JPH10158363A - Thermosetting resin composition and prepreg and laminated board produced by using the composition - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain the subject composition capable of improving the heat- resistance, mechanical properties and soldering heat-resistance by using a polymaleimide compound, a (hydroxyphenyl)-(maleimidophenyl)propane, a phenolic resin and an epoxy resin. SOLUTION: This composition contains (A) a polymaleimide compound of formula I (R1 is an m-valent organic group; Xa and Xb are each a univalent atom or group selected from H, halogen and organic group; (m) is an integer of >=2), (B) 2-(4-hydroxyphenyl)-2-(maleimidophenyl)propane of formula II, (C) a phenolic resin and (D) an epoxy resin having >=2 epoxy groups in one molecule. The composition has high Tg and, nevertheless, low hygroscopicity and good adhesivity. It has excellent soldering heat-resistance in moisture-absorbed state and is effectively usable as a resin material for laminated board.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The present invention relates to heat resistance, low moisture absorption,
The present invention relates to a resin composition, a prepreg, and a laminate having excellent adhesiveness, workability, toughness, and resistance to soldering heat after moisture absorption.
In other words, it relates to a resin composition for improving solder heat resistance after absorbing moisture as an insulating material for electronic / electric parts and semiconductor fields, a resin sealing material, and a laminated board material. The present invention relates to a resin composition useful for a board laminate, a prepreg and a laminate using the same.

[0002]

2. Description of the Related Art As for printed wiring boards widely used for electric / electronic devices, communication devices, computing devices, etc., the wiring density has been advanced and the integration has been advanced.
There is a growing demand for improved reliability by improving the heat resistance of wiring laminates. COB, PGA, BGA, MC
Applications for directly mounting a semiconductor chip on a substrate such as an M substrate have been increasing. In such a mounting process,
High temperature is required, and heat resistance is required for the substrate to be mounted. Conventionally, epoxy resins, unsaturated polyester resins, polyimide resins, phenolic resins, and the like have been used as resin materials constituting a laminate for a printed wiring board. Among these resins, epoxy resins and bismaleimides have been used. A polyaminobismaleimide resin obtained by reacting a resin with an aromatic diamine is widely used in high-density mounting and high-layer laminates.

[0003]

However, although the epoxy resin has relatively good heat resistance, it responds to the recent demand for improved heat resistance due to the high-density mounting of printed wiring boards and the high multilayer structure. Inevitably, there is a limit to the increase in heat resistance. Polyaminobismaleimide resins and the like have been proposed as materials for laminates having improved heat resistance (French Patent No. 1455514, JP-B-46-23250, JP-A-61-200149).
No.). In the case of this polyaminobismaleimide,
Although its heat resistance is very good, it has high hygroscopicity,
There is a problem in that the adhesiveness is disadvantageous, and a high temperature and a long time are required in laminating compared with the epoxy resin, so that there is a problem that the cost is increased. An imide-modified epoxy resin obtained by adding an epoxy resin to a polyaminobismaleimide resin (Japanese Patent Publication No. 47-42160) has been proposed to compensate for the drawbacks of the polyaminobismaleimide resin. And the heat resistance is insufficient.

For this reason, it is possible to cope with the future progress of high-density mounting and multi-layering, and it is possible to cope with an application for directly mounting a semiconductor chip. It has excellent heat resistance, low moisture absorption, and solder heat resistance after moisture absorption. There has been a strong demand for a low-cost resin material for laminates which has excellent mechanical properties such as excellent adhesiveness and toughness, and is inexpensive. The present invention has been made in view of such circumstances, and solves the drawbacks of conventional epoxy resins and polyimide resins, and provides a new resin material for a laminate having excellent heat resistance, particularly excellent solder heat resistance after moisture absorption. It is intended to provide.

[0005]

Means for Solving the Problems The present inventors have conducted intensive studies to solve the above-mentioned problems, and as a result, have found that a polymaleimide compound and 2- (4-hydroxyphenyl) -2-
By using (4-maleimidophenyl) propane, phenolic resin, and epoxy resin, heat resistance, mechanical properties, and solder heat resistance are exploited by taking advantage of the heat resistance of polymaleimide resin, adhesiveness of epoxy resin, and workability. We succeeded in improving it and completed the present invention.

That is, the present invention provides: 1) (a) a polymaleimide compound represented by the general formula (1)

[0007]

Embedded image (Wherein, R ₁ is an m-valent organic group, Xa and Xb are hydrogen atoms,
The same or different monovalent atoms or groups selected from halogen atoms and organic groups, m is an integer of 2 or more), and (b)
Formula (2)

[0008]

Embedded image 2- (4-hydroxyphenyl) -2- represented by
A thermosetting resin composition comprising (4-maleimidophenyl) propane, (c) a phenol resin, and (d) an epoxy resin having at least two epoxy groups in a molecule.

2) (a) a polymaleimide compound represented by the general formula (1); and (b) a 2-maleimide represented by the formula (2).
(4-hydroxyphenyl) -2- (4-maleimidophenyl) propane, (c) a phenolic resin, and (d)
Thermosetting resin composition comprising an epoxy resin having at least two or more epoxy groups in a molecule and (e) a modified imide resin obtained by modification with a compound having at least one active hydrogen in a molecule 3) The thermosetting resin composition according to claim 1 or 2, comprising a curing accelerator, a flame retardant, a filler and / or an additive. 4) The thermosetting resin composition according to (1), (2) or (3). A prepreg characterized by impregnating a base material with a resin material; 5) a thermosetting resin laminated plate characterized by being formed by laminating one or more prepregs of the above (4); and 6) The above (5) formed by laminating and integrating with the outermost metal foil
Is a thermosetting resin laminate.

[0010]

BEST MODE FOR CARRYING OUT THE INVENTION As the polymaleimide compound (a) used in the present invention, any compound having two or more maleimide groups in one molecule can be used. Such polymaleimide compounds include, for example, N, N'-
Ethylene bismaleimide, N, N'-hexamethylene bismaleimide, N, N '-(1,3-phenylene) bismaleimide, N,
N '-[1,3- (2-methylphenylene)] bismaleimide, N, N'
-(1,4-phenylene) bismaleimide, bis (4-maleimidophenyl) methane, bis (3-methyl-4-maleimidophenyl) methane, bis (4-maleimidophenyl) ether, bis (4-maleimidophenyl) sulfone , Screw (4-
(Maleimidophenyl) sulfide, bis (4-maleimidophenyl) ketone, bis (4-maleimidocyclohexyl) methane, 1,4-bis (4-maleimidophenyl) cyclohexane, 1,4-bis (maleimidomethyl) cyclohexane, 1,4 -Bis (maleimidomethyl) benzene, 1,3-bis
(4-maleimidophenoxy) benzene, 1,3-bis (3-maleimidophenoxy) benzene, bis [4- (3-maleimidophenoxy) phenyl] methane, bis [4- (4-maleimidophenoxy) phenyl] methane, 1 1,1-bis [4- (3-maleimidophenoxy) phenyl] ethane, 1,1-bis [4- (4-maleimidophenoxy) phenyl] ethane, 1,2-bis [4-
(3-maleimidophenoxy) phenyl] ethane, 1,2-bis [4- (4-maleimidophenoxy) phenyl] ethane, 2,
2-bis [4- (3-maleimidophenoxy) phenyl] propane, 2,2-bis [4- (4-maleimidophenoxy) phenyl]
Propane, 2,2-bis [4- (3-maleimidophenoxy) phenyl] butane, 2,2-bis [4- (4-maleimidophenoxy)
Phenyl] butane, 2,2-bis [4- (3-maleimidophenoxy) phenyl] -1,1,1,3,3,3-hexafluoropropane,
2,2-bis [4- (4-maleimidophenoxy) phenyl] -1,1,
1,3,3,3-hexafluoropropane, 4,4'-bis (3-maleimidophenoxy) biphenyl, 4,4'-bis (4-maleimidophenoxy) biphenyl, bis [4- (3-maleimidophenoxy) Phenyl] ketone, bis [4- (4-maleimidophenoxy) phenyl] ketone, bis [4- (3-maleimidophenoxy) phenyl] sulfide, bis [4- (4-maleimidophenoxy) phenyl] sulfide, bis [4- (3-maleimidophenoxy) phenyl] sulfoxide, bis [4-
(4-maleimidophenoxy) phenyl] sulfoxide,
Bis [4- (3-maleimidophenoxy) phenyl] sulfone, bis [4- (4-maleimidophenoxy) phenyl] sulfone, bis [4- (3-maleimidophenoxy) phenyl] ether, bis [4- (4-maleimide) Phenoxy) phenyl]
Ether, 1,4-bis [4- (4-maleimidophenoxy) -α,
α-Dimethylbenzyl] benzene, 1,3-bis [4- (4-maleimidophenoxy) -α, α-dimethylbenzyl] benzene, 1,4-bis [4- (3-maleimidophenoxy) -α, α- Dimethylbenzyl] benzene, 1,3-bis [4- (3-maleimidophenoxy) -α, α-dimethylbenzyl] benzene,
4-bis [4- (4-maleimidophenoxy) -3,5-dimethyl-
α, α-dimethylbenzyl] benzene, 1,3-bis [4- (4-
Maleimidophenoxy) -3,5-dimethyl-α, α-dimethylbenzyl] benzene, 1,4-bis [4- (3-maleimidophenoxy) -3,5-dimethyl-α, α-dimethylbenzyl] benzene, 1 , 3-bis [4- (3-maleimidophenoxy) -3,5-dimethyl-α, α-dimethylbenzyl] benzene, general formula (3)

[0011]

Embedded image (Wherein, n is an average value of 0 to 10), and a general formula (4) [Formula 6];

[0012]

Embedded image (Wherein, m is an average value of 0 to 10). These polymaleimide compounds may be used alone or as a mixture of two or more.

The component (b) is 2- (4-hydroxyphenyl) -2- (4-maleimidophenyl) propane represented by the formula (2).

The phenol resin as the component (c) includes phenols such as phenol, cresol, resorcinol, dihydroxybiphenyl and phenylphenol, naphthols such as 1-naphthol, 2-naphthol and dihydroxynaphthalene and formaldehyde, acetaldehyde and benzaldehyde. And novolak resins that are reaction products with aldehydes such as hydroxybenzaldehyde, gluoxal, and alkanedials, and aralkyl resins that are reaction products of the above phenols or naphthols with aralkyl alcohol derivatives or aralkyl halide derivatives. One or a mixture of two or more of these phenolic resins is used.

The epoxy resin as the component (c) includes:
All epoxy compounds having two or more epoxy groups in the molecule can be used. Examples of such an epoxy compound include phenols such as phenol, cresol, resorcinol, and naphthol, or phenols obtained by halogenating them, and aldehydes such as formaldehyde, acetaldehyde, benzaldehyde, tolualdehyde, glyoxal, and alkandial. An epoxy resin obtained by reacting a reaction product obtained by condensation reaction with epichlorohydrin. An epoxy resin obtained by reacting the above phenols with a reaction product of an aralkyl alcohol derivative or an aralkyl halide derivative.
Further, epoxy resins derived from the following compounds having two or more active hydrogens in one molecule, for example, bisphenol A, bisphenol F, resorcin, bishydroxydiphenyl ether, bishydroxybiphenyl, bishydroxynaphthalene, trihydroxy Polyphenols such as phenylmethane, ethylene glycol,
Polyhydric alcohols such as neopentyl glycol, glycerin, trimethylolpropane, pentaerythritol, diethylene glycol and polypropylene glycol;
Examples thereof include amines such as ethylenediamine, aniline, and bis (4-aminophenyl) methane; and epoxy resins obtained by reacting polychlorocarboxylic acids such as adipic acid, phthalic acid and isophthalic acid with epichlorohydrin. One or a mixture of two or more of these epoxy resins can be used. In addition, various halogenated epoxy resins such as a brominated phenol novolak resin and a brominated bisphenol A type epoxy resin can be used.

In the composition of the present invention, the polymaleimide compound represented by the general formula (1) of the component (a) and (b)
The mixing ratio of the component 2- (4-hydroxyphenyl) -2- (4-maleimidophenyl) propane is as follows:
1 to 50 parts by weight, preferably 2 to 100 parts by weight
To 40 parts by weight. The compounding amounts of the (c) phenol resin and the epoxy resin of the component (d) are as follows:
The total amount of the component (b) and the component (c) is 10 to 500 parts by weight, preferably 25 to 300 parts by weight, based on 0 part by weight, and the component (c) is based on the phenol resin of the component (b). The epoxy resin has an equivalent ratio in the range of 0.1 to 10, preferably 0.5 to 2.0. The resin composition of the present invention includes trihydroxyphenylmethane, tetrahydroxyphenylmethane, polyphenols such as tetrakisphenol, diaminodiphenylmethane, diaminodiphenylsulfone, amines represented by dicyandiamide, etc., phthalic anhydride, and pyromellitic anhydride. An acid anhydride such as an acid can be used in combination.

As the component (e) used in producing the modified imide resin, any compound having at least one active hydrogen in the molecule can be used. Compounds having at least one active hydrogen in the molecule include phenol, bisphenol A, bisphenol F, cresol, resorcinol, naphthol, phenols such as dihydroxynaphthol, aniline, aminophenol,
One alcohol in one molecule such as phenylenediamine, ethylenediamine, amines such as bis (4-aminophenyl) methane, glycidol, glycerin diglycidyl ether, ethylene glycol monoglycidyl ether, resorcinol monoglycidyl ether, naphthoresorcinol monoglycidyl ether, etc. A compound comprising an acidic or phenolic OH group and one or more epoxy groups,
Compounds having an OH group and an acetylene group such as propargyl alcohol are exemplified.

The method for producing the modified imide resin is as follows.
(A) a polymaleimide resin as a component, (b) a component,
Generally, all or a part of the component (c), the component (d) and the component (e) are heated and mixed at 80 to 200 ° C. for 0.1 to 10 hours, and further heated in an organic solvent. You may mix. When the mixture is heated and mixed in an organic solvent, it is generally 50 to 20 depending on the boiling point of the organic solvent used.
0.1 ° C. for 20 hours at 0 ° C. Although the content of the modified imide resin is not clear, it is considered to be mainly oligomerization of the polymaleimide resin. During the modification, the components (b), (c) and / or
Alternatively, it is difficult to produce a stable modified imide resin only with the component (d) or only the component (e).

The component (e) is preferably used in an amount of 5 to 100 parts by weight, based on 100 parts by weight of the polymaleimide resin.
It is preferred to use parts by weight. The amount of the phenol resin as the component (c) and the amount of the epoxy resin as the component (d) are preferably such that the total amount of the components (b) and (c) is 10 to 500 parts by weight, based on 100 parts by weight of the component (a). Is 25 to 300 parts by weight, and (c) with respect to the phenol resin of the component (b).
The equivalent ratio of the epoxy resin component is in the range of 0.1 to 10, preferably 0.5 to 2.0.

In the present invention, when the resin composition is cured, it is desirable to include a curing accelerator.
As such a curing accelerator, 2-methylimidazole,
Imidazoles such as 2-methyl-4-ethylimidazole and 2-heptadecylimidazole; amines such as triethanolamine, triethylenediamine and N-methylmorpholine; organic phosphines such as tributylphosphine, triphenylphosphine and tolylphosphine. ;
Tetraphenylphosphonium tetraphenylborate,
Tetraphenylboron salts such as triethylammonium tetraphenylborate; and 1,8-diaza-bicyclo (5,4,0) undecene-7 and derivatives thereof. These curing accelerators may be used alone or in combination of two or more, and if necessary, an organic peroxide or an azo compound may be used in combination. The content of these curing accelerators is 0.005 to 10 parts by weight per 100 parts by weight of the resin.
Used in parts by weight.

The resin material of the present invention may be used, if necessary, with an imide resin such as diallyl phthalate, triallyl isocyanurate, o, o'-diallylbisphenol A, bisphenol A diallyl ether, or bisphenol A dicyanate. Reactive diluents commonly used and used; various silicone oils; flame retardants such as bromo compounds, antimony, and phosphorus; fillers such as silica, talc, alumina, and aluminum nitride; polyether sulfone, polyphenylene ether, and aromatic polyester A linear polymer such as polysulfone, polyphenylene sulfide, polyetheretherketone, polyimide, polyetherimide, polyamideimide, and polyparabanic acid, and other appropriate additives may be blended.

In order to produce a prepreg using the resin composition of the present invention as described above, component (a), component (b), component (c), component (d),
A curing accelerator and other additives are dissolved in a solvent to form a resin varnish. Or (a) component, (b) component, (c) component,
A modified imide resin composed of the component (d) and the component (e), a curing accelerator and other additives are dissolved in a solvent to prepare a resin varnish. The polymaleimide compound as the component (a) is replaced with the component (b)
Component, component (c), component (d) or component (b), part or all of component (c) and component (d), and other additives were previously dissolved or reacted. After forming the prepolymer, it may be dissolved in a solvent to form a resin varnish. Further, the polymaleimide compound (a) is used as a component (b), a component (c), a component (d) or a part or all of the components (b), (c) and (d), and an additive in a solvent. In addition to the above, those reacted in a solvent may be used as a resin varnish.

The concentration of the thermosetting resin composition in the varnish is 4
A range of 0 to 70% by weight is desirable. As the solvent used at this time, ethylene glycol monoethyl ether, propylene glycol monomethyl ether, ethylene glycol monobutyl ether, N, N-dimethylformamide, N, N-dimethylacetamide, dioxane, acetone, N-methyl-2- Pyrrolidone, dimethyl sulfoxide, methyl ethyl ketone, methyl isobutyl ketone, cyclohexane, 2-heptanone and the like can be used.

As the substrate, all known substrates such as glass cloth, carbon fiber, organic fiber cloth, glass non-woven fabric and paper can be used. After applying and impregnating the varnish on the substrate, a prepreg is manufactured through a drying step, but the application method, impregnation method, and drying method are not particularly limited. The drying conditions are appropriately determined depending on the boiling point of the solvent used. However, a high temperature is not preferable, and the amount of the residual solvent in the prepreg is desirably 1% by weight or less.

The laminate is manufactured by heating and pressing one or a plurality of the above prepregs and integrating them. At this time, a metal foil or a metal plate is laminated on one side or both sides as the outermost layer. be able to. The heating temperature is 1
00 to 300 ° C, pressurization pressure is 5 to 100 kg /
cm ² is desirable. Copper, aluminum, iron, stainless steel or the like can be used as the metal foil or metal plate. Further, a laminated board for a multilayer printed wiring board may be formed by using an inner layer core material.

[0026]

The present invention will be described below in more detail with reference to examples. In addition, the test method of the performance in an Example is as follows. -Glass transition temperature: Dynamic viscoelasticity method-Copper foil peel test: JIS C-6481-Water absorption: JIS C-6481-Flexural strength: JIS C-6481-Solder heat resistance: Test according to JIS C-6481 The pieces were subjected to a water absorption treatment under the conditions of 120 ° C. and 100% RH for 3 hours, then floated in a solder bath at 300 ° C. for 120 seconds, and examined for abnormalities in the laminate.

The following raw materials were used in Examples and Comparative Examples.・ Polymaleimide compound; bis (4-maleimidophenyl) methane (manufactured by Mitsui Toatsu Chemicals, Inc.) ・ Phenol resin (1); naphthol / phenol novolak resin (Kayahard NHN, Nippon Kayaku Co., Ltd.) ・ Phenol resin (2) Phenol aralkyl resin (Mirex XL-225, manufactured by Mitsui Toatsu Chemicals, Inc.) Phenol resin (3) Phenol novolak resin (P
N-80, manufactured by Nippon Kayaku Co., Ltd.) Epoxy resin; bisphenol A type epoxy resin (Epicoat 1001, manufactured by Yuka Shell Epoxy Co., Ltd.) Glycidol; Epiol OH (manufactured by Nippon Oil & Fats Co., Ltd.) 6-dihydroxynaphthalene (manufactured by Kanto Chemical Co., Ltd.) Curing accelerator: 2-ethyl-4-methylimidazole (2E4MZ
, Shikoku Chemicals Co., Ltd.) ・ Polyaminobismaleimide resin; Kelimide 601A (Rhone Poulin)

Synthesis Example 2- (4-hydroxyphenyl) -2- (4-maleimidophenyl) propane was synthesized as follows. A reaction vessel equipped with a stirrer, a thermometer and an azeotropic distillation trap was charged with 60 g (0.61 mol) of maleic anhydride and 4 g of toluene.
80 g and 2.6 g of 95% sulfuric acid were inserted, and the mixture was heated to the reflux temperature with stirring, and 2- (4-hydroxyphenyl) -2-amine was added to 160 g of N, N-dimethylacetamide in advance.
A solution in which 114 g (0.5 mol) of (4-hydroxyphenyl) -2- (4-aminophenyl) propane was dissolved was added dropwise from a dropping funnel over 4 to 5 hours, and the reaction was carried out at the same temperature for 5 hours. Water generated by the reaction is removed azeotropically. After the completion of the reaction, the reaction solution was cooled to 80 to 90 ° C., and the solvent was immediately distilled off under reduced pressure. Subsequently, 100 ml of isopropyl alcohol was inserted into the obtained organic layer, and 300 ml of water was further added.
After stirring for 0.5 to 1 hour to precipitate crystals, the crystals were filtered and dried to give 2- (4-hydroxyphenyl) -2- (4-maleimidophenyl) propane as yellow crystals in 1 part.
47 g (96% yield) were obtained. The melting point of the obtained product was 168 to 171 ° C, and the result of purity analysis by gel permeation chromatography (GPC) was 99%.

Production Example of Modified Imide Resin (1) 90 parts by weight of a polymaleimide resin, 2- (4-hydroxyphenyl) -2 (4-maleimidophenyl) were placed in a reaction vessel equipped with a stirrer, thermometer and cooler. Propane 10
Parts by weight, 30 parts by weight of phenol resin (1), 50 parts by weight of epoxy resin, and 20 parts by weight of glycidol
The reaction was performed at 30 ° C. for 30 minutes to obtain a modified imide resin (1).

Production Example of Modified Imide Resin (2) 90 parts by weight of a polymaleimide resin, 2- (4-hydroxyphenyl) -2 (4-maleimidophenyl) were placed in a reaction vessel equipped with a stirrer, thermometer and cooler. Propane 10
Parts by weight, 30 parts by weight of phenolic resin (2), 60 parts by weight of epoxy resin, 10 parts by weight of 1,6 dihydroxynaphthalene, 90 parts by weight of methyl ethyl ketone, and 10 parts by weight of dimethylformamide, and reacted at 80 ° C. for 5 hours.
A modified imide resin (2) was obtained.

Examples 1 to 4 and Comparative Examples 1 to 4 Compounds having the compositions (parts by weight) shown in Table 1 were dissolved in a flask to obtain a thermosetting resin varnish. The thermosetting resin varnish thus obtained was impregnated with 104 g / m ² of glass cloth, dried at 140 ° C. for 5 minutes, and dried for about 190 minutes.
g / m ² of prepreg was obtained. The prepreg superimposed 16 sheets, by arranging further copper foil 18μ the outermost layer of the upper and lower, at a pressure of ^{40kg / cm 2, 180~200 ℃,} 1
Molding was performed under heating conditions for 20 minutes to obtain a 1.6 mm-thick copper-clad laminate. Table 1 shows the test results of the obtained laminates.
For comparison, a prepreg and a laminated board were also used for a polyaminobismaleimide resin having a composition similar to that of the example and not using 2- (4-hydroxyphenyl) -2- (4-maleimidophenyl) propane. It was manufactured and its resin properties were similarly evaluated. In the case of the polyaminobismaleimide resin of Comparative Example 3, 200 to 220
Molding was performed under heating conditions at 120 ° C. for 120 minutes.

As compared with the first to fourth embodiments of the present invention, 2- (4
When -hydroxyphenyl) -2- (4-maleimidophenyl) propane is not used, Tg measured by viscoelasticity is divided into a low temperature (about 150 ° C) and a high temperature (about 300 ° C), and the solder heat resistance is inferior. In the case of a polyaminobismaleimide resin, the water absorption is high and the solder heat resistance is poor. When no polymaleimide resin is contained, Tg is low and solder heat resistance is poor. As described above, the mechanical properties, the hygroscopicity, the adhesiveness, and the solder heat resistance were not at a level that satisfies all of the examples as compared with the present example.

[0033]

[Table 1]

[0034]

As described in Examples and Comparative Examples, the thermosetting resin composition according to the present invention has high Tg, low hygroscopicity, good adhesiveness, and low solder heat resistance after moisture absorption. It is an excellent thermosetting resin composition and is effective as a resin material for laminated boards.

──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. ⁶ Identification symbol FI C08L 71/10 C08L 71/10 // C08G 65/38 C08G 65/38

Claims (6)

[Claims] 1. A polymaleimide compound represented by the general formula (1): ## STR1 ## (Wherein, R ₁ is an m-valent organic group, Xa and Xb are hydrogen atoms,
The same or different monovalent atoms or groups selected from halogen atoms and organic groups, m is an integer of 2 or more), and (b)
Formula (2) [Formula 2] 2- (4-hydroxyphenyl) -2- represented by
A thermosetting resin composition comprising (4-maleimidophenyl) propane, (c) a phenol resin, and (d) an epoxy resin having at least two epoxy groups in a molecule. (2) A polymaleimide compound represented by the general formula (1) and (b) 2- (4-) represented by the formula (2)
(Hydroxyphenyl) -2- (4-maleimidophenyl) propane, (c) a phenolic resin, (d) an epoxy resin having at least two or more epoxy groups in a molecule, and (e) at least one epoxy resin in a molecule. A thermosetting resin composition comprising a modified imide resin obtained by modification with a compound having active hydrogen. 3. The thermosetting resin composition according to claim 1, further comprising a curing accelerator, a flame retardant, a filler and / or an additive. 4. A prepreg, wherein a base material is impregnated with the resin material according to claim 1, 2 or 3. 5. A thermosetting resin laminate, wherein one or more prepregs according to claim 4 are laminated. 6. The thermosetting resin laminate according to claim 5, which is formed by laminating and integrally forming the outermost metal foil.