JP7233189B2 - Photosensitive resin composition, dry film, cured product and electronic parts - Google Patents

Description

The present invention provides a photosensitive resin composition, a dry film having a resin layer formed from the photosensitive resin composition, a cured product formed from the photosensitive resin composition, and a printed wiring having the cured product as a forming material. It relates to electronic parts such as plates and semiconductor elements.

Polyimide is widely used in various fields due to its excellent properties such as high insulation, heat resistance and mechanical strength. For example, it is applied not only to the aerospace field but also to flexible printed wiring boards, buffer coat films for semiconductor elements, and insulating films for rewiring layers of wafer level packages (WLP).

Generally, polyimide has the aspect of poor thermoplasticity and poor solubility in organic solvents, and is difficult to process. Therefore, polyimide is used in the form of a liquid photosensitive resin composition obtained by blending an organic solvent-soluble polyimide precursor and a photoreactive compound.
Specifically, the photosensitive resin composition is applied onto a substrate such as a wafer and dried to form a dry coating film, and the dry coating film is exposed to active energy rays and then developed. Thus, after forming a desired pattern film, the polyimide precursor undergoes a ring closure reaction and is cured by heating at a high temperature to obtain polyimide.

As such a photosensitive resin composition, a positive photosensitive resin composition containing a polyimide precursor and naphthoquinonediazide has been conventionally proposed (see Patent Document 1).

However, in the photosensitive resin composition as proposed in this Patent Document 1, due to the carboxyl groups possessed by the polyimide precursor, even the unexposed areas are dissolved during development (film reduction phenomenon). There was a problem that a desired patterned film could not be obtained. In other words, there is a demand for a material that exhibits a large dissolution rate difference between an exposed area and an unexposed area during development (high dissolution contrast).

In addition, in the photosensitive resin composition as proposed in Patent Document 1, since the difference in linear thermal expansion coefficient between the cured film made of such a composition and the substrate such as a wafer is large, the thickness of the wafer is reduced. In recent years, as the size of the film has become larger, the heating and curing at the above-mentioned high temperature tends to cause warpage, which has been a factor in reducing the yield. That is, there is a demand for a material whose cured film exhibits a lower coefficient of linear thermal expansion.

Furthermore, in the photosensitive resin composition disclosed in Patent Document 1, the pattern film is melted and deformed due to heat curing at the above high temperature, which is a factor in reducing the yield. That is, there is a demand for a material that is excellent in high-temperature pattern retention.

Furthermore, from the viewpoint of cost reduction, such a photosensitive resin composition is required to have high sensitivity so that the exposed portion can be developed even with a lower exposure amount.

JP-A-52-13315

The present invention has been made to solve such problems, and its main purpose is to exhibit a dry coating film having high sensitivity and excellent dissolution contrast and high-temperature pattern retention and a low coefficient of linear thermal expansion. An object of the present invention is to provide a photosensitive resin composition effective for obtaining a cured film.

Another object of the present invention is to provide electronic parts such as dry films, printed wiring boards, and semiconductor elements using the photosensitive resin composition.

The present inventors have made intensive studies to achieve the above objects, and found that the dissolution contrast of the photosensitive resin composition can be significantly improved by including a polyimide precursor having a specific structure in the photosensitive resin composition. The present inventors have completed the present invention based on the finding that high-temperature pattern retention can be significantly improved, sensitivity can be significantly improved, and the coefficient of linear thermal expansion of the cured film can be significantly reduced.

（一般式（１）および（２）中、
Ｘ は、４価の有機基であり、
Ｒ_１およびＲ_２は、それぞれ独立して、水素原子、シリル基および炭素数１～２０の１価の有機基から選択され、
Ｒ_３～Ｒ_６のいずれかが、炭素数１～１２のアルキル基、炭素数１～１２のアルコキシ基、炭素数６～１０の芳香族基、炭素数６～１０のフェノキシ基、炭素数６～１０のベンジル基および炭素数６～１０のベンジルオキシ基から選択され、それ以外のＲ_３～Ｒ_６が水素原子であり、
ｎは、１以上の整数を示す。） That is, the photosensitive resin composition of the present invention is
(A) an ester group-containing polyimide precursor represented by the following general formula (1) or (2);
(B) a photosensitive agent.

(In general formulas (1) and (2),
X is a tetravalent organic group,
R.₁and R₂are each independently selected from a hydrogen atom, a silyl group and a monovalent organic group having 1 to 20 carbon atoms,
R.₃～R₆is an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an aromatic group having 6 to 10 carbon atoms, a phenoxy group having 6 to 10 carbon atoms, or a benzyl group having 6 to 10 carbon atoms. and a benzyloxy group having 6 to 10 carbon atoms, other than R₃～R₆is a hydrogen atom,
n represents an integer of 1 or more. )

In the present invention, in the above (1) and (2), either R ₃ or R ₅ is an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, or an aromatic group having 6 to 10 carbon atoms. phenoxy group having 6 to 10 carbon atoms, benzyl group having 6 to 10 carbon atoms and benzyloxy group having 6 to 10 carbon atoms, the other being a hydrogen atom, and R ₄ and R ₆ are hydrogen atoms is preferably

In the present invention, the photosensitizer is preferably a naphthoquinonediazide compound.

The dry film of the present invention is characterized by comprising a resin layer formed from the photosensitive resin composition on the film.

The cured product of the present invention is characterized by being formed from the resin layer of the above photosensitive resin composition or the above dry film.

Electronic parts of the present invention, such as printed wiring boards and semiconductor elements, are characterized by having the cured product as a forming material.

According to the present invention, there is provided a photosensitive resin composition which has high sensitivity and is effective in obtaining a dried coating film excellent in dissolution contrast and high-temperature pattern retention and a cured film exhibiting a low coefficient of linear thermal expansion. can do.

FIG. 1 is an image of a rectangular pattern film after heating formed from the photosensitive resin composition of Example 1. FIG. 2 is an image of a rectangular pattern film after heating formed from the photosensitive resin composition of Example 2. FIG. 3 is an image of a rectangular pattern film after heating formed from the photosensitive resin composition of Comparative Example 1. FIG.

[Photosensitive resin composition]
The photosensitive resin composition of the present invention contains (A) at least one of the ester group-containing polyimide precursors represented by formulas (1) and (2), and (B) a photosensitive agent.
By configuring the photosensitive resin composition in this way, the dissolution contrast and sensitivity of the photosensitive resin composition can be significantly improved, the resulting dried coating film has excellent high-temperature pattern retention, and the resulting cured film has the The coefficient of linear thermal expansion can be significantly reduced.

Specifically, as for the dissolution contrast, the ratio of the dissolution rate of the exposed area of the photosensitive resin composition to the dissolution rate of the unexposed area was able to be improved to 7 or more.
As for the sensitivity, the i-line transmittance of the photosensitive resin composition was improved to 60% or more, and in a preferred embodiment, to 80% or more.
Further, the reason why a dried coating film having excellent high-temperature pattern retention is obtained is that, according to the configuration of the photosensitive resin composition of the present invention, the glass transition temperature (Tg) of the cured product is 320° C. or higher, which is a preferred embodiment. This is considered to be due to the fact that the temperature rises to 340° C. or higher.
Furthermore, the linear thermal expansion coefficient of the resulting cured product can be reduced to less than 40 ppm/°C, preferably less than 25 ppm/°C. It can be expected to effectively prevent the occurrence of warping of the wafer due to heat curing.

The components contained in the photosensitive resin composition of the present invention are described in detail below.
[(A) ester group-containing polyimide precursor]
The photosensitive resin composition of the present invention contains at least one of ester group-containing polyimide precursors represented by the following general formulas (1) and (2).

In general formulas (1) and (2) above, R ₁ and R ₂ are each independently selected from a hydrogen atom, a silyl group and a monovalent organic group having 1 to 20 carbon atoms.
Silyl groups include trimethylsilyl, tri-t-butylsilyl, di-t-butylmethylsilyl, t-butyldimethylsilyl, triphenylsilyl, diphenylmethylsilyl and phenyldimethylsilyl groups.
Examples of monovalent organic groups having 1 to 20 carbon atoms include alkyl groups such as methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, pentyl group and hexyl group, phenyl group, tolyl group and naphthyl group. aryl groups such as, alkenyl groups, and alkynyl groups.

In the general formulas (1) and (2), any one of R ₃ to R ₆ , preferably R ₃ or R ₅ , particularly preferably R ₃ , is an alkyl group having 1 to 12 carbon atoms; selected from an alkoxy group having 1 to 12 carbon atoms, an aromatic group having 6 to 10 carbon atoms, a phenoxy group having 6 to 10 carbon atoms, a benzyl group having 6 to 10 carbon atoms and a benzyloxy group having 6 to 10 carbon atoms, Other R ₃ to R ₆ are hydrogen atoms.
Examples of alkyl groups having 1 to 12 carbon atoms include methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, pentyl group and hexyl group.
Examples of alkoxy groups having 1 to 12 carbon atoms include methoxy, ethoxy, propoxy, butoxy and pentoxy groups.
Aromatic groups having 6 to 10 carbon atoms include phenyl group, tolyl group, methylphenyl group, dimethylphenyl group, ethylphenyl group, diethylphenyl group, propylphenyl group, butylphenyl group, fluorophenyl group and pentafluorophenyl group. , chlorophenyl group, bromophenyl group, methoxyphenyl group, dimethoxyphenyl group, ethoxyphenyl group, diethoxyphenyl group, methoxybenzyl group, dimethoxybenzyl group, ethoxybenzyl group, diethoxybenzyl group, aminophenyl group, aminobenzyl group , nitrophenyl group, nitrobenzyl group, cyanophenyl group, cyanobenzyl group, phenethyl group, phenylpropyl group, phenylamino group, diphenylamino group, biphenyl group and naphthyl group.
The phenoxy group having 6 to 10 carbon atoms includes methylphenoxy group, ethylphenoxy group, propylphenoxy group, dimethylphenoxy group, diethylphenoxy group, methoxyphenoxy group, ethoxyphenoxy group and dimethoxyphenoxy group.
The benzyl group having 6 to 10 carbon atoms includes benzyl group, methylbenzyl group, ethylbenzyl group, propylbenzyl group, dimethylbenzyl group, methoxybenzyl group, ethoxybenzyl group and methoxybenzyl group.
benzyloxy group having 6 to 10 carbon atoms, methylbenzyloxy group, benzyloxy group, benzylbenzyloxy group, ethylbenzyloxy group, propylbenzyloxy group, dimethylbenzyloxy group, methoxybenzyloxy group and ethoxy group; A benzyloxy group and the like can be mentioned.
Among the above, from the viewpoint of the dissolution contrast of the photosensitive resin composition, high-temperature pattern retention, sensitivity and linear thermal expansion coefficient, any one of R ₃ to R ₆ is an aromatic group having 6 to 10 carbon atoms, carbon A phenoxy group having 6 to 10 carbon atoms, a benzyl group having 6 to 10 carbon atoms and a benzyloxy group having 6 to 10 carbon atoms are preferable, and an aromatic group having 6 to 10 carbon atoms is more preferable, and a phenyl group and a tolyl group. , a methylphenyl group, a dimethylphenyl group, an ethylphenyl group and a diethylphenyl group are more preferable, and a phenyl group is particularly preferable from the viewpoint of the effect of suppressing film reduction in unexposed areas.

The number average molecular weight (Mn) of the ester group-containing polyimide precursor is preferably 2,000 or more and 50,000 or less, more preferably 4,000 or more and 25,000 or less. This improves the solubility in an alkaline developer.
The weight average molecular weight (Mw) of the ester group-containing polyimide precursor is preferably 4,000 or more and 10,000 or less, more preferably 8,000 or more and 50,000 or less. Thereby, a good cured film free from cracks can be obtained.
Furthermore, Mw/Mn is preferably 1 or more and 5 or less, more preferably 1 or more and 3 or less.
In the present invention, the number average molecular weight and weight average molecular weight are numerical values measured by gel permeation chromatography (GPC) and converted to standard polystyrene.

The photosensitive resin composition of the present invention uses an ester group-containing polyimide precursor as described above as a polyimide precursor, so that the dissolution contrast and sensitivity of the photosensitive resin composition can be significantly improved, and the resulting drying The coating film is excellent in high-temperature pattern retention, and the resulting cured film can remarkably lower its coefficient of linear thermal expansion.
In addition, the photosensitive resin composition of the present invention may contain two or more kinds of ester group-containing polyimide precursors.

This ester group-containing polyimide body can be obtained by reacting at least a diamine compound represented by the following general formula (3) with an acid anhydride represented by the following general formula (4).
In the reaction, examples of the acid anhydride represented by the general formula (4) include pyromellitic anhydride, biphenyl-3,4,3′,4′-tetracarboxylic dianhydride, benzophenone-3 ,4,3′,4′-tetracarboxylic dianhydride, oxydiphthalic dianhydride, diphenylsulfone-3,4,3′,4′-tetracarboxylic dianhydride, 4,4′-(2, 2-hexafluoroisopropylidene)diphthalic dianhydride, butane-1,2,3,4-tetracarboxylic dianhydride, pentane-1,2,4,5-tetracarboxylic dianhydride, cyclobutanetetracarboxylic acid acid dianhydride, cyclopentane-1,2,3,4-tetracarboxylic dianhydride, cyclohexane-1,2,4,5-tetracarboxylic dianhydride, cyclohex-1-ene-2,3, 5,6-tetracarboxylic dianhydride, 3-ethylcyclohex-1-ene-3-(1,2),5,6-tetracarboxylic dianhydride, 1-methyl-3-ethylcyclohexane-3 -(1,2),5,6-tetracarboxylic dianhydride, 1-methyl-3-ethylcyclohex-1-ene-3-(1,2),5,6-tetracarboxylic dianhydride , 1-ethylcyclohexane-1-(1,2),3,4-tetracarboxylic dianhydride, 1-propylcyclohexane-1-(2,3),3,4-tetracarboxylic dianhydride, 1 ,3-dipropylcyclohexane-1-(2,3),3-(2,3)-tetracarboxylic dianhydride, dicyclohexyl-3,4,3′,4′-tetracarboxylic dianhydride, bicyclo [2.2.1] Heptane-2,3,5,6-tetracarboxylic dianhydride, 1-propylcyclohexane-1-(2,3),3,4-tetracarboxylic dianhydride, 1, 3-dipropylcyclohexane-1-(2,3),3-(2,3)-tetracarboxylic dianhydride, dicyclohexyl-3,4,3′,4′-tetracarboxylic dianhydride, bicyclo[ 2.2.1]heptane-2,3,5,6-tetracarboxylic dianhydride, bicyclo[2.2.2]octane-2,3,5,6-tetracarboxylic dianhydride, bicyclo[ 2.2.2]oct-7-ene-2,3,5,6-tetracarboxylic dianhydride and the like. ,4,3′,4′-tetracarboxylic dianhydride, and oxydiphthalic dianhydride is preferred in order to maintain high i-line transmittance. stomach. These acid anhydrides may be used alone or in combination of two or more.

In the general formulas (3) and (4), X and R ₃ to R ₆ are as described above.

This ester group-containing polyimide body can be combined with a diamine compound other than the diamine compound represented by the general formula (3) within a range that does not impair the characteristic effects and polymerization reactivity.
Examples of diamine compounds other than the diamine compound represented by the general formula (3) include 4,4′-bis(3-aminophenoxy)biphenyl, bis[4-(3-aminophenoxy)phenyl]ketone, bis[4- (3-aminophenoxy)phenyl]sulfide, bis[4-(3-aminophenoxy)phenyl]sulfone, 2,2-bis[4-(3-aminophenoxy)phenyl]propane, 2,2-bis[4- (3-aminophenoxy)phenyl]-1,1,1,3,3,3-hexafluoropropane, m-phenylenediamine, o-phenylenediamine, p-phenylenediamine, m-aminobenzylamine, p-aminobenzyl amine, 3,3'-diaminodiphenyl ether, 3,4'-diaminodiphenyl ether, 4,4'-diaminodiphenyl ether, 3,3'-diaminodiphenyl sulfide, 3,3'-diaminodiphenyl sulfoxide, 3,4'-diamino Diphenyl sulfoxide, 4,4'-diaminodiphenyl sulfoxide, 3,3'-diaminodiphenyl sulfone, 3,4'-diaminodiphenyl sulfone, 4,4'-diaminodiphenyl sulfone, 3,3'-diaminobenzophenone, 3,4 '-diaminobenzophenone, 4,4'-diaminobenzophenone, 3,3'-diaminodiphenylmethane, 3,4'-diaminodiphenylmethane, 4,4'-diaminodiphenylmethane, bis[4-(4-aminophenoxy)phenyl]methane , 1,1-bis[4-(4-aminophenoxy)phenyl]ethane, 1,2-bis[4-(4-aminophenoxy)phenyl]ethane, 1,1-bis[4-(4-aminophenoxy) ) phenyl]propane, 1,2-bis[4-(4-aminophenoxy)phenyl]propane, 1,3-bis[4-(4-aminophenoxy)phenyl]propane, 2,2-bis[4-( 4-aminophenoxy)phenyl]propane, 1,1-bis[4-(4-aminophenoxy)phenyl]butane, 1,3-bis[4-(4-aminophenoxy)phenyl]butane, 1,4-bis [4-(4-aminophenoxy)phenyl]butane, 2,2-bis[4-(4-aminophenoxy)phenyl]butane, 2,3-bis[4-(4-aminophenoxy)phenyl]butane, 2- [4-(4-aminophenoxy)phenyl]-2-[4-(4-aminophenoxy)-3-methylphenyl]pro Pan, 2,2-bis[4-(4-aminophenoxy)-3-methylphenyl]propane, 2-[4-(4-aminophenoxy)phenyl]-2-[4-(4-aminophenoxy)- 3,5-dimethylphenyl]propane, 2,2-bis[4-(4-aminophenoxy)-3,5-dimethylphenyl]propane, 2,2-bis[4-(4-aminophenoxy)phenyl]- 1,1,1,3,3,3-hexafluoropropane, 1,4-bis(3-aminophenoxy)benzene, 1,3-bis(3-aminophenoxy)benzene, 1,4-bis(4- aminophenoxy)benzene, 4,4′-bis(4-aminophenoxy)biphenyl, bis[4-(4-aminophenoxy)phenyl]ketone, bis[4-(4-aminophenoxy)phenyl]sulfide, bis[4 -(4-aminophenoxy)phenyl]sulfoxide, bis[4-(4-aminophenoxy)phenyl]sulfone, bis[4-(3-aminophenoxy)phenyl]ether, bis[4-(4-aminophenoxy)phenyl ] ether, 1,3-bis[4-(4-aminophenoxy)benzoyl]benzene, 1,3-bis[4-(3-aminophenoxy)benzoyl]benzene, 1,4-bis[4-(3- aminophenoxy)benzoyl]benzene, 4,4'-bis[(3-aminophenoxy)benzoyl]benzene, 1,1-bis[4-(3-aminophenoxy)phenyl]propane, 1,3-bis[4- (3-aminophenoxy)phenyl]propane, 3,4′-diaminodiphenyl sulfide, 2,2-bis[3-(3-aminophenoxy)phenyl]-1,1,1,3,3,3-hexafluoro Propane, bis[4-(3-aminophenoxy)phenyl]methane, 1,1-bis[4-(3-aminophenoxy)phenyl]ethane, 1,2-bis[4-(3-aminophenoxy)phenyl] ethane, bis[4-(3-aminophenoxy)phenyl]sulfoxide, 4,4'-bis[3-(4-aminophenoxy)benzoyl]diphenyl ether, 4,4'-bis[3-(3-aminophenoxy) benzoyl]diphenyl ether, 4,4'-bis[4-(4-amino-α,α-dimethylbenzyl)phenoxy]benzophenone, 4,4'-bis[4-(4-amino-α,α-dimethylbenzyl) phenoxy]diphenylsulfone, bis[4-{4-(4- aminophenoxy)phenoxy}phenyl]sulfone, 1,4-bis[4-(4-aminophenoxy)phenoxy-α,α-dimethylbenzyl]benzene, 1,3-bis[4-(4-aminophenoxy)phenoxy- α,α-dimethylbenzyl]benzene, 1,3-bis[4-(4-amino-6-trifluoromethylphenoxy)-α,α-dimethylbenzyl]benzene, 1,3-bis[4-(4- amino-6-fluorophenoxy)-α,α-dimethylbenzyl]benzene, 1,3-bis[4-(4-amino-6-methylphenoxy)-α,α-dimethylbenzyl]benzene, 1,3-bis [4-(4-amino-6-cyanophenoxy)-α,α-dimethylbenzyl]benzene, 3,3′-diamino-4,4′-diphenoxybenzophenone, 4,4′-diamino-5,5′ -diphenoxybenzophenone, 3,4'-diamino-4,5'-diphenoxybenzophenone, 3,3'-diamino-4-phenoxybenzophenone, 4,4'-diamino-5-phenoxybenzophenone, 3,4'- Diamino-4-phenoxybenzophenone, 3,4'-diamino-5'-phenoxybenzophenone, 3,3'-diamino-4,4'-dibiphenoxybenzophenone, 4,4'-diamino-5,5'-dibiphenoxy Benzophenone, 3,4'-diamino-4,5'-dibiphenoxybenzophenone, 3,3'-diamino-4-biphenoxybenzophenone, 4,4'-diamino-5-biphenoxybenzophenone, 3,4'-diamino -4-biphenoxybenzophenone, 3,4'-diamino-5'-biphenoxybenzophenone, 1,3-bis(3-amino-4-phenoxybenzoyl)benzene, 1,4-bis(3-amino-4- phenoxybenzoyl)benzene, 1,3-bis(4-amino-5-phenoxybenzoyl)benzene, 1,4-bis(4-amino-5-phenoxybenzoyl)benzene, 1,3-bis(3-amino-4 -biphenoxybenzoyl)benzene, 1,4-bis(3-amino-4-biphenoxybenzoyl)benzene, 1,3-bis(4-amino-5-biphenoxybenzoyl)benzene, 1,4-bis(4 -amino-5-biphenoxybenzoyl)benzene, 2,6-bis[4-(4-amino-α,α-dimethylbenzyl)phenoxy]benzonitrile and aromatics in the above aromatic diamines. some or all of the hydrogen atoms on the aromatic ring are substituted with halogen atoms, or some or all of the hydrogen atoms of an alkyl or alkoxyl group having 1 to 3 carbon atoms, a cyano group, or an alkyl or alkoxyl group are substituted with halogen atoms; 4,4'-methylenebis(cyclohexylamine), isophoronediamine, trans-1,4-diaminocyclohexane, cis-1,4- Diaminocyclohexane, 1,4-cyclohexanebis(methylamine), 2,5-bis(aminomethyl)bicyclo[2,2,1]heptane, 2,6-bis(aminomethyl)bicyclo[2,2,1] Heptane, 3,8-bis(aminomethyl)tricyclo[5,2,1,0]decane, 1,3-diaminoadamantane, 2,2-bis(4-aminocyclohexyl)propane, 2,2-bis(4 -aminocyclohexyl)hexafluoropropane, 1,3-propanediamine, 1,4-tetramethylenediamine, 1,5-pentamethylenediamine, 1,6-hexamethylenediamine, 1,7-heptamethylenediamine, 1, Aliphatic diamines such as 8-octamethylenediamine and 1,9-nonamethylenediamine are included. These diamine compounds other than the diamine compound represented by formula (3) may be used alone, or two or more of them may be used.

The diamine compound represented by the general formula (3) is obtained by reacting a compound represented by the following general formula (5) with a compound represented by the following general formula (6), and then reducing the nitro group. be able to.

In the general formula (6), R ₃ to R ₆ are as described above. In the general formula (5), Y is selected from a hydroxyl group, a fluoro group, a chloro group, a bromo group and an iodo group. represents a halogen group. Among these, a chloro group and a bromo group are preferable from the viewpoint of reactivity.

When Y is a hydroxyl group, the reaction of the compounds represented by the general formulas (5) and (6) is performed with a dehydration condensing agent such as N,N'-dicyclohexylcarbodiimide (DCC) or p-toluenesulfonic acid. It is preferable to carry out in the presence of an organic acid catalyst.
Moreover, when Y is a halogen group, the reaction of the compounds represented by the general formulas (5) and (6) is preferably carried out in the presence of an acid acceptor such as triethylamine.

The diamine compound is not limited to those synthesized by the above method, and commercially available ones may be used.

[(B) Photosensitizer]
The photosensitive resin composition of the present invention contains a photosensitive agent such as a photoacid generator, a photopolymerization initiator and a photobase generator. Among these, photoacid generators are preferred from the viewpoint of dissolution contrast.
This photosensitive agent can be blended in a known and commonly used ratio. For example, the photoacid generator is 5 to 40 parts by weight, preferably 10 to 30 parts by weight, with respect to 100 parts by weight of the polyimide precursor. It is preferable to blend with
Two or more kinds of such photosensitizers may be contained.

A photoacid generator is a compound that generates an acid upon irradiation with light such as ultraviolet light or visible light. Salts, aromatic tetracarboxylic acid esters, aromatic sulfonic acid esters, nitrobenzyl esters, aromatic N-oximidosulfonates, aromatic sulfamides and benzoquinone diazosulfonic acid esters can be mentioned.
Among the above, naphthoquinonediazide compounds are preferred from the viewpoint of dissolution contrast.
Specific examples of the naphthoquinonediazide compound include, for example, tris(4-hydroxyphenyl)-1-ethyl-4-isopropylbenzene naphthoquinonediazide adducts (for example, TS533, TS567, TS583, TS593), naphthoquinonediazide adducts of tetrahydroxybenzophenone (for example, BS550, BS570, BS599 from Sambo Kagaku Kenkyusho Co., Ltd.), and 4-{4-[1,1-bis(4-hydroxyphenyl)ethyl]-α ,α-dimethylbenzyl}phenol naphthoquinonediazide adducts (eg, TKF-428 and TKF-528 manufactured by Sambo Kagaku Kenkyusho Co., Ltd.).

Photopolymerization initiators are compounds that generate radicals and the like upon irradiation with light such as ultraviolet rays and visible light. Phosphine oxide-based photopolymerization initiators and titanocene-based photopolymerization initiators are included.
Examples of commercially available oxime ester photopolymerization initiators include Irgacure OXE01 and Irgacure OXE02 manufactured by BASF Japan, N-1919 and NCI-831 manufactured by ADEKA.
Specific examples of α-aminoacetophenone-based photopolymerization initiators include 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropanone-1, 2-benzyl-2-dimethylamino-1 -(4-morpholinophenyl)-butan-1-one, 2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-[4-(4-morpholinyl)phenyl]-1-butanone and and N,N-dimethylaminoacetophenone, commercially available products of which include Omnirad 907, Omnirad 369 and Omnirad 379 manufactured by IGM Resins.
Specific examples of acylphosphine oxide photopolymerization initiators include 2,4,6-trimethylbenzoyldiphenylphosphine oxide, bis(2,4,6-trimethylbenzoyl)-phenylphosphine oxide and bis(2,6- dimethoxybenzoyl)-2,4,4-trimethyl-pentylphosphine oxide, and the like, and commercially available products thereof include Omnirad TPO manufactured by IGM Resins and Omnirad 819 manufactured by IGM Resins. be able to.
Specific examples of titanocene-based photopolymerization initiators include bis(cyclopentadienyl)-di-phenyl-titanium, bis(cyclopentadienyl)-di-chloro-titanium, bis(cyclopentadienyl)- bis(2,3,4,5,6 pentafluorophenyl) titanium and bis(cyclopentadienyl)-bis(2,6-difluoro-3-(pyrrol-1-yl)phenyl) titanium, Commercially available products include Omnirad 784 manufactured by IGM Resins.

Photobase generators generate one or more basic substances (secondary amines, tertiary amines, etc.) by changing the molecular structure or by cleaving the molecules when irradiated with light such as ultraviolet rays or visible light. It is a compound that
The photobase generator may be an ionic photobase generator or a nonionic photobase generator, but from the viewpoint of the sensitivity of the photosensitive resin composition, the ionic photobase generator is preferred.
Examples of the ion-type photobase generator include salts of carboxylic acids containing aromatic components and tertiary amines. 167, WPBG-168, WPBG-266 and WPBG-300.
Examples of nonionic photobase generators include α-aminoacetophenone compounds, oxime ester compounds, N-formylated aromatic amino groups, N-acylated aromatic amino groups, nitrobenzyl carbamate groups and alkoxybenzyls. A compound having a substituent such as a carbamate group is included.
As other photobase generators, Wako Pure Chemical Industries, Ltd. WPBG-018 (trade name: 9-anthrylmethyl N, N'-diethylcarbamate), WPBG-027 (trade name: (E)-1-[3-(2 -hydroxyphenyl)-2-propenoyl]piperidine), WPBG-140 (trade name: 1-(anthraquinon-2-yl)ethyl imidazolecarboxylate) and WPBG-165.

[Other ingredients]
To the photosensitive resin composition of the present invention, as long as the effects of the present invention are not impaired, a known sensitizer for further improving photosensitivity, a silane coupling agent for improving adhesiveness with a substrate, etc. A known adhesion agent or the like may be blended.
Moreover, you may mix|blend polyimide precursors other than the polyimide precursor represented by General formula (1) to the photosensitive resin composition of this invention in the range which does not impair the effect of this invention.
Furthermore, various organic or inorganic low-molecular-weight or high-molecular-weight compounds may be added to the photosensitive resin composition of the present invention in order to impart processing characteristics and various functionalities, such as surfactants. , leveling agents, plasticizers, fine particles, and the like can be used. Fine particles include organic fine particles such as polystyrene and polytetrafluoroethylene, and inorganic fine particles such as colloidal silica, carbon, and layered silicate. Further, various coloring agents and fibers may be added to the photosensitive resin composition of the present invention.

[solvent]
The photosensitive resin composition of the present invention may contain a solvent. The solvent is not particularly limited as long as it can dissolve each of the above components. Examples include N,N'-dimethylformamide, N-methylpyrrolidone, N-ethyl-2-pyrrolidone, N,N'-dimethylacetamide, Diethylene glycol dimethyl ether, cyclopentanone, γ-butyrolactone, α-acetyl-γ-butyrolactone, tetramethylurea, 1,3-dimethyl-2-imidazolinone, N-cyclohexyl-2-pyrrolidone, dimethylsulfoxide, hexamethylphosphoramide , pyridine, γ-butyrolactone and diethylene glycol monomethyl ether.

The content of the solvent in the photosensitive resin composition is not particularly limited, and it is preferable to change it as appropriate according to its application. It can be 50 parts by mass or more and 9000 parts by mass or less.
In addition, the photosensitive resin composition may contain two or more solvents.

[Dry film]
The dry film of the present invention comprises a film (for example, a support (carrier) film) and a resin layer formed on the film using the photosensitive resin composition. The dry film may further include a protective film (so-called protective film) on the resin layer formed on the film.

[the film]
The film is not particularly limited, and for example, films made of thermoplastic resins such as polyester films such as polyethylene terephthalate and polyethylene naphthalate, polyimide films, polyamideimide films, polypropylene films, and polystyrene films can be used. can.
Among these, polyethylene terephthalate is preferable from the viewpoint of heat resistance, mechanical strength, handleability, and the like. A laminate of these films can also be used as a film.

From the viewpoint of improving mechanical strength, the thermoplastic resin film as described above is preferably a uniaxially or biaxially stretched film.

Although the thickness of the film is not particularly limited, it can be, for example, 10 to 150 μm.

[Resin layer]
The resin layer is formed using the photosensitive resin composition described above, and the thickness thereof is not particularly limited, and is preferably changed according to the application. can be:

The resin layer is coated on the film with a photosensitive resin composition to a uniform thickness using a comma coater, blade coater, lip coater, rod coater, squeeze coater, reverse coater, transfer roll coater, gravure coater, spray coater, or the like. It can be formed by coating and drying.
In another embodiment, the resin layer can be formed by applying a photosensitive resin composition on the protective film and drying it.

[Protective film]
In the present invention, it is preferable to laminate a peelable protective film on the surface of the resin layer for the purpose of preventing dust from adhering to the surface of the resin layer.

The peelable protective film is not particularly limited as long as the adhesive force between the resin layer and the protective film becomes smaller than the adhesive force between the resin layer and the film when the protective film is peeled off. For example, polyethylene film, polytetrafluoroethylene film, polypropylene film and surface-treated paper can be used.

Although the thickness of the protective film is not particularly limited, it can be, for example, 10 μm or more and 150 μm or less.

[Cured product]
The cured product of the present invention is characterized by being formed using the above photosensitive resin composition. Moreover, the cured product may be one in which a pattern is formed (hereinafter sometimes referred to as a pattern film).
The method for producing the cured product of the present invention is described below.

[First step]
In the method for producing a cured product of the present invention, a photosensitive resin composition is applied on a substrate to form a coating film, and then dried, or the resin layer is transferred from the dry film onto the substrate. This includes a step of forming a dry coating film.

The method of applying the photosensitive resin composition onto the substrate is not particularly limited, and for example, a method of applying using a spin coater, a bar coater, a blade coater, a curtain coater, a screen printer, etc., or a method of spraying with a spray coater. and an inkjet method.

As a method for drying the coating film, methods such as air drying, heat drying using an oven or a hot plate, and vacuum drying are used.
Moreover, it is desirable to dry the coating film under conditions that do not cause ring closure of the polyimide precursor in the photosensitive resin composition.
Specifically, natural drying, air drying, or heat drying is preferably carried out at 70 to 140° C. for 1 to 30 minutes. Moreover, since the operation method is simple, it is preferable to use a hot plate for drying for 1 to 20 minutes.
Vacuum drying is also possible, and in this case, it can be carried out at room temperature for 20 minutes to 1 hour.

The transfer of the dry film onto the substrate is preferably carried out under pressure and heat using a vacuum laminator or the like. By using such a vacuum laminator, even if the circuit board surface has irregularities, the resin layer of the dry film fills the irregularities of the circuit board under vacuum conditions. , there is no entrapment of air bubbles, and the filling of recesses on the substrate surface is improved.

As a base material, in addition to printed wiring boards and flexible printed wiring boards on which circuits are formed in advance with copper etc., paper phenol, paper epoxy, glass cloth epoxy, glass polyimide, glass cloth/non-woven cloth epoxy, glass cloth/paper epoxy, Copper-clad laminates of all grades (FR-4, etc.) using materials such as copper-clad laminates for high-frequency circuits using synthetic fiber epoxy, fluororesin, polyethylene, polyphenylene ether, polyphenylene oxide, cyanate, etc. , metal substrates, polyimide films, polyethylene terephthalate films, polyethylene naphthalate (PEN) films, glass substrates, ceramic substrates, wafer plates and the like.

[Second step]
Next, the coating film is exposed to active energy rays selectively through a photomask having a pattern or non-selectively through a photomask.

The active energy ray used has a wavelength capable of activating, for example, the photoacid generator as the photosensitizer (B). Specifically, the active energy ray preferably has a maximum wavelength in the range of 350 to 410 nm.
The amount of exposure varies depending on the film thickness, etc., but can generally be in the range of 10 to 1000 mJ/cm ² , preferably 20 to 800 mJ/cm ² .
The exposure machine used for the active energy ray irradiation may be a device equipped with a high-pressure mercury lamp, an ultra-high pressure mercury lamp, a metal halide lamp, a mercury short arc lamp, etc., and irradiating ultraviolet rays in the range of 350 to 450 nm. In addition, a direct writing device (eg, a laser direct imaging device that draws an image with a laser directly from CAD data from a computer) can also be used.

[Third step]
This step is carried out as necessary, and a portion of the polyimide precursor in the unexposed area may be ring-closed by heating the coating film for a short period of time. Here, the ring closure rate is about 30%. The heating time and heating temperature are appropriately changed depending on the type of polyimide precursor, coating film thickness, and (B) the type of photosensitive agent.

[Fourth step]
Then, the patterned film can be obtained by treating the exposed coating film with a developer to remove the exposed portions in the coating film.
In this step, any method can be selected from conventionally known photoresist development methods, such as the rotary spray method, the paddle method, and the immersion method accompanied by ultrasonic treatment.

Examples of the developer include inorganic alkalis such as sodium hydroxide, sodium carbonate, sodium silicate and aqueous ammonia; organic amines such as ethylamine, diethylamine, triethylamine and triethanolamine; tetramethylammonium hydroxide and tetrabutylammonium hydroxide. and aqueous solutions of quaternary ammonium salts such as
If necessary, a suitable amount of a water-soluble organic solvent such as methanol, ethanol or isopropyl alcohol or a surfactant may be added.

After that, the coating film is washed with a rinsing liquid as necessary to obtain a pattern film.
Distilled water, methanol, ethanol, isopropyl alcohol, and the like can be used alone or in combination as the rinsing liquid. Moreover, you may use the said solvent as a developer.

[Fifth step]
Next, the pattern film is heated to obtain a cured coating film (cured product).
Through the heating step, the ester group-containing polyimide precursor contained in the photosensitive resin composition is ring-closed to form a polyimide.

The heating conditions are preferably adjusted as appropriate, and can be set, for example, at a temperature of 150° C. or more and less than 300° C. for about 5 minutes to 120 minutes.
For heating, for example, a hot plate, an oven, and a temperature-programmable oven can be used.
It may be in a heated atmosphere (gas), in air, or in an inert gas such as nitrogen or argon.

[Use]
Applications of the photosensitive resin composition of the present invention are not particularly limited.

Specifically, materials for forming display devices include layer-forming materials and image-forming materials for color filters, films for flexible displays, resist materials, alignment films, and the like.
Materials for forming semiconductor elements include resist materials, buffer coat films, and layer forming materials for insulating films for rewiring layers of wafer level packages (WLP).
Materials for forming electronic components include sealing materials and layer-forming materials for printed wiring boards, interlayer insulating films, wiring coating films, and the like.
Materials for forming optical components include optical materials and layer-forming materials for holograms, optical waveguides, optical circuits, optical circuit components, antireflection films, and the like.
Furthermore, as building materials, it can be used for paints, coating agents, and the like.

INDUSTRIAL APPLICABILITY The photosensitive resin composition of the present invention is mainly used as a pattern forming material, and is used particularly for surface protective films, buffer coat films, interlayer insulating films, rewiring insulating films, and flip chips of semiconductor devices, display devices and light emitting devices. Appropriate as protective films for devices, protective films for devices having a bump structure, interlayer insulating films for multilayer circuits, insulating materials for passive components, protective films for printed wiring boards such as solder resists and coverlay films, and liquid crystal alignment films. Available.

EXAMPLES The present invention will be described in more detail below using examples, but the present invention is not limited to the examples. In the following description, "parts" and "%" are based on mass unless otherwise specified.

(Reference Example 1: Synthesis of ester group-containing polyimide precursor A)
A 0.1-liter flask equipped with a stirrer and a thermometer was charged with 40 g of N-methylpyrrolidone, and 15.00 g of (2-phenyl-4-aminophenyl)-4-aminobenzoate represented by the following chemical formula (7). mmol was dissolved with stirring.
After that, 13.70 mmol of biphenyl-3,4,3′,4′-tetracarboxylic dianhydride represented by the following chemical formula (8) was added as a solid in 0.5 g portions over 30 minutes. Stirring was continued for hours to obtain a varnish of an ester group-containing polyimide precursor A represented by the following chemical formula (9). The number average molecular weight (Mn) of the ester group-containing polyimide precursor A was 10,752, the weight average molecular weight (Mw) was 24,622, and Mw/Mn was 2.29.

(Reference Example 2: Synthesis of ester group-containing polyimide precursor B)
A 0.1-liter flask equipped with a stirrer and a thermometer was charged with 40 g of N-methylpyrrolidone, and 15.00 g of (2-phenyl-4-aminophenyl)-4-aminobenzoate represented by the above chemical formula (7) was added. mmol was dissolved with stirring. Thereafter, 13.72 mmol of oxydiphthalic dianhydride represented by the following chemical formula (10) was added as a solid in 0.5 g portions over 30 minutes, and the mixture was stirred at room temperature for 16 hours. A varnish of ester group-containing polyimide precursor B was obtained. The number average molecular weight (Mn) of the ester group-containing polyimide precursor B was 10,293, the weight average molecular weight (Mw) was 25,115, and Mw/Mn was 2.44.

(Reference Example 3: Synthesis of polyimide precursor a)
A 0.1-liter flask equipped with a stirrer and a thermometer was charged with 40 g of N-methylpyrrolidone, and 15.00 mmol of 4,4'-diaminodiphenyl ether represented by the following chemical formula (12) was stirred and dissolved. After that, 13.69 mmol of oxydiphthalic dianhydride represented by the above chemical formula (10) was added in 0.5 g portion over 30 minutes as a solid, and the stirring was continued at room temperature for 16 hours. A varnish of polyimide precursor a was obtained. The polyimide precursor a had a number average molecular weight (Mn) of 10,475, a weight average molecular weight (Mw) of 25,035, and Mw/Mn of 2.39.

<Example 1>
The ester group-containing polyimide precursor A obtained in Reference Example 1 above, a photosensitive agent, and a silane coupling agent having an arylamino group were mixed according to the following composition to obtain a photosensitive resin composition.
(Photosensitive resin composition composition)
・ Ester group-containing polyimide precursor A 100 parts by mass ・ Photosensitizer 20 parts by mass (TKF-525, naphthoquinone diazide compound, manufactured by Sambo Chemical Industry Co., Ltd.)
・ Silane coupling agent 5 parts by mass (manufactured by Shin-Etsu Silicone Co., Ltd., KBM-573)

<Example 2>
A photosensitive resin composition was obtained in the same manner as in Example 1, except that the ester group-containing polyimide precursor A was changed to the ester group-containing polyimide precursor B obtained in Reference Example 2 above.

<Comparative Example 1>
A photosensitive resin composition was obtained in the same manner as in Example 1, except that the ester group-containing polyimide precursor A was changed to the polyimide precursor a obtained in Reference Example 3 above.

<<Evaluation of linear thermal expansion coefficient and glass transition temperature>>
The photosensitive resin compositions obtained in the above Examples and Comparative Examples were applied onto a silicon substrate with a spin coater, and dried by heating at 120° C. for 4 minutes with a hot plate to form a dry coating film of the photosensitive resin composition. formed.
Next, the dried coating film formed on the silicon substrate was heated at 300° C. for 1 hour using a hot plate to obtain a cured film having a thickness of 30 μm.
After peeling off the cured film from the silicon substrate, it was cut into a test piece of 30 mm long×3 mm wide×30 μm thick.
The coefficient of linear thermal expansion of the test piece was measured using a thermomechanical analyzer (TMA'Q400, manufactured by TA Instruments Japan).
Specifically, after mounting the test piece on a thermomechanical analyzer, measurement was carried out from room temperature to 370° C. at a heating rate of 10° C./min under a nitrogen atmosphere (nitrogen flow rate: 100 mL/min).
Next, the average coefficient of linear thermal expansion in the range of 50°C to 200°C was calculated and evaluated according to the following evaluation criteria. The evaluation results are summarized in Table 1.
(Evaluation criteria)
A: The average coefficient of linear thermal expansion was less than 25 ppm/°C.
○: The average linear thermal expansion coefficient was 25 ppm/°C or more and less than 40 ppm/°C.
Δ: The average coefficient of linear thermal expansion was 40 ppm/°C or more and less than 55 ppm/°C.
x: The average coefficient of linear thermal expansion was less than 55 ppm/°C.

The maximum displacement point of the coefficient of linear thermal expansion in the measurement of the coefficient of linear thermal expansion was defined as the glass transition temperature, and evaluation was made according to the following evaluation criteria. The evaluation results are summarized in Table 1.
(Evaluation criteria)
A: The glass transition temperature was 340°C or higher.
○: The glass transition temperature was 320°C or more and less than 340°C.
Δ: The glass transition temperature was 300°C or more and less than 320°C.
x: The glass transition temperature was less than 300°C.

<<High temperature pattern maintenance evaluation>>
The photosensitive resin compositions obtained in the above Examples and Comparative Examples were applied onto a silicon substrate with a spin coater, and dried by heating at 120° C. for 4 minutes with a hot plate to form a dry coating film of the photosensitive resin composition. formed.
The dry coating film was irradiated with broad light through a patterned photomask using a high-pressure mercury lamp (with an i-line filter). Note that the exposure dose was 500 mJ/cm ² .
The dried coating film after exposure was developed using a 2.38% tetramethylammonium hydroxide (TMAH) aqueous solution and rinsed with water to form a positive rectangular pattern film.
The rectangular pattern film thus formed was heated at 300° C. for 1 hour with a hot plate.
The rectangular pattern film after heating was observed with an electron microscope (SEM "JSM-6010") and evaluated according to the following evaluation criteria. The evaluation results are summarized in Table 1. 1 is an image of the rectangular pattern film formed from the photosensitive resin composition of Example 1 after heating, and an image of the rectangular pattern film after heating formed from the photosensitive resin composition of Example 2 is shown in FIG. 2, and an image of the rectangular pattern film after heating formed from the photosensitive resin composition of Comparative Example 1 is attached as FIG.
(Evaluation criteria)
◯: No change in shape was observed in the rectangular pattern film.
x: In the rectangular pattern film, the corners were rounded or the shape was changed.

<<Evaluation of i-line transmittance>>
The photosensitive resin compositions obtained in the above Examples and Comparative Examples were applied onto quartz glass and dried by heating at 120° C. for 4 minutes using a hot plate to form a dry coating film of the photosensitive resin composition.
The dried coating film was irradiated with broad light using a high-pressure mercury lamp (with an i-line filter). The exposure amount was set to 1000 mJ/cm ² .
The transmission spectrum of the dried coating film after exposure was measured using an ultraviolet-visible spectrophotometer (Jasco V-570, manufactured by JASCO Corporation), and the measured value was normalized to a film thickness of 5 μm. The transmission spectrum was measured under the conditions of a bandwidth of 5 nm, a scanning speed of 400 nm/min, and a data reading interval of 1 nm.
The transmittance of i-line (wavelength: 365 nm), which is the exposure wavelength, was evaluated according to the following evaluation criteria. The evaluation results are summarized in Table 1.
(Evaluation criteria)
A: The i-line transmittance was 80% or more.
Good: The i-line transmittance was 60% or more and less than 80%.
x: The i-line transmittance was less than 60%.

<<Sensitivity Evaluation>>
The photosensitive resin compositions obtained in the above Examples and Comparative Examples were applied onto a silicon substrate with a spin coater, and dried by heating at 120° C. for 4 minutes with a hot plate to form a dry coating film of the photosensitive resin composition. formed.
The dry coating film was irradiated with broad light through a patterned photomask using a high-pressure mercury lamp (with an i-line filter). The exposure amount was increased by 25 mJ/cm ² in the range of 0 to 500 mJ/cm ² after passing through the photomask.
The dried coating film after exposure was developed using a 2.38% TMAH aqueous solution and rinsed with water to form a positive pattern film.
The amount of exposure at which the exposed portion was completely eluted was defined as the minimum amount of exposure, and evaluation was made according to the following evaluation criteria. The evaluation results are summarized in Table 1.
(Evaluation criteria)
A: The minimum exposure dose was less than 250 mJ/cm ² .
○: The minimum exposure dose was 250 mJ/cm ² or more and less than 500 mJ/cm ² .
x: The minimum exposure amount was 500 mJ/cm ² or more.

<<Dissolution contrast evaluation>>
The photosensitive resin compositions obtained in the above Examples and Comparative Examples were applied onto a silicon substrate and heated at 120° C. for 4 minutes using a hot plate to form a dry coating film.
The dry coating film was irradiated with broad light through a patterned photomask using a high-pressure mercury lamp (with an i-line filter). Note that the exposure dose was 500 mJ/cm ² .
The dried coating film after exposure is developed using a 2.38% TMAH aqueous solution at 25° C., and exposed and unexposed areas are measured using a development rate measuring device (RDA-790 manufactured by Litho Tech Japan Co., Ltd.). The dissolution rate of the dried coating film in parts was measured.
The dissolution rate (μm/min)=reduced film thickness (μm)/development time (min). In the formula, the reduced film thickness means the difference in the thickness of the dry coating film before and after development, and the development time means the time during which the dry coating film is immersed in the aqueous TMAH solution.

The ratio of the dissolution rate of the exposed area to the dissolution rate of the unexposed area (dissolution rate of unexposed area/dissolution rate of exposed area) was calculated and evaluated according to the following evaluation criteria. The evaluation results are summarized in Table 1.
(Evaluation criteria)
A: The dissolution rate ratio was 7 or more.
○: The dissolution rate ratio was 3 or more and less than 7.
x: The dissolution rate ratio was less than 3.

As is clear from the evaluation results shown in the table above, each example was confirmed to have high dissolution contrast, high-temperature pattern retention and sensitivity, and a low coefficient of linear thermal expansion.

Claims (6)

(A) at least one of ester group-containing polyimide precursors represented by the following general formulas (1) and (2);
(B) a photosensitive resin composition, comprising:

(In general formulas (1) and (2),
X is a tetravalent organic group,
R ₁ and R ₂ are each independently selected from a hydrogen atom, a silyl group and a monovalent organic group having 1 to 20 carbon atoms,
any one of R ₃ to R ₆ is selected from an aromatic group having 6 to 10 carbon atoms , a phenoxy group having 6 to 10 carbon atoms, a benzyl group having 6 to 10 carbon atoms and a benzyloxy group having 6 to 10 carbon atoms; , and the other R ₃ to R ₆ are hydrogen atoms,
n represents an integer of 1 or more. ) Either R ₃ or R ₅ is selected from an aromatic group having 6 to 10 carbon atoms , a phenoxy group having 6 to 10 carbon atoms, a benzyl group having 6 to 10 carbon atoms and a benzyloxy group having 6 to 10 carbon atoms. , the other is a hydrogen atom, and
The photosensitive resin composition according to claim 1, wherein _R4 and _R6 are hydrogen atoms. 3. The photosensitive resin composition according to claim 1, wherein the photosensitive agent is a naphthoquinonediazide compound. A dry film comprising a resin layer formed from the photosensitive resin composition according to any one of claims 1 to 3 on the film. A cured product characterized by being formed from the photosensitive resin composition according to any one of claims 1 to 3 or the resin layer of the dry film according to claim 4. An electronic component comprising the cured product according to claim 5 as a forming material.

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