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, and a cured product, a resin sheet, a circuit board, and a semiconductor device obtained using the resin composition. [Background technology]

[0002] Circuit boards such as printed wiring boards and rewiring boards for semiconductor chip packages are provided with insulating layers. In general, insulating layers are formed by curing a resin composition. Insulating layers for circuit boards are required to exhibit good dielectric properties (low dielectric constant, low dielectric dissipation factor) to reduce transmission loss when operating in a high-frequency environment. As a resin material that provides a cured product exhibiting 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] Japanese Patent Application Laid-Open No. 2012-116941 Summary of the Invention [Problem to be solved by the invention]

[0004] As disclosed in Patent Document 1, resin compositions containing maleimide resins generally produce cured products exhibiting good dielectric properties, but tend to be prone to cracking after desmearing. Furthermore, because maleimide resins usually have a high softening point, cured products of resin compositions containing maleimide resins tend to be brittle and have poor mechanical properties.

[0005] An object of the present invention is to provide a resin composition that can give a cured product that exhibits good dielectric properties and good mechanical properties, specifically high elongation at break and excellent crack resistance, as well as a cured product obtained using the resin composition, and a resin sheet, circuit board, and semiconductor device that each contain the resin composition. [Means for solving the problem]

[0006] The present inventors have conducted extensive research to solve the above-mentioned problems, and as a result, have found that the above-mentioned problems can be solved by a resin composition containing, in combination with a maleimide resin, a compound having a specific structure and a thermosetting resin other than a maleimide resin, and have completed the present invention. That is, the present invention includes the following.

[0007] [1] (A) Compound A represented by the following formula (A-1): [ka] (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): [ka] (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 be joined together to form a ring. a represents a number ranging from 0 to 5. [ka] (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 formula (A-4). b and c each independently represent a number ranging from 0 to 5. [ka] (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 be joined together to form a ring. d represents a number ranging from 0 to 5. (B) a maleimide resin, and (C) Thermosetting resins (excluding maleimide resins) A resin composition comprising: [2] R in formula (A-2) and formula (A-3) 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. [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. [4] L in formula (A-2) 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. [5] L in formula (A-2) 11 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.

[0022] 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): [ka] (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, and 21 When L is a divalent aliphatic group which may have a substituent, 21 and the benzene ring on the left may be bonded together to form a ring, n1 and n2 each independently represent a number ranging from 0 to 4, m represents a number ranging from 0 to 5; "*" represents a bond.) [7] The resin composition according to any one of [1] to [6], wherein the content of component (A) is 2% by mass or more and 12% by mass or less when the resin component in the resin composition is 100% by mass. [8] The resin composition according to any one of [1] to [7], wherein the content of component (B) is 20% by mass or more and 75% by mass or less when the resin component in the resin composition is 100% by mass. [9] The resin composition according to any one of [1] to [8], wherein the component (C) comprises at least one resin selected from the group consisting of epoxy resins, phenolic resins, and terminal double bond resins.

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

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

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

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

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

[13] The resin composition according to

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

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

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

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

[13] .

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

[13] .

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

[18] . [Effects of the Invention]

[0008] The resin composition of the present invention can provide a resin composition that can give a cured product that exhibits good dielectric properties and good mechanical properties, specifically high elongation at break and excellent crack resistance, as well as a cured product, resin sheet, circuit board, and semiconductor device obtained using the resin composition. DETAILED DESCRIPTION OF THE INVENTION

[0009] The present invention will be described below with reference to embodiments and examples. However, the present invention is not limited to the embodiments and examples shown below, and can be implemented with any modifications within the scope of the claims and their equivalents.

[0010] As used herein, the term "optionally substituted" in reference to a compound or group means both a case where the hydrogen atoms of the compound or group are not substituted with substituents, and a case where some or all of the hydrogen atoms of the compound or group are substituted with substituents.

[0011] In this specification, unless otherwise specified, the term "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, or an oxo group.

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

[0013] The alkyl group used as a substituent may be either linear or branched. The number of carbon atoms in the alkyl group is preferably 1 to 20, more preferably 1 to 14, even more preferably 1 to 12, still 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 in the cycloalkyl 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 cycloalkyl group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group.

[0015] The alkoxy group used as a substituent may be either linear or branched. The number of carbon atoms in the alkoxy group is preferably 1 to 20, more preferably 1 to 12, and even 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, and may be either linear or branched. The number of carbon atoms in 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 a vinyl group, an allyl group, a propenyl group, a butenyl group, a pentenyl group, a hexenyl group, a heptenyl group, an octenyl group, a nonenyl group, and a decenyl group.

[0017] The number of carbon atoms in 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 a cyclopropyloxy group, a cyclobutyloxy group, a cyclopentyloxy group, and a cyclohexyloxy group.

[0018] The aryl group used as a substituent is a group in which one hydrogen atom on the aromatic ring has been removed from an aromatic hydrocarbon. The number of carbon atoms in 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 a phenyl group, a naphthyl group, and an anthracenyl group.

[0019] The number of carbon atoms in 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 a phenoxy group, a 1-naphthyloxy group, and a 2-naphthyloxy group.

[0020] The number of carbon atoms in 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-C1-C 12 Alkyl groups, naphthyl-C1-C12 Alkyl groups and anthracenyl-C1-C 12 Examples of suitable alkyl groups include:

[0021] The number of carbon atoms in the arylalkoxy 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 arylalkoxy group include phenyl-C1-C 12 Alkoxy group, and naphthyl-C1-C 12 Examples include alkoxy groups.

[0022] The monovalent heterocyclic group used as a substituent refers to a group in which one hydrogen atom has been removed from the heterocycle of a heterocyclic compound. The number of carbon atoms in the monovalent heterocyclic group is preferably 3 to 21, more preferably 3 to 15, and even more preferably 3 to 9. The monovalent heterocyclic group also includes a monovalent aromatic heterocyclic group (heteroaryl group). Examples of the monovalent heterocycle include a thienyl group, a pyrrolyl group, a furanyl group, a furyl group, a pyridyl group, a pyridazinyl group, a pyrimidyl group, a pyrazinyl group, a triazinyl group, a pyrrolidyl group, a piperidyl group, a quinolyl group, and an isoquinolyl group.

[0023] The alkylidene group used as a substituent refers to a group in which two hydrogen atoms have been removed from the same carbon atom of an alkane. The number of carbon atoms in the alkylidene group is preferably 1 to 20, more preferably 1 to 14, even more preferably 1 to 12, still more preferably 1 to 6, and particularly preferably 1 to 3. Examples of the alkylidene group include a methylidene group, an ethylidene group, a propylidene group, an isopropylidene group, a butylidene group, a sec-butylidene group, an isobutylidene group, a tert-butylidene group, a pentylidene group, a hexylidene group, a heptylidene group, an octylidene group, a nonylidene group, and a 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 in the acyl group is preferably 2 to 20, more preferably 2 to 13, and even 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: -OC(=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 in the acyloxy group is preferably 2 to 20, more preferably 2 to 13, and even 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 a substituent (hereinafter, sometimes referred to as a "secondary substituent"). Unless otherwise specified, the secondary substituent may be the same as the above-mentioned substituent.

[0027] As used herein, the term "aromatic ring" refers to a ring that conforms to Hückel's rule, in which 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 carbocycle containing only carbon atoms as ring-constituting atoms, or an aromatic heterocycle containing heteroatoms such as oxygen atoms, nitrogen atoms, and sulfur atoms as ring-constituting atoms in addition to carbon atoms. The aromatic ring is preferably an aromatic carbocycle. Furthermore, the aromatic ring such as an aromatic carbocycle is preferably a 5- to 14-membered aromatic ring, more preferably a 6- to 14-membered aromatic ring, and even more preferably a 6- to 10-membered aromatic ring. Suitable specific examples of the aromatic carbocycle include a benzene ring, a naphthalene ring, an anthracene ring, and a phenanthrene ring, with a benzene ring being more preferred and a naphthalene ring being particularly preferred.

[0028] In this specification, the term "non-aromatic ring" means a ring other than an aromatic ring that has aromaticity throughout the ring. The non-aromatic ring may be a non-aromatic carbocyclic ring having only carbon atoms as ring-constituting atoms, or a non-aromatic heterocyclic ring having heteroatoms such as oxygen atoms, nitrogen atoms, and sulfur atoms as ring-constituting atoms in addition to carbon atoms. The non-aromatic ring is preferably a non-aromatic carbocyclic 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. Specific preferred examples of the non-aromatic ring (non-aromatic carbocycle) include monocyclic non-aromatic saturated carbocycles such as a cyclobutane ring, a cyclopentane ring, a cyclohexane ring, a cycloheptane ring, and a cyclooctane ring; monocyclic non-aromatic unsaturated carbocycles such as a cyclobutene ring, a cyclopentene ring, a cyclohexene ring, a cycloheptene ring, a cyclooctene ring, a cyclopentadiene ring, and a cyclohexadiene ring; bicyclo[2.2.1]heptane ring (norbornane ring), bicyclo[4.4.0]decane ring (decalin ring), bicyclo[5.3.0]decane ring, bicyclo[4.3.0]nonane ring (hydrindane ring), bicyclo[3.2.1]octane ring, bicyclo[5.4.0]undecane ring, bicyclo[3.3.0]octane ring, bicyclo[3.3.1]nonane ring, tricyclo[5.2.1.0 2,6] Decane ring (tetrahydrodicyclopentadiene ring), tricyclo[3.3.1.1 3,7 ] Decane ring (adamantane ring), tricyclo[6.2.1.0 2,7 and bicyclo[2.2.1]hept-2-ene (norbornene ring), bicyclo[2.2.2]oct-2-ene ring, bicyclo[4.4.0]dec-2-ene ring, and other non-aromatic unsaturated bicyclic or higher ring systems. The non-aromatic ring may be a non-aromatic ring partially fused with an aromatic ring. Examples of non-aromatic rings partially fused with an aromatic ring include an indane ring, an indene ring, a tetralin ring, a 1,2-dihydronaphthalene ring, a 1,4-dihydronaphthalene ring, a fluorene ring, a 9,10-dihydroanthracene ring, and a 9,10-dihydrophenanthrene ring.

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

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

[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] [ka]

[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] [ka]

[0035] (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 be joined together to form a ring. a represents a number ranging from 0 to 5.

[0036] [ka]

[0037] (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 formula (A-4). b and c each independently represent a number ranging from 0 to 5.

[0038] [ka]

[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 be joined together to form a ring. d represents a number ranging from 0 to 5.

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

[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. A divalent aromatic group refers to a group obtained by removing two hydrogen atoms from the aromatic ring of an aromatic compound. Examples of divalent aromatic groups 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 in the divalent aromatic group is preferably 3 or more, more preferably 4 or more or 5 or more, and even more preferably 6 or more, and the upper limit is preferably 30 or less, more preferably 24 or less, even more preferably 18 or less or 14 or less, and particularly preferably 10 or less. The number of carbon atoms in the substituent is not included in this number of carbon atoms.

[0043] In one preferred embodiment, R 11 , and R 12The divalent aromatic groups represented by the formula (I) are each independently an optionally substituted phenylene group, an optionally substituted naphthylene group, an optionally substituted phenylene-fluorenylidene-phenylene group, or an optionally substituted biphenylene group, more preferably an optionally substituted phenylene group or an optionally substituted naphthylene group, with an optionally substituted phenylene group being particularly preferred. When the divalent aromatic group has a substituent, the substituent is as described above, but 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 consisting of one or more (for example, 1 to 3000, 1 to 1000, 1 to 100, or 1 to 50) skeletal atoms selected from carbon atoms, oxygen atoms, nitrogen atoms, and sulfur atoms, 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 is preferred.

[0045] In one preferred embodiment, L 11 are each independently 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] L 11 Examples of the divalent aliphatic group in the formula (I) include an alkylene group, a cycloalkylene group, an alkenylene group, a cycloalkenylene group, and an alkapolyenylene group (the number of double bonds is preferably 2 to 10, more preferably 2 to 6, even more preferably 2 to 4, and still more preferably 2), and are preferably an alkylene group, a cycloalkylene group, an alkenylene group, or a cycloalkenylene group, more preferably an alkylene group or a cycloalkylene group, and even more preferably a cycloalkylene group.

[0047] L 11 The alkylene group in may be either linear or branched, and preferably has 1 to 12 carbon atoms, more preferably 1 to 6, and even more preferably 1 to 4. The number of carbon atoms does not include the number of carbon atoms of substituents. 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, and a hexylene group.

[0048] L 11 The number of carbon atoms in the cycloalkylene group in the formula (I) is preferably 3 to 15, more preferably 3 to 12, and even more preferably 3 to 10. The number of carbon atoms in 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 decahydronaphthalene group, a norbornanylene group, a dicyclopentanylene group, and an adamantanylene group, with a dicyclopentanylene group being preferred.

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

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

[0051] L 11Examples of the divalent aromatic group in the formula include an arylene group and a heteroarylene group, and an arylene group is preferred.

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

[0053] L 11 The number of carbon atoms in the heteroarylene group in the formula (I) is preferably 3 to 21, more preferably 3 to 15, and even more preferably 3 to 9. The number of carbon atoms in the substituent is not included in this number of carbon atoms. 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, and an isoquinolinediyl group.

[0054] R 11 and L 11 may be joined 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. 11 and L 11 When the phenylene and cyclopentylene groups are bonded together to form a ring, it is preferred that the phenylene and cyclopentylene groups be bonded to form an indane ring.

[0055] L 11Preferably, 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, more preferably 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 of 1 to 12 carbon atoms which may have a substituent, a cycloalkylene group of 3 to 15 carbon atoms which may have a substituent, or an arylene group of 6 to 24 carbon atoms which may have a substituent. 11 The substituents that may be possessed by the alkyl group 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.

[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 of R in formula (A-2) independently represents a divalent aromatic group which may have a substituent. 11 , R 12 In one preferred embodiment, R 13 , and R 14 The divalent aromatic groups represented by the formula (I) 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 R each independently represents a divalent aromatic group which may have a substituent. 15 , R 16 The divalent aromatic group in formula (A-2) is R 11 , R 12 In one preferred embodiment, R 15 , and R 16 The divalent aromatic group represented by the formula (I) 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 preferred, and one or more selected from the group consisting of a methyl group, an allyl group, and a hydroxy group are more preferred.

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

[0061] In formula (A-4), d represents a number in the range of 0 to 5, preferably 0 to 4, more preferably 0 to 3, or 0 to 2. R 15 and L 13 may be bonded 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. 15 and L 13 When the phenylene and cyclopentylene groups are bonded together to form a ring, it is preferred that the phenylene and cyclopentylene groups be bonded 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 0 to 4, more preferably 0 to 3 or 0 to 2.

[0063] In particular, from the viewpoint of realizing a resin composition that, in combination with the (B) component and the (C) component, exhibits good dielectric properties, as well as good mechanical properties (high elongation at break) and provides a cured product with excellent crack resistance, when X is a divalent group represented by formula (A-2), the divalent group represented by formula (A-2), i.e., 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 in formula (A-3) 12 That is, the divalent group represented by formula (A-4) is preferably a divalent group represented by the following formula (A-5).

[0064] [ka]

[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, and 21 When L is a divalent aliphatic group which may have a substituent, 21 and the benzene ring on the left may be bonded together to form a ring, n1 and n2 each independently represent a number ranging from 0 to 4, m represents a number ranging from 0 to 5; "*" represents a bond.)

[0066] Each Rs independently represents a substituent, as described above, and is preferably at least one selected from the group consisting of an alkyl group, an alkenyl group, and a hydroxy group, and more preferably at least one selected from the group consisting of a methyl group, an allyl group, and a hydroxy group.

[0067] L 21 L 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, 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. 21 The substituents that may be possessed by the alkyl group 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, 21 and the left benzene ring may be bonded together to form a ring, in which case it is preferred that the cyclopentylene group and the left benzene ring be bonded to form an indane ring.

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

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

[0071] In one particularly preferred embodiment from the viewpoint of further enjoying the effects of the present invention, X in formula (A-1) represents a divalent group represented by formula (A-2): R 11 , and R 12 each independently represents a phenylene group which may have a substituent, or a naphthylene group which may have a substituent, L 11 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; a represents a number ranging from 0 to 5, and R 11 and L 11 may bond 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 embodiment that is particularly preferable from the viewpoint of further enjoying the effects of the present invention, X in formula (A-1) represents a divalent group represented by formula (A-3): R 13 , and R 14 each independently represents a phenylene group which may have a substituent, b and c each independently represent a number ranging from 0 to 5; L 12 is a group represented by formula (A-4), R 15 , and R 16 each independently represents a phenylene group which may have a substituent, or a naphthylene group which may have a substituent, L 13 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; d represents a number ranging from 0 to 5, and R 15 and L 13may bond together to form a ring. Among them, the divalent group represented by formula (A-4) is preferably a divalent group represented by formula (A-5). In such an embodiment, the preferred types of substituents are as described above.

[0073] The component (A) is, for example, 1) 1-phenyl-1-propene-3-halide, 2) dihydric phenol compounds, can be obtained by a condensation reaction.

[0074] 1-Phenyl-1-propene-3-halides are compounds in which a halogen atom is bonded to the 3-terminus of 1-phenyl-1-propene. Examples of such compounds include 3-bromo-1-phenyl-1-propene.

[0075] The divalent phenol compound is a compound in which the phenol moiety of the compound can react with 1-phenyl-1-propene-3-halide, and can constitute X in 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, and polyphenylene ether compounds having hydroxy groups at both ends.

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

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

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

[0079] After the reaction is complete, if necessary, a purification step such as water washing or microfiltration may be performed to remove by-product salts and excess starting materials from the system. Specifically, an amount of water necessary to dissolve the by-product salts is added, the mixture is stirred, and the aqueous layer is discarded. The organic layer is then dried, and if necessary, the organic solvent is distilled off to obtain the compound of the present invention. The organic solvent may also be used as a solvent for the resin composition without being completely removed.

[0080] In combination with components (B) and (C), the resin composition exhibits good dielectric properties, and the incorporation of the alkylene ether backbone of (A) into the curing system reduces the rigidity of the maleimide, ensuring flexibility, thereby providing a cured product with good mechanical properties (high elongation at break) and excellent crack resistance. From this perspective, the content of component (A) in the resin composition, based on 100% by mass of the resin components in the resin composition, is preferably 2% or 3% by mass or more, more preferably 5% by mass or more, even more preferably 7% by mass or more, still more preferably 7.5% by mass or more, or 8% by mass or more, with the upper limit being preferably 15% by mass or less, more preferably 12% by mass or less, even more preferably 11% by mass or less, 10% by mass or less, or 9.5% by mass or less. Therefore, in one embodiment, the content of component (A) is 2% by mass or more and 12% by mass or less, based on 100% by mass of the resin components in the resin composition.

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

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

[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. Component (B) 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 an aliphatic maleimide resin not having a maleimide group directly bonded to an aromatic ring. When component (B) contains an aliphatic maleimide resin, the aliphatic maleimide resin preferably contains a maleimide resin having a carbon skeleton derived from a dimer acid. When component (B) contains an aromatic maleimide resin, the aromatic maleimide resin preferably contains a maleimide resin having one or more skeletons selected from a biphenyl skeleton and an indane skeleton. Therefore, component (B) preferably contains a maleimide resin having one or more skeletons selected from a carbon skeleton derived from a dimer acid, a biphenyl skeleton, and an indane skeleton.

[0085] A carbon skeleton derived from a dimer acid refers to a carbon skeleton obtained by removing the two terminal carboxyl groups (-COOH) of a dimer acid, or a carbon skeleton obtained by replacing the two terminal carboxyl groups (-COOH) with methylene groups (-CH2-). Dimer acids are known compounds obtained by dimerizing unsaturated fatty acids (preferably those having 11 to 22 carbon atoms, more preferably those having 14 to 20 carbon atoms, and particularly preferably those having 18 carbon atoms), and their industrial production process is largely standardized in the industry. Dimer acids are particularly readily available, primarily consisting of 36-carbon dimer acids obtained by dimerizing 18-carbon unsaturated fatty acids such as oleic acid and linoleic acid, which are inexpensive and readily available. Furthermore, dimer acids may contain arbitrary amounts of monomer acids, trimer acids, other polymerized fatty acids, etc., depending on the production method, degree of purification, etc. Furthermore, although double bonds remain after the polymerization reaction of unsaturated fatty acids, in this specification, hydrogenated products obtained by further hydrogenation to reduce the degree of unsaturation are also included in the term "dimer acid."

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

[0087] [ka]

[0088] (In formula (B1), n1+1 Xs each independently represent a divalent organic group consisting of five or more skeletal atoms selected from carbon atoms, nitrogen atoms (not forming an imide), oxygen atoms, and sulfur atoms, and non-skeletal atoms selected from hydrogen atoms and halogen atoms, and at least one of the n+1 Xs represents a divalent hydrocarbon group derived from a dimer acid; n1 Ys each independently represent a tetravalent organic group consisting of five or more skeletal atoms selected from carbon atoms, nitrogen atoms (not forming an imide), oxygen atoms, and sulfur atoms, and non-skeletal atoms selected from hydrogen atoms and halogen atoms; n1 represents an integer of 0 or 1 or more.

[0089] In formula (B1), n1+1 Xs each independently represent a divalent organic group consisting of five or more (preferably 5 to 200, more preferably 5 to 100, and even more preferably 5 to 50) skeletal atoms selected from carbon atoms, nitrogen atoms (not forming imides), oxygen atoms, and sulfur atoms, and non-skeletal atoms selected from hydrogen atoms and halogen atoms, and at least one of the n+1 Xs represents a divalent hydrocarbon group derived from a dimer acid.

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

[0091] The n1+1 Xs may have a divalent organic group other than a divalent hydrocarbon group derived from a dimer acid, but when the n1+1 Xs are taken as 100 mol%, it is preferable that 30 mol% or more of them are divalent hydrocarbon groups derived from a dimer acid, more preferably 60 mol% or more are divalent hydrocarbon groups derived from a dimer acid, even more preferably 90 mol% or more are divalent hydrocarbon groups derived from a dimer acid, and even more preferably that (all) the n1+1 Xs are divalent hydrocarbon groups derived from a dimer acid.

[0092] The divalent organic group other than the divalent hydrocarbon group derived from a dimer acid among the n1+1 Xs may be a divalent organic group without an aromatic ring, or may be a divalent organic group with an aromatic ring.

[0093] In formula (B1), n1 Ys each independently represent a tetravalent organic group consisting of five or more (preferably 5 to 200, more preferably 5 to 100, and even more preferably 5 to 50) skeletal atoms selected from carbon atoms, nitrogen atoms (not forming imides), oxygen atoms, and sulfur atoms, and non-skeletal atoms selected from hydrogen atoms and halogen atoms. The tetravalent organic group represented by Y may be a tetravalent organic group without an aromatic ring, or may be a tetravalent organic group with an aromatic ring.

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

[0095] [ka]

[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 Y 44 , ring Y 51 , ring Y 52 , ring Y 53 , 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 , Y 3a , Y 3b , Y 4a , Y 4b, Y 4c , Y 5a , Y 5b , Y 5c and Y 5d are each independently a single bond, -C(R y )2-, -O-, -CO-, -S-, -SO-, -SO2-, -CONH-, or -NHCO-; R y each independently represents a hydrogen atom or an alkyl group which may be substituted with a halogen atom, or two R y are bonded together to form a non-aromatic ring which may have a substituent; * indicates binding site; The two bonding sites on the same ring represented by * are bonding sites to two adjacent carbon atoms on the ring.

[0097] In the formulae (Y1) to (Y5), the 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 each 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 aromatic rings which may have a substituent, more preferably benzene rings which may have a substituent, and even more preferably benzene rings 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 Y43 , ring Y 44 , ring Y 51 , ring Y 52 , ring Y 53 , ring Y 54 and ring Y 55 The substituents that may be possessed by are not particularly limited, but include, for example, halogen atoms, -NO2, -CN, -COH, -OH, -SH, -NH2, -COOH, -R c , -COR c , -OR c , -SR c , -SOR c , -SO2R c , -NHR c , -NR c 2. -COOR c , -OCOR c , -CONH2, -CONHR c , -CONR c 2, -NHCOR c (However, R c is as described above.) It is a aryl group.

[0099] In formulas (Y1) to (Y5), Y 2a , Y 3a , Y 3b , Y 4a , Y 4b , Y 4c , Y 5a , Y 5b , Y 5c and Y 5d are each independently a single bond, -C(R y )2-, -O-, -CO-, -S-, -SO-, -SO2-, -CONH-, or -NHCO-, and in one embodiment, preferably represents a single bond, -C(R y )2-, or -O-.

[0100] R y each independently represents a hydrogen atom or an alkyl group which may be substituted with a halogen atom, or two R y are bonded together to form a non-aromatic ring which may have a substituent.c The alkyl group in R y are each independently 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; even more preferably a hydrogen atom, a methyl group, or a trifluoromethyl group; and particularly preferably a hydrogen atom or a methyl group.

[0101] R y The substituents that may be possessed by are not particularly limited, but include, for example, halogen atoms, -NO2, -CN, -COH, -OH, -SH, -NH2, -COOH, -R c , -COR c , -OR c , -SR c , -SOR c , -SO2R c , -NHR c , -NR c 2. -COOR c , -OCOR c , -CONH2, -CONHR c , -CONR c 2, -NHCOR c (However, R c is as described above.)

[0102] In formula (B1), n1 represents 0 or an integer of 1 or more, preferably 0 or an integer of 1 to 10, and more preferably 0.

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

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

[0105] The aromatic maleimide resin may be, for example, a maleimide resin represented by formula (B2).

[0106] [ka]

[0107] (In formula (B2), R 10 each independently represents a hydrogen atom or an alkyl group optionally substituted with a halogen atom; each ring D independently represents an aromatic carbocyclic ring which may have a substituent; n2 represents an integer of 1 or greater; The n2 units may be the same or different for each unit.

[0108] In formula (B2), R 10 are each independently a hydrogen atom or an alkyl group which may be substituted with a halogen atom. c The alkyl group in R 10 are each independently preferably a hydrogen atom or an alkyl group; more preferably a hydrogen atom or a methyl group; and even more preferably a hydrogen atom.

[0109] In formula (B2), each ring D independently represents an aromatic carbocyclic ring which may have a substituent. 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 "substituent" in ring D may be the same as the aromatic carbocyclic ring described in the section on the aromatic ring in11 , 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 may be the same as those in the "optionally substituted aromatic ring" in the above. Ring D preferably represents a benzene ring which may have a substituent; more preferably represents a benzene ring which may be substituted with a group selected from an alkyl group and an aryl group; and particularly preferably represents an (unsubstituted) benzene ring.

[0110] In formula (B2), n2 represents an integer of 1 or more, and is preferably an integer of 1 to 10.

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

[0112] [ka]

[0113] (In formula (B3), R 20 each independently represents a hydrogen atom or an alkyl group optionally substituted with a halogen atom; Ring E, ring F, and ring G each independently represent an aromatic carbocyclic ring which may have a substituent; n3 represents an integer equal to or greater than 1; The n3 units may be the same or different for each unit.

[0114] In formula (B3), R 20 are each independently a hydrogen atom or an alkyl group which may be substituted with a halogen atom.c The alkyl group in R 20 are each independently preferably 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 carbocyclic ring which may have a substituent. 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 It may be the same as the aromatic carbocyclic ring explained in the section on the aromatic ring in 1. Ring E, ring F and ring G are preferably benzene rings which may have a substituent, more preferably benzene rings which may be substituted with a group selected from an alkyl group and an aryl group, and further preferably (unsubstituted) benzene rings.

[0116] The substituents that may be possessed by ring E, ring F, and ring G are not particularly limited, but examples thereof include a halogen atom, -NO2, -CN, -COH, -OH, -SH, -NH2, -COOH, -R c , -COR c , -OR c , -SR c , -SOR c , -SO2R c , -NHR c , -NR c 2. -COOR c , -OCOR c , -CONH2, -CONHR c , -CONR c 2, -NHCOR c (However, R cis as described above).

[0117] In formula (B3), n3 represents an integer of 1 or more, and is preferably an integer of 1 to 10.

[0118] Commercially available maleimide resins having a biphenyl skeleton include, for example, "MIR-3000-70MT" and "MIR-5000-60T" 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 includes a maleimide resin represented by the following formula (B4).

[0121] [ka]

[0122] (In formula (B4), R 30 each independently represents an alkyl group; Ring H and ring I each independently represent an aromatic carbocyclic ring which may have a substituent; n4 represents an integer of 1 or greater; The n4 units may be the same or different for each unit.

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

[0124] In formula (B4), rings H each independently represent an 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 have a substituent with an alkyl group, and even more preferably a benzene ring substituted with an alkyl group.

[0125] In formula (B4), each ring I independently represents an 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 have an alkyl group, and further preferably an (unsubstituted) benzene ring.

[0126] Substituents that may be carried by ring H and ring I include, but are not limited to, halogen atoms, -NO2, -CN, -COH, -OH, -SH, -NH2, -COOH, -R c , -COR c , -OR c , -SR c , -SOR c , -SO2R c , -NHR c , -NR c 2. -COOR c , -OCOR c , -CONH2, -CONHR c , -CONR c 2, -NHCOR c (However, R c is as described above.)

[0127] In formula (B4), n4 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 the method described in the Japan Institute of Invention and Innovation's Disclosure Technical Bulletin No. 2020-500211 or a method equivalent 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, even more preferably 150 g / eq. or more, 200 g / eq. or more, 250 g / eq. or more, or 300 g / eq. or more, and its upper limit is preferably 2,000 g / eq. or less, more preferably 1,000 g / eq. or less, even more preferably 800 g / eq. or less, 600 g / eq. or less, 500 g / eq. or less, or 450 g / eq. The maleimide group equivalent is the mass of component (B) per 1 molar equivalent of maleimide groups.

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

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

[0133] From the viewpoint of being able to realize a resin composition that, in combination with the (C) component, exhibits even better dielectric properties, as well as even better mechanical properties (high elongation at break), and provides a cured product with even more excellent crack resistance, the mass ratio of the (A) component to the (B) component ((A) component / (B) component) is preferably 0.02 or more, more preferably 0.04, even more preferably 0.06 or more or 0.08 or more, still more preferably 0.1 or more, 0.12 or more, or 0.14 or more, and the upper limit thereof is preferably 0.4 or less, more preferably 0.3 or less, even 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), which does not include a maleimide resin.

[0135] Examples of component (C) include epoxy resins, phenolic resins, benzoxazine resins, active ester resins, cyanate ester resins, carbodiimide resins, amine resins, acid anhydride resins, and terminal double bond resins. The thermosetting resins may be used alone or in combination of two or more in any ratio. Among these, from the viewpoint of being able to further enjoy the effects of the present invention, one or more selected from the group consisting of epoxy resins, phenolic resins, and terminal double bond resins are preferred. Phenol 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 are collectively referred to as epoxy resin curing agents.

[0136] -Epoxy resin- The type of epoxy resin is not particularly limited as long as it has one or more (preferably two or more) epoxy groups per molecule. Examples of epoxy resins include bisphenol-type epoxy resins, dicyclopentadiene-type epoxy resins, trisphenol-type epoxy resins, naphthol novolac-type epoxy resins, phenol novolac-type epoxy resins, tert-butyl-catechol-type epoxy resins, naphthalene-type epoxy resins, naphthol-type epoxy resins, anthracene-type epoxy resins, glycidylamine-type epoxy resins, glycidyl ester-type epoxy resins, cresol novolac-type epoxy resins, biphenyl-type epoxy resins, linear aliphatic epoxy resins, epoxy resins having a butadiene structure, alicyclic epoxy resins, heterocyclic epoxy resins, spiro ring-containing epoxy resins, cyclohexane-type epoxy resins, cyclohexanedimethanol-type epoxy resins, naphthylene ether-type epoxy resins, trimethylol-type epoxy resins, and tetraphenylethane-type epoxy resins. Bisphenol-type epoxy resins refer to epoxy resins having a bisphenol structure, such as bisphenol A-type epoxy resins, bisphenol F-type epoxy resins, bisphenol S-type epoxy resins, and bisphenol AF-type epoxy resins. Biphenyl-type epoxy resins refer to epoxy resins having a biphenyl structure, where the biphenyl structure may have a substituent such as an alkyl group, an alkoxy group, or an aryl group. Therefore, bixylenol-type epoxy resins and biphenylaralkyl-type epoxy resins are also included in biphenyl-type epoxy resins.

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

[0138] The liquid epoxy resin is preferably a liquid epoxy resin having two or more epoxy groups in one molecule.

[0139] Preferred liquid epoxy resins include glycerol-type epoxy resins, bisphenol A-type epoxy resins, bisphenol F-type epoxy resins, bisphenol AF-type epoxy resins, naphthalene-type epoxy resins, glycidyl ester-type epoxy resins, glycidyl amine-type epoxy resins, phenol novolac-type epoxy resins, alicyclic epoxy resins having an ester skeleton, cyclohexanedimethanol-type epoxy resins, alicyclic glycidyl ethers, and epoxy resins having a butadiene structure.

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

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

[0142] Preferred solid epoxy resins include bixylenol-type epoxy resins, naphthalene-type epoxy resins, naphthalene-type tetrafunctional epoxy resins, naphthol novolac-type epoxy resins, cresol novolac-type epoxy resins, dicyclopentadiene-type epoxy resins, trisphenol-type epoxy resins, naphthol-type epoxy resins, biphenyl-type epoxy resins, naphthylene ether-type epoxy resins, anthracene-type epoxy resins, bisphenol A-type epoxy resins, bisphenol AF-type epoxy resins, phenol aralkyl-type epoxy resins, tetraphenylethane-type epoxy resins, and phenolphthalimidine-type epoxy resins.

[0143] Specific examples of solid epoxy resins include "HP4032H" (naphthalene type epoxy resin) manufactured by DIC Corporation; "HP-4700" and "HP-4710" (naphthalene type tetrafunctional epoxy resins) manufactured by DIC Corporation; "N-690" (cresol novolac type epoxy resin) manufactured by DIC Corporation; "N-695" (cresol novolac type epoxy resin) manufactured by DIC Corporation; "HP-7200", "HP-7200HH", "HP-7200H", and "HP-7200L" (dicyclopentadiene type epoxy resins) manufactured by DIC Corporation; and "EXA-7311" and "E" manufactured by DIC Corporation. XA-7311-G3, EXA-7311-G4, EXA-7311-G4S, HP-6000, and HP-6000L (naphthylene ether epoxy resins); Nippon Kayaku's EPPN-502H (trisphenol epoxy resin); Nippon Kayaku's NC7000L (naphthol novolac epoxy resin); Nippon Kayaku's NC3000H, NC3000, NC3000L, NC3000FH, and NC3100 (biphenyl epoxy resins); and Nippon Steel Chemical & Material's ESN475V. "ESN4100V" (naphthalene-type epoxy resin); "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", and "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. Examples of epoxy resins include "YX7700" (phenol aralkyl type epoxy resin) manufactured by Osaka Gas Chemicals Co., Ltd.; "PG-100" and "CG-500" manufactured by Osaka Gas Chemicals Co., Ltd.; "YL7760" (bisphenol AF type epoxy resin) manufactured by Mitsubishi Chemical Corporation; "YL7800" (fluorene 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; and "WHR991S" (phenolphthalimidine type epoxy resin) manufactured by Nippon Kayaku Co., Ltd.These may be used alone or in combination of two or more.

[0144] When a liquid epoxy resin and a solid epoxy resin are used in combination as the epoxy resin, the mass ratio thereof (liquid epoxy resin:solid epoxy resin) is preferably 10:1 to 1:50, more preferably 5:1 to 1:20, even 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., even 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 even more preferably 400 to 1500. The weight-average molecular weight of the resin can be measured by gel permeation chromatography (GPC) as a polystyrene-equivalent value.

[0147] -Phenol resin- The phenolic resin may be 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 per molecule. When combined with an epoxy resin, the phenolic resin may react with the epoxy resin to cure the resin composition, and is therefore sometimes referred to as a "phenolic curing agent." From the viewpoint of achieving the remarkable effects of the present invention, the phenolic resin is preferably a phenolic resin having a novolac structure. Furthermore, from the viewpoint of adhesion, nitrogen-containing phenolic resins are preferred, and triazine skeleton-containing phenolic resins are more preferred. Of these, triazine skeleton-containing phenolic novolac resins are preferred from the viewpoint of achieving the remarkable effects of the present invention. Specific examples of phenolic resins include "MEH-7700," "MEH-7810," and "MEH-7851" manufactured by Meiwa Chemical Industry Co., Ltd.; "NHN," "CBN," and "GPH" manufactured by Nippon Kayaku Co., Ltd.; "SN-170," "SN-180," "SN-190," "SN-475," "SN-485," "SN-495," "SN-375," and "SN-395" manufactured by Nippon Steel Chemical & Material Co., Ltd.; and "LA-7052," "LA-7054," "LA-3018," "LA-3018-50P," "LA-1356," "TD2090," "TD-2090-60M," and "KA-1163" manufactured by DIC Corporation.

[0148] -Cyanate ester resin- The cyanate ester resin may be a compound having one or more, preferably two or more, cyanate groups in one molecule. When combined with an epoxy resin, the cyanate ester resin reacts with the epoxy resin to cure the resin composition, and is therefore sometimes called a "cyanate ester curing agent." Examples of cyanate ester resins include bifunctional cyanate resins such as bisphenol A dicyanate, polyphenol cyanate (oligo(3-methylene-1,5-phenylene cyanate)), 4,4'-methylenebis(2,6-dimethylphenyl cyanate), 4,4'-ethylidene diphenyl dicyanate, hexafluorobisphenol A dicyanate, 2,2-bis(4-cyanate)phenylpropane, 1,1-bis(4-cyanatephenylmethane), bis(4-cyanate-3,5-dimethylphenyl)methane, 1,3-bis(4-cyanatephenyl-1-(methylethylidene))benzene, bis(4-cyanatephenyl)thioether, and bis(4-cyanatephenyl)ether; multifunctional cyanate resins derived from phenol novolac and cresol novolac; and prepolymers in which these cyanate resins are partially converted to triazine. Specific examples of cyanate ester resins include "PT30" and "PT60" manufactured by Lonza (both of which are phenol novolac-type multifunctional cyanate resins), "BA230" and "BA230S75" (prepolymers in which part or all of bisphenol A dicyanate has been triazine-converted to form a trimer).

[0149] - Active ester resin - As the activated ester resin, compounds having two or more highly reactive ester groups per molecule, such as phenol esters, thiophenol esters, N-hydroxyamine esters, and esters of heterocyclic hydroxy compounds, are generally preferred. When combined with an epoxy resin, activated ester resins react with the epoxy resin to cure the resin composition, and are therefore sometimes referred to as "activated ester curing agents." The activated ester resin is preferably one obtained by the condensation reaction of a carboxylic acid compound and / or a thiocarboxylic acid compound with a hydroxy compound and / or a thiol compound. From the perspective of improving heat resistance, activated ester resins obtained from a carboxylic acid compound and a hydroxy compound are preferred, and activated ester resins obtained from a carboxylic acid compound and a phenol compound and / or a naphthol compound are more preferred. As the carboxylic acid compound, either an aromatic carboxylic acid compound or an aliphatic carboxylic acid compound may be used, such as benzoic acid, acetic acid, succinic acid, maleic acid, itaconic acid, phthalic acid, isophthalic acid, terephthalic acid, pyromellitic acid, and halides thereof. Examples of aromatic hydroxy compounds include (i) polyaddition products of unsaturated aliphatic cyclic compounds containing two double bonds per molecule with phenols, (ii) various bisphenol compounds, (iii) aromatic polyols having two or more hydroxy groups bonded to a carbon atom on an aromatic ring, and (iv) aromatic monools having one hydroxy group bonded to a carbon atom on an aromatic ring. Examples of polyaddition products of unsaturated aliphatic cyclic compounds with phenols include polyaddition products of unsaturated aliphatic cyclic compounds such as dicyclopentadiene, tetrahydroindene, norbornadiene, limonene, and vinylcyclohexene with optionally substituted phenols (e.g., phenol, cresol, xylenol, ethylphenol, propylphenol, vinylphenol, allylphenol, phenylphenol, benzylphenol, and halophenols), and specific examples thereof include dicyclopentadiene-phenol polyaddition products.Examples of bisphenol compounds include bisphenol A, bisphenol F, bisphenol AF, bisphenol AP, bisphenol B, bisphenol BP, bisphenol C, and bisphenol M. Examples of aromatic polyols in which two or more hydroxy groups are bonded to carbon atoms on an aromatic ring include hydroquinone, resorcinol, catechol, 1,5-dihydroxynaphthalene, 1,6-dihydroxynaphthalene, 2,6-dihydroxynaphthalene, dihydroxybenzophenone, trihydroxybenzophenone, tetrahydroxybenzophenone, phloroglucinol, benzenetriol, and phenol novolak. Examples of aromatic monools having one hydroxy group bonded to a carbon atom on an aromatic ring include phenol, cresol, xylenol, ethylphenol, propylphenol, vinylphenol, allylphenol, phenylphenol, benzylphenol, halophenols, naphthol, methylnaphthol, dimethylnaphthol, ethylnaphthol, propylnaphthol, vinylnaphthol, allylnaphthol, phenylnaphthol, benzylnaphthol, and halonaphthol.

[0150] Specifically, the active ester resin is preferably 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 novolac, an active ester resin containing a benzoylated product of phenol novolac, or an active ester resin containing a styryl group and a naphthalene structure, and among these, at least one selected from dicyclopentadiene-type active ester resins and naphthalene-type active ester resins is more preferred. As the dicyclopentadiene-type active ester resin, an active ester resin containing a dicyclopentadiene-type diphenol structure is preferred.

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

[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. When combined with an epoxy resin, a carbodiimide resin can react with the epoxy resin to cure the resin composition, and therefore is sometimes called a "carbodiimide-based curing agent." Specific examples of carbodiimide resins include aliphatic biscarbodiimides such as tetramethylene-bis(t-butylcarbodiimide) and cyclohexane-bis(methylene-t-butylcarbodiimide); aromatic biscarbodiimides such as phenylene-bis(xylylcarbodiimide); aliphatic polycarbodiimides such as polyhexamethylenecarbodiimide, polytrimethylhexamethylenecarbodiimide, polycyclohexylenecarbodiimide, poly(methylenebiscyclohexylenecarbodiimide), and poly(isophoronecarbodiimide); poly(phenylenecarbodiimide), poly(naphthalenecarbodiimide); Examples of polycarbodiimides include aromatic polycarbodiimides such as poly(methylenediphenylenecarbodiimide), poly(tolylenecarbodiimide), poly(methyldiisopropylphenylenecarbodiimide), poly(triethylphenylenecarbodiimide), poly(diethylphenylenecarbodiimide), poly(triisopropylphenylenecarbodiimide), poly(diisopropylphenylenecarbodiimide), poly(xylylenecarbodiimide), poly(tetramethylxylylenecarbodiimide), poly(methylenediphenylenecarbodiimide), and poly[methylenebis(methylphenylene)carbodiimide]. 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 Inc.; and "Stavaxol P," "Stavaxol P400," and "Hykasil 510" manufactured by Lanxess AG.

[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. When combined with an epoxy group, the acid anhydride resin can react with the epoxy resin to cure the resin composition, and therefore is sometimes called an "acid anhydride curing agent." Specific examples of acid anhydride resins include phthalic anhydride, tetrahydrophthalic anhydride, hexahydrophthalic anhydride, methyltetrahydrophthalic anhydride, methylhexahydrophthalic anhydride, methylnadic anhydride, hydrogenated methylnadic anhydride, trialkyltetrahydrophthalic anhydride, dodecenyl succinic anhydride, 5-(2,5-dioxotetrahydro-3-furanyl)-3-methyl-3-cyclohexene-1,2-dicarboxylic anhydride, trimellitic anhydride, pyromellitic anhydride, and benzophenonetetracarboxylic anhydride. Examples of suitable anhydrides include hydrates, biphenyltetracarboxylic dianhydride, naphthalenetetracarboxylic dianhydride, oxydiphthalic dianhydride, 3,3'-4,4'-diphenylsulfonetetracarboxylic dianhydride, 1,3,3a,4,5,9b-hexahydro-5-(tetrahydro-2,5-dioxo-3-furanyl)-naphtho[1,2-C]furan-1,3-dione, ethylene glycol bis(anhydrotrimellitate), and polymeric anhydrides such as styrene-maleic acid resin, which is a copolymer of styrene and maleic acid. Commercially available acid anhydride resins include, for example, "HNA-100," "MH-700," "MTA-15," "DDSA," and "OSA" manufactured by New Japan Chemical Co., Ltd.; "YH-306" and "YH-307" manufactured by Mitsubishi Chemical Corporation; "HN-2200" and "HN-5500" manufactured by Resonac; and "EF-30," "EF-40," "EF-60," and "EF-80" manufactured by Cray Valley Chemical Industries, Ltd.

[0154] -Amine resin- The amine resin may be a compound having one or more, preferably two or more, amino groups in one molecule. When combined with an epoxy group, the amine resin may react with the epoxy resin to cure the resin composition, and is therefore sometimes referred to as an "amine-based curing agent." Examples of the amine resin include aliphatic amines, polyether amines, alicyclic amines, and aromatic amines, with aromatic amines being preferred. The amine resin is preferably a primary amine or secondary amine, with primary amines being more preferred. Specific examples of amine resins include 4,4'-methylenebis(2,6-dimethylaniline), 4,4'-diaminodiphenylmethane, 4,4'-diaminodiphenyl sulfone, 3,3'-diaminodiphenyl sulfone, m-phenylenediamine, m-xylylenediamine, diethyltoluenediamine, 4,4'-diaminodiphenyl ether, 3,3'-dimethyl-4,4'-diaminobiphenyl, 2,2'-dimethyl-4,4'-diaminobiphenyl, 3,3'-dihydroxybenzidine, and 2,2-bis(3-amino-4-hydroxyphenyl)propionate. Examples of suitable bis(4-aminophenoxy)benzene include bis(4-aminophenyl)propane, 3,3-dimethyl-5,5-diethyl-4,4-diphenylmethanediamine, 2,2-bis(4-aminophenyl)propane, 2,2-bis(4-(4-aminophenoxy)phenyl)propane, 1,3-bis(3-aminophenoxy)benzene, 1,3-bis(4-aminophenoxy)benzene, 1,4-bis(4-aminophenoxy)benzene, 4,4'-bis(4-aminophenoxy)biphenyl, bis(4-(4-aminophenoxy)phenyl)sulfone, and bis(4-(3-aminophenoxy)phenyl)sulfone. Commercially available amine resins include, for example, "SEIKACURE-S" manufactured by Seika Corporation; "KAYABOND C-200S," "KAYABOND C-100," "KAYAHARD AA," "KAYAHARD AB," and "KAYAHARD AS" manufactured by Nippon Kayaku Co., Ltd.; "Epicure W" manufactured by Mitsubishi Chemical Corporation; and "DTDA" manufactured by Sumitomo Seika Chemicals Co., Ltd.

[0155] -Benzoxazine resin- Benzoxazine resins, when combined with epoxy resins, can react with the epoxy resin to cure the resin composition, and are therefore sometimes called "benzoxazine-based curing agents." Specific examples of benzoxazine resins include "JBZ-OP100D" and "ODA-BOZ" manufactured by JFE Chemical Corporation; "HFB2006M" manufactured by Showa Polymer Co., Ltd.; and "Pd" and "Fa" manufactured by Shikoku Chemical Industry Co., Ltd.

[0156] Thiol resins are sometimes called "thiol-based curing agents" because they react with epoxy resins when combined with them to cure the resin composition. Examples of thiol resins include trimethylolpropane tris(3-mercaptopropionate), pentaerythritol tetrakis(3-mercaptobutyrate), and tris(3-mercaptopropyl)isocyanurate.

[0157] -Terminal double bond resin- The terminal double bond resin is a radical polymerizable resin having an ethylenically unsaturated group having one or more (preferably two or more) carbon-carbon double bonds in one molecule, or a radical polymerizable group containing an ethylenically unsaturated bond at the molecular end. Examples of the radical 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 these, from the viewpoint of being able to more effectively enjoy the effects of the present invention, one or more selected from a vinyl group, an allyl group, and a styryl group are preferred. Among these, from the viewpoint of being able to more easily enjoy the effects of the present invention, the terminal double bond resin is preferably an allyl resin, a vinyl resin, or a styryl resin.

[0158] The allyl resin is, for example, a compound having one or more, preferably two or more allyl groups. Examples of the allyl resin include aromatic carboxylic acid allyl ester compounds such as diallyl diphenate, triallyl trimellitate, diallyl phthalate, diallyl isophthalate, diallyl terephthalate, diallyl 2,6-naphthalenedicarboxylic acid, and diallyl 2,3-naphthalenecarboxylic acid; isocyanuric acid allyl ester compounds such as 1,3,5-triallyl isocyanurate and 1,3-diallyl-5-glycidyl isocyanurate; epoxy-containing aromatic allyl compounds such as 2,2-bis[3-allyl-4-(glycidyloxy)phenyl]propane; benzoxazine-containing aromatic allyl compounds such as bis[3-allyl-4-(3,4-dihydro-2H-1,3-benzoxazin-3-yl)phenyl]methane; ether-containing aromatic allyl compounds such as 1,3,5-triallyl ether benzene; and allyl silane compounds such as diallyldiphenylsilane. Commercially available allyl radical polymerizable compounds include "TAIC" (1,3,5-triallyl isocyanurate) manufactured by Nippon Kasei Chemical Industry Co., Ltd., "DAD" (diallyl diphenate) manufactured by Nisshoku Techno Fine Chemical Co., Ltd., "TRIAM-705" (triallyl trimellitate) manufactured by Fujifilm Wako Pure Chemical Industries, Ltd., "DAND" (2,3-naphthalene carboxylic acid diallyl) manufactured by Nisshoku Techno Fine Chemical Co., Ltd., "ALP-d" (bis[3-allyl-4-(3,4-dihydro-2H-1,3-benzoxazin-3-yl)phenyl]methane) manufactured by Shikoku Chemical Industry Co., Ltd., "RE-810NM" (2,2-bis[3-allyl-4-(glycidyloxy)phenyl]propane) manufactured by Nippon Kayaku Co., Ltd., and "DA-MGIC" (1,3-diallyl-5-glycidyl isocyanurate) manufactured by Shikoku Chemical Industry Co., Ltd.

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

[0160] The styryl resin may be a monomer or an oligomer, and may be any type, as long as it contains one or more (preferably two or more) styryl or vinylphenyl groups per molecule. Examples of the styryl resin include "OPE-2St," "OPE-2St 1200," and "OPE-2St 2200" (all manufactured by Mitsubishi Gas Chemical Company, Inc.). Examples of the styryl resin include, in addition to styrene monomers, 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, as well as copolymers of these aromatic divinyl compounds with aromatic monovinyl compounds such as styrene, vinyltoluene, ethylstyrene, and vinylnaphthalene.

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

[0162] From the viewpoint of being able to realize a resin composition that exhibits good dielectric properties, as well as good mechanical properties (high elongation at break), and that leads to a cured product with excellent crack resistance, when the resin components in the resin composition are taken as 100% by mass, the total content of components (A), (B), and (C) is preferably 60% by mass or more, more preferably 70% by mass or more, even more preferably 80% by mass or more, and still more preferably 85% by mass or more or 90% by mass or more; the upper limit is not particularly limited, and can be, for example, 99.8% by mass or less, 99.5% by mass or less, or 99% by mass or less.

[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 resins, oxazoline group-containing resins, polyimide resins, phenoxy resins, polyvinyl acetal resins, polyolefin resins, polybutadiene resins, polyamideimide resins, polyetherimide resins, polysulfone resins, polyethersulfone resins, polyphenylene ether resins, polycarbonate resins, polyetheretherketone resins, and polyester resins.

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

[0166] The polystyrene resin may be a commercially available product, and examples thereof include hydrogenated styrene-based thermoplastic elastomers "H1041," "Tuftec H1043," "Tuftec P2000," and "Tuftec MP10" (manufactured by Asahi Kasei Corporation); epoxidized styrene-butadiene thermoplastic elastomers "Epofriend AT501" and "CT310" (manufactured by Daicel Corporation); modified styrene-based elastomer having a hydroxyl group "Septon HG252" (manufactured by Kuraray Co., Ltd.); modified styrene-based elastomer having a carboxyl group "Tuftec N503M," modified styrene-based elastomer having an amino group "Tuftec N501," modified styrene-based elastomer having an acid anhydride group "Tuftec M1913" (manufactured by Asahi Kasei Corporation); and unmodified styrene-based elastomer "Septon S8104" (manufactured by Kuraray Co., Ltd.).

[0167] Examples of the oxazoline group-containing resin include 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, and 4-methyl-2-vinyl-2-oxazoline. These resins are obtained by polymerizing addition-polymerizable oxazoline compounds (vinyloxazoline skeleton-containing monomers) such as 4,4,5-trimethyl-2-vinyl-2-oxazoline and 4,4,5-trimethyl-2-vinyl-2-oxazoline, and may be copolymerized with 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, and m-divinylbenzene, as needed. Specific examples of oxazoline group-containing resins include "PX-3-RP-61" manufactured by Nippon Shokubai Co., Ltd.

[0168] Specific examples of polyimide resins include "SLK-6100" manufactured by Shin-Etsu Chemical Co., Ltd., "Rikacoat SN20" and "Rikacoat PN20" manufactured by New Japan Chemical Co., Ltd., and "PIAD200" manufactured by Arakawa Chemical Industries, Ltd.

[0169] Examples of phenoxy resins include phenoxy resins having one or more skeletons selected from the group consisting of bisphenol A, bisphenol F, bisphenol S, bisphenolacetophenone, novolac, biphenyl, fluorene, dicyclopentadiene, norbornene, naphthalene, anthracene, adamantane, terpene, and trimethylcyclohexane. 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 phenoxy resins include "1256" and "4250" manufactured by Mitsubishi Chemical Corporation (both of which are phenoxy resins containing a bisphenol A skeleton); "YX8100" manufactured by Mitsubishi Chemical Corporation (phenoxy resin containing a bisphenol S skeleton); "YX6954" manufactured by Mitsubishi Chemical Corporation (phenoxy resin containing a bisphenol acetophenone skeleton); "FX280" and "FX293" manufactured by Nippon Steel Chemical & Material Co., Ltd.; and "YX7200B35," "YL7500BH30," "YX6954BH30," "YX7553BH30," "YL7769BH30," "YL6794," "YL7213," "YL7290," and "YL7482" manufactured by Mitsubishi Chemical Corporation.

[0171] Examples of polyvinyl acetal resins include polyvinyl formal resins and polyvinyl butyral resins, with polyvinyl butyral resins being preferred. Specific examples of polyvinyl acetal resins include S-LEC BH series, BX series (e.g., BX-5Z), KS series (e.g., KS-1), BL series, and BM series manufactured by Sekisui Chemical Co., Ltd.

[0172] Examples of polyolefin resins include ethylene copolymer resins such as low-density polyethylene, very 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 hydrogenated polybutadiene skeleton-containing resins, hydroxy group-containing polybutadiene resins, phenolic hydroxy 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, and polyphenylene ether-polybutadiene resins.

[0174] Specific examples of polyamide-imide resins include "Vylomax HR11NN" and "Vylomax HR16NN" manufactured by Toyobo Co., Ltd. Specific examples of polyamide-imide resins also include modified polyamide-imides such as "KS9100" and "KS9300" (polysiloxane skeleton-containing polyamide-imides) manufactured by Resonac Corporation.

[0175] A specific example of the polyethersulfone resin is "PES5003P" manufactured by Sumitomo Chemical Co., Ltd.

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

[0177] A specific example of the polyphenylene ether resin is NORYL SA90 manufactured by SABIC, etc. A specific example of the polyetherimide resin is ULTEM manufactured by GE, etc.

[0178] Examples of polycarbonate resins include hydroxyl group-containing carbonate resins, phenolic hydroxyl group-containing carbonate resins, carboxyl group-containing carbonate resins, acid anhydride group-containing carbonate resins, isocyanate group-containing carbonate resins, and urethane group-containing carbonate resins. Specific examples of polycarbonate resins include "FPC0220" manufactured by Mitsubishi Gas Chemical Company, Inc., "T6002" and "T6001" (polycarbonate diols) manufactured by Asahi Kasei Corporation, and "C-1090," "C-2090," and "C-3090" (polycarbonate diols) manufactured by Kuraray Co., Ltd. Specific examples of polyether ether ketone resins include "Sumiploy K" manufactured by Sumitomo Chemical Co., Ltd.

[0179] Examples of polyester resins include polyethylene terephthalate resin, polyethylene naphthalate resin, polybutylene terephthalate resin, polybutylene naphthalate resin, polytrimethylene terephthalate resin, polytrimethylene naphthalate resin, and polycyclohexane dimethyl terephthalate resin.

[0180] The content of component (D) in the resin composition is, when the resin components in the resin composition are taken as 100% by mass, for example, 0% by mass or more, preferably 0.01% by mass or more, more preferably 0.1% by mass or more, even 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, even 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 inorganic fillers 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 titanate zirconate, 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. The inorganic fillers may be used alone or in combination of two or more.

[0183] Commercially available inorganic fillers include, for example, "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.; "Silfil NSS-3N," "Silfil NSS-4N," and "Silfil NSS-5N" manufactured by Tokuyama Corporation; "CellSpheres" and "MGH-005" manufactured by Taiheiyo Cement Corporation; and "Sferique" and "BA-1" manufactured by JGC Catalysts and Chemicals Co., 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, even 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, even more preferably 0.07 μm or more, 0.1 μm or more, or 0.2 μm or more. The average particle size of inorganic fillers can be measured using a laser diffraction / scattering method based on Mie scattering theory. Specifically, a volumetric particle size distribution of the inorganic filler is created using a laser diffraction / scattering particle size distribution analyzer, and the median diameter is used as the average particle size. A measurement sample can be prepared by weighing 100 mg of inorganic filler and 10 g of methyl ethyl ketone into a vial and dispersing the mixture ultrasonically for 10 minutes. The volumetric particle size distribution of the inorganic filler was measured using a laser diffraction particle size distribution analyzer with blue and red wavelength light sources using a flow cell system, and the average particle size was calculated as the median diameter from the particle size distribution obtained. Examples of laser diffraction particle size distribution analyzers include the 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 0.5m 2 / g or more, more preferably 1m 2 / g or more, 3m 2 / g or more or 5m 2 The upper limit of the specific surface area is not particularly limited, but is preferably 100 m 2 / g or less, more preferably 80m 2 / g or less, more preferably 60m 2 / g or less, 50m 2 / g or less or 40m 2 / g or less. The specific surface area of ​​the inorganic filler can be obtained according to the BET method by adsorbing nitrogen gas onto the surface of the sample using a specific surface area measuring device (Macsorb HM-1210 manufactured by Mountech Co., Ltd.) and calculating the specific surface area using the BET multipoint method.

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

[0187] Examples of commercially available surface treatment agents include "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., and "SZ-31" (hexamethyldisilazane) manufactured by Shin-Etsu Chemical Co., Ltd.

[0188] The degree of surface treatment with the surface treatment agent is preferably within a predetermined range from the viewpoint of improving the dispersibility of the inorganic filler. Specifically, 100% 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. From the viewpoint of improving the dispersibility of the inorganic filler, the amount of carbon per unit surface area of ​​the inorganic filler is set to 0.02 mg / m 2 More than 0.1 mg / m is preferable. 2 More preferably, 0.2 mg / m or more 2On the other hand, from the viewpoint of preventing an increase in the melt viscosity of the resin composition or the melt viscosity in the form of a sheet, it is more preferable that the melt viscosity is 1.0 mg / m 2 Preferably less than 0.8 mg / m 2 Less than 0.5 mg / m is more preferable. 2 The following is even more preferred. The carbon amount per unit surface area of ​​component (E) can be measured after the surface-treated inorganic filler is washed with a solvent (e.g., methyl ethyl ketone (MEK)). Specifically, a sufficient amount of MEK as a solvent is added to the inorganic filler that has been surface-treated with a surface treatment agent, and ultrasonic cleaning is performed at 25°C for 5 minutes. The supernatant is removed, the solid content is dried, and then the carbon amount per unit surface area of ​​the inorganic filler can be measured using a carbon analyzer. An "EMIA-320V" manufactured by Horiba, Ltd., or the like can be used as the carbon analyzer.

[0190] From the viewpoint of realizing a resin composition that, when combined with components (A) to (C), exhibits good dielectric properties, as well as good mechanical properties (high elongation at break), and provides a cured product with excellent crack resistance, the content of component (E) in the resin composition is preferably 50% by mass or more, more preferably 60% by mass or more, and even more preferably 70% by mass or more, when the total non-volatile components in the resin composition is 100% by mass, and the upper limit of the 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 component (F) include a thermal polymerization initiator that generates free radicals upon heating and a photopolymerization initiator that generates free radicals upon light irradiation, and among these, a thermal polymerization initiator is preferred from the viewpoint of being able to further enjoy the effects of the present invention. Component (F) may be used alone or in any combination of two or more types.

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

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

[0195] Examples of the azo radical polymerization initiator 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; 2,2'-azobis[2-methyl-N-[1,1-bis(hydroxymethyl)-2-hydroxyethyl]propionamide], and 2,2'-azobis[2-methyl-N-[1,1-bis(hydroxymethyl)-2-hydroxyethyl]propionamide]. azoamide compounds such as 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] Commercially available products of component (F) include, for example, NOF Corporation's "Perbutyl C," "Perbutyl A," "Perbutyl P," "Perbutyl L," "Perbutyl O," "Perbutyl ND," "Perbutyl Z," "Perbutyl I," "Percumyl P," "Percumyl D," "Perhexyl D," "Perhexyl A," "Perhexyl I," "Perhexyl Z," "Perhexyl ND," "Perhexyl O," and "Perhexyl PV."

[0197] The content of component (F) in the resin composition is not particularly limited, but is preferably 10% by mass or less, more preferably 5% by mass or less, even more preferably 3% by mass or less, and even more preferably 1.5% by mass or less, based on 100% by mass of the resin components in the resin composition. The lower limit of the content is not particularly limited, but may be, for example, 0% by mass or more, preferably 0.01% by mass or more, more preferably 0.05% by mass or more, even 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, based on 100% by mass of the resin components in the resin composition.

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

[0199] Examples of component (G) include phosphorus-based curing accelerators, amine-based curing accelerators, imidazole-based curing accelerators, guanidine-based curing accelerators, and metal-based curing accelerators, with amine-based curing accelerators, imidazole-based curing accelerators, and metal-based curing accelerators being preferred, and either amine-based curing accelerators or imidazole-based curing accelerators being 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, and butyltriphenylphosphonium thiocyanate, with triphenylphosphine and tetrabutylphosphonium decanoate being preferred.

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

[0202] Examples of the imidazole curing accelerator 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-undecylimidazole, 1-cyanoethyl-2-phenylimidazolium 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-4,5-dihydroxymethylimidazole, Examples of the imidazole compound include imidazole compounds such as 2-phenyl-4-methyl-5-hydroxymethylimidazole, 2,3-dihydro-1H-pyrrolo[1,2-a]benzimidazole, 1-dodecyl-2-methyl-3-benzylimidazolium chloride, 2-methylimidazoline, and 2-phenylimidazoline, as well as adducts of imidazole compounds with epoxy resins, and 2-ethyl-4-methylimidazole and 1-benzyl-2-phenylimidazole are preferred.

[0203] As the imidazole-based curing accelerator, commercially available products may be used, such as "P200-H50" manufactured by Mitsubishi Chemical Corporation and "1B2PZ" manufactured by Shikoku Chemicals Corporation.

[0204] Examples of 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, and 7-methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene. Examples of suitable biguanide include 1-methylbiguanide, 1-ethylbiguanide, 1-n-butylbiguanide, 1-n-octadecylbiguanide, 1,1-dimethylbiguanide, 1,1-diethylbiguanide, 1-cyclohexylbiguanide, 1-allylbiguanide, 1-phenylbiguanide, and 1-(o-tolyl)biguanide. Of these, dicyandiamide and 1,5,7-triazabicyclo[4.4.0]dec-5-ene are preferred.

[0205] Examples of metal-based curing accelerators include organometallic complexes or organometallic salts of metals such as cobalt, copper, zinc, iron, nickel, manganese, and tin. Specific examples of organometallic complexes include organic cobalt complexes such as cobalt(II) acetylacetonate and cobalt(III) acetylacetonate, organic copper complexes such as copper(II) acetylacetonate, organic zinc complexes such as zinc(II) acetylacetonate, organic iron complexes such as iron(III) acetylacetonate, organic nickel complexes such as nickel(II) acetylacetonate, and organic manganese complexes such as manganese(II) acetylacetonate. Examples of organometallic salts include zinc octoate, tin octoate, zinc naphthenate, cobalt naphthenate, tin stearate, and zinc stearate.

[0206] The content of component (G) in the resin composition is not particularly limited, but 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, when the resin components in the resin composition are taken as 100% by mass.

[0207] [Other additives] In addition to the above-mentioned components, the resin composition of the present invention may further contain other additives as optional components. Examples of the other additives include organometallic compounds such as organocopper compounds, organozinc compounds, and organocobalt compounds; colorants such as phthalocyanine blue, phthalocyanine green, iodine green, diazo yellow, crystal violet, titanium oxide, and carbon black; polymerization inhibitors such as hydroquinone, catechol, pyrogallol, and phenothiazine; leveling agents such as silicone-based leveling agents and acrylic polymer-based leveling agents; thickeners such as bentone 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 promoters such as triazole-based adhesion promoters, tetrazole-based adhesion promoters, and triazine-based adhesion promoters; and antioxidants such as hindered phenol-based antioxidants. surfactants such as fluorine-based surfactants and silicone-based surfactants; flame retardants such as phosphorus-based flame retardants (e.g., phosphate ester compounds, phosphazene compounds, phosphinic acid compounds, and red phosphorus), nitrogen-based flame retardants (e.g., melamine sulfate), halogen-based flame retardants, and inorganic flame retardants (e.g., antimony trioxide); dispersants such as phosphate ester-based dispersants, polyoxyalkylene-based dispersants, acetylene-based dispersants, silicone-based dispersants, anionic dispersants, and cationic dispersants; 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; photopolymerization initiation aids such as tertiary amines; and photosensitizers such as pyrarizones, anthracenes, coumarins, xanthones, and thioxanthones. The other additives may be used singly or in combination of two or more.

[0208] [solvent] The resin composition of the present invention may contain a solvent as a volatile component in addition to the non-volatile components described above. Any known solvent can be used as appropriate, and the type is not particularly limited. Organic solvents are preferred. Examples of the solvent include ketone-based solvents such as acetone, methyl ethyl ketone, methyl isobutyl ketone, and cyclohexanone; ester-based solvents such as methyl acetate, ethyl acetate, butyl acetate, isobutyl acetate, isoamyl acetate, methyl propionate, ethyl propionate, and γ-butyrolactone; ether-based solvents such as tetrahydropyran, tetrahydrofuran, 1,4-dioxane, diethyl ether, diisopropyl ether, dibutyl ether, diphenyl ether, and anisole; alcohol-based solvents such as methanol, ethanol, propanol, butanol, and ethylene glycol; 2-ethoxyethyl acetate, propylene glycol monomethyl ether acetate, diethylene glycol monoethyl ether acetate, ethyl diglycol acetate, γ-butyrolactone, and methyl methoxypropionate. Examples of suitable solvents include ether ester solvents such as ethanol; 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; and aromatic hydrocarbon solvents such as benzene, toluene, xylene, ethylbenzene, and trimethylbenzene. The (J) solvent may be used singly or in combination of two or more in any ratio.

[0209] The amount of solvent is not particularly limited, but when all components in the resin composition are taken as 100% by mass, it may be, for example, 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, or even 0% by mass.

[0210] [Method of producing resin composition] The resin composition of the present invention can be produced, for example, by mixing components that can be contained in the resin composition. The above-mentioned components may be mixed in part or all at the same time, or may be mixed sequentially. In the process of mixing each component, the temperature may be appropriately set, and thus heating and / or cooling may be performed temporarily or throughout. Furthermore, stirring or shaking may be performed in the process of mixing each component.

[0211] [Characteristics of resin composition] The cured product of the resin composition of the present invention can have a low dielectric loss tangent. Therefore, when an insulating layer is formed using this cured product, an insulating layer with a low dielectric loss tangent can be obtained. The dielectric loss 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. There is no particular lower limit, but it can be 0.0001 or more. The dielectric loss 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 high elongation at break. Therefore, when an insulating layer is formed using 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 is not particularly limited, but can be, for example, 10% or less. 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 excellent crack resistance. Therefore, when an insulating layer is formed using this cured product, an insulating layer with excellent crack resistance can be obtained. Specifically, the resin composition is laminated on an inner layer substrate on which a wiring pattern has been formed, and then thermally cured to obtain a cured product. The surface of the cured product is roughened to obtain a sample. 100 sections on the pattern of the sample inner layer substrate are checked for cracks along the pattern shape, and the number of sections on the pattern without cracks is counted. The percentage of crack-free sections out of the 100 sections is calculated as the "yield." In this case, the yield is preferably 40% or more, more preferably 60% or more, and even more preferably 80% or more. Crack resistance can be measured by the method described in the Examples below.

[0214] [Uses 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 an insulating layer of a printed wiring board), and more suitably used as a resin composition for forming an interlayer insulating layer of a printed wiring board (resin composition for an interlayer insulating layer of a printed wiring board). The resin composition of the present invention can also be suitably used when the printed wiring board is a circuit board with built-in components. The resin composition of the present invention can also be suitably used as a resin composition for forming an insulating layer of a rewiring board for a semiconductor package (resin composition for an insulating layer of a rewiring board). In the present invention, printed wiring boards and rewiring boards are collectively referred to as "circuit boards," and therefore the resin composition of the present invention can be suitably used for an insulating layer of a circuit board.

[0215] The resin composition of the present invention can further be used in a wide range of applications requiring a resin composition, such as sheet-like laminate materials such as resin sheets and prepregs, solder resists, underfill materials, die bonding materials, hole filling resins, sealing resins, and component embedding resins.

[0216] [Sheet-type laminated material] The resin composition may be used by applying it in the form of a varnish, but from an industrial perspective, it is preferable to use it in the form of a sheet-like laminate material containing the resin composition.

[0217] As the sheet-like laminate material, the following resin sheets and prepregs 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 from the resin composition described above. Therefore, the resin composition layer usually contains a resin composition, and preferably contains only a resin composition.

[0219] The thickness of the resin composition layer is preferably 50 μm or less, more preferably 40 μm or less, from the viewpoint of achieving a thinner film and being able to provide a cured product having excellent insulating properties even when thin, using the resin composition. 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 thermoplastic resin films, metal foils, and release papers, with thermoplastic resin films and metal foils being 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), polyether sulfide (PES), polyether ketone, polyimide, etc. Among these, polyethylene terephthalate and polyethylene naphthalate are preferred, with inexpensive polyethylene terephthalate being particularly preferred.

[0222] When a metal foil is used as the support, examples of the metal foil include copper foil and aluminum foil, with copper foil being preferred. The copper foil may be a foil made of a single metal, copper, or an alloy of copper and another metal (e.g., tin, chromium, silver, magnesium, nickel, zirconium, silicon, titanium, etc.).

[0223] The surface of the support that is to be bonded to the resin composition layer may be subjected to a matte treatment, a corona treatment, or an antistatic treatment.

[0224] The support may be a support with a release layer, which has a release layer on the surface that bonds with the resin composition layer. Examples of the release agent used in the release layer of the support with a release layer include one or more release agents selected from the group consisting of alkyd resins, polyolefin resins, urethane resins, and silicone resins. Commercially available products may be used as the support with a release layer, including, for example, "SK-1," "AL-5," and "AL-7" manufactured by Lintec Corporation, "Lumirror T60" manufactured by Toray Industries, Inc., "Purex" manufactured by Teijin Limited, and "Uni-Peel" manufactured by Unitika Limited, which are PET films having a release layer primarily composed of an alkyd resin-based release agent.

[0225] The thickness of the support is not particularly limited, but is preferably in the range of 5 μm to 75 μm, more preferably 10 μm to 60 μm. When a support with a release layer is used, it is preferable that the thickness of the entire support with a release layer is in the above range.

[0226] When a metal foil is used as the support, a metal foil with a support substrate may be used, which is a thin metal foil with a peelable support substrate attached thereto. In one embodiment, the metal foil with a support substrate includes a support substrate, a release layer provided on the support substrate, and a metal foil provided on the release layer. When a metal foil with a support substrate is used as the support, the resin composition layer is provided on the metal foil.

[0227] In the metal foil with a supporting substrate, the material of the supporting substrate is not particularly limited, but examples thereof include copper foil, aluminum foil, stainless steel foil, titanium foil, copper alloy foil, etc. When copper foil is used as the supporting substrate, it may be electrolytic copper foil or rolled copper foil. Furthermore, the release layer is not particularly limited as long as it allows the metal foil to be released from the supporting substrate, and examples thereof include an alloy layer of an element selected from the group consisting of Cr, Ni, Co, Fe, Mo, Ti, W, and P; an organic coating, etc.

[0228] In the metal foil with a supporting substrate, the material of the metal foil is preferably, for example, copper foil or copper alloy foil.

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

[0230] In one embodiment, the resin sheet may further include an optional layer as needed. Examples of such optional layers include a protective film conforming to the support and provided on the surface of the resin composition layer that is not bonded to the support (i.e., the surface opposite the support). The thickness of the protective film is not particularly limited, but is, for example, 1 μm to 40 μm. By laminating the protective film, it is possible to prevent dust from adhering to the surface of the resin composition layer and scratches.

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

[0232] The solvent may be the same as the solvent explained as a component of the resin composition. One type of solvent may be used alone, or two or more types may be used in combination.

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

[0234] The resin sheet can be stored in a rolled state. 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 substrate with the resin composition according to this embodiment.

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

[0237] The prepreg can be produced by a method such as a hot melt method or a solvent method.

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

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

[0240] [Circuit board] The resin composition of the present invention can be used to form an insulating layer for a circuit board. The present invention also provides such a circuit board, i.e., a circuit board comprising an insulating layer made of a cured product of the resin composition of the present invention.

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

[0243] The "inner layer substrate" used in step (I) is a member that will become the substrate of a printed wiring board, and examples thereof include glass epoxy substrates, metal substrates, polyester substrates, polyimide substrates, BT resin substrates, and thermosetting polyphenylene ether substrates. The substrate may have a conductor layer on one or both sides, and this conductor layer may be patterned. An inner layer substrate having a conductor layer (circuit) formed on one or both sides of the substrate may be referred to as an "inner layer circuit board." Furthermore, the "inner layer substrate" of the present invention also includes intermediate products on which an insulating layer and / or a conductor layer is to be further formed during the production of a printed wiring board. When the printed wiring board is a circuit board with built-in components, an inner layer substrate with built-in components may be used.

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

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

[0246] The lamination can be performed using a commercially available vacuum laminator, such as a vacuum pressure laminator manufactured by Meiki Seisakusho Co., Ltd., a vacuum applicator manufactured by Nikko Materials Co., Ltd., or a batch vacuum pressure laminator.

[0247] After lamination, the laminated resin sheets may be smoothed under normal pressure (atmospheric pressure), for example, by pressing a thermocompression member from the support side. The pressing conditions for the smoothing treatment may be the same as the thermocompression conditions for lamination. The smoothing treatment may be performed using a commercially available laminator. Note that lamination and smoothing treatment may be performed consecutively using the commercially available vacuum laminator.

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

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

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

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

[0253] In another embodiment, the printed wiring board of the present invention can be produced using the above-mentioned prepreg. The production method is basically the same as when a resin sheet is used.

[0254] Step (III) is a step of drilling holes in the insulating layer, thereby forming holes such as via holes and through holes in the insulating layer. Step (III) may be performed using, for example, a drill, a laser, plasma, or the like, depending on the composition of the resin composition used to form the insulating layer. The dimensions and shape of the holes may be determined appropriately depending on the design of the printed wiring board.

[0255] Step (IV) is a step of roughening the insulating layer. Usually, in this step (IV), smear removal (desmear) is also performed. The procedure and conditions of the roughening treatment are not particularly limited, and known procedures and conditions commonly used in forming insulating layers for printed wiring boards can be adopted. For example, the insulating layer can be roughened by performing a swelling treatment with a swelling liquid, a roughening treatment with an oxidizing agent, and a neutralization treatment with a neutralizing liquid in this order.

[0256] The swelling liquid used in the roughening treatment is not particularly limited, but examples thereof include alkaline solutions and surfactant solutions, and is preferably an alkaline solution, with sodium hydroxide solution and potassium hydroxide solution being more preferred. Commercially available swelling liquids include "Swelling Dip Securigance P" and "Swelling Dip Securigance SBU" manufactured by Atotech Japan. The swelling treatment using a swelling liquid is not particularly limited, but can be carried out by, for example, immersing the insulating layer in a swelling liquid at 30°C to 90°C for 1 to 20 minutes. From the viewpoint of suppressing swelling of the resin in the insulating layer to an appropriate level, it is preferable to immerse the insulating layer in a swelling liquid at 40°C to 80°C for 5 to 15 minutes.

[0257] The oxidizing agent used in the roughening treatment is not particularly limited, but examples include alkaline permanganate solutions prepared by dissolving potassium permanganate or sodium permanganate in an aqueous solution of sodium hydroxide. Roughening treatment using an oxidizing agent such as alkaline permanganate solution is preferably carried out by immersing the insulating layer in an oxidizing agent solution heated to 60°C to 100°C for 10 to 30 minutes. The concentration of permanganate in the alkaline permanganate solution is preferably 5% by mass to 10% by mass. Commercially available oxidizing agents include alkaline permanganate solutions such as "Concentrate Compact CP," "Concentrate Compact P," and "Dosing Solution Securigance P" manufactured by Atotech Japan.

[0258] The neutralizing solution used in the roughening treatment is preferably an acidic aqueous solution, and examples of commercially available products include "Reduction Solution Securigant P" manufactured by Atotech Japan.

[0259] Treatment with a neutralizing solution can be carried out by immersing the surface that has been roughened with an oxidizing agent in a neutralizing solution at 30° C. to 80° C. for 5 to 30 minutes. From the standpoint of workability, etc., a method in which the object that has been roughened with an oxidizing agent is immersed in a neutralizing solution at 40° C. to 70° C. for 5 to 20 minutes is preferred.

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

[0261] The conductor layer may have a single layer structure or a multi-layer structure in which two or more single metal layers or alloy layers made of different types of metals or alloys are laminated. When the conductor layer has a multi-layer structure, the layer in contact with the insulating layer is preferably a single metal layer of chromium, zinc, or titanium, or an alloy layer of a nickel-chromium alloy.

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

[0263] In one embodiment, the conductor layer may be formed by plating. From the viewpoint of facilitating the formation of fine wiring, it is preferable to form the conductor layer by a semi-additive method. An example of forming the conductor layer by a semi-additive method will be described below.

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

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

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

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

[0268] <Rewiring substrate for semiconductor packages> In one embodiment, the circuit board of the present invention is a rewiring substrate (rewiring layer) of a semiconductor package. Hereinafter, a method for manufacturing a semiconductor package will be described.

[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 a rewiring substrate. The semiconductor package may also include a sealing layer made of a cured product of the resin composition of the present invention.

[0270] A semiconductor package can be produced, for example, by a method including the following steps (1) to (6) using the resin composition and resin sheet of the present invention. The resin composition and resin sheet of the present invention can be used to form a rewiring formation layer (insulating layer for forming a rewiring substrate) in step (5) or a sealing layer in step (3). An example of forming a rewiring formation layer or a sealing layer using a resin composition or a resin sheet will be shown below. However, techniques for forming a rewiring formation layer or a sealing layer for a semiconductor package are known, and a person skilled in the art can produce a semiconductor package using the resin composition and resin sheet of the present invention according to known techniques. (1) a step of laminating a temporary fixing film on a substrate; (2) a step of temporarily fixing a semiconductor chip on a temporary fixing film; (3) forming an encapsulation layer on the semiconductor chip; (4) peeling the substrate and the temporary fixing film from the semiconductor chip; (5) forming a rewiring formation layer as an insulating layer on the surface of the semiconductor chip from which the base material and the temporary fixing film have been peeled off; and (6) A step of forming a rewiring layer as a conductor layer on the rewiring formation layer.

[0271] -Process (1)- The material used for the substrate is not particularly limited. Examples of the substrate include semiconductor wafers such as silicon wafers, glass wafers, glass substrates, metal substrates such as copper, titanium, stainless steel, and cold-rolled steel sheets (SPCC), substrates in which glass fibers are impregnated with epoxy resin or the like and then thermoset (e.g., FR-4 substrates), and substrates made of bismaleimide triazine resin (BT resin).

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

[0273] -Process (2)- The semiconductor chips can be temporarily fixed using known devices such as a flip chip bonder, a die bonder, etc. The layout and number of semiconductor chips to be arranged can be appropriately set depending on the shape and size of the temporary fixing film, the number of semiconductor packages to be produced, etc., and for example, the semiconductor chips can be temporarily fixed by arranging them in a matrix of multiple rows and multiple columns.

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

[0275] For example, lamination of a semiconductor chip and a resin sheet can be performed by removing the protective film from the resin sheet and then thermocompressing the resin sheet to the semiconductor chip from the support side. Examples of a member for thermocompressing the resin sheet to the semiconductor chip (hereinafter also referred to as a "thermocompression member") include a heated metal plate (such as a SUS plate) or a metal roll (SUS roll). It is preferable to press the thermocompression member not directly onto the resin sheet, but via an elastic material such as heat-resistant rubber, so that the resin sheet can adequately conform to the surface irregularities of the semiconductor chip. The semiconductor chip and resin sheet can also be laminated by a vacuum lamination method, and the lamination conditions and preferred ranges are the same as those described in relation to the method for manufacturing a printed wiring board.

[0276] After lamination, the resin composition is thermally cured to form the sealing layer under the same conditions as those described in relation to the method for producing a printed wiring board.

[0277] The support of the resin sheet may be peeled off after the resin sheet is laminated on the semiconductor chip and thermally cured, or the support may be peeled off before the resin sheet is laminated on the semiconductor chip.

[0278] When forming a sealing layer by applying the resin composition of the present invention, the application conditions are the same as the application conditions when forming the resin composition layer described in relation to the resin sheet of the present invention, and the preferred ranges are also the same.

[0279] -Process (4)- The method for peeling off the substrate and the temporary fixing film can be changed as appropriate depending on the material of the temporary fixing film, etc., and examples include a method in which the temporary fixing film is heated and foamed (or expanded) to peel it off, and a method in which ultraviolet light is irradiated from the substrate side to reduce the adhesive strength of the temporary fixing film and peel it off.

[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. In the method of irradiating ultraviolet light from the substrate side to reduce the adhesive strength of the temporary fixing film to peel it off, the irradiation dose of ultraviolet light is usually 10 mJ / cm. 2 ~1000mJ / cm 2 is.

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

[0282] After forming the redistribution layer, via holes may be formed in the redistribution layer to connect the semiconductor chip to a conductor layer (described later). The via holes may be formed by a known method depending on the material of the redistribution layer.

[0283] -Process (6)- The formation of the conductor layer on the rewiring formation layer may be carried out in the same manner as in step (V) described in relation to the method for producing a printed wiring board. Note that steps (5) and (6) may be repeated to alternately stack (build up) the conductor layer (rewiring layer) and the rewiring formation layer (insulating layer).

[0284] The manufacturing of the semiconductor package may further include steps of (7) forming a solder resist layer on the conductor layer (rewiring layer), (8) forming bumps, and (9) dicing the multiple semiconductor packages into individual semiconductor packages. These steps may be performed according to various methods known to those skilled in the art that are used in the manufacturing of semiconductor packages.

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

[0286] [Semiconductor Devices] The semiconductor device of the present invention includes a layer made of a cured product of the resin composition layer of the present invention. The semiconductor device of the present invention can be produced using the circuit board of the present invention.

[0287] Examples of semiconductor devices include various semiconductor devices used in electrical appliances (e.g., computers, mobile phones, smartphones, tablet devices, wearable devices, digital cameras, medical equipment, and televisions) and vehicles (e.g., motorcycles, automobiles, trains, ships, and aircraft). [Example]

[0288] The present invention will be specifically described below 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 "% by mass", respectively, unless otherwise specified. Unless otherwise specified, the temperature and pressure conditions 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 overnight at room temperature under a nitrogen gas atmosphere. Water was added to the reaction mixture, and the 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 desired resin A as white crystals. This resin A has the structure represented by the following formula:

[0290] [ka]

[0291] (Synthesis Example 2: Synthesis of Maleimide B) An MEK solution (70% by mass of non-volatile components) 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 the Japan Institute of Invention and Innovation's Technical Journal, Publication No. 2020-500211 was prepared. This maleimide B has the structure represented by the following formula. [ka]

[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. The reaction was allowed to proceed for 4 hours. The polymerization solution was terminated with aqueous sodium bicarbonate solution, and the oil layer was washed three times with pure water. The polymer was recovered by devolatilization under reduced pressure at 60 °C. The resulting product was weighed, confirming 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) (Adjustment of resin varnish) Each component was weighed out in the parts by mass shown in Table 1, and then mixed with 10 parts of MEK and 2 parts of cyclohexanone, and the mixture was uniformly dispersed using a high-speed rotating mixer to obtain a resin varnish.

[0294] [Table 1]

[0295] The details of each component listed in Table 1 are as follows: (A) A compound represented by formula (A-1) Resin A: Synthesized in Synthesis Example 1 (B) Maleimide resin MIR-3000-70MT: toluene solution with functional group equivalent weight of 275 and non-volatile content of 70% by mass, manufactured by Nippon Kayaku Co., Ltd. Maleimide B: Synthesized in Synthesis Example 2 SLK-6895-T90: Toluene solution with functional group equivalent weight of 345 and 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 weight of 151 and a non-volatile content of 50% by mass, manufactured by DIC Corporation HP-4032-SS: Functional group equivalent weight 144, manufactured by DIC Corporation HPC-8000-65T: Functional group equivalent weight 223, non-volatile content 62% toluene solution, manufactured by DIC V-03: Toluene solution with functional group equivalent weight of 216 and non-volatile content of 50% by mass, manufactured by Nisshinbo Chemical Inc. DAD: Functional group equivalent weight 161, manufactured by Nisshoku Techno Fine Chemical Co., Ltd. Vinyl resin C: toluene solution (non-volatile components 50% by mass) of the resin synthesized in Synthesis Example 3 OPE-2St: toluene solution with functional group equivalent of 590 and non-volatile content of 65% by mass, manufactured by Mitsubishi Gas Chemical Co., Ltd. (D) Thermoplastic resin P2000: Styrene butadiene elastomer, manufactured by Asahi Kasei Corporation PIAD200: Polyimide resin, 30% non-volatile mixed solution of cyclohexanone, dimethyl glycol and methylcyclohexane, manufactured by Arakawa Chemical Co., Ltd. YX7553BH30: Phenoxy resin, 1:1 solution of MEK and cyclohexanone with 30% non-volatile content, manufactured by Mitsubishi Chemical Corporation (E) Inorganic filler SO-C2: Spherical silica surface-treated with an amine-based alkoxysilane compound ("KBM573" manufactured by Shin-Etsu Chemical Co., Ltd.), average particle size 0.5 μm, specific surface area 5.8 m 2 / g, manufactured by Admatechs Co., Ltd. (F) Radical polymerization initiator Perhexyl D: NOF Corporation (G) Curing accelerator 1B2PZ: Shikoku Chemicals Corporation

[0296] <Test Example 1: Measurement of dielectric loss tangent (Df)> (1) Preparation of resin sheet A having a resin composition layer thickness of 40 μm A polyethylene terephthalate film ("AL5" manufactured by Lintec Corporation, thickness 38 μm) with a release layer was prepared as a support. The varnish-like resin compositions obtained in the Examples and Comparative Examples were uniformly applied onto the release layer of this support so 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 a support and a resin composition layer. (2) Preparation of hardened product The obtained resin sheet A was cured for 90 minutes in an oven at 190° C. The support was peeled off from the resin sheet A taken out of the oven to obtain a cured resin composition layer. (3) Measurement of dielectric loss tangent (Df) The cured product was cut into a piece of 80 mm long and 2 mm wide, and the dielectric loss tangent (Df value) was measured by the cavity resonance perturbation method using an Agilent Technologies HP8362B at a measurement frequency of 5.8 GHz and measurement temperatures of 23°C and 90°C. Measurements were performed on two test pieces, and the average was calculated.

[0297] <Test Example 2: Measurement of elongation at break> The cured product obtained in Test Example 1(2) was subjected to tensile strength measurement using an Orientec tensile testing machine "RTC-1250A" to measure the strength at break and elongation at break at 23°C. The measurement was carried out in accordance with JIS K7127. The measurement was carried out five times, and the average of the top three points was calculated.

[0298] <Test Example 3: Evaluation of crack resistance> (1) Laminating resin sheets An inner layer substrate ("MCL-E700G" manufactured by Resonac Corporation) having circuit conductors (copper) formed on both sides with a wiring pattern of L / S = 8 μm / 8 μm, conductor layer thickness 35 μm, total thickness 0.4 mm, residual copper ratio 40%) was prepared. Resin sheets were laminated on both sides of this inner layer substrate so that the resin composition layer was in contact with the inner layer substrate. This lamination was performed using a vacuum pressure laminator ("MVLP-500" manufactured by Meiki Seisakusho Co., Ltd.) by vacuum suction at a temperature of 120°C for 30 seconds, followed by lamination at a temperature of 120°C and a pressure of 7.0 kg / cm. 2Then, the substrate was pressed for 30 seconds using a heat-resistant rubber sheet under atmospheric pressure at a temperature of 120°C and a pressure of 5.5 kg / cm using a stainless steel end plate. 2 The press was performed for 60 seconds under the conditions. (2) Thermal curing of the resin composition layer The resin composition layer was thermally cured by heating at 130°C for 30 minutes, and then at 170°C for 30 minutes to obtain an insulating layer as a cured product layer made of the cured product of the resin composition. The support was then 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 roughened. Specifically, the sample substrate was immersed in a swelling solution, Securiganth P (Atotech Japan), at 60°C for 10 minutes. Next, it was immersed in a roughening solution, Concentrate Compact P (Atotech Japan), at 80°C for 20 minutes. Finally, it was immersed in a neutralizing solution, Reduction Solution Securiganth P (Atotech Japan), at 40°C for 5 minutes. (4) Crack evaluation After the roughening treatment, the insulating layer surface was observed on the L / S pattern of the inner layer substrate. The surface of 100 inner layer substrates was checked for cracks along the pattern shape, and the percentage of the number of areas on the pattern where cracks did not occur was counted. This percentage was calculated as the "yield." The calculated yield was then scored according to the following criteria. 1 point: 0% or more but less than 20%. 2 points: 20% or more but less than 40%. 3 points: 40% or more but less than 60%. 4 points: 60% or more but less than 80%. 5 points: 80% or above. A score of 4 or more was evaluated as ◎, a score of 3 as "○", and a score of 2 or less as "×".

Claims

1. (A) A compound represented by the following formula (A-1): 【Chemistry 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): 【Chemistry 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 be joined together to form a ring. a represents a number ranging from 0 to 5. 【Transformation 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 formula (A-4). b and c each independently represent a number ranging from 0 to 5. 【Chemistry 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 be joined together to form a ring. d represents a number ranging from 0 to 5. (B) a maleimide resin, and (C) Thermosetting resin (excluding maleimide resin) Contains The component (A) is 2 to 15% by mass when the resin component in the resin composition is 100% by mass, The (B) component is 20 to 80% by mass when the resin component in the resin composition is 100% by mass, A resin composition in which the component (C) is 5 to 60% by mass when the resin component in the resin composition is 100% by mass.

2. (A) A compound represented by the following formula (A-1): 【Transformation 5】 (In formula (A-1), X represents a divalent group represented by the following formula (A-5): 【Transformation 6】 (In formula (A-5), Each Rs independently represents 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, and 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 bonded together to form a ring; n1 and n2 each independently represent a number ranging from 0 to 4; m represents a number ranging from 1 to 5; "*" represents a bond.) (B) a maleimide resin, and (C) Thermosetting resin (excluding maleimide resin) Contains The component (A) is 2 to 15% by mass when the resin component in the resin composition is 100% by mass, The (B) component is 20 to 80% by mass when the resin component in the resin composition is 100% by mass, A resin composition in which the component (C) is 5 to 60% by mass when the resin component in the resin composition is 100% by mass.

3. (A) A compound represented by the following formula (A-1): 【Transformation 7】 (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): 【Transformation 8】 (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 be joined together to form a ring. a represents a number ranging from 0 to 5. 【Chemistry 9】 (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 formula (A-4). b and c each independently represent a number ranging from 0 to 5. 【Chemistry 10】 (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 be joined together to form a ring. d represents a number ranging from 0 to 5. (B) a maleimide resin, and (C) Thermosetting resin (excluding maleimide resin) Contains The component (A) is 2 to 15% by mass when the resin component in the resin composition is 100% by mass, The (B) component is 20 to 80% by mass when the resin component in the resin composition is 100% by mass, A resin composition for an insulating layer of a circuit board, wherein the component (C) is 5 to 60% by mass when the resin component in the resin composition is 100% by mass.

4. (A) A compound represented by the following formula (A-1): 【Chemistry 11】 (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): 【Chemistry 12】 (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 be joined together to form a ring. a represents a number ranging from 0 to 5. 【Chemistry 13】 (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 formula (A-4). b and c each independently represent a number ranging from 0 to 5. 【Chemistry 14】 (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 be joined together to form a ring. d represents a number ranging from 0 to 5. (B) a maleimide resin, and (C) Thermosetting resin (excluding maleimide resin) Contains The component (A) is 2 to 15% by mass when the resin component in the resin composition is 100% by mass, The (B) component is 20 to 80% by mass when the resin component in the resin composition is 100% by mass, The component (C) is 5 to 60% by mass when the resin component in the resin composition is 100% by mass, A resin composition in which the mass ratio of the component (A) to the component (B) (component (A) / component (B)) is 0.4 or less.

5. (A) A compound represented by the following formula (A-1): 【Chemistry 15】 (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): 【Chemistry 16】 (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 be joined together to form a ring. a represents a number ranging from 0 to 5. 【Chemistry 17】 (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 formula (A-4). b and c each independently represent a number ranging from 0 to 5. [Chemistry 18] (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 be joined together to form a ring. d represents a number ranging from 0 to 5. (B) a maleimide resin, and (C) Thermosetting resin (excluding maleimide resin) Contains The component (C) contains one or more resins selected from the group consisting of epoxy resins, phenolic resins, and terminal double bond resins, The component (A) is 2 to 15% by mass when the resin component in the resin composition is 100% by mass, The (B) component is 20 to 80% by mass when the resin component in the resin composition is 100% by mass, A resin composition in which the component (C) is 5 to 60% by mass when the resin component in the resin composition is 100% by mass.

6. R in formula (A-2) and formula (A-3) 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 any one of claims 1 and 3 to 5.

7. R in formula (A-4) 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 any one of claims 1 and 3 to 5.

8. L in formula (A-2) 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, or a sulfonyl group.

9. L in formula (A-2) 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.

10. The resin composition according to any one of claims 1 and 3 to 5, wherein X in formula (A-1) is a group represented by the following formula (A-5): 【Chemistry 19】 (In formula (A-5), Each Rs independently represents 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, and ２１ is a divalent aliphatic group which may have a substituent, L ２１ and the benzene ring on the left may be bonded together to form a ring, n1 and n2 each independently represent a number ranging from 0 to 4; m represents a number ranging from 0 to 5; "*" represents a bond.)

11. The resin composition according to any one of claims 1 to 5, wherein the content of component (A) is 2% by mass or more and 12% by mass or less, when the resin component in the resin composition is 100% by mass.

12. The resin composition according to any one of claims 1 to 5, wherein the content of the component (B) is 20% by mass or more and 75% by mass or less, when the resin component in the resin composition is 100% by mass.

13. The resin composition according to any one of claims 1 to 4, wherein the component (C) comprises at least one resin selected from the group consisting of epoxy resins, phenolic resins, and terminal double bond resins.

14. The resin composition according to any one of claims 1 to 5, wherein the content of the component (C) is 10% by mass or more and 50% by mass or less, when the resin component in the resin composition is 100% by mass.

15. The resin composition according to any one of claims 1 to 5, further comprising (D) a thermoplastic resin.

16. The resin composition according to any one of claims 1 to 5, further comprising (E) an inorganic filler.

17. The resin composition according to claim 16, wherein the content of the component (E) is 50% by mass or more when the nonvolatile components in the resin composition are 100% by mass.

18. The resin composition according to any one of claims 1 to 5, which is used for an insulating layer of a circuit board.

19. A cured product of the resin composition according to any one of claims 1 to 5.

20. A resin sheet comprising a support and a layer of the resin composition according to any one of claims 1 to 5 provided on the support.

21. The resin sheet according to claim 20, wherein the support is a thermoplastic resin film or a metal foil.

22. A circuit board comprising an insulating layer made of a cured product of the resin composition according to any one of claims 1 to 5.

23. A semiconductor device comprising the circuit board according to claim 22.

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