JP2001215695A - Photosensitive resin composition and method of producing the same - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a polyimide precursor developable with an aqueous alkali solution and having positive type pattern forming ability, and a method of stably producing the polyimide precursor. SOLUTION: The photosensitive resin composition contains (A) the polyimide precursor represented by formula 1 or 2 (where R1 is a tetravalent organic group such as a benzophenonetetracarboxylic acid dianhydride residue; R2 is a divalent organic group such as a diaminodiphenyl ether residue; R3 and R4 are each an alcoholic compound having a diazonaphtoquinone ring or an aromatic ring having a phenolic OH group; and (n) is an integer of >=1), (B) a dehydration condensing agent used in the synthesis of the polyimide precursor, e.g. diphenyl (2,3-dihydro-2-thioxo-3-benzoxazole)phosphonate, (C) a photosensitive agent which enhances sensitivity to active light, e.g. a diazonaphthoquinone compound and (D) a solvent.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a polyimide-based photosensitive resin composition used as an electric or electronic insulating material in the production of semiconductor devices and the like, and a method for producing the same. Things are
It is preferably applied to an insulating protective film formed on a semiconductor element such as an IC or an LSI, which requires processing of a fine pattern.

[0002]

2. Description of the Related Art In recent years, polyimide resins have been developed in the fields of electricity and electronics, including semiconductors, due to their high heat resistance, chemical resistance, electrical insulation, low dielectric constant, and the like. , IC, LSI and VLSI chips are used as interlayer insulating films and surface protective films. However, in the conventional pattern forming method for these films,
After coating and drying the polyimide precursor on the wafer, pattern etching had to be performed using photoresist, and harmful hydrazine solution had to be used as the polyimide etching solution .

[0003] For this reason, attempts to introduce a photosensitive group into a polyimide precursor to enable pattern formation of the polyimide itself have been made by various material manufacturers, and are in the practical stage in some product fields. However, photosensitive polyimides currently in practical use can be broadly classified into those in which photosensitive groups are introduced into the polyimide precursor through ionic bonds and those in which photosensitive groups are introduced through ester bonds. The sensitivity is low (the solubility difference is low) with respect to the exposure apparatus used in the process, and the process margin is low because the solubility of the resin decreases in the process. Also,
In the latter case, a complicated process is required for the production of the polyimide precursor, and a high-molecular-weight product having a practically sufficient high molecular weight cannot be obtained. Further, these resins employ a negative pattern forming method, and must be developed with an organic solvent when forming a pattern, which is a serious problem from the viewpoint of environmental conservation.

Recently, as a positive photosensitive resin composition, a composition in which a diazonaphthoquinone compound is added to polybenzoxazole has been proposed. However, this resin composition is inferior to polyimide resin in heat resistance and chemical resistance, and can be applied only to limited semiconductor products. From these problems, there is a strong demand for a positive photosensitive polyimide precursor that can use an aqueous alkaline solution at the time of pattern formation, and that does not swell with the developer and can increase the resolution.

[0005]

SUMMARY OF THE INVENTION It is an object of the present invention to solve the above-mentioned conventional disadvantages and to provide a polyimide precursor having a positive pattern forming ability capable of being developed with an aqueous alkali solution and a stable polyimide precursor. It is intended to provide a manufacturing method.

[0006]

Means for Solving the Problems As a result of intensive research aimed at achieving the above object, the present inventor has found that the above object can be achieved by employing a resin composition described below and a method for producing the same. The present invention has been completed.

That is, the photosensitive resin composition of the present invention comprises:
(A) a polyimide precursor represented by the following general formula:

Embedded image(However, in the formula, R¹Is a tetravalent aromatic group, a plurality of aromatic groups
A tetravalent organic group having a single bond or a plurality of aromatic rings
-O-, -CO-, -SO_Two-Or -CH_TwoNegative
A combined tetravalent organic group,^TwoIs divalent aromatic
Group, a divalent organic group in which a plurality of aromatic rings are single-bonded, or
Plural aromatic rings are -O-, -CO-, -SO _Two-Young
Is -CH_TwoA divalent organic group linked by-^Three,
R^FourIs a diazonaphthoquinone ring or phenolic OH
An organic group having an aromatic ring having a group, wherein n is one or more
(B) In synthesizing the above (A) polyimide precursor
Dehydrating condensing agent to be used, (C)
And (D) a solvent.
I do.

Further, the method for producing the photosensitive resin composition of the present invention comprises the steps of (1) preparing an acid dianhydride having an R ¹ skeleton and an alcoholic compound having an R ³ , R ⁴ skeleton represented by the following general formula: Esterification reaction step,

Embedded image(However, in the formula, R¹Is a tetravalent aromatic group, a plurality of aromatic groups
A tetravalent organic group having a single bond or a plurality of aromatic rings
-O-, -CO-, -SO_Two-Or -CH_TwoNegative
A combined tetravalent organic group,^TwoIs divalent aromatic
Group, a divalent organic group in which a plurality of aromatic rings are single-bonded, or
Plural aromatic rings are -O-, -CO-, -SO _Two-Young
Is -CH_TwoA divalent organic group linked by-^Three,
R^FourIs a diazonaphthoquinone ring or phenolic OH
An organic group having an aromatic ring having a group, wherein n is one or more
(2) Under the addition of a dehydrating condensing agent, the esterification reaction of (1)
And R in the above general formula^TwoDiamine compound with skeleton
(3) Polycondensation-reacted polyimide
Precursor purification process and (4) polyimide containing photosensitizer
It is characterized by comprising a step of preparing a precursor solution.

Hereinafter, the present invention will be described in detail.

First, the method for producing the photosensitive resin composition of the present invention will be described in the order of steps (1) to (4).

(1) An esterification reaction step between an acid dianhydride having an R ¹ skeleton and a compound having an R ³ , R ⁴ skeleton in the formula (4): An acid having an R ¹ skeleton of the polyimide precursor in the present invention As the component, for example, pyromellitic acid, 3,3 ′, 4,
4'-biphenyltetracarboxylic acid, 2,3,3 ',
4'-biphenyltetracarboxylic acid, 3,3 ', 4
4'-benzophenonetetracarboxylic acid, 4,4'-oxydiphthalic acid, 3,3 ', 4,4'-diphenylsulfonetetracarboxylic acid, 2,2-bis (3,4-dicarboxyphenyl) hexafluoropropane, 2,3
6,7-naphthalenetetracarboxylic acid, 1,2,5,6
-Naphthalenetetracarboxylic acid, 1,4,5,8-naphthalenetetracarboxylic acid, 1,2,3,4-cyclobutanetetracarboxylic acid, 1,2,3,4-butanetetracarboxylic acid, 1,2,4 , 5-cyclopentanetetracarboxylic acid, 1,2,4,5-cyclohexanetetracarboxylic acid, 3,3 ', 4,4'-bicyclohexyltetracarboxylic acid, 2,3,5-tricarboxycyclopentylacetic acid, , 4-Dicarboxy-1,2,3,4-tetrahydronaphthalene-1-succinic acid and its anhydrides, which can be used alone or in combination.

Further, R ³ and R ⁴ skeletons in which a diazonaphthoquinone ring (Group A) or an aromatic ring having a phenolic OH group (Group B) is introduced into the acid component serving as the R ¹ skeleton through an ester bond. Examples of the alcoholic compound having

Embedded image Group B

Embedded image And the like.

The introduction ratio of the groups A and B is preferably 5:90 to 30:70 by weight in terms of ester bond ratio. If the ratio of group A is high, the sensitivity to ultraviolet rays decreases, and B
When the group ratio is high, the obtained pattern swells. Also, A
The compounds in group B and group B can be used alone or as a mixture.

The acid component serving as the R ¹ skeleton and the R ³ , R
The esterification reaction with an alcoholic compound having a ⁴ skeleton is, for example, an acid dihydrate having an R ¹ skeleton and an alcohol having an R ³ or R ⁴ skeleton. The reaction is preferably carried out at room temperature in the presence of a polar solvent, for example, N-methyl-2-pyrrolidone, etc., in the presence of a basic catalyst for smoothly carrying out the reaction, for example, triethylamine, pyridine, triethanolamine or the like.
This basic catalyst can be used in a range of 1.5 to 3.0 times mol, preferably 2.0 to 2.5 times mol of the above acid component.

The R ³ and R ⁴ skeletons introduced into the acid component serving as the R ¹ skeleton through an ester bond may be introduced through an amide bond.

(2) Polycondensation reaction of the above esterification reaction product with a diamine compound serving as an R ² skeleton in the chemical formula 4 The diamine component serving as an R ² skeleton used in the present invention includes:
For example, m-phenylenediamine, p-phenylenediamine, 2,4-diaminotoluene, 2,5-diaminotoluene, 2,6-diaminotoluene, 3,5-diaminotoluene, 1-methoxy-2,4-diaminobenzene ,
1,4-diamino-2-methoxy-5-methylbenzene, 1,3-diamino-4,6-dimethylbenzene,
3,5-diaminobenzoic acid, 2,5-diaminobenzoic acid, 1,2-diaminonaphthalene, 1,4-diaminonaphthalene, 1,5-diaminonaphthalene, 1,6-diaminonaphthalene, 1,7-diaminonaphthalene , 1,8
-Diaminonaphthalene, 2,3-diaminonaphthalene,
2,6-diaminonaphthalene, 1,4-diamino-2-
Methyl naphthalene, 1,5-diamino-2-methylnaphthalene, 1,3-diamino-2-phenylnaphthalene,
2,2-bis (4-aminophenyl) propane, 1,1
-Bis (4-aminophenyl) ethane, 4,4'-diaminodiphenylmethane, 3,3'-dimethyl-4,4 '
-Diaminodiphenylmethane, 3,3 ', 5,5'-tetramethyl-4,4'-diaminodiphenylmethane,
3,3'-dimethyl-5,5'-diethyl-4,4'-
Diaminodiphenylmethane, 3,3 ', 5,5'-tetraethyl-4,4'-diaminodiphenylmethane, 4,
4'-methylenebis (cyclohexylamine), 4,
4'-methylenebis (3,3-dimethyl-cyclohexylamine), 2,4'-diaminodiphenyl sulfide, 4,4'-diaminodiphenyl sulfide, 3,
3'-diaminodiphenylsulfone, 4,4'-diaminodiphenylsulfone, 4,4'-diaminobenzanilide, 3,3'-diaminodiphenylether,
3,4'-diaminodiphenyl ether, 4,4'-diaminodiphenyl ether, bis (4-aminophenyl) diethylsilane, bis (4-aminophenyl) diphenylsilane, bis (4-aminophenyl) -N-methylamine, bis (4-aminophenyl) -N-phenylamine, 3,3'-diaminobenzophenone, 4,4 '
-Diaminobenzophenone, 2,6-diaminopyridine, 3,5-diaminopyridine, 4,4'-diaminobiphenyl, 3,3'-diaminobiphenyl, 3,3'-
Dimethyl-4,4'-diaminobiphenyl, 3,3'-
Dimethoxy-4,4'-diaminobiphenyl, 3,3 '
-Dihydroxy-4,4'-diaminobiphenyl, o-
Toluidine sulfone, 4,4'-bis (4-aminophenoxy) biphenyl, 2,2-bis [4- (4-aminophenoxy) phenyl] propane, bis [4- (4-
Aminophenoxy) phenyl] ether, bis [4-
(4-aminophenoxy) phenyl] sulfone, bis [4- (3-aminophenoxy) phenyl] sulfone, 1,4-bis (4-aminophenoxy) benzene,
1,3-bis (4-aminophenoxy) benzene, 9,
10-bis (4-aminophenyl) anthracene, 9,
9-bis (4-aminophenyl) fluorene, 2,2-
Bis (4-aminophenyl) hexafluoropropane,
2,2-bis (3-aminophenyl) hexafluoropropane, 1,1-bis (4-aminophenyl) -1-phenyl-2,2,2-trifluoroethane, 2,2-bis (3-amino -4-hydroxyphenyl) hexafluoropropane, 2,2-bis (3-amino-4-methylphenyl) hexafluoropropane, 2,2-bis [4
-(4-aminophenoxy) phenyl] hexafluoropropane and the like, and these can be used alone or as a mixture of two or more. These compounds are preferably used in an equimolar amount with respect to the above ester compound.
It can be used in the range of 1.5 moles.

Next, the dehydrating condensing agent used in the polycondensation reaction in the present invention will be described.

When the esterification reaction product and the diamine component are reacted by the polycondensation method, the reaction is usually carried out using an acid chloride. In the electric and electronic fields including semiconductor devices, the free chloride ion is used as a product. When performing polymerization by the acid chloride method, it is necessary to sufficiently wash with pure water after the polycondensation, since this causes poor reliability. In addition, a carbodiimide derivative such as DCC (dicyclohexylcarbodiimide) used as a dehydration condensing agent causes simultaneous side reactions, gelation of a polyimide precursor,
There are problems such as toxicity, and it is difficult to completely remove urea generated as a by-product. Therefore, it is used for cooling a reaction system, adding a dehydrating condensing agent in several portions, or breaking a molar balance between an acid component and a diamine component. Further, as another method, diphenyl (2,2) has recently been used as a dehydration condensing agent for which the present inventors have filed a patent.
3-dihydro-2-thioxo-3-benzoxazole) phosphonate and its derivatives, diphenyl (2,
3-dihydro-2-thioxo-3-benzothiazole)
A polycondensation method using a phosphonate or a derivative thereof is mentioned. In this method, stable production can be performed under mild conditions, and thus a polyimide precursor having high resolution and high film properties can be obtained. These can be used alone or in combination of two or more. These can be used in an amount of 1 to 3 moles, preferably 2 to 2.5 moles, per 1 mole of the ester compound.

As the solvent for the polycondensation reaction of the polyimide precursor used in the present invention, for example, N-methylpyrrolidone,
An aprotic polar solvent such as N, N'-dimethylacetamide and N, N'-dimethylformamide, cyclohexanone, cyclopentanone and the like are used, and these can be used alone or as a mixture of two or more.

(3) Purification of Polyimide Precursor After Polycondensation Reaction The obtained slurry polymer was treated with methanol, ethanol,
After stirring and washing in a poor solvent such as isopropyl alcohol and water, the precipitate is dried under reduced pressure to obtain a polyimide precursor represented by Chemical Formula 4.

(4) Preparation of Polyimide Precursor Solution Containing Photosensitizer The resin composition produced as described above is produced for the purpose of improving the sensitivity to actinic rays of an exposure machine used for semiconductor device production. The following photosensitizers can be added to the polyimide precursor.

[0022]

Embedded image

Embedded image These photosensitive agents are not limited to the above structure.
In use, they can be used alone or in combination of two or more. The addition amount is preferably 1 to 10 parts by weight. When the amount is less than 1 part by weight, the effect is not obtained.

The resin composition obtained by the present invention is used in the form dissolved in a solvent. Examples of the solvent used for dissolution include N-methylpyrrolidone,
Aprotic polar solvents such as N, N'-dimethylacetamide, N, N'-dimethylformamide, cyclohexanone, cyclopentanone, diethylene glycol diethyl ether, diethylene glycol dibutyl ether, propylene glycol monomethyl ether acetate, methyl lactate, ethyl lactate; Butyl lactate and the like can be mentioned, and these can be used alone or in combination of two or more.

Next, the method of using the resin composition of the present invention will be described.

When application to a semiconductor device is considered, first, this resin composition is coated on a target wafer using a spin coater, and then the coating film is dried at 90 to 120 ° C. An active ultraviolet ray having a wavelength of 365 nm or 436 nm is irradiated through a mask having a pattern drawn on the obtained coating film. Next, this coating film is applied to an alkaline aqueous solution, for example, sodium hydroxide, potassium hydroxide,
Inorganic alkaline aqueous solutions such as sodium carbonate, potassium carbonate and ammonia; primary amines such as ethylamine and n-propylamine; secondary amines such as diethylamine and di-n-propylamine; tertiary amines such as triethylamine and methyldimethylamine; dimethyl Only the active light-irradiated portion is dissolved and developed using an alcoholamine such as ethanolamine and triethanolamine, and a quaternary amine such as tetramethylammonium hydroxide and tetraethylammonium hydroxide, and rinsed with pure water. As a developing system, a system such as spray, paddle, immersion, and ultrasonic wave can be considered. Thereby, a desired positive pattern can be obtained on the target wafer. Further, by heat-treating the coating film, the resin composition can be imidized to form a polyimide film having excellent film properties.

[0026]

DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS Hereinafter, the present invention will be specifically described based on embodiments.

Example 1 A reaction flask equipped with a nitrogen inlet tube was charged with 1 mol of benzophenonetetracarboxylic dianhydride and 2 L of N-methyl-
2-Pyrrolidone, 0.3 mol of p-hydroxybenzyl alcohol ester of 1,2-diazonaphthoquinone-4-sulfonic acid, and 1.8 mol of 4-hydroxybenzyl alcohol were added, followed by stirring, followed by addition of 30 mol of 2.1 mol of triethylamine. Drop in minutes. 3 in this state
After leaving the reaction for 1 hour, 1 mol of 4,4-diaminodiphenyl ether is added, and the mixture is stirred and dissolved for 30 minutes.
Then 2.1 mol of diphenyl (2,3-dihydro-2
-Thioxo-3-benzoxazole) phosphonate is added in five portions, and a condensation reaction is carried out for 5 hours in this state. The obtained slurry mixture is poured into a large amount of methanol for washing, and the obtained solid resin is dried by a vacuum dryer for 12 hours. 30 g of dried solid resin
Was dissolved in 70 g of N-methyl-2-pyrrolidone, and the obtained slurry was filtered at 1 μm to give Sample 1.

This sample 1 was coated on a 6-inch silicon wafer using a spin coater, and dried by heating at 120 ° C. for 3 minutes on a bake plate to form a film having a thickness of 10 μm.
m was obtained. This coating film was 300 m thick by an ultraviolet exposure machine using a filter that transmits only 365 nm.
The test pattern was irradiated with an energy of j / cm ² , followed by paddle development with a 2.38% aqueous solution of TMAH (tetramethylammonium hydride) for 2 minutes. By this operation, a positive relief pattern in which only the ultraviolet irradiation part of the coating film was dissolved was obtained. When the obtained pattern was observed with an optical microscope,
It was confirmed that the pattern up to 1.0 μm was formed sharply.

Further, this pattern was subjected to a heat treatment at 150 ° C. for 1 hour, at 250 ° C. for 1 hour, and at 350 ° C. for 1 hour to complete the imidization of the coating film. This imide pattern was firmly adhered to the silicon wafer, and no resin crack or peeling was observed in the pattern.

Example 2 Into a reaction flask equipped with a nitrogen inlet tube, 1 mol of benzophenonetetracarboxylic dianhydride and 2 L of N-methyl-
2-Pyrrolidone, 0.3 mol of p-hydroxybenzyl alcohol ester of 1,2-diazonaphthoquinone-4-sulfonic acid, and 1.8 mol of 3,5-dihydroxybenzyl alcohol were added, and the mixture was stirred.
ol of triethylamine are added dropwise over 30 minutes. In this state, the mixture is left for 3 hours, and after completion of the reaction, 1 mol of 4,4-diaminodiphenyl ether is added and dissolved by stirring for 30 minutes. Next, 2.1 mol of diphenyl (2,3-dihydro-2-thioxo-3-benzoxazole) phosphonate is added in five portions, and a condensation reaction is carried out for 5 hours in that state. The obtained slurry mixture is poured into a large amount of methanol for washing, and the obtained solid resin is dried by a vacuum dryer for 12 hours. Further dried solid resin 30
g and 3 g of a benzophenone-type disubstituted diazonaphthoquinone compound were dissolved in 67 g of N-methyl-2-pyrrolidone, and the resulting slurry was filtered at 1 μm to give Sample 2.

Sample 2 was coated on a 6-inch silicon wafer using a spin coater, and dried by heating at 120 ° C. for 3 minutes on a baking plate to form a film having a thickness of 10 μm.
m was obtained. This coating film was exposed to an ultraviolet light using a filter that transmits only 365 nm to a thickness of 150 m.
The test pattern was irradiated with an energy of j / cm ² , followed by paddle development with a 2.38% aqueous solution of TMAH (tetramethylammonium hydride) for 1 minute. By this operation, a positive relief pattern in which only the ultraviolet irradiation part of the coating film was dissolved was obtained. When the obtained pattern was observed with an optical microscope,
It was confirmed that the pattern up to 1.0 μm was formed sharply.

Further, the pattern was subjected to a heat treatment at 150 ° C. for 1 hour, at 250 ° C. for 1 hour, and at 350 ° C. for 1 hour to complete the imidization of the coating film. This imide pattern was firmly adhered to the silicon wafer, and no resin crack or peeling was observed in the pattern.

Comparative Example A reaction flask equipped with a nitrogen inlet tube was charged with 1 mol of benzophenonetetracarboxylic dianhydride and 2 L of N-methyl-
2-Pyrrolidone and 2.1 mol of p-hydroxybenzyl alcohol were added and stirred, followed by 2.1 mol.
Of triethylamine is added dropwise over 30 minutes. In this state, the mixture is left for 3 hours, and after completion of the reaction, 1 mol of 4,4-diaminodiphenyl ether is added and dissolved by stirring for 30 minutes. Next, 2.1 mol of diphenyl (2,3-dihydro-2-thioxo-3-benzoxazole) phosphonate is added in five portions, and a condensation reaction is carried out for 5 hours in that state. The obtained slurry mixture is poured into a large amount of methanol for washing, and the obtained solid resin is dried by a vacuum dryer for 12 hours. 30 g of dried solid resin
And 3 g of a disubstituted diazonaphthoquinone compound of the benzophenone type were dissolved in 67 g of N-methyl-2-pyrrolidone, and the resulting slurry was filtered at 1 μm to obtain a sample 3
And

This sample 3 was coated on a 6-inch silicon wafer using a spin coater and dried by heating at 120 ° C. for 3 minutes on a bake plate to form a film having a thickness of 10 μm.
m was obtained. This coating film was 300 m thick by an ultraviolet exposure machine using a filter that transmits only 365 nm.
The test pattern was irradiated with an energy of j / cm ² , followed by paddle development with a 2.38% aqueous solution of TMAH (tetramethylammonium hydride) for 1 minute. By this operation, a positive relief pattern in which only the ultraviolet irradiation part of the coating film was dissolved was obtained. Observation of the obtained pattern with an optical microscope revealed that
It was confirmed that a pattern up to 5.0 μm was formed. However, this pattern was swollen and not a sharp shape.

Further, this pattern was subjected to a heat treatment at 150 ° C. for 1 hour, at 250 ° C. for 1 hour, and at 350 ° C. for 1 hour to complete the imidization of the coating film. This imide pattern was firmly adhered to the silicon wafer, and no resin crack or peeling was observed in the pattern.

[0036]

The present invention is a photosensitive polyimide precursor having a positive pattern forming ability, and an alkaline aqueous solution can be used for pattern formation. For this reason, not only can the obtained pattern swell little in the developing solution, and not only can a very sharp high-resolution pattern be obtained, but also industrial waste of organic solvents that has been generated in large quantities can be completely eliminated. Further, the polyimide coating finally obtained is excellent in heat resistance and chemical resistance, so that it can be used in the same manner as a commonly used semiconductor device protective film. The present invention relates to the resin skeleton itself used in the photosensitive resin composition and a method for producing the resin skeleton, but these are based on a completely new idea, and are very unique inventions like no other. It is easy to understand.

──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. ⁷ Identification symbol FI Theme coat ゛ (Reference) G03F 7/022 G03F 7/022 H01L 21/027 H01L 21/30 502R F-term (Reference) 2H025 AA00 AA01 AA06 AA07 AA08 AA10 AA20 AB16 AC01 AD03 BE01 BE02 BJ10 CC03 CC20 FA03 FA17 FA29 4J002 CM041 EV216 FD146 FD206 GP03 4J043 PA01 PC015 PC065 QB21 QB31 RA05 RA06 RA35 SA06 SA42 SA47 SA61 SA71 SA72 SB01 SB02 TA14 TA02 TA31 UA1 TA21 TA04 TA03 TA04 UA121 UA122 UA131 UA132 UA141 UA151 UA231 UA232 UA251 UA261 UA262 UA361 UB011 UB021 UB051 UB061 UB062 UB121 UB122 UB151 UB152 UB241 UB281 ZUB30 UB301 UB302 UB311 XA13 XA16 XA19 XB12 XA19 XB16

Claims (2)

[Claims] (A) a polyimide represented by the following general formula:
Precursor,(However, in the formula, R¹Is a tetravalent aromatic group, a plurality of aromatic groups
A tetravalent organic group having a single bond or a plurality of aromatic rings
-O-, -CO-, -SO_Two-Or -CH_TwoNegative
A combined tetravalent organic group,^TwoIs divalent aromatic
Group, a divalent organic group in which a plurality of aromatic rings are single-bonded, or
Plural aromatic rings are -O-, -CO-, -SO _Two-Young
Is -CH_TwoA divalent organic group linked by-^Three,
R^FourIs a diazonaphthoquinone ring or phenolic OH
An organic group having an aromatic ring having a group, wherein n is one or more
(B) The above (A) polyimide precursor is combined.
The dehydrating condensing agent used for forming
Consisting of a photosensitizer and a solvent (D) for improving sensitivity
A photosensitive resin composition comprising: (1) R represented by the following general formula:¹Skeleton
Acid dianhydride with R^Three, R^FourAlcoholic with skeleton
An esterification reaction step with a compound,(However, in the formula, R¹Is a tetravalent aromatic group, a plurality of aromatic groups
A tetravalent organic group having a single bond or a plurality of aromatic rings
-O-, -CO-, -SO_Two-Or -CH_TwoNegative
A combined tetravalent organic group,^TwoIs divalent aromatic
Group, a divalent organic group in which a plurality of aromatic rings are single-bonded, or
Plural aromatic rings are -O-, -CO-, -SO _Two-Young
Is -CH_TwoA divalent organic group linked by-^Three,
R^FourIs a diazonaphthoquinone ring or phenolic OH
An organic group having an aromatic ring having a group, wherein n is one or more
(2) Under the addition of a dehydrating condensing agent, the esterification reaction of (1)
And R in the above general formula^TwoDiamine compound with skeleton
(3) Polycondensation-reacted polyimide
Precursor purification process and (4) polyimide containing photosensitizer
Photosensitivity characterized by comprising a precursor solution preparation process
A method for producing a resin composition.