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

Abstract

Provided are 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. A resin composition containing: a resin (A) having a terminal group represented by formula (T1) and having an indane skeleton; a polyphenylene ether compound (B) having a carbon-carbon unsaturated double bond at the terminal; and at least one selected from the group consisting of an isocyanurate compound (C1) having two or more (meth) allyl groups, a glycoluril compound (C2) having two or more (meth) allyl groups, and a (meth) acrylate compound (C3) having three or more (meth) acryloyloxy groups.

Description

Technical Field

[0001] This invention relates to resin compositions, cured products, prepregs, metal foil laminates, resin composites, printed circuit boards, and semiconductor devices. Background Technology

[0002] In recent years, the integration and miniaturization of semiconductor components used in electronic and communication devices, exemplified by portable terminals, have been accelerating. This necessitates technologies capable of high-density mounting of semiconductor components, requiring improvements to the printed circuit boards, which occupy a crucial position in these devices.

[0003] On the other hand, the applications of electronic devices and the like are diversifying and continuing to expand. As a result, the required properties of printed circuit boards (PCBs), metal-clad laminates used in PCBs, and prepregs are becoming more diverse and stringent. To improve PCBs while taking these required properties into account, various materials and processing methods have been proposed. Among these, the improved development of resin materials constituting prepregs and resin composite sheets can be cited.

[0004] Patent Document 1 discloses a polyphenylene ether resin composition comprising polyphenylene ether and a crosslinking curing agent, wherein the polyphenylene ether is represented by the following formula (I) and has a number average molecular weight of 1000 to 7000.

[0005]

[0006] [In the formula, X represents aryl, (Y)] m Indicates the polyphenylene ether portion, R 1 ~R 3 Independently representing a hydrogen atom, alkyl, alkenyl, or ynyl group, n represents an integer from 1 to 6, q represents an integer from 1 to 4, and the portion shown in formula (II) below includes both p-vinylbenzyl and m-vinylbenzyl.

[0007]

[0008] Existing technical documents

[0009] Patent documents

[0010] Patent Document 1: Japanese Patent Application Publication No. 2008-260941 Summary of the Invention

[0011] The problem the invention aims to solve

[0012] The frequency bands used are increasingly higher, creating a demand for novel resin compositions that can provide cured products with excellent low dielectric properties (Dk and / or Df). For example, the dielectric loss tangent of the laminate described in Patent Document 1 is as low as about 0.0015, but this was measured at a frequency of 1 MHz; if measured at a frequency of 10 GHz, it would be a considerably high value. Therefore, there is a demand for resin compositions that can provide cured products with low dielectric properties (Dk and / or Df).

[0013] The object of the present invention is to solve the above-mentioned problems, and to provide a resin composition capable of providing a cured product with low dielectric properties (Dk and / or Df), as well as a cured product, prepreg, metal foil laminate, resin composite, printed circuit board, and semiconductor device obtained using the aforementioned resin composition.

[0014] Solution for solving the problem

[0015] Based on the above problems, the inventors conducted research and solved the above problems by compounding a polyphenylene ether compound with a carbon-carbon unsaturated double bond at the end and a specified allyl compound and / or a specified (meth)acrylate compound into a resin having an isopropylene group at the end and an indane skeleton.

[0016] Specifically, the above problems were solved through the following methods.

[0017] <1> A resin composition comprising:

[0018] A resin (A) having terminal groups as shown in formula (T1) and having an indane skeleton;

[0019] Polyphenylene ether compounds (B) with carbon-carbon unsaturated double bonds at the ends; and

[0020] It is selected from at least one of the following groups: isocyanurate compounds having two or more (meth)allyl groups (C1), glycourea compounds having two or more (meth)allyl groups (C2), and (meth)acrylate compounds having three or more (meth)acryloyloxy groups (C3).

[0021]

[0022] (In formula (T1), Ma independently represents a hydrocarbon group with 1 to 12 carbon atoms that are optionally substituted with halogen atoms, and x represents an integer from 0 to 4. * indicates the bonding position with other sites.)

[0023] <2> according to <1> The resin composition wherein the aforementioned resin (A) having terminal groups as shown in formula (T1) and having an indane skeleton comprises the resin shown in formula (T1-1).

[0024]

[0025] (In formula (T1-1), R is a group containing the structural unit shown in formula (Tx). Ma independently represents a hydrocarbon group with 1 to 12 carbon atoms that are optionally substituted with halogen atoms. x is an integer from 0 to 4).

[0026]

[0027] (In formula (Tx), n, o, and p are the average number of repeating units, where n represents a number greater than 0 and less than 20, o and p each independently represent a number from 0 to 20, and 1.0 ≤ n + o + p ≤ 20.0. Ma each independently represents a hydrocarbon group with 1 to 12 carbon atoms that are optionally substituted by a halogen atom. x represents an integer from 0 to 4. Structural units (a), (b), and (c) are bonded to structural units (a), (b), (c), or other groups at *, and each structural unit is optionally bonded randomly.)

[0028] <3> according to <1> or <2> The resin composition wherein the polyphenylene ether compound (B) having carbon-carbon unsaturated double bonds at the ends comprises the polyphenylene ether compound represented by formula (OP).

[0029]

[0030] (In formula (OP), X represents an aromatic group, -(YO) n1 - indicates a polyphenylene ether structure, n1 represents an integer from 1 to 100, and n2 represents an integer from 1 to 4. Rx is the group shown in formula (Rx-1) or formula (Rx-2).

[0031]

[0032] In equations (Rx-1) and (Rx-2), R 1 R 2 and R 3 Each group independently represents a hydrogen atom, alkyl, alkenyl, or alkynyl group. * indicates the bonding site with an oxygen atom. Mc independently represents a hydrocarbon group having 1 to 12 carbon atoms. z represents an integer from 0 to 4. r represents an integer from 0 to 6.

[0033] <4> according to <1> ~ <3> The resin composition according to any one of the above-mentioned resins (A) having the terminal groups shown in formula (T1) and having an indane skeleton, comprises, relative to 100 parts by weight of: 10 to 900 parts by weight of the above-mentioned polyphenylene ether compound (B) having carbon-carbon unsaturated double bonds at the ends, and a total of 10 to 900 parts by weight of the above-mentioned compound selected from the group consisting of isocyanurate compound (C1) having two or more (meth)allyl groups, glycourea compound (C2) having two or more (meth)allyl groups, and (meth)acrylate compound (C3) having three or more (meth)acryloyloxy groups.

[0034] <5> according to <1> ~ <4> The resin composition according to any one of the following, wherein the polyphenylene ether compound (B) having carbon-carbon unsaturated double bonds at the ends has a number average molecular weight (Mn) of 500 to 3000 and a weight average molecular weight (Mw) of 800 to 6000.

[0035] <6> according to <1> ~ <5> The resin composition according to any one of the following, wherein the number average molecular weight (Mn) of the resin (A) having the terminal group shown in formula (T1) and having an indane backbone is 400 to 3000.

[0036] <7> according to <1> ~ <6> The resin composition according to any one of the following, wherein the isocyanurate compound (C1) having two or more (meth)allyl groups is represented by formula (TA), the glycourea compound (C2) having two or more (meth)allyl groups is represented by formula (GU-O), and the (meth)acrylate compound (C3) having three or more (meth)acryloyloxy groups is represented by formula (MA).

[0037] Formula (TA)

[0038]

[0039] (In formula (TA), R A (Indicates substituent)

[0040] Formula(GU-0)

[0041]

[0042] (In formula (GU-0), R) 1 Each is independently a hydrogen atom or a substituent, R 1 At least two of them are groups containing (methyl)allyl groups.

[0043] Formula (MA)

[0044]

[0045] (In formula (MA), R) 1 R represents a hydrogen atom or substituent. 2 Each can independently represent a hydrogen atom or a methyl group.

[0046] <8> according to <1> ~ <7> The resin composition according to any one of the following, wherein the isocyanurate compound (C1) having two or more (meth)allyl groups is represented by formula (TA), the glycourea compound (C2) having two or more (meth)allyl groups is represented by formula (GU), and the (meth)acrylate compound (C3) having three or more (meth)acryloyloxy groups is represented by formula (MA).

[0047] Formula (TA)

[0048]

[0049] (In formula (TA), R A (Indicates substituent)

[0050] Formula(GU)

[0051]

[0052] (In formula (GU), each R is an independent hydrogen atom or substituent, and at least two of R are groups containing (methyl)allyl groups.)

[0053] Formula (MA)

[0054]

[0055] (In formula (MA), R) 1 R represents a hydrogen atom or substituent. 2 Each can independently represent a hydrogen atom or a methyl group.

[0056] <9> according to <1> ~ <8> In any one of the resin compositions, the isocyanurate compound (C1) having two or more (meth)allyl groups has a molecular weight of 200 to 3000, the glycourea compound (C2) having two or more (meth)allyl groups has a molecular weight of 195 to 1500, and the methacrylate compound (C3) having three or more (meth)acryloyloxy groups has a molecular weight of 300 to 3000.

[0057] <10> according to <1> ~ <9> The resin composition described in any one of the following statements further comprises other components (D), said other components (D) being selected from maleimide compounds, polymers having structural units shown in formula (V), epoxy resins, phenolic compounds, oxetane resins, benzoxazine compounds, cyanate ester compounds, arylcyclobutene resins, polyamide resins, polyimide resins, perfluorovinyl ether resins, styrene-based compounds other than the aforementioned polyphenylene ether compounds (B) with carbon-carbon unsaturated double bonds at the ends, isopropylene-based compounds other than the aforementioned resins (A) with indane skeletons, and other resins not described above. Compounds having carbon-carbon unsaturated double bonds at the end and having an indane skeleton other than (A), polyfunctional (meth)allyl compounds other than the aforementioned isocyanurate compounds having two or more (meth)allyl groups (C1) and the aforementioned glycourea compounds having two or more (meth)allyl groups (C2), polyfunctional (meth)acrylate compounds other than the aforementioned polyphenylene ether compounds having carbon-carbon unsaturated double bonds at the end (B) and the aforementioned (meth)acrylate compounds having three or more (meth)acryloyloxy groups (C3), elastomers, and petroleum resins are one or more of the following.

[0058]

[0059] (In formula (V), Ar represents an aromatic hydrocarbon linking group. * indicates a bonding position.)

[0060] <11> according to <1> ~ <10> The resin composition described in any one of the following statements further comprises filler (E).

[0061] <12> according to <11> The resin composition wherein the filler (E) comprises one or more selected from the group consisting of silica, aluminum hydroxide, aluminum nitride, boron nitride, magnesium olivine, titanium oxide, barium titanate, strontium titanate and calcium titanate.

[0062] <13> according to <11> or <12> The resin composition wherein, relative to 100 parts by mass of the resin solids in the resin composition, the content of the filler (E) in the resin composition is 1 to 1600 parts by mass.

[0063] <14> according to <1> ~ <13> The resin composition according to any one of the following methods, wherein, relative to 100 parts by weight of the resin solids in the resin composition, it further comprises 0.5 to 30 parts by weight of a monomer or oligomer having an olefinic unsaturated group.

[0064] <15> according to <1> ~ <14> The resin composition described in any one of the above statements further comprises a flame retardant, wherein the flame retardant comprises a phosphorus-based flame retardant.

[0065] <16> according to <1> ~ <15> In any one of the resin compositions, the mass ratio {(B) / [(C1)+(C2)+(C3)]} of the polyphenylene ether compound (B) having carbon-carbon unsaturated double bonds at the end is 1.0 to 9.0 relative to the total mass of the compounds selected from the group consisting of isocyanurate compounds (C1) having two or more (meth)allyl groups, glycourea compounds (C2) having two or more (meth)allyl groups, and (meth)acrylate compounds (C3) having three or more (meth)acryloyloxy groups.

[0066] <17> according to <1> ~ <16> The resin composition described in any one of the above descriptions, wherein the resin (A) having the terminal groups shown in formula (T1) and having an indane backbone comprises the resin shown in formula (T1-1).

[0067] The aforementioned polyphenylene ether compound (B) with a carbon-carbon unsaturated double bond at its end includes the polyphenylene ether compound represented by formula (OP).

[0068] Relative to 100 parts by mass of the resin (A) having the terminal group shown in formula (T1) and having an indane backbone, the resin comprises 10 to 900 parts by mass of the aforementioned polyphenylene ether compound (B) having a carbon-carbon unsaturated double bond at the end, and a total of 10 to 900 parts by mass of the aforementioned compound selected from the group consisting of isocyanurate compound (C1) having two or more (meth)allyl groups, glycourea compound (C2) having two or more (meth)allyl groups, and (meth)acrylate compound (C3) having three or more (meth)acryloyloxy groups.

[0069] The polyphenylene ether compound (B) with terminal carbon-carbon unsaturated double bonds has a number-average molecular weight (Mn) of 500–3000 and a weight-average molecular weight (Mw) of 800–6000.

[0070] The number-average molecular weight (Mn) of the resin (A) having the terminal group shown in formula (T1) and having an indane backbone is 400 to 3000.

[0071] The isocyanurate compound (C1) having two or more (meth)allyl groups is represented by formula (TA), the glycourea compound (C2) having two or more (meth)allyl groups is represented by formula (GU-O), and the (meth)acrylate compound (C3) having three or more (meth)acryloyloxy groups is represented by formula (MA).

[0072] The isocyanurate compound (C1) having two or more (meth)allyl groups has a molecular weight of 200-3000; the glycourea compound (C2) having two or more (meth)allyl groups has a molecular weight of 195-1500; and the methacrylate compound (C3) having three or more (meth)acryloyloxy groups has a molecular weight of 300-3000.

[0073] The resin composition also includes other components (D), which are selected from maleimide compounds, polymers having structural units shown in formula (V), epoxy resins, phenolic compounds, oxacyclobutane resins, benzoxazine compounds, cyanate ester compounds, arylcyclobutene resins, polyamide resins, polyimide resins, perfluorovinyl ether resins, styrene compounds other than the aforementioned polyphenylene ether compounds (B) with carbon-carbon unsaturated double bonds at the ends, isopropylene compounds other than the aforementioned resins (A) with indane skeletons, and other compounds other than the resins (A) with... The following are compounds having carbon-carbon unsaturated double bonds at the ends and having an indane skeleton: polyfunctional (meth)allyl compounds other than the isocyanurate compounds (C1) having two or more (meth)allyl groups and the glycourea compounds (C2) having two or more (meth)allyl groups; polyfunctional (meth)acrylate compounds other than the polyphenylene ether compounds (B) having carbon-carbon unsaturated double bonds at the ends and the (meth)acrylate compounds (C3) having three or more (meth)acryloyloxy groups; elastomers; and petroleum resins, comprising one or more of the following:

[0074] The mass ratio of the polyphenylene ether compound (B) having a carbon-carbon unsaturated double bond at the end to the total mass of the compounds selected from the group consisting of isocyanurate compounds (C1) having two or more (meth)allyl groups, glycourea compounds (C2) having two or more (meth)allyl groups, and (meth)acrylate compounds (C3) having three or more (meth)acryloyloxy groups {(B) / [(C1)+(C2)+(C3)]} is 1.0 to 9.0.

[0075]

[0076] (In formula (T1-1), R is a group containing the structural unit shown in formula (Tx). Ma independently represents a hydrocarbon group with 1 to 12 carbon atoms that are optionally substituted with halogen atoms. x is an integer from 0 to 4.)

[0077]

[0078] (In formula (Tx), n, o, and p are the average number of repeating units, where n represents a number greater than 0 and less than 20, o and p each independently represent a number from 0 to 20, and 1.0 ≤ n + o + p ≤ 20.0. Ma each independently represents a hydrocarbon group with 1 to 12 carbon atoms that are optionally substituted by a halogen atom. x represents an integer from 0 to 4. Structural units (a), (b), and (c) are bonded to structural units (a), (b), and (c) or other groups at *, and each structural unit is optionally bonded randomly.)

[0079]

[0080] (In formula (OP), X represents an aromatic group, -(YO) n1 - indicates a polyphenylene ether structure, n1 represents an integer from 1 to 100, and n2 represents an integer from 1 to 4. Rx is the group shown in formula (Rx-1) or formula (Rx-2).

[0081]

[0082] In equations (Rx-1) and (Rx-2), R 1 R 2 and R 3 Each group independently represents a hydrogen atom, alkyl, alkenyl, or alkynyl group. * indicates the bonding site with an oxygen atom. Mc independently represents a hydrocarbon group having 1 to 12 carbon atoms. z represents an integer from 0 to 4. r represents an integer from 0 to 6.

[0083] Formula (TA)

[0084]

[0085] (In formula (TA), R A (Indicates substituent)

[0086] Formula(GU-0)

[0087]

[0088] (In formula (GU-0), R) 1 Each is independently a hydrogen atom or a substituent, R 1 At least two of them are groups containing (methyl)allyl groups.

[0089] Formula (MA)

[0090]

[0091] (In formula (MA), R) 1 R represents a hydrogen atom or substituent. 2 Each can independently represent a hydrogen atom or a methyl group.

[0092]

[0093] (In formula (V), Ar represents an aromatic hydrocarbon linking group. * indicates a bonding position.)

[0094] <18> according to <17> The resin composition wherein the above-mentioned glycourea compound (C2) having two or more (methyl)allyl groups is represented by formula (GU).

[0095] Formula(GU)

[0096]

[0097] (In formula (GU), each R is an independent hydrogen atom or substituent, and at least two of R are groups containing (methyl)allyl groups.)

[0098] <19> according to <17> or <18> The resin composition wherein the aforementioned other component (D) is selected from maleimide compounds, polymers having structural units shown in formula (V), epoxy resins, phenolic compounds, oxacyclobutane resins, benzoxazine compounds, cyanate ester compounds, arylcyclobutene resins, polyamide resins, polyimide resins, perfluorovinyl ether resins, styrene-based compounds other than the aforementioned polyphenylene ether compound (B) with a carbon-carbon unsaturated double bond at the end, and isopropylene compounds other than the aforementioned resin (A) with an indane backbone. The compound is composed of one or more of the following: a compound with a base group, a polyfunctional (meth)allyl compound other than the aforementioned isocyanurate compound having two or more (meth)allyl groups (C1) and the aforementioned glycourea compound having two or more (meth)allyl groups (C2), a polyfunctional (meth)acrylate compound other than the aforementioned polyphenylene ether compound having a carbon-carbon unsaturated double bond at the end (B) and the aforementioned (meth)acrylate compound having three or more (meth)acryloyloxy groups (C3), an elastomer, and a petroleum resin.

[0099]

[0100] (In formula (V), Ar represents an aromatic hydrocarbon linking group. * indicates a bonding position.)

[0101] <20> according to <17> ~ <19> The resin composition according to any one of the following methods, wherein in formula (Rx-1), r represents an integer from 1 to 6.

[0102] <21> according to <1> ~ <20> The resin composition described in any one of the above statements is used in a printed circuit board.

[0103] <22> A solidified substance, which is <1> ~ <21> The cured product of the resin composition described in any one of the above statements.

[0104] <23> A prepreg comprising a substrate and <1> ~ <21> The resin composition described in any one of the above statements is formed.

[0105] <24> A metal foil-coated laminate comprising: at least one sheet <23> The prepreg shown, and the metal foil disposed on one or both sides of the prepreg.

[0106] <25> A resin composite sheet comprising: a support; and a substrate disposed on the surface of the support. <1> ~ <21> The layer formed by the resin composition described in any one of the above statements.

[0107] <26> A printed circuit board includes: an insulating layer and a conductor layer disposed on the surface of the insulating layer, the insulating layer comprising: <1> ~ <21> The layer formed by the resin composition described in any one of the above statements.

[0108] <27> A semiconductor device comprising <26> The printed circuit board mentioned above.

[0109] The effects of the invention

[0110] According to the present invention, it is possible to provide: resin compositions that can provide cured products with low dielectric properties (Dk and / or Df), and cured products, prepregs, metal foil laminates, resin composites, printed circuit boards, and semiconductor devices obtained using the above-described resin compositions. Attached Figure Description

[0111] Figure 1 The resin obtained in Synthesis Example 1 is shown. 1 H-NMR spectrum.

[0112] Figure 2 The resin obtained in Synthesis Example 1 1 The H-NMR plot shows the peak values ​​of parameters α and β. Detailed Implementation

[0113] The following describes in detail a method for implementing the present invention (hereinafter referred to as "this embodiment"). It should be noted that the following embodiment is an example for illustrating the present invention, and the present invention is not limited to this embodiment.

[0114] In addition, in this specification, “~” is used to include the values ​​described before and after it as the lower limit and upper limit values.

[0115] Unless otherwise specified, all physical property values ​​and characteristic values ​​in this specification are values ​​at 23°C.

[0116] In this specification, the descriptions of groups (atomic groups) including "unsubstituted" and "unsubstituted" include not only groups (atomic groups) without substituents but also groups (atomic groups) with substituents. For example, "alkyl" includes not only unsubstituted alkyl groups (unsubstituted alkyl groups) but also substituted alkyl groups (substituted alkyl groups). In this specification, the descriptions of "unsubstituted" and "unsubstituted" are preferably unsubstituted.

[0117] In this specification, (meth)allyl means either or both of allyl and methallyl, "(meth)acrylate" means either or both of acrylate and methacrylate, "(meth)acrylic acid" means either or both of acrylic acid and methacrylic acid, and "(meth)acryloyl" means either or both of acryloyl and methacryloyl.

[0118] In this specification, "compound" includes not only low molecular weight compounds, but also oligomers and polymers.

[0119] Unless otherwise specified, the measurement methods described in the standards shown in this instruction manual may vary from year to year, and are based on the standards as of January 1, 2023.

[0120] In this specification, the resin solids component refers to the components other than fillers and solvents. This means that, in addition to comprising at least one of the following: resin (A), polyphenylene ether compound (B), and isocyanurate compound (C1) selected from two or more (meth)allyl groups, glycourea compound (C2) selected from three or more (meth)acryloyloxy groups, and meth)acrylate compound (C3), it also includes other resin components (D) and other resin additive components (flame retardants and other additives, etc.) that need to be blended as needed.

[0121] The resin composition of this embodiment is characterized in that it comprises: a resin (A) having a terminal group shown in formula (T1) and having an indane skeleton (hereinafter sometimes simply referred to as "resin (A)"); a polyphenylene ether compound (B) having a carbon-carbon unsaturated double bond at the end; and at least one of the following: an isocyanurate compound (C1) having two or more (meth)allyl groups, a glycourea compound (C2) having two or more (meth)allyl groups, and a (meth)acrylate compound (C3) having three or more (meth)acryloyloxy groups.

[0122]

[0123] (In formula (T1), Ma independently represents a hydrocarbon group with 1 to 12 carbon atoms that are optionally substituted with halogen atoms, and x represents an integer from 0 to 4. * indicates the bonding position with other sites.)

[0124] By configuring it in this way, a resin composition that provides a cured product with excellent low dielectric properties (Dk and / or Df) can be obtained. Furthermore, a resin composition that provides a cured product with excellent heat resistance can be obtained.

[0125] Resin (A) having terminal groups as shown in formula (T1) and an indane backbone is difficult to polymerize alone. Furthermore, if not used in combination with a compound compatible with resin (A), phase separation is likely to occur. In this embodiment, it is contemplated that by mixing resin (A) with a polyphenylene ether compound (B) having carbon-carbon unsaturated double bonds at the ends, and at least one compound selected from the group consisting of an isocyanurate compound (C1) having two or more (meth)allyl groups, a glycidyl urea compound (C2) having two or more (meth)allyl groups, and a (meth)acrylate compound (C3) having three or more (meth)acryloyloxy groups, a resin composition with improved compatibility and excellent formability can be obtained. Furthermore, it is contemplated that because resin (A) has an indane backbone, a resin composition with low dielectric properties (Dk and / or Df) and excellent heat resistance when the cured product is obtained.

[0126] <Resin (A) having terminal groups as shown in formula (T1) and having an indane backbone>

[0127]

[0128] (In formula (T1), Ma independently represents a hydrocarbon group with 1 to 12 carbon atoms that are optionally substituted with halogen atoms, and x represents an integer from 0 to 4. * indicates the bonding position with other sites.)

[0129] In formula (T1), each Ma is preferably a hydrocarbon group with 1 to 10 carbon atoms that is optionally substituted with a halogen atom, more preferably a hydrocarbon group with 1 to 5 carbon atoms that is optionally substituted with a halogen atom, and even more preferably a hydrocarbon group with 1 to 3 carbon atoms that is optionally substituted with a halogen atom. Examples of halogen atoms include fluorine atoms, chlorine atoms, and bromine atoms, with fluorine atoms or chlorine atoms being preferred.

[0130] The aforementioned hydrocarbon group is preferably an alkyl group, more preferably a straight-chain alkyl group. Methyl or ethyl groups are preferred as Ma.

[0131] x is preferably an integer from 0 to 3, more preferably an integer from 0 to 2, further preferably 0 or 1, and even more preferably 0.

[0132] Regarding resin (A), each resin molecule may have terminal groups as shown in formula (T1) at all ends, or it may have terminal groups as shown in formula (T1) at only a portion of the ends.

[0133] The number of terminal groups represented by formula (T1) in the resin molecule of resin (A) is preferably 2 per molecule.

[0134] Resin (A) has an indane backbone. There is no particular limitation as long as at least one molecule of resin in resin (A) has at least one indane backbone, but the number of indane backbones per molecule of resin (A) is preferably 1 to 20. This configuration tends to more effectively utilize the benefits of the present invention.

[0135] The resin (A) preferably contains the structural unit shown in the following formula (Txn).

[0136]

[0137] (In formula (Txn), n is the average number of repeating units, representing a number greater than 0 and less than 20. Ma independently represents hydrocarbon groups with 1 to 12 carbon atoms arbitrarily substituted by halogen atoms, and x represents an integer from 0 to 4.)

[0138] In equation (Txn), Ma and x have the same meaning as Ma and x in equation (T1), and the preferred range is also the same.

[0139] The proportion of the structural unit represented by formula (Txn) in 100 parts by weight of resin (A) is preferably 20 parts by weight or more, more preferably 25 parts by weight or more, even more preferably 34 parts by weight or more, even more preferably 45 parts by weight or more, even more preferably 50 parts by weight or more, even more preferably 55 parts by weight or more, even more preferably 60 parts by weight or more, 65 parts by weight or more, or possibly 70 parts by weight or more, 75 parts by weight or more. In addition, it is preferably 100 parts by weight or less, or possibly 95 parts by weight or less, 90 parts by weight or less, 85 parts by weight or less, 82 parts by weight or less, or 80 parts by weight or less.

[0140] Resin (A) is more preferably the resin represented by formula (T1-1).

[0141]

[0142] (In formula (T1-1), R is a group containing the structural unit shown in formula (Tx). Ma independently represents a hydrocarbon group with 1 to 12 carbon atoms that are optionally substituted with halogen atoms. x is an integer from 0 to 4.)

[0143]

[0144] (In formula (Tx), n, o, and p are the average number of repeating units, where n represents a number greater than 0 and less than 20, o and p each independently represent a number from 0 to 20, and 1.0 ≤ n + o + p ≤ 20.0. Ma each independently represents a hydrocarbon group with 1 to 12 carbon atoms that are optionally substituted by a halogen atom. x represents an integer from 0 to 4. Structural units (a), (b), and (c) are bonded to structural units (a), (b), and (c) or other groups at *, and each structural unit is optionally bonded randomly.)

[0145] In formula (Tx), n, o, and p refer to the average number of repeating units in all molecules of the resin.

[0146] In formula (Tx), the sum of n, o, and p is preferably 1.1 ≤ n + o + p, more preferably 1.2 ≤ n + o + p, even more preferably 1.5 ≤ n + o + p, even more preferably 2.0 ≤ n + o + p, even more preferably 2.5 ≤ n + o + p, even more preferably 3.0 ≤ n + o + p, and even more preferably 3.3 ≤ n + o + p. In formula (Tx), the sum of n, o, and p is also preferably n + o + p ≤ 20.0, more preferably n + o + p ≤ 10.0, even more preferably n + o + p ≤ 8.0, even more preferably n + o + p ≤ 7.0, even more preferably n + o + p ≤ 6.4, and can also be n + o + p ≤ 4.0. The sum of n, o, and p can be calculated using the method described in the embodiments described later.

[0147] In formula (Tx), n is preferably 0.2 or more, more preferably 0.6 or more, even more preferably 1.0 or more, even more preferably 1.2 or more, even more preferably 1.6 or more, and can further be 2.2 or more or 2.4 or more. In addition, it is preferably 18.0 or less, more preferably 12.0 or less, even more preferably 9.0 or less, even more preferably 7.0 or less, even more preferably 6 or less, and can also be 5.0 or less, 4.0 or less, or 3.0 or less.

[0148] In formula (Tx), o is preferably 0 or more, more preferably 0.01 or more, even more preferably 0.03 or more, even more preferably 0.05 or more, even more preferably 0.07 or more, and preferably 10.0 or less, more preferably 5.0 or less, even more preferably 4.0 or less, even more preferably 2.0 or less, even more preferably 1.0 or less, and may also be 0.8 or less, 0.5 or less, 0.3 or less, 0.2 or less, or 0.1 or less.

[0149] In formula (Tx), p is preferably 0 or more, more preferably 0.01 or more, even more preferably 0.1 or more, even more preferably 0.2 or more, even more preferably 0.3 or more, and preferably 18.0 or less, more preferably 10.0 or less, even more preferably 5.0 or less, even more preferably 4.0 or less, even more preferably 3.0 or less, and may also be 2.5 or less, 2.0 or less, 1.0 or less, or 0.5 or less.

[0150] Furthermore, in equation (Tx), n / (n+o+p) is, for example, 0.2 or more, 0.25 or more, 0.3 or more, 0.34 or more, 0.4 or more, 0.45 or more, 0.5 or more, 0.55 or more, 0.6 or more, or 0.7 or more, and is less than 1.0. Among the structural units (a) to (c) included in equation (Tx), structural unit (a) with the lowest activation energy and the largest change in free energy is preferentially generated.

[0151] In formula (T1-1), the proportion of the structural unit represented by formula (Tx) (i.e., any one of structural units (a), (b), and (c)) in R 100 parts by mass is preferably 80 parts by mass, more preferably 90 parts by mass or more, even more preferably 95 parts by mass or more, even more preferably 97 parts by mass or more, even more preferably 99 parts by mass or more, and is 100 parts by mass or less.

[0152] In equations (T1-1) and (Tx), Ma and x have the same meaning as Ma and x in equation (T1), and the preferred range is also the same.

[0153] The resin represented by formula (T1-1) is further preferably in which the parameter α calculated by formula (α) is 0.55 or more and 1.00 or less, and the parameter β calculated by formula (β) is 0.20 or more and 3.00 or less. By setting the parameters α and β to the above ranges, the resulting cured product tends to have low dielectric properties (Dk and / or Df) and excellent heat resistance.

[0154]

[0155] (The parentheses in equations (α) and (β) indicate) 1 (The integral value between the corresponding chemical shift values ​​in H-NMR.)

[0156] Here, α represents the ratio of structural units with an indane framework (structural unit (a) in formula (Tx)) in the resin shown in formula (T1-1). More specifically, it is speculated that by adjusting the structural units with an indane framework to satisfy the range of the above parameter α, the resulting resin molecules have high rigidity, which can increase the glass transition temperature. Furthermore, it is speculated that since molecules with high rigidity have lower mobility compared to molecules with low rigidity, the dielectric relaxation time is longer, which can reduce Df. In the synthesis of the resin represented by formula (T1-1), α can be increased by reducing the concentration of raw materials, using highly polar solvents, increasing the amount of catalyst, and increasing the reaction temperature.

[0157] On the other hand, β specifies the ratio of terminal double bonds in the resin represented by formula (T1-1). More specifically, it is speculated that the functional groups of at least one of the following groups (C1, C2, C3, C4, C5, C6, C7, C8, C9, C9, C9) have more crosslinking points, making it easier to form a network during thermosetting, resulting in a cured product with a high glass transition temperature and low Df. β can be increased when synthesizing the resin represented by formula (T1-1) by reducing the amount of catalyst, lowering the reaction temperature, and using a low-polarity solvent.

[0158] More specifically, for the resin of Synthetic Example 1 described later, the above-mentioned 2.55ppm to 2.31ppm corresponds to the peak originating from structural unit (a), the above-mentioned 6.24ppm to 5.91ppm corresponds to the peak originating from structural unit (b), the above-mentioned 2.98ppm to 2.55ppm corresponds to the peak originating from structural unit (c), the above-mentioned 5.49ppm to 4.89ppm corresponds to the peak originating from isopropylene group and structural unit (c), the above-mentioned 4.89ppm to 4.45ppm corresponds to the peak originating from structural unit (c), and the above-mentioned 2.31ppm to 1.96ppm corresponds to the peak originating from isopropylene group and structural unit (a).

[0159] More specifically, the H used in the calculation of parameters α and β is described in the following structural formula.

[0160]

[0161] The above calculations of parameters α and β are used 1 H-NMR peaks can be assigned using the H values ​​described above, as follows.

[0162] • 2.55ppm~2.31ppm: H a1

[0163] • 6.24ppm~5.91ppm: H b1

[0164] • 2.98ppm~2.55ppm: H c1

[0165] • 5.49ppm~4.89ppm: H i2 H i3 and H c2

[0166] • 4.89ppm~4.45ppm: H c3

[0167] • 2.31ppm~1.96ppm: H a2 and H i1

[0168] Based on the above, the formulas for parameters α and β are expressed in terms of the amounts of each hydrogen atom shown below.

[0169] That is, H a1 The more elements there are, that is, the more five-element rings there are in the structural unit (a), the larger the parameter α will be.

[0170] Additionally, parameter β can be used to remove the H in the isopropenyl group. i1 The quantity is used as the denominator, and H is used as the denominator. i2 and H i3 The total amount is expressed as 1.5 times as the numerator in the calculation formula. That is, ideally (H) i2 and H i3 (1.5 times the total amount) ÷ (H) i1 The total amount is 1.

[0171] in addition, Figure 2 The resin obtained in Synthesis Example 1 described later is shown in the figure. 1 Peak values ​​of parameters α and β in the H-NMR image.

[0172] When synthesizing the resin represented by formula (T1-1), the parameters α and β of the resin represented by formula (T1-1) can be adjusted using the methods described above for increasing parameters α and β. Of course, parameters α and β can also be adjusted using methods other than those described above.

[0173] The parameter α is preferably 0.20 or higher, more preferably 0.25 or higher, even more preferably 0.34 or higher, even more preferably 0.45 or higher, even more preferably 0.50 or higher, even more preferably 0.55 or higher, even more preferably 0.57 or higher, even more preferably 0.59 or higher, 0.60 or higher, or 0.62 or higher. Depending on the application, it can be 0.65 or higher, 0.70 or higher, 0.75 or higher, or 0.80 or higher. By setting the parameter α to the lower limit value or higher, there is a tendency to further improve the heat resistance of the obtained cured product. Regarding the parameter α, there is a tendency for the obtained cured product to have low dielectric properties (Dk and / or Df) and excellent heat resistance, so the larger the parameter α, the better. However, depending on the application, it can be 0.95 or lower, 0.90 or lower, 0.85 or lower, 0.82 or lower, 0.80 or lower, 0.77 or lower, 0.75 or lower, 0.74 or lower, 0.70 or lower, or 0.65 or lower.

[0174] The parameter β is preferably 0.25 or higher, more preferably 0.30 or higher, even more preferably 0.35 or higher, even more preferably 0.40 or higher, even more preferably 0.43 or higher, even more preferably 0.50 or higher, and may also be 0.60 or higher, 0.65 or higher, 0.70 or higher, 0.77 or higher, 0.80 or higher, 0.90 or higher, or 0.95 or higher. By setting the parameter β to the lower limit value or higher, there is a tendency for the heat resistance of the obtained cured product to increase and the Df value to decrease. The parameter β is preferably 2.50 or lower, more preferably 2.00 or lower, even more preferably 1.50 or lower, even more preferably 1.30 or lower, even more preferably 1.20 or lower, even more preferably 1.10 or lower, and may further be 1.00 or lower, 0.95 or lower, 0.90 or lower, 0.85 or lower, 0.83 or lower, or 0.80 or lower. By setting the parameter β to the upper limit value or lower, there is a tendency for the heat resistance of the obtained cured product to increase and the Df value to decrease.

[0175] The number-average molecular weight (Mn) of resin (A) converted from polystyrene using GPC (gel permeation chromatography) (details according to the method described in the examples below) is preferably 400 or more, more preferably 500 or more, further preferably 550 or more, even more preferably 600 or more, and even more preferably 650 or more. By setting the number-average molecular weight to the above-mentioned lower limit or above, there is a tendency for the heat resistance of the obtained cured product to be improved and the dielectric constant (Df) to be lower. In addition, the upper limit of the number-average molecular weight (Mn) of resin (A) converted from polystyrene using GPC (gel permeation chromatography) is preferably 3000 or less, more preferably 2500 or less, further preferably 2000 or less, even more preferably 1500 or less, and even more preferably 1250 or less. Depending on the application, it can be 1000 or less or 800 or less. By setting the number-average molecular weight to the above-mentioned upper limit or below, there is a tendency for the heat resistance of the obtained cured product to be improved and the relative dielectric constant (Dk) and dielectric loss tangent (Df) to be lower.

[0176] Furthermore, the weight-average molecular weight (Mw) of resin (A) based on GPC-converted polystyrene (details according to the method described in the examples below) is preferably 500 or more, more preferably 800 or more, further preferably 900 or more, and even more preferably 1000 or more. By setting the weight-average molecular weight to the lower limit or above, there is a tendency for the heat resistance of the obtained cured product to increase and Df to decrease. The upper limit of the weight-average molecular weight (Mw) of resin (A) based on GPC-converted polystyrene (details according to the method described in the examples below) is preferably 6000 or less, more preferably 5000 or less, further preferably 4000 or less, even more preferably 3000 or less, and even more preferably 2800 or less. Depending on the application, it can be 2500 or less, 2000 or less, or 1500 or less. By setting the weight-average molecular weight to the upper limit or below, there is a tendency for the heat resistance of the obtained cured product to increase and the relative permittivity (Dk) and dielectric loss tangent (Df) to decrease.

[0177] The weight-average molecular weight to number-average molecular weight ratio (Mw / Mn) of resin (A) is preferably 1.1 to 3.0. More preferably, the Mw / Mn ratio of resin (A) is 1.2 or higher, even more preferably 1.3 or higher, even more preferably 1.4 or higher, even more preferably 1.5 or higher, and even more preferably 1.6 or higher. Furthermore, the Mw / Mn ratio of resin (A) is more preferably 2.5 or lower, even more preferably 2.4 or lower, and can be 2.3 or lower, 2.0 or lower, or 1.8 or lower.

[0178] The weight-average molecular weight and number-average molecular weight were determined according to the methods described in the examples below.

[0179] In this embodiment, the functional group equivalent (isopropenyl equivalent) of resin (A) is preferably 100 g / eq. or more, more preferably 150 g / eq. or more, even more preferably 200 g / eq. or more, even more preferably 250 g / eq. or more, even more preferably 275 g / eq. or more, even more preferably 300 g / eq. or more, and preferably 7500 eq. or less, more preferably 5000 eq. or less, even more preferably 4000 eq. or less, even more preferably 3000 g / eq. or less, even more preferably 2000 g / eq. or less, even more preferably 1500 g / eq. or less, even more preferably 1000 g / eq. or less, and can further be 800 g / eq. or less, 750 g / eq. or less, 700 g / eq. or less, or 500 g / eq. or less. By setting the functional group equivalent of resin (A) to or above the aforementioned lower limit, the resulting cured product tends to have superior low dielectric properties (Dk and / or Df, especially Df) and superior peel strength. Furthermore, by setting the functional group equivalent of resin (A) to or below the aforementioned upper limit, the resulting cured product tends to have superior low dielectric properties (Dk and / or Df, especially Df) and superior heat resistance (especially glass transition temperature). The functional group equivalent (isopropylene group equivalent) of resin (A) is determined according to the method described in the examples described later.

[0180] Relative to 100 parts by mass of the resin solids in the resin composition, the content of resin (A) in the resin composition of this embodiment is preferably 5 parts by mass or more, more preferably 8 parts by mass or more, and can be 10 parts by mass or more. Depending on the application, it can be 15 parts by mass or more, 20 parts by mass or more, or 25 parts by mass or more. By setting the content of resin (A) to the above-mentioned lower limit or above, there is a tendency to reduce the Df of the obtained cured product. In addition, relative to 100 parts by mass of the resin solids in the resin composition, the upper limit of the content of resin (A) is preferably 70 parts by mass or less, more preferably 55 parts by mass or less, even more preferably 50 parts by mass or less, even more preferably 45 parts by mass or less, even more preferably 40 parts by mass or less, and particularly preferably 35 parts by mass or less. By setting the content of resin (A) to the above-mentioned upper limit or less, there is a tendency to improve the formability of the resin composition and the heat resistance of the obtained cured product.

[0181] The resin composition of this embodiment may contain only one type of resin (A) or two or more types. When two or more types are contained, the total amount is preferably within the range described above.

[0182] The method for manufacturing resin (A) in this embodiment is not particularly limited, and resins obtained by known manufacturing methods can be used. Furthermore, the raw materials, reaction temperature, type of catalyst, amount of catalyst, reaction solvent, and concentration of raw materials used in the synthesis of resin (A) are not particularly limited, and can be appropriately selected or controlled according to the desired physical properties described above.

[0183] In this embodiment, as an example of a raw material for synthesizing resin (A), compounds represented by formula (DIP-S) can be cited, preferably m-bis(α-hydroxyisopropyl)benzene, p-bis(α-hydroxyisopropyl)benzene, 1,3-diisopropenylbenzene and 1,4-diisopropenylbenzene.

[0184]

[0185] (In formula (DIP-S), R) 1 Each is independently isopropenyl or hydroxyisopropyl, Ma independently represents a hydrocarbon group with 1 to 12 carbon atoms that are optionally substituted with halogen atoms, and x represents an integer from 0 to 4.

[0186] In formula (DIP-S), R 1 Preferably, it is isopropyl. Additionally, both R... 1 Preferably, it is in one R 1 When one is in position 1, the other is in position 3 or 4.

[0187] In formula (DIP-S), Ma and x have the same meaning as Ma and x in formula (T1), and the preferred range is also the same.

[0188] That is, an example of resin (A) is a polymer in which more than 50% by mass (preferably 60% by mass or more, more preferably 70% by mass or more, even more preferably 80% by mass or more, even more preferably 90% by mass or more, even more preferably 95% by mass or more) of the raw material monomer is a compound represented by formula (DIP-S).

[0189] In this embodiment, the reaction temperature for synthesizing resin (A) is preferably 40°C or higher, more preferably 50°C or higher, and even more preferably 60°C or higher. It can also be 70°C or higher, 80°C or higher, 90°C or higher, 100°C or higher, 110°C or higher, or 120°C or higher. Setting the temperature to the lower limit or higher tends to increase the reaction rate and the ratio of indene skeleton (structural unit (a) in formula (Tx)), which is preferred. Furthermore, the reaction temperature is preferably 180°C or lower, more preferably 150°C or lower, and even more preferably 140°C or lower. Setting the temperature to the upper limit or lower tends to effectively suppress the formation of byproducts.

[0190] Furthermore, the reaction temperature does not need to be the same from the beginning to the end; it can be varied. In this case, it is preferable that the average temperature of the reaction throughout all processes falls within the range described above.

[0191] The catalyst used in the synthesis of resin (A) in this embodiment is not particularly limited, and an acid catalyst can be cited as an example. As an acid catalyst, inorganic acids such as hydrochloric acid, sulfuric acid, and phosphoric acid, organic acids such as oxalic acid, benzenesulfonic acid, toluenesulfonic acid, methanesulfonic acid, and fluoromethanesulfonic acid, BF3 ether complexes, BF3 phenol complexes, Lewis acids such as aluminum chloride, zinc chloride, and indium chloride, solid acids such as activated clay, acid clay, silica alumina, and zeolite, heteropolyhydrochloric acid, and strong acid ion exchange resins can be used.

[0192] When using a catalyst, its amount can be listed as 0.01 to 20.0 parts by mass relative to 100 parts by mass of the above-mentioned raw material (A) of resin (A).

[0193] The catalyst is usually a single type, but two or more types can be used in combination. When used in combination, the preferred total amount is within the range described above.

[0194] In this embodiment, the reaction solvent used in the synthesis of resin (A) is not particularly limited. It can be used in combination with aromatic hydrocarbon solvents such as toluene, benzene, chlorobenzene, and xylene; halogenated hydrocarbon solvents such as dichloromethane and chloroform; aliphatic hydrocarbon solvents such as hexane and heptane; ester solvents such as ethyl acetate and propyl acetate; amide solvents such as dimethylformamide and dimethylacetamide; alcohol solvents; or ketone solvents. Water can also be added. Examples of alcohol solvents include methanol, ethanol, butanol, propanol, methyl propylene glycol, diethylene glycol ethyl ether, butyl propylene glycol, and propyl propylene glycol. Examples of ketone solvents include acetone, methyl ethyl ketone, diethyl ketone, methyl butyl ketone, and methyl isobutyl ketone. In addition, tetrahydrofuran and dioxane can be used, but it is not limited to these.

[0195] One example of the reaction solvent in this embodiment includes an aromatic hydrocarbon solvent.

[0196] In this embodiment, the concentration of the raw material used in the synthesis of resin (A) is preferably 5% or more, more preferably 8% or more, more preferably 10% or more, and can be 12% or more, 15% or more, 17% or more, 20% or more, 22% or more, or 25% or more. Setting it to the lower limit or above tends to increase the reaction rate and the ratio of indane skeleton (structural unit (a) in formula (Tx)), which is preferred. Furthermore, the concentration of the raw material is preferably 49% or less, more preferably 40% or less. Setting it to the upper limit or below tends to effectively suppress the formation of byproducts.

[0197] Furthermore, the concentration does not need to be the same from the beginning to the end of the reaction; the concentration can be varied.

[0198] <Polyphenylene ether compounds with carbon-carbon unsaturated double bonds at the ends (B)>

[0199] The resin composition of this embodiment contains a polyphenylene ether compound (B) having a carbon-carbon unsaturated double bond at the end (hereinafter, sometimes simply referred to as "polyphenylene ether compound (B)").

[0200] The polyphenylene ether compound (B) is preferably a polyphenylene ether compound having at its end a group selected from the group represented by vinylbenzyl (Rx-1), (meth)acryloyl (Rx-2), or maleimide.

[0201]

[0202] In equations (Rx-1) and (Rx-2), R 1 R 2 and R 3 Each group independently represents a hydrogen atom, alkyl, alkenyl, or alkynyl group. * indicates the bonding site with an oxygen atom. Mc independently represents a hydrocarbon group having 1 to 12 carbon atoms. z represents an integer from 0 to 4. r represents an integer from 0 to 6.

[0203] Furthermore, from the perspective of the low dielectric properties (Dk and / or Df) and heat resistance of the obtained cured product, the polyphenylene ether compound (B) is more preferably having two or more groups selected from the group consisting of vinylbenzyl (Rx-1), (meth)acryloyl (Rx-2), and maleimide at the end.

[0204] By using these polyphenylene ether compounds, there is a tendency to more effectively improve the dielectric properties and low water absorption of printed circuit boards, etc. In this embodiment, polyphenylene ether compounds having a group represented by the formula (Rx-2) with a (meth)acryloyl group at the end are particularly preferred. By using polyphenylene ether compounds having a group represented by the formula (Rx-2) with a (meth)acryloyl group, a resin composition that can provide a cured product with superior heat resistance can be obtained.

[0205] The following is a detailed explanation of them.

[0206] Polyphenylene ether compound (B) may be exemplified by compounds having a phenylene ether skeleton represented by the following formula (X1).

[0207]

[0208] (In formula (X1), R) 24 R 25 R 26 and R 27These can be the same or different, representing alkyl, aryl, halogen, or hydrogen atoms with 6 or fewer carbon atoms.

[0209] The polyphenylene ether compound (B) may also contain repeating units represented by formula (X2) and / or repeating units represented by formula (X3).

[0210]

[0211] (In formula (X2), R) 28 R 29 R 30 R 34 and R 35 They can be the same or different, representing alkyl or phenyl groups with 6 or fewer carbon atoms. R 31 R 32 and R 33 They can be the same or different, and can be hydrogen atoms, alkyl groups with 6 or fewer carbon atoms, or phenyl groups.

[0212]

[0213] (In formula (X3), R) 36 R 37 R 38 R 39 R 40 R 41 R 42 and R 43 They can be the same or different, consisting of hydrogen atoms, alkyl groups with 6 or fewer carbon atoms, or phenyl groups. -A- is a straight-chain, branched, or cyclic divalent hydrocarbon group with 20 or fewer carbon atoms.

[0214] Examples of polyphenylene ether compounds (B) include those represented by formula (OP).

[0215]

[0216] (In formula (OP), X represents an aromatic group, -(YO) n1 - indicates a polyphenylene ether structure, n1 represents an integer from 1 to 100, and n2 represents an integer from 1 to 4. Rx is the group represented by formula (Rx-1) or formula (Rx-2).

[0217]

[0218] In equations (Rx-1) and (Rx-2), R 1 R 2 and R 3 Each group independently represents a hydrogen atom, alkyl, alkenyl, or alkynyl group. * indicates the bonding site with an oxygen atom. Mc independently represents a hydrocarbon group having 1 to 12 carbon atoms. z represents an integer from 0 to 4. r represents an integer from 0 to 6.

[0219] The aromatic group X shown above may or may not have substituents on the benzene ring, but it is preferred to have substituents. When substituents are present, the substituent Z described above can be exemplified. It is preferably selected from at least one of the group consisting of alkyl, aryl and halogen atoms having 6 or fewer carbon atoms, more preferably alkyl having 3 or fewer carbon atoms, and even more preferably methyl.

[0220] Furthermore, the polyphenylene ether structure shown above (YO)n1- may or may not have substituents on the benzene ring, but it is preferable to have substituents. When substituents are present, the substituent Z described above can be exemplified, preferably an alkyl or phenyl group having 6 or fewer carbon atoms, more preferably an alkyl group having 3 or fewer carbon atoms, and even more preferably a methyl group.

[0221] When n1 and / or n2 are integers of 2 or more, the n1 structural units (YO) and / or n2 structural units can be the same or different. n2 is preferably 2 or more, and more preferably 2.

[0222] In equations (Rx-1) and (Rx-2), R 1 R 2 and R 3 Each can independently represent a hydrogen atom, alkyl group, alkenyl group, or alkynyl group.

[0223] R 1 Preferably, it is a hydrogen atom or an alkyl group, more preferably a hydrogen atom or a methyl group, and even more preferably a hydrogen atom.

[0224] R 2 and R 3 Each is independently preferred to have a hydrogen atom or an alkyl group, more preferably a hydrogen atom or a methyl group, and even more preferably a hydrogen atom.

[0225] As R 1 R 2 and R 3 The number of carbon atoms in the alkyl, alkenyl, or alkynyl groups is preferably 5 or less, and more preferably 3 or less.

[0226] In formula (Rx-1), r represents an integer from 0 to 6, which can be an integer greater than or equal to 1. In addition, it is preferably an integer less than or equal to 5, more preferably an integer less than or equal to 4, further preferably an integer less than or equal to 3, even more preferably 1 or 2, and even more preferably 1.

[0227] In formula (Rx-1), 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 straight-chain or branched alkyl group having 1 to 10 carbon atoms, further preferably methyl, ethyl, isopropyl, isobutyl, tert-butyl, pentyl, octyl or nonyl, and even more preferably methyl, ethyl, isopropyl, isobutyl or tert-butyl.

[0228] In formula (Rx-1), z represents an integer from 0 to 4, preferably an integer from 0 to 3, more preferably an integer from 0 to 2, even more preferably 0 or 1, and even more preferably 0.

[0229] Specific examples of the group represented by formula (Rx-1) are vinylbenzyl and specific examples of the group represented by formula (Rx-2) are (meth)acryloyl.

[0230] The group represented by the preferred formula (Rx-2) for Rx.

[0231] In the resin composition of this embodiment, as a polyphenylene ether compound having a carbon-carbon unsaturated double bond at the end, it is also preferable to include both the compound shown in formula (OP), the polyphenylene ether compound having a group represented by formula (Rx-1), and the compound having a polyphenylene ether group having a group represented by formula (Rx-2).

[0232] Examples of modified polyphenylene ether compounds (g) include compounds represented by formula (OP-1).

[0233]

[0234] In formula (OP-1), X represents an aromatic group, -(YO)n2- represents a polyphenylene ether structure, and R 1 R 2 and R 3 Each group independently represents a hydrogen atom, alkyl group, alkenyl group, or alkynyl group; n1 represents an integer from 0 to 6; n2 represents an integer from 1 to 100; and n3 represents an integer from 1 to 4.

[0235] The aromatic group X shown above may or may not have substituents on the benzene ring, but it is preferred to have substituents. When substituents are present, the substituent Z described above can be exemplified. It is preferably selected from at least one of the group consisting of alkyl, aryl and halogen atoms having 6 or fewer carbon atoms, more preferably alkyl having 3 or fewer carbon atoms, and even more preferably methyl.

[0236] Furthermore, the polyphenylene ether structure shown above (YO)n2- may or may not have substituents on the benzene ring, but it is preferable to have substituents. When substituents are present, the substituent Z described above can be exemplified, preferably an alkyl or phenyl group having 6 or fewer carbon atoms, more preferably an alkyl group having 3 or fewer carbon atoms, and even more preferably a methyl group.

[0237] When n2 and / or n3 are integers of 2 or more, the n2 structural units (YO) and / or n3 structural units can be the same or different. n3 is preferably 2 or more, and more preferably 2.

[0238] In this embodiment, the polyphenylene ether compound (B) is preferably the compound represented by formula (OP-2).

[0239]

[0240] Here, -(OXO)- is preferably represented by formula (OP-3) and / or formula (OP-4).

[0241]

[0242] (In formula (OP-3), R) 4 R 5 R 6 R 10 and R 11 They can be the same or different, and can be alkyl or phenyl with 6 or fewer carbon atoms. R 7 R 8 and R 9 They can be the same or different, and can be hydrogen atoms, alkyl groups with 6 or fewer carbon atoms, or phenyl groups.

[0243]

[0244] (In formula (OP-4), R) 12 R 13 R 14 R 15 R 16 R 17 R 18 and R 19 They can be the same or different, and can be hydrogen atoms, alkyl groups with 6 or fewer carbon atoms, or phenyl groups. -A- can be a straight-chain, branched, or cyclic divalent hydrocarbon group with 20 or fewer carbon atoms.

[0245] In addition, -(YO)- is preferably represented by formula (OP-5).

[0246]

[0247] (In formula (OP-5), R) 20 R 21 They can be the same or different, and can be alkyl or phenyl with 6 or fewer carbon atoms. R 22 R 23 They can be the same or different, and can be hydrogen atoms, alkyl groups with 6 or fewer carbon atoms, or phenyl groups. Especially R. 20 and R 21 Each of the groups has one or more methyl and / or cyclohexyl groups, resulting in a resin molecule with higher rigidity. Molecules with higher rigidity have lower mobility compared to molecules with lower rigidity, thus resulting in a longer relaxation time during dielectric relaxation and improved low dielectric properties (Dk and / or Df), which is therefore preferred.

[0248] An example of formula (OP-5) has the following structure.

[0249]

[0250] Regarding the polyphenylene ether compound having the above structure, the description in Japanese Patent Application Laid-Open No. 2019-194312 can be referred to, and its content is incorporated into this specification.

[0251] 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. a and b are each independently preferably an integer from 0 to 50, more preferably an integer from 1 to 30, and preferably an integer from 1 to 10. When a and / or b is an integer of 2 or more, two or more -(Y-O)- can be arranged independently of each other in one structure, or can be arranged in blocks or randomly in two or more structures.

[0252] In addition, in the case of containing a plurality of compounds represented by formula (OP-2), the average value of a is preferably 1 < a < 10, and the average value of b is preferably 1 < b < 10.

[0253] Examples of -A- in formula (OP-4) include divalent organic groups such as methylene, ethylidene, 1-methylethylidene, 1,1-propylidene, 1,4-phenylenebis(1-methylethylidene), 1,3-phenylenebis(1-methylethylidene), cyclohexylidene, benzylidene, naphthylidene, 1-benzylethylidene, etc., but are not limited to these. [[ID=1十七]] [[ID=1十八]]

[0254] [[ID=1十九]]Rx has the same meaning as Rx in formula (OP), and the preferred range is also the same.

[0255] In the compound represented by the above formula (OP-2), preferably R 4 , R 5 , R 6 , R 10 , R 11 , R 20 and R 21 are alkyl groups having 3 or less carbon atoms, 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 23The polyphenylene ether compound is a hydrogen atom or an alkyl group having 3 or fewer carbon atoms. Particularly preferred are -(OXO)- represented by formula (OP-3) or formula (OP-4) as formula (OP-9), formula (OP-10) and / or formula (OP-11), and -(YO)- represented by formula (OP-5) as formula (OP-12) or formula (OP-13). When a and / or b are integers of 2 or more, the two or more -(YO)- can each independently be a structure formed by arranging two or more of formula (OP-12) and / or formula (OP-13), or a structure formed by block or random arrangement of formula (OP-12) and formula (OP-13).

[0256]

[0257] (In formula (OP-10), R) 44 R 45 R 46 and R 47 They can be the same or different, consisting of a hydrogen atom or a methyl group. -B- is a straight-chain, branched, or cyclic divalent hydrocarbon group with 20 or fewer carbon atoms.

[0258] For -B-, as a specific example, we can give the same example as the specific example of -A- in equation (OP-4).

[0259]

[0260] (In formula (OP-11), -B- is a straight-chain, branched, or cyclic divalent hydrocarbon group with fewer than 20 carbon atoms.)

[0261] For -B-, as a specific example, we can give the same example as the specific example of -A- in equation (OP-4).

[0262]

[0263]

[0264] The polyphenylene ether compound (B) used in this embodiment is further preferably the compound shown in formula (OP-14) and / or the compound shown in formula (OP-15), and even more preferably the compound shown in formula (OP-14).

[0265]

[0266] (In equation (OP-14), a and b each independently represent integers from 0 to 100, and at least one of a and b is an integer from 1 to 100.)

[0267] In equation (OP-14), a and b have the same meaning as a and b in equation (OP-2), and the preferred range is also the same.

[0268]

[0269] (In formula (OP-15), a and b each independently represent integers from 0 to 100, and at least one of a and b is an integer from 1 to 100.)

[0270] In equation (OP-15), a and b have the same meaning as a and b in equation (OP-2), and the preferred range is also the same.

[0271] Polyphenylene ether compounds with carbon-carbon unsaturated double bonds at the ends can be manufactured by known methods or commercially available products can be used. Examples of commercially available products include "SA9000" manufactured by SABIC Innovative Plastics, a modified polyphenylene ether compound with a methacryloyl group at the end. Examples of modified polyphenylene ether compounds with a vinyl benzyl group at the end include "OPE-2St1200" and "OPE-2St2200" manufactured by Mitsubishi Gas Chemical Co., Ltd. Alternatively, a modified polyphenylene ether compound with a vinyl benzyl group at the end can be obtained by modifying a hydroxyl-terminated polyphenylene ether compound such as "SA90" manufactured by SABIC Innovative Plastics to a vinyl benzyl group using a vinyl benzyl chloride or similar substance.

[0272] Furthermore, details of polyphenylene ether compounds with carbon-carbon unsaturated double bonds at the ends can be found in Japanese Patent Application Publication No. 2006-028111, Japanese Patent Application Publication No. 2018-131519, International Publication No. 2019-138992, and International Publication No. 2022-054303, which are incorporated herein by reference.

[0273] The number-average molecular weight (Mn) of the polyphenylene ether compound (B) converted from polystyrene by GPC (gel permeation chromatography) (details according to the methods described in the examples below) is preferably 500 or more, more preferably 800 or more, and preferably 10,000 or less, more preferably 800 or more and 5,000 or less, and preferably 3,000 or less. By having a number-average molecular weight of 500 or more, there is a tendency to further suppress tackiness when the resin composition of this embodiment is formed into a coating film. By having a number-average molecular weight of 3,000 or less, there is a tendency to further improve solubility in solvents.

[0274] Furthermore, the weight-average molecular weight (Mw) of the polyphenylene ether compound (B) based on GPC-converted polystyrene (details are as described in the examples below) is preferably 800 or more and 10,000 or less, more preferably 800 or more and 5,000 or less. By setting the value to the lower limit or above, there is a tendency for the relative permittivity (Dk) and dielectric loss tangent (Df) of the cured resin composition to become lower, and by setting the value to the upper limit or below, there is a tendency for the solubility, low viscosity, and formability of the resin composition in solvents when producing varnishes, etc., as described below, to be further improved.

[0275] Furthermore, for the equivalent amount of carbon-carbon unsaturated double bonds at the ends of the polyphenylene ether compound (B), it is preferably 400 g to 5000 g per carbon-carbon unsaturated double bond, more preferably 400 g to 2500 g. By setting the value above the lower limit, there is a tendency for the relative permittivity (Dk) and / or dielectric loss tangent (Df) of the cured resin composition to become lower. By setting the value below the upper limit, there is a tendency for the solubility, low viscosity, and formability of the resin composition to be further improved.

[0276] For the functional group equivalent (equivalent of carbon-carbon unsaturated double bond) in polyphenylene ether compound (B) with carbon-carbon unsaturated double bond at the end, the double bond amount is determined by the measurement results based on the infrared spectrophotometer and then calculated by its reciprocal.

[0277] The double bond equivalent [g / eq.] is calculated as follows.

[0278] Weigh the polyphenylene ether compound powder and record the weight. Place the powder in a volumetric flask and dilute to the specified volume with carbon disulfide to prepare the test sample. Place the sample solution in the measurement cell and set it on an infrared spectrophotometer (FT / IR-4600, manufactured by Nippon Spectrophotometer Co., Ltd.). Then, perform infrared spectrophotometric determination of the sample solution. In the case of vinyl groups in the polyphenylene ether compound, record the value at 905 cm⁻¹. -1 Peak areas in the nearby spectrum. When the carbon-carbon unsaturated double bond is methacrylyl, the peak area is recorded at 1640 cm⁻¹. -1 The peak area of ​​the nearby spectrum. The double bond concentration [mol / L] is calculated from this area value and the standard curve as the measured value.

[0279] Next, the double bond equivalent is calculated using the following formula.

[0280] Double bond equivalent [g / eq.] = Weight of powder in the sample [g] / Double bond concentration [mol / L] × Volume of sample solution [L]

[0281] The functional group equivalent of other thermosetting compounds can also be determined using the method described above. However, for compounds (monomers) that can be expressed as a single molecular weight, the value obtained by calculating the functional group equivalent using (theoretical molecular weight ÷ number of functional groups) is preferred. When two or more thermosetting compounds are involved, the functional group equivalent of the thermosetting compound is set as the sum (weighted average) of the values ​​obtained by multiplying the functional group equivalent of each thermosetting compound by its mass fraction.

[0282] The lower limit of the content of polyphenylene ether compound (B) in the resin composition of this embodiment is preferably 10 parts by mass or more, more preferably 50 parts by mass or more, and even more preferably 100 parts by mass or more, or possibly 150 parts by mass or more, relative to 100 parts by mass of resin (A). By setting the content of polyphenylene ether compound (B) to the above-mentioned lower limit or above, there is a tendency to further improve the formability of the resin composition, the heat resistance of the obtained cured product, the low water absorption, and the low dielectric properties (Dk and / or Df). In addition, the upper limit of the content of polyphenylene ether compound (B) is preferably 900 parts by mass or less, more preferably 700 parts by mass or less, even more preferably 500 parts by mass or less, possibly 300 parts by mass or less, and further possibly 240 parts by mass or less, 220 parts by mass or less, 180 parts by mass or less, or 150 parts by mass or less, relative to 100 parts by mass of resin (A). By keeping the content of polyphenylene ether compound (B) below the aforementioned upper limit, there is a tendency for the low dielectric properties (Dk and / or Df, especially low dielectric loss tangent) and chemical resistance of the resulting cured product to be further improved.

[0283] Relative to 100 parts by mass of the resin solids in the resin composition of this embodiment, the total content of resin (A) and polyphenylene ether compound (B) is preferably 40 parts by mass or more, more preferably 45 parts by mass or more, even more preferably 50 parts by mass or more, even more preferably 55 parts by mass or more, and may also be 60 parts by mass or more. By making the total content of resin (A) and polyphenylene ether compound (B) at or above the above-mentioned lower limit, there is a tendency to further improve the low water absorption and low dielectric properties (Dk and / or Df) of the obtained cured product. In addition, relative to 100 parts by mass of the resin solids in the resin composition, the total content of resin (A) and polyphenylene ether compound (B) is preferably 90 parts by mass or less, more preferably 85 parts by mass or less. By making the total content of resin (A) and polyphenylene ether compound (B) at or below the above-mentioned upper limit, there is a tendency to have an excellent balance of the formability of the resin composition, the heat resistance of the obtained cured product, and the chemical resistance.

[0284] The lower limit of the content of polyphenylene ether compound (B) in the resin composition of this embodiment is preferably 25 parts by mass or more, and more preferably 30 parts by mass or more, relative to 100 parts by mass of the resin solids in the resin composition. By setting the content of polyphenylene ether compound (B) to the above-mentioned lower limit or above, there is a tendency to further improve the low water absorption and low dielectric properties (Dk and / or Df), heat resistance, and chemical resistance of the resulting cured product. Furthermore, the upper limit of the content of polyphenylene ether compound (B) is preferably 70 parts by mass or less, more preferably 65 parts by mass or less, and can be 60 parts by mass or less, and more preferably 55 parts by mass or less, relative to 100 parts by mass of the resin solids in the resin composition. By setting the content of polyphenylene ether compound (B) to the above-mentioned upper limit or less, there is a tendency to further improve the low dielectric properties (Dk and / or Df) of the resulting cured product.

[0285] The resin composition in this embodiment may contain only one polyphenylene ether compound (B), or it may contain two or more. When it contains two or more, the total amount is preferably within the range described above.

[0286] <Isocyanurate compounds having two or more (meth)allyl groups (C1), glycourea compounds having two or more (meth)allyl groups (C2), and (meth)acrylate compounds having three or more (meth)acryloyloxy groups (C3)>

[0287] The resin composition of this embodiment comprises at least one selected from the group consisting of an isocyanurate compound (C1) having two or more (meth)allyl groups (hereinafter, sometimes simply referred to as "isocyanurate compound (C1)"), a glycourea compound (C2) having two or more (meth)allyl groups (hereinafter, sometimes simply referred to as "glycourea compound (C2)"), and a (meth)acrylate compound (C3) having three or more (meth)acryloyloxy groups, preferably comprising an isocyanurate compound (C1).

[0288] Additionally, at least one of the following compounds selected from the group consisting of isocyanurate compounds having two or more (meth)allyl groups (C1), glycourea compounds having two or more (meth)allyl groups (C2), and (meth)acrylate compounds having three or more (meth)acryloyloxy groups (C3) preferably comprises isocyanurate compounds having two or more allyl groups (C1) and / or glycourea compounds having two or more allyl groups (C2).

[0289] The number of (methyl)allyl groups in the isocyanurate compound (C1) and the glycourea compound (C2) is preferably 2 to 10 each independently.

[0290] In this embodiment, the total content of the isocyanurate compound (C1), the glycourea compound (C2), and the methacrylate compound (C3) having three or more methacryloyloxy groups is preferably 10 parts by mass or more, more preferably 20 parts by mass or more, and even more preferably 30 parts by mass or more, relative to 100 parts by mass of resin (A) in the resin composition. Depending on the application, it can be 40 parts by mass or more, 50 parts by mass or more, or 55 parts by mass or more. By setting the total content of the isocyanurate compound (C1), the glycourea compound (C2), and the methacrylate compound (C3) having three or more methacryloyloxy groups to the above-mentioned lower limit value or above, there is a tendency to further improve the heat resistance and low thermal expansion properties of the obtained cured product. Furthermore, the upper limit of the total content of isocyanurate compound (C1), glycourea compound (C2), and (meth)acrylate compound (C3) having three or more (meth)acryloyloxy groups is preferably 900 parts by weight or less, more preferably 700 parts by weight or less, relative to 100 parts by weight of resin (A) in the resin composition. Depending on the application, it can be 600 parts by weight or less, 500 parts by weight or less, 400 parts by weight or less, 300 parts by weight or less, 240 parts by weight or less, 220 parts by weight or less, 180 parts by weight or less, 150 parts by weight or less, or 100 parts by weight or less. By keeping the total content of isocyanurate compound (C1), glycourea compound (C2), and (meth)acrylate compound (C3) having three or more (meth)acryloyloxy groups below the above-mentioned upper limit, there is a tendency to further improve the low dielectric properties (Dk and / or Df) of the obtained cured product.

[0291] In this embodiment, the total content of the isocyanurate compound (C1), the glycourea compound (C2), and the methacrylate compound (C3) having three or more methacryloyloxy groups is 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, and can be 10 parts by mass or more, relative to 100 parts by mass of the resin solids in the resin composition. By setting the total content of the isocyanurate compound (C1), the glycourea compound (C2), and the methacrylate compound (C3) having three or more methacryloyloxy groups to the above-mentioned lower limit value, there is a tendency to further improve the heat resistance and low thermal expansion of the obtained cured product. In addition, the upper limit value of the total content of the isocyanurate compound (C1), the glycourea compound (C2), and the methacrylate compound (C3) having three or more methacryloyloxy groups 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 can also be 20 parts by mass or less, relative to 100 parts by mass of the resin solids in the resin composition. By keeping the total content of isocyanurate compound (C1), glycourea compound (C2), and (meth)acrylate compound having three or more (meth)acryloyloxy groups below the above-mentioned upper limit, there is a tendency to further improve the low dielectric properties (Dk and / or Df) of the obtained cured product.

[0292] In this embodiment, the total content of the polyphenylene ether compound (B), isocyanurate compound (C1), glycourea compound (C2), and (meth)acrylate compound (C3) having three or more (meth)acryloyloxy groups is preferably 100 parts by mass or more, more preferably 125 parts by mass or more, further preferably 150 parts by mass or more, and may also be 200 parts by mass or more, relative to 100 parts by mass of resin (A) in the resin composition. By making the total content of the polyphenylene ether compound (B), isocyanurate compound (C1), glycourea compound (C2), and (meth)acrylate compound (C3) having three or more (meth)acryloyloxy groups at or above the above-mentioned lower limit value, there is a tendency to further improve the heat resistance and low thermal expansion of the obtained cured product. Furthermore, the total content of the polyphenylene ether compound (B), isocyanurate compound (C1), glycourea compound (C2), and (meth)acrylate compound (C3) having three or more (meth)acryloyloxy groups is preferably 900 parts by weight or less, more preferably 700 parts by weight or less, even more preferably 500 parts by weight or less, and may also be 300 parts by weight or less, relative to 100 parts by weight of resin (A) in the resin composition. By keeping the total content of the polyphenylene ether compound (B), isocyanurate compound (C1), glycourea compound (C2), and (meth)acrylate compound (C3) having three or more (meth)acryloyloxy groups below the above-mentioned upper limit, there is a tendency to further improve the low dielectric properties (Dk and / or Df) of the obtained cured product.

[0293] In this embodiment, the mass ratio {(B) / [(C1)+(C2)+(C3)]} of the total of the polyphenylene ether compound (B) with carbon-carbon unsaturated double bonds at the ends to the isocyanurate compound (C1) having two or more (meth)allyl groups and / or the glycourea compound (C2) having two or more (meth)allyl groups and the methacrylate compound (C3) having three or more (meth)acryloyloxy groups is preferably 1.0 to 9.0. By setting the mass ratio to the lower limit or above, the low dielectric properties (Dk and / or Df) and heat resistance of the obtained cured product tend to be further improved. In addition, by setting the mass ratio to the upper limit or below, the heat resistance and low thermal expansion tend to be further improved.

[0294] The aforementioned mass ratio {(B) / [(C1)+(C2)+(C3)]} is preferably 1.2 or more, more preferably 1.5 or more, and preferably 7.0 or less, more preferably 5.0 or less, even more preferably 3.0 or less, and even more preferably 2.5 or less.

[0295] In addition, in the resin composition of this embodiment, a portion of the isocyanurate compound (C1), the glycourea compound having two or more (meth)allyl groups (C2), and the (meth)acrylate compound (C3) may be oligomers or prepolymers.

[0296] <<Isocyanurate Compounds (C1)>>

[0297] As for the isocyanurate compound (C1), there are no particular limitations as long as it has two or more (methyl)allyl groups and an isocyanurate ring (isocyanurate (Nurette) skeleton). Because the isocyanurate compound (C1) has a large number of (methyl)allyl groups that serve as crosslinking points, it can be firmly cured with resin (A), polyphenylene ether compound (B), and other resin components, resulting in cured products with low dielectric properties (Dk and / or Df) and excellent heat resistance. As for the isocyanurate compound (C1), compounds represented by formula (TA) are preferred.

[0298] Formula (TA)

[0299]

[0300] (In formula (TA), R A (Indicates substituents).

[0301] In formula (TA), R A The term indicates a substituent, more preferably a substituent with a formula weight of 15 to 500.

[0302] R A The first example is an alkyl group having 1 to 22 carbon atoms or an alkenyl group having 2 to 22 carbon atoms. By using allyl compounds having 1 to 22 alkyl groups or 2 to 22 alkenyl groups, it is possible to provide resin compositions with excellent crosslinking properties and yield cured products with high toughness. As a result, even when the resin composition does not contain a substrate such as glass cloth, cracking during etching processes can be suppressed.

[0303] From the viewpoint of improving processability, the number of carbon atoms in the aforementioned alkyl and / or alkenyl groups is preferably 3 or more, more preferably 8 or more, further preferably 12 or more, and preferably 18 or less. Therefore, the resin composition exhibits better resin flowability, and the circuit filling properties, etc., are improved when using the resin composition of this embodiment to fabricate multilayer circuit boards, etc.

[0304] R A The second example is a group containing an allyl isocyanurate group. R A When allyl isocyanurate groups are included, the compound represented by formula (TA) is preferably the compound represented by formula (TA-1).

[0305] Formula (TA-1)

[0306]

[0307] (In formula (TA-1), R A2 (It is a divalent linker.)

[0308] In formula (TA-1), R A2 Preferably, it is a divalent linker with a formula weight of 54 to 250, more preferably a divalent linker with a formula weight of 54 to 250 and carbon atoms at both ends, and even more preferably an aliphatic hydrocarbon group with 2 to 20 carbon atoms (wherein, the aliphatic hydrocarbon group may include an ether group, and may also have a hydroxyl group). More specifically, R A2 Preferably, it is a group represented by any of the following formulas (i) to (iii).

[0309]

[0310] (In formulas (i) to (iii), p) c1 The number of repeating units of the methylene group is an integer from 2 to 18. c2 This indicates the number of repeating units of the oxyethylidene group, which is 0 or 1. * indicates the bonding site.

[0311] The above p c1 Preferably, it is an integer from 2 to 10, more preferably an integer from 3 to 8, and even more preferably an integer from 3 to 5.

[0312] The above p c2 It can be 0 or 1, but 1 is preferred.

[0313] R A The third example is a phosphorus-based substituent.

[0314] R A2 The first example is preferred.

[0315] In this embodiment, the equivalent of the reactive group (allyl) in the compound represented by formula (TA) is preferably 1000 g / eq. or less. It is believed that if the above equivalent is 1000 g / eq. or less, a high Tg can be obtained more reliably.

[0316] Examples of alkyl groups having 1 to 22 carbon atoms include straight-chain or branched alkyl groups, such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, dodecyl, tetradecyl, hexadecyl, octadecyl, eicosyl, and docosyl. Examples of alkenyl groups having 2 to 22 carbon atoms include allyl and decenyl.

[0317] Specific examples of compounds represented by formula (TA) include triallyl isocyanurate, 5-octyl-1,3-diallyl isocyanurate, 5-dodecyl-1,3-diallyl isocyanurate, 5-tetradecyl-1,3-diallyl isocyanurate, 5-hexadecyl-1,3-diallyl isocyanurate, 5-octadecyl-1,3-diallyl isocyanurate, 5-eicosyl-1,3-diallyl isocyanurate, 5-docenyl-1,3-diallyl isocyanurate, and the like. They can be used alone or in combination of two or more, and can also be used in the form of prepolymers.

[0318] There are no particular limitations on the method of preparing the compound shown in formula (TA). For example, it can be obtained by reacting diallyl isocyanurate with an alkyl halide in an aprotic polar solvent such as N,N'-dimethylformamide, in the presence of alkaline substances such as sodium hydroxide, potassium carbonate, and triethylamine, at a temperature of about 60°C to 150°C.

[0319] Furthermore, the compound represented by formula (TA) can also be a commercially available product. There are no particular limitations on the commercially available product; examples include L-DAIC manufactured by Shikoku Chemical Industry Co., Ltd., and P-DAIC manufactured by Shikoku Chemical Industry Co., Ltd., which has phosphorus-based substituents. As a triallyl isocyanurate, TAIC manufactured by Shin-Mitsubishi Corporation can be cited as an example. As a compound represented by formula (TA-1), DD-1 manufactured by Shikoku Chemical Industry Co., Ltd. can be cited as an example.

[0320] The isocyanurate compound (C1) (preferably the compound shown in formula (TA)) preferably has a molecular weight of 200 or more, more preferably 300 or more, further preferably 400 or more, and even more preferably 500 or more. By setting the molecular weight to the lower limit or above, the low dielectric properties (Dk and / or Df) and heat resistance of the obtained cured product tend to be further improved. Furthermore, the isocyanurate compound (C1) (preferably the compound shown in formula (TA)) preferably has a molecular weight of 3000 or less, more preferably 2000 or less, further preferably 1000 or less, and even more preferably 800 or less. By setting the molecular weight to the upper limit or below, the low thermal expansion of the obtained cured product tends to be further improved.

[0321] When the resin composition of this embodiment contains an isocyanurate compound (C1), its content is 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, and can be 10 parts by mass or more, relative to 100 parts by mass of the resin solids in the resin composition. By setting the content of the isocyanurate compound (C1) to the aforementioned lower limit value or above, there is a tendency to further improve the formability of the resin composition, the heat resistance of the obtained cured product, and the low thermal expansion. In addition, the upper limit value of the content of the isocyanurate compound (C1) relative to 100 parts by mass of the resin solids in the resin composition is preferably 40 parts by mass or less, more preferably 30 parts by mass or less, and can also be 20 parts by mass or less. By setting the content of the isocyanurate compound (C1) to the aforementioned upper limit value or less, there is a tendency to further improve the heat resistance and low dielectric properties (Dk and / or Df) of the obtained cured product.

[0322] The resin composition of this embodiment may contain only one isocyanurate compound (C1) or two or more. When containing two or more, the total amount is preferably within the range described above.

[0323] <Glycourea compound (C2)>

[0324] As for the glycourea compound (C2), there are no particular limitations as long as it contains a glycourea structure and two or more (methyl)allyl groups. When the glycourea compound (C2) is mixed into the resin composition, the number of (methyl)allyl groups can be increased, that is, the number of crosslinking points can be increased. Therefore, similar to the isocyanurate compound (C1), it can be firmly cured with resin (A), polyphenylene ether compound (B), and other resin components to obtain a cured product with low dielectric properties (Dk and / or Df) and excellent heat resistance.

[0325] In this embodiment, the glycourea compound (C2) is preferably a compound represented by formula (GU-0), and more preferably by formula (GU).

[0326] Formula(GU-0)

[0327]

[0328] (In formula (GU-0), R) 1 Each is independently a hydrogen atom or a substituent, R 1 At least two of them are groups containing (methyl)allyl groups.

[0329] In formula (GU-0), R 1 Each of the following is preferably a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, or an alkenyl group having 2 to 5 carbon atoms, preferably an alkenyl group having 2 to 5 carbon atoms, more preferably (methyl)allyl, and even more preferably allyl.

[0330] In formula (GU-0), R 1 Preferably, three or four groups are (methyl)allyl groups, more preferably four groups are (methyl)allyl groups.

[0331] In formula (GU-0), R 2 Each of the components is preferably a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or a phenyl group, and more preferably a hydrogen atom or a methyl group.

[0332] Formula(GU)

[0333]

[0334] (In formula (GU), each R is an independent hydrogen atom or substituent, and at least two of R are groups containing (methyl)allyl groups.)

[0335] In formula (GU), R is preferably a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, or an alkenyl group having 2 to 5 carbon atoms, preferably an alkenyl group having 2 to 5 carbon atoms, more preferably (methyl)allyl, and even more preferably allyl.

[0336] In formula (GU), R preferably consists of 3 or 4 groups containing (methyl)allyl groups, more preferably 4 groups containing (methyl)allyl groups.

[0337] As a specific example of a compound represented by formula (GU), 1,3,4,6-tetraallylglycourea (a compound in formula (GU) in which all R are allyl groups) can be cited.

[0338] Alternatively, the compound represented by formula (GU) can also be a commercially available product. There are no particular limitations on what constitutes a commercially available product; for example, TA-G manufactured by Shikoku Chemical Industry Co., Ltd. can be cited.

[0339] The molecular weight of the glycourea compound (C2) (preferably a compound represented by formula (GU-0), more preferably a compound represented by formula (GU)) is preferably 195 or more, more preferably 220 or more, and even more preferably 250 or more, and may also be 300 or more, or 400 or more. By setting the molecular weight of the glycourea compound (C2) to the lower limit or above, the heat resistance and low thermal expansion of the obtained cured product tend to be further improved. The molecular weight of the glycourea compound (C2) (preferably a compound represented by formula (GU)) is also preferably 1500 or less, more preferably 1000 or less, and even more preferably 800 or less, and may also be 700 or less, or 600 or less. By setting the molecular weight of the glycourea compound (C2) to the upper limit or below, the low dielectric properties (Dk and / or Df) and heat resistance of the obtained cured product tend to be further improved.

[0340] When the resin composition of this embodiment contains a glyceryl compound (C2) (preferably a compound represented by the formula (GU)), its content relative to 100 parts by mass of the resin solids in the resin composition is preferably 1 part by mass or more, more preferably 3 parts by mass or more, even more preferably 5 parts by mass or more, and can be 10 parts by mass or more. By setting the content of the glyceryl compound (C2) to the aforementioned lower limit value or above, the resin composition exhibits excellent formability, and tends to further improve the heat resistance and low thermal expansion of the obtained cured product. In addition, relative to 100 parts by mass of the resin solids in the resin composition, the upper limit value of the content of the glyceryl compound (C2) (preferably a compound represented by the formula (GU)) is preferably 40 parts by mass or less, more preferably 30 parts by mass or less, even more preferably 25 parts by mass or less, and can also be 20 parts by mass or less. By setting the content of the glyceryl compound (C2) to the aforementioned upper limit value or less, there is a tendency to further improve the low dielectric properties (Dk and / or Df) of the obtained cured product.

[0341] The resin composition of this embodiment may contain only one type of glycourea compound (C2), or it may contain two or more types. When it contains two or more types, the total amount is preferably within the range described above.

[0342] <<(Methacryloxy)acrylate compounds (C3) having 3 or more (meth)acryloyloxy groups>

[0343] The (meth)acrylate compound having three or more (meth)acryloyloxy groups is preferably a compound having three to five (meth)acryloyloxy groups, more preferably a compound having three or four (meth)acryloyloxy groups, and even more preferably a compound having three (meth)acryloyloxy groups. The (meth)acrylate compound (C3) is preferably a compound having a methacryloyloxy group.

[0344] (Methacryloxy)acrylate compounds (C3) having three or more (meth)acryloyloxy groups have a large number of (meth)acryloyl groups that serve as crosslinking points, thus they can be firmly cured with resin (A), polyphenylene ether compound (B), and other resin components, resulting in cured products with low dielectric properties (Dk and / or Df) and excellent heat resistance. As (meth)acrylate compounds (C3) having three or more (meth)acryloyloxy groups, compounds represented by formula (MA) are preferred.

[0345] Formula (MA)

[0346]

[0347] (In formula (MA), R) 1 R represents a hydrogen atom or substituent. 2 Each can independently represent a hydrogen atom or a methyl group.

[0348] In formula (MA), R 1 The substituent represents a hydrogen atom or a substituent, more preferably a substituent with a formula weight of 15 to 500, even more preferably a substituent with a formula weight of 15 to 300, even more preferably a substituent with a formula weight of 15 to 100, and even more preferably a substituent with a formula weight of 15 to 50.

[0349] R 1 Preferably, the compound is a hydrocarbon group or (meth)acryloyloxy group, more preferably a hydrocarbon group having 22 or fewer carbon atoms, and even more preferably an alkyl group having 1 to 22 carbon atoms or an alkenyl group having 2 to 22 carbon atoms. By using a compound having an alkyl group having 1 to 22 carbon atoms or an alkenyl group having 2 to 22 carbon atoms, a resin composition with excellent crosslinking properties and high toughness can be provided. Therefore, even when the resin composition does not contain a substrate such as glass cloth, cracking during etching processes can be suppressed.

[0350] From the viewpoint of improving processability, the number of carbon atoms in the alkyl and / or alkenyl groups is preferably 2 or more, can be 8 or more, further can be 12 or more, and can be 18 or less. Therefore, the resin composition exhibits better resin flowability, and the circuit filling properties, etc., are improved when using the resin composition of this embodiment to fabricate multilayer circuit boards, etc.

[0351] In this embodiment, the (meth)acryloyloxy equivalent of the compound represented by formula (MA) is preferably 1000 g / eq. or less. If the above equivalent is 1000 g / eq. or less, there is a tendency to obtain a high Tg more reliably. The lower limit of the (meth)acryloyloxy equivalent is, for example, 99 g / eq. or more.

[0352] As for the aforementioned alkyl groups having 1 to 22 carbon atoms, straight-chain or branched alkyl groups having 3 to 22 carbon atoms are preferred, and examples include methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, dodecyl, tetradecyl, hexadecyl, octadecyl, eicosyl, and docosyl. The aforementioned alkenyl groups having 2 to 22 carbon atoms are preferably alkenyl groups having 2 to 15 carbon atoms, and examples include allyl and decenyl.

[0353] Specific examples of compounds represented by formula (MA) include trimethylolpropane trimethacrylate, trimethylolpropane triacrylate, and pentaerythritol tetra(meth)acrylate. They can be used alone or in combination of two or more, and can also be used in the form of prepolymers.

[0354] Alternatively, commercially available products can be used as the compound represented by formula (MA). There are no particular limitations on what constitutes a commercially available product; for example, "NK Ester TMPT" manufactured by Shin-Nakamura Chemical Industry Co., Ltd. can be cited as a commercially available product.

[0355] The molecular weight of the (meth)acrylate compound (C3) having three or more (meth)acryloyloxy groups is preferably 300 or more, more preferably 330 or more, and can be 400 or more, or 500 or more. By setting the molecular weight to the lower limit or above, the low dielectric properties (Dk and / or Df) and heat resistance of the obtained cured product tend to be further improved. Furthermore, the molecular weight of the (meth)acrylate compound (C3) (preferably the compound shown in formula (MA)) is preferably 3000 or less, more preferably 2000 or less, more preferably 1000 or less, and even more preferably 800 or less. By setting the molecular weight to the upper limit or below, the low thermal expansion of the obtained cured product tends to be further improved.

[0356] When the resin composition of this embodiment contains a (meth)acrylate compound (C3) having three or more (meth)acryloyloxy groups, its content relative to 100 parts by mass of the resin solids in the resin composition is preferably 1 part by mass or more, more preferably 3 parts by mass or more, even more preferably 5 parts by mass or more, and can be 10 parts by mass or more. By setting the content of the (meth)acrylate compound (C3) having three or more (meth)acryloyloxy groups to the above-mentioned lower limit value or above, there is a tendency to further improve the formability of the resin composition, the heat resistance of the obtained cured product, and the low thermal expansion. In addition, the upper limit value of the content of the (meth)acrylate compound (C3) relative to 100 parts by mass of the resin solids in the resin composition is preferably 40 parts by mass or less, more preferably 30 parts by mass or less, and can also be 20 parts by mass or less. By setting the content of the (meth)acrylate compound (C3) having three or more (meth)acryloyloxy groups to the above-mentioned upper limit value or below, there is a tendency to further improve the heat resistance and low dielectric properties (Dk and / or Df) of the obtained cured product.

[0357] The resin composition of this embodiment may contain only one (meth)acrylate compound (C3) having three or more (meth)acryloyloxy groups, or it may contain two or more. When two or more are contained, the total amount is preferably within the range described above.

[0358] <Other Resin Components (D)>

[0359] The resin composition of this embodiment preferably comprises a maleimide compound, a polymer having a structural unit shown in formula (V), an epoxy resin, a phenolic compound, an oxacyclobutane resin, a benzoxazine compound, a cyanate ester compound, an arylcyclobutene resin, a polyamide resin, a polyimide resin, a perfluorovinyl ether resin, a styrene compound other than the aforementioned polyphenylene ether compound (B) with a carbon-carbon unsaturated double bond at the end, an isopropylene compound other than the aforementioned resin (A) with an indane backbone, and other compounds besides said resin (A). The group consisting of compounds having carbon-carbon unsaturated double bonds at the ends and having an indane skeleton; polyfunctional (meth)allylic compounds other than the isocyanurate compounds (C1) having two or more (meth)allylic groups and the glycourea compounds (C2) having two or more (meth)allylic groups; polyfunctional (meth)acrylate compounds other than the polyphenylene ether compounds (B) having carbon-carbon unsaturated double bonds at the ends and the (meth)acrylate compounds (C3) having three or more (meth)acryloyloxy groups; elastomers; and petroleum resins. One or more other components (D) preferably include those selected from maleimide compounds, polymers having structural units shown in formula (V), epoxy resins, phenolic compounds, oxetane resins, benzoxazine compounds, cyanate ester compounds, arylcyclobutene resins, polyamide resins, polyimide resins, perfluorovinyl ether resins, styrene compounds other than the polyphenylene ether compounds (B) with carbon-carbon unsaturated double bonds at the ends, isopropylene compounds other than the resins (A) with indane skeletons, and compounds other than those with two The composition includes one or more other components (D) from the group consisting of the above-mentioned (meth)allyl isocyanurate compound (C1) and the above-mentioned (meth)allyl glycourea compound (C2) having two or more (meth)allyl groups, polyfunctional (meth)acrylate compounds other than the above-mentioned polyphenylene ether compound (B) having a carbon-carbon unsaturated double bond at the end and the above-mentioned (meth)acrylate compound (C3) having three or more (meth)acryloyloxy groups, elastomers, and petroleum resins, and preferably includes a maleimide compound.

[0360]

[0361] (In formula (V), Ar represents an aromatic hydrocarbon linking group. * indicates a bonding position.)

[0362] By including such components, the desired performance required by the printed circuit board can be achieved more effectively. Other resin components (D) are typically thermosetting compounds.

[0363] The other resin components (D) mentioned above are preferably characterized by excellent low dielectric properties (Dk and / or Df) in their cured products. For example, the dielectric constant (Dk) of the cured products of each of the other resin components (D) at a frequency of 10 GHz, as measured by the resonant cavity perturbation method, is preferably 4.0 or less, more preferably 3.5 or less. Furthermore, the lower limit of the aforementioned dielectric constant (Dk) is, for example, 2.0 or more. Additionally, the dielectric loss tangent (Df) of the cured products of each of the other resin components (D) at a frequency of 10 GHz, as measured by the resonant cavity perturbation method, is preferably 0.003 or less, more preferably 0.002 or less. Furthermore, the lower limit of the dielectric loss tangent (Df) is, for example, 0.0001 or more. The dielectric constant and dielectric loss tangent can be measured, for example, according to the methods (curing conditions, measurement conditions) described in the examples.

[0364] Furthermore, other resin components (D) preferably have high heat resistance in their cured products. For example, the glass transition temperature of the cured products of each of the other resin components (D), as measured by dynamic viscoelasticity determination according to JIS C6481, is preferably 150°C or higher, more preferably 180°C or higher, and even more preferably 200°C or higher. By setting the glass transition temperature to or above the aforementioned lower limit, a cured product with superior heat resistance can be obtained. In addition, the aforementioned upper limit of the glass transition temperature is practically 400°C or lower.

[0365] When the resin composition of this embodiment includes other resin components (D), the total content of these components relative to 100 parts by mass of the resin solids in the resin composition is preferably 1 part by mass or more, more preferably 5 parts by mass or more, further preferably 10 parts by mass or more, even more preferably 15 parts by mass or more, and may also be 20 parts by mass or more. By setting the content of other resin components (D) to the above-mentioned lower limit or above, there is a tendency to further improve the heat resistance of the obtained cured product. In addition, the upper limit of the total content of other resin components (D) relative to 100 parts by mass of the resin solids in the resin composition is preferably 70 parts by mass or less, more preferably 60 parts by mass or less, further preferably 50 parts by mass or less, and may be 40 parts by mass or less, or 30 parts by mass or less. By setting the content of other resin components (D) to the above-mentioned upper limit or less, there is a tendency to further improve the low dielectric properties (Dk and / or Df) of the obtained cured product.

[0366] <<Maleimide Compounds>>

[0367] The resin composition of this embodiment may contain a maleimide compound.

[0368] Maleimide compounds are not particularly limited as long as one molecule contains one or more maleimide groups (preferably 2 to 12, more preferably 2 to 6, further preferably 2 to 4, even more preferably 2 or 3, and even more preferably 2), and can be widely used in the field of printed circuit boards.

[0369] In this embodiment, the maleimide compound preferably includes one or more compounds selected from the group consisting of a compound represented by formula (M0), a compound represented by formula (M1), a compound represented by formula (M2), a compound represented by formula (M3), a compound represented by formula (M4), a compound represented by formula (M5), a maleimide compound (M6), a maleimide compound (M7), and a maleimide compound (M8), and more preferably includes a compound selected from the group consisting of a compound represented by formula (M0), a compound represented by formula (M1), a compound represented by formula (M2), a compound represented by formula (M3), and a compound represented by formula (M8). The compound comprises one or more compounds selected from the group consisting of the compound shown in formula (M4) and the compound shown in formula (M5), more preferably comprising one or more compounds selected from the group consisting of the compound shown in formula (M0), the compound shown in formula (M1), the compound shown in formula (M3), the compound shown in formula (M4), and the compound shown in formula (M5), more preferably comprising one or more compounds selected from the group consisting of the compound shown in formula (M1), the compound shown in formula (M3), and the compound shown in formula (M5), and even more preferably comprising the compound shown in formula (M1) and / or the compound shown in formula (M3). When these maleimide compounds are used in materials for printed circuit boards (e.g., metal foil laminates), excellent heat resistance can be imparted.

[0370]

[0371] (In formula (M0), R) 51 Each independently represents a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or a phenyl group, R 52 Each atom can be independently represented by a hydrogen atom or a methyl group, and n1 represents an integer greater than or equal to 1.

[0372] R 51 Each is preferably selected independently from the group consisting of hydrogen atom, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl and phenyl, more preferably hydrogen atom and / or methyl, and even more preferably hydrogen atom.

[0373] R 52 Methyl is preferred.

[0374] n1 is preferably an integer from 1 to 10, more preferably an integer from 1 to 5, even more preferably an integer from 1 to 3, even more preferably 1 or 2, and even more preferably 1.

[0375] Specifically, the following compounds can be listed as preferred examples of formula (M0).

[0376]

[0377] In the above formula, R 8 Each can independently represent a hydrogen atom, a methyl group, or an ethyl group, with methyl being preferred.

[0378] The compound represented by formula (M0) can be a mixture of two or more compounds, in addition to being a single compound. Examples of mixtures include mixtures of compounds with n1 different values, and R... 51 and / or R 52 This includes mixtures of compounds with different types of substituents, mixtures of compounds with different bonding positions (meta, para, or ortho) of the maleimide group and oxygen atom relative to the benzene ring, and mixtures of compounds formed by combinations of two or more of the above-mentioned different positions. The same applies to compounds represented by formulas (M1) to (M8) below.

[0379]

[0380] (In formula (M1), R) M1 R M2 R M3 and R M4 Each can independently represent a hydrogen atom or an organic group. R M5 and R M6 Each can independently represent a hydrogen atom or an alkyl group. Ar M This indicates a divalent aromatic group. A is an alicyclic group with a 4- to 6-membered ring. R M7 and R M8 Each is an alkyl group independently. mx is 1 or 2, lx is 0 or 1. R M9 and R M10 Each can independently represent a hydrogen atom or an alkyl group. R M11 R M12 R M13 and R M14 Each can independently represent a hydrogen atom or an organic group. R M15 Each of these groups independently represents an alkyl group (1-10 carbon atoms), an alkoxy group (1-10 carbon atoms), an alkylthio group (1-10 carbon atoms), a cycloalkyl group (3-10 carbon atoms), an aryl group (6-10 carbon atoms), an aryloxy group (6-10 carbon atoms), an arylthio group (6-10 carbon atoms), a halogen atom, a hydroxyl atom, or a mercapto group. px represents an integer from 0 to 3. nx represents an integer from 1 to 20.

[0381] R in the formula M1 R M2 R M3 and R M4Each can independently represent a hydrogen atom or an organic group. The organic group here is preferably an alkyl group, more preferably an alkyl group having 1 to 12 carbon atoms, even more preferably an alkyl group having 1 to 6 carbon atoms, and even more preferably methyl, ethyl, propyl, or butyl, with methyl being particularly preferred. R M1 and R M3 Each is preferably an alkyl group, R M2 and R M4 Hydrogen atoms are preferred.

[0382] R M5 and R M6 Each of the terms independently represents a hydrogen atom or an alkyl group, preferably an alkyl group. The alkyl group here is preferably an alkyl group having 1 to 12 carbon atoms, more preferably an alkyl group having 1 to 6 carbon atoms, and even more preferably methyl, ethyl, propyl, or butyl, with methyl being particularly preferred.

[0383] Ar M The aromatic group representing the divalent group is preferably phenylene, naphthyl, phenanthrene, or anthracene, more preferably phenylene, and even more preferably m-phenylene. Ar M It may have substituents, preferably alkyl, more preferably alkyl with 1 to 12 carbons, even more preferably alkyl with 1 to 6 carbons, and even more preferably methyl, ethyl, propyl, or butyl, with methyl being particularly preferred. However, Ar M Preferably unsubstituted.

[0384] A is a 4- to 6-membered alicyclic group, more preferably a 5-membered alicyclic group (preferably a group that forms an inden ring together with the benzene ring). R M7 and R M8 Each of the components is 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.

[0385] mx is 1 or 2, preferably 2.

[0386] lx is 0 or 1, preferably 1.

[0387] R M9 and R M10 Each of the terms independently represents 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, and even more preferably methyl, ethyl, propyl, or butyl, with methyl being particularly preferred.

[0388] R M11 R M12 R M13 and R M14 Each can independently represent a hydrogen atom or an organic group. The organic group here is preferably an alkyl group, more preferably an alkyl group having 1 to 12 carbon atoms, even more preferably an alkyl group having 1 to 6 carbon atoms, and even more preferably methyl, ethyl, propyl, or butyl, with methyl being particularly preferred. RM12 and R M13 Each is preferably an alkyl group, R M11 and R M14 Hydrogen atoms are preferred.

[0389] R M15 Each of the following can be independently represented as an alkyl group having 1 to 10 carbon atoms, an alkoxy 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, 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.

[0390] px represents an integer from 0 to 3, preferably an integer from 0 to 2, more preferably 0 or 1, and even more preferably 0.

[0391] nx represents an integer from 1 to 20. nx can also be an integer less than 10.

[0392] It should be noted that the resin composition of this embodiment is a compound represented by formula (M1), which may contain only one compound with at least different values ​​of nx, or may contain two or more compounds. When two or more compounds are included, in order to achieve a low melting point (low softening point), low melt viscosity, and excellent processability, the average value (average number of repeating units) 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, further preferably 1.0 or more, and even more preferably 1.1 or more. Additionally, n is preferably 10.0 or less, more preferably 8.0 or less, further preferably 7.0 or less, even more preferably 6.0 or less, and may also be 5.0 or less. The same applies to formulas (M1-1) and the like described later.

[0393] The compound represented by formula (M1) is preferably the compound represented by the following formula (M1-1).

[0394]

[0395] (In formula (M1-1), R) M21 R M22 R M23 and R M24 Each can independently represent a hydrogen atom or an organic group. R M25 and R M26 Each can independently represent a hydrogen atom or an alkyl group. R M27 R M28 R M29 and R M30 Each can independently represent a hydrogen atom or an organic group. R M31 and R M32 Each can independently represent a hydrogen atom or an alkyl group. RM33 R M34 R M35 and R M36 Each can independently represent a hydrogen atom or an organic group. R M37 R M38 and R M39 Each can independently represent a hydrogen atom or an alkyl group. nx represents an integer greater than 1 and less than 20.

[0396] R in the formula M21 R M22 R M23 and R M24 Each can independently represent a hydrogen atom or an organic group. The organic group here is preferably an alkyl group, more preferably an alkyl group having 1 to 12 carbon atoms, even more preferably an alkyl group having 1 to 6 carbon atoms, and even more preferably methyl, ethyl, propyl, or butyl, with methyl being particularly preferred. R M21 and R M23 Preferably alkyl, R M22 and R M24 Hydrogen atoms are preferred.

[0397] R M25 and R M26 Each of the terms independently represents a hydrogen atom or an alkyl group, preferably an alkyl group. The alkyl group here is preferably an alkyl group having 1 to 12 carbon atoms, more preferably an alkyl group having 1 to 6 carbon atoms, and even more preferably methyl, ethyl, propyl, or butyl, with methyl being particularly preferred.

[0398] R M27 R M28 R M29 and R M30 Each can be independently represented by a hydrogen atom or an organic group, preferably a hydrogen atom. The organic group here is preferably an alkyl group, more preferably an alkyl group having 1 to 12 carbon atoms, even more preferably an alkyl group having 1 to 6 carbon atoms, and even more preferably methyl, ethyl, propyl, or butyl, with methyl being particularly preferred.

[0399] R M31 and R M32 Each of the terms independently represents a hydrogen atom or an alkyl group, preferably an alkyl group. The alkyl group here is preferably an alkyl group having 1 to 12 carbon atoms, more preferably an alkyl group having 1 to 6 carbon atoms, and even more preferably methyl, ethyl, propyl, or butyl, with methyl being particularly preferred.

[0400] R M33 R M34 R M35 and R M36 Each of these groups independently represents a hydrogen atom or an organic group. The organic group here is preferably an alkyl group, more preferably an alkyl group having 1 to 12 carbon atoms, even more preferably an alkyl group having 1 to 6 carbon atoms, and even more preferably methyl, ethyl, propyl, or butyl, with methyl being particularly preferred.

[0401] R M33 and R M36 Preferably, hydrogen atoms, R M34 and R M35 Alkyl groups are preferred.

[0402] R M37 R M38 and R M39 Each of the terms independently represents a hydrogen atom or an alkyl group, preferably an alkyl group. The alkyl group here is preferably an alkyl group having 1 to 12 carbon atoms, more preferably an alkyl group having 1 to 6 carbon atoms, and even more preferably methyl, ethyl, propyl, or butyl, with methyl being particularly preferred.

[0403] nx represents an integer greater than 1 and less than 20. nx can also be an integer less than 10.

[0404] The compound represented by formula (M1-1) is preferably the compound represented by formula (M1-2) below.

[0405]

[0406] (In formula (M1-2), R) M21 R M22 R M23 and R M24 Each can independently represent a hydrogen atom or an organic group. R M25 and R M26 Each can independently represent a hydrogen atom or an alkyl group. R M27 R M28 R M29 and R M30 Each can independently represent a hydrogen atom or an organic group. R M31 and R M32 Each can independently represent a hydrogen atom or an alkyl group. R M33 R M34 R M35 and R M36 Each can independently represent a hydrogen atom or an organic group. R M37 R M38 and R M39 Each can independently represent a hydrogen atom or an alkyl group. nx represents an integer greater than 1 and less than 20.

[0407] 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 M31R M32 R M33 R M34 R M35 R M36 R M37 R M38 R M39 and nx are respectively related to R in equation (M1-1) M21 R M22 R M23 R M24 R M25 R M26 R M27 R M28 R M29 R M30 R M31 R M32 R M33 R M34 R M35 R M36 R M37 R M38 R M39 The meanings of 'nx' and 'nx' are the same, and their preferred ranges are also the same.

[0408] The compound represented by formula (M1-1) is preferably the compound represented by formula (M1-3) below, and more preferably the compound represented by formula (M1-4) below.

[0409]

[0410] (In formula (M1-3), nx represents an integer greater than 1 and less than 20.)

[0411] nx can be an integer less than 10.

[0412]

[0413] (In formula (M1-4), nx represents an integer greater than 1 and less than 20.)

[0414] nx can be an integer less than 10.

[0415] The molecular weight of the compound represented by formula (M1) is preferably 500 or more, more preferably 600 or more, and even more preferably 700 or more. By setting the molecular weight to the lower limit or above mentioned above, there is a tendency to further improve the low dielectric properties (Dk and / or Df) and low water absorption of the obtained cured product. Furthermore, the molecular weight of the compound represented by formula (M1) is preferably 10,000 or less, more preferably 9,000 or less, even more preferably 7,000 or less, even more preferably 5,000 or less, and even more preferably 4,000 or less. By setting the molecular weight to the upper limit or below mentioned above, there is a tendency to further improve the heat resistance and workability of the obtained cured product.

[0416] The maleimide equivalent of the compound represented by formula (M1) is preferably 50 g / eq. or more, more preferably 100 g / eq. or more, and even more preferably 200 g / eq. or more. The upper limit of the maleimide equivalent is preferably 2000 g / eq. or less, more preferably 1000 g / eq. or less, and even more preferably 800 g / eq. or less. Here, the maleimide equivalent represents the mass of the maleimide compound per 1 equivalent of maleimide groups. When the maleimide equivalent of the compound represented by formula (M1) is within the above range, there is a tendency for further improvements in the low dielectric properties (Dk and / or Df), low water absorption, heat resistance, and workability of the resulting cured product.

[0417] The molecular weight distribution Mw / Mn of the compound represented by formula (M1), as determined by gel permeation chromatography (GPC), is preferably 1.0 to 4.0, more preferably 1.1 to 3.8, even more preferably 1.2 to 3.6, and still more preferably 1.3 to 3.4. When the Mw / Mn of the compound represented by formula (M1) is within the above range, there is a tendency for the resulting cured product to have further improved low dielectric properties (Dk and / or Df), low water absorption, heat resistance, and workability.

[0418] Furthermore, details of the compound represented by formula (M1) can be found in International Publication No. 2020-217679, which is incorporated herein by reference.

[0419]

[0420] (In formula (M2), R) 54 Each can independently represent a hydrogen atom or a methyl group, and n4 represents an integer greater than or equal to 1.

[0421] n4 is preferably an integer from 1 to 10, more preferably an integer from 1 to 5, even more preferably an integer from 1 to 3, and even more preferably 1 or 2, or it can be 1.

[0422] The compound represented by formula (M2) can be a mixture of n4 different compounds, preferably a mixture. Alternatively, as described in the part of the compound represented by formula (M0), it can be a mixture of compounds with different other parts.

[0423]

[0424] (In formula (M3), R) 55 Each of these can independently represent a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or a phenyl group; n5 represents an integer greater than 1 and less than 10.

[0425] R 55 Each is preferably selected independently from the group consisting of hydrogen atom, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl and phenyl, more preferably hydrogen atom and / or methyl, and even more preferably hydrogen atom.

[0426] n5 is preferably an integer greater than or equal to 1 and less than or equal to 5, more preferably an integer from 1 to 3, and even more preferably 1 or 2.

[0427] The compound represented by formula (M3) can be a mixture of n5 different compounds, preferably a mixture. Alternatively, as described in the part of the compound represented by formula (M0), it can be a mixture of compounds with different other parts.

[0428]

[0429] (In formula (M4), R) 56 Each can independently represent a hydrogen atom, a methyl group, or an ethyl group; R 57 Each can independently represent a hydrogen atom or a methyl group.

[0430] An example of the compound represented by formula (M4) is R. 56 Each is independently methyl or ethyl, R 57 It is methyl. The above R 56 More preferably, each of the two benzene rings is methyl and ethyl.

[0431] Another example of a compound represented by formula (M4) is R. 56 and R 57 It is a hydrogen atom.

[0432]

[0433] (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 can independently represent a hydrogen atom or a methyl group, and n6 represents an integer greater than or equal to 1.

[0434] R58 Each is preferably selected independently from the group consisting of hydrogen atom, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl and phenyl, more preferably hydrogen atom and / or methyl, and even more preferably hydrogen atom.

[0435] R 59 Methyl is preferred.

[0436] n6 is preferably an integer from 1 to 10, more preferably an integer from 1 to 5, even more preferably an integer from 1 to 3, and even more preferably 1 or 2, or it can be 1.

[0437] The compound represented by formula (M5) can be a mixture of n6 different compounds, preferably a mixture. Alternatively, as described in the part of the compound represented by formula (M0), it can be a mixture of compounds with different other parts.

[0438] Maleimide compound (M6) is a compound having a structural unit represented by formula (M6) and maleimide groups at both ends of the molecular chain.

[0439]

[0440] (In formula (M6), R) 61 R represents a straight-chain or branched alkylene group having 1 to 16 carbon atoms, or a straight-chain or branched alkenyl group having 2 to 16 carbon atoms. 62 R represents a straight-chain or branched alkylene group having 1 to 16 carbon atoms, or a straight-chain or branched alkenyl group having 2 to 16 carbon atoms. 63 Each group independently represents a straight-chain or branched alkyl group having 1 to 16 carbon atoms, or a straight-chain or branched alkenyl group having 2 to 16 carbon atoms. Each group independently represents an integer from 0 to 10.

[0441] For details of the maleimide compound (M6) and its manufacturing method, please refer to paragraphs 0061 to 0066 of International Publication No. 2020 / 262577, the contents of which are incorporated herein by reference.

[0442] The maleimide compound (M7) is a maleimide compound that uses an aromatic amine compound (a1) having one or more but three or fewer alkyl groups on an aromatic ring, an aromatic divinyl compound (a2) having two vinyl groups, and maleic anhydride as reactants (1).

[0443] The maleimide compound (M7) is preferably a compound represented by formula (M7).

[0444]

[0445] (In the above formula (M7), R)1 Each independently represents an alkyl group having 1 to 10 carbon atoms, R 2 Each of these groups independently represents an alkyl group (1-10 carbon atoms), an alkoxy group (1-10 carbon atoms), an alkylthio group (1-10 carbon atoms); an aryl group (6-10 carbon atoms), an aryloxy group (6-10 carbon atoms), an arylthio group (6-10 carbon atoms); a cycloalkyl group (3-10 carbon atoms); a halogen atom; a hydroxyl group; or a mercapto group.

[0446] R 3 R 4 R 5 and R 6 Each can independently represent a hydrogen atom or a methyl group, and R 3 and R 4 One of them is a hydrogen atom, and the other is a methyl group, R 5 and R 6 One of them is a hydrogen atom, and the other is a methyl group.

[0447] X 1 Each is an independent substituent as shown in equation (x) below.

[0448]

[0449] (In equation (x), R) 7 and R 8 Each can independently represent a hydrogen atom or a methyl group, and R 7 and R 8 One of them is a hydrogen atom, and the other is a methyl group, R 9 Each of these groups independently represents an alkyl group (1-10 carbon atoms), an alkoxy group (1-10 carbon atoms), an alkylthio group (1-10 carbon atoms); an aryl group (6-10 carbon atoms), an aryloxy group (6-10 carbon atoms), an arylthio group (6-10 carbon atoms); a cycloalkyl group (3-10 carbon atoms); a halogen atom; a hydroxyl group; or a mercapto group, where t represents an integer from 0 to 4.

[0450] r represents the number of X bonds per bond. 1 X of the benzene ring 1 The average of the substitution numbers, where p represents an integer from 1 to 3, q ​​represents an integer from 0 to 4, and k represents an integer from 1 to 100.

[0451] For details regarding the maleimide compound (M7) used in this embodiment, please refer to Japanese Patent No. 7160151, the contents of which are incorporated herein by reference.

[0452] Maleimide compound (M8) is a maleimide compound having eight or more hydrocarbon groups linked in a straight chain, preferably a compound represented by formula (M8). Such maleimide compound (M8) tends to have higher stress relief ability, resulting in a tendency for a further reduction in the thermal expansion coefficient of the cured product, and tends to have better dielectric constant and dielectric loss tangent isoelectric properties.

[0453]

[0454] (In formula (M8), R) 1 and R 3 Each can independently represent a hydrocarbon group consisting of eight or more atoms linked in a straight chain, R 2 Each group independently represents a cyclic hydrocarbon group, whether substituted or unsubstituted, consisting of 4 or more but less than 10 atoms forming the ring, and may contain heteroatoms; n represents a number from 1 to 10.

[0455] In formula (M8), R is preferred. 1 and R 3 For Yasinki, R 2 Cycloalkylene compounds with alkyl groups having 6 to 8 carbon atoms as substituents.

[0456] As for the maleimide compound (M8), please refer to paragraphs 0014 to 0022 of Japanese Patent Application Publication No. 2018-083893, which are incorporated herein by reference.

[0457] Maleimide compounds can be manufactured using known methods or commercially available products. Examples of commercially available products include: KI Chemical Co., Ltd.'s "BMI-80" (component of formula (M0)); DIC Co., Ltd.'s "NE-X-9470S" and "NE-X-9480S" (components of formula (M1)); Yamato Chemical Industry Co., Ltd.'s "BMI-2300" (component of formula (M2)); Nippon Kayaku Co., Ltd.'s "MIR-3000-70MT" (component of formula (M3)); and others. The compounds shown are: KI Chemical Co., Ltd.'s "BMI-70", Nippon Kayaku Co., Ltd.'s "MIR-5000", Nippon Kayaku Co., Ltd.'s "MIZ-001", Nippon Kayaku Co., Ltd.'s "MIZ-001", DIC Co., Ltd.'s "NE-X-9500", Resonac Co., Ltd.'s "SFR", DIC Co., Ltd.'s "SFR", Resonac Co., Ltd.'s "SFR", DIC Co., Ltd.'s "BMI-689", "BMI-1500", "BMI-2500", "BMI-3000", and "BMI-5000", all manufactured by DESIGNER MOLECULES INC.

[0458] In addition to the above, as maleimide compounds, reference can be made to compounds described in paragraphs 0061 to 0066 of International Publication No. 2020 / 262577 and Japanese Patent No. 7160151, the contents of which are incorporated herein by reference.

[0459] In addition, examples of maleimide compounds other than those mentioned above include, for example, N-phenylmaleimide, N-cyclohexylmaleimide, oligomers of phenylmethane maleimide, m-phenylene bismaleimide, 2,2-bis(4-(4-maleimidephenoxy)-phenyl)propane, 4-methyl-1,3-phenylene bismaleimide, 1,6-bismaleimide-(2,2,4-trimethyl)hexane, 4,4'-diphenyl ether bismaleimide, 4,4'-diphenyl sulfone bismaleimide, 1,3-bis(3-maleimidephenoxy)benzene, 1,3-bis(4-maleimidephenoxy)benzene, and their prepolymers, as well as prepolymers of these maleimides and amines.

[0460] Among them, monofunctional maleimide compounds such as N-phenylmaleimide and N-cyclohexylmaleimide tend to produce resin compositions that provide better low dielectric properties when used in combination with polymers having structural units shown in the following formula (V).

[0461] The maleimide equivalent of the maleimide compound is preferably 130 g / eq. or more, more preferably 150 g / eq. or more, further preferably 170 g / eq. or more, even more preferably 180 g / eq. or more, even more preferably 200 g / eq. or more, and preferably 1000 g / eq. or less, more preferably 800 g / eq. or less, even more preferably 700 g / eq. or less, even more preferably 600 g / eq. or less, and even more preferably 500 g / eq. or less. By setting the value above the lower limit, the resulting cured product tends to have superior low dielectric properties (Dk and / or Df, especially Df). Furthermore, by setting the value below the upper limit, the peel strength tends to be superior.

[0462] When the resin composition of this embodiment contains a maleimide compound (preferably a compound represented by formula (M1)), the lower limit of its content relative to 100 parts by mass of the resin solids in the resin composition is preferably 1 part by mass or more, more preferably 5 parts by mass or more, further preferably 10 parts by mass or more, and can be 20 parts by mass or more. By setting the content of the maleimide compound to the above-mentioned lower limit or above, there is a tendency for the resulting cured product to have improved low dielectric properties and flame retardancy. In addition, the upper limit of the content of the maleimide compound relative to 100 parts by mass of the resin solids in the resin composition is preferably 70 parts by mass or less, more preferably 60 parts by mass or less, further preferably 50 parts by mass or less, and can also be 40 parts by mass or less. By setting the content of the maleimide compound to the above-mentioned upper limit or less, there is a tendency for improved metal foil peel strength and low water absorption.

[0463] The resin composition in this embodiment may contain only one maleimide compound, or it may contain two or more. When it contains two or more, the total amount is preferably within the range described above.

[0464] <<Polymers with the structural units shown in formula (V)>>

[0465] The resin composition of this embodiment may contain a polymer having structural units shown in Formula (V). By containing a polymer having structural units shown in Formula (V), a resin composition capable of providing a cured product with excellent low dielectric properties (Dk and / or Df) can be obtained.

[0466]

[0467] (In formula (V), Ar represents an aromatic hydrocarbon linking group. * indicates a bonding position.)

[0468] The aromatic hydrocarbon linking group can be a group consisting only of aromatic hydrocarbons optionally having substituents, or a group consisting of an aromatic hydrocarbon optionally having substituents combined with other linking groups, preferably a group consisting only of aromatic hydrocarbons optionally having substituents. It should be noted that examples of substituents optionally present in the aromatic hydrocarbon include substituent Z (e.g., alkyl groups having 1 to 6 carbon atoms, alkenyl groups having 2 to 6 carbon atoms, alkynyl groups having 2 to 6 carbon atoms, alkoxy groups having 1 to 6 carbon atoms, hydroxyl groups, amino groups, carboxyl groups, halogen atoms, etc.). Furthermore, the aforementioned aromatic hydrocarbons preferably do not have substituents.

[0469] Aromatic hydrocarbons typically have a divalent linker group.

[0470] Specifically, the aromatic hydrocarbon linking group can be substituted with phenylene, naphthyl, anthracenediyl, phenanthrenediyl, biphenyldiyl, or fluorenediyl, with substituted phenylene being preferred. Substituents can be exemplified by the substituent Z described above, but the aforementioned phenylene and other groups are preferably unsubstituented.

[0471] The structural unit shown in equation (V) more preferably includes at least one of the structural unit shown in equation (V1), the structural unit shown in equation (V2), and the structural unit shown in equation (V3). Additionally, * in the following equations indicates a bonding position. Furthermore, hereinafter, the structural units represented by equations (V1) to (V3) are sometimes collectively referred to as "structural unit (a)".

[0472]

[0473] In equations (V1) to (V3), L 1 The linking group is an aromatic hydrocarbon (preferably 6 to 22 carbon atoms, more preferably 6 to 18, and even more preferably 6 to 10). Specifically, examples include phenylene, naphthyl, anthracenediyl, phenanthrenediyl, biphenyldiyl, and fluorenediyl, which are optionally substituents, with phenylene being the most preferred. Substituents can be exemplified by substituent Z described above, but the aforementioned phenylene and other groups are preferably unsubstituents.

[0474] The compound forming structural unit (a) is preferably a divinyl aromatic compound, such as divinylbenzene, bis(1-methylvinyl)benzene, divinylnaphthalene, divinylanthracene, divinylbiphenyl, divinylphenanthrene, etc. Divinylbenzene is particularly preferred. One of these divinyl aromatic compounds may be used, or two or more may be used as needed.

[0475] That is, the structural unit (a) is preferably a structural unit derived from a divinyl aromatic compound.

[0476] As described above, a polymer having the structural unit shown in formula (V) can be a homopolymer of structural unit (a) or a copolymer of structural units derived from other monomers.

[0477] When the polymer having the structural unit shown in formula (V) is a copolymer, regarding its copolymerization ratio, structural unit (a) is preferably 3 mol% or more, more preferably 5 mol% or more, even more preferably 10 mol% or more, and may also be 15 mol% or more. As an upper limit, it is preferably 90 mol% or less, more preferably 85 mol% or less, even more preferably 80 mol% or less, even more preferably 70 mol% or less, even more preferably 60 mol% or less, even more preferably 50 mol% or less, even more preferably 40 mol% or less, particularly preferably 30 mol% or less, and may further be 25 mol% or less, or 20 mol% or less.

[0478] As a structural unit derived from other monomers, an example can be given (b) of a structural unit derived from an aromatic compound having one vinyl group (monovinyl aromatic compound).

[0479] The structural unit (b) derived from a monovinyl aromatic compound is preferably the structural unit shown in the following formula (V4).

[0480]

[0481] In equation (V4), L 2 As a preferred example of an aromatic hydrocarbon linking group, the L group mentioned above can be cited. 1 Examples. * indicates the bonding location.

[0482] R V1 R represents a hydrogen atom or a hydrocarbon group (preferably an alkyl group) having 1 to 12 carbon atoms. V1 When it is a hydrocarbon group, the number of carbon atoms is preferably 1 to 6, more preferably 1 to 3. V1 and L 2 It can have the substituent Z mentioned above.

[0483] When the polymer having the structural unit shown in formula (V) is a copolymer containing structural unit (b) derived from a monovinyl aromatic compound, examples of monovinyl aromatic compounds include vinyl aromatic compounds such as styrene, vinylnaphthalene, and vinyl biphenyl; and nucleoalkyl-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 illustrated herein may suitably have the aforementioned substituent Z. Furthermore, one or more of these monovinyl aromatic compounds may be used. Preferably, structural unit (b) contains at least one structural unit derived from the group consisting of o-ethylvinylbenzene, m-ethylvinylbenzene, and p-ethylvinylbenzene, and more preferably, in addition to containing at least one structural unit derived from the group consisting of o-ethylvinylbenzene, m-ethylvinylbenzene, and p-ethylvinylbenzene, it also contains a structural unit derived from styrene.

[0484] When the polymer having the structural unit shown in formula (V) is a copolymer containing structural unit (b), the copolymerization ratio of structural unit (b) is preferably 10 mol% or more, more preferably 15 mol% or more, and may also be 20 mol% or more, 30 mol% or more, 40 mol% or more, 50 mol% or more, 60 mol% or more, 70 mol% or more, or 75 mol% or more. As an upper limit, it is preferably 98 mol% or less, more preferably 90 mol% or less, and even more preferably 85 mol% or less.

[0485] Polymers having the structural unit shown in formula (V) may also have structural units other than structural units (a) and (b). Examples of other structural units include structural units (c) derived from cyclic olefin compounds. Examples of cyclic olefin compounds include hydrocarbons having double bonds within a ring structure. Specifically, in addition to monocyclic cyclic olefins such as cyclobutene, cyclopentene, cyclohexene, and cyclooctene, examples include compounds with a norbornene ring structure such as norbornene and dicyclopentadiene, and cyclic olefin compounds formed by the fusion of aromatic rings such as indene and acenaphthene. Examples of norbornene compounds include compounds described in paragraphs 0037 to 0043 of Japanese Patent Application Publication No. 2018-039995, the contents of which are incorporated herein by reference. It should be noted that the cyclic olefin compounds illustrated herein may further have the aforementioned substituent Z.

[0486] When the polymer having the structural unit shown in formula (V) is a copolymer containing structural unit (c), the copolymerization ratio of structural unit (c) is preferably 10 mol% or more, more preferably 20 mol% or more, and even more preferably 30 mol% or more. As an upper limit, it is preferably 90 mol% or less, more preferably 80 mol% or less, even more preferably 70 mol% or less, and can be 50 mol% or less, or 30 mol% or less.

[0487] In polymers having the structural units shown in formula (V), structural units (d) derived from different polymeric compounds (hereinafter also referred to as other polymeric compounds) may be incorporated. Examples of other polymeric compounds (monomers) include compounds containing three vinyl groups. Specifically, examples include 1,3,5-trivinylbenzene, 1,3,5-trivinylnaphthalene, and 1,2,4-trivinylcyclohexane. Alternatively, examples include ethylene glycol diacrylate, butadiene (e.g., 1,3-butadiene), and isoprene. The copolymerization ratio of structural units (d) derived from other polymeric compounds is preferably 30 mol% or less, more preferably 20 mol% or less, and even more preferably 10 mol% or less.

[0488] As one embodiment of a polymer having the structural unit shown in formula (V), a polymer in which structural unit (a) is essential and includes at least one of structural units (b) and (c) can be exemplified. Furthermore, an embodiment in which the total of structural units (a) to (c) accounts for 90 mol% or more, more specifically 95 mol% or more, and particularly 98 mol% or more of all structural units can be exemplified.

[0489] As another embodiment of a polymer having the structural unit shown in formula (V), a polymer in which structural unit (a) is essential and includes at least one of structural units (b) to (d) can be exemplified. Furthermore, an embodiment in which the total of structural units (a) to (d) accounts for 95 mol% or more, and further 98 mol% or more of all structural units can be exemplified.

[0490] As another embodiment of a polymer having the structural unit shown in formula (V), it is preferably a polymer in which structural unit (a) is required and all structural units except the end contain aromatic rings, with a structural unit percentage of 90 mol% or more, more preferably 95 mol% or more, and may also be 100 mol% polymer.

[0491] It should be noted that when calculating the mole % relative to all structural units, one structural unit refers to one molecule of a monomer (e.g., a divinyl aromatic compound, a monovinyl aromatic compound, etc.) used in the manufacture of a polymer having the structural unit shown in formula (V).

[0492] There are no particular limitations on the method for manufacturing polymers having the structural units shown in formula (V). Conventional methods can be used, for example, polymerizing raw materials containing divinyl aromatic compounds (with monovinyl aromatic compounds, cycloolefin compounds, etc., coexisting as needed) in the presence of a Lewis acid catalyst. As a Lewis acid catalyst, metal fluorides such as boron trifluoride or their complexes can be used.

[0493] The structure of the chain ends of polymers having the structural units shown in formula (V) is not particularly limited. However, regarding the groups derived from divinyl aromatic compounds, structures of formula (E1) can be cited as examples. It should be noted that L in formula (E1)... 1 Same as specified in equation (V1) above. * indicates the bonding position.

[0494] *-CH=CH-L 1 -CH=CH2(E1)

[0495] When the group derived from a monovinyl aromatic compound becomes the chain terminator, a structure taking the form of the following formula (E2) can be cited. In the formula, L... 2 and R V1 These are the same as those defined in equation (V4) above. * indicates the bonding position.

[0496] *-CH=CH-L 2 -R V1 (E2)

[0497] The polymer having the structural unit shown in formula (V) preferably has a molecular weight of 300 or more, more preferably 500 or more, further preferably 1,000 or more, and more preferably 1,500 or more, in terms of number average molecular weight Mn. As an upper limit for the number average molecular weight Mn, it is preferably 130,000 or less, more preferably 120,000 or less, further preferably 110,000 or less, and even more preferably 100,000 or less, but can be 30,000 or less, 10,000 or less, or 5,000 or less.

[0498] The molecular weight of the polymer having the structural unit shown in Formula (V), expressed as weight-average molecular weight Mw, is preferably 3,000 or more, more preferably 5,000 or more, and even more preferably 10,000 or more. By setting the weight-average molecular weight Mw to the lower limit or above, the cured resin composition can effectively exhibit the excellent low dielectric properties (Dk and / or Df, especially Df) and moisture-absorbing dielectric properties of the polymer having the structural unit shown in Formula (V). As the upper limit of the weight-average molecular weight Mw, it 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 setting the weight-average molecular weight Mw to the upper limit or below, there is a tendency for poor embedding to occur when the prepreg or resin sheet is laminated on the circuit forming substrate.

[0499] The monodispersity (Mw / Mn), expressed as the ratio of weight-average molecular weight Mw to number-average molecular weight Mn, is preferably 100 or less, more preferably 50 or less, even more preferably 20 or less, and can be 15 or less, or 12 or less. As a lower limit, 1.1 or more is practical, preferably 2.0 or more, more preferably 4 or more, even more preferably 5 or more, even more preferably 7 or more, and even more preferably 8 or more. The above-described Mw and Mn are measured according to the embodiments described later.

[0500] When the resin composition of this embodiment contains two or more polymers having structural units shown in formula (V), it is preferable that the Mw, Mn, and Mw / Mn of the mixture satisfy the above range.

[0501] The vinyl equivalent of the polymer having the structural unit shown in formula (V) is preferably 200 g / eq. or more, more preferably 230 g / eq. or more, and even more preferably 250 g / eq. or more, and can be 300 g / eq. or more or 350 g / eq. Furthermore, the vinyl equivalent is preferably 1200 g / eq. or less, more preferably 1000 g / eq. or less, and even more preferably 800 g / eq. or less, 600 g / eq. or less, 400 g / eq. or less, or 300 g / eq. or less. By setting it to the lower limit or above, there is a tendency to improve the storage stability of the resin composition and the flowability of the resin composition. Therefore, the formability is improved, and voids are less likely to be generated during the formation of prepregs, etc., resulting in a tendency to obtain printed circuit boards with higher reliability. On the other hand, by setting it to the upper limit or below, there is a tendency to improve the heat resistance of the cured product.

[0502] The glass transition temperature of the polymer having the structural unit shown in formula (V) is preferably 170°C or higher, more preferably 180°C or higher, even more preferably 190°C or higher, and even more preferably 200°C or higher. As an upper limit for the glass transition temperature, it is preferably 350°C or lower, and may also be 300°C or lower. For the glass transition temperature, a dynamic viscoelasticity measuring device can be used, according to JIS-K7244-4:1999 (Plastics—Test methods for dynamic mechanical properties—Part 4: Non-resonance method), to measure the dynamic viscoelasticity of the sample under a nitrogen atmosphere at an initial temperature of 30°C, an ending temperature of 400°C, a heating rate of 5°C / min, a measuring frequency of 1Hz, and to determine the maximum value of the loss tangent (tanσ) obtained at this time as the glass transition temperature. As a dynamic viscoelasticity measuring device, the EXSTAR6000 DMS6100 manufactured by Seiko Instruments Co., Ltd. can be used.

[0503] Polymers having the structural unit shown in Formula (V) preferably exhibit excellent low dielectric properties in their cured products. For example, in this embodiment, the relative permittivity (Dk) of the cured product of the polymer having the structural unit shown in Formula (V) at 10 GHz, measured by the resonant cavity perturbation method, is preferably 2.80 or less, more preferably 2.60 or less, further preferably 2.50 or less, and even more preferably 2.40 or less. Furthermore, a lower limit value for the relative permittivity is, for example, 1.80 or more. Also, the dielectric loss tangent (Df) of the cured product of the polymer having the structural unit shown in Formula (V) at 10 GHz, measured by the resonant cavity perturbation method, is preferably 0.0030 or less, more preferably 0.0020 or less, and even more preferably 0.0010 or less. Furthermore, a lower limit value for the dielectric loss tangent is, for example, 0.0001 or more.

[0504] The relative permittivity (Dk) and dielectric loss tangent (Df) were determined by the following method.

[0505] 4.5g of resin powder was spread into a stainless steel mold with a height of 100mm×30mm×1.0mm, placed in a vacuum press (made by Kitagawa Seiki Co., Ltd.), and kept at 200℃, 220℃ and 240℃ for 1.5 hours. The mold was then pressed with a surface pressure of 1.9MPa to produce a cured board.

[0506] After reducing the size of the cured plate to 1.0 mm in width, it was dried at 120°C for 60 minutes. Then, the relative permittivity (Dk) and dielectric loss tangent (Df) of the dried plate were measured at 10 GHz using a perturbation method cavity resonator. The measurement temperature was set to 23°C.

[0507] The perturbation method cavity resonator used is the P5005A manufactured by Keysight Technology.

[0508] In this specification, for polymers having structural units represented by formula (V), reference can be made to compounds and their synthesis reaction conditions described in paragraphs 0029 to 0058 of International Patent Publication No. 2017 / 115813, compounds and their synthesis reaction conditions described in paragraphs 0013 to 0058 of Japanese Patent Application Publication No. 2018-039995, and compounds and their synthesis reaction conditions described in paragraphs 0008 to 0043 of Japanese Patent Application Publication No. 2018-168347. Compounds and their synthesis reaction conditions, compounds and their synthesis reaction conditions described in paragraphs 0014 to 0042 of Japanese Patent Application Publication No. 2006-070136, compounds and their synthesis reaction conditions described in paragraphs 0014 to 0061 of Japanese Patent Application Publication No. 2006-089683, and compounds and their synthesis reaction conditions described in paragraphs 0008 to 0036 of Japanese Patent Application Publication No. 2008-248001 are included in this specification.

[0509] Polymers having the structural units shown in formula (V) can also be commercially available, such as LF-310T50 manufactured by Nippon Steel Chemical Materials Co., Ltd.

[0510] When the resin composition of this embodiment contains a polymer having the structural unit shown in Formula (V), the lower limit of its content relative to 100 parts by mass of resin solids in the resin composition is preferably 1 part by mass or more, more preferably 10 parts by mass or more, and even more preferably 20 parts by mass or more. It can be 25 parts by mass or more, 30 parts by mass or more, 40 parts by mass or more, 50 parts by mass or more, or 60 parts by mass or more. By making the content of the polymer having the structural unit shown in Formula (V) at or above the above-mentioned lower limit, there is a tendency to effectively achieve low dielectric properties (Dk and / or Df), especially low relative permittivity, in the resulting cured product. In addition, the upper limit of the content of the polymer having the structural unit shown in Formula (V) relative to 100 parts by mass of resin solids in the resin composition is preferably 90 parts by mass or less, more preferably 80 parts by mass or less, and even more preferably 70 parts by mass or less, 60 parts by mass or less, 50 parts by mass or less, 40 parts by mass or less, or 30 parts by mass or less. By setting the content of the polymer having the structural unit shown in formula (V) below the above-mentioned upper limit, there is a tendency to improve the peel strength and low water absorption of the metal foil.

[0511] The resin composition in this embodiment may contain only one polymer having the structural unit shown in formula (V), or it may contain two or more polymers. When containing two or more polymers, the total amount is preferably within the range described above.

[0512] Alternatively, the resin composition in this embodiment may also be composed of polymers that substantially do not contain the structural units shown in formula (V). "Substantially not containing" means that the content of polymers having the structural units shown in formula (V) is less than 1 part by mass relative to 100 parts by mass of the resin solids component in the resin composition, preferably less than 0.1 parts by mass, and more preferably less than 0.01 parts by mass.

[0513] <<Epoxy Resin>>

[0514] The resin composition of this embodiment may contain epoxy resin.

[0515] Epoxy resin is not particularly limited as long as it is a compound or resin having one or more epoxy groups in one molecule (preferably 2 to 12, more preferably 2 to 6, further preferably 2 to 4, even more preferably 2 or 3, and even more preferably 2), and can be widely used in the field of printed circuit boards.

[0516] Examples of epoxy resins include bisphenol A type epoxy resin, bisphenol E type epoxy resin, bisphenol F type epoxy resin, bisphenol S type epoxy resin, phenolic varnish type epoxy resin, bisphenol A phenolic varnish type epoxy resin, glycidyl ester type epoxy resin, aralkyl phenolic varnish type epoxy resin, biphenyl aralkyl type epoxy resin, naphthyl ether type epoxy resin, cresol phenolic varnish type epoxy resin, polyfunctional phenol type epoxy resin, naphthalene type epoxy resin, anthracene type epoxy resin, naphthalene skeleton modified phenolic varnish type epoxy resin, phenolic aralkyl type epoxy resin, naphthol aralkyl type epoxy resin, dicyclopentadiene type epoxy resin, biphenyl type epoxy resin, alicyclic epoxy resin, polyol type epoxy resin, phosphorus-containing epoxy resin, compounds formed by epoxidation of double bonds of glycidylamine, glycidyl ester, butadiene, etc., and compounds obtained by the reaction of hydroxyl-containing organosilicon resins with epichlorohydrin, etc. From the viewpoint of further improving flame retardancy and heat resistance, the preferred types of epoxy resins are biphenyl aralkyl type epoxy resins, naphthyl ether type epoxy resins, polyfunctional phenol type epoxy resins, and naphthalene type epoxy resins, with biphenyl aralkyl type epoxy resins being more preferred.

[0517] The resin composition of this embodiment preferably includes epoxy resin within a range that does not impair the effects of the present invention. From the viewpoint of formability and adhesion, when the resin composition of this embodiment includes epoxy resin, its content relative to 100 parts by mass of the resin solids in the resin composition is preferably 0.1 parts by mass or more, more preferably 1 part by mass or more, and even more preferably 2 parts by mass or more. By making the epoxy resin content 0.1 parts by mass or more, there is a tendency to improve the peel strength and toughness of the metal foil. When the resin composition of this embodiment includes epoxy resin, the upper limit of the epoxy resin content relative to 100 parts by mass of the resin solids in the resin composition is preferably 50 parts by mass or less, more preferably 30 parts by mass or less, even more preferably 20 parts by mass or less, even more preferably 10 parts by mass or less, even more preferably 8 parts by mass or less, and even more preferably 5 parts by mass or less. By making the epoxy resin content 50 parts by mass or less, there is a tendency to improve the electrical properties.

[0518] The resin composition in this embodiment may contain only one type of epoxy resin, or it may contain two or more types. When it contains two or more types, the total amount is preferably within the range described above.

[0519] Alternatively, the resin composition in this embodiment may also be substantially free of epoxy resin. "Substantially free" means that the content of epoxy resin is less than 0.1 parts by weight relative to 100 parts by weight of the resin solids in the resin composition.

[0520] <<Phenolic Compounds>>

[0521] The resin composition of this embodiment may contain phenolic compounds.

[0522] Phenolic compounds are not particularly limited as long as they are compounds that have one or more phenolic hydroxyl groups in one molecule (preferably 2 to 12, more preferably 2 to 6, even more preferably 2 to 4, even more preferably 2 or 3, even more preferably 2), and can be widely used in the field of printed circuit boards.

[0523] Examples of the aforementioned phenolic compounds include phenolic varnish resins, bisphenol A type phenolic varnish resins, glycidyl ester type phenolic resins, aralkyl phenolic varnish resins, biphenyl aralkyl type phenolic resins, cresol phenolic varnish resins, polyfunctional phenolic resins, naphthol resins, naphthol phenolic varnish resins, polyfunctional naphthol resins, anthracene type phenolic resins, naphthalene skeleton modified phenolic varnish resins, phenolic aralkyl type phenolic resins, naphthol aralkyl type phenolic resins, dicyclopentadiene type phenolic resins, biphenyl type phenolic resins, alicyclic phenolic resins, polyol type phenolic resins, phosphorus-containing phenolic resins, and hydroxyl-containing organosilicon resins. From the viewpoint of further improving the flame retardancy of the obtained cured product, at least one type selected from the group consisting of biphenyl aralkyl type phenolic resins, naphthol aralkyl type phenolic resins, phosphorus-containing phenolic resins, and hydroxyl-containing organosilicon resins is preferred.

[0524] As another example of phenolic compounds that can be used in this embodiment, a resin having hydroxyl groups can be obtained by reacting a mixture of a compound containing formula (DIP) and a compound containing formula (P1).

[0525]

[0526] (In formula (DIP), Ma independently represents a hydrocarbon group with 1 to 12 carbon atoms that are optionally substituted with halogen atoms. x represents an integer from 0 to 4.)

[0527]

[0528] (In formula (P1), Mb independently represents a hydroxyl group, a halogen atom, or a hydrocarbon group with 1 to 20 carbon atoms that is optionally substituted by a hydroxyl or halogen atom. y represents an integer from 0 to 4.)

[0529] Formula (DIP) has the same meaning as that described in the resin (IP1) item, and the preferred range is also the same.

[0530] In formula (P1), Mb and y have the same meaning as Mb and y in formula (T-St), and the preferred range is also the same.

[0531] Details of the hydroxyl-containing resin obtained by reacting a mixture of the compound represented by formula (DIP) and the compound represented by formula (P1) can be found in Japanese Patent Application 2022-180443, the contents of which are incorporated herein by reference.

[0532] As another example of a phenolic compound that can be used in this embodiment, a hydroxyl resin represented by formula (T-OH) can be exemplified.

[0533]

[0534] In formula (T-OH), R is a group that contains the structural unit shown in formula (Tx). tp (Mb represents a hydrogen atom, hydroxyl group, isopropenyl group, or other group. Mb independently represents a hydroxyl group, a halogen atom, or a hydrocarbon group with 1 to 20 carbon atoms optionally substituted by a hydroxyl or halogen atom. y represents an integer from 0 to 4.)

[0535]

[0536] (In formula (Tx), n, o, and p are the average number of repeating units, where n represents a number greater than 0 and less than 20, o and p each independently represent a number from 0 to 20, and 1.0 ≤ n + o + p ≤ 20.0. Ma each independently represents a hydrocarbon group with 1 to 12 carbon atoms that are optionally substituted by a halogen atom. x represents an integer from 0 to 4. Structural units (a), (b), and (c) are bonded to structural units (a), (b), and (c) or other groups at *, and each structural unit is optionally bonded randomly.)

[0537] The formula (T-OH) is preferably represented by the formula (T-OH2), and more preferably by the formula (T-OH3).

[0538]

[0539] In formula (T-OH2), R' is a group that, together with the adjacent group on the left having an indane skeleton, forms a group containing the structural unit shown in the aforementioned formula (Tx). tp (Mb represents a hydrogen atom, hydroxyl group, isopropenyl group, or other group. Mb independently represents a hydroxyl group, a halogen atom, or a hydrocarbon group with 1 to 20 carbon atoms optionally substituted by a hydroxyl or halogen atom. y represents an integer from 0 to 4.)

[0540]

[0541] In formula (T-OH3), R' is a group that, together with the adjacent group on the left having an indene skeleton, forms a group containing the structural unit represented by the aforementioned formula (Tx). tp2 Indicates a hydroxyl or isopropenyl group. Mb independently represents a hydroxyl group, a halogen atom, or a hydrocarbon group with 1 to 20 carbon atoms optionally substituted by a hydroxyl or halogen atom. y represents an integer from 0 to 4.

[0542] In formula (T-OH), R has the same meaning as R in formula (T1-1) above, and the preferred range is also the same. Mb and y each independently have the same meaning as Mb and y in formula (T-St), and the preferred range is also the same. tp Preferably, it is hydroxyl or isopropenyl, more preferably hydroxyl.

[0543] In formulas (T-OH2) and (T-OH3), R' has the same meaning as R in formula (T1-1) above, and the preferred range is also the same. Mb and y each independently have the same meaning as Mb and y in formula (T-St), and the preferred range is also the same.

[0544] In formula (T-OH2), R tp Preferably, it is hydroxyl or isopropenyl, more preferably hydroxyl.

[0545] In formula (T-OH3), R tp2 Hydroxyl groups are preferred.

[0546] For details of the hydroxyl resins represented by formulas (T-OH1) to (T-OH3), please refer to the description in Japanese Patent Application 2022-180444, the contents of which are incorporated into this specification.

[0547] As another example of a phenolic compound that can be used in this embodiment, a hydroxyl resin of formula (T-OH4) can also be illustrated.

[0548]

[0549] (In formula (T-OH4), R is a group containing the structural unit shown in formula (Tx). Ma independently represents a hydrocarbon group of 1 to 12 carbons that is optionally substituted with a halogen atom. Mb independently represents a hydroxyl group, a halogen atom, or a hydrocarbon group of 1 to 20 carbons that is optionally substituted with a hydroxyl or halogen atom. x and y independently represent integers from 0 to 4.)

[0550]

[0551] (In formula (Tx), n, o, and p are the average number of repeating units, where n represents a number greater than 0 and less than 20, o and p each independently represent a number from 0 to 20, and 1.0 ≤ n + o + p ≤ 20.0. Ma each independently represents a hydrocarbon group with 1 to 12 carbon atoms that are optionally substituted by a halogen atom. x represents an integer from 0 to 4. Structural units (a), (b), and (c) are bonded to structural units (a), (b), and (c) or other groups at *, and each structural unit is optionally bonded randomly.)

[0552] In formula (T-OH4), Ma and x have the same meaning as Ma and x in formula (T1), and the preferred range is also the same.

[0553] In formula (T-OH4), Mb and y have the same meaning as Mb and y in formula (T-St) described later, and their preferred ranges are also the same.

[0554] In formula (T-OH4), R has the same meaning as R in formula (T-OH), and the preferred range is also the same.

[0555] For details of the hydroxyl resin represented by formula (T-OH4), please refer to paragraphs 0018 to 0019 of PCT / JP2023 / 009587, the contents of which are incorporated into this specification.

[0556] In addition to the above, detailed information about phenolic resins can be found in paragraph 0049 of International Publication No. 2021 / 172317, the contents of which are incorporated herein by reference.

[0557] The resin composition of this embodiment preferably contains a phenolic compound within a range that does not impair the effects of the present invention. When the resin composition of this embodiment contains a phenolic compound, its content is preferably 0.1 parts by weight or more, and more preferably 50 parts by weight or less, relative to 100 parts by weight of the resin solids in the resin composition.

[0558] The resin composition in this embodiment may contain only one phenolic compound, or it may contain two or more. When it contains two or more, the total amount is preferably within the range described above.

[0559] Alternatively, the resin composition in this embodiment may also be substantially free of phenolic compounds. "Substantially free" means that the content of phenolic compounds is less than 0.1 parts by mass relative to 100 parts by mass of the resin solids in the resin composition.

[0560] <<Oxycyclobutane Resins>>

[0561] The resin composition of this embodiment may contain an oxetane resin. Details of the oxetane resin can be found in paragraphs 0051 and 0052 of International Publication No. 2021 / 172317, the contents of which are incorporated herein by reference.

[0562] The resin composition of this embodiment preferably contains oxetane resin within a range that does not impair the effects of the present invention. When the resin composition of this embodiment contains oxetane resin, its content relative to 100 parts by mass of the resin solids in the resin composition is preferably 0.1 parts by mass or more, more preferably 1 part by mass or more, and even more preferably 2 parts by mass or more. With an oxetane resin content of 0.1 parts by mass or more, there is a tendency to improve the peel strength and toughness of the cured metal foil. When the resin composition of this embodiment contains oxetane resin, the upper limit of the oxetane resin content relative to 100 parts by mass of the resin solids in the resin composition is preferably 50 parts by mass or less, more preferably 30 parts by mass or less, even more preferably 20 parts by mass or less, even more preferably 10 parts by mass or less, and even more preferably 8 parts by mass or less. With an oxetane resin content of 50 parts by mass or less, there is a tendency to improve the electrical properties of the cured product.

[0563] The resin composition in this embodiment may contain only one type of oxetane resin, or it may contain two or more types. When it contains two or more types, the total amount is preferably within the range described above.

[0564] Alternatively, the resin composition in this embodiment may also be substantially free of oxetane resin. "Substantially free" means that the content of oxetane resin is less than 0.1 parts by weight relative to 100 parts by weight of the resin solids in the resin composition.

[0565] <<Benzoxazine Compounds>>

[0566] The resin composition of this embodiment may contain benzoxazine compounds.

[0567] As a benzoxazine compound, there are no particular limitations as long as it is a compound having two or more (preferably 2 to 12, more preferably 2 to 6, further preferably 2 to 4, even more preferably 2 or 3, even more preferably 2) dibenzoxazine rings in one molecule, and compounds commonly used in the field of printed circuit boards can be widely used.

[0568] Examples of benzoxazine compounds include bisphenol A type benzoxazine BA-BXZ (manufactured by Konishi Chemical Co., Ltd.), bisphenol F type benzoxazine BF-BXZ (manufactured by Konishi Chemical Co., Ltd.), and bisphenol S type benzoxazine BS-BXZ (manufactured by Konishi Chemical Co., Ltd.).

[0569] The resin composition of this embodiment preferably contains a benzoxazine compound within a range that does not impair the effects of the present invention. When the resin composition of this embodiment contains a benzoxazine compound, its content is preferably 0.1 parts by weight or more, and more preferably 50 parts by weight or less, relative to 100 parts by weight of the resin solids component in the resin composition.

[0570] The resin composition in this embodiment may contain only one benzoxazine compound, or it may contain two or more. When it contains two or more compounds, the total amount is preferably within the range described above.

[0571] Alternatively, the resin composition in this embodiment may also be substantially free of benzoxazine compounds. "Substantially free" means that the content of benzoxazine compounds is less than 0.1 parts by weight per 100 parts by weight of the resin solids in the resin composition.

[0572] <<Cyanate Compounds>>

[0573] The resin composition of this embodiment may contain cyanate ester compounds.

[0574] There are no particular limitations on cyanate compounds as long as they contain one or more cyanate groups (cyanoyl groups) in the molecule (preferably 2 to 12, more preferably 2 to 6, further preferably 2 to 4, even more preferably 2 or 3, even more preferably 2), and they can be widely used in the field of printed circuit boards.

[0575] The cyanate ester compound is preferably a cyanate ester compound commonly used in printed circuit boards that has two or more aromatic moieties that are substituted with at least one cyanoyl group.

[0576] Specifically, the lower limit of the number of cyanoyl groups in the cyanate ester compound is preferably 2 or more, more preferably 3 or more. By setting it to the above lower limit or above, there is a tendency to further improve the heat resistance. In addition, the upper limit of the number of cyanoyl groups is preferably 100 or less, more preferably 50 or less.

[0577] Furthermore, the cyanate ester compound preferably exhibits excellent low dielectric properties (Dk and / or Df) in its cured form. For example, the dielectric constant (Dk) of the cured cyanate ester compound at a frequency of 10 GHz, measured by the resonant cavity perturbation method, is preferably 4.0 or less, more preferably 3.5 or less. Additionally, a lower limit of 2.0 or more is practically acceptable for the dielectric constant. Furthermore, the dielectric loss tangent (Df) of the cured cyanate ester compound (B) at a frequency of 10 GHz, measured by the resonant cavity perturbation method, is preferably 0.02 or less, more preferably 0.015 or less. Additionally, a lower limit of 0.0001 or more is practically acceptable for the dielectric loss tangent. The dielectric constant and dielectric loss tangent can be measured, for example, according to the methods described in the examples (curing conditions, measurement conditions).

[0578] Furthermore, the cyanate ester compound preferably exhibits high heat resistance in its cured form. The glass transition temperature of the cured cyanate ester compound, as measured by dynamic viscoelasticity determination according to JISC 6481, is preferably 150°C or higher, more preferably 180°C or higher, and even more preferably 200°C or higher. By setting the glass transition temperature to or above the aforementioned lower limit, a cured form with excellent heat resistance can be obtained.

[0579] The weight-average molecular weight of the cyanate ester compound, converted from GPC-processed polystyrene, is preferably 200 or more, more preferably 300 or more, and even more preferably 400 or more. Setting the weight-average molecular weight to the lower limit or above tends to further improve heat resistance. Furthermore, the weight-average molecular weight of the cyanate ester compound is preferably 1000 or less, more preferably 900 or less, and even more preferably 800 or less. Setting the weight-average molecular weight to the upper limit or below tends to further improve formability and workability.

[0580] For a preferred range of cyanate compounds, reference can be made to paragraphs 0028 to 0033 of International Publication No. 2021 / 172317, the contents of which are incorporated herein by reference.

[0581] Preferred cyanate compounds include at least one selected from the group consisting of phenolic varnish-type cyanate compounds, naphthol aralkyl-type cyanate compounds (naphthol aralkyl-type cyanate compounds), naphthylene ether-type cyanate compounds, biphenyl aralkyl-type cyanate compounds, xylene resin-type cyanate compounds, triphenol methane-type cyanate compounds, adamantane skeleton-type cyanate compounds, bisphenol M-type cyanate compounds, and bisphenol A-type cyanate compounds. From the viewpoint of further improving low water absorption, the preferred option is at least one selected from the group consisting of phenolic varnish-type cyanate compounds, naphthol aralkyl-type cyanate compounds, naphthylene ether-type cyanate compounds, xylene resin-type cyanate compounds, bisphenol M-type cyanate compounds, and bisphenol A-type cyanate compounds. More preferably, it is at least one selected from the group consisting of phenolic varnish-type cyanate compounds, naphthol aralkyl-type cyanate compounds, naphthylene ether-type cyanate compounds, bisphenol A-type cyanate compounds, and bisphenol M-type cyanate compounds. Further preferably, it is at least one selected from the group consisting of phenolic varnish-type cyanate compounds, naphthol aralkyl-type cyanate compounds, and bisphenol A-type cyanate compounds. Even more preferably, it is a naphthol aralkyl-type cyanate compound and / or a bisphenol A-type cyanate compound. Even more preferably, it is a naphthol aralkyl-type cyanate compound.

[0582] As a naphthol aralkyl cyanate compound, a compound represented by formula (N1) is more preferred.

[0583] Equation (N1)

[0584]

[0585] (In formula (N1), R) 3 Each can independently represent a hydrogen atom or a methyl group, and n3 represents an integer greater than or equal to 1.

[0586] In equation (N1), R 3 Each can be independently represented by a hydrogen atom or a methyl group, with hydrogen atoms being preferred.

[0587] In formula (N1), n3 is an integer of 1 or more, preferably an integer of 1 to 50, more preferably an integer of 1 to 20, even more preferably an integer of 1 to 10, and even more preferably an integer of 1 to 6.

[0588] Furthermore, there are no particular limitations on the phenolic varnish-type cyanate ester compound, but compounds represented by formula (VII) are preferred.

[0589]

[0590] (In equation (VII), R) 6 Each can independently represent a hydrogen atom or a methyl group, and n7 represents an integer greater than or equal to 1.

[0591] In equation (VII), R 6 Each can be independently represented by a hydrogen atom or a methyl group, with hydrogen atoms being preferred.

[0592] In formula (VII), n7 is an integer of 1 or more, preferably an integer of 1 to 20, more preferably an integer of 1 to 10, and even more preferably an integer of 1 to 6.

[0593] As a bisphenol A type cyanate compound, one or more can be selected from the group consisting of prepolymers of 2,2-bis(4-cyanophenyl)propane and 2,2-bis(4-cyanophenyl)propane.

[0594] These cyanate compounds can be prepared using known methods or commercially available products. It should be noted that cyanate compounds with naphthol aralkyl, naphthylene ether, xylene, triphenol methane, or adamantane skeletons have a higher functional group equivalent number and fewer unreacted cyanate groups, thus resin compositions using them tend to have better low water absorption. Furthermore, mainly due to the presence of aromatic or adamantane skeletons, they tend to further improve coating adhesion.

[0595] When the resin composition of this embodiment contains a cyanate ester compound, the lower limit of its content relative to 100 parts by mass of the resin solids in the resin composition is preferably 1 part by mass or more, more preferably 5 parts by mass or more, even more preferably 10 parts by mass or more, and can be 20 parts by mass or more. By making the content of the cyanate ester compound at or above the above-mentioned lower limit, there is a tendency for improved heat resistance, flame resistance, chemical resistance, low dielectric constant, low dielectric loss tangent, and improved insulation. When the resin composition of this embodiment contains a cyanate ester compound, the upper limit of the content of the cyanate ester compound relative to 100 parts by mass of the resin solids in the resin composition is preferably 70 parts by mass or less, more preferably 60 parts by mass or less, even more preferably 50 parts by mass or less, and can be 40 parts by mass or less or 30 parts by mass or less.

[0596] The resin composition in this embodiment may contain only one cyanate ester compound, or it may contain two or more. When it contains two or more compounds, the total amount is preferably within the range described above.

[0597] Alternatively, the resin composition in this embodiment may also be substantially free of cyanate ester compounds. "Substantially free" means that the content of cyanate ester compounds is less than 1 part by weight relative to 100 parts by weight of the resin solids in the resin composition, preferably less than 0.1 parts by weight, and more preferably less than 0.01 parts by weight.

[0598] <<Arylcyclobutene resin>>

[0599] The resin composition of this embodiment may contain arylcyclobutene resin.

[0600] For detailed information, see paragraph 0042 of Japanese Patent Application Publication No. 2019-194312, which describes arylcyclobutene resins, etc., and its contents are incorporated into this specification.

[0601] <<Polyamide Resin>>

[0602] The resin composition of this embodiment may contain polyamide resin or thermosetting polyamide resin.

[0603] For details, please refer to the polyamide described in paragraph 0065 of Japanese Patent Application Publication No. 2019-194312 and the polyamide described in paragraph 0063 of Japanese Patent Application Publication No. 6951829, the contents of which are incorporated herein by reference.

[0604] <<Polyimide Resin>>

[0605] The resin composition of this embodiment may contain polyimide resin or thermosetting polyimide resin.

[0606] For details, please refer to paragraphs 0063-0064 of Japanese Patent No. 6951829, which describes polyimide and the like, and the contents of which are incorporated in this specification.

[0607] <<Perfluorovinyl ether resins>>

[0608] The resin composition of this embodiment may contain perfluorovinyl ether resin or perfluorovinyl benzyl ether resin.

[0609] Examples of its details include perfluorovinyl ether resins, as described in paragraph 0043 of Japanese Patent Application Publication No. 2019-194312, the contents of which are incorporated herein by reference.

[0610] <<Compounds with styrene groups other than polyphenylene ether compounds with carbon-carbon unsaturated double bonds at the ends (B)>>

[0611] The resin composition of this embodiment may contain compounds with styrene groups other than polyphenylene ether compounds (B) with carbon-carbon unsaturated double bonds at the ends.

[0612] Examples of such compounds include those with styrene at the end as described in International Publication No. 2022 / 210095 (e.g., the compounds described in Synthesis Examples 12-16 of the aforementioned publication), paragraphs 0029-0038 of Japanese Patent Application Publication No. 2022-85610, and the vinyl benzyl ether resin described in paragraph 0041 of Japanese Patent Application Publication No. 2019-194312, all of which are incorporated herein by reference.

[0613] <<Compounds with isopropylene groups other than resins (A) with an indane skeleton>>

[0614] The resin composition of this embodiment may contain compounds having isopropylene groups other than resin (A) having an indane skeleton.

[0615] Details of these resins can be exemplified by the isopropylene resins described in International Publication No. 2022 / 210095 (e.g., the compounds described in Synthesis Examples 1, 2, 7, and 8 of that publication), the contents of which are incorporated herein by reference.

[0616] <<Compounds other than resin (A) mentioned above that have carbon-carbon unsaturated double bonds at the ends and an indane skeleton>>

[0617] The resin composition of this embodiment may include compounds other than resin (A) that have carbon-carbon unsaturated double bonds at the ends and an indane skeleton.

[0618] As a compound other than resin (A) having carbon-carbon unsaturated double bonds at the ends and having an indane skeleton, the resin represented by formula (T-St) can be exemplified.

[0619]

[0620] In formula (T-St), R is a group containing the structural unit shown in formula (Tx-St). Arm is independently a benzene ring, naphthalene ring, or anthracene ring. Ma is independently a hydrocarbon group of 1 to 12 carbons, optionally substituted with a halogen atom. Mb is independently a hydroxyl group, a halogen atom, or a hydrocarbon group of 1 to 20 carbons, optionally substituted with a hydroxyl or halogen atom. Mc is independently a hydrocarbon group of 1 to 12 carbons. x, y, and z are independently integers from 0 to 4. r1 is an integer from 1 to 6. R 1 R 2 and R 3 Each can independently represent a hydrogen atom, alkyl group, alkenyl group, or alkynyl group.

[0621]

[0622] (In formula (Tx-St), n, o, and p are the average number of repeating units, where n represents a number greater than 0 and less than 20, o and p each independently represent a number from 0 to 20, and 1.0 ≤ n + o + p ≤ 20.0. Ma each independently represents a hydrocarbon group with 1 to 12 carbon atoms that are optionally substituted by a halogen atom. x represents an integer from 0 to 4. It is bonded to structural units (a), (b), (c), or other groups, and each structural unit is optionally bonded randomly.)

[0623] In formula (T-St), R is a group that contains the structural unit shown in formula (Tx-St).

[0624] In formula (Tx-St), n, o, and p refer to the average number of repeating units in all molecules of the resin.

[0625] In formula (Tx-St), the sum of n, o, and p is preferably 1.1 ≤ n + o + p, more preferably 1.2 ≤ n + o + p, even more preferably 1.5 ≤ n + o + p, even more preferably 2.0 ≤ n + o + p, even more preferably 2.5 ≤ n + o + p, even more preferably 3.0 ≤ n + o + p, even more preferably 3.3 ≤ n + o + p, and further preferably 3.5 ≤ n + o + p, 3.7 ≤ n + o + p, 4.0 ≤ n + o + p, and 4.2 ≤ n + o + p. In formula (Tx-St), the sum of n, o, and p is also preferably n + o + p ≤ 20.0, more preferably n + o + p ≤ 10.0, even more preferably n + o + p ≤ 8.0, even more preferably n + o + p ≤ 7.0, even more preferably n + o + p ≤ 6.5, and even more preferably n + o + p ≤ 6.4. The sum of n, o, and p can be calculated using the method described in the embodiments described later. Furthermore, the sum of n, o, and p in equation (Tx-St) is generally the same as the sum of n, o, and p in equation (Tx).

[0626] In formula (Tx-St), Ma and x have the same meaning as Ma and x in the above formula (Tx), and the preferred range is also the same.

[0627] In formula (T-St), each Arm is independently a benzene ring, a naphthalene ring, or an anthracene ring, preferably a benzene ring or a naphthalene ring, more preferably a benzene ring.

[0628] When Arm is a benzene ring and y is an integer from 1 to 4, it is preferred that the OH group bonded to Arm is bonded to one or two (preferably at least one or two) of Mb in the ortho or para positions.

[0629] In formula (T-St), Ma independently represents a hydrocarbon group with 1 to 12 carbon atoms that is optionally substituted with a halogen atom, which has the same meaning as Ma in formula (Tx) and the preferred range is also the same.

[0630] In formula (T-St), Mb independently represents a hydroxyl group, a halogen atom, or a hydrocarbon group with 1 to 20 carbon atoms optionally substituted with a hydroxyl or halogen atom. Preferably, it is a hydroxyl group, a halogen atom, or a hydrocarbon group with 1 to 20 carbon atoms optionally substituted with a halogen atom; more preferably, it is a hydroxyl group, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a straight-chain or branched alkyl group with 1 to 10 carbon atoms, an alicyclic alkyl group with 4 to 8 carbon atoms, a cumyl group, a phenyl group, or a benzyl group. As a halogen atom, fluorine, chlorine, bromine, or iodine are preferred, more preferably fluorine or chlorine. As a straight-chain or branched alkyl group with 1 to 10 carbon atoms, methyl, ethyl, isopropyl, isobutyl, tert-butyl, pentyl, octyl, or nonyl are preferred. For an alicyclic alkyl group with 4 to 8 carbon atoms, cyclohexyl is preferred. In this embodiment, Mb is more preferably a hydroxyl group, a straight-chain or branched alkyl group having 1 to 10 carbon atoms, or a benzyl group, and more preferably a hydroxyl group, a methyl group, an ethyl group, an isopropyl group, an isobutyl group, a tert-butyl group, or a benzyl group.

[0631] In formula (T-St), each Mc independently represents a hydrocarbon group having 1 to 12 carbon atoms, preferably a hydrocarbon group having 1 to 10 carbon atoms, more preferably a straight-chain or branched alkyl group having 1 to 10 carbon atoms, further preferably methyl, ethyl, isopropyl, isobutyl, tert-butyl, pentyl, octyl or nonyl, and even more preferably methyl, ethyl, isopropyl, isobutyl or tert-butyl.

[0632] In formula (T-St), x has the same meaning as x in formula (Tx) above, and the preferred range is also the same.

[0633] In formula (T-St), each y independently represents an integer from 0 to 4, preferably an integer from 0 to 3, and more preferably an integer from 0 to 2.

[0634] In formula (T-St), z independently represents an integer from 0 to 4, preferably an integer from 0 to 3, more preferably an integer from 0 to 2, even more preferably 0 or 1, and even more preferably 0.

[0635] In formula (T-St), r1 represents an integer from 1 to 6, preferably an integer from 1 to 5, further preferably an integer from 1 to 4, even more preferably an integer from 1 to 3, even more preferably 1 or 2, and even more preferably 1.

[0636] In formula (T-St), R 1 R 2 and R 3 Each of these groups independently represents a hydrogen atom, alkyl group, alkenyl group, or alkynyl group, preferably a hydrogen atom or alkyl group, more preferably a hydrogen atom or methyl group, and even more preferably a hydrogen atom. As R 1 R 2 and R 3 The alkyl, alkenyl, or alkynyl groups preferably have 5 or fewer carbon atoms, more preferably 3 or fewer.

[0637] In this embodiment, formula (T-St) is preferably represented by formula (T-St2).

[0638]

[0639] In formula (T-St2), R is a group containing the structural unit shown in formula (Tx-St). Ma independently represents a hydrocarbon group of 1 to 12 carbons, optionally substituted with a halogen atom. Mb independently represents a hydroxyl group, a halogen atom, or a hydrocarbon group of 1 to 20 carbons, optionally substituted with a hydroxyl or halogen atom. Mc independently represents a hydrocarbon group of 1 to 12 carbons. x, y, and z independently represent integers from 0 to 4. r1 represents an integer from 1 to 6. R 1 R 2 and R 3 Each can independently represent a hydrogen atom, alkyl group, alkenyl group, or alkynyl group.

[0640]

[0641] (In formula (Tx-St), n, o, and p are the average number of repeating units, where n represents a number greater than 0 and less than 20, o and p each independently represent a number from 0 to 20, and 1.0 ≤ n + o + p ≤ 20.0. Ma each independently represents a hydrocarbon group with 1 to 12 carbon atoms that are optionally substituted by a halogen atom. x represents an integer from 0 to 4. It is bonded to structural units (a), (b), (c) or other groups, and each structural unit is optionally bonded randomly.)

[0642] In equation (T-St2), R, Ma, Mb, Mc, x, y, z, r1, R 1 R 2 and R 3 Relative to R, Ma, Mb, Mc, x, y, z, r1, R in equation (T-St) 1 R 2 and R 3 They have the same meaning and the same preferred range.

[0643] Furthermore, the resin shown in formula (T-St) preferably has a parameter α calculated from formula (α) that is 0.55 or more and 1.00 or less.

[0644]

[0645] (The parentheses in equation (α) indicate) 1 (The integral value between the corresponding chemical shift values ​​in H-NMR.)

[0646] Here, α represents the ratio of structural units with an indane framework (structural unit (a) in formula (Tx-St)). More specifically, it is speculated that by adjusting the ratio of structural units with an indane framework in a manner that satisfies the range of the parameter α mentioned above, the resulting resin molecules have high rigidity and can increase the glass transition temperature of the cured product.

[0647] The parameter α of the resin represented by formula (T-St) is preferably 0.57 or higher, more preferably 0.59 or higher, even more preferably 0.60 or higher, even more preferably 0.62 or higher, and may also be 0.65 or higher, 0.70 or higher, 0.75 or higher, or 0.80 or higher. By setting it to the above lower limit value or higher, there is a tendency to further improve the low dielectric properties (low relative permittivity and / or low dielectric loss tangent) and heat resistance of the obtained cured product. From the perspective that the obtained cured product has excellent low dielectric properties and heat resistance, the parameter α is substantially better the larger it is, but it may also be 0.95 or lower, 0.94 or lower, 0.93 or lower, or 0.92 or lower.

[0648] As a compound other than resin (A) having carbon-carbon unsaturated double bonds at the end and having an indane skeleton, resins (hereinafter sometimes referred to as "resin (IP1)") with structural units derived from compounds represented by formula (DIP) as the main components and having structures represented by formula (In-1) and / or formula (In-2) ​​as the main components can also be exemplified.

[0649]

[0650] (In formula (DIP), Ma independently represents a hydrocarbon group with 1 to 12 carbon atoms that are optionally substituted with halogen atoms. x represents an integer from 0 to 4.)

[0651]

[0652] In formula (In-1), Mb independently represents a hydroxyl group, a halogen atom, or a hydrocarbon group with 1 to 20 carbon atoms that is optionally substituted by a hydroxyl or halogen atom. y represents an integer from 0 to 3. R x This refers to a group containing a carbon-carbon unsaturated double bond. * indicates a bonding site with other sites.

[0653]

[0654] In formula (In-2), Ma independently represents a hydrocarbon group with 1 to 12 carbon atoms that is optionally substituted with a halogen atom. x represents an integer from 0 to 3. Mb independently represents a hydroxyl group, a halogen atom, or a hydrocarbon group with 1 to 20 carbon atoms that is optionally substituted with a hydroxyl or halogen atom. y represents an integer from 0 to 4. R xThis refers to groups containing carbon-carbon unsaturated double bonds. xp represents the number of connecting bonds emanating from the benzene ring, an integer of 1 or 2. * indicates bonding sites with other sites.

[0655] Here, "other parts" refers to the portion of the resin (IP1) other than the structure represented by formula (In-1) and / or formula (In-2). The same applies to "other parts" in the section on resin (IP1) below.

[0656] It is speculated that the resin (IP1) is produced by the terminal group containing a carbon-carbon unsaturated double bond (R). x The resin composition containing resin (IP1) is bonded to structural units of the compound derived from formula (DIP) (especially structural units of the compound derived from formula (DIP) and having an indane backbone (preferably trimethyl indane structure (the same applies hereinafter))) via oxygen atoms and / or optionally low molecular weight structural units such as phenylene oxides with substituents. This results in a higher proportion of structural units of the compound derived from formula (DIP) (especially the indane backbone) in the cured product of the resin composition containing resin (IP1), which can reduce Df (dielectric loss tangent). In particular, it is speculated that a low Df can be achieved even at high curing temperatures. Furthermore, resin (IP1) exhibits excellent heat resistance. Additionally, resin (IP1) can also reduce Dk (relative permittivity).

[0657] It should be noted that the structural units derived from the compound represented by formula (DIP) can be synthesized from the compound represented by formula (DIP), or from other starting materials that provide the structural units derived from the compound represented by formula (DIP). Examples of compounds represented by formula (DIP) include 1,3-diisopropenylbenzene and 1,4-diisopropenylbenzene. Other raw materials that provide structural units derived from compounds represented by formula (DIP) include, for example, α,α'-dihydroxy-1,3-diisopropylbenzene, α,α'-dihydroxy-1,4-diisopropylbenzene, α,α'-dihalo-1,3-diisopropylbenzene (e.g., α,α'-dichloro-1,3-diisopropylbenzene), α,α'-dihalo-1,4-diisopropylbenzene (e.g., α,α'-dichloro-1,4-diisopropylbenzene), α,α'-dialkoxy-1,3-diisopropylbenzene (e.g., α,α'-dimethoxy-1,3-diisopropylbenzene), α,α'-dialkoxy-1,4-diisopropylbenzene (e.g., α,α'-dimethoxy-1,4-diisopropylbenzene), etc., which, through unit operations such as heating, provide equivalents of compounds represented by formula (DIP) to compounds represented by formula (DIP). In this embodiment, 1,3-diisopropenylbenzene and α,α'-dihydroxy-1,3-diisopropylbenzene are preferred among the above-mentioned compounds. Furthermore, one of the above-mentioned compounds may be used alone, or two or more may be used in combination.

[0658] First, let's explain the formula (DIP).

[0659]

[0660] (In formula (DIP), Ma independently represents a hydrocarbon group with 1 to 12 carbon atoms that are optionally substituted with halogen atoms. x represents an integer from 0 to 4.)

[0661] It should be noted that the resin (IP1) may contain multiple structural units derived from the compound shown in formula (DIP). In this case, each Ma and x may be the same or different.

[0662] In formula (DIP), Ma independently represents a hydrocarbon group with 1 to 12 carbon atoms that is optionally substituted with a halogen atom, which has the same meaning as Ma in formula (T1-1) and the preferred range is also the same.

[0663] In formula (DIP), x represents an integer from 0 to 4, preferably an integer from 0 to 3, more preferably an integer from 0 to 2, further preferably 0 or 1, and even more preferably 0.

[0664] In the resin (IP1), structural units derived from the compound represented by formula (DIP) are used as the main component. "Main component" means that, among all the structural units constituting the resin (IP1), the structural units derived from the compound represented by formula (DIP) constitute the largest proportion. More specifically, the content of the structural units derived from the compound represented by formula (DIP) in the resin (IP1) is preferably 50 mol% or more of all structural units, more preferably 60 mol% or more, even more preferably 70 mol% or more, even more preferably 80 mol% or more, even more preferably 82 mol% or more, even more preferably 83 mol% or more, and even more particularly preferably 85 mol% or more.

[0665] Here, "total structural units" refers to the total number of structural units derived from all monomer molecules used as raw materials for the resin (IP1).

[0666] The resin (IP1) also has structures represented by formulas (In-1) and / or (In-2). These groups are typically present as terminal groups. It is presumed that by giving the resin (IP1) the structure represented by formulas (In-1) and / or (In-2), the structural units derived from the compound shown in formula (DIP) are connected via low molecular weight structural units such as oxygen atoms and / or optionally substituent-containing phenylene oxides to groups (R) containing carbon-carbon unsaturated double bonds. x As mentioned above, bonding can reduce Df (dielectric loss tangent). Furthermore, it is speculated that even with high curing temperatures, low Df can still be achieved.

[0667] Furthermore, as long as the resin (IP1) has a structure represented by formula (In-1) and / or formula (In-2), the resin (IP1) may also have terminal groups with other structures.

[0668]

[0669] In formula (In-1), Mb independently represents a hydroxyl group, a halogen atom, or a hydrocarbon group with 1 to 20 carbon atoms that is optionally substituted by a hydroxyl or halogen atom. y represents an integer from 0 to 3. R x This refers to a group containing a carbon-carbon unsaturated double bond. * indicates a bonding site with other sites.

[0670]

[0671] In formula (In-2), Ma independently represents a hydrocarbon group with 1 to 12 carbon atoms that is optionally substituted with a halogen atom. x represents an integer from 0 to 3. Mb independently represents a hydroxyl group, a halogen atom, or a hydrocarbon group with 1 to 20 carbon atoms that is optionally substituted with a hydroxyl or halogen atom. y represents an integer from 0 to 4. R x This refers to groups containing carbon-carbon unsaturated double bonds. xp represents the number of connecting bonds emanating from the benzene ring, an integer of 1 or 2. * indicates bonding sites with other sites.

[0672] In formula (In-1), Mb independently represents a hydroxyl group, a halogen atom, or a hydrocarbon group with 1 to 20 carbon atoms that is optionally replaced by a hydroxyl or halogen atom, with the same meaning as Mb in the above formula (T-St), and the preferred range is also the same.

[0673] In formula (In-1), y represents an integer from 0 to 3, preferably an integer from 0 to 2, more preferably 0 or 2, and can also be 0. In addition, y is preferred from the viewpoint of dielectric properties.

[0674] Furthermore, when y is 1 or higher, Mb is preferred relative to R. x The carbon atom bonded to the O group is bonded to an adjacent position (ortho).

[0675] In equation (In-1), R x It is a group containing a carbon-carbon unsaturated double bond, more preferably a group with a formula weight of 27 to 120.

[0676] Specifically, R x Each group is preferably represented by a group of formula (Rx-11) or formula (Rx-2), more preferably vinylbenzyl or (meth)acryloyl, and even more preferably vinylbenzyl.

[0677]

[0678] In equations (Rx-11) and (Rx-2), R 1 R 2 and R 3 Each group independently represents a hydrogen atom, alkyl, alkenyl, or alkynyl group. * indicates the bonding site with an oxygen atom. Mc independently represents a hydrocarbon group with 1 to 12 carbon atoms. z represents an integer from 0 to 4. r1 represents an integer from 1 to 6.

[0679] Formulas (Rx-11) and (Rx-2), except for r1, have the same meaning as those described in the section on polyphenylene ether compounds above, and their preferred ranges are also the same. In formula (Rx-11), r1 is preferably an integer of 5 or less, more preferably an integer of 4 or less, even more preferably an integer of 3 or less, even more preferably 1 or 2, and even more preferably 1.

[0680] In formula (In-2), Ma independently represents a hydrocarbon group with 1 to 12 carbon atoms that is optionally substituted with a halogen atom, which is synonymous with Ma in formula (T1) and has the same preferred range.

[0681] In formula (In-2), x represents an integer from 0 to 3, preferably an integer from 0 to 2, more preferably 0 or 1, and can also be 0.

[0682] In equation (In-2), Mb and R x respectively with Mb and R in equation (In-1) x They have the same meaning and the same preferred range.

[0683] In formula (In-2), y represents an integer from 0 to 4, preferably an integer from 0 to 3, more preferably an integer from 0 to 2, and even more preferably 0 or 2, or 0. Furthermore, y being 2 is preferred from the viewpoint of dielectric properties.

[0684] Furthermore, when y is 1 or higher, Mb is preferred relative to R. x The carbon atom bonded to the O group is bonded to an adjacent position (ortho).

[0685] In formula (In-2), xp is the number of connecting bonds emanating from the benzene ring, which is an integer of 1 or 2. When xp is 2, for example, as shown below, two groups emanating from the benzene ring can bond together to form a ring.

[0686]

[0687] In the above formula, * represents the bonding site with other parts, R x The meanings of Ma, x, Mb, and y are the same as those of R in equation (In-2). x Ma, x, Mb, and y are the same, and their preferred ranges are also the same.

[0688] In formulas (In-1) and (In-2), R is more preferred. x Groups (containing carbon-carbon unsaturated double bonds) have a formula weight of 27 to 120, each independently.

[0689] In this embodiment, R in one molecule of resin (IP1) x The average number is preferably 2.5 or more, more preferably more than 2.5, further preferably 2.6 or more, even more preferably 2.7 or more, and even more preferably 2.8 or more. Additionally, R in one molecule of resin (IP1) x The average number is preferably 8.0 or less, more preferably 7.0 or less, further preferably 6.5 or less, even more preferably 6.0 or less, and may also be 5.5 or less. This is achieved by increasing the number of R molecules in one molecule of resin (IP1). x The quantity is set within the range described above, and there is a tendency for the obtained cured material to have lower dielectric properties (low relative permittivity and / or low dielectric loss tangent) and further improved heat resistance.

[0690] In this embodiment, the resin (IP1) preferably includes both the structure shown in formula (In-1) and the structure shown in formula (In-2).

[0691] The resin (IP1) typically contains an indane backbone in addition to the structures represented by formulas (In-1) and / or (In-2). Such an indane backbone, other than the structures represented by formulas (In-1) and / or (In-2), is typically formed through a cyclization reaction of a compound represented by formula (DIP). That is, the resin (IP1) of this embodiment preferably originates from at least a portion of the structural units of the compound represented by formula (DIP) containing an indane backbone, and more preferably contains the structure represented by formula (In-0).

[0692]

[0693] (In formula (In-0), Ma independently represents a hydrocarbon group with 1 to 12 carbon atoms that are optionally substituted with halogen atoms. x represents an integer from 0 to 3. xq is the number of connecting bonds emanating from the benzene ring, which is an integer of 1 or 2. * represents a bonding site with other sites. ** represents a bonding site with other sites or a methyl group bonded to the cyclopentane ring. At least one of the two ** is a bonding site with other sites.)

[0694] In equation (In-0), Ma has the same meaning as Ma in equation (DIP), and the preferred range is also the same.

[0695] In formula (In-0), x represents an integer from 0 to 3, preferably an integer from 0 to 2, more preferably 0 or 1, and can also be 0.

[0696] In formula (In-0), xq is the number of connecting bonds emanating from the benzene ring, which is an integer of 1 or 2. When xq is 2, as mentioned above, the two groups emanating from the benzene ring can bond together to form a ring.

[0697] The content of the indane skeleton in the resin (IP1) is not particularly limited, but when expressed by the above parameter α, α is preferably 0.35 or more and 1.00 or less.

[0698] As specific examples of structural units derived from the compound represented by formula (DIP) in resin (IP1), in addition to the structure represented by formula (In-0) above, the following structural units (a) to (c) (hereinafter sometimes referred to as formula (Tx)) can also be exemplified. In formula (Tx), * represents the bonding site with structural units (a) to (c), the structure represented by formula (In-1), the structure represented by formula (In-2), the structure represented by formula (In-0), and some of the structures exemplified below.

[0699]

[0700] In structural units (a) to (c), Ma and x have the same meaning as Ma and x in formula (DIP), and the preferred range is also the same.

[0701] Furthermore, as specific examples of structures in resin (IP1) containing structural units derived from the compound shown in formula (DIP), some of the structures illustrated below may also be listed. The structures in resin (IP1) containing structural units derived from the compound shown in formula (DIP) are, of course, not limited to these. In the following formulas, Ma and x each have the same meaning as Ma and x in formula (DIP), and the preferred range is also the same.

[0702]

[0703]

[0704] In the above formula, * represents the bonding site with other parts.

[0705] Another example of a compound other than resin (A) that has a carbon-carbon unsaturated double bond at the end and an indane skeleton is the resin shown in formula (D) (resin (IP2)). For such a resin (IP2), it is presumed that the terminal groups (R) containing carbon-carbon unsaturated double bonds... xThe resin (IP2) is bonded to structural units with an indane backbone via oxygen atoms and / or optionally, low molecular weight structural units such as phenylene oxides with substituents, thereby increasing the proportion of the indane backbone (preferably trimethyl indane structure) in the cured product of the composition containing the resin (IP2), which can reduce Df (dielectric loss tangent). In particular, it is speculated that a low Df can be achieved even at high curing temperatures. Furthermore, the resin of this embodiment can exhibit excellent heat resistance. In addition, the resin (IP2) can also reduce Dk (relative permittivity). The resin (IP2) can be the same resin as the resin (IP1).

[0706]

[0707] In formula (D), R is a group that contains the structural unit shown in formula (Tx). x It is a group containing a carbon-carbon unsaturated double bond. R y y represents a hydrogen atom, a group containing an -O-carbon-carbon unsaturated double bond, or other groups. y1 is an integer from 1 to 4. Mb independently represents a hydroxyl group, a halogen atom, or a hydrocarbon group with 1 to 20 carbon atoms optionally substituted by a hydroxyl or halogen atom. y represents an integer from 0 to 4.

[0708]

[0709] (In formula (Tx), n, o, and p are the average number of repeating units, where n represents a number greater than 0 and less than 20, o and p each independently represent a number from 0 to 20, and 1.0 ≤ n + o + p ≤ 20.0. Ma each independently represents a hydrocarbon group with 1 to 12 carbon atoms that are optionally substituted by a halogen atom. x represents an integer from 0 to 4. Structural units (a), (b), and (c) are bonded to structural units (a), (b), and (c) or other groups at *, and each structural unit is optionally bonded randomly.)

[0710] In formula (D), R is a group that contains the structural unit shown in formula (Tx).

[0711] That is, in the resin (IP2), R contains at least a portion of structural unit (a), and may also contain structural units (b) and / or (c), and may also have other structural units (hereinafter sometimes referred to as "other structural units") and other groups other than structural units (a), (b), and (c). Specifically, structural units (a), (b), and (c) may be bonded, respectively, to any of the structural units (a) to (c), other structural units other than structural units (a) to (c), other groups, and groups of formula (D) bonded to R.

[0712] Furthermore, in the resin (IP2), R does not necessarily have to be linear; it can also be bonded in two or three dimensions. In this embodiment, the resin (IP2) (especially the groups containing the structural units shown in formula (Tx)) is preferably linear. By making the structural units constituting the resin (IP2) linearly bonded, there is a tendency to improve the low dielectric properties, which is preferred.

[0713] Other structural units can be exemplified as structural units derived from compounds represented by formula (DIP) that are bonded to any of the structural units (a), (b), and (c).

[0714] It should be noted that the structural units derived from the compound represented by formula (DIP) can be synthesized from the compound represented by formula (DIP), or from other starting materials that provide the structural units derived from the compound represented by formula (DIP). Examples of other starting materials that provide the structural units derived from the compound represented by formula (DIP) include α,α'-dihydroxy-1,3-diisopropylbenzene, α,α'-dihalo-1,3-diisopropylbenzene, α,α'-dialkoxy-1,3-diisopropylbenzene, etc., which are equivalents of the compound represented by formula (DIP) obtained through unit operations such as heating.

[0715]

[0716] (In formula (DIP), Ma independently represents a hydrocarbon group with 1 to 12 carbon atoms that are optionally substituted with halogen atoms. x represents an integer from 0 to 4.)

[0717] The details of Formula (DIP) are the same as those described in the above-mentioned Resin (IP1), and the preferred range is also the same.

[0718] In addition, if the resin (IP2) has other structural units, the resin (IP2) may also have a branched structure.

[0719] Furthermore, in the resin (IP2), sometimes the double bonds of structural units (b) and / or (c) may react with structural units derived from the compound shown in formula (DIP) to form rings, thereby constituting structural units with an indane skeleton. As an example of such a structure, the following structure is illustrated.

[0720]

[0721] In the structure, Ma and x are each independently identical in meaning to Ma and x in the formula (Tx), and their preferred ranges are also the same.

[0722] In the above structure, *it is preferred to be bonded to any of the terminal groups in formula (D) that are bonded to R or to any of the structural units (a) to (c).

[0723] Furthermore, sometimes terminal groups are bonded to structural units (a), (b), or (c).

[0724] In addition, the resin (IP2) may contain the following compounds.

[0725]

[0726] In the compound, Ma and x have the same meaning as Ma and x in formula (Tx), and the preferred ranges are also the same. Furthermore, Mb and y each independently have the same meaning as Mb and y in formula (D) above, and the preferred ranges are also the same. R x It is a group containing a carbon-carbon unsaturated double bond.

[0727] Formula (Tx) has the same meaning as (Tx) in the resin (A) section, and the preferred range is also the same.

[0728] In equation (D), R x It is a group containing a carbon-carbon unsaturated double bond, more preferably a group with a formula weight of 27 to 120.

[0729] Specifically, R x Each group is preferably represented by a group of formula (Rx-11) or formula (Rx-2), more preferably vinylbenzyl or (meth)acryloyl, and even more preferably vinylbenzyl.

[0730]

[0731] In equations (Rx-11) and (Rx-2), R 1 R 2 and R 3 Each group independently represents a hydrogen atom, alkyl, alkenyl, or alkynyl group. * indicates the bonding site with an oxygen atom. Mc independently represents a hydrocarbon group with 1 to 12 carbon atoms. z represents an integer from 0 to 4. r1 represents an integer from 1 to 6.

[0732] Formulas (Rx-11) and (Rx-2), except for r1, have the same meaning as those described in the section on polyphenylene ether compounds above, and their preferred ranges are also the same. In formula (Rx-11), r1 is preferably an integer of 5 or less, more preferably an integer of 4 or less, even more preferably an integer of 3 or less, even more preferably 1 or 2, and even more preferably 1.

[0733] In equation (D), R y It is a hydrogen atom, a group containing an -O-carbon-carbon unsaturated double bond, or other groups.

[0734] R yThe resin can be bonded to R at any position, but it can also be bonded to any of the structural units (a), (b), (c) contained in R and any of the other structural units mentioned above. One example of bonding to R is bonding to the benzene ring contained in structural units (a), (b), or (c). Another example of bonding to R is bonding to structural units other than structural units (a), (b), and (c) contained in R. In this embodiment, the resin preferably contains R. y At least one of them is bonded to the benzene ring of structural unit (a), (b) or (c), more preferably R y At least one of them is bonded to the benzene ring of structural unit (a).

[0735] R y When the group is a group containing an -O-carbon-carbon unsaturated double bond, the group containing a carbon-carbon unsaturated double bond and the above-mentioned R x They have the same meaning and the same preferred range.

[0736] R y In the resin (IP2), the number of groups containing carbon-carbon unsaturated double bonds, calculated based on the average number of all molecules in the resin, is preferably 0.2 or more, more preferably 0.3 or more, further preferably 0.4 or more, even more preferably 0.5 or more, even more preferably 0.8 or more, and may also be 1.0 or more. Additionally, R... y The number of groups containing carbon-carbon unsaturated double bonds in the resin is preferably 7 or less, more preferably 6 or less, even more preferably 5 or less, even more preferably 4 or less, even more preferably 3 or less, and may further be 2.5 or less, 1.5 or less, less than 1.5, 1.4 or less, or 1.2 or less.

[0737] R y When other groups are present, examples of other groups include organic groups, hydroxyl groups, or halogen atoms. As the aforementioned organic groups, it is preferable to be a hydrocarbon group with 1 to 20 carbons that is optionally substituted with a hydroxyl or halogen atom, more preferably a hydrocarbon group with 1 to 5 carbons that is optionally substituted with a hydroxyl or halogen atom, even more preferably a saturated hydrocarbon group with 1 to 5 carbons, even more preferably a saturated hydrocarbon group with 1 to 3 carbons, and even more preferably propyl or isopropyl.

[0738] In formula (D), y1 is an integer from 1 to 4, preferably 1 or more, and preferably 3 or less, more preferably 2 or less, and even more preferably 1.

[0739] R in each molecule of resin (IP2) x and / or R yThe total number of groups containing carbon-carbon unsaturated double bonds in the resin (IP2), calculated on average among all molecules in the resin (IP2), is preferably 2.5 or less, more preferably less than 2.5, even more preferably 2.4 or less, and may also be 2.2 or less. Furthermore, the R in each molecule of the resin (IP2) x and / or R y The total number of groups containing carbon-carbon unsaturated double bonds is preferably 0.8 or more, more preferably 1.2 or more, even more preferably 1.3 or more, even more preferably 1.4 or more, even more preferably 1.5 or more, even more preferably 1.8 or more, and may also be 2.0 or more. By ensuring that the total number of groups containing carbon-carbon unsaturated double bonds is within the above-mentioned range, the cured product tends to have excellent low dielectric properties.

[0740] In formula (D), Mb independently represents a hydroxyl group, a halogen atom, or a hydrocarbon group with 1 to 20 carbon atoms that is optionally replaced by a hydroxyl or halogen atom, with the same meaning as Mb in the above formula (T-St), and the preferred range is also the same.

[0741] In formula (D), y represents an integer from 0 to 4, preferably an integer from 0 to 3, more preferably an integer from 0 to 2, and even more preferably 0 or 2, or 0. Furthermore, y being 2 is preferred from the viewpoint of dielectric properties.

[0742] Furthermore, when y is 1 or higher, Mb is preferred relative to R. x The carbon atom bonded to the O group is bonded to an adjacent position (ortho).

[0743] In the resin (IP2) of this embodiment, formula (D) is preferably represented by formula (D-1).

[0744]

[0745] In formula (D-1), R is a group containing the structural unit shown in formula (Tx) above. x Each group independently represents a carbon-carbon unsaturated double bond. Mb independently represents a hydroxyl group, a halogen atom, or a hydrocarbon group with 1 to 20 carbon atoms optionally substituted by a hydroxyl or halogen atom. y represents an integer from 0 to 4.

[0746] Therefore, equation (D-1) is preferably represented by equation (D-1-2).

[0747]

[0748] (In formula (D-1-2), R is a group containing the structural unit shown in formula (Tx) above. R xEach group independently represents a carbon-carbon unsaturated double bond. Mb independently represents a hydroxyl group, a halogen atom, or a hydrocarbon group with 1 to 20 carbon atoms optionally substituted by a hydroxyl or halogen atom. y represents an integer from 0 to 4.

[0749] Furthermore, in the resin (IP2) of this embodiment, formula (D) is preferably represented by formula (D-2).

[0750]

[0751] In formula (D-2), R' is a group that, together with the adjacent group on the left with an indene skeleton, forms a group containing the structural unit represented by the above formula (Tx). x Each group independently represents a carbon-carbon unsaturated double bond. Mb independently represents a hydroxyl group, a halogen atom, or a hydrocarbon group with 1 to 20 carbon atoms optionally substituted by a hydroxyl or halogen atom. y represents an integer from 0 to 4.

[0752] Therefore, equation (D-2) is preferably represented by equation (D-2-1).

[0753]

[0754] In formula (D-2-1), R' is a group that, together with the adjacent group on the left having an indene skeleton, forms a group containing the structural unit represented by the above formula (Tx). x Each group independently represents a carbon-carbon unsaturated double bond. Mb independently represents a hydroxyl group, a halogen atom, or a hydrocarbon group with 1 to 20 carbon atoms optionally substituted by a hydroxyl or halogen atom. y represents an integer from 0 to 4.

[0755] In equations (D-1), (D-1-2), (D-2), and (D-2-1), R x Each independently of R in equation (D) x They have the same meaning and the same preferred range.

[0756] In equations (D-1) and (D-1-2), R has the same meaning as R in equation (D) and the preferred range is also the same.

[0757] In formulas (D-2) and (D-2-1), R' is a group that, together with the adjacent group on the left having an indene skeleton, forms a group containing the structural unit represented by the above formula (Tx). That is, in formula (D), R y A group containing an -O-carbon-carbon unsaturated double bond is defined as a group whose oxygen atom must be bonded to the benzene ring of structural unit (a) in formula (Tx). Specifically, for example, in formula (D-2), the part enclosed in a circle below corresponds to R in formula (D).

[0758]

[0759] In equations (D-1), (D-1-2), (D-2), and (D-2-1), Mb and y have the same meaning as Mb and y in equation (D), and their preferred ranges are also the same.

[0760] In this embodiment, the resin (IP1) and / or resin (IP2) preferably have a parameter α calculated by formula (α) that is 0.35 or more and 1.00 or less.

[0761]

[0762] (The parentheses in equation (α) indicate) 1 (The integral value between the corresponding chemical shift values ​​in H-NMR.)

[0763] Here, α represents the ratio of structural units with an indane skeleton (mainly structural unit (a) in formula (Tx)) in resin (IP1) and / or resin (IP2). More specifically, it is speculated that by adjusting the ratio of structural units with an indane skeleton in resin (IP1) and / or resin (IP2) to satisfy the range of the above parameter α, the rigidity of the resulting resin molecules increases. Molecules with high rigidity have lower mobility compared to molecules with low rigidity, thus resulting in a longer relaxation time during dielectric relaxation and a reduction in dielectric loss tangent (Df). In addition, it is speculated that due to the increased rigidity of the resin molecules, the glass transition temperature of the cured product can be increased, resulting in excellent heat resistance. In this embodiment, R (a group containing a structural unit represented by formula (Tx)) in formula (D) is a low molecular weight structural unit such as an oxygen atom and / or optionally a substituent phenylene oxide, and a group containing a carbon-carbon unsaturated double bond (R x This bonding can increase the proportion of indane backbone in resins (IP1) and / or resin (IP2).

[0764] The parameter α of resin (IP1) and / or resin (IP2) is more preferably 0.36 or higher, more preferably 0.40 or higher, even more preferably 0.45 or higher, even more preferably 0.50 or higher, and can further be 0.55 or higher, 0.60 or higher, 0.65 or higher, or 0.70 or higher. By setting the parameter α to the lower limit value or above, there is a tendency to further improve the low dielectric properties (low relative permittivity and / or low dielectric loss tangent) and heat resistance of the obtained cured product. The parameter α substantially tends to have low dielectric properties and excellent heat resistance, so the larger the parameter α is, the better, but it can also be 0.98 or lower, 0.95 or lower, 0.90 or lower, 0.85 or lower, 0.84 or lower, or 0.82 or lower.

[0765] The number-average molecular weight of resins (IP1) and / or resin (IP2) is preferably 8000 or less, more preferably 4000 or less. By setting the number-average molecular weight to or above the aforementioned lower limit, there is a tendency to further improve the low dielectric properties (particularly the low dielectric loss tangent) of the resulting cured product. This is believed to be mainly because increasing the molecular weight increases the proportion of indane backbones (e.g., structural units (a) in formula (Tx)) contained in the molecule. Furthermore, by setting the number-average molecular weight to or below the aforementioned upper limit, there is a tendency to further improve the formability and solvent solubility of the resin. The lower limit of the number average molecular weight of resin (IP1) and / or resin (IP2) is more preferably 500 or more, further preferably 600 or more, even more preferably 700 or more, even more preferably 800 or more, and may also be 850 or more, 900 or more, 1000 or more, 1100 or more, 1200 or more, 1300 or more, 1400 or more, 1500 or more, 1600 or more, 1700 or more, 1800 or more, 1900 or more, 2000 or more, 2200 or more, 2300 or more, 2400 or more, 2500 or more, or 2600 or more. Furthermore, the upper limit of the number average molecular weight of resin (IP1) and / or resin (IP2) is more preferably 7000 or less, further preferably 6000 or less, even more preferably 5000 or less, even more preferably 4000 or less, and can be 3800 or less, 3500 or less, 3200 or less, 3000 or less, further preferably 2800 or less, 2600 or less, 2400 or less, 2200 or less, 2000 or less, 1900 or less, 1800 or less, 1700 or less, 1600 or less, or 1500 or less.

[0766] The method of manufacturing the resin represented by resin (IP1) and / or resin (IP2) is not particularly limited. For example, a hydroxyl resin in which the RxO and Ry portions of the above formula (D) are hydroxyl groups can be used to manufacture it.

[0767] A first embodiment of the method for manufacturing resin (IP1) and / or resin (IP2) can be described as follows: A mixture comprising a compound of formula (DIP) and a compound of formula (P1) is reacted to synthesize a resin having hydroxyl groups (hereinafter, sometimes referred to as "hydroxyl resin"); the hydroxyl resin is then reacted with a compound having groups comprising carbon-carbon unsaturated double bonds and groups that are released from the hydroxyl groups of the hydroxyl resin. Furthermore, the hydroxyl resin can also be synthesized by further reacting the compound of formula (DIP) with the compound of formula (P1) described later.

[0768]

[0769] (In formula (P1), Mb independently represents a hydroxyl group, a halogen atom, or a hydrocarbon group with 1 to 20 carbon atoms that is optionally substituted by a hydroxyl or halogen atom. y represents an integer from 0 to 4.)

[0770] The meanings of Mb and y in the above formula (P1) are the same as those of Mb and y in formula (D), and the preferred ranges are also the same.

[0771] Compounds having groups containing carbon-carbon unsaturated double bonds and groups that are removed by reaction with the hydroxyl groups of hydroxyl resins are described.

[0772] The group containing a carbon-carbon unsaturated double bond is preferably a group represented by formula (Rx-1) or formula (Rx-2), more preferably vinylbenzyl or (meth)acryloyl, and even more preferably vinylbenzyl.

[0773] On the other hand, examples of groups that can be removed by reacting with the hydroxyl group of the hydroxyl resin include halogen atoms, hydroxyl groups, alkoxy groups, and (meth)acryloyl groups, with halogen atoms being the most preferred. Examples of halogen atoms include chlorine atoms, bromine atoms, and iodine atoms, with chlorine atoms or bromine atoms being the most preferred.

[0774] As a first embodiment of the method for manufacturing resin (IP1) and / or resin (IP2), it can be manufactured as follows: a polymer (oligomer) with structural units derived from the compound shown in formula (DIP) as the main components is synthesized in advance from the compound shown in formula (DIP), and then the polymer is reacted with the compound shown in formula (P1) to synthesize a hydroxyl resin, and the resulting hydroxyl resin is reacted with a compound having groups containing carbon-carbon unsaturated double bonds and groups that are deactivated by reacting with the hydroxyl groups of the hydroxyl resin, thereby manufacturing resin (IP1) and / or resin (IP2).

[0775] When the resin composition of this embodiment contains a compound other than resin (A) having a carbon-carbon unsaturated double bond at the end and having an indane skeleton, its content is preferably 1 part by mass or more relative to 100 parts by mass of the resin solids in the resin composition, and preferably 50 parts by mass or less.

[0776] The resin composition in this embodiment may contain only one type of resin (A) that has carbon-carbon unsaturated double bonds at the ends and an indane skeleton, or it may contain two or more types. When two or more types are contained, the total amount is preferably within the range described above.

[0777] Alternatively, the resin composition in this embodiment may also be composed of compounds other than resin (A) that have carbon-carbon unsaturated double bonds at their ends and an indane skeleton, which substantially do not contain any of these compounds. "Substantially do not contain" means that the content of compounds other than resin (A) that have carbon-carbon unsaturated double bonds at their ends and an indane skeleton is less than 1 part by weight relative to 100 parts by weight of the resin solids in the resin composition, preferably less than 0.1 parts by weight, and more preferably less than 0.01 parts by weight.

[0778] <<Multifunctional (methyl)allyl compounds other than the isocyanurate compound (C1) having two or more (methyl)allyl groups and the glycourea compound (C2) having two or more (methyl)allyl groups>>

[0779] The resin composition of this embodiment may contain polyfunctional (methyl)allyl compounds (hereinafter sometimes referred to as "other polyfunctional (methyl)allyl compounds") other than the isocyanurate compound (C1) having two or more (methyl)allyl groups and the glycourea compound (C2) having two or more (methyl)allyl groups.

[0780] As other such multifunctional (methyl)allyl compounds, it is preferred to include at least one selected from the group consisting of tri(methyl)allyl cyanurate, (methyl)allyl-substituted nadicimide, and diallyl phthalate, more preferably including (methyl)allyl isocyanurate and / or (methyl)allyl-substituted nadicimide, and even more preferably including (methyl)allyl-substituted nadicimide.

[0781] Examples of cyanurate tri(methyl)allyl compounds include cyanurate tri(methyl)allyl compounds (e.g., cyanurate triallyl esters represented by the following structures).

[0782]

[0783] Furthermore, as compounds containing (methyl)allyl groups, examples include resins containing allyl groups as described in International Publication No. 2022 / 210095 (e.g., compounds described in Synthesis Examples 3, 4, 6, 20, and 22 of that publication), the contents of which are incorporated herein by reference.

[0784] <<(Methyl)allyl-substituted naldiximide compounds>

[0785] As for (methyl)allyl-substituted nadicimide compounds, there are no particular limitations as long as the molecule has two or more (methyl)allyl-substituted nadicimide groups. Specific examples include compounds represented by the following formula (AN).

[0786] Formula (AN)

[0787]

[0788] In formula (AN), R1 independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and R2 represents an alkylene group having 1 to 6 carbon atoms, a phenylene group, a biphenylene group, a naphthylene group, or a group represented by formula (AN-2) or (AN-3).

[0789] Formula (AN-2)

[0790]

[0791] (In formula (AN-2), R3 represents a group represented by methylene, isopropylidene group, -C(=O)-, -O-, -S-, or -S(=O)2-.)

[0792] Formula (AN-3)

[0793]

[0794] (In formula (AN-3), R4 independently represents an alkylene group having 1 to 4 carbon atoms or a cycloalkylene group having 5 to 8 carbon atoms.)

[0795] In addition, the compounds shown in formula (AN) may also be commercially available products. There are no particular limitations on what constitutes a commercially available product; examples include compounds shown in formula (AN-4) (BANI-M (manufactured by Maruzen Petrochemical Co., Ltd.)) and compounds shown in formula (AN-5) (BANI-X (manufactured by Maruzen Petrochemical Co., Ltd.)). One or more of these compounds may be used.

[0796] Formula (AN-4)

[0797]

[0798] Formula (AN-5)

[0799]

[0800] The molecular weight of the (methyl)allyl-substituted nadicimide compound (preferably the compound shown in formula (AN)) is preferably 400 or more, more preferably 500 or more, and may also be 550 or more. By setting the molecular weight of the (methyl)allyl-substituted nadicimide compound to the lower limit or above, there is a tendency to further improve the low dielectric properties (Dk and / or Df), low thermal expansion, and heat resistance of the obtained cured product. The molecular weight of the (methyl)allyl-substituted nadicimide compound (preferably the compound shown in formula (AN)) is also preferably 1500 or less, more preferably 1000 or less, more preferably 800 or less, and may also be 700 or less, or 600 or less. By setting the molecular weight of the (methyl)allyl-substituted nadicimide compound to the upper limit or below, there is a tendency to further improve the formability and peel strength of the obtained cured product.

[0801] When the resin composition of this embodiment contains other polyfunctional (methyl)allyl compounds (preferably (methyl)allyl-substituted nadicimide compounds, more preferably compounds represented by formula (AN)), the content of these compounds is 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, and may also be 10 parts by mass or more, relative to 100 parts by mass of the resin solids in the resin composition. By setting the content of other polyfunctional (methyl)allyl compounds (especially (methyl)allyl-substituted nadicimide compounds) to the aforementioned lower limit value or above, there is a tendency for excellent formability, low dielectric properties (Dk and / or Df) of the obtained cured product, low thermal expansion, and further improved heat resistance. Furthermore, relative to 100 parts by weight of the resin solids in the resin composition, the upper limit of the content of other polyfunctional (methyl)allyl compounds (preferably (methyl)allyl-substituted nadicimide compounds, more preferably compounds represented by formula (AN)) is preferably 40 parts by weight or less, more preferably 30 parts by weight or less, and even more preferably 25 parts by weight or less, or possibly 20 parts by weight or less. By setting the content of other polyfunctional (methyl)allyl compounds (especially (methyl)allyl-substituted nadicimide compounds) to the aforementioned upper limit, there is a tendency to further improve the formability and the peel strength of the obtained cured product.

[0802] The resin composition of this embodiment may contain only one other polyfunctional (methyl)allyl compound (preferably a (methyl)allyl-substituted nadicimide compound), or it may contain two or more. When two or more are contained, the total amount is preferably within the range described above.

[0803] Alternatively, the resin composition in this embodiment may also be substantially free of (methyl)allyl-substituted nadicimide compounds. "Substantially free" means that the content of the (methyl)allyl-substituted nadicimide compound is less than 1 part by weight relative to 100 parts by weight of the resin solids in the resin composition, preferably less than 0.1 parts by weight, and more preferably less than 0.01 parts by weight.

[0804] Furthermore, the resin composition of this embodiment may also be substantially free of other polyfunctional (methyl)allyl compounds. "Substantially free" means that the content of other polyfunctional (methyl)allyl compounds is less than 1 part by weight relative to 100 parts by weight of the resin solids in the resin composition, preferably less than 0.1 parts by weight, and more preferably less than 0.01 parts by weight.

[0805] <<Multifunctional (meth)acrylate compounds other than the polyphenylene ether compound (B) with a carbon-carbon unsaturated double bond at the end and the (meth)acrylate compound (C3) with three or more (meth)acryloyloxy groups>>

[0806] The resin composition of this embodiment may contain polyfunctional (meth)acrylate compounds other than the polyphenylene ether compound (B) with carbon-carbon unsaturated double bonds at the end and the (meth)acrylate compound (C3) with three or more (meth)acryloyloxy groups.

[0807] Details of these resins can be exemplified by the resins containing (meth)acryloyloxy groups described in International Publication No. 2022 / 210095 (e.g., the compounds described in Synthesis Examples 5 and 21 of that publication) and the resins containing (meth)acryloyloxy groups described in Japanese Patent No. 6962507 (e.g., the compounds described in Examples 1 to 9), the contents of which are incorporated herein by reference.

[0808] When the resin composition of this embodiment contains at least one of the following: a styrene-based compound other than a polyphenylene ether compound (B) having a carbon-carbon unsaturated double bond at the end; an isopropyl-based compound other than a resin (A) having an indane backbone; a polyfunctional (meth)allyl compound other than the isocyanurate compound (C1) having two or more (meth)allyl groups and the glycourea compound (C2) having two or more (meth)allyl groups; a polyfunctional (meth)acrylate compound other than the polyphenylene ether compound (B) having a carbon-carbon unsaturated double bond at the end and the (meth)acrylate compound (C3) having three or more (meth)acryloyloxy groups; an arylcyclobutene resin; and a perfluorovinyl ether resin, the total content of these compounds relative to 100 parts by mass of the resin solids in the resin composition is preferably 1 part by mass or more, more preferably 5 parts by mass or more, and even more preferably 8 parts by mass or more. Depending on the application, the total content may also be 10 parts by mass or more, or 12 parts by mass or more. By setting the content above the aforementioned lower limit, there is a tendency to further improve the low dielectric properties (Dk and / or Df, especially the low dielectric loss tangent). Furthermore, the upper limit of its content relative to 100 parts by weight of the total resin solids in the resin composition is preferably 50 parts by weight or less, more preferably 40 parts by weight or less, even more preferably 35 parts by weight or less, even more preferably 32 parts by weight or less, and even more preferably 28 parts by weight or less. By setting the content below the aforementioned upper limit, there is a tendency to further improve heat resistance.

[0809] The resin composition of this embodiment may contain only one of the above-mentioned compounds, or it may contain two or more of them.

[0810] Alternatively, the resin composition of this embodiment may also be substantially free of the following compounds: styrene-based compounds other than polyphenylene ether compounds (B) with terminal carbon-carbon unsaturated double bonds; isopropyl-based compounds other than resins (A) with indane skeletons; polyfunctional (meth)allyl compounds other than the aforementioned isocyanurate compounds (C1) with two or more (meth)allyl groups and the aforementioned glycourea compounds (C2) with two or more (meth)allyl groups; polyfunctional (meth)acrylate compounds other than the aforementioned polyphenylene ether compounds (B) with terminal carbon-carbon unsaturated double bonds and the aforementioned (meth)acrylate compounds (C3) with three or more (meth)acryloyloxy groups; arylcyclobutene resins; and perfluorovinyl ether resins. "Substantially free" means that its content is less than 1 part by weight, preferably less than 0.1 parts by weight, and more preferably less than 0.01 parts by weight, relative to 100 parts by weight of the resin solids in the resin composition.

[0811] <<Elastomers>>

[0812] The resin composition of this embodiment may contain an elastomer. The elastomer may be thermoplastic, thermosetting, or neither thermoplastic nor thermosetting, preferably thermoplastic.

[0813] The elastomer used in this embodiment is not particularly limited, but may include at least one selected from the group consisting of polyisoprene, polybutadiene, styrene-butadiene, butyl rubber, ethylene-propylene rubber, styrene-butadiene-ethylene, styrene-butadiene-styrene, styrene-isoprene-styrene, styrene-ethylene-butene-styrene, styrene-propylene-styrene, styrene-ethylene-propylene-styrene, fluororubber, silicone rubber, their hydrides, their alkyl compounds, and their copolymers.

[0814] Furthermore, examples of elastomers include oligomers or polymers with curable vinyl functional groups described in paragraphs 0044 and 0045 of Japanese Patent Application Publication No. 2019-194312, and polybutadiene resins, which are incorporated herein by reference.

[0815] The number-average molecular weight of the elastomer (preferably a thermoplastic elastomer) used in this embodiment is preferably 1000 or more. By having a number-average molecular weight of 1000 or more, the resulting cured product tends to have superior low dielectric properties (Dk and / or Df, especially low dielectric loss tangent). The number-average molecular weight is preferably 1500 or more, more preferably 2000 or more, and depending on the application, it may also be 600,000 or more, 700,000 or more, or 800,000 or more. The upper limit of the number-average molecular weight of the elastomer is preferably 400,000 or less, more preferably 350,000 or less, and even more preferably 300,000 or less. By setting it to the above-mentioned upper limit or below, the solubility of the elastomer component in the resin composition tends to increase.

[0816] When the resin composition of this embodiment contains two or more elastomers, it is preferable that the number average molecular weight of their mixture satisfies the above-mentioned range.

[0817] The elastomer used in this embodiment can be a resin containing a polybutadiene structure. Part or all of the polybutadiene structure can be hydrogenated. Specific examples include Nippon Soda Corporation's B-1000, B-2000, B-3000, BI-2000, BI-3000, CRAY VALLEY Corporation's Ricon100, Ricon130, Ricon131, Ricon142, Ricon150, Ricon181, and Ricon184.

[0818] The elastomers used in this embodiment can be resins containing a poly(meth)acrylate structure. Specific examples include Teisan Resin manufactured by Nagase ChemteX, and ME-2000, W-197C, KG-15, and KG-3000 manufactured by Negami Kogyo Co., Ltd.

[0819] The elastomer used in this embodiment can be a resin containing a polycarbonate structure. Sometimes, a resin containing a polycarbonate structure is referred to as a "polycarbonate resin." Examples of such resins include carbonate resins without reactive groups, hydroxyl-containing carbonate resins, phenolic hydroxyl-containing carbonate resins, carboxyl-containing carbonate resins, acid anhydride-containing carbonate resins, isocyanate-containing carbonate resins, urethane-containing carbonate resins, and epoxy-containing carbonate resins. Here, "reactive group" refers to functional groups such as hydroxyl, phenolic hydroxyl, carboxyl, acid anhydride, isocyanate, urethane, and epoxy groups that can react with other components.

[0820] Specific examples of polycarbonate resins include FPC0220 and FPC2136 manufactured by Mitsubishi Gas Chemical Co., Ltd., and T6002 and T6001 (polycarbonate diol) manufactured by Asahi Kasei Chemical Co., Ltd.

[0821] The elastomers used in this embodiment can be resins containing a polysiloxane structure. Specific examples include SMP-2006, SMP-2003PGMEA, SMP-5005PGMEA, KR-510, and SMP-7014-3S manufactured by Shin-Etsu Silicone.

[0822] Examples of elastomers used in this embodiment include resins containing polyalkylene structures and / or polyalkylene oxide structures. The polyalkylene oxide structure is preferably a polyalkylene oxide structure with 2 to 15 carbon atoms, more preferably a polyalkylene oxide structure with 3 to 10 carbon atoms, and particularly preferably a polyalkylene oxide structure with 5 to 6 carbon atoms. Specific examples of resins containing polyalkylene structures and / or polyalkylene oxide structures include PTXG-1000 and PTXG-1800 manufactured by Asahi Kasei Fibers Corporation.

[0823] The elastomer used in this embodiment can be a resin containing a polyisoprene structure. Specific examples include KL-610 and KL613 manufactured by Kuraray.

[0824] The elastomer used in this embodiment can be a resin containing a polyisobutylene structure. Specific examples include SIBSTAR-073T (styrene-isobutylene-styrene triblock copolymer) and SIBSTAR-042D (styrene-isobutylene diblock copolymer) manufactured by Kaneka Corporation.

[0825] In this embodiment, the elastomer is preferably an elastomer comprising styrene monomer units and conjugated diene monomer units (hereinafter referred to as "elastomer (e)"). By using such an elastomer (e), the resulting cured product exhibits superior low dielectric properties (Dk and / or Df, particularly low dielectric loss tangent).

[0826] The elastomer (e) described above comprises styrene monomer units. By including styrene monomer units, the solubility of the elastomer (e) in the resin composition is improved. Examples of styrene monomers include styrene, α-methylstyrene, p-methylstyrene, divinylbenzene (vinylstyrene), N,N-dimethyl-p-aminoethylstyrene, N,N-diethyl-p-aminoethylstyrene, etc., among which styrene, α-methylstyrene, and p-methylstyrene are preferred from the viewpoint of availability and productivity. Styrene is particularly preferred.

[0827] The content of styrene monomer units in the elastomer (e) described above is preferably in the range of 10 to 50% by mass of all 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. When the content of styrene monomer units is 50% by mass or less, the adhesion and bonding properties with the substrate, etc., become better. In addition, if it is 10% by mass or more, excessive adhesion can be suppressed, residue and stop marks are less likely to occur, and the ease of peeling between the bonded surfaces tends to improve, which is therefore preferred.

[0828] The elastomer (e) may contain only one type of styrene monomer unit or two or more types. When it contains two or more types, the total amount is preferably within the range described above.

[0829] The method for determining the content of styrene monomer units in the elastomer (e) of this embodiment can be found in International Publication No. 2017 / 126469, the contents of which are incorporated herein by reference. The same applies to conjugated diene monomer units, etc., which will be described later.

[0830] The elastomer (e) described above comprises a conjugated diene monomer unit. By including the conjugated diene monomer unit, the solubility of the elastomer (e) in the resin composition is improved. As a conjugated diene monomer, there is no particular limitation as long as it is a diene having a pair of conjugated double bonds. Examples of conjugated diene monomers include 1,3-butadiene, 2-methyl-1,3-butadiene (isoprene), 2,3-dimethyl-1,3-butadiene, 1,3-pentadiene, 2-methyl-1,3-pentadiene, 1,3-hexadiene, and farnesene, with 1,3-butadiene and isoprene being preferred, and 1,3-butadiene being more preferred.

[0831] The elastomer (e) may contain only one type of conjugated diene monomer unit or more than two types.

[0832] In the elastomer (e) described above, the mass ratio of styrene monomer units to conjugated diene monomer units is preferably in the range of 5 / 95 to 80 / 20, more preferably in the range of 7 / 93 to 77 / 23, and even more preferably in the range of 10 / 90 to 70 / 30. When the mass ratio of styrene polymer units to conjugated diene monomer units is in the range of 5 / 95 to 80 / 20, excessive adhesion reinforcement can be suppressed, high adhesive strength can be maintained, and the ease of peeling between the bonded surfaces becomes good.

[0833] The elastomer (e) mentioned above can be one in which all the conjugated diene bonds of the elastomer are hydrogenated, or only some of them are hydrogenated, or they can be unhydrogenated.

[0834] The elastomer (e) described above may contain other monomer units besides styrene monomer units and conjugated diene monomer units, or it may not contain other monomer units. Examples of other monomer units include aromatic vinyl compound units other than styrene monomer units.

[0835] The elastomer (e) preferably has a total of 90% by mass or more of styrene monomer units and conjugated diene monomer units, more preferably 95% by mass or more, even more preferably 97% by mass or more, and even more preferably 99% by mass or more.

[0836] As described above, the elastomer (e) may contain only one type of styrene monomer unit and one type of conjugated diene monomer unit, or it may contain two or more types. When it contains two or more types, the total amount is preferably within the range described above.

[0837] The elastomer (e) used in this embodiment can be a block polymer or a random polymer. Alternatively, it can be a hydrogenated elastomer in which the conjugated diene monomer unit is hydrogenated, an unhydrogenated elastomer, or a partially hydrogenated elastomer, preferably an unhydrogenated or partially hydrogenated elastomer.

[0838] In one embodiment of this invention, the elastomer (e) is a hydrogenated elastomer. Here, a hydrogenated elastomer refers, for example, to a substance in an elastomer in which the double bonds based on conjugated diene monomer units are hydrogenated, including substances with a hydrogenation rate (hydrogenation ratio) of 80% or more, in addition to substances with a hydrogenation rate of 100%. The hydrogenation rate of the hydrogenated elastomer is preferably 85% or more, more preferably 90% or more, and even more preferably 95% or more. In this embodiment, the hydrogenation rate is determined by… 1 The result is calculated from the measurement results of H-NMR spectroscopy.

[0839] In one embodiment of this invention, the elastomer (e) is an unhydrogenated elastomer. Here, an unhydrogenated elastomer refers to an elastomer in which the proportion of hydrogenated double bonds in the double bonds based on conjugated diene monomer units, i.e., the hydrogenation rate (hydrogenation ratio), is 20% or less. The hydrogenation rate is preferably 15% or less, more preferably 10% or less, and even more preferably 5% or less.

[0840] On the other hand, partially hydrogenated elastomers refer to elastomers in which a portion of the double bond based on the conjugated diene monomer unit is hydrogenated, typically referring to elastomers with a hydrogenation rate (hydrogenation rate) of less than 80% and greater than 20%.

[0841] Commercially available products that can be used as elastomers (e) in this embodiment include SEPTON (registered trademark) 2104, V9461, S8104 manufactured by Kuraray Co., Ltd.; SOE (registered trademark) S1606, S1613, S1609, S1605 manufactured by Asahi Kasei Corporation; H1041, H1043, P2000, MP10 manufactured by Tuftec (registered trademark) manufactured by Asahi Kasei Corporation; and DYNARON (registered trademark) 9901P, TR2250 manufactured by JSR Co., Ltd.

[0842] The elastomer used in this embodiment can also be a liquid diene. A liquid diene refers to a liquid elastomer containing conjugated diene monomer units. Examples of conjugated diene monomers include 1,3-butadiene, 2-methyl-1,3-butadiene (isoprene), 2,3-dimethyl-1,3-butadiene, 1,3-pentadiene, 2-methyl-1,3-pentadiene, 1,3-hexadiene, and farnesene, with 1,3-butadiene and isoprene being preferred, and 1,3-butadiene being more preferred.

[0843] Examples of liquid dienes used in this embodiment include liquid polybutadiene, liquid polyisoprene, modified liquid polybutadiene, modified liquid polyisoprene, a copolymer of liquid acrylonitrile-butadiene, and a copolymer of liquid styrene-butadiene.

[0844] Furthermore, there are no particular limitations on the number-average molecular weight of the liquid diene, as long as it is liquid at 20°C, but it is preferably 500 or more and 10,000 or less.

[0845] When the resin composition of this embodiment includes an elastomer (preferably elastomer (e)), its content relative to 100 parts by mass of the resin solids in the resin composition is preferably 1 part by mass or more, more preferably 5 parts by mass or more, and even more preferably 8 parts by mass or more. Depending on the application, it may also be 10 parts by mass or more, or 12 parts by mass or more. By setting it to the lower limit or above, there is a tendency to further improve the dielectric properties (low dielectric loss tangent). In addition, relative to 100 parts by mass of the resin solids in the resin composition, the upper limit of the elastomer content is preferably 45 parts by mass or less, more preferably 40 parts by mass or less, even more preferably 35 parts by mass or less, even more preferably 32 parts by mass or less, and even more preferably 28 parts by mass or less. By setting it to the upper limit or below, there is a tendency to further improve the heat resistance.

[0846] The resin composition of this embodiment may contain only one type of elastomer or two or more types. When containing two or more types, the total amount is preferably within the range described above.

[0847] Alternatively, the resin composition in this embodiment may also be substantially free of elastomers. "Substantially free" means that the content of elastomers is less than 1 part by weight relative to 100 parts by weight of the resin solids in the resin composition, preferably less than 0.1 parts by weight, and more preferably less than 0.01 parts by weight.

[0848] <<Petroleum Resins>>

[0849] The resin composition of this embodiment may contain petroleum resin. By containing petroleum resin, the melt viscosity can be reduced.

[0850] Petroleum resin is a resin obtained by polymerizing the remaining components after thermally decomposing naphtha and collecting necessary fractions without separating unsaturated hydrocarbons or in the presence of a catalyst. These remaining fractions mainly consist of C5 fractions (isoprene, isoprene, cyclopentadiene, pentenes, pentanes, etc.) or C9 fractions (vinyltoluene, indene, dicyclopentadiene, etc.).

[0851] The catalysts used in the manufacture of petroleum resins are preferably acidic catalysts. Specifically, Lewis acids such as boron trifluoride phenol complexes, boron trifluoride ether complexes, aluminum chloride, aluminum bromide, ferric chloride (III), and ferric bromide (III), zeolites, silica, montmorillonite, and alumina, fluorinated resins containing sulfonic acid groups, polystyrene resins containing sulfonic acid groups, and protic acids such as sulfuric acid, hydrochloric acid, acetic acid, phosphoric acid, oxalic acid, nitric acid, p-toluenesulfonic acid, and trifluoroacetic acid can be used. Among these, Lewis acids and solid acids that are less prone to side reactions and have fast reaction rates are preferred. Considering ease of acquisition and high reactivity, various boron trifluoride complexes and aluminum chloride are more preferred.

[0852] There is no particular limitation on the weight-average molecular weight of petroleum resins, but it is preferably 500 to 10,000, more preferably 500 to 5,000. By setting it below the upper limit, it tends to be more miscible with other resins and its solubility in solvents also increases. By setting it above the lower limit, the heat resistance and mechanical strength of the resulting cured product tend to be further improved.

[0853] There is no particular limitation on the softening point of petroleum resin, but a high softening point is preferred, preferably 80°C or higher, and more preferably 100°C or higher. By setting it to a value above the aforementioned lower limit, there is a tendency to improve the heat resistance of the obtained cured product.

[0854] Examples of petroleum resins include aliphatic petroleum resins, aromatic petroleum resins, copolymer petroleum resins, and dicyclopentadiene petroleum resins, with dicyclopentadiene petroleum resins being preferred.

[0855] Examples of dicyclopentadiene-based petroleum resins include resins obtained by polymerizing dicyclopentadiene fractions such as dicyclopentadiene, isopropenyl norbornene, dimethyldicyclopentadiene, and tricyclopentadiene, as well as resins obtained by polymerizing dicyclopentadiene fractions with other monomers having unsaturated bonds, preferably unsaturated cyclic olefins.

[0856] Examples of the aforementioned unsaturated cyclic olefins include cyclopentadiene; norbornene monomers such as 2-norbornene, 5-methyl-2-norbornene, 5-ethylidene-2-norbornene, 5-phenylnorbornene, 5-propenyl-2-norbornene, and 5-ethylidene-2-norbornene; furthermore, examples of norbornene monomers with tricyclic or higher structures include tricyclic compounds other than dicyclopentadiene fractions such as diethyldicyclopentadiene and dihydrodicyclopentadiene, tetracyclic compounds such as tetracyclododecene, pentacyclic compounds such as tricyclopentadiene, heptacyclic compounds such as tetracyclopentadiene, and alkyl-substituted, alkylidene-substituted, and aryl-substituted forms of these polycyclic compounds. Examples of alkyl-substituted polycyclic compounds include methyl, ethyl, propyl, and butyl-substituted polycyclic compounds. Examples of alkylene-substituted polycyclic compounds include ethylidene-substituted polycyclic compounds. Examples of aryl-substituted polycyclic compounds include phenyl, tolyl, and naphthyl-substituted polycyclic compounds.

[0857] Furthermore, as monomers other than unsaturated cyclic olefins, olefins with 3 to 12 carbon atoms can be copolymerized. Examples include propylene, butene-1, pentene-1, 1,3-pentadiene, hexene-1, heptene-1, octene-1, diisobutylene, nonene-1, decene-1, 4-phenyl-1-butene, 6-phenyl-1-hexene, 3-methyl-1-butene, 4-methyl-1-pentene, 3-methyl-1-pentene, 3-methyl-1-hexene, 4-methyl-1-hexene, 5-methyl-1-hexene, 3,3-dimethyl-1-pentene, 3,4-dimethyl-1-pentene, 4,4-dimethyl-1-pentene, vinylcyclohexane, vinylcyclohexene, and other α-olefins; hexafluoropropylene, 2-fluoropropylene, 3-fluoropropylene, 3,4-dichlorobutene-1, and other halogen-substituted α-olefins.

[0858] Other monomers with unsaturated bonds besides those mentioned above include, for example, ethylene, tetrafluoroethylene, fluoroethylene, 1,1-difluoroethylene, trifluoroethylene; styrene, p-methylstyrene, o-methylstyrene, m-methylstyrene, 2,4-dimethylstyrene, 2,5-dimethylstyrene, 3,4-dimethylstyrene, 3,5-dimethylstyrene, p-tert-butylstyrene, etc.; halogenated styrene such as p-chlorostyrene, m-chlorostyrene, o-chlorostyrene, p-bromostyrene, m-bromostyrene, o-bromostyrene, p-fluorostyrene, m-fluorostyrene, o-fluorostyrene, o-methylp-fluorostyrene; maleic anhydride, maleic acid, fumaric acid, allyl alcohol, 3-buten-2-ol, methylbuten-1-ol, vinyl acetate, vinyl chloride, etc.

[0859] The above monomers can be used alone or in combination of two or more.

[0860] Commercially available petroleum resins can be used appropriately. Examples of aliphatic petroleum resins include Quinton A100, Quinton B170, Quinton K100, Quinton M100, Quinton R100, and Quinton C200S manufactured by ZEON Corporation of Japan; Marukarez T-100AS and Marukarez R-100AS manufactured by Maruzen Petrochemical Co., Ltd.; and aromatic petroleum resins include Neopolymer L-90, Neopolymer 120, Neopolymer 130, Neopolymer 140, Neopolymer 150, Neopolymer 170S, Neopolymer 160, Neopolymer E-100, Neopolymer E-130, Neopolymer 130S, and Neopolymer S manufactured by JXTG Energy Co., Ltd.; and Petcoal LX, Petcoal LX-HS, and Petcoal... 100T, Petcoal 120, Petcoal 120HS, Petcoal 130, Petcoal 140, Petcoal 140HM, Petcoal 140HM5, Petcoal 150, Petcoal 150AS; Quinton D100, Quinton N180, Quinton P195N, Quinton S100, Quinton S195, Quinton U185, Quinton G100B, Quinton G115, Quinton D200, Quinton E200SN, Quinton N295; Petrotac 60, Petrotac 70, Petrotac 90, Petrotac 90V, Petrotac... (the list of petroleum resins is missing from the original text). 100, Petrotac 100V, Petrotac 90HM, as DCPD (dicyclopentadiene) petroleum resins, Marukarez M-890A and Marukarez M-845A manufactured by Maruzen Petrochemical Co., Ltd., Quinton 1325, Quinton 1345, Quinton 1500, Quinton 1525L and Quinton 1700 manufactured by ZEON Corporation of Japan, and HA085, HA103, HA105, HA125, HB103 and HB125 manufactured by ENEOS Corporation, etc.

[0861] Alternatively, the petroleum resin described in Organic Synthetic Chemistry, Volume 25, No. 6 (1967) can also be used as a petroleum resin.

[0862] When the resin composition of this embodiment contains petroleum resin, the lower limit of its content relative to 100 parts by mass of resin solids in the resin composition is preferably 1 part by mass or more, more preferably 5 parts by mass or more, further preferably 10 parts by mass or more, even more preferably 20 parts by mass or more, and even more preferably 25 parts by mass or more. By setting it to the lower limit or above, there is a tendency for the melt viscosity to decrease. In addition, the upper limit of the petroleum resin content relative to 100 parts by mass of resin solids in the resin composition is preferably 70 parts by mass or less, more preferably 50 parts by mass or less, and may also be 40 parts by mass or less. By setting it to the upper limit or below, there is a tendency for Df to decrease.

[0863] The resin composition in this embodiment may contain only one type of petroleum resin, or it may contain two or more types. When it contains two or more types, the total amount is preferably within the range described above.

[0864] Alternatively, the resin composition in this embodiment may also be substantially free of petroleum resin. "Substantially free" means that the content of petroleum resin is less than 1 part by weight relative to 100 parts by weight of the solid resin component in the resin composition, preferably less than 0.1 parts by weight, and more preferably less than 0.01 parts by weight.

[0865] <Packaging (E)>

[0866] The resin composition of this embodiment preferably includes filler (E). By including filler (E), the physical properties of the resin composition and its cured product, such as low dielectric properties (Dk and / or Df), flame retardancy, and low thermal expansion, can be further improved.

[0867] Furthermore, the filler (E) used in this embodiment preferably exhibits excellent low dielectric properties (Dk and / or Df). For example, the relative permittivity (Dk) of the filler (E) used in this embodiment at a frequency of 10 GHz, measured according to the cavity resonator perturbation method, is preferably 8.0 or less, more preferably 6.0 or less, and even more preferably 4.0 or less. Additionally, a lower limit value of the relative permittivity is, for example, 2.0 or more. Furthermore, the dielectric loss tangent (Df) of the filler (E) used in this embodiment at a frequency of 10 GHz, measured according to the cavity resonator perturbation method, is preferably 0.05 or less, more preferably 0.01 or less. Additionally, a lower limit value of the dielectric loss tangent is, for example, 0.0001 or more.

[0868] The type of filler (E) used in this embodiment is not particularly limited, and fillers commonly used in the art can be preferred. Specifically, examples include natural silica, fused silica, synthetic silica, amorphous silica, aerosil, hollow silica, and other silica; alumina, silica, titanium dioxide, titanium dioxide, zinc oxide, magnesium oxide, zirconium oxide, and other metal oxides; zinc borate, zinc stannate, magnesium olivine, barium titanate, strontium titanate, calcium titanate, and other composite oxides; boron nitride, aggregated boron nitride, silicon nitride, aluminum nitride, and other nitrides; aluminum hydroxide, heat-treated aluminum hydroxide (a product obtained by heat-treating aluminum hydroxide to reduce a portion of the water of crystallization); boehmite, magnesium hydroxide, and other metal hydroxides (including hydrates); molybdenum oxide, zinc molybdate, and other molybdenum compounds; barium sulfate; clay; kaolin; and others. Talc, calcined clay, calcined kaolin, calcined talc, mica, E-glass, A-glass, NE-glass, NER-glass, C-glass, L-glass, D-glass, S-glass, M-glass G20, glass short fibers (including E-glass, T-glass, D-glass, S-glass, Q-glass and other glass micropowders), insulating glass, spherical glass and other inorganic fillers, as well as styrene-type, butadiene-type, acrylic-type and other rubber powders, core-shell type rubber powders, organosilicon resin powders, silicone rubber powders, organosilicon composite powders, fluorine-containing powders, PTFE (tetrafluoroethylene resin) microparticles, and organic fillers such as AGC-made Fluon+EA2000 as a fluororesin, etc.

[0869] In this embodiment, the filler (E) preferably comprises an inorganic filler, more preferably one selected from the group consisting of silica, aluminum hydroxide, aluminum nitride, boron nitride, magnesium olivine, titanium oxide, barium titanate, strontium titanate, and calcium titanate. From the viewpoint of the low dielectric properties (Dk and / or Df) of the obtained cured product, it is more preferably one selected from the group consisting of silica and aluminum hydroxide, and even more preferably silica. By using these fillers, the heat resistance, low dielectric properties (Dk and / or Df) of the cured resin composition, thermal expansion characteristics, dimensional stability, flame retardancy, and other properties are further improved.

[0870] The content of filler (E) in the resin composition of this embodiment can be appropriately set according to the desired characteristics and is not particularly limited. Relative to 100 parts by mass of the resin solids in the resin composition, it is preferably 1 part by mass or more, more preferably 5 parts by mass or more, further preferably 10 parts by mass or more, even more preferably 30 parts by mass or more, even more preferably 50 parts by mass or more, even more preferably 80 parts by mass or more, even more preferably 100 parts by mass or more, and may also be 120 parts by mass or more. By setting the content of filler (E) to the above-mentioned lower limit value or above, there is a tendency to further improve low thermal expansion and low dielectric loss tangent. Furthermore, relative to 100 parts by mass of the resin solids in the resin composition, the upper limit value of the content of filler (E) is preferably 1600 parts by mass or less, more preferably 1200 parts by mass or less, further preferably 800 parts by mass or less, even more preferably 500 parts by mass or less, even more preferably 300 parts by mass or less, and even more preferably 200 parts by mass or less. By setting the content of filler (E) to the above-mentioned upper limit value or less, there is a tendency to further improve formability.

[0871] In the resin composition of this embodiment, as an example of a preferred embodiment, the content of filler (E) can be 1 to 95% by mass of the components other than the solvent, preferably 30% to 80% by mass.

[0872] The resin composition of this embodiment may contain only one type of filler (E) or two or more types. When two or more types are contained, the total amount is preferably within the range described above.

[0873] In the resin composition of this embodiment, when filler (E), particularly inorganic filler, is used, a silane coupling agent may be further included. By including a silane coupling agent, there is a tendency to further improve the dispersibility of filler (E) and the adhesion strength between the resin components and filler (E) and the substrate described later.

[0874] As a silane coupling agent, there is no particular limitation. Examples of silane coupling agents commonly used in the surface treatment of inorganic materials include aminosilane compounds (such as γ-aminopropyltriethoxysilane, N-β-(aminoethyl)-γ-aminopropyltrimethoxysilane, etc.), epoxysilane compounds (such as γ-epoxypropoxypropyltrimethoxysilane, etc.), vinylsilane compounds (such as vinyltrimethoxysilane, etc.), styrylsilane compounds (such as p-styryltrimethoxysilane, etc.), acrylic silane compounds (such as γ-acryloyloxypropyltrimethoxysilane, etc.), cationic silane compounds (such as N-β-(N-vinylbenzylaminoethyl)-γ-aminopropyltrimethoxysilane hydrochloride, etc.), and phenylsilane compounds. Silane coupling agents can be used alone or in combination of two or more.

[0875] In particular, by using at least one selected from the group consisting of vinyl silane compounds, acrylic silane compounds, and styrene silane compounds as a silane coupling agent, and by using a compound containing a vinyl aryl group (especially a polymer having the structural unit shown in formula (V)), there is a tendency to further improve the low dielectric properties (Dk and / or Df) of the obtained cured product. Furthermore, by using at least one selected from the group consisting of vinyl silane compounds, acrylic silane compounds, and styrene silane compounds, and by combining a compound containing a vinyl aryl group (especially a polymer having the structural unit shown in formula (V)) with an elastomer, there is a tendency to further improve the low dielectric properties (Dk and / or Df) of the obtained cured product.

[0876] The content of the silane coupling agent is not particularly limited, but can be 0.1 to 5.0 parts by mass relative to 100 parts by mass of the resin solids in the resin composition.

[0877] <Monomers or oligomers having olefinic unsaturated groups>

[0878] In the resin composition of this embodiment, monomers or oligomers having olefinic unsaturated groups may be used in combination to improve thermosetting properties and curability based on active energy rays (e.g., photocurability based on ultraviolet light). The oligomers or monomers having olefinic unsaturated groups used in this embodiment are not particularly limited as long as they have one or more olefinic unsaturated groups per molecule. Examples include monomers or oligomers having vinyl, isopropenyl, allyl, (meth)acryloyl, vinylidene, etc., preferably monomers or oligomers having vinyl, isopropenyl, allyl, (meth)acryloyl, etc., and more preferably monomers or oligomers having vinyl.

[0879] It should be noted that, in this specification, compounds that are monomers or oligomers having olefinic unsaturated groups and that also belong to polyphenylene ether compounds (B) are considered polyphenylene ether compounds (B).

[0880] More specifically, examples of monomers having olefinic unsaturated groups include compounds (F1) with a molecular weight of less than 1,000 and containing one organic group with an olefinic unsaturated bond within the molecule.

[0881] The olefinic unsaturated bonds constituting the aforementioned organic groups containing olefinic unsaturated bonds do not include olefinic unsaturated bonds that are part of an aromatic ring. On the other hand, they include olefinic unsaturated bonds that are part of a non-aromatic ring. Examples of olefinic unsaturated bonds that are part of a non-aromatic ring include cyclohexenyl groups in a molecule. In addition, they also include olefinic unsaturated bonds contained in the portion other than the ends of straight-chain or branched organic groups, that is, in the straight chain or branched chain.

[0882] The aforementioned organic group containing an olefinic unsaturated bond is more preferably selected from the group consisting of vinyl, isopropenyl, allyl, acryloyl, methacryloyl, and vinylidene, more preferably selected from the group consisting of vinyl, isopropenyl, allyl, acryloyl, and methacryloyl, and even more preferably vinyl.

[0883] In addition, in this specification, compounds that are monomers or oligomers having olefinic unsaturated groups and are also silane coupling agents are considered silane coupling agents.

[0884] The compound (F1) used in this embodiment is preferably composed only of atoms selected from carbon atoms, hydrogen atoms, oxygen atoms, nitrogen atoms, phosphorus atoms and silicon atoms, more preferably composed only of atoms selected from carbon atoms, hydrogen atoms, oxygen atoms, nitrogen atoms and silicon atoms, even more preferably composed only of atoms selected from carbon atoms, hydrogen atoms, oxygen atoms and silicon atoms, and even more preferably composed only of atoms selected from carbon atoms, hydrogen atoms and oxygen atoms.

[0885] The compound (F1) used in this embodiment may or may not have polar groups. Preferably, the compound (F1) used in this embodiment does not have polar groups. Examples of polar groups include amino, carboxyl, hydroxyl, and nitro groups.

[0886] In this embodiment, the molecular weight of compound (F1) is preferably 70 or more, more preferably 80 or more, and even more preferably 90 or more. By setting it to the lower limit or above, there is a tendency to suppress the volatilization of compound (F1) from the resin composition of this embodiment, its cured product, etc. The upper limit of the molecular weight of compound (F1) is preferably 500 or less, more preferably 400 or less, even more preferably 300 or less, and even more preferably 200 or less, and may also be 150 or less. By setting it to the upper limit or below, there is a tendency to further improve the effect of increasing reactivity with other resin components.

[0887] When the resin composition of this embodiment contains two or more compounds (F1), it is preferable that the average molecular weight of the compounds (F1) is within the above-mentioned range, and more preferably that the molecular weight of each compound is within the above-mentioned preferred range.

[0888] In this embodiment, the boiling point of compound (F1) is preferably 110°C or higher, more preferably 115°C or higher, and even more preferably 120°C or higher. By setting it to the lower limit or higher, the volatilization of compound (F1) during the thermosetting of the resin composition is suppressed, allowing other resin components (D) to react with compound (F1). The boiling point of compound (F1) is preferably 300°C or lower, more preferably 250°C or lower, and even more preferably 200°C or lower. By setting it to the upper limit or lower, it is less likely to remain as a residual solvent in the cured product.

[0889] When the resin composition of this embodiment contains two or more compounds (F1), the average boiling point should fall within the above-mentioned range, and preferably the boiling point of each compound should be within the above-mentioned preferred range.

[0890] Examples of compounds (F1) include (meth)acrylate compounds, aromatic vinyl compounds (preferably styrene compounds), compounds containing isopropenyl groups, saturated fatty acid vinyl ester compounds, cyanide vinyl compounds, olefinic unsaturated carboxylic acids, olefinic unsaturated carboxylic anhydrides, olefinic unsaturated dicarboxylic acid monoalkyl esters, olefinic unsaturated carboxylic amides, phosphorus-containing vinyl compounds, unsaturated polyester compounds based on maleic anhydride, fumaric acid, itaconic acid, and citraconic acid; unsaturated epoxy (meth)acrylate compounds containing acryloyl or methacryloyl groups; unsaturated epoxy compounds containing vinyl or (meth)allyl groups, urethane (meth)acrylate compounds, polyether (meth)acrylate compounds, polyol (meth)acrylate compounds, alkyd acrylate compounds, polyester acrylate compounds, spiroacetal acrylate compounds, and triphenylvinylsilanes, preferably at least one selected from the group consisting of (meth)acrylate compounds, aromatic vinyl compounds, and saturated fatty acid vinyl ester compounds, more preferably aromatic vinyl compounds.

[0891] Specific examples of compounds (F1) that are aromatic vinyl compounds include methylstyrene (e.g., 4-methylstyrene), ethyl vinylbenzene, diethyl-4-vinylbenzylphosphonate, 4-vinylbenzyl glycidyl ether, α-methylstyrene, 4-tert-butylstyrene, 4-tert-butoxystyrene, vinylnaphthalene, vinylphenyl acetate, (methacryloyloxymethyl)diphenylphosphine oxide, diphenylvinylphosphine oxide, diphenyl-p-vinylbenzylphosphine oxide, and p-styryl diphenylphosphine oxide.

[0892] Furthermore, as a specific example of compound (F1), reference can be made to paragraphs 0046 and 0049 of Japanese Patent Application Publication No. 2019-194312, the contents of which are incorporated herein by reference.

[0893] As a specific example of a compound (F1) having vinylidene, acenaphthene, indene, tetradecahydrocyclopentane[fg]acenaphthene are preferred, and acenaphthene is more preferred.

[0894] In this specification, compounds that are also equivalent to compounds having vinylidene, and compounds that are explicitly stated as components other than compounds having vinylidene (e.g., curing accelerators), are not compounds having vinylidene.

[0895] On the other hand, in order to improve the low dielectric constant and low dielectric loss tangent, the resin composition of this embodiment preferably also includes a styrene oligomer (F2). The styrene oligomer (F2) of this embodiment is preferably formed by polymerizing at least one selected from the group consisting of styrene, the aforementioned styrene derivatives, and vinyltoluene. The number average molecular weight of the styrene oligomer (F2) is preferably 178 or more, and more preferably 1600 or less. Furthermore, the styrene oligomer (F2) is preferably an unbranched compound with an average number of aromatic rings of 2 to 14, a total amount of 2 to 14 aromatic rings of 50% by mass or more, and a boiling point of 300°C or more.

[0896] Examples of styrene oligomers (F2) used in this embodiment include styrene polymers, vinyltoluene polymers, α-methylstyrene polymers, vinyltoluene-α-methylstyrene polymers, and styrene-α-styrene polymers. Commercially available styrene polymers can be used, such as Picolatic A5 (manufactured by Eastman Chemical Company), Picolatic A-75 (manufactured by Eastman Chemical Company), Picotex 75 (manufactured by Eastman Chemical Company), FTR-8100 (manufactured by Mitsui Chemicals Co., Ltd.), and FTR-8120 (manufactured by Mitsui Chemicals Co., Ltd.). Additionally, Picotex LC (manufactured by Eastman Chemical Company) can be used as a vinyltoluene-α-methylstyrene polymer. In addition, examples of α-methylstyrene polymers include Kristalex 3070 (manufactured by Eastman Chemical Company), Kristalex 3085 (manufactured by Eastman Chemical Company), Kristalex (3100), Kristalex 5140 (manufactured by Eastman Chemical Company), FMR-0100 (manufactured by Mitsui Chemicals Co., Ltd.), and FMR-0150 (manufactured by Mitsui Chemicals Co., Ltd.). Additionally, examples of styrene-α-styrene polymers include FTR-2120 (manufactured by Mitsui Chemicals Co., Ltd.). These styrene oligomers can be used alone or in combination of two or more.

[0897] In the resin composition of this embodiment, α-methylstyrene oligomers are preferred from the aspects of good geothermal curing, good embedding of microwires and solder heat resistance, low relative permittivity, and excellent low dielectric loss tangent.

[0898] In addition, in order to improve the low dielectric constant and low dielectric loss tangent, the resin composition of this embodiment preferably contains a divinyl compound (F3) as a monomer having an olefinic unsaturated group.

[0899] Divinyl compounds are low-molecular-weight compounds with two vinyl groups. By having two vinyl groups, a good crosslinking density is achieved without being excessively high. As a result, the free volume of the molecule increases, thus allowing for a smaller dielectric loss tangent (Df) in the cured product. Furthermore, it is believed that using divinyl compounds (F3) as a substitute for resin (A), polyphenylene ether compound (B), and other resin components (D) reduces the content of components with polar groups, which itself contributes to the reduction of dielectric loss tangent (Df). In addition, it is believed that by ensuring that both functional groups in the divinyl compound are vinyl groups, its reactivity with resin (A) and polyphenylene ether compound (B) becomes good, resulting in a tendency to easily improve heat resistance.

[0900] It should be noted that the divinyl compound (F3) referred to here is a compound with a molecular weight of less than 600, preferably less than 300, more preferably less than 250, and even more preferably less than 195. Furthermore, a lower limit of 54 for molecular weight is practically defined. Examples of divinyl compounds (F3) include dicyclopentadiene-type difunctional (meth)acrylates, diallyl phthalate compounds, diallyl tetrabromophthalate compounds, diethylene glycol dielyl carbonate, divinylbenzene, 1-ethynyl-4-[2-(4-ethynylphenyl)ethyl]benzene (BVPE), diphenyldimethyldivinylsiloxane, 1,3-divinyltetramethyldisiloxane, bis(1-methylvinyl)benzene, divinylnaphthalene, divinylanthracene, divinylbiphenyl, and divinylphenanthrene.

[0901] Furthermore, trivinylphenylsilane, 1,3-diisopropenylbenzene, and 1,4-diisopropenylbenzene are preferred as monomers or oligomers having olefinic unsaturated groups.

[0902] Furthermore, details of monomers or oligomers having olefinic unsaturated groups can be found in paragraphs 0069 to 0087 of International Publication No. 2017 / 135168 and paragraphs 0065 to 0067 of International Publication No. 2019 / 230945, the contents of which are incorporated herein by reference.

[0903] When the resin composition of this embodiment contains monomers or oligomers having olefinic unsaturated groups, the content of such monomers or oligomers relative to 100 parts by mass of the resin solids in the resin composition is preferably 0.5 parts by mass or more, more preferably 1 part by mass or more, further preferably 2 parts by mass or more, even more preferably 3 parts by mass or more, and even more preferably 5 parts by mass or more. By setting the content to the above-mentioned lower limit or above, there is a tendency to further improve the low dielectric properties (Dk and / or Df) of the obtained cured product. In addition, the upper limit of the content of monomers or oligomers having olefinic unsaturated groups relative to 100 parts by mass of the resin solids in the resin composition is preferably 30 parts by mass or less, more preferably 25 parts by mass or less, further preferably 20 parts by mass or less, even more preferably 15 parts by mass or less, and even more preferably 10 parts by mass or less. By setting the content to the above-mentioned upper limit or below, there is a tendency to further improve the heat resistance of the obtained cured product. In addition, there is a tendency to further improve the low dielectric constant, low dielectric loss tangent, and chemical resistance.

[0904] The resin composition of this embodiment may contain only one monomer or oligomer having an olefinically unsaturated group, or it may contain two or more. When containing two or more, the total amount is preferably within the range described above.

[0905] <Active Ester Compounds>

[0906] The resin composition of this embodiment may contain an active ester compound.

[0907] For details of the active ester compounds, please refer to paragraphs 0064 to 0066 of International Publication No. 2021 / 172317, the contents of which are incorporated herein by reference.

[0908] When an active ester compound is included, it is preferably 1 part by mass or more, and more preferably 50 parts by mass or less, relative to 100 parts by mass of the resin solids in the resin composition.

[0909] The resin composition in this embodiment may contain only one active ester compound, or it may contain two or more. When it contains two or more, the total amount is preferably within the range described above.

[0910] Alternatively, the resin composition in this embodiment may also be substantially free of active ester compounds. "Substantially free" means that the content of active ester compounds is less than 1 part by weight relative to 100 parts by weight of the resin solids in the resin composition, preferably less than 0.1 parts by weight, and more preferably less than 0.01 parts by weight.

[0911] <Dispersant>

[0912] The resin composition of this embodiment may contain a dispersant. As a dispersant, a dispersant commonly used in coatings is preferred, and its type is not particularly limited. Preferably, a copolymer-based wetting dispersant or a fluorinated dispersant is used.

[0913] Specific examples of dispersants include BYK-Chemie Japan Co., Ltd.'s DISPERBYK (registered trademark)-110, 111, 161, 180, 2009, 2152, 2155, BYK (registered trademark)-W996, W9010, W903, W940, Ftergent manufactured by NEOS Co., Ltd., and MPT manufactured by Mitsubishi Pencil Co., Ltd.

[0914] When the resin composition of this embodiment contains a dispersant, the lower limit of its content relative to 100 parts by weight of the resin solids in the resin composition is preferably 0.01 parts by weight or more, more preferably 0.1 parts by weight or more, and may also be 0.3 parts by weight or more. Furthermore, the upper limit of the dispersant content relative to 100 parts by weight of the resin solids in the resin composition is preferably 10 parts by weight or less, more preferably 5 parts by weight or less, and even more preferably 3 parts by weight or less.

[0915] One type of dispersant may be used alone or in combination of two or more. When two or more types are used, the total dosage shall be within the range described above.

[0916] <Curing Accelerator>

[0917] The resin composition of this embodiment may further include a curing accelerator. There are no particular limitations on the curing accelerator; examples include imidazoles such as 2-ethyl-4-methylimidazolium and triphenylimidazolium; benzoyl peroxide, bis(1-methyl-1-phenylethyl) peroxide, di-tert-butyl peroxide, lauroyl peroxide, acetyl peroxide, p-chlorobenzoyl peroxide, di-tert-butyl peroxyphthalate, α,α'-di(tert-butylperoxy)diisopropylbenzene, 2,5-dimethyl-2,5-di(tert-butylperoxy)hexane, 2,5-dimethyl... Organic peroxides such as 2,5-bis(tert-butylperoxy)hexyne-3; azobisnitrile compounds such as azobis(isobutyronitrile) and 2,2'-azobis(2,4,4-trimethylpentane); 4-hydroxy-2,2,6,6-tetramethylpiperidine 1-oxy radical (4-hydroxy-TEMPO radical), 2,2,6,6-tetramethylpiperidine 1-oxy radical (TEMPO radical), 4-hydroxy-2,2,6,6-tetramethylpiperidine 1-oxy radical Free radicals such as oxybenzoate free radicals, 1,1-diphenyl-2-picrylhydrazyl free radicals, and galvanoxy free radicals; tertiary amines such as N,N-dimethylbenzylamine, N,N-dimethylaniline, N,N-dimethyltoluidine, 2-N-ethylaniline ethanol, tri-n-butylamine, pyridine, quinoline, N-methylmorpholine, triethanolamine, triethylenediamine, tetramethylbutyldiamine, and N-methylpiperidine; and phenols such as phenol, xylenol, cresol, resorcinol, and catechol. High-temperature decomposition free radical generators such as 2,3-dimethyl-2,3-diphenylbutane; organometallic salts such as lead naphthenate, lead stearate, zinc naphthenate, zinc octanoate, manganese octanoate, tin oleate, dibutyltin maleate, manganese naphthenate, cobalt naphthenate, and iron acetylacetone; substances formed by dissolving these organometallic salts in phenol, bisphenol, and other hydroxyl-containing compounds; inorganic metal salts such as tin chloride, zinc chloride, and aluminum chloride; organotin compounds such as dioctyltin oxide, other alkyltin, and alkyltin oxide.

[0918] The curing accelerator is preferably selected from at least one of the groups consisting of imidazoles, organic peroxides and organometallic salts, more preferably selected from at least one of the groups consisting of imidazoles and organometallic salts, and even more preferably imidazoles.

[0919] Alternatively, in this embodiment, the composition may be substantially free of polymerization initiators such as organic peroxides and azo compounds. "Substantially free" means that the content of the polymerization initiator is less than 0.1 parts by weight per 100 parts by weight of the resin solids in the resin composition.

[0920] When the resin composition of this embodiment contains a curing accelerator, the lower limit of its content relative to 100 parts by weight of the resin solids in the resin composition is preferably 0.005 parts by weight or more, more preferably 0.01 parts by weight or more, and even more preferably 0.1 parts by weight or more. Furthermore, the upper limit of the content of the curing accelerator relative to 100 parts by weight of the resin solids in the resin composition is preferably 10 parts by weight or less, more preferably 5 parts by weight or less, even more preferably 3 parts by weight or less, even more preferably 2 parts by weight or less, even more preferably 1.5 parts by weight or less, even more preferably 1.0 parts by weight or less, even more preferably 0.8 parts by weight or less, and particularly preferably 0.7 parts by weight or less. The resin composition of this embodiment is preferred in that it allows the resin composition to be sufficiently cured even when the content of the curing accelerator is set to 0.8 parts by weight or less.

[0921] One type of curing accelerator can be used alone or in combination of two or more. When two or more types are used, the total dosage shall be within the range described above.

[0922] Flame retardants

[0923] The resin composition of this embodiment may contain a flame retardant. Examples of flame retardants include phosphorus-based flame retardants, halogen-based flame retardants, inorganic flame retardants, and organosilicon-based flame retardants, with phosphorus-based flame retardants being preferred.

[0924] As flame retardants, known flame retardants can be used, such as brominated epoxy compounds, brominated polycarbonates, brominated polystyrene, brominated styrene, brominated phthalimide, tetrabromobisphenol A, pentabromobenzyl methacrylate, pentabromotoluene, tribromophenol, hexabromobenzene, decabromodiphenyl ether, bis-1,2-pentabromophenylethane, chlorinated polystyrene, chlorinated paraffin and other halogenated flame retardants, red phosphorus and other phosphorus-containing flame retardants, tricresyl phosphate, triphenyl phosphate, 2,5-dihydroxyphenyl-10H-9-oxa-10-phosphaphenanthrene-10-oxide, toluene diphenyl phosphate, tri(xylyl) phosphate, trialkyl phosphate, dialkyl phosphate, tri(chloroethyl) phosphate and other monomeric phosphate esters, phosphazenes, phenoxyphosphazenes, 1,3-phenylenebis(2,6-dimethylyl) phosphate, and 1,3-phenylenebis(2,6-dixylenyl) phosphate. Phosphorus-based flame retardants include phosphates, bis(diphenylphosphine) oxides, condensed phosphates of di(dimethyl) phosphate esters, 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (6H-dibenz[c,e][1,2]oxaphosphorine), 6,6'-[1,4-phenylenebis(methylene)]bis-,6,6'-dioxide (6,6'-[1,4-phenylenebis(methylene)]bis-,6,6'-dioxide), phosphinate-based metal salts of dialkyl phosphinate aluminum salts, and other phosphorus-based flame retardants; inorganic flame retardants such as aluminum hydroxide, magnesium hydroxide, some boehmite, zinc borate, and antimony trioxide; and organosilicon-based flame retardants such as silicone rubber and organosilicon resins.

[0925] In this embodiment, 1,3-phenylenebis[bis(2,6-dimethylyl)phosphate] is preferred from the viewpoint of not impairing the low dielectric properties (Dk and / or Df) of the obtained cured product.

[0926] When the resin composition of this embodiment contains a flame retardant, its content is preferably 1 part by mass or more, more preferably 5 parts by mass or more, relative to 100 parts by mass of the resin solids in the resin composition. Furthermore, the lower limit of the flame retardant content is preferably 25 parts by mass or less, more preferably 20 parts by mass or less.

[0927] Flame retardants can be used alone or in combination of two or more. When two or more are used, the total amount shall be within the range mentioned above.

[0928] Solvent

[0929] The resin composition of this embodiment may contain a solvent, preferably an organic solvent. When a solvent is present, the resin composition of this embodiment is in a form (solution or varnish) in which at least a portion, preferably all, of the various resin solid components described above are dissolved or compatible with the solvent. As a solvent, there are no particular limitations as long as it is capable of dissolving or being compatible with at least a portion, preferably all, of the various resin solid components described above. Examples of polar organic solvents include ketones (e.g., acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, etc.), cellosols (e.g., propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, etc.), esters (e.g., ethyl lactate, methyl acetate, ethyl acetate, butyl acetate, isoamyl acetate, ethyl lactate, methyl methoxypropionate, methyl hydroxyisobutyrate, etc.), and amides (e.g., dimethoxyacetamide, dimethylformamide, etc.). Examples of non-polar organic solvents include aromatic hydrocarbons (e.g., toluene, xylene, etc.).

[0930] One solvent may be used alone or in combination of two or more. When two or more solvents are used, the total amount shall be within the range described above.

[0931] <Other Ingredients>

[0932] In addition to the components described above, the resin composition of this embodiment may also contain various polymeric compounds such as resins and their oligomers, and various additives. Examples of additives include ultraviolet absorbers, antioxidants, photopolymerization initiators, fluorescent whitening agents, photosensitizers, dyes, pigments, thickeners, flow modifiers, lubricants, defoamers, leveling agents, gloss agents, quinones, phenols, nitrosamines, hydroxylamines, and other polymerization inhibitors. These additives may be used individually or in combination of two or more.

[0933] <Application>

[0934] The resin composition of this embodiment is used as a cured product. Specifically, the resin composition of this embodiment is suitable for use as a resin composition for electronic materials such as materials with low relative permittivity and / or low dielectric loss tangent, insulating layers for printed circuit boards, and materials for semiconductor packaging. The resin composition of this embodiment is suitable for use as a prepreg, a metal foil laminate using prepreg, a resin composite sheet, and a material for printed circuit boards.

[0935] The cured resin composition of this embodiment can maintain a high glass transition temperature. Specifically, the glass transition temperature of the cured resin composition of this embodiment is preferably 180°C or higher, more preferably 190°C or higher, and even more preferably 200°C or higher. The upper limit of the above glass transition temperature is not particularly limited, and for example, it is practical to be 400°C or lower. In order to maintain a high glass transition temperature, the resin composition can be adjusted, especially when the polyphenylene ether compound (B) contains the polyphenylene ether compound represented by the above formula (OP) and Rx is a group represented by formula (Rx-2), a high glass transition temperature can be effectively maintained.

[0936] The resin composition of this embodiment is used as a prepreg, resin composite sheet, or other layered material (including film, sheet, etc.) that forms an insulating layer for a printed circuit board. When producing this layered material, its thickness is preferably 5 μm or more, more preferably 10 μm or more. As an upper limit for the thickness, it is preferably 200 μm or less, more preferably 180 μm or less. It should be noted that the thickness of the above-mentioned lay...

Claims

1. A resin composition comprising: Resin A having terminal groups as shown in formula (T1) and having an indane backbone; Polyphenylene ether compound B with carbon-carbon unsaturated double bonds at the ends; and The compound is selected from at least one of the following groups: isocyanurate compound C1 having two or more (meth)allyl groups, glycidyl urea compound C2 having two or more (meth)allyl groups, and (meth)acrylate compound C3 having three or more (meth)acryloyloxy groups. In formula (T1), Ma independently represents hydrocarbon groups with 1 to 12 carbon atoms that are arbitrarily substituted by halogen atoms, x represents an integer from 0 to 4, and * represents the bonding position with other sites.

2. The resin composition according to claim 1, wherein, The resin A having the terminal groups shown in formula (T1) and having an indene skeleton comprises the resin shown in formula (T1-1). In formula (T1-1), R is a group containing the structural unit shown in formula (Tx), Ma independently represents a hydrocarbon group with 1 to 12 carbon atoms that are optionally substituted with halogen atoms, and x is an integer from 0 to 4. In formula (Tx), n, o, and p are the average number of repeating units, n represents a number greater than 0 and less than 20, o and p each independently represent a number from 0 to 20, 1.0≤n+o+p≤20.0, Ma each independently represents a hydrocarbon group with 1 to 12 carbon atoms that are arbitrarily substituted by halogen atoms, x represents an integer from 0 to 4, and structural units (a), (b), and (c) are bonded to structural units (a), (b), (c), or other groups at *, respectively, and each structural unit is randomly bonded.

3. The resin composition according to claim 1 or 2, wherein, The polyphenylene ether compound B, which has a carbon-carbon unsaturated double bond at the end, includes the polyphenylene ether compound represented by formula (OP). In formula (OP), X represents an aromatic group, and -(YO) n1 - indicates a polyphenylene ether structure, n1 represents an integer from 1 to 100, n2 represents an integer from 1 to 4, and Rx is the group shown in formula (Rx-1) or formula (Rx-2). In equations (Rx-1) and (Rx-2), R 1 R 2 and R 3 Each group independently represents a hydrogen atom, alkyl, alkenyl, or alkynyl group, * represents the bonding site with an oxygen atom, Mc independently represents a hydrocarbon group with 1 to 12 carbon atoms, z represents an integer from 0 to 4, and r represents an integer from 0 to 6.

4. The resin composition according to claim 1 or 2, wherein, Relative to 100 parts by weight of resin A having the terminal groups shown in formula (T1) and having an indane backbone, it comprises: 10 to 900 parts by mass of the polyphenylene ether compound B having carbon-carbon unsaturated double bonds at the ends; and The total amount of 10 to 900 parts by mass of the compound selected from the group consisting of isocyanurate compound C1 having two or more (meth)allyl groups, glycourea compound C2 having two or more (meth)allyl groups, and (meth)acrylate compound C3 having three or more (meth)acryloyloxy groups.

5. The resin composition according to claim 1 or 2, wherein, The polyphenylene ether compound B with carbon-carbon unsaturated double bonds at the ends has a number-average molecular weight Mn of 500 to 3000 and a weight-average molecular weight Mw of 800 to 6000.

6. The resin composition according to claim 1 or 2, wherein, The number-average molecular weight Mn of the resin A having the terminal group shown in formula (T1) and having an indane skeleton is 400 to 3000.

7. The resin composition according to claim 1 or 2, wherein, The isocyanurate compound C1 having two or more (meth)allyl groups is represented by formula (TA), the glycourea compound C2 having two or more (meth)allyl groups is represented by formula (GU-O), and the (meth)acrylate compound C3 having three or more (meth)acryloyloxy groups is represented by formula (MA). Formula (TA) In formula (TA), R A Indicates substituent, Formula(GU-0) In formula (GU-0), R 1 Each is an independent hydrogen atom or substituent, R 1 At least two of them are groups containing (methyl)allyl groups. Formula (MA) In formula (MA), R 1 R represents a hydrogen atom or substituent. 2 Each can be used independently to represent a hydrogen atom or a methyl group.

8. The resin composition according to claim 1 or 2, wherein, The isocyanurate compound C1 having two or more (meth)allyl groups is represented by formula (TA), the glycourea compound C2 having two or more (meth)allyl groups is represented by formula (GU), and the (meth)acrylate compound C3 having three or more (meth)acryloyloxy groups is represented by formula (MA). Formula (TA) In formula (TA), R A Indicates substituent, Formula(GU) In formula (GU), each R is an independent hydrogen atom or substituent, and at least two of R are groups containing (methyl)allyl groups. Formula (MA) In formula (MA), R 1 R represents a hydrogen atom or substituent. 2 Each can be used independently to represent a hydrogen atom or a methyl group.

9. The resin composition according to claim 1 or 2, wherein, The isocyanurate compound C1 having two or more (meth)allyl groups has a molecular weight of 200 to 3000, the glycourea compound C2 having two or more (meth)allyl groups has a molecular weight of 195 to 1500, and the meth acrylate compound C3 having three or more (meth)acryloyloxy groups has a molecular weight of 300 to 3000.

10. The resin composition according to claim 1 or 2, further comprising other component D, said other component D being selected from maleimide compounds, polymers having structural units of formula (V), epoxy resins, phenolic compounds, oxacyclobutane resins, benzoxazine compounds, cyanate ester compounds, arylcyclobutene resins, polyamide resins, polyimide resins, perfluorovinyl ether resins, styrene-based compounds other than said polyphenylene ether compound B having carbon-carbon unsaturated double bonds at the ends, isopropylene-based compounds other than said resin A having an indane backbone, and other compounds... Compounds other than resin A that have carbon-carbon unsaturated double bonds at the ends and have an indane skeleton, polyfunctional (meth)allylic compounds other than the isocyanurate compound C1 having two or more (meth)allylic groups and the glycourea compound C2 having two or more (meth)allylic groups, polyfunctional (meth)acrylate compounds other than the polyphenylene ether compound B having carbon-carbon unsaturated double bonds at the ends and the (meth)acrylate compound C3 having three or more (meth)acryloyloxy groups, elastomers, and petroleum resins, comprising one or more of the following: In formula (V), Ar represents an aromatic hydrocarbon linking group, and * represents a bonding position.

11. The resin composition according to claim 1 or 2, further comprising filler E.

12. The resin composition according to claim 11, wherein, The filler E comprises one or more selected from the group consisting of silicon dioxide, aluminum hydroxide, aluminum nitride, boron nitride, magnesium olivine, titanium oxide, barium titanate, strontium titanate, and calcium titanate.

13. The resin composition according to claim 11, wherein, The content of filler E in the resin composition is 1 to 1600 parts by mass relative to 100 parts by mass of the resin solids component in the resin composition.

14. The resin composition according to claim 1 or 2, wherein, Relative to 100 parts by weight of the resin solids in the resin composition, it also contains 0.5 to 30 parts by weight of monomers or oligomers having olefinic unsaturated groups.

15. The resin composition according to claim 1 or 2, further comprising a flame retardant, said flame retardant comprising a phosphorus-based flame retardant.

16. The resin composition according to claim 1 or 2, wherein, The mass ratio of the polyphenylene ether compound B with a carbon-carbon unsaturated double bond at the end to the total mass of the compounds selected from the group consisting of isocyanurate compound C1 having two or more (meth)allyl groups, glycourea compound C2 having two or more (meth)allyl groups, and (meth)acrylate compound C3 having three or more (meth)acryloyloxy groups, is B / [C1+C2+C3] 1.0 to 9.

0.

17. The resin composition according to claim 1, wherein, The resin A having the terminal groups shown in formula (T1) and having an indene skeleton comprises the resin shown in formula (T1-1). The polyphenylene ether compound B, which has a carbon-carbon unsaturated double bond at the end, includes the polyphenylene ether compound represented by formula (OP). Relative to 100 parts by weight of resin A having the terminal group shown in formula (T1) and having an indane backbone, the resin A comprises 10 to 900 parts by weight of the polyphenylene ether compound B having a carbon-carbon unsaturated double bond at the end, and a total of 10 to 900 parts by weight of the compound selected from the group consisting of isocyanurate compound C1 having two or more (meth)allyl groups, glycourea compound C2 having two or more (meth)allyl groups, and (meth)acrylate compound C3 having three or more (meth)acryloyloxy groups. The polyphenylene ether compound B with terminal carbon-carbon unsaturated double bonds has a number-average molecular weight Mn of 500–3000 and a weight-average molecular weight Mw of 800–6000. The number-average molecular weight Mn of the resin A having the terminal groups shown in formula (T1) and having an indene skeleton is 400 to 3000. The isocyanurate compound C1 having two or more (meth)allyl groups is represented by formula (TA), the glycourea compound C2 having two or more (meth)allyl groups is represented by formula (GU-O), and the (meth)acrylate compound C3 having three or more (meth)acryloyloxy groups is represented by formula (MA). The isocyanurate compound C1 having two or more (meth)allyl groups has a molecular weight of 200-3000; the glycourea compound C2 having two or more (meth)allyl groups has a molecular weight of 195-1500; and the methacrylate compound C3 having three or more (meth)acryloyloxy groups has a molecular weight of 300-3000. The resin composition further comprises other components D, which are selected from maleimide compounds, polymers having structural units shown in formula (V), epoxy resins, phenolic compounds, oxacyclobutane resins, benzoxazine compounds, cyanate ester compounds, arylcyclobutene resins, polyamide resins, polyimide resins, perfluorovinyl ether resins, styrene-based compounds other than the polyphenylene ether compound B with a carbon-carbon unsaturated double bond at the end, isopropylene-based compounds other than the resin A with an indane backbone, and other compounds besides the resin A. The group consisting of one or more compounds having a carbon-carbon unsaturated double bond at the end and having an indene skeleton, polyfunctional (meth)allyl compounds other than the isocyanurate compound C1 having two or more (meth)allyl groups and the glycourea compound C2 having two or more (meth)allyl groups, polyfunctional (meth)acrylate compounds other than the polyphenylene ether compound B having a carbon-carbon unsaturated double bond at the end and the (meth)acrylate compound C3 having three or more (meth)acryloyloxy groups, elastomers, and petroleum resins. The mass ratio of the polyphenylene ether compound B, which has a carbon-carbon unsaturated double bond at the end, to the total mass of compounds selected from the group consisting of isocyanurate compound C1 having two or more (meth)allyl groups, glycourea compound C2 having two or more (meth)allyl groups, and (meth)acrylate compound C3 having three or more (meth)acryloyloxy groups, is B / [C1+C2+C3] 1.0 to 9.

0. In formula (T1-1), R is a group containing the structural unit shown in formula (Tx), Ma independently represents a hydrocarbon group with 1 to 12 carbon atoms that are optionally substituted with halogen atoms, and x is an integer from 0 to 4. In formula (Tx), n, o, and p are the average number of repeating units, where n represents a number greater than 0 and less than 20, o and p each independently represent a number from 0 to 20, 1.0 ≤ n + o + p ≤ 20.0, Ma each independently represents a hydrocarbon group with 1 to 12 carbon atoms arbitrarily substituted by a halogen atom, and x represents an integer from 0 to 4. Structural units (a), (b), and (c) are bonded to structural units (a), (b), and (c) or other groups at *, respectively. Each structural unit is randomly bonded. In formula (OP), X represents an aromatic group, and -(YO) n1 - indicates a polyphenylene ether structure, n1 represents an integer from 1 to 100, n2 represents an integer from 1 to 4, and Rx is the group shown in formula (Rx-1) or formula (Rx-2). In equations (Rx-1) and (Rx-2), R 1 R 2 and R 3 Each group independently represents a hydrogen atom, alkyl, alkenyl, or alkynyl group; * indicates the bonding site with an oxygen atom; Mc independently represents a hydrocarbon group with 1 to 12 carbon atoms; z represents an integer from 0 to 4; and r represents an integer from 0 to 6. Formula (TA) In formula (TA), R A Indicates substituent, Formula(GU-0) In formula (GU-0), R 1 Each is an independent hydrogen atom or substituent, R 1 At least two of them are groups containing (methyl)allyl groups. Formula (MA) In formula (MA), R 1 R represents a hydrogen atom or substituent. 2 Each can independently represent a hydrogen atom or a methyl group. In formula (V), Ar represents an aromatic hydrocarbon linking group, and * represents a bonding position.

18. The resin composition according to claim 17, wherein, The glycourea compound C2 having two or more (methyl)allyl groups is represented by formula (GU). Formula(GU) In formula (GU), each R is an independent hydrogen atom or substituent, and at least two of R are groups containing (methyl)allyl groups.

19. The resin composition according to claim 17, wherein, The other component D is selected from one or more of the following groups: maleimide compounds, polymers having structural units as shown in formula (V), epoxy resins, phenolic compounds, oxacyclobutane resins, benzoxazine compounds, cyanate compounds, arylcyclobutene resins, polyamide resins, polyimide resins, perfluorovinyl ether resins, styrene compounds other than the polyphenylene ether compound B with a carbon-carbon unsaturated double bond at the end, isopropyl compounds other than the resin A with an indane skeleton, polyfunctional (meth)allyl compounds other than the isocyanurate compound C1 with two or more (meth)allyl groups and the glycourea compound C2 with two or more (meth)allyl groups, polyfunctional (meth)acrylate compounds other than the polyphenylene ether compound B with a carbon-carbon unsaturated double bond at the end and the (meth)acrylate compound C3 with three or more (meth)acryloyloxy groups, elastomers, and petroleum resins. In formula (V), Ar represents an aromatic hydrocarbon linking group, and * represents a bonding position.

20. The resin composition according to claim 17, wherein, In equation (Rx-1), r represents an integer from 1 to 6.

21. The resin composition according to any one of claims 1, 2 and 17 to 20, used in a printed circuit board.

22. A cured product, which is a cured product of the resin composition according to any one of claims 1, 2 and 17 to 20.

23. A prepreg formed from a substrate and a resin composition according to any one of claims 1, 2 and 17 to 20.

24. A metal foil laminate comprising: at least one prepreg as described in claim 23, and a metal foil disposed on one or both sides of the prepreg.

25. A resin composite sheet comprising: a support; and a layer formed of the resin composition according to any one of claims 1, 2 and 17 to 20 disposed on the surface of the support.

26. A printed circuit board comprising: an insulating layer and a conductor layer disposed on a surface of the insulating layer. The insulating layer comprises a layer formed from the resin composition of any one of claims 1, 2 and 17 to 20.

27. A semiconductor device comprising the printed circuit board of claim 26.

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