JP2003066610A - Polyimide resin and photosensitive resin composition containing the same - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a new photosensitive resin composition free of swelling of a film in development, developable with an aqueous alkali solution safe in work, not requiring heating at a high temperature, ensuring little volume shrinkage particularly in curing and excellent in dimensional stability. SOLUTION: A polyimide film obtained by heating a polyimide resin having repeating units of formula (1) (where Ar is a tetravalent organic group; R1 is H, alkyl or perfluoroalkyl; R2 is H, alkyl, perfluoroalkyl or halogen; and (n) is an integer of 1-4) is highly valuable as an industrial material because it is suitable for use as a protective coat for electronic parts.

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to a novel polyimide resin effectively used for a protective film for semiconductor elements, an alignment film for liquid crystal display elements, an interlayer insulating film for multilayer printed wiring boards, and the like, and a novel polyimide resin containing the same. And a photosensitive resin composition.

[0002]

2. Description of the Related Art Conventionally, a polyimide resin having excellent heat resistance and excellent electrical and mechanical properties has been used for a surface protective film and an interlayer insulating film of a semiconductor element.
Due to recent high integration of semiconductor elements, thinning and miniaturization of encapsulation resin packages, transition to surface mounting by solder reflow, etc., there is a demand for remarkable improvement in heat cycle resistance, heat shock resistance, etc. Polyimide resins have become needed.

On the other hand, in recent years, a technique of so-called photosensitive polyimide, which is capable of simplifying part of the pattern forming process and shortening the process, has been attracting attention. For example, a material formed by introducing a photosensitive group to a carboxyl group of a polyamic acid, which is a precursor of polyimide according to JP-A-49-115541 and JP-A-55-45746, by an ester bond, JP-A-60- There are proposed materials and the like, which are prepared by introducing a photosensitive group to a carboxyl group of a polyamic acid by an amide bond according to Japanese Patent Publication No. 100143, but these materials have a swelling of a film during development, and Since it requires a solvent such as N-methyl-2-pyrrolidone, there is a problem in safety and pollution.

Therefore, in order to solve this problem, a positive type photosensitive resin which can be developed with an alkaline aqueous solution has been developed. For example, JP-A-2-181149 proposes a photosensitive resin composition comprising an esterified polyamic acid polymer and a photosensitive quinonediazide. Since this photosensitive resin composition is used to remove the via hole portion using an alkaline aqueous solution, an organic solvent is not required unlike the conventional photosensitive polyimide resin, so that the safety is further improved during work. However, all of these photosensitive polyimide resins are those obtained by imparting photosensitivity to polyamic acid, which is a precursor of polyimide resin, and finally 300 ° C. for conversion (imidization) of polyamic acid to polyimide resin. Since heat treatment (dehydration ring closure) must be performed at the above high temperature, it can only be used on substrates or elements that can withstand this heat, and the pattern obtained during imidization causes volume shrinkage due to heat, etc. However, there was a problem with dimensional stability.

In recent years, in order to solve these problems, for example, a main chain decomposition type photosensitive polyimide composed of a soluble polyimide having an acetal structure and a photoacid generator has been developed according to JP-A No. 11-315141. This photosensitive polyimide does not swell the film during development,
Further, since it does not require heat treatment at high temperature, it is a material excellent in dimensional stability with less volume shrinkage and the like as compared with the conventional photosensitive polyimide.

As described above, efforts have been made to improve the problems of the photosensitive polyimide, but with the recent trend toward higher integration and miniaturization of semiconductor elements, the demand for dimensional stability is particularly severe. Therefore, it has been desired to further improve the dimensional stability of the photosensitive polyimide.

[0007]

SUMMARY OF THE INVENTION The present invention has been made to solve the above-mentioned problems of the conventional photosensitive polyimide. That is, the object of the present invention is that the film does not swell at the time of development, it can be developed with an alkaline aqueous solution which is safe in terms of work, and it does not require heat treatment at high temperature. It is an object of the present invention to provide a novel photosensitive resin composition characterized by less shrinkage and excellent dimensional stability.

[0008]

As a result of earnest studies, the inventors of the present invention were able to solve the problems of the prior art. That is, the present invention, in claim 1, is represented by the above general formula (1) capable of generating a phenolic hydroxyl group by cleaving the acetal site in the main chain of the general formula (1) due to the presence of an acid. It is a novel polyimide resin characterized by having a repeating unit.

Further, in claim 2, a novel polyimide resin (A) having at least a repeating unit represented by the general formula (1) described in claim 1.
And a photodegradable acid generator (B) are contained in the photosensitive resin composition.

[0010]

BEST MODE FOR CARRYING OUT THE INVENTION Since the polyimide resin according to the present invention has a very high decomposition efficiency of the structure of the acetal moiety in the presence of an acid, when it is used as a photosensitive polyimide in combination with a photodegradable acid generator, Since it is possible to reduce the amount of photodegradable acid generator added compared to conventional methods, it is used as a permanent film. It is possible to further suppress the volume shrinkage.

Polyimide resin characterized by the above
By using the photosensitive resin composition, there is no swelling of the film at the time of development, development is possible with an alkaline aqueous solution that is safe for work, and heat treatment at high temperature is not required, and at the time of curing. The present invention provides a novel photosensitive resin composition characterized by having less volume shrinkage and excellent dimensional stability.

The polyimide resin according to the present invention, which will be described in more detail below, is represented by the above general formula (1) and can be easily produced, for example, from a diamine compound and a tetracarboxylic dianhydride. You can

Examples of the diamine compound include benzaldehyde-di-p-aminophenyl acetal, 2-methylbenzaldehyde-di-p-aminophenyl acetal, 2-trifluoromethylbenzaldehyde-di-p-aminophenyl acetal, benzaldehyde- Di-m-aminophenyl acetal, 2-methylbenzaldehyde-di-m-aminophenyl acetal, 2-trifluoromethylbenzaldehyde-di-m-aminophenyl acetal, 4-methylbenzaldehyde-di-p-aminophenyl acetal, 4 -Trifluoromethylbenzaldehyde-di-p-aminophenyl acetal, 4-methylbenzaldehyde-di-m-aminophenyl acetal, 4-trifluoromethylbenzaldehyde-di-m-aminophenyl acetal and the like diamine compounds may be exemplified. it can. These diamine compounds may be used alone or in combination of two or more.

The tetracarboxylic acid dianhydride represented by the above general formula (1) includes pyromellitic dianhydride, 3,4,
3 ', 4'-biphenyltetracarboxylic dianhydride, 3, 4,
3 ', 4'-diphenyl ether tetracarboxylic dianhydride, 3,4,3', 4'-benzophenone tetracarboxylic dianhydride, 3,4,3 ', 4'-diphenylsulfone tetracarboxylic dianhydride , 2,2-bis (2,3-dicarboxyphenyl) hexafluoropropane dianhydride, 2,2-bis (3,4-dicarboxyphenyl) hexafluoropropane dianhydride, 3, 4, 3 ", 4 "-terphenyl tetracarboxylic dianhydride, 1, 2,5, 6-naphthalene tetracarboxylic dianhydride, 2, 3, 6, 7-naphthalene tetracarboxylic dianhydride, 2, 3, 5, 6-pyridine tetracarboxylic dianhydride, 1, 4, 5, 8-naphthalene tetracarboxylic dianhydride,
3, 4, 9, 10-Perylene tetracarboxylic dianhydride, 2, 2
-Bis (3,4-dicarboxyphenyl) propane dianhydride, 2,2-bis (2,3-dicarboxyphenyl) propane dianhydride, 2,2-bis [4- (2,3-dicarboxy Phenoxy) phenyl] propane dianhydride, 2,2-bis [4-
(3,4-Dicarboxyphenoxy) phenyl] propane dianhydride, 2,2-bis [4- (2,3-dicarboxyphenoxy) phenyl] hexafluoropropane dianhydride, 2,
2-bis [4- (3,4-dicarboxyphenoxy) phenyl] hexafluoropropane dianhydride, the following general formula (2)

[0015]

[Chemical 2]

(Wherein R ₃ and R ₄ are each independently a monovalent hydrocarbon group, and n is 0 or an integer of 1 or more), such as tetracarboxylic dianhydride. Carboxylic dianhydrides, hydrogenated anhydrides of these aromatic tetracarboxylic acids, and alicyclic tetracarboxylic dianhydrides such as compounds represented by the following general formulas (3) to (4)

[0017]

[Chemical 3]

[0018]

[Chemical 4]

The following can be illustrated. In addition to these tetracarboxylic dianhydrides, aliphatic tetracarboxylic dianhydrides may be used to the extent that heat resistance and mechanical properties are not deteriorated. These tetracarboxylic acid dianhydrides may be used alone or in combination of two or more.

As an example of the method for producing the polyimide resin of the present invention, a polyimide precursor is prepared by reacting a diamine compound and a tetracarboxylic dianhydride in an organic solvent at -20 to 50 ° C for several minutes to several days. The body polyamic acid can be obtained.

Examples of the organic solvent which can be used in the synthesis reaction of polyamic acid include amide solvents such as N, N-dimethylacetamide and N-methyl-2-pyrrolidone, benzene, anisole, diphenyl ether, nitrobenzene, benzonitrile and pyridine. Aromatic solvent, chloroform, dichloromethane, 1,2-dichloroethane, 1,1,2,2
Examples thereof include halogen-based solvents such as tetrachloroethane, ether-based solvents such as tetrahydrofuran, dioxane, and diglyme. In particular, when an amide-based solvent such as N, N-dimethylacetamide or N-methyl-2-pyrrolidone is used, a highly polymerized polyamic acid can be obtained.

The polyamic acid obtained as described above is then converted into a polyimide resin by a known method such as heating or treatment with a dehydration ring-closing agent with acetic anhydride and pyridine. As an example of the dehydration ring-closing method, a thermal cyclization method by refluxing toluene, xylene or the like can be used. Since this polyimide resin contains toluene used for dehydration, xylene, etc., water, the polyimide resin solution is put into a poor solvent such as methanol, reprecipitation is performed, and this is further dried to obtain a polyimide resin powder. To do. This is dissolved in a desired organic solvent to obtain a solution of the polyimide resin used in the present invention.

In this method, the molecular weight of the polyimide resin of the present invention is limited by the amount of the diamine compound charged, and a high molecular weight polyimide resin can be produced when used in equimolar amounts.

In the present invention, as the photodecomposable acid generator (B) used in combination with the above-mentioned polyimide resin (A), allyldiazonium salt (ArN
₂ ⁺ X ⁻ ), diallyl iodonium salt (Ar ₂ I ⁺ X ⁻ ), triallyl sulfonyl salt (Ar ₃ S ⁺ X ⁻ ), aromatic sulfonic acid ester, and iron arene complex can be exemplified. These photodecomposable acid generators may be used alone or in combination of two or more. Further, a sensitizer can be used if necessary. These photodegradable acid generators generate an acid upon irradiation with actinic rays, and the acid generated from the photodegradable acid generators has the general formula (1)
It acts as a catalyst for the decomposition reaction of the acetal part of. Examples of the sensitizer include perylene, pyrene, anthracene, thioxanthone, Michler's ketone, benzophenone, 9-fluorenone, and anthrone.

The photosensitive resin composition of the present invention can be obtained by mixing the polyimide resin (A) represented by the general formula (1) and the photodegradable acid generator (B). The mixing ratio of both is arbitrary, but in order to obtain good photosensitivity and storage stability, 0.1 to 50 parts by weight of the photodegradable acid generator is added to 100 parts by weight of the polyimide resin (A). It is suitable to use in an amount, more preferably 0.5 to 30.
It is desirable to use parts by weight. The photodegradable acid generator is 0.1 parts by weight per 100 parts by weight of the polyimide resin (A).
If it is less than 50 parts by weight, good photosensitivity cannot be obtained, and if it is more than 50 parts by weight, heat resistance and storage stability are problematic.

The photosensitive resin composition of the present invention is generally used in the form of being dissolved in a suitable organic solvent and applied to a substrate. As the solvent used here, N-methyl-2-pyrrolidone, N, N-dimethylacetamide, γ-butyrolactone, dimethyl sulfoxide, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol dibutyl ether, diethylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, etc. Can be illustrated. These solvents may be used alone or in combination of two or more.

The method of using the photosensitive resin composition of the present invention is as follows:
First, the composition is applied to a suitable support, for example, a silicon wafer, a ceramic, an aluminum substrate or the like. The application method is
Spin coating using a spinner, spray coating using a spray coater, dipping, printing, roll coating and the like are performed. Next, after prebaking at 60 to 120 ° C. to dry the coating film, the desired pattern shape is irradiated with an actinic ray. Actinic rays include mercury lamps, xenon lamps, metal halide lamps, chemical lamps, carbon arc lamps, g rays, i
Lines, deep-UV light, high-density energy beams such as helium neon laser, argon ion laser, krypton ion laser, helium / cadmium ion laser, and KrF excimer laser can be exemplified. After irradiation with actinic rays, in order to promote the reaction of decomposing the acetal moiety in the main chain of the general formula (1) into a phenolic hydroxyl group, it is 0.5 to 30 in the range of 60 to 160 ° C.
It is preferable to heat for a minute.

Next, a relief pattern is obtained by dissolving and removing the irradiated portion with a developing solution. As the developer, sodium hydroxide, potassium hydroxide, sodium carbonate, sodium silicate, sodium metasilicate, inorganic alkalis such as aqueous ammonia, ethylamine, primary amines such as n-propylamine, diethylamine, di-n- Secondary amines such as propylamine, tertiary amines such as triethylamine and methyldiethylamine, dimethylethanolamine,
Alcohol amines such as triethanolamine, aqueous solutions of alkalis such as quaternary ammonium salts such as tetramethylammonium hydroxide and tetraethylammonium hydroxide, and water-soluble organic solvents such as alcohols such as methanol and ethanol. An aqueous solution containing an appropriate amount of a surfactant can be preferably used.
As a developing method, a method such as spraying, paddle, dipping, and ultrasonic wave can be used. Next, the relief pattern formed by development is rinsed. Distilled water is used as the rinse liquid.

Since the photosensitive resin composition of the present invention adopts a system of decomposing the main chain with an acid, an organic solvent can be used as a developing solution. N-methyl-2 as an organic solvent
-Pyrrolidone, N, N-dimethylacetamide, γ-butyrolactone, dimethylsulfoxide, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol dibutyl ether, diethylene glycol monomethyl ether, propylene glycol monomethyl ether acetate and the like can be exemplified. These solvents may be used alone or in combination of two or more. Further, in these organic solvents, alcohols such as methanol, ethanol, isopropanol, toluene, aromatic hydrocarbon compounds such as xylene, acetone, methyl ethyl ketone, ketones such as methyl isobutyl ketone, ethyl acetate, esters such as methyl propionate, A general solvent such as ether such as tetrahydrofuran or dioxane and water may be mixed.

Next, heat treatment is performed to obtain a final pattern having high heat resistance. The photosensitive resin composition according to the present invention is useful not only for semiconductor applications but also as an interlayer insulating film for a multilayer circuit, a cover coat for a flexible copper clad board, a solder resist film and a liquid crystal alignment film.

[0031]

EXAMPLES The present invention will now be described in more detail with reference to examples.

Example 1 Synthesis of Polyimide (A) 2.861 g (7.65 mmol) of 2-trifluoromethylbenzaldehyde-di-p-aminophenylacetal was dissolved in 6 mL of N, N-dimethylacetamide. To 3.398 g (7.65 mmol) of 2,2-bis (3,4)
Dicarboxyphenyl) hexafluoropropane dianhydride was added all at once as a solid. 1.5 hours at 0 ° C, 2
Stirring was carried out at 5 ° C. for 24 hours to prepare a polyamic acid solution. 50 mL of N, N-dimethylacetamide, 21 mL of acetic anhydride and 19 mL of pyridine were added to this polyamic acid solution, and the mixture was stirred at 100 ° C. for 24 hours. This reaction solution was poured into a large amount of methanol solution to reprecipitate a polyimide resin, which was further vacuum dried at 100 ° C. to obtain a polyimide resin powder. The intrinsic viscosity of the obtained polyimide is 0.3
It was 2 dL / g (measured in a N, N-dimethylacetamide solution at 30 ° C. and a concentration of 0.5 g / dL). The glass transition temperature measured by a differential scanning calorimeter was 221 ° C. The 10% weight loss temperature measured by a thermogravimetric analyzer was 438 ° C. in air and 434 ° C. in nitrogen.

Preparation of Photosensitive Resin Composition 18 parts by weight of synthesized polyimide and 2 parts by weight of photodegradable acid generator represented by the following general formula (5) are dissolved in 80 parts by weight of N-methyl-2-pyrrolidone, A photosensitive varnish was obtained by filtering with a 0.2-micron Teflon (registered trademark) filter.

[0034]

[Chemical 5]

Characteristic Evaluation This photosensitive varnish was applied on a silicon wafer to a thickness of about 5 μm using a spin coater and dried, and then an actinic ray having a wavelength of 436 nm was passed through a photomask and passed through a glass filter on an ultrahigh pressure mercury lamp. Irradiation, 150mJ
/ Make contact exposure of cm ^2, and the further heated for 10 minutes at 120 ° C.. Next, development was performed with a 2.38% tetramethylammonium hydroxide aqueous solution, and further rinsed with pure water, and the obtained line-and-space pattern shape and the obtained minimum line width were observed. Further, they were heat-treated in vacuum at 220 ° C. for 1 hour, and the film thickness before curing was standardized to 1 to obtain the residual film ratio. The results are shown in Table 1.

Example 2 The same as Example 1 except that benzaldehyde-di-p-aminophenylacetal was used instead of 2-trifluoromethylbenzaldehyde-di-p-aminophenylacetal of Example 1. To synthesize polyimide. The intrinsic viscosity of the obtained polyimide is 0.2
It was 8 dL / g (measured in a N, N-dimethylacetamide solution at 30 ° C. and a concentration of 0.5 g / dL). The glass transition temperature measured by a differential scanning calorimeter was 207 ° C. The 10% weight loss temperature measured by a thermogravimetric analyzer was 495 ° C in air and 450 ° C in nitrogen. Using the obtained polyimide, pattern formation was performed in the same manner as in Example 1 and characteristic evaluation was performed. The results are shown in Table 1.

<Embodiment 3> 2,2-bis (3, 4) of Embodiment 1
A polyimide was synthesized in the same manner as in Example 1 except that 3,4,3 ′, 4′-diphenylsulfone tetracarboxylic dianhydride was used instead of (dicarboxyphenyl) hexafluoropropane dianhydride. The intrinsic viscosity of the obtained polyimide was 0.29 dL / g (measured in a N, N-dimethylacetamide solution at 30 ° C. and a concentration of 0.5 g / dL). The glass transition temperature measured by a differential scanning calorimeter was 220 ° C. The 10% weight loss temperature measured by a thermogravimetric analyzer was 415 ° C. in air and 418 ° C. in nitrogen.
Using the obtained polyimide, pattern formation was performed in the same manner as in Example 1 and characteristic evaluation was performed. The results are shown in Table 1.

<Embodiment 4> 2,2-bis (3,4) of Embodiment 1
A polyimide was synthesized in the same manner as in Example 1 except that 3,4,3 ′, 4′-diphenyl ether tetracarboxylic acid dianhydride was used instead of (dicarboxyphenyl) hexafluoropropane dianhydride. The intrinsic viscosity of the obtained polyimide was 0.31 dL / g (measured in a N, N-dimethylacetamide solution at 30 ° C. and a concentration of 0.5 g / dL). The glass transition temperature measured by a differential scanning calorimeter was 198 ° C. The 10% weight loss temperature measured by a thermogravimetric analyzer was 425 ° C. in air and 419 ° C. in nitrogen.
Using the obtained polyimide, pattern formation was performed in the same manner as in Example 1 and characteristic evaluation was performed. The results are shown in Table 1.

<Embodiment 5> 2,2-bis (3,4) of Embodiment 1
A polyimide was synthesized in the same manner as in Example 1 except that 3,4,3 ′, 4′-benzophenonetetracarboxylic dianhydride was used instead of (dicarboxyphenyl) hexafluoropropane dianhydride. The intrinsic viscosity of the obtained polyimide was 0.29 dL / g (measured in a N, N-dimethylacetamide solution at 30 ° C. and a concentration of 0.5 g / dL).
The glass transition temperature measured by a differential scanning calorimeter is 20.
It was 2 ° C. The 10% weight loss temperature measured by a thermogravimetric analyzer was 426 ° C. in air and 415 ° C. in nitrogen. Using the obtained polyimide, pattern formation was performed in the same manner as in Example 1 and characteristic evaluation was performed. The results are shown in Table 1.

<Embodiment 6> 2,2-bis (3, 4) of Embodiment 1
A polyimide was synthesized in the same manner as in Example 1 except that 3,4,3 ", 4" -terphenyltetracarboxylic dianhydride was used instead of (dicarboxyphenyl) hexafluoropropane dianhydride. The intrinsic viscosity of the obtained polyimide was 0.31 dL / g (measured in a N, N-dimethylacetamide solution at 30 ° C. and a concentration of 0.5 g / dL). The glass transition temperature measured by a differential scanning calorimeter is 220.
It was ℃. The 10% weight loss temperature measured by a thermogravimetric analyzer was 462 ° C. in air and 456 ° C. in nitrogen. Using the obtained polyimide, pattern formation was performed in the same manner as in Example 1 and characteristic evaluation was performed. The results are shown in Table 1.

Comparative Example 1 The same procedure as in Example 1 was repeated except that bis (4-aminophenoxy) methane was used instead of 2-trifluoromethylbenzaldehyde-di-p-aminophenylacetal of Example 1. A polyimide was synthesized.
The intrinsic viscosity of the obtained polyimide was 0.38 dL / g (in N, N-dimethylacetamide solution at 30 ° C., 0.
(Measured at a concentration of 5 g / dL). The glass transition temperature measured by a differential scanning calorimeter was 230 ° C. The 10% weight loss temperature measured by a thermogravimetric analyzer was 495 ° C in air and 450 ° C in nitrogen. Using the obtained polyimide, pattern formation was performed in the same manner as in Example 1 and characteristic evaluation was performed. The results are shown in Table 1.

Comparative Example 2 The polyimide synthesized in Comparative Example 1 was used, except that the mixing ratio of the photosensitive resin solution was 16 parts by weight of the polyimide resin and 4 parts by weight of the photodegradable acid generator.
Pattern formation was performed in the same manner as in Example 1, and the characteristics were evaluated. The results are shown in Table 1.

[0043]

[Table 1]

From the above results, according to the present invention, in addition to the fact that the film does not swell at the time of development, it can be developed with an alkaline aqueous solution which is safe in terms of work, and the heat treatment at high temperature is not necessary, It has been found that a photosensitive resin composition characterized by less volume shrinkage during curing and excellent dimensional stability can be provided.

[0045]

EFFECT OF THE INVENTION The polyimide resin of the present invention and the photosensitive resin composition using the same have no swelling of the film at the time of development, which could not be achieved by the conventional one, and can be developed with a safe aqueous alkali solution. In addition, the photosensitive resin composition is characterized in that it does not require heat treatment at a high temperature and has little volume shrinkage during curing, and is excellent in dimensional stability. A polyimide film obtained by heating this photosensitive resin composition can be suitably used as a protective film for electronic parts, and thus has great value as an industrial material.

─────────────────────────────────────────────────── ─── Continuation of front page (51) Int.Cl. ⁷ Identification code FI theme code (reference) H01L 23/31 H01L 21/30 502R H05K 3/28 23/30 D 3/46 (72) Inventor temple boundary Mitsutoshi 6-21-9 Okusawa, Setagaya-ku, Tokyo 20C Jiyugaoka Takeo Corp 20C (72) Inventor Li Li 1-1-12 Ishikawadai-cho, Ota-ku, Tokyo C-302 International Exchange Hall C-302 (72) Inventor Andrew Son Tokyo 3-44-20-303 F term, Koenji Minami, Suginami-ku (reference) 2H025 AA04 AA10 AA13 AA20 AB14 AB15 AB16 AB17 AC01 AD03 BE00 BE10 BG00 CB25 FA17 4J043 PA01 PA02 PA04 QB26 QB31 RA34 SA06 SA47 SA54 TA22 TA71 TA132 TB01 TB02UA02 UA141 UA252 UA262 UA362 UB011 UB012 UB021 UB062 UB121 UB122 UB312 UB322 VA021 VA022 VA061 VA062 ZB22 4M109 ED03 5E314 AA27 AA36 DD07 GG24 5E346 AA12 CC10 CC52 HH11 HH 33

Claims (2)

[Claims] 1. The following general formula (1): (Wherein Ar is a tetravalent organic residue, R ₁ is hydrogen, an alkyl group, a perfluoroalkyl group, R ₂ is hydrogen, an alkyl group, a perfluoroalkyl group, or a halogen atom,
and n represents an integer of 1 to 4). 2. A photosensitive resin composition comprising at least the polyimide resin (A) according to claim 1 and a photodegradable acid generator (B).