Resin composition

Abstract

To provide a resin composition capable of yielding a cured product that exhibits favorable dielectric properties as well as favorable mechanical properties, specifically high elongation at break and excellent crack resistance.SOLUTION: A resin composition comprises: (A) a compound represented by the formula (A-1) in the figure, where X represents a specific divalent group; (B) a maleimide resin; and (C) a thermosetting resin (excluding the maleimide resin).SELECTED DRAWING: None

Description

Technical Field

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

Background Art

[0002] An insulating layer is provided on a circuit board such as a printed wiring board or a redistribution substrate of a semiconductor chip package. Generally, the insulating layer is formed by curing a resin composition. As the insulating layer of the circuit board, it is required to exhibit good dielectric properties (low dielectric constant, low dielectric tangent) in order to suppress transmission loss when operating in a high-frequency environment. As a resin material that provides a cured product having good dielectric properties, for example, a resin composition containing a maleimide resin has been reported (Patent Document 1).

Prior Art Documents

Patent Documents

[0003]

Patent Document 1

Summary of the Invention

Problems to be Solved by the Invention

[0004] As disclosed in Patent Document 1, a resin composition containing a maleimide resin generally provides a cured product having good dielectric properties, but tends to generate cracks after desmear treatment. In addition, since the maleimide resin usually has a high softening point, the cured product of the resin composition containing the maleimide resin is brittle and tends to have poor mechanical properties.

[0005] An object of the present invention is to provide a resin composition capable of obtaining a cured product that exhibits good dielectric properties, has good mechanical properties, specifically a high elongation at break, and excellent crack resistance, a cured product obtained using the resin composition, a resin sheet, a circuit board, and a semiconductor device containing the resin composition.

Means for Solving the Problems

[0006] The present inventor has intensively studied to solve the above problems. As a result, the present inventor has found that a resin composition containing a compound having a specific structure and a thermosetting resin other than the maleimide resin in combination with the maleimide resin can solve the above problems, and has completed the present invention. That is, the present invention includes the following.

[0007] [1] (A) Compound A represented by the following formula (A-1): [Chemical formula] (In formula (A-1), X represents a divalent group represented by the following formula (A-2) or a divalent group represented by the following formula (A-3).) [Chemical formula] (In formula (A-2), R 11 and R 12 each independently represent a divalent aromatic group which may have a substituent, L 11 each independently represents a single bond or a divalent linking group which may have a substituent, and R 11 and L 11 may combine together to form a ring. a represents a number in the range of 0 to 5.) [Chemical formula] (In formula (A-3), R 13 and R 14 each independently represent a divalent aromatic group which may have a substituent, L 12 represents a group represented by formula (A-4). b and c each independently represent a number in the range of 0 to 5.) [Chemical formula] (In formula (A-4), R 15 , and R 16 each independently represent a divalent aromatic group which may have a substituent, L 13 each independently represent a single bond or a divalent linking group which may have a substituent, R 15 and L 13 may combine together to form a ring. d represents a number in the range of 0 to 5.). (B) A maleimide resin, and (C) A thermosetting resin (excluding maleimide resins) A resin composition containing the same. [2] In formula (A-2) and formula (A-3), R 11 , R 12 , R 13 , and R 14 each independently represent a phenylene group which may have a substituent, or a naphthylene group which may have a substituent, the resin composition according to [1]. [3] In formula (A-4), R 15 , and R 16 each independently represent a phenylene group which may have a substituent, or a naphthylene group which may have a substituent, the resin composition according to [1] or [2]. [4] In formula (A-2), L 11 each independently represent a single bond, a divalent aliphatic group which may have a substituent, an oxygen atom, a divalent aromatic group which may have a substituent, a carbonyl group, and a sulfonyl group, the resin composition according to any one of [1] to [3]. [5] In formula (A-2), L 11 each independently represent a single bond, a divalent aliphatic group which may have a substituent, an oxygen atom, a phenylene group, a fluorenylidene group, a carbonyl group, or a sulfonyl group, the resin composition according to any one of [1] to [4]. [6] The resin composition according to any one of [1] to [5], wherein X in formula (A-1) is a group represented by the following formula (A-5).

Chemical formula

[10] The resin composition according to any one of [1] to [9], wherein when the resin component in the resin composition is 100% by mass, the thermosetting resin (C) is 10% by mass or more and 50% by mass or less.

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

[10] , further containing (D) a thermoplastic resin.

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

[11] , further containing (E) an inorganic filler.

[13] The resin composition according to

[12] , wherein when the non-volatile component in the resin composition is 100% by mass, the content of component (E) is 50% by mass or more.

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

[13] , which is for an insulating layer of a circuit board.

[15] The cured product of the resin composition according to any one of [1] to

[13] .

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

[13] provided on the support.

[17] The resin sheet according to

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

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

[13] .

[19] A semiconductor device including the circuit board according to

[18] . [Effect of the Invention]

[0008] According to the resin composition of the present invention, a resin composition capable of obtaining a cured product that exhibits good dielectric properties and has good mechanical properties, specifically, a high elongation at break and excellent crack resistance, a cured product obtained by using the resin composition, a resin sheet, a circuit board, and a semiconductor device can be provided. [Embodiments for Carrying Out the Invention]

[0009] Hereinafter, the present invention will be described with reference to embodiments and examples. However, the present invention is not limited to the embodiments and examples shown below, and can be arbitrarily modified and implemented without departing from the scope of the claims and their equivalent scope.

[0010] In this specification, the term "optionally having a substituent" for a compound or a group means both the case where the hydrogen atom of the compound or the group is not substituted with a substituent and the case where some or all of the hydrogen atoms of the compound or the group are substituted with a substituent.

[0011] In this specification, unless otherwise specified, the "substituent" means a halogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, an alkenyl group, a cycloalkyloxy group, an aryl group, an aryloxy group, an arylalkyl group, an arylalkoxy group, a monovalent heterocyclic group, an alkylidene group, an amino group, a silyl group, an acyl group, an acyloxy group, a carboxy group, a sulfo group, a cyano group, a nitro group, a hydroxy group, a mercapto group, and an oxo group.

[0012] Examples of the halogen atom used as the substituent include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0013] The alkyl group used as the substituent may be either linear or branched. The number of carbon atoms of the alkyl group is preferably 1 to 20, more preferably 1 to 14, still more preferably 1 to 12, even more preferably 1 to 6, and particularly preferably 1 to 3. Examples of the alkyl group include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, and a decyl group.

[0014] The number of carbon atoms of the cycloalkyl group used as the substituent is preferably 3 to 20, more preferably 3 to 12, and still more preferably 3 to 6. Examples of the cycloalkyl group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group.

[0015] The alkoxy group used as the substituent may be either linear or branched. The number of carbon atoms of the alkoxy group is preferably 1 to 20, more preferably 1 to 12, and still more preferably 1 to 6. Examples of the alkoxy group include a methoxy group, an ethoxy group, a propyloxy group, an isopropyloxy group, a butoxy group, a sec-butoxy group, an isobutoxy group, a tert-butoxy group, a pentyloxy group, a hexyloxy group, a heptyloxy group, an octyloxy group, a nonyloxy group, and a decyloxy group.

[0016] The alkenyl group used as a substituent is a monovalent unsaturated hydrocarbon group having one carbon-carbon double bond, which may be either linear or branched. The number of carbon atoms of the alkenyl group is preferably 2 to 20, more preferably 2 to 12, and even more preferably 2 to 6. Examples of the alkenyl group include vinyl group, allyl group, propenyl group, butenyl group, pentenyl group, hexenyl group, heptenyl group, octenyl group, nonenyl group, decenyl group, etc.

[0017] The number of carbon atoms of the cycloalkyloxy group used as a substituent is preferably 3 to 20, more preferably 3 to 12, and even more preferably 3 to 6. Examples of the cycloalkyloxy group include cyclopropyloxy group, cyclobutyloxy group, cyclopentyloxy group, and cyclohexyloxy group.

[0018] The aryl group used as a substituent is a group obtained by removing one hydrogen atom from an aromatic hydrocarbon on the aromatic ring. The number of carbon atoms of the aryl group used as a substituent is preferably 6 to 24, more preferably 6 to 18, even more preferably 6 to 14, and even more preferably 6 to 10. Examples of the aryl group include phenyl group, naphthyl group, and anthracenyl group.

[0019] The number of carbon atoms of the aryloxy group used as a substituent is preferably 6 to 24, more preferably 6 to 18, even more preferably 6 to 14, and even more preferably 6 to 10. Examples of the aryloxy group used as a substituent include phenoxy group, 1-naphthyloxy group, and 2-naphthyloxy group.

[0020] The number of carbon atoms of the arylalkyl group used as a substituent is preferably 7 to 25, more preferably 7 to 19, even more preferably 7 to 15, and even more preferably 7 to 11. Examples of the arylalkyl group include phenyl-C 1 ~C 12Alkyl group, naphthyl-C 1 ~C 12 Alkyl group, and anthracenyl-C 1 ~C 12 Examples of the alkyl group include those having the following carbon atom numbers.

[0021] The number of carbon atoms of the arylalkoxy group used as a substituent is preferably 7 to 25, more preferably 7 to 19, still more preferably 7 to 15, and even more preferably 7 to 11. Examples of the arylalkoxy group include phenyl-C 1 ~C 12 alkoxy group, and naphthyl-C 1 ~C 12 alkoxy group.

[0022] The monovalent heterocyclic group used as a substituent refers to a group obtained by removing one hydrogen atom from the heterocyclic ring of a heterocyclic compound. The number of carbon atoms of the monovalent heterocyclic group is preferably 3 to 21, more preferably 3 to 15, and still more preferably 3 to 9. The monovalent heterocyclic group includes a monovalent aromatic heterocyclic group (heteroaryl group). Examples of the monovalent heterocyclic group include thienyl group, pyrrolyl group, furanyl group, furyl group, pyridyl group, pyridazinyl group, pyrimidinyl group, pyrazinyl group, triazinyl group, pyrrolidyl group, piperidyl group, quinolyl group, and isoquinolyl group.

[0023] The alkylidene group used as a substituent refers to a group obtained by removing two hydrogen atoms from the same carbon atom of an alkane. The number of carbon atoms of the alkylidene group is preferably 1 to 20, more preferably 1 to 14, still more preferably 1 to 12, even more preferably 1 to 6, and particularly preferably 1 to 3. Examples of the alkylidene group include methylidene group, ethylidene group, propylidene group, isopropylidene group, butylidene group, sec-butylidene group, isobutylidene group, tert-butylidene group, pentylidene group, hexylidene group, heptylidene group, octylidene group, nonylidene group, and decylidene group.

[0024] The acyl group used as a substituent refers to a group represented by the formula: -C(=O)-R (wherein R is an alkyl group or an aryl group). The alkyl group represented by R may be either linear or branched. Examples of the aryl group represented by R include a phenyl group, a naphthyl group, and an anthracenyl group. The number of carbon atoms of the acyl group is preferably 2 to 20, more preferably 2 to 13, and still more preferably 2 to 7. Examples of the acyl group include an acetyl group, a propionyl group, a butyryl group, an isobutyryl group, a pivaloyl group, and a benzoyl group.

[0025] The acyloxy group used as a substituent refers to a group represented by the formula: -O-C(=O)-R (wherein R is an alkyl group or an aryl group). The alkyl group represented by R may be either linear or branched. Examples of the aryl group represented by R include a phenyl group, a naphthyl group, and an anthracenyl group. The number of carbon atoms of the acyloxy group is preferably 2 to 20, more preferably 2 to 13, and still more preferably 2 to 7. Examples of the acyloxy group include an acetoxy group, a propionyloxy group, a butyryloxy group, an isobutyryloxy group, a pivaloyloxy group, and a benzoyloxy group.

[0026] The above-mentioned substituents may further have substituents (hereinafter sometimes referred to as "secondary substituents"). As the secondary substituents, the same ones as the above-mentioned substituents may be used unless otherwise specified.

[0027] In this specification, the term "aromatic ring" means a ring that follows Hückel's rule, where the number of electrons contained in the π electron system on the ring is 4p + 2 (p is a natural number). The aromatic ring may be an aromatic hydrocarbon ring composed only of carbon atoms as ring-constituting atoms, or an aromatic heterocyclic ring having, in addition to carbon atoms, heteroatoms such as oxygen atoms, nitrogen atoms, sulfur atoms, etc. as ring-constituting atoms. The aromatic ring is preferably an aromatic hydrocarbon ring. Also, for aromatic rings such as aromatic hydrocarbon rings, 5- to 14-membered aromatic rings are preferred, 6- to 14-membered aromatic rings are more preferred, and 6- to 10-membered aromatic rings are even more preferred. Suitable specific examples of aromatic hydrocarbon rings include benzene rings, naphthalene rings, anthracene rings, phenanthrene rings, etc., more preferably benzene rings or naphthalene rings, and particularly preferably benzene rings.

[0028] In this specification, the term "non-aromatic ring" means a ring other than an aromatic ring having aromaticity throughout the ring. The non-aromatic ring may be a non-aromatic hydrocarbon ring composed only of carbon atoms as ring-constituting atoms, or a non-aromatic heterocyclic ring having, in addition to carbon atoms, heteroatoms such as oxygen atoms, nitrogen atoms, sulfur atoms, etc. as ring-constituting atoms. The non-aromatic ring is preferably a non-aromatic hydrocarbon ring. The non-aromatic ring may be a saturated ring or an unsaturated ring. The non-aromatic ring is preferably a 3- to 21-membered non-aromatic ring, more preferably a 4- to 17-membered non-aromatic ring, and even more preferably a 5- to 14-membered non-aromatic ring. Suitable specific examples of non-aromatic rings (non-aromatic hydrocarbon rings) include monocyclic non-aromatic saturated hydrocarbon rings such as cyclobutane rings, cyclopentane rings, cyclohexane rings, cycloheptane rings, cyclooctane rings; monocyclic non-aromatic unsaturated hydrocarbon rings such as cyclobutene rings, cyclopentene rings, cyclohexene rings, cycloheptene rings, cyclooctene rings, cyclopentadiene rings, cyclohexadiene rings; bicyclo[2.2.1]heptane rings (norbornane rings), bicyclo[4.4.0]decane rings (decalin rings), bicyclo[5.3.0]decane rings, bicyclo[4.3.0]nonane rings (hydrindane rings), bicyclo[3.2.1]octane rings, bicyclo[5.4.0]undecane rings, bicyclo[3.3.0]octane rings, bicyclo[3.3.1]nonane rings, tricyclo[5.2.1.0 2,6Decane ring (tetrahydrodicyclopentadiene ring), tricyclo[3.3.1.1 3,7 Decane ring (adamantane ring), tricyclo[6.2.1.0 2,7 Non-aromatic saturated carbon rings with two or more rings such as undecane rings; non-aromatic unsaturated carbon rings with two or more rings such as bicyclo[2.2.1]hept-2-ene ring (norbornene ring), bicyclo[2.2.2]oct-2-ene ring, bicyclo[4.4.0]dec-2-ene ring, etc. are exemplified. The non-aromatic ring may be a non-aromatic ring with an aromatic ring condensed in part. Examples of non-aromatic rings with an aromatic ring condensed in part include indane ring, indene ring, tetralin ring, 1,2-dihydronaphthalene ring, 1,4-dihydronaphthalene ring, fluorene ring, 9,10-dihydroanthracene ring, 9,10-dihydrophenanthrene ring, etc.

[0029] [Resin composition] The resin composition of the present invention contains (A) a compound represented by the following formula (A-1), (B) a maleimide resin, and (C) a thermosetting resin (excluding maleimide resins). In the present invention, by using a specific compound represented by formula (A-1) in combination with a maleimide resin, it is excellent in crack resistance after desmear treatment, and further, by containing a thermosetting resin (excluding maleimide resins), a cured product having good mechanical properties, specifically, a high elongation at break, can be obtained.

[0030] The resin composition may further contain an arbitrary component in addition to the above components (A) to (C). Examples of the arbitrary component include (D) a thermoplastic resin, (E) an inorganic filler, (F) a radical reaction initiator, (G) a curing accelerator, and other additives. Hereinafter, each component contained in the resin composition will be described in detail.

[0031] [(A) Compound represented by formula (A-1)] The resin composition of the present invention contains, as component (A), a compound represented by the following formula (A-1).

[0032] [Chemical formula]

[0033] (In formula (A-1), X represents a divalent group represented by the following formula (A-2) or a divalent group represented by the following formula (A-3).)

[0034]

Chemical formula

[0035] (In formula (A-2), R 11 and R 12 each independently represent a divalent aromatic group which may have a substituent, L 11 each independently represents a single bond or a divalent linking group which may have a substituent, and R 11 and L 11 may combine together to form a ring.) a represents a number in the range of 0 to 5.)

[0036]

Chemical formula

[0037] (In formula (A-3), R 13 and R 14 each independently represent a divalent aromatic group which may have a substituent, L 12 represents a group represented by formula (A-4).) b and c each independently represent a number in the range of 0 to 5.)

[0038]

Chemical formula

[0039] (In formula (A-4), R 15 and R 16each independently represents a divalent aromatic group which may have a substituent; L 13 each independently represents a single bond or a divalent linking group which may have a substituent, R 15 and L 13 may combine together to form a ring. d represents a number in the range of 0 to 5.)

[0040] Component (A) of the present invention functions as a crosslinking agent for the (B) maleimide resin. The resin composition of the present invention containing such component (A) in combination with a maleimide resin can provide a cured product having excellent crack resistance. Component (A) may be used alone or in combination of two or more.

[0041] In formula (A-1), X represents a divalent group represented by formula (A-2) or a divalent group represented by formula (A-3).

[0042] In formula (A-2), R 11 , and R 12 each independently represents a divalent aromatic group which may have a substituent. The divalent aromatic group means a group obtained by removing two hydrogen atoms from the aromatic ring of an aromatic compound. Examples of the divalent aromatic group which may have a substituent include an arylene group which may have a substituent and a heteroarylene group which may have a substituent. The number of carbon atoms of the divalent aromatic group is preferably 3 or more, more preferably 4 or more or 5 or more, still more preferably 6 or more, and the upper limit thereof is preferably 30 or less, more preferably 24 or less, still more preferably 18 or less or 14 or less, particularly preferably 10 or less. The number of carbon atoms of the substituent is not included in the number of carbon atoms.

[0043] In a preferred embodiment, R 11 , and R 12The divalent aromatic group represented by is, independently of each other, a phenylene group which may have a substituent; a naphthylene group which may have a substituent; a phenylene group-fluorenylidene group-phenylene group which may have a substituent; a biphenylene group which may have a substituent; preferably, a phenylene group which may have a substituent or a naphthylene group which may have a substituent, and a phenylene group which may have a substituent is particularly preferred. When the divalent aromatic group has a substituent, the substituent is as described above, and among them, one or more selected from the group consisting of an alkyl group, an alkenyl group, and a hydroxy group are preferred, and one or more selected from the group consisting of a methyl group, an allyl group, and a hydroxy group are more preferred.

[0044] In formula (A-2), L 11 each independently represents a single bond or a divalent linking group which may have a substituent. Examples of the divalent linking group which may have a substituent include a divalent organic group composed of one or more (for example, 1 to 3000, 1 to 1000, 1 to 100, 1 to 50) skeletal atoms selected from a carbon atom, an oxygen atom, a nitrogen atom, and a sulfur atom, and an oxygen atom, a carbonyl group, a sulfonyl group, a divalent aliphatic group which may have a substituent, or a divalent aromatic group which may have a substituent are preferred.

[0045] In a preferred embodiment, L 11 each independently represents a single bond, a divalent aliphatic group which may have a substituent, an oxygen atom, a divalent aromatic group which may have a substituent, a carbonyl group, or a sulfonyl group.

[0046] Examples of the divalent aliphatic group in L 11 include, for example, an alkylene group, a cycloalkylene group, an alkenylene group, a cycloalkenylene group, an alkapolyenylene group (the number of double bonds is preferably 2 to 10, more preferably 2 to 6, still more preferably 2 to 4, and even more preferably 2), etc. An alkylene group, a cycloalkylene group, an alkenylene group, and a cycloalkenylene group are preferred, an alkylene group and a cycloalkylene group are more preferred, and a cycloalkylene group is still more preferred.

[0047] L 11 The alkylene group in L may be either linear or branched, and the number of its carbon atoms is preferably 1 to 12, more preferably 1 to 6, and even more preferably 1 to 4. The number of carbon atoms of the substituent is not included in the number of carbon atoms. Examples of the alkylene group include a methylene group, an ethylene group, a propylene group, a 2-propylene group, a 1,1-dimethyl-3-methylpropylene group, a butylene group, a pentylene group, a hexylene group, and the like.

[0048] L 11 The number of carbon atoms of the cycloalkylene group in L is preferably 3 to 15, more preferably 3 to 12, and even more preferably 3 to 10. The number of carbon atoms of the substituent is not included in the number of carbon atoms. Examples of the cycloalkylene group include a cyclopropylene group, a cyclobutylene group, a cyclopentylene group, a cyclohexylene group, a decahydronaphthanylene group, a norbornanylene group, a dicyclopentanylene group, an adamantanylene group, and the like, and a dicyclopentanylene group is preferred.

[0049] L 11 The alkenylene group in L may be either linear or branched, and the number of its carbon atoms is preferably 2 to 12, more preferably 2 to 6, and even more preferably 2 to 4. The number of carbon atoms of the substituent is not included in the number of carbon atoms. Examples of the alkenylene group include an ethenylene group, a propenylene group, a butenylene group, a pentenylene group, a hexenylene group, and the like.

[0050] L 11 The number of carbon atoms of the cycloalkenylene group in L is preferably 3 to 15, more preferably 3 to 12, and even more preferably 3 to 10. The number of carbon atoms of the substituent is not included in the number of carbon atoms. Examples of the cycloalkenylene group include a cyclopropenylene group, a cyclobutenylene group, a cyclopentylene group, a cyclohexenylene group, a norbornenylene group, and the like.

[0051] L 11Examples of the divalent aromatic group in [compound name] include an arylene group and a heteroarylene group, with the arylene group being preferred.

[0052] L 11 The number of carbon atoms of the arylene group in [compound name] is preferably 6 to 24, more preferably 6 to 18, and even more preferably 6 to 14. The number of carbon atoms of the substituent is not included in this count. Examples of the arylene group include a phenylene group, a naphthylene group, an anthracenylene group, a fluorenediyl group (e.g., 9H-fluorene-9,9-diyl group), a fluorenylidene group, a phenanthrenediyl group, an indandiy group, a pyrenediyl group, etc., with the phenylene group and the fluorenylidene group being preferred.

[0053] L 11 The number of carbon atoms of the heteroarylene group in [compound name] is preferably 3 to 21, more preferably 3 to 15, and even more preferably 3 to 9. The number of carbon atoms of the substituent is not included in this count. Examples of the heteroarylene group include a pyrrolediyl group, a furandiyl group, a thiophenediyl group, a pyridinediyl group, a pyridazinediyl group, a pyrimidinediyl group, a pyrazinediyl group, a triazinediyl group, a piperidinediyl group, a triazolediyl group, a purinediyl group, a carbazolediyl group, a quinolinediyl group, an isoquinolinediyl group, etc.

[0054] R 11 and L 11 may combine together to form a ring. In this case, L 11 is preferably a divalent aliphatic group which may have a substituent, and more preferably an alkylene group which may have a substituent. When R 11 and L 11 combine together to form a ring, it is preferred that a phenylene group and a cyclopentylene group are bonded to form an indane ring.

[0055] L 11Each independently preferably represents a single bond, a divalent aliphatic group which may have a substituent, an oxygen atom, a divalent aromatic group which may have a substituent, a carbonyl group, or a sulfonyl group. Each independently more preferably represents a single bond, a divalent aliphatic group which may have a substituent, an oxygen atom, a phenylene group, a fluorenylidene group, a carbonyl group, or a sulfonyl group. A single bond, an oxygen atom, a carbonyl group, a sulfonyl group, an alkylene group having 1 to 12 carbon atoms which may have a substituent, a cycloalkylene group having 3 to 15 carbon atoms which may have a substituent, or an arylene group having 6 to 24 carbon atoms which may have a substituent is preferred. L 11 The substituent which it may have is as described above, and among them, one or more selected from the group consisting of an alkyl group, an alkenyl group, and a hydroxy group are preferred, and one or more selected from the group consisting of a methyl group, an allyl group, and a hydroxy group are more preferred.

[0056] In formula (A-2), a represents a number in the range of 0 to 5, preferably 0 to 4, more preferably 0 to 3, or 0 to 2.

[0057] In formula (A-3), R 13 , and R 14 each independently represents a divalent aromatic group which may have a substituent. The divalent aromatic group may be the same as the divalent aromatic group represented by R 11 , R 12 in formula (A-2). In a preferred embodiment, the divalent aromatic groups represented by R 13 , and R 14 are each independently a phenylene group which may have a substituent or a naphthylene group which may have a substituent, and more preferably a phenylene group which may have a substituent. When the divalent aromatic group has a substituent, the substituent is as described above, and among them, one or more selected from the group consisting of an alkyl group, an alkenyl group, and a hydroxy group are preferred, and one or more selected from the group consisting of a methyl group, an allyl group, and a hydroxy group are more preferred.

[0058] In formula (A-3), L12 represents a group represented by formula (A-4).

[0059] In formula (A-4), R 15 , and R 16 each independently represent a divalent aromatic group which may have a substituent. The divalent aromatic group in R 15 , R 16 may be the same as the divalent aromatic group in R 11 , R 12 in formula (A-2). In a preferred embodiment, the divalent aromatic group represented by R 15 , and R 16 is a phenylene group which may have a substituent or a naphthylene group which may have a substituent, and more preferably a phenylene group which may have a substituent. When the divalent aromatic group has a substituent, the substituent is as described above, and among them, one or more selected from the group consisting of an alkyl group, an alkenyl group, and a hydroxy group are preferable, and one or more selected from the group consisting of a methyl group, an allyl group, and a hydroxy group are more preferable.

[0060] In formula (A-4), L 13 each independently represent a single bond or a divalent linking group which may have a substituent. The divalent linking group in L 13 may be the same as the divalent linking group in L 11 in formula (A-2). In a preferred embodiment, the divalent linking group represented by L 13 is an alkylene group having 1 to 12 carbon atoms which may have a substituent. The substituent which L 13 may have is as described above, and may be the same as the substituent which L 11 may have.

[0061] In formula (A-4), d represents a number in the range of 0 to 5, preferably a number in the range of 0 to 4, more preferably a number in the range of 0 to 3, or 0 to 2. R 15 and L 13 may combine together to form a ring. In this case, L 13is preferably a divalent aliphatic group which may have a substituent, and more preferably an alkylene group which may have a substituent. In addition, R 15 and L 13 When they are combined together to form a ring, it is preferable that a phenylene group and a cyclopentylene group are combined to form an indane ring.

[0062] In formula (A-3), b and c each independently represent a number in the range of 0 to 5, preferably a number in the range of 0 to 4, more preferably a number in the range of 0 to 3, or 0 to 2.

[0063] Among them, from the viewpoint of realizing a resin composition that exhibits good dielectric properties, good mechanical properties (high elongation at break point), and excellent crack resistance in the combination of component (B) and component (C), when X is a divalent group represented by formula (A-2), the divalent group represented by the formula (A-2), that is, X is preferably a divalent group represented by the following formula (A-5). From the same viewpoint, when X is a divalent group represented by formula (A-3), L 12 in the formula (A-3), that is, the divalent group represented by formula (A-4) is preferably a divalent group represented by the following formula (A-5).

[0064] [Chemical formula]

[0065] (In formula (A-5), Rs each independently represent a substituent, L 21 each independently represents a single bond, a divalent aliphatic group which may have a substituent, an oxygen atom, a phenylene group, a fluorenylidene group, a carbonyl group, or a sulfonyl group. Here, when L 21 is a divalent aliphatic group which may have a substituent, L 21 and the benzene ring on the left side may be combined together to form a ring, n1 and n2 each independently represent a number in the range of 0 to 4, m represents a number in the range of 0 to 5, "*" represents a linking group. )

[0066] Rs each independently represent a substituent. The substituents are as described above, and among them, one or more selected from the group consisting of an alkyl group, an alkenyl group, and a hydroxy group are preferred, and one or more selected from the group consisting of a methyl group, an allyl group, and a hydroxy group are more preferred.

[0067] L 21 each independently represents a single bond, a divalent aliphatic group which may have a substituent, an oxygen atom, a phenylene group, a fluorenylidene group, a carbonyl group, or a sulfonyl group, and more preferably a single bond, an oxygen atom, a carbonyl group, a sulfonyl group, an alkylene group having 1 to 12 carbon atoms which may have a substituent, or a cycloalkylene group having 3 to 15 carbon atoms which may have a substituent, or an arylene group having 6 to 24 carbon atoms which may have a substituent. L 21 The substituents which L may have are as described above, and among them, one or more selected from the group consisting of an alkyl group, an alkenyl group, and a hydroxy group are preferred, and one or more selected from the group consisting of a methyl group, an allyl group, and a hydroxy group are more preferred.

[0068] L 21 When L is a divalent aliphatic group which may have a substituent, L 21 and the benzene ring on the left side may combine together to form a ring. In this case, it is preferable that a cyclopentylene group and the benzene ring on the left side are combined to form an indane ring.

[0069] n1 and n2 each independently represent a number in the range of 0 to 4, preferably a number in the range of 0 to 4, more preferably a number in the range of 0 to 3, or 0 to 2.

[0070] m represents a number in the range of 0 to 5, preferably a number in the range of 0 to 4, more preferably a number in the range of 0 to 3, 0 to 2. Among them, from the viewpoint of being able to more enjoy the effects of the present invention, m is preferably 1 or 2.

[0071] In a particularly preferred embodiment from the viewpoint of being able to more enjoy the effects of the present invention, In formula (A-1), X represents a divalent group represented by formula (A-2), R 11 , and R 12 are each independently a phenylene group which may have a substituent, or a naphthylene group which may have a substituent, L 11 are each independently a single bond, a divalent aliphatic group which may have a substituent, an oxygen atom, a phenylene group, a fluorenylidene group, a carbonyl group, or a sulfonyl group, a represents a number in the range of 0 to 5, and R 11 and L 11 may combine together to form a ring. Among them, the divalent group represented by formula (A-2) is preferably a divalent group represented by formula (A-5). In such an embodiment, the preferred types of substituents are as described above.

[0072] In another particularly preferred embodiment from the viewpoint of being able to more enjoy the effects of the present invention, In formula (A-1), X represents a divalent group represented by formula (A-3), R 13 , and R 14 are each independently a phenylene group which may have a substituent, b and c each independently represent a number in the range of 0 to 5, L 12 is a group represented by formula (A-4), R 15 , and R 16 are each independently a phenylene group which may have a substituent, or a naphthylene group which may have a substituent, L 13 are each independently a single bond, a divalent aliphatic group which may have a substituent, an oxygen atom, a phenylene group, a fluorenylidene group, a carbonyl group, or a sulfonyl group, d represents a number in the range of 0 to 5, and R 15 and L 13They may combine together to form a ring. Among them, the divalent group represented by the formula (A-4) is preferably the divalent group represented by the formula (A-5). In such an embodiment, the preferred types of substituents are as described above.

[0073] Component (A) can be obtained, for example, 1) by condensing 1-phenyl-1-propene-3-halide, 2) a divalent phenol compound. It can be obtained by subjecting them to a condensation reaction.

[0074] 1-Phenyl-1-propene-3-halide is a compound in which a halogen is bonded to the 3-position of 1-phenyl-1-propene. Examples of such compounds include 3-bromo-1-phenyl-1-propene and the like.

[0075] The divalent phenol compound is a compound capable of reacting with 1-phenyl-1-propene-3-halide at the phenol site thereof and can constitute X in the formula (A-1). Examples of such compounds include various bisphenol compounds such as 4,4'-methylenebis(2,6-dimethylphenol), 4,4'-(9-fluorenylidene)diphenol, 4,4'-dihydroxydiphenyl ether, 4,4'-dihydroxybenzophenone, bisphenol A, bisphenol F, 2,2'-diallylbisphenol A, and bisphenol S; various biphenyl compounds such as 4,4'-dihydroxybiphenyl; dihydroxyaryl compounds such as 2,7-naphthalenediol; polyphenylene ether compounds having hydroxy groups at both ends, and the like.

[0076] In the condensation reaction, a base may be used. Examples of the base include alkali metal hydroxides such as sodium hydroxide (caustic soda) and potassium hydroxide; tertiary amines such as triethylamine, pyridine, and N,N-diisopropylethylamine. The base may be used alone or in combination of two or more.

[0077] In addition, the condensation reaction may proceed in a solvent-free system without using a solvent, or may proceed in an organic solvent system using an organic solvent. Examples of the organic solvent include ketone solvents such as acetone, methyl ethyl ketone, methyl isobutyl ketone, and cyclohexanone; acetate solvents such as ethyl acetate, butyl acetate, cellosolve acetate, propylene glycol monomethyl ether acetate, and carbitol acetate; ether solvents such as tetrahydropyran, tetrahydrofuran, 1,4-dioxane, diethyl ether, diisopropyl ether, dibutyl ether, diphenyl ether, and anisole; carbitol solvents such as cellosolve and butyl carbitol; aromatic hydrocarbon solvents such as toluene and xylene; and amide solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, and N-methyl-2-pyrrolidone. The organic solvent may be used alone or in combination of two or more.

[0078] The reaction temperature may be, for example, in the range of 0 to 80°C. The reaction time may be, for example, in the range of 30 minutes to 24 hours.

[0079] After the reaction is completed, if necessary, a purification step such as washing with water or microfiltration may be performed to remove by-produced salts and excess starting materials from the system. Specifically, after adding an amount of water necessary to dissolve the by-produced salts and stirring, the aqueous layer is discarded. Thereafter, the organic layer is dried, and if necessary, the organic solvent is distilled off to obtain the compound of the present invention. The organic solvent may be used as it is without being completely removed as the solvent of the resin composition.

[0080] In combination with the (B) component and the (C) component, it exhibits good dielectric properties, and since the alkylene ether skeleton of (A) is incorporated into the curing system to relax the rigidity of maleimide and ensure flexibility, a resin composition can be realized that exhibits good mechanical properties (high elongation at break) and provides a cured product with excellent crack resistance. From this perspective, when the resin component in the resin composition is 100% by mass, the content of the (A) component is preferably 2% by mass or 3% by mass or more, more preferably 5% by mass or more, still more preferably 7% by mass or more, even more preferably 7.5% by mass or more or 8% by mass or more, and the upper limit is preferably 15% by mass or less, more preferably 12% by mass or less, still more preferably 11% by mass or less, 10% by mass or less, or 9.5% by mass or less. Therefore, in one embodiment, when the resin component in the resin composition is 100% by mass, the content of the (A) component is 2% by mass or more and 12% by mass or less.

[0081] In the present invention, the "resin component" referred to in the resin composition means the component excluding the inorganic filler described below among the non-volatile components constituting the resin composition.

[0082] [(B) Maleimide resin] The resin composition of the present invention contains a maleimide resin as the (B) component.

[0083] The type of maleimide resin is not particularly limited as long as it has one or more (preferably two or more) maleimide groups (2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl groups) in one molecule. The (B) component may be used alone or in combination of two or more.

[0084] (Component (B) may be an aromatic maleimide resin having a maleimide group directly bonded to an aromatic ring, or may be an aliphatic maleimide resin having no maleimide group directly bonded to an aromatic ring. When component (B) contains an aliphatic maleimide resin, the aliphatic maleimide resin preferably includes a maleimide resin having a carbon skeleton derived from dimer acid. When component (B) contains an aromatic maleimide resin, the aromatic maleimide resin preferably includes a maleimide resin having one or more skeletons selected from a biphenyl skeleton and an indane skeleton. Therefore, component (B) preferably includes a maleimide resin having one or more skeletons selected from a carbon skeleton derived from dimer acid, a biphenyl skeleton, and an indane skeleton.)

[0085] The carbon skeleton derived from dimer acid means a carbon skeleton obtained by removing two terminal carboxy groups (-COOH) of dimer acid, or a carbon skeleton obtained by replacing two terminal carboxy groups (-COOH) with methylene groups (-CH 2 -). Dimer acid is a known compound obtained by dimerizing an unsaturated fatty acid (preferably having 11 to 22 carbon atoms, more preferably 14 to 20 carbon atoms, and particularly preferably 18 carbon atoms), and its industrial manufacturing process is almost standardized in the industry. Dimer acid is mainly composed of a dimer acid having 36 carbon atoms obtained by dimerizing unsaturated fatty acids having 18 carbon atoms such as oleic acid and linoleic acid, which are particularly inexpensive and easily available. In addition, dimer acid may contain any amount of monomer acid, trimer acid, and other polymerized fatty acids depending on the manufacturing method, degree of purification, etc. Also, although double bonds remain after the polymerization reaction of unsaturated fatty acids, in this specification, hydrogenated products obtained by further hydrogenation reaction to reduce the degree of unsaturation are also included in dimer acid.)

[0086] The maleimide resin having a carbon skeleton derived from dimer acid preferably includes a maleimide resin represented by the following formula (B1).

[0087] [Chemical formula]

[0088] (In formula (B1), n 1 Each of the n + 1 Xs independently represents a divalent organic group composed of 5 or more skeletal atoms selected from a carbon atom, a nitrogen atom (not forming an imide), an oxygen atom, and a sulfur atom, and non-skeletal atoms selected from a hydrogen atom and a halogen atom, and at least one of the n + 1 Xs represents a divalent hydrocarbon group derived from dimer acid; n 1 Each of the n Ys independently represents a tetravalent organic group composed of 5 or more skeletal atoms selected from a carbon atom, a nitrogen atom (not forming an imide), an oxygen atom, and a sulfur atom, and non-skeletal atoms selected from a hydrogen atom and a halogen atom; n 1 represents an integer of 0 or 1 or more.)

[0089] In formula (B1), n 1 Each of the n + 1 Xs independently represents a divalent organic group composed of 5 or more (preferably 5 to 200, more preferably 5 to 100, still more preferably 5 to 50) skeletal atoms selected from a carbon atom, a nitrogen atom (not forming an imide), an oxygen atom, and a sulfur atom, and non-skeletal atoms selected from a hydrogen atom and a halogen atom, and at least one of the n + 1 Xs represents a divalent hydrocarbon group derived from dimer acid.

[0090] The divalent hydrocarbon group derived from dimer acid means a divalent hydrocarbon group obtained by removing two terminal carboxy groups (-COOH) of dimer acid, or a divalent hydrocarbon group obtained by replacing two terminal carboxy groups (-COOH) with a methylene group (-CH 2 -).

[0091] n 1 Each of the n + 1 Xs may have a divalent organic group other than the divalent hydrocarbon group derived from dimer acid, but n 1When the total amount of one X is 100 mol%, it is preferable that 30 mol% or more of them are divalent hydrocarbon groups derived from dimer acid, more preferably 60 mol% or more are divalent hydrocarbon groups derived from dimer acid, still more preferably 90 mol% or more are divalent hydrocarbon groups derived from dimer acid, n 1 It is even more preferable that all of the one X are divalent hydrocarbon groups derived from dimer acid.

[0092] n 1 The divalent organic group other than the divalent hydrocarbon group derived from dimer acid in one X may be a divalent organic group having no aromatic ring or a divalent organic group having an aromatic ring.

[0093] In formula (B1), n 1 Each of the n Ys independently represents a tetravalent organic group composed of 5 or more (preferably 5 to 200, more preferably 5 to 100, still more preferably 5 to 50) skeletal atoms selected from a carbon atom, a nitrogen atom (not forming an imide), an oxygen atom and a sulfur atom, and non-skeletal atoms selected from a hydrogen atom and a halogen atom. The tetravalent organic group represented by Y may be a tetravalent organic group having no aromatic ring or a tetravalent organic group having an aromatic ring.

[0094] In one embodiment, the tetravalent organic group represented by Y is preferably a tetravalent group selected from the following formulas (Y1) to (Y5).

[0095]

Chemical formula

[0096] (In formulas (Y1) to (Y5), Ring Y 11 Ring Y 21 Ring Y 22 Ring Y 31 Ring Y 32 Ring Y 33 Ring Y 41 Ring Y 42 Ring Y 43 Ring Y44 and ring Y 51 and ring Y 52 and ring Y 53 and ring Y 54 and ring Y 55 each independently represents an aromatic ring which may have a substituent, or a non-aromatic ring which may have a substituent; Y 2a and Y 3a and Y 3b and Y 4a and Y 4b and Y 4c and Y 5a and Y 5b and Y 5c and Y 5d each independently represents a single bond, -C(R y ) 2 -, -O-, -CO-, -S-, -SO-, -SO 2 -,-CONH-, or -NHCO-; R y each independently represents a hydrogen atom, or an alkyl group which may be substituted by a halogen atom, or two R y bonded to the same carbon atom are combined together to form a non-aromatic ring which may have a substituent; * indicates a bonding site; The two bonding sites on the same ring represented by * are the bonding sites with two adjacent carbon atoms on the ring respectively.)

[0097] In formulas (Y1) to (Y5), ring Y 11 and ring Y 21 and ring Y 22 and ring Y 31 and ring Y 32 and ring Y 33 and ring Y 41 and ring Y 42 and ring Y 43 and ring Y 44 and ring Y 51 and ring Y 52 and ring Y 53 and ring Y 54 and ring Y 55Each independently represents an aromatic ring which may have a substituent, or a non-aromatic ring which may have a substituent. These cyclic structures are preferably an aromatic ring which may have a substituent, more preferably a benzene ring which may have a substituent, and even more preferably a benzene ring which may be substituted with an alkyl group.

[0098] Ring Y 11 Ring Y 21 Ring Y 22 Ring Y 31 Ring Y 32 Ring Y 33 Ring Y 41 Ring Y 42 Ring Y 43 Ring Y 44 Ring Y 51 Ring Y 52 Ring Y 53 Ring Y 54 and Ring Y 55 The substituents that Ring Y may have are not particularly limited. For example, halogen atoms, -NO 2 , -CN, -COH, -OH, -SH, -NH 2 , -COOH, -R c , -COR c , -OR c , -SR c , -SOR c , -SO 2 R c , -NHR c , -NR c 2 , -COOR c , -OCOR c , -CONH 2 , -CONHR c , -CONR c 2 , -NHCOR c and other monovalent substituents can be mentioned (however, R c is as described above.). is a radical.

[0099] In formulas (Y1) to (Y5), Y 2a , Y 3a , Y 3b , Y 4a , Y4b , Y 4c , Y 5a , Y 5b , Y 5c and Y 5d is, independently of one another, a single bond, -C(R y ), 2 -, -O-, -CO-, -S-, -SO-, -SO 2 2-, -CONH-, or -NHCO-, and in one embodiment, preferably, a single bond, -C(R y ), 2 - or -O-.

[0100] R y is, independently of one another, a hydrogen atom or an alkyl group which may be substituted with a halogen atom, or two Rs bonded to the same carbon atom are joined together to form a non-aromatic ring which may have a substituent. The alkyl group may be the same as the alkyl group in R y . R c is, independently of one another, preferably a hydrogen atom or an alkyl group which may be substituted with a halogen atom; more preferably, a hydrogen atom or a methyl group which may be substituted with a halogen atom; still more preferably, a hydrogen atom, a methyl group, or a trifluoromethyl group; particularly preferably, a hydrogen atom or a methyl group.

[0101] R y The substituents which may be possessed by R y are not particularly limited, but examples thereof include a halogen atom, -NO 2 , -CN, -COH, -OH, -SH, -NH 2 , -COOH, -R c , -COR c , -OR c , -SR c , -SOR c , -SO 2 R c , -NHR c , -NR c 2 , -COOR c , -OCOR c , -CONH 2 , -CONHRc , -CONR c 2 , -NHCOR c and other monovalent substituents such as (however, R c is as described above.).

[0102] In formula (B1), n 1 represents an integer of 0 or 1 or more, preferably an integer of 0 or 1 to 10, and more preferably 0.

[0103] The maleimide resin having a carbon skeleton derived from dimer acid may be used alone or in combination of two or more.

[0104] Examples of commercially available maleimide resins having a carbon skeleton derived from dimer acid include "BMI-689", "BMI-1500", "BMI-1700", "BMI-3000J" manufactured by Designer Molecules, and "SLK-6895-T90" manufactured by Shin-Etsu Chemical Co., Ltd.

[0105] Examples of the aromatic maleimide resin include, for example, the maleimide resin represented by formula (B2).

[0106] [Chemical formula]

[0107] (In formula (B2), R 10 each independently represents a hydrogen atom or an alkyl group which may be substituted with a halogen atom; ring D each independently represents an aromatic carbon ring which may have a substituent; n 2 represents an integer of 1 or more; n 2 The units may be the same or different for each unit.)

[0108] In formula (B2), R 10Each independently represents a hydrogen atom or an alkyl group which may be substituted with a halogen atom. The alkyl group may be the same as the alkyl group in R c Each independently represents, preferably, a hydrogen atom or an alkyl group; more preferably, a hydrogen atom or a methyl group; still more preferably, a hydrogen atom. 10 In formula (B2), ring D each independently represents an aromatic carbocyclic ring which may have a substituent. The aromatic carbocyclic ring may be the same as the aromatic carbocyclic ring described in the item of aromatic ring in ring Y

[0109] , ring Y 11 , ring Y 21 , ring Y 22 , ring Y 31 , ring Y 32 , ring Y 33 , ring Y 41 , ring Y 42 , ring Y 43 , ring Y 44 , ring Y 51 , ring Y 52 , ring Y 53 , ring Y 54 and ring Y 55 . Also, the "substituent" in ring D may be the same as the substituent in the "aromatic ring which may have a substituent" in ring Y 11 , ring Y 21 , ring Y 22 , ring Y 31 , ring Y 32 , ring Y 33 , ring Y 41 , ring Y 42 , ring Y 43 , ring Y 44 , ring Y 51 , ring Y 52 , ring Y 53 , ring Y 54 and ring Y 55 . Ring D preferably represents a benzene ring which may have a substituent; more preferably, a benzene ring which may be substituted with a group selected from an alkyl group and an aryl group; particularly preferably, an unsubstituted benzene ring.

[0110] In formula (B2), n 2represents an integer of 1 or more, preferably an integer of 1 to 10.

[0111] The maleimide resin having a biphenyl skeleton preferably contains a maleimide resin represented by the following formula (B3).

[0112]

Chemical formula

[0113] (In formula (B3), R 20 each independently represents a hydrogen atom or an alkyl group which may be substituted with a halogen atom; Ring E, ring F and ring G each independently represent an aromatic carbon ring which may have a substituent; n 3 represents an integer of 1 or more; n 3 The units may be the same or different for each unit.)

[0114] In formula (B3), R 20 each independently represents a hydrogen atom or an alkyl group which may be substituted with a halogen atom. The alkyl group may be the same as the alkyl group in R c . R 20 is preferably each independently a hydrogen atom or an alkyl group, more preferably a hydrogen atom or a methyl group, and even more preferably a hydrogen atom.

[0115] In formula (B3), ring E, ring F and ring G each independently represent an aromatic carbon ring which may have a substituent. The aromatic carbon ring is ring Y 11 ring Y 21 ring Y 22 ring Y 31 ring Y 32 ring Y 33 ring Y 41 ring Y 42 ring Y 43 ring Y 44 ring Y 51 ring Y52 and ring Y 53 and ring Y 54 and ring Y 55 may be the same as the aromatic carbocyclic ring described in the section on aromatic rings in ring Y. Ring E, ring F, and ring G are preferably benzene rings which may have substituents, more preferably benzene rings which may be substituted with a group selected from an alkyl group and an aryl group, and even more preferably (unsubstituted) benzene rings.

[0116] The substituents that ring E, ring F, and ring G may have are not particularly limited. For example, a halogen atom, -NO 2 , -CN, -COH, -OH, -SH, -NH 2 , -COOH, -R c , -COR c , -OR c , -SR c , -SOR c , -SO 2 R c , -NHR c , -NR c 2 , -COOR c , -OCOR c , -CONH 2 , -CONHR c , -CONR c 2 , -NHCOR c and other monovalent substituents (where R c is as described above).

[0117] In formula (B3), n 3 represents an integer of 1 or more, preferably an integer of 1 to 10.

[0118] Commercially available products of maleimide resins having a biphenyl skeleton include, for example, "MIR-3000-70MT", "MIR-5000-60T", etc. manufactured by Nippon Kayaku Co., Ltd.

[0119] The maleimide resin having a biphenyl skeleton may be used alone or in combination of two or more.

[0120] The maleimide resin having an indane skeleton preferably contains a maleimide resin represented by the following formula (B4).

[0121]

Chemical formula

[0122] (In formula (B4), R 30 each independently represents an alkyl group; ring H and ring I each independently represent an aromatic carbon ring which may have a substituent; n 4 represents an integer of 1 or more; n 4 units may be the same or different for each unit.)

[0123] In formula (B4), R 30 each independently represents an alkyl group. R 30 is preferably a methyl group.

[0124] In formula (B4), ring H each independently represents an aromatic aromatic ring which may have a substituent. Ring H is preferably a benzene ring which may have a substituent, more preferably a benzene ring which may be substituted with an alkyl group, and even more preferably a benzene ring substituted with an alkyl group.

[0125] In formula (B4), ring I each independently represents an aromatic aromatic ring which may have a substituent. Ring I is preferably a benzene ring which may have a substituent, more preferably a benzene ring which may be substituted with an alkyl group, and even more preferably a (unsubstituted) benzene ring.

[0126] The substituents that ring H and ring I may have are not particularly limited. For example, a halogen atom, -NO 2, -CN, -COH, -OH, -SH, -NH 2 , -COOH, -R c , -COR c , -OR c , -SR c , -SOR c , -SO 2 R c , -NHR c , -NR c 2 , -COOR c , -OCOR c , -CONH 2 , -CONHR c , -CONR c 2 , -NHCOR c Examples of the monovalent substituents include (however, R c is as described above.).

[0127] In formula (B4), n 4 represents an integer of 1 or more, and is preferably an integer of 1 to 20.

[0128] The maleimide resin having an indane skeleton can be produced, for example, by using the method described in JP-A-2020-500211 or a method analogous thereto.

[0129] The maleimide resin having an indane skeleton may be used alone or in combination of two or more.

[0130] The maleimide group equivalent of component (B) is preferably 50 g / eq. or more, more preferably 100 g / eq. or more, still more preferably 150 g / eq. or more, 200 g / eq. or more, 250 g / eq. or more, or 300 g / eq. or more, and the upper limit is preferably 2,000 g / eq. or less, more preferably 1,000 g / eq. or less, still more preferably 800 g / eq. or less, 600 g / eq. or less, 500 g / eq. or less, or 450 g / eq. or less. The maleimide group equivalent is the mass of component (B) per 1 molar equivalent of the maleimide group.

[0131] (B) component preferably has a molecular weight of less than 5,000, more preferably less than 3,000, still more preferably less than 2,000, less than 1,500, less than 1,200 or less than 1,000. Its lower limit is not particularly limited and can be, for example, 300 or more, 400 or more, 500 or more, etc.

[0132] In combination with components (A) and (C), from the perspective of realizing a resin composition that exhibits good dielectric properties, exhibits good mechanical properties (high elongation at break), and provides a cured product with excellent crack resistance, when the resin component in the resin composition is 100% by mass, the content of component (B) in the resin composition is preferably 20% by mass or 30% by mass or more, more preferably 40% by mass or more, still more preferably 45% by mass or more or 50% by mass or more, and the upper limit of its content is preferably 80% by mass or less, more preferably 75% by mass or less, still more preferably 70% by mass or less or 65% by mass or less. Therefore, in one embodiment, when the resin component in the resin composition is 100% by mass, the content of component (B) is 20% by mass or more and 75% by mass or less.

[0133] In combination with component (C), from the perspective of realizing a resin composition that exhibits even better dielectric properties, exhibits even better mechanical properties (high elongation at break), and provides a cured product with even better crack resistance, the mass ratio of component (A) to component (B) ((A) component / (B) component) is preferably 0.02 or more, more preferably 0.04, still more preferably 0.06 or more or 0.08 or more, even more preferably 0.1 or more, 0.12 or more or 0.14 or more, and the upper limit is preferably 0.4 or less, more preferably 0.3 or less, still more preferably 0.25 or less or 0.2 or less.

[0134] [(C) Thermosetting resin] The resin composition of the present invention contains a thermosetting resin as component (C). The thermosetting resin as component (C) does not include a maleimide resin.

[0135] Examples of the component (C) include epoxy resins, phenolic resins, benzoxazine resins, active ester resins, cyanate ester resins, carbodiimide resins, amine resins, acid anhydride resins, terminal double bond resins, etc. The thermosetting resin may be used alone or in combination of two or more in any ratio. Among these, from the viewpoint of being able to enjoy the effects of the present invention more, it is preferably at least one selected from the group consisting of epoxy resins, phenolic resins, and terminal double bond resins. Note that phenolic resins, naphthol resins, benzoxazine resins, active ester resins, cyanate ester resins, carbodiimide resins, amine resins, and acid anhydride resins also function as curing agents for epoxy resins, and they are collectively referred to as epoxy resin curing agents.

[0136] - Epoxy resin - The type of the 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 the epoxy resin include bisphenol type epoxy resin, dicyclopentadiene type epoxy resin, trisphenol type epoxy resin, naphthol novolak type epoxy resin, phenol novolak type epoxy resin, tert-butyl-catechol type epoxy resin, naphthalene type epoxy resin, naphthol type epoxy resin, anthracene type epoxy resin, glycidylamine type epoxy resin, glycidyl ester type epoxy resin, cresol novolak type epoxy resin, biphenyl type epoxy resin, linear aliphatic epoxy resin, epoxy resin having a butadiene structure, alicyclic epoxy resin, heterocyclic epoxy resin, spiro ring-containing epoxy resin, cyclohexane type epoxy resin, cyclohexanedimethanol type epoxy resin, naphthylene ether type epoxy resin, trimethylol type epoxy resin, and tetraphenylethane type epoxy resin. The bisphenol type epoxy resin refers to an epoxy resin having a bisphenol structure, and examples thereof include bisphenol A type epoxy resin, bisphenol F type epoxy resin, bisphenol S type epoxy resin, and bisphenol AF type epoxy resin. The biphenyl type epoxy resin refers to an epoxy resin having a biphenyl structure, and the biphenyl structure may have a substituent such as an alkyl group, an alkoxy group, or an aryl group. Therefore, the bixylenol type epoxy resin and the biphenyl aralkyl type epoxy resin are also included in the biphenyl type epoxy resin.

[0137] The epoxy resin can be classified into a liquid epoxy resin (hereinafter referred to as "liquid epoxy resin") at a temperature of 20°C and a solid epoxy resin (hereinafter referred to as "solid epoxy resin") at a temperature of 20°C. However, the resin composition of the present invention may contain only the liquid epoxy resin, only the solid epoxy resin, or a combination of the liquid epoxy resin and the solid epoxy resin as the component (C).

[0138] As the liquid epoxy resin, a liquid epoxy resin having two or more epoxy groups in one molecule is preferable.

[0139] As the liquid epoxy resin, a glycerol type epoxy resin, bisphenol A type epoxy resin, bisphenol F type epoxy resin, bisphenol AF type epoxy resin, naphthalene type epoxy resin, glycidyl ester type epoxy resin, glycidyl amine type epoxy resin, phenol novolac type epoxy resin, alicyclic epoxy resin having an ester skeleton, cyclohexanedimethanol type epoxy resin, cyclic aliphatic glycidyl ether, and epoxy resin having a butadiene structure are preferable.

[0140] Specific examples of the liquid epoxy resin include "EX-992L" manufactured by Nagase ChemteX Corporation, "YX7400" manufactured by Mitsubishi Chemical Corporation, "HP4032", "HP4032D", "HP4032SS" (naphthalene-type epoxy resin) manufactured by DIC Corporation; "828US", "828EL", "825" (bisphenol A-type epoxy resin) manufactured by Mitsubishi Chemical Corporation; "jER807", "1750" (bisphenol F-type epoxy resin) manufactured by Mitsubishi Chemical Corporation; "jER152" (phenol novolac-type epoxy resin) manufactured by Mitsubishi Chemical Corporation; "630", "630LSD", "604" (glycidylamine-type epoxy resin) manufactured by Mitsubishi Chemical Corporation; "ED-523T" (glycerol-type epoxy resin) manufactured by ADEKA Corporation; "EP-3950L", "EP-3980S" (glycidylamine-type epoxy resin) manufactured by ADEKA Corporation; "EP-4088S" (dicyclopentadiene-type epoxy resin) manufactured by ADEKA Corporation; "ZX1059" (a mixture of bisphenol A-type epoxy resin and bisphenol F-type epoxy resin) manufactured by Nippon Steel Chemical & Material Co., Ltd.; "EX-721" (glycidyl ester-type epoxy resin) manufactured by Nagase ChemteX Corporation; "EX-991L" (epoxy resin containing an alkyleneoxy skeleton and a butadiene skeleton) manufactured by Nagase ChemteX Corporation; "Celoxide 2021P" (alicyclic epoxy resin having an ester skeleton) manufactured by Daicel Corporation; "PB-3600", "JP-100", "JP-200" (epoxy resin having a butadiene structure) manufactured by Nippon Soda Co., Ltd.; "ZX1658", "ZX1658GS" (liquid 1,4-glycidylcyclohexane-type epoxy resin) manufactured by Nippon Steel Chemical & Material Co., Ltd.; "EG-280" (epoxy resin containing a fluorene structure) manufactured by Osaka Gas Chemical Co., Ltd.; "EX-201" (cyclic aliphatic glycidyl ether) manufactured by Nagase ChemteX Corporation, and the like.

[0141] As the solid epoxy resin, a solid epoxy resin having three or more epoxy groups in one molecule is preferable, and an aromatic solid epoxy resin having three or more epoxy groups in one molecule is more preferable.

[0142] Examples of the solid epoxy resin include a vicxylenol type epoxy resin, a naphthalene type epoxy resin, a naphthalene type tetrafunctional epoxy resin, a naphthol novolak type epoxy resin, a cresol novolak type epoxy resin, a dicyclopentadiene type epoxy resin, a trisphenol type epoxy resin, a naphthol type epoxy resin, a biphenyl type epoxy resin, a naphthylene ether type epoxy resin, an anthracene type epoxy resin, a bisphenol A type epoxy resin, a bisphenol AF type epoxy resin, a phenol aralkyl type epoxy resin, a tetraphenylethane type epoxy resin, and a phenolphthalimide type epoxy resin.

[0143] Specific examples of the solid epoxy resin include "HP4032H" (naphthalene-type epoxy resin) manufactured by DIC Corporation; "HP-4700", "HP-4710" (naphthalene-type tetrafunctional epoxy resin) manufactured by DIC Corporation; "N-690" (cresol novolak-type epoxy resin) manufactured by DIC Corporation; "N-695" (cresol novolak-type epoxy resin) manufactured by DIC Corporation; "HP-7200", "HP-7200HH", "HP-7200H", "HP-7200L" (dicyclopentadiene-type epoxy resin) manufactured by DIC Corporation; "EXA-7311", "EXA-7311-G3", "EXA-7311-G4", "EXA-7311-G4S", "HP-6000", "HP-6000L" (naphthylene ether-type epoxy resin) manufactured by DIC Corporation; "EPPN-502H" (trisphenol-type epoxy resin) manufactured by Nippon Kayaku Co., Ltd.; "NC7000L" (naphthol novolak-type epoxy resin) manufactured by Nippon Kayaku Co., Ltd.; "NC3000H", "NC3000", "NC3000L", "NC3000FH", "NC3100" (biphenyl-type epoxy resin) manufactured by Nippon Kayaku Co., Ltd.; "ESN475V", "ESN4100V" (naphthalene-type epoxy resin) manufactured by Nippon Steel Chemical & Material Co., Ltd.; "ESN485" (naphthol-type epoxy resin) manufactured by Nippon Steel Chemical & Material Co., Ltd.; "ESN375" (dihydroxynaphthalene-type epoxy resin) manufactured by Nippon Steel Chemical & Material Co., Ltd.; "YX4000H", "YX4000", "YX4000HK", "YL7890" (bixylenol-type epoxy resin) manufactured by Mitsubishi Chemical Corporation; "YL6121" (biphenyl-type epoxy resin) manufactured by Mitsubishi Chemical Corporation; "YX8800" (anthracene-type epoxy resin) manufactured by Mitsubishi Chemical Corporation; "YX7700" (phenol aralkyl-type epoxy resin) manufactured by Mitsubishi Chemical Corporation; "PG-100", "CG-500" manufactured by Osaka Gas Chemical Co., Ltd.; "YL7760" (bisphenol AF-type epoxy resin) manufactured by Mitsubishi Chemical Corporation; "YL7800" (fluorene-type epoxy resin) manufactured by Mitsubishi Chemical Corporation; "jER1010" (bisphenol A-type epoxy resin) manufactured by Mitsubishi Chemical Corporation; "jER1031S" (tetraphenylethane-type epoxy resin) manufactured by Mitsubishi Chemical Corporation; "WHR991S" (phenolphthalimide-type epoxy resin) manufactured by Nippon Kayaku Co., Ltd., and the like.These may be used alone or in combination of two or more kinds.

[0144] When using a combination of a liquid epoxy resin and a solid epoxy resin as the epoxy resin, their mass ratio (liquid epoxy resin:solid epoxy resin) is preferably 10:1 to 1:50, more preferably 5:1 to 1:20, still more preferably 2:1 to 1:10, and particularly preferably 1:1 to 1:3.

[0145] The epoxy equivalent of the epoxy resin is preferably 50 g / eq. to 5,000 g / eq., more preferably 60 g / eq. to 2,000 g / eq., still more preferably 70 g / eq. to 1,000 g / eq., and even more preferably 80 g / eq. to 500 g / eq. The epoxy equivalent is the mass of the resin per equivalent of epoxy groups. This epoxy equivalent can be measured according to JIS K7236.

[0146] The weight average molecular weight of the epoxy resin is preferably 100 to 5,000, more preferably 250 to 3,000, and still more preferably 400 to 1,500. The weight average molecular weight of the resin can be measured as a value in terms of polystyrene by the gel permeation chromatography (GPC) method.

[0147] -Phenolic resin- As the phenolic resin, a compound having one or more, preferably two or more hydroxyl groups bonded to an aromatic ring such as a benzene ring or a naphthalene ring in one molecule can be used. Since the phenolic resin can react with an epoxy resin to cure the resin composition when combined with the epoxy resin, it is sometimes referred to as a "phenolic curing agent". From the viewpoint of significantly obtaining the effects of the present invention, a phenolic resin having a novolak structure is preferred. Further, from the viewpoint of adhesion, a nitrogen-containing phenolic resin is preferred, and a phenolic resin containing a triazine skeleton is more preferred. Among them, from the viewpoint of significantly obtaining the effects of the present invention, a phenolic novolak resin containing a triazine skeleton is preferred. Specific examples of the phenolic resin include, for example, "MEH-7700", "MEH-7810", "MEH-7851" manufactured by Meiwa Kasei Co., Ltd., "NHN", "CBN", "GPH" manufactured by Nippon Kayaku Co., Ltd., "SN-170", "SN-180", "SN-190", "SN-475", "SN-485", "SN-495", "SN-375", "SN-395" manufactured by Nippon Steel Chemical & Material Co., Ltd., "LA-7052", "LA-7054", "LA-3018", "LA-3018-50P", "LA-1356", "TD2090", "TD-2090-60M", "KA-1163" manufactured by DIC Corporation, and the like.

[0148] -cyanate ester resin- As the cyanate ester resin, a compound having one or more, preferably two or more cyanate groups in one molecule can be used. Since the cyanate ester resin can react with an epoxy resin to cure the resin composition when combined with the epoxy resin, it is sometimes referred to as a "cyanate ester-based curing agent". Examples of the cyanate ester resin 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'-ethylidenediphenyl 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; polyfunctional cyanate resins derived from phenol novolac and cresol novolac; prepolymers in which some of these cyanate resins are partially triazine-formed; and the like. Specific examples of the cyanate ester resin include "PT30" and "PT60" (both are phenol novolac type polyfunctional cyanate resins), "BA230", "BA230S75" (a prepolymer in which part or all of bisphenol A dicyanate is triazine-formed to form a trimer), etc. manufactured by Lonza

[0149] -Active Ester Resin- As the active ester resin, generally, compounds having two or more highly reactive ester groups in one molecule, such as phenol esters, thiophenol esters, N-hydroxyamine esters, esters of heterocyclic hydroxy compounds, etc., are preferably used. Since the active ester resin can react with an epoxy resin to cure the resin composition when combined with the epoxy resin, it is sometimes referred to as an "active ester-based curing agent". The active ester resin is preferably obtained by a condensation reaction of a carboxylic acid compound and / or a thiocarboxylic acid compound with a hydroxy compound and / or a thiol compound. Particularly from the viewpoint of improving heat resistance, an active ester resin obtained from a carboxylic acid compound and a hydroxy compound is preferred, and an active ester resin obtained from a carboxylic acid compound and a phenol compound and / or a naphthol compound is more preferred. As the carboxylic acid compound, either an aromatic carboxylic acid compound or an aliphatic carboxylic acid compound may be used, and examples thereof include benzoic acid, acetic acid, succinic acid, maleic acid, itaconic acid, phthalic acid, isophthalic acid, terephthalic acid, pyromellitic acid, and their halides. Examples of the aromatic hydroxy compound include (i) an addition reaction product of an unsaturated aliphatic cyclic compound containing two double bonds in one molecule and phenols, (ii) various bisphenol compounds, (iii) an aromatic polyol having two or more hydroxy groups bonded to a carbon atom on the aromatic ring, (iv) an aromatic monool having one hydroxy group bonded to a carbon atom on the aromatic ring, etc. Examples of the addition reaction product of an unsaturated aliphatic cyclic compound and phenols include addition reaction products of unsaturated aliphatic cyclic compounds such as dicyclopentadiene, tetrahydroindene, norbornadiene, limonene, vinylcyclohexene, etc. and phenols which may have substituents (for example, phenol, cresol, xylenol, ethylphenol, propylphenol, vinylphenol, allylphenol, phenylphenol, benzylphenol, halophenol, etc.), and specifically, for example, dicyclopentadiene-phenol addition products.Examples of bisphenol compounds include bisphenol A, bisphenol F, bisphenol AF, bisphenol AP, bisphenol B, bisphenol BP, bisphenol C, bisphenol M, etc. Examples of aromatic polyols having two or more hydroxy groups bonded to carbon atoms on the aromatic ring include hydroquinone, resorcinol, catechol, 1,5-dihydroxynaphthalene, 1,6-dihydroxynaphthalene, 2,6-dihydroxynaphthalene, dihydroxybenzophenone, trihydroxybenzophenone, tetrahydroxybenzophenone, phloroglucin, benzenetriol, phenol novolak, etc. Examples of aromatic monools having one hydroxy group bonded to a carbon atom on the aromatic ring include phenol, cresol, xylenol, ethylphenol, propylphenol, vinylphenol, allylphenol, phenylphenol, benzylphenol, halophenol, naphthol, methylnaphthol, dimethylnaphthol, ethylnaphthol, propylnaphthol, vinylnaphthol, allylnaphthol, phenylnaphthol, benzylnaphthol, halonaphthol, etc.

[0150] Specifically, as the active ester resin, a dicyclopentadiene type active ester resin, a naphthalene type active ester resin containing a naphthalene structure, an active ester resin containing an acetylated product of phenol novolak, an active ester resin containing a benzoylated product of phenol novolak, and an active ester resin containing a styryl group and a naphthalene structure are preferable, and among them, at least one selected from a dicyclopentadiene type active ester resin and a naphthalene type active ester resin is more preferable. As the dicyclopentadiene type active ester resin, an active ester resin containing a dicyclopentadiene type diphenol structure is preferable.

[0151] Examples of commercially available active ester resins include, for example, as active ester resins containing a dicyclopentadiene-type diphenol structure, "EXB9451", "EXB9460", "EXB9460S", "EXB-8000L", "EXB-8000L-65M", "EXB-8000L-65TM", "HPC-8000L-65TM", "HPC-8000L-65T", "HPC-8000", "HPC-8000-65T", "HPC-8000H", "HPC-8000H-65TM" (manufactured by DIC Corporation); as active ester resins containing a naphthalene structure, "HP-B-8151-62T", "EXB-8100L-65T", "EXB-8150-60T", "EXB-8150-62T", "EXB-9416-70BK", "HPC-8150-60T", "HPC-8150-62T", "EXB-8" (manufactured by DIC Corporation); as phosphorus-containing active ester resins, "EXB9401" (manufactured by DIC Corporation); as active ester resins that are acetylated products of phenol novolac, "DC808" (manufactured by Mitsubishi Chemical Corporation); as active ester resins that are benzoylated products of phenol novolac, "YLH1026", "YLH1030", "YLH1048" (manufactured by Mitsubishi Chemical Corporation); as active ester resins containing a styryl group and a naphthalene structure, "PC1300-02-65MA" (manufactured by Air Water Incorporated), and the like.

[0152] - Carbodiimide Resin - As the carbodiimide resin, a compound having one or more, preferably two or more carbodiimide structures in one molecule can be used. Since the carbodiimide resin can react with an epoxy resin to cure the resin composition when combined with the epoxy resin, it is sometimes referred to as a "carbodiimide-based curing agent". Specific examples of the carbodiimide resin include aliphatic biscarbodiimides such as tetramethylene-bis(t-butylcarbodiimide) and cyclohexane bis(methylene-t-butylcarbodiimide); biscarbodiimides such as aromatic biscarbodiimides like phenylene-bis(xilylcarbodiimide); aliphatic polycarbodiimides such as polyhexamethylene carbodiimide, polytrimethylhexamethylene carbodiimide, polycyclohexylene carbodiimide, poly(methylenebiscyclohexylene carbodiimide), and poly(isophorone carbodiimide); aromatic polycarbodiimides such as poly(phenylene carbodiimide), poly(naphthylene carbodiimide), poly(tolylene carbodiimide), poly(methyldiisopropylphenylene carbodiimide), poly(triethylphenylene carbodiimide), poly(diethylphenylene carbodiimide), poly(triisopropylphenylene carbodiimide), poly(diisopropylphenylene carbodiimide), poly(xylene carbodiimide), poly(tetramethylxylene carbodiimide), poly(methylenediphenylene carbodiimide), and poly[methylenebis(methylphenylene) carbodiimide]. Examples of commercially available carbodiimide resins include, for example, "Carbodilite V-02B", "Carbodilite V-03", "Carbodilite V-04K", "Carbodilite V-07", and "Carbodilite V-09" manufactured by Nisshinbo Chemical Co., Ltd.; "Stabaxol P", "Stabaxol P400", "Highcadil 510", etc. manufactured by LANXESS Co., Ltd.

[0153] -Acid anhydride resin- As the acid anhydride resin, a compound having one or more, preferably two or more acid anhydride groups in one molecule can be used. Since the acid anhydride resin can react with an epoxy resin when combined with an epoxy group to cure the resin composition, it is sometimes referred to as an "acid anhydride-based curing agent". Specific examples of the acid anhydride resin 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, benzophenone tetracarboxylic dianhydride, 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 polymer-type acid anhydrides such as styrene-maleic acid resin copolymerized from styrene and maleic acid. Commercially available products of the acid anhydride resin include, for example, "HNA-100", "MH-700", "MTA-15", "DDSA", "OSA" manufactured by Shin Nippon Rika Co., Ltd.; "YH-306", "YH-307" manufactured by Mitsubishi Chemical Corporation; "HN-2200", "HN-5500" manufactured by Resonaak; "EF-30", "EF-40", "EF-60", "EF-80" manufactured by Cray Valley Co., Ltd., etc.

[0154] -amine resin- As the amine resin, a compound having one or more, preferably two or more amino groups in one molecule can be used. Since the amine resin can react with an epoxy resin to cure the resin composition when combined with an epoxy group, it is sometimes referred to as an "amine-based curing agent". Examples of the amine resin include aliphatic amines, polyether amines, alicyclic amines, aromatic amines, etc. Among them, aromatic amines are preferred. The amine resin is preferably a primary amine or a secondary amine, and more preferably a primary amine. Specific examples of the amine resin 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, 2,2-bis(3-amino-4-hydroxyphenyl)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, etc. Commercially available products of the amine resin include, for example, "SEIKACURE-S" manufactured by Seika Corporation; "KAYABOND C-200S", "KAYABOND C-100", "KAYAHARD A-A", "KAYAHARD A-B", "KAYAHARD A-S" manufactured by Nippon Kayaku Co., Ltd.; "EPICURE W" manufactured by Mitsubishi Chemical Corporation; "DTDA" manufactured by Sumitomo Seika Chemicals Co., Ltd., etc.

[0155] -Benzoxazine Resin- Since benzoxazine resin can react with epoxy resin to cure the resin composition when combined with epoxy resin, it is sometimes referred to as a "benzoxazine-based curing agent". Specific examples of benzoxazine resin include "JBZ-OP100D" and "ODA-BOZ" manufactured by JFE Chemical Corporation; "HFB2006M" manufactured by Showa High Polymer Co., Ltd.; "P-d" and "F-a" manufactured by Shikoku Kasei Kogyo Co., Ltd., etc.

[0156] Since thiol resin can react with epoxy resin to cure the resin composition when combined with epoxy resin, it is sometimes referred to as a "thiol-based curing agent". Examples of thiol resin include trimethylolpropane tris(3-mercaptopropionate), pentaerythritol tetrakis(3-mercaptobutyrate), tris(3-mercaptopropyl) isocyanurate, etc.

[0157] -Terminal double bond resin- A terminal double bond resin is a radically polymerizable resin having one or more (preferably two or more) ethylenically unsaturated groups having a carbon-carbon double bond in one molecule, or a radically polymerizable group containing an ethylenically unsaturated bond at the molecular terminal. Examples of the radically polymerizable group include one or more selected from a vinyl group, a propenyl group (1-propenyl group), an allyl group (2-propenyl group), a styryl group, a vinylphenyl group, an acryloyl group, and a methacryloyl group. Among them, from the viewpoint of more enjoying the effects of the present invention, one or more selected from a vinyl group, an allyl group, and a styryl group are preferable. Among them, from the viewpoint of easily enjoying the effects of the present invention, the terminal double bond resin is preferably an allyl resin, a vinyl resin, or a styryl resin.

[0158] An allyl resin is, for example, a compound having one or more, preferably two or more allyl groups. Examples of allyl 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-naphthalenedicarboxylate; allyl ester compounds of isocyanuric acid 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 diallyl diphenylsilane. Commercially available products of allyl radical polymerizable compounds include, for example, "TAIC" (1,3,5-triallyl isocyanurate) manufactured by Nippon Kasei Co., Ltd., "DAD" (diallyl diphenate) manufactured by Nisshoku Fine Chemical Co., Ltd., "TRIAM-705" (triallyl trimellitate) manufactured by Fujifilm Wako Pure Chemical Corporation, the product name "DAND" (diallyl 2,3-naphthalenedicarboxylate) manufactured by Nisshoku Fine Chemical Co., Ltd., "ALP-d" (bis[3-allyl-4-(3,4-dihydro-2H-1,3-benzoxazin-3-yl)phenyl]methane) manufactured by Shikoku Kasei Kogyo Co., Ltd., "RE-810NM" (2,2-bis[3-allyl-4-(glycidyloxy)phenyl]propane) manufactured by Nippon Kayaku Co., Ltd., "DA-MGIC" (1,3-diallyl-5-glycidyl isocyanurate) manufactured by Shikoku Kasei Kogyo Co., Ltd., and the like.

[0159] Examples of vinyl resins include trialkenyl isocyanurate compounds such as triallyl isocyanurate, polybutadiene resins having repeating units of 1,2-butadiene, cis-1,4-butadiene, and trans-1,4-butadiene, and vinyl benzyl compounds such as styrene and divinylbenzene having a vinyl benzyl group in the molecule.

[0160] As the styryl resin, as long as it has one or more (preferably two or more) styryl groups or vinylphenyl groups in one molecule, its type is not particularly limited, and it may be a monomer or an oligomer. Examples of the styryl resin include "OPE-2St", "OPE-2St 1200", "OPE-2St 2200" (all manufactured by Mitsubishi Gas Chemical Company). The styryl resin also includes, in addition to the styrene monomer, for example, homopolymers of aromatic divinyl 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, or copolymers of these aromatic divinyl compounds and aromatic monovinyl compounds such as styrene, vinyltoluene, ethylstyrene, and vinylnaphthalene.

[0161] (From the viewpoint of realizing a resin composition that exhibits good dielectric properties, exhibits good mechanical properties (high elongation at break point), and provides a cured product with excellent crack resistance in combination with the component (A) and the component (B), when the resin component in the resin composition is 100% by mass, the content of the component (C) in the resin composition is preferably 5% by mass or more, more preferably 10% by mass or more, still more preferably 15% by mass or more, and even more preferably 20% by mass or more. The upper limit of its content is preferably 60% by mass or less, more preferably 50% by mass or less, still more preferably 40% by mass or less or 35% by mass or less. Therefore, in one embodiment, when the resin component in the resin composition is 100% by mass, the content of the component (C) is 10% by mass or more and 50% by mass or less.

[0162] From the perspective of realizing a resin composition that exhibits good dielectric properties, exhibits good mechanical properties (high elongation at break), and provides a cured product with excellent crack resistance, when the resin component in the resin composition is 100% by mass, the total content of component (A), component (B), and component (C) is preferably 60% by mass or more, more preferably 70% by mass or more, still more preferably 80% by mass or more, even more preferably 85% by mass or more or 90% by mass or more, and the upper limit is not particularly limited and can be, for example, 99.8% by mass or less, 99.5% by mass or less, 99% by mass or less, etc.

[0163] [(D) Thermoplastic resin] The resin composition of the present invention may contain a thermoplastic resin as component (D).

[0164] Examples of component (D) include polystyrene resin, oxazoline group-containing resin, polyimide resin, phenoxy resin, polyvinyl acetal resin, polyolefin resin, polybutadiene resin, polyamideimide resin, polyetherimide resin, polysulfone resin, polyethersulfone resin, polyphenylene ether resin, polycarbonate resin, polyetheretherketone resin, polyester resin, etc.

[0165] In one embodiment, component (D) preferably contains one or more selected from the group consisting of polystyrene resin, oxazoline group-containing resin, polyimide resin, and phenoxy resin, more preferably contains one or more selected from the group consisting of polyimide resin and phenoxy resin, and particularly preferably contains phenoxy resin. Further, component (D) may be used alone or in combination of two or more.

[0166] Polystyrene resin may be a commercially available product. For example, hydrogenated styrene-based thermoplastic elastomers such as "H1041", "Tuftec H1043", "Tuftec P2000", "Tuftec MP10" (manufactured by Asahi Kasei Corporation); epoxidized styrene-butadiene thermoplastic elastomers such as "Epofrend AT501", "CT310" (manufactured by Daicel Corporation); modified styrene-based elastomers having a hydroxyl group such as "Septon HG252" (manufactured by Kuraray Co., Ltd.); modified styrene-based elastomers having a carboxyl group such as "Tuftec N503M", modified styrene-based elastomers having an amino group such as "Tuftec N501", modified styrene-based elastomers having an acid anhydride group such as "Tuftec M1913" (manufactured by Asahi Kasei Corporation); unmodified styrene-based elastomers such as "Septon S8104" (manufactured by Kuraray Co., Ltd.) and the like can be mentioned.

[0167] The oxazoline group-containing resin is obtained, for example, by polymerizing addition-polymerizable oxazoline compounds (monomers containing a vinyl oxazoline skeleton) such as 2-isopropenyl-2-oxazoline, 5-methyl-2-isopropenyl-2-oxazoline, 4,4-dimethyl-2-isopropenyl-2-oxazoline, 4-methyl-2-isopropenyl-2-oxazoline, 4,4,5-trimethyl-2-isopropenyl-2-oxazoline, 2-vinyl-2-oxazoline, 5-methyl-2-vinyl-2-oxazoline, 4,4-dimethyl-2-vinyl-2-oxazoline, 4-methyl-2-vinyl-2-oxazoline, 4,4,5-trimethyl-2-vinyl-2-oxazoline, and other monomers such as styrene-based monomers such as styrene, α-methylstyrene, 4-methylstyrene, 3-methylstyrene, 2-methylstyrene, 4-ethylstyrene, 4-tert-butylstyrene, p-divinylbenzene, m-divinylbenzene may be copolymerized as necessary. Specific examples of the oxazoline group-containing resin include "PX-3-RP-61" manufactured by Nippon Shokubai Co., Ltd.

[0168] Specific examples of the polyimide resin include "SLK-6100" manufactured by Shin-Etsu Chemical Co., Ltd., "Ricacote SN20" and "Ricacote PN20" manufactured by Shin Nippon Rika Co., Ltd., "PIAD200" manufactured by Arakawa Chemical Co., Ltd., and the like.

[0169] Examples of the phenoxy resin include phenoxy resins having one or more skeletons selected from the group consisting of a bisphenol A skeleton, a bisphenol F skeleton, a bisphenol S skeleton, a bisphenol acetophenone skeleton, a novolak skeleton, a biphenyl skeleton, a fluorene skeleton, a dicyclopentadiene skeleton, a norbornene skeleton, a naphthalene skeleton, an anthracene skeleton, an adamantane skeleton, a terpene skeleton, and a trimethylcyclohexane skeleton. The terminal of the phenoxy resin may be any functional group such as a phenolic hydroxyl group or an epoxy group.

[0170] Specific examples of the phenoxy resin include "1256" and "4250" manufactured by Mitsubishi Chemical Corporation (both are bisphenol A skeleton-containing phenoxy resins); "YX8100" manufactured by Mitsubishi Chemical Corporation (bisphenol S skeleton-containing phenoxy resin); "YX6954" manufactured by Mitsubishi Chemical Corporation (bisphenol acetophenone skeleton-containing phenoxy resin), "FX280" and "FX293" manufactured by Nippon Steel Chemical & Material Co., Ltd.; "YX7200B35", "YL7500BH30", "YX6954BH30", "YX7553BH30", "YL7769BH30", "YL6794", "YL7213", "YL7290", and "YL7482" manufactured by Mitsubishi Chemical Corporation, etc.

[0171] Examples of the polyvinyl acetal resin include polyvinyl formal resin and polyvinyl butyral resin, and polyvinyl butyral resin is preferred. Specific examples of the polyvinyl acetal resin include Esrec BH series, BX series (e.g., BX-5Z), KS series (e.g., KS-1), BL series, BM series manufactured by Sekisui Chemical Co., Ltd.; etc.

[0172] Examples of polyolefin resins include ethylene-based copolymer resins such as low-density polyethylene, ultra-low density polyethylene, high-density polyethylene, ethylene-vinyl acetate copolymer, ethylene-ethyl acrylate copolymer, and ethylene-methyl acrylate copolymer; and polyolefin polymers such as polypropylene and ethylene-propylene block copolymer.

[0173] Examples of polybutadiene resins include resins containing a hydrogenated polybutadiene backbone, hydroxy group-containing polybutadiene resins, phenolic hydroxyl group-containing polybutadiene resins, carboxy group-containing polybutadiene resins, acid anhydride group-containing polybutadiene resins, epoxy group-containing polybutadiene resins, isocyanate group-containing polybutadiene resins, urethane group-containing polybutadiene resins, polyphenylene ether-polybutadiene resins, and the like.

[0174] Specific examples of polyamideimide resins include "Vironmax HR11NN" and "Vironmax HR16NN" manufactured by Toyobo Co., Ltd. Specific examples of polyamideimide resins also include modified polyamideimides such as "KS9100" and "KS9300" (polyamideimide containing a polysiloxane backbone) manufactured by Resona Co., Ltd.

[0175] Specific examples of polyethersulfone resins include "PES5003P" manufactured by Sumitomo Chemical Co., Ltd.

[0176] Specific examples of polysulfone resins include polysulfones "P1700", "P3500", etc. manufactured by Solvay Advanced Polymers, LLC.

[0177] Specific examples of polyphenylene ether resins include "NORYL SA90" manufactured by SABIC. Specific examples of polyetherimide resins include "ULTEM" manufactured by GE.

[0178] Examples of the polycarbonate resin include a hydroxy group-containing carbonate resin, a phenolic hydroxyl group-containing carbonate resin, a carboxy group-containing carbonate resin, an acid anhydride group-containing carbonate resin, an isocyanate group-containing carbonate resin, a urethane group-containing carbonate resin, and the like. Specific examples of the polycarbonate resin include "FPC0220" manufactured by Mitsubishi Gas Chemical Company, "T6002", "T6001" (polycarbonate diol) manufactured by Asahi Kasei Corporation, "C-1090", "C-2090", "C-3090" (polycarbonate diol) manufactured by Kuraray Co., Ltd., and the like. Specific examples of the polyetheretherketone resin include "Sumipro EK" manufactured by Sumitomo Chemical Company, and the like.

[0179] Examples of the polyester resin include polyethylene terephthalate resin, polyethylene naphthalate resin, polybutylene terephthalate resin, polybutylene naphthalate resin, polytrimethylene terephthalate resin, polytrimethylene naphthalate resin, polycyclohexanedimethylene terephthalate resin, and the like.

[0180] When the resin component in the resin composition is 100% by mass, the content of the component (D) in the resin composition is, for example, 0% by mass or more, preferably 0.01% by mass or more, more preferably 0.1% by mass or more, still more preferably 0.5% by mass or more, 1% by mass or more, 2% by mass or more, or 3% by mass or more, and the upper limit of the content is preferably 30% by mass or less, more preferably 25% by mass or less, still more preferably 20% by mass or less, 15% by mass or less, or 10% by mass or less.

[0181] [(E) Inorganic filler] The resin composition of the present invention may contain an inorganic filler as the component (E).

[0182] Examples of the inorganic filler include silica, alumina, glass, cordierite, silicon oxide, barium sulfate, barium carbonate, talc, clay, mica powder, zinc oxide, hydrotalcite, boehmite, aluminum silicate, aluminum hydroxide, magnesium hydroxide, calcium carbonate, magnesium carbonate, magnesium oxide, boron nitride, aluminum nitride, manganese nitride, aluminum borate, strontium carbonate, strontium titanate, calcium titanate, magnesium titanate, bismuth titanate, titanium oxide, zirconium oxide, barium titanate, barium zirconate titanate, barium zirconate, calcium zirconate, zirconium phosphate, and zirconium tungstate phosphate. Among these, silica is particularly preferred. Examples of silica include amorphous silica, fused silica, crystalline silica, synthetic silica, and hollow silica. Spherical silica is preferred as the silica. The inorganic filler may be used alone or in combination of two or more.

[0183] Examples of commercially available products of the inorganic filler include "SP60-05" and "SP507-05" manufactured by Nippon Steel Chemical & Material Co., Ltd.; "YC100C", "YA050C", "YA050C-MJE", "YA010C", "SC2500SQ", "SO-C4", "SO-C2", and "SO-C1" manufactured by Admatechs Co., Ltd.; "UFP-30", "DAW-03", and "FB-105FD" manufactured by Denka Co., Ltd.; "Silfill NSS-3N", "Silfill NSS-4N", and "Silfill NSS-5N" manufactured by Tokuyama Corporation; "Celspheres" and "MGH-005" manufactured by Taiheiyo Cement Corporation; "Esferique" and "BA-1" manufactured by JGC Catalysts & Chemicals Ltd.

[0184] The average particle size of the inorganic filler is not particularly limited, but is preferably 10 μm or less, more preferably 5 μm or less, still more preferably 3 μm or less, 2 μm or less, 1 μm or less, or 0.7 μm or less. The lower limit of the average particle size is not particularly limited, but is preferably 0.01 μm or more, more preferably 0.05 μm or more, still more preferably 0.07 μm or more, 0.1 μm or more, or 0.2 μm or more. The average particle diameter of the inorganic filler can be measured by a laser diffraction / scattering method based on the Mie scattering theory. Specifically, the particle size distribution of the inorganic filler is created on a volume basis by a laser diffraction / scattering type particle size distribution measuring device, and the median diameter thereof is taken as the average particle diameter for measurement. As the measurement sample, 100 mg of the inorganic filler and 10 g of methyl ethyl ketone can be weighed into a vial and dispersed by ultrasonic waves for 10 minutes for use. The measurement sample is measured for the volume-based particle size distribution of the inorganic filler by a flow cell method using a laser diffraction type particle size distribution measuring device with the wavelengths of the light sources used being blue and red, and the average particle diameter is calculated as the median diameter from the obtained particle size distribution. Examples of the laser diffraction type particle size distribution measuring device include "LA-960" manufactured by Horiba, Ltd.

[0185] The specific surface area of the inorganic filler is not particularly limited, but is preferably 0.1 m 2 / g or more, more preferably 0.5 m 2 / g or more, still more preferably 1 m 2 / g or more, 3 m 2 / g or more or 5 m 2 / g or more. The upper limit of the specific surface area is not particularly limited, but is preferably 100 m 2 / g or less, more preferably 80 m 2 / g or less, still more preferably 60 m 2 / g or less, 50 m 2 / g or less or 40 m 2 / g or less. The specific surface area of the inorganic filler is obtained by adsorbing nitrogen gas on the sample surface in accordance with the BET method using a specific surface area measuring device (Macsorb HM-1210 manufactured by Mountech Co., Ltd.) and calculating the specific surface area using the BET multi-point method.

[0186] The inorganic filler is preferably surface-treated with a suitable surface treatment agent. By being surface-treated, the moisture resistance and dispersibility of the inorganic filler can be enhanced. Examples of the surface treatment agent include silane coupling agents such as vinyl-based silane coupling agents, epoxy-based silane coupling agents, styryl-based silane coupling agents, (meth)acrylic-based silane coupling agents, amino-based silane coupling agents, isocyanurate-based silane coupling agents, ureido-based silane coupling agents, mercapto-based silane coupling agents, isocyanate-based silane coupling agents, acid anhydride-based silane coupling agents; non-silane coupling - alkoxysilane compounds such as methyltrimethoxysilane and phenyltrimethoxysilane; silazane compounds, etc. The surface treatment agent may be used alone or in combination of two or more.

[0187] Examples of commercially available surface treatment agents include, for example, "KBM403" (3-glycidoxypropyltrimethoxysilane) manufactured by Shin-Etsu Chemical Co., Ltd., "KBM803" (3-mercaptopropyltrimethoxysilane) manufactured by Shin-Etsu Chemical Co., Ltd., "KBE903" (3-aminopropyltriethoxysilane) manufactured by Shin-Etsu Chemical Co., Ltd., "KBM573" (N-phenyl-3-aminopropyltrimethoxysilane) manufactured by Shin-Etsu Chemical Co., Ltd., "SZ-31" (hexamethyldisilazane) manufactured by Shin-Etsu Chemical Co., Ltd., etc.

[0188] From the viewpoint of improving the dispersibility of the inorganic filler, the degree of surface treatment with the surface treatment agent preferably falls within a predetermined range. Specifically, 100% by mass of the inorganic filler is preferably surface-treated with 0.2 to 5% by mass of the surface treatment agent.

[0189] 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. The amount of carbon per unit surface area of the inorganic filler is preferably 0.02 mg / m 2 or more from the viewpoint of improving the dispersibility of the inorganic filler, more preferably 0.1 mg / m 2 or more, and still more preferably 0.2 mg / m 2The above is more preferable. On the other hand, from the viewpoint of preventing an increase in the melt viscosity of the resin composition and the melt viscosity in the sheet form, 1.0 mg / m 2 or less is preferable, 0.8 mg / m 2 or less is more preferable, and 0.5 mg / m 2 or less is even more preferable. The amount of carbon per unit surface area of the component (E) can be measured after washing the surface-treated inorganic filler with a solvent (for example, methyl ethyl ketone (MEK)). Specifically, a sufficient amount of MEK as a solvent is added to the inorganic filler 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. As the carbon analyzer, "EMIA-320V" manufactured by Horiba, Ltd. can be used.

[0190] In combination with the components (A) to (C), from the viewpoint of realizing a resin composition that exhibits good dielectric properties, exhibits good mechanical properties (high elongation at break), and provides a cured product excellent in crack resistance, the content of the component (E) in the resin composition, when the non-volatile components in the resin composition are 100% by mass, is preferably 50% by mass or more, more preferably 60% by mass, even more preferably 70% by mass or more, and the upper limit of its content is preferably 85% by mass or less, more preferably 80% by mass or less.

[0191] [(F) Radical polymerization initiator] The resin composition of the present invention may contain a radical polymerization initiator as the component (F).

[0192] Examples of the component (F) include a thermal polymerization initiator that generates free radicals upon heating and a photoinitiator that generates free radicals upon light irradiation. Among them, from the viewpoint of being able to more enjoy the effects of the present invention, a thermal polymerization initiator is preferable. The component (F) may be used alone or in any combination of two or more.

[0193] (F) Examples of the component include peroxide-based radical polymerization initiators, azo-based radical polymerization initiators, etc. Among them, peroxide-based radical polymerization initiators are preferred.

[0194] Examples of the peroxide-based radical polymerization initiator include hydroperoxide compounds such as 1,1,3,3-tetramethylbutyl hydroperoxide; dialkyl peroxide compounds such as tert-butyl cumyl peroxide, di-tert-butyl peroxide, di-tert-hexyl peroxide, dicumyl peroxide, 1,4-bis(1-tert-butylperoxy-1-methylethyl)benzene, 2,5-dimethyl-2,5-bis(tert-butylperoxy)hexane; diacyl peroxide compounds such as dilauroyl peroxide, didecanoyl peroxide, dicyclohexyl peroxydicarbonate, bis(4-tert-butylcyclohexyl) peroxydicarbonate; peroxyester compounds such as tert-butyl peroxyacetate, tert-butyl peroxybenzoate, tert-butyl peroxyisopropyl monocarbonate, tert-butyl peroxy-2-ethylhexanoate, tert-butyl peroxyneodecanoate, tert-hexyl peroxyisopropyl monocarbonate, tert-butyl peroxylaurate, (1,1-dimethylpropyl) 2-ethylperhexanoate, tert-butyl 2-ethylperhexanoate, tert-butyl 3,5,5-trimethylperhexanoate, tert-butyl peroxy-2-ethylhexyl monocarbonate, tert-butyl peroxymaleic acid; etc.

[0195] Examples of azo radical polymerization initiators include azonitrile compounds such as 2,2'-azobis(4-methoxy-2,4-dimethylvaleronitrile), 2,2'-azobis(2,4-dimethylvaleronitrile), 2,2'-azobisisobutyronitrile, 2,2'-azobis(2-methylbutyronitrile), 1,1'-azobis(cyclohexane-1-carbonitrile), 1-[(1-cyano-1-methylethyl)azo]formamide, and 2-phenylazo-4-methoxy-2,4-dimethyl-valeronitrile; azoamide compounds such as 2,2'-azobis[2-methyl-N-[1,1-bis(hydroxymethyl)-2-hydroxyethyl]propionamide], 2,2'-azobis[2-methyl-N-[1,1-bis(hydroxymethyl)ethyl]propionamide], 2,2'-azobis[2-methyl-N-[2-(1-hydroxybutyl)]-propionamide], 2,2'-azobis[2-methyl-N-(2-hydroxyethyl)-propionamide], 2,2'-azobis(2-methylpropionamide) dihydrate, 2,2'-azobis[N-(2-propenyl)-2-methylpropionamide], 2,2'-azobis(N-butyl-2-methylpropionamide), and 2,2'-azobis(N-cyclohexyl-2-methylpropionamide); alkyl azo compounds such as 2,2'-azobis(2,4,4-trimethylpentane) and 2,2'-azobis(2-methylpropane); and the like.

[0196] Examples of commercially available products of component (F) include "Perbutyl C", "Perbutyl A", "Perbutyl P", "Perbutyl L", "Perbutyl O", "Perbutyl ND", "Perbutyl Z", "Perbutyl I", "Parkmill P", "Parkmill D", "Perhexyl D", "Perhexyl A", "Perhexyl I", "Perhexyl Z", "Perhexyl ND", "Perhexyl O", "Perhexyl PV", etc. manufactured by NOF Corporation.

[0197] The content of component (F) in the resin composition is not particularly limited. However, when the resin component in the resin composition is 100% by mass, it is preferably 10% by mass or less, more preferably 5% by mass or less, still more preferably 3% by mass or less, and even more preferably 1.5% by mass or less. The lower limit of the content is not particularly limited. However, when the resin component in the resin composition is 100% by mass, for example, it is 0% by mass or more, preferably 0.01% by mass or more, more preferably 0.05% by mass or more, still more preferably 0.1% by mass or more, 0.3% by mass or more, 0.5% by mass or more, or 0.8% by mass or more, etc.

[0198] [(G) Curing accelerator] The resin composition of the present invention may contain a curing accelerator as component (G).

[0199] Examples of component (G) include phosphorus-based curing accelerators, amine-based curing accelerators, imidazole-based curing accelerators, guanidine-based curing accelerators, metal-based curing accelerators, etc. Amine-based curing accelerators, imidazole-based curing accelerators, and metal-based curing accelerators are preferred, and either an amine-based curing accelerator or an imidazole-based curing accelerator is more preferred. Component (B) may be used alone or in combination of two or more.

[0200] Examples of phosphorus-based curing accelerators include triphenylphosphine, phosphonium borate compounds, tetraphenylphosphonium tetraphenylborate, n-butylphosphonium tetraphenylborate, tetrabutylphosphonium decanoate, (4-methylphenyl)triphenylphosphonium thiocyanate, tetraphenylphosphonium thiocyanate, butyltriphenylphosphonium thiocyanate, etc. Triphenylphosphine and tetrabutylphosphonium decanoate are preferred.

[0201] Examples of the amine-based curing accelerator include trialkylamines such as triethylamine and tributylamine, 4-dimethylaminopyridine, benzyldimethylamine, 2,4,6-tris(dimethylaminomethyl)phenol, 1,8-diazabicyclo(5,4,0)undecene, etc., and 4-dimethylaminopyridine and 1,8-diazabicyclo(5,4,0)undecene are preferred.

[0202] Examples of imidazole-based curing accelerators include 2-methylimidazole, 2-undecylimidazole, 2-heptadecylimidazole, 1,2-dimethylimidazole, 2-ethyl-4-methylimidazole, 1,2-dimethylimidazole, 2-ethyl-4-methylimidazole, 2-phenylimidazole, 2-phenyl-4-methylimidazole, 1-benzyl-2-methylimidazole, 1-benzyl-2-phenylimidazole, 1-cyanoethyl-2-methylimidazole, 1-cyanoethyl-2-undecylimidazole, 1-cyanoethyl-2-ethyl-4-methylimidazole, 1-cyanoethyl-2-phenylimidazole, 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, 2-phenyl-4-methyl-5-hydroxymethylimidazole, 2,3-dihydro-1H-pyrrolo[1,2-a]benzimidazole, 1-dodecyl-2-methyl-3-benzylimidazolium chloride, 2-methylimidazoline, 2-phenylimidazoline and adducts of imidazole compounds and epoxy resins. 2-Ethyl-4-methylimidazole and 1-benzyl-2-phenylimidazole are preferred.

[0203] As the imidazole-based curing accelerator, commercially available products may be used. Examples include "P200-H50" manufactured by Mitsubishi Chemical Corporation and "1B2PZ" manufactured by Shikoku Kasei Kogyo Co., Ltd.

[0204] Examples of the guanidine-based 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, 1-(o-tolyl)biguanide, etc., and dicyandiamide and 1,5,7-triazabicyclo[4.4.0]dec-5-ene are preferred.

[0205] Examples of the metal-based curing accelerators include organometallic complexes or organometallic salts of metals such as cobalt, copper, zinc, iron, nickel, manganese, tin, etc. Specific examples of the organometallic complexes include organocobalt complexes such as cobalt(II) acetylacetonate and cobalt(III) acetylacetonate, organocopper complexes such as copper(II) acetylacetonate, organozinc complexes such as zinc(II) acetylacetonate, organoiron complexes such as iron(III) acetylacetonate, organonickel complexes such as nickel(II) acetylacetonate, organomanganese complexes such as manganese(II) acetylacetonate, etc. Examples of the organometallic salts include zinc octylate, tin octylate, zinc naphthenate, cobalt naphthenate, tin stearate, zinc stearate, etc.

[0206] The content of the component (G) in the resin composition is not particularly limited, but when the resin component in the resin composition is 100% by mass, it is preferably 0.1% by mass or more, more preferably 0.2% by mass or more, and preferably 2% by mass or less, more preferably 1% by mass or less.

[0207] [Other Additives] In addition to the above-described components, the resin composition of the present invention may further contain other additives as optional components. Examples of other additives include organometallic compounds such as organic copper compounds, organic zinc compounds, and organic cobalt 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-based leveling agents and acrylic polymer-based leveling agents; thickeners such as benton and montmorillonite; antifoaming agents such as silicone-based antifoaming agents, acrylic-based antifoaming agents, fluorine-based antifoaming agents, and vinyl resin-based antifoaming agents; ultraviolet absorbers such as benzotriazole-based ultraviolet absorbers; adhesion improvers such as urea silane; adhesion imparting agents such as triazole-based adhesion imparting agents, tetrazole-based adhesion imparting agents, and triazine-based adhesion imparting agents; 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, red phosphorus), nitrogen-based flame retardants (e.g., melamine sulfate), halogen-based flame retardants, and inorganic-based 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; stabilizers such as borate-based stabilizers, titanate-based stabilizers, aluminate-based stabilizers, zirconate-based stabilizers, isocyanate-based stabilizers, carboxylic acid-based stabilizers, and carboxylic anhydride-based stabilizers; photoinitiator aids such as tertiary amines; photosensitizers such as pyrazolones, anthracenes, coumarins, xanthones, and thioxanthones. These other additives may be used alone or in combination of two or more.

[0208] [Solvent] In addition to the non-volatile components described above, the resin composition of the present invention may contain a solvent as a volatile component. As the solvent, known solvents can be appropriately used, the type thereof is not particularly limited, and it is preferably an organic solvent. Examples of the solvent include ketone solvents such as acetone, methyl ethyl ketone, methyl isobutyl ketone, and cyclohexanone; ester solvents such as methyl acetate, ethyl acetate, butyl acetate, isobutyl acetate, isoamyl acetate, methyl propionate, ethyl propionate, and γ-butyrolactone; ether solvents such as tetrahydropyran, tetrahydrofuran, 1,4-dioxane, diethyl ether, diisopropyl ether, dibutyl ether, diphenyl ether, and anisole; alcohol solvents such as methanol, ethanol, propanol, butanol, and ethylene glycol; ether ester solvents such as 2-ethoxyethyl acetate, propylene glycol monomethyl ether acetate, diethylene glycol monoethyl ether acetate, ethyl diglycol acetate, γ-butyrolactone, and methyl methoxypropionate; ester alcohol solvents such as methyl lactate, ethyl lactate, and methyl 2-hydroxyisobutyrate; ether alcohol solvents such as 2-methoxypropanol, 2-methoxyethanol, 2-ethoxyethanol, propylene glycol monomethyl ether, and diethylene glycol monobutyl ether (butyl carbitol); amide solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, and N-methyl-2-pyrrolidone; sulfoxide solvents such as dimethyl sulfoxide; nitrile solvents such as acetonitrile and propionitrile; aliphatic hydrocarbon solvents such as hexane, cyclopentane, cyclohexane, and methylcyclohexane; aromatic hydrocarbon solvents such as benzene, toluene, xylene, ethylbenzene, and trimethylbenzene, etc. (J) The solvent may be used alone or in combination of two or more in any ratio.

[0209] The amount of the solvent is not particularly limited. When the total components in the resin composition are 100% by mass, for example, it may be 60% by mass or less, 40% by mass or less, 30% by mass or less, 20% by mass or less, 15% by mass or less, 10% by mass or less, etc., and may even be 0% by mass.

[0210] [Method for producing resin composition] The resin composition of the present invention can be produced, for example, by mixing the components that can be contained in the resin composition. The above-described components may be mixed partially or entirely simultaneously, or may be mixed in sequence. During the process of mixing each component, the temperature may be appropriately set, and thus, heating and / or cooling may be performed temporarily or throughout. Further, stirring or shaking may be performed during the process of mixing each component.

[0211] [Properties of resin composition] The cured product of the resin composition of the present invention can have a low dielectric tangent. Therefore, when an insulating layer is formed with this cured product, an insulating layer with a low dielectric tangent can be obtained. The dielectric tangent of the cured product of the resin composition is preferably 0.003 or less, more preferably 0.0028 or less, and even more preferably 0.0025 or less. The lower limit is not particularly limited, but can be 0.0001 or more, etc. The dielectric tangent can be measured by the method described in the examples below.

[0212] The cured product of the resin composition of the present invention exhibits the characteristic of having a high elongation at break. Therefore, when an insulating layer is formed with this cured product, an insulating layer with excellent mechanical strength can be obtained. The elongation at break of the cured product of the resin composition is preferably 1.4% or more, more preferably 1.5% or more, 1.6% or more, 1.8% or more, or 2% or more. The upper limit value is not particularly limited, but can be, for example, 10% or less, etc. The elongation at break can be measured by the method described in the examples below.

[0213] The cured product of the resin composition of the present invention exhibits the property of excellent crack resistance. Therefore, when an insulating layer is formed of this cured product, an insulating layer excellent in crack resistance can be obtained. Specifically, the resin composition is laminated on an inner layer substrate on which a wiring pattern is formed and thermally cured to obtain a cured product. The surface of the cured product is roughened to obtain a sample. In 100 portions on the pattern of the inner layer substrate of the sample, it is confirmed whether cracks are generated on the surface along the pattern shape, the number of portions on the pattern where cracks are not generated is counted, and the ratio of the portions where cracks are not generated among the 100 portions is calculated as the "yield". At this time, the yield is preferably 40% or more, more preferably 60% or more, and still more preferably 80% or more. The crack resistance can be measured by the method described in the examples described later.

[0214] [Use of Resin Composition] 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 insulating layer of printed wiring board), and can be more suitably used as a resin composition for forming an interlayer insulating layer of a printed wiring board (resin composition for interlayer insulating layer of printed wiring board). The resin composition of the present invention can also be suitably used when the printed wiring board is a component-mounted circuit board. The resin composition of the present invention can also be suitably used as a resin composition for forming an insulating layer of a redistribution substrate of a semiconductor package (resin composition for insulating layer of redistribution substrate). In the present invention, a printed wiring board and a redistribution substrate are collectively referred to as a "circuit board". Therefore, the resin composition of the present invention can be suitably used for the insulating layer of a circuit board.

[0215] The resin composition of the present invention can also be widely used in applications where a resin composition is required, such as resin sheets, sheet-like laminated materials such as prepregs, solder resists, underfill materials, die bonding materials, hole filling resins, encapsulating resins, component embedding resins, and the like.

[0216] [Sheet-like Laminated Material] The resin composition may be applied and used in a varnish state, but industrially, it is preferably used in the form of a sheet-like laminated material containing the resin composition.

[0217] As the sheet-like laminated material, the resin sheets and prepregs shown below are preferred.

[0218] In one embodiment, the resin sheet includes a support and a resin composition layer provided on the support. The resin composition layer is formed of the resin composition described above. Therefore, the resin composition layer usually contains the resin composition and preferably contains only the resin composition.

[0219] From the viewpoints of thinning and providing a cured product with excellent insulation even when thinned by the resin composition, the thickness of the resin composition layer is preferably 50 μm or less, more preferably 40 μm or less. The lower limit of the thickness of the resin composition layer is not particularly limited, but may be 5 μm or more, 10 μm or more, etc.

[0220] Examples of the support include a thermoplastic resin film, a metal foil, and a release paper, and a thermoplastic resin film and a metal foil are preferred.

[0221] When a thermoplastic resin film is used as the support, examples of the thermoplastic resin include polyesters such as polyethylene terephthalate (PET) and polyethylene naphthalate (PEN), acrylics such as polycarbonate (PC) and polymethyl methacrylate (PMMA), cyclic polyolefins, triacetyl cellulose (TAC), polyethersulfide (PES), polyether ketone, polyimide, etc. Among them, polyethylene terephthalate and polyethylene naphthalate are preferred, and inexpensive polyethylene terephthalate is particularly preferred.

[0222] When using a metal foil as the support, examples of the metal foil include, for example, copper foil, aluminum foil, etc., and copper foil is preferred. As the copper foil, a foil made of single metal copper may be used, or a foil made of an alloy of copper and other metals (for example, tin, chromium, silver, magnesium, nickel, zirconium, silicon, titanium, etc.) may be used.

[0223] The support may be subjected to matting treatment, corona treatment, or antistatic treatment on the surface that joins the resin composition layer.

[0224] As the support, a support with a release layer having a release layer on the surface that joins the resin composition layer may be used. Examples of the release agent used for the release layer of the support with a release layer include one or more release agents selected from the group consisting of alkyd resin, polyolefin resin, urethane resin, and silicone resin. As the support with a release layer, commercially available products may be used. For example, "SK-1", "AL-5", "AL-7" manufactured by Lintec Corporation, which are PET films having a release layer mainly composed of an alkyd resin-based release agent, "Lumirror T60" manufactured by Toray Industries, Inc., "Purex" manufactured by Teijin Limited, "Unipile" manufactured by Unitika Ltd., etc.

[0225] The thickness of the support is not particularly limited, but a range of 5 μm to 75 μm is preferred, and a range of 10 μm to 60 μm is more preferred. When using a support with a release layer, it is preferable that the total thickness of the support with a release layer is within the above range.

[0226] When using a metal foil as the support, a metal foil with a support substrate laminated on a thin metal foil that can be peeled off may be used. 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 using a metal foil with a support substrate as the support, the resin composition layer is provided on the metal foil.

[0227] In the metal foil with a support substrate, the material of the support substrate is not particularly limited, and examples thereof include copper foil, aluminum foil, stainless steel foil, titanium foil, copper alloy foil, and the like. When using copper foil as the support substrate, it may be an electrolytic copper foil or a rolled copper foil. Further, the release layer is not particularly limited as long as the metal foil can be peeled from the support 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 film, and the like.

[0228] In the metal foil with a support substrate, as the material of the metal foil, for example, copper foil and copper alloy foil are preferable.

[0229] In the metal foil with a support substrate, the thickness of the support substrate is not particularly limited, but the range of 10 μm to 150 μm is preferable, and the range of 10 μm to 100 μm is more preferable. Further, the thickness of the metal foil may be, for example, in the range of 0.1 μm to 10 μm.

[0230] In one embodiment, the resin sheet may further include an arbitrary layer as needed. Examples of such an arbitrary layer include a protective film similar to the support provided on the surface of the resin composition layer that is not joined to the support (that is, the surface opposite to the support). The thickness of the protective film is not particularly limited, but is, for example, 1 μm to 40 μm. By laminating the protective film, it is possible to suppress the adhesion of dust and scratches to the surface of the resin composition layer.

[0231] The resin sheet can be produced, for example, by directly using a liquid (varnish-like) resin composition or by dissolving the resin composition in a solvent to prepare a liquid (varnish-like) resin composition, applying this onto a support using a die coater or the like, and further drying to form a resin composition layer.

[0232] Examples of the solvent include the same solvents as those described as components of the resin composition. The solvent may be used alone or in combination of two or more.

[0233] Drying may be carried out by methods such as heating and hot air blowing. The drying conditions are not particularly limited, but the drying is carried out so that the content of the solvent in the resin composition layer is usually 10% by mass or less, preferably 5% by mass or less. Although it varies depending on the boiling point of the solvent in the resin composition, for example, when using a resin composition containing 30% to 60% by mass of the solvent, the resin composition layer can be formed by drying at 50°C to 150°C for 3 minutes to 10 minutes.

[0234] The resin sheet can be wound up and stored in a roll shape. When the resin sheet has a protective film, it can usually be used by peeling off the protective film.

[0235] In one embodiment, the prepreg is formed by impregnating a sheet-like fiber base material with the resin composition according to this embodiment.

[0236] As the sheet-like fiber base material used for the prepreg, for example, those commonly used as prepreg base materials such as glass cloth, aramid non-woven fabric, and liquid crystal polymer non-woven fabric can be used. From the viewpoint of thinning, the thickness of the sheet-like fiber base material is preferably 50 μm or less, more preferably 40 μm or less, still more preferably 30 μm or less, and particularly preferably 20 μm or less. The lower limit of the thickness of the sheet-like fiber base material is not particularly limited and is usually 10 μm or more.

[0237] The prepreg can be manufactured by methods such as the hot melt method and the solvent method.

[0238] The thickness of the prepreg can be in the same range as the resin composition layer in the resin sheet described above.

[0239] The sheet-like laminated material can be suitably used for forming the insulating layer of a printed wiring board (for the insulating layer of a printed wiring board), and can be more suitably used for forming the interlayer insulating layer of a printed wiring board (for the interlayer insulating layer of a printed wiring board). The sheet-like laminated material of the present invention can also be suitably used for forming the insulating layer of a redistribution substrate of a semiconductor package (for the insulating layer of a redistribution substrate). That is, the sheet-like laminated material of the present invention can be suitably used as the insulating layer of a circuit board.

[0240] [Circuit board] The insulating layer of a circuit board can be formed using the resin composition of the present invention. The present invention also provides such a circuit board, that is, a circuit board including an insulating layer made of a cured product of the resin composition of the present invention.

[0241] [Printed wiring board] In one embodiment, the circuit board of the present invention is a printed wiring board.

[0242] The printed wiring board can be manufactured, for example, by a method including the following steps (I) and (II) using the above resin sheet. (I) A step of laminating a resin sheet on an inner layer substrate so that the resin composition layer of the resin sheet is joined to the inner layer substrate (II) A step of curing (for example, thermally curing) the resin composition layer to form an insulating layer

[0243] The "inner layer substrate" used in step (I) is a member serving as the substrate of a printed wiring board. Examples thereof include glass epoxy substrates, metal substrates, polyester substrates, polyimide substrates, BT resin substrates, thermosetting polyphenylene ether substrates, and the like. Further, the substrate may have a conductor layer on one or both of its surfaces, and this conductor layer may be pattern-processed. An inner layer substrate having a conductor layer (circuit) formed on one or both surfaces of the substrate may be referred to as an "inner layer circuit board". Further, in the production of a printed wiring board, an intermediate product on which an insulating layer and / or a conductor layer is to be further formed is also included in the "inner layer substrate" as referred to in the present invention. When the printed wiring board is a circuit board with built-in components, an inner layer substrate with built-in components may be used.

[0244] The lamination of the inner layer substrate and the resin sheet can be carried out, for example, by thermocompression bonding the resin sheet to the inner layer substrate from the support side. Examples of the member for thermocompression bonding the resin sheet to the inner layer substrate (hereinafter also referred to as the "thermocompression bonding member") include a heated metal plate (such as a SUS mirror plate) or a metal roll (SUS roll). Note that the thermocompression bonding member may be pressed directly against the resin sheet, or may be pressed via an elastic material such as heat-resistant rubber so that the resin sheet sufficiently follows the surface unevenness of the inner layer substrate.

[0245] 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 bonding temperature is preferably in the range of 60°C to 160°C, more preferably in the range of 80°C to 140°C, the thermocompression bonding pressure is preferably in the range of 0.098 MPa to 1.77 MPa, more preferably in the range of 0.29 MPa to 1.47 MPa, and the thermocompression bonding time is preferably in the range of 20 seconds to 400 seconds, more preferably in the range of 30 seconds to 300 seconds. The lamination can preferably be carried out under reduced pressure conditions of a pressure of 26.7 hPa or less.

[0246] The lamination can be carried out using a commercially available vacuum laminator. Examples of commercially available vacuum laminators include a vacuum pressure type laminator manufactured by Meiki Seisakusho Co., Ltd., a vacuum applicator manufactured by Nichco Materials Co., Ltd., a batch type vacuum pressure laminator, and the like.

[0247] After lamination, under normal pressure (atmospheric pressure), for example, by pressing a heat-bonding member from the support side, a smoothing process of the laminated resin sheet may be performed. The pressing conditions for the smoothing process can be the same as the heat-bonding conditions for the above lamination. The smoothing process can be performed by a commercially available laminator. Note that the lamination and the smoothing process may be continuously performed using the above-mentioned commercially available vacuum laminator.

[0248] The support may be removed between step (I) and step (II), or may be removed after step (II). Note that when a metal foil is used as the support, a conductor layer may be formed using the metal foil without peeling the support. Also, when a metal foil with a support substrate is used as the support, the support substrate (and the release layer) may be peeled off. And a conductor layer can be formed using the metal foil.

[0249] In step (II), the resin composition layer is cured (for example, thermally cured) to form an insulating layer made of a cured product of the resin composition. The curing conditions of the resin composition layer are not particularly limited, and the conditions usually employed when forming an insulating layer of a printed wiring board may be used.

[0250] For example, the thermal curing conditions of the resin composition layer vary depending on the type of the resin composition and the like. In one embodiment, the curing temperature is preferably 140°C to 250°C, more preferably 150°C to 240°C, and even more preferably 160°C to 230°C. The curing time can be preferably 5 minutes to 240 minutes, more preferably 10 minutes to 150 minutes, and even more preferably 15 minutes to 120 minutes.

[0251] 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.

[0252] When manufacturing a printed wiring board, the steps of (III) drilling holes in the insulating layer, (IV) roughening the insulating layer, and (V) forming the conductor layer may be further performed. These steps (III) to (V) may be performed according to various methods known to those skilled in the art used for manufacturing printed wiring boards. When removing the support after step (II), the removal of the support may be performed between step (II) and step (III), between step (III) and step (IV), or between step (IV) and step (V). Further, if necessary, the formation of the insulating layer and the conductor layer in steps (I) to (V) may be repeatedly performed to form a multilayer wiring board.

[0253] In another embodiment, the printed wiring board of the present invention can be manufactured using the above-described prepreg. The manufacturing method is basically the same as the case of using a resin sheet.

[0254] Step (III) is a step of drilling holes in the insulating layer, whereby holes such as via holes and through holes can be formed in the insulating layer. Step (III) may be performed using, for example, a drill, a laser, a plasma, etc., according to the composition of the resin composition used for forming the insulating layer. The dimensions and shapes of the holes may be appropriately determined according to the design of the printed wiring board.

[0255] Step (IV) is a step of roughening the insulating layer. Usually, in this step (IV), removal of smear (desmear) is also performed. The procedures and conditions for the roughening treatment are not particularly limited, and known procedures and conditions usually used when forming the insulating layer of a printed wiring board 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.

[0256] The swelling liquid used for the roughening treatment is not particularly limited, and examples thereof include an alkaline solution and a surfactant solution. An alkaline solution is preferable, and as the alkaline solution, a sodium hydroxide solution and a potassium hydroxide solution are more preferable. Examples of commercially available swelling liquids include "Swelling Dip·Security Gun P" and "Swelling Dip·Security Gun SBU" manufactured by Atotech Japan Co., Ltd. The swelling treatment with the swelling liquid is not particularly limited, but for example, it can be performed by immersing the insulating layer in the swelling liquid at 30°C to 90°C for 1 minute to 20 minutes. From the viewpoint of suppressing the swelling of the resin of the insulating layer to an appropriate level, it is preferable to immerse the insulating layer in the swelling liquid at 40°C to 80°C for 5 minutes to 15 minutes.

[0257] The oxidizing agent used for the roughening treatment is not particularly limited, and examples thereof include an alkaline permanganate solution in which potassium permanganate or sodium permanganate is dissolved in an aqueous solution of sodium hydroxide. The roughening treatment with an oxidizing agent such as an alkaline permanganate solution is preferably performed by immersing the insulating layer in the oxidizing agent solution heated to 60°C to 100°C for 10 minutes to 30 minutes. Further, the concentration of the permanganate in the alkaline permanganate solution is preferably 5% by mass to 10% by mass. Examples of commercially available oxidizing agents include alkaline permanganate solutions such as "Concentrate·Compact CP", "Concentrate·Compact P", and "Dosing Solution·Security Gun P" manufactured by Atotech Japan Co., Ltd.

[0258] Further, as the neutralizing liquid used for the roughening treatment, an acidic aqueous solution is preferable, and examples of commercially available products include "Reduction Solution·Security T P" manufactured by Atotech Japan Co., Ltd.

[0259] The treatment with the neutralizing liquid can be performed by immersing the treated surface, which has been roughened with the oxidizing agent, in the neutralizing liquid at 30°C to 80°C for 5 minutes to 30 minutes. From the viewpoint of workability and the like, a method of immersing the object roughened with the oxidizing agent in the neutralizing liquid at 40°C to 70°C for 5 minutes to 20 minutes is preferable.

[0260] 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 the alloy layer include layers formed from alloys of two or more metals selected from the above group (for example, nickel-chromium alloy, copper-nickel alloy, and copper-titanium alloy). Among them, from the viewpoints of versatility, cost, ease of patterning, etc. of conductor layer formation, a single-metal layer of chromium, nickel, titanium, aluminum, zinc, gold, palladium, silver, or copper, or an alloy layer of nickel-chromium alloy, copper-nickel alloy, or 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 nickel-chromium alloy is more preferred, and a single-metal layer of copper is even more preferred.

[0261] The conductor layer may have a single-layer structure or a multilayer 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 multilayer structure, the layer in contact with the insulating layer is preferably a single-metal layer of chromium, zinc, or titanium, or an alloy layer of nickel-chromium alloy.

[0262] The thickness of the conductor layer depends on the design of the desired printed wiring board, but is generally 3 μm to 35 μm, preferably 5 μm to 30 μm.

[0263] In one embodiment, the conductor layer may be formed by plating. From the viewpoint of easy formation of fine wiring, it is preferably formed by the semi-additive method. Hereinafter, an example of forming the conductor layer by the semi-additive method is shown.

[0264] First, a plating seed layer is formed on the surface of the insulating layer by electroless plating. Next, a mask pattern is formed on the formed plating seed layer to expose a part of the plating seed layer corresponding to a desired wiring pattern. After forming a metal layer by electrolytic plating on the exposed plating seed layer, the mask pattern is removed. Thereafter, an unnecessary plating seed layer can be removed by etching or the like to form a conductor layer having a desired wiring pattern.

[0265] In another embodiment, the conductor layer may be formed using a metal foil. When forming the conductor layer using a metal foil, step (V) is preferably carried out between step (I) and step (II). For example, after step (I), the support is removed, and a metal foil is laminated on the surface of the exposed resin composition layer. The lamination of the resin composition layer and the metal foil may be carried out by a vacuum lamination method. The lamination conditions may be the same as those described for step (I). Next, step (II) is carried out to form an insulating layer. Thereafter, using the metal foil on the insulating layer, a conductor layer having a desired wiring pattern can be formed by a conventionally known technique such as the modified semi-additive method.

[0266] The metal foil can be manufactured by a known method such as an electrolytic method or a rolling method. Examples of commercially available metal foils include HLP foil manufactured by JX Metals, JXUT-III foil, 3EC-III foil manufactured by Mitsui Mining & Smelting Co., Ltd., and TP-III foil.

[0267] Alternatively, as described above, when a metal foil or a metal foil with a support substrate is used as the support of the resin sheet, the conductor layer may be formed using the metal foil.

[0268] <Redistribution Substrate of Semiconductor Package> In one embodiment, the circuit board of the present invention is a redistribution substrate (redistribution layer) of a semiconductor package. Hereinafter, it will be described in accordance with the manufacturing method of the semiconductor package.

[0269] 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 the redistribution substrate. Note that the semiconductor package may include a sealing layer made of a cured product of the resin composition of the present invention.

[0270] The semiconductor package can be manufactured, 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 may be used to form the redistribution formation layer (insulating layer for forming the redistribution substrate) in step (5) or the sealing layer in step (3). Hereinafter, an example of forming the redistribution formation layer and the sealing layer using the resin composition and resin sheet is shown. However, the technology for forming the redistribution formation layer and the sealing layer of the semiconductor package is known, and those skilled in the art can manufacture the semiconductor package according to the known technology using the resin composition and resin sheet of the present invention. (1) Step of laminating a temporary fixing film on a base material (2) Step of temporarily fixing a semiconductor chip on the temporary fixing film (3) Step of forming a sealing layer on the semiconductor chip (4) Step of peeling the base material and the temporary fixing film from the semiconductor chip (5) Step of forming a redistribution formation layer as an insulating layer on the surface of the base material and the temporary fixing film of the semiconductor chip from which they have been peeled, and (6) Step of forming a redistribution layer as a conductor layer on the redistribution formation layer

[0271] - Step (1) - The material used for the base material is not particularly limited. Examples of the base material 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 impregnated with epoxy resin or the like in glass fibers and subjected to thermosetting treatment (for example, FR-4 substrates); substrates made of bismaleimide triazine resin (BT resin), and the like.

[0272] The temporary fixing film can be peeled off from the semiconductor chip in step (4), and the material is not particularly limited as long as it can temporarily fix the semiconductor chip. A commercially available product can be used as the temporary fixing film. Examples of commercially available products include Rivar Alpha manufactured by Nitto Denko Corporation.

[0273] - Step (2)- The temporary fixing of the semiconductor chip can be performed using a known apparatus such as a flip chip bonder or a die bonder. The layout and the number of arrangements of the semiconductor chips can be appropriately set according to the shape and size of the temporary fixing film, the production number of the target semiconductor package, etc. For example, they can be temporarily fixed by aligning them in a matrix form with multiple rows and multiple columns.

[0274] - Step (3)- The resin composition layer of the resin sheet of the present invention is laminated on the semiconductor chip, or the resin composition of the present invention is applied on the semiconductor chip and cured (for example, thermally cured) to form a sealing layer.

[0275] For example, the lamination of the semiconductor chip and the resin sheet can be performed by removing the protective film of the resin sheet and then thermocompression bonding the resin sheet to the semiconductor chip from the support side. Examples of the member for thermocompression bonding the resin sheet to the semiconductor chip (hereinafter also referred to as "thermocompression bonding member") include a heated metal plate (such as a SUS mirror plate) or a metal roll (SUS roll). It is preferable to press through an elastic material such as heat-resistant rubber so that the resin sheet can sufficiently follow the surface unevenness of the semiconductor chip instead of pressing the thermocompression bonding member directly against the resin sheet. The lamination of the semiconductor chip and the resin sheet may be carried out by the vacuum lamination method, and the lamination conditions are the same as the lamination conditions described in relation to the manufacturing method of the printed wiring board, and the preferable ranges are also the same.

[0276] After the lamination, the resin composition is thermally cured to form a sealing layer. The thermal curing conditions are the same as the thermal curing conditions described in relation to the manufacturing method of the printed wiring board.

[0277] The support of the resin sheet may be peeled off after laminating and thermosetting the resin sheet on the semiconductor chip, or the support may be peeled off before laminating the resin sheet on the semiconductor chip.

[0278] When forming the sealing layer by applying the resin composition of the present invention, the coating conditions are the same as those for forming the resin composition layer described in relation to the resin sheet of the present invention, and the preferable ranges are also the same.

[0279] - Step (4)- The method of peeling the base material and the temporary fixing film can be appropriately changed according to the material of the temporary fixing film, etc. For example, methods such as heating and foaming (or expanding) the temporary fixing film to peel it off, and irradiating ultraviolet rays from the base material side to reduce the adhesive force of the temporary fixing film and peel it off can be mentioned.

[0280] 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. Also, in the method of irradiating ultraviolet rays from the base material side to reduce the adhesive force of the temporary fixing film and peel it off, the irradiation amount of ultraviolet rays is usually 10 mJ / cm 2 ~1000 mJ / cm 2 is.

[0281] - Step (5)- The resin composition and resin sheet of the present invention are used to form a redistribution formation layer (insulating layer of the redistribution substrate).

[0282] After forming the redistribution formation layer, in order to layer-connect the semiconductor chip and the conductor layer described later, via holes may be formed in the redistribution formation layer. The via holes may be formed by a known method according to the material of the redistribution formation layer.

[0283] - Step (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 manufacturing 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).

[0284] In manufacturing a semiconductor package, (7) a step of forming a solder resist layer on the conductor layer (rewiring layer), (8) a step of forming bumps, and (9) a step of dicing and singulating a plurality of semiconductor packages into individual semiconductor packages may be further carried out. These steps may be carried out according to various methods known to those skilled in the art used for manufacturing semiconductor packages.

[0285] By forming a rewiring formation layer (insulating layer) using the resin composition and resin sheet of the present invention, which can provide a cured product exhibiting good dielectric properties, good mechanical properties, and crack resistance, a semiconductor package with extremely low transmission loss can be realized without concern about cracks, regardless of whether it is a Fan-In type package or a Fan-Out type package. In one embodiment, the semiconductor package of the present invention is a Fan-Out type package. The resin composition and resin sheet of the present invention can be applied regardless of whether it is a Fan-Out panel level package (FOPLP) or 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).

[0286] [Semiconductor device] 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 manufactured using the circuit board of the present invention.

[0287] Examples of semiconductor devices include various semiconductor devices used in electrical products (such as computers, mobile phones, smartphones, tablet devices, wearable devices, digital cameras, medical devices, and televisions, etc.) and vehicles (such as motorcycles, automobiles, trains, ships, and aircraft, etc.).

Example

[0288] Hereinafter, the present invention will be specifically described with reference to examples. However, the present invention is not limited to the following examples. In the following description, "parts" and "%" representing amounts mean "parts by mass" and "mass %", respectively, unless otherwise specified. The temperature conditions and pressure conditions in the case where no temperature is specified are room temperature (25 °C) and atmospheric pressure (1 atm).

[0289] (Synthesis Example 1: Synthesis of Resin A) 10 g of 4,4'-methylenebis(2,6-dimethylphenol) was dissolved in 390 mL of tetrahydrofuran, 15 g of 3-bromo-1-phenyl-1-propene was added, and the mixture was cooled to 0 °C. 3.4 g of sodium hydride was added, and the mixture was stirred at room temperature overnight under a nitrogen gas atmosphere. Water was added to the reaction mixture, tetrahydrofuran was removed by concentration under reduced pressure, dichloromethane was added, and the organic layer was washed with water and saturated brine, and dried over anhydrous sodium sulfate. After filtering off the desiccant, the mixture was concentrated under reduced pressure to obtain 15 g of the target resin A as white crystals. This resin A has a structure represented by the following formula.

[0290]

Chemical formula

[0291] (Synthesis Example 2: Synthesis of Maleimide B) A MEK solution (non-volatile component 70 mass %) of maleimide B (Mw / Mn = 1.81, t'' = 1.47 (mainly 1, 2 or 3)) synthesized by the method described in Synthesis Example 1 of JP-A-2020-500211 was prepared. This maleimide B has a structure represented by the following formula.

Chemical formula

[0292] (Synthesis Example 3: Synthesis of Vinyl Resin C) 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, followed by reacting for 4 hours. After terminating the polymerization solution with an aqueous sodium hydrogen carbonate solution, the oil layer was washed three times with pure water, and volatile components were removed under reduced pressure at 60°C to recover the polymer. The obtained product was weighed, and it was confirmed that 896.7 g of vinyl resin C was obtained. The weight average molecular weight (Mw) of vinyl resin C was 41,300.

[0293] (Examples 1 to 13, Comparative Examples 1 to 3) (Preparation of Resin Varnish) Each component was weighed in the parts by mass described in Table 1, and further 10 parts of MEK and 2 parts of cyclohexanone were mixed and uniformly dispersed using a high-speed rotary mixer to obtain a resin varnish.

[0294] [Table 1]

[0295] The details of each component described in Table 1 are as follows. (A) Compound Represented by Formula (A-1) · Resin A: The one synthesized in Synthesis Example 1 (B) Maleimide Resin · MIR-3000-70MT: Toluene solution with a functional group equivalent of 275 and a non-volatile content of 70% by mass, manufactured by Nippon Kayaku Co., Ltd. · Maleimide B: The one synthesized in Synthesis Example 2 · SLK-6895-T90: Toluene solution with a functional group equivalent of 345 and a non-volatile content of 90% by mass, manufactured by Shin-Etsu Chemical Co., Ltd. (C) Thermosetting Resin · LA-3018-50P: 1-methoxy-2-propanol solution with a functional group equivalent of 151 and a non-volatile content of 50% by mass, manufactured by DIC Corporation · HP-4032-SS: Functional group equivalent 144, manufactured by DIC Corporation · HPC-8000-65T: Toluene solution with a functional group equivalent of 223 and a non-volatile content of 62%, manufactured by DIC Corporation · V-03: Toluene solution with a functional group equivalent of 216 and a non-volatile content of 50% by mass, manufactured by Nisshinbo Chemicals, Inc. · DAD: Functional group equivalent 161, manufactured by Nippon Shokubai Fine Chemical Co., Ltd. · Vinyl resin C: Toluene solution (non-volatile component 50% by mass) synthesized in Synthesis Example 3 · OPE-2St: Toluene solution with a functional group equivalent of 590 and a non-volatile content of 65% by mass, manufactured by Mitsubishi Gas Chemical Company, Inc. (D) Thermoplastic resin · P2000: Styrene-butadiene elastomer, manufactured by Asahi Kasei Corporation · PIAD200: Polyimide resin, a mixed solution of cyclohexanone, dimethyl glycol, and methylcyclohexane with a non-volatile content of 30%, manufactured by Arakawa Chemical Industries, Ltd. · YX7553BH30: Phenoxy resin, a 1:1 solution of MEK and cyclohexanone with a non-volatile content of 30% by mass, manufactured by Mitsubishi Chemical Corporation (E) Inorganic filler · SO-C2: Spherical silica surface-treated with an amine-based alkoxysilane compound (Shin-Etsu Chemical Co., Ltd.'s "KBM573"), average particle size 0.5 μm, specific surface area 5.8 m 2 / g, manufactured by Admatechs Co., Ltd. (F) Radical polymerization initiator · Perhexyne D: Manufactured by NOF Corporation (G) Curing accelerator · 1B2PZ: Manufactured by Shikoku Kasei Kogyo Co., Ltd.

[0296] [[Test Example 1: Measurement of Dielectric Dissipation Factor (Df)]] (1) Preparation of resin sheet A with a resin composition layer thickness of 40 μm As the support, a polyethylene terephthalate film with a release layer (「AL5」manufactured by Lintec Corporation, thickness 38 μm) was prepared. Onto the release layer of this support, the varnish-like resin compositions obtained in the examples and comparative examples were uniformly applied such that the thickness of the resin composition layer after drying would be 40 μm. Thereafter, the resin composition was dried at 80°C to 100°C (average 90°C) for 2 minutes to obtain a resin sheet A including the support and the resin composition layer. (2) Preparation of the cured product The obtained resin sheet A was cured in an oven at 190°C for 90 minutes. By peeling off the support from the resin sheet A taken out of the oven, a cured product of the resin composition layer was obtained. (3) Measurement of the dielectric dissipation factor (Df) The cured product was cut out into pieces 80 mm long and 2 mm wide, and using 「HP8362B」manufactured by Agilent Technologies, the value of the dielectric dissipation factor (Df value) was measured at a measurement frequency of 5.8 GHz, measurement temperatures of 23°C and 90°C by the cavity resonance perturbation method. The measurement was carried out on two test pieces, and the average was calculated.

[0297] <Test Example 2: Measurement of the elongation at break point> Using a tensile testing machine 「RTC-1250A」manufactured by Orientec Corporation, the tensile strength of the cured product obtained in Test Example 1(2) was measured, and the strength at break point and the elongation at break point at 23°C were measured. The measurement was carried out in accordance with JIS K7127. The measurement was carried out 5 times, and the average value of the top 3 points was calculated.

[0298] <Test Example 3: Evaluation of crack resistance> (1) Lamination of the resin sheet An inner layer substrate (「MCL-E700G」manufactured by Resonac Corporation, conductor layer thickness 35 μm, total thickness 0.4 mm, residual copper rate 40%) having circuit conductors (copper) with a wiring pattern of L / S = 8 μm / 8 μm formed on both sides was prepared. Onto both sides of this inner layer substrate, a resin sheet was laminated such that the resin composition layer would be in contact with the inner layer substrate. Such lamination was carried out using a vacuum pressure laminator (「MVLP-500」manufactured by Meiki Seisakusho Co., Ltd.), with vacuum suction at a temperature of 120°C for 30 seconds, followed by a temperature of 120°C and a pressure of 7.0 kg / cm 2Under the conditions, it was carried out by pressing for 30 seconds from above the support through a heat-resistant rubber. Next, under atmospheric pressure, using a SUS mirror plate, at a temperature of 120 °C and a pressure of 5.5 kg / cm 2 pressing was carried out for 60 seconds under the conditions. (2) Thermosetting of the resin composition layer It was heated at 130 °C for 30 minutes, and then heated at 170 °C for 30 minutes to thermoset the resin composition layer, and an insulating layer as a cured layer composed of a cured product of the resin composition was obtained. Then, the support was peeled off to obtain a sample substrate having a layer structure of insulating layer / inner layer substrate / insulating layer. (3) Roughening treatment The insulating layer of the sample substrate was subjected to a roughening treatment. Specifically, the sample substrate was immersed in Swelling Dip & Securigant P manufactured by Atotech Japan Co., Ltd., which is a swelling liquid, at 60 °C for 10 minutes. Next, it was immersed in Concentrate Compact P manufactured by Atotech Japan Co., Ltd., which is a roughening liquid (aqueous solution of KMnO4: 60 g / L, NaOH: 40 g / L), at 80 °C for 20 minutes. Finally, it was immersed in Reduction Solution & Securigant P manufactured by Atotech Japan Co., Ltd., which is a neutralizing liquid, at 40 °C for 5 minutes. (4) Evaluation of cracks Among the surfaces of the insulating layer after the roughening treatment, the portion on the L / S pattern of the inner layer substrate was observed. It was confirmed whether cracks (fissures) occurred on the surface along the pattern shapes of 100 inner layer substrates, and the ratio of the number of portions on the patterns where cracks did not occur was counted. This ratio was calculated as the "yield". Also, the calculated yield was scored according to the following criteria. 1 point: 0% or more and less than 20%. 2 points: 20% or more and less than 40%. 3 points: 40% or more and less than 60%. 4 points: 60% or more and less than 80%. 5 points: 80% or more. Evaluation was made with 4 points or more as ◎, 3 points as "○", and 2 points or less as "×".

Claims

1. (A) A compound represented by the following formula (A-1): 【Chemical 1】 (In formula (A-1), X represents a divalent group represented by the following formula (A-2) or a divalent group represented by the following formula (A-3).) [Chemical Formula 2] (In formula (A-2), R １１ and R １２ each independently represents a divalent aromatic group which may have a substituent, L １１ each independently represents a single bond or a divalent linking group which may have a substituent, R １１ and L １１ may combine together to form a ring. a represents a number in the range of 0 to 5.) 【Chemical Formula 3】 (In formula (A-3), R １３ 、and R １４ each independently represents a divalent aromatic group which may have a substituent, L １２ represents a group represented by the formula (A-4). b and c each independently represent a number in the range of 0 to 5.) 【Chemical 4】 (In formula (A-4), R １５ and R １６ each independently represents a divalent aromatic group which may have a substituent L １３ each independently represents a single bond or a divalent linking group which may have a substituent, R １５ and L １３ may combine together to form a ring. d represents a number in the range of 0 to 5.), (B) A maleimide resin, and (C) A thermosetting resin (excluding maleimide resin) A resin composition containing the same.

2. In formula (A-2) and formula (A-3), R １１ , R １２ , R １３ , and R １４ each independently represents a phenylene group which may have a substituent or a naphthylene group which may have a substituent, the resin composition according to claim 1.

3. R in formula (A-4) １５ , and R １６ each independently represents a phenylene group which may have a substituent or a naphthylene group which may have a substituent. The resin composition according to claim 1

4. L in formula (A-2) １１ The resin composition according to claim 1, wherein each independently represents a single bond, a divalent aliphatic group which may have a substituent, an oxygen atom, a divalent aromatic group which may have a substituent, a carbonyl group, and a sulfonyl group.

5. L in formula (A-2) １１ The resin composition according to claim 1, wherein each independently represents a single bond, a divalent aliphatic group which may have a substituent, an oxygen atom, a phenylene group, a fluorenylidene group, a carbonyl group, or a sulfonyl group.

6. The resin composition according to claim 1, wherein X in formula (A-1) is a group represented by the following formula (A-5). 【Chemical Formula 5】 (In formula (A-5), Rs each independently represent a substituent, L ２１ each independently represents a single bond, a divalent aliphatic group which may have a substituent, an oxygen atom, a phenylene group, a fluorenylidene group, a carbonyl group, or a sulfonyl group, where L ２１ when it is a divalent aliphatic group which may have a substituent, L ２１ and the benzene ring on the left side may combine together to form a ring n1 and n2 each independently represent a number in the range of 0 to 4, m represents a number in the range of 0 to 5, "*" represents a bond.)

7. The resin composition according to claim 1, wherein when the resin components in the resin composition are 100% by mass, the content of component (A) is 2% by mass or more and 12% by mass or less.

8. The resin composition according to claim 1, wherein when the resin components in the resin composition are 100% by mass, the content of component (B) is 20% by mass or more and 75% by mass or less.

9. The resin composition according to any one of claims 1 to 8, wherein component (C) includes one or more selected from the group consisting of an epoxy resin, a phenol resin, and a terminal double bond resin.

10. The resin composition according to claim 1, wherein when the resin components in the resin composition are 100% by mass, the content of component (C) is 10% by mass or more and 50% by mass or less.

11. The resin composition according to claim 1, further containing (D) a thermoplastic resin.

12. The resin composition according to claim 1, further containing (E) an inorganic filler.

13. The resin composition according to claim 12, wherein when the non-volatile components in the resin composition are 100% by mass, the content of component (E) is 50% by mass or more.

14. The resin composition according to any one of claims 1 to 13, which is for an insulating layer of a circuit board.

15. A cured product of the resin composition according to any one of claims 1 to 13.

16. A resin sheet including a support and a layer of the resin composition according to any one of claims 1 to 13 provided on the support.

17. The resin sheet according to claim 16, wherein the support is a thermoplastic resin film or a metal foil.

18. A circuit board including an insulating layer made of a cured product of the resin composition according to any one of claims 1 to 13.

19. A semiconductor device including the circuit board according to claim 18.

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