JPH0827427A - Heat-resistant film adhesive and its production - Google Patents

Abstract

PURPOSE:To obtain a heat-resistant film adhesive, excellent in low-temperature processabillty, bonding operation efficiency and reliability and useful for electron ics, etc., by flow-casting a solution of a specific heat-resistant resin composition onto the surface of a support. CONSTITUTION:This heat-resistant film adhesive contains (A) 100 pts.wt. polyimide resin, soluble in organic solvents, having <=350 deg.C glass transition temperature and comprising a siloxane compound of the formula [R1 and R2 are each a bivalent 1-4C aliphatic or aromatic group; R3 to R5 are each a monovalent aliphatic or aromatic group; (k) is 1-20] such as alpha,omega-bis(3-aminopropyl) polydimethylsiloxane in an amount of 5-50mol% based on the total amount of the amine component, (B) 5-100 pts.wt. epoxy compound having >=2 epoxy groups in one molecule such as a bisphenol A type epoxy resin and (C) 0.1-50 pts.wt. coupling agent such as a silane coupling agent as principal components. Furthermore, the method for producing the heat-resistant film adhesive is to flow-cast a solution of a heat-resistant resin composition containing the components (A), (B) and (C) onto one or both surfaces of a support.

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a film adhesive which has both heat resistance and low-temperature processability and is suitable for electronics, especially as a semiconductor mounting material, and has excellent adhesiveness to silicon substrates and metals, and a method for producing the same. Is.

[0002]

2. Description of the Related Art In recent years, while semiconductor chips have become larger due to higher functionality and larger capacity, the size of the package has not changed from the conventional one due to restrictions on printed circuit design, demand for miniaturization of electronic equipment, or a rather small external shape. Is being requested. In response to this tendency, some new mounting methods have been proposed for high density and high density mounting of semiconductor chips. One is a COL that mounts a chip on a lead frame without a die pad proposed for memory devices.
(Chip-on-lead) structure and LOC (lead-on-chip) structure in which leads are mounted on a chip, which is a development of the structure. On the other hand, the logic element has a multi-layered lead frame structure in which a power source and a ground are provided in different frames and a metal plate for heat dissipation is multi-layered. According to these, it is possible to rationalize the wiring in the chip and wire bonding, to speed up the signal by shortening the wiring, to dissipate heat generated due to the increase in power consumption, and to reduce the element size.

In this new mounting mode, there are bonding interfaces of the same kind and different materials such as a semiconductor chip and a lead frame, a lead frame and a plate, and lead frames, and the bonding reliability greatly affects the reliability of the device. . Not only the reliability of withstanding the process temperature at the time of assembling the element, but also the bonding reliability at the time of moisture absorption, heat and humidity. Further, the workability of bonding is also an important item.

Conventionally, a paste-like adhesive or a heat-resistant base material coated with an adhesive has been used for these adhesions. Epoxy resin-based, acrylic resin-based, and rubber-phenol resin-based thermosetting resins are used as adhesives, but there are many ionic impurities, heat curing requires high temperature and long time, and productivity is poor, heat curing It is hard to say that the requirements for a highly reliable adhesive such as a large amount of volatile components that contaminate leads and high hygroscopicity are satisfied, and no satisfactory material is found. There is a demand for the development of adhesives suitable for new mounting forms. One of such methods is a hot-melt type film adhesive using a polyimide resin (see JP-A-5-105850, 112760, 112761). A hot-melt type adhesive can be thermocompression-bonded to an adherend in a short time, and a heat-curing step after adhesion is not required, which is considered to greatly contribute to improvement in productivity and reliability. . However, since it is a hot-melt type, if the glass transition temperature of the adhesive resin is high, it takes a very high temperature for processing, and there is a great possibility that the adherend is thermally damaged. On the other hand, if the glass transition temperature is lowered in order to impart low-temperature processability, there is a problem that the heat resistance is lowered, and thus the reliability is lowered.

[0005]

DISCLOSURE OF THE INVENTION The present invention has been earnestly studied to obtain a film adhesive which can be bonded at a low temperature in a short time and is excellent in heat resistance. As a result, an epoxy compound and a coupling agent are added to a polyimide resin having a specific structure. The inventors have found that the above-mentioned problems can be solved by adding an agent, and arrived at the present invention.

[0006]

The present invention provides a polyimide resin 100 having a glass transition temperature of 350 ° C. or lower and soluble in an organic solvent.
Parts by weight, 5 to 100 parts by weight of an epoxy compound having at least two epoxy groups in one molecule, and a coupling agent.
The present invention relates to a heat-resistant film adhesive containing 1 to 50 parts by weight as a main adhesive resin component and a method for producing the same.

The component (A) polyimide resin which is an essential component of the adhesive resin of the present invention is 3,3 ', 4,4'-biphenyltetracarboxylic dianhydride, 3,3', 4,4'- One or more tetracarboxylic dianhydrides and aromatics selected from the group consisting of benzophenone tetracarboxylic dianhydride, 4,4'-oxydiphthalic dianhydride and ethylene glycol bistrimellitic dianhydride It is preferably obtained by polymerizing with a diamine.

Examples of the aromatic diamine used for producing the polyimide include, for example, 2,2-bis (4- (4-aminophenoxy) phenyl) propane, 1,3-bis (3-aminophenoxy) benzene, 2, 2-bis (4- (4-aminophenoxy) phenyl) hexafluoropropane, 2,2-bis (4-aminophenoxy) hexafluoropropane, bis-4- (4-aminophenoxy) phenyl sulfone, bis-4- Examples thereof include (3-aminophenoxy) phenyl sulfone, and these can be used alone or in combination.

It is more preferable to use the siloxane compound represented by the formula (1) as one component of the diamine component of the polyimide in an amount of 5 to 50 mol% of the total amount of the diamine component.

[0010]

Embedded image (In the formula, R ₁ and R ₂ : a divalent aliphatic group having 1 to 4 carbon atoms or an aromatic group R ₃ , R ₄ , R ₅ , and R ₆ : a monovalent aliphatic group or an aromatic group k: (An integer from 1 to 20)

The siloxane compound represented by the formula (1) is
If it is less than 5 mol% of the total amount of the diamine component, the solubility of the obtained polyimide in an organic solvent will be lowered, and if it exceeds 50 mol%, the glass transition temperature will be remarkably lowered and heat resistance will be a problem. Further, as the siloxane compound represented by the general formula (1), specifically, α represented by the following general formula (2),
ω-bis (3-aminopropyl) polydimethylsiloxane (APPS) is preferable, and a value of k in the range of 4 to 10 is particularly preferable from the viewpoint of glass transition temperature, adhesiveness and heat resistance. These siloxane compounds may be used alone or in combination of two or more. Especially k = 1
It is preferable to blend and use the above k = 4 to 10 in applications where importance is attached to adhesiveness.

[0012]

Embedded image (In the formula, k: an integer of 1 to 20)

The equivalent ratio of the acid component and the amine component in the polycondensation reaction is an important factor that determines the molecular weight of the polyamic acid obtained. It is well known that there is a correlation between polymer molecular weight and physical properties, especially number average molecular weight and mechanical properties. The larger the number average molecular weight, the better the mechanical properties. Therefore, in order to obtain practically excellent strength, it is necessary that the polymer has a high molecular weight to some extent. In the present invention,
The equivalent ratio r of the acid component and the amine component is preferably in the range of 0.900 ≤ r ≤ 1.060, more preferably 0.975 ≤ r ≤ 1.025. However, r = [equivalent number of all acid components] / [equivalent number of all amine components]. r is 0.
If it is less than 900, the molecular weight is low and it becomes brittle, so the adhesive strength becomes weak. On the other hand, if it exceeds 1.06, unreacted carboxylic acid may be decarboxylated during heating to cause gas generation and foaming, which is not preferable.

Addition of dicarboxylic acid anhydride or monoamine for controlling the molecular weight of the polyimide resin of the present invention is not particularly hindered if the acid / amine molar ratio is within the above range.

The reaction between the tetracarboxylic dianhydride and the diamine is carried out by a known method in an aprotic polar solvent. The aprotic polar solvent is N, N-dimethylformamide (DMF), N, N-dimethylacetamide (DMA
C), N-methyl-2-pyrrolidone (NMP), tetrahydrofuran (THF), diglyme, cyclohexanone,
1,4-dioxane (1,4-DO) and the like. The aprotic polar solvent may be used alone or in combination of two or more. At this time, a non-polar solvent compatible with the aprotic polar solvent may be mixed and used. Aromatic hydrocarbons such as toluene, xylene and solvent naphtha are often used. The proportion of the non-polar solvent in the mixed solvent is preferably 30% by weight or less. This is because if the amount of the nonpolar solvent is 30% by weight or more, the solubility of the solvent may decrease and polyamic acid may precipitate. The reaction of the tetracarboxylic acid dianhydride and the diamine is carried out by dissolving the well-dried diamine component in the dehydrated and purified reaction solvent described above, and the ring closure rate of 98%, more preferably 99% or more of the well-dried tetracarboxylic acid dianhydride. Anhydrous is added to drive the reaction.

The polyamic acid solution thus obtained is subsequently heated to dehydration and cyclization in an organic solvent to form an imidized polyimide. Since the water generated by the imidization reaction interferes with the ring-closing reaction, an organic solvent that is not compatible with water is added to the system to azeotropically evaporate it and use a device such as a Dean-Stark tube to remove it from the system. To discharge. Dichlorobenzene is known as an organic solvent that is incompatible with water,
For electronics use, the above-mentioned aromatic hydrocarbons are preferably used because chlorine components may be mixed therein.
Further, the use of compounds such as acetic anhydride, β-picoline and pyridine as a catalyst for the imidization reaction is not hindered.

In the present invention, the higher the degree of imide ring closure, the better, and if the imidization ratio is low, imidization occurs due to heat during use and water is not generated, which is not preferable. Therefore, 95% or more, more preferably 98% or more. It is desirable that the imidization ratio of is achieved.

In the present invention, an epoxy compound or a coupling agent may be added to the obtained polyimide solution as it is, and a resin varnish may be prepared and coated on a support, but the polyimide solution is put into a poor solvent. The polyimide resin is preferably reprecipitated to remove unreacted monomers for purification. The purified and dried polyimide resin, epoxy compound and coupling agent are dissolved in an organic solvent to prepare a coating varnish. The solvent used at this time may be the same as the reaction solvent,
Considering workability in the coating and drying step, it is preferable to select a solvent having a low boiling point, preferably a boiling point of 200 ° C. or less. 200 ° C
As the following solvent, in the present invention, as a ketone solvent, acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclopentanone, cyclohexanone, as an ether solvent, 1,4-dioxane, tetrahydrofuran,
Examples of amide solvents containing diglyme include N, N-dimethylformamide and N, N-dimethylacetamide. These solvents may be used alone or in combination of two or more.

The component (B) epoxy compound used in the adhesive resin of the present invention is not particularly limited as long as it has at least two epoxy groups in one molecule, but it may be used as a solvent for the polyimide resin. Those having good solubility are preferred. Examples thereof include bisphenol A type diglycidyl ether, bisphenol F type diglycidyl ether, phenol novolac type epoxy resin, and biphenyl type epoxy resin.

The compounding amount of the epoxy compound is the component (A).
5-100 parts by weight to 100 parts by weight of polyimide resin,
In particular, it is preferably in the range of 10 to 70 parts by weight. If it is less than 5 parts by weight, the effect of adding an uncured epoxy compound and lowering the softening temperature of the resin composition to improve low-temperature processability is unlikely to appear, and if it exceeds 100 parts by weight, the heat resistance of the polyimide resin is impaired, which is preferable. Absent.

The component (C) coupling agent used in the adhesive resin of the present invention has compatibility with the component (A) polyimide resin and the component (B) epoxy resin, and the solubility of the polyimide resin in a solvent. Good ones are preferred. For example, a silane-based coupling agent, a titanium-based coupling agent, a zircon-based coupling agent, or the like may be used. Particularly, a silane coupling agent is preferable in terms of compatibility and solubility. The mixing ratio of the coupling agent is 0.1 to 50 parts by weight, more preferably 0.5 to 30 parts by weight, based on 100 parts by weight of the component (A) polyimide resin. If it is less than 0.1 parts by weight, it is difficult to control the resin flow when the elastic modulus of the resin at high temperature is lowered, and when the resin composition is used for bonding, the adhesion with the adherend is improved. The effect that causes it does not appear. If it exceeds 50 parts by weight, the heat resistance of the resin composition is impaired, which is not preferable.

The heat-resistant resin composition of the present invention may contain a fine inorganic filler as long as the processability and heat resistance thereof are not impaired.

Various additives such as a leveling agent, a leveling agent and a defoaming agent for providing surface smoothness can be added to the resin varnish as required. Further, an aromatic hydrocarbon solvent can be used within a range in which the solvent is uniformly dissolved in order to control the evaporation rate of the solvent.

In the present invention, the resin varnish is used as a film adhesive, which is obtained by casting or coating a resin varnish. For example, a heat-resistant film base material is used as a support, and a film layer is similarly formed on one side or both sides thereof. To form a film adhesive with the support, rolls, metal sheets,
Form a film on a release sheet such as a polyester sheet with a flow coater, roll coater, etc.,
It can be obtained by a method such as heating, drying and peeling to obtain a film adhesive.

The heat-resistant film base material used in the present invention is that the polyimide resin film has a small coefficient of thermal expansion and is excellent in dimensional stability with respect to temperature changes, is flexible and easy to handle, and is the resin of the present invention. Is preferable because it has excellent adhesion. In particular, a polyimide resin having a glass transition temperature of 350 ° C or higher is excellent in workability and stability in the step of drying the coating varnish.

The coating and drying of the resin varnish can be carried out by using an apparatus in which coating equipment such as a flow coater or roll coater and a hot air drying oven are combined. After coating the resin varnish on the support, the resin varnish is introduced into a hot air drying oven and dried at a temperature and an air volume sufficient to vaporize the solvent of the varnish.

The method of using the film adhesive of the present invention is not particularly limited, but it can be used as an adhesive tape, such as by thermocompression bonding with a heat block that is cut into a predetermined shape and heated. .

[0028]

The film adhesive of the present invention is a polyimide resin which is soluble in an organic solvent and has a glass transition temperature of 350 ° C or lower.
It is characterized by containing 5 to 100 parts by weight of an epoxy compound having at least two epoxy groups in one molecule and 0.1 to 50 parts by weight of a coupling agent as a main resin component with respect to parts by weight. . The apparent glass transition temperature of this resin is lower than the glass transition temperature of the main component polyimide resin, and the low temperature processability is improved. On the other hand, the adhesive strength in the temperature range higher than the glass transition temperature is higher than that of the polyimide resin,
Improves physical properties in a high temperature range, such as no peeling observed even when subjected to thermal shock such as IR reflow. Although the detailed mechanism for this peculiar phenomenon is not yet clear, the low molecular weight product obtained by reacting the epoxy compound and the coupling agent acts as a plasticizer on the polyimide resin having a specific structure, It lowers the elastic modulus at a temperature lower than the glass transition temperature of the resin, thus improving workability at low temperature such as adhesiveness and processability. On the other hand, in a temperature range higher than the glass transition temperature, it is considered that a three-dimensional network structure is formed by the applied heat and the fluidity of the polyimide resin is lowered, and thus the heat resistance of the polyimide resin is maintained or improved. By the above mechanism, both low temperature processability and heat resistance reliability at high temperature can be achieved. Further, it can be bonded in an extremely short time as compared with a thermosetting adhesive which involves a chemical reaction. By processing into a tape shape, the workability of bonding and the dimensional accuracy of the bonded portion can be made excellent. The present invention is described in detail below with reference to examples, but the present invention is not limited to these examples.

[0029]

【Example】

(Synthesis of Polyimide Resin PI-1) In a four-necked flask equipped with a dry nitrogen gas introduction tube, a cooler, a thermometer, and a stirrer,
Add 716 g of dehydrated and purified NMP, and stir vigorously for 10 minutes while flowing nitrogen gas. Next, 2,2-bis (4- (4-aminophenoxy) phenyl) propane (BAPP) 24.631
g (0.060 mol), 1,3-bis (3-aminophenoxy) benzene (APB) 48.236 g (0.165 mol), α, ω-bis (3-
Aminopropyl) polydimethylsiloxane (APPS formula
(2)) 57.753 g (average molecular weight 837, 0.069 mol), 1.3-bis (3-aminopropyl) tetramethyldimethylsiloxane (APPS, k = 1 in formula (2)) 1.491 g (0.006 mol), Heat the system to 60 ° C and stir until uniform. After uniform dissolution, the system was cooled to 5 ° C in an ice-water bath,
3 ', 4,4'-biphenyltetracarboxylic dianhydride (BPD
A) 52.960 g (0.180 mol), 3,3 ', 4,4'-benzophenone tetracarboxylic dianhydride (BTDA) 38.668 g
(0.120 mol) was added as a powder over 15 minutes, and then stirring was continued for 3 hours. During this time, the flask was kept at 5 ° C.

Then, the nitrogen gas introducing pipe and the cooler were removed,
A Dean-Stark tube filled with xylene was attached to the flask, and 179 g of xylene was added to the system. Instead of the oil bath, the system was heated to 175 ° C. and the water generated was removed from the system. After heating for 4 hours, generation of water from the system was not observed. After cooling, this reaction solution was poured into a large amount of methanol to precipitate a polyimide resin. After filtering the solids, 80
After removing the solvent by drying under reduced pressure at ℃ for 12 hours, 204.72 g (yield 91.5
%) Solid resin was obtained. When the infrared absorption spectrum was measured by the KBr tablet method, it was found to be 5.6
Absorption of μm was observed, but 6.06 μm derived from amide bond
It was confirmed that the resin was almost 100% imidized.

The polyimide resin thus obtained has a glass transition temperature of 133 ° C., a tensile elastic modulus of 170 kgf / mm ² ,
Dimethylformamide (DMF), 1,4-dioxane (1,
It was confirmed that it was well dissolved in 4-DO).

(Synthesis of Polyimide Resin PI-2) In the same manner as the synthesis of the above-mentioned polyimide resin PI-1, NMP67
61.391 g (0.210 mol) of 1,3-bis (3-aminophenoxy) benzene (APB) as a diamine component in 4 g of 2,2-bis (4- (4-aminophenoxy) phenyl) propane (BA
PP) 18.473 g (0.045 mol), α, ω-bis (3-aminopropyl) polydimethylsiloxane (APPS) 37.665 g
(0.045 mol) was added, 93.067 g (0.300 mol) of 4,4'-oxydiphthalic acid dianhydride (ODPA) was added as an acid component, and the stirring was continued for 3 hours thereafter. Then, the system was heated for imidization to obtain 195.22 g (yield 92.7%) of a solid resin.

(Synthesis of Polyimide Resin PI-3) NMP65 was prepared in the same manner as the synthesis of the polyimide resin PI-1.
4,617 g (0.050 mol) of 1,3-bis (3-aminophenoxy) benzene (APB) as a diamine component in 4 g of 2,2-
Bis (4- (4-aminophenoxy) phenyl) propane (B
APP) 61.577 g (0.150 mol), α, ω-bis (3-aminopropyl) polydimethylsiloxane (APPS) 41.850
g (0.050 mol), ethylene glycol bistrimellitic dianhydride (TMEG) 50.261 as an acid component
g (0.125 mol) and 30.042 g (0.125 mol) of 3,3 ', 4,4'-biphenyltetracarboxylic dianhydride (BPDA) were added, and stirring was continued for 3 hours thereafter. Then, the system was heated and imidized to obtain a polyimide resin. Table 1 shows the properties of the polyimide resins PI-1, PI-2 and PI-3.

[0034]

[Table 1]

(Example 1) (Preparation of coating varnish) 100 g of polyimide resin PI-1 and 450 g of DMF were placed in a glass flask and sufficiently stirred at room temperature to completely dissolve the polyimide. After uniform dissolution, bisphenol A type epoxy resin (Epicoat 82
8 、 Okaka Shell Epoxy Co., Ltd.) 50g was added and it was 2 at room temperature.
Stirred for hours. Then, after confirming that the system was uniformly dissolved, 1 g of a silane coupling agent (triethoxyvinylsilane, KBE1003, manufactured by Shin-Etsu Chemical Co., Ltd.) was gradually added while stirring the system. Subsequently, the mixture was stirred for 2 hours to prepare a coating varnish. The solution composition did not gel even after standing at room temperature for 10 days and remained in a uniform solution state.

(Production of Heat-Resistant Film Adhesive) A polyimide film (trade name UPILEX SGA, thickness 50 μm, Ube Industries, Ltd.) was prepared by applying the above varnish to a reverse roll coater.
(Manufactured by K.K.) to obtain an adhesive tape having an adhesive layer with a thickness of 30 μm. The maximum drying temperature was 185 ° C and the drying time was 6 minutes. This film adhesive was thermocompression bonded to a 35 μm copper foil to prepare a test piece (thermocompression bonded to the treated surface of the copper foil for 2 seconds at 250 ° C., after releasing the pressure, annealed at 250 ° C. for 30 seconds. Is the result of calculation from the gauge pressure and the adhesion area 4kg
It was f / cm ² . ), And 180 degree peel strength was measured with Tensilon (tensile speed 50 mm / min). 180 degree peel strength is
It was 3.24 kgf / cm, and showed excellent adhesive strength. At the fracture surface, the adhesive resin layer was cohesively destroyed and no foaming was observed.
In addition, the pressure cooker (125
The 180-degree peel strength after treatment at ℃, 48 hours, saturation 100%) was 2.86 kgf / cm, which shows that it has excellent adhesive strength.

Example 2 The varnish of Example 1 was applied to a biaxially stretched polyester film (trade name: Diamond foil, thickness 50 μm, Mitsubishi Rayon Co., Ltd.) with a reverse roll coater, and peeled from the polyester film after drying. , 30μ
An m-thick uniform single-layer film adhesive without a support was obtained. Peeling was easy and there was no particular problem. Table 2 shows the results of adhesion to the shiny side of the copper foil as in Example 1.

(Examples 3 to 5) In the same manner as in Examples 1 and 2, coating varnishes were prepared with the formulations shown in Table 2 to obtain film adhesives. Table 2 shows the obtained evaluation results.

[0039]

[Table 2]

S in the solubility column indicates that the compound is soluble in the corresponding solvent. The glass transition temperature was determined by DSC measurement. The tensile test was performed at room temperature and a tensile speed of 5 mm / min. Regarding the component (B) epoxy compound used, YX
-4000H is a biphenyl type epoxy compound Epicoat YX-4000H, manufactured by Yuka Shell Epoxy Co., Ltd., EOC
N-1020 is a phenol novolac type epoxy compound EOCN-1020, manufactured by Nippon Kayaku Co., Ltd., respectively. The component (C) coupling agent used is KBC10.
03 (Trismethoxyethoxyvinylsilane), KBE
1003 (triethoxyvinylsilane), KBM573
(N-phenyl-γ-aminopropyltrimethoxysilane) manufactured by Shin-Etsu Chemical Co., Ltd. was used.

(Comparative Examples 1, 2, 3) Polyimide resin PI
-1, PI-2 and PI-3 were applied on one surface of a polyimide film (Upilex) to obtain a film adhesive. The adhesive strength with copper was measured in the same manner as in the example, and the results are shown in Table 1.

From the results shown in Tables 1 and 2, the adhesive strength of the film adhesives of the examples is slightly decreased even after the moisture absorption and heating, but the adhesive strength of the film of the comparative polyimide resin only is normal. Compared to the above, the value after heating by moisture absorption is significantly decreased. From the above, it is shown that the present invention can provide a film adhesive excellent in heat resistance and molding processability.

[0043]

According to the present invention, it is possible to provide a highly reliable film adhesive having both heat resistance and molding processability. Since it is soluble in a low boiling point solvent, it is possible to almost completely eliminate the residual solvent, and since it has already been imidized, a high temperature process for imidization is not required during processing and no water is generated. Since it can be used as a tack-free film, it is very effective when continuous workability and a clean environment are required. Therefore, it is industrially extremely useful as a material for electronics that requires high reliability and heat resistance.

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Claims (7)

[Claims] 1. (A) 100 parts by weight of a polyimide resin soluble in an organic solvent and having a glass transition temperature of 350 ° C. or lower;
5 to 100 parts by weight of an epoxy compound having at least two epoxy groups in one molecule, and (C) a coupling agent 0.1.
A heat-resistant film adhesive whose main component is -50 parts by weight. 2. The heat-resistant film adhesive according to claim 1, wherein the component (A) is a polyimide resin containing a siloxane compound represented by the general formula (1) in an amount of 5 to 50 mol% of the total amount of amine components. . Embedded image (In the formula, R ₁ and R ₂ : a divalent aliphatic group or an aromatic group having 1 to 4 carbon atoms R ₃ , R ₄ , R ₅ and R ₆ : a monovalent aliphatic group or an aromatic group k : Integer from 1 to 20) 3. The heat resistant film adhesive according to claim 1, wherein the component (C) is a silane coupling agent. 4. (A) 100 parts by weight of a polyimide resin which is soluble in an organic solvent and has a glass transition temperature of 350 ° C. or lower,
A solution of a heat resistant resin composition containing (B) 5 to 100 parts by weight of an epoxy compound having at least two epoxy groups in one molecule and (C) a coupling agent of 0.1 to 50 parts by weight as main components. A method for producing a heat-resistant film adhesive, comprising casting on one or both sides of a support. 5. The heat-resistant film adhesive according to claim 4, wherein the component (A) is a polyimide resin containing the siloxane compound represented by the general formula (1) in an amount of 5 to 50 mol% of the total amount of the amine components. Manufacturing method. 6. The method for producing a heat resistant film adhesive according to claim 4, wherein the component (C) is a silane coupling agent. 7. The heat-resistant film adhesive according to claim 4, 5 or 6, which is obtained by casting on a support using an organic solvent having a boiling point of 200 ° C. or lower, drying and peeling from the support. Method of manufacturing agent.