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

Abstract

Provided are a resin composition, and a cured product, a prepreg, a metal foil-clad laminate, a resin composite sheet, a printed wiring board, and a semiconductor device. The resin composition comprises: a maleimide compound (A) having an aliphatic hydrocarbon group with 8 or more carbon atoms in the molecule and having two or more maleimide groups, a maleimide compound (B) having an aliphatic hydrocarbon group with 7 or less carbon atoms in the molecule and having two or more maleimide groups, a block copolymer (C) having a styrene skeleton, and a resin (D) other than the block copolymer (C) having a styrene skeleton and containing an aromatic ring and two or more polymerizable unsaturated groups, wherein the difference in relative dielectric constant between the maleimide compound (A) and the maleimide compound (B) is 0.3 or less.

Description

[Technical field]

[0001] The present invention relates to a resin composition, a cured product, a prepreg, a metal foil-clad laminate, a resin composite sheet, a printed wiring board, and a semiconductor device. [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, such as substrates for mounting semiconductor elements, which occupy an important position in such technology. On the other hand, the applications of electronic devices and the like are becoming more diverse and expanding. In response to this, the properties required for printed wiring boards such as substrates for mounting semiconductor elements, and metal foil-clad laminates and prepregs used therein, are 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 development of improved resin materials that constitute prepregs and resin composite sheets. Such materials are described in Patent Documents 1 to 4. [Prior art documents] [Patent documents]

[0003] [Patent Document 1] Patent Publication No. 2022-058409 [Patent Document 2] JP 2021-187893 A [Patent Document 3] International Publication No. 2019 / 188189 [Patent Document 4] JP 2018-090728 A 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 materials for resin compositions that can provide cured products that have excellent moisture absorption and heat resistance and peel strength with metal foils while maintaining excellent low dielectric properties (Dk and / or Df). The present invention has an object to solve the above-mentioned problems, and to provide a resin composition capable of providing a cured product having excellent moisture absorption heat resistance and peel strength with metal foil while maintaining excellent low dielectric properties (Dk and / or Df, especially Dk), as well as a cured product, a prepreg, a metal foil-clad laminate, a resin composite sheet, a printed wiring board, and a semiconductor device. [Means for solving the problem]

[0005] In light of the above-mentioned problems, the present inventors have conducted studies and have found that by using a maleimide compound having a relatively long aliphatic chain in combination with a maleimide compound having a relatively short aliphatic chain, and by reducing the difference in the relative dielectric constants of the cured products thereof, it is possible to obtain a resin composition that is capable of providing a cured product that has excellent moisture absorption heat resistance and peel strength with metal foil, while maintaining excellent low dielectric properties (Dk and / or Df, particularly Dk). Specifically, the above problems were solved by the following means. <1> A maleimide compound (A) having an aliphatic hydrocarbon group having 8 or more carbon atoms and having two or more maleimide groups in the molecule; A maleimide compound (B) having an aliphatic hydrocarbon group having 7 or less carbon atoms and having two or more maleimide groups in the molecule; A block copolymer (C) having a styrene skeleton; and a resin (D) containing an aromatic ring and two or more polymerizable unsaturated groups other than the block copolymer (C) having a styrene skeleton, A resin composition, in which the difference between the dielectric constant at a frequency of 10 GHz of a cured product of the maleimide compound (A) as measured according to a cavity resonance perturbation method and the dielectric constant at a frequency of 10 GHz of a cured product of the maleimide compound (B) as measured according to a cavity resonance perturbation method is 0.3 or less. <2> The cured product of the maleimide compound (A) has a relative dielectric constant of 2.1 to 2.5 at a frequency of 10 GHz measured according to a cavity resonance perturbation method. <1> The resin composition according to claim 1. <3> The cured product of the maleimide compound (B) has a relative dielectric constant of 2.2 to 2.6 at a frequency of 10 GHz measured according to a cavity resonance perturbation method. <1> or <2> The resin composition according to claim 1. <4> a difference between a dielectric constant at a frequency of 10 GHz of the block copolymer (C) having a styrene skeleton, as measured according to a cavity resonance perturbation method, and a dielectric constant at a frequency of 10 GHz of a cured product of the maleimide compound (B), as measured according to a cavity resonance perturbation method, is 0.6 or less. <1> ~ <3> 10. The resin composition according to claim 9 . <5> The block copolymer (C) having a styrene skeleton has a relative dielectric constant of 1.9 to 2.2 at a frequency of 10 GHz measured according to a cavity resonance perturbation method. <1> ~ <4> 10. The resin composition according to claim 9 . <6> a difference between a dielectric constant at a frequency of 10 GHz of a cured product of the resin (D) containing an aromatic ring and two or more polymerizable unsaturated groups, as measured according to a cavity resonance perturbation method, and a dielectric constant at a frequency of 10 GHz of a cured product of the maleimide compound (B), as measured according to a cavity resonance perturbation method, is 0.3 or less; a cured product of the resin (D) containing an aromatic ring and two or more polymerizable unsaturated groups has a relative dielectric constant of 2.2 to 2.6 at a frequency of 10 GHz measured according to a cavity resonance perturbation method; <1> ~ <5> 10. The resin composition according to claim 9 . <7> a dielectric constant at a frequency of 10 GHz of a cured product of the maleimide compound (A), measured according to a cavity resonance perturbation method, a dielectric constant at a frequency of 10 GHz of a cured product of the maleimide compound (B), a dielectric constant at a frequency of 10 GHz of the block copolymer (C) having a styrene skeleton, measured according to a cavity resonance perturbation method, and a dielectric constant at a frequency of 10 GHz of a cured product of the resin (D) containing an aromatic ring and two or more polymerizable unsaturated groups, measured according to a cavity resonance perturbation method, are each independently 2.0 to 2.6. <1> ~ <6> 10. The resin composition according to claim 9 . <8> the content of the maleimide compound (A) is 5 to 40 parts by mass relative to 100 parts by mass of the resin solid content, the content of the maleimide compound (B) is 5 to 40 parts by mass relative to 100 parts by mass of the resin solid content, the content of the block copolymer (C) having a styrene skeleton is 3 to 40 parts by mass relative to 100 parts by mass of a resin solid content, The content of the resin (D) containing an aromatic ring and two or more polymerizable unsaturated groups is 5 to 50 parts by mass relative to 100 parts by mass of the resin solid content. <1> ~ <7> 10. The resin composition according to claim 9 . <9> a mass ratio ((A) / (B)) of the content of the maleimide compound (A) to the content of the maleimide compound (B) is 30 / 70 to 70 to 30; <1> ~ <8> 10. The resin composition according to claim 9 . <10> The maleimide compound (A) has two or more divalent linear aliphatic hydrocarbon groups having 8 to 20 carbon atoms in the molecule. <1> ~ <9> 10. The resin composition according to claim 9 . <11> The maleimide compound (A) has a weight average molecular weight of 2,000 to 30,000. <1> ~ <10> 10. The resin composition according to claim 9 . <12> the maleimide compound (A) has one or more groups represented by formula (1), and each maleimide group is independently linked to a group represented by formula (1) via at least an aliphatic hydrocarbon group having 8 or more carbon atoms; <1> ~ <11> 10. The resin composition according to claim 9 . [ka] <13> The maleimide compound (A) has a constitutional unit represented by formula (2): <1> ~ <12> 10. The resin composition according to claim 9 . [ka] (In formula (2), R 1 and R 3 each independently represents a linear aliphatic hydrocarbon group having 8 or more carbon atoms; R 2 represents a hydrocarbon group having an alicyclic structure of a 4- to 10-membered ring. <14> The maleimide compound (A) contains a compound represented by formula (3): <1> ~ <13> 10. The resin composition according to claim 9 . [ka] (In formula (3), R 1 and R 3 each independently represents a linear aliphatic hydrocarbon group having 8 or more carbon atoms; R 2 represents a hydrocarbon group having an alicyclic structure of a 4- to 10-membered ring, and n represents a number from 1 to 10. <15> The maleimide compound (B) has a weight average molecular weight of 350 to 5,000. <1> ~ <14> 10. The resin composition according to claim 9 . <16> The maleimide compound (B) contains a compound represented by formula (M1). <1> ~ <15> 10. The resin composition according to claim 9 . [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 M8are 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 6 to 10 carbon atoms, an arylthio group having 6 to 10 carbon atoms, a halogen atom, a hydroxyl group, or a mercapto group. px represents an integer of 0 to 3. nx represents an integer of 1 to 20.) <17> The maleimide compound (A) contains a compound represented by formula (3), and the maleimide compound (B) contains a compound represented by formula (M1). <1> ~ <16> 10. The resin composition according to claim 9 . [ka] (In formula (3), R 1 and R 3 each independently represents a linear aliphatic hydrocarbon group having 8 or more carbon atoms; R 2 represents a hydrocarbon group having an alicyclic structure of a 4- to 10-membered ring, and n represents a number from 1 to 10. [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 6 to 10 carbon atoms, an arylthio group having 6 to 10 carbon atoms, a halogen atom, a hydroxyl group, or a mercapto group. px represents an integer of 0 to 3. nx represents an integer of 1 to 20.) <18> The resin (D) containing an aromatic ring and two or more polymerizable unsaturated groups contains at least one of a polymer (V) having a structural unit represented by formula (V) and a polyphenylene ether compound containing two or more carbon-carbon unsaturated double bonds. <1> ~ <17> 10. The resin composition according to claim 9 . [ka] (In formula (V), Ar represents an aromatic hydrocarbon linking group. * represents a bonding position.) <19> The resin (D) containing an aromatic ring and two or more polymerizable unsaturated groups contains at least one of a polymer (V) having a structural unit represented by formula (V) and a polyphenylene ether compound containing two or more carbon-carbon unsaturated double bonds represented by formula (OP-1). <1> ~ <18> 10. The resin composition according to claim 9 . [ka] (In formula (V), Ar represents an aromatic hydrocarbon linking group. * represents a bonding position.) [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 3each 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 1 to 4.) <20> Further, the composition further comprises a cyanate ester compound (E), <1> ~ <19> 10. The resin composition according to claim 9 . <21> The cured product of the cyanate ester compound (E) has a relative dielectric constant of 2.4 to 3.0 at a frequency of 10 GHz, as measured according to a cavity resonance perturbation method. <20> The resin composition according to claim 1. <22> Further, the present invention includes a compound (F) having one polymerizable unsaturated group in the molecule. <1> ~ <21> 10. The resin composition according to claim 9 . <23> Further, the filler (G) is contained. <1> ~ <22> 10. The resin composition according to claim 9 . <24> The content of the filler (G) in the resin composition is 10 to 1600 parts by mass per 100 parts by mass of the resin solid content. <23> The resin composition according to claim 1. <25> the cured product of the maleimide compound (A) has a relative dielectric constant of 2.1 to 2.5 at a frequency of 10 GHz measured according to a cavity resonance perturbation method; the cured product of the maleimide compound (B) has a relative dielectric constant of 2.2 to 2.6 at a frequency of 10 GHz measured according to a cavity resonance perturbation method; a difference between a dielectric constant at a frequency of 10 GHz of the block copolymer (C) having a styrene skeleton, as measured according to a cavity resonance perturbation method, and a dielectric constant at a frequency of 10 GHz of a cured product of the maleimide compound (B), as measured according to a cavity resonance perturbation method, is 0.6 or less; The block copolymer (C) having a styrene skeleton has a relative dielectric constant of 1.9 to 2.2 at a frequency of 10 GHz measured according to a cavity resonance perturbation method, a difference between a dielectric constant at a frequency of 10 GHz of a cured product of the resin (D) containing an aromatic ring and two or more polymerizable unsaturated groups, as measured according to a cavity resonance perturbation method, and a dielectric constant at a frequency of 10 GHz of a cured product of the maleimide compound (B), as measured according to a cavity resonance perturbation method, is 0.3 or less; a cured product of the resin (D) containing an aromatic ring and two or more polymerizable unsaturated groups has a relative dielectric constant of 2.2 to 2.6 at a frequency of 10 GHz measured according to a cavity resonance perturbation method; a dielectric constant at a frequency of 10 GHz of a cured product of the maleimide compound (A), measured according to a cavity resonance perturbation method, a dielectric constant at a frequency of 10 GHz of a cured product of the maleimide compound (B), a dielectric constant at a frequency of 10 GHz of the block copolymer (C) having a styrene skeleton, measured according to a cavity resonance perturbation method, and a dielectric constant at a frequency of 10 GHz of a cured product of the resin (D) containing an aromatic ring and two or more polymerizable unsaturated groups, measured according to a cavity resonance perturbation method, are each independently 2.0 to 2.6; the content of the maleimide compound (A) is 5 to 40 parts by mass relative to 100 parts by mass of the resin solid content, the content of the maleimide compound (B) is 5 to 40 parts by mass relative to 100 parts by mass of the resin solid content, the content of the block copolymer (C) having a styrene skeleton is 3 to 40 parts by mass relative to 100 parts by mass of a resin solid content, the content of the resin (D) containing an aromatic ring and two or more polymerizable unsaturated groups is 5 to 50 parts by mass relative to 100 parts by mass of the resin solid content, a mass ratio ((A) / (B)) of the content of the maleimide compound (A) to the content of the maleimide compound (B) is 30 / 70 to 70 to 30; The maleimide compound (A) has two or more divalent linear aliphatic hydrocarbon groups having 8 to 20 carbon atoms in the molecule, The maleimide compound (A) has a weight average molecular weight of 2,000 to 30,000; The maleimide compound (A) contains a compound represented by formula (3), and the maleimide compound (B) contains a compound represented by formula (M1), the resin (D) containing an aromatic ring and two or more polymerizable unsaturated groups comprises at least one of a polymer (V) having a structural unit represented by formula (V) and a polyphenylene ether compound containing two or more carbon-carbon unsaturated double bonds represented by formula (OP-1), Further, the composition contains a cyanate ester compound (E), the cured product of the cyanate ester compound (E) has a relative dielectric constant of 2.4 to 3.0 at a frequency of 10 GHz measured according to a cavity resonance perturbation method; Further, the present invention includes a compound (F) having one polymerizable unsaturated group in the molecule. <1> ~ <24> 10. The resin composition according to claim 9 . [ka] (In formula (3), R 1 and R 3 each independently represents a linear aliphatic hydrocarbon group having 8 or more carbon atoms; R 2 represents a hydrocarbon group having an alicyclic structure of a 4- to 10-membered ring, and n represents a number from 1 to 10. [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. 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 6 to 10 carbon atoms, an arylthio group having 6 to 10 carbon atoms, a halogen atom, a hydroxyl group, or a mercapto group. px represents an integer of 0 to 3. nx represents an integer of 1 to 20.) [ka] (In formula (V), Ar represents an aromatic hydrocarbon linking group. * represents a bonding position.) [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 1 to 4.) <26> Further, the resin composition contains a filler (G), and the content of the filler (G) in the resin composition is 10 to 1600 parts by mass per 100 parts by mass of a resin solid content. <25> The resin composition according to claim 1. <27> <1> ~ <26> 2. A cured product of the resin composition according to claim 1. <28> A substrate; <1> ~ <26> and a prepreg formed from the resin composition according to any one of the above. <29> <28> 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. <30> A support and a substrate disposed on the surface of the support. <1> ~ <26> and a layer formed from the resin composition according to any one of the above. <31> 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> ~ <26> A printed wiring board comprising a layer formed from the resin composition according to any one of claims 1 to 5. <32> <31> 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 capable of providing a cured product that has excellent moisture absorption heat resistance and peel strength with metal foil while maintaining excellent low dielectric properties (Dk and / or Df, especially Dk), as well as a cured product, a prepreg, a metal foil-clad laminate, a resin composite sheet, a printed wiring board, and a semiconductor device. 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 dielectric constant refers to the ratio of the dielectric constant of a substance to the dielectric constant of a vacuum. In this specification, the dielectric constant may be simply referred to as "dielectric constant." Furthermore, unless otherwise specified, the dielectric constant in this specification refers to the dielectric constant at a frequency of 10 GHz measured according to the cavity resonance perturbation method. In this specification, "(meth)acrylic" refers to both or either of acrylic and methacrylic, and "(meth)allyl" refers to both or either of allyl and methallyl. In cases where the standards shown in this specification differ depending on the year and the measurement method, etc., they will be based on the standards as of January 1, 2023, unless otherwise stated.

[0008] In this specification, the resin solids content refers to components excluding fillers and solvents, and is intended to include the maleimide compound (A), the maleimide compound (B), the block copolymer (C), and the resin (D) containing a polymerizable unsaturated group, as well as other thermosetting compounds that are blended as necessary, and other resin additive components (additives such as flame retardants, etc.).

[0009] <Resin composition> The resin composition of the present embodiment comprises a maleimide compound (A) (sometimes referred to herein as "maleimide compound (A)") having an aliphatic hydrocarbon group having 8 or more carbon atoms in its molecule and having two or more maleimide groups, a maleimide compound (B) (sometimes referred to herein as "maleimide compound (B)") having an aliphatic hydrocarbon group having 7 or less carbon atoms in its molecule and having two or more maleimide groups, a block copolymer (C) (sometimes referred to herein as "block copolymer (C)") having a styrene skeleton, and a resin (D) (sometimes referred to herein as "resin (D) containing a polymerizable unsaturated group) other than the block copolymer (C) having a styrene skeleton), the resin composition being characterized in that the difference between the relative dielectric constant at a frequency of 10 GHz measured according to a cavity resonance perturbation method and the relative dielectric constant at a frequency of 10 GHz measured according to a cavity resonance perturbation method of a cured product of the maleimide compound (A) is 0.3 or less. By adopting such a configuration, it is possible to obtain a resin composition that can provide a cured product that has excellent moisture absorption and heat resistance and peel strength with metal foil while maintaining excellent low dielectric properties (Dk and / or Df, especially Dk). In order to obtain a cured product of a resin composition having excellent low dielectric properties, it is advantageous that the resin components constituting the resin composition have fewer polar groups. In this embodiment, by using a maleimide compound (A) having an aliphatic hydrocarbon group with 8 or more carbon atoms and two or more maleimide groups in the molecule and a block copolymer (C) having a styrene skeleton, the dielectric properties (Dk and / or Df, especially Dk) of the obtained cured product can be reduced. In addition, since the maleimide compound (A) has an aliphatic hydrocarbon group with 8 or more carbon atoms, the compound has viscosity and the peel strength of the obtained cured product against the metal foil can be increased. The block copolymer (C) having a styrene skeleton can also increase the adhesion to the metal foil and increase the peel strength. On the other hand, the maleimide compound (A) has an aliphatic hydrocarbon group having 8 or more carbon atoms, and therefore tends to have poor heat resistance. In this embodiment, the resin composition is sufficiently cured by blending the maleimide compound (B) having an aliphatic hydrocarbon group having 7 or less carbon atoms and having two or more maleimide groups in the molecule and the resin (D) containing a polymerizable unsaturated group. As a result, the heat resistance can be improved. In addition, compounds with low polarity are easily compatible with each other, and as a result, the heat resistance is likely to be good. Here, a resin composition that does not contain the maleimide compound (A) and contains the maleimide compound (B), the block copolymer (C), and the resin (D) containing a polymerizable unsaturated group tends to have poor moisture absorption heat resistance when cured, because the maleimide compound (B), which has high polarity and high dielectric constant, is separated and a site showing low dielectric properties is locally formed. In this embodiment, it is presumed that by adopting a combination of the maleimide compound (A) and the maleimide compound (B) having a small difference in relative dielectric constant, localized curing in the resin composition is suppressed, thereby solving the above-mentioned problem.

[0010] <Maleimide compound (A)> The resin composition of the present embodiment contains a maleimide compound (A) having, in the molecule, two or more aliphatic hydrocarbon groups having 8 or more carbon atoms and two or more maleimide groups. The maleimide compound (A) has two or more aliphatic hydrocarbon groups having 8 or more carbon atoms in the molecule (per molecule). Since the maleimide compound (A) contains an aliphatic hydrocarbon group having 8 or more carbon atoms, it has low polarity and can reduce the dielectric properties (Dk and / or Df, especially Dk) of the obtained cured product. Furthermore, since the maleimide compound (A) has an aliphatic hydrocarbon group having 8 or more carbon atoms, the compound itself has viscosity, and the peel strength of the obtained cured product against metal foil can be increased. The maleimide compound (A) has two or more maleimide groups in the molecule (per molecule). The maleimide compound (A) is a compound having 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 the molecule.

[0011] The aliphatic hydrocarbon group contained in the maleimide compound (A) may be any one of a linear, branched, or cyclic aliphatic hydrocarbon group, or may be a combination of linear, branched, or cyclic aliphatic hydrocarbon groups.

[0012] The aliphatic hydrocarbon group of the maleimide compound (A) is preferably a combination of a linear and / or branched aliphatic hydrocarbon group (preferably a linear aliphatic hydrocarbon group, more preferably a linear aliphatic hydrocarbon group having 8 to 20 carbon atoms, and even more preferably a divalent linear aliphatic hydrocarbon group having 8 to 20 carbon atoms) and a 4- to 10-membered cyclic aliphatic hydrocarbon group which may have a substituent (preferably a 6-membered cyclic aliphatic hydrocarbon group which may have a substituent). Examples of the substituent of the 4- to 10-membered cyclic aliphatic hydrocarbon group which may have a substituent include an alkyl group having 1 to 10 carbon atoms, preferably an alkyl group having 6 to 10 carbon atoms, and more preferably an n-hexyl group and / or an n-octyl group. The number of substituents is preferably 1 to 3 per cyclic aliphatic hydrocarbon group (preferably a 6-membered cyclic aliphatic hydrocarbon group). In the present embodiment, the aliphatic hydrocarbon group contained in the maleimide compound (A) may contain a carbon-carbon unsaturated bond, but it is preferable that it does not contain such a bond.

[0013] The number of carbon atoms in the aliphatic hydrocarbon group of the maleimide compound (A) is 8 or more, preferably 10 or more, and more preferably 12 or more, for each aliphatic hydrocarbon group. By making it equal to or more than the lower limit, the low dielectric properties (Dk and / or Df, especially Dk) of the obtained cured product and the peel strength against metal foil tend to be more excellent. In addition, the number of carbon atoms in the aliphatic hydrocarbon group of the maleimide compound (A) is preferably 50 or less, more preferably 40 or less, even more preferably 35 or less, even more preferably 30 or less, and even more preferably 25 or less. By making it equal to or less than the upper limit, the heat resistance of the obtained cured product tends to be further improved.

[0014] The number of aliphatic hydrocarbon groups in the molecule of the maleimide compound (A) is 2 or more, preferably 6 or more, more preferably 9 or more, even more preferably 12 or more, even more preferably 15 or more, and even more preferably 20 or more. By making it equal to or more than the lower limit, the low dielectric properties (Dk and / or Df, especially Dk) of the obtained cured product and the peel strength against metal foil tend to be more excellent. In addition, the number of aliphatic hydrocarbon groups in the molecule of the maleimide compound (A) is preferably 100 or less, more preferably 75 or less, even more preferably 60 or less, even more preferably 50 or less, and even more preferably 40 or less. By making it equal to or less than the upper limit, the compatibility with other resins when mixing the resins tends to be improved.

[0015] The maleimide compound (A) preferably has 2 or more, more preferably 6 or more, and even more preferably 8 or more, and preferably 40 or less, more preferably 30 or less, and even more preferably 20 or less, of the divalent linear aliphatic hydrocarbon groups having 8 to 20 carbon atoms in the molecule. By setting the number of the divalent linear aliphatic hydrocarbon groups having 8 to 20 carbon atoms to the lower limit or more, the low dielectric properties (Dk and / or Df, especially Dk) of the obtained cured product and the peel strength against metal foil tend to be more excellent. In addition, by setting the number of the divalent linear aliphatic hydrocarbon groups having 8 to 20 carbon atoms to the upper limit or less, the compatibility with other resins when mixing the resins tends to be more improved.

[0016] In this embodiment, the maleimide compound (A) has one or more groups represented by formula (1), and each maleimide group is preferably linked to the group represented by formula (1) through at least an aliphatic hydrocarbon group having 8 or more carbon atoms. In this embodiment, it is more preferable that the maleimide group is linked to the group represented by formula (1) through a group consisting of a combination of a divalent linear aliphatic hydrocarbon group having 8 to 20 carbon atoms and a cyclic 6-membered aliphatic hydrocarbon group which may have a substituent, and it is even more preferable that the maleimide group is linked to the group represented by formula (1) only through a group consisting of a combination of a divalent linear aliphatic hydrocarbon group having 8 to 20 carbon atoms and a cyclic 6-membered aliphatic hydrocarbon group which may have a substituent. By having such a structure, the low dielectric properties (Dk and / or Df, especially Dk) and peel strength against metal foil of the obtained cured product tend to be more excellent. [ka]

[0017] The maleimide compound (A) preferably has a constitutional unit represented by formula (2). [ka] (In formula (2), R 1 and R 3each independently represents a linear aliphatic hydrocarbon group having 8 or more carbon atoms; R 2 represents a hydrocarbon group having an alicyclic structure of a 4- to 10-membered ring. Maleimide compounds having a structural unit represented by formula (2) tend to have higher stress relaxation ability, and as a result, the obtained cured product tends to have better low dielectric properties (Dk and / or Df, especially Dk) and peel strength against metal foil, as well as a lower thermal expansion coefficient. When the maleimide compound having a constitutional unit represented by formula (2) contains a plurality of constitutional units represented by formula (2), the constitutional units represented by formula (2) may be the same or different.

[0018] The linear aliphatic hydrocarbon group having 8 or more carbon atoms is more preferably a divalent linear aliphatic hydrocarbon group having 8 to 20 carbon atoms, and even more preferably a divalent linear aliphatic hydrocarbon group having 8 to 15 carbon atoms. The hydrocarbon group having a 4- to 10-membered alicyclic structure is preferably a 6-membered cyclic hydrocarbon group which may have a substituent. Examples of the substituent include an alkyl group having 1 to 10 carbon atoms, preferably an alkyl group having 6 to 10 carbon atoms, more preferably an n-hexyl group and / or an n-octyl group. The number of substituents is preferably 1 to 3 per 6-membered ring.

[0019] The maleimide compound (A) preferably contains a compound represented by formula (3). Compounds represented by formula (3) tend to have higher stress relaxation ability, and as a result, the obtained cured product tends to have better low dielectric properties (Dk and / or Df, especially Dk) and peel strength against metal foil, and also tends to have a lower coefficient of thermal expansion. [ka] (In formula (3), R 1 and R 3 each independently represents a linear aliphatic hydrocarbon group having 8 or more carbon atoms; R 2represents a hydrocarbon group having an alicyclic structure of a 4- to 10-membered ring, and n represents a number from 1 to 10. In formula (3), when n is 2 or more, the n constitutional units may be the same or different.

[0020] R in Equation (3) 1 ~R 3 each independently represents R in the above formula (2). 1 ~R 3 The same definition and preferred range are also the same. In formula (3), R 1 and R 3 is an octylene group, and R 2 is preferably a cycloalkylene group (preferably a cyclohexylene group) having an n-hexyl group and / or an n-octyl group as a substituent.

[0021] The compound represented by formula (3) is not particularly limited, but examples that can be used include "BMI-3000" and "BMI-5000" manufactured by Designer Molecules Inc., and "SLK-3000" manufactured by Shin-Etsu Chemical Co., Ltd. By using such compounds, the thermal expansion coefficient tends to be further reduced.

[0022] The weight average molecular weight of the maleimide compound (A) is preferably 2000 or more, more preferably 3000 or more, even more preferably 4000 or more, even more preferably 5000 or more, even more preferably 6000 or more, and even more preferably 7000 or more. By making the weight average molecular weight equal to or more than the lower limit, the low dielectric properties (Dk and / or Df, especially Dk) of the obtained cured product and the peel strength against metal foil tend to be more excellent. In addition, the weight average molecular weight of the maleimide compound (A) is preferably 30000 or less, more preferably 27000 or less, even more preferably 25000 or less, and even more preferably 20000 or less. By making the weight average molecular weight equal to or less than the upper limit, the compatibility with other resins when mixing the resins tends to be improved. When the resin composition of the present embodiment contains two or more types of maleimide compounds (A), the weight average molecular weight of the mixture of maleimide compounds (A) preferably falls within the above range.

[0023] The dielectric constant of the cured product of the maleimide compound (A) at a frequency of 10 GHz measured according to the cavity resonance perturbation method is preferably 2.5 or less, more preferably 2.4 or less, even more preferably less than 2.4, and even more preferably 2.3 or less. By making it equal to or less than the upper limit, the dielectric constant (Dk) of the obtained cured product tends to be better. In addition, the dielectric constant of the cured product of the maleimide compound (A) is preferably 2.1 or more. By making it equal to or more than the lower limit, the compatibility with other resins when mixing the resin is further improved, and the electrical properties such as low dielectric properties, peel strength against metal foil, and heat resistance of the obtained cured product tend to be better. When the resin composition of the present embodiment contains two or more types of maleimide compounds (A), the dielectric constant is a weighted average value of the relative dielectric constants of the cured products of the maleimide compounds (A).

[0024] The content of the maleimide compound (A) in the resin composition of the present embodiment is preferably 5 parts by mass or more, more preferably 7 parts by mass or more, even more preferably 8 parts by mass or more, even more preferably 9 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. By making the content of the maleimide compound (A) equal to or more than the lower limit, the low dielectric properties (Dk and / or Df, especially Dk) of the obtained cured product and the peel strength against the metal foil tend to be more excellent. In addition, the upper limit of the content of the maleimide compound (A) is preferably 40 parts by mass or less, more preferably 30 parts by mass or less, even more preferably 25 parts by mass or less, and even more preferably 20 parts by mass or less, relative to 100 parts by mass of the resin solid content. By making the content of the maleimide compound (A) equal to or less than the upper limit, the moisture absorption heat resistance of the obtained cured product tends to be further improved. The resin composition of the present embodiment may contain only one type of maleimide compound (A), or may contain two or more types. When two or more types are contained, the total amount is preferably within the above range.

[0025] <Maleimide compound (B)> The resin composition of the present embodiment contains a maleimide compound (B) having an aliphatic hydrocarbon group having 7 or less carbon atoms and two or more maleimide groups in the molecule. The maleimide compound (B) is a compound that does not have an aliphatic hydrocarbon group having 8 or more carbon atoms in the molecule. The resin composition of this embodiment contains the maleimide compound (B) that does not have an aliphatic hydrocarbon group having 8 or more carbon atoms, and thus the moisture absorption heat resistance of the obtained cured product can be improved. In addition, the maleimide compound (A) has a long-chain aliphatic hydrocarbon group, and therefore tends to have poor curability. In this embodiment, the use of the maleimide compound (B) that does not have a long aliphatic hydrocarbon group can promote curing of the resin composition, and can improve the moisture absorption heat resistance of the obtained cured product. Furthermore, in this embodiment, the difference between the dielectric constant at a frequency of 10 GHz measured according to the cavity resonance perturbation method of the cured product of the maleimide compound (A) and the dielectric constant at a frequency of 10 GHz measured according to the cavity resonance perturbation method of the cured product of the maleimide compound (B) is 0.3 or less. Compounds having such a small difference in dielectric constant tend to be easily compatible with each other because the difference in polarity is also small as described above, and as a result, it is presumed that a cured product having low dielectric properties (Dk and / or Df, especially Dk), excellent peel strength with metal foil, and excellent moisture absorption and heat resistance can be obtained. The maleimide compound (B) has two or more maleimide groups in the molecule. The number of maleimide groups in the maleimide compound (B) used in the present embodiment is preferably 2 to 12, more preferably 2 to 6, further preferably 2 to 4, even more preferably 2 or 3, and may be 2. The lower limit of the carbon number of the aliphatic hydrocarbon group having 7 or less carbon atoms is preferably 1 or more.

[0026] The dielectric constant of the cured product of the maleimide compound (B) used in this embodiment at a frequency of 10 GHz measured according to the cavity resonance perturbation method is preferably 2.6 or less, more preferably 2.5 or less, even more preferably less than 2.5, and even more preferably 2.4 or less. By making it equal to or less than the upper limit, the compatibility with the maleimide compound (A) is improved, and the obtained cured product tends to have better moisture absorption heat resistance. In addition, the dielectric constant of the cured product of the maleimide compound (B) is preferably 2.2 or more, more preferably 2.3 or more. By making it equal to or more than the lower limit, the compatibility with other resins when mixing the resins is improved, and the obtained cured product tends to have better electrical properties such as low dielectric properties, peel strength against metal foil, and heat resistance. When the resin composition of the present embodiment contains two or more types of maleimide compounds (B), it is defined as a weighted average value of the relative dielectric constants of the cured products of the maleimide compounds (B).

[0027] A first embodiment of the maleimide compound (B) includes a compound 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. M15each independently represents an alkyl group having 1 to 10 carbon atoms, an alkyloxy group having 1 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, an aryloxy group having 6 to 10 carbon atoms, an arylthio group having 6 to 10 carbon atoms, a halogen atom, a hydroxyl group, or a mercapto group. px represents an integer of 0 to 3. nx represents an integer of 1 to 20.) Here, R M15 preferably 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 6 to 10 carbon atoms, an arylthio group having 6 to 10 carbon atoms, a halogen atom, a hydroxyl group, or a mercapto group.

[0028] 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. Mmay 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 M15each independently represents an alkyl group having 1 to 10 carbon atoms, an alkyloxy group having 1 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, an aryloxy group having 6 to 10 carbon atoms, an arylthio group having 6 to 10 carbon atoms, a halogen atom, a hydroxyl group, or a mercapto group, and is preferably 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 6 to 10 carbon atoms, an arylthio group having 6 to 10 carbon atoms, a halogen atom, a hydroxyl group, or a mercapto group, and more 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 different values ​​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 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 provide a low melting point (low softening point), 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 formula (M1-2) and the like described below.

[0029] The compound represented by formula (M1) is preferably a compound represented by the following formula (M1-1). [ka] (In formula (M1-1), R M21 , R M22 , RM23 , 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 R M39 Each independently represents a hydrogen atom or an alkyl group. nx represents an integer of 1 or more and 20 or less.

[0030] 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 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. R M27 , R M28 , R M29 , and R M30each 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 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. R M33 , R M34 , R M35 , and R M36 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 , and R M39 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. nx represents an integer of 1 or more and 20 or less. nx may be an integer of 10 or less.

[0031] 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 M36 R each independently represents a hydrogen atom or an organic group. M37 , R M38 , and R M39 Each independently represents a hydrogen atom or an alkyl group. nx represents an integer of 1 or more and 20 or less.

[0032] 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 , RM31 , 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.

[0033] 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.) nx may be an integer less than or equal to 10. The compound represented by formula (M1) is x The compound represented by formula (M1) may be a mixture of compounds having different n, and is preferably a mixture. The compound represented by formula (M1) may be a mixture of two or more compounds, or may be a mixture of only one compound. Examples of the mixture include compounds having n x A mixture of compounds with different M7 , R M8 , R M15 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 other groups on the benzene ring, and a mixture of compounds having a combination of two or more of the above differences.

[0034] A second embodiment of the maleimide compound (B) includes a compound represented by formula (M5).

[0035] [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 are each independently preferably one selected from the group consisting of 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, and a phenyl group, more preferably a hydrogen atom and / or 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 The compound represented by formula (M5) may be a mixture of compounds having different n, and is preferably a mixture. The compound represented by formula (M5) may be a mixture of two or more compounds, or may be a mixture of only one compound. Examples of the mixture include compounds having n 6 A mixture of compounds with different 58 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 other groups on the benzene ring, and a mixture of compounds having a combination of two or more of the above differences.

[0036] The maleimide compound (B) may be produced by a known method, or a commercially available product may be used. Examples of commercially available products include "NE-X-9470S", "NE-X-9480S", "X9-450" and "X9-470" manufactured by DIC Corporation as the compound represented by formula (M1), and "MIR-5000" manufactured by Nippon Kayaku Co., Ltd. as the compound represented by formula (M5). In this embodiment, the maleimide compound (B) preferably contains at least a compound represented by formula (M1).

[0037] The weight average molecular weight of the maleimide compound (B) used in this embodiment is preferably 350 or more, more preferably 400 or more, and even more preferably 450 or more. By making it equal to or more than the lower limit, the low dielectric properties and moisture absorption heat resistance of the obtained cured product tend to be further improved. In addition, the molecular weight of the maleimide compound (B) is preferably 5000 or less, more preferably 4000 or less, even more preferably 3500 or less, and even more preferably 3000 or less. By making it equal to or less than the upper limit, the solubility in solvents is increased, and the handleability of the resin composition tends to be further improved. When the resin composition of the present embodiment contains two or more types of maleimide compounds (B), the weight average molecular weight of the mixture of maleimide compounds (B) preferably falls within the above range.

[0038] The content of the maleimide compound (B) in the resin composition of the present embodiment is preferably 5 parts by mass or more, more preferably 6 parts by mass or more, even more preferably 8 parts by mass or more, even more preferably 10 parts by mass or more, even more preferably 12 parts by mass or more, and may be 16 parts by mass or more, based on 100 parts by mass of the resin solid content. By making the content of the maleimide compound (B) equal to or more than the lower limit, the moisture absorption heat resistance of the obtained cured product tends to be improved. In addition, the upper limit of the content of the maleimide compound (B) is preferably 40 parts by mass or less, more preferably 30 parts by mass or less, even more preferably 25 parts by mass or less, even more preferably 22 parts by mass or less, and even more preferably 20 parts by mass or less, based on 100 parts by mass of the resin solid content. By making the content of the maleimide compound (B) equal to or less than the upper limit, the compatibility with the maleimide compound (A) tends to be further improved. The resin composition of the present embodiment may contain only one type of maleimide 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.

[0039] In the resin composition of the present embodiment, the mass ratio ((A) / (B)) of the content of the maleimide compound (A) to the content of the maleimide compound (B) is preferably 30 / 70 to 70 to 30. Furthermore, the content of the maleimide compound (A) relative to 100 parts by mass of the total of the content of the maleimide compound (A) and the content of the maleimide compound (B) is more preferably 35 parts by mass or more, even more preferably 40 parts by mass or more, and is preferably 65 parts by mass or less, and more preferably 60 parts by mass or less. By setting it in the above range, the effects of the present invention can be improved in a well-balanced manner.

[0040] The resin composition of the present embodiment may or may not contain a maleimide compound having one maleimide group in the molecule, and a maleimide compound having two or more maleimide groups in the molecule other than maleimide compound (A) and maleimide compound (B) (other polyfunctional maleimide compound). As other polyfunctional maleimide compounds, compounds described in paragraphs 0050 to 0053 of WO 2023 / 026829 can be used, the contents of which are incorporated herein by reference. The resin composition of the present embodiment may be configured to be substantially free of maleimide compounds other than maleimide compound (A) and maleimide compound (B). "Substantially free" means that the total amount of maleimide compounds other than maleimide compound (A) and maleimide compound (B) is less than 10 parts by mass, preferably less than 5 parts by mass, more preferably less than 3 parts by mass, even more preferably less than 1 part by mass, and even more preferably less than 0.1 parts by mass, relative to 100 parts by mass of the total amount of maleimide compound (A) and maleimide compound (B) contained in the resin composition. The resin composition of the present embodiment may be configured to be substantially free of maleimide compounds having a high dielectric constant. Substantially free means that the total amount of maleimide compounds having a high dielectric constant is less than 10 parts by mass, preferably less than 5 parts by mass, more preferably less than 3 parts by mass, even more preferably less than 1 part by mass, and even more preferably less than 0.1 parts by mass, relative to 100 parts by mass of the total amount of maleimide compounds contained in the resin composition. Here, the maleimide compound having a high dielectric constant means that the cured product of the maleimide compound has a dielectric constant of more than 2.6 at a frequency of 10 GHz measured according to a cavity resonance perturbation method, preferably more than 2.5, and more preferably more than 2.4. The upper limit of the dielectric constant of the cured product of the maleimide compound having a high dielectric constant is not particularly specified, but is usually 4.0 or less.

[0041] <Block copolymer having a styrene skeleton (C)> The resin composition of the present embodiment contains a block copolymer (C) having a styrene skeleton (block copolymer (C)). By containing the block copolymer (C), the peel strength of the obtained cured product against metal foil is improved, and excellent low dielectric properties (Dk and / or Df, especially Dk) can be achieved. This is because the toughness of the obtained cured product is improved, and the adhesion to the metal foil is improved.

[0042] The weight average molecular weight of the block copolymer (C) used in this embodiment is preferably 1,000 or more. By making the weight average molecular weight 1,000 or more, the appearance, low thermal expansion, and crack resistance of the cured product tend to be further improved. The weight average molecular weight is more preferably 5,000 or more, more preferably 8,000 or more, even more preferably 10,000 or more, and may be 50,000 or more, or 100,000 or more. The upper limit of the weight average molecular weight of the block copolymer (C) is preferably 500,000 or less, more preferably 300,000 or less, and even more preferably 250,000 or less. By making the weight average molecular weight equal to or less than the upper limit, the compatibility with other components tends to be further improved. When the resin composition of the present embodiment contains two or more types of block copolymers (C), it is preferable that the weight average molecular weight of the mixture thereof falls within the above range.

[0043] The block copolymer (C) is a block polymer having at least a styrene skeleton, and is preferably an elastomer containing a styrene monomer unit and a conjugated diene monomer unit (hereinafter referred to as "elastomer (c)"). By using such an elastomer (c), the low dielectric properties (Dk and / or Df, especially Dk) of the obtained cured product and the peel strength against metal foil tend to be excellent.

[0044] Examples of the styrene monomer contained in the elastomer (c) include styrene, α-methylstyrene, p-methylstyrene, divinylbenzene (vinylstyrene), N,N-dimethyl-p-aminoethylstyrene, N,N-diethyl-p-aminoethylstyrene, etc., and among these, from the viewpoints of availability and productivity, styrene, α-methylstyrene, and p-methylstyrene are preferred. Among these, styrene is particularly preferred. The content of the styrene monomer unit in the elastomer (c) 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 elastomer (c) may contain only one type of styrene monomer unit, or may contain two or more types. When it contains two or more types, the total amount is preferably within the above range. The method for measuring the content of the styrene monomer unit in the elastomer (c) of this embodiment can be found in International Publication No. 2017 / 126469, the contents of which are incorporated herein by reference. The same applies to the conjugated diene monomer unit and the like described below.

[0045] The elastomer (c) contains a conjugated diene monomer unit. The inclusion of the conjugated diene monomer unit improves the solubility of the elastomer (c) in the resin composition. The conjugated diene monomer is not particularly limited as long as it is a diolefin having one pair of conjugated double bonds. Examples of the conjugated diene monomer include 1,3-butadiene, 2-methyl-1,3-butadiene (isoprene), 2,3-dimethyl-1,3-butadiene, 1,3-pentadiene, 2-methyl-1,3-pentadiene, 1,3-hexadiene, and farnesene, with 1,3-butadiene and isoprene being preferred, and 1,3-butadiene being more preferred. The elastomer (c) may contain only one type of conjugated diene monomer unit, or may contain two or more types.

[0046] In the above elastomer (c), 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. If the mass ratio of the styrene polymer 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.

[0047] The above-mentioned elastomer (c) 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.

[0048] The elastomer (c) 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 above elastomer (c), 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. As described above, the elastomer (c) 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, it is preferable that the total amount is within the above range.

[0049] The elastomer (c) used in the present embodiment may be a block polymer or a random polymer. In addition, it may be a hydrogenated elastomer in which the conjugated diene monomer unit is hydrogenated, an unhydrogenated elastomer in which the conjugated diene monomer unit is not hydrogenated, or a partially hydrogenated elastomer in which the conjugated diene monomer unit is partially hydrogenated, and is preferably an unhydrogenated elastomer or a partially hydrogenated elastomer. In one embodiment of this embodiment, the elastomer (c) is a hydrogenated elastomer. Here, the hydrogenated elastomer means, for example, an elastomer in which double bonds based on conjugated diene monomer units in the elastomer 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 elastomer (c) is an unhydrogenated elastomer. Here, the unhydrogenated elastomer refers to an elastomer in which the proportion of hydrogenated double bonds based on conjugated diene monomer units in the elastomer, i.e., the hydrogenation rate (hydrogenation rate) is 20% or less. The hydrogenation rate is preferably 15% or less, more preferably 10% or less, and even more preferably 5% or less. On the other hand, a partially hydrogenated elastomer means an elastomer in which some of the double bonds based on the conjugated diene monomer units in the elastomer are hydrogenated, and usually refers to an elastomer in which the hydrogenation rate (hydrogenation rate) is less than 80% and more than 20%.

[0050] Commercially available elastomers (c) used in the present embodiment include SEPTON (registered trademark) 2104, V9461, and S8104 manufactured by Kuraray Co., Ltd.; Tuftec (registered trademark) H1041, H1043, P2000, and MP10 manufactured by Asahi Kasei Corporation; and DYNARON (registered trademark) 9901P and TR2250 manufactured by JSR Corporation.

[0051] The elastomer used in this embodiment may also be a liquid diene. The liquid diene refers to a liquid elastomer containing a conjugated diene monomer unit. 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, with 1,3-butadiene and isoprene being preferred, and 1,3-butadiene being more preferred. Examples of the liquid diene used in this embodiment include liquid polybutadiene, liquid polyisoprene, modified liquid polybutadiene, modified liquid polyisoprene, liquid acrylonitrile-butadiene copolymer, and liquid styrene-butadiene copolymer. The number average molecular weight of the liquid diene is not particularly limited as long as it is liquid at 20° C., but is preferably 500 or more and 10,000 or less.

[0052] The block copolymer (C) having a styrene skeleton used in this embodiment has a dielectric constant at a frequency of 10 GHz measured according to a cavity resonance perturbation method, which is preferably 2.2 or less, more preferably less than 2.2, and preferably 1.9 or more, more preferably 2.0 or more. By making it equal to or less than the upper limit, the dielectric constant (Dk) of the obtained cured product tends to be better. In addition, by making it equal to or more than the lower limit, the compatibility with other resins when mixing the resin is improved, and the electrical properties such as low dielectric properties, peel strength against metal foil, and heat resistance of the obtained cured product tend to be better.

[0053] When the resin composition of the present embodiment contains two or more types of block copolymers (C), the above-mentioned relative dielectric constant is a weighted average value.

[0054] The content of the block copolymer (C) in the resin composition of the present embodiment is preferably 3 parts by mass or more, more preferably 5 parts by mass or more, even more preferably 7 parts by mass or more, even more preferably 10 parts by mass or more, and even more preferably 12 parts by mass or more, based on 100 parts by mass of the resin solid content. By making it equal to or more than the lower limit, the low dielectric properties (Dk and / or Df, especially Dk) of the obtained cured product and the peel strength against the metal foil tend to be improved. In addition, the upper limit of the content of the block copolymer (C) is preferably 40 parts by mass or less, more preferably 30 parts by mass or less, even more preferably 25 parts by mass or less, even more preferably 20 parts by mass or less, and even more preferably 18 parts by mass or less, based on 100 parts by mass of the resin solid content. By making it equal to or less than the upper limit, the moisture absorption heat resistance of the obtained cured product tends to be improved. The resin composition of the present embodiment may contain only one type of block copolymer (C), or may contain two or more types. When two or more types are contained, the total amount is preferably within the above range. In addition, the resin composition of the present embodiment may contain a random copolymer in addition to the block copolymer (C) within a range that does not impair the effects of the present invention. Examples of the random copolymer include SOE (registered trademark) S1606, S1613, S1609, and S1605 manufactured by Asahi Kasei Corporation.

[0055] <Resin (D) containing an aromatic ring and two or more polymerizable unsaturated groups other than the block copolymer (C) having a styrene skeleton> The resin composition of this embodiment contains a resin (D) (resin (D) containing a polymerizable unsaturated group) containing an aromatic ring and two or more polymerizable unsaturated groups other than the block copolymer (C) having a styrene skeleton. By containing the resin (D) containing a polymerizable unsaturated group, the heat resistance of the obtained cured product is improved and excellent low dielectric properties (particularly Dk) can be achieved. The reason for this is that the degree of curing of the resin composition is improved by containing a functional group different from the maleimide group that reacts with the maleimide group. The aromatic ring contained in the resin (D) containing a polymerizable unsaturated group is preferably a benzene ring. The polymerizable unsaturated group is preferably a group having a carbon-carbon unsaturated double bond, more preferably a group selected from the group consisting of a (meth)acrylic group, a (meth)allyl group, and a vinylbenzyl group, and even more preferably a group selected from the group consisting of a (meth)acrylic group and a vinylbenzyl group. In addition, the resin (D) containing a polymerizable unsaturated group in this embodiment preferably has the polymerizable unsaturated group at a terminal. Furthermore, the resin (D) containing a polymerizable unsaturated group in this embodiment preferably contains two or more of the polymerizable unsaturated groups in one molecule in order to improve the heat resistance of the resulting cured product.

[0056] The resin (D) containing a polymerizable unsaturated group used in this embodiment preferably contains at least one of a polymer (V) having a structural unit represented by formula (V) and a polyphenylene ether compound containing two or more carbon-carbon unsaturated double bonds, and more preferably contains at least one of a polymer (V) having a structural unit represented by formula (V) and a polyphenylene ether compound containing two or more carbon-carbon unsaturated double bonds represented by formula (OP-1). [ka] (In formula (V), Ar represents an aromatic hydrocarbon linking group. * represents a bonding position.) [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 1 to 4.)

[0057] The resin (D) containing an aromatic ring and two or more polymerizable unsaturated groups used in this embodiment has a dielectric constant of 2.6 or less, more preferably 2.5 or less, even more preferably 2.4 or less, and may be less than 2.4, at a frequency of 10 GHz, measured according to a cavity resonance perturbation method. By making it equal to or less than the upper limit, the compatibility with the maleimide compound (A) tends to be improved. In addition, the resin (D) containing an aromatic ring and two or more polymerizable unsaturated groups used in this embodiment has a dielectric constant of 2.2 or more, and may be 2.3 or more, at the cured product. By making it equal to or less than the upper limit, the dielectric constant (Dk) of the obtained cured product tends to be better. In addition, by making it equal to or more than the lower limit, the compatibility with other resins when mixing the resin is improved, and the electrical properties such as low dielectric properties, peel strength against metal foil, and heat resistance of the obtained cured product tend to be better.

[0058] When the resin composition of the present embodiment contains two or more types of resins (D) containing a polymerizable unsaturated group, the above-mentioned relative dielectric constant is a weighted average value.

[0059] The content of the resin (D) containing a polymerizable unsaturated group in the resin composition of this embodiment is preferably 5 parts by mass or more, more preferably 10 parts by mass or more, even more preferably 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. The upper limit of the content of the resin (D) containing a polymerizable unsaturated group is preferably 50 parts by mass or less, more preferably 40 parts by mass or less, even more preferably 35 parts by mass or less, and even more preferably 30 parts by mass or less, relative to 100 parts by mass of the resin solid content. The resin (D) containing an aromatic ring and two or more polymerizable unsaturated groups may contain only one type or two or more types in the resin composition. When two or more types are contained, it is preferable that the total amount is within the above range.

[0060] <<Polymer (V) Having a Structural Unit Represented by Formula (V)>> The resin composition of the present embodiment preferably contains a polymer (V) having a structural unit represented by formula (V). By containing the polymer (V) having a structural unit represented by formula (V), a resin composition having excellent low dielectric properties (low dielectric constant, low dielectric loss tangent) can be obtained as a cured product. [ka] (In formula (V), Ar represents an aromatic hydrocarbon linking group. * represents a bonding position.)

[0061] 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. The aromatic hydrocarbon linking group 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.

[0062] 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.

[0063] 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)".

[0064] [ka] In formulas (V1) to (V3), L 1 is 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. In other words, the structural unit (a) is preferably a structural unit derived from a divinyl aromatic compound.

[0065] As described above, the polymer (V) having a 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 (V) 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.

[0066] 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).

[0067] The structural unit (b) derived from a monovinyl aromatic compound is preferably a structural unit represented by the following formula (V4).

[0068] [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.

[0069] When the polymer (V) having a structural unit represented by formula (V) is a copolymer containing a structural unit (b) derived from a monovinyl aromatic compound, examples of the monovinyl aromatic compound include vinyl aromatic compounds such as styrene, vinylnaphthalene, and vinylbiphenyl; and 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. Among these, the structural unit (b) preferably contains a structural unit derived from at least one selected from the group consisting of o-ethylvinylbenzene, m-ethylvinylbenzene, and p-ethylvinylbenzene, and more preferably contains a structural unit derived from styrene in addition to a structural unit derived from at least one selected from the group consisting of o-ethylvinylbenzene, m-ethylvinylbenzene, and p-ethylvinylbenzene.

[0070] When the polymer (V) 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.

[0071] The polymer (V) 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.

[0072] When the polymer (V) 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.

[0073] The polymer (V) 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, butadiene (e.g., 1,3-butadiene), and isoprene. 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.

[0074] An embodiment of the polymer (V) having a structural unit represented by formula (V) is a polymer essentially comprising the structural unit (a) and at least one of the structural units (b) to (d). Further, the total of the structural units (a) to (d) is 95 mol % or more, and further 98 mol % or more of all the structural units. In another embodiment of the polymer (V) having a structural unit represented by formula (V), the structural unit (a) is essential, and among 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 (V) having a structural unit represented by formula (V).

[0075] The method for producing the polymer (V) 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.

[0076] The structure of the chain end of the polymer (V) 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)

[0077] 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)

[0078] The molecular weight of the polymer (V) having a constitutional unit represented by formula (V), in terms of number average molecular weight Mn, is 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 (V) having the structural unit represented by formula (V) is preferably 3,000 or more, more preferably 5,000 or more, and even more preferably 10,000 or more, in terms of weight average molecular weight Mw. By making it equal to or greater than the lower limit, the excellent low dielectric properties (Dk and / or Df) of the polymer (V) having the structural unit represented by formula (V), especially Df and the dielectric properties after moisture absorption, can be effectively exhibited in the cured product of the resin composition. The upper limit is preferably 130,000 or less, more preferably 100,000 or less, even more preferably 80,000 or less, and even more preferably 50,000 or less. By 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 expressed by the ratio of the weight average molecular weight Mw to the number average molecular weight Mn, is preferably 100 or less, more preferably 50 or less, even more preferably 20 or less, and may be 15 or less, or may be 12 or less. As for the lower limit, a practical value is 1.1 or more, and it is preferably 2.0 or more, more preferably 4 or more, even more preferably 5 or more, even more preferably 7 or more, and even more preferably 10 or more. 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 polymers (V) 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.

[0079] The vinyl group equivalent of the polymer (V) having a structural unit represented by formula (V) is preferably 200 g / eq. or more, more preferably 230 g / eq. or more, even more preferably 250 g / eq. or more, and may be 300 g / eq. or more, or 350 g / eq. or more. The vinyl group equivalent is preferably 1200 g / eq. or less, more preferably 1000 g / eq. or less, and may be 800 g / eq. or less, 600 g / eq. or less, 500 g / eq. 400 g / eq. or less, 350 g / eq. or less, or 300 g / eq. or less. By making it equal to or more than the lower limit, the storage stability of the resin composition is 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 upper limit, the heat resistance of the obtained cured product tends to be improved.

[0080] The polymer (V) having the structural unit represented by formula (V) preferably has excellent low dielectric properties when cured. For example, the cured polymer (V) 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 having the structural unit represented by formula (V) 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 dielectric constant (Dk) and the dielectric loss tangent (Df) are measured by the following method. 4.5 g of resin powder is spread into a stainless steel mold measuring 100 mm x 30 mm x 1.0 mm high, set in a vacuum press (Kitagawa Seiki Co., Ltd.), and held at 200°C, 220°C, and 240°C for 1.5 hours, then pressed at a surface pressure of 1.9 MPa to produce a hardened plate. The cured plate is downsized to a width of 1.0 mm, dried at 120°C for 60 minutes, and then the relative dielectric constant (Dk) and dielectric loss tangent (Df) after drying are measured at 10 GHz using a perturbation method cavity resonator. The measurement temperature is 23°C.

[0081] For the polymer (V) having a constitutional unit represented by the 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.

[0082] The lower limit of the content of the polymer (V) having the structural unit represented by formula (V) is more preferably 1 part by mass or more, more preferably 3 parts by mass or more, and even more preferably 5 parts by mass or more, relative to 100 parts by mass of the resin solid content. The upper limit of the content of the polymer (V) having the structural unit represented by formula (V) is preferably 50 parts by mass or less, more preferably 45 parts by mass or less, more preferably 35 parts by mass or less, even more preferably 25 parts by mass or less, and even more preferably 20 parts by mass or less, relative to 100 parts by mass of the resin solid content. By making the content of the polymer (V) having the structural unit represented by formula (V) equal to or more than the above lower limit, the obtained cured product tends to have excellent low dielectric properties (Dk and / or Df, especially Dk) and desmear resistance. In addition, by making it equal to or less than the above upper limit, the peel strength and moisture absorption heat resistance of the obtained cured product against metal foil can be effectively increased. The polymer (V) 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.

[0083] <<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 carbon-carbon unsaturated double bonds at the terminal, more preferably a polyphenylene ether compound having two or more groups selected from the group consisting of (meth)acrylic groups, (meth)allyl groups, and vinylbenzyl groups at the terminal, and even more preferably a polyphenylene ether compound having two or more groups selected from the group consisting of (meth)acrylic groups and vinylbenzyl groups. 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.

[0084] 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).

[0085] [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.

[0086] 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 structural 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 43may 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.

[0087] 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)"). More preferably, the modified polyphenylene ether compound has two or more groups selected from the group consisting of (meth)acrylic groups, (meth)allyl groups, and vinylbenzyl groups at the terminals. More preferably, the modified polyphenylene ether compound has two or more groups selected from the group consisting of (meth)acrylic groups and vinylbenzyl groups at the terminals. By adopting such 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 improve the low water absorption and peel strength against metal foil. These may be used alone or in combination of two or more.

[0088] The modified polyphenylene ether compound (g) may be a polyphenylene ether compound represented by the formula (OP). [ka] (In formula (OP), X represents an aromatic group, -(YO) n1 - represents a polyphenylene ether structure, n1 represents an integer of 1 to 100, and n2 represents an integer of 1 to 4. Rx is a group represented by formula (Rx-1) or formula (Rx-2). [ka] (In formula (Rx-1) and formula (Rx-2), R 1 , R 2 , and R 3each independently represents a hydrogen atom, an alkyl group, an alkenyl group, or an alkynyl group. * is a bonding site with an oxygen atom. each Mc independently represents a hydrocarbon group having 1 to 12 carbon atoms. z represents an integer of 0 to 4. r represents an integer of 1 to 6.

[0089] n 1 and / or n 2 If is an integer greater than or equal to 2, n 1 Units (YO) and / or n 2 The constituent units may be the same or different. 2 is preferably 2 or more, and more preferably 2.

[0090] In formula (Rx-1) and formula (Rx-2), R 1 , R 2 , and R 3 each independently represents a hydrogen atom, an alkyl group, an alkenyl group, or an alkynyl group. R 1 is preferably a hydrogen atom or an alkyl group, more preferably a hydrogen atom or a methyl group, and further preferably a hydrogen atom. R 2 and R 3 are each independently preferably a hydrogen atom or an alkyl group, more preferably a hydrogen atom or a methyl group, and further preferably a hydrogen atom. R 1 , R 2 , and R 3 The number of carbon atoms in the alkyl group, alkenyl group, or alkynyl group is preferably 5 or less, and more preferably 3 or less.

[0091] In formula (Rx-1), r represents an integer of 1 to 6, preferably an integer of 1 to 5, more preferably an integer of 1 to 4, even more preferably an integer of 1 to 3, still more preferably 1 or 2, and even more preferably 1.

[0092] In formula (Rx-1), each Mc independently represents a hydrocarbon group having 1 to 12 carbon atoms, preferably a hydrocarbon group having 1 to 10 carbon atoms, more preferably a linear or branched alkyl group having 1 to 10 carbon atoms, further preferably a methyl group, ethyl group, isopropyl group, isobutyl group, t-butyl group, pentyl group, octyl group, or nonyl group, and still more preferably a methyl group, ethyl group, isopropyl group, isobutyl group, or t-butyl group. In formula (Rx-1), z represents an integer of 0 to 4, preferably an integer of 0 to 3, more preferably an integer of 0 to 2, further preferably 0 or 1, and even more preferably 0.

[0093] A specific example of the group represented by formula (Rx-1) is a vinylbenzyl group, and a specific example of the group represented by formula (Rx-2) is a (meth)acryloyl group.

[0094] The modified polyphenylene ether compound (g) is preferably 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 1 to 4.) n 2 and / or n 3 If is an integer greater than or equal to 2, n 2 Units (YO) and / or n 3 The constituent units may be the same or different. 3 is preferably 2 or more, and more preferably 2.

[0095] 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.

[0096] 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 23may be the same or different and is a hydrogen atom, an alkyl group having 6 or less carbon atoms, or a phenyl group, and is preferably represented by ). In particular, R 20 and R 21 are each independently a group having one or more methyl groups and / or cyclohexyl groups. By doing so, the rigidity of the resulting resin molecules increases. Since molecules with high rigidity have lower mobility than molecules with low rigidity, the relaxation time during dielectric relaxation becomes longer, which is preferable because it has excellent low dielectric properties (Dk and / or Df, particularly Dk). An example of the formula (OP-5) has the following structure.

Chemical formula

[0097] In formula (OP-2), a and b each independently represent an integer from 0 to 100, and at least one of a and b is an integer from 1 to 100. Preferably, a and b are each independently an integer from 0 to 50, more preferably an integer from 1 to 30, and still more preferably an integer from 1 to 10. When a and / or b is an integer of 2 or more, two or more -(Y-O)- may each independently have one kind of structure arranged, or two or more kinds of structures may be arranged in blocks or randomly. Further, when a plurality of compounds represented by formula (OP-2) are included, the average value of a is preferably 1 < a < 10, and the average value of b is preferably 1 < b < 10.

[0098] 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 thereto.

[0099] Among the compounds represented by the above formula (OP-2), R 4 , R 5 , R 6 , R 10 , R 11 , R 20 , and R 21 is an alkyl group having 3 or less carbon atoms, and R 7 , R 8 , R 9 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 , R 18 , R 19 , R 22 , and R 23 is a hydrogen atom or an alkyl group having 3 or less carbon atoms, and it is particularly preferred that -(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.

[0100] [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]

[0101] The polyphenylene ether compound used in this embodiment is more preferably a compound represented by formula (OP-14) and / or a compound represented by formula (OP-15), and even more preferably a compound represented by formula (OP-15). [ka] (In formula (OP-14), a and b each independently represent an integer of 0 to 100, and at least one of a and b is an integer of 1 to 100.) In formula (OP-14), a and b each independently have the same definition as a and b in formula (OP-2), and the preferred ranges are also the same. [ka] (In formula (OP-15), a and b each independently represent an integer of 0 to 100, and at least one of a and b is an integer of 1 to 100.) In formula (OP-15), a and b each independently have the same definition as a and b in formula (OP-2), and the preferred ranges are also the same.

[0102] The polyphenylene ether compound containing two or more carbon-carbon unsaturated double bonds may be produced by a known method, or a commercially available product may be used. For example, a commercially available product is a modified polyphenylene ether compound having a methacrylic group at the end, such as "SA9000" manufactured by SABIC Innovative Plastics. In addition, a modified polyphenylene ether compound having a vinylbenzyl group at the end, such as "OPE-2St1200" and "OPE-2st2200" manufactured by Mitsubishi Gas Chemical. In addition, a modified polyphenylene ether compound having a hydroxyl group at the end, such as "SA90" manufactured by SABIC Innovative Plastics, modified to a vinylbenzyl group using vinylbenzyl chloride or the like, may be used as the modified polyphenylene ether compound having a vinylbenzyl group at the end.

[0103] In addition, for details of the polyphenylene ether compound containing two or more carbon-carbon unsaturated double bonds, the descriptions in JP 2006-028111 A, JP 2018-131519 A, WO 2019-138992, and WO 2022-054303 can be referred to, the contents of which are incorporated herein by reference.

[0104] The polyphenylene ether compound containing two or more carbon-carbon unsaturated double bonds (preferably modified polyphenylene ether compound (g)) preferably has a polystyrene-equivalent number average molecular weight (details follow the method described in the Examples below) by GPC (gel permeation chromatography) method of 500 or more and 3,000 or less. 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 polystyrene-equivalent weight average molecular weight by GPC of the polyphenylene ether compound containing two or more carbon-carbon unsaturated double bonds (preferably modified polyphenylene ether compound (g)) (details are in accordance with the method described in the Examples below) 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 / or dielectric loss tangent (Df) (particularly Dk) of the cured product of the resin composition tends 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 / or dielectric loss tangent (Df), (particularly Dk) of the cured product of the resin composition tends to be lower. By making it equal to or less than the upper limit, the solubility in a solvent, low viscosity, and moldability of the resin composition tend to be improved.

[0105] The functional group equivalent (carbon-carbon unsaturated double bond equivalent) of a polyphenylene ether compound containing two or more carbon-carbon unsaturated double bonds is calculated from the reciprocal of the amount of double bonds determined from the results of measurement using an infrared spectrometer. The double bond equivalent [g / eq.] was calculated as follows. The powder of the polyphenylene ether compound is weighed and the weight is recorded. This powder is placed in a measuring flask, and then the powder is made up to a specified amount with carbon disulfide to prepare a measurement sample. This sample liquid is placed in a measurement cell and set in an infrared spectrophotometer (FT / IR-4600, manufactured by JASCO Corporation). Next, infrared spectroscopy of the sample liquid is performed. In the case of vinyl groups in the polyphenylene ether compound, the 905 cm -1 Record the area of ​​the peak in the spectrum around 1640 cm. -1The area of ​​the peak in the spectrum is recorded. The double bond concentration [mol / L] is calculated from this area and the calibration curve. Next, the double bond equivalent is calculated according to the following formula. Double bond equivalent [g / eq.] = powder weight in measurement sample [g] / double bond concentration [mol / L] × measurement sample liquid volume [L] The functional group equivalent of other resin components (thermosetting resins) can also be measured by following the above method. However, for compounds (monomers) that can be expressed by a single molecular weight, the value of the functional group equivalent calculated by (theoretical molecular weight ÷ number of functional groups) should be used preferentially.

[0106] When the resin composition of the present embodiment contains 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 5 parts by mass or more, even more preferably 8 parts by mass or more, even more preferably 10 parts by mass or more, and even more preferably 13 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 dielectric properties (Dk and / or Df, especially Dk) and moisture absorption heat resistance of the obtained cured product tend to be more excellent. In addition, the upper limit of the content of the polyphenylene ether compound having two or more carbon-carbon unsaturated double bonds is preferably 50 parts by mass or less, more preferably 45 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 30 parts by mass or less, and even more preferably 25 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 upper limit, the heat resistance and chemical resistance of the resulting cured product tend to be superior. 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.

[0107] <Difference in dielectric ratio of components (A) to (D)> In the resin composition of the present embodiment, the difference between the dielectric constant of the cured product of the maleimide compound (A) and the dielectric constant of the cured product of the maleimide compound (B) is 0.3 or less, preferably 0.2 or less, more preferably less than 0.2, and even more preferably 0.1 or less. By making it equal to or less than the above upper limit, the compatibility between the maleimide compound (A) and the maleimide compound (B) is improved, so that the low dielectric properties (Dk and / or Df, especially Dk), moisture absorption heat resistance, and peel strength against metal foil of the obtained cured product tend to be more excellent. The lower limit of the difference between the dielectric constant of the cured product of the maleimide compound (A) and the dielectric constant of the cured product of the maleimide compound (B) is 0. Moreover, usually, the dielectric constant of the cured product of the maleimide compound (A)≦the dielectric constant of the cured product of the maleimide compound (B).

[0108] In the resin composition of the present embodiment, the difference between the dielectric constant of the block copolymer (C) having a styrene skeleton and the dielectric constant of the cured product of the maleimide compound (B) is preferably 0.6 or less, more preferably 0.5 or less, even more preferably 0.4 or less, even more preferably less than 0.4, and even more preferably 0.3 or less. By making it equal to or less than the upper limit, the compatibility between the block copolymer (C) and the maleimide compound (B) is improved, so that the low dielectric properties (Dk and / or Df, especially Dk), moisture absorption heat resistance, and peel strength against metal foil of the obtained cured product tend to be more excellent. The lower limit of the difference between the relative dielectric constant of the block copolymer (C) having a styrene skeleton and the relative dielectric constant of a cured product of the maleimide compound (B) is zero. Moreover, usually, the relative dielectric constant of the block copolymer (C) having a styrene skeleton≦the relative dielectric constant of the cured product of the maleimide compound (B).

[0109] In the resin composition of the present embodiment, the difference between the dielectric constant of the cured product of the resin (D) containing an aromatic ring and two or more polymerizable unsaturated groups and the dielectric constant of the cured product of the maleimide compound (B) is preferably 0.3 or less, more preferably 0.2 or less, even more preferably less than 0.2, and even more preferably 0.1 or less. By making it equal to or less than the upper limit, the compatibility between the resin (D) containing a polymerizable unsaturated group and the maleimide compound (B) is improved, so that the low dielectric properties (Dk and / or Df, especially Dk), moisture absorption heat resistance, and peel strength against metal foil of the obtained cured product tend to be more excellent. The lower limit of the difference between the dielectric constant of the cured product of the resin (D) containing an aromatic ring and two or more polymerizable unsaturated groups and the dielectric constant of the cured product of the maleimide compound (B) is zero. In particular, it is preferable that the difference between the dielectric constant of the cured product of the resin (D) containing an aromatic ring and two or more polymerizable unsaturated groups and the dielectric constant of the cured product of the maleimide compound (B) is satisfied, and that the cured product of the resin (D) containing an aromatic ring and two or more polymerizable unsaturated groups has a dielectric constant of 2.2 to 2.6.

[0110] Furthermore, in the resin composition of this embodiment, the dielectric constant of the cured product of each of the maleimide compound (A), the maleimide compound (B), the block copolymer (C) having a styrene skeleton, and the resin (D) containing an aromatic ring and two or more polymerizable unsaturated groups is preferably 2.6 or less, more preferably 2.5 or less, even more preferably less than 2.5, and even more preferably 2.4 or less, and the lower limit is preferably 1.9 or more, more preferably 2.0 or more, and even more preferably more than 2.0. By making the dielectric constant of each component equal to or less than the upper limit, the low dielectric properties (Dk and / or Df, especially Dk), moisture absorption heat resistance, and peel strength against metal foil of the obtained cured product tend to be more excellent. In addition, from the viewpoint of suppressing localized decrease in dielectric constant of the cured product and improving moisture absorption and heat resistance, it is preferable that the difference in the dielectric constant of each component is not large. From this viewpoint, and taking into consideration practical circumstances, the lower limit of the dielectric constant of each component is preferably 2.0 or more.

[0111] In the resin composition of this embodiment, of the total amount of the maleimide compound (A), the maleimide compound (B), the block copolymer (C) having a styrene skeleton, and the resin (D) containing an aromatic ring and two or more polymerizable unsaturated groups contained in the resin composition, 90 mass % or more (preferably 95 mass % or more, more preferably 97 mass % or more) preferably has a relative dielectric constant of a cured product of 2.6 or less, more preferably 2.5 or less, even more preferably less than 2.5, and even more preferably 2.4 or less, and the lower limit is preferably 1.9 or more, more preferably 2.0 or more, and even more preferably greater than 2.0.

[0112] <Cyanate ester compounds (E)> The resin composition of the present embodiment preferably contains a cyanate ester compound (E). The cyanate ester compound (E) is not particularly limited as long as it is a compound containing 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 (E) is preferably a compound in which a cyanate group is directly bonded to an aromatic skeleton (aromatic ring). Examples of the cyanate ester compound (E) 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. In this embodiment, a naphthol aralkyl cyanate ester represented by formula (7) is particularly preferred. [ka] (In formula (7), R 6 Each independently represents a hydrogen atom or a methyl group, and among these, a hydrogen atom is preferable. 2 represents an integer of 1 or more. 2 The upper limit is usually 10, preferably 6. In addition to the above, in this embodiment, the cyanate ester compounds described in WO 2021 / 172317 can be used, the contents of which are incorporated herein by reference.

[0113] The relative dielectric constant at a frequency of 10 GHz of the cured product of the cyanate ester compound (E) used in this embodiment, measured according to a cavity resonance perturbation method, is preferably 3.0 or less, more preferably 2.9 or less, and even more preferably less than 2.9, and the lower limit is practically 2.4 or more.

[0114] The resin composition of the present embodiment preferably contains a cyanate ester compound (E) 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 (E), the lower limit of the content is preferably 0.1 parts by mass or more, more preferably 1 part by mass or more, more preferably 2 parts by mass or more, and more preferably 3 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 (E) 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 property of the obtained cured product tend to be excellent. When the resin composition of the present embodiment contains a cyanate ester compound (E), the upper limit of the content of the cyanate ester compound (E) 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 6 parts by mass or less, relative to 100 parts by mass of the resin solid content in the resin composition. The resin composition in this embodiment may contain only one type of cyanate ester compound (E), or may contain two or more types. When two or more types are contained, the total amount is preferably within the above range.

[0115] <Compound (F) Having One Polymerizable Unsaturated Group in the Molecule> The resin composition of this embodiment preferably contains a compound (F) having one polymerizable unsaturated group in the molecule (hereinafter, sometimes referred to as "compound (F) containing a polymerizable unsaturated group"). By blending the compound (F) containing a polymerizable unsaturated group, the moisture absorption heat resistance of the obtained cured product tends to be further improved. Such a compound reacts with the polymerizable unsaturated group that is likely to remain unreacted when the resin composition is cured, and can reduce the polymerizable unsaturated group in the cured product. In particular, by adopting a compound containing a carbon-carbon unsaturated bond at the end of the molecule, it reacts with the resin (D) containing an aromatic ring and two or more polymerizable unsaturated groups, and the moisture absorption heat resistance of the obtained cured product tends to be further improved. The polymerizable unsaturated group is preferably a group having a carbon-carbon unsaturated double bond, more preferably a group selected from the group consisting of a (meth)acrylic group, a (meth)allyl group, and a vinylbenzyl group, even more preferably a group selected from the group consisting of a (meth)acrylic group and a vinylbenzyl group, and even more preferably a vinylbenzyl group.

[0116] The compound (F) containing a polymerizable unsaturated group used in this embodiment is preferably composed only of atoms selected from the group consisting of carbon atoms, hydrogen atoms, oxygen atoms, nitrogen atoms, and silicon atoms, more preferably composed only of atoms selected from the group consisting of carbon atoms, hydrogen atoms, oxygen atoms, and silicon atoms, and even more preferably composed only of atoms selected from the group consisting of carbon atoms, hydrogen atoms, and oxygen atoms. The compound (F) containing a polymerizable unsaturated group used in this embodiment may or may not have a polar group.The compound containing a polymerizable unsaturated group used in this embodiment is preferably not having a polar group.The polar group is exemplified by an amino group, a carboxyl group, a hydroxyl group, and a nitro group.

[0117] In this embodiment, the molecular weight of the compound (F) containing a polymerizable unsaturated group 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 (F) containing a polymerizable unsaturated group from the resin composition of this embodiment or its cured product can be suppressed. The upper limit of the molecular weight of the compound (F) containing a polymerizable unsaturated group 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 resin (D) containing a polymerizable unsaturated group is further improved. When the resin composition of the present embodiment contains two or more compounds (F) containing a polymerizable unsaturated group, it is preferable that the average molecular weight value of the compounds (F) containing a polymerizable unsaturated group falls within the above range, and it is more preferable that the molecular weight of each compound falls within the above preferred range.

[0118] In this embodiment, the compound (F) containing a polymerizable unsaturated group preferably has a boiling point of 110°C or more, more preferably 115°C or more, and even more preferably 120°C or more. By making the boiling point equal to or more than the lower limit, the volatilization of the compound (F) containing a polymerizable unsaturated group during thermal curing of the resin composition is suppressed, and the compound (F) can be more effectively reacted with the polymerizable unsaturated group of the resin (D) containing a polymerizable unsaturated group. The boiling point of the compound (F) containing a polymerizable unsaturated group is preferably 300°C or less, more preferably 250°C or less, and even more preferably 200°C or less. By making the boiling point equal to or less than the upper limit, the compound (F) is less likely to remain as a residual solvent in the cured product. When the resin composition of the present embodiment contains two or more compounds (F) containing a polymerizable unsaturated group, 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.

[0119] Examples of the compound (F) containing a polymerizable unsaturated group 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.), styryl silane compounds (e.g., styryl trialkoxy silane, etc.), and the like, with aromatic vinyl compounds (preferably styrene-based compounds) being preferred. Specific examples of aromatic vinyl compounds include o-methylstyrene, m-methylstyrene, p-methylstyrene (4-methylstyrene), o,p-dimethylstyrene, o-ethylvinylbenzene, m-ethylvinylbenzene, p-ethylvinylbenzene, methylvinylbiphenyl, and ethylvinylbiphenyl, with p-methylstyrene (4-methylstyrene) being preferred.

[0120] In the resin composition of the present embodiment, the content of the compound (F) containing a polymerizable unsaturated group 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 improve. In addition, the upper limit of the content of the compound (F) containing a polymerizable unsaturated group 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, especially Dk) of the obtained cured product tend to be more excellent. The resin composition of the present embodiment may contain only one type of compound (F) containing a polymerizable unsaturated group, or may contain two or more types. When two or more types are contained, the total amount is preferably within the above range.

[0121] <Filling material (G)> The resin composition of the present embodiment preferably contains a filler (G). By containing the filler (G), the resin composition and its cured product can have improved physical properties such as dielectric properties (low dielectric constant, low dielectric tangent, etc.), flame resistance, and low thermal expansion. Moreover, the filler (G) used in this embodiment is more preferably excellent in low dielectric properties (Dk and / or Df). For example, the filler (G) used in this embodiment has a relative dielectric constant (Dk) of preferably 8.0 or less, more preferably 6.0 or less, and even more preferably 4.0 or less at a frequency of 10 GHz measured according to the cavity resonator perturbation method. The lower limit of the relative dielectric constant is, for example, 2.0 or more. The filler (G) used in this embodiment has a dielectric loss tangent (Df) of preferably 0.05 or less, more preferably 0.01 or less at a frequency of 10 GHz measured according to the cavity resonator perturbation method. The lower limit of the dielectric loss tangent is, for example, 0.0001 or more.

[0122] The filler (G) used in this embodiment is not particularly limited in type, and can be suitably used in the art.Specifically, natural silica, fused silica, synthetic silica, amorphous silica, aerosil, hollow silica, and other silica, 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, and aluminum nitride, and other nitrides, aluminum hydroxide, aluminum hydroxide heat-treated product (aluminum hydroxide heat-treated to remove a portion of the crystal water), boehmite, magnesium hydroxide, and other metal hydroxides (including hydrates), oxides, Examples of fillers include inorganic fillers such as molybdenum and molybdenum compounds such as 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, silicone composite powder, and fluororesin fillers. 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 (Dk and / or Df), more preferably contain one or more selected from the group consisting of silica and aluminum hydroxide, and even more preferably contain silica. 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.

[0123] The content of the filler (G) in the resin composition of this embodiment can be appropriately set according to the desired properties, and is not particularly limited. However, it is preferably 10 parts by mass or more, more preferably 20 parts by mass or more, even more preferably 40 parts by mass or more, even more preferably 60 parts by mass or more, and even more preferably 80 parts by mass or more, relative to 100 parts by mass of the resin solid content in the resin composition. By setting it to the lower limit or more, the low thermal expansion and low dielectric loss tangent of the obtained cured product tend to be more excellent. In addition, the upper limit of the content of the filler (G) is preferably 1600 parts by mass or less, more preferably 1000 parts by mass or less, even more preferably 500 parts by mass or less, even more preferably 300 parts by mass or less, even more preferably 250 parts by mass or less, and may be 200 parts by mass or less, 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, the moldability of the resin composition tends to be further improved. In the resin composition of this embodiment, one preferred embodiment is one in which the content of the filler (G) is 1 to 95 mass % of the components excluding the solvent, and preferably 30 to 80 mass %. The resin composition of the present embodiment may contain only one type of filler (G), or may contain two or more types. When two or more types are contained, the total amount is preferably within the above range.

[0124] In the resin composition of the present embodiment, when the filler (G), 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 (G) and the adhesive strength between the resin component and the filler (G) 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 (e.g., p-styryltrimethoxysilane, etc.), acrylsilane 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.

[0125] <Other thermosetting compounds> The resin composition of the present embodiment may or may not contain a thermosetting compound (another thermosetting compound) other than the maleimide compound (A), the maleimide compound (B), the block copolymer (C), the resin containing a polymerizable unsaturated group (D), the cyanate ester compound (E), and the compound having one polymerizable unsaturated group in its molecule (F). Examples of other thermosetting compounds include one or more selected from the group consisting of epoxy compounds, phenolic compounds, oxetane resins, and benzoxazine compounds. For details of these components, refer to paragraphs 0055 to 0062 of International Publication No. 2023 / 026829, the contents of which are incorporated herein by reference. In the resin composition of this embodiment, of the total amount of the maleimide compound (A), the maleimide compound (B), the block copolymer (C) having a styrene skeleton, the resin (D) containing an aromatic ring and two or more polymerizable unsaturated groups, the cyanate ester compound (E), the compound (F) having one polymerizable unsaturated group in the molecule, and other thermosetting compounds contained in the resin composition, 90 mass % or more (preferably 95 mass % or more, more preferably 97 mass % or more) of the cured product has a relative dielectric constant at a frequency of 10 GHz measured according to a cavity resonance perturbation method of preferably 2.6 or less, more preferably 2.5 or less, even more preferably less than 2.5, and even more preferably 2.4 or less, and the lower limit is preferably 2.0 or more, and more preferably greater than 2.0.

[0126] In the resin composition of this embodiment, the total amount of the maleimide compound (A), the maleimide compound (B), the block copolymer (C), the resin containing a polymerizable unsaturated group (D), the cyanate ester compound (E), and the compound having one polymerizable unsaturated group in the molecule (F) preferably accounts for 50 mass% or more of the resin solids, more preferably 60 mass% or more, and even more preferably 70 mass% or more, and may be 80 mass% or more, but is 100 mass% or less.

[0127] <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 (Dk and / or Df).

[0128] 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, even more preferably 10 parts by mass or more, and may be 15 parts by mass or more, relative to 100 parts by mass of the resin solid content in the resin composition. The lower limit of the content of the flame retardant is preferably 30 parts by mass or less, more preferably 25 parts by mass or less, relative to 100 parts by mass of the resin solid content in the resin composition. 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.

[0129] <Active ester compounds> The resin composition of the present embodiment may contain an active ester compound within a range that does not impair the effects of the present invention. The active ester compound is not particularly limited, and for example, the description in paragraphs 0064 to 0066 of WO 2021 / 172317 can be referred to, the contents of which are incorporated herein by reference.

[0130] When the resin composition of the present embodiment contains an active ester compound, the amount thereof is preferably 1 part 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 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.

[0131] <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.

[0132] 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 may be 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.

[0133] <Curing accelerator> The resin composition of the present embodiment may further include a curing accelerator. The curing accelerator is not particularly limited, but may include imidazoles such as 2-ethyl-4-methylimidazole and triphenylimidazole; organic peroxides such as benzoyl peroxide, lauroyl peroxide, acetyl peroxide, parachlorobenzoyl peroxide, di-tert-butyl-di-perphthalate, α,α'-di(t-butylperoxy)diisopropylbenzene, 2,5-dimethyl-2,5-di(t-butylperoxy)hexane, and 2,5-dimethyl-2,5-bis(t-butylperoxy)hexyne-3; azo compounds such as azobisnitrile; N,N-dimethylbenzylamine, N,N-dimethylaniline, N,N-dimethyltoluidine, 2-N-ethylanilinoethanol, tri-n-butylamine, pyridine, quinoline, and N-methylmorpholine. , triethanolamine, triethylenediamine, tetramethylbutanediamine, N-methylpiperidine and other tertiary amines; phenols such as phenol, xylenol, cresol, resorcin, catechol; high-temperature decomposition type radical generators such as 2,3-dimethyl-2,3-diphenylbutane; organic metal salts such as lead naphthenate, lead stearate, zinc naphthenate, zinc octylate, manganese octylate, tin oleate, dibutyltin maleate, manganese naphthenate, cobalt naphthenate, and acetylacetonate iron; dissolving these organic metal salts in hydroxyl-containing compounds such as phenol and bisphenol; inorganic metal salts such as tin chloride, zinc chloride, and aluminum chloride; dioctyltin oxide, other alkyl tins, alkyl tin oxides and other organic tin compounds. Among them, preferred curing accelerators are imidazoles and organic metal salts, and imidazoles are more preferred.

[0134] 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.

[0135] <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, cyclohexanone, etc.), cellosolves (e.g., propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, etc.), esters (e.g., ethyl lactate, methyl acetate, ethyl acetate, butyl acetate, isoamyl acetate, ethyl lactate, methyl methoxypropionate, methyl hydroxyisobutyrate, etc.), 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.

[0136] <Other ingredients> In addition to the above components, the resin composition of the present embodiment may contain various polymer compounds such as thermoplastic resins and their oligomers, petroleum resins, and various additives. Examples of additives include ultraviolet absorbers, antioxidants, photopolymerization initiators, fluorescent whitening agents, 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.

[0137] <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.

[0138] The resin composition of the present embodiment preferably has a low dielectric constant (Dk) of the cured product. Specifically, the dielectric constant (Dk) at a frequency of 10 GHz measured according to a cavity resonator perturbation method when molded into a cured plate with a thickness of 0.8 mm is preferably less than 2.45. The lower limit of the dielectric constant (Dk) is not particularly specified, but for example, 0.01 or more is practical. More specifically, the dielectric constant (Dk) of the cured sheet is measured by the method described in the Examples below.

[0139] 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.

[0140] <<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 (G)) 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.

[0141] The substrate is not particularly limited as long as it is a substrate used in various printed wiring board materials. Examples of the substrate material include glass fibers (e.g., E-glass, D-glass, L-glass, S-glass, T-glass, Q-glass, UN-glass, NE-glass, NER-glass, spherical glass, etc.), inorganic fibers other than glass (e.g., quartz, etc.), and organic fibers (e.g., polyimide, polyamide, polyester, liquid crystal polyester, polytetrafluoroethylene, etc.). The form of the substrate is not particularly limited, and examples 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 2The 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, NER-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 a frequency of 10 GHz using a perturbation method cavity resonator.

[0142] <<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 arranged on one or both sides of the layer formed from the prepreg. For example, the metal foil-clad laminate of this embodiment may be produced by arranging at least one prepreg of this embodiment (preferably two or more sheets are stacked), arranging 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 arranging a metal foil such as copper or aluminum on one or both sides of the prepreg and laminating and molding the laminate. 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 thereof include copper foils such as rolled copper foil and electrolytic copper foil. The thickness of the metal foil (preferably, copper foil) is not particularly limited and may be about 1.5 to 70 μm. In addition, when copper foil is used as the metal foil, it is preferable that the copper foil has a surface roughness Rz of 0.2 to 4.0 μm measured according to JIS B0601:2013. By setting the surface roughness Rz to 0.2 μm or more, the surface roughness of the copper foil becomes moderate, and the copper foil peel strength tends to be further improved. On the other hand, by setting the surface roughness Rz to 4.0 μm or less, the surface roughness of the copper foil becomes moderate, and the dielectric loss tangent characteristics of the obtained cured product tend to be further improved. From the viewpoint of reducing the dielectric tangent, the roughness Rz of the copper foil surface is more preferably 0.5 μm or more, even more preferably 0.6 μm or more, and particularly preferably 0.7 μm or more, and more preferably 3.5 μm or less, even more preferably 3.0 μm or less, and particularly preferably 2.0 μm or less.

[0143] Examples of the lamination molding method include methods commonly used for molding laminates and multilayer boards for printed wiring boards. More specifically, a multistage press machine, a multistage vacuum press machine, a continuous molding machine, an autoclave molding machine, or the like is used to perform lamination molding 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. 2 A 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.

[0144] The metal foil-clad laminate of this embodiment has a peel strength measured in accordance with the provision of 5.7 "Peel strength" of JIS C6481 of preferably 0.28 kN / m or more, more preferably 0.38 kN / m or more, and even more preferably 0.50 kN / m or more. The upper limit of the peel strength is not particularly specified, but is, for example, 2.00 kN / m or more. Peel strength is measured as described in the Examples section below.

[0145] As described above, the resin composition for electronic materials obtained using the resin composition of the present embodiment (a resin composition including a combination of specific components) can provide a cured product having excellent properties such as low dielectric characteristics (low dielectric constant, low dielectric tangent, particularly low dielectric constant), moisture absorption heat resistance, and peel strength against metal foil, as well as excellent heat resistance, desmear resistance, crack resistance, appearance of the cured product, and low thermal expansion.

[0146] <<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 copper 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.

[0147] 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. The present embodiment also 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.

[0148] In addition, it is preferable that the insulating layer formed of the cured product of the resin composition of this embodiment has a small surface roughness after roughening treatment. Specifically, the arithmetic mean roughness Ra of the surface of the insulating layer after roughening treatment is preferably 200 nm or less, more preferably 150 nm or less, and particularly preferably 100 nm or less. The lower limit of the arithmetic mean roughness Ra is not particularly limited, but may be, for example, 10 nm or more. The arithmetic mean roughness Ra of the surface of the insulating layer is measured using a non-contact surface roughness meter in VSI mode with a 50x lens. The non-contact surface roughness meter used is WYKONT3300 manufactured by B-COIN Instruments.

[0149] <<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.

[0150] 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.

[0151] 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.

[0152] 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

[0153] 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.

[0154] <Measurement of weight average molecular weight and number average molecular weight> The weight average molecular weight (Mw) and number average molecular weight (Mn) of the resin component 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.

[0155] <Measurement of the relative dielectric constant of resin components> The resin component was powdered, and the resulting powder was filled into a mold with sides of 100 mm and a thickness of 0.8 mm. Copper foil with a thickness of 12 μm (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 relative dielectric constant (Dk) was evaluated as follows. After removing the copper foil on both sides of the obtained cured plate by etching, the plate was downsized to 10mm x 1mm to obtain an evaluation sample. The obtained evaluation sample was dried at 120°C for 60 minutes, and then the relative dielectric constant (Dk) after drying at a frequency of 10GHz was measured using a perturbation method cavity resonator. The measurement temperature was 23°C. The perturbation method cavity resonator used was Agilent8722ES manufactured by Agilent Technologies Inc. The evaluation results are shown in Table 1. However, the dielectric constant of the block copolymer (C) having a styrene skeleton or the resin that cannot be cured by the vacuum press was measured by drying the pellets at 120°C for 60 minutes and then measuring the dielectric constant (Dk) at a frequency of 10 GHz using a perturbation method cavity resonator. The measurement temperature was 23°C.

[0156] <Synthesis Example 1: 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.

[0157] 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 %). The relative dielectric constant measured according to the above method was 2.3.

[0158] <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. 2 9.36g (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.

[0159] <<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 number average molecular weight of the modified polyphenylene ether compound in terms of polystyrene by the GPC method was 2,250, the weight average molecular weight in terms of polystyrene by the GPC method was 3,920, and the vinyl group equivalent was 1189 g / vinyl group. The relative dielectric constant measured according to the above method was 2.4.

[0160] <Synthesis Example 3: Synthesis of naphthol aralkyl cyanate ester compound (SNCN)> 300 g (1.28 mol in terms of OH groups) of 1-naphthol aralkyl resin (manufactured by Nippon Steel & Sumikin Chemical Co., Ltd.) and 194.6 g (1.92 mol) of triethylamine (1.5 mol per 1 mol of hydroxyl groups) were dissolved in 1800 g of dichloromethane to prepare solution 1. 125.9g (2.05mol) of cyanogen chloride (1.6mol per 1mol of hydroxyl groups), 293.8g of dichloromethane, 194.5g (1.92mol) of 36% hydrochloric acid (1.5mol per 1mol of hydroxyl groups), and 1205.9g of water were poured in over 30 minutes while stirring and keeping the liquid temperature between -2℃ and -0.5℃. After the pouring of solution 1 was completed, the mixture was stirred at the same temperature for 30 minutes, and then a solution (solution 2) in which 65g (0.64mol) of triethylamine (0.5mol per 1mol of hydroxyl groups) was dissolved in 65g of dichloromethane was poured in over 10 minutes. After the pouring of solution 2 was completed, the mixture was stirred at the same temperature for 30 minutes to complete the reaction. The reaction solution was then left to stand to separate the organic and aqueous phases. The resulting organic phase was washed five times with 1300 g of water. The electrical conductivity of the wastewater from the fifth wash was 5 μS / cm, confirming that the ionic compounds were sufficiently removed by washing with water. The organic phase after washing with water was concentrated under reduced pressure and finally concentrated to dryness at 90°C for 1 hour to obtain 331 g of the desired naphthol aralkyl cyanate ester compound (SNCN) (orange viscous material). The weight average molecular weight of the obtained SNCN was 600. In addition, the IR spectrum of SNCN was 2250 cm -1 (cyanate ester group) absorption and no hydroxyl group absorption was observed. The relative dielectric constant measured according to the above method was 2.8.

[0161] Example 1 14.0 parts by mass of a maleimide compound (ma) having the structure shown below (a compound represented by formula (3), manufactured by Designer Molecules Inc., "BMI-5000", having a weight average molecular weight of 17,000 and a relative dielectric constant measured according to the above method of 2.3), 19.0 parts by mass of a maleimide compound (mb) having the structure shown below (manufactured by DIC Corporation, "NE-X-9470S", a compound represented by formula (M1), having a weight average molecular weight of 2,500 and a relative dielectric constant measured according to the above method of 2.4), 15.0 parts by mass of a block copolymer (SBS, manufactured by JSR Corporation, TR2250, having a weight average molecular weight of 120,000 and a relative dielectric constant measured according to the above method of 2.1). parts by mass, 5.0 parts by mass of the polymer (va) having a structural unit represented by formula (V) obtained in the above synthesis example 1, 19.0 parts by mass of the modified polyphenylene ether compound obtained in the above synthesis example 2, 5.0 parts by mass of the naphthol aralkyl cyanate ester compound (SNCN) obtained in the above synthesis example 3, 3.0 parts by mass of 4-methylstyrene (Tokyo Chemical Industry Co., Ltd.), 20.0 parts by mass of a phosphorus-based flame retardant (PX-200, Daihachi Chemical Industry Co., Ltd.), and 0.25 parts by mass of an imidazole-based catalyst (Shikoku Chemical Industry Co., Ltd.) were dissolved in methyl ethyl ketone (solvent) and mixed to obtain a varnish. Note that the above-mentioned amounts of each additive indicate the solid content.

[0162] Maleimide compounds (ma) [ka] The maleimide compound (ma) is represented by the formula (3): 1 and R 3 is an octylene group, and R 2 is a cyclohexylene group having an n-hexyl group and an n-octyl group as substituents, and is a compound having a weight average molecular weight of 17,000.

[0163] Maleimide compounds (mb) [ka] n is an integer from 1 to 20.

[0164] <Production of hardened plate test pieces with a thickness of 0.8 mm> The solvent was evaporated from the obtained varnish to obtain a resin composition powder. The resin composition powder was filled into a mold having a side of 100 mm and a thickness of 0.8 mm, and copper foil having a thickness of 12 μm (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 sheets were evaluated for dielectric constant (Dk), peel strength, and moisture absorption and heat resistance. The evaluation results are shown in Table 1.

[0165] <Measurement and evaluation methods> (1) Dielectric constant (Dk) After removing the copper foil on both sides of the obtained cured plate by etching, the plate was downsized to 10mm x 1mm to obtain an evaluation sample. The obtained evaluation sample was dried at 120°C for 60 minutes, and then the relative dielectric constant (Dk) after drying at a frequency of 10GHz was measured using a perturbation method cavity resonator. The measurement temperature was 23°C. The perturbation method cavity resonator used was Agilent8722ES manufactured by Agilent Technologies. A: Less than 2.45 B:2.45 or more

[0166] (2) Peel strength The copper foil peel strength (adhesive strength) was measured twice using the cured plate (10mm x 100mm x 0.8mm) obtained as described above in accordance with JIS C6481, 5.7 "Peel strength", and the average value was calculated. The measurement temperature was 23°C. The evaluation was as follows: A: 0.4kN / m or more B: Less than 0.4kN / m

[0167] (3) Moisture absorption and heat resistance The obtained hardened plate was cut to 50mm x 50mm (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 then immersed (dipped) in a solder bath at 260°C for 30 seconds, and the presence or absence of abnormal changes in appearance was visually observed. The pressure cooker tester used was a PC-3 model manufactured by Hirayama Seisakusho. For each measurement, three sheets were tested, and if there was no swelling among the three sheets, it was evaluated as "A", and if swelling was observed, it was evaluated as "B". The appearance was observed by five experts and the majority vote was used.

[0168] Example 2 In Example 1, the content of the maleimide compound (ma) was 10.5 parts by mass, the content of the maleimide compound (mb) was 15.5 parts by mass, the content of the polymer (va) having a structural unit represented by formula (V) was 15.5 parts by mass, and the content of the modified polyphenylene ether compound was 15.5 parts by mass, but the rest was the same.

[0169] Example 3 In Example 1, the maleimide compound (ma) was not included, the content of the maleimide compound (compound represented by formula (3), Shin-Etsu Chemical Co., Ltd., "SLK-3000", the relative dielectric constant measured according to the above method is 2.3, the structure is the same as that of the maleimide compound (ma) except for the value of n) was 10.5 parts by mass, the content of the maleimide compound (mb) was 15.5 parts by mass, the content of the polymer (va) having a structural unit represented by formula (V) was 15.5 parts by mass, and the content of the modified polyphenylene ether compound was 15.5 parts by mass. The rest was performed in the same manner.

[0170] Comparative Example 1 The same procedure was carried out in Example 1, except that the maleimide compound (ma) was not included and the content of the polymer (va) having a structural unit represented by formula (V) was 19.0 parts by mass.

[0171] Comparative Example 2 In Example 1, the content of the maleimide compound (ma) was changed to 19.0 parts by mass, and the content of the polymer (va) not containing the maleimide compound (mb) and having a structural unit represented by formula (V) was changed to 19.0 parts by mass, but the rest was carried out in the same manner.

[0172] Comparative Example 3 In Example 1, the content of the maleimide compound (ma) was 19.0 parts by mass, the content of the maleimide compound (mb) was 24.0 parts by mass, the content of the polymer (va) not containing a block copolymer and having a structural unit represented by formula (V) was 10.0 parts by mass, and the content of the modified polyphenylene ether compound was 24.0 parts by mass, but the rest was similarly changed.

[0173] Comparative Example 4 In Example 1, the content of the maleimide compound (ma) was 27.0 parts by mass, the content of the maleimide compound (mb) was 30.0 parts by mass, and the polymer (va) having a structural unit represented by formula (V) and the modified polyphenylene ether compound were not contained. The rest was the same.

[0174] Comparative Example 5 In Example 1, the maleimide compound (mb) was not included, and the content of the maleimide compound (mc) shown in the structure below (manufactured by Nippon Kayaku Co., Ltd., MIR-3000, relative dielectric constant measured according to the above method is 2.7) was changed to 19.0 parts by mass, but the rest was performed in the same manner. Maleimide compounds (MC) [ka]

[0175] Comparative Example 6 In Example 1, the maleimide compound (mb) was not included, and the content of the maleimide compound (md) shown in the structure below (manufactured by Daiwa Chemical Industry Co., Ltd., BMI-2300, relative dielectric constant measured according to the above method is 2.9) was changed to 19.0 parts by mass, but the rest was performed in the same manner. Maleimide compounds (MD) [ka]

[0176] [Table 1]

Claims

1. 1. A resin composition comprising: a maleimide compound (A) having an aliphatic hydrocarbon group having 8 or more carbon atoms in the molecule and having two or more maleimide groups; a maleimide compound (B) having an aliphatic hydrocarbon group having 7 or less carbon atoms in the molecule, no aliphatic hydrocarbon group having 8 or more carbon atoms, and having two or more maleimide groups; a block copolymer (C) having a styrene skeleton; and a resin (D) containing an aromatic ring and two or more polymerizable unsaturated groups other than the block copolymer (C) having a styrene skeleton, wherein the difference between the dielectric constant at a frequency of 10 GHz of a cured product of the maleimide compound (A) as measured according to a cavity resonance perturbation method and the dielectric constant at a frequency of 10 GHz of a cured product of the maleimide compound (B) as measured according to a cavity resonance perturbation method is 0.3 or less.

2. 2. The resin composition according to claim 1, wherein the cured product of the maleimide compound (A) has a relative dielectric constant of 2.1 to 2.5 at a frequency of 10 GHz measured according to a cavity resonance perturbation method.

3. 3. The resin composition according to claim 1, wherein the cured product of the maleimide compound (B) has a relative dielectric constant of 2.2 to 2.6 at a frequency of 10 GHz as measured according to a cavity resonance perturbation method.

4. 3. The resin composition according to claim 1, wherein a difference between a dielectric constant at a frequency of 10 GHz of the block copolymer (C) having a styrene skeleton, as measured according to a cavity resonance perturbation method, and a dielectric constant at a frequency of 10 GHz of a cured product of the maleimide compound (B), as measured according to a cavity resonance perturbation method, is 0.6 or less.

5. 3. The resin composition according to claim 1, wherein the block copolymer (C) having a styrene skeleton has a relative dielectric constant of 1.9 to 2.2 at a frequency of 10 GHz measured according to a cavity resonance perturbation method.

6. a difference between a dielectric constant at a frequency of 10 GHz of a cured product of the resin (D) containing an aromatic ring and two or more polymerizable unsaturated groups, as measured according to a cavity resonance perturbation method, and a dielectric constant at a frequency of 10 GHz of a cured product of the maleimide compound (B), as measured according to a cavity resonance perturbation method, is 0.3 or less; The resin composition according to claim 1 or 2, wherein the cured product of the resin (D) containing an aromatic ring and two or more polymerizable unsaturated groups has a relative dielectric constant of 2.2 to 2.6 at a frequency of 10 GHz measured according to a cavity resonance perturbation method.

7. The resin composition according to claim 1 or 2, wherein the dielectric constant at a frequency of 10 GHz of a cured product of the maleimide compound (A), measured according to a cavity resonance perturbation method, the dielectric constant at a frequency of 10 GHz of a cured product of the maleimide compound (B), the dielectric constant at a frequency of 10 GHz of the block copolymer (C) having a styrene skeleton, measured according to a cavity resonance perturbation method, and the dielectric constant at a frequency of 10 GHz of a cured product of the resin (D) containing an aromatic ring and two or more polymerizable unsaturated groups, measured according to a cavity resonance perturbation method, are each independently 2.0 to 2.

6.

8. The content of the maleimide compound (A) is 5 to 40 parts by mass based on 100 parts by mass of the resin solid content, The content of the maleimide compound (B) is 5 to 40 parts by mass relative to 100 parts by mass of the resin solid content, the content of the block copolymer (C) having a styrene skeleton is 3 to 40 parts by mass relative to 100 parts by mass of a resin solid content, The resin composition according to claim 1 or 2, wherein the content of the resin (D) containing an aromatic ring and two or more polymerizable unsaturated groups is 5 to 50 parts by mass per 100 parts by mass of resin solids.

9. The resin composition according to claim 1 or 2, wherein a mass ratio ((A) / (B)) of a content of the maleimide compound (A) to a content of the maleimide compound (B) is 30 / 70 to 70 to 30.

10. 3. The resin composition according to claim 1, wherein the maleimide compound (A) has two or more divalent linear aliphatic hydrocarbon groups having 8 to 20 carbon atoms in the molecule.

11. The resin composition according to claim 1 or 2, wherein the maleimide compound (A) has a weight average molecular weight of 2,000 to 30,000.

12. 3. The resin composition according to claim 1, wherein the maleimide compound (A) has one or more groups represented by formula (1), and the maleimide groups are each independently linked to the group represented by formula (1) via at least an aliphatic hydrocarbon group having 8 or more carbon atoms. 【Chemistry 1】

13. The resin composition according to claim 1 or 2, wherein the maleimide compound (A) has a structural unit represented by formula (2). 【Chemistry 2】 (In formula (2), R １ and R ３ each independently represents a linear aliphatic hydrocarbon group having 8 or more carbon atoms; R ２ represents a hydrocarbon group having an alicyclic structure of 4 to 10 members.

14. The resin composition according to claim 1 or 2, wherein the maleimide compound (A) comprises a compound represented by formula (3). 【Chemistry 3】 (In formula (3), R １ and R ３ each independently represents a linear aliphatic hydrocarbon group having 8 or more carbon atoms; R ２ represents a hydrocarbon group having an alicyclic structure of 4 to 10 members, and n represents a number from 1 to 10.

15. The resin composition according to claim 1 or 2, wherein the maleimide compound (B) has a weight average molecular weight of 350 to 5000.

16. The resin composition according to claim 1 or 2, wherein the maleimide compound (B) comprises a compound represented by formula (M1): 【Chemistry 4】 (In formula (M1), R Ｍ１ , R Ｍ２ , R Ｍ３ , and R Ｍ４ R each independently represents a hydrogen atom or an organic group. Ｍ５ and R Ｍ６ Each independently represents a hydrogen atom or an alkyl group. Ｍ represents a divalent aromatic group. A is a 4- to 6-membered alicyclic group. R Ｍ７ and R Ｍ８ are each independently an alkyl group. mx is 1 or 2, and lx is 0 or 1. R Ｍ９ and R Ｍ１０ Each of R independently represents a hydrogen atom or an alkyl group. Ｍ１１ , R Ｍ１２ , R Ｍ１３ , and R Ｍ１４ R each independently represents a hydrogen atom or an organic group. Ｍ１５ each independently represents an alkyl group having 1 to 10 carbon atoms, an alkyloxy group having 1 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, an aryloxy group having 6 to 10 carbon atoms, an arylthio group having 6 to 10 carbon atoms, a halogen atom, a hydroxyl group, or a mercapto group. px represents an integer of 0 to 3. nx represents an integer of 1 to 20.)

17. The resin composition according to claim 1 or 2, wherein the maleimide compound (A) comprises a compound represented by formula (3), and the maleimide compound (B) comprises a compound represented by formula (M1). 【Chemistry 5】 (In formula (3), R １ and R ３ each independently represents a linear aliphatic hydrocarbon group having 8 or more carbon atoms; R ２ represents a hydrocarbon group having an alicyclic structure of 4 to 10 members, and n represents a number from 1 to 10. 【Chemistry 6】 (In formula (M1), R Ｍ１ , R Ｍ２ , R Ｍ３ , and R Ｍ４ R each independently represents a hydrogen atom or an organic group. Ｍ５ and R Ｍ６ Each independently represents a hydrogen atom or an alkyl group. Ｍ represents a divalent aromatic group. A is a 4- to 6-membered alicyclic group. R Ｍ７ and R Ｍ８ are each independently an alkyl group. mx is 1 or 2, and lx is 0 or 1. R Ｍ９ and R Ｍ１０ Each of R independently represents a hydrogen atom or an alkyl group. Ｍ１１ , R Ｍ１２ , R Ｍ１３ , and R Ｍ１４ R each independently represents a hydrogen atom or an organic group. Ｍ１５ each independently represents an alkyl group having 1 to 10 carbon atoms, an alkyloxy group having 1 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, an aryloxy group having 6 to 10 carbon atoms, an arylthio group having 6 to 10 carbon atoms, a halogen atom, a hydroxyl group, or a mercapto group. px represents an integer of 0 to 3. nx represents an integer of 1 to 20.)

18. The resin composition according to claim 1 or 2, wherein the resin (D) containing an aromatic ring and two or more polymerizable unsaturated groups contains at least one of a polymer (V) having a structural unit represented by formula (V) and a polyphenylene ether compound containing two or more carbon-carbon unsaturated double bonds. 【Chemistry 7】 (In formula (V), Ar represents an aromatic hydrocarbon linking group. * represents a bonding position.)

19. The resin (D) containing an aromatic ring and two or more polymerizable unsaturated groups contains at least one of a polymer (V) having a structural unit represented by formula (V) and a polyphenylene ether compound containing two or more carbon-carbon unsaturated double bonds represented by formula (OP-1). The resin composition according to claim 1 or 2. 【Chemistry 8】 (In formula (V), Ar represents an aromatic hydrocarbon linking group. * represents a bonding position.) 【Chemistry 9】 In formula (OP-1), X represents an aromatic group, -(Y-O)n ２ - represents a polyphenylene ether structure, 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; n ２ represents an integer from 1 to 100; n ３ represents an integer from 1 to 4.)

20. The resin composition according to claim 1 or 2, further comprising a cyanate ester compound (E).

21. The resin composition according to claim 20, wherein the cured product of the cyanate ester compound (E) has a relative dielectric constant of 2.4 to 3.0 at a frequency of 10 GHz measured according to a cavity resonance perturbation method.

22. The resin composition according to claim 1 or 2, further comprising a compound (F) having one polymerizable unsaturated group in the molecule.

23. The resin composition according to claim 1 or 2, further comprising a filler (G).

24. The resin composition according to claim 23, wherein the content of the filler (G) in the resin composition is 10 to 1600 parts by mass per 100 parts by mass of resin solids.

25. the cured product of the maleimide compound (A) has a relative dielectric constant of 2.1 to 2.5 at a frequency of 10 GHz as measured according to a cavity resonance perturbation method; the cured product of the maleimide compound (B) has a relative dielectric constant of 2.2 to 2.6 at a frequency of 10 GHz as measured according to a cavity resonance perturbation method; a difference between a dielectric constant at a frequency of 10 GHz of the block copolymer (C) having a styrene skeleton, as measured according to a cavity resonance perturbation method, and a dielectric constant at a frequency of 10 GHz of a cured product of the maleimide compound (B), as measured according to a cavity resonance perturbation method, is 0.6 or less; the block copolymer (C) having a styrene skeleton has a relative dielectric constant of 1.9 to 2.2 at a frequency of 10 GHz as measured according to a cavity resonance perturbation method; a difference between a dielectric constant at a frequency of 10 GHz of a cured product of the resin (D) containing an aromatic ring and two or more polymerizable unsaturated groups, as measured according to a cavity resonance perturbation method, and a dielectric constant at a frequency of 10 GHz of a cured product of the maleimide compound (B), as measured according to a cavity resonance perturbation method, is 0.3 or less; a cured product of the resin (D) containing an aromatic ring and two or more polymerizable unsaturated groups has a relative dielectric constant of 2.2 to 2.6 at a frequency of 10 GHz, as measured according to a cavity resonance perturbation method; a dielectric constant at a frequency of 10 GHz of a cured product of the maleimide compound (A), measured according to a cavity resonance perturbation method, a dielectric constant at a frequency of 10 GHz of a cured product of the maleimide compound (B), a dielectric constant at a frequency of 10 GHz of the block copolymer (C) having a styrene skeleton, measured according to a cavity resonance perturbation method, and a dielectric constant at a frequency of 10 GHz of a cured product of the resin (D) containing an aromatic ring and two or more polymerizable unsaturated groups, measured according to a cavity resonance perturbation method, are each independently 2.0 to 2.6, The content of the maleimide compound (A) is 5 to 40 parts by mass based on 100 parts by mass of the resin solid content, The content of the maleimide compound (B) is 5 to 40 parts by mass relative to 100 parts by mass of the resin solid content, the content of the block copolymer (C) having a styrene skeleton is 3 to 40 parts by mass relative to 100 parts by mass of a resin solid content, the content of the resin (D) containing an aromatic ring and two or more polymerizable unsaturated groups is 5 to 50 parts by mass relative to 100 parts by mass of the resin solid content, a mass ratio ((A) / (B)) of the content of the maleimide compound (A) to the content of the maleimide compound (B) is 30 / 70 to 70 to 30; The maleimide compound (A) has two or more divalent linear aliphatic hydrocarbon groups having 8 to 20 carbon atoms in the molecule, The maleimide compound (A) has a weight average molecular weight of 2,000 to 30,000; The maleimide compound (A) contains a compound represented by formula (3), and the maleimide compound (B) contains a compound represented by formula (M1), the resin (D) containing an aromatic ring and two or more polymerizable unsaturated groups contains at least one of a polymer (V) having a structural unit represented by formula (V) and a polyphenylene ether compound containing two or more carbon-carbon unsaturated double bonds represented by formula (OP-1), Further, the composition contains a cyanate ester compound (E), the cured product of the cyanate ester compound (E) has a relative dielectric constant of 2.4 to 3.0 at a frequency of 10 GHz, as measured according to a cavity resonance perturbation method; The resin composition according to claim 1 , further comprising a compound (F) having one polymerizable unsaturated group in the molecule. 【Chemistry 10】 (In formula (3), R １ and R ３ each independently represents a linear aliphatic hydrocarbon group having 8 or more carbon atoms; R ２ represents a hydrocarbon group having an alicyclic structure of 4 to 10 members, and n represents a number from 1 to 10. 【Chemistry 11】 (In formula (M1), R Ｍ１ , R Ｍ２ , R Ｍ３ , and R Ｍ４ R each independently represents a hydrogen atom or an organic group. Ｍ５ and R Ｍ６ Each independently represents a hydrogen atom or an alkyl group. Ｍ represents a divalent aromatic group. A is a 4- to 6-membered alicyclic group. R Ｍ７ and R Ｍ８ are each independently an alkyl group. mx is 1 or 2, and lx is 0 or 1. R Ｍ９ and R Ｍ１０ Each of R independently represents a hydrogen atom or an alkyl group. Ｍ１１ , R Ｍ１２ , R Ｍ１３ , and R Ｍ１４ R each independently represents a hydrogen atom or an organic group. Ｍ１５ each independently represents an alkyl group having 1 to 10 carbon atoms, an alkyloxy group having 1 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, an aryloxy group having 6 to 10 carbon atoms, an arylthio group having 6 to 10 carbon atoms, a halogen atom, a hydroxyl group, or a mercapto group. px represents an integer of 0 to 3. nx represents an integer of 1 to 20.) 【Chemistry 12】 (In formula (V), Ar represents an aromatic hydrocarbon linking group. * represents a bonding position.) 【Chemistry 13】 In formula (OP-1), X represents an aromatic group, -(Y-O)n ２ - represents a polyphenylene ether structure, 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; n ２ represents an integer from 1 to 100; n ３ represents an integer of 1 to 4.)

26. The resin composition according to claim 25, further comprising a filler (G), and the content of the filler (G) in the resin composition is 10 to 1600 parts by mass per 100 parts by mass of resin solids.

27. A cured product of the resin composition according to any one of claims 1, 2, 25 and 26.

28. A prepreg formed from a substrate and the resin composition according to any one of claims 1, 2, 25, and 26.

29. 30. A metal foil clad laminate comprising at least one layer formed from the prepreg of claim 28 and metal foil disposed on one or both sides of the layer formed from the prepreg.

30. A resin composite sheet comprising a support and a layer formed from the resin composition according to any one of claims 1, 2, 25 and 26, which is disposed on a surface of the support.

31. A printed wiring board comprising an insulating layer and a conductor layer disposed on a surface of the insulating layer, the insulating layer comprising a layer formed from a resin composition according to any one of claims 1, 2, 25, and 26.

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

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