JPH07278258A - Thermosetting resin composition, adhesive sheet, metal foil with adhesive, polyimide film, and metal-foil-laminated polyimide film - Google Patents

Abstract

PURPOSE:To improve the heat resistance of an adhesive contg. a high-mol.-wt. linear epoxy resin as the essential component. CONSTITUTION:A linear epoxy polymer obtd. by copolymerizing a diepoxy resin and a dihydric phenol in an equivalent ratio of epoxy group/phenolic hydroxyl group of (1:0.9)-(1:1.1) is compounded with a polymaleimide or an aminobismaleimide, a polyepoxy resin, and a curative.

Description

Detailed Description of the Invention

[0001]

FIELD OF THE INVENTION The present invention relates to a thermosetting resin composition having film forming ability. INDUSTRIAL APPLICABILITY The resin composition of the present invention is useful as a thermosetting adhesive having excellent heat resistance, which can be used for printed circuit boards, TABs, composite lead frames, laminated materials and the like.

[0002]

2. Description of the Related Art As an insulating adhesive for electronic materials, a hot melt adhesive, a resin adhesive such as an acrylic adhesive, a phenol adhesive, an epoxy adhesive, a polyimide adhesive, or a resin adhesive combining them is used. Has been done. A resin composition in which a maleimide or an epoxy resin is mixed with a polyimide resin or a resin composition in which an epoxy resin is mixed with a maleimide is used as a heat resistant adhesive.

Among these adhesives, the hot melt adhesive has a high bonding temperature of around 300 ° C. and is restricted by the adherend and the heating device. Further, since it is a hot melt, it is exposed to a high temperature again after bonding. And the adhesive softens and the strength cannot be maintained. Acrylic, phenol, and epoxy adhesives have excellent adhesiveness but poor heat resistance. Although it is known that polyimide adhesives can be heated and pressed to be bonded at 180 ° C., when they are used in TAB or the like, it is difficult to bond them with a roll toe roll. A resin composition in which an epoxy resin is mixed with a maleimide, which is also known for heat-resistant laminated plates, has excellent adhesiveness and heat resistance, but the resin alone cannot be formed into a sheet and impregnated into a glass cloth or the like. Since it has to be used as a prepreg, it is difficult to use it in TAB or the like which requires flexibility, and its application is limited.

Therefore, an epoxy resin composition containing a high molecular weight epoxy polymer capable of forming a film, a polyfunctional epoxy resin and a curing agent has been proposed (Japanese Patent Laid-Open No. 5-253).
68 publication). The high molecular weight epoxy polymer capable of forming a film is obtained by polymerizing a bifunctional epoxy resin and a bifunctional phenol in an amide solvent in the presence of a catalyst (see JP-A-4-120124). .

[0005]

However, an epoxy resin composition containing a high molecular weight epoxy polymer, a polyfunctional epoxy resin and a curing agent is a resin composition for use in the field of electronic parts such as TAB and composite lead frames. However, there is a drawback in that the elastic modulus at high temperature cannot be maintained, and defective wire bonding at the time of chip mounting cannot be avoided.

The present invention has excellent heat resistance and adhesiveness, and
It is intended to provide a thermosetting resin composition which can be adhered at a low temperature of 80 ° C. or lower and can be adhered by a roll tow roll, and an application product of the thermosetting resin composition as an adhesive.

[0007]

The present invention is obtained by polymerizing a bifunctional epoxy resin and a bifunctional phenol at an equivalent ratio of epoxy group / phenolic hydroxyl group = 1 / (0.9 to 1.1). A gist is a thermosetting resin composition in which a polymaleimide or amino bismaleimide, a polyfunctional epoxy resin and a curing agent are mixed with a linear epoxy polymer.

The linear epoxy polymer used in the present invention is
The bifunctional epoxy resin and the bifunctional phenols are mixed with each other, and the compounding equivalent ratio of the bifunctional epoxy resin and the bifunctional phenols is epoxy group / phenolic hydroxyl group = 1 / (0.9 to 1.1),
In the presence of a catalyst, in an amide solvent having a boiling point of 130 ° C. or higher,
It is obtained by heating and polymerizing at a reaction solid content concentration of 5 to 50% by weight.

The bifunctional epoxy resin may be any compound as long as it is a compound having two epoxy groups in the molecule. For example, bisphenol A type epoxy resin, bisphenol F type epoxy resin, bisphenol S type epoxy resin, Alicyclic epoxy resin, aliphatic chain epoxy resin, diglycidyl ether of bifunctional phenols,
There are diglycidyl ether compounds of difunctional alcohols, halides thereof, hydrogenated products thereof, and the like. There is no limitation on the molecular weight of these compounds. Moreover, several kinds of these compounds can be used together. Components other than the bifunctional epoxy resin may be included as impurities.

The bifunctional phenols may be any compounds having two phenolic hydroxyl groups, for example, monocyclic bifunctional phenols such as hydroquinone, resorcinol, catechol and polycyclic bifunctional phenols. Examples include bisphenol A, bisphenol F and their halides and alkyl-substituted compounds. There is no limitation on the molecular weight of these compounds. Similar to the bifunctional epoxy resin, several kinds of these compounds can be used together. Further, a component other than the bifunctional phenol may be contained as an impurity.

The catalyst for polymerizing the bifunctional epoxy resin and the bifunctional phenol may be any compound having a catalytic function for promoting the etherification reaction of the epoxy group and the phenolic hydroxyl group. Examples thereof include alkali metal compounds, alkaline earth metal compounds, imidazoles, organic phosphorus compounds, secondary amines, tertiary amines, and quaternary ammonium salts. Examples of alkali metal compounds include hydroxides, halides, organic acid salts, alcoholates, phenolates, hydrides, borohydrides and amides of sodium, lithium or potassium. These catalysts can be used in combination.

The amide-based solvent may be any one as long as it can dissolve the bifunctional epoxy resin as a raw material and the bifunctional phenols. For example, formamide, N-methylformamide, N, N-dimethylformamide, acetamide, N
-Methylacetamide, N, N-dimethylacetamide, N, N, N ', N'-tetramethylurea, 2-pyrrolidone, N-methylpyrrolidone, carbamic acid ester and the like. These solvents can be used in combination. Further, it may be used in combination with another solvent represented by a ketone solvent or an ether solvent.

The compounding equivalent ratio of the bifunctional epoxy resin and the bifunctional phenols is epoxy group / phenolic hydroxyl group = 1.
/(0.9-1.1). If the equivalent of the phenolic hydroxyl group is less than 0.9 equivalent, the polymer does not linearly polymerize,
Side reactions occur and crosslink, making the resin insoluble in the solvent. When the equivalent of the phenolic hydroxyl group is larger than 1.1 equivalent, the resin does not have a high molecular weight.

The amount of the catalyst to be blended is not particularly limited, but in general, the amount of the catalyst is 0.00 based on 1 mol of the bifunctional epoxy resin.
It is about 01 to 0.2 mol. If the amount of the catalyst compounded is less than 0.0001 mol per mol of the bifunctional epoxy resin, the high molecular weight reaction is remarkably slow, and if it is more than 0.2 mol, side reactions increase and the linearity increases. May not be molecular weight.

The solid content concentration in the polymerization reaction using the amide-based solvent may be 50% (wt%, the same applies hereinafter) or less, but preferably 10 to 30%. As the concentration becomes higher, side reactions increase, and it becomes difficult to form a linear polymer having a high molecular weight. When the concentration is lower than 10%, the reaction is slow and it is difficult to increase the molecular weight. Therefore, when the polymerization reaction is carried out at a relatively high concentration and a linear high molecular weight epoxy polymer is to be obtained, the reaction temperature may be lowered and the catalyst amount may be reduced. The molecular weight of the high molecular weight epoxy polymer is
There is no problem as long as the resin alone has a film-forming ability and a molecular weight capable of obtaining a sheet-shaped adhesive. Such a molecular weight is approximately 70,000 or more. More preferably,
It is 100,000-150,000. The upper limit of the molecular weight of the high molecular weight epoxy polymer is not particularly limited. However, in reality, when the molecular weight is 150,000 or more, it is difficult to accurately measure the molecular weight and the viscosity becomes high, so that it becomes difficult to handle as a varnish.

The polymaleimides to be blended with the high molecular weight epoxy polymer include the following compounds.
These may be used alone or in combination of two or more. N,
N '-(4,4'-diphenylmethane) bismaleimide, N, N'-(4,4'-diphenyloxy) bismaleimide, N, N'-p-phenylene bismaleimide,
N, N'-m-phenylene bismaleimide, N, N'-
2,4-tolylene bismaleimide, N, N'-2,6-
Tolylene bismaleimide, N, N′-ethylene bismaleimide, N, N ′-{4,4 ′-[2,2′-bis (4,4′-phenoxyphenyl) isopropylidene]} bismaleimide, N, N '-{4,4'-[2
2'-bis (4,4'-phenoxyphenyl) hexafluoroisopropylidene]} bismaleimide, N, N '
-[4,4'-Bis (3,5-dimethylphenyl) methane] bismaleimide, N, N '-[4,4'-bis (3,5-diethylphenyl) methane] bismaleimide, N, N' -[4,4 '-(3-Methyl-5-ethylphenyl) methane] bismaleimide, N, N'-[4
4′-bis (3,5-diisopropylphenyl) methane] bismaleimide, a maleimide represented by Chemical formula 1 to Chemical formula 6.

[0017]

[Chemical 1]

[0018]

[Chemical 2]

[0019]

[Chemical 3]

[0020]

[Chemical 4]

[0021]

[Chemical 5]

[0022]

[Chemical 6] (In chemical formula 6, r is an integer of 1 or more.)

The aminobismaleimide to be added to the high molecular weight epoxy polymer can be obtained by heating and reacting bismaleimide and diamine in an organic solvent. The bismaleimide used in this reaction is
Of the polymaleimides shown above, difunctional compounds can be used. Further, as the diamine,
4,4'-diaminodiphenyl ether, 4,4'-diaminodiphenylmethane, 4,4'-diaminodiphenyl sulfone, 2,2-bis [4- (4-aminophenoxy) phenyl] propane, 2,2-bis [3 -Methyl-
4- (4-aminophenoxy) phenyl] propane,
2,2-bis [4- (4-aminophenoxy) phenyl] butane, 2,2-bis [3-methyl-4- (4-aminophenoxy) phenyl] butane, 2,2-bis [3,5- Dimethyl-4- (4-aminophenoxy) phenyl] butane, 2,2-bis [3,5-dibromo-4
-(4-aminophenoxy) phenyl] butane, 1,
1,1,3,3,3-hexafluoro-2,2-bis [3-methyl-4- (4-aminophenoxy) phenyl] propane, bis [4- (4-aminophenoxy) phenyl] sulfone, bis [4- (4-aminophenoxy) phenyl] ether, bis [4- (3-aminophenoxy) phenyl] sulfone, 4,4′-carbonylbis (p-phenyleneoxy) dianiline, 4,4′-bis (4 -Aminophenoxy) biphenyl, metaphenylenediamine, hexamethylenediamine, tetramethylenediamine and the like.

The mixing ratio of bismaleimide and diamine is preferably in the range of 1: 0.1 to 1: 1 in terms of molar ratio. When the compounding amount of the diamine is 0.1 mol or less with respect to 1 mol of the bismaleimide, the solubility of the produced amino bismaleimide in the solvent is lowered and the compound is precipitated during the reaction. On the other hand, if it is more than 1 mol, the reaction is so fast that a crosslinking reaction is likely to occur and the desired aminobismaleimide cannot be obtained.

Examples of the polyfunctional epoxy resin to be blended with the high molecular weight epoxy polymer include the following epoxy compounds having an average of two or more epoxy groups per molecule. Bisphenol epoxy resin, halogenated bisphenol epoxy resin, bisphenol novolac epoxy resin, halogenated bisphenol novolac epoxy resin, phenol novolac epoxy resin, halogenated phenol novolac epoxy resin,
Alkylphenol novolac epoxy resin, polyphenol epoxy resin, polyglycol epoxy resin, cycloaliphatic epoxy resin. These may be used alone or in combination of two or more.

The epoxy resin curing agent is not particularly limited as long as it is one generally used as an epoxy resin curing agent such as dicyandiamide, polyphenols and acid anhydrides. Further, the curing accelerator is also 2-methylimidazole, 2-methyl-4-ethylimidazole,
Imidazoles such as 2-undecylimidazole and 2-heptadecylimidazole and their derivatives, diethylamine, triethylamine, monoethanolamine,
Amines such as diethanolamine, BF ₃ amine complex and the like can be used and are not particularly limited.

The blending ratio of the high molecular weight epoxy polymer, maleimides or aminobismaleimide, and the polyfunctional epoxy resin is preferably 40 to 80% by weight of the high molecular weight epoxy polymer. When the content of the high molecular weight epoxy polymer is 40% by weight or less, the resin composition becomes brittle and the handling becomes difficult. 8
When it is 0% by weight or more, the adhesiveness is poor, and the softening temperature of the resin composition after heat curing is lowered, so that the elastic modulus at high temperature cannot be maintained. It is preferable that maleimides or aminobismaleimide and a polyfunctional epoxy resin are used in combination, and each is blended in an amount of 10% by weight or more.

If maleimides or aminobismaleimide are not blended, the softening temperature of the resin composition after heat curing is lowered, and the elastic modulus at high temperature cannot be maintained. If a polyfunctional epoxy resin is not added, the adhesiveness will be poor.

It is convenient that the thermosetting resin composition of the present invention is formed into a sheet shape in advance and used as a sheet adhesive. Further, the thermosetting resin composition of the present invention is impregnated into a glass cloth, a glass mat, an aromatic polyamide fiber cloth, an aromatic polyamide fiber mat or the like as a varnish,
It is also possible to semi-cure the resin and use it as a fiber-reinforced sheet adhesive.

The thermosetting resin composition of the present invention may be used as a varnish, which is directly applied to an adherend, dried, and heated and pressed to adhere to another adherend. At that time, the temperature is 100 to 25
It is preferable to heat and pressurize at 0 ° C. and a pressure of 0.1 to 10 MPa for 20 minutes or more. Especially, the temperature is 150 ~ 200 ℃, the pressure is 1
It is more preferable to heat and pressurize at ~ 4 MPa for 60 to 90 minutes.

The thermosetting resin composition of the present invention is used as a varnish, and the varnish is applied to one side or both sides of a polyimide film and dried. It is useful for manufacturing flexible printed circuit boards, TAB tapes, etc. by pressing.

Further, the double-sided adhesive layer-attached polyimide film is adhered to the printed circuit boards or to the printed circuit boards with a metal foil such as a copper foil, an aluminum foil, or a 42 alloy foil,
It is possible to manufacture thin film multilayer circuit boards and metal composite boards. The adhesive varnish of the present invention is coated on one side of a polyimide film on which the metal foil of the polyimide film is not stretched, and the dried adhesive layer-attached one-sided metal foil of the polyimide film is a flexible printed circuit board or The 42 alloy foil is particularly useful for manufacturing a thin film multilayer circuit board, a composite lead frame and the like by heating and pressing.

[0033]

【Example】

Example 1 (Synthesis of high molecular weight epoxy resin) Bisphenol A type epoxy resin (epoxy equivalent:
177.5) 177.5 g, bisphenol A as a bifunctional phenol (hydroxyl equivalent: 115.5) 115.
5 g, sodium hydroxide 1.77 as etherification catalyst
g was dissolved in N, N-dimethylformamide 547.9 g which is an amide solvent, and the solid content concentration in the reaction system was adjusted to 30
%. While mechanically stirring this, the temperature in the reaction system was kept at 120 ° C. in an oil bath at 125 ° C., and the mixture was stirred as it was for 4 hours. As a result, the viscosity is 12,800 mP
The reaction was completed after saturation with a.s. The weight average molecular weight of the obtained high molecular weight epoxy polymer was 72,500 as a result of measurement by gel permeation chromatography and 59,200 as a result of measurement by a light scattering method. The reduced viscosity of the dilute solution of the high molecular weight epoxy resin was 0.770 dl / g.

The resulting high molecular weight epoxy polymer solution (3
0% by weight solution) 15 g of bisphenol A type epoxy resin (epoxy equivalent 177.5) and N, N'-
(4,4′-diphenylmethane) bismaleimide 15
g, dicyandiamide 1 g and N, N-dimethylformamide 69 g were added and stirred to obtain a varnish. The obtained varnish was cast on a glass plate, dried at 100 ° C. for 10 minutes, peeled from the glass plate, fixed on an iron frame, and
It was dried at 0 ° C. for 20 minutes to obtain a sheet having a thickness of 25 μm.
A 35 μm-thick copper foil was placed on the outside of the two obtained sheets and heated and pressed at 180 ° C. and 3 MPa for 90 minutes to obtain a double-sided copper-clad flexible laminate.

Example 2 The varnish obtained in Example 1 was applied to the film side of a single-sided copper-clad polyimide film and heated at 100 ° C. for 10 minutes and then at 150 ° C. for 20 minutes to form an adhesive layer having a thickness of 10 μm. Provided. Two pieces of the obtained single-sided copper-clad polyimide film with an adhesive layer were put together on the adhesive layer side, and the temperature was 150 ° C.
Lamination was performed with a roll laminator under the conditions of a cylinder pressure of 0.5 MPa and a speed of 1 m / min. Then temperature 180
It was cured for 90 minutes in a dryer at 0 ° C. to obtain a double-sided copper-clad flexible laminate.

Example 3 The varnish obtained in Example 1 was applied to one side of a polyimide film having a thickness of 75 μm and heated at 100 ° C. for 10 minutes and then at 150 ° C. for 20 minutes to form an adhesive layer having a thickness of 20 μm. It was The obtained single-sided polyimide film with an adhesive layer and a 35 μm copper foil were heated at 150 ° C. and a cylinder pressure of 0.5 M.
Lamination was performed with a roll laminator under the conditions of Pa and speed of 1 m / min. Then, in a dryer at a temperature of 180 ° C, 90
After curing for 1 minute, a single-sided copper-clad polyimide film was obtained.

Example 4 The varnish obtained in Example 1 was applied to the roughened surface side of a copper foil having a thickness of 35 μm and heated at 100 ° C. for 10 minutes and subsequently at 150 ° C. for 20 minutes to obtain an adhesive having a thickness of 20 μm. Layers were provided. The obtained copper foil with an adhesive layer and the glass-based epoxy resin laminate were placed at a temperature of 150 ° C., a cylinder pressure of 0.5 MPa, and a speed of 1
Lamination was performed by a roll laminator under the condition of m / min. Then, it was cured for 90 minutes in a dryer at a temperature of 180 ° C. to obtain a single-sided copper-clad laminate.

Example 5 (Synthesis of aminobismaleimide) To 60 g of N, N '-(4,4'-diphenylmethane) bismaleimide, 80 g of N, N-dimethylformamide was added and dissolved, and the mixture was heated to 120 ° C. 20 g of 2,2-bis [4- (4-aminophenoxy) phenyl] propane was added, and the reaction was carried out for 60 minutes while maintaining the temperature at 120 ° C. Then, it cooled to room temperature and the amino bismaleimide solution (50 weight% solution) was obtained.

36 g of the obtained amino bismaleimide solution
100 g of the polymer epoxy resin solution obtained in Example 1
And bisphenol A type epoxy resin (epoxy equivalent 17
7.5) 12 g and N, N-dimethylformamide 5
2 g was added and dissolved to give a varnish. The resulting varnish was cast on a glass plate, dried at 100 ° C. for 10 minutes, peeled from the glass plate, fixed on an iron frame, and dried at 150 ° C. for 20 minutes to obtain a sheet having a thickness of 25 μm. A copper foil having a thickness of 35 μm is arranged on the outside of the two obtained sheets, and 180
By heating and pressing at 90 ° C. and 3 MPa for 90 minutes, a double-sided copper-clad flexible laminate was obtained.

Example 6 The varnish obtained in Example 5 was applied to the film surface of a single-sided copper-clad polyimide film and heated at 100 ° C. for 10 minutes and then at 150 ° C. for 20 minutes to form an adhesive layer having a thickness of 10 μm. Provided. Two pieces of the obtained single-sided copper-clad polyimide film with an adhesive layer were put together on the adhesive layer side, and the temperature was 150 ° C.
Lamination was performed with a roll laminator under the conditions of a cylinder pressure of 0.5 MPa and a speed of 1 m / min. Then temperature 180
It was cured for 90 minutes in a dryer at 0 ° C. to obtain a double-sided copper-clad flexible laminate.

Example 7 The varnish obtained in Example 5 was applied to one surface of a polyimide film having a thickness of 75 μm and heated at 100 ° C. for 10 minutes and then at 150 ° C. for 20 minutes to form an adhesive layer having a thickness of 20 μm. It was The obtained single-sided polyimide film with an adhesive layer and a 35 μm copper foil were heated at 150 ° C. and a cylinder pressure of 0.5 M.
Lamination was performed with a roll laminator under the conditions of Pa and speed of 1 m / min. Then, in a dryer at a temperature of 180 ° C, 90
After curing for 1 minute, a single-sided copper-clad polyimide film was obtained.

Example 8 The varnish obtained in Example 5 was applied to the roughened surface side of a copper foil having a thickness of 35 μm and heated at 100 ° C. for 10 minutes and then at 150 ° C. for 20 minutes to obtain an adhesive having a thickness of 20 μm. Layers were provided. The obtained copper foil with an adhesive layer and the glass-based epoxy resin laminate were placed at a temperature of 150 ° C., a cylinder pressure of 0.5 MPa, and a speed of 1
Lamination was performed by a roll laminator under the condition of m / min. Then, it was cured for 90 minutes in a dryer at a temperature of 180 ° C. to obtain a single-sided copper-clad laminate.

With respect to the flexible laminate, the one-sided copper-clad polyimide film and the one-sided copper-clad laminate obtained in each of the above examples, peel strength and solder heat resistance (28
The appearance after being floated in a solder bath at 8 ° C. for 1 minute) and the wire bonding property (connection state of the chip and the pattern at a bonding temperature of 180 ° C.) were examined. The results are shown in Table 1.

[0044]

[Table 1] ━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━ Example 1 2 3 4 5 6 7 8 ─ ────────────────────────────────── Peeling strength (kN / m) 1.75 1.62 1.53 1.72 1.92 1.85 1.80 1.90 Solder Heat Resistance Good Good Good Good Good Good Good Good Good Wire Bonding Good Good Good Good Good Good Good Good Good ━━━━━━━━━━━━━━━━━━━━━━━━━━━ ━━━━━━━━

Comparative Example 1 High molecular weight epoxy polymer solution 100 obtained in Example 1
bisphenol A type epoxy resin (epoxy equivalent 1
77.5) 30 g and N, N-dimethylformamide 70
g was added to form a varnish. An adhesive sheet was obtained under the same conditions as in Example 1 and heated and pressed under the same configuration and conditions to obtain a double-sided copper-clad flexible laminate. The peel strength of this flexible laminate was 2.5 kN / m. However, after floating in a solder bath at 288 ° C. for 1 minute, blistering occurred. Further, in wire bonding at 180 ° C., the adhesive layer was softened and the defective bonding rate was 50% or more.

Comparative Example 2 High molecular weight epoxy polymer solution 100 obtained in Example 1
To g, 60 g of the aminobismaleimide resin solution obtained in Example 5 and 40 g of N, N-dimethylformamide were added to give a varnish. An adhesive sheet was obtained under the same conditions as in Example 1 and heated and pressed under the same configuration and conditions to obtain a double-sided copper-clad flexible laminate. The peel strength of this flexible laminate was only 0.7 kN / m. Also, 2
After floating in a solder bath at 88 ° C for 1 minute, blistering occurred. Also, in wire bonding at 180 ° C,
The adhesive layer was softened and the defective bonding rate was 30% or more.

Comparative Example 3 A commercially available acrylic adhesive sheet was used and heated and pressed under the same constitution and conditions as in Example 1 to obtain a double-sided copper-clad flexible laminate. The peel strength of this flexible laminate was 2.2 kN / m. However, after floating in a solder bath at 288 ° C. for 1 minute, blistering occurred. Also,
In wire bonding at 180 ° C., the adhesive layer softened and bonding was impossible.

Comparative Example 4 A double-sided copper-clad flexible laminate was obtained by using a commercially available epoxy adhesive sheet and heating and pressing under the same structure and conditions as in Example 1. The peel strength of this flexible laminate was 1.9 kN / m. However, after floating in a solder bath at 288 ° C. for 1 minute, blistering occurred. Also,
In wire bonding at 180 ° C., the adhesive layer softened and the bonding failure rate was 50% or more.

Comparative Example 5 A commercially available polyimide-based adhesive sheet was used and heated and pressed under the same structure and under the same conditions as in Example 1, but no adhesion occurred and a double-sided copper-clad flexible laminate could not be obtained.

[0050]

The thermosetting resin composition of the present invention can be adhered at a temperature of about 180 ° C. when used as an adhesive. Unlike conventional heat-resistant adhesives, it does not require high temperature for adhesion, and can be pasted with roll-toe rolls, making it easy to handle. Moreover, the adhesive does not soften even at high temperatures, and the wire bondability is excellent. Further, it can be processed into a sheet shape in advance. Further, since it is soluble in a solvent, it can be applied to an adherend in advance and adhered to another adherend.

─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. ⁶ Identification number Office reference number FI technical display location C09J 7/02 JHX JKA 163/00 JFM

Claims (7)

[Claims] 1. An epoxy group / phenolic hydroxyl group = 1 / (0.9 to 0.9) containing a bifunctional epoxy resin and a bifunctional phenol.
A thermosetting resin composition in which polymaleimides or amino bismaleimide, a polyfunctional epoxy resin and a curing agent are mixed with a linear epoxy polymer obtained by polymerizing at an equivalent ratio of 1.1). 2. The linear epoxy polymer has a molecular weight of 70,
The thermosetting resin composition according to claim 1, which is 000 or more. 3. An adhesive sheet in which the thermosetting resin composition according to claim 1 or 2 is formed into a sheet. 4. A metal foil with an adhesive, wherein an adhesive layer made of the thermosetting resin composition according to claim 1 is provided on one surface of the metal foil. 5. A polyimide film with an adhesive, wherein an adhesive layer made of the thermosetting resin composition according to claim 1 is provided on one side or both sides of the polyimide film. 6. A one-sided metal-clad polyimide film comprising a polyimide film covered with a metal foil on one side and the other side provided with an adhesive layer comprising the thermosetting resin composition according to claim 1. 7. A metal-clad polyimide film obtained by laminating a metal foil to one or both sides of a polyimide film using the resin composition according to claim 1 as an adhesive.