resin composition

Abstract

The objective of this invention is to provide a resin composition that yields a cured product that maintains high peel strength and has a low dielectric tangent, even under high temperature and high humidity conditions. The solution of this invention is a resin composition comprising (A) a cyclic carbonate compound, (B) an epoxy resin, and (C) an inorganic filler.

Description

Technical Field

[0001] This invention relates to resin compositions comprising epoxy resin. Further, it relates to resin films, printed wiring boards, and semiconductor devices obtained using the resin compositions. Prior Technology

[0002] As a manufacturing technology for printed circuit boards (PCBs), a manufacturing method using alternating layers of insulating and conductive materials in a buildup manner is known. In this buildup method, the insulating layer is generally formed by curing a resin composition containing epoxy resin and inorganic fillers. In recent years, with the further miniaturization, high density, and high frequency of signals in PCB wiring, there is a growing demand for further reductions in the dielectric tangent of the insulating layer. Furthermore, PCBs are generally exposed to high temperature and high humidity environments, thus requiring high peel strength resistance to such environments.

[0003] Currently, various cyclic carbonate compounds are known (Patent Documents 1-5).

[0004] Previous technical documents Patent documents Patent Document 1: Japanese Patent No. 6141261 Patent Document 2: Japanese Patent Application Publication No. 2018-118946 Patent Document 3: Japanese Patent Application Publication No. 5-209041 Patent Document 4: Japanese Patent No. 4273530 Patent Document 5: Japanese Patent No. 6635668 Summary of the Invention

[0005] The problem that the invention aims to solve

[0006] The objective of this invention is to provide a resin composition that can produce a cured product that maintains high peel strength and has a low dielectric tangent even when exposed to high temperature and high humidity environments. Solution for solving the problem

[0007] The inventors conducted diligent research in order to achieve the objectives of this invention, and as a result, they discovered that by using a cyclic carbonate compound (A) in a resin composition comprising (B) epoxy resin and (C) inorganic filler, they unexpectedly obtained a cured material that maintains high peel strength and has its dielectric tangent suppressed to a low value even when exposed to high temperature and high humidity environments, thus completing this invention.

[0008] That is, the present invention includes the following contents. [1] A resin composition comprising (A) a cyclic carbonate compound, (B) an epoxy resin, and (C) an inorganic filler; [2] The resin composition as described in [1] above further comprises (D) an active ester compound; [3] As described in [2] above, when the total amount of components (A), (B) and (D) is set to 100% by mass, the content of component (A) is 1% to 10% by mass; [4] As described in [2] or [3] above, when the non-volatile component in the resin composition is set to 100% by mass, the content of component (D) is 12% by mass or more; [5] The resin composition described in any of [1] to [4] above, wherein component (A) comprises a compound selected from 5-membered cyclic carbonate compounds and 6-membered cyclic carbonate compounds. [6] The resin composition described in any of [1] to [5] above, wherein, (A) The components include the compound shown in formula (1),

[0009]

[0010] [In the formula, R1, R2, R3, R4, R5, and R6 are each represented independently. (1) Hydrogen atom, (2) Alkyl groups optionally substituted with groups selected from RO-, RCO-, RCOO-, and ROCO- (3) Alkenes substituted with groups selected from RO-, RCO-, RCOO-, and ROCO-, by choice (4) Aryl groups optionally substituted with groups selected from R-, RO-, RCO-, RCOO-, and ROCO- (5) The group shown in formula (2-1), or (6) The group shown in formula (2-2); The aforementioned equation (2-1) is:

[0011] []

[0012] The aforementioned equation (2-2) is:

[0013]

[0014] [] R1', R2', R3', R4', R5', and R6' are each represented independently. (1) Hydrogen atom, (2) Alkyl groups optionally substituted with groups selected from RO-, RCO-, RCOO-, and ROCO- (3) An alkenyl group optionally substituted with a group selected from RO-, RCO-, RCOO-, and ROCO-, or (4) An aralkyl group optionally substituted with a group selected from R-, RO-, RCO-, RCOO-, and ROCO-; A1 and A2 each independently represent -O-, -CO-, -COO-, or -OCO-; X and Y are represented independently. (1) An alkyl group optionally substituted with a group selected from RO-, RCO-, RCOO-, and ROCO-, or (2) An alkenyl group optionally substituted with a group selected from RO-, RCO-, RCOO-, and ROCO-; R independently represents alkyl, alkenyl, aralkyl, or aryl, which is optionally substituted with a group selected from halogen atom, alkyl-oxy, alkenyl-oxy, aryl-oxy, aralkyl-oxy, alkyl-carbonyl, alkenyl-carbonyl, aryl-carbonyl, aralkyl-carbonyl, alkyl-oxy-carbonyl, alkenyl-oxy-carbonyl, aryl-oxy-carbonyl, aralkyl-oxy-carbonyl, alkyl-carbonyl-oxy, alkenyl-oxy-carbonyl, aryl-oxy-carbonyl, aralkyl-oxy-carbonyl, alkyl-carbonyl-oxy, alkenyl-carbonyl-oxy, aryl-carbonyl-oxy, and aralkyl-carbonyl-oxy. Z represents an independently chosen divalent hydrocarbon group with substituents; n represents 0, 1, 2, or 3; * indicates a bonding location. [7] The resin composition described in any of [1] to [6] above, wherein when the non-volatile component in the resin composition is set to 100% by mass, the content of component (B) is 1% to 20% by mass. [8] The resin composition described in any of [1] to [7] above, wherein when the non-volatile component in the resin composition is set to 100% by mass, the content of component (C) is 60% by mass or more. [9] The resin composition described in any of [1] to [8] above, further comprising a curing agent selected from phenolic curing agents and carbodiimide curing agents.

[10] The resin composition described in any of [1] to [9] above, wherein the dielectric tangent (Df) of the cured resin composition is 0.0030 or less when measured at 5.8 GHz and 23 °C;

[11] The resin composition described in any of [1] to

[10] above, wherein the elongation at break of the hardened resin composition is 0.2% or more when measured at 23°C according to JIS K7127.

[12] The resin composition described in any of [1] to

[11] above is used to form an insulating layer, which is an insulating layer used to form a conductor layer.

[13] The resin composition described in any of [1] to

[11] above is used to form an insulating layer on a printed wiring board;

[14] A hardened material, which is a hardened material of a resin composition as described in any one of [1] to

[13] above;

[15] A sheet-like laminate material, wherein it contains a resin composition as described in any one of [1] to

[13] above;

[16] A resin sheet having: Support and A resin composition layer formed of a resin composition as described in any of [1] to

[13] above is disposed on the support;

[17] A printed wiring board having an insulating layer formed of a hardened resin composition as described in any one of [1] to

[13] above;

[18] A semiconductor device comprising a printed wiring board as described above in

[17] . The effects of the invention

[0015] According to the resin composition of the present invention, a cured material can be obtained that maintains high peel strength and has low dielectric tangent even when exposed to high temperature and high humidity environments. Implementation

[0016] The present invention will now be described in detail according to its preferred embodiments. However, the present invention is not limited to the embodiments and examples described below, and can be implemented in any way without departing from the scope of the claims and their equivalents.

[0017] <Resin Composition> The resin composition of the present invention comprises (A) a cyclic carbonate compound, (B) an epoxy resin, and (C) an inorganic filler. According to this resin composition, a cured product can be obtained that maintains high peel strength and has its dielectric tangent suppressed to a low value even when exposed to high temperature and high humidity environments.

[0018] In addition to (A) cyclic carbonate compounds, (B) epoxy resins, and (C) inorganic fillers, the resin composition of the present invention may further contain any other components. Examples of such components include (D) reactive ester compounds, (D') other curing agents, (E) compounds containing free radical polymerizable groups, (F) thermoplastic resins, (G) curing accelerators, (H) other additives, and (I) organic solvents.

[0019] The following is a detailed description of each component contained in the resin composition.

[0020] <(A) Cyclic carbonate compounds> The resin composition of the present invention contains (A) a cyclic carbonate compound. (A) The cyclic carbonate compound is a compound comprising a cyclic structure, wherein the cyclic structure comprises a carbonate backbone (-OC(=O)-O-). The (A) cyclic carbonate compound has one or more cyclic structures comprising a carbonate backbone in one molecule; in one embodiment, it is preferable to have one or two. In one embodiment, the (A) cyclic carbonate compound preferably comprises a compound selected from 5-membered cyclic carbonate compounds having an ethylene carbonate backbone and 6-membered cyclic carbonate compounds having a trimethylene carbonate backbone; more preferably, it comprises a compound selected from 5-membered cyclic carbonate compounds having one or two ethylene carbonate backbones in one molecule and 6-membered cyclic carbonate compounds having one or two trimethylene carbonate backbones in one molecule; and even more preferably, it comprises a 6-membered cyclic carbonate compound having one or two trimethylene carbonate backbones in one molecule.

[0021] In a particularly preferred embodiment, (A) the cyclic carbonate compound comprises the compound shown in formula (1).

[0022] []

[0023] R1, R2, R3, R4, R5, and R6 are each represented independently. (1) Hydrogen atom, (2) Alkyl groups optionally substituted with groups selected from RO-, RCO-, RCOO-, and ROCO- (3) Alkenes substituted with groups selected from RO-, RCO-, RCOO-, and ROCO-, by choice (4) Aryl groups optionally substituted with groups selected from R-, RO-, RCO-, RCOO-, and ROCO- (5) The group shown in formula (2-1), or

[0024]

[0025] (6) The group shown in formula (2-2).

[0026]

[0027] * indicates a bonding location.

[0028] Alkyl groups refer to straight-chain, branched-chain, and / or cyclic monovalent aliphatic saturated hydrocarbon groups. Unless otherwise specified, alkyl groups are preferably alkyl groups with 1 to 14 carbon atoms, more preferably alkyl groups with 1 to 10 carbon atoms, and even more preferably alkyl groups with 1 to 6 carbon atoms. Examples of alkyl groups include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, sec-pentyl, neopentyl, tert-pentyl, hexyl, isohexyl, heptyl, isohexyl, octyl, isooctyl, tert-octyl, cyclopentyl, and cyclohexyl.

[0029] An alkenyl group refers to a straight-chain, branched-chain, and / or cyclic monovalent aliphatic unsaturated hydrocarbon group having at least one carbon-carbon double bond. Unless otherwise specified, an alkenyl group is preferably an alkenyl group with 2 to 14 carbon atoms, more preferably an alkenyl group with 2 to 10 carbon atoms, and even more preferably an alkenyl group with 2 to 6 carbon atoms. Examples of alkenyl groups include vinyl, propenyl (allyl, 1-propenyl, isopropenyl), butenyl (1-butenyl, crotonyl, methyl allyl (metallyl), isocrotonyl, etc.), pentenyl (1-pentenyl, etc.), hexenyl (1-hexenyl, etc.), heptenyl (1-heptenyl, etc.), octenyl (1-octenyl, etc.), cyclopentenyl (2-cyclopentenyl, etc.), cyclohexenyl (3-cyclohexenyl, etc.), etc.

[0030] An aryl group is a monovalent aromatic hydrocarbon group formed by removing one hydrogen atom from an aromatic carbon ring. Unless otherwise specified, aryl groups are preferably 6 to 14 carbon atoms, and particularly preferably 6 to 10 carbon atoms. Examples of aryl groups include phenyl, 1-naphthyl, and 2-naphthyl.

[0031] Araneyl groups are alkyl groups that have been substituted by one or more aryl groups (preferably one). Unless otherwise specified, araneyl groups are preferably araneyl groups with 7 to 15 carbon atoms, and particularly preferably araneyl groups with 7 to 11 carbon atoms. Examples of araneyl groups include benzyl, phenethyl, hydrogenated cinnamyl, α-methylbenzyl, α-cumyl, 1-naphthylmethyl, 2-naphthylmethyl, etc.

[0032] In one embodiment, R1, R2, R5 and R6 are each preferably (1) a hydrogen atom or (2) an alkyl group optionally substituted with a group selected from RO-, RCO-, RCOO- and ROCO-; more preferably (1) a hydrogen atom or (2) an alkyl group optionally substituted with RO-; particularly preferably (1) a hydrogen atom or (2) an alkyl group.

[0033] In one embodiment, R3 and R4 are each preferably independently (1) a hydrogen atom, (2) an alkyl group optionally substituted with a group selected from RO-, RCO-, RCOO-, and ROCO-, (3) a group shown in formula (2-1), or (4) a group shown in formula (2-2); more preferably (1) a hydrogen atom, (2) an alkyl group optionally substituted with RO-, (3) a group shown in formula (2-1), or (4) a group shown in formula (2-2); even more preferably (1) a hydrogen atom, (2) an alkyl group, or (3) a group shown in formula (2-2).

[0034] R1', R2', R3', R4', R5' and R6' each independently represent (1) a hydrogen atom, (2) an alkyl group optionally substituted with a group selected from RO-, RCO-, RCOO-, and ROCO-, (3) an alkenyl group optionally substituted with a group selected from RO-, RCO-, RCOO-, and ROCO-, or (4) an aralkyl group optionally substituted with a group selected from R-, RO-, RCO-, RCOO-, and ROCO-.

[0035] In one embodiment, R1', R2', R3', R4', R5' and R6' are each preferably (1) a hydrogen atom or (2) an alkyl group optionally substituted with a group selected from RO-, RCO-, RCOO-, and ROCO-; more preferably (1) a hydrogen atom or (2) an alkyl group optionally substituted with RO-; particularly preferably (1) a hydrogen atom or (2) an alkyl group.

[0036] A1 and A2 each independently represent -O-, -CO-, -COO-, or -OCO-. In one embodiment, A1 and A2 are preferably -O-.

[0037] X and Y each independently represent (1) an enyl group optionally substituted with a group selected from RO-, RCO-, RCOO-, and ROCO-, or (2) an enyl group optionally substituted with a group selected from RO-, RCO-, RCOO-, and ROCO-.

[0038] Alkyl groups refer to straight-chain, branched-chain, and / or cyclic divalent aliphatic saturated hydrocarbon groups. Unless otherwise specified, alkyl groups are preferably alkyl groups with 1 to 14 carbon atoms, more preferably alkyl groups with 1 to 10 carbon atoms, and even more preferably alkyl groups with 1 to 6 carbon atoms. Examples of alkyl groups include straight-chain alkyl groups such as methylene, ethyl alkyl, trimethylene, tetramethylene, pentamethylene, hexamethylene, heptamethylene, octamethylene, nonamethylene, and decamethylene; and branched-chain alkyl groups such as ethoxyyl, propylene, isopropylene, ethylmethylmethylene, and diethylmethylene.

[0039] Alkenylene refers to a straight-chain, branched-chain, and / or cyclic divalent aliphatic unsaturated hydrocarbon group having at least one carbon-carbon double bond. Unless otherwise specified, alkenylene is preferably an alkenylene with 2 to 14 carbon atoms, more preferably an alkenylene with 2 to 10 carbon atoms, and even more preferably an alkenylene with 2 to 6 carbon atoms. Examples of enyl groups include -CH=CH-, -CH 2CH=CH-, -CH=C(CH 3)-, -C(CH 3)=CH-, -CH 2CH 2CH=CH-, -CH 2CH=CHCH 2-, -CH=CHCH 2CH 2-, -CH 2CH=C(CH 3)-, -C(CH 3)=CHCH 2-, -CH 2C(CH 3)=CH-, -CH=C(CH 3)CH 2-, -CH(CH 3)CH=CH-, and -CH=CHCH(CH 3)-.

[0040] In one embodiment, X and Y are each preferably independently alkyl groups optionally substituted with groups selected from RO-, RCO-, RCOO-, and ROCO-; more preferably alkyl groups optionally substituted with RO-; and even more preferably alkyl groups.

[0041] R independently represents alkyl, alkenyl, aralkyl, or aryl, wherein the aforementioned alkyl, alkenyl, aralkyl, or aryl is optionally substituted with a group selected from halogen atom, alkyl-oxy, alkenyl-oxy, aryl-oxy, aralkyl-oxy, alkyl-carbonyl, alkenyl-carbonyl, aryl-carbonyl, aralkyl-carbonyl, alkyl-oxy-carbonyl, alkenyl-oxy-carbonyl, aryl-oxy-carbonyl, aralkyl-oxy-carbonyl, alkyl-carbonyl-oxy, alkenyl-carbonyl-oxy, aryl-carbonyl-oxy, and aralkyl-carbonyl-oxy.

[0042] In one embodiment, R is preferably alkyl, alkenyl, aralkyl or aryl, and more preferably alkyl.

[0043] Z represents each of the optional divalent hydrocarbon groups with substituents.

[0044] A divalent hydrocarbon group is a divalent hydrocarbon group whose backbone consists of only one or more carbon atoms (e.g., 1-100, 2-50, or 2-30). Divalent hydrocarbon groups can have straight-chain, branched-chain, and / or cyclic structures. A divalent hydrocarbon group can be a hydrocarbon group without an aromatic ring or a hydrocarbon group containing an aromatic ring.

[0045] Examples of divalent hydrocarbon groups include alkyl, alkenyl, aromatic carbocyclic, non-aromatic carbocyclic, alkyl-aromatic carbocyclic-alkyl, alkenyl-aromatic carbocyclic-alkenyl, alkyl-non-aromatic carbocyclic-alkyl, alkenyl-non-aromatic carbocyclic-alkenyl, aromatic carbocyclic-aromatic carbocyclic, non-aromatic carbocyclic-non-aromatic carbocyclic, aromatic carbocyclic-alkyl-aromatic carbocyclic, aromatic carbocyclic-alkenyl-aromatic carbocyclic, aromatic carbocyclic-aromatic carbocyclic-aromatic carbocyclic, and aromatic carbocyclic-aromatic carbocyclic-aromatic carbocyclic. The compounds include aromatic carbocyclic ring-non-aromatic carbocyclic ring-aromatic carbocyclic group, non-aromatic carbocyclic ring-alkyl-non-aromatic carbocyclic group, non-aromatic carbocyclic ring-alkyl-non-aromatic carbocyclic group, non-aromatic carbocyclic ring-aromatic carbocyclic ring-non-aromatic carbocyclic group, and non-aromatic carbocyclic ring-non-aromatic carbocyclic ring-non-aromatic carbocyclic group. Among these, the non-aromatic carbocyclic ring can be fused with the aromatic carbocyclic ring or can be substituted by groups selected from alkyl, alkenyl, and aryl groups. The aromatic carbocyclic ring can be fused with the non-aromatic carbocyclic ring or can be substituted by groups selected from alkyl, alkenyl, and aryl groups.

[0046] An aromatic carbon ring is a carbon ring that follows Hückel's rule, where the π-electron system of the ring contains 4p+2 electrons (p being a natural number). An aromatic carbon ring uses only carbon atoms as ring-forming atoms. In one embodiment, the aromatic carbon ring is preferably a 6- to 14-membered aromatic carbon ring, more preferably a 6- to 10-membered aromatic carbon ring. Preferred examples of aromatic carbon rings include benzene rings, naphthalene rings, anthracene rings, phenanthrene rings, etc., with benzene rings or naphthalene rings being more preferred, and benzene rings being particularly preferred.

[0047] A non-aromatic carbon ring is a carbon ring that does not possess aromatic properties throughout the entire ring. A non-aromatic carbon ring uses only carbon atoms as ring-forming atoms. A non-aromatic carbon ring can be a saturated carbon ring formed solely by single bonds, or it can be a non-aromatic unsaturated carbon ring having at least one of double or triple bonds. Preferably, the non-aromatic carbon ring has 3 to 20 carbon atoms, more preferably 4 to 15 carbon atoms, and even more preferably 4 to 10 carbon atoms. Specific examples of preferred non-aromatic carbon rings include monocyclic saturated carbon rings such as cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, cyclononane, cyclodecane, cycloundecane, cyclododecane, cyclotridecane, cyclotetradecane, cyclopentadecanane, cyclohexadecane, cycloheptadecane, cyclooctadecanane, and cyclononadecanane; bicyclic saturated carbon rings such as [2.2.1]heptane (norbornene), [4.4.0]decane (decahydronaphthalene), [5.3.0]decane, [4.3.0]nonane (hexahydroindene), [3.2.1]octane, [5.4.0]undecane, [3.3.0]octane, and [3.3.1]nonane; and tricyclic saturated carbon rings such as [5.2.1.0]... Saturated carbon rings of tricyclic systems, such as [2,6]decane ring (tetrahydrodicyclopentadiene ring), tricyclic [3.3.1.1 3,7]decane ring (adamantane ring), and tricyclic [6.2.1.0 2,7]undecane ring; saturated carbon rings of tetracyclic systems, such as [6.2.1.1 3,6.0 2,7]dodecane ring; and saturated carbon rings of pentacyclic systems, such as [9.2.1.1 4,7.0 2,10.0 3,8]pentadecane ring and [6.5.1.1 3,6.0 2,7.0 9,13]pentadecane ring (tetrahydrotricyclopentadiene ring).

[0048] The "substituents" that can be optionally present in the divalent hydrocarbon group of Z are not particularly limited, and examples include halogen atoms, alkyl-oxygen groups, alkenyl-oxygen groups, aryl-oxygen groups, aralkyl-oxygen groups, alkyl-carbonyl groups, alkenyl-carbonyl groups, aryl-carbonyl groups, aralkyl-carbonyl groups, alkyl-oxygen-carbonyl groups, alkenyl-oxygen-carbonyl groups, aryl-oxygen-carbonyl groups, aralkyl-oxygen-carbonyl groups, alkyl-carbonyl-oxygen groups, alkenyl-carbonyl-oxygen groups, aryl-carbonyl-oxygen groups, aralkyl-carbonyl-oxygen groups, and groups shown in formula (Z-1).

[0049]

[0050] Groups shown in formula (Z-2), etc. [] []

[0051]

[0052] * indicates a bonding location.

[0053] Halogen atoms refer to fluorine, chlorine, bromine, or iodine atoms, preferably fluorine atoms.

[0054] R1'', R2'', R3'', R4'', R5'' and R6'' each independently represent (1) a hydrogen atom, (2) an alkyl group optionally substituted with a group selected from RO-, RCO-, RCOO-, and ROCO-, (3) an alkenyl group optionally substituted with a group selected from RO-, RCO-, RCOO-, and ROCO-, or (4) an aralkyl group optionally substituted with a group selected from R-, RO-, RCO-, RCOO-, and ROCO-, in one embodiment, the preferred range is the same as that of R1', R2', R3', R4', R5' and R6'.

[0055] A3 can be independently represented as -O-, -CO-, -COO-, or -OCO-, and in one embodiment, the preferred range is the same as that of A1 and A2.

[0056] Y' independently represents (1) an enyl group optionally substituted with a group selected from RO-, RCO-, RCOO-, and ROCO-, or (2) an enyl group optionally substituted with a group selected from RO-, RCO-, RCOO-, and ROCO-, in one embodiment, the preferred range being the same as X and Y.

[0057] In one embodiment, Z is preferably an independent group represented by formula (Z1).

[0058]

[0059] Z is preferably the group shown in formula (Z2) independently.

[0060]

[0061] Z is each independently and even more preferably a group represented by any of the formulas (Z3-1) to (Z3-36).

[0062]

[0063]

[0064]

[0065] Z is preferably a group represented by formula (Z3-25) independently. * indicates a bonding location.

[0066] Rings Za and Zb each independently represent an aromatic carbon ring optionally having substituents. In one embodiment, rings Za and Zb are preferably benzene rings optionally having substituents, more preferably benzene rings optionally alkyl-substituted, and particularly preferably (unsubstituted) benzene rings.

[0067] X z represents a single bond or -CR z1R z2-, and in one embodiment, it is preferred to be -CR z1R z2-.

[0068] nz represents 0, 1, 2, or 3. In one implementation, it is preferable to be 0, 1, or 2, and even more preferably 0 or 1. For nz units, the units can be the same or different.

[0069] R z1 and R z2 each independently represent a hydrogen atom, optionally an alkyl group with a substituent, optionally an alkenyl group with a substituent, optionally an aryl group with a substituent, or optionally an aralkyl group with a substituent, or R z1 and R z2 are bonded together to represent a non-aromatic carbide ring optionally with a substituent and optionally fused to an aromatic carbide ring. For R z1 and R z2, in one embodiment, R z1 and R z2 are bonded together, preferably a non-aromatic carbide ring optionally with a substituent and optionally fused to an aromatic carbide ring, more preferably a monocyclic saturated carbide ring optionally with a substituent and optionally fused to a benzene ring, particularly preferably a cyclopentane ring optionally fused to a benzene ring.

[0070] R z each independently represents a substituent. In one embodiment, R z is preferably an alkyl group.

[0071] The "substituents" optionally present in the aromatic carbon rings of rings Za and Zb, the alkyl, alkenyl, aryl, aralkyl groups in Rz1 and Rz2, and the "substituents" optionally present in the non-aromatic carbon rings optionally fused with the aromatic carbon rings, and the "substituents" in Rz are not particularly limited, and examples include halogen atoms, alkyl, alkenyl, aryl, aralkyl, alkyl-oxy, alkenyl-oxy, aryl-oxy, aralkyl-oxy, alkyl-carbonyl, alkenyl-carbonyl, aryl-carbonyl, aralkyl-carbonyl, alkyl-oxy-carbonyl, alkenyl-oxy-carbonyl, aryl-oxy-carbonyl, aryl-oxy-carbonyl, aralkyl-oxy-carbonyl, alkyl-carbonyl-oxy, alkenyl-carbonyl-oxy, aryl-carbonyl-oxy, aralkyl-carbonyl-oxy, etc.

[0072] Each z independently represents 0, 1, 2, or 3. In one embodiment, each z is preferably 0, 1, or 2, more preferably 0 or 1, and especially preferably 0.

[0073] n represents 0, 1, 2, or 3. In one implementation, n is preferably 0 or 1 independently. For n units, the units can be the same or different.

[0074] (A) The molecular weight of the cyclic carbonate compound is preferably below 10,000, more preferably below 5,000, even more preferably below 2,000, and particularly preferably below 1,000. The lower limit may be set, for example, above 88 (molecular weight of ethyl carbonate) or above, or above 102 (molecular weight of trimethylolpropene carbonate), etc.

[0075] As specific examples of (A) cyclic carbonate compounds, compounds represented by formulas (A1) to (A17) can be cited.

[0076]

[0077]

[0078] The content of (A) cyclic carbonate compounds in the resin composition is not particularly limited. When the non-volatile component in the resin composition is set to 100% by mass, it is preferably 20% by mass or less, more preferably 15% by mass or less, further preferably 10% by mass or less, even more preferably 5% by mass or less, and particularly preferably 2.5% by mass or less. The lower limit of the content of (A) cyclic carbonate compounds in the resin composition is not particularly limited. When the non-volatile component in the resin composition is set to 100% by mass, it is preferably 0.01% by mass or more, more preferably 0.05% by mass or more, further preferably 0.1% by mass or more, even more preferably 0.5% by mass or more, and particularly preferably 0.8% by mass or more.

[0079] The content of (A) cyclic carbonate compound relative to the total amount of (A) cyclic carbonate compound and (B) epoxy resin (or, when using (D) reactive ester compound, the total amount of (A) cyclic carbonate compound, (B) epoxy resin and (D) reactive ester compound) is not particularly limited. When the total amount of (A) cyclic carbonate compound and (B) epoxy resin (the total amount of (A) cyclic carbonate compound, (B) epoxy resin and (D) reactive ester compound) is set to 100% by mass, the content of (A) cyclic carbonate compound is preferably 0.01% to 50% by mass, more preferably 0.1% to 20% by mass, even more preferably 0.5% to 15% by mass, and particularly preferably 1% to 10% by mass.

[0080] <(B) Epoxy Resin> The resin composition of the present invention contains (B) epoxy resin. (B) epoxy resin is a curable resin having epoxy groups with an epoxy equivalent of 5000 g / eq. or less.

[0081] Examples of epoxy resins (B) include bixylenol type epoxy resin, bisphenol A type epoxy resin, bisphenol F type epoxy resin, bisphenol S type epoxy resin, bisphenol AF type epoxy resin, dicyclopentadiene type epoxy resin, triphenol type epoxy resin, naphthol novolac type epoxy resin, phenol novolac type epoxy resin, tert-butyl-catechol type epoxy resin, naphthalene type epoxy resin, naphthol type epoxy resin, anthracene type epoxy resin, glycidylamine type epoxy resin, glycidyl ester type epoxy resin, and cresol novolac. Novolac type epoxy resin, phenolic alkyl type epoxy resin, biphenyl type epoxy resin, linear aliphatic epoxy resin, epoxy resin with butadiene structure, alicyclic epoxy resin, heterocyclic epoxy resin, spirocyclic epoxy resin, cyclohexane type epoxy resin, cyclohexanediol type epoxy resin, naphthyl ether type epoxy resin, tris(hydroxymethyl) type epoxy resin, tetraphenylethane type epoxy resin, isocyanurate type epoxy resin, phenolphthalimidine type epoxy resin, etc. (B) Epoxy resin can be used alone or in combination of two or more types.

[0082] In the resin composition, the epoxy resin (B) is preferably an epoxy resin having two or more epoxy groups per molecule. The proportion of the epoxy resin having two or more epoxy groups per molecule is preferably 50% by mass or more, more preferably 60% by mass or more, and particularly preferably 70% by mass or more, relative to 100% by mass of the non-volatile components of the epoxy resin (B).

[0083] The epoxy resin includes an epoxy resin that is liquid at a temperature of 20°C (hereinafter sometimes referred to as "liquid epoxy resin") and an epoxy resin that is solid at a temperature of 20°C (hereinafter sometimes referred to as "solid epoxy resin"). For the resin composition of the present invention, the epoxy resin may comprise only liquid epoxy resin, or only solid epoxy resin, or a combination of liquid and solid epoxy resin.

[0084] As a liquid epoxy resin, it is preferable to be a liquid epoxy resin having two or more epoxy groups in one molecule.

[0085] As liquid epoxy resins, glycerol-type epoxy resins, bisphenol A-type epoxy resins, bisphenol F-type epoxy resins, bisphenol AF-type epoxy resins, and naphthalene-type epoxy resins are preferred; glycidyl ester-type epoxy resins, glycidylamine-type epoxy resins, phenolic varnish-type epoxy resins, alicyclic epoxy resins with ester skeletons, cyclohexanediol-type epoxy resins, cyclic aliphatic glycidyl ethers, and epoxy resins with butadiene structures are even more preferred. Glycerol-type epoxy resins, cyclic aliphatic glycidyl ethers, bisphenol A-type epoxy resins, and bisphenol F-type epoxy resins are also preferred.

[0086] Specific examples of liquid epoxy resins include Nagase ChemteX's "EX-992L", Mitsubishi Chemical's "YX7400", DIC's "HP4032", "HP4032D", and "HP4032SS" (naphthalene-type epoxy resin); and Mitsubishi Chemical's "828US", "828EL", "jER828EL", "825", and "EPIKOTE". 828EL (Bisphenol A type epoxy resin); "jER807" and "1750" (Bisphenol F type epoxy resin) manufactured by Mitsubishi Chemical Corporation; "jER152" (Phenolic varnish type epoxy resin) manufactured by Mitsubishi Chemical Corporation; "630", "630LSD", and "604" (Glycidylamine type epoxy resin) manufactured by Mitsubishi Chemical Corporation; "ED-523T" (Glyceryl type epoxy resin) manufactured by ADEKA Corporation; "EP-3950L" and "EP-3980S" (Glycidylamine type epoxy resin) manufactured by ADEKA Corporation; "EP-4088S" (Dicyclopentadiene type epoxy resin) manufactured by ADEKA Corporation; "ZX1059" (a mixture of bisphenol A type epoxy resin and bisphenol F type epoxy resin) manufactured by Nippon Steel Chemical Materials Co., Ltd.; "EX-721" (Glycidyl ester type epoxy resin) manufactured by Nagase ChemteX Corporation; Nagase ChemteX's "EX-991L" (an epoxy resin containing an alkyloxy group backbone and a butadiene backbone); Daicel's "Celloxide 2021P" (an alicyclic epoxy resin with an ester backbone); Daicel's "PB-3600"; Nippon Soda's "JP-100" and "JP-200" (epoxy resins with a butadiene structure); Nippon Steel Chemical Materials' "ZX1658" and "ZX1658GS" (liquid 1,4-glycidylcyclohexane type epoxy resin); Osaka Gas Chemical's "EG-280" (an epoxy resin containing a fluorene structure); and Nagase ChemteX's "EX-201" (a cyclic aliphatic glycidyl ether), etc.

[0087] As a solid epoxy resin, it is preferable to be a solid epoxy resin having three or more epoxy groups in one molecule, and more preferably an aromatic solid epoxy resin having three or more epoxy groups in one molecule.

[0088] As solid epoxy resins, the preferred types are xylenol-type epoxy resins, naphthalene-type epoxy resins, naphthalene-type tetrafunctional epoxy resins, naphthol phenolic varnish-type epoxy resins, cresol phenolic varnish-type epoxy resins, dicyclopentadiene-type epoxy resins, triphenol-type epoxy resins, naphthol-type epoxy resins, biphenyl-type epoxy resins, naphthylene ether-type epoxy resins, anthracene-type epoxy resins, bisphenol A-type epoxy resins, bisphenol AF-type epoxy resins, phenol aralkyl-type epoxy resins, tetraphenylethane-type epoxy resins, and phenol benzopyrrolidone-type epoxy resins.

[0089] Specific examples of solid epoxy resins include DIC's "HP4032H" (naphthalene-type epoxy resin); DIC's "HP-4700" and "HP-4710" (naphthalene-type tetrafunctional epoxy resins); DIC's "N-690" (cresol phenolic varnish type epoxy resin); and DIC's "N-695" (cresol phenolic varnish type epoxy resin). The following are epoxy resins manufactured by DIC: "HP-7200", "HP-7200HH", "HP-7200H", and "HP-7200L" (dicyclopentadiene type epoxy resins); "EXA-7311", "EXA-7311-G3", "EXA-7311-G4", "EXA-7311-G4S", and "HP6000" (naphthalene ether type epoxy resins); "EPPN-502H" (triphenol type epoxy resin) manufactured by Nippon Kayaku Co., Ltd.; "NC7000L" (naphthol phenolic varnish type epoxy resin) manufactured by Nippon Kayaku Co., Ltd.; and "NC3000H", "NC3000", "NC3000L", "NC3000FH", and "NC3100" (biphenyl type epoxy resins). The following are epoxy resins manufactured by Nippon Steel Chemical Materials Co., Ltd.: "ESN475V" and "ESN4100V" (naphthalene-type epoxy resin); "ESN485" (naphthol-type epoxy resin); "ESN375" (dihydroxynaphthalene-type epoxy resin); and "YX4000H," "YX4000," and "YX4000HK" (Mitsubishi Chemical Co., Ltd.). "YL7890" (Bis(xylenol) type epoxy resin); "YL6121" (Biphenyl) type epoxy resin manufactured by Mitsubishi Chemical Company; "YX8800" (Anthracene type epoxy resin) manufactured by Mitsubishi Chemical Company; "YX7700" (Phenolic alkyl group type epoxy resin) manufactured by Mitsubishi Chemical Company; "PG-100" and "CG-500" manufactured by Osaka Gas Chemical Company; and other epoxy resins manufactured by Mitsubishi Chemical Company. "YL7760" (bisphenol AF type epoxy resin); "YL7800" (fluorene type epoxy resin) manufactured by Mitsubishi Chemical Corporation; "jER1010" (bisphenol A type epoxy resin) manufactured by Mitsubishi Chemical Corporation; "jER1031S" (tetraphenylethane type epoxy resin) manufactured by Mitsubishi Chemical Corporation; "WHR991S" (phenolbenzopyrrolidone type epoxy resin) manufactured by Nippon Kayaku Co., Ltd., etc. They can be used individually or in combination of two or more.

[0090] When using solid and liquid epoxy resins in combination as (B) epoxy resins, the preferred ratio of their mass (solid epoxy resin: liquid epoxy resin) is 100:1 to 1:100, more preferably 50:1 to 1:50, and especially preferably 10:1 to 1:10.

[0091] (B) The epoxy equivalent of the epoxy resin is preferably 50 g / eq. to 5,000 g / eq., more preferably 60 g / eq. to 2,000 g / eq., further preferably 70 g / eq. to 1,000 g / eq., and even more preferably 80 g / eq. to 500 g / eq. Epoxy equivalent is the mass of resin per equivalent of epoxy groups. This epoxy equivalent can be determined according to JIS K7236.

[0092] (B) The weight-average molecular weight (Mw) of the epoxy resin is preferably 100-5000, more preferably 250-3000, and even more preferably 400-1500. The weight-average molecular weight of the resin can be determined by gel permeation chromatography (GPC) as a value converted from polystyrene.

[0093] The content of (B) epoxy resin in the resin composition is not particularly limited. When the non-volatile component in the resin composition is set to 100% by mass, it is preferably 30% by mass or less, more preferably 25% by mass or less, further preferably 20% by mass or less, even more preferably 15% by mass or less, and particularly preferably 10% by mass or less. The lower limit of the content of (B) epoxy resin in the resin composition is not particularly limited. When the non-volatile component in the resin composition is set to 100% by mass, it is preferably 0.01% by mass or more, more preferably 0.1% by mass or more, further preferably 1% by mass or more, even more preferably 5% by mass or more, and particularly preferably 7% by mass or more.

[0094] The mass ratio of (B) epoxy resin to (A) cyclic carbonate compound in the resin composition ((B) component / (A) component) is not particularly limited, but it is preferably 0.1 or more, more preferably 0.5 or more, and particularly preferably 1 or more. The upper limit of the mass ratio of (B) epoxy resin to (A) cyclic carbonate compound in the resin composition ((B) component / (A) component) is not particularly limited, but it is preferably 100 or less, more preferably 50 or less, and particularly preferably 10 or less.

[0095] <(C) Inorganic filler materials> The resin composition of the present invention contains (C) an inorganic filler. (C) The inorganic filler is contained in the resin composition in the form of particles.

[0096] Inorganic compounds are used as the inorganic filler material in (C). Examples of inorganic filler materials in (C) include silica, alumina, aluminosilicates, glass, cordierite, silica, barium sulfate, barium carbonate, talc, clay, mica powder, zinc oxide, hydrotalcite, boehmite, aluminum hydroxide, magnesium hydroxide, calcium carbonate, magnesium carbonate, magnesium oxide, boron nitride, aluminum nitride, manganese nitride, aluminum borate, strontium carbonate, strontium titanate, calcium titanate, magnesium titanate, bismuth titanate, titanium oxide, zirconium oxide, barium titanate, barium zirconate titanate, barium zirconate, calcium zirconate, zirconium phosphate, and zirconium tungstate phosphate. Among these, silica or aluminosilicates are particularly preferred. Examples of silica include amorphous silica, fused silica, crystalline silica, synthetic silica, and hollow silica. In addition, spherical silicon dioxide is preferred as the silicon dioxide. (C) One type of inorganic filler material may be used alone, or two or more types may be used in any ratio.

[0097] Commercially available products as (C) inorganic filler materials include, for example, “SP60-05” and “SP507-05” manufactured by Nippon Steel Chemical Materials Co., Ltd.; “YC100C”, “YA050C”, “YA050C-MJE” and “YA010C” manufactured by Admatechs Co., Ltd.; “UFP-30” manufactured by DENKA Co., Ltd.; “Silfil NSS-3N”, “Silfil NSS-4N” and “Silfil NSS-5N” manufactured by Tokuyama Co., Ltd.; “SC2500SQ”, “SO-C4”, “SO-C2” and “SO-C1” manufactured by Admatechs Co., Ltd.; “DAW-03” and “FB-105FD” manufactured by DENKA Co., Ltd.; “BA-S” manufactured by Nippon Chemicals Co., Ltd.; and “MG-005” manufactured by Taiheiyo-Cement Co., Ltd.

[0098] (C) The average particle size of the inorganic filler material is not particularly limited, but it is preferably below 10 μm, more preferably below 5 μm, further preferably below 4 μm, even more preferably below 3 μm, and particularly preferably below 2.7 μm. (C) The lower limit of the average particle size of the inorganic filler material is not particularly limited, but it is preferably above 0.01 μm, more preferably above 0.05 μm, further preferably above 0.1 μm, and particularly preferably above 0.2 μm. (C) The average particle size of the inorganic filler material can be determined using a laser diffraction-scattering method based on the Mie scattering theory. Specifically, it can be determined by: using a laser diffraction-scattering particle size distribution measuring device, preparing a particle size distribution of the inorganic filler material on a volume basis, and taking the median particle size as the average particle size. The sample for measurement can be a sample obtained by: weighing 100 mg of the inorganic filler material and 10 g of methyl ethyl ketone into a vial, and dispersing it using ultrasound for 10 minutes. For the sample being measured, a laser diffraction particle size distribution measuring device is used. The light source wavelength is set to blue and red, and the particle size distribution of the inorganic filler material is measured in a flow cell manner based on a volume reference. The average particle size is calculated from the obtained particle size distribution as the median particle size. Examples of laser diffraction particle size distribution measuring devices include the "LA-960" manufactured by Horiba Manufacturing Co., Ltd.

[0099] (C) The specific surface area of ​​the inorganic filler material is not particularly limited, but it is preferably 0.1 m² / g or higher, more preferably 0.5 m² / g or higher, further preferably 1 m² / g or higher, and particularly preferably 3 m² / g or higher. (C) The upper limit of the specific surface area of ​​the inorganic filler material is not particularly limited, but it is preferably below 100 m² / g, more preferably below 70 m² / g, further preferably below 50 m² / g, and particularly preferably below 40 m² / g. The specific surface area of ​​the inorganic filler material can be obtained by using a specific surface area measuring device (Macsorb HM-1210 manufactured by Mountech) to adsorb nitrogen gas onto the sample surface and calculating the specific surface area using the BET multi-point method.

[0100] (C) The inorganic filler material can be a non-hollow inorganic filler material with a porosity of 0% by volume (preferably non-hollow silica or non-hollow aluminosilicate), or a hollow inorganic filler material with a porosity greater than 0% by volume (preferably hollow silica or hollow aluminosilicate), or a combination of both. From the viewpoint of suppressing the dielectric constant to a lower value, the inorganic filler material preferably contains only hollow inorganic filler material (preferably hollow silica or hollow aluminosilicate), or contains both non-hollow inorganic filler material (preferably non-hollow silica or non-hollow aluminosilicate) and hollow inorganic filler material (preferably hollow silica or hollow aluminosilicate). The porosity of the hollow inorganic filler material is preferably 90% by volume or less, and more preferably 85% by volume or less. (C) The lower limit of the porosity of inorganic filler materials can be set, for example, as greater than 0% by volume, greater than 1% by volume, greater than 5% by volume, greater than 10% by volume, greater than 20% by volume, etc. The porosity P (volume %) of inorganic filler materials is defined as the volume reference ratio (total volume of pores / volume of particles) of the total volume of one or more pores existing inside the particles relative to the volume of the particles as a whole with reference to the outer surface of the particles. For example, it can be calculated using the measured value of the actual density of the inorganic filler material DM (g / cm3) and the theoretical value of the material density of the material forming the inorganic filler material DT (g / cm3) using the following formula (I).

[0101]

[0102] The actual density of inorganic filler materials can be measured, for example, using a true density measuring device. Examples of true density measuring devices include the ULTRAPYCNOMETER 1000 manufactured by QUANTACHROME. Nitrogen gas can be used as the measuring gas, for example.

[0103] From the perspective of improving moisture resistance and dispersibility, (C) inorganic filler materials are preferably treated with surface treatment agents. Examples of surface treatment agents include fluorosilane coupling agents, aminosilane coupling agents, epoxysilane coupling agents, mercaptosilane coupling agents, silane coupling agents, alkoxysilanes, organosilazane compounds, and titanate coupling agents. Furthermore, a single surface treatment agent can be used, or two or more can be used in combination.

[0104] Commercially available surface treatment agents include, for example: KBM403 (3-epoxypropoxypropyltrimethoxysilane) manufactured by Shin-Etsu Chemical Industry Co., Ltd., KBM803 (3-mercaptopropyltrimethoxysilane) manufactured by Shin-Etsu Chemical Industry Co., Ltd., KBE903 (3-aminopropyltriethoxysilane) manufactured by Shin-Etsu Chemical Industry Co., Ltd., KBM573 (N-phenyl-3-aminopropyltrimethoxysilane) manufactured by Shin-Etsu Chemical Industry Co., Ltd., SZ-31 (hexamethyldisilazane) manufactured by Shin-Etsu Chemical Industry Co., Ltd., KBM103 (phenyltrimethoxysilane) manufactured by Shin-Etsu Chemical Industry Co., Ltd., KBM-4803 (long-chain epoxy silane coupling agent) manufactured by Shin-Etsu Chemical Industry Co., Ltd., and KBM-7103 (3,3,3-trifluoropropyltrimethoxysilane) manufactured by Shin-Etsu Chemical Industry Co., Ltd.

[0105] From the perspective of improving the dispersibility of inorganic filler materials, it is preferable to control the degree of surface treatment using surface treatment agents within a specified range. Specifically, for 100% by mass of inorganic filler material, it is preferable to have surface treated with 0.2% to 5% by mass of surface treatment agent, more preferably with 0.2% to 3% by mass, and even more preferably with 0.3% to 2% by mass.

[0106] The degree of surface treatment using surface treatment agents can be evaluated by the carbon content per unit surface area of ​​the inorganic filler. From the viewpoint of improving the dispersibility of the inorganic filler, the carbon content per unit surface area of ​​the inorganic filler is preferably 0.02 mg / m² or more, more preferably 0.1 mg / m² or more, and even more preferably 0.2 mg / m² or more. On the other hand, from the viewpoint of preventing an increase in the melt viscosity of the resin composition, or the melt viscosity in flake form, it is preferably 1.0 mg / m² or less, more preferably 0.8 mg / m² or less, and even more preferably 0.5 mg / m² or less.

[0107] (C) The carbon content per unit surface area of ​​the inorganic filler material can be determined after washing the surface-treated inorganic filler material with a solvent (e.g., methyl ethyl ketone (MEK)). Specifically, sufficient MEK as a solvent is added to the surface-treated inorganic filler material, and ultrasonic washing is performed at 25°C for 5 minutes. The supernatant is removed, the solid components are dried, and then the carbon content per unit surface area of ​​the inorganic filler material can be determined using a carbon analyzer. A carbon analyzer such as the "EMIA-320V" manufactured by Horiba Manufacturing Co., Ltd. can be used.

[0108] The content of (C) inorganic filler material in the resin composition is not particularly limited. When the non-volatile component in the resin composition is set to 100% by mass, it is preferably 90% by mass or less, more preferably 85% by mass or less, even more preferably 80% by mass or less, and particularly preferably 78% by mass or less. The lower limit of the content of (C) inorganic filler material in the resin composition is not particularly limited. When the non-volatile component in the resin composition is set to 100% by mass, it is, for example, preferably 5% by mass or more or 10% by mass or more, more preferably 20% by mass or more or 30% by mass or more, even more preferably 40% by mass or more or 50% by mass or more, even more preferably 55% by mass or more or 60% by mass or more, and particularly preferably 65% ​​by mass or more or 70% by mass or more.

[0109] The mass ratio ((C) component / (A) component) of the inorganic filler material to the cyclic carbonate compound in the resin composition is not particularly limited, but it is preferably 1 or more, more preferably 5 or more, and particularly preferably 10 or more. The upper limit of the mass ratio ((C) component / (A) component) of the inorganic filler material to the cyclic carbonate compound in the resin composition is not particularly limited, but it is preferably 1000 or less, more preferably 500 or less, and particularly preferably 100 or less.

[0110] <(D) Active Ester Compounds> The resin composition of the present invention preferably contains (D) active ester compound. One (D) active ester compound may be used alone, or two or more may be used in any proportion. The (D) active ester compound may function as an epoxy resin curing agent that reacts with (B) epoxy resin to cure it.

[0111] As (D) reactive ester compounds, compounds having two or more highly reactive ester groups in one molecule, such as phenolic esters, thiophenolic esters, N-hydroxyamine esters, or heterocyclic hydroxyl compounds, are generally preferred. These reactive ester compounds are preferably obtained through the condensation reaction of carboxylic acid compounds and / or thiocarboxylic acid compounds with hydroxyl compounds and / or thiols. Particularly from the viewpoint of improved heat resistance, reactive ester compounds obtained from carboxylic acid compounds and hydroxyl compounds are preferred, and reactive ester compounds obtained from carboxylic acid compounds and phenolic compounds and / or naphthol compounds are even more preferred. Examples of carboxylic acid compounds include benzoic acid, acetic acid, succinic acid, maleic acid, itaconic acid, phthalic acid, isophthalic acid, terephthalic acid, and pyromellitic acid. Examples of phenolic or naphthol compounds include hydroquinone, resorcinol, bisphenol A, bisphenol F, bisphenol S, phenolphthalein, methylated bisphenol A, methylated bisphenol F, methylated bisphenol S, phenol, o-cresol, m-cresol, p-cresol, catechol, α-naphthol, β-naphthol, 1,5-dihydroxynaphthol, 1,6-dihydroxynaphthol, 2,6-dihydroxynaphthol, dihydroxybenzophenone, trihydroxybenzophenone, tetrahydroxybenzophenone, phloroglucinol, pyroglucinol, dicyclopentadiene-type diphenol compounds, and phenol novolac. Here, "dicyclopentadiene-type diphenol compounds" refers to diphenol compounds obtained by condensing one molecule of dicyclopentadiene with two molecules of phenol.

[0112] Specifically, as (D) the active ester compound, it is preferably a dicyclopentadiene-type active ester compound, a naphthalene-type active ester compound containing a naphthalene structure, an active ester compound containing an acetylated compound of phenolic varnish, or an active ester compound containing a benzoylated compound of phenolic varnish, wherein it is more preferably selected from at least one of dicyclopentadiene-type active ester compounds and naphthalene-type active ester compounds. As a dicyclopentadiene-type active ester compound, it is preferably an active ester compound containing a dicyclopentadiene-type diphenol structure.

[0113] Commercially available (D) active ester compounds include, for example, "EXB9451", "EXB9460", "EXB9460S", "HPC-8000L-65TM", "HPC-8000-65T", "HPC-8000H", and "HPC-8000H-65TM" (manufactured by DIC); and for, "HP-B-8151-62T", "EXB-8100L-65T", "EXB-9416-70BK", and "HPC-815". Examples of active ester compounds that contain phosphorus include "0-62T" and "EXB-8" (manufactured by DIC Corporation); examples of active ester compounds that contain phosphorus include "EXB9401" (manufactured by DIC Corporation); examples of active ester compounds that contain acetylated compounds in phenolic varnishes include "DC808" (manufactured by Mitsubishi Chemical Corporation); examples of active ester compounds that contain benzoyl compounds in phenolic varnishes include "YLH1026", "YLH1030", and "YLH1048" (manufactured by Mitsubishi Chemical Corporation); and examples of active ester compounds that contain styrene and naphthalene structures include "PC1300-02-65MA" (manufactured by AIR&WATER Corporation).

[0114] (D) The reactive ester equivalent (reactive group equivalent as a hardener) of the reactive ester compound is preferably 50 g / eq. to 500 g / eq., more preferably 50 g / eq. to 400 g / eq., and even more preferably 100 g / eq. to 300 g / eq. The reactive ester equivalent is the mass of the reactive ester compound per 1 reactive ester equivalent.

[0115] There is no particular limitation on the content of (D) active ester compounds in the resin composition. When the non-volatile components in the resin composition are set to 100% by mass, it is preferably 1% by mass or more, more preferably 5% by mass or more, even more preferably 10% by mass or more, even more preferably 12% by mass or more, and particularly preferably 13% by mass or more. There is no particular limitation on the upper limit of the content of (D) active ester compounds in the resin composition. When the non-volatile components in the resin composition are set to 100% by mass, it is preferably 50% by mass or less, more preferably 40% by mass or less, even more preferably 30% by mass or less, even more preferably 25% by mass or less, and particularly preferably 20% by mass or less.

[0116] The mass ratio of (D) active ester compound to (A) cyclic carbonate compound in the resin composition ((D) component / (A) component) is not particularly limited, but it is preferably 0.5 or more, more preferably 1 or more, and particularly preferably 5 or more. The upper limit of the mass ratio of (D) active ester compound to (A) cyclic carbonate compound in the resin composition ((D) component / (A) component) is not particularly limited, but it is preferably 100 or less, more preferably 30 or less, and particularly preferably 15 or less.

[0117] <(D') Other hardeners> The resin composition of the present invention may further include (D') curing agents as optional components other than (D). One (D') curing agent may be used alone, or two or more may be used in arbitrary combinations. The (D') curing agents may function similarly to the (D) reactive ester curing agents as epoxy resin curing agents that react with (B) epoxy resin to cure it.

[0118] Other curing agents (D') are not particularly limited, and examples include phenolic curing agents, carbodiimide curing agents, acid anhydride curing agents, amine curing agents, benzoxazine curing agents, cyanate ester curing agents, and thiol curing agents. Preferably, the curing agent is selected from phenolic and carbodiimide curing agents, and the resin composition of the present invention more preferably includes both phenolic and carbodiimide curing agents.

[0119] From the viewpoint of heat resistance and water resistance, phenolic curing agents with a novolac structure are preferred as phenolic curing agents. Furthermore, from the viewpoint of adhesion to the substrate, nitrogen-containing phenolic curing agents are preferred, and those containing a triazine skeleton are even more preferred. Among these, from the viewpoint of highly satisfying heat resistance, water resistance, and adhesion, phenolic novolac resins containing a triazine skeleton are preferred. Specific examples of phenolic curing agents include MEH-7700, MEH-7810, MEH-7851 manufactured by Meiwa Kasei Corporation; NHN, CBN, and GPH manufactured by Nippon Kayaku Co., Ltd.; SN-170, SN-180, SN-190, SN-475, SN-485, SN-495, SN-375, and SN-395 manufactured by Nippon Steel Chemical Materials Co., Ltd.; and LA-7052, LA-7054, LA-3018, LA-3018-50P, LA-1356, TD2090, and KA-1160 manufactured by DIC Corporation.

[0120] As a carbodiimide-based curing agent, examples include curing agents having one or more, preferably two or more, carbodiimide structures within one molecule. Examples include aliphatic bis(tert-butylcarbodiimide), cyclohexanebis(methylene-tert-butylcarbodiimide), etc.; aromatic bis(xylylcarbodiimide), etc.; and aliphatic poly(methylene-tert-butylcarbodiimide), etc. Carbodiimides; poly(phenylcarbodiimide), poly(naphthylcarbodiimide), poly(tolylcarbodiimide), poly(methyldiisopropylphenylcarbodiimide), poly(triethylphenylcarbodiimide), poly(diethylphenylcarbodiimide), poly(triisopropylphenylcarbodiimide), poly(diisopropylphenylcarbodiimide), poly(xylylcarbodiimide), poly(tetramethylxylylcarbodiimide), poly(methylenediphenylcarbodiimide), poly[methylenebis(methylphenyl)carbodiimide] and other aromatic polycarbodiimides.

[0121] Commercially available carbodiimide-based curing agents include, for example, "CARBODILITE V-02B", "CARBODILITE V-03", "CARBODILITE V-04K", "CARBODILITE V-07" and "CARBODILITE V-09" manufactured by Nisshinbo Chemical Co., Ltd.; and "Stabaxol P", "Stabaxol P400" and "Hycasyl 510" manufactured by Rhein-Chemie Co., Ltd.

[0122] As an anhydride-based curing agent, examples include curing agents having one or more anhydride groups per molecule, preferably curing agents having two or more anhydride groups per molecule. Specific examples of anhydride-based curing agents include phthalic anhydride, tetrahydrophthalic anhydride, hexahydrophthalic anhydride, methyltetrahydrophthalic anhydride, methylhexahydrophthalic anhydride, methylnadic anhydride, hydrogenated methylnadic anhydride, trialkyltetrahydrophthalic anhydride, dodecenylsuccinic anhydride, 5-(2,5-dioxotetrahydro-3-furanyl)-3-methyl-3-cyclohexene-1,2-dicarboxylic anhydride, trimellitic anhydride, pyromellitic anhydride, and diphenyltrioxide. Benzophenone tetracarboxylic dianhydride, biphenyl tetracarboxylic dianhydride, naphthalene tetracarboxylic dianhydride, oxydiphthalic dianhydride, 3,3'-4,4'-diphenyltristyric dianhydride, 1,3,3a,4,5,9b-hexahydro-5-(tetrahydro-2,5-dioxo-3-furanyl)-naphtho[1,2-C]furan-1,3-dione, ethylene glycol bis(trimethicone ester), styrene-maleic acid resin obtained by copolymerization of styrene and maleic acid, and other polymeric anhydrides. Commercially available anhydride-based curing agents include: "HNA-100", "MH-700", "MTA-15", "DDSA", and "OSA" manufactured by New Japan Rika Co., Ltd.; "YH-306" and "YH-307" manufactured by Mitsubishi Chemical Co., Ltd.; "HN-2200" and "HN-5500" manufactured by Hitachi Chemical Co., Ltd.; and "EF-30", "EF-40", "EF-60", and "EF-80" manufactured by Cray Valley Co., Ltd.

[0123] As amine-based curing agents, examples include curing agents having one or more, preferably two or more, amine groups within one molecule. Examples include aliphatic amines, polyether amines, alicyclic amines, and aromatic amines. From the viewpoint of achieving the desired effect of the present invention, aromatic amines are preferred. The amine-based curing agent is preferably a primary or secondary amine, and more preferably a primary amine. Specific examples of amine-based curing agents include 4,4'-methylenebis(2,6-dimethylaniline), 4,4'-diaminodiphenylmethane, 4,4'-diaminodiphenyl sulfone, 3,3'-diaminodiphenyl sulfone, m-phenylenediamine, m-xylenediamine, diethyltoluenediamine, 4,4'-diaminodiphenyl ether, 3,3'-dimethyl-4,4'-diaminobiphenyl, 2,2'-dimethyl-4,4'-diaminobiphenyl, 3,3'-dihydroxybenzidine, and 2,2-bis(3-amino-4-hydroxy) 2,2-bis(4-aminophenyl)propane, 3,3-dimethyl-5,5-diethyl-4,4-diphenylmethanediamine, 2,2-bis(4-aminophenyl)propane, 2,2-bis(4-(4-aminophenoxy)phenyl)propane, 1,3-bis(3-aminophenoxy)benzene, 1,3-bis(4-aminophenoxy)benzene, 1,4-bis(4-aminophenoxy)benzene, 4,4'-bis(4-aminophenoxy)biphenyl, bis(4-(4-aminophenoxy)phenyl) benzoxide, bis(4-(3-aminophenoxy)phenyl) benzoxide, etc. Amine-based hardeners can be commercially available products, such as SEIKA's "SEIKACURE-S", Nippon Kayaku Co.'s "KAYABOND C-200S", "KAYABOND C-100", "KAYAHARD AA", "KAYAHARD AB", "KAYAHARD AS", and Mitsubishi Chemical's "Epicure W".

[0124] Specific examples of benzoxazine-based hardeners include "JBZ-OP100D" and "ODA-BOZ" manufactured by JFE Chemical Co., Ltd.; "HFB2006M" manufactured by Showa Polymer Co., Ltd.; and "Pd" and "Fa" manufactured by Shikoku Chemical Industry Co., Ltd.

[0125] Examples of cyanate ester curing agents include: bisphenol A dicyanate, polyphenol cyanates (oligomeric (3-methylene-1,5-phenyl cyanate)), 4,4'-methylenebis(2,6-dimethylphenyl cyanate), 4,4'-ethylidene diphenyl dicyanate, hexafluorobisphenol A dicyanate, 2,2-bis(4-cyanate)phenylpropane, 1,1-bis(4-cyanate phenylmethane), bis(4-cyanate-3,5-dimethylphenyl)methane, 1,3-bis(4-cyanate phenyl-1-(methylethylidene))benzene, bis(4-cyanate phenyl) sulfide, and bis(4-cyanate phenyl) ether, etc., difunctional cyanate ester resins; multifunctional cyanate ester resins derived from phenolic varnishes and cresol varnishes, etc.; and prepolymers formed by partially triazinizing these cyanate ester resins. Specific examples of cyanate ester-based curing agents include Lonza Japan's "PT30" and "PT60" (both phenolic varnish-type multifunctional cyanate ester resins), "BA230", and "BA230S75" (prepolymers of bisphenol A dicyanate that have undergone triazinization to become trimers).

[0126] Examples of thiol-based curing agents include trimethylolpropane tris(3-mercaptopropionate), pentaerythritol tetra(3-mercaptobutyrate), and tris(3-mercaptopropyl)isocyanurate.

[0127] (D') The reactive group equivalent of other hardeners is preferably 50 g / eq. to 3000 g / eq., more preferably 100 g / eq. to 1000 g / eq., even more preferably 100 g / eq. to 500 g / eq., and particularly preferably 100 g / eq. to 300 g / eq. The reactive group equivalent is the mass of hardener per 1 equivalent of reactive group. A reactive group refers to the group that reacts with the epoxy resin; if it is a phenolic hardener, it is a phenolic hydroxyl group; if it is a carbodiimide hardener, it is a carbodiimide group, depending on the type of hardener.

[0128] The content of other curing agents (D') in the resin composition is not particularly limited. When the non-volatile component in the resin composition is set to 100% by mass, it is preferably 15% by mass or less, more preferably 10% by mass or less, further preferably 5% by mass or less, and particularly preferably 3.5% by mass or less. The lower limit of the content of other curing agents (D') in the resin composition is not particularly limited. When the non-volatile component in the resin composition is set to 100% by mass, it can be, for example, 0% by mass or more, 0.1% by mass or more, 1% by mass or more, 1.5% by mass or more, 2% by mass or more, 2.5% by mass or more, etc.

[0129] When the total amount of (D) active ester compound and (D') other curing agent in the resin composition is set to 100% by mass, the content of (D) active ester compound in the resin composition is preferably 10% by mass or more, more preferably 30% by mass or more, even more preferably 40% by mass or more, and particularly preferably 50% by mass or more.

[0130] The ratio (curing agent reactive groups / epoxy groups) of the total molar equivalent number of curing agent reactive groups in the resin composition to the total molar equivalent number of epoxy groups in the (B) epoxy resin is preferably in the range of 0.2 to 2, more preferably in the range of 0.5 to 1.8, and even more preferably in the range of 1 to 1.5. The total molar equivalent number of epoxy groups in the (B) epoxy resin represents the total value obtained by dividing the mass of the (B) epoxy resin present in the resin composition by the epoxy equivalent. Furthermore, the total molar equivalent number of curing agent reactive groups in the (D) reactive ester compound and (D') other curing agents represents the total value obtained by dividing the mass of the (D) reactive ester compound present in the resin composition by the reactive ester group equivalent, and the total value obtained by dividing the mass of the (D') other curing agents by the reactive group equivalent.

[0131] <(E) Compounds containing free radical polymerizable groups> The resin composition of the present invention may also include (E) compounds containing free radical polymerizable groups. (E) Compounds containing free radical polymerizable groups are compounds containing one or more (preferably two or more) free radical polymerizable groups in one molecule. (E) Compounds containing free radical polymerizable groups may be used alone or in combination of two or more.

[0132] Free radical polymerizable groups refer to groups with vinyl unsaturated bonds that have free radical polymerizability, without any particular limitation.

[0133] As an example, one could cite: (1) The group shown in formula (R), (2) Maleimino (2,5-dihydro-2,5-dioxo-1H-pyrrole-1-yl), etc. The aforementioned formula (R) is

[0134] [In the formula, Ra independently represents a hydrogen atom or a methyl group; Xa independently represents a carbonyl group, a methylene group, or a phenyl group; * indicates a bonding site].

[0135] In the first embodiment, (E) the compound containing free radical polymerizable groups is preferably a thermoplastic resin (e.g., a number-average molecular weight of 800 or more) containing two or more groups shown in the above formula (R). Thermoplastic resins are not particularly limited, and examples include phenoxy resins, polyvinyl acetal resins, polystyrene resins, polyethylene resins, polypropylene resins, polybutadiene resins, polyimide resins, polyamide-imide resins, polyether-imide resins, polyphenylene ether resins, polyether ether ketone resins, polyester resins, etc. In this embodiment, (E) the compound containing free radical polymerizable groups comprises modified resins of these resins having two or more groups shown in the above formula (R).

[0136] In the first embodiment, (E) the compound containing free radical polymerizable groups is preferably a resin selected from modified polyphenylene ether resins having two or more groups shown in the above formula (R) and modified polystyrene resins having two or more groups shown in the above formula (R), more preferably a modified polyphenylene ether resin having two or more groups shown in the above formula (R), and particularly preferably a resin shown in formula (2).

[0137]

[0138] [In the formula, Rb independently represents a hydrogen atom or a methyl group; Xb independently represents a carbonyl group, methylene group, phenyl group, or phenyl-methylene group (the bonding direction is not particularly limited, but it is preferred that the phenyl side is bonded to the C in "RbC"); R11 and R12 independently represent alkyl groups; R13, R14, R21, R22, R23 and R24 independently represent hydrogen atoms or alkyl groups; A represents a single bond, -C(Rc)2-, -O-, -CO-, -S-, -SO- or -SO2-; Rc independently represents a hydrogen atom or an alkyl group; p represents 0 or 1; q and r independently represent integers greater than 1.] For q units and r units respectively, the units can be the same or different.

[0139] R b independently represents either a hydrogen atom or a methyl group. X b independently represents either a carbonyl group, a methylene group, a phenyl group, or a phenyl-methylene group (the bonding direction is not particularly limited, but it is preferred that the phenyl side is bonded to the C in "R bC"), preferably a carbonyl group or a phenyl-methylene group.

[0140] R 11 and R 12 each independently represent an alkyl group, preferably a methyl group. R 13 and R 14 each independently represent a hydrogen atom or an alkyl group, preferably a hydrogen atom. R 21 and R 22 each independently represent a hydrogen atom or an alkyl group, preferably a hydrogen atom or a methyl group, more preferably a methyl group. R 23 and R 24 each independently represent a hydrogen atom or an alkyl group, preferably a hydrogen atom or a methyl group.

[0141] A represents a single bond, -C(Rc)²⁻, -O⁻, -CO⁻, -S⁻, -SO⁻, or -SO₂⁻, preferably a single bond, -C(Rc)²⁻, or -O⁻. Rc independently represents a hydrogen atom or an alkyl group, preferably a hydrogen atom or a methyl group. p represents 0 or 1, preferably 1. q and r independently represent integers greater than 1, preferably integers from 1 to 200, and more preferably integers from 1 to 100.

[0142] In the first embodiment (E), the free radical polymerizable group equivalent of the compound is preferably 300 g / eq. to 2500 g / eq., more preferably 400 g / eq. to 2000 g / eq. The free radical polymerizable group equivalent indicates the mass of resin (compound) per 1 equivalent of free radical polymerizable groups.

[0143] The number-average molecular weight of the compound containing free radical polymerizable groups in embodiment (E) is preferably 800-10000, more preferably 900-5000. The number-average molecular weight of the resin can be determined by gel permeation chromatography (GPC) as a value converted from polystyrene.

[0144] Commercially available products containing free radical polymerizable groups as described in the first embodiment (E) include, for example, “OPE-2St 1200” and “OPE-2St 2200” (vinyl benzyl modified polyphenylene ether resin) manufactured by Mitsubishi Gas Chemical Co., Ltd.; and “SA9000” and “SA9000-111” (methacrylic acid modified polyphenylene ether resin) manufactured by SABIC Innovative Plastics Co., Ltd.

[0145] In the second embodiment, (E) the compound containing a free radical polymerizable group is preferably a maleimide compound having a partial structure shown in formula (3').

[0146]

[0147] [In the formula, ring B represents a monocyclic alkane ring optionally having a substituent, or a monocyclic alkene ring optionally having a substituent; i and j each independently represent an integer of 0 or more, and the sum of i and j is 6 or more; * indicates a bonding site.] Maleimine compounds refer to compounds containing at least one maleimine group (2,5-dihydro-2,5-dioxo-1H-pyrrole-1-yl) in one molecule. In the second embodiment, the number of maleimine groups in one molecule of the maleimine compound is preferably 2 or more, particularly preferably 2. The maleimine compound in the second embodiment can be used alone or in combination of two or more in any proportion.

[0148] A monocyclic alkane ring refers to a monocyclic aliphatic saturated hydrocarbon ring. Preferably, the monocyclic alkane ring has 4 to 14 carbon atoms, more preferably 4 to 10 carbon atoms, and particularly preferably 5 or 6 carbon atoms. Examples of monocyclic alkane rings include cyclobutane, cyclopentane, cyclohexane, cycloheptane, and cyclooctane. A monocyclic alkene ring refers to a monocyclic aliphatic unsaturated hydrocarbon ring having at least one carbon-carbon double bond. Preferably, the monocyclic alkene ring has 4 to 14 carbon atoms, more preferably 4 to 10 carbon atoms, and particularly preferably 5 or 6 carbon atoms. Examples of monocyclic alkene rings include cyclobutene, cyclopentene, cyclohexene, cycloheptene, cyclooctene, cyclopentadiene, and cyclohexadiene.

[0149] As a "substituent" for monocyclic alkane rings and monocyclic olefin rings, examples can be given of groups that are the same as the "substituents" optionally present in the aromatic carbon rings of the aforementioned ring Z'.

[0150] Ring B represents a monocyclic alkane ring optionally having substituents, or a monocyclic alkene ring optionally having substituents. Ring B is preferably a monocyclic alkane ring optionally substituted with a group selected from alkyl and alkenyl groups; or a monocyclic alkene ring optionally substituted with a group selected from alkyl and alkenyl groups. Ring B is more preferably a monocyclic alkane ring optionally substituted with a group selected from alkyl groups having 1 to 14 carbon atoms and alkenyl groups having 2 to 14 carbon atoms; or a monocyclic alkene ring optionally substituted with a group selected from alkyl groups having 1 to 14 carbon atoms and alkenyl groups having 2 to 14 carbon atoms.

[0151] i and j each independently represent an integer greater than or equal to 0 or 1, and the sum of i and j is 6 or greater (preferably 8 or greater, more preferably 10 or greater). i and j preferably each independently represent an integer from 0 to 20, and the sum of i and j is 6 or greater (preferably 8 or greater, more preferably 10 or greater). i and j preferably each independently represent an integer from 1 to 20, and the sum of i and j is 6 or greater (preferably 8 or greater, more preferably 10 or greater). i and j are further preferably each independently represent an integer from 5 to 10. i and j are particularly preferably 8.

[0152] In the second embodiment, (E) the compound containing a free radical polymerizable group is particularly preferably a maleimide compound represented by formula (3).

[0153]

[0154] [In the formula, R10 independently represents a substituent; each ring C independently represents an aromatic ring optionally having a substituent; D1 and D2 independently represent a single bond, -C(Rx)2-, -O-, -CO-, -S-, -SO-, -SO2-, -CONH-, -NHCO-, -COO-, or -OCO-; Rx independently represents a hydrogen atom or an alkyl group; a independently represents 0 or 1; b independently represents an integer greater than or equal to 0 or 1; c independently represents 0, 1, or 2; m represents an integer greater than or equal to 0 or 1; other symbols have the same meaning as the corresponding symbols above.] For units b, c, and m respectively, the units can be the same or different.

[0155] An aromatic ring is a ring whose π-electron system contains 4p+2 electrons (p being a natural number) and follows Hückel's rule. The aromatic ring can be an aromatic carbon ring with only carbon atoms as ring-forming atoms, or an aromatic heteroring with heteroatoms such as oxygen, nitrogen, and sulfur atoms as ring-forming atoms in addition to carbon atoms. In one embodiment, an aromatic carbon ring is preferred. In one embodiment, the aromatic ring is preferably a 5-14 member aromatic ring, more preferably a 6-14 member aromatic ring, and even more preferably a 6-10 member aromatic ring. Preferred examples of aromatic rings include benzene rings, naphthalene rings, anthracene rings, and phenanthrene rings, with benzene rings or naphthalene rings being more preferred, and benzene rings being particularly preferred.

[0156] As a "substituent" in R 10 and a "substituent" in the aromatic ring, the same group as the "substituent" optionally present in the aromatic carbon ring of the aforementioned ring Z' can be cited.

[0157] Each ring C independently represents an aromatic ring optionally having substituents, preferably a benzene ring optionally substituted with a group selected from alkyl groups. D1 and D2 independently represent a single bond, -C(Rx)2-, -O-, -CO-, -S-, -SO-, -SO2-, -CONH-, -NHCO-, -COO-, or -OCO-, preferably a single bond, -C(Rx)2-, or -O-. Rx independently represents a hydrogen atom or an alkyl group, preferably a hydrogen atom or a methyl group. a independently represents 0 or 1, preferably 0. b independently represents an integer greater than or equal to 0 or 1, preferably 0, 1, 2, or 3, more preferably 0, 1, or 2. c independently represents 0, 1, or 2, preferably 0. m represents an integer greater than or equal to 0 or 1, preferably 0.

[0158] As part of the structure shown in equation (D) included in equation (3), there are no particular limitations.

[0159]

[0160] [In the formula, * indicates the bonding location; other symbols have the same meaning as the corresponding symbols mentioned above.] Examples of the partial structures shown in the aforementioned equation (D) are those shown in equations (D-1) to (D-3).

[0161]

[0162] [In the formula, * has the same meaning as above].

[0163] In the second embodiment, the free radical polymerizable group equivalent of the compound containing free radical polymerizable groups (E) is preferably 200 g / eq. to 2500 g / eq., more preferably 250 g / eq. to 2000 g / eq., and even more preferably 300 g / eq. to 1500 g / eq. The free radical polymerizable group equivalent of the compound containing free radical polymerizable groups (E) indicates the mass of resin per 1 equivalent of free radical polymerizable groups.

[0164] The weight average molecular weight of the compound containing a free radical polymerizable group in the second embodiment (E) is preferably 400 to 10,000, more preferably 500 to 7,000, and particularly preferably 600 to 5,000.

[0165] Commercially available products containing free radical polymerizable groups as (E) in the second embodiment include, for example, “BMI-689”, “BMI-1500”, “BMI-1700”, “BMI-3000J” manufactured by Designer Molecules Co., Ltd., and “SLK-6895-T90” manufactured by Shin-Etsu Chemical Co., Ltd.

[0166] In the third embodiment, (E) the compound containing a free radical polymerizable group is preferably a maleimide compound represented by formula (4).

[0167]

[0168] [In the formula, R20 each independently represents a hydrogen atom or an alkyl group; ring E, ring F, and ring G each independently represent an aromatic ring optionally having substituents; Z1 each independently represents a single bond, -C(Rz)2-, -O-, -CO-, -S-, -SO-, -SO2-, -CONH-, or -NHCO-; Rz each independently represents a hydrogen atom or an alkyl group; s represents an integer greater than 1; t each independently represents 0 or 1; u each independently represents 0, 1, 2, or 3.] For both s and u units, the units can be the same or different. In the third embodiment, the maleimine compound can be used alone or in combination of two or more compounds in any proportion.

[0169] R 20 each independently represents a hydrogen atom or an alkyl group, preferably a hydrogen atom or a methyl group, and more preferably a hydrogen atom. Ring E, ring F and ring G each independently represent an aromatic ring optionally having substituents, preferably a benzene ring optionally having substituents, more preferably a benzene ring optionally substituted with groups selected from alkyl and aryl groups, and particularly preferably an (unsubstituted) benzene ring.

[0170] Z 1 independently represents a single bond, -C(R z) 2-, -O-, -CO-, -S-, -SO-, -SO 2-, -CONH-, or -NHCO-, preferably a single bond, -C(R z) 2-, or -O-, more preferably a single bond or -C(R z) 2-, and especially preferably a single bond. R z independently represents a hydrogen atom or an alkyl group, preferably a hydrogen atom or a methyl group.

[0171] s represents an integer greater than or equal to 1, preferably an integer from 1 to 10. t represents 0 or 1 independently, preferably 1. u represents 0, 1, 2, or 3 independently, preferably 0, 1, or 2, more preferably 0 or 1, and especially preferably 1.

[0172] In the third embodiment (E), the amount of free radical polymerizable groups in the compound is preferably 150 g / eq. to 1000 g / eq., more preferably 200 g / eq. to 500 g / eq.

[0173] The weight average molecular weight of the compound containing a free radical polymerizable group in the third embodiment (E) is preferably 100 to 10,000, more preferably 150 to 5,000, and particularly preferably 200 to 3,000.

[0174] Commercially available products containing free radical polymerizable groups as the third embodiment (E) include, for example, "MIR-3000-70MT" and "MIR-5000-60T" manufactured by Nippon Kayaku Co., Ltd.

[0175] (E) The compound containing free radical polymerizable groups may individually comprise any one of the preferred thermoplastic resin of the first embodiment, the preferred maleimide compound of the second embodiment, and the preferred maleimide compound of the third embodiment, or may comprise two or more of them in any proportion.

[0176] (E) The free radical polymerizable group equivalent of the compound containing the free radical polymerizable group is preferably 30 g / eq. to 2500 g / eq., and particularly preferably 75 g / eq. to 2000 g / eq.

[0177] The content of compounds containing free radical polymerizable groups (E) in the resin composition is not particularly limited. When the non-volatile component in the resin composition is set to 100% by mass, it is preferably 50% by mass or less, more preferably 30% by mass or less, further preferably 20% by mass or less, even more preferably 10% by mass or less, and particularly preferably 5% by mass or less. The lower limit of the content of compounds containing free radical polymerizable groups (E) in the resin composition is not particularly limited. When the non-volatile component in the resin composition is set to 100% by mass, it can be set to, for example, 0.01% by mass or more, 0.1% by mass or more, 0.5% by mass or more, 1% by mass or more, etc.

[0178] <(F) Thermoplastic Resins> The resin composition of the present invention may further include (F) thermoplastic resin as an optional component. (F) thermoplastic resin is not a component of (B) epoxy resin described above.

[0179] Examples of thermoplastic resins (F) include polyimide resins, phenoxy resins, polyvinyl acetal resins, polyolefin resins, polybutadiene resins, polyamide-imide resins, polyether-imide resins, polyurethane resins, polyether resins, polyphenylene ether resins, polycarbonate resins, polyetheretherketone resins, and polyester resins. In one embodiment, the thermoplastic resin (F) preferably includes a thermoplastic resin selected from polyimide resins and phenoxy resins, and more preferably includes phenoxy resins. Furthermore, one type of thermoplastic resin may be used alone, or two or more types may be used in combination.

[0180] Specific examples of polyimide resins include Shin-Etsu Chemical Co., Ltd.'s "SLK-6100", Shin Nippon Rikka Co., Ltd.'s "RIKACOAT SN20" and "RIKACOAT PN20".

[0181] Examples of phenoxy resins include those having one or more skeletons selected from the following: bisphenol A skeleton, bisphenol F skeleton, bisphenol S skeleton, bisphenol acetophenone skeleton, phenolic varnish skeleton, biphenyl skeleton, fluorene skeleton, dicyclopentadiene skeleton, norbornene skeleton, naphthalene skeleton, anthracene skeleton, adamantane skeleton, terpene skeleton, and trimethylcyclohexane skeleton. The terminal end of the phenoxy resin may have any functional group such as a phenolic hydroxyl group or an epoxy group.

[0182] Specific examples of phenoxy resins include: Mitsubishi Chemical's "1256" and "4250" (both phenoxy resins containing a bisphenol A backbone); Mitsubishi Chemical's "YX8100" (phenoxy resin containing a bisphenol S backbone); Mitsubishi Chemical's "YX6954" (phenoxy resin containing a bisphenol acetophenone backbone); Nippon Steel Chemical Materials' "FX280" and "FX293"; and Mitsubishi Chemical's "YX7200B35", "YL7500BH30", "YX6954BH30", "YX7553BH30", "YL7769BH30", "YL6794", "YL7213", "YL7290", and "YL7482", etc.

[0183] Examples of polyvinyl alcohol acetal resins include polyvinyl alcohol formal resin and polyvinyl alcohol butyral resin, with polyvinyl alcohol butyral resin being preferred. Specific examples of polyvinyl alcohol acetal resins include: "Denka Butyral 4000-2", "Denka Butyral 5000-A", "Denka Butyral 6000-C", and "Denka Butyral 6000-EP" manufactured by Denka Kogyo Co., Ltd.; and the S-LEC BH series, BX series (e.g., BX-5Z), KS series (e.g., KS-1), BL series, and BM series manufactured by Sekisui Chemicals Co., Ltd., etc.

[0184] Examples of polyolefin resins include low-density polyethylene, ultra-low-density polyethylene, high-density polyethylene, ethylene-vinyl acetate copolymer, ethylene-ethyl acrylate copolymer, ethylene-methyl acrylate copolymer, and other ethylene-based copolymer resins; and polyolefin polymers such as polypropylene and ethylene-propylene block copolymers.

[0185] Examples of polybutadiene resins include: resins containing a hydrogenated polybutadiene backbone, hydroxyl-containing polybutadiene resins, phenolic hydroxyl-containing polybutadiene resins, carboxyl-containing polybutadiene resins, acid anhydride-containing polybutadiene resins, epoxy-containing polybutadiene resins, isocyanate-containing polybutadiene resins, urethane-containing polybutadiene resins, and polyphenylene ether-polybutadiene resins.

[0186] Specific examples of polyamide-imide resins include "VYLOMAX HR11NN" and "VYLOMAX HR16NN" manufactured by Toyobo Co., Ltd. Other specific examples of polyamide-imide resins include modified polyamides such as "KS9100" and "KS9300" (polyamide-imide containing a polysiloxane backbone) manufactured by Hitachi Chemical Co., Ltd.

[0187] Specific examples of polyether resins include "PES5003P" manufactured by Sumitomo Chemical Co., Ltd.

[0188] Specific examples of polyurethane resins include "P1700" and "P3500" manufactured by Solvay Advanced Polymers.

[0189] Specific examples of polyphenylene ether resins include SABIC's "NORYL SA90". Specific examples of polyetherimide resins include GE's "ULTEM".

[0190] Examples of polycarbonate resins include: hydroxyl-containing carbonate resins, phenolic hydroxyl-containing carbonate resins, carboxyl-containing carbonate resins, anhydride-containing carbonate resins, isocyanate-containing carbonate resins, and aminocarbamate-containing carbonate resins. Specific examples of polycarbonate resins include "FPC0220" manufactured by Mitsubishi Gas Chemical Co., Ltd., "T6002" and "T6001" (polycarbonate diol) manufactured by Asahi Kasei Chemical Co., Ltd., and "C-1090," "C-2090," and "C-3090" (polycarbonate diol) manufactured by Kuraray Co., Ltd. Specific examples of polyetheretherketone (PEEK) resins include "SUMIPLOY K" manufactured by Sumitomo Chemical Co., Ltd.

[0191] Examples of polyester resins include polyethylene terephthalate resin, polyethylene naphthalate resin, polybutylene terephthalate resin, polybutylene naphthalate resin, polypropylene terephthalate resin, and polycyclohexanedimethyl terephthalate resin.

[0192] From the viewpoint of further improving the film-forming properties of the film, (F) the weight average molecular weight (Mw) of the thermoplastic resin is preferably 5,000 or more, more preferably 8,000 or more, even more preferably 10,000 or more, especially preferably 20,000 or more, preferably 100,000 or less, even more preferably 70,000 or less, even more preferably 60,000 or less, and especially preferably 50,000 or less.

[0193] (F) The content of thermoplastic resin relative to all non-volatile components in the resin composition is not particularly limited. When the non-volatile components in the resin composition are set to 100% by mass, the content of (F) thermoplastic resin is preferably 20% by mass or less, more preferably 15% by mass or less, even more preferably 10% by mass or less, even more preferably 5% by mass or less, and particularly preferably 3% by mass or less. The lower limit of the content of (F) thermoplastic resin relative to all non-volatile components is not particularly limited. When the non-volatile components in the resin composition are set to 100% by mass, the content of (F) thermoplastic resin is, for example, 0% by mass or more, 0.01% by mass or more, 0.1% by mass or more, etc.

[0194] <(G) Hardening Accelerator> The resin composition of the present invention may further include (G) a curing accelerator as an optional component. The (G) curing accelerator functions as a curing catalyst that promotes the curing of (B) epoxy resin.

[0195] Examples of (G) curing accelerators include: phosphorus-based curing accelerators, urea-based curing accelerators, guanidine-based curing accelerators, imidazole-based curing accelerators, metal-based curing accelerators, and amine-based curing accelerators. Preferably, the (G) curing accelerator includes a curing accelerator selected from imidazole-based and amine-based curing accelerators, and particularly preferably includes an imidazole-based curing accelerator. A single (G) curing accelerator can be used alone, or two or more can be used in combination.

[0196] Examples of phosphorus-based hardening accelerators include: tetrabutylphosphonium bromide, tetrabutylphosphonium chloride, tetrabutylphosphonium acetate, tetrabutylphosphonium decanoate, tetrabutylphosphonium laurate, bis(tetrabutylphosphonium)pyromellitic tert-butylphosphonium, tetrabutylphosphonium hexahydrophthalate, tetrabutylphosphonium 2,6-bis[(2-hydroxy-5-methylphenyl)methyl]-4-methylphenolate, di-tert-butylmethylphosphonium tetraphenylborate, and other aliphatic phosphonium salts; methyltriphenylphosphonium bromide, ethyltriphenylphosphonium bromide, propyltriphenylphosphonium bromide, butyltriphenylphosphonium bromide, benzyltriphenylphosphonium chloride, tetraphenylphosphonium bromide, and p-toluene. Aromatic phosphonium salts of triphenylphosphonium tetratolylborate, tetraphenylphosphonium tetraphenylborate, tetraphenylphosphonium tetratolylborate, triphenylethylphosphonium tetraphenylborate, tri(3-methylphenyl)ethylphosphonium tetraphenylborate, tri(2-methoxyphenyl)ethylphosphonium tetraphenylborate, (4-methylphenyl)triphenylphosphonium thiocyanate, tetraphenylphosphonium thiocyanate, butyltriphenylphosphonium thiocyanate, etc.; aromatic phosphine-borane complexes of triphenylphosphine-triphenylborane, etc.; aromatic phosphine-quinone addition reactants of triphenylphosphine-p-benzoquinone, etc.; tributylphosphine, tri-tert-butylphosphine, trioctylphosphine, di-tert-butylphosphine, etc. Aliphatic phosphines such as butyl(2-butenyl)phosphine, di-tert-butyl(3-methyl-2-butenyl)phosphine, and tricyclohexylphosphine; and tributylphenylphosphine, di-tert-butylphenylphosphine, methyldiphenylphosphine, ethyldiphenylphosphine, butyldiphenylphosphine, diphenylcyclohexylphosphine, triphenylphosphine, tri-o-tolylphosphine, tri-m-tolylphosphine, tri-p-tolylphosphine, tri(4-ethylphenyl)phosphine, tri(4-propylphenyl)phosphine, tri(4-isopropylphenyl)phosphine, tri(4-butylphenyl)phosphine, tri(4-tert-butylphenyl)phosphine, tri(2,4-dimethylphenyl)phosphine, tri(2,5-dimethylphenyl)phosphine, tri(2,6- Aromatic phosphines such as dimethylphenylphosphine, tris(3,5-dimethylphenyl)phosphine, tris(2,4,6-trimethylphenyl)phosphine, tris(2,6-dimethyl-4-ethoxyphenyl)phosphine, tris(2-methoxyphenyl)phosphine, tris(4-methoxyphenyl)phosphine, tris(4-ethoxyphenyl)phosphine, tris(4-tert-butoxyphenyl)phosphine, diphenyl-2-pyridylphosphine, 1,2-bis(diphenylphosphino)ethane, 1,3-bis(diphenylphosphino)propane, 1,4-bis(diphenylphosphino)butane, 1,2-bis(diphenylphosphino)acetylene, and 2,2'-bis(diphenylphosphino)diphenyl ether.

[0197] Examples of urea-based hardening accelerators include: 1,1-dimethylurea; aliphatic dimethylureas such as 1,1,3-trimethylurea, 3-ethyl-1,1-dimethylurea, 3-cyclohexyl-1,1-dimethylurea, and 3-cyclooctyl-1,1-dimethylurea; 3-phenyl-1,1-dimethylurea, 3-(4-chlorophenyl)-1,1-dimethylurea, 3-(3,4-dichlorophenyl)-1,1-dimethylurea, 3-(3-chloro-4-methylphenyl)-1,1-dimethylurea, 3-(2-methylphenyl)-1,1-dimethylurea, 3-(4-methylphenyl)-1,1-dimethylurea, and 3-(3,4-dimethylphenyl)-1,1-dimethylurea. Aromatic dimethylureas such as 1-dimethylurea, 3-(4-isopropylphenyl)-1,1-dimethylurea, 3-(4-methoxyphenyl)-1,1-dimethylurea, 3-(4-nitrophenyl)-1,1-dimethylurea, 3-[4-(4-methoxyphenoxy)phenyl]-1,1-dimethylurea, 3-[4-(4-chlorophenoxy)phenyl]-1,1-dimethylurea, 3-[3-(trifluoromethyl)phenyl]-1,1-dimethylurea, N,N-(1,4-epenylphenyl)bis(N',N'-dimethylurea), N,N-(4-methyl-1,3-epenylphenyl)bis(N',N'-dimethylurea)[toluenebisdimethylurea], etc.

[0198] Examples of guanidine-based hardening promoters include: dicyandiamide, 1-methylguanidine, 1-ethylguanidine, 1-cyclohexylguanidine, 1-phenylguanidine, 1-(o-tolyl)guanidine, dimethylguanidine, diphenylguanidine, trimethylguanidine, tetramethylguanidine, pentamethylguanidine, 1,5,7-triazabicyclo[4.4.0]dec-5-ene, 7-methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene, 1-methylbiguanidine, 1-ethylbiguanidine, 1-n-butylbiguanidine, 1-n-octadecylbiguanidine, 1,1-dimethylbiguanidine, 1,1-diethylbiguanidine, 1-cyclohexylbiguanidine, 1-allylbiguanidine, 1-phenylbiguanidine, 1-(o-tolyl)biguanidine, etc.

[0199] Examples of imidazole-based hardening accelerators include: 2-methylimidazolium, 2-undecylimidazolium, 2-heptadecylimidazolium, 1,2-dimethylimidazolium, 2-ethyl-4-methylimidazolium, 1,2-dimethylimidazolium, 2-ethyl-4-methylimidazolium, 2-phenylimidazolium, 2-phenyl-4-methylimidazolium, 1-benzyl-2-methylimidazolium, 1-benzyl-2-phenylimidazolium, 1-cyanoethyl-2-methylimidazolium, 1-cyanoethyl-2-undecylimidazolium, 1-cyanoethyl-2-ethyl-4-methylimidazolium, 1-cyanoethyl-2-phenylimidazolium, 1-cyanoethyl-2-undecylimidazolium trimellitate, 1-cyanoethyl-2-phenylimidazolium trimellitate, 2,4-diamino-6-[2'-methylimidazolium-(1')] [Ethyl-triazine, 2,4-diamino-6-[2'-undecylimidazolyl-(1')]-ethyl-triazine, 2,4-diamino-6-[2'-ethyl-4'-methylimidazolyl-(1')]-ethyl-triazine, 2,4-diamino-6-[2'-methylimidazolyl-(1')]-ethyl-triazine isocyanuric acid adduct, 2-phenylimidazolyl isocyanuric acid adduct, 2-phenyl-4,5-dihydroxymethylimidazolium, 2-phenyl-4-methyl-5-hydroxymethylimidazolium, 2,3-dihydro-1H-pyrrolo[1,2-a]benzimidazole, 1-dodecyl-2-methyl-3-benzylimidazolium chloride, 2-methylimidazoline, 2-phenylimidazoline and other imidazole compounds and adducts of imidazole compounds with epoxy resins.

[0200] As imidazole-based hardening accelerators, commercially available products can be used, such as "1B2PZ", "2MZA-PW", "2PHZ-PW", and "C11Z-A" manufactured by Shikoku Chemical Industry Co., Ltd., and "P200-H50" manufactured by Mitsubishi Chemical Co., Ltd.

[0201] Examples of organometallic hardening accelerators include organometallic complexes or organometallic salts of metals such as cobalt, copper, zinc, iron, nickel, manganese, and tin. Specific examples of organometallic complexes include: cobalt(II) acetoacetone, cobalt(III) acetoacetone, copper(II) acetoacetone, zinc(II) acetoacetone, iron(III) acetoacetone, nickel(II) acetoacetone, and manganese(II) acetoacetone. Examples of organometallic salts include zinc octoate, tin octoate, zinc naphthenate, cobalt naphthenate, tin stearate, and zinc stearate.

[0202] Examples of amine-based hardening accelerators include trialkylamines such as triethylamine and tributylamine, 4-dimethylaminopyridine, benzyldimethylamine, 2,4,6-tris(dimethylaminomethyl)phenol, and 1,8-diazabicyclo(5,4,0)-undecene.

[0203] As an amine-based hardening accelerator, commercially available products can be used, such as "MY-25" manufactured by Ajinomoto Fine-Techno.

[0204] The content of (G) curing accelerator in the resin composition is not particularly limited. When the non-volatile component in the resin composition is set to 100% by mass, it is preferably 5% by mass or less, more preferably 1% by mass or less, further preferably 0.5% by mass or less, and particularly preferably 0.3% by mass or less. The lower limit of the content of (G) curing accelerator in the resin composition is not particularly limited. When the non-volatile component in the resin composition is set to 100% by mass, it can be set to 0% by mass or more, 0.001% by mass or more, 0.01% by mass or more, etc.

[0205] <(H) Other Additives> The resin composition of the present invention may further include any additives. Examples of such additives include: free radical polymerization initiators such as peroxide-based free radical polymerization initiators and azo-based free radical polymerization initiators; thermosetting resins other than epoxy resins such as epoxy acrylate resins, urethane acrylate resins, urethane resins, cyanate ester resins, benzoxazine resins, unsaturated polyester resins, phenolic resins, melamine resins, and organosilicon resins; phenoxy resins, polyvinyl acetal resins, polyolefin resins, polyurethane resins, and rubber. Organic fillers such as particles; organometallic compounds such as organocopper compounds, organozinc compounds, and organocobalt compounds; colorants such as phthalocyanine blue, phthalocyanine green, iodine green, diazo yellow, crystal violet, titanium dioxide, and carbon black; polymerization inhibitors such as hydroquinone, catechol, pyrogallol, and phenothiazine; homogenizing agents such as organosilicon homogenizers and acrylic polymer homogenizers; thickeners such as Benton and montmorillonite; defoamers such as organosilicon defoamers, acrylic defoamers, fluorinated defoamers, and vinyl resin defoamers. Defoamers such as lipid-based defoamers; ultraviolet absorbers such as benzotriazole-based ultraviolet absorbers; adhesion enhancers such as ureasilanes; adhesion enhancers such as triazole-based, tetraazole-based, and triazine-based adhesion enhancers; antioxidants such as hindered phenolic antioxidants; fluorescent whitening agents such as zirconia derivatives; surfactants such as fluorinated surfactants and organosilicone surfactants; phosphorus-based flame retardants (e.g., phosphate ester compounds, phosphazene compounds, hypophosphite compounds). Flame retardants such as red phosphorus, nitrogen-based flame retardants (e.g., melamine sulfate), halogen-based flame retardants, and inorganic flame retardants (e.g., antimony trioxide); dispersants such as phosphate ester dispersants, polyoxyethylene dispersants, alkyne dispersants, organosilicon dispersants, anionic dispersants, and cationic dispersants; stabilizers such as borate ester stabilizers, titanate stabilizers, aluminate stabilizers, zirconate stabilizers, isocyanate stabilizers, carboxylic acid stabilizers, and carboxylic anhydride stabilizers. (H) Other additives may be used alone or in combination of two or more in any proportion. (H) The content of other additives can be appropriately set by those skilled in the art.

[0206] <(I) Organic Solvents> The resin composition of the present invention may sometimes also contain any organic solvent. As (I) the organic solvent, known organic solvents may be appropriately used, and their types are not particularly limited. Examples of (I) organic solvents include: ketone solvents such as acetone, methyl ethyl ketone, methyl isobutyl ketone, and cyclohexanone; ester solvents such as methyl acetate, ethyl acetate, butyl acetate, isobutyl acetate, isoamyl acetate, methyl propionate, ethyl propionate, and γ-butyrolactone; ether solvents such as tetrahydropyran, tetrahydrofuran, 1,4-dioxane, diethyl ether, diisopropyl ether, dibutyl ether, diphenyl ether, and anisole; alcohol solvents such as methanol, ethanol, propanol, butanol, and ethylene glycol; and 2-ethoxyethyl acetate, propylene glycol monomethyl ether acetate, diethylene glycol monoethyl ether acetate, and diethylene glycol monoethyl ether acetate. Ether ester solvents such as acetate, γ-butyrolactone, and methyl methoxypropionate; ester alcohol solvents such as methyl lactate, ethyl lactate, and methyl 2-hydroxyisobutyrate; ether alcohol solvents such as 2-methoxypropanol, 2-methoxyethanol, 2-ethoxyethanol, propylene glycol monomethyl ether, and diethylene glycol monobutyl ether (butyl carbitol); acetylamine solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, and N-methyl-2-pyrrolidone; arginine solvents such as dimethyl sulfoxide; nitrile solvents such as acetonitrile and propionitrile; aliphatic hydrocarbon solvents such as hexane, cyclopentane, cyclohexane, and methylcyclohexane; and aromatic hydrocarbon solvents such as benzene, toluene, xylene, ethylbenzene, and trimethylbenzene. (I) One organic solvent may be used alone, or two or more may be combined in any proportion.

[0207] The content of (I) organic solvent in the varnish-like resin composition before drying is not particularly limited, but when all components in the resin composition are set to 100% by mass, it is, for example, 40% by mass or less, 30% by mass or less, preferably 20% by mass or less, more preferably 10% by mass or less, even more preferably 8% by mass or less, and particularly preferably 6% by mass or less. The content of (I) organic solvent in the resin composition forming the dried resin composition layer in the resin sheet is not particularly limited, but when all components in the resin composition are set to 100% by mass, it is preferably 5% by mass or less, more preferably 3% by mass or less, even more preferably 2% by mass or less, and particularly preferably 1% by mass or less.

[0208] <Method for manufacturing resin composition> The resin composition of the present invention can be manufactured, for example, by simultaneously adding (A) a cyclic carbonate compound, (B) an epoxy resin, (C) an inorganic filler, (D) an active ester compound as needed, (D') other curing agents as needed, (E) a compound containing free radical polymerizable groups as needed, (F) a thermoplastic resin as needed, (G) a curing accelerator as needed, (H) other additives as needed, and (I) an organic solvent as needed, in any preparation container in any order and / or simultaneously, and mixing them. Furthermore, during the addition and mixing of the components, the temperature can be appropriately set, and heating and / or cooling can be performed temporarily or continuously. Additionally, during or after the addition and mixing, the resin composition can be stirred or agitated using a stirring device or oscillating device, such as a mixer, to ensure uniform dispersion. Furthermore, degassing can be performed under low-pressure conditions such as vacuum while stirring or agitating.

[0209] <Properties of Resin Composition> The resin composition of the present invention comprises (A) a cyclic carbonate compound, (B) an epoxy resin, and (C) an inorganic filler. According to such a resin composition, a cured product can be obtained that maintains high peel strength and has its dielectric tangent suppressed to a low value even when exposed to high temperature and high humidity environments.

[0210] The cured resin composition of the present invention can have the characteristic of maintaining high peel strength even when exposed to high temperature and high humidity environments. Therefore, in one embodiment, for example, as in test examples 4 and 5 below, the peel strength at 25°C, calculated from the load during the vertical peeling of a copper-plated conductor layer formed on a hardened material, is preferably 0.2 kgf / cm or more, more preferably 0.25 kgf / cm or more, even more preferably 0.3 kgf / cm or more, even more preferably 0.35 kgf / cm or more, and particularly preferably 0.4 kgf / cm or more. In contrast, after 100 hours of accelerated environmental testing (HAST) at 130°C and 85% RH, it is preferably maintained at 0.1 kgf / cm or more, more preferably 0.15 kgf / cm or more, even more preferably 0.2 kgf / cm or more, even more preferably 0.25 kgf / cm or more, and particularly preferably 0.3 kgf / cm or more. There is no specific upper limit; it can be below 10 kgf / cm before and after the accelerated environmental testing (HAST). The reduction rate (%) of peel strength value before and after the HAST is preferably below 45%, more preferably below 40%, further preferably below 35%, even more preferably below 30%, and particularly preferably below 25% or 20%. Furthermore, the reduction rate (%) of peel strength value is calculated as the percentage decrease (%) of the peel strength (kgf / cm) after the HAST compared to the peel strength (kgf / cm) before the HAST.

[0211] The cured resin composition of the present invention can have a low dielectric tangent (Df). Therefore, in one embodiment, the dielectric tangent (Df) of the cured resin composition when measured at 5.8 GHz and 23 °C as in Test Example 1 below is not particularly limited, but is preferably 0.0100 or less, more preferably 0.0080 or less, even more preferably 0.0060 or less, even more preferably 0.0050 or less or 0.0040 or less, and particularly preferably 0.0035 or less or 0.0030 or less.

[0212] In one embodiment, the cured resin composition of the present invention may have a low relative permittivity (Dk). Therefore, in one embodiment, the relative permittivity (Dk) of the cured resin composition measured at 5.8 GHz and 23 °C as described in Test Example 1 below is not particularly limited, but it is preferably 5.0 or less, more preferably 4.0 or less, even more preferably 3.5 or less, and particularly preferably 3.0 or less.

[0213] In one embodiment, the cured product of the resin composition of the present invention may possess excellent mechanical strength. Therefore, in one embodiment, the elongation at break of the cured product measured at 23°C according to Japanese Industrial Standard JIS K7127, as in Test Example 2 below, is not particularly limited, but preferably 0.05% or more, more preferably 0.1% or more, further preferably 0.15% or more, even more preferably 0.2% or more, and particularly preferably 0.22% or more. The upper limit of the elongation at break is not particularly limited, and is generally set to 10% or less, 5% or less, etc.

[0214] In one embodiment, the cured resin composition of the present invention may have the characteristic of a low arithmetic mean roughness (Ra) of the surface of the roughened insulating layer. Therefore, in one embodiment, the arithmetic mean roughness (Ra) of the surface of the roughened insulating layer, as measured as in Test Example 3 below, is not particularly limited, but preferably is 500 nm or less, more preferably 400 nm or less, further preferably 300 nm or less, even more preferably 200 nm or less, and particularly preferably 100 nm or less. The lower limit is not particularly limited, for example, it may be set to 1 nm or more, 2 nm or more, etc.

[0215] <Applications of Resin Compositions> The resin composition of the present invention can be suitably used as a resin composition for insulating purposes, particularly for forming insulating layers. Specifically, it can be suitably used as a resin composition for forming an insulating layer (a resin composition for forming an insulating layer for forming a conductor layer), wherein the aforementioned insulating layer is an insulating layer for forming a conductor layer (including a rewiring layer), and the aforementioned conductor layer is formed on the insulating layer. Furthermore, in the printed wiring board described later, it can be suitably used as a resin composition for forming an insulating layer of the printed wiring board (a resin composition for forming an insulating layer of the printed wiring board). In addition, the resin composition of the present invention can also be widely used in applications requiring resin compositions, such as sheet-like laminates of resin sheets and prepregs, solder resists, underfill materials, wafer bonding materials, semiconductor sealing materials, via-filling resins, and component embedding resins.

[0216] Furthermore, when manufacturing a semiconductor wafer package, for example, through steps (1) to (6) below, the resin composition of the present invention can also be suitably used as: a resin composition for forming a rewiring layer as an insulating layer for forming a rewiring layer (resin composition for forming a rewiring layer); and a resin composition for sealing a semiconductor wafer (resin composition for sealing a semiconductor wafer). During the manufacturing of a semiconductor wafer package, a rewiring layer can be further formed on the sealing layer; (1) The step of laminating a temporary fixing film on the substrate, (2) The step of temporarily fixing the semiconductor wafer onto the temporary fixing film. (3) The step of forming a sealing layer on a semiconductor wafer. (4) The step of peeling the substrate and temporary fixing film from the semiconductor wafer. (5) The step of forming a rewiring layer as an insulating layer on the surface of a semiconductor wafer where the substrate and temporary fixing film have been stripped, and (6) The step of forming a rewiring layer as a conductor layer on the rewiring forming layer.

[0217] Furthermore, the resin composition of the present invention provides an insulating layer with good component embedding properties, so it can be used appropriately even when the printed wiring board is a circuit board with components embedded in it.

[0218] <Thin laminated materials> The resin composition of the present invention can also be used by coating in the form of a varnish, but in industry, it is generally preferred to use it in the form of a sheet-like laminate containing the resin composition.

[0219] As a sheet-like laminated material, the resin sheet or prepreg shown below is preferred.

[0220] In one embodiment, the resin sheet includes a support and a resin composition layer disposed on the support, the resin composition layer being formed from the resin composition of the present invention.

[0221] From the perspective of making printed circuit boards thinner and providing a cured material with excellent insulation even when the cured resin composition is a thin film, the thickness of the resin composition layer is preferably 50 μm or less, and more preferably 40 μm or less. There is no particular limitation on the lower limit of the resin composition layer thickness; it can typically be set to 5 μm or more, 10 μm or more, etc.

[0222] Examples of supports include films made of plastic materials, metal foils, and release paper, with films and metal foils made of plastic materials being preferred.

[0223] When using a film formed from a plastic material as a support, examples of plastic materials include: polyesters such as polyethylene terephthalate (hereinafter sometimes abbreviated as "PET") and polyethylene naphthalate (hereinafter sometimes abbreviated as "PEN"), acrylic polymers such as polycarbonate (hereinafter sometimes abbreviated as "PC") and polymethyl methacrylate (PMMA), cyclic polyolefins, triacetin (TAC), polyether sulfide (PES), polyether ketone, and polyimide. Among these, polyethylene terephthalate and polyethylene naphthalate are preferred, and inexpensive polyethylene terephthalate is particularly preferred.

[0224] When using metal foil as a support, examples of metal foils include copper foil and aluminum foil, with copper foil being preferred. Copper foil can be used as the support, either as a single metal of copper or as an alloy of copper with other metals (such as tin, chromium, silver, magnesium, nickel, zirconium, silicon, titanium, etc.).

[0225] For the support, matte finish, corona treatment, and antistatic treatment can be applied to the surface that bonds with the resin composition layer.

[0226] Additionally, as a support, a support with a release layer can be used on the surface bonded to the resin composition layer. Examples of release agents for the release layer of the support with the release layer include, for example, one or more release agents selected from alkyd resins, polyolefin resins, urethane resins, and silicone resins. Commercially available products can be used as the support with the release layer, such as "SK-1," "AL-5," and "AL-7" manufactured by Lintec Corporation, "LUMIRROR T60" manufactured by Toray Industries, Ltd., "Purex" manufactured by Teijin Corporation, and "Unipeel" manufactured by Unitika Corporation, all of which are PET films having a release layer with an alkyd resin-based release agent as the main component.

[0227] The thickness of the support is not particularly limited, but it is preferably in the range of 5μm to 75μm, and more preferably in the range of 10μm to 60μm. Furthermore, when using a support with a release layer, it is preferable that the overall thickness of the support with the release layer is within the above-mentioned range.

[0228] In one embodiment, the resin sheet may further comprise any layer as needed. Examples of such arbitrary layers include, for instance, a protective film, selected according to the support, applied to the side of the resin composition layer that is not bonded to the support (i.e., the side opposite to the support). The thickness of the protective film is not particularly limited, and is, for example, 1 μm to 40 μm. By laminating the protective film, it is possible to suppress the adhesion of debris or damage to the surface of the resin composition layer.

[0229] Resin sheets can be manufactured, for example, by directly coating a liquid (varnish-like) resin composition onto a support using a die coater or similar machine, or by preparing a liquid (varnish-like) resin composition obtained by dissolving the resin composition in an organic solvent and coating it onto a support using a die coater or similar machine, and then drying it to form a resin composition layer.

[0230] As an organic solvent, examples can be made that are the same organic solvents listed in the composition description of the resin. One organic solvent may be used alone, or two or more may be used in combination.

[0231] Drying can be carried out by known methods such as heating or hot air blowing. There are no particular limitations on the drying conditions; drying should be carried out in a manner that ensures the content of organic solvent in the resin composition layer is 10% by mass or less, preferably 5% by mass or less. Depending on the boiling point of the organic solvent in the resin composition, for example, if a resin composition containing 30% to 60% by mass of organic solvent is used, the resin composition layer can be formed by drying at 50°C to 150°C for 3 to 10 minutes.

[0232] Resin sheets can be stored in rolls. If the resin sheets have a protective film, they can be used by peeling off the protective film.

[0233] In one embodiment, the prepreg is formed by impregnating the resin composition of the present invention into a sheet-like fiber substrate.

[0234] There are no particular limitations on the sheet-like fiber substrate used in prepregs; commonly used materials such as glass cloth, aromatic polyamide nonwoven fabric, and liquid crystal polymer nonwoven fabric can be used. From the viewpoint of thinning printed circuit boards, the thickness of the sheet-like fiber substrate is preferably less than 50 μm, more preferably less than 40 μm, further preferably less than 30 μm, and particularly preferably less than 20 μm. There is no particular limitation on the lower limit of the thickness of the sheet-like fiber substrate. It is usually 10 μm or more.

[0235] Prepregs can be manufactured using known methods such as hot-melt methods and solvent methods.

[0236] The thickness of the prepreg can be set to the same range as the resin composition layer in the resin sheet described above.

[0237] The sheet-like laminate material of the present invention can be suitably used to form the insulating layer of a printed wiring board (for the insulating layer of a printed wiring board), and is more suitable for forming the interlayer insulating layer of a printed wiring board (for the interlayer insulating layer of a printed wiring board).

[0238] Printed Wiring Board The printed wiring board of the present invention includes an insulating layer formed from a hardened material obtained by curing the resin composition of the present invention.

[0239] For printed wiring boards, for example, the resin sheet described above can be used to manufacture them using a method including the steps (I) and (II) below: (I) The step of laminating a resin sheet onto an inner substrate by bonding a resin composition layer of the resin sheet to the inner substrate. (II) The step of curing the resin composition layer (e.g., thermosetting) to form an insulating layer.

[0240] The "inner layer substrate" used in step (I) refers to a component that becomes the substrate of a printed wiring board, such as a glass epoxy substrate, a metal substrate, a polyester substrate, a polyimide substrate, a BT resin substrate, or a thermosetting polyphenylene ether substrate. Furthermore, this substrate may have a conductor layer on one or both sides, and this conductor layer may be patterned. Sometimes, an inner layer substrate with conductor layers (circuit) formed on one or both sides of the substrate is called an "inner layer circuit substrate." Additionally, intermediate components for which insulating layers and / or conductor layers are to be further formed during the manufacture of the printed wiring board are also included in the "inner layer substrate" described in this invention. When the printed wiring board is a component-integrated circuit board, an inner layer substrate with integrated components can be used.

[0241] The lamination of the inner substrate and the resin sheet can be performed, for example, by heating and pressing the resin sheet onto the inner substrate from the support side. Examples of components for heating and pressing the resin sheet onto the inner substrate (hereinafter also referred to as "heat-pressing components") include, for example, heated metal plates (SUS end plates, etc.) or metal rollers (SUS rollers). Preferably, instead of directly pressing the heat-pressing component onto the resin sheet, the resin sheet is pressed through an elastic material such as heat-resistant rubber, so that the resin sheet fully follows the surface irregularities of the inner substrate.

[0242] The lamination of the inner substrate and the resin sheet can be carried out by vacuum lamination. In vacuum lamination, the heating and pressing temperature is preferably 60℃~160℃, more preferably 80℃~140℃; the heating and pressing pressure is preferably 0.098MPa~1.77MPa, more preferably 0.29MPa~1.47MPa; and the heating and pressing time is preferably 20 seconds~400 seconds, more preferably 30 seconds~300 seconds. Lamination is preferably carried out under reduced pressure conditions below 26.7 hPa.

[0243] Lamination can be performed using commercially available vacuum laminators. Examples of commercially available vacuum laminators include the vacuum pressure laminator manufactured by Meiki Manufacturing Co., Ltd., the vacuum applicator manufactured by Nikko-Materials Co., Ltd., and batch vacuum pressure laminators.

[0244] After lamination, under normal pressure (atmospheric pressure), for example, the heated pressing component is stamped from the support side, thereby performing a smoothing treatment on the laminated resin sheet. The stamping conditions for the smoothing treatment can be set to the same conditions as the heated pressing conditions for lamination described above. The smoothing treatment can be performed using a commercially available laminator. Alternatively, lamination and smoothing treatment can be performed continuously using the aforementioned commercially available vacuum laminator.

[0245] The support can be removed between step (I) and step (II), or after step (II).

[0246] In step (II), the resin composition layer is cured (e.g., thermosetting) to form an insulating layer formed from the cured resin composition. The curing conditions for the resin composition layer are not particularly limited, and conditions typically used when forming insulating layers for printed wiring boards can be used.

[0247] For example, although the thermosetting conditions of the resin composition layer vary depending on the type of resin composition, in one embodiment, the curing temperature is preferably 120°C to 240°C, more preferably 150°C to 220°C, and even more preferably 170°C to 210°C. The curing time is preferably set to 5 minutes to 120 minutes, more preferably 10 minutes to 100 minutes, and even more preferably 15 minutes to 100 minutes.

[0248] Before heat curing the resin composition layer, the resin composition layer can be preheated at a temperature below the curing temperature. For example, before heat curing the resin composition layer, the resin composition layer can be preheated at a temperature of 50°C to 120°C, preferably 60°C to 115°C, more preferably 70°C to 110°C for at least 5 minutes, preferably 5 minutes to 150 minutes, more preferably 15 minutes to 120 minutes, and even more preferably 15 minutes to 100 minutes.

[0249] In manufacturing a printed wiring board, steps (III) of creating holes in the insulating layer, (IV) of roughening the insulating layer, and (V) of forming a conductor layer can be further performed. These steps (III) to (V) can be performed according to various methods known to those skilled in the art that are applicable in the manufacture of printed wiring boards. Furthermore, if the support is removed after step (II), the removal of the support can be performed between steps (II) and (III), between steps (III) and (IV), or between steps (IV) and (V). Additionally, steps (II) to (V) can be repeatedly performed as needed to form a multilayer wiring board.

[0250] In other embodiments, the printed wiring board of the present invention can be manufactured using the prepreg described above. The manufacturing method is essentially the same as that used in the case of resin sheets.

[0251] Step (III) involves creating openings in the insulating layer, thereby forming through holes, vias, or other holes. Step (III) can be performed using tools such as drills, lasers, or plasma, depending on the composition of the resin used in forming the insulating layer. The size and shape of the holes can be appropriately determined based on the design of the printed circuit board.

[0252] Step (IV) is a roughening process for the insulating layer. Typically, step (IV) also includes the removal of adhesive residue. The order and conditions of the roughening process are not particularly limited; well-known sequences and conditions commonly used in forming the insulating layer of printed wiring boards can be employed. For example, the insulating layer can be roughened by sequentially performing a swelling treatment with a swelling solution, a roughening treatment with an oxidizing agent, and a neutralization treatment with a neutralizing solution.

[0253] The swelling solution used in the roughening treatment is not particularly limited, and examples include alkaline solutions and surfactant solutions. Alkaline solutions are preferred, and sodium hydroxide or potassium hydroxide solutions are even more suitable. Commercially available swelling solutions include, for example, "Swelling Dip Securiganth P" and "Swelling Dip Securiganth SBU" manufactured by ATOTECH Japan. The swelling treatment using the swelling solution is not particularly limited; for example, it can be performed by immersing the insulating layer in a swelling solution at 30°C to 90°C for 1 to 20 minutes. From the viewpoint of suppressing the swelling of the resin in the insulating layer to a suitable level, it is preferable to immerse the insulating layer in a swelling solution at 40°C to 80°C for 5 to 15 minutes.

[0254] The oxidant used in the roughening treatment is not particularly limited, and examples include alkaline permanganate solutions prepared by dissolving potassium permanganate or sodium permanganate in an aqueous solution of sodium hydroxide. Roughening treatment using oxidants such as alkaline permanganate solutions is preferably carried out by immersing the insulating layer in an oxidant solution heated to 60°C to 100°C for 10 to 30 minutes. Furthermore, the concentration of permanganate in the alkaline permanganate solution is preferably 5% to 10% by mass. Commercially available oxidants include alkaline permanganate solutions such as "Concentrate Compact CP" and "Dosing Solution Securiganth P" manufactured by Ammet Japan Co., Ltd.

[0255] In addition, the neutralizing solution used in the roughening process is preferably an acidic aqueous solution. For example, commercially available products include "Reduction Solution Securiganth P" manufactured by Ammet Japan Co., Ltd.

[0256] The neutralization treatment can be carried out by immersing the roughened surface treated with the oxidant in a neutralization solution at 30°C to 80°C for 5 to 30 minutes. From an operational perspective, it is preferable to immerse the roughened surface treated with the oxidant in a neutralization solution at 40°C to 70°C for 5 to 20 minutes.

[0257] In one embodiment, the root mean square roughness (Rq) of the roughened insulating layer surface is preferably below 500 nm, more preferably below 400 nm, and even more preferably below 300 nm. There is no particular limitation on the lower limit; for example, it can be set to above 1 nm, above 2 nm, etc. The root mean square roughness (Rq) of the insulating layer surface can be measured using a non-contact surface roughness meter.

[0258] Step (V) is the step of forming a conductor layer, which is formed on the insulating layer. The conductor material used in the conductor layer is not particularly limited. In a preferred embodiment, the conductor layer comprises one or more metals selected from the group consisting of gold, platinum, palladium, silver, copper, aluminum, cobalt, chromium, zinc, nickel, titanium, tungsten, iron, tin, and indium. The conductor layer can be a single metal layer or an alloy layer. Examples of alloy layers include layers formed from alloys of two or more metals selected from the above group (e.g., nickel-chromium alloys, copper-nickel alloys, and copper-titanium alloys). From the viewpoints of versatility, cost, and ease of patterning in conductor layer formation, a single metal layer of chromium, nickel, titanium, aluminum, zinc, gold, palladium, silver, or copper, or an alloy layer of nickel-chromium, copper-nickel, or copper-titanium alloys, is preferred. More preferably, a single metal layer of chromium, nickel, titanium, aluminum, zinc, gold, palladium, silver, or copper, or an alloy layer of nickel-chromium alloys, is even more preferred. A single metal layer of copper is even more preferred.

[0259] The conductor layer can be a single-layer structure or a multi-layer structure composed of two or more single-metal or alloy layers of different types of metals or alloys. When the conductor layer is a multi-layer structure, the layer in contact with the insulating layer is preferably a single-metal layer of chromium, zinc, or titanium, or an alloy layer of nickel-chromium alloy.

[0260] The thickness of the conductor layer depends on the desired design of the printed wiring board, typically 3μm to 35μm, preferably 5μm to 30μm.

[0261] In one embodiment, the conductor layer can be formed by plating. For example, known techniques such as semi-additive and fully additive methods can be used to plate the surface of the insulating layer to form a conductor layer with the desired wiring pattern. From the viewpoint of ease of manufacturing, it is preferable to use the semi-additive method. The following shows an example of forming a conductor layer using the semi-additive method.

[0262] First, a seed layer is formed on the surface of an insulating layer using electroless plating. Next, a masking pattern is formed on the formed seed layer, corresponding to the desired wiring pattern, exposing a portion of the seed layer. A metal layer is formed on the exposed seed layer using electroplating, and then the masking pattern is removed. Finally, the unwanted seed layer is removed using etching or the like, resulting in a conductor layer with the desired wiring pattern.

[0263] In other embodiments, the conductor layer can be formed using metal foil. When using metal foil to form the conductor layer, step (V) is preferably performed between steps (I) and (II). For example, after step (I), the support is removed, and metal foil is laminated onto the surface of the exposed resin composition layer. The lamination of the resin composition layer and the metal foil can be performed using vacuum lamination. The lamination conditions can be the same as those described for step (I). Next, step (II) is performed to form an insulating layer. Then, using the metal foil on the insulating layer, a conductor layer with the desired wiring pattern can be formed using existing known techniques such as subtractive processing or modified semi-additive processing.

[0264] Metal foils can be manufactured using known methods such as electrolysis and rolling. Commercially available metal foils include, for example, HLP foil and JXUT-III foil manufactured by JX Minerals & Metals Corporation, and 3EC-III foil and TP-III foil manufactured by Mitsui Mining & Metals Corporation.

[0265] Semiconductor Devices The semiconductor device of the present invention includes the printed wiring board of the present invention. The semiconductor device of the present invention can be manufactured using the printed wiring board of the present invention.

[0266] Examples of semiconductor devices include various semiconductor devices used in electrical products (e.g., computers, mobile phones, digital cameras, and televisions) and vehicles (e.g., motorcycles, automobiles, trams, ships, and airplanes). [Example]

[0267] The present invention will now be specifically described through examples. The present invention is not limited to these examples. Furthermore, in the following description, unless otherwise explicitly stated, "parts" and "%" refer to "parts by mass" and "% by mass," respectively. The temperature condition, unless otherwise specified, is room temperature (23°C), and the pressure condition, unless otherwise specified, is atmospheric pressure (1 atm).

[0268] <Example 1> While stirring, 15 parts of biphenyl-type epoxy resin (NC3000L manufactured by Nippon Kayaku Co., Ltd., epoxy equivalent approximately 269 g / eq.) were heated and dissolved in 20 parts of solvent naphtha. The solution was cooled to room temperature to prepare the epoxy resin solution composition. This epoxy resin solution composition contained 2 parts of cyclic carbonate compound 1 (4,4,6-trimethyl-1,3-dioxane-2-one manufactured by JNC Co., Ltd., compound shown in formula (A4)), 45 parts of an active ester compound (HPC-8000-65T manufactured by DIC Co., Ltd., active ester equivalent approximately 223 g / eq., toluene solution with 65% non-volatile component), and spherical silica (SO-C2 manufactured by Yaduma Co., Ltd., average particle size 0.5 μm, specific surface area 5.8 m²) surface-treated with a silane coupling agent (KBM-573 manufactured by Shin-Etsu Chemical Co., Ltd.). 130 parts of a phenolic curing agent containing a triazine skeleton (DIC Corporation's "LA-3018-50P", active group equivalent of approximately 151 g / eq., 2-methoxypropanol solution with 50% non-volatile component) 3 parts of a carbodiimide curing agent (Nisshinbo Chemical Co., Ltd.'s "V-03", active group equivalent of approximately 216 g / eq., toluene solution with 50% non-volatile component) 8 parts of an imidazole curing accelerator (Shikoku Chemical Industry Co., Ltd.'s "1B2PZ", 1-benzyl-2-phenylimidazolium) 0.2 parts of a phenoxy resin (Mitsubishi Chemical Co., Ltd.'s "YX7553BH30", 1:1 solution of MEK and cyclohexanone with 30% by mass of non-volatile component) were uniformly dispersed using a high-speed rotary mixer to prepare a resin composition.

[0269] <Example 2> Instead of 15 parts of biphenyl-type epoxy resin (NC3000L manufactured by Nippon Kayaku Co., Ltd.), 15 parts of naphthalene-type epoxy resin (HP-4032-SS manufactured by DIC Co., Ltd., 1,6-bis(glycidyloxy)naphthalene, epoxy equivalent of about 145 g / eq.) were used, and the amount of cyclic carbonate compound 1 (4,4,6-trimethyl-1,3-dioxane-2-one manufactured by JNC Co., Ltd.) was changed from 2 parts to 4 parts. Otherwise, the resin composition was prepared in the same manner as in Example 1.

[0270] <Example 3> Instead of 2 parts of cyclic carbonate compound 1 ("4,4,6-trimethyl-1,3-dioxane-2-one" manufactured by JNC), 1 part of cyclic carbonate compound 2 ("DEPPO" manufactured by JNC, compound shown in formula (A11) and 1 part of cyclic carbonate compound 3 ("DXC" manufactured by JNC, compound shown in formula (A10)) were used; instead of 45 parts of the active ester compound ("HPC-8000-65T" manufactured by DIC), 45 parts of an active ester compound ("HPC-8150-62T" manufactured by DIC, toluene solution with an active ester equivalent of approximately 220 g / eq. and a non-volatile component percentage of 62% by mass) were used; furthermore, spherical silica ("SO-C2" manufactured by Yaduma, average particle size 0.5 μm, specific surface area 5.8 m²) surface-treated with silane coupling agent ("KBM-573" manufactured by Shin-Etsu Chemical Co., Ltd.) was used. The amount of 2 / g used was changed from 130 parts to 155 parts, and the resin composition was prepared in the same manner as in Example 1.

[0271] <Example 4> 15 parts of biphenyl-type epoxy resin (NC3000L, manufactured by Nippon Chemical Co., Ltd.) were replaced with 12 parts of naphthol-type epoxy resin (ESN475V, manufactured by Nippon Steel & Sumitomo Chemical Co., Ltd., epoxy equivalent approximately 330 g / eq.) and 3 parts of bisphenol-type epoxy resin (ZX1059, manufactured by Nippon Steel & Sumitomo Chemical Co., Ltd., a 1:1 mixture of bisphenol A and bisphenol F types, epoxy equivalent approximately 169 g / eq.); 1 part of cyclic carbonate compound 1 (4,4,6-trimethylolpropagated by JNC Corporation) was replaced with cyclocarbonate compound 1. Two parts of cyclic carbonate compound 3 ("DXC" manufactured by JNC) were used instead of 2 parts of active ester compound ("HPC-8000-65T" manufactured by DIC). 45 parts of active ester compound ("HPC-8150-62T" manufactured by DIC, with an active ester equivalent of approximately 220 g / eq. and a non-volatile component percentage of 62% by mass in toluene solution) were used. Otherwise, the resin composition was prepared in the same manner as in Example 1.

[0272] <Example 5> Instead of 2 parts of cyclic carbonate compound 3 ("DXC" manufactured by JNC Corporation), 2 parts of cyclic carbonate compound 4 (a compound synthesized by the same method as described in Example 13 of Japanese Patent No. 6141261, the compound shown in formula (A16)) were used, and the resin composition was prepared in the same manner as in Example 4.

[0273] <Example 6> Instead of 2 parts of cyclic carbonate compound 3 ("DXC" manufactured by JNC Corporation), 2 parts of cyclic carbonate compound 5 (a compound synthesized by the same method as described in the examples of Japanese Patent Application Publication No. 2018-118946, the compound shown in formula (A17)) were used, and the resin composition was prepared in the same manner as in Example 4.

[0274] <Example 7> Instead of 45 parts of the active ester compound ("HPC-8000-65T" manufactured by DIC), 45 parts of an active ester compound ("HPC-8150-62T" manufactured by DIC, with an active ester equivalent of approximately 220 g / eq. and a non-volatile component content of 62% by mass in toluene solution) were used; furthermore, 4 parts of a biphenyl alkylphenol varnish-type maleimide ("MIR-3000-70MT" manufactured by Nippon Kayaku Co., Ltd., with a non-volatile component content of 70% in MEK / toluene mixed solution) were used. Otherwise, the resin composition was prepared in the same manner as in Example 1.

[0275] <Example 8> Instead of 15 parts of biphenyl-type epoxy resin (NC3000L manufactured by Nippon Kayaku Co., Ltd.), 15 parts of naphthalene-type epoxy resin (HP-4032-SS manufactured by DIC Co., Ltd., 1,6-bis(glycidyloxy)naphthalene, epoxy equivalent of about 145 g / eq.) were used; instead of 4 parts of biphenyl aralkylphenol varnish-type maleimide (MIR-3000-70MT manufactured by Nippon Kayaku Co., Ltd., MEK / toluene mixed solution with 70% non-volatile component) were used, 3 parts of maleimide-terminated polyimide compound (BMI-1500 manufactured by DMI Co., Ltd.) were used. Otherwise, the resin composition was prepared in the same manner as in Example 7.

[0276] <Example 9> Instead of 15 parts of biphenyl-type epoxy resin (NC3000L manufactured by Nippon Chemical Co., Ltd.), 12 parts of naphthol-type epoxy resin (ESN475V manufactured by Nippon Steel & Sumitomo Chemical Co., Ltd., epoxy equivalent of approximately 330 g / eq.) and 3 parts of bisphenol-type epoxy resin (ZX1059 manufactured by Nippon Steel & Sumitomo Chemical Co., Ltd., a 1:1 mixture of bisphenol A and bisphenol F types, epoxy equivalent of approximately 169 g / eq.) were used; instead of 4 parts of biphenyl aralkylphenol varnish-type maleimide (MIR-3000-70MT manufactured by Nippon Chemical Co., Ltd.), 3 parts of methacrylic acid-modified polyphenylene ether (SA9000-111 manufactured by SABIC Innovative Plastics Co., Ltd.) were used. Otherwise, the resin composition was prepared in the same manner as in Example 7.

[0277] <Example 10> The amount of biphenyl-type epoxy resin (NC3000L manufactured by Nippon Kayaku Co., Ltd.) was changed from 15 parts to 10 parts, and 5 parts of naphthalene-type epoxy resin (HP-4032-SS manufactured by DIC Co., Ltd., 1,6-bis(glycidyloxy)naphthalene, epoxy equivalent of about 145 g / eq.) were used instead of biphenyl aralkylphenol varnish-type maleimide (MIR-3000-70MT manufactured by Nippon Kayaku Co., Ltd.), and 4 parts of vinyl benzyl modified polyphenylene ether (OPE-2St 2200 manufactured by Mitsubishi Gas Chemical Co., Ltd., toluene solution with a non-volatile component rate of 65%) were used. Otherwise, the resin composition was prepared in the same manner as in Example 7.

[0278] <Example 11> The amount of biphenyl-type epoxy resin (NC3000L manufactured by Nippon Kayaku Co., Ltd.) was changed from 15 parts to 10 parts, and 5 parts of naphthalene-type epoxy resin (HP-4032-SS manufactured by DIC Co., Ltd., 1,6-bis(glycidyloxy)naphthalene, epoxy equivalent of about 145 g / eq.) were used; the amount of spherical silica (SO-C2 manufactured by Yaduma Co., Ltd., average particle size 0.5 μm, specific surface area 5.8 m² / g) surface-treated with silane coupling agent (KBM-573 manufactured by Shin-Etsu Chemical Co., Ltd.) was changed from 130 parts to 100 parts, and 7 parts of hollow aluminosilicate particles (MG-005 manufactured by Pacific Cement Co., Ltd., average particle size 1.6 μm, porosity 80% by volume) were used. Otherwise, the resin composition was prepared in the same manner as in Example 1.

[0279] <Comparative Example 1> The resin composition was prepared in the same manner as in Example 1, except that two parts of cyclic carbonate compound 1 ("4,4,6-trimethyl-1,3-dioxane-2-one" manufactured by JNC Corporation) were not used.

[0280] <Comparative Example 2> Two parts of cyclic carbonate compound 1 ("4,4,6-trimethyl-1,3-dioxane-2-one" manufactured by JNC) and three parts of maleimide-terminated polyimide compound ("BMI-1500" manufactured by DMI) were not used; and the amount of spherical silica ("SO-C2" manufactured by Yaduma, with an average particle size of 0.5 μm and a specific surface area of ​​5.8 m² / g) surface-treated with silane coupling agent ("KBM-573" manufactured by Shin-Etsu Chemical Co., Ltd.) was changed from 130 parts to 150 parts, and the resin composition was prepared in the same manner as in Example 8.

[0281] <Comparative Example 3> Instead of 15 parts of naphthalene-type epoxy resin (DIC Corporation's "HP-4032-SS", 1,6-bis(glycidoxy)naphthalene, epoxy equivalent approximately 145 g / eq.), 12 parts of naphthol-type epoxy resin (Nippon Steel & Sumitomo Chemical Co., Ltd.'s "ESN475V", epoxy equivalent approximately 330 g / eq.) and bisphenol-type epoxy resin (Nippon Steel & Sumitomo Chemical Co., Ltd.'s "ZX1059", a 1:1 mixture of bisphenol A and bisphenol F, epoxy equivalent approximately 145 g / eq.) were used. Approximately 169 g / eq.) 3 parts; 45 parts of the active ester compound (DIC Corporation's "HPC-8150-62T", an active ester equivalent of approximately 220 g / eq., and a toluene solution with a non-volatile content of 62% by mass) were reduced to 20 parts; further, 150 parts of spherical silica (Yaduma Corporation's "SO-C2", average particle size 0.5 μm, specific surface area 5.8 m² / g) surface-treated with a silane coupling agent (Shin-Etsu Chemical Industry Co., Ltd.'s "KBM-573") were reduced to 90 parts. Except for the above, the resin composition was prepared in the same manner as in Comparative Example 2.

[0282] <Comparative Example 4> The amount of spherical silica (SO-C2, 0.5 μm average particle size, 5.8 m² / g), which had been surface-treated with a silane coupling agent (KBM-573, Shin-Etsu Chemical Co., Ltd.), was changed from 150 parts to 125 parts; and 2 parts of a polyester compound (TESRAC 5001-40T, 27,000 number-average molecular weight, 40% by mass of non-volatile components in a toluene solution) were used. Otherwise, the resin composition was prepared in the same manner as in Comparative Example 2.

[0283] <Example 1: Fabrication of Resin Sheets> As a support, a polyethylene terephthalate film (Lintec "AL5", 38 μm thick) with a release layer was prepared. The resin composition obtained in the examples and comparative examples was uniformly coated onto the release layer of this support, so that the thickness of the dried resin composition layer was 40 μm. Then, the resin composition was dried at 80°C to 100°C (average 90°C) for 4 minutes to obtain a resin sheet comprising the support and the resin composition layer.

[0284] <Experimental Example 1: Determination of Relative Permittivity (Dk) and Dielectric Tangent (Df)> The protective film was peeled off from the resin sheet prepared in Example 1, and heated at 200°C for 90 minutes to thermally harden the resin composition layer. The support was then peeled off, thereby obtaining a hardened film formed from the hardened resin composition. For Comparative Example 4, a hardened film could not be obtained. The hardened film was cut into pieces 2 mm wide and 80 mm long to obtain evaluation hardened material A.

[0285] For the obtained evaluation hardened material A, the relative permittivity (Dk value) and dielectric tangent (Df value) were measured using an Agilent Technologies HP8362B instrument with resonant cavity perturbation method at a measurement frequency of 5.8 GHz and a measurement temperature of 23 °C. Measurements were performed on three samples, and the average value was calculated.

[0286] <Experimental Example 2: Determination of Elongation at Break> For the evaluation hardened material A obtained using the same method as in Test Example 1, a tensile test was performed at 23°C using a Tensilon universal testing machine (Orientec "RTC-1250A") according to Japanese Industrial Standard JIS K7127, and the elongation at break (%) was determined.

[0287] <Experimental Example 3: Determination of Arithmetic Mean Roughness (Ra)> (1) Substrate treatment of the internal substrate: As the inner layer substrate, a double-sided copper-clad laminate (copper foil thickness 18 μm, substrate thickness 0.8 mm, Panasonic "R1515A") was prepared on a glass cloth substrate with copper foil on the surface. The copper foil on the surface of the inner layer substrate was roughened by etching with a 1 μm copper etchant (MEC "CZ8101"). Then, it was dried at 190°C for 30 minutes.

[0288] (2) Lamination and hardening of resin sheets The resin sheet prepared in Example 1 was laminated onto both sides of the inner layer substrate using a batch vacuum pressure laminator (Nikko-Materials, 2-stage stacking laminator "CVP700") in a manner that bonded the resin composition layer to the aforementioned inner layer substrate. The lamination was performed as follows: after depressurization for 30 seconds to bring the pressure down to below 13 hPa, it was pressed at a temperature of 100°C and a pressure of 0.74 MPa for 30 seconds.

[0289] Next, the laminated resin sheet is smoothed by hot pressing at 100°C and 0.5MPa for 60 seconds under atmospheric pressure. Then, it is heated in an oven at 130°C for 30 minutes, and then transferred to an oven at 170°C for 30 minutes.

[0290] (3) Formation of through holes Using a CO2 laser processing machine (LK-2K212 / 2C) manufactured by Via Machinery Co., Ltd., the insulating layer was processed under the conditions of 2000Hz frequency, 3 microsecond pulse width, 0.95W output power, and 3 shots to form through holes with a top diameter of 50μm and a bottom diameter of 40μm on the surface of the insulating layer. Then, the PET film was peeled off.

[0291] (4) Roughening treatment The inner layer substrate was immersed in Swelling Dip Securiganth P manufactured by Amtec Japan Co., Ltd. at 60°C for 10 minutes as a swelling solution. Next, it was immersed in Concentrate Compact P (an aqueous solution of KMnO4: 60 g / L and NaOH: 40 g / L) manufactured by Amtec Japan Co., Ltd. as a roughening solution at 80°C for 20 minutes. Finally, it was immersed in Reduction Solution Securiganth P manufactured by Amtec Japan Co., Ltd. as a neutralizing solution at 40°C for 5 minutes. The resulting substrate was used as evaluation substrate A.

[0292] (5) Determination of arithmetic mean roughness (Ra) A non-contact surface roughness meter (Veeco Instruments WYKO NT3300) was used in VSI mode with a 50x lens. The measurement range was set to 121μm × 92μm. The values ​​were measured on the evaluation substrate A, and the Ra value was calculated from these values. The average value of 10 randomly selected points was then calculated.

[0293] <Example 4: Determination of the peel strength of the plated conductor layer before HAST test> Evaluation substrate A, obtained using the same method as in Experimental Example 3(4), was immersed in an electroless plating solution containing PdCl₂ at 40°C for 5 minutes, followed by immersion in an electroless copper plating solution at 25°C for 20 minutes. After annealing at 150°C for 30 minutes, a resist layer was formed. After pattern formation using etching, copper sulfate electrolytic plating was performed to form a conductor layer with a thickness of 30 μm. Next, an annealing treatment was performed at 200°C for 60 minutes, and the resulting substrate was used as evaluation substrate B.

[0294] A 10mm wide and 150mm long cut was made in the conductor layer of the obtained evaluation substrate B, which does not contain through holes. One end of the cut was peeled off and clamped with a jig (TSE Company, AUTO COM type AC-50C-SL testing machine). The load (kgf / cm) when peeling 100mm vertically at a speed of 50mm / min was measured at room temperature (25℃).

[0295] <Example 5: Determination of the peel strength of the plated conductor layer after HAST test> Evaluation substrate B, prepared using the same method as in Test Example 4, underwent a 100-hour accelerated environmental test (HAST) at 130°C and 85%RH using a high-accelerated life testing apparatus (PM422, manufactured by Kusumoto Chemical Co., Ltd.). Then, a notch was cut into the HASTed evaluation substrate B in the same manner as described above, and one end of the notch was peeled off as in Test Example 4. The substrate was then clamped in the jig of the tensile testing machine described above, and the load (kgf / cm) was measured when 35 mm was peeled off vertically at a speed of 50 mm / min at room temperature. The measurement was performed according to Japanese Industrial Standard JIS C6481.

[0296] The amount of raw materials used in the resin compositions of each embodiment and comparative example, and the test results are summarized in Table 1 below.

[0297]

[0298] As shown in Table 1 above, in the resin composition containing (B) epoxy resin and (C) inorganic filler, when using (A) cyclic carbonate compound, compared with the case where (A) cyclic carbonate compound is not used, a cured product that maintains high peel strength even after the HAST test and has a low dielectric tangent value can be obtained. Furthermore, in Example 11, which contains hollow inorganic filler as (C) inorganic filler, the relative dielectric constant is further reduced compared to Example 1.

[0299] This application is based on Japanese Patent Application No. 2021-191494 filed with the Japan Patent Office (filed on November 25, 2021), the contents of which are contained in this specification.

Claims

1. A resin composition, wherein, The compound comprises (A) a cyclic carbonate compound, (B) an epoxy resin, and (C) an inorganic filler, wherein (C) comprises silicon dioxide, and (A) comprises a compound of formula (1), wherein in formula (1), R1, R2, R3, R4, R5, and R6 each independently represent (1) a hydrogen atom, (2) an alkyl group optionally substituted with a group selected from RO-, RCO-, RCOO-, and ROCO-, (3) an alkenyl group optionally substituted with a group selected from RO-, RCO-, RCOO-, and ROCO-, (4) an aralkyl group optionally substituted with a group selected from R-, RO-, RCO-, RCOO-, and ROCO-, (5) a group of formula (2-1), or (6) a group of formula (2-2), wherein formula (2-1) is: and formula (2-2) is: R1', R2', R3', R4', R5' and R6' each independently represent (1) a hydrogen atom, (2) an alkyl group optionally substituted with a group selected from RO-, RCO-, RCOO-, and ROCO-, (3) an alkenyl group optionally substituted with a group selected from RO-, RCO-, RCOO-, and ROCO-, or (4) an aralkyl group optionally substituted with a group selected from R-, RO-, RCO-, RCOO-, and ROCO-; A1 and A2 each independently represent -O-, -CO-, -COO-, or -OCO-; X and Y each independently represent (1) an alkenyl group optionally substituted with a group selected from RO-, RCO-, RCOO-, and ROCO-, or (2) an alkenyl group optionally substituted with a group selected from RO-, RCO-, RCOO-, and ROCO-; R independently represents an alkyl, alkenyl, aralkyl, or aryl group, which is optionally substituted by a group selected from halogen atoms, alkyl-oxy, alkenyl-oxy, aryl-oxy, aralkyl-oxy, alkyl-carbonyl, alkenyl-carbonyl, aryl-carbonyl, aralkyl-carbonyl, alkyl-oxy-carbonyl, alkenyl-oxy-carbonyl, aryl-oxy-carbonyl, aralkyl-oxy-carbonyl, alkyl-carbonyl-oxy, alkenyl-oxy-carbonyl, aryl-oxy-carbonyl, aralkyl-oxy-carbonyl, alkyl-carbonyl-oxy, alkenyl-carbonyl-oxy, aryl-carbonyl-oxy, and aralkyl-carbonyl-oxy; Z independently represents a divalent hydrocarbon group optionally having a substituent; n represents 0, 1, 2, or 3; * represents a bonding site.

2. A resin composition, wherein, The compound comprises (A) a cyclic carbonate compound, (B) an epoxy resin, (C) an inorganic filler, and (D) an active ester compound. The component (A) comprises a compound of formula (1), in which R1, R2, R3, R4, R5, and R6 each independently represent (1) a hydrogen atom, (2) an alkyl group optionally substituted with a group selected from RO-, RCO-, RCOO-, and ROCO-, (3) an alkenyl group optionally substituted with a group selected from RO-, RCO-, RCOO-, and ROCO-, (4) an aralkyl group optionally substituted with a group selected from R-, RO-, RCO-, RCOO-, and ROCO-, (5) a group of formula (2-1), or (6) a group of formula (2-2). Formula (2-1) is: Formula (2-2) is: R1', R2', R3', R4', R5' and R6' each independently represent (1) a hydrogen atom, (2) an alkyl group optionally substituted with a group selected from RO-, RCO-, RCOO-, and ROCO-, (3) an alkenyl group optionally substituted with a group selected from RO-, RCO-, RCOO-, and ROCO-, or (4) an aralkyl group optionally substituted with a group selected from R-, RO-, RCO-, RCOO-, and ROCO-; A1 and A2 each independently represent -O-, -CO-, -COO-, or -OCO-; X and Y each independently represent (1) an alkenyl group optionally substituted with a group selected from RO-, RCO-, RCOO-, and ROCO-, or (2) an alkenyl group optionally substituted with a group selected from RO-, RCO-, RCOO-, and ROCO-; R independently represents an alkyl, alkenyl, aralkyl, or aryl group, which is optionally substituted by a group selected from halogen atoms, alkyl-oxy, alkenyl-oxy, aryl-oxy, aralkyl-oxy, alkyl-carbonyl, alkenyl-carbonyl, aryl-carbonyl, aralkyl-carbonyl, alkyl-oxy-carbonyl, alkenyl-oxy-carbonyl, aryl-oxy-carbonyl, aralkyl-oxy-carbonyl, alkyl-carbonyl-oxy, alkenyl-oxy-carbonyl, aryl-oxy-carbonyl, aralkyl-oxy-carbonyl, alkyl-carbonyl-oxy, alkenyl-carbonyl-oxy, aryl-carbonyl-oxy, and aralkyl-carbonyl-oxy; Z independently represents a divalent hydrocarbon group optionally having a substituent; n represents 0, 1, 2, or 3; * represents a bonding site.

3. The resin composition as described in claim 1, wherein, It further includes (D) active ester compounds.

4. The resin composition as described in claim 2 or 3, wherein, When the total amount of components (A), (B), and (D) is set to 100% by mass, the content of component (A) is 1% to 10% by mass.

5. The resin composition as described in claim 2 or 3, wherein, When the non-volatile components in the resin composition are set at 100% by mass, the content of component (D) is 12% by mass or more.

6. The resin composition as described in claim 1 or 2, wherein, In formula (1), R1, R2, R5 and R6 are each independently (1) a hydrogen atom and (2) an alkyl group having 1 to 10 carbon atoms; In formulas (2-1) and (2-2), R1', R2', R5' and R6' are each independently (1) a hydrogen atom and (2) an alkyl group having 1 to 10 carbon atoms.

7. The resin composition as described in claim 1 or 2, wherein, (A) The compound represented by formula (1) in the composition is selected from the compounds represented by (A1) to (A17).

8. The resin composition as described in claim 1 or 2, wherein, When the non-volatile component in the resin composition is set to 100% by mass, the content of component (B) is 1% to 20% by mass.

9. The resin composition as described in claim 1 or 2, wherein, (C) The average particle size of the component is greater than 0.2 μm.

10. The resin composition as described in claim 1 or 2, wherein, When the non-volatile components in the resin composition are set at 100% by mass, the content of component (C) is 5% by mass or more.

11. The resin composition as described in claim 1 or 2, wherein, When the non-volatile components in the resin composition are set at 100% by mass, the content of component (C) is 60% by mass or more.

12. The resin composition as described in claim 1 or 2, wherein, It further includes a curing agent selected from phenolic curing agents and carbodiimide curing agents.

13. The resin composition as described in claim 1 or 2, wherein, When measured at 5.8 GHz and 23 °C, the dielectric tangent (Df) of the cured resin composition was below 0.0030.

14. The resin composition as described in claim 1 or 2, wherein, When measured at 23°C according to JIS K7127, the elongation at break of the cured resin composition is ≥0.2%.

15. The resin composition described in claim 1 or 2 is used to form an insulating layer, wherein the insulating layer is an insulating layer for forming a conductor layer.

16. The resin composition described in claim 1 or 2, used to form an insulating layer for a printed wiring board.

17. A cured compound, which is a cured compound of the resin composition described in any one of claims 1 to 16.

18. A sheet-like laminated material, wherein, It contains a resin composition as described in any one of claims 1 to 16.

19. A resin sheet comprising: a support and a resin composition layer disposed on the support, formed of a resin composition as described in any one of claims 1 to 16.

20. A printed wiring board having an insulating layer formed from a cured resin composition comprising (A) a cyclic carbonate compound, (B) an epoxy resin, and (C) an inorganic filler material, wherein (A) comprises a compound of formula (1), wherein in formula (1), R1, R2, R3, R4, R5, and R6 each independently represent (1) a hydrogen atom, (2) an alkyl group optionally substituted with a group selected from RO-, RCO-, RCOO-, and ROCO-, (3) an alkenyl group optionally substituted with a group selected from RO-, RCO-, RCOO-, and ROCO-, (4) an aralkyl group optionally substituted with a group selected from R-, RO-, RCO-, RCOO-, and ROCO-, (5) a group of formula (2-1), or (6) a group of formula (2-2), wherein formula (2-1) is: and formula (2-2) is: R1', R2', R3', R4', R5' and R6' each independently represent (1) a hydrogen atom, (2) an alkyl group optionally substituted with a group selected from RO-, RCO-, RCOO-, and ROCO-, (3) an alkenyl group optionally substituted with a group selected from RO-, RCO-, RCOO-, and ROCO-, or (4) an aralkyl group optionally substituted with a group selected from R-, RO-, RCO-, RCOO-, and ROCO-; A1 and A2 each independently represent -O-, -CO-, -COO-, or -OCO-; X and Y each independently represent (1) an alkenyl group optionally substituted with a group selected from RO-, RCO-, RCOO-, and ROCO-, or (2) an alkenyl group optionally substituted with a group selected from RO-, RCO-, RCOO-, and ROCO-; R independently represents an alkyl, alkenyl, aralkyl, or aryl group, which is optionally substituted by a group selected from halogen atoms, alkyl-oxy, alkenyl-oxy, aryl-oxy, aralkyl-oxy, alkyl-carbonyl, alkenyl-carbonyl, aryl-carbonyl, aralkyl-carbonyl, alkyl-oxy-carbonyl, alkenyl-oxy-carbonyl, aryl-oxy-carbonyl, aralkyl-oxy-carbonyl, alkyl-carbonyl-oxy, alkenyl-oxy-carbonyl, aryl-oxy-carbonyl, aralkyl-oxy-carbonyl, alkyl-carbonyl-oxy, alkenyl-carbonyl-oxy, aryl-carbonyl-oxy, and aralkyl-carbonyl-oxy; Z independently represents a divalent hydrocarbon group optionally having a substituent; n represents 0, 1, 2, or 3; * represents a bonding site.

21. A printed wiring board having an insulating layer formed from a cured form of a resin composition as described in any one of claims 1 to 16.

22. A semiconductor device comprising a printed wiring board as described in claim 20 or 21.