JP7703000B2 - Polymers, photosensitive compositions, dry film photoresists, and methods of lithography - Google Patents

Description

This technical field relates to polymers, and more particularly to the application of polymers to photosensitive compositions.

Photoresists used in lithography processes are generally divided into positive photoresists and negative photoresists. Most positive photoresists are applied using a wet process and developed using tetramethylammonium hydroxide (TMAH) solution, and cannot be used in printed circuit board (PCB) processes. Negative photoresists can be made into dry film photoresists and developed using sodium carbonate solution. Thus, negative photoresists can be used in PCB processes, but the resolution after development is poor.

U.S. Patent No. 6,783,828 B2 Taiwan Patent No. I396043B Specification

New photoresist compositions are needed to form positive photoresists that can be developed using sodium carbonate solutions for use in PCB processes.

One embodiment of the present disclosure provides a polymer formed by reacting a phenolic or bisphenolic epoxy resin with a carboxylic acid. The phenolic epoxy resin has the following chemical structure:

であり、ｎ＝１から８である。 In the formula, W is H, an alkyl group, or a halogen; R ¹ is methylene, dimethylenediphenyl, dimethylenebenzene, tetrahydrodicyclopentadiene, or

where n=1 to 8.

Bisphenol-type epoxy resin has the following chemical structure:

wherein Z is H or an alkyl group, R ⁴ is methylene, methylmethylene, dimethylmethylene, ethylmethylmethylene, bi(trifluoromethyl)methylene, fluorenylidene, or a sulfonyl group, and p=1 to 10.

Carboxylic acids have one of the following chemical structures or a combination of these:

wherein Ar is benzene or naphthalene, X is a hydroxy group, an alkoxy group, or an alkyl group, and at least one X is a hydroxy group, and m=1 to 3. ^R2 is a _C3-7 alkyl group.

One embodiment of the present disclosure provides a photosensitive composition comprising 100 parts by weight of a polymer and 15 to 90 parts by weight of a photosensitive compound.

One embodiment of the present disclosure provides a dry film photoresist including a photosensitive film interposed between a support film and a protective film, the photosensitive film including a photosensitive composition.

One embodiment of the present disclosure provides a method of lithography that includes the steps of: providing a material layer; forming a photoresist layer on the material layer, the photoresist layer including a photosensitive composition; exposing the photoresist layer such that the photoresist layer has exposed and unexposed portions; and developing the photoresist layer with an alkaline solution to remove the exposed portions of the photoresist layer while leaving the unexposed portions of the photoresist layer, thereby exposing a portion of the material layer.

The positive photoresist of the present disclosure can be developed in a sodium carbonate solution and can be used in PCB processes.

A detailed explanation is given in the following embodiments.

In the following detailed description, for purposes of explanation, numerous specific details are set forth in order to provide a more thorough understanding of the disclosed embodiments. However, it will be apparent that one or more embodiments may be practiced without these specific details.

One embodiment of the present disclosure provides a polymer formed by reacting a phenolic or bisphenolic epoxy resin with a carboxylic acid. The phenolic epoxy resin has the following chemical structure:

）、ジメチレンベンゼン（

）、テトラヒドロジシクロペンタジエン（

）、または

であり、ｎ＝１から８である。ｎが大きすぎると、ポリマーを含む感光性組成物の溶解度および現像解像度が低下してしまう。ビスフェノール型エポキシ樹脂は次の化学構造を有する。 In the formula, W is H, an alkyl group, or a halogen. R ¹ is methylene (-CH ₂ -), dimethylene diphenyl (

), dimethylenebenzene (

), tetrahydrodicyclopentadiene (

),or

and n=1 to 8. If n is too large, the solubility and development resolution of the photosensitive composition containing the polymer decrease. The bisphenol type epoxy resin has the following chemical structure:

）、またはスルホニル基（－ＳＯ₂－）である。ｐ＝１から１０である。ｐが大きすぎると、ポリマーを含む感光性組成物の溶解度および現像解像度が低下してしまう。カルボン酸は次の化学構造のいずれか、またはこれらの組み合わせを有する。 In the formula, Z is H or an alkyl group. ^R4 is methylene, methylmethylene (-CH( _CH3 )-), dimethylmethylene (-C( _CH3 ) _2- ), ethylmethylmethylene (-C( _CH3 ) _{( C2H5} )-), bi(trifluoromethyl)methylene (-C( _CF3 ) _2- ), fluorenylidene (

), or a sulfonyl group (-SO ₂ -). p=1 to 10. If p is too large, the solubility and development resolution of the photosensitive composition containing the polymer decrease. Carboxylic acids have any of the following chemical structures or a combination thereof:

Ar is benzene or naphthalene. X is a hydroxy group, an alkoxy group, or an alkyl group, at least one X is a hydroxy group, m=1 to 3, and ^R2 is a _C3-7 alkyl group. If Ar does not have a hydroxy group, the image on the mask cannot be transferred to a polymer used as a positive dry film photoresist. If the carbon number of ^R2 is too small or too large, the image on the mask cannot be transferred to a polymer used as a positive dry film photoresist.

In some embodiments, the phenolic epoxy resin is a cresol-based phenolic epoxy resin, a biscresol-based phenolic epoxy resin, a tricresol-based phenolic epoxy resin, or a combination thereof. In some embodiments, the bisphenol-based epoxy resin is a bisphenol A epoxy resin, a bisphenol E epoxy resin, a bisphenol F epoxy resin, a bisphenol B epoxy resin, a bisphenol AF epoxy resin, a bisphenol S epoxy resin, or a combination thereof. In some embodiments, the carboxylic acid is a hydroxy aromatic acid, such as hydroxybenzoic acid, dihydroxybenzoic acid, trihydroxybenzoic acid, hydroxynaphthoic acid, or a combination thereof.

In some embodiments, the polymer has one of the following chemical structures:

であり、Ｒ¹²はメチレン、ジメチレンジフェニル、ジメチレンベンゼン、テトラヒドロジシクロペンタジエン、または

であり、Ｒ¹³はメチレン、 ジメチレンジフェニル、ジメチレンベンゼン、テトラヒドロジシクロペンタジエン、または

である。 In the formula, R ¹¹ is methylene, dimethylenediphenyl, dimethylenebenzene, tetrahydrodicyclopentadiene, or

and R ¹² is methylene, dimethylenediphenyl, dimethylenebenzene, tetrahydrodicyclopentadiene, or

and R ¹³ is methylene, dimethylenediphenyl, dimethylenebenzene, tetrahydrodicyclopentadiene, or

It is.

In some embodiments, the polymer is further reacted with an anhydride to form a modified polymer. The anhydride has the following chemical structure:

またはこれらの組み合わせであり、かつ変性ポリマーの酸価は０から１００ｍｇ ＫＯＨ／ｇである。変性ポリマーの酸価が高すぎると、感光性組成物が現像に耐えられないものとなってしまう。いくつかの実施形態において、無水物はヘキサヒドロ無水フタル酸、テトラヒドロ無水フタル酸、無水フタル酸またはこれらの組み合わせである。いくつかの実施形態において、ポリマーまたは変性ポリマーの重量平均分子量は２０００から５００００である。ポリマーまたは変性ポリマーの重量平均分子量が低すぎると、感光性組成物をフィルムに形成できなくなってしまう。 In the formula, Y is

or a combination thereof, and the acid value of the modified polymer is 0 to 100 mg KOH/g. If the acid value of the modified polymer is too high, the photosensitive composition cannot withstand development. In some embodiments, the anhydride is hexahydrophthalic anhydride, tetrahydrophthalic anhydride, phthalic anhydride, or a combination thereof. In some embodiments, the weight average molecular weight of the polymer or modified polymer is 2,000 to 50,000. If the weight average molecular weight of the polymer or modified polymer is too low, the photosensitive composition cannot be formed into a film.

In some embodiments, the modified polymer has one of the following chemical structures:

であり、Ｒ²²はメチレン、ジメチレンジフェニル、ジメチレンベンゼン、テトラヒドロジシクロペンタジエン、または

であり、Ｒ²³はメチレン、ジメチレンジフェニル、ジメチレンベンゼン、テトラヒドロジシクロペンタジエン、または

であり、Ｒ³は

である。
In the formula, R ²¹ is methylene, dimethylenediphenyl, dimethylenebenzene, tetrahydrodicyclopentadiene, or

R ²² is methylene, dimethylenediphenyl, dimethylenebenzene, tetrahydrodicyclopentadiene, or

R ²³ is methylene, dimethylenediphenyl, dimethylenebenzene, tetrahydrodicyclopentadiene, or

and ^R3 is

It is.

One embodiment of the present disclosure provides a photosensitive composition comprising 100 parts by weight of a polymer and 15 to 90 parts by weight of a photosensitive compound. If the amount of the photosensitive compound is too low, the photosensitive composition will not be sufficiently photosensitive and will not withstand development. If the amount of the photosensitive compound is too high, the solubility and developability of the photosensitive composition will be poor. In some embodiments, the photosensitive compound comprises a diazonaphthoquinone-based compound.

In some embodiments, the photosensitive composition further comprises 200 to 1000 parts by weight of a solvent. If the amount of solvent is too small, the polymer and the photosensitive compound may not be uniformly dispersed in the solvent, and the composition of the photoresist layer (formed by applying and drying the photosensitive composition) may be non-uniform. If the amount of solvent is too large, the cost of subsequent solvent removal increases and it becomes difficult to form a thick photoresist layer. In some embodiments, the solvent comprises propylene glycol monomethyl ether acetate, n-butyl acetate, ethyl acetate, gamma-butyrolactone, cyclohexanone, or a combination thereof.

In some embodiments, the photosensitive composition may further include 40 to 200 parts by weight of a phenolic resin. The phenolic resin may be cresol, bis-cresol, tricresol, or a combination thereof. If the amount of phenolic resin is too high, the developability of the photosensitive composition may be poor. The weight average molecular weight of the phenolic resin may be 5,000 to 50,000. If the weight average molecular weight of the phenolic resin is too low, the photosensitive composition may not be able to be formed into a film. If the weight average molecular weight of the phenolic resin is too high, the photosensitive composition may not be able to be developed.

One embodiment of the present disclosure provides a dry film photoresist including a photosensitive film interposed between a support film and a protective film, the photosensitive film including a photosensitive composition. The release force of the support film is 150 g to 500 g, and the release force of the protective film is 1 g to 100 g. In some embodiments, the thickness of the photosensitive film can be 6 micrometers to 18 micrometers, depending on the thickness required for the photoresist layer in the actual lithography process.

For example, a solution of a photosensitive composition can be applied to a support film and dried, and a protective film can be applied to the dried photosensitive composition (photosensitive film), forming a positive dry film photoresist. In a transfer process, the protective film is peeled off and the dried photosensitive composition (photosensitive film) is applied to a material layer, such as a wafer or copper-clad laminate. A heated roller is used to apply pressure to the support film to transfer the dried photosensitive composition (photosensitive film) onto the material layer. The support film is then peeled off and a subsequent exposure and development process is performed.

One embodiment of the present disclosure provides a method of lithography, comprising preparing a material layer and forming a photoresist layer on the material layer, the photoresist layer comprising a photosensitive composition. The method of forming the photoresist layer can be wet coating or transfer of a photoresist film in the positive dry film photoresist onto the material layer. The photoresist layer is exposed to light so that the photoresist layer has exposed and unexposed portions. The photoresist layer is developed with an alkaline solution to expose a portion of the material layer by removing the exposed portions of the photoresist layer while leaving the unexposed portions of the photoresist layer. In some embodiments, the alkaline solution is a sodium carbonate solution, a sodium hydroxide solution, a potassium hydroxide solution, or a combination thereof. It is noted that prior to the present disclosure, there was no positive dry film photoresist that could be developed with a sodium carbonate solution. In some embodiments, the method further comprises etching the exposed portions of the material layer, implanting the exposed portions of the material layer, or depositing another material layer on the exposed portions of the material layer. For example, the material layer may be a substrate material, or a conductive, dielectric, or semiconducting layer formed on a substrate.

Below, exemplary embodiments are described in detail so that those of ordinary skill in the art can easily understand. The concept of the present invention may be embodied in various forms without being limited to the exemplary embodiments shown herein. For clarity, descriptions of well-known parts are omitted, and similar reference numerals refer to similar components throughout.

In the following examples, the phenolic epoxy resin was commercially available from Nippon Kayaku. The bisphenolic epoxy resin was EPON 828 (commercially available from Shell Chemical). The catalyst was chromium(III) acetylacetonate-triphenyl phosphite. The inhibitor was hydroquinone (abbreviated as HQ). The weight average molecular weight of the polymer was measured by GPC, and the standard was polystyrene. The photosensitive compound was 2,3,4-trihydroxybenzophenone naphthoquinone-1,2-diazide-5 sulfonate (abbreviated as DNQ).

To form the positive dry film photoresist, the support film was a PET film (commercially available from Nanya Plastics Co. or Shinkong Synthetic Fibers Co.) with a release force of 300 g, and the protective film was a PET film (commercially available from Nanya Plastics Co. or Shinkong Synthetic Fibers Co.) with a release force of 30 g. The solution of the photosensitive composition was applied to the support film and then dried to form a photosensitive film (i.e., a dried photosensitive composition). The protective film was then attached to the photosensitive film to form the positive dry film photoresist. In the transfer process, the protective film was peeled off, the photosensitive film was attached to the wafer, and a pressure of 2.5 kg/ ^cm2 was applied to the support film by a roller at 95°C to ensure that the photosensitive film was transferred to the wafer. The support film was then peeled off to carry out the subsequent exposure and development processes.

Example 1
24.4 g of phenolic epoxy resin EPPN-502H (commercially available from Nippon Kayaku), 20.1 g of 4-hydroxybenzoic acid (4-HBA), 0.13 g of catalyst, 0.04 g of HQ, and 47 g of propylene glycol monomethyl ether acetate (PGMEA) were mixed in a reaction bottle. The mixture was heated to 140° C. and reacted with stirring for 7 hours to form a polymer. 8.3 g of hexahydrophthalic anhydride was then added to the reaction bottle and reacted with stirring for 3 hours to form a modified polymer. The acid value of the modified polymer was 83 mg KOH/g and the weight average molecular weight was 6500. The phenolic epoxy resin EPPN-502H has the following chemical structure:

n=1 to 3.

23 parts by weight of the modified polymer, 6.9 parts by weight of DNQ, and 70.1 parts by weight of a solvent (PGMEA and n-butyl acetate (BA), v/v=9/1) were mixed, and the solubility of DNQ was good (no precipitate was observed by visual inspection). The solution of the photosensitive composition was made into a positive dry film photoresist, which was then transferred onto a wafer to form a photoresist layer. The photoresist layer was exposed to ghi radiation (exposure dose 100 mJ/ ^cm2 ) and developed with 1% sodium carbonate solution for 20 to 40 seconds. This resulted in a pattern with a resolution of 8 micrometers.

Example 2
25.0 g of phenolic epoxy resin EPPN-502H, 20.6 g of 4-HBA, 0.14 g of catalyst, 0.04 g of HQ, and 48 g of PGMEA were mixed in a reaction bottle. The mixture was heated to 140° C. and reacted with stirring for 7 hours to form a polymer. 6.2 g of hexahydrophthalic anhydride was then added to the reaction bottle and reacted with stirring for 3 hours to form a modified polymer. The acid value of the modified polymer was 58 mg KOH/g and the weight average molecular weight was 5200.

23 parts by weight of modified polymer, 6.9 parts by weight of DNQ, and 70.1 parts by weight of solvent (PGMEA and BA, v/v=9/1) were mixed, and the solubility of DNQ was good (no precipitate was observed by visual inspection). The solution of the photosensitive composition was made into a positive dry film photoresist, which was then transferred onto a wafer to form a photoresist layer. The photoresist layer was exposed to ghi radiation (exposure dose 100 mJ/ ^cm2 ) and developed with 1% sodium carbonate solution for 30 to 50 seconds. This resulted in a pattern with a resolution of 8 micrometers.

Example 3
25.7 g of phenolic epoxy resin EPPN-502H, 21.2 g of 4-HBA, 0.14 g of catalyst, 0.04 g of HQ, and 49.4 g of PGMEA were mixed in a reaction bottle. The mixture was heated to 140° C. and reacted with stirring for 7 hours to form a polymer. 3.5 g of hexahydrophthalic anhydride was then added to the reaction bottle and reacted with stirring for 3 hours to form a modified polymer. The acid value of the modified polymer was 50 mg KOH/g and the weight average molecular weight was 5,300.

23 parts by weight of modified polymer, 8 parts by weight of DNQ, and 69 parts by weight of solvent (PGMEA and BA, v/v=9/1) were mixed, and the solubility of DNQ was good (no precipitate was observed by visual inspection). The solution of the photosensitive composition was made into a positive dry film photoresist, which was then transferred onto a wafer to form a photoresist layer. The photoresist layer was exposed to ghi radiation (exposure dose 100 mJ/ ^cm2 ) and developed with 1% sodium carbonate solution for 30 to 50 seconds. This resulted in a pattern with a resolution of 8 micrometers.

Example 4
30.0 g of phenolic epoxy resin EPPN-502H, 24.8 g of 4-HBA, 0.03 g of catalyst, 0.06 g of HQ, and 45 g of PGMEA were mixed in a reaction bottle. The mixture was heated to 140° C. and stirred for 7 hours to react and form a polymer. The acid value of the polymer was 27 mg KOH/g and the weight average molecular weight was 5700.

23 parts by weight of polymer, 6.9 parts by weight of DNQ, and 70.1 parts by weight of solvent (PGMEA and BA, v/v=9/1) were mixed, and DNQ had good solubility (no visible precipitate). The solution of the photosensitive composition was made into a positive dry film photoresist, which was then transferred onto a wafer to form a photoresist layer. The photoresist layer was exposed to ghi radiation (exposure dose 200 mJ/ ^cm2 ) and developed with 1% sodium carbonate solution for 40 to 60 seconds. This resulted in a pattern with a resolution of 8 micrometers.

Example 5
27.3 g of phenolic epoxy resin EPPN-502H, 22.5 g of 4-HBA, 0.14 g of catalyst, 0.04 g of HQ, and 50 g of PGMEA were mixed in a reaction bottle. The mixture was heated to 140° C. and stirred for 7 hours to react and form a polymer. The acid value of the polymer was 0 mg KOH/g and the weight average molecular weight was 5,500.

23 parts by weight of polymer, 6.0 parts by weight of DNQ, and 71 parts by weight of solvent (PGMEA and BA, v/v=9/1) were mixed, and DNQ had good solubility (no visible precipitate). The solution of the photosensitive composition was made into a positive dry film photoresist, which was then transferred onto a wafer to form a photoresist layer. The photoresist layer was exposed to ghi radiation (exposure dose 200 mJ/ ^cm2 ) and developed with 1% sodium carbonate solution for 30 to 50 seconds. This resulted in a pattern with a resolution of 8 micrometers.

Example 6
24.6 g of phenolic epoxy resin EPPN-502H, 20.3 g of 3-hydroxybenzoic acid (3-HBA), 0.13 g of catalyst, 0.04 g of HQ, and 45.2 g of PGMEA were mixed in a reaction bottle. The mixture was heated to 140° C. and reacted with stirring for 7 hours to form a polymer. 9.8 g of hexahydrophthalic anhydride was then added to the reaction bottle and reacted with stirring for 3 hours to form a modified polymer. The acid value of the modified polymer was 80 mg KOH/g and the weight average molecular weight was 2900.

23 parts by weight of modified polymer, 6.0 parts by weight of DNQ, and 71 parts by weight of solvent (PGMEA and BA, v/v=9/1) were mixed, and the solubility of DNQ was good (no precipitate was observed by visual inspection). The solution of the photosensitive composition was made into a positive dry film photoresist, which was then transferred onto a wafer to form a photoresist layer. The photoresist layer was exposed to ghi radiation (exposure dose 100 mJ/ ^cm2 ) and developed with 1% sodium carbonate solution for 20 to 40 seconds. This resulted in a pattern with a resolution of 8 micrometers.

Example 7
24.5 g of phenolic epoxy resin EPPN-502H, 20.2 g of 3-HBA, 0.13 g of catalyst, 0.04 g of HQ, and 47.2 g of PGMEA were mixed in a reaction bottle. The mixture was heated to 140° C. and reacted with stirring for 7 hours to form a polymer. 8.0 g of hexahydrophthalic anhydride was then added to the reaction bottle and reacted with stirring for 3 hours to form a modified polymer. The acid value of the modified polymer was 65 mg KOH/g and the weight average molecular weight was 3,300.

23 parts by weight of the modified polymer, 6.0 parts by weight of DNQ, and 71 parts by weight of a solvent (PGMEA and BA, v/v=9/1) were mixed, and the solubility of DNQ was good (no precipitate was observed by visual inspection). The solution of the photosensitive composition was made into a positive dry film photoresist, which was then transferred onto a wafer to form a photoresist layer. The photoresist layer was exposed to ghi radiation (exposure dose 100 mJ/ ^cm2 ) and developed with 1% sodium carbonate solution for 30 to 50 seconds. This resulted in a pattern with a resolution of 8 micrometers.

Example 8
26.2 g of phenolic epoxy resin EPPN-502H, 21.6 g of 3-HBA, 0.14 g of catalyst, 0.04 g of HQ, and 48 g of PGMEA were mixed in a reaction bottle. The mixture was heated to 140° C. and reacted with stirring for 7 hours to form a polymer. 4.0 g of hexahydrophthalic anhydride was then added to the reaction bottle and reacted with stirring for 3 hours to form a modified polymer. The acid value of the modified polymer was 37 mg KOH/g and the weight average molecular weight was 2700.

23 parts by weight of modified polymer, 3.5 parts by weight of DNQ, and 73.5 parts by weight of solvent (PGMEA and BA, v/v=9/1) were mixed, and the solubility of DNQ was good (no precipitate was observed by visual inspection). The solution of the photosensitive composition was made into a positive dry film photoresist, which was then transferred onto a wafer to form a photoresist layer. The photoresist layer was exposed to ghi radiation (exposure dose 100 mJ/ ^cm2 ) and developed with 1% sodium carbonate solution for 60 to 80 seconds. This resulted in a pattern with a resolution of 8 micrometers.

Example 9
30 g of phenolic epoxy resin EPPN-502H, 24.8 g of 3-HBA, 0.03 g of catalyst, 0.06 g of HQ, and 45 g of PGMEA were mixed in a reaction bottle. The mixture was heated to 140° C. and stirred for 7 hours to react and form a polymer. The acid value of the polymer was 7 mg KOH/g and the weight average molecular weight was 3000.

23 parts by weight of polymer, 5.1 parts by weight of DNQ, and 71.9 parts by weight of solvent (PGMEA and BA, v/v=9/1) were mixed, and DNQ had good solubility (no visible precipitate). The solution of the photosensitive composition was made into a positive dry film photoresist, which was then transferred onto a wafer to form a photoresist layer. The photoresist layer was exposed to ghi radiation (exposure dose 100 mJ/ ^cm2 ) and developed with 1% sodium carbonate solution for 100 to 120 seconds. This resulted in a pattern with a resolution of 8 micrometers.

Example 10
27.3 g of phenolic epoxy resin EPPN-502H, 22.5 g of 3-HBA, 0.14 g of catalyst, 0.04 g of HQ, and 50 g of PGMEA were mixed in a reaction bottle. The mixture was heated to 140° C. and stirred for 7 hours to react and form a polymer. The acid value of the polymer was 0 mg KOH/g and the weight average molecular weight was 2800.

23 parts by weight of polymer, 6.9 parts by weight of DNQ, and 70.1 parts by weight of solvent (PGMEA and BA, v/v=9/1) were mixed, and DNQ had good solubility (no visible precipitate). The solution of the photosensitive composition was made into a positive dry film photoresist, which was then transferred onto a wafer to form a photoresist layer. The photoresist layer was exposed to ghi radiation (exposure dose 200 mJ/ ^cm2 ) and developed with 1% sodium carbonate solution for 40 to 60 seconds. This resulted in a pattern with a resolution of 8 micrometers.

Example 11
24.5 g of phenolic epoxy resin EPPN-502H, 20.2 g of 2-hydroxybenzoic acid (2-HBA), 0.13 g of catalyst, 0.04 g of HQ, and 47.2 g of PGMEA were mixed in a reaction bottle. The mixture was heated to 140° C. and reacted with stirring for 7 hours to form a polymer. 8.0 g of hexahydrophthalic anhydride was then added to the reaction bottle and reacted with stirring for 3 hours to form a modified polymer. The acid value of the modified polymer was 88 mg KOH/g and the weight average molecular weight was 3500.

23 parts by weight of modified polymer, 6.9 parts by weight of DNQ, and 70.1 parts by weight of solvent (PGMEA and BA, v/v=9/1) were mixed, and the solubility of DNQ was poor (a precipitate was visible). The solution of the photosensitive composition was made into a positive dry film photoresist, which was then transferred onto a wafer to form a photoresist layer. The photoresist layer was exposed to ghi radiation (exposure dose 1000 mJ/ ^cm2 ) and developed with 1% sodium carbonate solution for 100 to 150 seconds. This resulted in a pattern with a resolution of 50 micrometers.

Example 12
26 g of phenolic epoxy resin EPPN-502H, 23.8 g of 2,6-dihydroxybenzoic acid (2,6-DHBA), 0.14 g of catalyst, 0.04 g of HQ, and 50 g of PGMEA were mixed in a reaction bottle. The mixture was heated to 140° C. and stirred for 7 hours to react and form a polymer. The acid value of the polymer was 7 mg KOH/g and the weight average molecular weight was 46,000.

23 parts by weight of polymer, 6.9 parts by weight of DNQ, and 70.1 parts by weight of solvent (PGMEA and BA, v/v=9/1) were mixed, and DNQ had good solubility (no visible precipitate). The solution of the photosensitive composition was made into a positive dry film photoresist, which was then transferred onto a wafer to form a photoresist layer. The photoresist layer was exposed to ghi radiation (exposure dose 1000 mJ/ ^cm2 ) and developed with 1% sodium carbonate solution for 100 to 150 seconds. This resulted in a pattern with a resolution of 50 micrometers.

Example 13
26 g of phenolic epoxy resin EPPN-502H, 23.8 g of 2,4-dihydroxybenzoic acid (2,4-DHBA), 0.14 g of catalyst, 0.04 g of HQ, and 50 g of PGMEA were mixed in a reaction bottle. The mixture was heated to 140° C. and stirred for 7 hours to react and form a polymer. The acid value of the polymer was 49 mg KOH/g and the weight average molecular weight was 11,000.

23 parts by weight of polymer, 6.0 parts by weight of DNQ, and 71 parts by weight of solvent (PGMEA and BA, v/v=9/1) were mixed, and DNQ had good solubility (no visible precipitate). The solution of the photosensitive composition was made into a positive dry film photoresist, which was then transferred onto a wafer to form a photoresist layer. The photoresist layer was exposed to ghi radiation (exposure dose 200 mJ/ ^cm2 ) and developed with 1% sodium carbonate solution for 90 to 120 seconds. This resulted in a pattern with a resolution of 50 micrometers.

Example 14
26 g of phenolic epoxy resin EPPN-502H, 23.8 g of 3,5-dihydroxybenzoic acid (3,5-DHBA), 0.14 g of catalyst, 0.04 g of HQ, and 50 g of PGMEA were mixed in a reaction bottle. The mixture was heated to 140° C. and stirred for 7 hours to react and form a polymer. The acid value of the polymer was 9 mg KOH/g and the weight average molecular weight was 3000.

23 parts by weight of polymer, 5.1 parts by weight of DNQ, and 71.9 parts by weight of solvent (PGMEA and BA, v/v=9/1) were mixed, and DNQ had good solubility (no visible precipitate). The solution of the photosensitive composition was made into a positive dry film photoresist, which was then transferred onto a wafer to form a photoresist layer. The photoresist layer was exposed to ghi radiation (exposure dose 200 mJ/ ^cm2 ) and developed with 1% sodium carbonate solution for 90 to 120 seconds. This resulted in a pattern with a resolution of 50 micrometers.

Example 15
23.5 g of phenolic epoxy resin EPPN-502H, 26.3 g of 3-hydroxy-2-naphthoic acid (3H2NA), 0.12 g of catalyst, 0.04 g of HQ, and 50 g of PGMEA were mixed in a reaction bottle. The mixture was heated to 140° C. and stirred for 7 hours to react and form a polymer. The acid value of the polymer was 52 mg KOH/g and the weight average molecular weight was 11,800.

23 parts by weight of polymer, 6.9 parts by weight of DNQ, and 70.1 parts by weight of solvent (PGMEA and BA, v/v=9/1) were mixed, and the solubility of DNQ was poor (a precipitate was visible). The solution of the photosensitive composition was made into a positive dry film photoresist, which was then transferred onto a wafer to form a photoresist layer. The photoresist layer was exposed to ghi radiation (exposure dose 1000 mJ/ ^cm2 ) and developed with 1% sodium carbonate solution for 100 to 150 seconds. This resulted in a pattern with a resolution of 50 micrometers.

Example 16
40.2 g of phenolic epoxy resin EPPN-502H, 24.5 g of pentanoic acid, 0.06 g of catalyst, 0.07 g of HQ, and 35.2 g of PGMEA were mixed in a reaction bottle. The mixture was heated to 140° C. and stirred for 7 hours to react and form a polymer. The acid value of the polymer was 25 mg KOH/g and the weight average molecular weight was 2400.

12 parts by weight of the polymer, 10.2 parts by weight of phenolic resin PR56001 (weight average molecular weight 5000, commercially available from Sumitomoto Bakelite), 6.7 parts by weight of DNQ, and 71.1 parts by weight of a solvent (PGMEA and BA, v/v=9/1) were mixed, and the solubility of DNQ was good (no precipitate was observed by visual inspection). The solution of the photosensitive composition was made into a positive dry film photoresist, which was then transferred onto a wafer to form a photoresist layer. The photoresist layer was exposed to ghi radiation (exposure dose 400 mJ/ ^cm2 ) and developed with 1% sodium carbonate solution for 60 to 90 seconds. This resulted in a pattern with a resolution of 8 micrometers.

Example 17
7.5 parts by weight of the polymer synthesized in Example 16, 15 parts by weight of phenolic resin PR56001 (weight average molecular weight is 5000), 6.7 parts by weight of DNQ, and 70.8 parts by weight of a solvent (PGMEA and BA, v/v=9/1) were mixed, and the solubility of DNQ was good (no precipitate was observed by visual inspection). The solution of the photosensitive composition was made into a positive dry film photoresist, which was then transferred onto a wafer to form a photoresist layer. The photoresist layer was exposed to ghi radiation (exposure dose 400 mJ/ ^cm2 ) and developed with 1% sodium carbonate solution for 60 to 90 seconds. This resulted in a pattern with a resolution of 8 micrometers.

Example 18
15 parts by weight of the polymer synthesized in Example 16, 7.5 parts by weight of phenolic resin PR56001 (weight average molecular weight is 5000), 3.5 parts by weight of DNQ, and 74.3 parts by weight of a solvent (PGMEA and BA, v/v=9/1) were mixed, and the solubility of DNQ was good (no precipitate was observed by visual inspection). The solution of the photosensitive composition was made into a positive dry film photoresist, which was then transferred onto a wafer to form a photoresist layer. The photoresist layer was exposed to ghi radiation (exposure dose 400 mJ/ ^cm2 ) and developed with 1% sodium carbonate solution for 60 to 90 seconds. This resulted in a pattern with a resolution of 8 micrometers.

Example 19
36.4 g of phenolic epoxy resin EPPN-502H, 22.2 g of pentanoic acid, 0.19 g of catalyst, 0.07 g of HQ, and 35.0 g of PGMEA were mixed in a reaction bottle. The mixture was heated to 140° C. and reacted with stirring for 7 hours to form a polymer. 6.1 g of hexahydrophthalic anhydride was then added to the reaction bottle and reacted with stirring for 3 hours to form a modified polymer. The acid value of the modified polymer was 61 mg KOH/g and the weight average molecular weight was 2500.

12 parts by weight of the modified polymer, 10.2 parts by weight of phenolic resin PR56032 (weight average molecular weight 50000, commercially available from Sumitomoto Bakelite), 8 parts by weight of DNQ, and 69.8 parts by weight of a solvent (PGMEA and BA, v/v=9/1) were mixed, and the solubility of DNQ was good (no precipitate was observed by visual inspection). The solution of the photosensitive composition was made into a positive dry film photoresist, which was then transferred onto a wafer to form a photoresist layer. The photoresist layer was exposed to ghi radiation (exposure dose 400 mJ/ ^cm2 ) and developed with 1% sodium carbonate solution for 60 to 90 seconds. This resulted in a pattern with a resolution of 8 micrometers.

Example 20
7.5 parts by weight of the polymer synthesized in Example 19, 15 parts by weight of phenolic resin PR56032 (weight average molecular weight is 50000), 6.7 parts by weight of DNQ, and 70.8 parts by weight of a solvent (PGMEA and BA, v/v=9/1) were mixed, and the solubility of DNQ was good (no precipitate was observed by visual inspection). The solution of the photosensitive composition was made into a positive dry film photoresist, which was then transferred onto a wafer to form a photoresist layer. The photoresist layer was exposed to ghi radiation (exposure dose 400 mJ/ ^cm2 ) and developed with 1% sodium carbonate solution for 60 to 90 seconds. This resulted in a pattern with a resolution of 8 micrometers.

Example 21
15 parts by weight of the polymer synthesized in Example 19, 7.5 parts by weight of phenolic resin PR56032 (weight average molecular weight is 50000), 6.7 parts by weight of DNQ, and 70.8 parts by weight of a solvent (PGMEA and BA, v/v=9/1) were mixed, and the solubility of DNQ was good (no precipitate was observed by visual inspection). The solution of the photosensitive composition was made into a positive dry film photoresist, which was then transferred onto a wafer to form a photoresist layer. The photoresist layer was exposed to ghi radiation (exposure dose 400 mJ/ ^cm2 ) and developed with 1% sodium carbonate solution for 60 to 90 seconds. This resulted in a pattern with a resolution of 8 micrometers.

Example 22
40.2 g of phenolic epoxy resin EPPN-502H, 17.7 g of propanoic acid, 0.21 g of catalyst, 0.07 g of HQ, and 35.0 g of PGMEA were mixed in a reaction bottle. The mixture was heated to 140° C. and reacted with stirring for 7 hours to form a polymer. 6.7 g of hexahydrophthalic anhydride was then added to the reaction bottle and reacted with stirring for 3 hours to form a modified polymer. The acid value of the modified polymer was 55 mg KOH/g and the weight average molecular weight was 2700.

When 12 parts by weight of the modified polymer, 10.2 parts by weight of phenolic resin PR56001 (weight average molecular weight 5000), 6.7 parts by weight of DNQ, and 71.1 parts by weight of a solvent (PGMEA and BA, v/v = 9/1) were mixed, the solubility of DNQ was good (no precipitate was observed visually). A solution of the photosensitive composition was made into a positive dry film photoresist, but it could not be transferred onto a wafer to form a photoresist layer.

Example 23
When 12 parts by weight of the modified polymer synthesized in Example 22, 10.2 parts by weight of phenol resin PR56032 (weight average molecular weight is 50,000), 6.7 parts by weight of DNQ, and 71.1 parts by weight of a solvent (PGMEA and BA, v/v=9/1) were mixed, the solubility of DNQ was good (no precipitate was observed by visual inspection). The solution of the photosensitive composition was made into a positive dry film photoresist, but it could not be transferred onto a wafer to form a photoresist layer.

Example 24
29 g of phenolic epoxy resin EPPN-502H, 21.1 g of benzoic acid, 0.15 g of catalyst, 0.06 g of HQ, and 40.0 g of PGMEA were mixed in a reaction bottle. The mixture was heated to 140° C. and reacted with stirring for 7 hours to form a polymer. 9.7 g of hexahydrophthalic anhydride was then added to the reaction bottle and reacted with stirring for 3 hours to form a modified polymer. The acid value of the modified polymer was 80 mg KOH/g and the weight average molecular weight was 2500.

When 12 parts by weight of the modified polymer, 10.2 parts by weight of phenolic resin PR56001 (weight average molecular weight 5000), 6.7 parts by weight of DNQ, and 71.1 parts by weight of a solvent (PGMEA and BA, v/v = 9/1) were mixed, the solubility of DNQ was good (no precipitate was observed visually). A solution of the photosensitive composition was made into a positive dry film photoresist, but it could not be transferred onto a wafer to form a photoresist layer.

Example 25
When 12 parts by weight of the modified polymer synthesized in Example 24, 10.2 parts by weight of phenol resin PR56032 (weight average molecular weight is 50,000), 6.7 parts by weight of DNQ, and 71.1 parts by weight of a solvent (PGMEA and BA, v/v=9/1) were mixed, the solubility of DNQ was good (no precipitate was observed by visual inspection). The solution of the photosensitive composition was made into a positive dry film photoresist, but it could not be transferred onto a wafer to form a photoresist layer.

Example 26
31.5 g of phenolic epoxy resin EPPN-502H, 22.9 g of benzoic acid, 0.16 g of catalyst, 0.07 g of HQ, and 40.0 g of PGMEA were mixed in a reaction bottle. The mixture was heated to 140° C. and reacted with stirring for 7 hours to form a polymer. 5.3 g of hexahydrophthalic anhydride was then added to the reaction bottle and reacted with stirring for 3 hours to form a modified polymer. The acid value of the modified polymer was 46 mg KOH/g and the weight average molecular weight was 2500.

When 12 parts by weight of the modified polymer, 10.2 parts by weight of phenolic resin PR56032 (weight average molecular weight 50,000), 6.7 parts by weight of DNQ, and 71.1 parts by weight of a solvent (PGMEA and BA, v/v = 9/1) were mixed, the solubility of DNQ was good (no precipitate was observed visually). A solution of the photosensitive composition was made into a positive dry film photoresist, but it could not be transferred onto a wafer to form a photoresist layer.

Example 27
28.8 g of phenolic epoxy resin EPPN-201 (commercially available from Nippon Kayaku), 21 g of 4-HBA, 0.13 g of catalyst, 0.04 g of HQ, and 50 g of PGMEA were mixed in a reaction bottle. The mixture was heated to 140° C. and stirred for 7 hours to react and form a polymer. The acid value of the polymer was 0 mg KOH/g and the weight average molecular weight was 5200. The phenolic epoxy resin EPPN-201 has the following chemical structure:

n≒6.

23 parts by weight of polymer, 6.0 parts by weight of DNQ, and 71 parts by weight of solvent (PGMEA and BA, v/v=9/1) were mixed, and DNQ had good solubility (no visible precipitate). The solution of the photosensitive composition was made into a positive dry film photoresist, which was then transferred onto a wafer to form a photoresist layer. The photoresist layer was exposed to ghi radiation (exposure dose 100 mJ/ ^cm2 ) and developed with 1% sodium carbonate solution for 70 to 90 seconds. This resulted in a pattern with a resolution of 8 micrometers.

Example 28
Phenolic epoxy resin EOCN-102S (commercially available from Nippon Kayaku) 30.1 g, 4-HBA 19.8 g, catalyst 0.13 g, HQ 0.04 g, and PGMEA 50 g were mixed in a reaction bottle. The mixture was heated to 140° C. and stirred for 7 hours to react and form a polymer. The polymer had an acid value of 3 mg KOH/g and a weight average molecular weight of 5600. The phenolic epoxy resin EOCN-102S has the following chemical structure:

n≒4 to 6.

23 parts by weight of polymer, 6.0 parts by weight of DNQ, and 71 parts by weight of solvent (PGMEA and BA, v/v=9/1) were mixed, and DNQ had good solubility (no visible precipitate). The solution of the photosensitive composition was made into a positive dry film photoresist, which was then transferred onto a wafer to form a photoresist layer. The photoresist layer was exposed to ghi radiation (exposure dose 100 mJ/ ^cm2 ) and developed with 1% sodium carbonate solution for 70 to 90 seconds. This resulted in a pattern with a resolution of 8 micrometers.

Example 29
33.2 g of phenolic epoxy resin BREN-105 (commercially available from Nippon Kayaku), 16.7 g of 4-HBA, 0.11 g of catalyst, 0.04 g of HQ, and 50 g of PGMEA were mixed in a reaction bottle. The mixture was heated to 140° C. and stirred for 7 hours to react and form a polymer. The acid value of the polymer was 5 mg KOH/g and the weight average molecular weight was 5900. The phenolic epoxy resin BREN-105 has the following chemical structure:

n≒2.

23 parts by weight of polymer, 5.1 parts by weight of DNQ, and 71.9 parts by weight of solvent (PGMEA and BA, v/v=9/1) were mixed, and DNQ had good solubility (no visible precipitate). The solution of the photosensitive composition was made into a positive dry film photoresist, which was then transferred onto a wafer to form a photoresist layer. The photoresist layer was exposed to ghi radiation (exposure dose 100 mJ/ ^cm2 ) and developed with 1% sodium carbonate solution for 70 to 90 seconds. This resulted in a pattern with a resolution of 8 micrometers.

Example 30
Phenolic epoxy resin XD-1000 (commercially available from Nippon Kayaku) 33.2 g, 4-HBA 17.7 g, catalyst 0.11 g, HQ 0.04 g, and PGMEA 50 g were mixed in a reaction bottle. The mixture was heated to 140° C. and stirred for 7 hours to react and form a polymer. The polymer had an acid value of 5 mg KOH/g and a weight average molecular weight of 5700. The phenolic epoxy resin XD-1000 has the following chemical structure:

n=1 to 3.

23 parts by weight of polymer, 6.0 parts by weight of DNQ, and 71 parts by weight of solvent (PGMEA and BA, v/v=9/1) were mixed, and DNQ had good solubility (no visible precipitate). The solution of the photosensitive composition was made into a positive dry film photoresist, which was then transferred onto a wafer to form a photoresist layer. The photoresist layer was exposed to ghi radiation (exposure dose 200 mJ/ ^cm2 ) and developed with 1% sodium carbonate solution for 60 to 80 seconds. This resulted in a pattern with a resolution of 8 micrometers.

Example 31
Phenolic epoxy resin NC-2000-L (commercially available from Nippon Kayaku) 31.4 g, 4-HBA 18.5 g, catalyst 0.12 g, HQ 0.04 g, and PGMEA 50 g were mixed in a reaction bottle. The mixture was heated to 140° C. and stirred for 7 hours to react and form a polymer. The polymer had an acid value of 3 mg KOH/g and a weight average molecular weight of 5100. The phenolic epoxy resin NC-2000-L has the following chemical structure:

n=1 to 3.

23 parts by weight of polymer, 6.0 parts by weight of DNQ, and 71 parts by weight of solvent (PGMEA and BA, v/v=9/1) were mixed, and DNQ had good solubility (no visible precipitate). The solution of the photosensitive composition was made into a positive dry film photoresist, which was then transferred onto a wafer to form a photoresist layer. The photoresist layer was exposed to ghi radiation (exposure dose 200 mJ/ ^cm2 ) and developed with 1% sodium carbonate solution for 60 to 80 seconds. This resulted in a pattern with a resolution of 8 micrometers.

Example 32
Phenolic epoxy resin NC-3000-L (commercially available from Nippon Kayaku) 33.0 g, 4-HBA 16.9 g, catalyst 0.11 g, HQ 0.04 g, and PGMEA 50 g were mixed in a reaction bottle. The mixture was heated to 140° C. and stirred for 7 hours to react and form a polymer. The polymer had an acid value of 5 mg KOH/g and a weight average molecular weight of 6000. The phenolic epoxy resin NC-3000-L has the following chemical structure:

n=1 to 3.

23 parts by weight of polymer, 6.9 parts by weight of DNQ, and 70.1 parts by weight of solvent (PGMEA and BA, v/v=9/1) were mixed, and DNQ had good solubility (no visible precipitate). The solution of the photosensitive composition was made into a positive dry film photoresist, which was then transferred onto a wafer to form a photoresist layer. The photoresist layer was exposed to ghi radiation (exposure dose 200 mJ/ ^cm2 ) and developed with 1% sodium carbonate solution for 40 to 60 seconds. This resulted in a pattern with a resolution of 8 micrometers.

Example 33
Phenolic epoxy resin NC-7300L (commercially available from Nippon Kayaku) 30.2 g, 4-HBA 19.6 g, catalyst 0.13 g, HQ 0.04 g, and PGMEA 50 g were mixed in a reaction bottle. The mixture was heated to 140° C. and stirred for 7 hours to react and form a polymer. The polymer had an acid value of 4 mg KOH/g and a weight average molecular weight of 5800. The phenolic epoxy resin NC-7300L has the following chemical structure:

n=1 to 3.

23 parts by weight of polymer, 6.9 parts by weight of DNQ, and 70.1 parts by weight of solvent (PGMEA and BA, v/v=9/1) were mixed, and DNQ had good solubility (no visible precipitate). The solution of the photosensitive composition was made into a positive dry film photoresist, which was then transferred onto a wafer to form a photoresist layer. The photoresist layer was exposed to ghi radiation (exposure dose 200 mJ/ ^cm2 ) and developed with 1% sodium carbonate solution for 40 to 60 seconds. This resulted in a pattern with a resolution of 8 micrometers.

Example 34
26.5 g of phenolic epoxy resin EPPN-502H, 19.3 g of 4-HBA, 0.12 g of catalyst, 0.04 g of HQ, and 46.0 g of PGMEA were mixed in a reaction bottle. The mixture was heated to 140° C. and reacted with stirring for 7 hours to form a polymer. 8 g of hexahydrophthalic anhydride was then added to the reaction bottle and reacted with stirring for 3 hours to form a modified polymer. The acid value of the modified polymer was 82 mg KOH/g and the weight average molecular weight was 6100.

23 parts by weight of modified polymer, 6.0 parts by weight of DNQ, and 71 parts by weight of solvent (PGMEA and BA, v/v=9/1) were mixed, and the solubility of DNQ was good (no precipitate was observed by visual inspection). The solution of the photosensitive composition was made into a positive dry film photoresist, which was then transferred onto a wafer to form a photoresist layer. The photoresist layer was exposed to ghi radiation (exposure dose 100 mJ/ ^cm2 ) and developed with 1% sodium carbonate solution for 70 to 90 seconds. This resulted in a pattern with a resolution of 8 micrometers.

Example 35
27.8 g of phenolic epoxy resin EOCN-102S, 18.3 g of 4-HBA, 0.12 g of catalyst, 0.04 g of HQ, and 46.2 g of PGMEA were mixed in a reaction bottle. The mixture was heated to 140° C. and reacted with stirring for 7 hours to form a polymer. 7.5 g of hexahydrophthalic anhydride was then added to the reaction bottle and reacted with stirring for 3 hours to form a modified polymer. The acid value of the modified polymer was 83 mg KOH/g and the weight average molecular weight was 6500.

23 parts by weight of modified polymer, 6.0 parts by weight of DNQ, and 71 parts by weight of solvent (PGMEA and BA, v/v=9/1) were mixed, and the solubility of DNQ was good (no precipitate was observed by visual inspection). The solution of the photosensitive composition was made into a positive dry film photoresist, which was then transferred onto a wafer to form a photoresist layer. The photoresist layer was exposed to ghi radiation (exposure dose 100 mJ/ ^cm2 ) and developed with 1% sodium carbonate solution for 70 to 90 seconds. This resulted in a pattern with a resolution of 8 micrometers.

Example 36
31.1 g of phenolic epoxy resin BREN-105, 15.6 g of 4-HBA, 0.10 g of catalyst, 0.04 g of HQ, and 46.8 g of PGMEA were mixed in a reaction bottle. The mixture was heated to 140° C. and reacted with stirring for 7 hours to form a polymer. 6.4 g of hexahydrophthalic anhydride was then added to the reaction bottle and reacted with stirring for 3 hours to form a modified polymer. The acid value of the modified polymer was 80 mg KOH/g and the weight average molecular weight was 5900.

23 parts by weight of modified polymer, 5.1 parts by weight of DNQ, and 71.9 parts by weight of solvent (PGMEA and BA, v/v=9/1) were mixed, and DNQ had good solubility (no visible precipitate). The solution of the photosensitive composition was made into a positive dry film photoresist, which was then transferred onto a wafer to form a photoresist layer. The photoresist layer was exposed to ghi radiation (exposure dose 100 mJ/ ^cm2 ) and developed with 1% sodium carbonate solution for 70 to 90 seconds. This resulted in a pattern with a resolution of 8 micrometers.

Example 37
30.0 g of phenolic epoxy resin XD-1000, 16.5 g of 4-HBA, 0.11 g of catalyst, 0.04 g of HQ, and 46.6 g of PGMEA were mixed in a reaction bottle. The mixture was heated to 140° C. and reacted with stirring for 7 hours to form a polymer. 6.8 g of hexahydrophthalic anhydride was then added to the reaction bottle and reacted with stirring for 3 hours to form a modified polymer. The acid value of the modified polymer was 80 mg KOH/g and the weight average molecular weight was 6700.

23 parts by weight of modified polymer, 6.0 parts by weight of DNQ, and 71 parts by weight of solvent (PGMEA and BA, v/v=9/1) were mixed, and the solubility of DNQ was good (no precipitate was observed by visual inspection). The solution of the photosensitive composition was made into a positive dry film photoresist, which was then transferred onto a wafer to form a photoresist layer. The photoresist layer was exposed to ghi radiation (exposure dose 200 mJ/ ^cm2 ) and developed with 1% sodium carbonate solution for 60 to 80 seconds. This resulted in a pattern with a resolution of 8 micrometers.

Example 38
29.2 g of phenolic epoxy resin NC-2000-L, 17.2 g of 4-HBA, 0.11 g of catalyst, 0.04 g of HQ, and 46.4 g of PGMEA were mixed in a reaction bottle. The mixture was heated to 140° C. and reacted with stirring for 7 hours to form a polymer. 7.1 g of hexahydrophthalic anhydride was then added to the reaction bottle and reacted with stirring for 3 hours to form a modified polymer. The acid value of the modified polymer was 82 mg KOH/g and the weight average molecular weight was 6,300.

23 parts by weight of modified polymer, 6.0 parts by weight of DNQ, and 71 parts by weight of solvent (PGMEA and BA, v/v=9/1) were mixed, and the solubility of DNQ was good (no precipitate was observed by visual inspection). The solution of the photosensitive composition was made into a positive dry film photoresist, which was then transferred onto a wafer to form a photoresist layer. The photoresist layer was exposed to ghi radiation (exposure dose 200 mJ/ ^cm2 ) and developed with 1% sodium carbonate solution for 60 to 80 seconds. This resulted in a pattern with a resolution of 8 micrometers.

Example 39
30.8 g of phenolic epoxy resin NC-3000-L, 15.8 g of 4-HBA, 0.10 g of catalyst, 0.04 g of HQ, and 46.8 g of PGMEA were mixed in a reaction bottle. The mixture was heated to 140° C. and reacted with stirring for 7 hours to form a polymer. 6.5 g of hexahydrophthalic anhydride was then added to the reaction bottle and reacted with stirring for 3 hours to form a modified polymer. The acid value of the modified polymer was 78 mg KOH/g and the weight average molecular weight was 6500.

23 parts by weight of modified polymer, 6.9 parts by weight of DNQ, and 70.1 parts by weight of solvent (PGMEA and BA, v/v=9/1) were mixed, and the solubility of DNQ was good (no precipitate was observed by visual inspection). The solution of the photosensitive composition was made into a positive dry film photoresist, which was then transferred onto a wafer to form a photoresist layer. The photoresist layer was exposed to ghi radiation (exposure dose 200 mJ/ ^cm2 ) and developed with 1% sodium carbonate solution for 40 to 60 seconds. This resulted in a pattern with a resolution of 8 micrometers.

Example 40
28.0 g of phenolic epoxy resin NC-7300L, 18.2 g of 4-HBA, 0.12 g of catalyst, 0.04 g of HQ, and 46.2 g of PGMEA were mixed in a reaction bottle. The mixture was heated to 140° C. and reacted with stirring for 7 hours to form a polymer. 7.5 g of hexahydrophthalic anhydride was then added to the reaction bottle and reacted with stirring for 3 hours to form a modified polymer. The acid value of the modified polymer was 77 mg KOH/g and the weight average molecular weight was 6600.

23 parts by weight of modified polymer, 6.9 parts by weight of DNQ, and 70.1 parts by weight of solvent (PGMEA and BA, v/v=9/1) were mixed, and the solubility of DNQ was good (no precipitate was observed by visual inspection). The solution of the photosensitive composition was made into a positive dry film photoresist, which was then transferred onto a wafer to form a photoresist layer. The photoresist layer was exposed to ghi radiation (exposure dose 200 mJ/ ^cm2 ) and developed with 1% sodium carbonate solution for 40 to 60 seconds. This resulted in a pattern with a resolution of 8 micrometers.

Example 41
34.5 g of bisphenol type epoxy resin EPON828, 25.3 g of 4-HBA, 0.18 g of catalyst, 0.07 g of HQ, and 40.0 g of PGMEA were mixed in a reaction bottle. The mixture was heated to 140° C. and stirred for 7 hours to react and form a polymer. The acid value of the polymer was 3 mg KOH/g and the weight average molecular weight was 2100.

17.4 parts by weight of the polymer, 8.7 parts by weight of phenolic resin PR56001 (weight average molecular weight is 5000), 6.3 parts by weight of DNQ, and 67.6 parts by weight of a solvent (PGMEA and BA, v/v=9/1) were mixed, and the solubility of DNQ was good (no precipitate was observed by visual inspection). The solution of the photosensitive composition was made into a positive dry film photoresist, which was then transferred onto a wafer to form a photoresist layer. The photoresist layer was exposed to ghi radiation (exposure dose 100 mJ/ ^cm2 ) and developed with 1% sodium carbonate solution for 40 to 60 seconds. This resulted in a pattern with a resolution of 8 micrometers.

Example 42
18.3 parts by weight of the polymer of Example 41, 9.1 parts by weight of phenolic resin PR56001 (weight average molecular weight is 5000), 4.8 parts by weight of DNQ, and 67.8 parts by weight of a solvent (PGMEA and BA, v/v=9/1) were mixed, and the solubility of DNQ was good (no precipitate was observed by visual inspection). The solution of the photosensitive composition was made into a positive dry film photoresist, which was then transferred onto a wafer to form a photoresist layer. The photoresist layer was exposed to ghi radiation (exposure dose 200 mJ/ ^cm2 ) and developed with 1% sodium carbonate solution for 40 to 60 seconds. This resulted in a pattern with a resolution of 8 micrometers.

Example 43
17.4 parts by weight of the polymer of Example 41, 8.7 parts by weight of phenolic resin PR56032 (weight average molecular weight is 50000), 6.3 parts by weight of DNQ, and 67.6 parts by weight of a solvent (PGMEA and BA, v/v=9/1) were mixed, and the solubility of DNQ was good (no precipitate was observed by visual inspection). The solution of the photosensitive composition was made into a positive dry film photoresist, which was then transferred onto a wafer to form a photoresist layer. The photoresist layer was exposed to ghi radiation (exposure dose 100 mJ/ ^cm2 ) and developed with 1% sodium carbonate solution for 40 to 60 seconds. This resulted in a pattern with a resolution of 8 micrometers.

Example 44
18.3 parts by weight of the polymer of Example 41, 9.1 parts by weight of phenolic resin PR56032 (weight average molecular weight is 50000), 4.8 parts by weight of DNQ, and 67.8 parts by weight of a solvent (PGMEA and BA, v/v=9/1) were mixed, and the solubility of DNQ was good (no precipitate was observed by visual inspection). The solution of the photosensitive composition was made into a positive dry film photoresist, which was then transferred onto a wafer to form a photoresist layer. The photoresist layer was exposed to ghi radiation (exposure dose 200 mJ/ ^cm2 ) and developed with 1% sodium carbonate solution for 40 to 60 seconds. This resulted in a pattern with a resolution of 8 micrometers.

Example 45
26.1 parts by weight of the polymer of Example 41, 6.3 parts by weight of DNQ, and 67.6 parts by weight of a solvent (PGMEA and BA, v/v=9/1) were mixed, and the solubility of DNQ was good (no precipitate was observed by visual inspection). The solution of the photosensitive composition was made into a positive dry film photoresist, which was then transferred onto a wafer to form a photoresist layer. The photoresist layer was exposed to ghi radiation (exposure dose 100 mJ/ ^cm2 ) and developed with 1% sodium carbonate solution for 40 to 60 seconds. This resulted in a pattern with a resolution of 8 micrometers.

Example 46
27.4 parts by weight of the polymer of Example 41, 4.8 parts by weight of DNQ, and 67.8 parts by weight of a solvent (PGMEA and BA, v/v=9/1) were mixed, and the solubility of DNQ was good (no precipitate was observed by visual inspection). The solution of the photosensitive composition was made into a positive dry film photoresist, which was then transferred onto a wafer to form a photoresist layer. The photoresist layer was exposed to ghi radiation (exposure dose 200 mJ/ ^cm2 ) and developed with 1% sodium carbonate solution for 20 to 40 seconds. This resulted in a pattern with a resolution of 8 micrometers.

Example 47
28.2 g of bisphenol type epoxy resin EPON828, 20.7 g of 4-HBA, 0.15 g of catalyst, 0.07 g of HQ, and 40.0 g of PGMEA were mixed in a reaction bottle. The mixture was heated to 140° C. and reacted with stirring for 7 hours to form a polymer. 10.9 g of hexahydrophthalic anhydride was then added to the reaction bottle and reacted with stirring for 3 hours to form a modified polymer. The acid value of the modified polymer was 81 mg KOH/g and the weight average molecular weight was 2800.

17.4 parts by weight of the modified polymer, 8.7 parts by weight of phenolic resin PR56001 (weight average molecular weight is 5000), 6.3 parts by weight of DNQ, and 67.6 parts by weight of a solvent (PGMEA and BA, v/v=9/1) were mixed, and the solubility of DNQ was good (no precipitate was observed by visual inspection). The solution of the photosensitive composition was made into a positive dry film photoresist, which was then transferred onto a wafer to form a photoresist layer. The photoresist layer was exposed to ghi radiation (exposure dose 100 mJ/ ^cm2 ) and developed with 1% sodium carbonate solution for 40 to 60 seconds. This resulted in a pattern with a resolution of 8 micrometers.

Example 48
18.3 parts by weight of the modified polymer of Example 47, 9.1 parts by weight of phenolic resin PR56032 (weight average molecular weight is 50000), 4.8 parts by weight of DNQ, and 67.8 parts by weight of a solvent (PGMEA and BA, v/v=9/1) were mixed, and the solubility of DNQ was good (no precipitate was observed by visual inspection). The solution of the photosensitive composition was made into a positive dry film photoresist, which was then transferred onto a wafer to form a photoresist layer. The photoresist layer was exposed to ghi radiation (exposure dose 200 mJ/ ^cm2 ) and developed with 1% sodium carbonate solution for 40 to 60 seconds. This resulted in a pattern with a resolution of 8 micrometers.

Example 49
26.1 parts by weight of the modified polymer of Example 47, 6.3 parts by weight of DNQ, and 67.6 parts by weight of a solvent (PGMEA and BA, v/v=9/1) were mixed, and the solubility of DNQ was good (no precipitate was observed by visual inspection). The solution of the photosensitive composition was made into a positive dry film photoresist, which was then transferred onto a wafer to form a photoresist layer. The photoresist layer was exposed to ghi radiation (exposure dose 100 mJ/ ^cm2 ) and developed with 1% sodium carbonate solution for 40 to 60 seconds. This resulted in a pattern with a resolution of 8 micrometers.

Example 50
34.5 g of bisphenol type epoxy resin EPON828, 25.3 g of 3-HBA, 0.18 g of catalyst, 0.07 g of HQ, and 40.0 g of PGMEA were mixed in a reaction bottle. The mixture was heated to 140° C. and stirred for 7 hours to react and form a polymer. The acid value of the polymer was 0 mg KOH/g and the weight average molecular weight was 2300.

17.4 parts by weight of the polymer, 8.7 parts by weight of phenolic resin PR56001 (weight average molecular weight is 5000), 6.3 parts by weight of DNQ, and 67.6 parts by weight of a solvent (PGMEA and BA, v/v=9/1) were mixed, and the solubility of DNQ was good (no precipitate was observed by visual inspection). The solution of the photosensitive composition was made into a positive dry film photoresist, which was then transferred onto a wafer to form a photoresist layer. The photoresist layer was exposed to ghi radiation (exposure dose 100 mJ/ ^cm2 ) and developed with 1% sodium carbonate solution for 40 to 60 seconds. This resulted in a pattern with a resolution of 8 micrometers.

Example 51
18.3 parts by weight of the polymer of Example 50, 9.1 parts by weight of phenolic resin PR56032 (weight average molecular weight is 50000), 4.8 parts by weight of DNQ, and 67.8 parts by weight of a solvent (PGMEA and BA, v/v=9/1) were mixed, and the solubility of DNQ was good (no precipitate was observed by visual inspection). The solution of the photosensitive composition was made into a positive dry film photoresist, which was then transferred onto a wafer to form a photoresist layer. The photoresist layer was exposed to ghi radiation (exposure dose 200 mJ/ ^cm2 ) and developed with 1% sodium carbonate solution for 40 to 60 seconds. This resulted in a pattern with a resolution of 8 micrometers.

Example 52
26.1 parts by weight of the polymer of Example 50, 6.3 parts by weight of DNQ, and 67.6 parts by weight of a solvent (PGMEA and BA, v/v=9/1) were mixed, and the solubility of DNQ was good (no precipitate was observed by visual inspection). The solution of the photosensitive composition was made into a positive dry film photoresist, which was then transferred onto a wafer to form a photoresist layer. The photoresist layer was exposed to ghi radiation (exposure dose 100 mJ/ ^cm2 ) and developed with 1% sodium carbonate solution for 40 to 60 seconds. This resulted in a pattern with a resolution of 8 micrometers.

Example 53
28.2 g of bisphenol type epoxy resin EPON828, 20.7 g of 3-HBA, 0.15 g of catalyst, 0.07 g of HQ, and 40.0 g of PGMEA were mixed in a reaction bottle. The mixture was heated to 140° C. and reacted with stirring for 7 hours to form a polymer. 10.9 g of hexahydrophthalic anhydride was then added to the reaction bottle and reacted with stirring for 3 hours to form a modified polymer. The acid value of the modified polymer was 77 mg KOH/g and the weight average molecular weight was 2900.

17.4 parts by weight of the modified polymer, 8.7 parts by weight of phenolic resin PR56001 (weight average molecular weight is 5000), 6.3 parts by weight of DNQ, and 67.6 parts by weight of a solvent (PGMEA and BA, v/v=9/1) were mixed, and the solubility of DNQ was good (no precipitate was observed by visual inspection). The solution of the photosensitive composition was made into a positive dry film photoresist, which was then transferred onto a wafer to form a photoresist layer. The photoresist layer was exposed to ghi radiation (exposure dose 100 mJ/ ^cm2 ) and developed with 1% sodium carbonate solution for 40 to 60 seconds. This resulted in a pattern with a resolution of 8 micrometers.

Example 54
18.3 parts by weight of the modified polymer of Example 53, 9.1 parts by weight of phenolic resin PR56032 (weight average molecular weight is 50000), 4.8 parts by weight of DNQ, and 67.8 parts by weight of a solvent (PGMEA and BA, v/v=9/1) were mixed, and the solubility of DNQ was good (no precipitate was observed by visual inspection). The solution of the photosensitive composition was made into a positive dry film photoresist, which was then transferred onto a wafer to form a photoresist layer. The photoresist layer was exposed to ghi radiation (exposure dose 200 mJ/ ^cm2 ) and developed with 1% sodium carbonate solution for 40 to 60 seconds. This resulted in a pattern with a resolution of 8 micrometers.

Example 55
26.1 parts by weight of the modified polymer of Example 53, 6.3 parts by weight of DNQ, and 67.6 parts by weight of a solvent (PGMEA and BA, v/v=9/1) were mixed, and the solubility of DNQ was good (no precipitate was observed by visual inspection). The solution of the photosensitive composition was made into a positive dry film photoresist, which was then transferred onto a wafer to form a photoresist layer. The photoresist layer was exposed to ghi radiation (exposure dose 100 mJ/ ^cm2 ) and developed with 1% sodium carbonate solution for 40 to 60 seconds. This resulted in a pattern with a resolution of 8 micrometers.

Example 56
33.5 g of bisphenol type epoxy resin EPON828, 27.3 g of 2,6-DHBA, 0.18 g of catalyst, 0.07 g of HQ, and 38.9 g of PGMEA were mixed in a reaction bottle. The mixture was heated to 140° C. and stirred for 7 hours to react and form a polymer. The acid value of the polymer was 0 mg KOH/g and the weight average molecular weight was 2500.

17.4 parts by weight of polymer, 8.7 parts by weight of phenolic resin PR56001 (weight average molecular weight is 5000), 6.3 parts by weight of DNQ, and 67.6 parts by weight of solvent (PGMEA and BA, v/v=9/1) were mixed, and the solubility of DNQ was good (no precipitate was observed by visual inspection). The solution of the photosensitive composition was made into a positive dry film photoresist, which was then transferred onto a wafer to form a photoresist layer. The photoresist layer was exposed to ghi radiation (exposure dose 100 mJ/ ^cm2 ) and developed with 1% sodium carbonate solution for 40 to 60 seconds. This resulted in a pattern with a resolution of 8 micrometers.

Example 57
18.3 parts by weight of the polymer of Example 56, 9.1 parts by weight of phenolic resin PR56032 (weight average molecular weight is 50000), 4.8 parts by weight of DNQ, and 67.8 parts by weight of a solvent (PGMEA and BA, v/v=9/1) were mixed, and the solubility of DNQ was good (no precipitate was observed by visual inspection). The solution of the photosensitive composition was made into a positive dry film photoresist, which was then transferred onto a wafer to form a photoresist layer. The photoresist layer was exposed to ghi radiation (exposure dose 200 mJ/ ^cm2 ) and developed with 1% sodium carbonate solution for 40 to 60 seconds. This resulted in a pattern with a resolution of 8 micrometers.

Example 58
26.1 parts by weight of the polymer of Example 56, 6.3 parts by weight of DNQ, and 67.6 parts by weight of a solvent (PGMEA and BA, v/v=9/1) were mixed, and the solubility of DNQ was good (no precipitate was observed by visual inspection). The solution of the photosensitive composition was made into a positive dry film photoresist, which was then transferred onto a wafer to form a photoresist layer. The photoresist layer was exposed to ghi radiation (exposure dose 100 mJ/ ^cm2 ) and developed with 1% sodium carbonate solution for 40 to 60 seconds. This resulted in a pattern with a resolution of 8 micrometers.

Example 59
33.5 g of bisphenol type epoxy resin EPON828, 27.3 g of 2,4-DHBA, 0.18 g of catalyst, 0.07 g of HQ, and 38.9 g of PGMEA were mixed in a reaction bottle. The mixture was heated to 140° C. and stirred for 7 hours to react and form a polymer. The acid value of the polymer was 2 mg KOH/g and the weight average molecular weight was 2600.

17.4 parts by weight of the polymer, 8.7 parts by weight of phenolic resin PR56001 (weight average molecular weight is 5000), 6.3 parts by weight of DNQ, and 67.6 parts by weight of a solvent (PGMEA and BA, v/v=9/1) were mixed, and the solubility of DNQ was good (no precipitate was observed by visual inspection). The solution of the photosensitive composition was made into a positive dry film photoresist, which was then transferred onto a wafer to form a photoresist layer. The photoresist layer was exposed to ghi radiation (exposure dose 100 mJ/ ^cm2 ) and developed with 1% sodium carbonate solution for 40 to 60 seconds. This resulted in a pattern with a resolution of 8 micrometers.

Example 60
18.3 parts by weight of the polymer of Example 59, 9.1 parts by weight of phenolic resin PR56032 (weight average molecular weight is 50000), 4.8 parts by weight of DNQ, and 67.8 parts by weight of a solvent (PGMEA and BA, v/v=9/1) were mixed, and the solubility of DNQ was good (no precipitate was observed by visual inspection). The solution of the photosensitive composition was made into a positive dry film photoresist, which was then transferred onto a wafer to form a photoresist layer. The photoresist layer was exposed to ghi radiation (exposure dose 200 mJ/ ^cm2 ) and developed with 1% sodium carbonate solution for 40 to 60 seconds. This resulted in a pattern with a resolution of 8 micrometers.

Example 61
26.1 parts by weight of the polymer of Example 59, 6.3 parts by weight of DNQ, and 67.6 parts by weight of a solvent (PGMEA and BA, v/v=9/1) were mixed, and the solubility of DNQ was good (no precipitate was observed by visual inspection). The solution of the photosensitive composition was made into a positive dry film photoresist, which was then transferred onto a wafer to form a photoresist layer. The photoresist layer was exposed to ghi radiation (exposure dose 100 mJ/ ^cm2 ) and developed with 1% sodium carbonate solution for 40 to 60 seconds. This resulted in a pattern with a resolution of 8 micrometers.

Example 62
33.5 g of bisphenol type epoxy resin EPON828, 27.3 g of 3,5-DHBA, 0.18 g of catalyst, 0.07 g of HQ, and 38.9 g of PGMEA were mixed in a reaction bottle. The mixture was heated to 140° C. and stirred for 7 hours to react and form a polymer. The acid value of the polymer was 3 mg KOH/g and the weight average molecular weight was 2300.

17.4 parts by weight of the polymer, 8.7 parts by weight of phenolic resin PR56001 (weight average molecular weight is 5000), 6.3 parts by weight of DNQ, and 67.6 parts by weight of a solvent (PGMEA and BA, v/v=9/1) were mixed, and the solubility of DNQ was good (no precipitate was observed by visual inspection). The solution of the photosensitive composition was made into a positive dry film photoresist, which was then transferred onto a wafer to form a photoresist layer. The photoresist layer was exposed to ghi radiation (exposure dose 100 mJ/ ^cm2 ) and developed with 1% sodium carbonate solution for 40 to 60 seconds. This resulted in a pattern with a resolution of 8 micrometers.

Example 63
18.3 parts by weight of the polymer of Example 62, 9.1 parts by weight of phenolic resin PR56032 (weight average molecular weight is 50000), 4.8 parts by weight of DNQ, and 67.8 parts by weight of a solvent (PGMEA and BA, v/v=9/1) were mixed, and the solubility of DNQ was good (no precipitate was observed by visual inspection). The solution of the photosensitive composition was made into a positive dry film photoresist, which was then transferred onto a wafer to form a photoresist layer. The photoresist layer was exposed to ghi radiation (exposure dose 200 mJ/ ^cm2 ) and developed with 1% sodium carbonate solution for 40 to 60 seconds. This resulted in a pattern with a resolution of 8 micrometers.

Example 64
26.1 parts by weight of the polymer of Example 62, 6.3 parts by weight of DNQ, and 67.6 parts by weight of a solvent (PGMEA and BA, v/v=9/1) were mixed, and the solubility of DNQ was good (no precipitate was observed by visual inspection). The solution of the photosensitive composition was made into a positive dry film photoresist, which was then transferred onto a wafer to form a photoresist layer. The photoresist layer was exposed to ghi radiation (exposure dose 100 mJ/ ^cm2 ) and developed with 1% sodium carbonate solution for 40 to 60 seconds. This resulted in a pattern with a resolution of 8 micrometers.

Example 65
31.6g of bisphenol type epoxy resin EPON828, 31.6g of 3H2NA, 0.17g of catalyst, 0.07g of HQ, and 36.6g of PGMEA were mixed in a reaction bottle. The mixture was heated to 140°C and stirred for 7 hours to react and form a polymer. The acid value of the polymer was 0 mg KOH/g and the weight average molecular weight was 2800.

17.4 parts by weight of the polymer, 8.7 parts by weight of phenolic resin PR56001 (weight average molecular weight is 5000), 6.3 parts by weight of DNQ, and 67.6 parts by weight of a solvent (PGMEA and BA, v/v=9/1) were mixed, and the solubility of DNQ was good (no precipitate was observed by visual inspection). The solution of the photosensitive composition was made into a positive dry film photoresist, which was then transferred onto a wafer to form a photoresist layer. The photoresist layer was exposed to ghi radiation (exposure dose 100 mJ/ ^cm2 ) and developed with 1% sodium carbonate solution for 40 to 60 seconds. This resulted in a pattern with a resolution of 8 micrometers.

Example 66
18.3 parts by weight of the polymer of Example 65, 9.1 parts by weight of phenolic resin PR56032 (weight average molecular weight is 50000), 4.8 parts by weight of DNQ, and 67.8 parts by weight of a solvent (PGMEA and BA, v/v=9/1) were mixed, and the solubility of DNQ was good (no precipitate was observed by visual inspection). The solution of the photosensitive composition was made into a positive dry film photoresist, which was then transferred onto a wafer to form a photoresist layer. The photoresist layer was exposed to ghi radiation (exposure dose 200 mJ/ ^cm2 ) and developed with 1% sodium carbonate solution for 40 to 60 seconds. This resulted in a pattern with a resolution of 8 micrometers.

Example 67
26.1 parts by weight of the polymer of Example 65, 6.3 parts by weight of DNQ, and 67.6 parts by weight of a solvent (PGMEA and BA, v/v=9/1) were mixed, and the solubility of DNQ was good (no precipitate was observed by visual inspection). The solution of the photosensitive composition was made into a positive dry film photoresist, which was then transferred onto a wafer to form a photoresist layer. The photoresist layer was exposed to ghi radiation (exposure dose 100 mJ/ ^cm2 ) and developed with 1% sodium carbonate solution for 40 to 60 seconds. This resulted in a pattern with a resolution of 8 micrometers.

Comparative Example 1
When 22.5 parts by weight of phenolic resin PR56001 (weight average molecular weight is 5000), 6.7 parts by weight of DNQ, and 70.8 parts by weight of a solvent (PGMEA and BA, v/v=9/1) were mixed, the solubility of DNQ was good (no precipitate was observed by visual inspection). The solution of the photosensitive composition was made into a positive dry film photoresist, but it could not be transferred onto a wafer to form a photoresist layer.

Comparative Example 2
When 22.5 parts by weight of phenolic resin PR56032 (weight average molecular weight is 50,000), 6.7 parts by weight of DNQ, and 70.8 parts by weight of a solvent (PGMEA and BA, v/v=9/1) were mixed, the solubility of DNQ was good (no precipitate was observed by visual inspection). The solution of the photosensitive composition was made into a positive dry film photoresist, but it could not be transferred onto a wafer to form a photoresist layer.

It will be apparent to those skilled in the art that various modifications and variations can be made to the disclosed methods and materials. It is intended that the specification and examples be considered as exemplary, with the true scope of the disclosure being indicated by the following claims and their equivalents.

Claims (12)

A polymer formed by reacting a phenolic epoxy resin with a carboxylic acid,
The phenolic epoxy resin has the following chemical structure:

(Wherein, W is H, an alkyl group, or a halogen; ^R is dimethylenebenzene or

and n=1 to 8.
The carboxylic acid has any one of the following chemical structures, or a combination thereof:

wherein Ar is benzene or naphthalene, X is a hydroxy group, an alkoxy group, or an alkyl group, and at least one X is a hydroxy group; m=1 to 3; ^{and R2} is a C4 _alkyl group.
polymer. The polymer of claim 1 having any of the following chemical structures:

(wherein R ¹¹ is dimethylenebenzene or

R ¹² is dimethylenebenzene or

R ¹³ is dimethylenebenzene or

It is.)
and further reacting with an anhydride to form a modified polymer, said anhydride having the chemical structure:

(Wherein, Y is

or a combination of these.)
The polymer according to claim 1 , wherein the acid value of the modified polymer is greater than 0 mg KOH/g and less than or equal to 100 mg KOH/g. The polymer of claim 3 , wherein the modified polymer has any of the following chemical structures:

(wherein R ²¹ is dimethylenebenzene or

R ²² is dimethylenebenzene or

R ²³ is dimethylenebenzene or

and ^R3 is

It is.)
100 parts by weight of the polymer of claim 1;
and 15 to 90 parts by weight of a photosensitive compound. The photosensitive composition according to claim 5, wherein the photosensitive compound includes a diazonaphthoquinone-based compound. The photosensitive composition of claim 5, further comprising 200 to 1000 parts by weight of a solvent. The photosensitive composition of claim 7, wherein the solvent includes propylene glycol monomethyl ether acetate, n-butyl acetate, ethyl acetate, gamma-butyrolactone, cyclohexanone, or a combination thereof. The photosensitive composition according to claim 5, further comprising 40 to 200 parts by weight of a phenolic resin. A dry film photoresist comprising a photosensitive film interposed between a support film and a protective film, the photosensitive film comprising the photosensitive composition according to claim 5. 1. A method of lithography comprising the steps of:
Providing a layer of material;
forming a photoresist layer on the material layer, the photoresist layer comprising the photosensitive composition of claim 5;
exposing the photoresist layer such that the photoresist layer has exposed and unexposed portions;
developing the photoresist layer with an alkaline solution to remove the exposed portions of the photoresist layer while leaving the unexposed portions of the photoresist layer, thereby exposing a portion of the material layer;
A lithography method comprising: The lithographic method of claim 11, wherein the alkaline solution is a sodium carbonate solution, a sodium hydroxide solution, a potassium hydroxide solution, or a combination thereof.