, except that the content of the resin (A) obtained in Synthesis Example 1 above was changed to 30 parts by mass, the maleimide compound (ma) was not blended, and the content of the hydrogenated styrene-based thermoplastic elastomer (SEPTON 2104) was changed to 70 parts by mass.

[0326] Comparative Example 6 The same procedure as in Example 1 was carried out, except that the resin (A) obtained in Synthesis Example 1 was not blended, the content of the maleimide compound (ma) was changed to 80 parts by mass, and the content of the hydrogenated styrene-based thermoplastic elastomer (SEPTON 2104) was changed to 20 parts by mass.

[0327]

[0328]

[0329]

Claims

1. A resin composition comprising: a resin (A) having a terminal group represented by formula (T1) and having an indane skeleton; a thermoplastic elastomer (B); and at least one thermosetting compound (C) selected from the group consisting of a compound having a polymerizable carbon-carbon unsaturated double bond at an end other than that of the resin (A), a maleimide compound, and a cyanate ester compound, wherein the thermoplastic elastomer (B) contains hydrogenated butadiene monomer units and / or hydrogenated isoprene monomer units. (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 hydrogenation rate of the thermoplastic elastomer (B) is 70% or more.

3. The resin composition according to claim 1 or 2, wherein the thermoplastic elastomer (B) contains styrene monomer units and hydrogenated butadiene monomer units and / or hydrogenated isoprene monomer units.

4. The resin composition according to claim 1 or 2, wherein the thermoplastic elastomer (B) has a number average molecular weight of 2,000 or more.

5. The resin composition according to claim 1 or 2, wherein the thermoplastic elastomer (B) is contained in an amount of 2.5 to 50 parts by mass per 100 parts by mass of resin solids in the resin composition.

6. The resin composition according to claim 1 or 2, 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.) 7. The resin composition according to claim 1 or 2, wherein the resin (A) is contained in an amount of 1 to 90 parts by mass per 100 parts by mass of resin solids in the resin composition.

8. The resin composition according to claim 1 or 2, wherein the thermosetting compound (C) comprises at least one selected from the group consisting of a maleimide compound, a polymer having a structural unit represented by formula (V), a polyphenylene ether compound having a carbon-carbon unsaturated double bond at its terminal, a (meth)allyl compound, a (meth)acrylate compound, a compound having an indane skeleton having a carbon-carbon unsaturated double bond at its terminal other than the resin (A), and a cyanate ester compound. (In formula (V), Ar represents an aromatic hydrocarbon linking group. * represents a bonding position.) 9. The resin composition according to claim 1 or 2, wherein the thermosetting compound (C) comprises at least one 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 (M4), a compound represented by formula (M5), a polymer having a structural unit represented by formula (V), and a compound represented by formula (OP). (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 (M4), R ５６ each independently represents a hydrogen atom, a methyl group, or an ethyl group; R ５７ each independently represents a hydrogen atom or a methyl group. (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 formula (V), Ar represents an aromatic hydrocarbon linking group. * represents a bonding position.) (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.

10. The resin composition according to claim 1 or 2, comprising 5 to 90 parts by mass of said thermosetting compound (C) per 100 parts by mass of resin solids in said resin composition.

11. The hydrogenation rate of the thermoplastic elastomer (B) is 70% or more, the thermoplastic elastomer (B) contains a styrene monomer unit, a hydrogenated butadiene monomer unit and / or a hydrogenated isoprene monomer unit, the number average molecular weight of the thermoplastic elastomer (B) is 2,000 or more, the thermoplastic elastomer (B) is contained in a ratio of 2.5 to 50 parts by mass relative to 100 parts by mass of resin solid content in the resin composition, the resin (A) contains a resin represented by formula (T1-1), and the resin (A) is contained in a ratio of 1 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 thermosetting compound (C) comprises at least one selected from the group consisting of a maleimide compound, a polymer having a structural unit represented by formula (V), a polyphenylene ether compound having a carbon-carbon unsaturated double bond at a terminal, a (meth)allyl compound, a (meth)acrylate compound, a compound having an indane skeleton having a carbon-carbon unsaturated double bond at a terminal other than the resin (A), and a cyanate ester compound, and the resin composition contains 1 to 90 parts by mass of the thermosetting compound (C) per 100 parts by mass of a resin solid content in the resin composition. (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 (V), Ar represents an aromatic hydrocarbon linking group. * represents a bonding position.) 12. The resin composition according to claim 11, wherein the thermosetting compound (C) comprises at least one 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 (M4), a compound represented by formula (M5), a polymer having a structural unit represented by formula (V), and a compound represented by formula (OP). (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 (M4), R ５６ each independently represents a hydrogen atom, a methyl group, or an ethyl group; R ５７ each independently represents a hydrogen atom or a methyl group. (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 formula (V), Ar represents an aromatic hydrocarbon linking group. * represents a bonding position.) (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.

13. The resin composition according to claim 1, 2, 11, or 12, further comprising a flame retardant.

14. The resin composition according to claim 1, 2, 11, or 12, further comprising a filler.

15. The resin composition according to claim 14, wherein the content of said filler is 10 to 1600 parts by mass per 100 parts by mass of resin solids in said resin composition.

16. The resin composition according to claim 1, 2, 11, or 12, further comprising a curing accelerator.

17. The resin composition according to claim 16, wherein the content of the curing accelerator is 0.1 to 0.8 parts by mass per 100 parts by mass of resin solids in the resin composition.

18. A cured product of the resin composition according to claim 1, 2, 11 or 12.

19. A prepreg formed from a substrate and the resin composition according to claim 1, 2, 11, or 12.

20. A metal foil clad laminate comprising at least one layer formed from the prepreg of claim 19 and metal foil disposed on one or both sides of the layer formed from the prepreg.

21. A resin composite sheet comprising a support and a layer formed from the resin composition according to claim 1, 2, 11 or 12, disposed on a surface of the support.

22. A printed wiring board comprising an insulating layer and a conductor layer disposed on a surface of the insulating layer, the insulating layer comprising a layer formed from a resin composition according to claim 1, 2, 11, or 12.

23. A semiconductor device comprising the printed wiring board according to claim 22.

Images