Resin compositions, varnishes, prepregs, cured products, films, laminates, metal-clad laminates, printed circuit boards and electronic devices

Abstract

This invention provides a resin composition with an improved balance of low dielectric properties and miscibility. [Solution] A resin composition comprising a cyclic olefin polymer (m) having a crosslinkable group, and an aromatic polymer (n) containing repeating units (D) derived from an aromatic compound having carbon-hydrogen groups with 1 to 20 carbon atoms on a benzene ring.

Description

[Technical Field]

[0001] The present invention relates to resin compositions, varnishes, prepregs, cured products, films, laminates, metal-clad laminates, printed circuit boards, and electronic devices. [Background technology]

[0002] In recent years, with the increase in wireless communication equipment using high-frequency bands and the resulting increase in communication speeds, higher frequency bands have inevitably become more common. Consequently, in order to minimize transmission loss at high frequencies, materials constituting printed circuit boards are required to have a low dielectric loss tangent.

[0003] Patent Document 1 describes a cyclic olefin copolymer having crosslinkable groups, which can be obtained to obtain a crosslinked body that is excellent in the time-dependent stability and heat resistance of dielectric properties, as well as excellent in transparency, mechanical properties, dielectric properties and gas barrier properties, and further provides a crosslinked body with excellent properties. The objective is to provide a crosslinked body with excellent properties. The cyclic olefin copolymer having crosslinkable groups comprises (A) one or more repeating units derived from an olefin represented by a specific chemical formula (I), (B) a repeating unit derived from a cyclic non-conjugated diene represented by a specific chemical formula (III), and (C) one or more repeating units derived from a cyclic olefin represented by a specific chemical formula (V), wherein when the total number of moles of repeating units is 100 mol%, the repeating units derived from the cyclic non-conjugated diene (B) are contained in an amount of 19 mol% to 36 mol%.

[0004] Furthermore, Patent Document 2 addresses the objective of providing a resin composition that can yield a crosslinked material suitable for circuit boards, such as an interlayer insulating film (also called an interlayer insulating layer in a circuit board) for a circuit board for a highly integrated computing device, and excellent dielectric properties, heat resistance, and mechanical properties in the high-frequency range, and is a cyclic olefin copolymer resin composition comprising a cyclic olefin copolymer (M) and a maleimide compound (L), wherein the cyclic olefin copolymer (M) comprises a cyclic olefin copolymer (m) comprising one or more repeating units derived from an olefin represented by a specific chemical formula (I), one or more repeating units derived from a cyclic non-conjugated diene represented by a specific chemical formula (III), and one or more repeating units derived from a cyclic olefin represented by a specific chemical formula (V), and the maleimide compound (L) has a solubility parameter (SP value) of 19 J as determined by the Fedors method. 1 / 2 / cm 3 / 2 Above, 26J 1 / 2 / cm 3 / 2 The following describes a cyclic olefin copolymer resin composition comprising a maleimide compound (l), which is a bismaleimide compound having at least two maleimide groups in its molecule, wherein the content of the maleimide compound (L) is 1 part by mass or more and 50 parts by mass or less when the total amount of the cyclic olefin copolymer (M) and the maleimide compound (L) is 100 parts by mass. [Prior art documents] [Patent Documents]

[0005] [Patent Document 1] International Publication No. 2012 / 046443 [Patent Document 2] International Publication No. 2020 / 110958 [Overview of the Initiative] [Problems that the invention aims to solve]

[0006] According to the inventors' investigation, when a cyclic olefin polymer with good low dielectric properties and heat resistance is mixed with an aromatic polymer with good low dielectric properties, the two polymers do not mix well, indicating that there is room for improvement in miscibility.

[0007] This invention provides a resin composition with an improved balance of low dielectric properties and miscibility.

[0008] As a result of diligent research to solve the above problems, the present inventors have found that the miscibility of the resulting resin composition can be improved by combining a cyclic olefin polymer having a crosslinkable group with an aromatic polymer having a specific structure, and have completed the present invention. In this specification, miscibility of the resin composition means the property of mixing the cyclic olefin polymer and the aromatic polymer.

[0009] The present invention is as follows.

[0010] [1] A cyclic olefin polymer (m) having a crosslinkable group, A resin composition comprising an aromatic polymer (n) containing repeating units (D) derived from one or more aromatic compounds represented by the following general formula (X). [ka] [In the general formula (X), R 1 R is a hydrocarbon group having 1 to 20 carbon atoms. 2 ~R 4 These may be the same or different atoms, and are hydrogen atoms or hydrocarbon groups having 1 to 20 carbon atoms. [2] When the total number of moles of repeating units in the aromatic polymer (n) is set to 100 mol%, The resin composition according to [1], wherein the content of repeating units (D) derived from the aromatic compound in the aromatic polymer (n) is 50 mol% or more. [3] The aromatic polymer (n) is the R 1The resin composition according to [1] or [2], comprising a repeating unit (d1) derived from an aromatic compound having an aliphatic hydrocarbon group without an unsaturated double bond. [4] The aromatic polymer (n) is the R 1 The resin composition according to [3], further comprising a repeating unit (d2) derived from an aromatic compound having an aliphatic hydrocarbon group with an unsaturated double bond. [5] When the total number of moles of the repeating units in the aromatic polymer (n) is 100 mol%, The resin composition according to [4], wherein the ratio (D2 / D1) of the content D2 of the repeating unit (d2) to the content D1 of the repeating unit (d1) in the aromatic polymer (n) is 0 or more and 2.0 or less. [6] When the content of the cyclic olefin polymer (m) in the resin composition is 100 parts by mass, the content of the aromatic polymer (n) in the resin composition is 1 part by mass or more and 300 parts by mass or less. The resin composition according to any one of [1] to [5]. [7] The resin composition according to any one of [1] to [6], wherein the number average molecular weight (Mn) in terms of polystyrene measured by gel permeation chromatography of the aromatic polymer (n) is 400 or more. [8] The cyclic olefin polymer (m) is One or more repeating units (A) derived from olefins represented by the following general formula (I), One or more repeating units (B) derived from cyclic non-conjugated dienes represented by the following general formula (III), One or more repeating units (C) derived from cyclic olefins represented by the following general formula (V). The resin composition according to any one of [1] to [7].

Chemical formula

[10] The cyclic olefin constituting the repeating unit (C) derived from the cyclic olefin is bicyclo[2.2.1]-2-heptene and tetracyclo[4.4.0.1 2,5 .1 7,10 The resin composition according to [8] or [9], comprising at least one selected from the group consisting of ]-3-dodecene.

[11] The cyclic olefin constituting the repeating unit (C) derived from the cyclic olefin is tetracyclo[4.4.0.1 2,5 .1 7,10 A resin composition according to any one of [8] to

[10] , comprising ]-3-dodecene.

[12] The resin composition according to any one of [1] to

[11] , wherein the number-average molecular weight (Mn) of the cyclic olefin polymer (m), measured on a polystyrene basis by gel permeation chromatography, is 5000 or more.

[13] A resin composition according to any one of [1] to

[12] , further comprising an antioxidant.

[14] The resin composition according to any one of [1] to

[13] , wherein the dielectric loss tangent of the cured resin composition at 10 GHz is less than 0.0030.

[15] A resin composition according to any one of [1] to

[14] , further comprising a radical polymerization initiator.

[16] The resin composition according to

[15] , comprising the radical polymerization initiator bibenzyl compounds.

[17] A varnish comprising a resin composition described in any of [1] to

[16] and a solvent.

[18] A prepreg comprising a fibrous substrate impregnated with a resin composition described in any of [1] to

[16] or a varnish containing the resin composition and a solvent.

[19] A cured product of any of the resin compositions described in [1] to

[16] .

[20] A film comprising a resin composition described in any of [1] to

[16] or a cured product of the resin composition. [twenty one] A laminate comprising the prepreg described in

[18] or the film described in

[20] . [twenty two] A metal-clad laminate comprising a metal foil on at least one side of the laminate described in

[21] . [twenty three] A printed circuit board manufactured using the metal-clad laminate described in

[22] . [twenty four]

[19] An electronic device containing the cured product described above. [twenty five] The electronic device described in

[24] includes a high-speed communication module. [Effects of the Invention]

[0011] According to the present invention, it is possible to provide a resin composition with an improved balance of low dielectric properties and miscibility. [Modes for carrying out the invention]

[0012] The present invention will be described below based on embodiments. In these embodiments, unless otherwise specified, "A~B" indicating a numerical range represents A or greater and B or less. Furthermore, in this specification, "cyclic olefin polymer" means at least one polymer selected from the group consisting of homopolymers of cyclic olefins and copolymers of cyclic olefins and monomer components other than cyclic olefins. Furthermore, each monomer constituting the cyclic olefin polymer (m) according to the present invention may be a monomer obtained from fossil raw materials or a monomer obtained from animal or plant raw materials. Furthermore, in this embodiment, the -CH=CH2 group in the (meth)acrylic group is not included in the vinyl group. Furthermore, in this embodiment, crosslinking refers to the property of a compound in which crosslinking groups undergo a curing reaction to form crosslink bonds, thereby yielding a cured product. It is also an indicator of how little thermal energy is required to obtain the desired cured product in the curing reaction. The better the crosslinking, the lower the thermal energy required to obtain the cured product.

[0013] <Resin composition> The resin composition of this embodiment comprises a cyclic olefin polymer (m) having a crosslinkable group and an aromatic polymer (n) containing repeating units (D) derived from one or more aromatic compounds represented by the following general formula (X).

[0014] [ka]

[0015] In the above general formula (X), R 1 R is a hydrocarbon group having 1 to 20 carbon atoms. 2 ~R 4 These may be the same or different from each other, and are hydrogen atoms or hydrocarbon groups having 1 to 20 carbon atoms.

[0016] The resin composition of this embodiment offers an improved balance between low dielectric properties and miscibility. For example, using the resin composition of this embodiment, it is possible to obtain a cured product with improved uniformity. The following provides a detailed explanation of each component.

[0017] (Cyclic olefin polymer having crosslinkable groups (m)) The resin composition of this embodiment contains a cyclic olefin polymer (m) having crosslinkable groups (hereinafter also simply referred to as "cyclic olefin polymer (m)"). The cyclic olefin polymer (m) can be used without particular limitations as long as it is curable and contains repeating units derived from a cyclic olefin. For example, it may be a ring-opening polymer of a cyclic olefin, or it may be an addition polymer of a monomer such as an α-olefin and a cyclic olefin. Furthermore, the cyclic olefin polymer (m) has a crosslinkable group, which is a functional group that can be used in the crosslinking reaction, from the viewpoint of improving the heat resistance of the cured product obtained by forming a crosslinked structure. Examples of crosslinkable groups include vinyl groups, vinylidene groups, vinylene groups, vinylen groups substituted with alkyl groups, phenyl groups, or alkylphenyl groups, vinylidene groups substituted with alkyl groups, phenyl groups, or alkylphenyl groups, vinylene groups substituted with alkyl groups, phenyl groups, or alkylphenyl groups, maleimide groups, thiol groups, thienyl groups, silyl groups, epoxy groups, oxazoline groups, (meth)acrylic groups, and carboxyl groups, with vinyl groups being preferred. A single molecule of the cyclic olefin polymer (m) may have one or more crosslinkable groups, and if a single molecule has multiple crosslinkable groups, there may be one type or two or more types.

[0018] The cyclic olefin polymer (m) of this embodiment preferably includes, from the viewpoint of further improving the balance between low dielectric properties and miscibility, one or more repeating units (A) derived from an olefin represented by the following general formula (I), a repeating unit (B) derived from a cyclic non-conjugated diene represented by the following general formula (III), and one or more repeating units (C) derived from a cyclic olefin represented by the following general formula (V).

[0019] [ka]

[0020] In the above general formula (I), R 300 This represents a hydrogen atom or a linear or branched hydrocarbon group having 1 to 29 carbon atoms.

[0021] [ka]

[0022] In the above general formula (III), u is 0 or 1, v is 0 or a positive integer, preferably an integer between 0 and 2, more preferably 0 or 1, w is 0 or 1, R61 ~R 76 Furthermore, R a1 and R b1 These may be the same or different from each other, and are a hydrogen atom, a halogen atom, an alkyl group having 1 to 20 carbon atoms, a halogenated alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 15 carbon atoms, or an aromatic hydrocarbon group having 6 to 20 carbon atoms, R 104 is a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, t is a positive integer from 0 to 10, and R 75 and R 76 These elements may be bonded to each other to form a monocycle or polycycle.

[0023] [ka]

[0024] In the above general formula (V), u is 0 or 1, v is 0 or a positive integer, preferably an integer between 0 and 2, more preferably 0 or 1, w is 0 or 1, R 61 ~R 78 Furthermore, R a1 and R b1 These may be the same or different from each other, and are a hydrogen atom, a halogen atom, an alkyl group having 1 to 20 carbon atoms, a halogenated alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 15 carbon atoms, or an aromatic hydrocarbon group having 6 to 20 carbon atoms, R 75 ~R 78 These elements may be bonded to each other to form a monocycle or polycycle.

[0025] When the cyclic olefin polymer (m) is a polymer (m) containing the above repeating units (A) to (C), and the total number of moles of repeating units in the cyclic olefin polymer (m) is taken as 100 mol%, the content of olefin-derived repeating units (A) is preferably 10 mol% to 90 mol%, more preferably 20 mol% to 85 mol%, even more preferably 30 mol% to 80 mol%, even more preferably 40 mol% to 70 mol%, even more preferably 50 mol% to 70 mol%, and even more preferably 55 mol% to 65 mol%, and the content of cyclic non-conjugated diene-derived repeating units (B) is preferably 1 mol% to 40 mol%, more preferably 5 mol% or less. The content of repeating units (C) derived from cyclic olefins is preferably 40 mol% or less, more preferably 5 mol% to 35 mol%, more preferably 7 mol% to 30 mol%, more preferably 10 mol% to 30 mol%, more preferably 15 mol% to 30 mol%, and more preferably 20 mol% to 30 mol%, with the content of repeating units (C) derived from cyclic olefins being preferably 1 mol% to 50 mol%, more preferably 3 mol% to 40 mol%, more preferably 10 mol% to 35 mol%, more preferably 10 mol% to 30 mol%, more preferably 10 mol% to 25 mol%, more preferably 10 mol% to 20 mol%, and more preferably 10 mol% to 15 mol%. When the content of each repeating unit in the cyclic olefin polymer (m) is within the above range, the cured product obtained from the resin composition can have improved dielectric properties and improved heat resistance. Furthermore, a cured product with an improved balance of mechanical properties, dielectric properties, transparency, and gas barrier properties can be obtained.

[0026] An olefin monomer that can be used as a copolymerizing raw material for a cyclic olefin polymer (m) is a monomer that undergoes addition copolymerization to give a skeleton represented by the above general formula (I), and can be an olefin represented by the following general formula (Ia).

[0027] [ka]

[0028] In the above general formula (Ia), R 300 ∫ represents a hydrogen atom or a linear or branched hydrocarbon group having 1 to 29 carbon atoms. Examples of olefins represented by general formula (Ia) include ethylene, propylene, 1-butene, 1-pentene, 1-hexene, 3-methyl-1-butene, 3-methyl-1-pentene, 3-ethyl-1-pentene, 4-methyl-1-pentene, 4-methyl-1-hexene, 4,4-dimethyl-1-hexene, 4,4-dimethyl-1-pentene, 4-ethyl-1-hexene, 3-ethyl-1-hexene, 1-octene, 1-decene, 1-dodecene, 1-tetradecene, 1-hexadecene, 1-octadecene, and 1-eicosene. From the viewpoint of obtaining a cured product with superior heat resistance, mechanical properties, dielectric properties, transparency, and gas barrier properties, one or two of these, consisting of ethylene and propylene, are preferred, with ethylene being more preferred. Two or more types of olefin monomers represented by the above formula (Ia) may be used.

[0029] A cyclic non-conjugated diene monomer, which can be one of the copolymerization raw materials for a cyclic olefin polymer (m), can be subjected to addition copolymerization to form a structural unit represented by the above general formula (III). Specifically, a cyclic non-conjugated diene represented by the following general formula (IIIa), which corresponds to the above general formula (III), can be used.

[0030] [ka]

[0031] In the above general formula (IIIa), u is 0 or 1, v is 0 or a positive integer, preferably an integer between 0 and 2, more preferably 0 or 1, w is 0 or 1, R 61 ~R 76 Furthermore, R a1 and R b1These may be the same or different from each other, and are a hydrogen atom, a halogen atom, an alkyl group having 1 to 20 carbon atoms, a halogenated alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 15 carbon atoms, or an aromatic hydrocarbon group having 6 to 20 carbon atoms, R 104 is a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, t is a positive integer from 0 to 10, and R 75 and R 76 These elements may be bonded to each other to form a monocycle or polycycle.

[0032] The cyclic non-conjugated diene represented by the above general formula (IIIa) is not particularly limited, but examples include the cyclic non-conjugated diene represented by the following chemical formula. Of these, the cyclic non-conjugated diene represented by the general formula (IIIa), that is, the cyclic non-conjugated diene constituting the repeating unit (B) derived from the cyclic non-conjugated diene, is preferably 5-vinyl-2-norbornene, 8-vinyl-9-methyltetracyclo[4.4.0.1 2,5 .1 7,10 ]-3-dodecene, 5-allyl-2-norbornene and 8-vinyl-tetracyclo[4.4.0.1 2,5 .1 7,10 It comprises at least one selected from the group consisting of ]-3-dodecene, more preferably at least one selected from the group consisting of 5-vinyl-2-norbornene and 5-allyl-2-norbornene, and even more preferably 5-vinyl-2-norbornene. The cyclic non-conjugated diene constituting the repeating unit (B) derived from the cyclic non-conjugated diene is 5-vinyl-2-norbornene, 8-vinyl-9-methyltetracyclo[4.4.0.1 2,5 .1 7,10 ]-3-dodecene, 5-allyl-2-norbornene and 8-vinyl-tetracyclo[4.4.0.1 2,5 .1 7,10 If it includes at least one selected from the group consisting of ]-3-dodecene, the repeating unit (C) derived from the cyclic olefin described below is preferably tetracyclo[4.4.0.1 2,5 .1 7,10 Contains ]-3-dodecene.

[0033] [ka]

[0034] [ka]

[0035] The cyclic non-conjugated dienes represented by the above general formula (IIIa) can also be specifically represented by the following general formula (IIIb).

[0036] [ka]

[0037] In general formula (IIIb), n is an integer between 0 and 10, R1 is a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, and R2 is a hydrogen atom or an alkyl group having 1 to 5 carbon atoms.

[0038] When the cyclic olefin polymer (m) of this embodiment contains a structural unit derived from a cyclic non-conjugated diene represented by general formula (III), it has a double bond in the side chain portion, i.e., in the portion other than the main chain of the copolymer. A functional group containing such a double bond can be one of the crosslinkable groups.

[0039] When a cyclic olefin polymer (m) contains repeating units (C) derived from a cyclic olefin, a cyclic olefin monomer, which may be one of the copolymerization raw materials for the cyclic olefin polymer (m), can be added copolymerized to form a constituent unit represented by the above general formula (V). Specifically, a cyclic olefin monomer represented by the following general formula (Va), which corresponds to the above general formula (V), can be used.

[0040] [ka]

[0041] In the above general formula (Va), u is 0 or 1, v is 0 or a positive integer, preferably an integer between 0 and 2, more preferably 0 or 1, w is 0 or 1, R 61 ~R 78 Furthermore, R a1 and R b1 These may be the same or different from each other, and are a hydrogen atom, a halogen atom, an alkyl group having 1 to 20 carbon atoms, a halogenated alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 15 carbon atoms, or an aromatic hydrocarbon group having 6 to 20 carbon atoms, R 75 ~R 78 These elements may be bonded to each other to form a monocycle or polycycle.

[0042] For specific examples of cyclic olefins represented by the above general formula (Va), compounds described in International Publication No. 2006 / 118261 can be used. The cyclic olefin represented by the above general formula (Va), that is, the cyclic olefin constituting the repeating unit (C) derived from the cyclic olefin, is bicyclo[2.2.1]-2-heptene (also called norbornene) and tetracyclo[4.4.0.1 2,5 .1 7,10 Preferably, it contains at least one selected from the group consisting of ]-3-dodecene (also called tetracyclododecene), and tetracyclo[4.4.0.1 2,5 .1 7,10 It is more preferable to include ]-3-dodecene.

[0043] The number-average molecular weight (Mn) of the cyclic olefin polymer (m), measured by gel permeation chromatography in terms of polystyrene, is preferably 5,000 or more, more preferably 10,000 or more, even more preferably 15,000 or more, and even more preferably 18,000 or more, from the viewpoint of further improving the balance of performance of low dielectric properties, low thermal expansion properties, and mechanical properties. Furthermore, from the viewpoint of further improving moldability such as impregnation into the fiber substrate and wiring embedding properties when manufacturing printed circuit boards, it is preferably 100,000 or less, more preferably 80,000 or less, even more preferably 60,000 or less, even more preferably 40,000 or less, even more preferably 30,000 or less, and even more preferably 25,000 or less. The number-average molecular weight (Mn) of a cyclic olefin polymer (m) can be controlled by polymerization conditions such as polymerization catalyst, co-catalyst, H2 addition amount, and polymerization temperature. The number-average molecular weight (Mn) of a cyclic olefin polymer (m) can be controlled by polymerization conditions such as polymerization catalyst, co-catalyst, H2 addition amount, and polymerization temperature.

[0044] The cyclic olefin polymer (m) of this embodiment can be produced, for example, by the method described in Japanese Patent Application Publication No. 2004-331965.

[0045] (Aromatic polymer(n)) The resin composition of this embodiment comprises an aromatic polymer (n) containing one or more repeating units (D) derived from aromatic compounds represented by the following general formula (X).

[0046] [ka]

[0047] In the above general formula (X), R 1 R is a hydrocarbon group having 1 to 20 carbon atoms. 2 ~R 4 These may be the same or different from each other, and are hydrogen atoms or hydrocarbon groups having 1 to 20 carbon atoms.

[0048] The number-average molecular weight (Mn) of the aromatic polymer (n), measured by gel permeation chromatography on a polystyrene basis, is preferably 400 to 5000, more preferably 500 to 3000, even more preferably 600 to 2000, even more preferably 600 to 1500, and even more preferably 600 to 1200.

[0049] When the content of the cyclic olefin polymer (m) in the resin composition of this embodiment is 100 parts by mass, the content of the aromatic polymer (n) in the resin composition of this embodiment is preferably 1 part by mass or more and 300 parts by mass or less, more preferably 2 parts by mass or more and 250 parts by mass or less, even more preferably 3 parts by mass or more and 200 parts by mass or less, even more preferably 4 parts by mass or more and 150 parts by mass or less, even more preferably 5 parts by mass or more and 100 parts by mass or less, even more preferably 6 parts by mass or more and 80 parts by mass or less, even more preferably 7 parts by mass or more and 60 parts by mass or less, even more preferably 7 parts by mass or more and 40 parts by mass or less, and even more preferably 7 parts by mass or more and 20 parts by mass or less.

[0050] When the total number of moles of repeating units in the aromatic polymer (n) is set to 100 mol%, the content of repeating units (D) derived from aromatic compounds in the aromatic polymer (n) is preferably 50 mol% to 100 mol%, more preferably 60 mol% to 100 mol%, even more preferably 70 mol% to 100 mol%, even more preferably 80 mol% to 100 mol%, and even more preferably 90 mol% to 100 mol%. The content of each repeating unit in the aromatic polymer (n) can be calculated, for example, from the amount of monomer used before polymerization.

[0051] From the viewpoint of improving miscibility, the aromatic polymer (n) is preferably R 1 It contains repeating units (d1) derived from aromatic compounds, which are aliphatic hydrocarbon groups that do not have unsaturated double bonds. The aliphatic hydrocarbon group having no unsaturated double bond includes one selected from the group consisting of an alkyl group having 1 to 20 carbon atoms and an alicyclic hydrocarbon group having 3 to 20 carbon atoms. From the viewpoint of further improving miscibility, it preferably includes an alkyl group having 1 to 20 carbon atoms, more preferably includes an alkyl group having 1 to 10 carbon atoms, still more preferably includes an alkyl group having 1 to 5 carbon atoms, and still more preferably includes a methyl group. R in the repeating unit (d1) 2 ~R 4 is preferably at least one is a hydrogen atom, more preferably at least two are hydrogen atoms, and still more preferably two of R 2 ~R 4 are hydrogen atoms. Among R 2 ~R 4 in the repeating unit (d1), the hydrocarbon group is preferably an alkyl group having 1 to 20 carbon atoms, more preferably an alkyl group having 1 to 10 carbon atoms, still more preferably an alkyl group having 1 to 5 carbon atoms, and still more preferably a methyl group. The aromatic compound forming the repeating unit (d1) includes one or more selected from the group consisting of vinyltoluene and isopropenyltoluene from the viewpoint of further improving the performance balance of low dielectric characteristics, miscibility and heat resistance, and more preferably includes isopropenyltoluene.

[0052] The aromatic polymer (n) may further contain a repeating unit (d2) derived from an aromatic compound in which R 1 is an aliphatic hydrocarbon group having an unsaturated double bond. The aliphatic hydrocarbon group having an unsaturated double bond preferably includes an alkenyl group having 1 to 20 carbon atoms, more preferably includes an alkenyl group having 1 to 10 carbon atoms, still more preferably includes an alkenyl group having 1 to 5 carbon atoms, and still more preferably includes a vinyl group from the viewpoint of further improving the heat resistance of the obtained cured product. When the aromatic polymer (n) contains the repeating unit (d2), preferably at least one of R 2 ~R 4 in the repeating unit (d2) is a hydrogen atom, more preferably 2 ~R 4At least two of them are hydrogen atoms, and more preferably R 2 ~R 4 All of them are hydrogen atoms. From the viewpoint of further improving the balance of low dielectric properties, miscibility, and heat resistance, the aromatic compounds that form the repeating unit (d2) preferably include divinyl aromatic compounds, and more preferably divinylbenzene (e.g., o-divinylbenzene, m-divinylbenzene, p-divinylbenzene), diisopropenylbenzene (e.g., 1,2-diisopropenylbenzene, 1,3-diisopropenylbenzene, 1,4-diisopropenylbenzene), divinylnaphthalene (e.g., 1,3-divinylnaphthalene, 1,8-divinylnaphthalene, 1,4-divinylnaphthalene, 1,5-divinylnaphthalene, 2,3-divinylnaphthalene, 2,7-di The material comprises one or more selected from the group consisting of vinylnaphthalene (2,6-divinylnaphthalene), divinylbiphenyl (e.g., 4,4'-divinylbiphenyl, 4,3'-divinylbiphenyl, 4,2'-divinylbiphenyl, 3,2'-divinylbiphenyl, 3,3'-divinylbiphenyl, 2,2'-divinylbiphenyl, 2,4-divinylbiphenyl), 1,2-divinyl-3,4-dimethylbenzene, 1,3-divinyl-4,5,8-tributylnaphthalene, and 2,2'-divinyl-4-ethyl-4'-propylbiphenyl, more preferably divinylbenzene, and even more preferably p-divinylbenzene.

[0053] When the total number of moles of repeating units in the aromatic polymer (n) is set to 100 mol%, the ratio of the content of repeating units (d2) to the content of repeating units (d1) D1 (D2 / D1) in the aromatic polymer (n) is preferably 0 to 2.0, more preferably 0 to 1.5, even more preferably 0 to 1.0, and even more preferably 0 to 0.7, from the viewpoint of further improving the heat resistance of the resulting cured product.

[0054] <Other ingredients> The aromatic polymer (n) may contain repeating units other than the repeating unit (D) derived from the aromatic compound represented by the general formula (X) above (hereinafter also referred to as repeating units derived from other components).

[0055] Other components include, for example, indene and unsaturated aliphatic hydrocarbons, preferably unsaturated aliphatic hydrocarbons.

[0056] Unsaturated aliphatic hydrocarbons are copolymerizable components with repeating units (d1) and (d2), such as C4 and C5 fractions. Repeating units derived from other components in the aromatic polymer (n) may include repeating units derived from one or more selected from the group consisting of C4 and C5 fractions, preferably including repeating units derived from one or more selected from the group consisting of C5 fractions.

[0057] The C4 fraction is obtained by refining and / or cracking petroleum. The C4 fraction is a fraction with a boiling point range of typically -15°C to 45°C under normal pressure, and includes, for example, carbon-4 unsaturated aliphatic hydrocarbons that do not contain conjugated double bonds, and carbon-4 unsaturated aliphatic hydrocarbons that contain conjugated double bonds.

[0058] Examples of unsaturated aliphatic hydrocarbons with four carbon atoms that do not contain conjugated double bonds include 1-butene, isobutene, and 2-butene.

[0059] Examples of unsaturated aliphatic hydrocarbons with four carbon atoms containing a conjugated double bond include 1,3-butadiene.

[0060] The C5 fraction is obtained by refining and / or cracking petroleum. The C5 fraction is a fraction with a boiling point range of typically -15°C to 45°C under normal pressure, and includes, for example, unsaturated aliphatic hydrocarbons with 5 carbon atoms that do not contain conjugated double bonds, and unsaturated aliphatic hydrocarbons with 5 carbon atoms that contain conjugated double bonds.

[0061] Examples of unsaturated aliphatic hydrocarbons with 5 carbon atoms that do not contain conjugated double bonds include 1-pentene, 2-methyl-1-butene, 3-methyl-1-butene, and 2-pentene.

[0062] Examples of unsaturated aliphatic hydrocarbons with 5 carbon atoms containing a conjugated double bond include isoprene, 1,3-pentadiene, and cyclopentadiene.

[0063] When the total number of moles of repeating units in the aromatic polymer (n) is taken as 100 mol%, the content of repeating units derived from other components is preferably 0 mol% to 10 mol%, more preferably 0 mol% to 8 moles, and more preferably 0 mol% to 6 moles.

[0064] Furthermore, all or part of the repeating units in the aromatic polymer (n) may be derived from fossil fuels or biomass.

[0065] Fossil fuels include petroleum, coal, natural gas, shale gas, or combinations thereof. Biomass refers to all renewable natural raw materials and their residues, including plant-derived or animal-derived materials such as fungi, yeasts, algae, and bacteria.

[0066] Furthermore, aromatic polymers (n) can be obtained by polymerizing each monomer in the presence of a Friedel-Crafts catalyst.

[0067] Examples of Friedel-Crafts catalysts include phenolic complexes (e.g., boron trifluoride phenolate complexes).

[0068] The proportion of the Friedel-Crafts catalyst used is, for example, 0.01 to 1 part by mass per 100 parts by mass of the polymerization component.

[0069] The polymerization conditions include a polymerization temperature of, for example, -50°C to 50°C, preferably -30°C to 30°C, and more preferably -10°C to 10°C. The polymerization time is, for example, 10 minutes to 10 hours.

[0070] Furthermore, the above reaction may be carried out in the presence or absence of a solvent. Preferably, the above reaction is carried out in the presence of a solvent.

[0071] Examples of solvents include aliphatic hydrocarbons, alicyclic hydrocarbons, aromatic hydrocarbons, ketones, and alkyl esters. Aromatic hydrocarbons are preferred as solvents. Examples of aromatic hydrocarbons include toluene and xylene. Toluene is preferred as an aromatic hydrocarbon.

[0072] Solvents can be used alone or in combination of two or more types.

[0073] (Antioxidant) The resin composition of this embodiment preferably further contains an antioxidant. The antioxidant preferably includes one or more selected from the group consisting of phenolic antioxidants, phosphorus-based antioxidants, sulfur-based antioxidants, and thioether-based antioxidants, and more preferably includes a phenolic antioxidant. This further improves the storage stability of the resin composition during storage and after it has been formed into a film.

[0074] Examples of phenolic antioxidants include acrylate-based phenolic compounds described in Japanese Patent Publication No. 63-179953 and Japanese Patent Publication No. 1-168643, such as 2-t-butyl-6-(3-t-butyl-2-hydroxy-5-methylbenzyl)-4-methylphenyl acrylate and 2,4-di-t-amyl-6-(1-(3,5-di-t-amyl-2-hydroxyphenyl)ethyl)phenyl acrylate; 2,6-di-t-butyl-4-methylphenol, 2,6-di-t-butyl-4-ethylphenol, octadecyl-3-(3, 5-di-t-butyl-4-hydroxyphenyl)propionate, 2,2'-methylene-bis(4-methyl-6-t-butylphenol), 4,4'-butylidene-bis(6-t-butyl-m-cresol), 4,4'-thiobis(3-methyl-6-t-butylphenol), bis(3-cyclohexyl-2-hydroxy-5-methylphenyl)methane, 3,9-bis(2-(3-(3-t-butyl-4-hydroxy-5-methylphenyl)propionyloxy)-1,1-dimethylethyl)-2,4,8,10-tetraoxaspiro[5.5] Alkyl-substituted phenolic compounds such as undecane, 1,1,3-tris(2-methyl-4-hydroxy-5-t-butylphenyl)butane, 1,3,5-trimethyl-2,4,6-tris(3,5-di-t-butyl-4-hydroxybenzyl)benzene, tetrakis(methylene-3-(3',5'-di-t-butyl-4'-hydroxyphenylpropionate)methane [i.e., pentaerythrimethyl-tetrakis(3-(3,5-di-t-butyl-4-hydroxyphenylpropionate)], pentaerythritol=tetrakis[3-(3',5'-di-tert-butyl-4'-hydroxyphenyl)propionate, triethylene glycol bis(3-(3-t-butyl-4-hydroxy-5-methylphenyl)propionate), tocopherol; 6 At least one triazine group-containing phenolic compounds such as -(4-hydroxy-3,5-di-t-butylanilino)-2,4-bisoctylthio-1,3,5-triazine, 6-(4-hydroxy-3,5-dimethylanilino)-2,4-bisoctylthio-1,3,5-triazine, 6-(4-hydroxy-3-methyl-5-t-butylanilino)-2,4-bisoctylthio-1,3,5-triazine, and 2-octylthio-4,6-bis-(3,5-di-t-butyl-4-oxyanilino)-1,3,5-triazine can be selected from the group consisting of these. Among these, at least one selected from the group consisting of acrylate-based phenolic compounds and alkyl-substituted phenolic compounds is preferred, and alkyl-substituted phenolic compounds are more preferred.

[0075] Examples of phosphorus-based antioxidants include triphenyl phosphite, diphenylisodecyl phosphite, phenyl diisodecyl phosphite, tris(nonylphenyl) phosphite, tris(dinonylphenyl) phosphite, tris(2,4-di-t-butylphenyl) phosphite, tris(2-t-butyl-4-methylphenyl) phosphite, tris(cyclohexylphenyl) phosphite, and 2,2-methylenebis(4,6-di-t-butylphenyl) Monophosphine compounds such as cultyl phosphite, 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide, 10-(3,5-di-t-butyl-4-hydroxybenzyl)-9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide, and 10-decyloxy-9,10-dihydro-9-oxa-10-phosphaphenanthrene; 4,4'-butylidene-bis(3-methyl-6-t-butylphenyl-di-tridecyl 4,4'-isopropylidene-bis(phenyl-di-alkyl(C12~C15) phosphite), 4,4'-isopropylidene-bis(diphenylmonoalkyl(C12~C15) phosphite), 1,1,3-tris(2-methyl-4-di-tridecylphosphite-5-t-butylphenyl)butane, tetrakis(2,4-di-t-butylphenyl)-4,4'-biphenylenediphosphite, cyclic neopentanetetraylbis(iso) At least one compound selected from the group consisting of diphosphite compounds such as decyl phosphite, cyclic neopentanetetraylbis(nonylphenyl phosphite), cyclic neopentanetetraylbis(2,4-di-t-butylphenyl phosphite), cyclic neopentanetetraylbis(2,4-dimethylphenyl phosphite), and cyclic neopentanetetraylbis(2,6-di-t-butylphenyl phosphite) is mentioned. Among these, monophosphite compounds are preferred, and at least one compound selected from the group consisting of tris(nonylphenyl) phosphite, tris(dinonylphenyl) phosphite, and tris(2,4-di-t-butylphenyl) phosphite is more preferred.

[0076] Examples of sulfur-based antioxidants include at least one selected from the group consisting of dilauryl 3,3-thiodipropionate, dimyristyl 3,3'-thiodipropionate, distearyl 3,3-thiodipropionate, laurylstearyl 3,3-thiodipropionate, pentaerythritol-tetrakis-(β-lauryl-thio-propionate), and 3,9-bis(2-dodecylthioethyl)-2,4,8,10-tetraoxaspiro[5,5]undecane. Examples of thioether-based antioxidants include at least one selected from the group consisting of tetrakis{methylene-3-(laurylthio)propionate}methane, bis[methyl-4-{3-n-alkyl(C12 or C14)thiopropioniodyl}-5-t-butylphenyl]sulfide, and ditridecyl-3,3'-thiodipropionate.

[0077] If the resin composition of this embodiment contains an antioxidant, the amount of antioxidant in the resin composition of this embodiment is preferably 0.001 parts by mass or more, more preferably 0.005 parts by mass or more, even more preferably 0.01 parts by mass or more, even more preferably 0.02 parts by mass or more, and preferably 1.0 part by mass or less, more preferably 0.50 parts by mass or less, even more preferably 0.30 parts by mass or less, even more preferably 0.20 parts by mass or less, and even more preferably 0.10 parts by mass or less, based on 100 parts by mass of the cyclic olefin polymer (m).

[0078] (Radical polymerization initiator) The resin composition of this embodiment preferably further contains a radical initiator, and from the viewpoint of obtaining a cured product with a better balance between heat resistance and electrical properties, the radical initiator preferably contains bibenzyl compounds, and more preferably contains a compound represented by the following general formula (1).

[0079] [ka]

[0080] In general formula (1), R1 to R 10 are each independently a hydrogen atom, a halogen atom, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms, or a halogenated alkyl group having 1 to 20 carbon atoms, and R 11 to R 14 are each independently an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms, or a halogenated alkyl group having 1 to 20 carbon atoms, and at least one of R 11 to R 14 is each independently an alkyl group having 2 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms, or a halogenated alkyl group having 1 to 20 carbon atoms.

[0081] In general formula (1), R1 to R 10 are preferably each independently a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, or an aromatic hydrocarbon group having 6 to 20 carbon atoms from the viewpoint of obtaining a cured product with further improved heat resistance, and more preferably a hydrogen atom.

[0082] In general formula (1), R 11 to R 14 are preferably each independently an alkyl group having 2 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms, or a halogenated alkyl group having 1 to 20 carbon atoms from the viewpoint of obtaining a cured product with further improved heat resistance, more preferably each independently an alkyl group having 1 to 20 carbon atoms, still more preferably each independently an alkyl group having 1 to 4 carbon atoms, and still more preferably each independently a methyl group or an ethyl group.

[0083] The content of the radical initiator in the resin composition of this embodiment is preferably 0 parts by mass or more and 20.0 parts by mass or less, more preferably 0.05 parts by mass or more and 20.0 parts by mass or less, even more preferably 0.1 parts by mass or more and 20.0 parts by mass or less, even more preferably 0.5 parts by mass or more and 20.0 parts by mass or less, even more preferably 1.0 parts by mass or more and 10.0 parts by mass or less, even more preferably 1.5 parts by mass or more and 10.0 parts by mass or less, even more preferably 2.0 parts by mass or more and 10.0 parts by mass or less, even more preferably 2.5 parts by mass or more and 5.0 parts by mass or less, even more preferably 3.0 parts by mass or more and 5.0 parts by mass or less, and even more preferably 3.5 parts by mass or more and 5.0 parts by mass or less, per 100 parts by mass of the cyclic olefin polymer (m).

[0084] (Other ingredients) The resin composition of this embodiment may further contain various additives depending on the purpose. The amount of additives added is appropriately selected according to the application, within a range that does not impair the purpose of the present invention. The above-mentioned additives include one or more additives selected from the group consisting of heat stabilizers, weather stabilizers, radiation stabilizers, plasticizers, lubricants, mold release agents, nucleating agents, friction wear improvers, flame retardants, foaming agents, antistatic agents, colorants, antifogging agents, antiblocking agents, impact resistant agents, surface wetting improvers, fillers, crosslinking aids, crosslinking agents, hydrochloric acid absorbers, and metal deactivators. For example, heat stabilizers, light stabilizers, ultraviolet absorbers, radiation resistant agents, plasticizers, lubricants, mold release agents, nucleating agents, friction wear improvers, flame retardants, foaming agents, antistatic agents, colorants, antifogging agents, antiblocking agents, impact resistant agents, surface wetting improvers, fillers, hydrochloric acid absorbers, metal deactivators, etc., as described in paragraphs 0085 to 0120 of International Publication No. 2017 / 150218, can be used.

[0085] The resin composition of this embodiment can be prepared, for example, by mixing a cyclic olefin polymer (m), an aromatic polymer (n), and other components as needed. The aromatic polymer (n) may contain impurities and other components as optional components. Examples of optional components include indene and unsaturated aliphatic hydrocarbons. As for the mixing method, a melt blending method using an extruder or the like can be employed, or a solution blending method in which the mixture is dissolved and dispersed in a suitable solvent, such as saturated hydrocarbons like heptane, hexane, decane, or cyclohexane; or aromatic hydrocarbons like toluene, benzene, or xylene.

[0086] The dielectric loss tangent of the cured resin composition of this embodiment at 10 GHz is preferably less than 0.0030, more preferably less than 0.0025, even more preferably less than 0.0020, even more preferably less than 0.0018, even more preferably less than 0.0015, even more preferably less than 0.0012, and even more preferably less than 0.0010. For example, it may be 0.0001 or more, 0.0003 or more, or 0.0005 or more.

[0087] The dielectric loss tangent of the cured resin composition of this embodiment at 10 GHz can be measured, for example, by the following <Method 1>. <Method 1> First, the resin composition of this embodiment is coated onto a release-treated PET film at a speed of 10 mm / second, and then dried in a forced-air dryer under a nitrogen flow at 150°C for 4 minutes to obtain a laminated film of the PET film and the resin composition of this embodiment. The two resulting laminated films are stacked so that the resin compositions are in contact with each other, and then pressurized to 3.5 MPa using a vacuum press. The temperature is raised at a constant rate from room temperature (25°C) and held at 180°C for 60 minutes. After that, the film is peeled off the PET film to obtain a pre-cured laminated film. Next, the pre-curing laminated film is sandwiched between polyimide films, pressurized to 3.5 MPa using a vacuum press, heated at a constant rate from room temperature (25°C), held at 220°C for 120 minutes, and then peeled off from the polyimide films to obtain the post-curing laminated film. Next, the dielectric loss tangent Df of the cured laminated film at 10 GHz is measured using the cylindrical cavity resonator method.

[0088] The storage modulus of the cured resin composition of this embodiment at 200°C is preferably 1.0 × 10⁻⁶. 6 Pa or more 1.0×1010 Pa or less, more preferably 1.3 × 10 6 Pa or more 5.0×10 9 Pa or less, more preferably 1.5 × 10 6 Pa or more 2.0×10 9 Pa or less, more preferably 2.0 × 10 6 Pa or more 1.5×10 9 Pa or less, more preferably 2.5 × 10 6 Pa or more 1.0×10 9 Pa or less, more preferably 3.0 × 10 6 Pa or more 3.0×10 9 Pa or less, more preferably 5.0 × 10 6 Pa or more 1.0×10 9 It is below Pa.

[0089] The storage modulus of the cured resin composition of this embodiment at 200°C can be measured by the following <Method 2>. <Method 2> The solid viscoelastic temperature dispersion measurement of the cured laminated film obtained by the above-mentioned Method 1 was performed under the following conditions, and the storage modulus at 200°C was determined. Deformation mode: Tension Temperature range: 25℃~300℃ Heating rate: 3°C / min Frequency: 1Hz Setting distortion: 0.1% Environment: Under a nitrogen atmosphere

[0090] <Varnish> The varnish of this embodiment comprises the resin composition of this embodiment and a solvent.

[0091] The solvent of this embodiment includes, for example, one or more selected from the group consisting of saturated hydrocarbons such as heptane, hexane, octane, and decane; alicyclic hydrocarbons such as cyclohexane, methylcyclohexane, and decahydronaphthalene; aromatic hydrocarbons such as toluene, benzene, xylene, mesitylene, and pseudocumene; alcohols such as methanol, ethanol, isopropyl alcohol, butanol, pentanol, hexanol, propanediol, and phenol; ketone solvents such as acetone, methyl isobutyl ketone, methyl ethyl ketone, pentanone, hexanone, cyclohexanone, isophorone, and acetophenone; cellsolves such as methyl cellsolve and ethyl cellsolve; esters such as methyl acetate, ethyl acetate, butyl acetate, methyl propionate, and butyl formate; and halogenated hydrocarbons such as trichloroethylene, dichloroethylene, and chlorobenzene. The solvent in this embodiment preferably comprises one or more selected from the group consisting of heptane, decane, cyclohexane, methylcyclohexane, decahydronaphthalene, toluene, benzene, xylene, mesitylene, and pseudocumene, and more preferably comprises toluene, from the viewpoint of further improving the solubility and availability of the resin composition.

[0092] Furthermore, when the total amount of the varnish of this embodiment is 100 parts by mass, the content of the resin composition of this embodiment in the varnish is preferably 5 parts by mass or more and 80 parts by mass or less, more preferably 10 parts by mass or more and 70 parts by mass or less, even more preferably 15 parts by mass or more and 60 parts by mass or less, and even more preferably 18 parts by mass or more and 55 parts by mass or less.

[0093] In this embodiment, the method for preparing the varnish may be any method, but for example, it may include a step of mixing the resin composition and the solvent. There are no restrictions on the order in which the components are mixed, and it can be done in any way, such as all at once or in stages. There are also no restrictions on the apparatus for preparing the varnish, and it may be carried out using any batch or continuous apparatus capable of stirring and mixing. The temperature when preparing the varnish can be arbitrarily selected within the range from room temperature to the boiling point of the solvent. Alternatively, the varnish may be prepared by using the reaction solution obtained when the cyclic olefin polymer (m) or aromatic polymer (n) is obtained as the solvent.

[0094] <Prepreg> The prepreg of this embodiment is obtained by impregnating a fibrous substrate with the resin composition or varnish of this embodiment.

[0095] The prepreg of this embodiment is preferably formed by compounding the resin composition of this embodiment with a sheet-like fibrous substrate. The method for manufacturing the prepreg is not particularly limited, and various known methods can be applied. For example, one method includes the steps of impregnating a sheet-like fibrous substrate with the aforementioned varnish to obtain an impregnated body, and heating the obtained impregnated body to dry the solvent contained in the varnish. The impregnation of a sheet-like fibrous substrate with varnish can be carried out, for example, by applying a predetermined amount of varnish to the sheet-like fibrous substrate using known methods such as spray coating, dip coating, roll coating, curtain coating, die coating, or slit coating, and if necessary, by placing a protective film on top and pressing it from above with a roller or the like. Furthermore, the process of heating the impregnated material and drying the solvent contained in the varnish is not particularly limited, but examples of methods include drying in air or nitrogen using a forced-air dryer in a batch process, or drying by passing it through a heating furnace in a continuous process. After impregnating a sheet-like fibrous substrate with varnish, the resulting impregnated material is heated to a predetermined temperature, causing the solvent contained in the varnish to evaporate and yielding a prepreg.

[0096] The fibers constituting the sheet-like fibrous substrate can be inorganic or organic, and are not particularly limited. Examples include organic fibers such as PET (polyethylene terephthalate) fibers, polystyrene fibers, aramid fibers, ultra-high molecular weight polyethylene fibers, polyamide (nylon) fibers, and liquid crystal polyester fibers; and inorganic fibers such as glass fibers, carbon fibers, alumina fibers, tungsten fibers, molybdenum fibers, titanium fibers, steel fibers, boron fibers, silicon carbide fibers, and silica fibers. Among these, preferably at least one selected from the group consisting of organic fibers and glass fibers, and more preferably at least one selected from the group consisting of aramid fibers, liquid crystal polyester fibers, and glass fibers. Examples of glass fibers include E glass, NE glass, S glass, D glass, H glass, T glass, etc. The impregnation of the sheet-like fibrous substrate with varnish is carried out, for example, by dipping and coating. Impregnation may be repeated multiple times as needed. These sheet-like fibrous substrates can be used individually or in combination of two or more types. The amount used can be appropriately selected as desired, but is, for example, 10% by mass or more, preferably 20% by mass or more, more preferably 30% by mass or more, and also, for example, 90% by mass or less, preferably 80% by mass or less, more preferably 70% by mass or less, in the prepreg or laminate. Within this range, the dielectric properties and mechanical strength of the resulting laminate are well balanced and therefore preferable.

[0097] The thickness of the prepreg is appropriately selected depending on the intended use, but is, for example, 0.001 mm or more, preferably 0.005 mm or more, more preferably 0.01 mm or more, and also, for example, 10 mm or less, preferably 1 mm or less, more preferably 0.5 mm or less. Within this range, the shapeability during lamination and the properties such as mechanical strength and toughness of the resulting laminate are fully exhibited, making it suitable.

[0098] <Cured products and films> The film of this embodiment includes the resin composition of this embodiment or a cured product of the resin composition of this embodiment.

[0099] The cured product obtained by curing the resin composition of this embodiment can be formed into a film and used for various applications. In this embodiment, "film" is a general term for planar molded products and includes sheets, membranes, tapes, etc. Various known methods can be applied to cure the resin composition of this embodiment into a cured product and form it into a film. For example, one method involves applying the above-mentioned varnish to a support substrate such as a thermoplastic resin film, drying it, and then crosslinking the resin composition by heat treatment or the like to obtain a cured product and form a film made of the resin composition of this embodiment. As the thermoplastic resin film, PET film, polyimide resin film, etc., can be used. The method of applying the varnish to the support substrate is not particularly limited, but examples include application using a spin coater, application using a spray coater, application using a bar coater, etc. Another method involves melt-molding the resin composition of this embodiment to obtain a film, and then curing the resin composition by crosslinking it through heat treatment or the like to form a film made of the resin composition of this embodiment.

[0100] <Laminate> The laminate of this embodiment includes the prepreg of this embodiment or the film of this embodiment.

[0101] The film or prepreg of this embodiment can be laminated onto a substrate and used as a laminate for various applications. For example, it can be used as an organic insulating film requiring low dielectric properties, or as a curable adhesive sheet for devices having an adhesive layer. Various known methods can be applied to form the laminate in this embodiment. For example, a laminate can be produced by laminating a film manufactured by the above method onto a substrate and then heat-curing it by pressing or other means as needed. Furthermore, a laminate can also be fabricated by laminating an electrical insulating layer containing the aforementioned cured material onto a conductive layer.

[0102] The cured product obtained by curing the resin composition of this embodiment may be formed on the surface layer of various multilayer molded articles or multilayer laminated films. Examples of various multilayer molded articles or multilayer laminated films include, for example, a multilayer molded article for optical lenses in which the film of this embodiment is formed on the surface of a resin optical lens, and a multilayer gas barrier film in which the film of this embodiment is formed on the surface of a resin film such as a PET film or a PE film to impart gas barrier properties.

[0103] <Metal-clad laminate> The metal-clad laminate of this embodiment includes a metal foil on at least one side of the laminate of this embodiment.

[0104] The laminate of this embodiment may be a metal-clad laminate obtained by laminating a metal foil onto at least one surface of the laminate of this embodiment and then heat-curing it by lamination pressing or the like. Alternatively, the metal foil may be bonded to both sides of the laminate. Examples of metal foils include copper foil, aluminum foil, nickel foil, gold foil, silver foil, and stainless steel foil. From the viewpoint of economy, processability, thermal conductivity, and electrical conductivity, electrolytic copper foil is preferred. Various known methods can be applied to produce the metal-clad laminate of this embodiment. For example, a metal-clad laminate can be produced by laminating a metal foil onto the laminate of this embodiment and then heat-curing it by pressing or other means as needed.

[0105] The metal-clad laminate of this embodiment uses a cured product obtained by curing the resin composition of this embodiment, and therefore has low dielectric properties and heat resistance in the high-frequency range, making it suitable for printed circuit boards. Therefore, the metal-clad laminate of this embodiment can be suitably used as an insulating layer material for printed circuit boards.

[0106] <Printed Wiring Board> The printed circuit board of this embodiment is manufactured using the prepreg of this embodiment or the metal-clad laminate of this embodiment.

[0107] The cured product obtained by curing the resin composition of this embodiment has a good balance of low dielectric properties and heat resistance in the high-frequency range, and therefore can be suitably used in printed circuit boards. A generally known method can be used as the manufacturing method for a printed circuit board, and is not particularly limited. For example, a film or laminate manufactured by the aforementioned method is heat-cured by lamination press or the like to form an electrical insulating layer. Next, a conductor layer is laminated onto the obtained electrical insulating layer by a known method to create a laminate. After that, a printed circuit board can be obtained by processing the conductor layer in the laminate into a circuit.

[0108] Examples of metals that can be used for the conductive layer include copper, aluminum, nickel, gold, silver, and stainless steel. Methods for forming the conductive layer include, for example, heat-sealing the metals in foil form onto the electrical insulating layer, bonding the metals in foil form onto the electrical insulating layer using an adhesive, or forming a conductive layer made of the metals on the electrical insulating layer by sputtering, vapor deposition, plating, etc. The printed circuit board can be either single-sided or double-sided.

[0109] <Electronic equipment> The electronic device of this embodiment includes the cured product of this embodiment or the printed circuit board of this embodiment.

[0110] The electronic device of this embodiment can be manufactured based on publicly known information. Examples of such electronic devices include ICT infrastructure equipment such as servers, routers, supercomputers, mainframes, and workstations; antennas such as GPS antennas, base station antennas, millimeter-wave antennas, and RFID antennas; communication devices such as mobile phones, smartphones, PHS phones, PDAs, and tablet terminals; digital devices such as personal computers, televisions, digital cameras, digital video cameras, POS terminals, wearable devices, and digital media players; in-vehicle electronic equipment such as electronic control systems, in-vehicle communication equipment, car navigation equipment, millimeter-wave radar, and in-vehicle camera modules; semiconductor testing equipment, high-frequency measuring equipment, etc.; and high-speed communication modules.

[0111] The electronic device of this embodiment preferably includes a high-speed communication module.

[0112] The high-speed communication module of this embodiment is a high-speed communication module manufactured using the cured product of this embodiment or the printed circuit board of this embodiment. The high-speed communication module of this embodiment is, for example, a communication module formed by mounting semiconductor chips on the printed circuit board of this embodiment, and is particularly suitable for applications that utilize high-frequency signals such as wireless communication equipment and network infrastructure equipment, and have a large amount of information to communicate and high speed.

[0113] The cured product obtained by curing the resin composition of this embodiment has a good balance of low dielectric properties and heat resistance in the high-frequency range, and can therefore be used in applications such as optical fibers, optical waveguides, optical disc substrates, optical filters, lenses, optical adhesives, optical filters for PDPs, coating materials for organic ELs, base film substrates for solar cells in the aerospace field, coating materials for solar cells and thermal control systems, semiconductor elements, light-emitting diodes, various memory devices and other electronic elements, hybrid ICs, MCMs, printed circuit boards, prepregs and laminates used to form insulating layers of printed circuit boards, overcoat materials or interlayer insulating materials for display components, substrates for liquid crystal displays and solar cells, medical devices, automotive components, resin modifiers, transparent substrates for displays, gas barrier coating materials, aerospace components, semiconductor process materials, wire coating materials, lithium-ion battery components, fuel cell components, capacitor films, flexible display components, anchor coating materials, transparent adhesives, and hard coating materials. In particular, the cured product obtained by curing the resin composition of this embodiment has excellent heat resistance, low dielectric properties in the high-frequency range, and a good balance of performance such as insulation and mechanical properties, so it can be suitably used in printed circuit boards, and is even more suitably used in high-frequency applications such as high-frequency printed circuit boards.

[0114] The embodiments of the present invention have been described above, but these are merely examples, and various other configurations can also be adopted. Furthermore, the present invention is not limited to the embodiments described above, and any modifications, improvements, etc., that do not impair the effects of the present invention are included in the present invention. [Examples]

[0115] This embodiment will be described in detail below with reference to examples and other relevant information. However, this embodiment is not limited in any way to the descriptions of these examples.

[0116] (raw materials) Cyclic olefin polymer (m): Synthesis method will be described later. Aromatic polymer (n-1): Synthesis method will be described later. Aromatic polymer (n-2): Synthesis method will be described later. Aromatic polymer (n-3): Synthesis method will be described later. Aromatic polymer (n-4): Synthesis method will be described later. Aromatic polymer (n-5): Synthesis method will be described later. Radical initiator 1: 2,3-dimethyl-2,3-diphenylhexane (manufactured by Acros Organics) Antioxidant 1: Phenolic antioxidant (Pentaerythritol = Tetrakis[3-(3',5'-di-tert-butyl-4'-hydroxyphenyl)propionate), Product name: Irganox 1010, manufactured by BASF)

[0117] The following raw materials were used in the synthesis of the cyclic olefin polymer (m). Transition metal compounds (1): It was synthesized by the method described in Japanese Patent Publication No. 2004-331965.

[0118] [ka]

[0119] Modified methylaluminoxane (MMAO, manufactured by Tosoh Finechem Co., Ltd.) Toluene (manufactured by Wako Pure Chemical Industries, Ltd.: Wako Special Grade) 5-Vinyl-2-norbornene (hereinafter referred to as VNB) (manufactured by Tokyo Chemical Industry Co., Ltd.) Tetracyclo[4.4.0.1 2,5 .1 7,10 ]-3-Dodecene (hereinafter referred to as TD) (manufactured by Mitsui Chemicals, Inc.) Isobutyl alcohol (manufactured by Tokyo Chemical Industry Co., Ltd.) Methanol (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.: Wako Special Grade)

[0120] <Method for measuring the content of each repeating unit constituting a cyclic olefin polymer (m)> The content of repeating units derived from VNB and TD in the cyclic olefin polymer (m) was measured using a JEOL EXcalibur270 nuclear magnetic resonance spectrometer under the following conditions. Cumulative number of times: 16-64 Measurement temperature: room temperature The above measurements 1 The content of each hydrogen atom was calculated from the 1H-NMR spectrum based on the intensity of the peaks derived from hydrogen directly bonded to the double bond carbon and the peaks of other hydrogen atoms. The results are shown in Table 1.

[0121] <Method for calculating the content of each repeating unit constituting the aromatic polymer (n-1) to (n-5)> For aromatic polymers (n-1) to (n-5), the content of constituent units derived from IPT, C5 fraction, DVB, αMS, and styrene was calculated from the amounts of IPT, C5 fraction, DVB, αMS, and styrene used. The results are shown in Table 1.

[0122] <Method for measuring the number-average molecular weight (Mn) of cyclic olefin polymers (m)> The number-average molecular weight (Mn) of the cyclic olefin polymer (m) was measured by GPC and determined as a standard polystyrene equivalent. The GPC measurement was performed under the following conditions. Equipment: GPC HLC-8321 (manufactured by Tosoh Corporation) Solvent: o-dichlorobenzene Columns: TSKgel, GMH6-HT x 2, TSKgel, GMH6-HTL x 2 (all manufactured by Tosoh Corporation) Flow rate: 1.0mL / min Sample: 1 mg / mL o-dichlorobenzene solution Temperature: 140℃

[0123] <Method for measuring the number-average molecular weight (Mn) of aromatic polymers (n-1) to (n-5)> The number-average molecular weight (Mn) of aromatic polymers (n-1) to (n-5) was measured by GPC and determined as a standard polystyrene equivalent. The GPC measurements were performed under the following conditions. (Measurement conditions) Equipment: GPC HLC-8320 (manufactured by Tosoh Corporation) Detector: Differential refractometer (RI detector) Solvent: Tetrahydrofuran Columns: TSKgel G7000 x 1, TSKgel G4000 x 2, TSKgel G2000 x 1 (all manufactured by Tosoh Corporation) Flow rate: 1.0mL / min Sample: 20 mg / mL tetrahydrofuran solution Temperature: Room temperature or 40℃ Sample concentration: 2.2% by mass Injection volume: 50μL

[0124] [Synthesis Example 1 (Cyclic Olefin Polymer (m))] In a 1 L stainless steel autoclave that had been thoroughly purged with nitrogen, a hexane solution of 450 mL of toluene, 30 mL of VNB, 16 mL of TD, and MMAO (0.9 mmol in Al equivalent) and 360 mL of hydrogen were added. Then, ethylene was introduced into the system until the total pressure reached 0.6 MPa. A toluene solution of 0.028 mmol of transition metal compound (1) was added, and polymerization was carried out at 35°C for 180 minutes. Polymerization was then stopped by injecting 1 mL of methanol under pressure. After polymerization was complete, deionized water was added to the resulting polymer solution and stirred for 1 hour, then the organic layer was filtered through filter paper. This organic layer was placed in acetone to precipitate the polymer, stirred, and then filtered through filter paper. The resulting polymer was dried under reduced pressure at 80°C for 10 hours to obtain an ethylene / TD / VNB copolymer (hereinafter referred to as cyclic olefin polymer (m)), which is a cyclic olefin polymer (m).

[0125] [Synthesis example 2 (aromatic polymer (n-1))] In the first stage of a 1270 ml autoclave equipped with stirring blades, polymerization components (isopropenyltoluene and C5 fraction) and dehydrated purified toluene were mixed to obtain a mixture. Next, a boron trifluoride phenolate complex (1.7 times the phenol equivalent), diluted 10-fold with dehydrated purified toluene, was continuously supplied to this mixture, and the polymerization reaction was carried out at 5°C (polymerization temperature) to obtain a reaction solution containing the reaction product. At this time, the mass ratio of isopropenyltoluene to the C5 fraction (isopropenyltoluene / C5 fraction) was 9. The catalyst supply rate was 105 ml / hour. Next, this reaction solution was transferred to the second stage autoclave, and the polymerization reaction was continued at 5°C. When the total residence time in the first and second stage autoclaves reached 2 hours, the reaction solution was continuously discharged from the autoclaves, and then, when the residence time reached three times the total residence time, 1 liter of the reaction solution was taken to terminate the polymerization reaction. Subsequently, a 1 N aqueous NaOH solution was added to the reaction mixture to demineralize the catalyst residue. Furthermore, the reaction product was washed five times with a large amount of water, and then the solvent and unreacted monomers were removed under reduced pressure using an evaporator. This yielded an aromatic polymer (n-1), a copolymer of isopropenyltoluene and the C5 fraction.

[0126] [Synthesis example 3 (aromatic polymer (n-2))] Aromatic polymer (n-2) was prepared using the same procedure as in Synthesis Example 2, except that the polymerization component was changed to isopropenyltoluene only.

[0127] [Synthesis example 4 (aromatic polymer (n-3))] A mixture of polymerization components (isopropenyltoluene and divinylbenzene) and dehydrated purified toluene (polymerization component / toluene = 2 / 3 (volume ratio)) and a boron trifluoride phenolate complex (phenol 1.7 equivalents) diluted 10-fold with dehydrated purified toluene were continuously supplied to the first stage of a 1270 ml autoclave equipped with a stirring blade, and the polymerization reaction was carried out at 5°C. The mass ratio of isopropenyltoluene to divinylbenzene (isopropenyltoluene / divinylbenzene) was 70 / 30, the supply rate of the polymerization component and toluene mixture was 1.0 liter / hour, and the supply rate of the diluted catalyst was 71 milliliters / hour. The reaction mixture was transferred to a second autoclave, and the polymerization reaction was continued at 5°C. When the total residence time in the first and second autoclaves reached 2 hours, the reaction mixture was continuously discharged from the autoclaves. When the residence time reached three times the total residence time, 1 liter of the reaction mixture was collected to terminate the polymerization reaction. After polymerization was complete, a 1 N aqueous NaOH solution was added to the collected reaction mixture to deash the catalyst residue. Furthermore, the obtained reaction mixture was washed five times with a large amount of water, the organic layer was diluted with toluene, and the polymer was added to methanol to precipitate the polymer. After stirring, the mixture was filtered through filter paper. The obtained polymer was dried under reduced pressure at 80°C for 10 hours to obtain an aromatic polymer (n-3) having vinyl groups derived from divinylbenzene.

[0128] [Synthesis example 5 (aromatic polymer (n-4))] A 1270 ml autoclave equipped with a stirring blade was subjected to a polymerization reaction at 5°C. A mixture of polymerization component (α-methylstyrene) and dehydrated purified toluene (polymerization component / toluene = 1 / 1 (volume ratio)) and a boron trifluoride phenolate complex (phenol 1.7 equivalents) diluted 10-fold with dehydrated purified toluene were continuously supplied to the first stage. The polymerization reaction was carried out at 5°C. The supply rate of the polymerization component and toluene mixture was 1.0 liter / hour, and the supply rate of the diluted catalyst was 105 milliliters / hour. A reaction mixture was obtained. Next, the reaction mixture was transferred to a second autoclave, and the polymerization reaction was continued at 5°C. When the total residence time in the first and second autoclaves reached 2 hours, the reaction mixture was continuously discharged from the autoclaves. When the residence time reached three times the total residence time, 1 liter of the reaction mixture was collected to terminate the polymerization reaction. After polymerization was complete, a 1 N aqueous NaOH solution was added to the collected reaction mixture to deash the catalyst residue. Furthermore, the obtained reaction mixture was washed five times with a large amount of water, and then the solvent and unreacted monomers were removed by vacuum distillation in an evaporator to obtain the aromatic polymer (n-4).

[0129] [Synthesis example 6 (aromatic polymer (n-5))] Following the same procedure as in Synthesis Example 5, an aromatic polymer (n-5), a copolymer of α-methylstyrene and styrene, was prepared. However, the supply rate of the diluted catalyst was changed to 75 ml / hour, the temperature of the polymerization reaction in the second autoclave was changed to 25°C, the polymerization components were changed to α-methylstyrene and styrene, and the mass ratio of α-methylstyrene / styrene was set to 60 / 40.

[0130] [Table 1]

[0131] [Example 1] (Varnish preparation) The cyclic olefin polymer (m) obtained in Synthesis Example 1 was dissolved in toluene to a solid content of 20% by mass. The mixture was then weighed according to the composition shown in Table 2. The weighed samples were stirred until fully dissolved to obtain the desired varnish-like resin composition. Note that the units for the mixing ratio of each raw material in Table 2 are parts by mass.

[0132] (Fabrication of laminated films) The obtained varnish-like resin composition was coated onto a release-treated PET film at a speed of 10 mm / second, and then dried in a forced-air dryer under a nitrogen flow at 150°C for 4 minutes. Two of the obtained films (hereinafter sometimes referred to as film (1)) were stacked and pressed to 3.5 MPa using a vacuum press, the temperature was raised at a constant rate from room temperature (25°C), and held at 180°C for 60 minutes. The film was then removed and separated from the PET film, and subsequently pressed to 3.5 MPa using a vacuum press while sandwiched between polyimide films, the temperature was raised at a constant rate from room temperature (25°C), and held at 220°C for 120 minutes to obtain a laminated film. The dielectric loss tangent, heat resistance, and miscibility of the obtained laminated film were evaluated according to the following procedure. The results are shown in Table 2.

[0133] <Evaluation of dielectric loss tangent> The dielectric loss tangent Df at 10 GHz was measured for the laminated films obtained in the examples and comparative examples using the cylindrical cavity resonator method, and evaluated as follows. Materials with a dielectric loss tangent of less than 0.0010 were classified as "A" for particularly good low dielectric properties in the high-frequency range, materials with a dielectric loss tangent of 0.0010 or more and less than 0.0030 were classified as "B" for good low dielectric properties in the high-frequency range, and materials with a dielectric loss tangent of 0.0030 or more were classified as "C" for poor low dielectric properties in the high-frequency range. The obtained results are shown in Table 2.

[0134] <Heat resistance evaluation> The obtained laminated films were subjected to solid viscoelastic temperature dispersion measurements under the following conditions to evaluate their heat resistance. According to the following criteria, those meeting category A were considered to have particularly good heat resistance, and those meeting category B were considered to have particularly good heat resistance. The results are shown in Table 1. (standard) A: The storage modulus at 200℃ is 1.0 × 10⁻⁶ 7 More than Pa B: Storage modulus at 200℃ is 1.0 × 10⁻⁶ 6 Pa or more 1.0×10 7 Less than Pa C: Storage modulus at 200℃ is 1.0 × 10⁻⁶ 6 Less than Pa (conditions) Equipment: RSA-III (manufactured by T.A. Instruments Corporation) Deformation mode: Tension Temperature range: 25℃~300℃ Heating rate: 3°C / min Frequency: 1Hz Setting distortion: 0.1% Environment: Under a nitrogen atmosphere

[0135] <Miscibility Assessment> The film (1) obtained during the preparation of the laminated film was observed, and the miscibility of the resin composition was evaluated. The appearance of film (1) was visually observed. Films that were transparent and uniform were classified as "A," those that were opaque and uniform were classified as "B," and those that showed both transparent and opaque areas and were non-uniform were classified as "C." Films classified as A were considered to have particularly good miscibility, and those classified as B were considered to have good miscibility. The results are shown in Table 2.

[0136] [Examples 2-6 and Comparative Examples 1 and 2] Except for the changes in the compound composition shown in Table 1, varnishes and laminated films were prepared and evaluated in the same manner as in Example 1. The results are shown in Table 2.

[0137] [Table 2]

Claims

1. A cyclic olefin polymer (m) having a crosslinkable group, A resin composition comprising an aromatic polymer (n) containing one or more repeating units (D) derived from aromatic compounds represented by the following general formula (X). 【Chemistry 1】 [In the general formula (X), R １ R is a hydrocarbon group having 1 to 20 carbon atoms. ２ ~R ４ These may be the same or different atoms, and are hydrogen atoms or hydrocarbon groups having 1 to 20 carbon atoms.

2. When the total number of moles of repeating units in the aromatic polymer (n) is set to 100 mol%, The resin composition according to claim 1, wherein the content of repeating units (D) derived from the aromatic compound in the aromatic polymer (n) is 50 mol% or more.

3. The aromatic polymer (n) is the R １ The resin composition according to claim 1 or 2, comprising a repeating unit (d1) derived from an aromatic compound, which is an aliphatic hydrocarbon group that does not have an unsaturated double bond.

4. The aromatic polymer (n) is the R １ The resin composition according to claim 3, further comprising a repeating unit (d2) derived from an aromatic compound in which is an aliphatic hydrocarbon group having an unsaturated double bond.

5. When the total number of moles of repeating units in the aromatic polymer (n) is set to 100 mol%, The content D of the repeating unit (d1) in the aromatic polymer (n) １ and the content D of the repeating unit (d2) relative thereto ２ The ratio (D ２ / D １ ) is 0 or more and 2.0 or less. The resin composition according to claim 4.

6. The resin composition according to claim 1 or 2, wherein when the content of the cyclic olefin polymer (m) in the resin composition is 100 parts by mass, the content of the aromatic polymer (n) in the resin composition is 1 part by mass or more and 300 parts by mass or less.

7. The resin composition according to claim 1 or 2, wherein the number-average molecular weight (Mn) of the aromatic polymer (n), measured by gel permeation chromatography on a polystyrene basis, is 400 or more.

8. The aforementioned cyclic olefin polymer (m) One or more repeating units (A) derived from olefins represented by the following general formula (I), The repeating unit (B) derived from a cyclic non-conjugated diene represented by the following general formula (III), A resin composition according to claim 1 or 2, comprising one or more repeating units (C) derived from a cyclic olefin represented by the following general formula (V). 【Chemistry 2】 [In the above general formula (I), R ３００ This represents a hydrogen atom or a linear or branched hydrocarbon group having 1 to 29 carbon atoms. 【Transformation 3】 [In the above general formula (III), u is 0 or 1, v is 0 or a positive integer, w is 0 or 1, R ６１ ~R ７６ And R ａ１ and R ｂ１ These may be the same or different from each other, and are a hydrogen atom, a halogen atom, an alkyl group having 1 to 20 carbon atoms, a halogenated alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 15 carbon atoms, or an aromatic hydrocarbon group having 6 to 20 carbon atoms, R １０４ is a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, t is a positive integer from 0 to 10, and R ７５ and R ７６ These may be bonded to each other to form a monocycle or polycycle. 【Chemistry 4】 [In the above general formula (V), u is 0 or 1, v is 0 or a positive integer, w is 0 or 1, R ６１ ~R ７８ And R ａ１ and R ｂ１ These may be the same or different from each other, and are a hydrogen atom, a halogen atom, an alkyl group having 1 to 20 carbon atoms, a halogenated alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 15 carbon atoms, or an aromatic hydrocarbon group having 6 to 20 carbon atoms, R ７５ ~R ７８ These may be bonded to each other to form a monocycle or polycycle.

9. The cyclic non-conjugated diene constituting the repeating unit (B) derived from the cyclic non-conjugated diene is 5-vinyl-2-norbornene, 8-vinyl-9-methyltetracyclo[4.4.0.1 ２，５ 1. ７，１０ ]-3-dodecene, 5-allyl-2-norbornene and 8-vinyl-tetracyclo[4.4.0.1 ２，５ 1. ７，１０ The resin composition according to claim 8, comprising at least one selected from the group consisting of ]-3-dodecene.

10. The cyclic olefin constituting the repeating unit (C) derived from the cyclic olefin is bicyclo[2.2.1]-2-heptene and tetracyclo[4.4.0.1 ２，５ 1. ７，１０ The resin composition according to claim 8, comprising at least one selected from the group consisting of ]-3-dodecene.

11. The cyclic olefin constituting the repeating unit (C) derived from the cyclic olefin is tetracyclo[4.4.0.1 ２，５ 1. ７，１０ The resin composition according to claim 9, comprising ]-3-dodecene.

12. The resin composition according to claim 1 or 2, wherein the number-average molecular weight (Mn) of the cyclic olefin polymer (m), measured by gel permeation chromatography on a polystyrene basis, is 5000 or more.

13. The resin composition according to claim 1 or 2, further comprising an antioxidant.

14. The resin composition according to claim 1 or 2, wherein the dielectric loss tangent of the cured resin composition at 10 GHz is less than 0.0030.

15. The resin composition according to claim 1 or 2, further comprising a radical polymerization initiator.

16. The resin composition according to claim 15, wherein the radical polymerization initiator comprises bibenzyl compounds.

17. A varnish comprising the resin composition according to claim 1 or 2 and a solvent.

18. A prepreg comprising a fibrous substrate impregnated with the resin composition described in claim 1 or a varnish containing the resin composition and a solvent.

19. A cured product of the resin composition according to claim 1 or 2.

20. A film comprising the resin composition described in claim 1 or a cured product of the resin composition.

21. A laminate comprising the prepreg described in claim 18 or the film described in claim 20.

22. A metal-clad laminate containing a metal foil on at least one side of the laminate according to claim 21.

23. A printed circuit board manufactured using the metal-clad laminate described in claim 22.

24. An electronic device comprising the cured product described in claim 19.

25. The electronic device according to claim 24, wherein the electronic device includes a high-speed communication module.

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