JPH0689118B2 - Epoxy resin composition - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION <Field of Industrial Application> The present invention relates to an epoxy resin composition, and more particularly to an epoxy resin composition suitable for lamination and molding.

<Prior art> Laminated boards and I used for industrial equipment and consumer equipment.
Epoxy resin has been used for sealing semiconductor elements such as C and LSI.

<Problems to be Solved by the Invention> However, due to the low heat resistance of the cured product, the laminated plate has a large dimensional change in the direction perpendicular to the substrate, and has problems of plating connection reliability and smear. In addition, the thermal expansion of IC and LSI encapsulation materials is large, and when connecting components such as IC and LSI to a circuit, there is a problem such as cracking due to the heat of solder.

On the other hand, an imide resin is known as a thermosetting resin having a heat resistance higher than that of an epoxy resin, but a conventional thermosetting polyimide resin has a problem in adhesion to a metal surface, water resistance, and the like. .

<Means for Solving the Problems> From such a background, the present inventor diligently studied a resin composition which is superior in heat resistance to an epoxy resin and has adhesiveness and water resistance equivalent or superior to those of an epoxy resin. As a result, they have found that a resin composition comprising an epoxy resin, a specific imide compound and a specific phenolic compound is suitable for the above purpose, and completed the present invention.

(1) That is, the present invention is an epoxy comprising an epoxy resin (A), an imide compound (B) represented by the following general formula (I), and a polymaleimide compound (C) having two or more maleimide groups in the molecule. A resin composition (α) is provided.

(2) The present invention also includes an epoxy resin (A), an imide compound (B) represented by the following general formula (I), and a compound (D) having two or more phenolic OH groups in the molecule (hereinafter referred to as polyphenol compound). .) As an essential component
(β) is provided.

The present invention further provides an epoxy resin composition comprising a combination of (1) and (2), that is, (A), (B), (C), and (D).
(γ) is provided.

[In the formula, X represents an —NH ₂ group and / or an —OH group, and A
r ₁ and Ar ₂ are each independently an aromatic residue, R ₁ is a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, R ₂ is a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an alkoxy group or a hydroxyl group. , M and n represent a number of 0 to 30. ] In more detail about the Ar ₁ and Ar _2, Ar ₁ and A
Each r ₂ is independently a mononuclear or polynuclear divalent aromatic residue, and the aromatic ring includes those substituted with a lower alkyl group, halogen, lower alkoxy group, etc. and those not substituted. . More specifically, Ar ₁ and Ar ₂ are both aromatic amine residues, Ar ₂ is an aromatic diamine residue, and Ar ₁ is an aromatic monoamine or diamine residue. Examples of these aromatic amines include, for aromatic diamines, 4,4'-diaminodiphenylmethane, 3,3'-diaminodiphenylmethane, 4,4'-diaminodiphenyl ether, 3,4'-diaminodiphenyl ether, 4,4 '. ′ -Diaminodiphenylpropane, 4,
4'-diaminodiphenyl sulfone, 3,3'-diaminodiphenyl sulfone, 2,4-toluenediamine, 2,6-
Toluene diamine, m-phenylenediamine, p-phenylenediamine, benzidine, 4,4'-diaminodiphenyl sulfide, 3,3'-dichloro-4,4'-diaminodiphenyl sulfone, 3,3'-dichloro-4, 4'-diaminodiphenylpropane, 3,3'-dimethyl-4,4'-diaminodiphenylmethane, 3,3'-dimethoxy-4,4'-
Diaminobiphenyl, 3,3'-dimethyl-4,4'-diaminobiphenyl, 1,3-bis (4-aminophenoxy) benzene, 1,3-bis (3-aminophenoxy) benzene, 1,4-bis ( 4-aminophenoxy) benzene, 2,2
-Bis (4-aminophenoxyphenyl) propane, 4,
4'-bis (4-aminophenoxy) diphenyl sulfone, 4,4'-bis (3-aminophenoxy) diphenyl sulfone, 9,9'-bis (4-aminophenyl) anthracene, 9,9'-bis (4 -Aminophenyl) fluorene, 3,3'-dicarboxy-4,4'-diaminodiphenylmethane, 2,4-diaminoanisole, bis (3-aminophenyl) methylphosphine oxide, 3,3'-
Diaminobenzophenone, o-toluidine sulfone,
4,4'-methylene-bis-o-chloroaniline, tetrachlorodiaminodiphenylmethane, m-xylylenediamine, p-xylylenediamine, 4,4 ',-diaminostilbene, 5-amino-1- (4'- Aminophenyl-
1,3,3-trimethylindane, 6-amino-1- (4 '
-Aminophenyl) -1,3,3-trimethylindane, 5
-Amino-6-methyl-1- (3'-amino-4'-methylphenyl) -1,3,3-tolumethylindane, 7-amino-6-methyl-1- (3'-amino-4 ' -Methylphenyl) -1,3,3-trimethylindane, 6-amino-5-methyl-1- (4'-amino-3'-methylphenyl) -1,3,3-trimethylindane, 6-amino- 7
-Methyl-1- (4'-amino-3'-methylphenyl) -1,3,3-trimethylindane and the like.

On the other hand, regarding aromatic monoamines, o-aminophenol, m-aminophenol, p-aminophenol,
6-amino-m-cresol, 4-amino-m-cresol, 2,2- (4-hydroxyphenyl-4-aminophenyl) -propane, 2,2- (4-hydroxyphenyl-2'-methyl-4) ′ -Aminophenyl) -propane,
2,2- (3-methyl-4-hydroxyphenyl-4'-
Aminophenyl) -propane, 3-amino-1-naphthol, 8-amino-2-naphthol, 5-amino-1-
There are one kind or two or more kinds of naphthol, 4-amino-2-methyl-1-naphthol and the like.

Although R ₁ and R ₂ are as described above, R ₁ is particularly preferably an alkyl group having 1 to 3 carbon atoms.

R ₂ is preferably a hydrogen atom or an alkyl group having 1 to 5 carbon atoms.

Further, m and n in the general formula (I) are as described above, but preferably m and n are numbers from 0 to 8, particularly preferably 0 to 5.

The method for producing the terminal functional imide compound (B) of the present invention will be illustrated.

(1) When the formula X is —NH ₂ , the above aromatic diamine and the formula [In the formula, R ₁ and R ₂ are the same as described above. ] The compound shown below (hereinafter referred to as B ₁ and the isomers as the Y component or the Z component, respectively) can be synthesized by carrying out a usual imidization reaction with an excess of the aromatic diamine.

When X in the formula (1) is —OH, the above aromatic monoamine having an —OH group and the above aromatic diamine are combined with B ₁
In addition, the aromatic diamine / B ₁ molar ratio is (m + n) / (m + n + 1) and the aromatic monoamine / B ₁ molar ratio is 2 / (m + n + 1) (m, n
Is the same as above. In addition, the compound can be synthesized by performing an ordinary imidization reaction.

Although the method for synthesizing the terminal functional imide compound used in the present invention has been illustrated above, the method is not limited to these.

Here, exemplifying the synthesis method of B ₁ , [In the formula, R ₁ and R ₂ are the same as described above. (Or less B _3.) A compound represented by] and obtained by reacting maleic anhydride in the absence of a radical polymerization catalyst molar ratio is 1/2, and in the presence or absence of a radical polymerization inhibitor To be Examples of B ₃ include styrene, α-methylstyrene, α, p-dimethylstyrene, α, m-dimethylstyrene, isopropylstyrene, vinyltoluene, pt-butylstyrene, p-isopropenylphenol, m-isopropenyl. There are one or more of phenol, 1-methoxy-3-isopropenylbenzene, 1-methoxy-4-isopropenylbenzene, vinylxylene and the like.

The terminal functional type imide compound used in the present invention thus obtained is soluble at a high concentration in a low boiling point solvent such as acetone, methyl ethyl ketone, methyl isobutyl ketone, methyl cellosolve, ethyl cellosolve, methylene chloride and chloroform. Furthermore, the compatibility with the epoxy resin is excellent.

The epoxy resin (A) used in the present invention is a compound having two or more epoxy groups in the molecule, and is exemplified by bisphenol A, bisphenol F, hydroquinone, resorcin, phloroglycine, tris- (4-hydroxyphenyl) methane. , 1,1,2,2-Tetrakis (4-hydroxyphenyl) ethane and other divalent or trivalent phenols, or glycidyl ethers derived from halogenated polyphenols such as tetrabromobisphenol A and brominated phenol novolac Compounds, novolac-based epoxy resins derived from novolac resins which are reaction products of phenols such as phenol and o-cresol with formaldehyde, aniline, p-aminophenol, m-aminophenol, 4-amino-m-cresol, 6-amino-m -Cresol, 4,4'-diaminodiphenylmethane, 3,3'-diaminodiphenylmethane, 4,4'-diaminodiphenyl ether, 3,4'-diaminodiphenyl ether, 1,4-bis (4-aminophenoxy) benzene, 1, 4-bis (3-aminophenoxy) benzene, 1,3-bis (4-aminophenoxy) benzene, 1,3-bis (3-aminophenoxy) benzene, 2,2-bis (4-aminophenoxyphenyl) propane , P-phenylenediamine, m-phenylenediamine, 2,4-toluenediamine, 2,6-toluenediamine,
p-xylylenediamine, m-xylylenediamine, 1,
4-cyclohexane-bis (methylamine), 1,3-cyclohexane-bis (methylamine), 5-amino-1-
(4'-aminophenyl) -1,3,3-trimethylindane, 6-amino-1- (4'-aminophenyl) -1,3,
Amine-based epoxy resin derived from 3-tolumethylindane, p-oxybenzoic acid, m-oxybenzoic acid,
Glycidyl ester compounds derived from aromatic carboxylic acids such as terephthalic acid and isophthalic acid, hydantoin-based epoxy resins derived from 5,5-dimethylhydantoin, etc., 2,2'-bis (3,4-epoxycyclohexyl) ) Propane, 2,2-bis [4- (2,3-epoxypropyl) cyclohexyl] propane, vinylcyclohexenedioxide, 3,4-epoxycyclohexylmethyl-3,4
An alicyclic epoxy resin such as epoxycyclohexanecarboxylate, and triglycidyl isocyanurate, 1 such as 2,4,6-triglycidoxy-S-triazine
There can be mentioned one kind or two or more kinds.

The component (C) used in the present invention is a compound containing two or more maleimide groups represented by the general formula (II) in the molecule.

(In the formula, R ₃ represents a hydrogen atom or a lower alkyl group.) Specific examples thereof include N, N′-diphenylmethane bismaleimide and N, N′-diphenylmethane bismaleimide.
N'-phenylene bismaleimide, N, N'-diphenyl ether bismaleimide, N, N'-diphenylsulfone bismaleimide, N, N'-dicyclohexylmethane bismaleimide, N, N'-xylene bismaleimide, N, N'- Tolylene bismaleimide, N, N'-xylylene bismaleimide, N, N'-diphenylcyclohexane bismaleimide, N, N'-dichloro-diphenylmethane bismaleimide, N, N'-diphenylcyclohexane bismaleimide, N, N ' -Diphenylmethanebismethylmaleimide,
N, N′-diphenyl ether bismethylmaleimide, N,
N'-diphenylsulfone bismethylmaleimide, (each including isomers), N, N'-ethylene bismaleimide, N, N'-hexamethylene bismaleimide, N, N'-hexamethylene bismethylmaleimide, and these N , N ′
-A prepolymer having an N, N'-bismaleimide bone nucleus obtained by adding a bismaleimide compound and a diamine, and a maleimide compound or a methylmaleimide compound of aniline / formalin polycondensation can be exemplified.

Especially N, N'-diphenylmethane bismaleimide, N, N'-
Diphenyl ether bismaleimide is preferred.

Component (D) used in the present invention is a compound having two or more phenolic OH groups in the molecule, and exemplarily includes bisphenol A, bisphenol F, hydroquinone, resorcin phloroglycine, tris- (4-hydroxyphenyl) methane, Divalent or trivalent phenols such as 1,1,2,2-tetrakis (4-hydroxyphenyl) ethane, halogenated bisphenols such as tetrabromobisphenol A, and reaction products of phenol and formaldehyde A certain novolak type initial condensate, specifically, phenol, cresol (including various isomers), xylenol (including various isomers), hydroquinone, resorcin, pt-butylphenol, p-
Examples are novolak type initial condensates such as t-octylphenol, allylphenol (including various isomers), bisphenol A, and vinylphenol.

The quantitative ratio of each component of the resin composition of the present invention is not limited. However, there are generally preferable conditions, and for the epoxy resin composition (α), the ratio of the epoxy resin (A) and the imide compound (B) is (A) 1 g equivalent, and (B) is 0.6.
g equivalent to 1.2 g equivalent, and the ratio of polymaleimide compound (C) and imide compound (B) is 1 with respect to the number of double bonds in (C).
The number of active hydrogen H in the terminal functional group X of (B) is 0.6 to 1, and the weight ratio (A) / (C) of (A) and (C) is 95/5 to 40/60. It is preferable. However, in the case of using an epoxy curing agent described below, the ratio of the epoxy resin (A) and the terminal functional imide compound (B) is (A) 1 g equivalent to the total of (B) and other curing agents. It is preferably 0.6 g equivalent to 1.2 g equivalent.

Regarding the resin composition β, the ratio of the number of active hydrogens in the terminal functional group X of the imide compound (B) and the number of —OH groups in the polyphenol compound (D) was (B) / (D) = 2/1. It is preferable to select such that the sum of the active hydrogen equivalents of (B) and (D) is 0.6 to 1.2 g equivalent to 1 g equivalent of the epoxy resin (A).

Similarly, for the quantitative ratio of each component of the resin composition γ, generally, 1 g equivalent of the epoxy resin (A), active hydrogen equivalent of the imide compound (B) and the active hydrogen equivalent of the polyphenol compound (D). Is 0.6 to 1.2 g equivalent, and the ratio of active hydrogen equivalents of (B) and (D) is preferably (B) / (D) = 2/1 to 4/1. . The polymaleimide compound (C) is preferably selected so as to be 5 to 30% of the total weight.

The composition of the present invention has the above-described epoxy resin, terminal functional imide compound, polymaleimide compound or polyphenol compound as an essential component, but if necessary, known epoxy resin curing agent or curing accelerator, filling Agents, flame retardants, reinforcing materials, surface treatment agents, pigments and the like can be used in combination.

Known epoxy curing agents include amine-based curing agents such as aromatic amines and aliphatic amines such as xylylenediamine,
Examples thereof include acid anhydrides, dicyandiamide, hydrazide compounds and the like.

As a curing accelerator, benzyldimethylamine, 2,4,6-
Amines such as tris (dimethylaminomethyl) phenol and 1,8-diazabicycloundecene, and imidazole compounds such as 2-ethyl-4-methylimidazole,
A boron trifluoride amine complex etc. can be illustrated. Examples of the filler include silica and calcium carbonate, and examples of the flame retardant include aluminum hydroxide, antimony trioxide, red phosphorus and the like. As a reinforcing agent, glass fiber, polyester fiber,
Examples of the cloth include organic cloth such as polyamide fiber and alumina fiber, non-woven cloth, mat, paper, or a combination thereof. Further, the composition of the present invention can be used in combination with an imide resin prepolymer obtained by reacting an unsaturated bisimide compound with a diamine.

<Effects of the Invention> The composition according to the present invention comprising the components described above gives a cured product having an extremely high heat resistance which has never been obtained, and has a high industrial value as a laminate or a molding material.

For example, an epoxy resin copper-clad laminate using the epoxy resin composition of the present invention has extremely high heat resistance which has never been obtained,
It also has excellent adhesion to copper foil and excellent water resistance. Here, this epoxy resin copper-clad laminate is a substrate for laminate,
It is obtained by impregnating a resin composition of the present invention dissolved in an organic solvent, drying the solvent to obtain a prepreg, and then heat laminating and molding the prepreg and a copper foil. Examples of the substrate for the laminated plate include woven or non-woven fabrics or mats made of glass fibers, polyester fibers, polyamide fibers and other inorganic fibers, organic fibers, paper, or a combination thereof. In addition, organic solvents include acetone, methyl ethyl ketone, methyl isobutyl ketone,
Examples include methyl cellosolve, ethyl cellosolve, dimethylformamide and the like. Examples of the heat molding conditions include press molding at a temperature of 150 to 250 ° C. and a pressure of 10 to 100 kg / cm ² for 20 to 300 minutes.

<Examples> Hereinafter, the present invention will be described in more detail with reference to Examples.

Reference Example-1 [Synthesis of Raw Material B ₁ ] In a 500 ml four-necked flask equipped with a stirrer, a thermometer, and a cooling condenser, maleic anhydride 110.8 g (1.125 mol),
N, N'-diphenyl-1,4-phenylenediamine 3.90 g,
Charge 100 g of toluene and 50 g of methyl isobutyl ketone. Subsequently, the temperature was raised to 120 ° C., 59.1 g (0.5 mol) of α-methylstyrene was added dropwise over 8 hours while maintaining the same temperature, and the temperature was kept at the same temperature for another 2 hours after completion of the addition. After the reaction, 50 g of toluene and 25 g of methyl isobutyl ketone were added and cooled to precipitate crystals. The crystals were separated by filtration, washed with toluene several times, and dried to obtain 55.7 g of powder crystals close to white.

In this product, the purity of B ₁ by GPC was 97.2%, the composition ratio of the isomers of B ₁ by GC was Y component / Z component 0.45 / 0.55, and the melting point was 206 to 208 ° C.

Reference Example-2 A flask equipped with a stirrer, a thermometer, a cooling liquid separator,
4-Toluenediamine (26.2 g, 0.215 mol) and m-cresol (117 g) were charged and the temperature was raised to 70 ° C. to dissolve 2,4-toluenediamine, and then the raw material 45.0 obtained in Reference Example-1 was used.
Charge g (0.148 mol) to form the polyamic acid.
Then, 25.2 g of toluene was charged, the temperature was raised to 150 ° C., and the dehydration reaction was continued at the same temperature for 10 hours.

After the reaction, the obtained resin solution was precipitated in 750 g of isopropanol, washed twice and dried under reduced pressure to obtain an imide compound.
This had an amine equivalent of 524 g / eq and a melting point of about 260 ° C.

Examples-1,2,3 Sumiepoxy ELA-128 (bisphenol A type epoxy resin, epoxy equivalent 186g / eq, Sumitomo Chemical Co., Ltd. product)
And the imide compound obtained in Reference Example-2 and N, N'-diphenylmethane bismaleimide (hereinafter abbreviated as BMI, manufactured by Sumitomo Chemical Co., Ltd.) at a ratio shown in Table 1 and uniformly dissolved in dimethylformamide. Let A glass cloth (WE18K, BZ-2 manufactured by Nitto Boseki Co., Ltd.) was impregnated with the solution and treated in an oven at 180 ° C. for 5 minutes to obtain a prepreg. 6 pieces of prepreg and copper foil (Furukawa Saki Kit Foil Co., Ltd., TAI treatment, 3
5 μm thick) were stacked and pressed at 200 ° C. under a pressure of 50 kg / cm ² for 5 hours to obtain a copper-clad laminate having a thickness of 1 mm. The physical properties of this laminated plate were measured according to JIS-C-6481 and the results shown in Table 1 were obtained.

Comparative Example-1 Sumiepoxy ESA-011 (bisphenol A type epoxy resin, epoxy equivalent 489 g / eq, product of Sumitomo Chemical Co., Ltd.) 240 g, Sumiepoxy ESCN-220 (o-cresol novolac type epoxy resin, epoxy equivalent 210 g / eq, product of Sumitomo Chemical Co., Ltd.) 20g, dicyandiamide 9g,
2-phenyl-4-methyl-5-hydroxymethylimidazole 1 g, dimethylformamide 40 g, ethylene glycol monomethyl ether 60 g, methyl ethyl ketone 60 g
Glass cloth was impregnated with this solution in the same manner as in Example-1, treated in an oven at 160 ° C. for 5 minutes to obtain a prepreg, and press-molded under the conditions of 180 ° C. and 50 kg / cm ² for 5 hours. Then, a laminated plate was produced. The physical properties of the laminate are shown in Table-1.

When the composition of the present invention is used as shown in Table-1,
It is clear that it exhibits excellent heat resistance, and also has excellent adhesiveness and water resistance.

Examples 4 to 8 Sumiepoxy ELA-128 (bisphenol A type epoxy resin, epoxy equivalent 186 g / eq, product of Sumitomo Chemical Co., Ltd.)
And Sumiepoxy ESB-400 (brominated bisphenol A type epoxy resin, epoxy equivalent 400g / eq, Sumitomo Chemical Co., Ltd. product) and the imide compound obtained in Reference Example-2 and o-cresol novolac resin (softening point 105 ° C) Alternatively, bisphenol A was blended in a ratio shown in Table 2 and uniformly dissolved in dimethylformamide. Glass cloth (WE18K, BZ-2, Nittobo Co., Ltd.) was impregnated with the solution at 180 ° C.
It was treated in an oven for 5 minutes to obtain a prepreg. Six prepregs and copper foil (Furukawa Circuit Foil Co., Ltd., TAI treatment, 35μ thickness) were layered and pressed at 180 ° C under a pressure of 50kg / cm ² for 5 hours to obtain a 1mm thick copper clad laminate. . The physical properties of this laminate were measured according to JIS-C-6481 and the results shown in Table 2 were obtained.

Comparative Example-2 Sumiepoxy ESA-011 (bisphenol A type epoxy resin, epoxy equivalent 489 g / eq, product of Sumitomo Chemical Co., Ltd.) 2
40 g, Sumiepoxy ESCN-220 (o-cresol novolac type epoxy resin, epoxy equivalent 210 g / eq, Sumitomo Chemical Co., Ltd. product) 20 g, dicyandiamide 9 g, 2-phenyl-4-methyl-5-hydroxymethylimidazole 1 g
Was dissolved in a mixed solvent of 40 g of dimethylformamide, 60 g of ethylene glycol monomethyl ether and 60 g of methyl ethyl ketone, glass cloth was impregnated with this solution in the same manner as in Example-4, and treated for 5 minutes in a 160 ° C. oven to obtain a prepreg. A laminated plate was prepared by press molding for 5 hours at 50 ° C. and 50 kg / cm ² . The physical properties of the laminate are shown in Table-2.

When the composition of the present invention is used as shown in Table-2,
It is clear that it exhibits excellent heat resistance, and also has excellent adhesiveness and water resistance.

Examples-9, 10 Sumiepoxy ELA-128 (bisphenol A type epoxy resin, epoxy equivalent 186 g / eq, product of Sumitomo Chemical Co., Ltd.)
And Sumiepoxy ESB-400 (brominated bisphenol A type epoxy resin, epoxy equivalent of 400 g / eq, a product of Sumitomo Chemical Co., Ltd.) and the imide compound obtained in Reference Example-2 and an o-cresol novolac resin (softening point 105 ° C.), And N, N′-diphenylmethane bismaleimide (hereinafter abbreviated as BMI, manufactured by Sumitomo Chemical Co., Ltd.) were mixed in the proportions shown in Table 3 and uniformly dissolved in dimethylformamide. A glass cloth (WE18K, BZ-2 manufactured by Nitto Boseki Co., Ltd.) was impregnated with the solution and treated in an oven at 180 ° C. for 5 minutes to obtain a prepreg. Six prepregs and copper foil (Furukawa Circuit Foil Co., Ltd., TAI treatment, 35μ thickness) were layered and pressed at 180 ° C under a pressure of 50kg / cm ² for 5 hours to obtain a 1mm thick copper clad laminate. . The physical properties of this laminate were measured according to JIS-C-6481 and the results shown in Table 3 were obtained.

Comparative Example-3 Sumiepoxy ESA-011 (bisphenol A type epoxy resin, epoxy equivalent 489 g / eq, product of Sumitomo Chemical Co., Ltd.) 2
40 g, Sumiepoxy ESCN-220 (o-cresol novolac type epoxy resin, epoxy equivalent 210 g / eq, Sumitomo Chemical Co., Ltd. product) 20 g, dicyandiamide 9 g, 2-phenyl-4-methyl-5-hydroxymethylimidazole 1 g
Was dissolved in a mixed solvent of 40 g of dimethylformamide, 60 g of ethylene glycol monomethyl ether, and 60 g of methyl ethyl ketone, glass cloth was impregnated with this solution in the same manner as in Example-9, and treated for 5 minutes in an oven at 160 ° C. to obtain prepreg. A laminate was prepared by press molding for 5 hours at 50 ° C. and 50 kg / cm ² . The physical properties of the laminate are shown in Table-3.

As shown in Table 3, it is apparent that when the composition according to the present invention is used, it exhibits excellent heat resistance, and also has excellent adhesiveness and water resistance.

─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. ⁵ Identification code Internal reference number FI Technical display location C08G 73/10 NTG 9285-4J H01L 23/29 23/31 (56) References Japanese Patent Laid-Open No. 50- 130851 (JP, A) JP 61-218626 (JP, A) JP 56-88420 (JP, A) JP 62-29584 (JP, A) JP 63-93784 (JP, A) JP 63-264631 (JP, A)

Claims (7)

[Claims] 1. An epoxy resin composition containing an epoxy resin (A), an imide compound (B) represented by the following general formula (I), and a polyimide compound (C) having two or more maleimide groups in the molecule. . [In the formula, X represents an —NH ₂ group and / or an —OH group, and Ar ₁ ,
Ar ₂ is independently an aromatic residue, R ₁ is a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, R ₂ is a hydrogen atom, and 1 carbon atom
~ 20 represents an alkyl group, an alkoxy group or a hydroxyl group, and m and n represent a number from 0 to 30. ] 2. The ratio of epoxy resin (A) to imide compound (B) is 0.6 g equivalent to 1.2 g equivalent to (g) (A) 1 g equivalent, and polymaleimide compound (C) and imide. The ratio of the compound (B) is 1 to the number of double bonds in (C), the number of active hydrogen H in the terminal functional group X of (B) is 0.6 to 1, and (A) and (C The epoxy resin composition according to claim 1, wherein the weight ratio (A) / (C) of) is 95/5 to 40/60. 3. An epoxy resin composition containing an epoxy resin (A), an imide compound (B) defined in claim 1 and a compound (D) having two or more phenolic hydroxyl groups in the molecule. 4. The ratio of the number of active hydrogens in the terminal functional group X of the imide compound (B) to the number of hydroxyl groups in the polyphenol compound (D) is (B) / (D) = 2/1 to 4/1. Yes, and epoxy resin (A)
The sum of active hydrogen equivalents of (B) and (D) is 0.6 to 1 g equivalent.
The epoxy resin composition according to claim 3, which has an equivalent weight of 1.2 g. 5. The epoxy resin composition according to claim 1 or 3, wherein m and n represent a number of 0-5. 6. The epoxy resin composition according to claim 1 or 3, wherein R ₁ is an alkyl group having 1 to 3 carbon atoms. 7. The epoxy resin composition according to claim 1 or _3, wherein R _{2 is a} hydrogen atom or an alkyl group having 1 to 5 carbon atoms.