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

Abstract

To provide: a resin composition having excellent hygroscopicity and heat resistance while maintaining excellent dielectric properties; a prepreg; a metal foil-clad laminate; a resin composite sheet; a printed wiring board; and a semiconductor device.SOLUTION: A resin composition comprises: a polymer (A) having a structural unit represented by formula (V); and a compound (B) having a molecular weight of less than 1,000 and containing, in its molecule, one organic group that contains a carbon-carbon unsaturated bond. In formula (V), Ar represents an aromatic hydrocarbon linking group. * represents a binding position.SELECTED DRAWING: None

Description

[Technical field]

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

[0002] In recent years, there has been an accelerating trend toward higher integration and finer design of semiconductor elements used in mobile terminals, electronic devices, communication devices, etc. Accordingly, there is a demand for technology that enables high-density mounting of semiconductor elements, and there is also a demand for improvements in printed wiring boards, which play an important role in such mounting. On the other hand, the applications of electronic devices are becoming more diverse and expanding. In response to this, the properties required for printed wiring boards, metal foil-clad laminates, prepregs, etc. used therein are also becoming more diverse and stricter. In order to obtain improved printed wiring boards while taking into account such required properties, various materials and processing methods have been proposed. One of these is the improvement and development of the resin materials that make up prepregs and resin composite sheets. For example, Patent Document 1 discloses a novel soluble polyfunctional vinyl aromatic copolymer having improved heat resistance, compatibility, transparency and toughness, a production method thereof, and a curable composition containing the copolymer. [Prior art documents] [Patent documents]

[0003] [Patent Document 1] International Publication No. 2017 / 115813 Summary of the Invention [Problem to be solved by the invention]

[0004] As mentioned above, the applications of electronic devices and the like are diversifying and expanding, and new resin materials are being demanded for the resin materials that make up prepregs, etc. In particular, there is a demand for further development of resin compositions that have excellent moisture absorption and heat resistance while maintaining excellent dielectric properties. The present invention has an object to solve the above-mentioned problems, and to provide a resin composition having excellent moisture absorption and heat resistance while maintaining excellent dielectric properties, as well as a prepreg, a metal foil-clad laminate, a resin composite sheet, a printed wiring board, and a semiconductor device. [Means for solving the problem]

[0005] In view of the above-mentioned problems, the present inventors have conducted research and found that the above-mentioned problems can be solved by blending a compound (B) having a molecular weight of less than 1000 and containing one organic group containing a carbon-carbon unsaturated bond in the molecule with a specific aromatic vinyl compound. Specifically, the above problems were solved by the following means. <1> A polymer (A) having a structural unit represented by formula (V), and a compound (B) having a molecular weight of less than 1,000 and containing one organic group containing a carbon-carbon unsaturated bond in the molecule. [ka] (In formula (V), Ar represents an aromatic hydrocarbon linking group. * represents a bonding position.) <2> The weight average molecular weight of the polymer (A) is 1,000 to 160,000. <1> The resin composition according to claim 1. <3> The content of the polymer (A) is 5 to 70 parts by mass relative to 100 parts by mass of resin solid content in the resin composition. <1> or <2> The resin composition according to claim 1. <4> The organic group containing a carbon-carbon unsaturated bond is CH 2 Has the structure =C(X)- (X is a hydrogen atom or a methyl group). <1> ~ <3> 10. The resin composition according to claim 9 . <5> The organic group containing a carbon-carbon unsaturated bond is one selected from the group consisting of a vinyl group, an allyl group, an acryl group, and a methacryl group. <1> ~ <4> 10. The resin composition according to claim 9 . <6> The molecular weight of the compound (B) is 70 to 500. <1> ~ <5> 10. The resin composition according to claim 9 . <7> The boiling point of the compound (B) is 110 to 300° C. <1> ~ <6> 10. The resin composition according to claim 9 . <8> The content of the compound (B) is 1 to 10 parts by mass relative to 100 parts by mass of the resin solid content in the resin composition. <1> ~ <7> 10. The resin composition according to claim 9 . <9> a mass ratio of the polymer (A) to the compound (B) in the resin composition is 1:0.025 to 0.7; <1> ~ <8> 10. The resin composition according to claim 9 . <10> Further, the composition further includes another thermosetting compound (C) which does not fall under the polymer (A) and the compound (B), <1> ~ <9> 10. The resin composition according to claim 9 . <11> the other thermosetting compound (C) includes at least one selected from the group consisting of a maleimide compound, a polyphenylene ether compound containing two or more carbon-carbon unsaturated double bonds, a cyanate ester compound, an epoxy compound, a phenol compound, an alkenyl-substituted nadimide compound, an oxetane resin, and a benzoxazine compound; <10> The resin composition according to claim 1. <12> The other thermosetting compound (C) includes at least one selected from the group consisting of a compound (M1) represented by formula (M1), a compound represented by formula (M3), a compound represented by formula (M5), and a compound represented by formula (OP-1). <10> The resin composition according to claim 1. [ka] (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 RM10 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, an aryl group having 6 to 10 carbon atoms, an aryloxy group having 1 to 10 carbon atoms, an arylthio group having 1 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.) [ka] (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 between 1 and 10.) [ka] (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 greater.) [ka] In formula (OP-1), X represents an aromatic group, -(YO)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 from 1 to 6, and n 2 represents an integer from 1 to 100, and n 3 represents an integer from 2 to 4.) <13> The other thermosetting compound (C) includes at least one selected from the group consisting of a compound (M1) represented by formula (M1), a compound represented by formula (M3), and a compound represented by formula (OP-1). <10> The resin composition according to claim 1. [ka] (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, an aryl group having 6 to 10 carbon atoms, an aryloxy group having 1 to 10 carbon atoms, an arylthio group having 1 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.) [ka] (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 between 1 and 10.) [ka] In formula (OP-1), X represents an aromatic group, -(YO)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 from 1 to 6, and n 2 represents an integer from 1 to 100, and n 3 represents an integer from 2 to 4.) <14> The content of the thermosetting compound (C) is 5 to 95 parts by mass relative to 100 parts by mass of resin solid content in the resin composition. <10> The resin composition according to claim 1. <15> The other thermosetting compound (C) contains at least one selected from the group consisting of compounds represented by formula (OP-1), and the content thereof is 3 to 50 parts by mass relative to 100 parts by mass of a resin solid content in the resin composition. <10> The resin composition according to claim 1. [ka] (In formula (OP-1), X represents an aromatic group, -(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 from 1 to 6, and n 2 represents an integer from 1 to 100, and n 3 represents an integer from 2 to 4.) <16> Further, the filler (D) is contained. <1> ~ <15> 10. The resin composition according to claim 9 . <17> The content of the filler (D) is 10 to 500 parts by mass relative to 100 parts by mass of the resin solid content in the resin composition. <16> The resin composition according to claim 1. <18> The content of the polymer (A) is 5 to 70 parts by mass, and the content of the compound (B) is 1 to 10 parts by mass, relative to 100 parts by mass of a resin solid content in the resin composition. <1> ~ <17> 10. The resin composition according to claim 9 . <19> Substantially free of polymerization initiators; <1> ~ <18> 10. The resin composition according to claim 9 . <20> The weight average molecular weight of the polymer (A) is 1,000 to 160,000, the content of the polymer (A) is 5 to 70 parts by mass relative to 100 parts by mass of a resin solid content in the resin composition, the organic group containing a carbon-carbon unsaturated bond is one selected from the group consisting of a vinyl group, an allyl group, an acrylic group, and a methacrylic group, the molecular weight of the compound (B) is 70 to 500, the boiling point of the compound (B) is 110 to 300° C., the content of the compound (B) is 1 to 10 parts by mass relative to 100 parts by mass of a resin solid content in the resin composition, and a mass ratio of the above is 1:0.025 to 0.7, and the resin composition further contains another thermosetting compound (C) which does not fall under the category of the polymer (A) and the compound (B), the other thermosetting compound (C) containing at least one selected from the group consisting of a maleimide compound, a polyphenylene ether compound containing two or more carbon-carbon unsaturated double bonds, a cyanate ester compound, an epoxy compound, a phenol compound, an alkenyl-substituted nadimide compound, an oxetane resin, and a benzoxazine compound, and the content of the thermosetting compound (C) relative to 100 parts by mass of a resin solid content in the resin composition is 5 to 95 parts by mass. <1> The resin composition according to claim 1. <21> The other thermosetting compound (C) includes at least one selected from the group consisting of compounds represented by formula (OP-1), and the content thereof is 3 to 50 parts by mass relative to 100 parts by mass of a resin solid content in the resin composition. <20> The resin composition according to claim 1. [ka] (In formula (OP-1), X represents an aromatic group, -(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 from 1 to 6, and n2 represents an integer from 1 to 100, and n 3 represents an integer from 2 to 4.) <22> Substantially free of polymerization initiators; <21> The resin composition according to claim 1. <23> A substrate; <1> ~ <22> and a prepreg formed from the resin composition according to any one of the above. <24> <23> 13. A metal foil-clad laminate comprising: at least one layer formed from the prepreg according to claim 12; and metal foil disposed on one or both sides of the layer formed from the prepreg. <25> A support and a substrate disposed on the surface of the support. <1> ~ <22> and a layer formed from the resin composition according to any one of the above. <26> A printed wiring board including an insulating layer and a conductor layer disposed on a surface of the insulating layer, the insulating layer comprising: <1> ~ <22> A printed wiring board comprising a layer formed from the resin composition according to any one of claims 1 to 5. <27> <26> A semiconductor device comprising the printed wiring board according to claim 1. Effect of the Invention

[0006] The present invention makes it possible to provide a resin composition that has excellent moisture absorption and heat resistance while maintaining excellent dielectric properties, as well as a prepreg, a metal foil-clad laminate, a resin composite sheet, a printed wiring board, and a semiconductor device. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0007] Hereinafter, an embodiment of the present invention (hereinafter, simply referred to as "the present embodiment") will be described in detail. Note that the present embodiment is an example for explaining the present invention, and the present invention is not limited to the present embodiment. In this specification, the use of "to" means that the numerical values ​​before and after it are included as the lower limit and upper limit. In this specification, various physical properties and characteristic values ​​are those at 23° C. unless otherwise specified. In the description of groups (atomic groups) in this specification, when the description does not indicate whether the group is substituted or unsubstituted, the description also includes groups (atomic groups) that have a substituent as well as groups (atomic groups) that have no substituent. For example, the term "alkyl group" includes not only alkyl groups that have no substituent (unsubstituted alkyl groups), but also alkyl groups that have a substituent (substituted alkyl groups). In this specification, when the description does not indicate whether the group is substituted or unsubstituted, the description is preferably unsubstituted. In this specification, the relative dielectric constant refers to the ratio of the dielectric constant of a substance to the dielectric constant of a vacuum. In addition, in this specification, the relative dielectric constant may be simply referred to as the "dielectric constant." In this specification, "(meth)acrylic" refers to both or either of acrylic and methacrylic. In cases where the standards shown in this specification differ depending on the year and the measurement method, etc., they shall be based on the standards as of January 1, 2021, unless otherwise stated.

[0008] In this specification, the resin solids refers to components excluding the filler (D) and the solvent, and is intended to include the polymer (A) having a structural unit represented by formula (V), the compound (B) having a molecular weight of less than 1000 and containing one organic group containing a carbon-carbon unsaturated bond in its molecule, as well as other thermosetting compounds (C), elastomers, silane coupling agents, and other resin additive components (such as flame retardants and other additives) that are blended as necessary.

[0009] The resin composition of the present embodiment is characterized by containing a polymer (A) having a structural unit represented by formula (V) and a compound (B) (hereinafter sometimes simply referred to as "compound (B)") having a molecular weight of less than 1000 and containing one organic group containing a carbon-carbon unsaturated bond in the molecule. [ka] (In formula (V), Ar represents an aromatic hydrocarbon linking group. * represents a bonding position.) By adopting such a configuration, it is possible to provide a resin composition that has excellent moisture absorption and heat resistance while maintaining excellent dielectric properties. The polymer (A) having the structural unit represented by formula (V) has excellent dielectric properties, but tends to have poor moisture absorption and heat resistance. It was speculated that this is because the polymer (A) having the structural unit represented by formula (V) is a polymer and has many vinyl groups in the molecular chain. That is, if the vinyl group remains unreacted during curing, it will deteriorate the moisture absorption and heat resistance. In this embodiment, it was speculated that the unreacted vinyl groups of the polymer (A) having the structural unit represented by formula (V) could be capped by blending the compound (B). As a result, it was speculated that the unreacted vinyl groups in the obtained cured product were reduced, and the moisture absorption and heat resistance was greatly improved. In addition, since the compound (B) is a small molecule with a molecular weight of less than 1000, it was speculated that the mobility and diffusion were high, and the probability of reacting with the unreacted vinyl groups was also increased. It is assumed that the above-mentioned capping effect improves the moisture absorption heat resistance if the functional group is a functional group that caps the vinyl group in the polymer (A) other than the organic group containing a carbon-carbon unsaturated bond. However, depending on the type of functional group, it is assumed that a highly polar site remains even after capping, which may adversely affect the dielectric properties of the cured product. In contrast, in this embodiment, it is assumed that the use of a compound having an organic group containing a carbon-carbon unsaturated bond makes it possible to make the obtained cured product less likely to have polarity.

[0010] <Polymer (A) Having a Structural Unit Represented by Formula (V)> The resin composition of the present embodiment contains a polymer (A) having a structural unit represented by formula (V). By containing the polymer (A) having a structural unit represented by formula (V), a resin composition excellent in low dielectric properties (low dielectric constant, low dielectric loss tangent) can be obtained. [ka] (In formula (V), Ar represents an aromatic hydrocarbon linking group. * represents a bonding position.) The aromatic hydrocarbon linking group may be a group consisting of only aromatic hydrocarbons which may have a substituent, or may be a group consisting of a combination of aromatic hydrocarbons which may have a substituent and other linking groups, and is preferably a group consisting of only aromatic hydrocarbons which may have a substituent. The substituent that the aromatic hydrocarbon may have includes a substituent Z (for example, 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.

[0011] Specific examples of the aromatic hydrocarbon linking group include phenylene, naphthalenediyl, anthracenediyl, phenanthrenediyl, biphenyldiyl, and fluorenediyl groups, which may have a substituent, and among these, phenylene groups which may have a substituent are preferred. Examples of the substituent include the above-mentioned substituent Z, but it is preferred that the above-mentioned phenylene groups and other groups do not have a substituent.

[0012] The constitutional unit represented by formula (V) more preferably includes at least one of a constitutional unit represented by the following formula (V1), a constitutional unit represented by the following formula (V2), and a constitutional unit represented by the following formula (V3). In the following formula, * represents a bonding position. In addition, hereinafter, the constitutional units represented by formulas (V1) to (V3) may be collectively referred to as "constituent unit (a)".

[0013] [ka] In formulas (V1) to (V3), L 1is an aromatic hydrocarbon linking group (preferably having 6 to 22 carbon atoms, more preferably having 6 to 18 carbon atoms, and even more preferably having 6 to 10 carbon atoms). Specific examples 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. The compound forming the structural unit (a) is preferably a divinyl aromatic compound, such as divinylbenzene, bis(1-methylvinyl)benzene, divinylnaphthalene, divinylanthracene, divinylbiphenyl, and divinylphenanthrene. Among them, divinylbenzene is particularly preferred. These divinyl aromatic compounds may be used alone or in combination as necessary.

[0014] As described above, the polymer (A) having the structural unit represented by formula (V) may be a homopolymer of the structural unit (a), or may be a copolymer with a structural unit derived from another monomer. When the polymer (A) having the structural unit represented by formula (V) is a copolymer, the copolymerization ratio of the structural unit (a) is preferably 3 mol% or more, more preferably 5 mol% or more, even more preferably 10 mol% or more, and may 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, 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.

[0015] An example of a structural unit derived from another monomer is the structural unit (b) derived from an aromatic compound having one vinyl group (monovinyl aromatic compound).

[0016] The structural unit (b) derived from a monovinyl aromatic compound is preferably a structural unit represented by the following formula (V4).

[0017] [ka] In formula (V4), L 2 is an aromatic hydrocarbon linking group, and preferred examples thereof include the above L 1 Examples include: R V1 R 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, and more preferably has 1 to 3 carbon atoms. V1 and L 2 may have the above-mentioned substituent Z.

[0018] When the polymer (A) having the structural unit represented by formula (V) is a copolymer containing the 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 nucleus 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 have the above-mentioned substituent Z as appropriate. In addition, these monovinyl aromatic compounds may be used alone or in combination.

[0019] When the polymer (A) 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 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.

[0020] The polymer (A) having a structural unit represented by formula (V) may have other structural units other than the structural unit (a) and the structural unit (b). Examples of other structural units include structural units (c) derived from cycloolefin compounds. Examples of cycloolefin compounds include hydrocarbons having a double bond in a ring structure. Specifically, in addition to monocyclic olefins such as cyclobutene, cyclopentene, cyclohexene, and cyclooctene, compounds having a norbornene ring structure such as norbornene and dicyclopentadiene, and cycloolefin compounds in which aromatic rings such as indene and acenaphthylene are condensed can be mentioned. Examples of norbornene compounds include those described in paragraphs 0037 to 0043 of JP 2018-39995 A, the contents of which are incorporated herein. The cycloolefin compounds exemplified here may further have the above-mentioned substituent Z.

[0021] When the polymer (A) 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.

[0022] The polymer (A) having the 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 and butadiene. The copolymerization ratio of the structural unit (d) derived from other polymerizable compounds is preferably 30 mol% or less, more preferably 20 mol% or less, and even more preferably 10 mol% or less.

[0023] An example of an embodiment of the polymer (A) having a structural unit represented by formula (V) is a polymer that essentially contains the structural unit (a) and at least one of the structural units (b) to (d). Further, an example is one in which the total of the structural units (a) to (d) accounts for 95 mol % or more, and further 98 mol % or more, of all the structural units. In another embodiment of the polymer (A) having a structural unit represented by formula (V), the structural unit (a) is essential, and of all structural units excluding the terminals, structural units containing an aromatic ring preferably account for 90 mol % or more, more preferably 95 mol % or more, and may even be 100 mol %. In calculating the mole percentage per total structural units, one structural unit is defined as being derived from one molecule of a monomer (e.g., a divinyl aromatic compound, a monovinyl aromatic compound, etc.) used in the production of polymer (A) having a structural unit represented by formula (V).

[0024] The method for producing the polymer (A) having the structural unit represented by formula (V) is not particularly limited and may be a conventional method, for example, a raw material containing a divinyl aromatic compound (if necessary, a monovinyl aromatic compound, a cycloolefin compound, etc. may be coexisted) in the presence of a Lewis acid catalyst. As the Lewis acid catalyst, a metal fluoride such as boron trifluoride or a complex thereof can be used.

[0025] The structure of the chain end of the polymer (A) having the structural unit represented by formula (V) is not particularly limited, but in terms of the group derived from the above-mentioned divinyl aromatic compound, it may have the structure of the following formula (E1). 1 is the same as defined in formula (V1) above. * represents a bond position. *-CH=CH-L 1 -CH=CH 2 (E1)

[0026] 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 formula (V4) above. * represents a bond position. *-CH=CH-L 2 -R V1 (E2)

[0027] The molecular weight of the polymer (A) having a constitutional unit represented by formula (V) is, in number average molecular weight Mn, preferably 300 or more, more preferably 500 or more, even more preferably 1,000 or more, and even more preferably 1,500 or more. The upper limit is preferably 130,000 or less, more preferably 120,000 or less, even more preferably 110,000 or less, and even more preferably 100,000 or less. The molecular weight of the polymer (A) having the structural unit represented by formula (V) is preferably 1,000 or more, more preferably 1,500 or more, more preferably 2,000 or more, more preferably 2,500 or more, even more preferably 3,000 or more, and may be 3,500 or more or 4,000 or more. By making it equal to or greater than the lower limit, the excellent low dielectric properties of the polymer (A) 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 is preferably 160,000 or less, more preferably 150,000 or less, even more preferably 140,000 or less, even more preferably 130,000 or less, and may be 120,000 or less, or 110,000 or less. By making it equal to or less than the upper limit, embedding defects tend to be less likely to occur when the prepreg or resin sheet is laminated on a circuit-forming board. The monodispersity (Mw / Mn), which is 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, and even more preferably 20 or less. As for the lower limit, a practical value is 1.1 or more, and it may be 5 or more, 7 or more, and even if it is 10 or more, the required performance is satisfied. The above Mw and Mn are measured according to the description in the Examples section below. When the resin composition of the present embodiment contains two or more types of polymer (A) 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.

[0028] The vinyl group equivalent of the polymer (A) having the 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 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. By making it equal to or greater than the above 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, by making it equal to or less than the above upper limit, the heat resistance of the obtained cured product tends to be improved.

[0029] In addition, the polymer (A) having the structural unit represented by formula (V) used in this embodiment preferably has excellent low dielectric properties when cured. For example, the cured polymer (A) having the structural unit represented by formula (V) used in this embodiment preferably has a relative dielectric constant (Dk) of 2.80 or less at 10 GHz measured according to the cavity resonator perturbation method, more preferably 2.60 or less, even more preferably 2.50 or less, and even more preferably 2.40 or less. In addition, the lower limit of the relative dielectric constant is, for example, 1.80 or more in practical use. In addition, the cured polymer (A) having the structural unit represented by formula (V) used in this embodiment preferably has a dielectric loss tangent (Df) of 0.0030 or less at 10 GHz measured according to the cavity resonator perturbation method, more preferably 0.0020 or less, and even more preferably 0.0010 or less. In addition, the lower limit of the dielectric loss tangent is, for example, 0.0001 or more in practical use. The relative dielectric constant (Dk) and the dielectric loss tangent (Df) are measured according to the method described in the examples below.

[0030] For the polymer (A) having a constitutional unit represented by formula (V) in this specification, the compounds described in paragraphs 0029 to 0058 of International Publication No. 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.

[0031] In the resin composition of the present embodiment, when the resin solid content in the resin composition is 100 parts by mass, the content of the polymer (A) having the structural unit represented by formula (V) is preferably 5 to 70 parts by mass. The lower limit of the content of the polymer (A) having the structural unit represented by formula (V) is more preferably 7 parts by mass or more, even more preferably 9 parts by mass or more, even more preferably 10 parts by mass or more, even more preferably 15 parts by mass or more, even more preferably 20 parts by mass or more, and particularly more preferably 25 parts by mass or more, when the resin solid content in the resin composition is 100 parts by mass. By making the content of the polymer (A) having the structural unit represented by formula (V) equal to or more than the above lower limit, low dielectric properties, in particular low relative dielectric constant, can be effectively achieved. On the other hand, the upper limit of the content of the polymer (A) having the structural unit represented by formula (V) is preferably 65 parts by mass or less, more preferably 60 parts by mass or less, even more preferably 50 parts by mass or less, still more preferably 40 parts by mass or less, even more preferably 35 parts by mass or less, and may be 20 parts by mass or less, based on 100 parts by mass of the resin solid content in the resin composition. By setting the content to the upper limit or less, the metal foil peel strength of the obtained cured product can be effectively increased. The polymer (A) having the structural unit represented by formula (V) may be contained in the resin composition in one type or in two or more types. When two or more types are contained, it is preferable that the total amount is within the above range.

[0032] <Compound (B) having a molecular weight of less than 1000 and containing one organic group containing a carbon-carbon unsaturated bond in the molecule> The resin composition of the present embodiment contains a compound (B) (compound (B)) having a molecular weight of less than 1000 and containing one organic group containing a carbon-carbon unsaturated bond in the molecule. It is presumed that the carbon-carbon unsaturated bond of compound (B) reacts with a vinyl group of polymer (A) having a structural unit represented by formula (V), thereby improving the moisture absorption and heat resistance of the obtained cured product. The carbon-carbon unsaturated bond constituting the organic group containing the carbon-carbon unsaturated bond does not include those contained as part of an aromatic ring. On the other hand, it includes carbon-carbon unsaturated bonds contained as part of a non-aromatic ring. An example of a carbon-carbon unsaturated bond contained as part of a non-aromatic ring is a cyclohexenyl group in a molecule. It also includes carbon-carbon unsaturated bonds contained in parts other than the terminals of a linear or branched organic group, i.e., in a linear or branched chain. In this embodiment, the organic group containing a carbon-carbon unsaturated bond is CH 2 It is preferable that the compound has a =C(X)- (X is a hydrogen atom or a methyl group) structure. By adopting a compound containing a carbon-carbon unsaturated bond at the end of the molecule in this manner, it becomes possible to react more effectively with the vinyl group of the polymer (A) having the structural unit represented by formula (V). The organic group containing a carbon-carbon unsaturated bond is more preferably one selected from the group consisting of a vinyl group, an allyl group, an acryl group, and a methacryl group, and is further preferably a vinyl group.

[0033] The compound (B) used in this embodiment is preferably composed only of atoms selected from carbon atoms, hydrogen atoms, oxygen atoms, and silicon atoms. The compound (B) used in this embodiment may or may not have a polar group. It is preferable that the compound (B) used in this embodiment does not have a polar group. Examples of the polar group include an amino group, a carboxyl group, a hydroxyl group, and a nitro group.

[0034] In this embodiment, the molecular weight of the compound (B) is preferably 70 or more, more preferably 80 or more, and even more preferably 90 or more. By making it equal to or more than the lower limit, there is a tendency that the volatilization of the compound (B) from the resin composition of this embodiment or its cured product can be suppressed. The upper limit of the molecular weight of the compound (B) is preferably 500 or less, more preferably 400 or less, even more preferably 300 or less, even more preferably 200 or less, and may be 150 or less. By making it equal to or less than the upper limit, there is a tendency that the effect of increasing the reactivity with the polymer (A) having the structural unit represented by formula (V) is further improved. When the resin composition of the present embodiment contains two or more types of compound (B), it is preferable that the average molecular weight value of the compound (B) falls within the above range, and it is more preferable that the molecular weight of each compound falls within the above preferred range.

[0035] In this embodiment, the boiling point of the compound (B) is preferably 110°C or higher, more preferably 115°C or higher, and even more preferably 120°C or higher. By making it equal to or higher than the lower limit, the volatilization of the compound (B) during thermal curing of the resin composition is suppressed, and the vinyl group of the polymer (A) having the structural unit represented by formula (V) can be reacted with the compound (B) more effectively. The boiling point of the compound (B) is preferably 300°C or lower, more preferably 250°C or lower, and even more preferably 200°C or lower. By making it equal to or lower than the upper limit, it is possible to make it difficult for the compound (B) to remain as a residual solvent in the cured product. When the resin composition of the present embodiment contains two or more compounds (B), the average boiling point may be within the above range, but it is preferable that the boiling point of each compound is within the above preferred range.

[0036] Examples of the compound (B) include (meth)acrylic acid ester compounds, aromatic vinyl compounds (preferably styrene-based compounds), saturated fatty acid vinyl compounds, vinyl cyanide compounds, ethylenically unsaturated carboxylic acids, ethylenically unsaturated carboxylic acid anhydrides, ethylenically unsaturated dicarboxylic acid monoalkyl esters, ethylenically unsaturated carboxylic acid amides, vinyl silane compounds (e.g., vinyl trialkoxy silane, etc.), acrylic silane compounds (e.g., acrylic trialkoxy silane, etc.), methacryl silane compounds (e.g., methacryl trialkoxy silane, etc.), and styryl silane compounds (e.g., styryl trialkoxy silane, etc.). At least one selected from the group consisting of (meth)acrylic acid ester compounds, aromatic vinyl compounds, saturated fatty acid vinyl compounds, vinyl silane compounds, acrylic silane compounds, methacryl silane compounds, and styryl silane compounds is preferred, and aromatic vinyl compounds and / or vinyl silane compounds are more preferred. Specific examples of the compound (B) include methylstyrene, ethylvinylbenzene, vinyltrimethoxysilane, and vinyltriethoxysilane.

[0037] In the resin composition of the present embodiment, the content of the compound (B) is preferably 1 part by mass or more, more preferably 2 parts by mass or more, and even more preferably 2.5 parts by mass or more, relative to 100 parts by mass of the resin solid content. By making it equal to or more than the lower limit, the unreacted functional groups in the obtained cured product tend to decrease, and the moisture absorption heat resistance tends to be significantly improved. In addition, the upper limit of the content of the compound (B) is preferably 30 parts by mass or less, more preferably 20 parts by mass or less, even more preferably 10 parts by mass or less, even more preferably 8 parts by mass or less, and even more preferably 5 parts by mass or less, relative to 100 parts by mass of the resin solid content. By making it equal to or less than the 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 type of compound (B), or may contain two or more types. When two or more types are contained, the total amount is preferably within the above range.

[0038] In the resin composition of this embodiment, the mass ratio of the polymer (A) to the compound (B) is preferably 0.025 or more, more preferably 0.05 or more, even more preferably 0.1 or more, even more preferably 0.15 or more, and may be 0.2 or more, relative to 1 of the polymer (A). By making it equal to or greater than the lower limit, the amount of unreacted functional groups in the obtained cured product tends to decrease, and the moisture absorption heat resistance tends to be significantly improved. The upper limit of the mass ratio of the polymer (A) to the compound (B) is preferably 0.7 or less, more preferably 0.5 or less, even more preferably 0.4 or less, even more preferably 0.3 or less, and may be 0.25 or less, relative to 1 of the polymer (A). By making it equal to or less than the upper limit, the low dielectric properties (Dk and / or Df) of the obtained cured product tend to be further improved.

[0039] In addition, the resin composition in the present embodiment has a molecular weight of less than 1000 and is 2 The composition may be substantially free of a compound (B') containing two or more organic groups having a =C(X)- (X is a hydrogen atom or a methyl group) structure in the molecule. Specific examples of the compound (B') include aromatic divinyl compounds, particularly divinylbenzene. The term "substantially free of compound (B')" means that the content of the compound (B') is less than 1 part by mass, preferably less than 0.1 part by mass, more preferably less than 0.01 part by mass, and even more preferably less than 0.001 part by mass, relative to 100 parts by mass of the resin solid content in the resin composition.

[0040] <Other thermosetting compounds (C)> The resin composition of the present embodiment preferably further contains another thermosetting compound (C) that does not fall under the polymer (A) and the compound (B). By containing such a component, other desired performance required for the printed wiring board can be more effectively exhibited. In particular, in this embodiment, the weight average molecular weight of the other thermosetting compound (C) is preferably 100 or more, more preferably 200 or more, and even more preferably 300 or more. The upper limit of the weight average molecular weight of the other thermosetting compound (C) is preferably 5,000 or less, more preferably 4,000 or less. The equivalent weight of the functional group of the other thermosetting compound (C) is preferably 100 g / eq. or more, more preferably 150 g / eq. or more, and even more preferably 200 g / eq. or more. The upper limit of the equivalent weight of the functional group of the other thermosetting compound (C) is preferably 1,500 g / eq. or less, more preferably 1,300 g / eq. or less. In this embodiment, it is particularly preferable that the other thermosetting compound (C) satisfies the above weight average molecular weight and functional group equivalent. Such other thermosetting compound (C) tends to have a smaller weight average molecular weight than the polymer (A) having the structural unit represented by formula (V), and has a higher functional group concentration, resulting in more crosslinking points, and thus more effectively improving the moisture absorption heat resistance of the obtained cured product. In this embodiment, the other thermosetting compound (C) preferably includes at least one selected from the group consisting of a maleimide compound, a polyphenylene ether compound having two or more carbon-carbon unsaturated double bonds, a cyanate ester compound, an epoxy compound, a phenol compound, an alkenyl-substituted nadimide compound, an oxetane resin, and a benzoxazine compound, more preferably includes a maleimide compound and / or a polyphenylene ether compound having two or more carbon-carbon unsaturated double bonds, even more preferably includes at least one selected from the group consisting of a compound (M1) represented by formula (M1), a compound represented by formula (M3), a compound represented by formula (M5), and a compound represented by formula (OP-1), even more preferably includes at least one selected from the group consisting of a compound (M1) represented by formula (M1), a compound represented by formula (M3), and a compound represented by formula (OP-1), and from the viewpoint of low dielectric properties, even more preferably includes a compound (M1) represented by formula (M1). [ka] (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, an aryl group having 6 to 10 carbon atoms, an aryloxy group having 1 to 10 carbon atoms, an arylthio group having 1 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.) [ka] (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 between 1 and 10.) [ka] (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 greater.) [ka] In formula (OP-1), X represents an aromatic group, -(YO)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 from 1 to 6, and n 2 represents an integer from 1 to 100, and n 3 represents an integer from 2 to 4.)

[0041] <<Maleimide compounds>> The resin composition of the present embodiment may contain a maleimide compound. The resin composition of the present embodiment is not particularly limited as long as it is a compound having one or more (preferably 2 to 12, more preferably 2 to 6, even more preferably 2 to 4, still more preferably 2 or 3, and even more preferably 2) maleimide groups in one molecule, and a wide variety of compounds commonly used in the field of printed wiring boards can be used. In this embodiment, the compounds represented by formulae (M0) to (M5) are preferred, the compounds represented by formulae (M1) to (M4) are more preferred, the compounds represented by formulae (M1) and / or (M3) are even more preferred, and the compound (M1) represented by formula (M1) is even more preferred. When these maleimide compounds are used in materials for printed wiring boards (e.g., metal foil-clad laminates), etc., excellent heat resistance can be imparted. In particular, when the compound (M1) represented by formula (M1) is used, low dielectric properties tend to be more effectively achieved. [ka] (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 greater.) R 51is 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. R 52 is preferably a methyl group. n 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 n 1 A mixture of compounds with different 51 and / or R 52 Examples of the compound include a mixture of compounds having different types of substituents, a mixture of compounds having different bonding positions (meta, para, ortho positions) of the maleimide group and the oxygen atom on 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 the formulae (M1) to (M5) below. [ka] (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 M14R 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, an aryl group having 6 to 10 carbon atoms, an aryloxy group having 1 to 10 carbon atoms, an arylthio group having 1 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.)

[0042] 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 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, and particularly preferably a methyl group. M1 and R M3 are each independently preferably an alkyl group, and R M2 and R M4 is preferably a hydrogen atom. R M5 and R M6 are each independently a hydrogen atom or an alkyl group, preferably an alkyl group. The alkyl group here is preferably an alkyl group having 1 to 12 carbon atoms, more preferably an alkyl group having 1 to 6 carbon atoms, further preferably a methyl group, an ethyl group, a propyl group, or a butyl group, and particularly preferably a methyl group. Ar M represents a divalent aromatic group, preferably a phenylene group, a naphthalenediyl group, a phenanthrenediyl group, or an anthracenediyl group, more preferably a phenylene group, and further 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 is preferably unsubstituted. A is a 4- to 6-membered alicyclic group, and more preferably a 5-membered alicyclic group (preferably a group which forms an indan 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, and is preferably 2. lx is 0 or 1, and is preferably 1. R M9 and R M10 are each independently a hydrogen atom or an alkyl group, more preferably an alkyl group. The alkyl group here is preferably an alkyl group having 1 to 12 carbon atoms, more preferably an alkyl group having 1 to 6 carbon atoms, further preferably a methyl group, an ethyl group, a propyl group, or a butyl group, and particularly preferably a methyl group. R M11 , R M12 , R M13 , and R M14 R each independently represents a hydrogen atom or an organic group. The organic group 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, and particularly preferably a methyl group. M12 and R M13 are each independently preferably an alkyl group, and R M11 and R M14 is preferably a hydrogen atom. R 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, an aryl group having 6 to 10 carbon atoms, an aryloxy group having 1 to 10 carbon atoms, an arylthio group having 1 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 the present embodiment may contain only one compound (M1) represented by formula (M1) having at least one different value of nx, or may contain two or more. When two or more compounds are contained, the average value (average number of repeating units) n of nx in the compound (M1) 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 obtain a low melting point (low softening point), a low melt viscosity, and excellent handleability. In addition, 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 the formula (M1-1) described later.

[0043] The compound (M1) represented by formula (M1) is preferably a compound represented by the following formula (M1-1). [ka] (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 M32 R 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 RM39 Each independently represents a hydrogen atom or an alkyl group. nx represents an integer of 1 or more and 20 or less.

[0044] 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 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, R M22 and R M24 is preferably a hydrogen atom. R M25 and R M26 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. R M27 , R M28 , R M29 , and R M30 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, further preferably an alkyl group having 1 to 6 carbon atoms, still more preferably a methyl group, an ethyl group, a propyl group, or a butyl group, and particularly preferably a methyl group. R M31 and R M32 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. R M33 , R M34 , R M35 , and RM36 each independently represents a hydrogen atom or an organic group. The organic group here is preferably an alkyl group, more preferably an alkyl group having 1 to 12 carbon atoms, still more preferably an alkyl group having 1 to 6 carbon atoms, still more preferably a methyl group, an ethyl group, a propyl group, or a butyl group, and particularly preferably a methyl group. R M33 and R M36 is preferably a hydrogen atom, R M34 and R M35 is preferably an alkyl group. R M37 , R M38 , R M39 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. nx represents an integer of 1 or more and 20 or less. nx may be an integer of 10 or less.

[0045] The compound represented by formula (M1-1) is preferably a compound represented by the following formula (M1-2). [ka] (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 M32 R each independently represents a hydrogen atom or an alkyl group. M33 , R M34 , R M35 , and R M36R 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. nx represents an integer of 1 or more and 20 or less.

[0046] 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), 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.

[0047] 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). [ka] (In formula (M1-3), nx represents an integer of 1 or more and 20 or less.) nx may be an integer less than or equal to 10. [ka] (In formula (M1-4), nx represents an integer of 1 or more and 20 or less.)

[0048] The molecular weight of the compound (M1) represented by formula (M1) is preferably 500 or more, more preferably 600 or more, and even more preferably 700 or more. By making it equal to or more than the lower limit, the low dielectric properties and low water absorption of the obtained cured product tend to be further improved. In addition, the molecular weight of the compound (M1) represented by formula (M1) is preferably 10000 or less, more preferably 9000 or less, even more preferably 7000 or less, even more preferably 5000 or less, and even more preferably 4000 or less. By making it equal to or less than the upper limit, the heat resistance and handleability of the obtained cured product tend to be further improved. [ka] (In formula (M2), R 54 each independently represents a hydrogen atom or a methyl group; n 4 represents an integer of 1 or greater.) n 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, and even more preferably 1 or 2. [ka] (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 between 1 and 10.) R 55 is 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. n 5 is preferably an integer of 1 or more and 5 or less, more preferably an integer of 1 to 3, and even more preferably 1 or 2. [ka] (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.

[0049] [ka] (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 greater.) R 58 is 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. R 59 is preferably a methyl group. n 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. The compound represented by formula (M5) is 6 It may be, and is preferably, a mixture of compounds having different moieties. As described in the compound represented by formula (M0), it may also be a mixture of compounds having different other moieties.

[0050] 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. Kasei Co., Ltd. as a compound represented by formula (M0), "NE-X-9470S" manufactured by DIC Corporation as a compound (M1) represented by formula (M1), "BMI-2300" manufactured by Daiwa Kasei Kogyo Co., Ltd. as a compound represented by formula (M2), "MIR-3000-70MT" manufactured by Nippon Kayaku Co., Ltd. as a compound represented by formula (M3), "BMI-70" manufactured by K.I. Kasei Co., Ltd. as a compound represented by formula (M4), and "MIR-5000" manufactured by Nippon Kayaku Co., Ltd. as a compound represented by formula (M5).

[0051] Examples of maleimide compounds other than those mentioned above include N-phenylmaleimide, phenylmethanemaleimide oligomers, 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.

[0052] When the resin composition of the present embodiment contains a maleimide compound, the lower limit of the content of the maleimide compound 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, relative to 100 parts by mass of the resin solid content in the resin composition. When the content of the maleimide compound is 1 part by mass or more, the flame resistance of the obtained cured product tends to be improved. In addition, the upper limit of the content of the maleimide compound is preferably 70 parts by mass or less, more preferably 50 parts by mass or less, and may be 40 parts by mass or less, relative to 100 parts by mass of the resin solid content in the resin composition. When the content of the maleimide compound is 70 parts by mass or less, the metal foil peel strength and low water absorption tend to be improved. The resin composition in the present embodiment may contain only one type of maleimide compound, or may contain two or more types. When two or more types are contained, the total amount is preferably in the above range. In addition, the resin composition in this embodiment may be configured to be substantially free of maleimide compounds, particularly monofunctional maleimide compounds. Substantially free means that the content of the monofunctional maleimide compound, and further the maleimide compound, is less than 1 part by mass relative to 100 parts by mass of the resin solid content in the resin composition, preferably less than 0.1 parts by mass, and more preferably less than 0.01 parts by mass. By substantially not including a monofunctional maleimide, the reaction between the vinyl groups proceeds preferentially over the reaction between the maleimide group of the maleimide compound and the vinyl group of the polymer (A) having the structural unit represented by formula (V) or the inorganic filler (B), and a cured product with excellent low dielectric properties tends to be obtained. In addition, when the reaction between the vinyl groups proceeds preferentially, the degree of curing after heating tends to be improved from the viewpoint of steric hindrance.

[0053] <<Polyphenylene ether compounds containing two or more carbon-carbon unsaturated double bonds>> The resin composition of the present embodiment may contain a polyphenylene ether compound containing two or more carbon-carbon unsaturated double bonds. The polyphenylene ether compound containing two or more carbon-carbon unsaturated double bonds is preferably a polyphenylene ether compound having two or more groups selected from the group consisting of (meth)acrylic groups, maleimide groups, and vinylbenzyl groups at its terminals. By using these polyphenylene ether compounds, the dielectric properties and low water absorption of printed wiring boards and the like tend to be more effectively improved. These will be explained in detail below.

[0054] An example of the polyphenylene ether compound containing two or more carbon-carbon unsaturated double bonds is a compound having a phenylene ether skeleton represented by the following formula (X1).

[0055] [ka] (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.

[0056] The polyphenylene ether compound containing two or more carbon-carbon unsaturated double bonds has the formula (X2): [ka] (In formula (X2), R 28 , R 29 , R 30 , R 34 , and R 35 R may be the same or different and represents 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 the formula (X3): [ka] (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 straight-chain, branched or cyclic divalent hydrocarbon group having 20 or less carbon atoms.

[0057] The polyphenylene ether compound containing two or more carbon-carbon unsaturated double bonds is preferably a modified polyphenylene ether compound in which a part or all of the terminals are functionalized with an ethylenically unsaturated group (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)acrylic groups, maleimide groups, and vinylbenzyl groups at the terminals. By adopting such a modified polyphenylene ether compound (g), it becomes possible to further reduce the dielectric loss tangent (Df) of the cured product of the resin composition, and to increase the low water absorption and metal foil peel strength. These may be used alone or in combination of two or more kinds.

[0058] The modified polyphenylene ether compound (g) may be a compound represented by the formula (OP-1). [ka] In formula (OP-1), X represents an aromatic group, -(YO)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 from 1 to 6, and n 2 represents an integer from 1 to 100, and n 3 represents an integer from 2 to 4.) n2 If n is an integer greater than or equal to 2, 3 About n 2 Structural units (YO) and / or n 3 The structural units may be the same or different. 3 is preferably 2.

[0059] The modified polyphenylene ether compound (g) in this embodiment is preferably a compound represented by formula (OP-2). [ka] Here, -(OXO)- is represented by the formula (OP-3): [ka] (In formula (OP-3), R 4 , R 5 , R 6 , R 10 , and R 11 R may be the same or different and is an alkyl group or a phenyl group 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 formula (OP-4): [ka] (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.

[0060] Also, -(YO)- is a group represented by the formula (OP-5): [ka] (In formula (OP-5), R 20 , R 21 R may be the same or different and is an alkyl group or a phenyl group 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. In formula (OP-2), a and b, at least one of which is not 0, represent an integer of 0 to 100, preferably an integer of 0 to 50, and more preferably an integer of 1 to 30. When a and / or b are an integer of 2 or more, two or more -(YO)- may each independently represent an arrangement of one type of structure, or two or more types of structures may be arranged in a block or random manner.

[0061] 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.

[0062] Among the above modified polyphenylene ether compounds (g), 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 , R18 , 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 -(OXO)- represented by formula (OP-3) or formula (OP-4) is formula (OP-9), formula (OP-10), and / or formula (OP-11), and -(YO)- 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 -(YO)- 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.

[0063] [ka] [ka] (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). [ka] (In formula (OP-11), -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). [ka] [ka]

[0064] For details of the polyphenylene ether compound containing two or more carbon-carbon unsaturated double bonds, refer to the description of JP 2018-016709 A, the contents of which are incorporated herein by reference.

[0065] The polyphenylene ether compound containing two or more carbon-carbon unsaturated double bonds (preferably modified polyphenylene ether compound (g)) preferably has a number average molecular weight of 500 or more and 3,000 or less in terms of polystyrene measured by a GPC (gel permeation chromatography) method. When the number average molecular weight is 500 or more, stickiness tends to be further suppressed when the resin composition of the present embodiment is formed into a coating film. When the number average molecular weight is 3,000 or less, solubility in a solvent tends to be further improved. Furthermore, the weight average molecular weight of the polystyrene-equivalent weight average molecular weight by GPC of the polyphenylene ether compound containing two or more carbon-carbon unsaturated double bonds (preferably the modified polyphenylene ether compound (g)) is preferably 800 to 10,000, more preferably 800 to 5,000. By making it equal to or more than the lower limit, the relative dielectric constant (Dk) and dielectric loss tangent (Df) of the cured product of the resin composition tend to be lower, and by making it equal to or less than the upper limit, the solubility, low viscosity, and moldability of the resin composition in a solvent when preparing a varnish or the like described below tend to be improved. Furthermore, in the case of the modified polyphenylene ether compound (g), the terminal carbon-carbon unsaturated double bond equivalent is preferably 400 to 5000 g per carbon-carbon unsaturated double bond, more preferably 400 to 2500 g. By making it equal to or greater than the lower limit, the relative dielectric constant (Dk) and dielectric loss tangent (Df) of the cured product of the resin composition tend to be lower. By making it equal to or less than the upper limit, the solubility in the solvent, low viscosity, and moldability of the resin composition tend to be improved.

[0066] When the resin composition of the present embodiment includes a polyphenylene ether compound having two or more carbon-carbon unsaturated double bonds, the lower limit of the content of the polyphenylene ether compound having two or more carbon-carbon unsaturated double bonds 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, even more preferably 7 parts by mass or more, and even more preferably 10 parts by mass or more, relative to 100 parts by mass of the resin solid content in the resin composition. By setting the content to the lower limit or more, the low water absorption and low dielectric properties (Dk and / or Df) of the obtained cured product tend to be further improved. In addition, the upper limit of the content of the polyphenylene ether compound having two or more carbon-carbon unsaturated double bonds is preferably 70 parts by mass or less, more preferably 60 parts by mass or less, even more preferably 50 parts by mass or less, even more preferably 40 parts by mass or less, even more preferably 35 parts by mass or less, even more preferably 25 parts by mass or less, and may be 20 parts by mass or less, relative to 100 parts by mass of the resin solid content in the resin composition. By ensuring that the content is equal to or less than the above upper limit, the heat resistance and chemical resistance of the resulting cured product tend to be further improved. The resin composition in the present embodiment may contain only one type of polyphenylene ether compound containing two or more carbon-carbon unsaturated double bonds, or may contain two or more types. When two or more types are contained, the total amount is preferably within the above range.

[0067] <<Cyanate ester compounds>> The resin composition of the present embodiment may contain a cyanate ester compound. The cyanate ester compound is not particularly limited as long as it contains one or more (preferably 2 to 12, more preferably 2 to 6, even more preferably 2 to 4, still more preferably 2 or 3, and even more preferably 2) 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. In addition, the cyanate ester compound is preferably a compound in which a cyanate group is directly bonded to an aromatic skeleton (aromatic ring). Examples of the cyanate ester compound include at least one selected from the group consisting of phenol novolac type cyanate ester compounds, naphthol aralkyl type cyanate ester compounds (naphthol aralkyl type cyanates), naphthylene ether type cyanate ester compounds, biphenyl aralkyl type cyanate ester compounds, xylene resin type cyanate ester compounds, trisphenolmethane type cyanate ester compounds, adamantane skeleton type cyanate ester compounds, bisphenol M type cyanate ester compounds, bisphenol A type cyanate ester compounds, and diallyl bisphenol A type cyanate ester compounds. Among these, from the viewpoint of further improving the low water absorption of the obtained cured product, it is preferable to use at least one selected from the group consisting of phenol novolac type cyanate ester compounds, naphthyl ether type cyanate ester compounds, xylene resin type cyanate ester compounds, bisphenol M type cyanate ester compounds, bisphenol A type cyanate ester compounds, and diallyl bisphenol A type cyanate ester compounds, more preferably at least one selected from the group consisting of phenol novolac type cyanate ester compounds and naphthyl aralkyl type cyanate ester compounds, and even more preferably naphthyl aralkyl type cyanate ester compounds. These cyanate ester compounds may be prepared by a known method, or a commercially available product may be used. Note that cyanate ester compounds having a naphthyl aralkyl skeleton, naphthyl ether skeleton, xylene skeleton, trisphenol methane skeleton, or adamantane skeleton have a relatively large functional group equivalent number and a small number of unreacted cyanate ester groups, so that the cured product of the resin composition using these tends to have even better low water absorption. Furthermore, due mainly to the presence of an aromatic skeleton or an adamantane skeleton, plating adhesion tends to be further improved.

[0068] As the naphthol aralkyl cyanate ester compound, a compound represented by the following formula (1) is more preferable.

[0069] [ka] (In formula (1), R 3 each independently represents a hydrogen atom or a methyl group, and n3 represents an integer of 1 or greater.

[0070] 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 is an integer of 1 or more, and is preferably an integer of 1-20, more preferably an integer of 1-10, and further preferably an integer of 1-6.

[0071] The novolac-type cyanate ester compound is not particularly limited, but is preferably, for example, a compound represented by the following formula (VII). [ka] (In formula (VII), R 6 each independently represents a hydrogen atom or a methyl group, and n7 represents an integer of 1 or greater.

[0072] In formula (VII), R 6 each independently represents a hydrogen atom or a methyl group, and among these, a hydrogen atom is preferred. In formula (VII), n7 is an integer of 1 or more, and is 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.

[0073] 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.

[0074] The resin composition of the present embodiment preferably contains a cyanate ester compound in a range that does not impair the effects of the present invention. When the resin composition of the present embodiment contains a cyanate ester compound, the lower limit of the content is preferably 0.1 parts by mass or more, more preferably 0.2 parts by mass or more, and even more preferably 0.5 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 cyanate ester compound is 0.1 parts by mass or more, the heat resistance, flame resistance, chemical resistance, low relative dielectric constant, low dielectric loss tangent, and insulating properties of the obtained cured product tend to be improved. When the resin composition of the present embodiment contains a cyanate ester compound, the upper limit of the content of the cyanate ester compound 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, even more preferably 20 parts by mass or less, and may be 10 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. The resin composition in the present embodiment may contain only one type of cyanate ester compound, or may contain two or more types. When two or more types are contained, the total amount is preferably in the above range.

[0075] <<Epoxy compounds>> The resin composition of the present embodiment may contain an epoxy compound. The epoxy compound is not particularly limited as long as it is a compound or resin having one or more (preferably 2 to 12, more preferably 2 to 6, even more preferably 2 to 4, still more preferably 2 or 3, and even more preferably 2) epoxy groups in one molecule, and a wide range of compounds commonly used in the field of printed wiring boards can be used. Examples of the epoxy compound include bisphenol A type epoxy resin, bisphenol E type epoxy resin, bisphenol F type epoxy resin, bisphenol S type epoxy resin, phenol novolac type epoxy resin, bisphenol A novolac type epoxy resin, glycidyl ester type epoxy resin, aralkyl novolac type epoxy resin, biphenyl aralkyl type epoxy resin, naphthylene ether type epoxy resin, cresol novolac type epoxy resin, multifunctional phenol type epoxy resin, naphthalene type epoxy resin, anthracene type epoxy resin, naphthalene skeleton modified novolac type epoxy resin, phenol aralkyl type epoxy resin, naphthol aralkyl type epoxy resin, dicyclopentadiene type epoxy resin, biphenyl type epoxy resin, alicyclic epoxy resin, polyol type epoxy resin, phosphorus-containing epoxy resin, glycidyl amine, glycidyl ester, compounds in which the double bond of butadiene is epoxidized, compounds obtained by reacting hydroxyl group-containing silicone resins with epichlorohydrin, etc. By using these, the moldability and adhesion of the resin composition are improved. Among these, from the viewpoint of further improving flame retardancy and heat resistance, biphenyl aralkyl type epoxy resins, naphthylene ether type epoxy resins, polyfunctional phenol type epoxy resins, and naphthalene type epoxy resins are preferred, and biphenyl aralkyl type epoxy resins are more preferred.

[0076] The resin composition of the present embodiment preferably contains an epoxy compound in a range that does not impair the effects of the present invention. When the resin composition of the present embodiment contains an epoxy compound, the content 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, the metal foil peel strength and toughness tend to be improved. When the resin composition of the present embodiment contains an epoxy compound, 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, even more preferably 10 parts by mass or less, even more preferably 8 parts by mass or less, and even more preferably 5 parts by mass or less, 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 in the present 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 in the above range. The resin composition in the present embodiment may be configured to be substantially free of epoxy compounds. Substantially free means that the content of the epoxy compounds 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.

[0077] <<Phenol compounds>> The resin composition of the present embodiment may contain a phenol compound. The phenol compound is not particularly limited as long as it has one 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) phenolic hydroxyl groups in one molecule, and a wide range of compounds commonly used in the field of printed wiring boards can be used. Examples of the phenol compound include bisphenol A type phenolic resin, bisphenol E type phenolic resin, bisphenol F type phenolic resin, bisphenol S type phenolic resin, phenol novolac resin, bisphenol A novolac type phenolic resin, glycidyl ester type phenolic resin, aralkyl novolac phenolic resin, biphenyl aralkyl type phenolic resin, cresol novolac type phenolic resin, polyfunctional phenolic resin, naphthol resin, naphthol novolac resin, polyfunctional naphthol resin, anthracene type phenolic resin, naphthalene skeleton modified novolac type phenolic resin, phenol aralkyl type phenolic resin, naphthol aralkyl type phenolic resin, dicyclopentadiene type phenolic resin, biphenyl type phenolic resin, alicyclic phenolic resin, polyol type phenolic resin, phosphorus-containing phenolic resin, and hydroxyl group-containing silicone resins. Among these, from the viewpoint of further improving the flame resistance of the obtained cured product, it is preferable to use at least one type selected from the group consisting of biphenyl aralkyl type phenolic resins, naphthol aralkyl type phenolic resins, phosphorus-containing phenolic resins, and hydroxyl group-containing silicone resins.

[0078] The resin composition of the present embodiment preferably contains a phenolic compound in an amount not impairing the effects of the present invention. When the resin composition of the present embodiment contains a phenolic compound, the content of the phenolic compound is preferably 0.1 parts by mass or more and 50 parts by mass or less per 100 parts by mass of the resin solid content in the resin composition. The resin composition in the present embodiment may contain only one type of phenol compound, or may contain two or more types. When two or more types are contained, the total amount is preferably in the above range. The resin composition of the present embodiment may be configured to be substantially free of phenol compounds, which means that the content of phenol compounds is less than 0.1 parts by mass per 100 parts by mass of the resin solid content in the resin composition.

[0079] <<Alkenyl-substituted nadimide compounds>> The alkenyl-substituted nadiimide compound is not particularly limited as long as it is a compound having one or more alkenyl-substituted nadiimide groups in the molecule.Among these, the compound represented by formula (AN-1) is preferred.By using such an alkenyl-substituted nadiimide compound, the thermal expansion coefficient of the obtained cured product tends to be further reduced and the heat resistance tends to be further improved. [ka] (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, a group represented by formula (AN-2), or a group represented by formula (AN-3). [ka] (In formula (AN-2), R 3 is a methylene group, an isopropylidene group, -C(=O)-, -O-, -S-, or -S(=O) 2 - indicates.) [ka] (In formula (AN-3), R 4 each independently represents an alkylene group having 1 to 4 carbon atoms or a cycloalkylene group having 5 to 8 carbon atoms.

[0080] Among the compounds represented by formula (AN-1), the compounds represented by formula (AN-4) and (AN-5) are preferred. By using such alkenyl-substituted nadimide compounds, the thermal expansion coefficient of the obtained cured product tends to be further reduced and the heat resistance tends to be further improved. [ka] [ka]

[0081] In addition, the alkenyl-substituted nadiimide compound may be commercially available. Examples of commercially available alkenyl-substituted nadiimide compounds include, but are not limited to, BANI-M (manufactured by Maruzen Petrochemical Co., Ltd., a compound represented by formula (AN-4)), BANI-X (manufactured by Maruzen Petrochemical Co., Ltd., a compound represented by formula (AN-5)), and the like.

[0082] The resin composition of the present embodiment preferably contains an alkenyl-substituted nadimide compound in an amount not impairing the effects of the present invention. When the resin composition of the present embodiment contains an alkenyl-substituted nadimide compound, the content is preferably 0.1 parts by mass or more and 50 parts by mass or less relative to 100 parts by mass of the resin solid content in the resin composition. The resin composition in the present embodiment may contain only one type of alkenyl-substituted nadimide compound, or may contain two or more types. When two or more types are contained, the total amount is preferably in the above range. The resin composition of the present embodiment may be configured to be substantially free of an alkenyl-substituted nadimide compound, where "substantially free" means that the content of the alkenyl-substituted nadimide compound is less than 0.1 parts by mass per 100 parts by mass of the resin solid content in the resin composition.

[0083] <<Oxetane resin>> The resin composition of the present embodiment may contain an oxetane resin. The oxetane resin 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, still 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 oxetane resins include oxetane, alkyl oxetane (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-type oxetane, OXT-101 (manufactured by Toagosei Co., Ltd.), and OXT-121 (manufactured by Toagosei Co., Ltd.).

[0084] The resin composition of the present embodiment preferably contains an oxetane resin in a range that does not impair the effects of the present invention. When the resin composition of the present embodiment contains an oxetane resin, the content 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 resin is 0.1 parts by mass or more, the metal foil peel strength and toughness tend to be improved. When the resin composition of the present embodiment contains an oxetane resin, the upper limit of the content of the oxetane resin is preferably 50 parts by mass or less, more preferably 30 parts by mass or less, even more preferably 20 parts by mass or less, even more preferably 10 parts by mass or less, and even more preferably 8 parts by mass or less, relative to 100 parts by mass of the resin solid content in the resin composition. When the content of the oxetane resin is 50 parts by mass or less, the electrical properties of the obtained cured product tend to be improved. The resin composition in the present embodiment may contain only one type of oxetane resin, or may contain two or more types. When two or more types are contained, the total amount is preferably in the above range. The resin composition in this embodiment may be configured to be substantially free of oxetane resin. Substantially free means that the content of oxetane resin is less than 0.1 parts by mass per 100 parts by mass of the resin solid content in the resin composition.

[0085] <<Benzoxazine compounds>> The resin composition of the present embodiment may contain a benzoxazine compound. The benzoxazine compound is not particularly limited as long as it has two or more (preferably 2 to 12, more preferably 2 to 6, even more preferably 2 to 4, still more preferably 2 or 3, and even more preferably 2) dihydrobenzoxazine rings in one molecule, and a wide variety of compounds commonly used in the field of printed wiring boards can be used. Examples of the benzoxazine compound include bisphenol A-type benzoxazine BA-BXZ (manufactured by Konishi Chemical Co., Ltd.), bisphenol F-type benzoxazine BF-BXZ (manufactured by Konishi Chemical Co., Ltd.), and bisphenol S-type benzoxazine BS-BXZ (manufactured by Konishi Chemical Co., Ltd.).

[0086] The resin composition of the present embodiment preferably contains a benzoxazine compound in an amount not impairing the effects of the present invention. When the resin composition of the present embodiment contains a benzoxazine compound, the content is preferably 0.1 parts by mass or more and preferably 50 parts by mass or less relative to 100 parts by mass of the resin solid content in the resin composition. The resin composition in the present embodiment may contain only one type of benzoxazine compound, or may contain two or more types. When two or more types are contained, the total amount is preferably in the above range. The resin composition of the present embodiment may be configured to be substantially free of benzoxazine compounds, meaning that the content of the benzoxazine compounds is less than 0.1 parts by mass per 100 parts by mass of the resin solid content in the resin composition.

[0087] When the resin composition of the present embodiment contains a thermosetting compound (C), its content (total amount) is preferably 3 parts 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 even more preferably 30 parts by mass or more, relative to 100 parts by mass of resin solid content. By making it equal to or more than the lower limit, heat resistance, plating adhesion, low thermal expansion, etc. tend to be further improved. In addition, the upper limit of the content of the thermosetting compound (C) is preferably 95 parts by mass or less, more preferably 85 parts by mass or less, even more preferably 75 parts by mass or less, even more preferably 65 parts by mass or less, and even more preferably 50 parts by mass or less, relative to 100 parts by mass of resin solid content. By making it equal to or less than the upper limit, low dielectric properties and low water absorption tend to be further improved. The resin composition of the present 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.

[0088] <Filling material (D)> The resin composition of the present embodiment preferably contains a filler (D). By containing the filler (D), the resin composition and its cured product can have improved physical properties such as dielectric properties (low dielectric constant, low dielectric loss tangent, etc.), flame resistance, and low thermal expansion. Moreover, the filler (D) used in this embodiment is more preferably excellent in low dielectric properties. For example, the filler (D) used in this embodiment has a relative dielectric constant (Dk) measured according to the cavity resonator perturbation method of preferably 8.0 or less, more preferably 6.0 or less, and even more preferably 4.0 or less. The lower limit of the relative dielectric constant is, for example, 2.0 or more in practical use. The filler (D) used in this embodiment has a dielectric loss tangent (Df) measured according to the cavity resonator perturbation method of preferably 0.05 or less, more preferably 0.01 or less. The lower limit of the dielectric loss tangent is, for example, 0.0001 or more in practical use.

[0089] The filler (D) used in this embodiment is not particularly limited in type, and can be suitably used in the industry.Specifically, natural silica, fused silica, synthetic silica, amorphous silica, aerosil, hollow silica, and other silicas, alumina, white carbon, titanium white, titanium oxide, zinc oxide, magnesium oxide, zirconium oxide, and other metal oxides, zinc borate, zinc stannate, forsterite, barium titanate, strontium titanate, calcium titanate, and other composite oxides, boron nitride, aggregated boron nitride, silicon nitride, aluminum nitride, and other nitrides, aluminum hydroxide, aluminum hydroxide heat treatment product (aluminum hydroxide heat treatment, part of crystal water is reduced), boehmite, magnesium hydroxide, and other metal hydroxides (including hydrates). Examples of fillers include inorganic fillers such as molybdenum compounds such as molybdenum oxide and zinc molybdate, barium sulfate, clay, kaolin, talc, calcined clay, calcined kaolin, calcined talc, mica, E-glass, A-glass, NE-glass, C-glass, L-glass, D-glass, S-glass, M-glass G20, 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 powder, silicone rubber powder, and silicone composite powder. In this embodiment, inorganic fillers are preferred, and more preferably contain one or more selected from the group consisting of silica, aluminum hydroxide, aluminum nitride, boron nitride, forsterite, titanium oxide, barium titanate, strontium titanate, and calcium titanate, and from the viewpoint of low dielectric properties, more preferably contain one or more selected from the group consisting of silica and aluminum hydroxide, and even more preferably contain silica. By using these inorganic fillers, the properties such as heat resistance, dielectric properties, thermal expansion properties, dimensional stability, and flame retardancy of the cured product of the resin composition are further improved.

[0090] The content of the filler (D) in the resin composition of this embodiment can be appropriately set according to the desired properties, and is not particularly limited, but 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 it to the lower limit or more, low thermal expansion and low dielectric loss tangent tend to be further improved. In addition, the upper limit of the content of the filler (D) is preferably 500 parts by mass or less, more preferably 300 parts by mass or less, even more preferably 200 parts by mass or less, even more preferably 150 parts by mass or less, and even more preferably 120 parts by mass or less, relative to 100 parts by mass of the resin solid content. By setting it to the upper limit or less, moldability tends to be further improved. In the resin composition of this embodiment, one preferred embodiment is one in which the content of the filler (D) is 30% by mass to 80% by mass of the components excluding the solvent. The resin composition of the present embodiment may contain only one type of filler (D), or may contain two or more types. When two or more types are contained, the total amount is preferably within the above range.

[0091] In the resin composition of the present embodiment, when the filler (D), particularly an inorganic filler, is used, a silane coupling agent may be further included. By including a silane coupling agent, the dispersibility of the filler (D) and the adhesive strength between the resin component and the filler (D) and the substrate described below tend to be further improved. The silane coupling agent is not particularly limited, and includes silane coupling agents generally used for 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, etc.), styrylsilane compounds, acrylicsilane compounds (e.g., γ-acryloxypropyltrimethoxysilane, etc.), cationic silane compounds (e.g., N-β-(N-vinylbenzylaminoethyl)-γ-aminopropyltrimethoxysilane hydrochloride, etc.), phenylsilane compounds, etc. The silane coupling agents are 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 with respect to 100 parts by mass of the resin solid content.

[0092] <Elastomer> The resin composition of the present embodiment may contain an elastomer. In the present embodiment, the elastomer is not particularly limited, and examples thereof include at least one selected from the group consisting of polyisoprene, polybutadiene, styrene butadiene, butyl rubber, ethylene propylene rubber, styrene butadiene ethylene, styrene butadiene styrene, styrene isoprene styrene, styrene ethylene butylene styrene, styrene propylene styrene, styrene ethylene propylene styrene, fluororubber, silicone rubber, hydrogenated compounds thereof, alkyl compounds thereof, and copolymers thereof. In addition, the elastomer may be a thermoplastic elastomer or a thermosetting elastomer, but a thermoplastic elastomer is preferred.

[0093] The number average molecular weight of the elastomer used in this embodiment is preferably 50,000 or more. By setting the number average molecular weight to 50,000 or more, the low dielectric properties of the obtained cured product tend to be more excellent. The number average molecular weight is preferably 60,000 or more, more preferably 70,000 or more, and even more preferably 80,000 or more. The upper limit of the number average molecular weight of the thermal elastomer is preferably 400,000 or less, more preferably 350,000 or less, and even more preferably 300,000 or less. By setting it to the upper limit or less, the solubility of the elastomer component in the resin composition tends to be improved. When the resin composition of the present embodiment contains two or more types of elastomers, it is preferable that the number average molecular weight of the mixture thereof falls within the above range.

[0094] In this embodiment, the elastomer is preferably a thermoplastic elastomer containing a styrene monomer unit and a conjugated diene monomer unit (hereinafter referred to as "thermoplastic elastomer (E)"). By using such a thermoplastic elastomer (E), the low dielectric properties of the obtained cured product are more excellent.

[0095] The thermoplastic elastomer (E) contains a styrene monomer unit. By containing the styrene monomer unit, the solubility of the thermoplastic elastomer (E) in the resin composition is improved. Examples of the styrene monomer include styrene, α-methylstyrene, p-methylstyrene, divinylbenzene (vinylstyrene), N,N-dimethyl-p-aminoethylstyrene, and N,N-diethyl-p-aminoethylstyrene. Among these, from the viewpoints of availability and productivity, one or more selected from the group consisting of styrene, α-methylstyrene, and p-methylstyrene are preferred. Among these, styrene is particularly preferred. The content of the styrene monomer unit in the thermoplastic elastomer (E) is preferably in the range of 10 to 50% by mass of the total monomer units, more preferably in the range of 13 to 45% by mass, and even more preferably in the range of 15 to 40% by mass. If the content of the styrene monomer unit is 50% by mass or less, the adhesion and tackiness to the substrate and the like will be better. Also, if it is 10% by mass or more, the adhesion can be suppressed, adhesive residue and stop marks are unlikely to occur, and the adhesive surfaces tend to be easily peeled from each other, which is preferable. The thermoplastic elastomer (E) may contain only one type of styrene monomer unit, or may contain two or more types. When two or more types are contained, the total amount is preferably within the above range. The method for measuring the content of the styrene monomer unit in the thermoplastic elastomer (E) can be found in International Publication No. 2017 / 126469, the contents of which are incorporated herein by reference. The same applies to the conjugated diene monomer units and the like described below.

[0096] The thermoplastic elastomer (E) contains a conjugated diene monomer unit. By containing the conjugated diene monomer unit, the solubility of the thermoplastic elastomer (E) in the resin composition is improved. The conjugated diene monomer is not particularly limited as long as it is a diolefin having one pair of conjugated double bonds. Examples of the conjugated diene monomer include 1,3-butadiene, 2-methyl-1,3-butadiene (isoprene), 2,3-dimethyl-1,3-butadiene, 1,3-pentadiene, 2-methyl-1,3-pentadiene, 1,3-hexadiene, and farnesene, and 1,3-butadiene and / or isoprene are preferred, and 1,3-butadiene is more preferred. The thermoplastic elastomer (E) may contain only one type of conjugated diene monomer unit, or may contain two or more types.

[0097] In the thermoplastic elastomer (E), the mass ratio of the styrene monomer unit to the conjugated diene monomer unit is preferably in the range of 5 / 95 to 80 / 20, more preferably in the range of 7 / 93 to 77 / 23, and even more preferably in the range of 10 / 90 to 70 / 30. When the mass ratio of the styrene monomer unit to the conjugated diene monomer unit is in the range of 5 / 95 to 80 / 20, the adhesion can be suppressed from increasing, the adhesion strength can be maintained high, and the adhesive surfaces can be easily peeled from each other.

[0098] The thermoplastic elastomer (E) may have all of its conjugated diene bonds hydrogenated, or may have only a portion of its conjugated diene bonds hydrogenated, or may not have any conjugated diene bonds hydrogenated.

[0099] The thermoplastic elastomer (E) may or may not contain other monomer units in addition to the styrene monomer units and the conjugated diene monomer units. Examples of other monomer units include aromatic vinyl compound units other than the styrene monomer units. In the thermoplastic elastomer (E), the sum of styrene monomer units and conjugated diene monomer units preferably accounts for 90 mass% or more of all monomer units, more preferably 95 mass% or more, even more preferably 97 mass% or more, and still more preferably 99 mass% or more. The thermoplastic elastomer (E) may contain only one type of styrene monomer unit and one type of conjugated diene monomer unit, or may contain two or more types. When two or more types are contained, the total amount is preferably within the above range.

[0100] The thermoplastic elastomer (E) may be a block polymer or a random polymer, and may be a hydrogenated elastomer in which the conjugated diene monomer units are hydrogenated, a non-hydrogenated elastomer in which the conjugated diene monomer units are not hydrogenated, or a partially hydrogenated elastomer in which the conjugated diene monomer units are partially hydrogenated. In one embodiment of this embodiment, the thermoplastic elastomer (E) is a hydrogenated elastomer. Here, the hydrogenated elastomer means, for example, a thermoplastic elastomer in which double bonds based on conjugated diene monomer units are hydrogenated, and includes elastomers with a hydrogenation rate (hydrogenation rate) of 100% or more as well as elastomers with a hydrogenation rate of 80% or more. The hydrogenation rate in the hydrogenated elastomer is preferably 85% or more, more preferably 90% or more, and even more preferably 95% or more. In this embodiment, the hydrogenation rate is 1 It is calculated from the results of H-NMR spectroscopy. In one embodiment of this embodiment, the thermoplastic elastomer (E) is an unhydrogenated elastomer. Here, the unhydrogenated elastomer includes an elastomer having a ratio of hydrogenated double bonds based on conjugated diene monomer units in the elastomer, that is, a hydrogenation rate (hydrogenation rate) of 20% or less. The hydrogenation rate in the unhydrogenated elastomer is preferably 15% or less, more preferably 10% or less, and even more preferably 5% or less. On the other hand, a partially hydrogenated elastomer means a thermoplastic elastomer in which some of the double bonds based on the conjugated diene monomer units are hydrogenated, and usually refers to a hydrogenation rate of less than 80% and more than 20%.

[0101] Examples of commercially available thermoplastic elastomers (E) used in the present embodiment include SEPTON (registered trademark) 2104 manufactured by Kuraray Co., Ltd., SOE (registered trademark) S1606, S1613, S1609, and S1605 manufactured by Asahi Kasei Corporation, and DYNARON (registered trademark) 9901P and TR2250 manufactured by JSR Corporation.

[0102] When the resin composition of the present embodiment contains an elastomer (preferably, a thermoplastic elastomer (E)), 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 15 parts by mass or more, and even more preferably 20 parts by mass or more, relative to 100 parts by mass of the resin solid content. By making the content equal to or more than the lower limit, the low dielectric properties tend to be further improved. In addition, the upper limit of the content of the elastomer is preferably 45 parts by mass or less, more preferably 40 parts by mass or less, even more preferably 35 parts by mass or less, even more preferably 32 parts by mass or less, and even more preferably 28 parts by mass or less, relative to 100 parts by mass of the resin solid content. By making the content equal to or less than the upper limit, the heat resistance tends to be further improved. The resin composition of the present embodiment may contain only one type of elastomer, or may contain two or more types. When two or more types are contained, the total amount is preferably in the above range.

[0103] <Active ester compounds> The resin composition of the present embodiment may contain an active ester compound. The active ester compound is not particularly limited, and examples thereof include compounds having two or more (preferably 2 to 12, more preferably 2 to 6, even more preferably 2 to 4, still more preferably 2 or 3, and even more preferably 2) active ester groups in one molecule. The active ester compound may be a straight-chain, branched or cyclic compound. Among these, from the viewpoint of further improving the heat resistance of the obtained cured product, the active ester compound obtained by reacting a carboxylic acid compound and / or a thiocarboxylic acid compound with a hydroxyl compound and / or a thiol compound is preferred, the active ester compound obtained by reacting a carboxylic acid compound with one or more compounds selected from the group consisting of a phenol compound, a naphthol compound and a thiol compound is more preferred, the aromatic compound obtained by reacting a carboxylic acid compound with an aromatic compound having a phenolic hydroxyl group and having two or more active ester groups in one molecule is more preferred, and the aromatic compound obtained by reacting a compound having two or more carboxylic acids in one molecule with an aromatic compound having a phenolic hydroxyl group and having two or more active ester groups in one molecule is particularly preferred. The above-mentioned carboxylic acid compound may be one or more selected from the group consisting of benzoic acid, acetic acid, succinic acid, maleic acid, itaconic acid, phthalic acid, isophthalic acid, terephthalic acid, and pyromellitic acid. Among these, from the viewpoint of further improving the heat resistance of the obtained cured product, one or more selected from the group consisting of succinic acid, maleic acid, itaconic acid, phthalic acid, isophthalic acid, and terephthalic acid are preferred, and one or more selected from the group consisting of isophthalic acid and terephthalic acid are more preferred. The thiocarboxylic acid compound may be one or more selected from thioacetic acid and thiobenzoic acid. The phenol compound or naphthol compound may be at least one selected from the group consisting of hydroquinone, resorcin, bisphenol A, bisphenol F, bisphenol S, phenolphthaline, methylated bisphenol A, methylated bisphenol F, methylated bisphenol S, phenol, o-cresol, m-cresol, p-cresol, catechol, α-naphthol, β-naphthol, 1,5-dihydroxynaphthalene, 1,6-dihydroxynaphthalene, 2,6-dihydroxynaphthalene, dihydroxybenzophenone, trihydroxybenzophenone, tetrahydroxybenzophenone, phloroglucin, benzenetriol, dicyclopentadienyldiphenol, and phenol novolak. From the viewpoint of further improving the heat resistance and solvent solubility of the obtained cured product, bisphenol A, bisphenol F, bisphenol S, methylated bisphenol S, phenol, o-cresol, m-cresol, p-cresol, catechol, α-naphthol, β-naphthol, 1,5-dihydroxynaphthalene, 1,6-dihydroxynaphthalene, 2,6-dihydroxynaphthalene, dihydroxybenzophenone, trihydroxybenzophenone, tetrahydroxybenzophenone, phloroglucin, benzenetriol, dicyclopentadienyldiphenol, and phenol novolak may be used. Preferred are bisphenol A, methylated bisphenol F, methylated bisphenol S, catechol, α-naphthol, β-naphthol, 1,5-dihydroxynaphthalene, 1,6-dihydroxynaphthalene, 2,6-dihydroxynaphthalene, dihydroxybenzophenone, trihydroxybenzophenone, tetrahydroxybenzophenone, phloroglucinone, benzenetriol, dicyclopentadienyl diphenol, and phenol novolak, and more preferred are one or more selected from the group consisting of catechol, 1,5-dihydroxynaphthalene, 1,6-dihydroxynaphthalene, 2,6-dihydroxynaphthalene, dihydroxybenzophenone, trihydroxybenzophenone, tetrahydroxybenzophenone, phloroglucinone, benzenetriol, dicyclopentadienyl diphenol, and phenol novolak.More preferably, the compound is at least one selected from the group consisting of 6-dihydroxynaphthalene, dihydroxybenzophenone, trihydroxybenzophenone, tetrahydroxybenzophenone, dicyclopentadienyl diphenol, and phenol novolac, and particularly preferably at least one selected from the group consisting of dihydroxybenzophenone, trihydroxybenzophenone, tetrahydroxybenzophenone, dicyclopentadienyl diphenol, and phenol novolac (preferably at least one selected from the group consisting of dicyclopentadienyl diphenol and phenol novolac, more preferably dicyclopentadienyl diphenol). The thiol compound may be one or more compounds selected from the group consisting of benzenedithiol and triazinedithiol. In addition, the active ester compound is preferably a compound having two or more carboxylic acids in one molecule and containing an aliphatic chain from the viewpoint of further improving compatibility with the epoxy compound, and is preferably a compound having an aromatic ring from the viewpoint of further improving heat resistance. More specific examples of the active ester compound include the active ester compounds described in JP-A-2004-277460.

[0104] The active ester compound may be a commercially available product, or may be prepared by a known method. Commercially available products include compounds containing dicyclopentadienyldiphenol structure (e.g., EXB9451, EXB9460, EXB9460S, HPC-8000-65T (all manufactured by DIC Corporation)), acetylated phenol novolac (e.g., DC808 (manufactured by Mitsubishi Chemical Corporation)), and benzoylated phenol novolac (e.g., YLH1026, YLH1030, YLH1048 (manufactured by Mitsubishi Chemical Corporation)). From the viewpoint of further improving the storage stability of the varnish and the low thermal expansion of the resin composition when it is cured (cured product), EXB9460S is preferred.

[0105] The active ester compound can be prepared by a known method, for example, by a condensation reaction between a carboxylic acid compound and a hydroxy compound. A specific example is a method in which (a) a carboxylic acid compound or its halide, (b) a hydroxy compound, and (c) an aromatic monohydroxy compound are reacted in a ratio of 0.05 to 0.75 mol of the phenolic hydroxyl group of (b) and 0.25 to 0.95 mol of (c) to 1 mol of the carboxyl group or acid halide group of (a).

[0106] The active ester compound is preferably contained within a range that does not impair the effects of the present invention. When the resin composition of the present embodiment contains an active ester compound, the amount of the active ester compound is preferably 1 part by mass or more and 90 parts by mass or less per 100 parts by mass of the resin solid content in the resin composition. The resin composition in the present embodiment may contain only one type of active ester compound, or may contain two or more types. When two or more types are contained, the total amount is preferably in the above range. The resin composition in the present embodiment may be configured to be substantially free of an active ester compound, which means that the content of the active ester compound is less than 1 part by mass, preferably less than 0.1 part by mass, and more preferably less than 0.01 part by mass, per 100 parts by mass of the resin solid content in the resin composition.

[0107] <Flame retardants> The resin composition of the present embodiment may contain a flame retardant. Examples of the flame retardant include phosphorus-based flame retardants, halogen-based flame retardants, inorganic flame retardants, and silicone-based flame retardants, and phosphorus-based flame retardants are preferred. As the flame retardant, known ones can be used, for example, halogen-based flame retardants such as brominated epoxy resin, brominated polycarbonate, brominated polystyrene, brominated styrene, brominated phthalimide, tetrabromobisphenol A, pentabromobenzyl (meth)acrylate, pentabromotoluene, tribromophenol, hexabromobenzene, decabromodiphenyl ether, bis-1,2-pentabromophenylethane, chlorinated polystyrene, and chlorinated paraffin, red phosphorus, tricresyl phosphate, triphenyl phosphate, and cresyl diphenyl phosphe phosphorus-based flame retardants such as phosphate, trixylenyl phosphate, trialkyl phosphate, dialkyl phosphate, tris(chloroethyl)phosphate, phosphazene, 1,3-phenylenebis(2,6-dixylenyl phosphate), 10-(2,5-dihydroxyphenyl)-10H-9-oxa-10-phosphaphenanthrene-10-oxide, 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. Among these, 1,3-phenylenebis(2,6-dixylenyl phosphate) is preferable in this embodiment because it does not impair the low dielectric properties.

[0108] When the resin composition of the present embodiment contains a flame retardant, the content thereof is preferably 1 part by mass or more, more preferably 5 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 25 parts by mass or less, more preferably 20 parts by mass or less. The flame retardants may 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.

[0109] <Dispersant> The resin composition of the present 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 Co., Ltd.

[0110] When the resin composition of the present 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, relative to 100 parts by mass of the resin solid content in the resin composition. The upper limit of the content of the dispersant is preferably 10 parts by mass or less, more preferably 5 parts by mass or less, and even more preferably 3 parts by mass or less, relative to 100 parts by mass of the resin solid content in the resin composition. The dispersant may 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.

[0111] <Curing accelerator> The resin composition of the present embodiment may further include a curing accelerator. The curing accelerator is not particularly limited, but may be, for example, imidazoles such as 2-ethyl-4-methylimidazole and triphenylimidazole; organic peroxides such as benzoyl peroxide, lauroyl peroxide, acetyl peroxide, parachlorobenzoyl peroxide, and di-tert-butyl-di-perphthalate; azo compounds such as azobisisobutyronitrile; N,N-dimethylbenzylamine, N,N-dimethylaniline, N,N-dimethyltoluidine, 2-N-ethylanilinoethanol, tri-n-butylamine, pyridine, quinoline, N-methylmorpholine, triethanolamine, triethylenediamine, tetramethylphenyl ... Examples of suitable organic metal salts include tertiary amines such as methylbutanediamine and N-methylpiperidine; phenols such as phenol, xylenol, cresol, resorcin and catechol; organic metal salts such as lead naphthenate, lead stearate, zinc naphthenate, zinc octoate, manganese octoate, tin oleate, dibutyltin malate, manganese naphthenate, cobalt naphthenate and ferric acetylacetonate; these organic metal salts dissolved in hydroxyl group-containing compounds such as phenol and bisphenol; inorganic metal salts such as tin chloride, zinc chloride and aluminum chloride; and organic tin compounds such as dioctyltin oxide, other alkyl tins and alkyl tin oxides. Preferred curing accelerators are imidazoles and organometallic salts, and it is more preferred to use both imidazoles and organometallic salts in combination. The resin composition of the present embodiment may be configured to be substantially free of organic peroxides (for example, organic peroxides having a molecular weight of 30 to 500). "Substantially free" means that the amount is less than 0.1 parts by mass, and preferably 0.01 parts by mass or less, per 100 parts by mass of the resin solid content contained in the resin composition of the present embodiment. By setting the amount within such a range, a cured product having various excellent properties can be obtained. The resin composition of the present embodiment may be configured to be substantially free of azo compounds (for example, azo compounds having a molecular weight of 30 to 500). "Substantially free" means that the amount is less than 0.1 parts by mass, and preferably 0.01 parts by mass or less, per 100 parts by mass of the resin solid content contained in the resin composition of the present embodiment. By setting the amount within such a range, a cured product having various excellent properties can be obtained.

[0112] When the resin composition of the present embodiment contains a curing accelerator, the lower limit of the content is preferably 0.005 parts by mass or more, more preferably 0.01 parts by mass or more, and even more preferably 0.1 parts by mass or more, relative to 100 parts by mass of the resin solid content in the resin composition. The upper limit of the content of the curing accelerator is preferably 10 parts by mass or less, more preferably 5 parts by mass or less, and even more preferably 2 parts by mass or less, relative to 100 parts by mass of the resin solid content in the resin composition. The curing accelerator may 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.

[0113] <Solvent> The resin composition of the present embodiment may contain a solvent, and preferably contains an organic solvent. When a solvent is contained, the resin composition of the present embodiment is in a form (solution or varnish) in which at least a part, preferably all, of the above-mentioned various resin solid contents 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 part, preferably all, of the above-mentioned various resin solid contents. Examples of polar organic solvents include ketones (e.g., acetone, methyl ethyl ketone, methyl isobutyl ketone, 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.), amides (e.g., dimethoxyacetamide, dimethylformamides, etc.), and examples of non-polar organic solvents include aromatic hydrocarbons (e.g., toluene, xylene, etc.). The solvent may 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.

[0114] <Other ingredients> In addition to the above components, the resin composition of the present 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 control agents, lubricants, defoamers, leveling agents, gloss agents, and polymerization inhibitors. These additives may be used alone or in combination of two or more. The resin composition of the present embodiment may be configured to be substantially free of a polymerization initiator. Substantially free means that the content of the polymerization initiator is less than 0.1 parts by mass, preferably 0.01 parts by mass or less, per 100 parts by mass of the resin solid content contained in the resin composition of the present embodiment. By setting the content in this range, a cured product having more excellent properties can be obtained.

[0115] <Application> The resin composition of the present embodiment is used as a cured product. Specifically, the resin composition of the present embodiment can be suitably used as a low dielectric constant material and / or a low dielectric loss tangent material, such as an insulating layer for a printed wiring board, a material for a semiconductor package, or a resin composition for electronic materials. The resin composition of the present 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.

[0116] The resin composition of the present embodiment preferably has a low dielectric constant (Dk) when molded into a cured plate having a thickness of 0.8 mm. Specifically, the dielectric constant (Dk) of the cured plate at 10 GHz measured according to a cavity resonator perturbation method is preferably 2.50 or less, more preferably 2.45 or less. The lower limit of the dielectric constant (Dk) is not particularly determined, but for example, 0.01 or more is practical. In addition, the resin composition of the present embodiment preferably has a low dielectric loss tangent (Df) when molded into a cured plate having a thickness of 0.8 mm. Specifically, the dielectric loss tangent (Df) at 10 GHz measured according to the cavity resonator perturbation method is preferably 0.0020 or less, more preferably 0.0018 or less. The lower limit of the dielectric loss tangent (Df) is not particularly determined, but for example, 0.0001 or more is practical. More specifically, the dielectric constant (Dk) and dielectric loss tangent (Df) of the cured sheet are measured by the method described in the Examples below.

[0117] The resin composition of the present embodiment is used as a layered material (including film, sheet, etc.) such as a prepreg or a resin composite sheet that becomes an insulating layer of a printed wiring board, and when it is used as such a layered material, its 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. The thickness of the layered material means the thickness including the glass cloth, for example, when the resin composition of the present embodiment is impregnated into a glass cloth or the like. The material formed from the resin composition of the present embodiment may be used for applications in which a pattern is formed by exposure and development, or for applications in which no exposure and development is required. It is particularly suitable for applications in which no exposure and development is required.

[0118] <<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 (for example, impregnating and / or coating) the resin composition of this embodiment to the substrate, and then semi-curing by heating (for example, a method of drying at 120 to 220°C for 2 to 15 minutes, etc.). In this case, the amount of the resin composition attached to the substrate, that is, the amount of the resin composition (including the filler (D)) relative to the total amount of the semi-cured prepreg, is preferably in the range of 20 to 99% by mass, more preferably in the range of 20 to 80% by mass.

[0119] 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, 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 thereof 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 ultra-opening treatment and clogging treatment are preferred, and 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 a low dielectric loss tangent, such as L-glass, NE-glass, and Q-glass, are more preferred. An example of a substrate with a low relative dielectric constant is a substrate with a relative dielectric constant of 5.0 or less (preferably 3.0 to 4.9). An example of a substrate with a low dielectric loss tangent is a substrate with a dielectric loss tangent of 0.006 or less (preferably 0.001 to 0.005). The relative dielectric constant and the dielectric loss tangent are values ​​measured at 10 GHz using a perturbation method cavity resonator.

[0120] <<Metal foil 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. The metal foil-clad laminate of this embodiment can be produced, for example, by disposing at least one prepreg of this embodiment (preferably two or more sheets are stacked), disposing a metal foil on one or both sides of the prepreg, and laminating and molding the laminate. 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 laminating and molding 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 is not particularly limited as long as it is used as a material for printed wiring boards, and examples of the metal foil include copper foil such as rolled copper foil and electrolytic copper foil. The thickness of the metal foil (preferably copper foil) is not particularly limited, and may be about 1.5 to 70 μm. The molding method includes a method commonly used for molding laminates for printed wiring boards. More specifically, a multi-stage press machine, a multi-stage vacuum press machine, a continuous molding machine, an autoclave molding machine, or the like is used to mold the laminate at a temperature of about 180 to 350°C, a heating time of about 100 to 300 minutes, and a surface pressure of 20 to 100 kg / cm. 2A method of laminating and molding the prepreg of this embodiment at a thickness of about 100 μm can be used. A multilayer board can also be produced by combining and laminating the prepreg of this embodiment and a separately prepared wiring board for an inner layer. As a method for producing a multilayer board, for example, a copper foil of about 35 μm is placed on both sides of one prepreg of this embodiment, and the laminate is formed by the above-mentioned molding method, and then an inner layer circuit is formed, and a blackening treatment is performed on this circuit to form an inner layer circuit board, and then the inner layer circuit board and the prepreg of this embodiment are alternately arranged one by one, and copper foil is further arranged on the outermost layer, and laminated and molded under the above-mentioned 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.

[0121] As described above, the resin composition for electronic materials obtained using the resin composition of this embodiment (a resin composition consisting of a combination of specific components) can provide a cured product having excellent properties such as dielectric characteristics (low dielectric tangent) and moisture absorption heat resistance, as well as excellent crack resistance, appearance of the cured product, and low thermal expansion.

[0122] <<Printed wiring board>> The printed wiring board of the present embodiment is a printed wiring board including an insulating layer and a conductor layer disposed on the surface of the insulating layer, and the insulating layer includes at least one of a layer formed from the resin composition of the present embodiment and a layer formed from the prepreg of the present embodiment. Such a printed wiring board can be manufactured according to a conventional method, and the manufacturing method is not particularly limited. Hereinafter, an example of a method for manufacturing a printed wiring board will be described. First, a metal foil-clad laminate such as the above-mentioned metal foil-clad laminate is prepared. Next, an etching treatment is performed on the surface of the metal foil-clad laminate to form an inner layer circuit, and an inner layer substrate is manufactured. If necessary, a surface treatment is performed on the inner layer circuit surface of this inner layer substrate to increase the adhesive strength, and then a required number of the above-mentioned prepregs are stacked on the surface of the inner layer circuit, and a metal foil for an outer layer circuit is further stacked on the outside thereof, and the laminate is heated and pressed to form an integral body. In this way, a multi-layer laminate is manufactured in which an insulating layer made of a base material and a cured product of a resin composition is formed between the inner layer circuit and the metal foil for the outer layer circuit. Next, this multi-layer laminate is subjected to a hole drilling process for through holes and via holes, and then a plated metal coating 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. Furthermore, the metal foil for the outer layer circuit is etched to form the outer layer circuit, thereby producing a printed wiring board.

[0123] The printed wiring board obtained in the above manufacturing example has an insulating layer and a conductor layer formed on the surface of the insulating layer, and the insulating layer contains the above-mentioned resin composition of the present embodiment and / or its cured product. That is, the above-mentioned prepreg of the present embodiment (for example, a prepreg formed from a base material and the resin composition of the present embodiment impregnated or applied thereto) and the layer formed from the resin composition of the above-mentioned metal foil-clad laminate of the present embodiment are the insulating layer of the present embodiment. In addition, the present embodiment relates to a semiconductor device including the printed wiring board. For details of the semiconductor device, refer to paragraphs 0200 to 0202 of JP 2021-021027 A, the contents of which are incorporated herein by reference.

[0124] <<Resin composite sheet>> The resin composite sheet of the present embodiment includes a support and a layer formed from the resin composition of the present embodiment arranged on the surface of the support. The resin composite sheet can be used as a build-up film or a dry film solder resist. The method for producing the resin composite sheet is not particularly limited, but for example, a method of obtaining a resin composite sheet by applying (coating) a solution in which the resin composition of the present embodiment is dissolved in a solvent to a support and drying the solution can be mentioned.

[0125] 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 supports.

[0126] Examples of the application method (coating method) include a method in which a solution in which the resin composition of this embodiment is dissolved in a solvent is applied onto a support using a bar coater, a die coater, a doctor blade, a baker applicator, or the like. In addition, 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. Note that a single-layer sheet can also be obtained without using a support by supplying a solution in which the resin composition of this embodiment is dissolved in a solvent into a mold having a sheet-shaped cavity and drying it to form it into a sheet.

[0127] In the preparation of the monolayer sheet or resin composite sheet of this embodiment, the drying conditions for removing the solvent are not particularly limited, but since low temperatures tend to leave the solvent in the resin composition, and high temperatures tend to promote 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 in which the solvent has simply been dried, or can be used in a semi-cured (B-stage) state as necessary. The thickness of the resin layer in the monolayer sheet or resin composite sheet of this embodiment can be adjusted by the concentration of the solution of the resin composition of this embodiment used for coating (coating) and the coating thickness, and is not particularly limited, but is preferably 0.1 to 500 μm, since the solvent tends to remain in the resin composition when the coating thickness is large. EXAMPLES

[0128] The present invention will be described in more detail below with reference to examples. The materials, amounts, ratios, processing contents, processing procedures, etc. shown in the following examples can be appropriately changed without departing from the spirit of the present invention. Therefore, the scope of the present invention is not limited to the specific examples shown below. If the measuring instruments used in the examples are difficult to obtain due to discontinuation or the like, measurements can be made using other instruments with equivalent performance.

[0129] <Synthesis Example 1: Synthesis of naphthol aralkyl cyanate ester compound (SNCN)> 0.47 moles (OH group equivalent) of α-naphthol aralkyl resin (SN495V, OH group equivalent: 236g / eq., manufactured by Nippon Steel Chemical Co., Ltd.: the number of repeating units of naphthol aralkyl includes 1 to 5) was dissolved in 500mL of chloroform, and 0.7 moles of triethylamine was added to this solution to prepare solution 1. While keeping the temperature at -10°C, solution 1 was dropped over 1.5 hours into 300g of a chloroform solution of 0.93 moles of cyanogen chloride placed in a reactor, and after the dropwise addition, the mixture was stirred for 30 minutes. Thereafter, a mixed solution of 0.1 moles of triethylamine and 30g of chloroform was further dropped into the reactor, and the mixture was stirred for 30 minutes to complete the reaction. The by-produced triethylamine hydrochloride was filtered out from the reaction solution, and the obtained filtrate was washed with 500mL of 0.1N hydrochloric acid, and then washed with 500mL of water four times. This was dried over sodium sulfate, evaporated at 75°C, and further degassed under reduced pressure at 90°C to obtain a naphthol aralkyl cyanate ester compound represented by formula (S1) (R C1 ~R C4 are all hydrogen atoms, and n c The naphthol aralkyl cyanate ester compound thus obtained was analyzed by infrared absorption spectroscopy, revealing a peak at 2264 cm -1 Absorption of cyanate ester groups was confirmed in the vicinity. [ka]

[0130] <Synthesis Example 2: Synthesis of modified polyphenylene ether compound> <<Synthesis of difunctional phenylene ether oligomers>> CuBr was placed in a 12 L vertical reactor equipped with a stirrer, thermometer, air inlet tube, and baffle. 29.36g (42.1mmol), N,N'-di-t-butylethylenediamine 1.81g (10.5mmol), n-butyldimethylamine 67.77g (671.0mmol), and toluene 2,600g were charged and stirred at a reaction temperature of 40°C. 129g of 2,2',3,3',5,5'-hexamethyl-(1,1'-biphenol)-4,4'-diol dissolved in 2,300g of methanol was added. A mixed solution of 878.4g (7.2mol) of 2,6-dimethylphenol, 1.22g (7.2mmol) of N,N'-di-t-butylethylenediamine, and 26.35g (260.9mmol) of n-butyldimethylamine was added dropwise over 230 minutes while bubbling a mixed gas adjusted to an oxygen concentration of 8% by volume by mixing nitrogen and air at a flow rate of 5.2L / min, and the mixture was stirred. After the dropwise addition was completed, 1,500g of water in which 48.06g (126.4mmol) of tetrasodium ethylenediaminetetraacetate was dissolved was added to stop the reaction. The aqueous layer and the organic layer were separated, and the organic layer was washed with 1N aqueous hydrochloric acid solution and then with pure water. The obtained solution was concentrated to 50% by mass using an evaporator, and 1981g of a toluene solution of a bifunctional phenylene ether oligomer (resin "A") was obtained. The number average molecular weight of resin "A" calculated as polystyrene by the GPC method was 1,975, the weight average molecular weight calculated as polystyrene by the GPC method was 3,514, and the hydroxyl equivalent was 990.

[0131] <<Synthesis of modified polyphenylene ether compounds>> In a reactor equipped with a stirrer, a thermometer, and a reflux tube, 833.4 g of a toluene solution of resin "A", 76.7 g of vinylbenzyl chloride (AGC Seimi Chemical Co., Ltd., "CMS-P"), 1,600 g of methylene chloride, 6.2 g of benzyldimethylamine, 199.5 g of pure water, and 83.6 g of a 30.5 mass% NaOH aqueous solution were charged, and the mixture was stirred at a reaction temperature of 40 ° C. After stirring for 24 hours, the organic layer was washed with a 1N aqueous hydrochloric acid solution and then with pure water. The resulting solution was concentrated with an evaporator, dropped into methanol to solidify, and the solid was collected by filtration and vacuum dried to obtain 450.1 g of a modified polyphenylene ether compound. The modified polyphenylene ether compound had a number average molecular weight of 2250 in terms of polystyrene by the GPC method, a weight average molecular weight of 3920 in terms of polystyrene by the GPC method, and a vinyl group equivalent of 1189 g / vinyl group.

[0132] <<Measurement of weight average molecular weight and number average molecular weight>> The weight average molecular weight (Mw) and number average molecular weight (Mn) were measured by gel permeation chromatography (GPC) using a liquid delivery pump (Shimadzu Corporation, LC-20AD), a differential refractive index detector (Shimadzu Corporation, RID-10A), and GPC columns (Showa Denko K.K., GPC KF-801, 802, 803, 804), 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.

[0133] <Synthesis Example 3: Synthesis of polymer (va) having a structural unit represented by formula (V)> 2.25 mol (292.9 g) of divinylbenzene, 1.32 mol (172.0 g) of ethylvinylbenzene, 11.43 mol (1190.3 g) of styrene, and 15.0 mol (1532.0 g) of n-propyl acetate were charged into a reactor, and 600 mmol of a diethyl ether complex of boron trifluoride was added at 70 ° C. and reacted for 4 hours. After the polymerization reaction was stopped with an aqueous solution of sodium bicarbonate, the oil layer was washed three times with pure water, and the mixture was volatilized under reduced pressure at 60 ° C. to recover a polymer (va) having a structural unit represented by formula (V). The obtained polymer (va) having a structural unit represented by formula (V) was weighed, and it was confirmed that 860.8 g of a polymer (va) having a structural unit represented by formula (V) was obtained.

[0134] 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 Mw / Mn of 14.9. 13 C-NMR and 1 By carrying out H-NMR analysis, the polymer (va) having the structural unit represented by formula (V) was observed to have resonance lines derived from each monomer unit used as a raw material. Based on the NMR measurement results and the GC analysis results, the proportion of each monomer unit (structural unit derived from each raw material) in the polymer (va) having the structural unit represented by formula (V) was calculated as follows. Divinylbenzene-derived structural units: 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%) Furthermore, the content of structural units having a residual vinyl group derived from divinylbenzene was 16.7 mol % (18.5 mass %).

[0135] Example 1 30 parts by mass of a maleimide compound (ma) having the structure shown below (manufactured by DIC Corporation, "NE-X-9470S", a compound represented by formula (M1)), 1 part by mass of a maleimide compound (manufactured by Nippon Kayaku Co., Ltd., MIR-3000-70MT, corresponding to a compound represented by formula (M3)), 1 part by mass of a cyanate ester compound (naphthol aralkyl-type cyanate ester compound (SNCN) obtained in Synthesis Example 1), 15 parts by mass of the modified polyphenylene ether compound obtained in Synthesis Example 2 above, and 15 parts by mass of a phosphorus-based flame retardant (PX-200, Daihachi Chemical Industry Co., Ltd.) 25 parts by mass of unhydrogenated styrene-based thermoplastic elastomer (SBS, TR2250, Mn115000, manufactured by JSR Corporation), 10 parts by mass of polymer (va) having a structural unit represented by formula (V) obtained in Synthesis Example 3, 3 parts by mass of 4-methylstyrene (boiling point 175°C), 0.005 parts by mass of manganese octylate, 0.6 parts by mass of TPIZ (2,4,5-triphenylimidazole, catalyst), and 0.25 parts by mass of imidazole catalyst (manufactured by Shikoku Kasei Co., Ltd., 2E4MZ (trade name)) (catalyst) were dissolved in methyl ethyl ketone and mixed to obtain a varnish. The amounts of each of the above additions indicate the solid content.

[0136] Maleimide compounds (ma) [ka] n is an integer from 1 to 20.

[0137] <Production of hardened plate test pieces with a thickness of 0.8 mm> The solvent was evaporated from the obtained varnish to obtain a mixed resin powder. The mixed resin powder was filled into a mold with a side of 100 mm and a thickness of 0.8 mm, and 12 μm copper foil (3EC-M2S-VLP, manufactured by Mitsui Mining & Smelting Co., Ltd.) was placed on both sides and a pressure of 30 kg / cm was applied. 2 The mixture was then vacuum pressed at 220°C for 120 minutes to obtain a hardened plate with a side length of 100 mm and a thickness of 0.8 mm. The obtained cured plate was used to evaluate the relative dielectric constant (Dk), dielectric loss tangent (Df), and moisture absorption and heat resistance. The evaluation results are shown in Table 1.

[0138] <Measurement and evaluation methods> (1) Dielectric constant (Dk) and dielectric loss tangent (Df) The copper foil of the cured plate was removed by etching, and the plate was dried at 120°C for 60 minutes, after which the relative dielectric constant (Dk) and dielectric loss tangent (Df) after drying were measured at 10 GHz using a perturbation method cavity resonator. The measurement temperature was 23°C. The perturbation method cavity resonator used was Agilent8722ES manufactured by Agilent Technologies. Dielectric constant (Dk) A: 2.45 or less B: More than 2.45 and less than 2.50 C: over 2.50 Dissipation factor (Df) A: 0.0018 or less B: More than 0.0018 and less than 0.0020 C: over 0.0020

[0139] (2) Moisture absorption and heat resistance The hardened plate was cut to 50 mm x 50 mm (downsizing), and all the copper foil on one side was removed by etching, and on the other side, half of the copper foil was removed by etching to obtain a sample for measuring moisture absorption and heat resistance. The obtained sample was dried at 120°C for 60 minutes, and then left to stand for 5 hours in the presence of saturated steam at 121°C and 2 atm using a pressure cooker tester, and further immersed (dipped) in a solder bath at 260°C for 30 seconds, and the presence or absence of abnormalities in appearance was visually observed. The pressure cooker tester used was a PC-3 model manufactured by Hirayama Seisakusho Co., Ltd. For each measurement, three sheets were tested, and if there were no abnormalities in the appearance of the three sheets, they were evaluated as "A", if there were 1 to 2 abnormalities in the appearance, they were evaluated as "B", and if there were 3 abnormalities in the appearance, they were evaluated as "C". The appearance was observed by five experts and the majority vote was used.

[0140] Example 2 The same procedure was carried out in Example 1, except that 4-methylstyrene was replaced with the same amount of vinyltrimethoxysilane (KBM-1003, manufactured by Shin-Etsu Chemical Co., Ltd., boiling point 123° C.).

[0141] Example 3 The same procedures were carried out in Example 1, except that the content of the polymer (va) having a structural unit represented by formula (V) obtained in Synthesis Example 3 was changed to 20 parts by mass, and the content of the maleimide compound (ma) (manufactured by DIC Corporation, "NE-X-9470S", a compound represented by formula (M1)) was changed to 20 parts by mass.

[0142] Comparative Example 1 The same procedures were carried out in Example 1, except that 4-methylstyrene was not added and the content of the maleimide compound (MIR-3000-70MT, manufactured by Nippon Kayaku Co., Ltd., corresponding to the compound represented by formula (M3)) was changed to 4 parts by mass.

[0143] Comparative Example 2 In Comparative Example 1, the content of the polymer (va) having a structural unit represented by formula (V) obtained in Synthesis Example 3 was changed to 20 parts by mass, and the content of the maleimide compound (ma) (manufactured by DIC Corporation, "NE-X-9470S", a compound represented by formula (M1)) was changed to 20 parts by mass. The rest was the same.

[0144] Comparative Example 3 In Comparative Example 1, the polymer (va) having a structural unit represented by formula (V) obtained in Synthesis Example 3 was not blended, and the content of the modified polyphenylene ether compound obtained in Synthesis Example 2 was changed to 25 parts by mass, and the rest was performed in the same manner.

[0145] Comparative Example 4 The same procedure was carried out as in Example 1, except that 4-methylstyrene was not added and 3 parts by mass of 3-glycidoxypropyltrimethoxysilane (manufactured by Shin-Etsu Silicones, "KBM-403") was added.

[0146] [Table 1]

Claims

1. A polymer (A) having a structural unit represented by formula (V), A compound (B) having a molecular weight of less than 1000 and containing one organic group having a carbon-carbon unsaturated bond in the molecule, Containing another thermosetting compound (C) not corresponding to the polymer (A) and the compound (B), The other thermosetting compound (C) is selected from at least one selected from the group consisting of a maleimide compound having two or more maleimide groups in one molecule, a polyphenylene ether compound containing two or more carbon-carbon unsaturated double bonds, a cyanate ester compound having two or more cyanate groups in one molecule, an alkenyl-substituted nadimide compound having two or more alkenyl-substituted nadimide groups in one molecule, and a benzoxazine compound having two or more dihydrobenzoxazine rings in one molecule, a resin composition. 【Chemical formula 1】 (In formula (V), Ar represents an aromatic hydrocarbon linking group. * represents a bonding position.)

2. The resin composition according to claim 1, wherein the weight average molecular weight of the polymer (A) is 1,000 to 160,000.

3. The resin composition according to claim 1, wherein the content of the polymer (A) with respect to 100 parts by mass of the resin solid content in the resin composition is 5 to 70 parts by mass.

4. The organic group containing a carbon-carbon unsaturated bond is CH ２ =C(X)-(X is a hydrogen atom or a methyl group), the resin composition according to claim 1.

5. The organic group containing a carbon-carbon unsaturated bond is one selected from the group consisting of a vinyl group, an allyl group, an acrylic group, and a methacrylic group, the resin composition according to claim 1.

6. The resin composition according to claim 1, wherein the molecular weight of the compound (B) is 70 to 500.

7. The resin composition according to claim 1, wherein the boiling point of the compound (B) is 110 to 300 °C.

8. The resin composition according to claim 1, wherein the content of the compound (B) is 1 to 10 parts by mass with respect to 100 parts by mass of the resin solid content in the resin composition.

9. The resin composition according to claim 1, wherein the mass ratio of the polymer (A) to the compound (B) in the resin composition is 1:0.025 to 0.

7.

10. The resin composition according to claim 1, wherein the other thermosetting compound (C) contains at least one selected from the group consisting of a compound (M1) represented by formula (M1), a compound represented by formula (M3), a compound represented by formula (M5), and a compound represented by formula (OP-1). 【Chemical formula 2】 (In formula (M1), R Ｍ１ , R Ｍ２ , R Ｍ３ , and R Ｍ４ each independently represent a hydrogen atom or an organic group. R Ｍ５ and R Ｍ６ each independently represent a hydrogen atom or an alkyl group. Ar Ｍ represents a divalent aromatic group. A is a 4- to 6-membered alicyclic group. R Ｍ７ and R Ｍ８ are each independently an alkyl group. mx is 1 or 2, and lx is 0 or 1. R Ｍ９ and R Ｍ１０ each independently represent a hydrogen atom or an alkyl group. R Ｍ１１ , R Ｍ１２ , R Ｍ１３ , and R Ｍ１４ each independently represent a hydrogen atom or an organic group. R 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, an aryl group having 6 to 10 carbon atoms, an aryloxy group having 1 to 10 carbon atoms, an arylthio group having 1 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.) [Chemical Formula 3] (In formula (M3), R ５５ Each independently represents a hydrogen atom, an alkyl group having 1 to 8 carbon atoms or a phenyl group, and n ５ represents an integer of 1 or more and 10 or less.) [Chemical Formula 4] (In formula (M5), R ５８ Each independently represents a hydrogen atom, an alkyl group having 1 to 8 carbon atoms or a phenyl group, and R ５９ Each independently represents a hydrogen atom or a methyl group, and n ６ represents an integer of 1 or more.) [Chemical Formula 5] (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 1 to 6, n ２ represents an integer of 1 to 100, and n ３ represents an integer of 2 to 4.)

11. The resin composition according to claim 1, wherein the content of the thermosetting compound (C) is 5 to 95 parts by mass with respect to 100 parts by mass of the resin solid content in the resin composition.

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

13. The resin composition according to claim 12, wherein the content of the filler (D) is 10 to 500 parts by mass with respect to 100 parts by mass of the resin solid content in the resin composition.

14. The polymer (A) contains a structural unit (a) derived from a divinyl aromatic compound in a proportion of 3 mol% or more and 40 mol% or less, and among all the structural units excluding the terminals, the structural units containing an aromatic ring are 90 mol% or more. The resin composition according to claim 1.

15. In the resin composition, the content of the polymer (A) is 5 to 70 parts by mass and the content of the compound (B) is 1 to 10 parts by mass with respect to 100 parts by mass of the resin solid content. The resin composition according to claim 1.

16. The resin composition according to claim 1, which substantially does not contain a polymerization initiator.

17. The weight average molecular weight of the polymer (A) is 1,000 to 160,000, the content of the polymer (A) is 5 to 70 parts by mass with respect to 100 parts by mass of the resin solid content in the resin composition, the organic group containing a carbon-carbon unsaturated bond is one selected from the group consisting of a vinyl group, an allyl group, an acrylic group, and a methacrylic group, the molecular weight of the compound (B) is 70 to 500, the boiling point of the compound (B) is 110 to 300 °C, the content of the compound (B) is 1 to 10 parts by mass with respect to 100 parts by mass of the resin solid content in the resin composition, the mass ratio of the polymer (A) and the compound (B) in the resin composition is 1:0.025 to 0.7, further, it contains another thermosetting compound (C) that does not correspond to the polymer (A) and the compound (B), the content of the thermosetting compound (C) is 5 to 95 parts by mass with respect to 100 parts by mass of the resin solid content in the resin composition, The resin composition according to claim 1.

18. The resin composition according to claim 17, wherein the other thermosetting compound (C) contains at least one selected from the group consisting of compounds represented by the formula (OP-1), and the content thereof is 3 to 50 parts by mass with respect to 100 parts by mass of the resin solid content in the resin composition. 【Chemical Formula 6】 (In the formula (OP-1), X represents an aromatic group, and -(Y-О)n ２ - represents a polyphenylene ether structure, and R １ , R ２ , and R ３ each independently represent a hydrogen atom, an alkyl group, an alkenyl group or an alkynyl group, and n １ represents an integer of 1 to 6, n ２ represents an integer of 1 to 100, and n ３ represents an integer of 2 to 4.)

19. The resin composition according to claim 18, which substantially does not contain a polymerization initiator.

20. A prepreg formed from a base material and the resin composition according to any one of claims 1 to 19.

21. A metal foil-clad laminate including at least one layer formed from the prepreg according to claim 20 and a metal foil disposed on one or both sides of the layer formed from the prepreg.

22. A resin composite sheet including a support and a layer formed from the resin composition according to any one of claims 1 to 19 disposed on the surface of the support.

23. A printed wiring board including an insulating layer and a conductor layer disposed on the surface of the insulating layer, wherein the insulating layer includes a layer formed from the resin composition according to any one of claims 1 to 19.

24. A semiconductor device including the printed wiring board according to claim 23.

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