JP6718588B2 - Resin composition, prepreg, metal foil-clad laminate, resin sheet and printed wiring board - Google Patents

Description

TECHNICAL FIELD The present invention relates to a resin composition, a prepreg, a metal foil-clad laminate using the resin composition and the prepreg, a resin sheet, and a printed wiring board using the same.

In recent years, high integration and miniaturization of semiconductors widely used in electronic devices, communication devices, personal computers, etc. have been accelerated. Along with this, various characteristics required for semiconductor package laminates used for printed wiring boards are becoming more and more severe. The properties required include, for example, properties such as low water absorption, moisture absorption heat resistance, flame retardancy, low dielectric constant, low dielectric loss tangent, low thermal expansion coefficient, heat resistance, chemical resistance, and high plating peel strength. However, so far, these required characteristics have not necessarily been satisfied.

Conventionally, cyanate ester compounds have been known as resins for printed wiring boards that are excellent in heat resistance and electrical characteristics, and in recent years, resin compositions in which cyanate ester compounds have been used in combination with epoxy resins, bismaleimide compounds, etc. are semiconductor plastic packages. It is widely used as a high-performance printed wiring board material for automobiles.
Further, due to the miniaturization and high density of the multilayer printed wiring board, the build-up layers used for the multilayer printed wiring board are multi-layered, and miniaturization and high density of wiring are required. Along with this, studies for thinning the laminated plate used for the build-up layer are being actively conducted.
Further, since a problem of expansion of warpage occurs in a multilayer printed wiring board, a resin composition used as a material for an insulating layer is required to have a high glass transition temperature.

International Publication No. 2013/065694 Pamphlet International publication 2014/203866 pamphlet

For example, Patent Documents 1 and 2 propose a resin composition composed of a cyanate ester compound and an epoxy resin, which has excellent properties such as adhesion, low water absorption, heat resistance after moisture absorption, and insulation reliability. Since the heat resistance is still insufficient, further improvement in properties is required. Among them, the epoxy resin is generally a resin having excellent adhesion, fluidity and processability, and various epoxy resins having different structures have been used for the purpose of imparting further properties.

It is an object of the present invention to provide a resin composition capable of realizing a printed wiring board having an excellent glass transition temperature, a prepreg and a single layer or laminated sheet using the same, and a metal foil-clad using the prepreg. It is to provide a laminated board, a printed wiring board, and the like.

As a result of diligent studies on the above problems, the inventors of the present invention have achieved high glass by using a resin composition containing an epoxy resin (A) represented by the general formula (1) and a cyanate ester compound (B). They have found that a cured product having a transition temperature can be obtained and have reached the present invention. That is, the present invention is as follows.

1. A resin composition containing an epoxy resin (A) represented by the following general formula (1) and a cyanate ester compound (B).
(In the formula, R represents an alkyl group having 1 to 3 carbon atoms, n represents an integer of 1 to 20, and n may be a different mixture.)

2. The content of the epoxy resin (A) in the resin composition is 1 to 90 parts by mass with respect to 100 parts by mass of the resin solid content. The resin composition according to.

3. Further, containing a filler (C), 1. Or 2. The resin composition according to.

4. Furthermore, among the group selected from epoxy resins other than the epoxy resin (A) represented by the general formula (1), maleimide compounds, phenol resins, oxetane resins, benzoxazine compounds, and compounds having a polymerizable unsaturated group. , Containing any one or more of: ~3. The resin composition according to any one of 1.

5. 2. The content of the filler (C) in the resin composition is 50 to 1600 parts by mass with respect to 100 parts by mass of the resin solid content. Or 4. The resin composition according to.

6. 1. A base material and, if impregnated or applied to the base material, 1. ~5. A prepreg having the resin composition according to any one of 1.

7. At least one or more sheets are laminated 6. A metal foil-clad laminate comprising the prepreg according to claim 1 and a metal foil arranged on one side or both sides of the prepreg.

8. A support and a surface of the support, ~5. A resin sheet having the resin composition according to claim 1.

9. An insulating layer and a conductor layer formed on the surface of the insulating layer, wherein the insulating layer is 1. ~5. A printed wiring board comprising the resin composition according to claim 1.

According to the present invention, it is possible to realize a prepreg excellent in glass transition temperature, a resin sheet, a metal foil-clad laminate, etc., and it is possible to realize a high-performance printed wiring board, and its industrial practicality is extremely high. It is expensive.

Hereinafter, embodiments of the present invention will be described. The following embodiments are examples for explaining the present invention, and the present invention is not limited to the embodiments.

The epoxy resin (A) used in this embodiment is represented by the following general formula (1).
(In the formula, R represents an alkyl group having 1 to 3 carbon atoms, n represents an integer of 1 to 20, and n may be a different mixture.)
The resin cured product containing the epoxy resin (A) represented by the general formula (1) has an effect of improving the glass transition temperature.

R in the formula of the epoxy resin (A) represented by the general formula (1) has a carbon number of 1 to 3 which can be substituted at any position other than the site where the methylene group or glycidyl group of the aromatic ring to be substituted is substituted. Indicates an alkyl group. The carbon number is preferably 1 to 2, and more preferably 1. n is an integer of 1 to 20, preferably 1 to 15, and more preferably 1 to 10. When n is in the above range, the glass transition temperature of the obtained resin composition is improved.

As the epoxy resin (A) represented by the general formula (1), a commercially available epoxy resin may be used. An equivalent weight of 226 g/eq) can be preferably used.

The content of the epoxy resin (A) represented by the general formula (1) in the resin composition of the present embodiment can be appropriately set according to the desired characteristics, and is not particularly limited, but in the resin composition When the resin solid content is 100 parts by mass, 1 to 90 parts by mass is preferable. When the content is in the range of 1 to 90 parts by mass, a resin composition having excellent heat resistance can be obtained.
Here, unless otherwise specified, the "resin solid content in the resin composition" means a component in the resin composition excluding the solvent and the filler (C), and the resin solid content 100 parts by mass. The total of the components excluding the solvent and the filler (C) in the resin composition is 100 parts by mass.

The cyanate ester compound (B) used in the present embodiment is not particularly limited as long as it is a resin having in its molecule an aromatic moiety substituted with at least one cyanato group (cyanate ester group).

For example, those represented by the general formula (3) can be mentioned.
(In the formula, Ar ₁ represents a benzene ring, a naphthalene ring, or a single bond of two benzene rings. When there are a plurality of rings, they may be the same or different. Ra is each independently. Hydrogen atom, alkyl group having 1 to 6 carbon atoms, aryl group having 6 to 12 carbon atoms, alkoxyl group having 1 to 4 carbon atoms, alkyl group having 1 to 6 carbon atoms and aryl group having 6 to 12 carbon atoms The aromatic ring in Ra may have a substituent, and the substituent in Ar ₁ and Ra can be selected at any position, and p represents the number of cyanato groups bonded to Ar ₁ , Each of them is independently an integer of ₁ to 3. q represents the number of Ras bonded to Ar ₁ , 4-p when Ar ₁ is a benzene ring, 6-p when Ar ₁ is a naphthalene ring, and 2 benzene rings are When it is a single bond, it is 8-p, t is the average number of repetitions and is an integer of 0 to 50, and the other cyanate ester compound may be a mixture of compounds having different t. When there are a plurality of them, each independently, a single bond, a divalent organic group having 1 to 50 carbon atoms (a hydrogen atom may be substituted with a hetero atom), a divalent organic group having 1 to 10 nitrogen atoms. (For example, -N-R-N- (wherein R represents organic gas)), carbonyl group (-CO-), carboxy group (-C(=O)O-), carbonyldioxide group (-OC). (= O) O-), a sulfonyl group _(-SO 2 -), divalent indicate either a sulfur atom or a divalent oxygen atom).

The alkyl group represented by Ra in the general formula (3) may have either a linear or branched chain structure or a cyclic structure (for example, a cycloalkyl group).
Further, the hydrogen atom in the alkyl group in the general formula (3) and the aryl group in Ra is substituted with a halogen atom such as a fluorine atom or a chlorine atom, an alkoxyl group such as a methoxy group or a phenoxy group, or a cyano group or the like. Good.
Specific examples of the alkyl group include methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, n-pentyl group, 1-ethylpropyl group, 2,2-dimethylpropyl group. Group, cyclopentyl group, hexyl group, cyclohexyl group, and trifluoromethyl group.
Specific examples of the aryl group include phenyl group, xylyl group, mesityl group, naphthyl group, phenoxyphenyl group, ethylphenyl group, o-, m- or p-fluorophenyl group, dichlorophenyl group, dicyanophenyl group, trifluorophenyl group. Group, a methoxyphenyl group, and an o-, m- or p-tolyl group. Furthermore, examples of the alkoxyl group include a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, an n-butoxy group, an isobutoxy group, and a tert-butoxy group.
Specific examples of the divalent organic group having 1 to 50 carbon atoms in X of the general formula (3) include methylene group, ethylene group, trimethylene group, cyclopentylene group, cyclohexylene group, trimethylcyclohexylene group, biphenylyl. Examples thereof include a methylene group, a dimethylmethylene-phenylene-dimethylmethylene group, a fluorenediyl group, and a phthalidodiyl group. The hydrogen atom in the divalent organic group may be substituted with a halogen atom such as a fluorine atom and a chlorine atom, an alkoxyl group such as a methoxy group and a phenoxy group, a cyano group and the like.
Examples of the divalent organic group having 1 to 10 nitrogen atoms in X in the general formula (3) include an imino group and a polyimide group.

Examples of the organic group represented by X in the general formula (3) include those having a structure represented by the following general formula (4) or the following general formula (5).
Here, in the formula, Ar ₂ represents a benzenetetrayl group, a naphthalenetetrayl group or a biphenyltetrayl group, and when u is 2 or more, they may be the same or different from each other. Rb, Rc, Rf, and Rg are each independently a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 12 carbon atoms, a trifluoromethyl group, or an aryl having at least one phenolic hydroxy group. Indicates a group. Rd and Re are each independently selected from any one of a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 12 carbon atoms, an alkoxyl group having 1 to 4 carbon atoms, and a hydroxy group. .. u shows the integer of 0-5.
Here, in the formula, Ar ₃ represents a benzenetetrayl group, a naphthalenetetrayl group or a biphenyltetrayl group, and when v is 2 or more, they may be the same or different from each other. Ri and Rj are each independently a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 12 carbon atoms, a benzyl group, an alkoxyl group having 1 to 4 carbon atoms, a hydroxy group, a trifluoromethyl group, Alternatively, it represents an aryl group in which at least one cyanato group is substituted. v represents an integer of 0 to 5, but may be a mixture of compounds having different v.

Further, as X in the general formula (3), a divalent group represented by the following formula can be mentioned.
In the formula, z represents an integer of 4 to 7. Each Rk independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.
Specific examples of Ar ₂ of the general formula (4) and Ar ₃ of the general formula (5) include two carbon atoms represented by the general formula (4) or two oxygen atoms represented by the general formula (5). , A benzenetetrayl group bonded to the 1,4 position or the 1,3 position, the two carbon atoms or the two oxygen atoms are 4,4′ position, 2,4′ position, 2,2′ position, 2 , 3'-position, 3, 3'-position, or biphenyltetrayl group bonded to 3, 4'-position, and the above-mentioned two carbon atoms or two oxygen atoms are 2, 6-position, 1, 5-position .. Examples thereof include a naphthalenetetrayl group bonded to the 1,6 position, 1,8 position, 1,3 position, 1,4 position, or 2,7 position.
The alkyl group and aryl group in Rb, Rc, Rd, Re, Rf and Rg of the general formula (4), and Ri and Rj of the general formula (5) have the same meanings as in the above general formula (3).

Specific examples of the cyanato-substituted aromatic compound represented by the general formula (3) include cyanatobenzene, 1-cyanato-2-,1-cyanato-3-, or 1-cyanato-4-methylbenzene. -Cyanato-2-,1-cyanato-3-, or 1-cyanato-4-methoxybenzene, 1-cyanato-2,3-,1-cyanato-2,4-,1-cyanato-2,5-, 1-cyanato-2,6-,1-cyanato-3,4- or 1-cyanato-3,5-dimethylbenzene, cyanatoethylbenzene, cyanatobutylbenzene, cyanatooctylbenzene, cyanatononylbenzene, 2- (4-Cyanaphenyl)-2-phenylpropane (4-α-cumylphenol cyanate), 1-cyanato-4-cyclohexylbenzene, 1-cyanato-4-vinylbenzene, 1-cyanato-2- or 1- Cyanato-3-chlorobenzene, 1-cyanato-2,6-dichlorobenzene, 1-cyanato-2-methyl-3-chlorobenzene, cyanatonitrobenzene, 1-cyanato-4-nitro-2-ethylbenzene, 1-cyanato-2 -Methoxy-4-allylbenzene (cyanate of eugenol), methyl (4-cyanatophenyl) sulfide, 1-cyanato-3-trifluoromethylbenzene, 4-cyanatobiphenyl, 1-cyanato-2- or 1-cyanato -4-Acetylbenzene, 4-cyanatobenzaldehyde, 4-cyanatobenzoic acid methyl ester, 4-cyanatobenzoic acid phenyl ester, 1-cyanato-4-acetaminobenzene, 4-cyanatobenzophenone, 1-cyanato-2, 6-di-tert-butylbenzene, 1,2-dicyanatobenzene, 1,3-dicyanatobenzene, 1,4-dicyanatobenzene, 1,4-dicyanato-2-tert-butylbenzene, 1,4- Dicyanato-2,4-dimethylbenzene, 1,4-dicyanato-2,3,4-dimethylbenzene, 1,3-dicyanato-2,4,6-trimethylbenzene, 1,3-dicyanato-5-methylbenzene, 1-cyanato or 2-cyanatonaphthalene, 1-cyanato 4-methoxynaphthalene, 2-cyanato-6-methylnaphthalene, 2-cyanato-7-methoxynaphthalene, 2,2'-dicyanato-1,1'-binaphthyl, 1,3-,1,4-,1,5-,1,6-,1,7-,2,3-,2,6- or 2,7-dicyanatosinaphthalene, 2,2'-or 4,4'-dishes Anatobiphenyl, 4,4'-dicyanatooctafluorobiphenyl, 2,4'- or 4,4'-dicyanatodiphenylmethane, bis(4-cyanato-3,5-dimethylphenyl)methane, 1,1-bis( 4-cyanatophenyl)ethane, 1,1-bis(4-cyanatophenyl)propane, 2,2-bis(4-cyanatophenyl)propane, 2,2-bis(4-cyanato-3-methylphenyl) ) Propane, 2,2-bis(2-cyanato-5-biphenylyl)propane, 2,2-bis(4-cyanatophenyl)hexafluoropropane, 2,2-bis(4-cyanato-3,5-) Dimethylphenyl)propane, 1,1-bis(4-cyanatophenyl)butane, 1,1-bis(4-cyanatophenyl)isobutane, 1,1-bis(4-cyanatophenyl)pentane, 1,1 -Bis(4-cyanatophenyl)-3-methylbutane, 1,1-bis(4-cyanatophenyl)-2-methylbutane, 1,1-bis(4-cyanatophenyl)-2,2-dimethylpropane 2,2-bis(4-cyanatophenyl)butane, 2,2-bis(4-cyanatophenyl)pentane, 2,2-bis(4-cyanatophenyl)hexane, 2,2-bis(4) -Cyanatophenyl)-3-methylbutane, 2,2-bis(4-cyanatophenyl)-4-methylpentane, 2,2-bis(4-cyanatophenyl)-3,3-dimethylbutane, 3, 3-bis(4-cyanatophenyl)hexane, 3,3-bis(4-cyanatophenyl)heptane, 3,3-bis(4-cyanatophenyl)octane, 3,3-bis(4-cyanato) Phenyl)-2-methylpentane, 3,3-bis(4-cyanatophenyl)-2-methylhexane, 3,3-bis(4-cyanatophenyl)-2,2-dimethylpentane, 4,4- Bis(4-cyanatophenyl)-3-methylheptane, 3,3-bis(4-cyanatophenyl)-2-methylheptane, 3,3-bis(4-cyanatophenyl)-2,2-dimethyl Hexane, 3,3-bis(4-cyanatophenyl)-2,4-dimethylhexane, 3,3-bis(4-cyanatophenyl)-2,2,4-trimethylpentane, 2,2-bis( 4-cyanatophenyl)-1,1,1,3,3,3-hexafluoropropane, bis(4-cyanatophenyl)phenylmethane, 1,1-bis(4-cyanatophenyl)-1-phenyl Ethane, screw (4 -Cyanatophenyl)biphenylmethane, 1,1-bis(4-cyanatophenyl)cyclopentane, 1,1-bis(4-cyanatophenyl)cyclohexane, 2,2-bis(4-cyanato-3-isopropyl) Phenyl)propane, 1,1-bis(3-cyclohexyl-4-cyanatophenyl)cyclohexane, bis(4-cyanatophenyl)diphenylmethane, bis(4-cyanatophenyl)-2,2-dichloroethylene, 1,3 -Bis[2-(4-cyanatophenyl)-2-propyl]benzene, 1,4-bis[2-(4-cyanatophenyl)-2-propyl]benzene, 1,1-bis(4-si) Anatophenyl)-3,3,5-trimethylcyclohexane, 4-[bis(4-cyanatophenyl)methyl]biphenyl, 4,4-dicyanatobenzophenone, 1,3-bis(4-cyanatophenyl)-2 -Propen-1-one, bis(4-cyanatophenyl)ether, bis(4-cyanatophenyl)sulfide, bis(4-cyanatophenyl)sulfone, 4-cyanatobenzoic acid-4-cyanatophenyl ester ( 4-cyanatophenyl-4-cyanatobenzoate), bis-(4-cyanatophenyl)carbonate, 1,3-bis(4-cyanatophenyl)adamantane, 1,3-bis(4-cyanatophenyl) -5,7-Dimethyladamantane, 3,3-bis(4-cyanatophenyl)isobenzofuran-1(3H)-one (cyanate of phenolphthalein), 3,3-bis(4-cyanato-3-methyl) Phenyl)isobenzofuran-1(3H)-one (cyanate of o-cresolphthalein), 9,9′-bis(4-cyanatophenyl)fluorene, 9,9-bis(4-cyanato-3-methylphenyl) ) Fluorene, 9,9-bis(2-cyanato-5-biphenylyl)fluorene, tris(4-cyanatophenyl)methane, 1,1,1-tris(4-cyanatophenyl)ethane, 1,1, 3-tris(4-cyanatophenyl)propane, α,α,α′-tris(4-cyanatophenyl)-1-ethyl-4-isopropylbenzene, 1,1,2,2-tetrakis(4-si) Anatophenyl)ethane, tetrakis(4-cyanatophenyl)methane, 2,4,6-tris(N-methyl-4-cyanatoanilino)-1,3,5-triazine, 2,4-bis(N-methyl-). 4-Cyanatoanilino)-6-(N-methylanili) No)-1,3,5-triazine, bis(N-4-cyanato-2-methylphenyl)-4,4'-oxydiphthalimide, bis(N-3-cyanato-4-methylphenyl)-4, 4'-oxydiphthalimide, bis(N-4-cyanatophenyl)-4,4'-oxydiphthalimide, bis(N-4-cyanato-2-methylphenyl)-4,4'-(hexafluoroisopropyl) Ridene) diphthalimide, tris(3,5-dimethyl-4-cyanatobenzyl) isocyanurate, 2-phenyl-3,3-bis(4-cyanatophenyl)phthalimidine, 2-(4-methylphenyl)-3 , 3-bis(4-cyanatophenyl)phthalimidine, 2-phenyl-3,3-bis(4-cyanato-3-methylphenyl)phthalimidine, 1-methyl-3,3-bis(4-cyanatophenyl) Examples include indoline-2-one and 2-phenyl-3,3-bis(4-cyanatophenyl)indoline-2-one. Another specific example of the compound represented by the general formula (3) is a phenol novolac resin and a cresol novolac resin (phenol, alkyl-substituted phenol or halogen-substituted phenol, and formalin, paraformaldehyde, etc., by known methods). Formaldehyde compound of 1) in an acidic solution), trisphenol novolac resin (hydroxybenzaldehyde and phenol reacted in the presence of an acidic catalyst), fluorene novolac resin (fluorenone compound and 9,9- Bis(hydroxyaryl)fluorenes reacted in the presence of an acidic catalyst), phenol aralkyl resin, cresol aralkyl resin, naphthol aralkyl resin and biphenyl aralkyl resin (Ar ₂ -(CH ₂ Y) by a known method) ₂ (Ar ₂ represents a phenyl group, Y represents a halogen atom, and the same shall apply in this paragraph hereinafter), and a bishalogenomethyl compound and a phenol compound are reacted with an acidic catalyst or without a catalyst. , A bis(alkoxymethyl) compound represented by Ar ₂ —(CH ₂ OR) ₂ and a phenol compound in the presence of an acidic catalyst, or Ar ₂ —(CH ₂ OH) ₂ Represented by a reaction of a bis(hydroxymethyl) compound and a phenol compound in the presence of an acidic catalyst, or a polycondensation of an aromatic aldehyde compound, an aralkyl compound and a phenol compound), and phenol-modified xylene Formaldehyde resin (which is obtained by reacting a xylene formaldehyde resin and a phenol compound in the presence of an acidic catalyst by a known method), modified naphthalene formaldehyde resin (a naphthalene formaldehyde resin and a hydroxy-substituted aromatic compound are acid-catalyzed by a known method) A phenol-modified dicyclopentadiene resin, a phenol resin having a polynaphthylene ether structure (a polyvalent hydroxynaphthalene compound having two or more phenolic hydroxy groups in one molecule by a known method) To a cyanate of a phenol resin such as that obtained by dehydration condensation in the presence of a basic catalyst) by a method similar to the above, and prepolymers thereof. These are not particularly limited. These other cyanate ester compounds can be used alone or in combination of two or more.

Among these, phenol novolac type cyanate ester compounds, naphthol aralkyl type cyanate ester compounds, biphenylaralkyl type cyanate ester compounds, naphthylene ether type cyanate ester compounds, xylene resin type cyanate ester compounds, adamantane skeleton type cyanate esters A compound is preferable, and a naphthol aralkyl type cyanate ester compound is particularly preferable.

A resin cured product using these cyanate ester compounds has excellent properties such as glass transition temperature, low thermal expansion, and plating adhesion.

The content of the cyanate ester compound (B) in the resin composition of the present embodiment can be appropriately set according to the desired characteristics and is not particularly limited, but the resin solid content in the resin composition is 100 parts by mass. In that case, 1 to 90 parts by mass is preferable.

As the filler (C) used in this embodiment, known fillers can be appropriately used, and the type thereof is not particularly limited. In particular, a filler generally used in laminated plate applications can be preferably used as the filler (C). Specific examples of the filler (C) include silicas such as natural silica, fused silica, synthetic silica, amorphous silica, aerosil and hollow silica, and oxides such as white carbon, titanium white, zinc oxide, magnesium oxide and zirconium oxide. , Boron nitride, agglomerated boron nitride, silicon nitride, aluminum nitride, barium sulfate, aluminum hydroxide, aluminum hydroxide heat treated product (aluminum hydroxide heat treated to reduce part of crystal water), boehmite, water Metal hydrates such as magnesium oxide, molybdenum compounds such as molybdenum oxide and zinc molybdate, zinc borate, zinc stannate, alumina, clay, kaolin, talc, calcined clay, calcined kaolin, calcined talc, mica, E-glass , A-glass, NE-glass, C-glass, L-glass, D-glass, S-glass, M-glass G20, glass short fibers (E glass, T glass, D glass, S glass, Q glass, etc. (Including fine glass powders), hollow glass, spherical glass, and other inorganic fillers, styrene-type, butadiene-type, acrylic-type rubber powders, core-shell type rubber powders, and silicone resin powders and silicone rubber powders. Examples include organic fillers such as silicone composite powder. These fillers may be used alone or in combination of two or more.
Among these, one or more selected from the group consisting of silica, aluminum hydroxide, boehmite, magnesium oxide and magnesium hydroxide is preferable. By using these fillers, properties such as thermal expansion characteristics, dimensional stability, and flame retardancy of the resin composition are improved.

The content of the filler (C) in the resin composition of the present embodiment can be appropriately set according to the desired characteristics and is not particularly limited, but the resin solid content in the resin composition is 100 parts by mass. In this case, when the amount is 50 to 1600 parts by mass, the moldability of the resin composition becomes good.

Here, when the filler (C) is contained in the resin composition, it is preferable to use a silane coupling agent or a wetting dispersant together. As the silane coupling agent, those generally used for surface treatment of inorganic substances can be preferably used, and the type thereof is not particularly limited. Specific examples of the silane coupling agent include γ-aminopropyltriethoxysilane, N-β-(aminoethyl)-γ-aminopropyltrimethoxysilane and other aminosilanes, γ-glycidoxypropyltrimethoxysilane, Epoxysilanes such as β-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, vinylsilanes such as γ-methacryloxypropyltrimethoxysilane and vinyltri(β-methoxyethoxy)silane, N-β-(N- Examples include cationic silanes such as vinylbenzylaminoethyl)-γ-aminopropyltrimethoxysilane hydrochloride, and phenylsilanes. The silane coupling agent may be used alone or in combination of two or more. As the wetting and dispersing agent, those generally used for paints can be preferably used, and the type thereof is not particularly limited. As the wetting and dispersing agent, a copolymer-based wetting and dispersing agent is preferably used, and may be a commercially available product. Specific examples of commercially available products include Disperbyk-110, 111, 161, 180, BYK-W996, BYK-W9010, BYK-W903, and BYK-W940 manufactured by BYK Japan KK. The wetting and dispersing agent may be used alone or in combination of two or more.

Further, in the resin composition of the present embodiment, an epoxy resin other than the epoxy resin (A) represented by the general formula (1) (hereinafter, referred to as “other epoxy resin”) is used as long as the desired characteristics are not impaired. ,), a maleimide compound, a phenol resin, an oxetane resin, a benzoxazine compound, a compound having a polymerizable unsaturated group, and the like.
By using these in combination, desired properties such as flame retardancy and low dielectric property of the cured product obtained by curing the resin composition can be improved.

The other epoxy resin is not represented by the general formula (1), and any known epoxy resin can be appropriately used as long as it is an epoxy resin having two or more epoxy groups in one molecule. The type is not particularly limited. Specifically, bisphenol A type epoxy resin, bisphenol E type epoxy resin, bisphenol F type epoxy resin, bisphenol S type epoxy resin, phenol novolac type epoxy resin, bisphenol A novolac type epoxy resin, glycidyl ester type epoxy resin, aralkyl novolak. Type epoxy resin, biphenyl aralkyl type epoxy resin, naphthylene ether type epoxy resin, cresol novolac type epoxy resin, polyfunctional phenol type epoxy resin, naphthalene type epoxy resin, anthracene type epoxy resin, naphthalene skeleton modified novolac type epoxy resin, phenol aralkyl type Type epoxy resin, naphthol aralkyl type epoxy resin, dicyclopentadiene type epoxy resin, biphenyl type epoxy resin, alicyclic epoxy resin, polyol type epoxy resin, phosphorus-containing epoxy resin, glycidyl amine, glycidyl ester, butadiene etc. double bond Examples thereof include compounds obtained by epoxidizing, and compounds obtained by reacting hydroxyl group-containing silicone resins with epichlorohydrin. Among these epoxy resins, biphenylaralkyl type epoxy resins, naphthylene ether type epoxy resins, polyfunctional phenol type epoxy resins, and naphthalene type epoxy resins are preferable in terms of flame retardancy and heat resistance. These epoxy resins can be used alone or in combination of two or more.

As the maleimide compound, generally known compounds can be used as long as they are compounds having one or more maleimide groups in one molecule. For example, 4,4-diphenylmethane bismaleimide, phenylmethane maleimide, m-phenylene bismaleimide, 2,2-bis(4-(4-maleimidophenoxy)-phenyl)propane, 3,3-dimethyl-5,5-diethyl. -4,4-Diphenylmethane bismaleimide, 4-methyl-1,3-phenylene bismaleimide, 1,6-bismaleimide-(2,2,4-trimethyl)hexane, 4,4-diphenyl ether bismaleimide, 4,4 -Diphenyl sulfone bismaleimide, 1,3-bis(3-maleimidophenoxy)benzene, 1,3-bis(4-maleimidophenoxy)benzene, polyphenylmethane maleimide, novolac type maleimide, biphenylaralkyl type maleimide, and these maleimide compounds Examples thereof include a prepolymer of 1), a prepolymer of a maleimide compound and an amine compound, and the like, but are not particularly limited. These maleimide compounds may be used alone or in combination of two or more. Among these, novolac type maleimide compounds and biphenylaralkyl type maleimide compounds are particularly preferable.

As the phenol resin, a generally known one can be used as long as it is a phenol resin having two or more hydroxy groups in one molecule. For example, bisphenol A type phenol resin, bisphenol E type phenol resin, bisphenol F type phenol resin, bisphenol S type phenol resin, phenol novolac resin, bisphenol A novolac type phenol resin, glycidyl ester type phenol resin, aralkyl novolak type phenol resin, biphenyl Aralkyl type phenol resin, cresol novolac type phenol resin, polyfunctional phenol resin, naphthol resin, naphthol novolac resin, polyfunctional naphthol resin, anthracene type phenol resin, naphthalene skeleton modified novolac type phenol resin, phenol aralkyl type phenol resin, naphthol aralkyl type Examples thereof include phenol resins, dicyclopentadiene type phenol resins, biphenyl type phenol resins, alicyclic phenol resins, polyol type phenol resins, phosphorus-containing phenol resins, hydroxyl group-containing silicone resins, etc., but are not particularly limited. Among these phenol resins, biphenyl aralkyl type phenol resin, naphthol aralkyl type phenol resin, phosphorus-containing phenol resin, and hydroxyl group-containing silicone resin are preferable in terms of flame retardancy. These phenol resins may be used alone or in combination of two or more.

As the oxetane resin, a generally known one can be used. For example, oxetane, 2-methyloxetane, 2,2-dimethyloxetane, 3-methyloxetane, alkyl oxetane such as 3,3-dimethyloxetane, 3-methyl-3-methoxymethyloxetane, 3,3-di(trifluoro) Methyl)perfluoxetane, 2-chloromethyloxetane, 3,3-bis(chloromethyl)oxetane, biphenyl type oxetane, OXT-101 (trade name of Toagosei Co., Ltd.), OXT-121 (trade name of Toagosei Co., Ltd.), etc. There is no particular limitation to be mentioned. These oxetane resins can be used alone or in combination of two or more.

As the benzoxazine compound, generally known compounds can be used as long as they are compounds having two or more dihydrobenzoxazine rings in one molecule. For example, bisphenol A-type benzoxazine BA-BXZ (trade name, manufactured by Konishi Chemical), bisphenol F-type benzoxazine BF-BXZ (trade name, manufactured by Konishi Chemical), bisphenol S-type benzoxazine BS-BXZ (trade name, manufactured by Konishi Chemical), P Examples thereof include -d type benzoxazine (trade name manufactured by Shikoku Chemicals Co., Ltd.) and Fa type benzoxazine (trade name manufactured by Shikoku Chemicals Co., Ltd.), which are not particularly limited. These benzoxazine compounds can be used alone or in combination of two or more.

As the compound having a polymerizable unsaturated group, generally known compounds can be used. For example, vinyl compounds such as ethylene, propylene, styrene, divinylbenzene and divinylbiphenyl, methyl (meth)acrylate, 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, polypropylene glycol di(meth)acrylate, (Meth)acrylates of monohydric or polyhydric alcohols such as trimethylolpropane di(meth)acrylate, trimethylolpropane tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol hexa(meth)acrylate, bisphenol Examples thereof include epoxy-type (meth)acrylates such as A-type epoxy (meth)acrylate and bisphenol F-type epoxy (meth)acrylate, and benzocyclobutene resin (, but are not particularly limited to these unsaturated groups. The compound having a can be used alone or in combination of two or more. Incidentally, the above-mentioned “(meth)acrylate” is a concept including acrylate and corresponding methacrylate.

Further, the resin composition of the present embodiment may contain a curing accelerator for appropriately adjusting the curing rate, if necessary. As the curing accelerator, those generally used as curing accelerators such as cyanate ester compounds and epoxy resins can be preferably used, and the type thereof is not particularly limited. Specific examples of the curing accelerator include zinc octylate, zinc naphthenate, cobalt naphthenate, copper naphthenate, iron acetylacetone, nickel octylate, organic metal salts such as manganese octylate, phenol, xylenol, cresol, resorcin, catechol. Phenol compounds such as octylphenol and nonylphenol, alcohols such as 1-butanol and 2-ethylhexanol, 2-methylimidazole, 2-ethyl-4-methylimidazole, 2-phenylimidazole, 1-cyanoethyl-2-phenylimidazole, Imidazoles such as 1-cyanoethyl-2-ethyl-4-methylimidazole, 2-phenyl-4,5-dihydroxymethylimidazole and 2-phenyl-4-methyl-5-hydroxymethylimidazole, and carboxylic acids of these imidazoles Alternatively, derivatives such as adducts of acid anhydrides thereof, amines such as dicyandiamide, benzyldimethylamine, 4-methyl-N,N-dimethylbenzylamine, phosphine compounds, phosphine oxide compounds, phosphonium salt compounds, diphosphine. Compounds such as phosphorus compounds, epoxy-imidazole adduct compounds, benzoyl peroxide, p-chlorobenzoyl peroxide, di-t-butyl peroxide, diisopropyl peroxycarbonate, di-2-ethylhexyl peroxycarbonate, etc. Or an azo compound such as azobisisobutyronitrile. The curing accelerator may be used alone or in combination of two or more.
The amount of the curing accelerator used can be appropriately adjusted in consideration of the degree of curing of the resin, the viscosity of the resin composition, etc., and is not particularly limited. The amount of the curing accelerator used may be 0.005 to 10 parts by mass with respect to 100 parts by mass of the resin solid content in the resin composition.

Furthermore, the resin composition of the present embodiment, other than the thermosetting resin, thermoplastic resin and its oligomer, various polymer compounds such as elastomers, flame retardant compounds, etc. , And various additives can be used in combination. These are not particularly limited as long as they are commonly used. For example, specific examples of flame-retardant compounds include bromine compounds such as 4,4′-dibromobiphenyl, phosphoric acid esters, melamine phosphate, phosphorus-containing epoxy resins, nitrogen compounds such as melamine and benzoguanamine, oxazine ring-containing compounds, In addition, silicone compounds and the like can be mentioned. Examples of various additives include ultraviolet absorbers, antioxidants, photopolymerization initiators, fluorescent whitening agents, photosensitizers, dyes, pigments, thickeners, flow control agents, lubricants, defoaming agents. , Dispersants, leveling agents, brighteners, polymerization inhibitors and the like. These may be used alone or in combination of two or more as desired.

The resin composition of the present embodiment can contain an organic solvent, if necessary. In this case, the resin composition of the present embodiment can be used as a mode (solution or varnish) in which at least a part, preferably all of the various resin components described above are dissolved or compatible with an organic solvent. As the organic solvent, any known solvent can be appropriately used as long as it can dissolve or be compatible with at least a part, preferably all of the various resin components described above, and the type thereof is not particularly limited. .. Specific examples of the organic solvent include ketones such as acetone, methyl ethyl ketone and methyl isobutyl ketone, cellosolve solvents such as propylene glycol monomethyl ether and propylene glycol monomethyl ether acetate, ethyl lactate, methyl acetate, ethyl acetate, butyl acetate and acetic acid. Isoamyl, ethyl lactate, methyl methoxypropionate, ester solvents such as methyl hydroxyisobutyrate, polar solvents such as amides such as dimethylacetamide and dimethylformamide, non-polar solvents such as aromatic hydrocarbons such as toluene and xylene Can be mentioned. These may be used alone or in combination of two or more.

The resin composition of the present embodiment can be prepared according to a conventional method, and the epoxy resin (A) represented by the general formula (1) and the cyanate ester compound (B) and the above-mentioned other optional components are uniformly added. The method for adjusting the resin composition is not particularly limited as long as it is a method for obtaining the resin composition contained in the above. For example, the resin composition of the present embodiment can be easily prepared by sequentially mixing the epoxy resin (A) represented by the general formula (1) and the cyanate ester compound (B) in a solvent and stirring the mixture sufficiently. You can

In addition, at the time of preparing the resin composition, a known treatment (stirring, mixing, kneading treatment, etc.) for uniformly dissolving or dispersing each component can be performed. For example, when the filler (C) is uniformly dispersed, the dispersibility in the resin composition is enhanced by performing the stirring dispersion treatment using a stirring tank equipped with a stirrer having an appropriate stirring ability. The above stirring, mixing, and kneading treatments can be appropriately performed using, for example, an apparatus for mixing such as a ball mill and a bead mill, or a known apparatus such as an orbital/spinning type mixing apparatus.

The resin composition of this embodiment can be used as a constituent material of a prepreg, a metal foil-clad laminate, a printed wiring board, and a semiconductor package. For example, a prepreg can be obtained by impregnating or coating a substrate with a solution prepared by dissolving the resin composition of the present embodiment in a solvent and drying the substrate.
In addition, a peelable plastic film is used as equipment, and a solution prepared by dissolving the resin composition of the present embodiment in a solvent is applied to the plastic film and dried to obtain a build-up film or a dry film solder resist. You can Here, the solvent can be dried by drying at a temperature of 20° C. to 150° C. for 1 to 90 minutes.
Further, the resin composition of the present embodiment can be used in an uncured state in which the solvent is just dried, or can be used in a semi-cured (B stage) state if necessary.

Hereinafter, the prepreg of this embodiment will be described in detail. The prepreg of the present embodiment has a base material and the above resin composition impregnated or applied to the base material. The method for producing the prepreg of the present embodiment is not particularly limited as long as it is a method of producing the prepreg by combining the resin composition of the present embodiment and the substrate. Specifically, after impregnating or coating the substrate with the resin composition of the present embodiment, it is semi-cured by a method of drying for about 2 to 15 minutes in a dryer at 120 to 220° C. The prepreg of the embodiment can be manufactured. At this time, the amount of the resin composition attached to the base material, that is, the content of the resin composition (including the filler (C)) with respect to the total amount of the semi-cured prepreg is in the range of 20 to 99 mass %. Is preferred.

The base material used when manufacturing the prepreg of the present embodiment may be a known base material used for various printed wiring board materials. Examples of such a substrate include glass fibers such as E glass, D glass, L glass, S glass, T glass, Q glass, UN glass, NE glass and spherical glass, and inorganic fibers other than glass such as quartz, Examples thereof include organic fibers such as polyimide, polyamide, and polyester, and woven fabric such as liquid crystal polyester, but are not particularly limited thereto. As the shape of the base material, woven cloth, non-woven cloth, roving, chopped strand mat, surfacing mat, and the like are known, and any of these may be used. The base material may be used alone or in an appropriate combination of two or more kinds. Among the woven fabrics, the woven fabric subjected to the super-opening treatment or the filling treatment is particularly preferable from the viewpoint of dimensional stability. Furthermore, a glass woven fabric surface-treated with a silane coupling agent such as an epoxysilane treatment or an aminosilane treatment is preferable from the viewpoint of moisture absorption heat resistance. A liquid crystal polyester woven fabric is preferable from the viewpoint of electrical characteristics. Further, the thickness of the base material is not particularly limited, but in the case of laminated board use, the range of 0.01 to 0.2 mm is preferable.

The metal foil-clad laminate of the present embodiment has at least one or more of the above-mentioned prepregs and the metal foil arranged on one side or both sides of the prepreg. Specifically, it is prepared by arranging a metal foil such as copper or aluminum on one surface or both surfaces of one prepreg described above or a plurality of prepregs stacked and laminating the foil. be able to. The metal foil used here is not particularly limited as long as it is used for a printed wiring board material, but a copper foil such as a rolled copper foil and a copper foil is preferable. The thickness of the metal foil is not particularly limited, but is preferably 2 to 70 μm, more preferably 3 to 35 μm. As a molding condition, a method used in the production of ordinary laminated boards for printed wiring boards and multilayer boards can be adopted. For example, using a multi-stage press machine, a multi-stage vacuum press machine, a continuous molding machine, an autoclave molding machine, or the like, lamination molding is performed under the conditions of a temperature of 180 to 350° C., a heating time of 100 to 300 minutes, and a surface pressure of 20 to 100 kg/cm ^2. As a result, the metal foil-clad laminate according to this embodiment can be manufactured. A multilayer board can also be manufactured by laminating and molding the above prepreg and a wiring board for an inner layer, which is separately manufactured. As a method for producing a multilayer board, for example, 35 μm copper foil is arranged on both sides of one prepreg described above, and after forming a laminate under the above conditions, an inner layer circuit is formed and blackening treatment is performed on this circuit. To form an inner layer circuit board. Further, this inner layer circuit board and the above-mentioned prepreg are alternately arranged one by one, and further, a copper foil is arranged on the outermost layer, and laminated and molded under the above conditions, preferably under vacuum. In this way, a multilayer board can be manufactured.

The metal foil-clad laminate of the present embodiment can be suitably used as a printed wiring board by further forming a pattern. The printed wiring board can be manufactured according to a conventional method, and its manufacturing method is not particularly limited. Hereinafter, an example of a method for manufacturing a printed wiring board will be shown. First, the metal foil-clad laminate described above is prepared. Next, an inner layer substrate is produced by performing an etching process on the surface of the metal foil-clad laminate to form an inner layer circuit. The inner layer circuit surface of this inner layer substrate is subjected to a surface treatment for increasing the adhesive strength, if necessary, and then the required number of the above-mentioned prepregs are stacked on the inner layer circuit surface. Further, a metal foil for the outer layer circuit is laminated on the outer side thereof and heated and pressed to be integrally molded. In this way, a multilayer laminate having an insulating layer formed of a base material and a cured product of a thermosetting resin composition between the inner layer circuit and the metal foil for the outer layer circuit is manufactured. Then, after performing a drilling process for through holes and via holes on the multilayer laminated plate, a plated metal film for conducting the inner layer circuit and the metal foil for the outer layer circuit is formed on the wall surface of the hole. Furthermore, the printed wiring board is manufactured by performing an etching process on the metal foil for the outer layer circuit to form the outer layer circuit.

The printed wiring board obtained in the above Production Example has an insulating layer and a conductor layer formed on the surface of the insulating layer, and the insulating layer contains the resin composition of the present embodiment described above. That is, the prepreg (the substrate and the resin composition of the present embodiment impregnated or applied thereto) of the present embodiment described above, the layer of the resin composition of the metal foil-clad laminate of the present embodiment described above (the present embodiment The layer composed of the resin composition of 1) is composed of an insulating layer containing the resin composition of the present embodiment.

The resin composite sheet of the present embodiment has a support and the above resin composition provided on the surface of the support. This resin composite sheet can be obtained by applying a solution prepared by dissolving the above resin composition in a solvent onto a support and drying it. The support used here is not particularly limited, and examples thereof include a polyethylene film, a polypropylene film, a polycarbonate film, a polyethylene terephthalate film, an ethylene tetrafluoroethylene copolymer film, and a release agent applied to the surface of these films. Examples include release films, organic film bases such as polyimide films, conductor foils such as copper foil and aluminum foil, and plate-shaped inorganic films such as glass plates, SUS plates and FRP. As a coating method, for example, a solution obtained by dissolving the above resin composition in a solvent is coated on a support with a bar coater, a die coater, a doctor blade, a baker applicator or the like, whereby the support and the resin sheet are integrated. The method for producing the laminated sheet can be mentioned. Further, a single layer sheet (resin sheet) can be obtained by peeling or etching the support from the resin composite sheet obtained by further drying after coating. The solution obtained by dissolving or compatibilizing the resin composition of the present embodiment in a solvent is fed into a mold having a sheet-shaped cavity and dried to form a sheet, thereby forming a support. It is also possible to obtain a single-layer sheet (resin sheet) without using.

In the production of the resin composite sheet or the single layer sheet of the present embodiment, the drying conditions for removing the solvent are not particularly limited, but it is preferable to dry at a temperature of 20°C to 200°C for 1 to 90 minutes. When the temperature is 20° C. or higher, the solvent can be prevented from remaining in the resin composition, and when the temperature is 200° C. or lower, the progress of curing of the resin composition can be suppressed. Further, the thickness of the resin layer in the resin composite sheet or the single-layer sheet of the present embodiment can be adjusted by the concentration of the solution of the resin composition of the present embodiment and the coating thickness, and is not particularly limited. However, the thickness is preferably 0.1 to 500 μm. When the thickness of the resin layer is 500 μm or less, it becomes more difficult for the solvent to remain during drying.

Hereinafter, the embodiments of the present invention will be described in more detail by showing synthesis examples, examples and comparative examples, but the present invention is not limited thereto.

(Synthesis Example 1) Synthesis of cyanate ester compound 1-naphthol aralkyl resin (manufactured by Nippon Steel & Sumikin Chemical Co., Ltd.) 300 g (OH group conversion 1.28 mol) and triethylamine 194.6 g (1.92 mol) (per 1 mol of hydroxy group) 1.5 mol) was dissolved in 1800 g of dichloromethane to obtain a solution 1.
125.9 g (2.05 mol) of cyanogen chloride (1.6 mol per 1 mol of hydroxy group), 293.8 g of dichloromethane, 194.5 g (1.92 mol) of 36% hydrochloric acid (1.5 mol per 1 mol of hydroxy group) ), and 1205.9 g of water were poured over 30 minutes while maintaining the liquid temperature at -2 to -0.5°C under stirring. After the completion of pouring Solution 1, after stirring at the same temperature for 30 minutes, a solution (Solution 2) in which 65 g (0.64 mol) of triethylamine (0.5 mol per 1 mol of hydroxy group) was dissolved in 65 g of dichloromethane was added for 10 minutes. I poured over it. After pouring the solution 2, the reaction was completed by stirring at the same temperature for 30 minutes.
After that, the reaction solution was allowed to stand and the organic phase and the aqueous phase were separated. The obtained organic phase was washed 5 times with 1300 g of water. The electric conductivity of the wastewater after the fifth washing with water was 5 μS/cm, and it was confirmed that the ionic compounds that could be removed were sufficiently removed by washing with water.
The organic phase after washing with water was concentrated under reduced pressure, and finally concentrated and dried at 90° C. for 1 hour to obtain 331 g of a target naphthol aralkyl type cyanate ester compound (SNCN) (orange viscous substance). The obtained SNCN had a mass average molecular weight Mw of 600. In addition, the IR spectrum of SNCN showed an absorption of 2250 cm ⁻¹ (cyanate ester group) and no absorption of a hydroxy group.

(Example 1)
50 parts by mass of SNCN obtained by Synthesis Example 1, 50 parts by mass of an epoxy resin (NC-7700, manufactured by Nippon Kayaku Co., Ltd.) represented by the formula (2), 100 parts by mass of fused silica (SC2050MB, manufactured by Admatex). Parts and 0.15 parts by mass of zinc octylate (manufactured by Nippon Kagaku Sangyo Co., Ltd.) were mixed to obtain a varnish. This varnish was diluted with methyl ethyl ketone, impregnated and coated on a 0.1 mm-thick E glass woven fabric, and dried by heating at 150° C. for 5 minutes to obtain a prepreg having a resin content of 50% by mass.
(N in the formula is an integer of 1 to 20.)

Eight pieces of the obtained prepregs were stacked and electrolytic copper foils (3EC-M3-VLP, manufactured by Mitsui Kinzoku Co., Ltd.) having a thickness of 12 μm were arranged on the top and bottom, and laminated molding for 120 minutes at a pressure of 30 kgf/cm ² and a temperature of 220° C. Then, a metal foil-clad laminate having an insulating layer thickness of 0.8 mm was obtained. The glass transition temperature was evaluated using the obtained metal foil-clad laminate. The results are shown in Table 1.

(Comparative Example 1)
In Example 1, instead of using 50 parts by mass of the epoxy resin represented by the general formula (1), 50 parts by mass of a biphenylaralkyl type epoxy resin (NC-3000-FH, manufactured by Nippon Kayaku Co., Ltd.), octyl acid. A metal foil-clad laminate having a thickness of 0.8 mm was obtained in the same manner as in Example 1 except that 0.12 parts by mass of zinc was used. Table 1 shows the evaluation results of the obtained metal foil-clad laminate.

(Measurement method and evaluation method)
1) The glass transition temperature of the obtained 8-layer metal foil-clad laminate was measured by a DMA method using a dynamic viscoelasticity analyzer (TA Instruments) according to JIS C6481.

As is clear from Table 1, it was confirmed that by using the resin composition of the present invention, it is possible to realize a prepreg, a printed wiring board and the like having an excellent glass transition temperature.

As described above, the resin composition of the present invention is used in various applications such as electric/electronic materials, machine tool materials, aviation materials, and the like, for example, electrical insulating materials, semiconductor plastic packages, sealing materials, adhesives, laminated materials, It can be widely and effectively used as a resist, build-up laminated board material, etc. Especially, it can be particularly effectively used as a printed wiring board material for high integration and high density of recent information terminal equipment and communication equipment. Is. Further, since the laminated plate, the metal foil-clad laminated plate and the like of the present invention have excellent glass transition temperature performance, their industrial practicability is extremely high.

Claims (9)

A resin composition comprising an epoxy resin (A) represented by the following general formula (1) and a naphthol aralkyl type cyanate ester compound (B).
(In the formula, R represents an alkyl group having 1 to 3 carbon atoms, n represents an integer of 1 to 20, and n may be a different mixture.) The resin composition according to claim 1, wherein the content of the epoxy resin (A) in the resin composition is 1 to 90 parts by mass with respect to 100 parts by mass of the resin solid content. The resin composition according to claim 1 or 2, further comprising a filler (C). Furthermore, among the group selected from epoxy resins other than the epoxy resin (A) represented by the general formula (1), maleimide compounds, phenol resins, oxetane resins, benzoxazine compounds, and compounds having a polymerizable unsaturated group. The resin composition according to any one of claims 1 to 3, containing any one or more thereof. The resin composition according to claim 3 or 4, wherein the content of the filler (C) in the resin composition is 50 to 1600 parts by mass with respect to 100 parts by mass of the resin solid content. A prepreg comprising a base material and the resin composition according to claim 1, which is impregnated or applied to the base material. A metal foil-clad laminate comprising at least one prepreg according to claim 6 and a metal foil disposed on one or both sides of the prepreg. A resin sheet comprising a support and the resin composition according to any one of claims 1 to 5, which is disposed on the surface of the support. A printed wiring board comprising an insulating layer and a conductor layer formed on the surface of the insulating layer, wherein the insulating layer contains the resin composition according to any one of claims 1 to 5.