Resin composition

Abstract

To provide a resin composition which provides a cured product having a low dielectric loss tangent and achieving both excellent smear removability and high heat resistance (glass transition temperature).SOLUTION: (1A) a maleimide compound having a partial structure represented by Formula (1), a partial structure represented by Formula (T-1) chemically bonded to the partial structure represented by Formula (1), and a partial structure represented by Formula (T-2) chemically bonded to the partial structure represented by Formula (1), (B) an epoxy compound, and (D) a curing agent, in which the (D) ingredient includes (D1) an active ester compound.SELECTED DRAWING: Figure 1

Description

[Technical Field]

[0001] The present invention relates to a resin composition, and further to a resin sheet, a cured product, a circuit board, and a semiconductor device obtained using the resin composition. [Background technology]

[0002] Resin compositions containing epoxy resins produce cured products with excellent insulating properties, and have therefore been widely used as insulating materials for circuit boards such as printed wiring boards and rewiring boards for semiconductor packages.

[0003] On the other hand, with the recent increase in communication speeds, insulating materials for circuit boards are required to have excellent dielectric properties (low dielectric dissipation factor) in order to reduce transmission loss when operating in a high-frequency environment. As insulating materials with excellent dielectric properties, those that use specific curing agents such as active ester resins that can reduce or suppress the generation of polar groups such as secondary hydroxyl groups during the curing reaction of epoxy resins have been reported (for example, Patent Documents 1 and 2). [Prior art documents] [Patent documents]

[0004] [Patent Document 1] Japanese Patent Application Publication No. 2019-157027 [Patent Document 2] Japanese Patent Publication No. 2020-094213 Summary of the Invention [Problem to be solved by the invention]

[0005] However, as mentioned above, when an active ester resin or the like is used as a curing agent to obtain a cured product with a low dielectric loss tangent, there is a problem that smear residue is likely to remain when via holes are formed. In addition, the amount of heat generated by electronic components tends to increase when they are operated in a high-frequency environment, and further improvement in heat resistance is also required for insulating materials used in high-speed communication applications.

[0006] The present invention has been made in view of the above-mentioned problems, and an object of the present invention is to provide a resin composition that provides a cured product having a low dielectric loss tangent, and that has both excellent smear removability and high heat resistance (glass transition temperature). [Means for solving the problem]

[0007] As a result of extensive investigations, the present inventors have found that the above-mentioned problems can be solved by a resin composition containing a maleimide compound having a specific structure, an epoxy resin, and an active ester resin, and have thus completed the present invention.

[0008] That is, the present invention includes the following. [1] (1A) A maleimide compound having a partial structure represented by the following formula (1), a partial structure represented by the following formula (T-1) that is chemically bonded to the partial structure represented by the formula (1), and a partial structure represented by the following formula (T-2) that is chemically bonded to the partial structure represented by the formula (1): (B) an epoxy resin, and (D) a curing agent; A resin composition comprising: A resin composition, wherein the component (D) comprises an active ester resin (D1). [ka] (In formula (1), R 13 Each independently represents a hydrocarbon group having 1 to 18 carbon atoms. 2 each independently represents an integer of 0 to 4, and n 1 represents the number of repeating units. Two * symbols each represent a bond, and one bond corresponds to L in the following formula (T-1). 13 or L 14 and the other bond is L in the following formula (T-2): 11 or L 12 ) [ka] (In the above formulas (T-1) and (T-2), R 11 and R15 R each independently represents a hydrocarbon group having 1 to 18 carbon atoms. 12 and R 14 each independently represents a hydrocarbon group having 1 to 18 carbon atoms. 11 , L 12 , L 13 and L 14 Each independently represents a bond. 11 or L 12 is chemically bonded to the partial structure represented by formula (1) at the position of L 13 or L 14 At the position m, the compound is chemically bonded to the partial structure represented by formula (1). 1 and m 3 each independently represents an integer of 0 to 2.) [2] In formulas (T-1) and (T-2), L which is not chemically bonded to the partial structure represented by formula (1) 11 , L 12 , L 13 and L 14 is bonded to a hydrogen atom or a monovalent group represented by the following formula (4): [ka] (In formula (4), R 16 Each independently represents a hydrocarbon group having 1 to 18 carbon atoms. 4 represents an integer from 0 to 5. * represents a bond. [3] In formulas (T-1) and (T-2), L which is not chemically bonded to the partial structure represented by formula (1) 11 , L 12 , L 13 and L 14 is bonded to a hydrogen atom. [4] (2A) a maleimide compound having a structural unit represented by the following formula (2): (B) an epoxy resin, and (D) a curing agent; A resin composition comprising: A resin composition, wherein the component (D) comprises an active ester resin (D1). [ka] (In formula (2), R 11 R each independently represents a hydrocarbon group having 1 to 18 carbon atoms. 12 R each independently represents a hydrocarbon group having 1 to 18 carbon atoms. 13 R each independently represents a hydrocarbon group having 1 to 18 carbon atoms. 16 Each independently represents a hydrocarbon group having 1 to 18 carbon atoms. 1 each independently represents an integer of 0 to 2, m 6 each independently represents an integer of 0 to 2, m 1 +m 6 ≦2. m 2 each independently represents an integer of 0 to 4, and m 4 each independently represents an integer of 0 to 5, and n 1 Each independently represents the number of repeating units.) [5] The resin composition according to [4], wherein the component (2A) is a maleimide compound having a structure represented by the following formula (3): [ka] [ka] (In formula (3), formula (4) and formula (5), R 11 R each independently represents a hydrocarbon group having 1 to 18 carbon atoms. 12 R each independently represents a hydrocarbon group having 1 to 18 carbon atoms. 13 R each independently represents a hydrocarbon group having 1 to 18 carbon atoms. 16 Each independently represents a hydrocarbon group having 1 to 18 carbon atoms. 1 each independently represents an integer of 0 to 2, m 6 each independently represents an integer of 0 to 2, m 5 each independently represents an integer of 0 to 3, and m 1 +m 6 ≦2 and m 1 +m 5 ≦3. m 2 each independently represents an integer of 0 to 4, and m 4each independently represents an integer of 0 to 5, and n 1 Each "n" independently represents the number of repeating units, and each "n" independently represents an integer of 1 or more. M1 represents a hydrogen atom or a monovalent group represented by formula (4). M2 represents a hydrogen atom or a monovalent group represented by formula (5). * represents a bond. [6] In formula (3), X M1 is a hydrogen atom, and X M2 The resin composition according to [5], wherein is a monovalent group represented by formula (5). [7] R 13 The resin composition according to any one of [1] to [6], wherein each of the groups independently represents an alkyl group having 1 to 18 carbon atoms. [8] The resin composition according to any one of [1] to [7], wherein the component (D1) is an activated ester resin containing a naphthalene structure. [9] The resin composition according to any one of [1] to [3], [7] and [8], wherein the mass ratio of the component (1A) to the component (D1) [component (1A) / component (D1)] is 0.01 to 5.

[10] The resin composition according to any one of [4] to [8], wherein the mass ratio of the component (2A) to the component (D1) [component (2A) / component (D1)] is 0.01 to 5.

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

[10] , wherein the component (D) further contains a curing agent other than the component (D1) (hereinafter referred to as "other curing agent (D2)").

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

[11] , wherein the ratio of the number of moles of active groups in the curing agent (D) to the number of moles of epoxy groups in the epoxy resin (B) (number of moles of active groups in the curing agent / number of moles of epoxy groups in the epoxy resin) is 1 or more.

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

[12] , further comprising (E) an inorganic filler.

[14] The resin composition according to

[13] , wherein the content of component (E) is 80% by mass or less when the total amount of non-volatile components in the resin composition is 100% by mass.

[15] The resin composition according to any one of [1] to [3], [7] to [9], and

[11] to

[14] , further containing a maleimide compound other than the component (1A) (hereinafter referred to as "(1F) other maleimide compound").

[16] The resin composition according to any one of [4] to [8] and

[10] to

[14] , further comprising a maleimide compound other than the component (2A) (hereinafter referred to as "(2F) other maleimide compound").

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

[16] , further comprising (G) a radically polymerizable resin.

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

[17] , further comprising (H) an organic filler.

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

[18] , further comprising (I) a curing accelerator.

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

[19] , which is for use in an insulating layer of a circuit board.

[21] A resin sheet comprising a support and a layer of the resin composition according to any one of [1] to

[20] provided on the support.

[22] The resin sheet according to

[21] , wherein the support is a thermoplastic resin film or a metal foil.

[23] A cured product of the resin composition according to any one of [1] to

[20] .

[24] A circuit board comprising an insulating layer made of a cured product of the resin composition according to any one of [1] to

[20] .

[25] A semiconductor device comprising the circuit board according to

[24] . [Effects of the Invention]

[0009] According to the present invention, it is possible to provide a resin composition that provides a cured product having a low dielectric tangent and that combines excellent smear removability and high heat resistance (glass transition temperature), as well as a resin sheet, a cured product, a circuit board, and a semiconductor device obtained using the resin composition. [Brief explanation of the drawings]

[0010] [Figure 1]FIG. 1 is a top view schematically showing a glass fabric-based epoxy resin double-sided copper-clad laminate on which an inner layer circuit is formed and which is used when carrying out a reflow test. DETAILED DESCRIPTION OF THE INVENTION

[0011] The present invention will be described in detail below with reference to embodiments and examples. However, the present invention is not limited to the embodiments and examples described below, and can be implemented with any modifications within the scope of the claims and their equivalents.

[0012] [Terminology] In the following description, unless otherwise specified, the expressions "XX to YY" or "XX to YY" representing a numerical range mean a numerical range including the lower and upper limits, which are the endpoints. When a numerical range is described in stages, the upper and lower limits of each numerical range can be combined in any way.

[0013] In the following description, "dielectric constant" refers to "relative dielectric constant" unless otherwise specified.

[0014] In the following description, the term "non-volatile components" refers to all components constituting the resin composition other than the organic solvent, which will be described later. The term "resin components" refers to all non-volatile components constituting the resin composition excluding the inorganic filler, which will be described later.

[0015] In the following description, unless otherwise specified, the term "optionally substituted" in reference to a compound or group means both a case where the hydrogen atoms of the compound or group are not substituted with a substituent and a case where some or all of the hydrogen atoms of the compound or group are substituted with a substituent. Furthermore, when the number of constituent atoms or carbon atoms of the compound or group is stated, the number of constituent atoms or carbon atoms does not include the number of constituent atoms or carbon atoms of substituents, unless otherwise specified.

[0016] In the following description, the term "aromatic ring" refers to a ring conforming to Hückel's rule, in which the number of electrons contained in the π-electron system on the ring is 4r+2 (r is a natural number), and includes monocyclic aromatic rings and fused aromatic rings in which two or more monocyclic aromatic rings are fused. Unless otherwise specified, the aromatic ring is preferably a monocyclic aromatic ring. The aromatic ring may be an aromatic carbocyclic ring having only carbon atoms as ring-constituting atoms, or an aromatic heterocyclic ring having heteroatoms such as oxygen atoms, nitrogen atoms, and sulfur atoms as ring-constituting atoms in addition to carbon atoms. Unless otherwise specified, the aromatic ring is preferably an aromatic carbocyclic ring. The number of carbon atoms in the aromatic ring is preferably 3 or more, more preferably 4 or more or 5 or more, and even more preferably 6 or more, unless otherwise specified, and the upper limit is preferably 24 or less, more preferably 18 or less or 14 or less, and even more preferably 10 or less. The number of carbon atoms does not include the number of carbon atoms of substituents.

[0017] Examples of the monocyclic aromatic ring include a benzene ring, a furan ring, a thiophene ring, a pyrrole ring, a pyrazole ring, an oxazole ring, an isoxazole ring, a furazan ring, a thiazole ring, an isothiazole ring, a thiadiazole ring, an imidazole ring, a triazole ring, a tetrazole ring, a pyridine ring, a pyridazine ring, a pyrimidine ring, a pyrazine ring, and a pyridazine ring. Examples of fused aromatic rings in which two or more monocyclic aromatic rings are fused include a naphthalene ring, an anthracene ring, a phenanthrene ring, a benzofuran ring, an isobenzofuran ring, an indole ring, an isoindole ring, a benzothiophene ring, a benzimidazole ring, an indazole ring, a benzoxazole ring, a benzisoxazole ring, a benzothiazole ring, a quinoline ring, an isoquinoline ring, a quinoxaline ring, an acridine ring, a quinazoline ring, a cinnoline ring, a phthalazine ring, a pyridothiazole ring, a benzotriazole ring, an imidazopyridine ring, a triazopyridine ring, a purine ring, etc. Unless otherwise specified, the aromatic ring is preferably a benzene ring or a naphthalene ring, more preferably a benzene ring.

[0018] In the following description, the "alkyl group" may be linear, branched, or cyclic, and examples thereof include a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a tert-pentyl group, a neopentyl group, a 1,2-dimethylpropyl group, an n-hexyl group, an isohexyl group, a (n-)heptyl group, a (n-)octyl group, a (n-)nonyl group, a (n-)decyl group, a (n-)undecyl group, a (n-)dodecyl group, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, a cyclononyl group, a cyclodecyl group, a norbornyl group, and an adamantyl group.

[0019] In the following description, the (1A) component and the (2A) component may be collectively referred to as the "(A) component." The (1F) component and the (2F) component may be collectively referred to as the "(F) component." The resin composition according to the first embodiment and the resin composition according to the second embodiment may be collectively referred to as the "resin composition."

[0020] [Resin composition according to the first embodiment] A resin composition according to a first embodiment of the present invention comprises (1A) a maleimide compound having a first specific structure, (B) an epoxy resin, and (D) a curing agent, wherein the component (D) comprises (D1) an active ester resin. The first specific structure will be described later. By incorporating the components (1A), (B), and (D1) in combination into a resin composition, a cured product can be obtained that has a low dielectric tangent, excellent smear removability, and high heat resistance (glass transition temperature). The present inventors have also confirmed that the cured product (insulating layer) provided by the present invention has a low dielectric constant, excellent reflow resistance, high adhesion strength to a conductor layer, a low coefficient of linear thermal expansion (CTE), and reduced warpage.

[0021] In the present invention, "adhesion strength" refers to the adhesion strength between an insulating layer and a conductor layer formed from a cured product of the resin composition of the present invention. The present inventors have confirmed that the adhesion strength is particularly excellent when the conductor layer is copper. Examples of the adhesion strength between an insulating layer and copper include "CZ copper peel strength" and "plating peel strength." "CZ copper peel strength" refers to the adhesion strength between an insulating layer and a conductor layer (copper) when they are joined by lamination. "Plating peel strength" refers to the adhesion strength between an insulating layer and a conductor layer (copper) when the conductor layer (copper) is formed on the insulating layer by plating. According to the present invention, a cured product (insulating layer) with excellent both CZ copper peel strength and plating peel strength can be obtained, and a cured product (insulating layer) with particularly excellent CZ copper peel strength can be obtained. Furthermore, a cured product exhibiting high adhesion strength (CZ copper peel strength) can also be obtained even when exposed to a high-temperature, high-humidity environment.

[0022] When curing a resin composition, it may first be cured at a relatively low temperature (pre-cure) and then cured at a relatively high temperature (full cure). Generally, a cured product after full cure tends to warp more, but the resin composition according to the first embodiment of the present invention can suppress both warpage of the cured product after pre-cure and warpage of the cured product after full cure.

[0023] The resin composition according to the first embodiment may contain, as the component (D), a curing agent other than the component (D1) (hereinafter referred to as "(D2) other curing agent"). Furthermore, the resin composition according to the first embodiment may further contain optional components in addition to a combination of the components (1A), (B), and (D). Examples of optional components include (E) inorganic fillers, (1F) other maleimide compounds, (G) radically polymerizable resins, (H) organic fillers, (I) curing accelerators, (J) organic solvents, and (K) other additives. Each component contained in the resin composition according to the first embodiment will be described in detail below.

[0024] <(1A) Maleimide Compound Having a First Specific Structure> The resin composition according to the first embodiment of the present invention contains (1A) a maleimide compound (maleimide compound having a first specific structure) having a partial structure represented by the following formula (1), a partial structure represented by the following formula (T-1) that is chemically bonded to the partial structure represented by formula (1), and a partial structure represented by the following formula (T-2) that is chemically bonded to the partial structure represented by formula (1). The component (1A) may be used singly or in combination of two or more. [ka] (In formula (1), R 13 Each independently represents a hydrocarbon group having 1 to 18 carbon atoms. 2 each independently represents an integer of 0 to 4, and n 1 represents the number of repeating units. Two * symbols each represent a bond, and one bond corresponds to L in the following formula (T-1). 13 or L 14 and the other bond is L in the following formula (T-2): 11 or L 12 ) [ka] (In the above formulas (T-1) and (T-2), R 11 and R 15 R each independently represents a hydrocarbon group having 1 to 18 carbon atoms. 12 and R 14 each independently represents a hydrocarbon group having 1 to 18 carbon atoms. 11 , L 12 , L 13 and L 14 Each independently represents a bond. 11 or L 12 is chemically bonded to the partial structure represented by formula (1) at the position of L 13 or L 14 At the position m, the compound is chemically bonded to the partial structure represented by formula (1). 1 and m 3 each independently represents an integer of 0 to 2.)

[0025] In formula (1), two *'s each represent a bond. One of the two bonds is L in formula (T-1). 13 or L 14 The other bond is chemically bonded at the position of L in the above formula (T-2). 11 or L 12 Therefore, the component (1A) has a structural unit in which a partial structure represented by formula (T-1) and a partial structure represented by formula (T-2) are linked by the partial structure represented by formula (1), and the partial structure represented by formula (1) is chemically bonded at the para-position or one ortho-position relative to the maleimide group on the benzene ring in formula (T-1) and formula (T-2).

[0026] In formula (1), R 13 Each independently represents a hydrocarbon group having 1 to 18 carbon atoms. 2 or n 1 is an integer greater than or equal to 2, there are multiple R 13 may be the same or different, but are preferably the same. Examples of the hydrocarbon group include an alkyl group, an alkenyl group, and an aromatic hydrocarbon group, and an alkyl group is preferred. That is, R 13 is preferably an alkyl group having 1 to 18 carbon atoms. The upper limit of the number of carbon atoms in the hydrocarbon group is preferably 12 or less or 10 or less, more preferably 6 or less, and even more preferably 5 or less, 4 or less, 3 or less, or 2 or less. In one embodiment, R 13 It is particularly preferable that the hydrocarbon group in the formula (I) has one carbon atom.

[0027] R 13The alkyl group in the formula (I) is a chain (straight-chain or branched) alkyl group or a cyclic alkyl group, preferably a chain alkyl group, more preferably a straight-chain alkyl group. The alkyl group has 1 to 18 carbon atoms, preferably 1 to 12 or 1 to 10, more preferably 1 to 6, even more preferably 1 to 5, 1 to 4, 1 to 3, or 1 to 2, and particularly preferably 1. Examples of the chain alkyl group include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, an s-butyl group, a t-butyl group, an n-pentyl group, an isopentyl group, an t-pentyl group, a neopentyl group, a hexyl group, a 2-ethylhexyl group, an octyl group, and a decyl group. Preferred are a methyl group, an ethyl group, an n-propyl group, an isopropyl group, and an t-butyl group. More preferred are a methyl group or an ethyl group, and even more preferred is a methyl group. Examples of the cyclic alkyl group include a cyclopentyl group, a cyclohexyl group, and a cyclooctyl group, with a cyclohexyl group being preferred.

[0028] R 13 The alkenyl group in the formula (I) is a linear, branched, and / or cyclic monovalent aliphatic unsaturated hydrocarbon group having at least one non-aromatic carbon-carbon double bond. The alkenyl group has 2 to 18 carbon atoms, preferably 2 to 12 or 2 to 10, more preferably 2 to 6, still more preferably 2 to 5, 2 to 4, or 2 to 3, and particularly preferably 2. Examples of alkenyl groups include vinyl groups, propenyl groups (allyl groups, 1-propenyl groups, isopropenyl groups), butenyl groups (1-butenyl groups, crotyl groups, methallyl groups, isocrotyl groups, etc.), pentenyl groups (1-pentenyl groups, etc.), hexenyl groups (1-hexenyl groups, etc.), heptenyl groups (1-heptenyl groups, etc.), octenyl groups (1-octenyl groups, etc.), cyclopentenyl groups (2-cyclopentenyl groups, etc.), and cyclohexenyl groups (3-cyclohexenyl groups).

[0029] R 13The aromatic hydrocarbon group in the formula (I) is a group in which one hydrogen atom on an aromatic ring has been removed from an aromatic carbon ring. The aromatic hydrocarbon group has 6 to 18 carbon atoms, preferably 6 to 12 or 6 to 10, and more preferably 6. Examples of the aromatic hydrocarbon group include a phenyl group, a naphthyl group, and an anthracenyl group, with a phenyl group or a naphthyl group being preferred, and a phenyl group being more preferred.

[0030] In addition, R in formula (1) 13 The benzene ring to which is bonded can be the benzene ring of a compound (b) having a benzyl ether skeleton, which will be described later.

[0031] In formula (1), m 2 Each independently represents an integer of 0 to 4. 1 If m is an integer greater than or equal to 2, there are multiple m 2 may be the same or different, and are preferably the same. 2 The lower limit of m is preferably 1 or more. 2 The upper limit of m is preferably 3 or less, more preferably 2 or less. 2 More preferably, m is 2. In another embodiment, m 2 may be 0.

[0032] In formula (1), n 1 represents the number of repeating units. 1 From the viewpoint of adjusting the viscosity of the resin composition, the upper limit of n is preferably 50 or less, more preferably 30 or less, and even more preferably 15 or less. 1 The lower limit of n is preferably 1 or more. 1 The number of repeating units n may be 1. 1 can be calculated from the charge ratio, NMR, etc.

[0033] In formulas (T-1) and (T-2), R 11 and R 15 Each independently represents a hydrocarbon group having 1 to 18 carbon atoms. 1 If is 2, then two R 11may be the same or different, and are preferably the same. 3 If is 2, then two R 15 may be the same or different, and are preferably the same. 11 and R 15 A preferred embodiment of R 13 is the same as

[0034] In formulas (T-1) and (T-2), m 1 and m 3 Each independently represents an integer of 0 to 2. 1 and m 3 may be the same or different, and are preferably the same. 1 and m 3 is preferably 0 or 1, and more preferably 0.

[0035] In formulas (T-1) and (T-2), R 12 and R 14 R each independently represents a hydrocarbon group having 1 to 18 carbon atoms. 12 and R 14 may be the same or different, and are preferably the same. Examples of the hydrocarbon group include an alkyl group, an alkenyl group, and an aromatic hydrocarbon group, and an alkyl group is preferred. The upper limit of the number of carbon atoms in the hydrocarbon group is preferably 12 or less or 10 or less, more preferably 6 or less, and even more preferably 5 or less, 4 or less, or 3 or less. The lower limit of the number of carbon atoms in the hydrocarbon group is preferably 2 or more. In one embodiment, R 12 and R 14 It is particularly preferable that the hydrocarbon group in the formula (I) has 2 carbon atoms.

[0036] R 12 and R 14The alkyl group in is a chain (straight-chain or branched) alkyl group or a cyclic alkyl group, preferably a chain alkyl group, and more preferably a straight-chain alkyl group. The upper limit of the number of carbon atoms in the alkyl group is 18 or less, preferably 12 or less or 10 or less, more preferably 6 or less, and even more preferably 5 or less, 4 or less, or 3 or less. The lower limit of the number of carbon atoms in the alkyl group is preferably 2 or more. In one embodiment, R 12 and R 14 In the above formula, it is particularly preferred that the number of carbon atoms in the alkyl group is 2. Examples of the chain alkyl group include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, an s-butyl group, a t-butyl group, an n-pentyl group, an isopentyl group, an t-pentyl group, a neopentyl group, a hexyl group, a 2-ethylhexyl group, an octyl group, and a decyl group, with a methyl group, an ethyl group, an n-propyl group, an isopropyl group, and a t-butyl group being preferred, a methyl group or an ethyl group being more preferred, and an ethyl group being even more preferred. Furthermore, examples of the cyclic alkyl group include a cyclopentyl group, a cyclohexyl group, and a cyclooctyl group, with a cyclohexyl group being preferred.

[0037] R 12 and R 14 The alkenyl group in the formula (I) is a linear, branched, and / or cyclic monovalent aliphatic unsaturated hydrocarbon group having at least one non-aromatic carbon-carbon double bond. The alkenyl group has 2 to 18 carbon atoms, preferably 2 to 12 or 2 to 10, more preferably 2 to 6, still more preferably 2 to 5, 2 to 4, or 2 to 3, and particularly preferably 2. Examples of alkenyl groups include vinyl groups, propenyl groups (allyl groups, 1-propenyl groups, isopropenyl groups), butenyl groups (1-butenyl groups, crotyl groups, methallyl groups, isocrotyl groups, etc.), pentenyl groups (1-pentenyl groups, etc.), hexenyl groups (1-hexenyl groups, etc.), heptenyl groups (1-heptenyl groups, etc.), octenyl groups (1-octenyl groups, etc.), cyclopentenyl groups (2-cyclopentenyl groups, etc.), and cyclohexenyl groups (3-cyclohexenyl groups).

[0038] R 12and R 14 The aromatic hydrocarbon group in the formula (I) is a group in which one hydrogen atom on an aromatic ring has been removed from an aromatic carbon ring. The aromatic hydrocarbon group has 6 to 18 carbon atoms, preferably 6 to 12 or 6 to 10, and more preferably 6. Examples of the aromatic hydrocarbon group include a phenyl group, a naphthyl group, and an anthracenyl group, with a phenyl group or a naphthyl group being preferred, and a phenyl group being more preferred.

[0039] In formula (T-1), L 13 and L 14 Each independently represents a bond. 13 or L 14 At least one of the positions of the partial structure represented by formula (1) and the partial structure represented by formula (T-1) is chemically bonded. 13 and L 14 The partial structure represented by formula (1) may be chemically bonded to each of the two positions.

[0040] In formula (T-2), L 11 and L 12 Each independently represents a bond. 11 or L 12 At least one of the positions of the partial structure represented by formula (1) and the partial structure represented by formula (T-2) is chemically bonded. 11 and L 12 The partial structure represented by formula (1) may be chemically bonded to each of the two positions.

[0041] By allowing a bonding site with the partial structure represented by formula (1) at the ortho position (6-position) relative to the maleimide group of the benzene ring of formula (T-1) and formula (T-2), the polymer has higher solubility in organic solvents and exhibits excellent low dielectric tangent and high heat resistance upon curing. 14 is bonded to a benzene ring, and R in formula (T-2) 12 The benzene ring to which is bonded can be the benzene ring of the aromatic amine compound (a) described below.

[0042] In formulas (T-1) and (T-2), L which is not chemically bonded to the partial structure represented by formula (1) 11 , L 12 , L 13 and L 14 is preferably bonded to a hydrogen atom or a monovalent group represented by the following formula (4), and more preferably bonded to a hydrogen atom. [ka] (In formula (4), R 16 Each independently represents a hydrocarbon group having 1 to 18 carbon atoms. 4 represents an integer from 0 to 5. * represents a bond.

[0043] In formula (4), R 16 Each independently represents a hydrocarbon group having 1 to 18 carbon atoms. 4 is an integer greater than or equal to 2, there are multiple R 16 may be the same or different, and are preferably the same. Examples of the hydrocarbon group include an alkyl group, an alkenyl group, and an aromatic hydrocarbon group, and an alkyl group is preferred. The upper limit of the number of carbon atoms in the hydrocarbon group is preferably 12 or less or 10 or less, more preferably 6 or less, and even more preferably 5 or less, 4 or less, or 3 or less. The lower limit of the number of carbon atoms in the hydrocarbon group is preferably 2 or more. In one embodiment, R 12 and R 14 It is particularly preferable that the hydrocarbon group in the formula (I) has 2 carbon atoms.

[0044] R 16 The alkyl group in is a chain (straight-chain or branched) alkyl group or a cyclic alkyl group, preferably a chain alkyl group, and more preferably a straight-chain alkyl group. The upper limit of the number of carbon atoms in the alkyl group is 18 or less, preferably 12 or less or 10 or less, more preferably 6 or less, and even more preferably 5 or less, 4 or less, or 3 or less. The lower limit of the number of carbon atoms in the alkyl group is preferably 2 or more. In one embodiment, R 16In the above formula, it is particularly preferred that the number of carbon atoms in the alkyl group is 2. Examples of the chain alkyl group include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, an s-butyl group, a t-butyl group, an n-pentyl group, an isopentyl group, an t-pentyl group, a neopentyl group, a hexyl group, a 2-ethylhexyl group, an octyl group, and a decyl group, with a methyl group, an ethyl group, an n-propyl group, an isopropyl group, and a t-butyl group being preferred, a methyl group or an ethyl group being more preferred, and an ethyl group being even more preferred. Furthermore, examples of the cyclic alkyl group include a cyclopentyl group, a cyclohexyl group, and a cyclooctyl group, with a cyclohexyl group being preferred.

[0045] R 16 The alkenyl group in the formula (I) is a linear, branched, and / or cyclic monovalent aliphatic unsaturated hydrocarbon group having at least one non-aromatic carbon-carbon double bond. The alkenyl group has 2 to 18 carbon atoms, preferably 2 to 12 or 2 to 10, more preferably 2 to 6, still more preferably 2 to 5, 2 to 4, or 2 to 3, and particularly preferably 2. Examples of alkenyl groups include vinyl groups, propenyl groups (allyl groups, 1-propenyl groups, isopropenyl groups), butenyl groups (1-butenyl groups, crotyl groups, methallyl groups, isocrotyl groups, etc.), pentenyl groups (1-pentenyl groups, etc.), hexenyl groups (1-hexenyl groups, etc.), heptenyl groups (1-heptenyl groups, etc.), octenyl groups (1-octenyl groups, etc.), cyclopentenyl groups (2-cyclopentenyl groups, etc.), and cyclohexenyl groups (3-cyclohexenyl groups).

[0046] R 16 The aromatic hydrocarbon group in the formula (I) is a group in which one hydrogen atom on an aromatic ring has been removed from an aromatic carbon ring. The aromatic hydrocarbon group has 6 to 18 carbon atoms, preferably 6 to 12 or 6 to 10, and more preferably 6. Examples of the aromatic hydrocarbon group include a phenyl group, a naphthyl group, and an anthracenyl group, with a phenyl group or a naphthyl group being preferred, and a phenyl group being more preferred.

[0047] In formula (4), m 4represents an integer from 0 to 5. m 4 The upper limit of m is preferably 4 or less, more preferably 3 or less, even more preferably 2 or less, and particularly preferably 1 or less. 4 may be 0 or 1.

[0048] In the component (1A), the partial structure represented by formula (T-1) preferably accounts for 1 to 99 mass%, more preferably 3 to 97 mass%, and even more preferably 5 to 95 mass%, of the total amount (100 mass%) of the component (1A).

[0049] In the component (1A), the partial structure represented by formula (T-2) preferably accounts for 1 to 99 mass%, more preferably 3 to 97 mass%, and even more preferably 5 to 95 mass%, of the total amount (100 mass%) of the component (1A).

[0050] Specific examples of the component (1A) include maleimide compounds represented by the following formula (3-1). [ka]

[0051] The number average molecular weight (Mn) of component (1A) is preferably in the range of 200 to 1,500, and more preferably in the range of 300 to 800. The weight average molecular weight (Mw) of component (1A) is preferably in the range of 280 to 2,000, and more preferably in the range of 330 to 1,200.

[0052] In view of excellent solvent solubility, heat resistance, and low dielectric tangent, the molecular weight distribution (weight average molecular weight (Mw) / number average molecular weight (Mn)) of component (1A) calculated by gel permeation chromatography (GPC) measurement is preferably in the range of 1.01 to 4.0, more preferably 1.05 to 2.0, and even more preferably 1.10 to 1.8. Note that when the molecular weight distribution is wide and there is a large amount of high molecular weight components as seen in the GPC chart obtained from GPC measurement, the proportion of high molecular weight components that contribute to flexibility increases, and therefore, compared to cured products using conventional maleimides, brittleness is reduced, and a cured product with excellent flexibility and pliability can be obtained, which is a preferred embodiment.

[0053] The number average molecular weight (Mn), weight average molecular weight (Mw), and molecular weight distribution (weight average molecular weight (Mw) / number average molecular weight (Mn)) of component (1A) can be measured using gel permeation chromatography (hereinafter abbreviated as "GPC").

[0054] The content of component (1A) in the resin composition, when the resin components in the resin composition are taken as 100% by mass, is preferably 0.1% by mass or more, more preferably 1% by mass or more or 2% by mass or more, even more preferably 3% by mass or more or 4% by mass or more, and particularly preferably 5% by mass or more or 6% by mass or more, from the viewpoint of significantly achieving the effects of the present invention. In one embodiment, it may be 7% by mass or more, 8% by mass or more, etc. The upper limit is preferably 50% by mass or less or 45% by mass or less, more preferably 40% by mass or less or 35% by mass or less, even more preferably 30% by mass or less or 25% by mass or less, and particularly preferably 20% by mass or less, 15% by mass or less, 14% by mass or less, or 13% by mass or less. In one embodiment, it may be 12% by mass or less, 11% by mass or less, 10% by mass or less, etc.

[0055] The content of component (1A) in the resin composition, based on 100% by mass of the nonvolatile components in the resin composition, is preferably 0.01% by mass or more or 0.1% by mass or more, more preferably 0.2% by mass or more or 0.5% by mass or more, even more preferably 0.8% by mass or more or 1% by mass or more, and particularly preferably 1.2% by mass or more or 1.5% by mass or more, from the viewpoint of significantly achieving the effects of the present invention. In one embodiment, the content may be 1.8% by mass or more, 2% by mass or more, 2.2% by mass or more, or 2.5% by mass or more. The upper limit is preferably 20% by mass or less or 18% by mass or less, more preferably 15% by mass or less or 12% by mass or less, even more preferably 10% by mass or less or 8% by mass or less, and particularly preferably 5% by mass or less, 4% by mass or less, 3.8% by mass or less, or 3.5% by mass or less. In one embodiment, the content may be 3.2% by mass or less, or 3% by mass or less.

[0056] <(1A) Method for producing a maleimide compound having a first specific structure> There are no limitations on the method for producing component (1A). In one embodiment, component (1A) can be produced using, for example, an aromatic amine compound (a) represented by the following formula (a1) (hereinafter also simply referred to as "aromatic amine compound (a)"), a compound (b) having a benzyl ether skeleton, and maleic anhydride as reaction raw materials (1). [ka] (In formula (a1), R a7 and R a8 each independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms; R 1 represents a hydrocarbon group having 1 to 18 carbon atoms, and R 2 and R 3 each independently represents a hydrogen atom or a hydrocarbon group having 1 to 18 carbon atoms.

[0057] In addition, component (1A) preferably uses, as reaction raw materials (2), an intermediate amine compound (c) in which aromatic amine compounds (a) are linked together via a structural unit derived from compound (b) having a benzyl ether skeleton, and maleic anhydride. Furthermore, the intermediate amine compound (c) is preferably a compound obtained by using, as reaction raw materials (3), aromatic amine compound (a) and compound (b) having a benzyl ether skeleton.

[0058] In other words, the intermediate amine compound (c) in this embodiment preferably has a structural unit in which a structural unit of an aromatic amine compound (a) having an aromatic ring to which an amino group is bonded and a structural unit derived from a compound (b) having a benzyl ether skeleton are chemically linked. The component (1A) has a structure in which the amino group bonded to the aromatic ring of the intermediate amine compound (c) is substituted with an N-substituted maleimide ring. The term "amino group" as used herein also includes a substituted amino group in which the hydrogen atom of -NH2 is further substituted with an alkyl group having 1 to 6 carbon atoms.

[0059] Therefore, the "maleimide compound" component (1A) and the "intermediate amine compound (c)" that is the precursor of the "maleimide compound" are polymer compounds that differ in that the amino group bonded to the aromatic ring is replaced with an N-substituted maleimide ring. The structural unit of the aromatic amine compound (a) refers to a group obtained by removing at least one hydrogen atom from the aromatic ring of the aromatic amine compound (a). For example, when the aromatic amine compound (a) is represented by the formula (a1) described below, the group obtained by removing at least one hydrogen atom from the benzene ring of the formula (a1) is referred to as the structural unit of the aromatic amine compound (a). The structural unit derived from the compound (b) having a benzyl ether skeleton refers to a group obtained by replacing -(CHO)- with -(CH)- except for the terminal group in the compound (b) having a benzyl ether skeleton, and by replacing -(CHO)-R directly bonded to the benzene ring. b is a group in which all of R are substituted with -(CH2)-. b represents a hydrogen atom or a hydrocarbon group having 1 to 18 carbon atoms.

[0060] In the present embodiment, the aromatic amino compound (a) having an aromatic ring structure with a substituent at a specific position is used as a reaction raw material. This makes it easier to control the reaction site with the compound (b) having a benzyl ether skeleton, which will be described later. This makes it easier to obtain a linear maleimide compound with a homogeneous chemical structure. As a result, a maleimide compound (component (1A)) can be provided that exhibits excellent solubility in solvents, high heat resistance during curing, and a low dielectric loss tangent.

[0061] The aromatic amine compound (a) represented by formula (a1), the compound (b) having a benzyl ether skeleton, and maleic anhydride, which are constituents of the reaction raw material (1) of the maleimide compound (component (1A)), will be described below.

[0062] <<Aromatic amine compound (a) represented by formula (a1)>> The aromatic amine compound (a) in this embodiment has an aromatic ring to which an amino group is bonded, and a structure in which a hydrocarbon group having 1 to 18 carbon atoms is bonded to one of the ortho positions of the aromatic ring, as represented by the following formula (a1): [ka] (In formula (a1), R a7 and R a8 each independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms; R 1 represents a hydrocarbon group having 1 to 18 carbon atoms, and R 2 and R 3 each independently represents a hydrogen atom or a hydrocarbon group having 1 to 18 carbon atoms.

[0063] In the aromatic amine compound (a) of the present embodiment, a hydrocarbon group (R 2 , R 3) includes linear, branched, or cyclic hydrocarbon groups having 1 to 18 carbon atoms, preferably linear or branched hydrocarbon groups having 1 to 12 carbon atoms, and more preferably linear or branched alkyl groups having 1 to 6 carbon atoms. As shown in the above formula (a1), it has a bonding site with the compound (b) having a benzyl ether skeleton at each of the ortho- and para-positions of the aromatic ring.

[0064] In the above formula (a1), R 1 represents a hydrocarbon group having 1 to 18 carbon atoms, preferably a hydrocarbon group having 1 to 12 carbon atoms, and more preferably a hydrocarbon group having 1 to 6 carbon atoms.

[0065] In the above formula (a1), R 2 represents a hydrogen atom or a hydrocarbon group having 1 to 18 carbon atoms, preferably a hydrocarbon group having 1 to 12 carbon atoms, and more preferably a hydrocarbon group having 1 to 6 carbon atoms.

[0066] In the above formula (a1), R 3 represents a hydrogen atom or a hydrocarbon group having 1 to 18 carbon atoms, preferably a hydrocarbon group having 1 to 12 carbon atoms, and more preferably a hydrocarbon group having 1 to 6 carbon atoms.

[0067] Furthermore, by making the number of hydrocarbon groups (e.g., alkyl groups) substituted on the aromatic ring of the aromatic amine compound (a) one or more, it becomes easier to control the reaction site with the compound (b) having a benzyl ether skeleton, which will be described later, and it becomes easier to obtain a maleimide compound (component (1A)) having a specific chemical structure. As a result, the cured product of the resin composition tends to exhibit solvent solubility, heat resistance, and excellent high-frequency electrical properties. In particular, the substituent (R 1 ), after the amino group derived from the aromatic amine compound (a) is maleimidized, the dihedral angle formed by the plane of the aromatic ring of the aniline skeleton and the plane of the nitrogen-containing five-membered ring of the maleimide becomes large, which is thought to make the crystallinity derived from the maleimide group more likely to collapse, thereby improving the solubility.

[0068] In this embodiment, it is preferred that, among the carbon atoms in the benzene ring constituting the aromatic amine compound (a), one or more carbon atoms having the largest HOMO electron density (Huckel coefficient) are unsubstituted (substituted with a hydrogen atom). Therefore, it is preferred that the aromatic amine compound (a) represented by formula (a1) has any two of the 2-, 4-, and 6-positions substituted with a hydrogen atom. A particularly preferred form of the aromatic amine compound (a) represented by formula (a1) is one in which the 2-position is substituted with an alkyl group and the 4- and 6-positions are hydrogen atoms. This allows for the formation of ArS by a cationoid reagent formed from the compound (b) having a benzyl ether skeleton, which will be described later. E This makes it easier to control the reaction and molecular design. As a result, the cured product of the resin composition is more likely to exhibit solvent solubility, heat resistance, and excellent high-frequency electrical properties. In particular, by substituting hydrogen atoms at the 4- and 6-positions of the benzene ring of formula (a1), a maleimide compound (or intermediate amine compound) with an elongated linear molecule can be obtained.

[0069] Specific examples of the aromatic amine compound (a) of the present embodiment include, for example, o-toluidine, 2-ethylaniline, 2-propylaniline, 2-butylaniline, 2-cyclobutylaniline, 2-cyclopentylaniline, 2-cyclohexylaniline, dimethylaniline (2,3-xylidine, 2,4-xylidine, or 2,5-xylidine), diethylaniline (2,3-diethylaniline, 2,4-diethylaniline, or 2,5-diethylaniline), diisopropylaniline (2,3-diisopropylaniline, 2,4-diisopropylaniline, or Examples of aromatic amine compounds that can be used include 2,5-diisopropylaniline, ethylmethylaniline (e.g., ethylmethylaniline having a methyl group at one of the 2,3-, 2,4-, or 2,5-positions and an ethyl group at the other), methylisopropylaniline (e.g., methylisopropylaniline having a methyl group at one of the 2,3-, 2,4-, or 2,5-positions and an isopropyl group at the other), and ethylbutylaniline (e.g., ethylbutylaniline having an ethyl group at one of the 2,3-, 2,4-, or 2,5-positions and a butyl group at the other). The butyl group includes n-butyl, tert-butyl, and sec-butyl. The aromatic amine compounds (a) of the present embodiment may be used alone or in combination of two or more thereof.

[0070] For example, in the case of a chemical structure in which a maleimide group is directly bonded to an unsubstituted benzene ring, such as N-phenylmaleimide, the benzene ring and the five-membered maleimide ring are stable when aligned on the same plane, which facilitates stacking and results in high crystallinity. This results in poor solvent solubility. In contrast, in the case of the present disclosure, for example, when an alkyl group (e.g., an ethyl group) is substituted on the benzene ring, such as in 2-ethylaniline, the steric hindrance of the ethyl group causes the benzene ring and the five-membered maleimide ring to assume a twisted conformation, making stacking difficult. This reduces crystallinity and improves solvent solubility, making this a preferred embodiment. However, if the steric hindrance is too great or depending on the substitution position of the alkyl group, there is a concern that the reactivity during maleimide synthesis may be hindered or the curability of the maleimide group may be impaired when preparing a cured product. Therefore, it is preferable to use, for example, an aromatic amine compound (a) having a hydrocarbon group having 1 to 6 carbon atoms. In this embodiment, the aromatic amine compound (a) represented by the above formula (a1) may be used alone or in combination of two or more kinds.

[0071] <<Compound (b) having a benzyl ether skeleton>> The compound (b) having a benzyl ether skeleton in this embodiment may be a single compound or a mixture. When the compound (b) having a benzyl ether skeleton in this embodiment is a single compound, it is preferably a compound having a partial structure represented by formula (b) described below, more preferably a compound represented by formula (b1) described below, and even more preferably a compound represented by formula (b2) described below.

[0072] On the other hand, when the compound (b) having a benzyl ether skeleton in this embodiment is a mixture, it is preferably not only a mixture containing a compound having a partial structure represented by the following formula (b) and / or a compound having a benzyl ether skeleton represented by the following formula (b1), but also a mixture in which a component having a partial structure represented by the following formula (b3) accounts for 95% by mass or more and 100% by mass or less of the total. The compound (b) having a benzyl ether skeleton in this embodiment is preferably a compound having a benzyl ether skeleton represented by the following formula (b): [ka] (In formula (b), R b3 each independently represents an alkyl group having 1 to 18 carbon atoms, m b2 represents an integer between 0 and 4, and j 1 and j 2 are each independently an integer of 0 to 4, 1 +j 2 ≧1, and k 1 and k 2 are each independently 0 or 1, and * represents a bond to another atom.

[0073] The compound (b) having a benzyl ether skeleton in this embodiment is preferably a product obtained by reacting alkylbenzene with formaldehyde in the presence of an acid catalyst.

[0074] The compound (b) having a benzyl ether skeleton in this embodiment preferably has a benzyl ether skeleton represented by the above formula (b) and satisfies at least one of the following physical properties, thereby enabling the synthesis of a resin that can exhibit better solvent solubility, heat resistance, and dielectric properties.

[0075] In the present embodiment, the upper limit of the number average molecular weight (Mn) of the compound (b) having a benzyl ether skeleton is preferably 1,200 or less, more preferably 800 or less, and even more preferably 500 or less. The lower limit of the number average molecular weight (Mn) of the compound (b) having a benzyl ether skeleton is preferably 200 or more, more preferably 240 or more, and even more preferably 250 or more.

[0076] In this embodiment, the upper limit of the oxygen content of the compound (b) having a benzyl ether skeleton is preferably 15% by mass or less, more preferably 13% by mass or less, and even more preferably 12% by mass or less. The lower limit of the oxygen content of the compound (b) having a benzyl ether skeleton is preferably 4% by mass or more, more preferably 5% by mass or more, and even more preferably 7% by mass or more.

[0077] In this embodiment, the upper limit of the specific gravity of the compound (b) having a benzyl ether skeleton is preferably less than 1.2, more preferably less than 1.15, and even more preferably less than 1.10. The lower limit of the specific gravity of the compound (b) having a benzyl ether skeleton is preferably 1.0 or more, more preferably 1.01 or more, and even more preferably 1.02 or more.

[0078] In this embodiment, the upper limit of the viscosity (75°C) of the compound (b) having a benzyl ether skeleton is preferably 1,500 mPa·s or less, more preferably 1,000 mPa·s or less, and even more preferably 900 mPa·s or less. The lower limit of the viscosity (75°C) of the compound (b) having a benzyl ether skeleton is preferably 30 mPa·s or more, more preferably 50 mPa·s or more, and even more preferably 70 mPa·s or more.

[0079] In this embodiment, the upper limit of the indirect viscosity (20°C) of the compound (b) having a benzyl ether skeleton is preferably 1,000 mPa·s or less, more preferably 800 mPa·s or less, and even more preferably 500 mPa·s or less. The lower limit of the indirect viscosity (20°C) of the compound (b) having a benzyl ether skeleton is preferably 10 mPa·s or more, more preferably 20 mPa·s or more, and even more preferably 30 mPa·s or more. The hydroxyl value of the compound (b) having a benzyl ether skeleton in this embodiment is preferably 16 to 50 (mgKOH / g), more preferably 18 to 40 (mgKOH / g), and even more preferably 22 to 35 (mgKOH / g).

[0080] A preferred example of the compound (b) having a benzyl ether skeleton, which is the reaction raw material (1) of the component (1A), is a compound having a structural unit represented by the following formula (b1). [ka] (In the above formula (b1), R b1 each independently represents a hydrogen atom or an alkyl group having 1 to 11 carbon atoms, and one or more -CH2- in the alkyl group may be replaced with -O- or -C(=O)- so that they are not adjacent to each other; R b2 and R b3 each independently represents a hydrocarbon group having 1 to 18 carbon atoms, L 1 each independently represents an alkylene group having 1 to 11 carbon atoms, and one or more -CH2- in the alkylene group may be replaced with -O- so that they are not adjacent to each other, L 2 represents a single bond or an alkylene group having 1 to 11 carbon atoms, in which one or more -CH2- groups may be replaced with -O- or -(C=O)- so that they are not adjacent to each other, Z 1 each independently represents a hydrogen atom or a hydrocarbon group having 1 to 11 carbon atoms, k represents an integer between 0 and 20, m b1 and mb2 each independently represents an integer of 0 to 4, R b1 or L 2 At least one of them has a —CHO— group.

[0081] R in the above formula (b1) b1 represents preferably a hydrogen atom or a hydrocarbon group having 1 to 11 carbon atoms, more preferably a hydrogen atom or a hydrocarbon group having 1 to 9 carbon atoms, and one or more -CH2- in the hydrocarbon group may be replaced with -O- so that they are not adjacent to each other. b1 represents a hydrogen atom, an alkyl group having 1 to 9 carbon atoms, an alkoxy group having 1 to 9 carbon atoms, a hydroxyalkyl group having 1 to 9 carbon atoms, -(CHO) p1 -C(=O)-R b4 , -(CHO) p1 -R b4 , -(CHO) p1 -(CH2) p2 -R b4 , -(CH2) p3 -(CH2O) p1 -(CH2) p2 -R b4 , -(OCH2) q1 -R b4 , -(OCH2) q1 -(CH2) q2 -R b4 and -(CH2) q3 -(OCH2) q1 -(CH2) q2 -R b4 Preferably, the R b4 represents a hydrogen atom or an alkyl group having 1 to 5 carbon atoms. Furthermore, p1 to p3 and q1 to q3 each independently preferably represent an integer of 1 to 11, more preferably an integer of 1 to 6, even more preferably an integer of 1 to 3, and particularly preferably an integer of 1 or 2.

[0082] Furthermore, R b1 or L 2 Preferably, at least one of Rb1 and L 2 It is more preferable that both of the above have a —CH2O— group.

[0083] R in the above formula (b1) b2 and R b3 are each independently R in the above formula (1). 13 Therefore, R in the above formula (b1) b2 and R b3 are each independently preferably an alkyl group having 1 to 18 carbon atoms, more preferably an alkyl group having 1 to 12 carbon atoms, and even more preferably an alkyl group having 1 to 6 carbon atoms. b1 is an integer equal to or greater than 2, R equal to or greater than 2 b2 may be the same or different groups. b2 is an integer equal to or greater than 2, R equal to or greater than 2 b3 may be the same as each other or may be different groups.

[0084] In the above formula (b1), L 1 are each independently an alkylene group preferably having 1 to 11 carbon atoms, more preferably an alkylene group having 1 to 9 carbon atoms, and one or more -CH2- in the alkylene group may be replaced with -O- so that they are not adjacent to each other. 1 represents an alkylene group having 1 to 11 carbon atoms, an alkyleneoxy group having 1 to 11 carbon atoms, -(CHO) p1 -C(=O)-R b4 , -(CHO) p1 -R b4 , -(CHO) p1 -(CH2) p2 -, -(CH2) p3 -(CH2O) p1 -(CH2) p2 -, -(OCH2) q1 -, -(OCH2) q1 -(CH2) q2 - and -(CH2) q3 -(OCH2) q1 -(CH2) q2-, and -. Furthermore, p1 to p3 and q1 to q3 each independently preferably represent an integer of 1 to 11, more preferably an integer of 1 to 6, even more preferably an integer of 1 to 3, and particularly preferably an integer of 1 to 2.

[0085] In the above formula (b1), L 2 are each independently preferably a single bond or an alkylene group having 1 to 11 carbon atoms, more preferably a single bond or an alkylene group having 1 to 9 carbon atoms, and one or more -CH2- in the alkylene group may be replaced with -O- so that they are not adjacent to each other. 2 represents a single bond, an alkylene group having 1 to 11 carbon atoms, an alkyleneoxy group having 1 to 11 carbon atoms, -(CHO) p1 -C(=O)-, -(CHO) p1 -, -(CHO) p1 -(CH2) p2 -, -(CH2) p3 -(CH2O) p1 -(CH2) p2 -, -(OCH2) q1 -, -(OCH2) q1 -(CH2) q2 - and -(CH2) q3 -(OCH2) q1 -(CH2) q2 -, and -. Furthermore, p1 to p3 and q1 to q3 each independently preferably represent an integer of 1 to 11, more preferably an integer of 1 to 6, even more preferably an integer of 1 to 3, and particularly preferably an integer of 1 to 2.

[0086] Furthermore, R b1 or L 2 Preferably, at least one of R b1 and L 2 It is more preferable that both of the above have a —CH2O— group.

[0087] Z in the above formula (b1) 1preferably represents a hydrogen atom or an alkyl group having 1 to 11 carbon atoms, and more preferably represents a hydrogen atom or an alkyl group having 1 to 9 carbon atoms.

[0088] In the above formula (b1), k is preferably an integer of 0 to 20, more preferably an integer of 0 to 15, and even more preferably an integer of 0 to 10. When k is 2 or more, the number of L 1 may be the same group or different groups.

[0089] A preferred embodiment of the compound (b) having a benzyl ether skeleton of this embodiment may be a compound having a structural unit represented by the following formula (b2). [ka] (In formula (b2), R b1 each independently represents a hydrogen atom or an alkyl group having 1 to 11 carbon atoms, and one or more -CH2- in the alkyl group may be replaced with -O- or -C(=O)- so that they are not adjacent to each other; R b2 and R b3 each independently represents an alkyl group having 1 to 18 carbon atoms, L 1 each independently represents an alkylene group having 1 to 11 carbon atoms, and one or more -CH2- in the alkylene group may be replaced with -O- so that they are not adjacent to each other, L 2 represents a single bond or an alkylene group having 1 to 11 carbon atoms, in which one or more -CH2- groups may be replaced with -O- or -(C=O)- so that they are not adjacent to each other, Z 1 each independently represents a hydrogen atom or an alkyl group having 1 to 11 carbon atoms, k represents an integer between 0 and 20, m b1 and m b2 each independently represents an integer of 0 to 4, R b1 or L 2At least one of them has a —CHO— group.

[0090] In the above formula (b2), R b1 , R b2 and R b3 , L 1 , L 2 , Z 1 , k, and m b1 and m b2 The preferred form of is the same as that of the above formula (b1).

[0091] In this embodiment, the compound (b) having a benzyl ether skeleton may be used alone or in combination of two or more types, or may be a mixture containing two or more compounds (b) having different benzyl ether skeletons. For ease of explanation, the term "compound (b) having a benzyl ether skeleton" used herein refers to a mixture containing two or more compounds (b) having different benzyl ether skeletons as a "mixture (b) having a benzyl ether skeleton." Therefore, the term "compound (b) having a benzyl ether skeleton" does not only refer to a single compound, but also encompasses a mixture (b) having a benzyl ether skeleton.

[0092] The mixture (b) having a benzyl ether skeleton of this embodiment has a partial structure represented by the following formula (b3): [ka] (In formula (b3), L 3 and L 4 are linking groups, each independently representing one type of group selected from the group consisting of -CH-, -CHO-CH-, -(CHO)-CH-, and -(CHO)-CH-, and * represents a bond to another atom.) preferably accounts for 95% by mass or more and 100% by mass or less of the entire mixture (b) having a benzyl ether skeleton.

[0093] In the mixture (b) having a benzyl ether skeleton of the present embodiment, the component having the partial structure represented by the above formula (b3) accounts for 95% by mass or more and 100% by mass or less of the entire mixture (b) having a benzyl ether skeleton, and it is preferable that the mixture (b) satisfies the following requirement (I) or (II): (I) The number of linking groups per molecule constituting the component having the partial structure represented by the above formula (b3) (L 3 and L 4 The total number of (a) is between 1.1 and 2.4. (II) The number of terminal groups bonded to the terminals of the molecules constituting the component having the partial structure represented by the above formula (b3) is 0.5 or more and 1.5 or less per molecule.

[0094] In this embodiment, the linking group (L 3 and L 4 ) includes one group selected from the group consisting of -CH2-, -CH2O-CH2-, -(CH2O)2-CH2- and -(CH2O)3-CH2-.

[0095] In the entire mixture (b) having a benzyl ether skeleton, the following linking group (L 3 and L 4 The number of the components (total number of components) is preferably one of the following compositions (1) to (4). (1) The number of linking groups "-CH2-" is preferably 0.65 or more and 1.4 or less. (2) The number of linking groups "-CH2O-CH2-" is preferably 0.07 or more and 0.2 or less, and more preferably 0.08 or more and 0.14 or less. (3) The number of linking groups "-(CH2O)2-CH2-" is preferably 0.10 or more and 0.8 or less, more preferably 0.2 or more and 0.8 or less. In another embodiment, it is preferably more than 0.41 and 0.8 or less. (4) The number of linking groups "-(CH2O)3-CH2-" is preferably 0.05 or more and 0.65 or less, more preferably 0.09 or more and 0.6 or less, and even more preferably 0.10 or more and 0.55 or less.

[0096] In the mixture (b) having a benzyl ether skeleton of this embodiment, it is preferable that one or more groups selected from the group consisting of -CH2-OH, -CHO-CH3, -(CHO)2-CH3, -(CHO)3-CH3, and -(CHO)-COH be present as a terminal group bonded to the end of a molecule constituting a component having a partial structure represented by formula (b3) above.

[0097] The entire mixture (b) having a benzyl ether skeleton preferably has a benzyl ether skeleton represented by the above formula (b3), and the number of terminal groups per molecule is preferably 0.5 to 1.5. The entire mixture (b) having a benzyl ether skeleton preferably has the following number of terminal groups per molecule having a benzyl ether skeleton in the composition of (5) to (9) below. (5) The number of terminal groups "-CH2-OH" is preferably 0.17 or more and 0.4 or less, and more preferably 0.18 or more and 0.25 or less. (6) The number of terminal groups "-CH2O-CH3" is preferably 0.17 or more and 0.7 or less, and more preferably 0.18 or more and 0.44 or less. (7) The number of terminal groups "-(CH2O)2-CH3" is preferably 0.08 or more and 0.6 or less, and more preferably 0.09 or more and 0.3 or less. (8) The number of terminal groups "-(CHO)-CH" is preferably substantially zero, more preferably 0.3 or less, and even more preferably 0.2 or less. (9) The number of terminal groups "-(CHO)-COH" is preferably 0 or more and 0.1 or less, and more preferably 0.01 or more and 0.1 or less.

[0098] In the mixture (b) having a benzyl ether skeleton of this embodiment, the chemical structure and number of linking groups, and the chemical structure and number of terminal groups can be calculated from NMR, as shown in the Examples section below, or can be obtained by referring to the manufacturer's catalog.

[0099] In the present embodiment, the compound (b) having a benzyl ether skeleton may be a synthetic product or a commercially available product. A preferred example of the commercially available compound (b) having a benzyl ether skeleton is a xylene resin (trade name: Nikanol (Y-50, Y-100, Y-300, Y-1000, LLL, LL, L, or H)) manufactured by Fudow Co., Ltd.

[0100] In this embodiment, the structural unit of the compound (b) having a benzyl ether skeleton is preferably contained in an amount of 1 to 99 mass %, more preferably 5 to 95 mass %, relative to the total amount (100 mass %) of the component (1A). The structural unit of the compound (b) having a benzyl ether skeleton refers to a group represented by the above formula (1).

[0101] <<Maleic anhydride>> In this embodiment, maleic anhydride is included in the reaction raw material (1) of the component (1A), and is used in the reaction of maleimidizing the amino group derived from the aromatic amine compound (a), as described below.

[0102] A specific embodiment of the method for producing the component (1A) includes, for example, a production method comprising the following steps (1) and (2). Step (1): As a reaction raw material (2), an aromatic amine compound (a) represented by the above formula (a1) is reacted with a compound (b) having a benzyl ether skeleton to obtain the compound (a) of this embodiment. A step of obtaining the intermediate amine compound (c) in the above step. Step (2): A step of reacting the intermediate amine compound (c) obtained in the above step (1) as the reaction raw material (3) with maleic anhydride to obtain component (1A).

[0103] Specifically, the method for producing component (1A) preferably comprises step (1) (also referred to as the "crosslinking step") of reacting aromatic amine compound (a) represented by formula (a1) with compound (b) having a benzyl ether skeleton in the presence of a solid acid catalyst, and step (2) (also referred to as the "condensation step") of condensing intermediate amine compound (c) produced in step (1) with maleic anhydride. Each step in the method for producing component (1A) will be explained below in order.

[0104] <<Step (1): Production process of intermediate amine compound (c)>> The steps for producing the intermediate amine compound (c) in this embodiment are described below. Step (1) is a step of reacting the aromatic amine compound (a) described above with the compound (b) having a benzyl ether skeleton described above (e.g., nicanol) and other compounds added as needed in the presence of an acid catalyst. This reaction produces the intermediate amine compound (c).

[0105] The blending ratio of the aromatic amine compound (a) and the compound having a benzyl ether skeleton (b) is preferably 0.001 to 1 mol, more preferably 0.1 to 0.5 mol, as the molar ratio of the compound having a benzyl ether skeleton (b) to 1 mol of the aromatic amine compound (a), taking into consideration the balance of physical properties such as moldability during production and curability of the resulting cured product.

[0106] Furthermore, when a mixture such as the above-mentioned mixture (b) having a benzyl ether skeleton is used as the compound (b) having a benzyl ether skeleton, the reactive site with the aromatic amine compound (a) may be a methyleneoxy moiety (e.g., a benzyl ether moiety (Ph-CHO-CH-), a benzyl alcohol moiety (Ph-CHO-H), or a methyleneoxy moiety (-CH-O-)) in the compound (b) having a benzyl ether skeleton contained in the mixture. Furthermore, when the total number of these reactive sites is taken as 1, the amount of the aromatic amine compound (a) is preferably equal to or more than 10 times the total amount, and for example, the amount of the aromatic amine compound (a) is preferably 1 to 10 moles per mole of the total number of the reactive sites.

[0107] In addition, specific methods for carrying out the above reaction include charging all raw materials at once and reacting them at a predetermined temperature, or charging either aromatic amine compound (a) or compound (b) having a benzyl ether skeleton with an acid catalyst and maintaining the temperature at a predetermined level while adding dropwise the other aromatic amine compound (a) or compound (b) having a benzyl ether skeleton. The dropwise addition time is typically 0.1 to 12 hours, preferably 6 hours or less. After the reaction, if a solvent is used, the intermediate amine compound (c) can be obtained by distilling off the solvent and unreacted materials, if necessary. If no solvent is used, the intermediate amine compound (c), which is the target product, can be obtained by distilling off the unreacted materials.

[0108] The acid catalyst used in step (1) of this embodiment can be any of organic acids, inorganic acids, and solid acids. Examples of the organic acid include aliphatic sulfonic acids such as methanesulfonic acid and fluoromethanesulfonic acid; aromatic sulfonic acids such as 3-morpholinopropanesulfonic acid, piperazine-1,4-bis(2-ethanesulfonic acid), 10-camphorsulfonic acid, 4-chlorobenzenesulfonic acid, benzenesulfonic acid, p-toluenesulfonic acid, and trifluoromethanesulfonic acid; alkyl phosphoric acids such as dimethyl phosphate and diethyl phosphate; alkyl sulfuric acids such as dimethyl sulfate, diethyl sulfate, and lauryl sulfate; aromatic sulfuric acids such as phenyl sulfate and phenyl fluoride sulfate; and various acids such as oxalic acid. Examples of the inorganic acid include phosphoric acid, hydrochloric acid, sulfuric acid, nitric acid, and boric acid. Examples of the solid acid include activated clay, acid clay, alumina, silica alumina, zeolite, layered silicates, heteropolyhydrochloric acid, and strongly acidic ion exchange resins. Examples of the layered silicates include kaolin group (e.g., dickite, nacrite, kaolinite, anoxite, metahalloysite, and halloysite); serpentine group (e.g., chrysotile, lisardite, and antigorite); smectite group (e.g., montmorillonite, sauconite, beidellite, nontronite, saponite, taeniolite, hectorite, and stevensite); vermiculite group (e.g., vermiculite); mica group (e.g., mica, illite, sericite, and glauconite); attapulgite, sepiolite, palygorskite, bentonite, pyrophyllite, talc, and chlorite. These layered silicates may form mixed layers. The acid catalysts may be used alone or in combination. From the viewpoint of handling, solid acids that can be easily removed by filtration after the reaction in step (1) are preferred. When other acids are used, neutralization with a base and washing with water after the reaction are preferred.

[0109] The base is not particularly limited and may be an organic base or an inorganic salt. Examples of the organic base include alkali metal alkoxides such as sodium methoxide, lithium methoxide, sodium ethoxide, lithium ethoxide, sodium tertiary-butoxide, and potassium tertiary-butoxide; trialkylamines such as triethylamine and ethyldiisopropylamine; aniline derivatives having an alkyl group having 1 to 4 carbon atoms such as N,N-dimethylaniline and N,N-diethylaniline; pyridine derivatives which may have an alkyl substituent having 1 to 4 carbon atoms such as pyridine and 2,6-lutidine; and nitrogen-containing heterocyclic compounds such as 1,8-diazabicyclo[5.4.0]-7-undecene. On the other hand, examples of the inorganic base include alkali metal hydrides such as sodium hydride and lithium hydride; alkaline earth metal hydrides such as calcium hydride; alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; alkali metal or alkaline earth metal carbonates or bicarbonates such as sodium carbonate, potassium carbonate, sodium bicarbonate and potassium bicarbonate; and alkali metal or alkaline earth metal halide compounds such as potassium fluoride, cesium fluoride and potassium iodide. These bases may be used alone or in combination of two or more.

[0110] In this embodiment, the amount of the acid catalyst is in the range of 0.1 to 50 parts by mass per 100 parts by mass of the total amount of the raw materials (the compound (b) having a benzyl ether skeleton and the aromatic amine compound (a)). From the viewpoints of ease of handling and economy, the range of 1 to 20 parts by mass is preferred. The reaction temperature is usually in the range of 100 to 300°C, but in order to suppress the formation of isomeric structures and avoid side reactions such as thermal decomposition, the range of 120 to 250°C is preferred.

[0111] In step (1) of the present embodiment, the reaction time of the mixture of the compound (b) having a benzyl ether skeleton and the aromatic amine compound (a), i.e., the time of the crosslinking reaction, is usually in the range of 1 to 60 hours in total under the above reaction temperature conditions, and preferably in the range of 1 to 20 hours in total, because the reaction does not proceed completely if it is short and side reactions such as thermal decomposition of the product occur if it is long.

[0112] In the method for producing intermediate amine compound (c) in this embodiment, since aromatic amine compound (a) or a derivative thereof also serves as a solvent, other solvents are not necessarily used, but it is also possible to use a solvent. For example, when reacting Nikanol L as a raw material to produce compound (b) having a benzyl ether skeleton, a method may be employed in which an azeotropically dehydrating solvent such as toluene, xylene, or chlorobenzene is used, water contained in the catalyst, etc. is azeotropically dehydrated as necessary, the solvent is distilled off, and the reaction is then carried out within the above-mentioned reaction temperature range.

[0113] The intermediate amine compound (c) obtained by the above step (1) preferably has a partial structure represented by the following formula (1), a partial structure represented by formula (t-1) that is chemically bonded to the partial structure represented by formula (1), and a partial structure represented by formula (t-2) that is chemically bonded to the partial structure represented by formula (1). [ka] (In formula (1), R 13 Each independently represents a hydrocarbon group having 1 to 18 carbon atoms. 2 each independently represents an integer of 0 to 4, and n 1 represents the number of repeating units. Two * symbols each represent a bond, and one bond corresponds to L in the following formula (t-1). 13 or L 14 and the other bond is L in the following formula (t-2): 11 or L 12 ) [ka] (In the above formulas (t-1) and (t-2), R 11 and R 15 R each independently represents a hydrocarbon group having 1 to 18 carbon atoms. 12 and R 14 each independently represents a hydrocarbon group having 1 to 18 carbon atoms. 11 , L 12 , L 13 and L 14 Each independently represents a bond. 11 or L 12 is chemically bonded to the partial structure represented by formula (1) at the position of L 13 or L 14 At the position m, the compound is chemically bonded to the partial structure represented by formula (1). 1 and m 3 each independently represents an integer of 0 to 2.)

[0114] R in formula (1) relating to intermediate amine compound (c) 13 , m 2 and n 1 represents R in formula (1) relating to component (1A). 13 , m 2 and n 1 is the same as

[0115] R in formulas (t-1) and (t-2) 11 and R 15 , R 12 and R 14 , L 11 , L 12 , L 13 and L 14 , m 1 and m 3 is R in formulas (T-1) and (T-2). 11 and R 15 , R 12 and R 14 , L 11 , L 12 , L 13 and L 14 , m 1 and m 3 is the same as

[0116] In this embodiment, the amine equivalent of the intermediate amine compound (c) is preferably 160 to 1,200 g / equivalent, more preferably 180 to 600 g / equivalent. In this specification, the amine equivalent of the intermediate amine compound (c) is measured by a method based on the neutralization titration method specified in JIS K0070 (1992).

[0117] <<Step (2): Maleimidation>> Step (2) in this embodiment is a step of reacting the intermediate amine compound (c) obtained in step (1) with maleic anhydride. The amino group of the intermediate amine compound (c) undergoes a maleimidation reaction to form a chemical structure in which the amino group is substituted with an N-substituted maleimide ring, thereby obtaining the maleimide compound of the present disclosure.

[0118] In this embodiment, the intermediate amine compound (c) obtained in step (1) and having the partial structure represented by formula (1), the partial structure represented by formula (t-1), and the partial structure represented by formula (t-2) is charged into a reactor, dissolved in a suitable solvent, and then reacted with maleic anhydride in the presence of a catalyst. After the reaction, unreacted maleic anhydride or other impurities are removed by washing with water or the like, and the solvent is removed under reduced pressure to obtain the target maleimide compound. A dehydrating agent may also be used during the reaction, if necessary.

[0119] Examples of the organic solvent used in step (2) of this embodiment include ketones such as acetone, methyl ethyl ketone (MEK), methyl isobutyl ketone, cyclohexanone, and acetophenone; aprotic solvents such as N,N-dimethylformamide (DMF), N,N-dimethylacetamide, dimethyl sulfoxide, N-methyl-2-pyrrolidone, acetonitrile, and sulfolane; cyclic ethers such as dioxane and tetrahydrofuran; esters such as ethyl acetate and butyl acetate; and aromatic solvents such as benzene, toluene, and xylene. These may be used alone or in combination.

[0120] In step (2) of the present embodiment, the intermediate amine compound (c) and maleic anhydride are preferably mixed in such a manner that the equivalent ratio of maleic anhydride to the amino equivalent of intermediate amine compound (c) is in the range of 1 to 5, more preferably 1 to 3, and the reaction is carried out in an organic solvent in a mass ratio of 0.1 to 10, preferably 0.2 to 5, relative to the total amount of intermediate amine compound (c) and maleic anhydride.

[0121] Examples of catalysts that can be used in step (2) of this embodiment include inorganic salts such as acetates, chlorides, bromides, sulfates, and nitrates of nickel, cobalt, sodium, calcium, iron, lithium, manganese, and the like; inorganic acids such as phosphoric acid, hydrochloric acid, and sulfuric acid; organic acids such as oxalic acid, benzenesulfonic acid, toluenesulfonic acid, methanesulfonic acid, and fluoromethanesulfonic acid; solid acids such as activated clay, acid clay, silica alumina, zeolites, and strongly acidic ion exchange resins; and heteropolyhydrochloric acids. Toluenesulfonic acid is preferred, and p-toluenesulfonic acid is more preferred.

[0122] Examples of dehydrating agents used in step (2) of this embodiment include lower aliphatic carboxylic acid anhydrides such as acetic anhydride, propionic anhydride, and butyric anhydride; oxides such as phosphorus pentoxide, calcium oxide, and barium oxide; inorganic acids such as sulfuric acid; and porous ceramics such as molecular sieves, with acetic anhydride being preferred. There are no particular restrictions on the amounts of catalyst and dehydrating agent used in step (2) of this embodiment, but typically, 0.0001 to 1 mol, preferably 0.01 to 0.3 mol, of catalyst and 1 to 3 mol, preferably 1 to 1.5 mol, of dehydrating agent are used relative to 1 equivalent of the amino group (—NH2) of intermediate amine compound (c).

[0123] In step (2) of this embodiment, the maleimidation reaction conditions are as follows: the intermediate amine compound (c) and maleic anhydride are charged and reacted at a temperature of 10 to 100°C, preferably 30 to 60°C, for 0.5 to 12 hours, preferably 1 to 4 hours, and then the catalyst is added and the reaction is continued at a temperature of 90 to 130°C, preferably 105 to 120°C, for 1 to 24 hours, preferably 1 to 10 hours.

[0124] <(B) Epoxy resin> The resin composition according to the first embodiment of the present invention contains an epoxy resin (B). The epoxy resin (B) may be used singly or in combination of two or more. In one embodiment, it is preferable to use a combination of two or more epoxy resins (B).

[0125] The type of (B) epoxy resin is not particularly limited as long as it has one or more (preferably two or more) epoxy groups in one molecule. Examples of (B) epoxy resins include bixylenol-type epoxy resins, bisphenol A-type epoxy resins, bisphenol F-type epoxy resins, bisphenol C-type epoxy resins, bisphenol S-type epoxy resins, bisphenol AF-type epoxy resins, dicyclopentadiene-type epoxy resins, trisphenol-type epoxy resins, naphthol novolac-type epoxy resins, phenol novolac-type epoxy resins, tert-butyl-catechol-type epoxy resins, naphthalene-type epoxy resins, naphthol-type epoxy resins, anthracene-type epoxy resins, glycidylamine-type epoxy resins, glycidyl ester-type epoxy resins, cresol novolac-type epoxy resins, phenol aralkyl-type epoxy resins, biphenyl-type epoxy resins, biphenyl aralkyl-type epoxy resins, linear Examples of epoxy resins include aliphatic epoxy resins, epoxy resins having a butadiene structure, alicyclic epoxy resins, heterocyclic epoxy resins, spiro ring-containing epoxy resins, cyclohexane-type epoxy resins, cyclohexanedimethanol-type epoxy resins, naphthylene ether-type epoxy resins, trimethylol-type epoxy resins, tetraphenylethane-type epoxy resins, isocyanurate-type epoxy resins, phenolphthalimidine-type epoxy resins, glycerol-type epoxy resins, alkyleneoxy skeleton-containing epoxy resins, fluorene structure-containing epoxy resins, halogenated epoxy resins, and resorcinol-type epoxy resins. Of these, bisphenol A-type epoxy resins, naphthalene-type epoxy resins, and biphenyl-type epoxy resins are preferred, with naphthalene-type epoxy resins and biphenyl-type epoxy resins being more preferred. In one embodiment, component (B) preferably contains an epoxy resin having an aromatic skeleton.

[0126] The resin composition of the present invention preferably contains, as component (B), an epoxy resin having two or more epoxy groups per molecule. From the viewpoint of significantly achieving the desired effects of the present invention, the proportion of the epoxy resin having two or more epoxy groups per molecule relative to 100% by mass of the epoxy resin (B) is preferably 50% by mass or more, more preferably 60% by mass or more, and particularly preferably 70% by mass or more.

[0127] (B) Epoxy resins include epoxy resins that are liquid at a temperature of 20°C (hereinafter sometimes referred to as "liquid epoxy resins") and epoxy resins that are solid at a temperature of 20°C (hereinafter sometimes referred to as "solid epoxy resins"). The resin composition of the present invention may contain, as component (B), only a liquid epoxy resin, only a solid epoxy resin, or a combination of a liquid epoxy resin and a solid epoxy resin. In one embodiment, the resin composition of the present invention preferably contains a combination of a liquid epoxy resin and a solid epoxy resin.

[0128] The liquid epoxy resin is preferably a liquid epoxy resin having two or more epoxy groups in one molecule.

[0129] Examples of liquid epoxy resins include glycerol-type epoxy resins, bisphenol A-type epoxy resins, bisphenol F-type epoxy resins, bisphenol AF-type epoxy resins, naphthalene-type epoxy resins, glycidyl ester-type epoxy resins, glycidylamine-type epoxy resins, phenol novolac-type epoxy resins, alicyclic epoxy resins having an ester skeleton, cyclohexanedimethanol-type epoxy resins, cyclic aliphatic glycidyl ethers, epoxy resins having a butadiene structure, dicyclopentadiene-type epoxy resins, alkyleneoxy-skeleton-containing epoxy resins, fluorene-structure-containing epoxy resins, and resorcinol-type epoxy resins. Bisphenol A-type epoxy resins or naphthalene-type epoxy resins are preferred, and naphthalene-type epoxy resins are more preferred.

[0130] Specific examples of liquid epoxy resins include "EX-992L" manufactured by Nagase ChemteX Corporation, "YX7400" manufactured by Mitsubishi Chemical Corporation, "HP4032", "HP4032D", and "HP-4032SS" (naphthalene-type epoxy resins) manufactured by DIC Corporation; "828US", "jER828EL", "828EL", "825", and "Epikote 828EL" manufactured by Mitsubishi Chemical Corporation, and "850S" (bisphenol A-type epoxy resin) manufactured by DIC Corporation; and "jER807" and "175" manufactured by Mitsubishi Chemical Corporation. 0" (bisphenol F type epoxy resin); "YL9133" (bisphenol C type epoxy resin) manufactured by Mitsubishi Chemical Corporation; "jER152" (phenol novolac type epoxy resin) manufactured by Mitsubishi Chemical Corporation; "630", "630LSD", and "604" (glycidylamine type epoxy resins) manufactured by Mitsubishi Chemical Corporation; "ED-523T" (glycirol type epoxy resin) manufactured by ADEKA Corporation; "EP-3950L" and "EP-3980S" (glycidylamine type epoxy resins) manufactured by ADEKA Corporation. Resin); ADEKA's "EP-4088S" (dicyclopentadiene type epoxy resin); Nippon Steel Chemical & Material's "ZX-1059" (mixture of bisphenol A type epoxy resin and bisphenol F type epoxy resin); Nagase ChemteX's "EX-721" (glycidyl ester type epoxy resin); Nagase ChemteX's "EX-991L" (alkyleneoxy skeleton-containing epoxy resin); Daicel's "Celloxide 2021P" (ester skeleton-containing epoxy resin) alicyclic epoxy resins containing cycloaliphatic epoxy resins); "PB-3600" manufactured by Daicel Corporation, "JP-100" and "JP-200" manufactured by Nippon Soda Co., Ltd. (epoxy resins having a butadiene structure); "ZX1658" and "ZX1658GS" (liquid 1,4-glycidylcyclohexane-type epoxy resins) manufactured by Nippon Steel Chemical & Material Co., Ltd.; "EG-280" (fluorene structure-containing epoxy resin) manufactured by Osaka Gas Chemicals Co., Ltd.; and "EX-201" (resorcinol-type epoxy resin) manufactured by Nagase ChemteX Corporation. These may be used alone or in combination of two or more.

[0131] As the solid epoxy resin, a solid epoxy resin having two or more epoxy groups in one molecule is preferred, and an aromatic solid epoxy resin having three or more epoxy groups in one molecule is more preferred.

[0132] Examples of solid epoxy resins include bixylenol-type epoxy resins, naphthalene-type epoxy resins, naphthalene-type tetrafunctional epoxy resins, naphthol novolac-type epoxy resins, cresol novolac-type epoxy resins, dicyclopentadiene-type epoxy resins, trisphenol-type epoxy resins, naphthol-type epoxy resins, biphenyl-type epoxy resins, biphenylaralkyl-type epoxy resins, naphthylene ether-type epoxy resins, anthracene-type epoxy resins, bisphenol A-type epoxy resins, bisphenol AF-type epoxy resins, phenolaralkyl-type epoxy resins, tetraphenylethane-type epoxy resins, phenolphthalimidine-type epoxy resins, and fluorene-structure-containing epoxy resins, of which biphenylaralkyl-type epoxy resins or biphenyl-type epoxy resins are preferred, and biphenyl-type epoxy resins are more preferred.

[0133] Specific examples of solid epoxy resins include "HP4032H" (naphthalene-type epoxy resin) manufactured by DIC Corporation; "HP-4700" and "HP-4710" (naphthalene-type tetrafunctional epoxy resins) manufactured by DIC Corporation; "N-690" and "N-695" (cresol novolac-type epoxy resins) manufactured by DIC Corporation; "HP-7200", "HP-7200HH", "HP-7200H", and "HP-7200L" (dicyclopentadiene-type epoxy resins) manufactured by DIC Corporation; and "EXA-7311", "EXA-7311-G3", and "EXA-7311-G4" manufactured by DIC Corporation. "EXA-7311-G4S", "HP-6000", "HP-6000L" (naphthylene ether type epoxy resin); "EPPN-502H" (trisphenol type epoxy resin) manufactured by Nippon Kayaku Co., Ltd.; "NC-7000L" (naphthol novolac type epoxy resin) manufactured by Nippon Kayaku Co., Ltd.; "NC-3000", "NC-3000L", "NC-3000FH", "NC-3100" (biphenyl type epoxy resin) manufactured by Nippon Kayaku Co., Ltd.; "NC-3000H" (biphenyl aralkyl type epoxy resin) manufactured by Nippon Steel Chemical & Material Co., Ltd.; "ESN4" manufactured by Nippon Steel Chemical & Material Co., Ltd. 75V, ESN4100V (naphthalene-type epoxy resin); Nippon Steel Chemical & Material's "ESN485" (naphthol-type epoxy resin); Nippon Steel Chemical & Material's "ESN375" (dihydroxynaphthalene-type epoxy resin); Mitsubishi Chemical's "YX4000H", "YX4000", "YX4000HK", and "YL7890" (bixylenol-type epoxy resin); Mitsubishi Chemical's "YL6121" (biphenyl-type epoxy resin); Mitsubishi Chemical's "YX8800" (anthracene-type epoxy resin); Mitsubishi Chemical's Examples include "YX7700" (phenol aralkyl type epoxy resin); "PG-100" and "CG-500" manufactured by Osaka Gas Chemicals Co., Ltd.; "YL7760" (bisphenol AF type epoxy resin) manufactured by Mitsubishi Chemical Corporation; "YL7800" (fluorene structure-containing 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; and "WHR991S" (phenolphthalimidine type epoxy resin) manufactured by Nippon Kayaku Co., Ltd.These may be used alone or in combination of two or more.

[0134] The epoxy equivalent of the (B) epoxy resin is preferably 50 to 5,000 g / eq. The lower limit of the epoxy equivalent is more preferably 60 g / eq. or more, even more preferably 80 g / eq. or more, and particularly preferably 110 g / eq. or more. The upper limit of the epoxy equivalent is preferably 3,000 g / eq. or less, more preferably 2,000 g / eq. or less, even more preferably 1,000 g / eq. or less, and particularly preferably 500 g / eq. or less, 400 g / eq. or less, or 300 g / eq. or less. The epoxy equivalent is the mass of the epoxy resin containing one equivalent of epoxy groups, and can be measured according to JIS K7236.

[0135] The weight average molecular weight (Mw) of the (B) epoxy resin is preferably 100 to 5,000, more preferably 250 to 3,000, and even more preferably 400 to 1,500. The weight average molecular weight (Mw) of the epoxy resin can be measured by the GPC method as a polystyrene-equivalent value.

[0136] The content of component (B) in the resin composition, when the resin components in the resin composition are taken as 100% by mass, is preferably 1% by mass or more, more preferably 5% by mass or more or 10% by mass or more, even more preferably 15% by mass or more or 20% by mass or more, and particularly preferably 25% by mass or more or 30% by mass or more, with the upper limit being preferably 70% by mass or less or 65% by mass or less, more preferably 60% by mass or less or 55% by mass or less, even more preferably 50% by mass or less or 45% by mass or less, and particularly preferably 40% by mass or less or 35% by mass or less, from the viewpoint of significantly achieving the effects of the present invention.

[0137] The content of component (B) in the resin composition, when the total nonvolatile components in the resin composition is taken as 100% by mass, is preferably 0.1% by mass or more or 0.5% by mass or more, more preferably 1% by mass or more or 2% by mass or more, even more preferably 3% by mass or more, 4% by mass or more or 5% by mass or more, particularly preferably 6% by mass or more, 7% by mass or more or 8% by mass or more, and the upper limit is preferably 40% by mass or less, more preferably 35% by mass or more or 30% by mass or less, even more preferably 25% by mass or more or 20% by mass or less, and particularly preferably 15% by mass or more or 10% by mass or less, from the viewpoint of significantly achieving the effects of the present invention.

[0138] <(D) Curing agent> The resin composition according to the first embodiment of the present invention contains a (D) curing agent. The (D) curing agent may be used alone or in combination of two or more. In one embodiment, it is preferable to use a combination of two or more (D) curing agents. In one embodiment, it is preferable that the (D) curing agent contains an epoxy resin curing agent, and it is more preferable that the (D) curing agent is an epoxy resin curing agent.

[0139] The reactive group equivalent of the (D) curing agent is preferably 50 g / eq. to 3,000 g / eq., more preferably 100 g / eq. to 1,000 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 the (D) curing agent per equivalent of the reactive group.

[0140] In the resin composition according to the first embodiment of the present invention, the curing agent (D) contains the active ester resin (D1). When the curing agent (D) contains the active ester resin (D1), a cured product with high reflow resistance can be obtained.

[0141] As the (D1) active ester resin, a compound having one or more active ester groups per molecule can be used. Among these, preferred active ester resins are compounds having two or more highly reactive ester groups per molecule, such as phenol esters, thiophenol esters, N-hydroxyamine esters, and esters of heterocyclic hydroxy compounds. The active ester resin is preferably one obtained by a condensation reaction between a carboxylic acid compound and / or a thiocarboxylic acid compound and a hydroxy compound and / or a thiol compound. In particular, from the viewpoint of improving heat resistance, active ester resins obtained from a carboxylic acid compound and a hydroxy compound are preferred, and active ester resins obtained from a carboxylic acid compound and a phenol compound and / or a naphthol compound are more preferred.

[0142] Examples of the carboxylic acid compound include benzoic acid, acetic acid, succinic acid, maleic acid, itaconic acid, phthalic acid, isophthalic acid, terephthalic acid, and pyromellitic acid.

[0143] Examples of phenol compounds or naphthol compounds include hydroquinone, resorcinol, bisphenol A, bisphenol F, bisphenol S, phenolphthalene, methylated bisphenol A, methylated bisphenol F, methylated bisphenol S, phenol, o-cresol, m-cresol, p-cresol, catechol, α-naphthol, β-naphthol, 1,5-dihydroxynaphthalene, 1,6-dihydroxynaphthalene, 2,6-dihydroxynaphthalene, dihydroxybenzophenone, trihydroxybenzophenone, tetrahydroxybenzophenone, phloroglucin, benzenetriol, dicyclopentadiene-type diphenol compounds, and phenol novolak. Here, "dicyclopentadiene-type diphenol compounds" refers to diphenol compounds obtained by condensing one dicyclopentadiene molecule with two phenol molecules.

[0144] Preferred specific examples of the (D1) active ester resin include an active ester resin containing a dicyclopentadiene-type diphenol structure (hereinafter also referred to as "dicyclopentadiene-type active ester resin"), an active ester resin containing a naphthalene structure, a phosphorus-containing active ester resin, an active ester resin containing an acetylated product of phenol novolac, an active ester resin containing a benzoylated product of phenol novolac, and an active ester resin containing a butadiene structure. Among these, an active ester resin containing a naphthalene structure, an active ester resin containing a dicyclopentadiene-type diphenol structure, or an active ester resin containing a butadiene structure is preferred, and an active ester resin containing a naphthalene structure is more preferred. The "dicyclopentadiene-type diphenol structure" refers to a divalent structural unit consisting of phenylene-dicyclopentylene-phenylene.

[0145] (D1) Commercially available active ester resins include "EXB9451", "EXB9460", "EXB9460S", "HPC-8000-65T", "EXB-8000H", "HPC-8000L-65MT", and "EXB-8000L-65TM" (manufactured by DIC Corporation) as active ester resins containing a dicyclopentadiene-type diphenol structure; and "EXB-9416-70BK", "EXB-8100L-65T", "EXB-8150L-65T", "HPC-8150-62T", "EXB-8100L-65T", and "E Examples of active ester resins that can be used include "XB-8" (manufactured by DIC Corporation), "PC1300-02-65T", and "PC1300-02-65MA" (manufactured by Air Water Inc.); "EXB-9401" (manufactured by DIC Corporation) as a phosphorus-containing active ester resin; "DC808" (manufactured by Mitsubishi Chemical Corporation) as an active ester resin containing an acetylated product of phenol novolac; and "YLH1026" (manufactured by Mitsubishi Chemical Corporation), "YLH1030" (manufactured by Mitsubishi Chemical Corporation), "YLH1048" (manufactured by Mitsubishi Chemical Corporation), and "EXB-8500-65T" (manufactured by DIC Corporation) as active ester resins that are benzoylated products of phenol novolac.

[0146] In the resin composition according to the first embodiment of the present invention, the (D) curing agent may further include a curing agent other than the (D1) component (hereinafter referred to as "(D2) other curing agent"). Examples of curing agents other than the (D1) active ester resin include phenol-based curing agents, carbodiimide-based curing agents, acid anhydride-based curing agents, amine-based curing agents, benzoxazine-based curing agents, cyanate ester-based curing agents, and thiol-based curing agents. In one embodiment, in the resin composition according to the first embodiment of the present invention, the (D) curing agent preferably includes an active ester resin and a phenol-based curing agent.

[0147] As the phenolic curing agent, a curing agent having one or more, preferably two or more, hydroxyl groups (phenolic hydroxyl groups) bonded to an aromatic ring such as a benzene ring or a naphthalene ring per molecule can be used. From the viewpoint of heat resistance and water resistance, phenolic curing agents having a novolac structure are preferred. Furthermore, from the viewpoint of adhesion to the adherend, nitrogen-containing phenolic curing agents are preferred, and triazine skeleton-containing phenolic curing agents are more preferred. Among these, triazine skeleton-containing phenolic novolac resins are preferred from the viewpoint of highly satisfying heat resistance, water resistance, and adhesion.

[0148] Specific examples of phenolic curing agents include "MEH-7700", "MEH-7810", "MEH-7851", "MEH-7600", "MEH-7851", and "MEH-8000H" manufactured by UBE Corporation; "NHN", "CBN", "GPH", "GPH-65", and "GPH-103" manufactured by Nippon Kayaku Co., Ltd.; and "SN-170", "SN-180", "SN-190", and "S" manufactured by Nippon Steel Chemical & Material Co., Ltd. Examples of such acrylic resins include "SN-475," "SN-485," "SN-495," "SN-495V," "SN-375," and "SN-395" manufactured by DIC Corporation; and "LA-7052," "LA-7054," "LA-3018," "LA-3018-50P," "LA-1356," "TD-2090," "TD2131," "TD-2090-60M," "KA-1160," "KA-1163," and "KA-1165" manufactured by DIC Corporation. These acrylic resins may be used alone or in combination of two or more.

[0149] Examples of carbodiimide curing agents include curing agents having one or more, preferably two or more, carbodiimide structures in one molecule, such as aliphatic biscarbodiimides such as tetramethylene-bis(t-butylcarbodiimide) and cyclohexane-bis(methylene-t-butylcarbodiimide); biscarbodiimides such as aromatic biscarbodiimides such as phenylene-bis(xylylcarbodiimide); aliphatic polycarbodiimides such as polyhexamethylenecarbodiimide, polytrimethylhexamethylenecarbodiimide, polycyclohexylenecarbodiimide, poly(methylenebiscyclohexylenecarbodiimide), and poly(isophoronecarbodiimide); Examples of suitable polycarbodiimides include aromatic polycarbodiimides such as poly(phenylenecarbodiimide), poly(naphthylenecarbodiimide), poly(tolylenecarbodiimide), poly(methyldiisopropylphenylenecarbodiimide), poly(triethylphenylenecarbodiimide), poly(diethylphenylenecarbodiimide), poly(triisopropylphenylenecarbodiimide), poly(diisopropylphenylenecarbodiimide), poly(xylylenecarbodiimide), poly(tetramethylxylylenecarbodiimide), poly(methylenediphenylenecarbodiimide), and poly[methylenebis(methylphenylene)carbodiimide]. These may be used alone or in combination of two or more.

[0150] Commercially available carbodiimide 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 Inc.; and "Stavaxol P," "Stavaxol P400," and "Hykasil 510" manufactured by Lanxess AG. These may be used alone or in combination of two or more.

[0151] The acid anhydride curing agent may be a curing agent having one or more acid anhydride groups in one molecule, and a curing agent having two or more acid anhydride groups in one molecule is preferred. Specific examples of the acid anhydride curing agent include phthalic anhydride, tetrahydrophthalic anhydride, hexahydrophthalic anhydride, methyltetrahydrophthalic anhydride, methylhexahydrophthalic anhydride, methylnadic anhydride, hydrogenated methylnadic anhydride, trialkyltetrahydrophthalic anhydride, dodecenyl succinic anhydride, 5-(2,5-dioxotetrahydro-3-furanyl)-3-methyl-3-cyclohexene-1,2-dicarboxylic anhydride, trimellitic anhydride, pyromellitic anhydride, and benzophenonetetracarboxylic dianhydride. Examples of suitable acid anhydrides include anhydrides, biphenyltetracarboxylic dianhydride, naphthalenetetracarboxylic dianhydride, oxydiphthalic dianhydride, 3,3'-4,4'-diphenylsulfonetetracarboxylic 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(anhydrotrimellitate), and polymeric acid anhydrides such as styrene-maleic acid resins, which are copolymers of styrene and maleic acid. These may be used alone or in combination of two or more.

[0152] Commercially available acid anhydride curing agents include "HNA-100," "MH-700," "MTA-15," "DDSA," and "OSA" manufactured by New Japan Chemical Co., Ltd.; "YH-306" and "YH-307" manufactured by Mitsubishi Chemical Corporation; "HN-2200" and "HN-5500" manufactured by Resonac Corporation; and "EF-30," "EF-40," "EF-60," and "EF-80" manufactured by Cray Valley Chemical Industries, Ltd. These may be used alone or in combination of two or more.

[0153] Examples of amine-based curing agents include curing agents having one or more, preferably two or more, amino groups in one molecule. The amino group of the amine-based curing agent is preferably a primary amino group or a secondary amino group, more preferably a primary amino group. Examples of amine-based curing agents include aliphatic amines, polyether amines, alicyclic amines, and aromatic amines, and among these, aromatic amines are preferred from the viewpoint of achieving the desired effects of the present invention. The amine-based curing agent is preferably a primary amine or a secondary amine, more preferably a primary amine.

[0154] 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-xylylenediamine, 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-hydroxyphenyl)propane. 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)sulfone, bis(4-(3-aminophenoxy)phenyl)sulfone, and the like. Commercially available amine-based curing agents may be used, and examples thereof include "SEIKACURE-S" manufactured by Seika Corporation, "KAYABOND C-200S," "KAYABOND C-100," "KAYAHARD AA," "KAYAHARD AB," and "KAYAHARD AS" manufactured by Nippon Kayaku Co., Ltd., "Epicure W" manufactured by Mitsubishi Chemical Corporation, and "DTDA" manufactured by Sumitomo Seika Chemicals Co., Ltd. These may be used alone or in combination of two or more.

[0155] Specific examples of benzoxazine curing agents include "JBZ-OP100D" and "ODA-BOZ" manufactured by JFE Chemical Corporation, "HFB2006M" manufactured by Showa Polymer Co., Ltd., and "Pd" and "Fa" manufactured by Shikoku Chemicals Corporation. These may be used alone or in combination of two or more.

[0156] Examples of cyanate ester curing agents include bifunctional cyanate resins such as bisphenol A dicyanate, polyphenol cyanate (oligo(3-methylene-1,5-phenylene 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-cyanatephenylmethane), bis(4-cyanate-3,5-dimethylphenyl)methane, 1,3-bis(4-cyanatephenyl-1-(methylethylidene))benzene, bis(4-cyanatephenyl)thioether, and bis(4-cyanatephenyl)ether; multifunctional cyanate resins derived from phenol novolac and cresol novolac; and prepolymers in which these cyanate resins are partially converted to triazine. Specific examples of cyanate ester curing agents include "PT30" and "PT60" (both phenol novolac type multifunctional cyanate ester resins) manufactured by Arxada, "BA230" and "BA230S75" (prepolymers in which part or all of bisphenol A dicyanate is triazinated to form a trimer), etc. These may be used alone or in combination of two or more.

[0157] Examples of thiol-based curing agents include trimethylolpropane tris(3-mercaptopropionate), pentaerythritol tetrakis(3-mercaptobutyrate), tris(3-mercaptopropyl)isocyanurate, etc. These may be used alone or in combination of two or more.

[0158] The content of component (D) in the resin composition, when the resin components in the resin composition are taken as 100% by mass, is preferably 1% by mass or more or 5% by mass or more, more preferably 10% by mass or more or 15% by mass or more, even more preferably 20% by mass or more or 25% by mass or more, particularly preferably 30% by mass or more, 35% by mass or more, 40% by mass or more or 45% by mass or more, and the upper limit is preferably 80% by mass or less, more preferably 75% by mass or less or 70% by mass or less, even more preferably 65% ​​by mass or less or 60% by mass or less, and particularly preferably 55% by mass or less or 50% by mass or less, from the viewpoint of significantly achieving the effects of the present invention.

[0159] The content of component (D) in the resin composition is preferably 0.1% by mass or more, more preferably 1% by mass or more, even more preferably 3% by mass or more or 5% by mass or more, particularly preferably 8% by mass or more, 10% by mass or more, or 12% by mass or more, based on 100% by mass of the nonvolatile components in the resin composition, from the viewpoint of significantly achieving the effects of the present invention. The upper limit is preferably 30% by mass or less, more preferably 25% by mass or less, even more preferably 20% by mass or less or 18% by mass or less, and particularly preferably 15% by mass or less or 14% by mass or less.

[0160] The total content of components (1A), (B), and (D) in the resin composition is preferably 50% by mass or more, more preferably 60% by mass or more or 70% by mass or more, even more preferably 75% by mass or more or 80% by mass or more, and particularly preferably 85% by mass or more or 90% by mass or more, based on 100% by mass of the resin components in the resin composition. There is no particular upper limit, but it may be 100% by mass, or may be 99% by mass or less, 98% by mass or less, 97% by mass or less, 96% by mass or less, 95% by mass or less, etc.

[0161] The content of component (D1) in the resin composition, when the resin components in the resin composition are taken as 100% by mass, is preferably 1% by mass or more or 5% by mass or more, more preferably 10% by mass or more or 15% by mass or more, even more preferably 20% by mass or more or 25% by mass or more, particularly preferably 30% by mass or more, 35% by mass or more, or 40% by mass or more, and the upper limit is preferably 80% by mass or less, more preferably 75% by mass or less or 70% by mass or less, even more preferably 65% ​​by mass or less or 60% by mass or less, particularly preferably 55% by mass or less, 50% by mass or less, or 46% by mass or less, from the viewpoint of significantly achieving the effects of the present invention.

[0162] The content of component (D1) in the resin composition is preferably 0.1% by mass or more, more preferably 1% by mass or more, even more preferably 3% by mass or more or 5% by mass or more, particularly preferably 8% by mass or more, 10% by mass or more, or 11% by mass or more, based on 100% by mass of the nonvolatile components in the resin composition, from the viewpoint of significantly achieving the effects of the present invention. The upper limit is preferably 30% by mass or less, more preferably 25% by mass or less, even more preferably 20% by mass or less or 18% by mass or less, particularly preferably 15% by mass or less, 14% by mass or less, or 13% by mass or less.

[0163] When the resin composition according to the first embodiment of the present invention contains an active ester resin having a naphthalene structure, the content of the active ester resin having a naphthalene structure in the resin composition, when the resin components in the resin composition are taken as 100% by mass, is preferably 1% by mass or more or 5% by mass or more, more preferably 10% by mass or more or 15% by mass or more, even more preferably 20% by mass or more or 25% by mass or more, particularly preferably 30% by mass or more, 35% by mass or more, or 40% by mass or more, from the viewpoint of significantly achieving the effects of the present invention. The upper limit is preferably 80% by mass or less, more preferably 75% by mass or less or 70% by mass or less, even more preferably 65% ​​by mass or less or 60% by mass or less, and particularly preferably 55% by mass or less, 50% by mass or less, or 46% by mass or less.

[0164] When the resin composition according to the first embodiment of the present invention contains an active ester resin having a naphthalene structure, the content of the active ester resin having a naphthalene structure in the resin composition is, from the viewpoint of significantly achieving the effects of the present invention, preferably 0.1% by mass or more, more preferably 1% by mass or more, even more preferably 3% by mass or more or 5% by mass or more, particularly preferably 8% by mass or more, 10% by mass or more, or 11% by mass or more, when the total non-volatile components in the resin composition is taken as 100% by mass. The upper limit is preferably 30% by mass or less, more preferably 25% by mass or less, even more preferably 20% by mass or less or 18% by mass or less, and particularly preferably 15% by mass or less, 14% by mass or less, or 13% by mass or less.

[0165] When the resin composition according to the first embodiment of the present invention contains another curing agent (D2), the content of the component (D2) in the resin composition, when the resin components in the resin composition are taken as 100% by mass, is preferably 0.1% by mass or more, more preferably 1% by mass or more or 2% by mass or more, even more preferably 3% by mass or more or 4% by mass or more, and particularly preferably 5% by mass or more or 6% by mass or more, from the viewpoint of significantly achieving the effects of the present invention. The upper limit is preferably 30% by mass or less or 25% by mass or less, more preferably 20% by mass or less or 15% by mass or less, even more preferably 10% by mass or less or 9% by mass or less, and particularly preferably 8% by mass or less or 7% by mass or less.

[0166] When the resin composition according to the first embodiment of the present invention contains another curing agent (D2), the content of the component (D2) in the resin composition is, from the viewpoint of significantly achieving the effects of the present invention, preferably 0.01% by mass or more or 0.05% by mass or more, more preferably 0.1% by mass or more or 0.2% by mass or more, even more preferably 0.5% by mass or more or 0.8% by mass or more, and particularly preferably 1.2% by mass or more or 1.5% by mass or more, based on 100% by mass of the non-volatile components in the resin composition. The upper limit is preferably 15% by mass or less or 12% by mass or less, more preferably 10% by mass or less or 8% by mass or less, even more preferably 5% by mass or less or 4% by mass or less, and particularly preferably 3% by mass or less, 2% by mass or less, or 1.8% by mass or less.

[0167] From the viewpoint of significantly achieving the effects of the present invention, the mass ratio of component (1A) to component (D1) in the resin composition [component (1A) / component (D1)] is preferably 0.01 or more, more preferably 0.02 or more, even more preferably 0.05 or more, and particularly preferably 0.08 or more or 0.12 or more. In one embodiment, it may be 0.15 or more, 0.2 or more, etc. The upper limit is preferably 5 or less or 3 or less, more preferably 2 or less or 1 or less, even more preferably 0.8 or less or 0.5 or less, and particularly preferably 0.4 or less or 0.3 or less. In one embodiment, it may be 0.25 or less, etc.

[0168] In order to achieve the effects of the present invention, the ratio of the moles of active groups in the (D) curing agent to the moles of epoxy groups in the (B) epoxy resin in the resin composition (moles of active groups in the curing agent / moles of epoxy groups in the epoxy resin) is preferably 0.01 or more or 0.05 or more, more preferably 0.1 or more or 0.2 or more, even more preferably 0.5 or more or 0.8 or more, and particularly preferably 1 or more, 1.05 or more, 1.1 or more, 1.2 or more, 1.3 or more, or 1.4 or more. The upper limit is preferably 100 or less or 50 or less, more preferably 10 or less or 8 or less, even more preferably 5 or less, 3 or less or 2 or less, and particularly preferably 1.8 or less or 1.6 or less. The "moles of active groups in the curing agent" can be calculated by dividing the "amount of curing agent" by the reactive group equivalent of the curing agent. The "moles of epoxy groups in the epoxy resin" can be calculated by dividing the "amount of epoxy resin" by the epoxy equivalent of the epoxy resin.

[0169] <(E) Inorganic filler> The resin composition according to the first embodiment of the present invention may contain an inorganic filler (E) as an optional component, and preferably contains an inorganic filler (E). By including an inorganic filler (E) in the resin composition, the dielectric loss tangent of the cured product can be further reduced.

[0170] (E) Inorganic fillers can be inorganic compounds. Examples of (E) inorganic fillers include silica, alumina, aluminosilicate, glass, cordierite, silicon oxide, 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 titanate zirconate, barium zirconate, calcium zirconate, zirconium phosphate, and zirconium tungstate phosphate. Among these, silica is preferred. Examples of silica include amorphous silica, fused silica, crystalline silica, synthetic silica, and hollow silica. Furthermore, spherical silica is preferred. The (E) inorganic filler may be used alone or in combination of two or more kinds in any ratio.

[0171] (E) Examples of commercially available inorganic fillers include "SP60-05" and "SP507-05" manufactured by Nippon Steel Chemical & Material Co., Ltd.; "YC100C", "YA050C", "YA050C-MJE", "YA010C", "SC2500SQ", "SO-C4", "SO-C2", "SO-C1", "SC2300-SVJ", "SC2050-SXF", and "180nmSX-C1" manufactured by Admatechs Co., Ltd.; "UFP-30", "DAW-03", and "FB-105FD" manufactured by Denka Co., Ltd.; "Silfil NSS-3N", "Silfil NSS-4N", and "Silfil NSS-5N" manufactured by Tokuyama Corporation; and "CellSpheres" and "MGH-005" manufactured by Taiheiyo Cement Corporation.

[0172] The average particle size of the (E) inorganic filler is preferably 10 μm or less, more preferably 5 μm or less, even more preferably 2 μm or less, even more preferably 1 μm or less, and particularly preferably 0.7 μm or less or 0.6 μm or less, from the viewpoint of achieving low surface roughness of the cured product (insulating layer) and facilitating the formation of fine wiring. The lower limit of the average particle size of the (E) inorganic filler is not particularly limited, but is preferably 0.01 μm or more, more preferably 0.05 μm or more, even more preferably 0.1 μm or more, and particularly preferably 0.15 μm or more, 0.2 μm or more, 0.3 μm or more, or 0.4 μm or more. The average particle size of the (E) inorganic filler can be measured by a laser diffraction / scattering method based on Mie scattering theory. Specifically, the particle size distribution of the inorganic filler is prepared on a volume basis using a laser diffraction / scattering particle size distribution analyzer, and the median diameter is used as the average particle size. The measurement sample can be prepared by weighing 100 mg of inorganic filler and 10 g of methyl ethyl ketone into a vial and dispersing them ultrasonically for 10 minutes. The wavelength of the light source used in the laser diffraction particle size distribution analyzer can be blue or red, and the measurement can be performed using a flow cell system. An example of a laser diffraction particle size distribution analyzer is the "LA-960" manufactured by Horiba, Ltd.

[0173] The specific surface area of ​​the (E) inorganic filler is not particularly limited, but is preferably 0.1 m 2 / g or more, more preferably 0.5m 2 / g or more, more preferably 1m 2 / g or more or 3m 2 The upper limit of the specific surface area of ​​the (E) inorganic filler is not particularly limited, but is preferably 100 m 2 / g or less, more preferably 70m 2 / g or less, more preferably 50m 2 / g or less, particularly preferably 40m 2 / g or less, 30m 2 / g or less, 20m 2 / g or less or 10m 2The specific surface area of ​​the inorganic filler can be calculated according to the BET method by adsorbing nitrogen gas onto the surface of a sample using a specific surface area measuring device (Macsorb HM-1210 manufactured by Mountech Co., Ltd.) and then using the BET multipoint method.

[0174] The inorganic filler (E) is preferably surface-treated with a surface treatment agent. This surface treatment can improve the moisture resistance and dispersibility of the inorganic filler (E). Examples of the surface treatment agent include vinyl-based silane coupling agents such as vinyltrimethoxysilane and vinyltriethoxysilane; epoxy-based silane coupling agents such as 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropylmethyldiethoxysilane, and 3-glycidoxypropyltriethoxysilane; and styryl-based silane coupling agents such as p-styryltrimethoxysilane. coupling agents; methacrylic silane coupling agents such as 3-methacryloxypropylmethyldimethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3-methacryloxypropylmethyldiethoxysilane, and 3-methacryloxypropyltriethoxysilane; acrylic silane coupling agents such as 3-acryloxypropyltrimethoxysilane; N-(2-aminoethyl)-3-aminopropylmethyldimethoxysilane, N-(2-aminoethyl)-3-aminopropyltrimethoxysilane, and 3-aminopropyltriethoxysilane; Amino-based silane coupling agents such as propyltrimethoxysilane, 3-aminopropyltriethoxysilane, 3-triethoxysilyl-N-(1,3-dimethylbutylidene)propylamine, N-phenyl-3-aminopropyltrimethoxysilane, N-phenyl-8-aminooctyltrimethoxysilane, and N-(vinylbenzyl)-2-aminoethyl-3-aminopropyltrimethoxysilane; isocyanurate-based silane coupling agents such as tris(trimethoxysilylpropyl)isocyanurate; ureido-based silane coupling agents such as ureidopropyltrialkoxysilane; mercapto-based silane coupling agents such as 3-mercaptopropylmethyldimethoxysilane and 3-mercaptopropyltrimethoxysilane; isocyanate-based silane coupling agents such as 3-isocyanatepropyltriethoxysilane; acid anhydride-based silane coupling agents such as 3-trimethoxysilylpropylsuccinic anhydride; sulfide-based silane coupling agents such as bis(triethoxysilylpropyl)tetrasulfide;Examples of suitable surface treatment agents include silane coupling agents such as methyltrimethoxysilane and phenyltrimethoxysilane, non-silane coupling alkoxysilane compounds such as methyltrimethoxysilane and phenyltrimethoxysilane, organosilazane compounds, and titanate-based coupling agents. The surface treatment agents may be used alone or in combination of two or more in any ratio. In one embodiment, the inorganic filler (E) is preferably surface-treated with an amino-based silane coupling agent, and more preferably surface-treated with N-phenyl-3-aminopropyltrimethoxysilane.

[0175] The degree of surface treatment with the surface treatment agent is preferably within a predetermined range from the viewpoint of improving the dispersibility of the inorganic filler. Specifically, 100 parts by mass of the inorganic filler is preferably surface-treated with 0.2 to 5 parts by mass of the surface treatment agent, more preferably 0.2 to 3 parts by mass, and even more preferably 0.3 to 2 parts by mass.

[0176] The degree of surface treatment with the surface treatment agent can be evaluated by the amount of carbon per unit surface area of ​​the inorganic filler. From the viewpoint of improving the dispersibility of the inorganic filler, the amount of carbon per unit surface area of ​​the inorganic filler is set to 0.02 mg / m 2 More than 0.1 mg / m is preferable. 2 More preferably, 0.2 mg / m or more 2 More preferably, the upper limit is 1 mg / m 2 Less than 0.8 mg / m is preferred 2 Less than 0.5 mg / m is more preferable. 2 The following is even more preferred:

[0177] (E) The amount of carbon per unit surface area of ​​the inorganic filler can be measured after the surface-treated inorganic filler is washed with a solvent (e.g., methyl ethyl ketone (MEK)). Specifically, a sufficient amount of MEK as a solvent is added to the inorganic filler that has been surface-treated with a surface treatment agent, and ultrasonic cleaning is performed at 25°C for 5 minutes. After removing the supernatant and drying the solid content, the amount of carbon per unit surface area of ​​the inorganic filler can be measured using a carbon analyzer. The carbon analyzer that can be used is the "EMIA-320V" manufactured by Horiba, Ltd.

[0178] When the resin composition according to the first embodiment of the present invention contains an inorganic filler (E), the content of the component (E) in the resin composition, when the total nonvolatile components in the resin composition is taken as 100% by mass, is preferably 10% by mass or more or 20% by mass or more, more preferably 30% by mass or more or 40% by mass or more, even more preferably 45% by mass or more, 50% by mass or more or 55% by mass or more, particularly preferably 60% by mass or more, 65% by mass or more or 70% by mass or more, and the upper limit 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 75% by mass or less, from the viewpoint of significantly achieving the effects of the present invention.

[0179] When the resin composition according to the first embodiment of the present invention contains an inorganic filler (E), the total content of components (1A), (B), (D), and (E) in the resin composition is preferably 50% by mass or more, more preferably 60% by mass or more or 65% by mass or more, even more preferably 70% by mass or more or 75% by mass or more, and particularly preferably 80% by mass or more, 85% by mass or more, 90% by mass or more, or 95% by mass or more, based on 100% by mass of the nonvolatile components in the resin composition. There is no particular upper limit, but it may be 100% by mass or may be 99.5% by mass or less, 99% by mass or less, 98.5% by mass or less, etc.

[0180] <(1F) Other maleimide compounds> The resin composition according to the first embodiment of the present invention may contain, as an optional component, a maleimide compound other than the component (1A) (hereinafter referred to as "(1F) other maleimide compound"). The (1F) other maleimide compound may be used alone or in combination of two or more.

[0181] (1F) Other maleimide compounds have one or more (preferably two or more) maleimide groups (2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl groups) in one molecule, and the type is not particularly limited as long as they do not fall under the category of component (1A). Examples of maleimide compounds include "BMI-3000J", "BMI-5000", "BMI-1400", "BMI-1500", "BMI-1700", and "BMI-689" (all manufactured by Designer Molecules). maleimide compounds having an aliphatic skeleton with 36 carbon atoms derived from dimer diamine, such as "SLK-1500" (manufactured by Shin-Etsu Chemical Co., Ltd.), "SLK-6895" (manufactured by Shin-Etsu Chemical Co., Ltd.), and "BMI-TMH" (manufactured by Daiwa Chemical Industry Co., Ltd.); maleimide compounds having an indane skeleton, as described in the Japan Institute of Invention and Innovation Disclosure Technical Bulletin No. 2020-500211; maleimide compounds having an aromatic ring skeleton directly bonded to the nitrogen atom of the maleimide group, such as "MIR-3000-70MT," "MIR-5000-60T" (manufactured by Nippon Kayaku Co., Ltd.), "BMI-4000," "BMI-2300" (manufactured by Daiwa Chemical Industry Co., Ltd.), "BMI-80," and "BMI-70" (manufactured by Keiai Chemical Industry Co., Ltd.);

[0182] When the resin composition according to the first embodiment of the present invention contains another maleimide compound (1F), the content of component (1F) in the resin composition, based on 100% by mass of the resin components in the resin composition, is preferably 0.01% by mass or more, more preferably 0.05% by mass or more, even more preferably 0.1% by mass or more or 0.2% by mass or more, and particularly preferably 0.5% by mass or more or 0.8% by mass or more, from the viewpoint of significantly achieving the effects of the present invention. In one embodiment, the content may be 1% by mass or more, 1.5% by mass or more, 2% by mass or more, 2.5% by mass or more, 3% by mass or more, etc. The upper limit is preferably 20% by mass or less, more preferably 18% by mass or less or 15% by mass or less, even more preferably 12% by mass or less or 10% by mass or less, and particularly preferably 8% by mass or less or 7% by mass or less. In one embodiment, the content may be 6% by mass or less, 5.5% by mass or less, 5% by mass or less, 4.5% by mass or less, 4% by mass or less, etc.

[0183] When the resin composition according to the first embodiment of the present invention contains another maleimide compound (1F), the content of component (1F) in the resin composition, based on 100% by mass of the nonvolatile components in the resin composition, is preferably 0.001% by mass or more, more preferably 0.005% by mass or more or 0.01% by mass or more, even more preferably 0.05% by mass or more or 0.1% by mass or more, and particularly preferably 0.2% by mass or more or 0.25% by mass or more, from the viewpoint of significantly achieving the effects of the present invention. In one embodiment, the content may be 0.3% by mass or more, 0.5% by mass or more, 0.8% by mass or more, 1% by mass or more, etc. The upper limit is preferably 10% by mass or less, more preferably 8% by mass or less, even more preferably 5% by mass or less or 3% by mass or less, and particularly preferably 2% by mass or less or 1.9% by mass or less. In one embodiment, the content may be 1.8% by mass or less, 1.5% by mass or less, 1.2% by mass or less, etc.

[0184] <(G) Radical Polymerizable Resin> The resin composition according to the first embodiment of the present invention may contain a (G) radical polymerizable resin as an optional component. However, components (1A) and (1F) are excluded from component (G). The (G) radical polymerizable resin may be used singly or in combination of two or more.

[0185] The (G) radical polymerizable resin may contain an ethylenically unsaturated bond. Therefore, the (G) radical polymerizable resin may have a radical polymerizable group containing an ethylenically unsaturated bond. Examples of the radical polymerizable group include unsaturated hydrocarbon groups such as vinyl, allyl, 1-propenyl, 3-cyclohexenyl, 3-cyclopentenyl, 2-vinylphenyl, 3-vinylphenyl, and 4-vinylphenyl; and α,β-unsaturated carbonyl groups such as acryloyl and methacryloyl. The (G) radical polymerizable resin preferably has two or more radical polymerizable groups.

[0186] Examples of the (G) radical polymerizable resin include a (meth)acrylic radical polymerizable resin, a styrene radical polymerizable resin, an allyl radical polymerizable resin, etc. The (G) component preferably contains any one of a styrene radical polymerizable resin, an allyl radical polymerizable resin, and a styrene radical polymerizable resin, and more preferably contains a styrene radical polymerizable resin.

[0187] The (meth)acrylic radical polymerizable resin is, for example, a compound having one or more, preferably two or more, acryloyl groups and / or methacryloyl groups. Examples of the (meth)acrylic radical polymerizable resin include cyclohexane-1,4-dimethanol di(meth)acrylate, cyclohexane-1,3-dimethanol di(meth)acrylate, tricyclodecane dimethanol di(meth)acrylate, neopentyl glycol di(meth)acrylate, 1,4-butanediol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, 1,8-octanediol di(meth)acrylate, 1,9-nonane diol di(meth)acrylate, and the like. Low molecular weight (molecular weight less than 1000) aliphatic (meth)acrylic acid ester compounds such as diol di(meth)acrylate, 1,10-decanediol di(meth)acrylate, trimethylolpropane tri(meth)acrylate, trimethylolethane tri(meth)acrylate, glycerin tri(meth)acrylate, and pentaerythritol tetra(meth)acrylate; dioxane glycol di(meth)acrylate, 3,6-dioxa-1,8-octanediol di(meth)acrylate, ) acrylate, 3,6,9-trioxaundecane-1,11-diol di(meth)acrylate, polyethylene glycol di(meth)acrylate, polypropylene glycol di(meth)acrylate, 9,9-bis[4-(2-acryloyloxyethoxy)phenyl]fluorene, ethoxylated bisphenol A di(meth)acrylate, propoxylated bisphenol A di(meth)acrylate, and other low molecular weight (molecular weight less than 1000) ether-containing (meth)acrylic acid ester compounds; low molecular weight (molecular weight less than 1000) isocyanurate-containing (meth)acrylic acid ester compounds such as tris(3-hydroxypropyl)isocyanurate tri(meth)acrylate, tris(2-hydroxyethyl)isocyanurate tri(meth)acrylate, and ethoxylated isocyanuric acid tri(meth)acrylate; and high molecular weight (molecular weight 1000 or more) acrylic acid ester compounds such as (meth)acrylic-modified polyphenylene ether resins.Commercially available (meth)acrylic radical polymerizable resins include, for example, "A-DOG" (dioxane glycol diacrylate) manufactured by Shin-Nakamura Chemical Co., Ltd., "DCP-A" (tricyclodecane dimethanol diacrylate) and "DCP" (tricyclodecane dimethanol dimethacrylate) manufactured by Kyoeisha Chemical Co., Ltd., "KAYARAD R-684" (tricyclodecane dimethanol diacrylate) and "KAYARAD R-604" (dioxane glycol diacrylate) manufactured by Nippon Kayaku Co., Ltd., and "SA9000" and "SA9000-111" (methacrylic-modified polyphenylene ether) manufactured by SABIC.

[0188] The styrene radical polymerizable resin is, for example, a compound having one or more, preferably two or more, vinyl groups directly bonded to an aromatic carbon atom. Examples of the styrene radical polymerizable resin include low-molecular-weight (molecular-weight less than 1000) styrene compounds such as divinylbenzene, 2,4-divinyltoluene, 2,6-divinylnaphthalene, 1,4-divinylnaphthalene, 4,4'-divinylbiphenyl, 1,2-bis(4-vinylphenyl)ethane, 2,2-bis(4-vinylphenyl)propane, and bis(4-vinylphenyl)ether; and high-molecular-weight (molecular-weight 1000 or more) styrene compounds such as styrene-modified polyphenylene ether resin and styrene-divinylbenzene copolymer. Commercially available styrene-based radical polymerizable resins include, for example, "ODV-XET(X03)", "ODV-XET(X04)", and "ODV-XET(X05)" (styrene-divinylbenzene copolymers) manufactured by Nippon Steel Chemical & Material Co., Ltd., and "OPE-2St 1200" and "OPE-2St 2200" (styrene-modified polyphenylene ether resins) manufactured by Mitsubishi Gas Chemical Company, Inc. Examples of styrene-based radical polymerizable resins include Copolymer A described in WO 2017 / 115813.

[0189] The allyl radical polymerizable resin is, for example, a compound having one or more, preferably two or more, allyl groups. Examples of allyl radical polymerizable resins include aromatic carboxylic acid allyl ester compounds such as diallyl diphenate, triallyl trimellitate, diallyl phthalate, diallyl isophthalate, diallyl terephthalate, diallyl 2,6-naphthalenedicarboxylate, and diallyl 2,3-naphthalenecarboxylate; isocyanuric acid allyl ester compounds such as 1,3,5-triallyl isocyanurate and 1,3-diallyl-5-glycidyl isocyanurate; epoxy-containing aromatic allyl compounds such as 2,2-bis[3-allyl-4-(glycidyloxy)phenyl]propane; benzoxazine-containing aromatic allyl compounds such as bis[3-allyl-4-(3,4-dihydro-2H-1,3-benzoxazin-3-yl)phenyl]methane; ether-containing aromatic allyl compounds such as 1,3,5-triallyl ether benzene; and allyl silane compounds such as diallyldiphenylsilane. Commercially available allyl radical polymerizable resins include "TAIC" (1,3,5-triallyl isocyanurate) manufactured by Nippon Kasei Chemical Industry Co., Ltd., "DAD" (diallyl diphenate) manufactured by Nisshoku Techno Fine Chemical Co., Ltd., "TRIAM-705" (triallyl trimellitate) manufactured by Fujifilm Wako Pure Chemical Industries, Ltd., "DAND" (2,3-naphthalene carboxylic acid diallyl) manufactured by Nisshoku Techno Fine Chemical Co., Ltd., "ALP-d" (bis[3-allyl-4-(3,4-dihydro-2H-1,3-benzoxazin-3-yl)phenyl]methane) manufactured by Shikoku Chemical Industry Co., Ltd., "RE-810NM" (2,2-bis[3-allyl-4-(glycidyloxy)phenyl]propane) manufactured by Nippon Kayaku Co., Ltd., and "DA-MGIC" (1,3-diallyl-5-glycidyl isocyanurate) manufactured by Shikoku Chemical Industry Co., Ltd.

[0190] The ethylenically unsaturated bond equivalent of the (G) radically polymerizable resin is preferably 20 g / eq to 3,000 g / eq, more preferably 50 g / eq to 2,500 g / eq, even more preferably 70 g / eq to 2,000 g / eq, and particularly preferably 90 g / eq to 1,500 g / eq. The ethylenically unsaturated bond equivalent represents the mass of the radically polymerizable resin per equivalent of ethylenically unsaturated bonds.

[0191] The weight average molecular weight (Mw) of the (G) radical polymerizable resin is preferably 100,000 or less, 80,000 or less, 50,000 or less, or 40,000 or less, more preferably 10,000 or less, even more preferably 5,000 or less, and particularly preferably 3,000 or less. The lower limit is not particularly limited, but may be, for example, 150 or more. The weight average molecular weight can be measured as a polystyrene-equivalent value by gel permeation chromatography (GPC).

[0192] When the resin composition according to the first embodiment of the present invention contains a radically polymerizable resin (G), the content of the component (G) in the resin composition, when the resin components in the resin composition are taken as 100% by mass, is preferably 0.1% by mass or more or 0.5% by mass or more, more preferably 1% by mass or more or 2% by mass or more, even more preferably 3% by mass or more or 4% by mass or more, and particularly preferably 5% by mass or more or 6% by mass or more, from the viewpoint of significantly achieving the effects of the present invention. The upper limit is preferably 30% by mass or less or 25% by mass or less, more preferably 20% by mass or less or 15% by mass or less, even more preferably 10% by mass or less or 15% by mass or less, and particularly preferably 10% by mass or less or 8% by mass or less.

[0193] When the resin composition according to the first embodiment of the present invention contains a radically polymerizable resin (G), the content of the component (G) in the resin composition is, relative to 100% by mass of the nonvolatile components in the resin composition, preferably 0.01% by mass or more, more preferably 0.05% by mass or more or 0.1% by mass or more, even more preferably 0.5% by mass or more or 1% by mass or more, and particularly preferably 1.2% by mass or more or 1.5% by mass or more. The upper limit is preferably 15% by mass or less or 12% by mass or less, more preferably 10% by mass or less or 8% by mass or less, even more preferably 5% by mass or less or 4% by mass or less, and particularly preferably 3% by mass or less, 2% by mass or less, or 1.8% by mass or less.

[0194] <(H)Organic filler> The resin composition according to the first embodiment of the present invention may contain, as an optional component, an organic filler (H), and preferably contains an organic filler (H). The organic filler (H) may be used singly or in combination of two or more.

[0195] The (H) organic filler is present in the resin composition in the form of particles. Examples of the (H) organic filler include rubber particles, polyamide fine particles, silicone particles, and core-shell particles. In the present invention, from the viewpoint of significantly achieving the desired effects of the present invention, the (H) organic filler preferably contains either rubber particles or core-shell particles, more preferably rubber particles, and even more preferably core-shell rubber particles.

[0196] Examples of the rubber component contained in the rubber particles include olefin-based thermoplastic elastomers such as polybutadiene, polyisoprene, polychlorobutadiene, ethylene-vinyl acetate copolymer, styrene-butadiene copolymer, styrene-isoprene copolymer, styrene-isobutylene copolymer, acrylonitrile-butadiene copolymer, isoprene-isobutylene copolymer, isobutylene-butadiene copolymer, ethylene-propylene-diene terpolymer, and ethylene-propylene-butene terpolymer; and acrylic thermoplastic elastomers such as polypropyl(meth)acrylate, polybutyl(meth)acrylate, polycyclohexyl(meth)acrylate, and polyoctyl(meth)acrylate; with acrylic thermoplastic elastomers being preferred. Rubber particles containing an acrylic thermoplastic elastomer as the rubber component are referred to as "acrylic rubber particles." Core-shell particles containing an acrylic thermoplastic elastomer as the rubber component are referred to as "acrylic core-shell particles." Core-shell rubber particles containing an acrylic thermoplastic elastomer as the rubber component are referred to as "acrylic core-shell rubber particles." That is, the (H) organic filler preferably contains either acrylic rubber particles or acrylic core-shell particles, more preferably acrylic rubber particles, and even more preferably acrylic core-shell rubber particles. Furthermore, the rubber component may be mixed with a silicone rubber such as polyorganosiloxane rubber. The rubber component contained in the rubber particles preferably has a glass transition temperature of 0°C or lower, more preferably -10°C or lower, even more preferably -20°C or lower, and particularly preferably -30°C or lower.

[0197] Commercially available rubber particles may be used, such as "EXL-2655" manufactured by Dow Chemical Japan, and "Staphyloid AC3401N" and "Staphyloid AC3816N" manufactured by Aica Kogyo Co., Ltd. "Staphyloid AC3816N" also falls under the category of core-shell type rubber particles.

[0198] Core-shell particles are particulate organic fillers consisting of a core particle containing a rubber component as described above and one or more shell layers covering the core particle. Furthermore, the core-shell particles are preferably core-shell graft copolymer particles consisting of a core particle containing a rubber component as described above and a shell formed by graft copolymerization of a monomer component copolymerizable with the rubber component contained in the core particle. The term "core-shell" as used here does not necessarily refer only to particles in which the core particle and the shell are clearly distinguishable, but also includes particles in which the boundary between the core particle and the shell is unclear, and the core particle does not necessarily have to be completely covered by the shell.

[0199] The rubber component is preferably contained in the core-shell graft copolymer particles in an amount of 40% by mass or more, more preferably 50% by mass or more, and even more preferably 60% by mass or more. The upper limit of the rubber component content in the core-shell graft copolymer particles is not particularly limited, but from the viewpoint of sufficiently covering the core particles with the shell portion, it is preferably, for example, 95% by mass or less, and more preferably 90% by mass.

[0200] Examples of monomer components that form the shell portion of the core-shell graft copolymer particles include (meth)acrylic acid esters such as methyl (meth)acrylate, ethyl (meth)acrylate, butyl (meth)acrylate, cyclohexyl (meth)acrylate, octyl (meth)acrylate, and glycidyl (meth)acrylate; (meth)acrylic acid; N-substituted maleimides such as N-methylmaleimide and N-phenylmaleimide; maleimide; α,β-unsaturated carboxylic acids such as maleic acid and itaconic acid; aromatic vinyl compounds such as styrene, 4-vinyltoluene, and α-methylstyrene; and (meth)acrylonitrile, among which (meth)acrylic acid esters are preferred, and methyl (meth)acrylate is more preferred.

[0201] Commercially available core-shell graft copolymer particles include, for example, "CHT" manufactured by Samsung SDI; "B602" manufactured by Techno UMG; "Paraloid EXL2602," "Paraloid EXL2603," "Paraloid EXL-2655," "Paraloid EXL2311," "Paraloid EXL2313," "Paraloid EXL2315," "Paraloid KM330," "Paraloid KM336P," and "Paraloid KCZ201" manufactured by Dow Chemical Japan; "Metablen C-223A," "Metablen E-901," "Metablen S-2001," "Metablen W-450A," and "Metablen SRK-200" manufactured by Mitsubishi Chemical Corporation; and "Kane Ace M-511," "Kane Ace M-600," "Kane Ace M-400," "Kane Ace M-580," and "Kane Ace MR-01" manufactured by Kaneka Corporation. These may be used alone or in combination of two or more.

[0202] The average particle size (average primary particle size) of the core-shell graft copolymer particles is not particularly limited, but is preferably 20 nm or more, more preferably 50 nm or more, even more preferably 80 nm or more, and particularly preferably 100 nm or more. The upper limit is preferably 5,000 nm or less, more preferably 2,000 nm or less, even more preferably 1,000 nm or less, and particularly preferably 500 nm or less. The average particle size (average primary particle size) of the core-shell graft copolymer particles can be measured using a zeta potential particle size distribution analyzer or the like.

[0203] When the resin composition according to the first embodiment of the present invention contains an organic filler (H), the content of component (H) in the resin composition, when the resin components in the resin composition are taken as 100% by mass, is preferably 0.1% by mass or more, more preferably 0.5% by mass or more, even more preferably 1% by mass or more or 2% by mass or more, and particularly preferably 3% by mass or more or 4% by mass or more, from the viewpoint of significantly achieving the effects of the present invention. In one embodiment, the content may be 5% by mass or more, 5.5% by mass or more, 6% by mass or more, etc. The upper limit is preferably 30% by mass or less, more preferably 25% by mass or less or 20% by mass or less, even more preferably 15% by mass or less or 10% by mass or less, and particularly preferably 9% by mass or less or 8% by mass or less. In one embodiment, the content may be 7% by mass or less, 6.8% by mass or less, etc.

[0204] When the resin composition according to the first embodiment of the present invention contains an organic filler (H), the content of the component (H) in the resin composition, when the total nonvolatile components in the resin composition is taken as 100% by mass, is preferably 0.01% by mass or more or 0.05% by mass or more, more preferably 0.1% by mass or more or 0.2% by mass or more, even more preferably 0.5% by mass or more or 0.8% by mass or more, and particularly preferably 1% by mass or more or 1.2% by mass or more, from the viewpoint of significantly achieving the effects of the present invention. In one embodiment, the content may be 1.5% by mass or more. The upper limit is preferably 15% by mass or less or 12% by mass or less, more preferably 10% by mass or less or 8% by mass or less, even more preferably 5% by mass or less or 4% by mass or less, and particularly preferably 3% by mass or less or 2% by mass or less.

[0205] <(I) Curing accelerator> The resin composition according to the first embodiment of the present invention may contain, as an optional component, (I) a curing accelerator, and preferably contains (I) a curing accelerator. (I) The curing accelerator may be used singly or in combination of two or more.

[0206] Examples of the (I) curing accelerator 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. The (I) curing accelerators may be used alone or in combination of two or more. The (I) curing accelerator preferably contains an amine-based curing accelerator or an imidazole-based curing accelerator, and more preferably contains an imidazole-based curing accelerator.

[0207] Examples of the amine curing accelerator include trialkylamines such as triethylamine and tributylamine, pyridines such as 4-dimethylaminopyridine, benzyldimethylamine, 2,4,6-tris(dimethylaminomethyl)phenol, and 1,8-diazabicyclo(5,4,0)-undecene, among which pyridines are preferred, and 4-dimethylaminopyridine is more preferred. These may be used alone or in combination of two or more.

[0208] As the amine-based curing accelerator, commercially available products may be used, such as "MY-25" manufactured by Ajinomoto Fine-Techno Co., Ltd. and "DMAP" manufactured by Koei Chemical Industry Co., Ltd.

[0209] Examples of the phosphorus-based curing accelerator include aliphatic phosphonium salts such as tetrabutylphosphonium bromide, tetrabutylphosphonium chloride, tetrabutylphosphonium acetate, tetrabutylphosphonium decanoate, tetrabutylphosphonium laurate, bis(tetrabutylphosphonium)pyromellitate, tetrabutylphosphonium hydrogenhexahydrophthalate, tetrabutylphosphonium 2,6-bis[(2-hydroxy-5-methylphenyl)methyl]-4-methylphenolate, and di-tert-butylmethylphosphonium tetraphenylborate; methyltriphenylphosphonium bromide, ethyltriphenylphosphonium bromide, propyltriphenylphosphonium bromide, butyltriphenylphosphonium bromide, benzyltriphenylphosphonium chloride, tetraphenylphosphonium bromide, p-tolyltriphenylphosphonium tetra-p-tolylborate, and tetraphenylphosphonium bromide. aromatic phosphonium salts such as tetraphenylborate, tetraphenylphosphonium tetra-p-tolylborate, triphenylethylphosphonium tetraphenylborate, tris(3-methylphenyl)ethylphosphonium tetraphenylborate, tris(2-methoxyphenyl)ethylphosphonium tetraphenylborate, (4-methylphenyl)triphenylphosphonium thiocyanate, tetraphenylphosphonium thiocyanate, and butyltriphenylphosphonium thiocyanate; aromatic phosphine-borane complexes such as triphenylphosphine-triphenylborane; aromatic phosphine-quinone adducts such as triphenylphosphine-p-benzoquinone adduct; aliphatic phosphines such as tributylphosphine, tri-tert-butylphosphine, trioctylphosphine, di-tert-butyl(2-butenyl)phosphine, di-tert-butyl(3-methyl-2-butenyl)phosphine, and tricyclohexylphosphine;Dibutylphenylphosphine, di-tert-butylphenylphosphine, methyldiphenylphosphine, ethyldiphenylphosphine, butyldiphenylphosphine, diphenylcyclohexylphosphine, triphenylphosphine, tri-o-tolylphosphine, tri-m-tolylphosphine, tri-p-tolylphosphine, tris(4-ethylphenyl)phosphine, tris(4-propylphenyl)phosphine, tris(4-isopropylphenyl)phosphine, tris(4-butylphenyl)phosphine, tris(4-tert-butylphenyl)phosphine, tris(2,4-dimethylphenyl)phosphine, tris(2,5-dimethylphenyl)phosphine, tris(2,6-dimethylphenyl)phosphine Examples of aromatic phosphines include 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. These may be used alone or in combination of two or more.

[0210] Examples of the urea-based curing accelerator 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. and aromatic dimethylureas such as toluenebis(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-phenylene)bis(N',N'-dimethylurea), and N,N-(4-methyl-1,3-phenylene)bis(N',N'-dimethylurea) [toluenebisdimethylurea]. These may be used alone or in combination of two or more.

[0211] Examples of guanidine curing accelerators 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-methylbiguanide, 1-ethylbiguanide, 1-n-butylbiguanide, 1-n-octadecylbiguanide, 1,1-dimethylbiguanide, 1,1-diethylbiguanide, 1-cyclohexylbiguanide, 1-allylbiguanide, 1-phenylbiguanide, and 1-(o-tolyl)biguanide. These may be used alone or in combination of two or more.

[0212] Examples of imidazole-based curing accelerators include 2-methylimidazole, 2-undecylimidazole, 2-heptadecylimidazole, 1,2-dimethylimidazole, 2-ethyl-4-methylimidazole, 2-phenylimidazole, 2-phenyl-4-methylimidazole, 1-benzyl-2-methylimidazole, 1-benzyl-2-phenylimidazole, and 1-cyanoethyl-2-methylimidazole. , 1-cyanoethyl-2-undecylimidazole, 1-cyanoethyl-2-ethyl-4-methylimidazole, 1-cyanoethyl-2-phenylimidazole, 1-cyanoethyl-2-undecylimidazole, 1-cyanoethyl-2-undecylimidazolium trimellitate, 1-cyanoethyl-2-phenylimidazolium trimellitate, 2,4-diamino-6-[2'-methylimidazolyl-(1')]-ethyl-s-triazine, 2,4-diamino-6 -[2'-Undecylimidazolyl-(1')]-ethyl-s-triazine, 2,4-diamino-6-[2'-ethyl-4'-methylimidazolyl-(1')]-ethyl-s-triazine, 2,4-diamino-6-[2'-methylimidazolyl-(1')]-ethyl-s-triazine isocyanuric acid adduct, 2-phenylimidazole isocyanuric acid adduct, 2-phenyl-4,5-dihydroxymethylimidazole imidazole compounds such as 2-phenyl-4-methyl-5-hydroxymethylimidazole, 2,3-dihydro-1H-pyrrolo[1,2-a]benzimidazole, 1-dodecyl-2-methyl-3-benzylimidazolium chloride, 2-methylimidazoline, and 2-phenylimidazoline, as well as adducts of imidazole compounds with epoxy resins, with 1-benzyl-2-phenylimidazole being preferred.

[0213] Commercially available imidazole curing accelerators include, for example, "1B2PZ," "2P4MZ," "2M4MZ," "2E4MZ," "2MZA-PW," "2MZ-OK," "2MA-OK," "2MA-OK-PW," "2PHZ," "2PHZ-PW," "Cl1Z," "Cl1Z-CN," "Cl1Z-CNS," and "C11Z-A" manufactured by Shikoku Chemical Industry Co., Ltd.; and "P200-H50" manufactured by Mitsubishi Chemical Corporation. These may be used alone or in combination of two or more.

[0214] Examples of metal-based curing 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 organic cobalt complexes such as cobalt(II) acetylacetonate and cobalt(III) acetylacetonate, organic copper complexes such as copper(II) acetylacetonate, organic zinc complexes such as zinc(II) acetylacetonate, organic iron complexes such as iron(III) acetylacetonate, organic nickel complexes such as nickel(II) acetylacetonate, and organic manganese complexes such as manganese(II) acetylacetonate. Examples of organometallic salts include zinc octoate, tin octoate, zinc naphthenate, cobalt naphthenate, tin stearate, and zinc stearate. These may be used alone or in combination of two or more.

[0215] When the resin composition according to the first embodiment of the present invention contains a curing accelerator (I), the content of the component (I) in the resin composition, when the resin components in the resin composition are taken as 100% by mass, is preferably 0.01% by mass or more or 0.02% by mass or more, more preferably 0.05% by mass or more or 0.08% by mass or more, even more preferably 0.1% by mass or more or 0.2% by mass or more, and particularly preferably 0.5% by mass or more or 0.8% by mass or more, from the viewpoint of significantly achieving the effects of the present invention. The upper limit is preferably 20% by mass or less, 18% by mass or less or 15% by mass or less, more preferably 12% by mass or less, 10% by mass or less or 8% by mass or less, even more preferably 5% by mass or less, 4% by mass or less or 3% by mass or less, and particularly preferably 2% by mass or less, 1.5% by mass or less, 1.2% by mass or less or 1.0% by mass or less.

[0216] When the resin composition according to the first embodiment of the present invention contains a curing accelerator (I), the content of the component (I) in the resin composition, based on 100% by mass of the nonvolatile components in the resin composition, is preferably 0.001% by mass or more or 0.005% by mass or more, more preferably 0.01% by mass or more or 0.02% by mass or more, even more preferably 0.05% by mass or more, 0.08% by mass or more or 0.1% by mass or more, particularly preferably 0.15% by mass or more, 0.2% by mass or more, or 0.22% by mass or more, from the viewpoint of significantly achieving the effects of the present invention. The upper limit is preferably 10% by mass or less or 8% by mass or less, more preferably 5% by mass or less or 2% by mass or less, even more preferably 1% by mass or less or 0.8% by mass or less, and particularly preferably 0.5% by mass or less, 0.4% by mass or less or 0.3% by mass or less.

[0217] <(J) Organic Solvent> The resin composition according to the first embodiment of the present invention may contain an organic solvent (J) as an optional component. The organic solvent (J) may be used singly or in combination of two or more. In one embodiment, it is preferable to use two or more organic solvents (J) in combination.

[0218] Examples of the (J) organic solvent include organic solvents composed of atoms selected from carbon, oxygen, nitrogen, phosphorus, sulfur, halogen, and hydrogen atoms. From the viewpoint of safety, the (J) organic solvent is preferably an organic solvent composed of atoms selected from carbon, oxygen, and hydrogen atoms, and more preferably an organic solvent composed of carbon, oxygen, and hydrogen atoms.

[0219] Examples of (J) organic solvents include glycol-based organic solvents, glycol ether-based organic solvents, glycol ether ester-based organic solvents, ketone-based organic solvents, ester-based organic solvents, ether-based organic solvents, alcohol-based organic solvents, aliphatic hydrocarbon-based organic solvents, aromatic organic solvents, nitrogen-based organic solvents, sulfur-based organic solvents, and halogen-based organic solvents. Examples of nitrogen-based organic solvents include amide-based organic solvents, urea-based organic solvents, and nitrile-based organic solvents. From the viewpoint of safety, (J) organic solvents are preferably ester-based organic solvents, ketone-based organic solvents, glycol-based organic solvents, glycol ether-based organic solvents, glycol ether ester-based organic solvents, or aromatic organic solvents, more preferably ester-based organic solvents, glycol ether ester-based organic solvents, ketone-based organic solvents, or aromatic organic solvents, even more preferably ketone-based organic solvents or aromatic organic solvents, and particularly preferably ketone-based organic solvents.

[0220] Examples of glycol-based organic solvents include ethylene glycol, diethylene glycol, propylene glycol, dipropylene glycol, and trimethylene glycol.

[0221] Examples of glycol ether organic solvents include cellosolves such as ethylene glycol monomethyl ether (also known as methyl cellosolve), ethylene glycol monoethyl ether (also known as cellosolve), ethylene glycol monopropyl ether (also known as propyl cellosolve), ethylene glycol monobutyl ether (also known as butyl cellosolve), ethylene glycol monoisobutyl ether (also known as isobutyl cellosolve), ethylene glycol mono-tert-butyl ether (also known as tert-butyl cellosolve), and ethylene glycol monohexyl ether; diethylene glycol monomethyl ether (also known as methyl carbitol), diethylene glycol monoethyl ether (also known as carbitol), and diethylene glycol monopropyl ether (also known as propyl carbitol), diethylene glycol monobutyl ether (DB) (also known as butyl carbitol), and other carbitols; propylene glycol ethers such as propylene glycol monomethyl ether (PGM, also known as 1-methoxy-2-propanol), propylene glycol monoethyl ether, propylene glycol monopropyl ether, and propylene glycol monobutyl ether; and dipropylene glycol ethers such as dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether, dipropylene glycol monopropyl ether, and dipropylene glycol monobutyl ether, with propylene glycol ethers being preferred, and propylene glycol monomethyl ether (1-methoxy-2-propanol) being more preferred.

[0222] Examples of glycol ether ester organic solvents include cellosolve esters such as ethylene glycol monomethyl ether acetate (also known as methyl cellosolve acetate), ethylene glycol monoethyl ether acetate (also known as cellosolve acetate), and ethylene glycol monobutyl ether acetate (also known as butyl cellosolve acetate); carbitol esters such as diethylene glycol monoethyl ether acetate (EDGAc) (also known as carbitol acetate) and diethylene glycol monobutyl ether acetate (also known as butyl carbitol acetate); propylene glycol ether esters such as propylene glycol monomethyl ether acetate (PGMEAc) and propylene glycol monoethyl ether acetate; and dipropylene glycol ether esters such as dipropylene glycol monomethyl ether acetate, with carbitol esters being preferred and more preferred than diethylene glycol monoethyl ether acetate.

[0223] Examples of ketone-based organic solvents include aliphatic acyclic ketones such as acetone, methyl ethyl ketone (MEK), diethyl ketone, 2-pentanone, methyl isobutyl ketone, 2-hexanone, 2-heptanone (MAK), and diisobutyl ketone; aliphatic cyclic ketones such as cyclopentanone, cyclohexanone (Anone), and 2-methylcyclohexanone; and aromatic ketones such as acetophenone, with methyl ethyl ketone (MEK) or cyclohexanone being preferred. The lower limit of the number of carbon atoms in the ketone-based organic solvent is preferably 2 or more, more preferably 3 or more, and even more preferably 4 or more. The upper limit of the number of carbon atoms in the ketone-based organic solvent is preferably 10 or less, more preferably 8 or less, and even more preferably 6 or less.

[0224] Ester-based organic solvents are organic solvents having an ester structure that do not fall under the category of glycol ether ester-based organic solvents. Examples include fatty acid alkyl esters such as methyl acetate, ethyl acetate, n-propyl acetate, isopropyl acetate, n-butyl acetate, isobutyl acetate, sec-butyl acetate, tert-butyl acetate, n-pentyl acetate, isopentyl acetate, ethyl propionate, propyl propionate, and isopropyl propionate; hydroxy acid alkyl esters such as methyl lactate, ethyl lactate, and butyl lactate; keto acid alkyl esters such as methyl acetoacetate and ethyl acetoacetate; lactones such as γ-butyrolactone and α-acetyl-γ-butyrolactone; and aromatic esters such as methyl benzoate and ethyl benzoate. Lactones are preferred as ester-based organic solvents. Furthermore, the number of carbon atoms in the ester-based organic solvent is preferably 3 to 9.

[0225] The ether-based organic solvent is an organic solvent having an ether structure that does not fall under the category of glycol ether-based organic solvents or glycol ether ester-based organic solvents, and examples thereof include aliphatic acyclic ethers such as dimethyl ether, diethyl ether, methyl ethyl ether, diisopropyl ether, dibutyl ether, methyl tert-butyl ether, ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, and triethylene glycol dimethyl ether; aliphatic cyclic ethers such as tetrahydrofuran, 1,4-dioxane, and 1,3-dioxolane; and aromatic ethers such as anisole and phenetole. The number of carbon atoms in the ether-based organic solvent is preferably 2 to 9.

[0226] Alcohol-based organic solvents are organic solvents having an alcohol structure that does not fall under the category of glycol-based organic solvents and glycol ether-based organic solvents, and examples thereof include aliphatic acyclic alcohols such as methanol, ethanol, n-propanol, isopropanol, n-butyl alcohol, isobutyl alcohol, sec-butyl alcohol, tert-butyl alcohol, n-pentyl alcohol, isopentyl alcohol, sec-pentyl alcohol, tert-pentyl alcohol, neopentyl alcohol, n-hexyl alcohol, n-heptyl alcohol, isoheptyl alcohol, n-octyl alcohol, and 2-ethylhexyl alcohol; aliphatic cyclic alcohols such as cyclohexanol; and aromatic alcohols such as benzyl alcohol and phenethyl alcohol.

[0227] Examples of aliphatic hydrocarbon organic solvents include n-pentane, n-hexane, 2-methylpentane (also known as isohexane), n-heptane, n-octane, cyclopentane, cyclohexane, methylcyclohexane, ethylcyclohexane, decalin, etc. The aliphatic hydrocarbon organic solvent preferably has 5 to 10 carbon atoms.

[0228] Examples of aromatic organic solvents include C benzene, toluene, o-xylene, m-xylene, p-xylene, and ethylbenzene. 6-8 Aromatic hydrocarbons: C9 aromatic hydrocarbons such as 1,2,3-trimethylbenzene, 1,3,5-trimethylbenzene (also known as mesitylene), 1,2,4-trimethylbenzene, 4-ethyltoluene, 3-ethyltoluene, and 2-ethyltoluene; C1 aromatic hydrocarbons such as 1,2-diethylbenzene, 1,3-diethylbenzene, 1,4-diethylbenzene, 3-ethyl-o-xylene, 4-ethyl-o-xylene, 2-ethyl-p-xylene, 1,2,3,5-tetramethylbenzene, and tetralin. 10 Aromatic hydrocarbons include aromatic heterocyclic compounds such as pyridine, furan, and thiophene, and toluene is preferred. The aromatic organic solvent preferably has 6 to 10 carbon atoms.

[0229] Examples of amide-based organic solvents include aliphatic acyclic amides such as N,N-dimethylacetamide and N,N-dimethylformamide, lactams such as N-methyl-2-pyrrolidone and N-cyclohexyl-2-pyrrolidone, and phosphoric acid amides such as hexamethylphosphoramide. The number of carbon atoms in the amide-based organic solvent is preferably 2 to 10.

[0230] Examples of urea-based organic solvents include tetramethylurea and 1,3-dimethyl-2-imidazolinone.

[0231] Examples of the nitrile organic solvent include acetonitrile, propionitrile, benzonitrile, etc. The nitrile organic solvent preferably has 2 to 10 carbon atoms.

[0232] An example of the sulfur-based organic solvent is dimethyl sulfoxide.

[0233] Examples of halogen-based organic solvents include chloroform, methylene chloride, carbon tetrachloride, 1,2-dichloroethane, etc. The halogen-based organic solvent preferably has 1 to 10 carbon atoms.

[0234] Among these, the (J) organic solvent is preferably γ-butyrolactone, methyl ethyl ketone (MEK), cyclopentanone, cyclohexanone, propylene glycol, diethylene glycol monoethyl ether acetate, propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, or toluene, more preferably methyl ethyl ketone (MEK), cyclohexanone, diethylene glycol monoethyl ether acetate, γ-butyrolactone, propylene glycol monomethyl ether, or toluene, still more preferably methyl ethyl ketone (MEK), cyclohexanone, propylene glycol monomethyl ether, or toluene, and particularly preferably methyl ethyl ketone (MEK) or cyclohexanone.

[0235] <(K) Other additives> The resin composition according to the first embodiment of the present invention may further contain (K) other additives as optional components to the extent that the object of the present invention is not impaired. Examples of such additives include radical polymerization initiators such as peroxide radical polymerization initiators and azo radical polymerization initiators; thermoplastic resins such as phenoxy resins, polyvinyl acetal resins, polysulfone resins, polyethersulfone resins, polyetheretherketone resins, and polyester resins; 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 oxide, and carbon black; polymerization inhibitors such as hydroquinone, catechol, pyrogallol, and phenothiazine; leveling agents such as silicone leveling agents and acrylic polymer leveling agents; thickeners such as bentone and montmorillonite; antifoaming agents such as silicone antifoaming agents, acrylic antifoaming agents, fluorine-based antifoaming agents, and vinyl resin antifoaming agents; and ultraviolet absorbers such as benzotriazole-based ultraviolet absorbers. Examples of suitable additives include ultraviolet absorbers; adhesion improvers such as urea silane; adhesion promoters such as triazole-based adhesion promoters, tetrazole-based adhesion promoters, and triazine-based adhesion promoters; antioxidants such as hindered phenol-based antioxidants; fluorescent brighteners such as stilbene derivatives; surfactants such as fluorine-based surfactants and silicone-based surfactants; flame retardants such as phosphorus-based flame retardants (e.g., phosphate ester compounds, phosphazene compounds, phosphinic acid compounds, and 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-based dispersants, polyoxyalkylene-based dispersants, acetylene-based dispersants, silicone-based dispersants, anionic dispersants, and cationic dispersants; and stabilizers such as borate-based stabilizers, titanate-based stabilizers, aluminate-based stabilizers, zirconate-based stabilizers, isocyanate-based stabilizers, carboxylic acid-based stabilizers, and carboxylic acid anhydride-based stabilizers. The content of such additives may be determined depending on the properties required for the resin composition.Furthermore, the components (1A) to (J) may have the functions of a radical polymerization initiator, a thermoplastic resin, an organometallic compound, a colorant, a polymerization inhibitor, a leveling agent, a thickener, an antifoaming agent, an ultraviolet absorber, an adhesion improver, an adhesion imparting agent, an antioxidant, a fluorescent brightener, a surfactant, a flame retardant, a dispersant, a stabilizer, etc. In such cases, such components are considered to be part of the components (1A) to (J) rather than the component (K).

[0236] [Resin composition according to the second embodiment] A resin composition according to a second embodiment of the present invention comprises (2A) a maleimide compound having a second specific structure, (B) an epoxy resin, and (D) a curing agent, wherein the component (D) comprises (D1) an active ester resin. The second specific structure will be described later. By incorporating the components (2A), (B), and (D1) in combination into a resin composition, a cured product can be obtained that has a low dielectric tangent, excellent smear removability, and high heat resistance (glass transition temperature). The present inventors have also confirmed that the cured product (insulating layer) provided by the present invention has a low dielectric constant, excellent reflow resistance, high adhesion strength with a conductor layer, a low coefficient of linear thermal expansion (CTE), and reduced warpage.

[0237] In the present invention, "adhesion strength" refers to the adhesion strength between an insulating layer and a conductor layer formed from a cured product of the resin composition of the present invention. The present inventors have confirmed that the adhesion strength is particularly excellent when the conductor layer is copper. Examples of the adhesion strength between an insulating layer and copper include "CZ copper peel strength" and "plating peel strength." "CZ copper peel strength" refers to the adhesion strength between an insulating layer and a conductor layer (copper) when they are joined by lamination. "Plating peel strength" refers to the adhesion strength between an insulating layer and a conductor layer (copper) when the conductor layer (copper) is formed on the insulating layer by plating. According to the present invention, a cured product (insulating layer) with excellent both CZ copper peel strength and plating peel strength can be obtained, and a cured product (insulating layer) with particularly excellent CZ copper peel strength can be obtained. Furthermore, a cured product exhibiting high adhesion strength (CZ copper peel strength) can also be obtained even when exposed to a high-temperature, high-humidity environment.

[0238] When curing a resin composition, it may first be cured at a relatively low temperature (pre-cure) and then cured at a relatively high temperature (full cure). Generally, a cured product after full cure tends to warp more, but the resin composition according to the first embodiment of the present invention can suppress both warpage of the cured product after pre-cure and warpage of the cured product after full cure.

[0239] The resin composition according to the second embodiment may contain, as the component (D), a curing agent other than the component (D1) (hereinafter referred to as "(D2) other curing agent"). Furthermore, the resin composition according to the second embodiment may further contain optional components in addition to a combination of the components (2A), (B), and (D). Examples of optional components include (E) inorganic fillers, (2F) other maleimide compounds, (G) radically polymerizable resins, (H) organic fillers, (I) curing accelerators, (J) organic solvents, and (K) other additives. Each component contained in the resin composition according to the first embodiment will be described below.

[0240] <(2A) Maleimide Compound Having a Second Specific Structure> The resin composition according to the second embodiment of the present invention contains (2A) a maleimide compound having a structural unit represented by the following formula (2): The component (2A) may be used alone or in combination of two or more. [ka] (In formula (2), R 11 R each independently represents a hydrocarbon group having 1 to 18 carbon atoms. 12 R each independently represents a hydrocarbon group having 1 to 18 carbon atoms. 13 R each independently represents a hydrocarbon group having 1 to 18 carbon atoms. 16 Each independently represents a hydrocarbon group having 1 to 18 carbon atoms. 1 each independently represents an integer of 0 to 2, m 6 each independently represents an integer of 0 to 2, m 1 +m 6 ≦2. m2 each independently represents an integer of 0 to 4, and m 4 each independently represents an integer of 0 to 5, and n 1 Each independently represents the number of repeating units.)

[0241] In formula (2), R 11 each independently represents a hydrocarbon group having 1 to 18 carbon atoms, and R in formula (T-2) 11 is the same as

[0242] In formula (2), R 12 each independently represents a hydrocarbon group having 1 to 18 carbon atoms, and R in formula (T-2) 12 is the same as

[0243] In formula (2), R 13 each independently represents a hydrocarbon group having 1 to 18 carbon atoms, and R in formula (1) 13 is the same as

[0244] In formula (2), R 16 each independently represents a hydrocarbon group having 1 to 18 carbon atoms, and R in formula (4) 16 is the same as

[0245] In formula (2), m 1 each independently represents an integer of 0 to 2, m 6 each independently represents an integer of 0 to 2, m 1 +m 6 ≦2. m 1 is preferably 0 or 1, and more preferably 0. 6 is preferably 0 or 1, and more preferably 0.

[0246] In formula (2), m 2 each independently represents an integer of 0 to 4, and m in formula (1) 2 is the same as

[0247] In formula (2), m 4 each independently represents an integer of 0 to 5, and m in formula (4) 4 is the same as

[0248] In formula (2), n 1 Each independently represents the number of repeating units, and n in formula (1) 1 is the same as

[0249] In one embodiment, the component (2A) is preferably a maleimide compound having a structure represented by the following formula (3): [ka] [ka] (In formula (3), formula (4) and formula (5), R 11 R each independently represents a hydrocarbon group having 1 to 18 carbon atoms. 12 R each independently represents a hydrocarbon group having 1 to 18 carbon atoms. 13 R each independently represents a hydrocarbon group having 1 to 18 carbon atoms. 16 Each independently represents a hydrocarbon group having 1 to 18 carbon atoms. 1 each independently represents an integer of 0 to 2, m 6 each independently represents an integer of 0 to 2, m 5 each independently represents an integer of 0 to 3, and m 1 +m 6 ≦2 and m 1 +m 5 ≦3. m 2 each independently represents an integer of 0 to 4, and m 4 each independently represents an integer of 0 to 5, and n 1 Each "n" independently represents the number of repeating units, and each "n" independently represents an integer of 1 or more. M1 represents a hydrogen atom or a monovalent group represented by formula (4). M2 represents a hydrogen atom or a monovalent group represented by formula (5). * represents a bond.

[0250] In formula (3), formula (4) and formula (5), R 11 each independently represents a hydrocarbon group having 1 to 18 carbon atoms, and R in formula (T-2) 11 is the same as

[0251] In formula (3), R 12 each independently represents a hydrocarbon group having 1 to 18 carbon atoms, and R in formula (T-2) 12 is the same as

[0252] In formula (3), R 13 each independently represents a hydrocarbon group having 1 to 18 carbon atoms, and R in formula (1) 13 is the same as

[0253] In formula (3), formula (4) and formula (5), R 16 each independently represents a hydrocarbon group having 1 to 18 carbon atoms, and R in formula (4) 16 is the same as

[0254] In formula (3) and formula (5), m 1 each independently represents an integer of 0 to 2, m 6 each independently represents an integer of 0 to 2, m 5 each independently represents an integer of 0 to 3, and m 1 +m 6 ≦2 and m 1 +m 5 ≦3. m in formula (3) and formula (5) 1 and m 6 is m in equation (2) 1 and m 6 is the same as m 5 is preferably 0 to 2, more preferably 0 or 1, and even more preferably 0.

[0255] In formula (3), m 2 each independently represents an integer of 0 to 4, and m in formula (1) 2 is the same as

[0256] In formula (4) and formula (5), m 4 each independently represents an integer of 0 to 5, and m in formula (4) according to the first embodiment 4 is the same as

[0257] In formula (3), n 1Each independently represents the number of repeating units, and n in formula (1) 1 is the same as

[0258] In formula (3), X M1 represents a hydrogen atom or a monovalent group represented by formula (4). M1 is preferably a hydrogen atom.

[0259] In formula (3), X M2 represents a hydrogen atom or a monovalent group represented by formula (5). M2 is preferably a monovalent group represented by formula (5).

[0260] Specific examples of the component (2A), the preferred embodiments of the number average molecular weight and weight average molecular weight, and the preferred embodiments of the content are the same as those of the component (1A).

[0261] <(2A) Method for producing a maleimide compound having a second specific structure> There are no limitations on the method for producing the component (2A). The component (2A) can be produced, for example, by the production method described in the section <(1A) Production method for maleimide compound having first specific structure>.

[0262] <(B) Epoxy resin> The resin composition according to the second embodiment of the present invention contains an epoxy resin (B). The epoxy resin (B) according to the second embodiment is the same as the epoxy resin (B) according to the first embodiment.

[0263] <(D) Curing agent> The resin composition according to the second embodiment of the present invention contains a curing agent (D). The curing agent (D) according to the second embodiment is the same as the curing agent (D) according to the first embodiment.

[0264] <(D1) Active ester resin> The component (D) according to the second embodiment of the present invention includes an active ester resin (D1). The active ester resin (D1) according to the second embodiment is the same as the active ester resin (D1) according to the first embodiment. That is, in one embodiment, the mass ratio of the component (2A) to the component (D1) in the resin composition [component (2A) / component (D1)] is preferably 0.01 to 5.

[0265] <(D2) Other hardeners> The component (D) according to the second embodiment of the present invention may further contain a curing agent other than the component (D1) (hereinafter referred to as "other curing agent (D2)"). The other curing agent (D2) according to the second embodiment is the same as the other curing agent (D2) according to the first embodiment.

[0266] <(E) Inorganic filler> The resin composition according to the second embodiment of the present invention may contain an inorganic filler (E) as an optional component, and preferably contains an inorganic filler (E). The inorganic filler (E) according to the second embodiment is the same as the inorganic filler (E) according to the first embodiment.

[0267] <(2F) Other maleimide compounds> The resin composition according to the second embodiment of the present invention may contain, as an optional component, a maleimide compound other than the component (2A) (hereinafter referred to as "(2F) other maleimide compound"). The preferred aspects and preferred content of the (2F) other maleimide compound are the same as those of the (1F) other maleimide compound.

[0268] <(G) Radical Polymerizable Resin> The resin composition according to the second embodiment of the present invention may contain a (G) radical polymerizable resin as an optional component. However, components (2A) and (2F) are excluded from the component (G). The (G) radical polymerizable resin according to the second embodiment is the same as the (G) radical polymerizable resin according to the first embodiment.

[0269] <(H)Organic filler> The resin composition according to the second embodiment of the present invention may contain an organic filler (H) as an optional component, and preferably contains an organic filler (H). The organic filler (H) according to the second embodiment is the same as the organic filler (H) according to the first embodiment.

[0270] <(I) Curing accelerator> The resin composition according to the second embodiment of the present invention may contain, as an optional component, a curing accelerator (I), and preferably contains a curing accelerator (I). The curing accelerator (I) according to the second embodiment is the same as the curing accelerator (I) according to the first embodiment.

[0271] <(J) Organic Solvent> The resin composition according to the second embodiment of the present invention may contain an organic solvent (J) as an optional component. The organic solvent (J) according to the second embodiment is the same as the organic solvent (J) according to the first embodiment.

[0272] <(K) Other additives> The resin composition according to the second embodiment of the present invention may further contain (K) other additives as optional components to the extent that the object of the present invention is not impaired. The (K) other additives according to the second embodiment are the same as the (K) other additives according to the first embodiment.

[0273] [Method of producing resin composition] The resin composition of the present invention can be prepared by appropriately mixing the necessary components among the above components (A) to (K), and kneading or mixing them as needed using kneading means such as a triple roll mill, ball mill, bead mill, or sand mill, or stirring means such as a super mixer, planetary mixer, or high-speed rotary mixer.

[0274] [Physical properties and applications of resin compositions] In one embodiment, a cured product of the resin composition according to the present invention is characterized by excellent smear removability. For example, as described in the section <Evaluation Test for Smear Removability> below, when a via hole is formed in the cured product and subjected to a desmear treatment, the longest smear extending from the wall surface at the bottom of the via hole preferably has a length of less than 5 μm.

[0275] In one embodiment, a cured product of the resin composition according to the present invention is characterized by excellent heat resistance (high glass transition temperature). For example, as described in the section below entitled "Measurement Test of Glass Transition Temperature (Tg) and Coefficient of Linear Thermal Expansion (CTE)," when measured using a thermomechanical analyzer, the glass transition temperature (Tg) of a cured product of the resin composition according to the present invention is preferably 130°C or higher or 140°C or higher, more preferably 150°C or higher or 155°C or higher, even more preferably 160°C or higher or 165°C or higher, and particularly preferably 170°C or higher, 175°C or higher, or 180°C or higher. The upper limit is not particularly limited, but may be 400°C or lower, 300°C or lower, etc.

[0276] In one embodiment, a cured product of the resin composition according to the present invention is characterized by high CZ copper peel strength. For example, as described in the section below entitled "Measurement of Adhesion Strength (CZ Copper Peel Strength) with a Conductor Layer Before and After Exposure to a High-Temperature, High-Humidity Environment (HAST)," the load applied when measuring the copper foil peel strength of the cured product after curing (before exposure to a high-temperature, high-humidity environment (HAST)) is preferably 0.30 kgf / cm or more, more preferably 0.40 kgf / cm or more, even more preferably 0.50 kgf / cm or more or 0.60 kgf / cm or more, and particularly preferably 0.65 kgf / cm or more or 0.70 kgf / cm or more. The upper limit is not particularly limited, but may be 10 kgf / cm or less, 1 kgf / cm or less, or the like.

[0277] In one embodiment, a cured product of the resin composition according to the present invention exhibits a high CZ copper peel strength even after exposure to a high-temperature, high-humidity environment (HAST). For example, as described in the section "Measurement of Adhesion Strength (CZ Copper Peel Strength) with a Conductor Layer Before and After Exposure to a High-Temperature, High-Humidity Environment (HAST)" below, the load applied when measuring the copper foil peel strength of a cured product after exposure to a high-temperature, high-humidity environment (HAST) is preferably 0.20 kgf / cm or more, more preferably 0.30 kgf / cm or more, even more preferably 0.40 kgf / cm or more, and particularly preferably 0.45 kgf / cm or more or 0.50 kgf / cm or more. The upper limit is not particularly limited, but may be 10 kgf / cm or less, 1 kgf / cm or less, or the like.

[0278] In one embodiment, a cured product of the resin composition according to the present invention exhibits a low dielectric constant (Dk) even at high temperatures. For example, as described in the section below entitled "Measurement Test of Dielectric Constant and Dielectric Loss Tangent," when measured at a measurement frequency of 10 GHz and a measurement temperature of 90°C, the dielectric constant (Dk) of a cured product of the resin composition according to the present invention is preferably 5 or less or 4.5 or less, more preferably 4 or less or 3.9 or less, even more preferably 3.8 or less or 3.7 or less, and particularly preferably 3.6 or less or 3.5 or less. The lower limit is not particularly limited, but may be 0.1 or more, 1.0 or more, etc.

[0279] In one embodiment, a cured product of the resin composition according to the present invention exhibits a low dielectric loss tangent (Df) even at high temperatures. For example, as described in the section below entitled "Measurement Test of Dielectric Constant and Dielectric Loss Tangent," when measured at a measurement frequency of 10 GHz and a measurement temperature of 90°C, the dielectric loss tangent (Df) of a cured product of the resin composition according to the present invention is preferably 0.0100 or less, more preferably 0.0080 or 0.0060 or less, even more preferably 0.0040 or 0.0035 or less, and particularly preferably 0.0030 or 0.0027 or less. The lower limit is not particularly limited, but may be 0.0001 or more, 0.0010 or more, etc.

[0280] In one embodiment, a cured product of the resin composition according to the present invention is characterized by a low coefficient of linear thermal expansion (CTE). For example, as described in the section "Measurement Tests for Glass Transition Temperature (Tg) and Coefficient of Linear Thermal Expansion (CTE)" below, when measured using a thermomechanical analyzer, the coefficient of linear thermal expansion (CTE) of a cured product of the resin composition according to the present invention is preferably 30 ppm / °C or less, more preferably 25 ppm / °C or less, even more preferably 20 ppm / °C or less or 18 ppm / °C or less, and particularly preferably 17 ppm / °C or less or 16 ppm / °C or less. The lower limit is not particularly limited, but may be 0.1 ppm / °C or more, 1 ppm / °C or more, 3 ppm / °C or more, etc.

[0281] In one embodiment, the cured product of the resin composition according to the present invention is characterized by reduced warpage. For example, when measured as described in the section "Warpage Measurement" below, the warpage of the cured product after pre-curing (curing at 170°C for 30 minutes) on an inner layer substrate cut to a size of 120 mm x 160 mm is preferably 40 mm or less or 35 mm or less, more preferably 30 mm or less or 25 mm or less, even more preferably 22 mm or less or 20 mm or less, and particularly preferably 18 mm or less, 16 mm or less, 15 mm or less, 14 mm or less, or 13 mm or less. The lower limit is not particularly limited, but may be 0.1 mm or more, 1 mm or more, etc.

[0282] In one embodiment, the cured product of the resin composition according to the present invention is characterized by reduced warpage. For example, when measured as described in the <Warpage Measurement> section below, the warpage of the cured product on an inner layer substrate cut to a size of 120 mm x 160 mm after full curing (curing at 200°C for 90 minutes) is preferably 40 mm or less or 35 mm or less, more preferably 30 mm or less or 25 mm or less, even more preferably 22 mm or less or 20 mm or less, and particularly preferably 18 mm or less or 16 mm or less. The lower limit is not particularly limited, but may be 0.1 mm or more, 1 mm or more, etc.

[0283] In one embodiment, the cured product of the resin composition according to the present invention is characterized by high plating peel strength. For example, when measured as described in the section <Measurement of Plating Peel Strength> below, the load applied when measuring the peel strength between the insulating layer (cured product) and the plating conductor layer is preferably 0.15 kgf / cm or more, more preferably 0.20 kgf / cm or more, even more preferably 0.25 kgf / cm or more or 0.30 kgf / cm or more, and particularly preferably 0.32 kgf / cm or more or 0.34 kgf / cm or more. The upper limit is not particularly limited, but may be 10 kgf / cm or less, 1 kgf / cm or less, etc.

[0284] In one embodiment, a cured product of the resin composition according to the present invention is characterized by excellent reflow resistance. For example, as described in the <Reflow Test> section below, when the cured product is subjected to moisture absorption for 19 hours in a thermo-hygrostat chamber at a humidity of 85% RH and a temperature of 55°C, followed by reflow at a peak temperature of 260°C, preferably no swelling occurs after 10 reflow cycles, and more preferably no swelling occurs after 20 reflow cycles.

[0285] Here, in the reflow test, as described in the <Reflow Test> section below, an inner layer substrate is used in which copper foil is laminated on both sides of a resin substrate, and an inner layer circuit may be formed on the copper foil. When the resin substrate is exposed due to the formation of an inner layer circuit (inner layer circuits 2 to 4 in FIG. 1), swelling is likely to occur during the reflow test due to the tendency for moisture to be absorbed from the exposed portion. On the other hand, when the resin substrate is not exposed (inner layer circuit 1 in FIG. 1), swelling is likely to occur due to the lack of an escape route for gas generated in the resin composition layer during the reflow test. In other words, although swelling during the reflow test can occur due to the above two causes, it is preferable that swelling does not occur due to either cause. In other words, it is preferable that swelling does not occur during the reflow test when any of the inner layer circuits 1 to 4 in FIG. 1 is used.

[0286] As described above, the resin composition of the present invention can provide a cured product that has a low dielectric loss tangent, excellent smear removability, and high heat resistance (glass transition temperature). Therefore, the resin composition of the present invention can be suitably used as a resin composition for forming an insulating layer of a printed wiring board (resin composition for an insulating layer of a printed wiring board), and more suitably used as a resin composition for forming an interlayer insulating layer of a printed wiring board (resin composition for an insulating interlayer of a printed wiring board). The resin composition of the present invention can also be suitably used when the printed wiring board is a circuit board with built-in components. The resin composition of the present invention can also be suitably used as a resin composition for forming an insulating layer of a rewiring board for a semiconductor package (resin composition for an insulating layer of a rewiring board). In the present invention, printed wiring boards and rewiring boards are collectively referred to as "circuit boards," and therefore the resin composition of the present invention can be suitably used for an insulating layer of a circuit board.

[0287] The resin composition of the present invention can be further used in a wide range of applications requiring a resin composition, such as sheet-like laminate materials such as resin sheets and prepregs, solder resists, underfill materials, die bonding materials, hole filling resins, sealing resins, and component embedding resins.

[0288] [Sheet-type laminated materials (resin sheets, prepregs)] The resin composition of the present invention can be used as it is, but may also be used in the form of a sheet-like laminate material containing the resin composition.

[0289] As the sheet-like laminate material, the following resin sheets and prepregs are preferred.

[0290] In one embodiment, the resin sheet includes a support and a layer of a resin composition (hereinafter simply referred to as a "resin composition layer") provided on the support, and is characterized in that the resin composition layer is formed from the resin composition of the present invention.

[0291] The thickness of the resin composition layer varies depending on the application, and may be appropriately determined depending on the application. For example, from the viewpoint of thinning printed wiring boards and semiconductor packages, the thickness of the resin composition layer is preferably 100 μm or less, 80 μm or less, 60 μm or less, 50 μm or less, 40 μm or less, or 30 μm or less. The lower limit of the thickness of the resin composition layer is not particularly limited, but may usually be 1 μm or more, 5 μm or more, etc.

[0292] Examples of the support include a thermoplastic resin film, a metal foil, and a release paper, and a thermoplastic resin film or a metal foil is preferred. Therefore, in a preferred embodiment, the support is a thermoplastic resin film or a metal foil.

[0293] When a thermoplastic resin film is used as the support, examples of the thermoplastic resin include polyester resins such as polyethylene terephthalate (PET) and polyethylene naphthalate (PEN), polycarbonate (PC), acrylic resins such as polymethyl methacrylate (PMMA), cyclic polyolefins, triacetyl cellulose (TAC), polyether sulfide (PES), polyether ketone, polyimide, etc. Among these, polyester resins are preferred, polyethylene terephthalate or polyethylene naphthalate are more preferred, and inexpensive polyethylene terephthalate is particularly preferred.

[0294] When a metal foil is used as the support, examples of the metal foil include copper foil and aluminum foil, with copper foil being preferred. The copper foil may be a foil made of a single metal, copper, or an alloy of copper and another metal (e.g., tin, chromium, silver, magnesium, nickel, zirconium, silicon, titanium, etc.).

[0295] The support may be subjected to a matte treatment, a corona treatment, or an antistatic treatment on the surface that will be bonded to the resin composition layer. Alternatively, a support with a release layer, which has a release layer on the surface that will be bonded to the resin composition layer, may be used. Examples of the release agent used in the release layer of the support with a release layer include one or more release agents selected from the group consisting of alkyd resins, polyolefin resins, urethane resins, and silicone resins. Commercially available release agents include "SK-1," "AL-5," and "AL-7" manufactured by Lintec Corporation. Alternatively, a commercially available support with a release layer may be used, such as "Purex" manufactured by Toyobo Co., Ltd. or "Uni-Peel" manufactured by Unitika Ltd., which are PET films having a release layer primarily composed of an alkyd resin-based release agent or a polyolefin resin-based release agent.

[0296] The thickness of the support is not particularly limited, but is preferably in the range of 5 μm to 75 μm, more preferably 10 μm to 60 μm. When a support with a release layer is used, it is preferable that the thickness of the entire support with a release layer is in the above range.

[0297] When a metal foil is used as the support, a metal foil with a support substrate may be used, which is a thin metal foil with a peelable support substrate attached thereto. In one embodiment, the metal foil with a support substrate includes a support substrate, a release layer provided on the support substrate, and a metal foil provided on the release layer. When a metal foil with a support substrate is used as the support, the resin composition layer is provided on the metal foil.

[0298] In the metal foil with a supporting substrate, the material of the supporting substrate is not particularly limited, but examples thereof include copper foil, aluminum foil, stainless steel foil, titanium foil, copper alloy foil, etc. When copper foil is used as the supporting substrate, it may be electrolytic copper foil or rolled copper foil. Furthermore, the release layer is not particularly limited as long as it allows the metal foil to be released from the supporting substrate, and examples thereof include an alloy layer of an element selected from the group consisting of Cr, Ni, Co, Fe, Mo, Ti, W, and P; an organic coating, etc.

[0299] In the metal foil with a supporting substrate, the material of the metal foil is preferably, for example, copper foil or copper alloy foil.

[0300] In the metal foil with a supporting substrate, the thickness of the supporting substrate is not particularly limited, but is preferably in the range of 10 μm to 150 μm, more preferably in the range of 10 μm to 100 μm. The thickness of the metal foil may be, for example, in the range of 0.1 μm to 10 μm.

[0301] In one embodiment, the resin sheet may further include an optional layer, if necessary. Examples of such optional layers include a protective film provided on the surface of the resin composition layer that is not bonded to the support (i.e., the surface opposite the support). The thickness of the protective film is not particularly limited, but is, for example, 1 μm to 75 μm, and preferably 1 μm to 40 μm. By laminating the protective film, adhesion of dust and the like to the surface of the resin composition layer and scratches can be suppressed.

[0302] The resin sheet can be produced, for example, by preparing a liquid resin composition as is or a resin varnish by dissolving the resin composition in an organic solvent, applying this onto a support using a die coater or the like, and then drying to form a resin composition layer.

[0303] The organic solvent may be the same as the organic solvent described as a component of the resin composition. The organic solvent may be used alone or in combination of two or more.

[0304] Drying may be carried out by known methods such as heating or hot air blowing. Drying conditions are not particularly limited, but drying is carried out so that the content of organic solvent in the resin composition layer becomes 10% by mass or less, preferably 5% by mass or less. Although this varies depending on the boiling point of the organic solvent in the resin composition or resin varnish, for example, when a resin composition or resin varnish containing 30% by mass 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.

[0305] The resin sheet can be stored in a rolled state. When the resin sheet has a protective film, it can be used by peeling off the protective film.

[0306] In one embodiment, the prepreg is formed by impregnating a sheet-like fiber substrate with the resin composition of the present invention.

[0307] The sheet-like fiber substrate used for the prepreg is not particularly limited, and commonly used prepreg substrates such as glass cloth, aramid nonwoven fabric, and liquid crystal polymer nonwoven fabric can be used. From the viewpoint of thinning printed wiring boards and semiconductor packages, the thickness of the sheet-like fiber substrate is preferably 50 μm or less, more preferably 40 μm or less, even more preferably 30 μm or less, and particularly preferably 20 μm or less. There is no particular lower limit to the thickness of the sheet-like fiber substrate. It is usually 10 μm or more.

[0308] The prepreg can be produced by a known method such as a hot melt method or a solvent method.

[0309] The thickness of the prepreg may be in the same range as that of the resin composition layer in the resin sheet described above.

[0310] The sheet-like laminate material of the present invention can be suitably used to form an insulating layer of a printed wiring board (for the insulating layer of a printed wiring board), and can be more suitably used to form an interlayer insulating layer of a printed wiring board (for the insulating interlayer of a printed wiring board). The sheet-like laminate material of the present invention can also be suitably used to form an insulating layer of a rewiring board of a semiconductor package (for the insulating layer of a rewiring board). That is, the sheet-like laminate material of the present invention can be suitably used as an insulating layer of a circuit board.

[0311] [Circuit board] The resin composition of the present invention can be used to form an insulating layer for a circuit board. The present invention also provides such a circuit board, i.e., a circuit board comprising an insulating layer made of a cured product of the resin composition of the present invention.

[0312] <Printed wiring board> In one embodiment, the circuit board of the present invention is a printed wiring board.

[0313] The printed wiring board can be produced, for example, by using the above-mentioned resin sheet by a method including the following steps (I) and (II). (I) A step of laminating a resin sheet on an inner layer substrate so that the resin composition layer of the resin sheet is bonded to the inner layer substrate. (II) A step of curing (e.g., thermally curing) the resin composition layer to form an insulating layer.

[0314] The "inner layer substrate" used in step (I) is a member that will become the substrate of a printed wiring board, and examples thereof include glass epoxy substrates, metal substrates, polyester substrates, polyimide substrates, BT resin substrates, and thermosetting polyphenylene ether substrates. The substrate may have a conductor layer on one or both sides, and this conductor layer may be patterned. An inner layer substrate having a conductor layer (circuit) formed on one or both sides of the substrate may be referred to as an "inner layer circuit board." Furthermore, the "inner layer substrate" of the present invention also includes intermediate products on which an insulating layer and / or a conductor layer is to be further formed during the production of a printed wiring board. When the printed wiring board is a circuit board with built-in components, an inner layer substrate with built-in components may be used.

[0315] The inner layer substrate and the resin sheet can be laminated, for example, by thermocompression bonding the resin sheet to the inner layer substrate from the support side. Examples of a member for thermocompression bonding the resin sheet to the inner layer substrate (hereinafter also referred to as a "thermocompression bonding member") include a heated metal plate (such as a SUS end plate) or a metal roll (SUS roll). The thermocompression bonding member may be pressed directly onto the resin sheet, or may be pressed via an elastic material such as heat-resistant rubber so that the resin sheet can sufficiently conform to the surface irregularities of the inner layer substrate.

[0316] The lamination of the inner layer substrate and the resin sheet may be carried out by a vacuum lamination method. In the vacuum lamination method, the thermocompression temperature is preferably in the range of 60°C to 160°C, more preferably 80°C to 140°C, the thermocompression pressure is preferably in the range of 0.098MPa to 1.77MPa, more preferably 0.29MPa to 1.47MPa, and the thermocompression time is preferably in the range of 20 seconds to 400 seconds, more preferably 30 seconds to 300 seconds. The lamination may be carried out under reduced pressure conditions, preferably at a pressure of 26.7hPa or less.

[0317] The lamination can be performed using a commercially available vacuum laminator, such as a vacuum pressure laminator manufactured by Meiki Seisakusho Co., Ltd., a vacuum applicator manufactured by Nikko Materials Co., Ltd., or a batch vacuum pressure laminator.

[0318] After lamination, the laminated resin sheets may be smoothed under normal pressure (atmospheric pressure), for example, by pressing a thermocompression member from the support side. The pressing conditions for the smoothing treatment may be the same as the thermocompression conditions for lamination. The smoothing treatment may be performed using a commercially available laminator. Note that lamination and smoothing treatment may be performed consecutively using the commercially available vacuum laminator.

[0319] The support may be removed between step (I) and step (II), or after step (II). When a metal foil is used as the support, the conductor layer may be formed using the metal foil without peeling off the support. When a metal foil with a supporting substrate is used as the support, the supporting substrate (and the release layer) may be peeled off. Then, the conductor layer can be formed using the metal foil.

[0320] In step (II), the resin composition layer is cured (for example, by heat curing) to form an insulating layer made of a cured product of the resin composition. The curing conditions for the resin composition layer are not particularly limited, and conditions typically employed for forming insulating layers for printed wiring boards may be used.

[0321] For example, the thermal curing conditions for the resin composition layer vary depending on the type of resin composition, etc., but in one embodiment, the curing temperature is preferably 140° C. to 250° C., more preferably 150° C. to 240° C., and even more preferably 180° C. to 230° C. The curing time is preferably 5 minutes to 240 minutes, more preferably 10 minutes to 150 minutes, and even more preferably 15 minutes to 120 minutes.

[0322] Before thermally curing the resin composition layer, the resin composition layer may be preheated at a temperature lower than the curing temperature. For example, prior to thermally curing the resin composition layer, the resin composition layer may be preheated at a temperature of 50°C to 140°C, preferably 60°C to 135°C, more preferably 70°C to 130°C for 5 minutes or more, preferably 5 minutes to 150 minutes, more preferably 15 minutes to 120 minutes, and even more preferably 15 minutes to 100 minutes.

[0323] When manufacturing a printed wiring board, the following steps may be further performed: (III) drilling holes in the insulating layer, (IV) roughening the insulating layer, and (V) forming a conductor layer. These steps (III) to (V) may be performed according to various methods known to those skilled in the art and used in manufacturing printed wiring boards. When the support is removed after step (II), the removal of the support may be performed between steps (II) and (III), between steps (III) and (IV), or between steps (IV) and (V). Furthermore, if necessary, the formation of the insulating layer and the conductor layer in steps (I) to (V) may be repeated to form a multilayer wiring board.

[0324] In another embodiment, the printed wiring board of the present invention can be produced using the above-mentioned prepreg. The production method is basically the same as when a resin sheet is used.

[0325] Step (III) is a step of drilling holes in the insulating layer, thereby forming holes such as via holes and through holes in the insulating layer. Step (III) may be performed using, for example, a drill, a laser, plasma, or the like, depending on the composition of the resin composition used to form the insulating layer. The dimensions and shape of the holes may be determined appropriately depending on the design of the printed wiring board.

[0326] Step (IV) is a step of roughening the insulating layer. Usually, in this step (IV), smear removal (desmear) is also performed. The procedure and conditions of the roughening treatment are not particularly limited, and known procedures and conditions commonly used in forming insulating layers for printed wiring boards can be adopted. For example, the insulating layer can be roughened by performing a swelling treatment with a swelling liquid, a roughening treatment with an oxidizing agent, and a neutralization treatment with a neutralizing liquid in this order.

[0327] The swelling liquid used in the roughening treatment is not particularly limited, but examples thereof include alkaline solutions and surfactant solutions, and is preferably an alkaline solution, with sodium hydroxide solution and potassium hydroxide solution being more preferred. Commercially available swelling liquids include "Swelling Dip Securigance P" and "Swelling Dip Securigance SBU" manufactured by Atotech Japan. The swelling treatment using a swelling liquid is not particularly limited, but can be carried out by, for example, immersing the insulating layer in a swelling liquid at 30°C to 90°C for 1 to 20 minutes. To keep the swelling of the resin in the insulating layer to an appropriate level, it is preferable to immerse the insulating layer in a swelling liquid at 40°C to 80°C for 5 to 15 minutes.

[0328] The oxidizing agent used in the roughening treatment is not particularly limited, but examples thereof include alkaline permanganate solutions prepared by dissolving potassium permanganate or sodium permanganate in an aqueous solution of sodium hydroxide. Roughening treatment using an oxidizing agent such as alkaline permanganate solution is preferably carried out by immersing the insulating layer in an oxidizing agent solution heated to 60°C to 100°C for 10 to 30 minutes. The concentration of permanganate in the alkaline permanganate solution is preferably 5% by mass to 10% by mass. Commercially available oxidizing agents include alkaline permanganate solutions such as "Concentrate Compact CP" and "Dosing Solution Securigance P" manufactured by Atotech Japan.

[0329] The neutralizing solution used in the roughening treatment is preferably an acidic aqueous solution, and examples of commercially available products include "Reduction Solution Securigant P" manufactured by Atotech Japan.

[0330] Treatment with a neutralizing solution can be carried out by immersing the surface that has been roughened with an oxidizing agent in a neutralizing solution at 30° C. to 80° C. for 5 to 30 minutes. From the standpoint of workability, etc., a method in which the object that has been roughened with an oxidizing agent is immersed in a neutralizing solution at 40° C. to 70° C. for 5 to 20 minutes is preferred.

[0331] Step (V) is a step of forming a conductor layer, and the conductor layer is formed on the insulating layer. The conductor material used for the conductor layer is not particularly limited. In a preferred embodiment, the conductor layer contains 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 may 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). Among these, from the viewpoints of versatility in forming the conductor layer, cost, ease of patterning, etc., a single metal layer of chromium, nickel, titanium, aluminum, zinc, gold, palladium, silver, or copper, or an alloy layer of a nickel-chromium alloy, a copper-nickel alloy, or a copper-titanium alloy is preferred, a single metal layer of chromium, nickel, titanium, aluminum, zinc, gold, palladium, silver, or copper, or an alloy layer of a nickel-chromium alloy is more preferred, and a single metal layer of copper is even more preferred.

[0332] The conductor layer may have a single layer structure or a multi-layer structure in which two or more single metal layers or alloy layers made of different types of metals or alloys are laminated. When the conductor layer has 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 a nickel-chromium alloy.

[0333] The thickness of the conductor layer depends on the desired design of the printed wiring board, but is generally 3 μm to 35 μm, preferably 5 μm to 30 μm.

[0334] In one embodiment, the conductor layer may be formed by plating. From the viewpoint of facilitating the formation of fine wiring, it is preferable to form the conductor layer by a semi-additive method. An example of forming the conductor layer by a semi-additive method will be described below.

[0335] First, a plating seed layer is formed on the surface of an insulating layer by electroless plating. Next, a mask pattern is formed on the formed plating seed layer, exposing a portion of the plating seed layer corresponding to the desired wiring pattern. After a metal layer is formed on the exposed plating seed layer by electrolytic plating, the mask pattern is removed. Thereafter, unnecessary plating seed layer is removed by etching or the like, thereby forming a conductor layer having the desired wiring pattern.

[0336] In another embodiment, the conductor layer may be formed using a metal foil. When a metal foil is used 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 a metal foil is laminated on the exposed surface of the resin composition layer. The lamination of the resin composition layer and the metal foil may be performed by a vacuum lamination method. The lamination conditions may be the same as those described for step (I). Next, step (II) is performed to form an insulating layer. Thereafter, a conductor layer having a desired wiring pattern can be formed using the metal foil on the insulating layer by a conventional known technique such as a modified semi-additive method.

[0337] The metal foil can be produced by a known method such as an electrolytic method, a rolling method, etc. Examples of commercially available metal foils include HLP foil and JXUT-III foil manufactured by JX Nippon Mining & Metals Corporation, and 3EC-III foil and TP-III foil manufactured by Mitsui Mining & Smelting Co., Ltd.

[0338] Alternatively, when a metal foil or a metal foil with a supporting substrate is used as the support for the resin sheet, the conductor layer may be formed using the metal foil, as described above.

[0339] <Rewiring substrate for semiconductor packages> In one embodiment, the circuit board of the present invention is a rewiring substrate (rewiring layer) of a semiconductor package. Hereinafter, a method for manufacturing a semiconductor package will be described.

[0340] The semiconductor package includes an insulating layer made of a cured product of the resin composition of the present invention as an insulating layer of a rewiring substrate. The semiconductor package may also include a sealing layer made of a cured product of the resin composition of the present invention.

[0341] A semiconductor package can be produced, for example, by a method including the following steps (1) to (6) using the resin composition and resin sheet of the present invention. The resin composition and resin sheet of the present invention can be used to form a rewiring formation layer (insulating layer for forming a rewiring substrate) in step (5) or a sealing layer in step (3). An example of forming a rewiring formation layer or a sealing layer using a resin composition or a resin sheet will be shown below. However, techniques for forming a rewiring formation layer or a sealing layer for a semiconductor package are known, and a person skilled in the art can produce a semiconductor package using the resin composition and resin sheet of the present invention according to known techniques. (1) a step of laminating a temporary fixing film on a substrate; (2) a step of temporarily fixing a semiconductor chip on a temporary fixing film; (3) forming an encapsulation layer on the semiconductor chip; (4) peeling the substrate and the temporary fixing film from the semiconductor chip; (5) forming a rewiring formation layer as an insulating layer on the surface of the semiconductor chip from which the base material and the temporary fixing film have been peeled off; and (6) A step of forming a rewiring layer as a conductor layer on the rewiring formation layer.

[0342] <<Process (1)>> The material used for the substrate is not particularly limited. Examples of the substrate include semiconductor wafers such as silicon wafers, glass wafers, glass substrates, metal substrates such as copper, titanium, stainless steel, and cold-rolled steel sheets (SPCC), substrates in which glass fibers are impregnated with epoxy resin or the like and then thermoset (e.g., FR-4 substrates), and substrates made of bismaleimide triazine resin (BT resin).

[0343] The material of the temporary fixing film is not particularly limited as long as it can be peeled off from the semiconductor chip in step (4) and can temporarily fix the semiconductor chip. Commercially available products can be used as the temporary fixing film. Examples of commercially available products include Riva Alpha manufactured by Nitto Denko Corporation.

[0344] <<Process (2)>> The semiconductor chips can be temporarily fixed using known devices such as a flip chip bonder, a die bonder, etc. The layout and number of semiconductor chips to be arranged can be appropriately set depending on the shape and size of the temporary fixing film, the number of semiconductor packages to be produced, etc., and for example, the semiconductor chips can be temporarily fixed by arranging them in a matrix of multiple rows and multiple columns.

[0345] <<Process (3)>> The resin composition layer of the resin sheet of the present invention is laminated on a semiconductor chip, or the resin composition of the present invention is applied to a semiconductor chip and cured (for example, thermally cured) to form a sealing layer.

[0346] For example, lamination of a semiconductor chip and a resin sheet can be performed by removing the protective film from the resin sheet and then thermocompressing the resin sheet to the semiconductor chip from the support side. Examples of a member for thermocompressing the resin sheet to the semiconductor chip (hereinafter also referred to as a "thermocompression member") include a heated metal plate (such as a SUS plate) or a metal roll (SUS roll). It is preferable to press the thermocompression member not directly onto the resin sheet, but via an elastic material such as heat-resistant rubber, so that the resin sheet can adequately conform to the surface irregularities of the semiconductor chip. The semiconductor chip and resin sheet can also be laminated by a vacuum lamination method, and the lamination conditions and preferred ranges are the same as those described in relation to the method for manufacturing a printed wiring board.

[0347] After lamination, the resin composition is thermally cured to form the sealing layer under the same conditions as those described in relation to the method for producing a printed wiring board.

[0348] The support of the resin sheet may be peeled off after the resin sheet is laminated on the semiconductor chip and thermally cured, or the support may be peeled off before the resin sheet is laminated on the semiconductor chip.

[0349] When forming a sealing layer by applying the resin composition of the present invention, the application conditions are the same as the application conditions when forming the resin composition layer described in relation to the resin sheet of the present invention, and the preferred ranges are also the same.

[0350] <<Process (4)>> The method for peeling off the substrate and the temporary fixing film can be changed as appropriate depending on the material of the temporary fixing film, etc., and examples include a method in which the temporary fixing film is heated and foamed (or expanded) to peel it off, and a method in which ultraviolet light is irradiated from the substrate side to reduce the adhesive strength of the temporary fixing film and peel it off.

[0351] In the method of heating and foaming (or expanding) the temporary fixing film to peel it off, the heating conditions are usually 100 to 250°C for 1 to 90 seconds or 5 to 15 minutes. In the method of irradiating ultraviolet light from the substrate side to reduce the adhesive strength of the temporary fixing film to peel it off, the irradiation dose of ultraviolet light is usually 10 mJ / cm. 2 ~1000mJ / cm 2 is.

[0352] <<Process (5)>> The resin composition and resin sheet of the present invention are used to form a rewiring formation layer (insulating layer of a rewiring substrate).

[0353] After forming the redistribution layer, via holes may be formed in the redistribution layer to connect the semiconductor chip to a conductor layer (described later). The via holes may be formed by a known method depending on the material of the redistribution layer.

[0354] <<Process (6)>> The formation of the conductor layer on the rewiring formation layer may be carried out in the same manner as in step (V) described in relation to the method for producing a printed wiring board. Note that steps (5) and (6) may be repeated to alternately stack (build up) the conductor layer (rewiring layer) and the rewiring formation layer (insulating layer).

[0355] The manufacturing of the semiconductor package may further include steps of (7) forming a solder resist layer on the conductor layer (rewiring layer), (8) forming bumps, and (9) dicing the multiple semiconductor packages into individual semiconductor packages. These steps may be performed according to various methods known to those skilled in the art that are used in the manufacturing of semiconductor packages.

[0356] By forming a rewiring formation layer (insulating layer) using the resin composition or resin sheet of the present invention, which can provide a cured product exhibiting a low dielectric loss tangent, excellent smear removal properties, and high heat resistance (glass transition temperature), a semiconductor package with extremely low transmission loss can be realized without concerns about cracks or circuit distortion, regardless of whether the semiconductor package is a fan-in package or a fan-out package. In one embodiment, the semiconductor package of the present invention is a fan-out package. The resin composition or resin sheet of the present invention can be applied to both a fan-out panel level package (FOPLP) and a fan-out wafer level package (FOWLP). In one embodiment, the semiconductor package of the present invention is a fan-out panel level package (FOPLP) or a fan-out wafer level package (FOWLP).

[0357] [Semiconductor Devices] The semiconductor device of the present invention includes a layer made of a cured product of the resin composition layer of the present invention. The semiconductor device of the present invention can be produced using the circuit board of the present invention.

[0358] Examples of semiconductor devices include various semiconductor devices used in electrical appliances (for example, computers, mobile phones, digital cameras, and televisions) and vehicles (for example, motorcycles, automobiles, trains, ships, and aircraft). [Example]

[0359] The present invention will be described in more detail below with reference to examples. However, the present invention is not limited to these examples. In the following description, "parts" and "%" representing amounts mean "parts by mass" and "% by mass", respectively, unless otherwise specified. Furthermore, unless otherwise specified, the temperature and pressure conditions are room temperature (23°C) and atmospheric pressure (1 atm).

[0360] <Synthesis Example 1: Synthesis of maleimide compound (A-1)> (I) Synthesis of intermediate amine compound (a-1) A flask equipped with a thermometer, a condenser, a Dean-Stark trap, and a stirrer was charged with 400 g (3.3 mol) of 2-ethylaniline, 127 g of a compound (b) having a benzyl ether skeleton (Nikanol L, manufactured by Fudow Corporation), 193 g of toluene, and 53 g of activated clay. The mixture was heated to 120°C with stirring and held for 30 minutes. The mixture was then heated to 150°C and held for 3 hours. After the hold, the mixture was heated to 200°C over 30 minutes and held for 10 hours. After the hold, the mixture was diluted with 193 g of toluene, and the activated clay was filtered off. The solvent and excess 2-ethylaniline were distilled off from the filtrate by heating under reduced pressure, yielding intermediate amine compound (a-1) (amine equivalent: 209 g / eq.).

[0361] (II) Maleimidation A 2-L flask equipped with a thermometer, condenser, Dean-Stark trap, and stirrer was charged with 73.2 g (126 mol, 1.3 equivalents) of maleic anhydride and 461 g of toluene and stirred at room temperature. Next, a mixed solution of 209 g (1 equivalent) of intermediate amine compound (a-1) and 57.7 g of N,N-dimethylformamide (DMF) was added dropwise over 1 hour, followed by a 2-hour reaction. 9.72 g of p-toluenesulfonic acid monohydrate was added to the reaction solution, and the reaction solution was heated to 115°C. The resulting azeotropic water and toluene were cooled and separated under reflux. The toluene alone was then returned to the system and the dehydration reaction was carried out for 5 hours. After cooling to room temperature, the mixture was concentrated under reduced pressure. The resulting brown solution was dissolved in 600 g of ethyl acetate and washed three times with 200 g of ion-exchanged water and three times with 150 g of 2% by weight aqueous sodium bicarbonate solution. After adding sodium sulfate to dry, the reaction mixture was concentrated under reduced pressure and then vacuum dried at 80° C. for 4 hours to obtain maleimide compound (A-1). [ka]

[0362] <Synthesis Example 2: Synthesis of Active Ester Resin (D-1)> A flask equipped with a thermometer, dropping funnel, condenser, distillation column, and stirrer was charged with 320 g (2.0 mol) of 2,7-dihydroxynaphthalene, 184 g (1.7 mol) of benzyl alcohol, and 5.0 g of p-toluenesulfonic acid monohydrate. The mixture was stirred at room temperature while blowing in nitrogen. The temperature was then raised to 150 °C, and the mixture was stirred for 4 hours while distilling off the resulting water. After the reaction was completed, 900 g of methyl isobutyl ketone and 5.4 g of 20% aqueous sodium hydroxide solution were added for neutralization. The aqueous layer was then removed by separation, washed three times with 280 g of water, and the methyl isobutyl ketone was removed under reduced pressure to obtain 460 g of benzyl-modified naphthalene compound (D'). The resulting benzyl-modified naphthalene compound (D') was a black solid with a hydroxyl equivalent of 180 g / eq.

[0363] A flask equipped with a thermometer, dropping funnel, condenser, distillation column, and stirrer was charged with 203.0 g of isophthalic acid chloride (molar number of acid chloride groups: 2.0 mol) and 1,400 g of toluene. The system was then purged with nitrogen under reduced pressure and dissolved. Next, 113.9 g (0.67 mol) of orthophenylphenol and 240 g of benzyl-modified naphthalene compound (D') (molar number of phenolic hydroxyl groups: 1.33 mol) were charged and the system was then purged with nitrogen under reduced pressure and dissolved. Then, 0.70 g of tetrabutylammonium bromide was dissolved. While purging with nitrogen gas, the system was controlled to below 60°C, and 400 g of 20% aqueous sodium hydroxide solution was added dropwise over 3 hours. The reaction was then allowed to proceed under these conditions with stirring for 1 hour.

[0364] After the reaction was completed, the mixture was allowed to stand for separation, and the aqueous layer was removed. Furthermore, water was added to the toluene layer in which the reactant was dissolved, and the mixture was stirred and mixed for 15 minutes. The mixture was then allowed to stand for separation, and the aqueous layer was removed. This procedure was repeated until the pH of the aqueous layer reached 7. The water was then removed by decanting, yielding an active ester resin (D-1) in the form of a toluene solution with a non-volatile content of 65% by mass. The active ester group equivalent of the obtained active ester resin (D-1) was 238 g / eq. [ka]

[0365] <Synthesis Example 3: Synthesis of Active Ester Resin (D-3)> A flask equipped with a thermometer, dropping funnel, condenser, distillation column, and stirrer was charged with 165 g of a polyaddition resin (hydroxyl equivalent: 165 g / eq., softening point: 85°C) of dicyclopentadiene and phenol, 134 g (1.0 mol) of ortho-allylphenol, and 1200 g of toluene. The system was then purged with nitrogen under reduced pressure. Next, 203 g (1.0 mol) of isophthalic acid chloride was added, and the system was purged with nitrogen under reduced pressure. 0.6 g of tetrabutylammonium bromide was added, and while purging with nitrogen gas, the system was maintained at 60°C or below. 412 g of 20% aqueous sodium hydroxide solution was added dropwise over 3 hours. After the addition, the mixture was stirred for 1.0 hour. After the reaction was complete, the aqueous layer was removed by static separation. Water was added to the resulting toluene layer and stirred for 15 minutes. The aqueous layer was then removed by static separation. This procedure was repeated until the pH of the aqueous layer reached 7. The nonvolatile content was then adjusted to 70% by mass by heat drying to obtain an active ester resin (D-3) represented by the following formula: s represents an integer of 0 or 1 or greater, and the average value of r calculated from the charge ratio is 1. The wavy line represents a structure obtained by reaction of isophthalic acid chloride with a phenol polyaddition reaction resin and / or ortho-allylphenol. [ka]

[0366] <Synthesis Example 4: Synthesis of other maleimide compounds (F-1)> According to Synthesis Example 1 in Japan Institute of Invention and Innovation Disclosure Technical Bulletin No. 2020-500211, an MEK solution (non-volatile components 62% by mass) of a maleimide compound (F-1) represented by the following formula was prepared. The Mw / Mn of this maleimide compound (F-1) was 1.81, and t'' in the formula was 1.47 (mainly 1, 2, or 3). [ka]

[0367] <Synthesis Example 5: Synthesis of vinyl resin (G-1)> 3.0 mol (390.6 g) of divinylbenzene, 1.8 mol (229.4 g) of ethylvinylbenzene, 10.2 mol (1066.3 g) of styrene, and 15.0 mol (1532.0 g) of n-propyl acetate were charged into a 5.0 L reactor, and 600 mmol of boron trifluoride diethyl ether complex was added at 70 °C and reacted for 4 hours. The polymerization solution was terminated with aqueous sodium bicarbonate solution. The oil layer was then washed three times with pure water, and the polymer was recovered by devolatilization under reduced pressure at 60 °C. The resulting polymer was weighed, confirming that 896.7 g of vinyl resin (G-1) was obtained. The weight-average molecular weight (Mw) of vinyl resin (G-1) was 41,300.

[0368] <Synthesis Example 6: Synthesis of vinyl resin (G-2)> 1,1-bis(4-hydroxy-3-methylphenyl)-3,3,5-trimethylcyclohexane (33.85 g), 4,6-dichloro-2-phenylpyrimidine (16.66 g), and potassium carbonate (18.66 g) were weighed into a four-neck separable flask equipped with a stirrer, and N-methyl-2-pyrrolidone (42.50 g) was added, followed by reaction for 6 hours at 10°C under a nitrogen atmosphere. After the reaction, m,p-(chloromethyl)styrene (8.68 g) was added dropwise with the vessel cooled to 10°C, and the reaction was continued for 4 hours at 100°C.

[0369] The resulting reaction solution was diluted with N-methyl-2-pyrrolidone (55.0 g), and the salt was removed by filtration. The resulting solution was then poured into methanol (6900 g). The precipitated solid was filtered off, washed with a small amount of methanol, and filtered again to recover the solid. The solid was then dried under reduced pressure at 60°C for 12 hours using a vacuum dryer to obtain vinyl resin (G-2) (yield: 46.55 g, yield: 90%). The weight-average molecular weight Mw of vinyl resin (G-2) was 3,400.

[0370] <Examples 1 to 15 and Comparative Examples 1 to 4> (1) Production of resin composition Each component was weighed and mixed according to the formulation shown in Table 1 below, and then 10 parts of MEK (methyl ethyl ketone) and 10 parts of cyclohexanone were added and uniformly dispersed using a high-speed rotary mixer to obtain a resin composition (resin varnish). The formulation shown in Table 1 indicates the amount (parts by mass) of nonvolatile components. [Table 1]

[0371] The details of each component listed in Table 1 are as follows: (A) Maleimide compound having a specific structure Maleimide compound (A-1): Maleimide compound (A-1) synthesized in Synthesis Example 1

[0372] (B) Epoxy resin HP-4032SS: Epoxy equivalent weight 144g / eq., manufactured by DIC, naphthalene-type epoxy resin NC-3000L: Epoxy equivalent 270g / eq., manufactured by Nippon Kayaku Co., Ltd., biphenyl type epoxy resin

[0373] (D1) Active ester resin Active ester resin (D-1): Active ester group equivalent weight 238 g / eq., active ester resin (D-1) synthesized in Synthesis Example 2 Active ester resin (D-2): an active ester resin having an active ester group equivalent of 250 g / eq. and represented by the following formula (wherein n≧0), with a non-volatile content of 60% by mass in toluene [ka] Active ester resin (D-3): Active ester group equivalent weight 214 g / eq., active ester resin (D-3) synthesized in Synthesis Example 3, toluene solution with 70% nonvolatile content Active ester resin (D-4): Active ester resin with an active ester group equivalent of 248 g / eq., represented by the following formula, toluene solution of 70% non-volatile components [ka] Active ester resin (D-5): Active ester resin with an active ester group equivalent of 1002 g / eq., represented by the following formula: [ka] HPC-8000L-65MT: Active ester resin containing dicyclopentadiene-type diphenol structure, toluene / MEK solution with an active ester group equivalent of 223 g / eq. and 65% non-volatile content, manufactured by DIC Corporation.

[0374] (D2) Other hardeners LA-3018-50P: phenolic hydroxyl equivalent weight 151 g / eq., 1-methoxy-2-propanol solution with 50% non-volatile content, manufactured by DIC Corporation, phenolic resin

[0375] (E) Inorganic filler SO-C2: Spherical silica surface-treated with an amino-silane coupling agent (Shin-Etsu Chemical Co., Ltd. "KBM573"), average particle size 0.5 μm, specific surface area 5.8 m 2 / g, manufactured by Admatechs Co., Ltd.

[0376] (F) Other maleimide compounds Other maleimide compounds (F-1): Other maleimide compounds (F-1) synthesized in Synthesis Example 4 MIR-3000-70MT: toluene / MEK solution with 70% by mass of non-volatile components, manufactured by Nippon Kayaku Co., Ltd., a maleimide compound having a structure represented by the following formula (in the following formula, n represents 1 to 100): [ka] SLK-6895: Shin-Etsu Chemical Co., Ltd., aliphatic maleimide compound SLK-1500: Shin-Etsu Chemical Co., Ltd., aliphatic maleimide compound

[0377] (G) Radical polymerizable resin OPE-2St 1200: toluene solution with 65% non-volatile content, manufactured by Mitsubishi Gas Chemical Company, Inc., a styrene-based radical polymerizable resin with a polyphenylene ether skeleton Vinyl resin (G-1): Resin (G-1) synthesized in Synthesis Example 5 Vinyl resin (G-2): Resin (G-2) synthesized in Synthesis Example 6

[0378] (H) Organic filler EXL-2655: Organic filler containing rubber components, manufactured by Dow

[0379] (I) Curing accelerator 1B2PZ: Shikoku Chemicals Corporation, imidazole-based curing accelerator (1-benzyl-2-phenylimidazole)

[0380] (2) Resin sheet manufacturing: A polyethylene terephthalate film (thickness: 38 μm) that had been release-treated with an alkyd resin-based release agent ("AL-5" manufactured by Lintec Corporation) was prepared as a support. The obtained resin composition was uniformly applied onto the release layer of this support so that the thickness of the resin composition layer after drying would be 40 μm. The resin composition was then dried at 80°C to 100°C (average 90°C) for 4 minutes to obtain a resin sheet A having a layer structure of a resin composition layer / support. Resin sheet B was produced using the same production method as resin sheet A, except that the coating thickness of the resin composition was changed so that the thickness of the resin composition layer after drying would be 27.5 μm.

[0381] <Dielectric loss tangent measurement test> Resin sheet A was heated in an oven at 190°C for 90 minutes to cure the resin composition layer. The support was then peeled off to obtain a cured resin composition layer. The cured product was cut into a length of 30 mm and a width of 40 mm to obtain a cured product sample for measuring dielectric loss tangent.

[0382] The dielectric loss tangent Df of the cured sample was measured by the split cylinder method using a measuring device ("HP8362B" manufactured by Agilent Technologies) at a measurement frequency of 10 GHz and a measurement temperature of 90° C. Measurement was performed on two test pieces, and the average was calculated.

[0383] <Measurement test of glass transition temperature (Tg) and coefficient of linear thermal expansion (CTE)> Resin sheet A was cured in an oven at 190°C for 90 minutes, and the support was then peeled off to obtain a cured film. This cured film was cut into a length of 20 mm and a width of 6 mm to obtain a cured sample for measuring the glass transition temperature and linear thermal expansion coefficient. This cured sample was measured using a TMA device (thermomechanical analyzer, manufactured by Rigaku Corporation) by heating from 25°C to 220°C at a heating rate of 5°C / min. The same test piece was then measured by heating from 25°C to 250°C at a heating rate of 5°C / min, and Tg and CTE were calculated from the results of the second measurement.

[0384] <Measurement of adhesion strength (CZ copper peel strength) with the conductor layer before and after exposure to a high temperature, high humidity environment (HAST)> (1) Laminating resin sheet A onto the inner layer substrate A glass cloth-based epoxy resin double-sided copper-clad laminate (copper foil thickness 18 μm, substrate thickness 0.8 mm, Panasonic "R1515A") was prepared as an inner layer substrate. The copper foil on this surface was roughened by etching using a microetching agent (MEC "CZ8101") to remove 1 μm of copper.

[0385] The resin sheet A obtained above was laminated onto both sides of the inner layer substrate using a batch-type vacuum pressure laminator (Nikko Materials Co., Ltd., two-stage build-up laminator "CVP1700") so that the resin composition layer of resin sheet A was in contact with the inner layer substrate. The lamination was performed by reducing the pressure to 13 hPa or less for 30 seconds, and then pressing at a temperature of 100°C and a pressure of 0.74 MPa for 30 seconds.

[0386] The laminated resin sheet A was then heat-pressed at atmospheric pressure at 100°C and a pressure of 0.5 MPa for 60 seconds to smooth the surface. The support was then peeled off to obtain an "intermediate multilayer body I" comprising a resin composition layer / inner layer substrate / resin composition layer in this order.

[0387] (2) Copper foil lamination A copper foil (35 μm thick, manufactured by Mitsui Mining & Smelting Co., Ltd., "3EC-III") with a shiny surface was prepared. The shiny surface of this copper foil was roughened by etching with a microetching agent (manufactured by MEC Co., Ltd., "CZ8401") to an etching amount of 0.1 μm. The copper foil thus obtained is referred to as "roughened copper foil."

[0388] This roughened copper foil was laminated on both sides of intermediate multilayer body I so that the roughened surfaces of the roughened copper foil were bonded to the resin composition layers of intermediate multilayer body I. This lamination was carried out under the same conditions as for laminating resin sheet A to the inner layer substrate. In this way, an "intermediate multilayer body II" containing roughened copper foil / resin composition layer / inner layer substrate / resin composition layer / roughened copper foil in this order was obtained.

[0389] (3) Thermal curing of the resin composition layer The obtained intermediate laminate II was placed in a 130 ° C oven and heated for 30 minutes, then transferred to a 170 ° C oven and heated for 30 minutes. Next, the intermediate laminate II was removed from the oven under room temperature atmosphere, and then placed in a 190 ° C oven and heated for an additional 90 minutes. This resulted in thermal curing of the resin composition layer, and an "evaluation substrate" was obtained containing, in this order: roughened copper foil / insulating layer as a cured product of the resin composition layer / inner layer substrate / insulating layer as a cured product of the resin composition layer / roughened copper foil. In this evaluation substrate, the roughened copper foil corresponds to the conductor layer.

[0390] (4) Measurement of adhesion strength with the conductor layer (CZ copper peel strength) The peel strength between the roughened copper foil and the insulating layer was measured using the obtained evaluation board. This peel strength measurement was performed in accordance with JIS C6481. Specifically, the peel strength measurement was performed by the following procedure.

[0391] A slit was made in the roughened copper foil of the evaluation board, surrounding a rectangular area 10 mm wide and 100 mm long. One end of this rectangular area was peeled off and gripped with a gripper (TSE Autocom type testing machine "AC-50C-SL"). A 35 mm long area of ​​this rectangular area was peeled off vertically, and the load (kgf / cm) at the time of peeling was measured as the peel strength. The peeling was performed at room temperature at a rate of 50 mm / min. Furthermore, a high-temperature, high-humidity environmental test (HAST) was performed for 100 hours at a temperature of 130°C and a humidity of 85% RH, and then the peel strength was measured using the same procedure as above.

[0392] <Smear removal evaluation test> (1) Preparation of inner layer board Both sides of a glass cloth-based epoxy resin double-sided copper-clad laminate (copper foil thickness 18 μm, substrate thickness 0.8 mm, Panasonic "R1515A") with an inner layer circuit formed thereon were etched by 1 μm with a microetching agent (MEC "CZ8101") to roughen the copper surface, thereby obtaining an inner layer substrate.

[0393] (2) Lamination of resin sheet B Using a batch-type vacuum pressure laminator (Nikko Materials Co., Ltd., two-stage build-up laminator "CVP1700"), resin sheet B was laminated on both sides of the inner layer substrate so that the resin composition layer was in contact with the inner layer substrate. Lamination was performed by reducing the pressure for 30 seconds to adjust the air pressure to 13 hPa or less, followed by pressure bonding at 120°C and a pressure of 0.74 MPa for 30 seconds. The resin composition layer was then smoothed by heat pressing at 100°C and a pressure of 0.5 MPa for 60 seconds.

[0394] (3) Thermal curing of the resin composition layer The inner layer substrate laminated with resin sheet B was then placed in an oven at 130°C and heated for 30 minutes, and then transferred to an oven at 170°C and heated for 30 minutes to thermally cure the resin composition layer and form an insulating layer. The support was then peeled off to obtain a cured substrate X having a structure of insulating layer / inner layer substrate / insulating layer.

[0395] (4) Formation of via holes The insulating layer of the obtained cured substrate X was drilled using a CO2 laser processing machine ("LK-2K212 / 2C" manufactured by Via Mechanics) under the conditions of a frequency of 2000 Hz, a pulse width of 3 μs, an output of 0.95 W, and a shot count of 3, to form via holes. The opening diameter (diameter, top diameter) of the formed via hole on the surface of the insulating layer was 50 μm, and the diameter (bottom diameter) at the bottom of the insulating layer was 40 μm.

[0396] (5) Roughening treatment The insulating layer of the cured substrate having the via holes formed therein was subjected to a desmear treatment as a roughening treatment, which was the following wet desmear treatment.

[0397] (wet desmear treatment) The cured substrate with the via holes formed was immersed in a swelling solution (Atotech Japan's "Swelling Dip Securigant P," an aqueous solution of diethylene glycol monobutyl ether and sodium hydroxide) at 60°C for 10 minutes. The cured substrate was then immersed in an oxidizing solution (Atotech Japan's "Concentrate Compact P," an aqueous solution of approximately 6% potassium permanganate and 4% sodium hydroxide) at 80°C for 25 minutes. Finally, the cured substrate was immersed in a neutralizing solution (Atotech Japan's "Reduction Solution Securigant P," an aqueous sulfuric acid solution) at 40°C for 5 minutes. The cured substrate was then dried at 80°C for 15 minutes. The cured substrate after this desmearing process is hereinafter referred to as "Evaluation Substrate A."

[0398] (6) Evaluation of smear removal The periphery of the bottom of the via hole of evaluation substrate A was observed with a scanning electron microscope (SEM). From the obtained image, the length of the longest smear (resin residue) extending from the wall surface of the bottom of the via hole (maximum smear length) was measured and evaluated according to the following criteria. "No smear residue": Maximum smear length is less than 5 μm. "Smear residue present": Maximum smear length is 5 μm or more.

[0399] <Measurement of plating peel strength> (1) Roughening treatment The cured substrate X was immersed in a swelling solution (Atotech Japan's "Swelling Dip Securigant P," an aqueous solution of diethylene glycol monobutyl ether and sodium hydroxide) at 60°C for 10 minutes. The cured substrate was then immersed in a roughening solution (Atotech Japan's "Concentrate Compact P," an aqueous solution of KMnO4: 60 g / L and NaOH: 40 g / L) at 80°C for 20 minutes. The cured substrate was then immersed in a neutralizing solution (Atotech Japan's "Reduction Solution Securigant P," an aqueous sulfuric acid solution) at 40°C for 5 minutes. The cured substrate was then dried at 80°C for 30 minutes to obtain "Evaluation Substrate A'."

[0400] (2) Semi-additive plating Evaluation substrate A' was immersed in an electroless plating solution containing palladium chloride (PdCl2) at 40°C for 5 minutes, and then in an electroless copper plating solution at 25°C for 20 minutes. It was then heated at 150°C for 30 minutes for annealing. An etching resist was then formed, and a pattern was formed by etching. Copper sulfate electroplating was then performed to form a conductor layer with a thickness of 20 μm. An annealing treatment was then performed at 190°C for 90 minutes to obtain "evaluation substrate B'."

[0401] (3) Measurement of plating peel strength A cut was made in the conductor layer of evaluation board B' to surround a rectangular area 10 mm wide and 100 mm long. One end of the rectangular area was peeled off and gripped with a gripper (TSE Corporation, Autocom type testing machine "AC-50C-SL"). The rectangular area was peeled off vertically using the gripper at a rate of 50 mm / min at room temperature, and the load (kgf / cm) when 35 mm was peeled off was measured as the plating peel strength.

[0402] <Warpage measurement> (1) Preparation of inner layer board The copper was removed from both sides of a glass cloth-based epoxy resin double-sided copper-clad laminate (copper foil thickness 18 μm, substrate thickness 0.2 mm, "E700G" manufactured by Resonac Co., Ltd.) by etching to obtain an inner layer substrate.

[0403] (2) Lamination of resin sheet A Using a batch-type vacuum pressure laminator (Nikko Materials Co., Ltd., two-stage build-up laminator "CVP1700"), resin sheet A cut to a size of 110 mm x 150 mm was laminated to the center of one side of an inner layer substrate cut to a size of 120 mm x 160 mm, so that the resin composition layer was in contact with the inner layer substrate. Lamination was performed by reducing the pressure for 30 seconds to 13 hPa or less, and then pressing at 140°C and a pressure of 0.74 MPa for 10 seconds.

[0404] (3) Thermal curing of the resin composition layer The inner layer substrate on which resin sheet A was laminated was then placed in a 130°C oven and heated for 30 minutes, and then transferred to a 170°C oven and heated for 30 minutes to thermally cure the resin composition layer and form an insulating layer. The support was then peeled off to obtain a cured substrate Y having an insulating layer / inner layer substrate structure.

[0405] (4) Evaluation of warping after pre-cure The cured substrate Y was placed on a flat table, and two adjacent sides were fixed to the table. The distance from the table to the cured substrate Y was measured with a ruler, and the value was recorded as the amount of warping.

[0406] (5) Evaluation of warpage after full cure Cured substrate Y was placed in an oven at 200°C and heated for 90 minutes to obtain cured substrate Y'. Cured substrate Y' was placed on a flat table and two adjacent sides were fixed to the table. The distance from the table to cured substrate Y' was measured with a ruler and recorded as the amount of warping.

[0407] <Reflow test> (1) Preparation of inner layer board As shown in Figure 1, a double-sided copper-clad glass fabric epoxy resin laminate (copper foil thickness: 35 μm, substrate thickness: 0.2 mm, "E700G" manufactured by Resonac) with inner layer circuits formed on it was etched 1 μm on both sides with a microetching agent ("CZ8101" manufactured by MEC) to roughen the copper surface, resulting in an inner layer substrate. As shown in Figure 1, four types of inner layer circuits were formed on this inner layer substrate. Point 10 in Figure 1 indicates that holes have been formed in the copper foil attached to the surface of the glass fabric epoxy resin, exposing the glass fabric epoxy resin. Specifically, inner layer circuit 1 has no holes in the copper foil, inner layer circuit 2 has holes at 1.5 mm intervals, inner layer circuit 3 has holes at 1 mm intervals, and inner layer circuit 4 has holes at 0.5 mm intervals.

[0408] (2) Lamination of resin sheet A Using a batch-type vacuum pressure laminator (Nikko Materials Co., Ltd., two-stage build-up laminator "CVP1700"), resin sheet A was laminated on both sides of the inner layer substrate so that the resin composition layer was in contact with the inner layer substrate. Lamination was performed by reducing the pressure for 30 seconds to adjust the air pressure to 13 hPa or less, followed by pressure bonding at 140°C and a pressure of 0.74 MPa for 10 seconds. The resin composition layer was then smoothed by heat pressing at 110°C and a pressure of 0.5 MPa for 60 seconds.

[0409] (3) Thermal curing of the resin composition layer The inner layer substrate on which the resin sheet A was laminated was then placed in an oven at 130°C and heated for 30 minutes, and then transferred to an oven at 170°C and heated for 30 minutes to thermally cure the resin composition layer and form an insulating layer. The support was then peeled off to obtain a cured substrate P having a structure of insulating layer / inner layer substrate / insulating layer.

[0410] (4) Roughening treatment The cured substrate P was immersed in a swelling solution (Atotech Japan's "Swelling Dip Securigant P," an aqueous solution of diethylene glycol monobutyl ether and sodium hydroxide) at 60°C for 10 minutes. The cured substrate was then immersed in a roughening solution (Atotech Japan's "Concentrate Compact P," an aqueous solution of KMnO4: 60 g / L and NaOH: 40 g / L) at 80°C for 20 minutes. The cured substrate was then immersed in a neutralizing solution (Atotech Japan's "Reduction Solution Securigant P," an aqueous sulfuric acid solution) at 40°C for 5 minutes. The cured substrate was then dried at 80°C for 30 minutes to obtain "Evaluation Substrate Q."

[0411] (5) Semi-additive plating Evaluation substrate Q was immersed in an electroless plating solution containing palladium chloride (PdCl2) at 40°C for 5 minutes, and then in an electroless copper plating solution at 25°C for 20 minutes. It was then heated at 150°C for 30 minutes for annealing. An etching resist was then formed, and a pattern was formed by etching. Copper sulfate electroplating was then performed to form a conductor layer with a thickness of 20 μm. An annealing treatment was then performed at 190°C for 90 minutes to obtain "evaluation substrate R."

[0412] (6) Reflow test Evaluation board R was cut out to accommodate the four types of inner layer circuits described above, and allowed to absorb moisture for 19 hours in a constant temperature and humidity chamber at 85% RH and 55°C. After that, reflow was performed using a reflow oven at a peak temperature of 260°C. Reflow was performed 20 times on the same test piece, and the presence or absence of swelling was recorded and evaluated according to the following criteria. "○": No swelling after 20 times "△": No swelling after 10 times, swelling after 20 times "×": Swelling occurs after 10 times or less

[0413] As shown in Table 1, Examples 1 to 15, which contained (A) a maleimide compound having a specific structure, (B) an epoxy resin, and (D1) an active ester resin, exhibited low dielectric loss tangents and were able to achieve both excellent smear removability and high heat resistance (glass transition temperature). On the other hand, Comparative Examples 1 to 4, which did not contain (A) a maleimide compound having a specific structure, were inferior in at least one of the dielectric loss tangent, smear removability, and glass transition temperature, and were not at a satisfactory level. [Explanation of symbols]

[0414] 1. Inner layer circuit without exposed resin substrate 2. Resin substrate exposed inner layer circuit with 1.5mm spacing 3. Inner layer circuit with exposed resin substrate at 1.0 mm intervals 4. Inner layer circuit with exposed resin substrate at 0.5mm intervals 10 Exposed area of ​​resin substrate (0.2 mm diameter)

Claims

1. (1A) A maleimide compound having a partial structure represented by the following formula (1), a partial structure represented by the following formula (T-1) that is chemically bonded to the partial structure represented by formula (1), and a partial structure represented by the following formula (T-2) that is chemically bonded to the partial structure represented by formula (1): (B) an epoxy resin, and (D) a curing agent, A resin composition comprising: A resin composition, wherein the component (D) comprises an active ester resin (D1). 【Chemistry 1】 (In formula (1), R １３ Each independently represents a hydrocarbon group having 1 to 18 carbon atoms. ２ each independently represents an integer of 0 to 4, １ represents the number of repeating units. Two * symbols each represent a bond, and one bond corresponds to L in the following formula (T-1): １３ or L １４ and the other bond is L in the following formula (T-2): １１ or L １２ It indicates that the bond is chemically bonded at the position.) 【Chemistry 2】 (In the above formulas (T-1) and (T-2), R １１ and R １５ R each independently represents a hydrocarbon group having 1 to 18 carbon atoms. １２ and R １４ each independently represents a hydrocarbon group having 1 to 18 carbon atoms. １１ , L １２ , L １３ and L １４ each independently represents a bond. １１ or L １２ and is chemically bonded to the partial structure represented by formula (1) at the position of L １３ or L １４ At the position m, the partial structure represented by formula (1) is chemically bonded. １ and m ３ each independently represents an integer of 0 to 2.

2. In formulas (T-1) and (T-2), L which is not chemically bonded to the partial structure represented by formula (1) １１ , L １２ , L １３ and L １４ The resin composition according to claim 1, wherein is bonded to a hydrogen atom or a monovalent group represented by the following formula (4): 【Transformation 3】 (In formula (4), R １６ Each independently represents a hydrocarbon group having 1 to 18 carbon atoms. ４ represents an integer of 0 to 5. * represents a bond.

3. In formulas (T-1) and (T-2), L which is not chemically bonded to the partial structure represented by formula (1) １１ , L １２ , L １３ and L １４ The resin composition according to claim 1 , wherein is bonded to a hydrogen atom.

4. (2A) a maleimide compound having a structural unit represented by the following formula (2): (B) an epoxy resin, and (D) a curing agent, A resin composition comprising: A resin composition, wherein the component (D) comprises an active ester resin (D1). 【Chemistry 4】 (In formula (2), R １１ R each independently represents a hydrocarbon group having 1 to 18 carbon atoms. １２ R each independently represents a hydrocarbon group having 1 to 18 carbon atoms. １３ R each independently represents a hydrocarbon group having 1 to 18 carbon atoms. １６ Each independently represents a hydrocarbon group having 1 to 18 carbon atoms. １ each independently represents an integer of 0 to 2, m ６ each independently represents an integer of 0 to 2, m １ +m ６ ≦2. ２ each independently represents an integer of 0 to 4, m ４ each independently represents an integer of 0 to 5, １ each independently represents the number of repeating units.)

5. The resin composition according to claim 4, wherein the component (2A) is a maleimide compound having a structure represented by the following formula (3): 【Transformation 5】 【Transformation 6】 (In formula (3), formula (4) and formula (5), R １１ R each independently represents a hydrocarbon group having 1 to 18 carbon atoms. １２ R each independently represents a hydrocarbon group having 1 to 18 carbon atoms. １３ R each independently represents a hydrocarbon group having 1 to 18 carbon atoms. １６ Each independently represents a hydrocarbon group having 1 to 18 carbon atoms. １ each independently represents an integer of 0 to 2, m ６ each independently represents an integer of 0 to 2, m ５ each independently represents an integer of 0 to 3, m １ +m ６ ≦2 and m １ +m ５ ≦3. ２ each independently represents an integer of 0 to 4, m ４ each independently represents an integer of 0 to 5, １ Each "n" independently represents the number of repeating units, and each "n" independently represents an integer of 1 or more. Ｍ１ represents a hydrogen atom or a monovalent group represented by formula (4). Ｍ２ represents a hydrogen atom or a monovalent group represented by formula (5). * represents a bond.

6. In formula (3), X Ｍ１ is a hydrogen atom, and X Ｍ２ The resin composition according to claim 5 , wherein is a monovalent group represented by formula (5):

7. R １３ The resin composition according to any one of claims 1 to 6, wherein each of the groups independently represents an alkyl group having 1 to 18 carbon atoms.

8. The resin composition according to any one of claims 1 to 6, wherein the component (D1) is an active ester resin containing a naphthalene structure.

9. 4. The resin composition according to claim 1, wherein the mass ratio of the component (1A) to the component (D1) [component (1A) / component (D1)] is 0.01 to 5.

10. 7. The resin composition according to claim 4, wherein the mass ratio of the component (2A) to the component (D1) [component (2A) / component (D1)] is 0.01 to 5.

11. The resin composition according to any one of claims 1 to 6, wherein the component (D) further comprises a curing agent other than the component (D1) (hereinafter referred to as "other curing agent (D2)").

12. The resin composition according to any one of claims 1 to 6, wherein the ratio of the number of moles of active groups in the curing agent (D) to the number of moles of epoxy groups in the epoxy resin (B) (number of moles of active groups in the curing agent / number of moles of epoxy groups in the epoxy resin) is 1 or more.

13. The resin composition according to any one of claims 1 to 6, further comprising (E) an inorganic filler.

14. The resin composition according to claim 13, wherein the content of the component (E) is 80% by mass or less when the total amount of nonvolatile components in the resin composition is 100% by mass.

15. The resin composition according to any one of claims 1 to 3, further comprising a maleimide compound other than the component (1A) (hereinafter referred to as "(1F) other maleimide compound").

16. The resin composition according to any one of claims 4 to 6, further comprising a maleimide compound other than the component (2A) (hereinafter referred to as "(2F) other maleimide compound").

17. The resin composition according to any one of claims 1 to 6, further comprising (G) a radically polymerizable resin.

18. The resin composition according to any one of claims 1 to 6, further comprising (H) an organic filler.

19. The resin composition according to any one of claims 1 to 6, further comprising (I) a curing accelerator.

20. The resin composition according to any one of claims 1 to 6, which is used for an insulating layer of a circuit board.

21. A resin sheet comprising a support and a layer of the resin composition according to any one of claims 1 to 6 provided on the support.

22. The resin sheet according to claim 21, wherein the support is a thermoplastic resin film or a metal foil.

23. A cured product of the resin composition according to any one of claims 1 to 6.

24. A circuit board comprising an insulating layer made of a cured product of the resin composition according to any one of claims 1 to 6.

25. A semiconductor device comprising the circuit board according to claim 24.

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