Radiation-sensitive resin composition

• US 5,958,645 A
• Filed: 08/27/1997
• Issued: 09/28/1999
• Est. Priority Date: 08/28/1996
• Status: Expired due to Term

• Current Assignee: JSR Corporation
• Original Assignee: Japan Synthetic Rubber Co., Ltd. (JSR Corporation)
• Inventors: Akiyama, Masahiro, Hirose, Kouichi, Inomata, Katsumi, Yumoto, Yoshiji
• Primary Examiner(s): CHU, JOHN S Y
• Application Number:
  US08/917,727
• Time in Patent Office: 762 Days
• Field of Search: 430/165, 430/191, 430/192, 430/193, 430/326
• US Class Current: 430/191
• CPC Class Codes: G03F 7/0226 characterised by the non-macromolecular additives

Abstract

A radiation-sensitive resin composition comprising:

(i) an alkali-soluble resin;

(ii) a phenol compound represented by the following formula (1): ##STR1## wherein R₁ to R₄ each represent halogen, alkyl, alkoxyl, aryl, nitro, cyano, hydroxyalkyl, hydroxyalkoxyl or hydroxyl; a, b, c and d each represent an integer of 0 to 4 and satisfying 0≦a+b≦4 and 0≦c+d≦4, provided that when a+b is 1 and c+d is 1 at least one of R₁ (or R₂) and R₃ (or R₄) is alkyl, hydroxyalkyl or hydroxyalkoxyl; R₅ to R₁₀ each represent hydrogen, alkyl or aryl; and X₁ and X₂ each represent oxygen or sulfur atom; and

(iii) a 1,2-quinonediazide compound. This composition has good resolution, sensitivity and developability, as well as has as a positive resist good focal latitude and heat resistance. The patterns formed have good shapes, and the composition may cause no fine particles during storage.

Claims

1. A radiation-sensitive resin composition comprising:

(i) an alkali-soluble resin;

(ii) a phenol compound represented by the following formula (1);

##STR14## wherein R₁ to R₄ are the same or different and each represent a halogen atom, an alkyl group, an alkoxyl group, an aryl group, a nitro group, a cyano group, a hydroxyalkyl group, a hydroxyalkoxyl group or a hydroxyl group;

a, b, c and d independently represent an integer of 0 to 4 and satisfying 0≦

a+b≦

4 and 0≦

c+d≦

4, provided that when a+b is 1 and c+d is 1 at least one of R₁ or R₂ and R₃ or R₄ to be present is an alkyl group, a hydroxyalkyl group or a hydroxyalkoxyl group;

R₅ to R₁₀ are the same or different and each represent a hydrogen atom, an alkyl group or an aryl group; and

X₁ and X₂ are the same or different and each represent an oxygen atom or a sulfur atom; and

(iii) a 1,2-quinonediazide compound.

3. The composition of claim 1, which is a radiation-sensitive photoresist composition.

4. The composition of claim 1, wherein the component-(i) alkali-soluble resin is selected from the group consisting of an alkali-soluble phenol resin, polyvinyl phenol, a derivative of the polyvinyl phenol, a styrene-maleic anhydride copolymer, a derivative of the styrene-maleic anhydride copolymer, polyvinyl hydroxybenzoate and an acrylic acid resin containing a carboxyl group.

5. The composition of claim 1, wherein the component-(i) alkali-soluble resin is a resin having a weight average molecular weight of from 2,000 to 20,000 in terms of polystyrene.

6. The composition of claim 1, wherein the component-(i) alkali-soluble resin is an alkali-soluble phenol resin having an average molecular weight of from 5,000 to 14,000 in terms of polystyrene.

7. The composition of claim 1, wherein the component-(ii) phenol compound is a compound selected from the group consisting of compounds represented by the following formulas (4-1) to (4-8), ##STR16##

8. The composition of claim 7, wherein the component-(ii) phenol compound is a compound selected from the group consisting of compounds represented by the formulas (4-1), (4-2), (4-3) and (4-7).

9. The composition of claim 1, wherein the component-(iii) 1,2-quinonediazide compound is a 1,2-benzoquinonediazidosulfonic acid ester of a compound selected from the group consisting of 2,3,4-trihydroxybenzophenone, 2,3,4,4'"'"'-tetrahydroxybenzophenone, 2,3,4,2'"'"',4'"'"'-pentahydroxybenzophenone, tris(4-hydroxyphenyl)methane, 1,3,5-tris(4-hydroxy-α

,α

-dimethylbenzyl)benzene, 1,1-bis-(4-hydroxyphenyl)-1- 4-{1-(4-hydroxyphenyl)-1-methylethyl}phenyl!ethane, 2-(3,4-dihydroxyphenyl)-2-(4-hydroxyphenyl)propane, 2,4,4-trimethyl-2-(2,4-dihydroxyphenyl)-7-hydroxycumarone and the phenol compound represented by the formula (1) defined in claim 1.

10. The composition of claim 9, wherein said 1,2-benzoquinonediazidosulfonic acid ester is 1,2-benzoquinonediazido-4-sulfonic acid ester or 1,2-benzoquinonediazido-5-sulfonic acid ester.

11. The composition of claim 1, wherein the component-(i), the component-(ii) and the component-(iii) are present in an amount of 100 parts by weight, from 1 part by weight to 50 parts by weight and from 10 parts by weight to 50 parts by weight, respectively.

12. The composition of claim 1, which further comprises a dissolution accelerator.

13. The composition of claim 12, wherein said dissolution accelerator comprises a low-molecular weight phenol compound other than the component-(ii) represented by the formula (1) defined in claim 1.

14. The composition of claim 13, wherein said low-molecular weight phenol compound is selected from the group consisting of compounds represented by the following formulas (5-1) to (5-9), wherein e and f are independently an integer of 0 to 3, x and y are independently an integer of 0 to 3, provided that e and f are not 0 at the same time, e+x≦

5 and f+y≦

7, ##STR17## wherein e, f and g are independently an integer of 0 to 3, x, y and z are independently an integer of 0 to 3, provided that e, f and g are not 0 at the same time, e+x≦

5, f+y≦

4 and g+z≦

5, ##STR18## wherein e, f and g are independently an integer of 0 to 3, x, y and z are independently an integer of 0 to 3, provided that e, f and g are not 0 at the same time, e+x≦

5, f+y≦

5 and g+z≦

5, ##STR19## wherein e, f, g and h are independently an integer of 0 to 3, w, x, y and z are independently an integer of 0 to 3, provided that e, f, g and h are not 0 at the same time, e+w≦

5, f+x≦

5, g+y≦

5 and h+z≦

5.

15. The composition of claim 13, wherein said low-molecular weight phenol compound is selected from the group consisting of the compounds represented by the formulas (5-3), (5-5), (5-6) and (5-7).

16. A pattern-forming process comprising the steps of:

coating on a substrate the radiation-sensitive resin composition according to claim 1 to form a coating;

prebaking the coating to form a resist film;

selectively exposing the resist film to radiation to form a given resist pattern; and

developing the resist pattern by the use of a developing solution.

17. The process of claim 16, wherein said radiation is ultraviolet radiation, X-radiation or charged-particle radiation.

18. A radiation-sensitive resin composition comprising:

(i) an alkali-soluble resin; and

(iiia) a 1,2-benzoquinonediazidosulfonic acid ester of the compound represented by the formula (1) defined in claim 1.

19. The composition of claim 18, wherein the component-(iiia) is present in an amount of from 1 part by weight to 30 parts by weight based on 100 parts by weight of the component (i).

20. A pattern-forming process comprising the steps of:

coating on a substrate the radiation-sensitive resin composition according to claim 16 to form a coating;

prebaking the coating to form a resist film;

selectively exposing the resist film to radiation to form a given resist pattern; and

developing the resist pattern by the use of a developing solution.

21. The process of claim 20, wherein said radiation is ultraviolet radiation, X-radiation or charged-particle radiation.

2. A radiation-sensitive resin composition comprising:

(i) an alkali-soluble resin;

(ii) a phenol compound represented by the following formula (1);

##STR15## wherein R₁ to R₄ are the same or different and each represent a halogen atom, an alkyl group, an alkoxyl group, an aryl group, a nitro group, a cyano group, a hydroxyalkyl group, a hydroxyalkoxyl group or a hydroxyl group;

a, b, c and d independently represent an integer of 0 to 4 and satisfying 0≦

a+b≦

4 and 0≦

c+d≦

4, provided that when a+b is 1 and at least one of R₁ or R₂ and R₃ or R₄ to be present is an alkyl group, a hydroxyalkyl group or a hydroxyalkoxyl group;

R₅ to R₁₀ are the same or different and each represent a hydrogen atom, an alkyl group or an aryl group; and

X₁ and X₂ are the same or different and each represent an oxygen atom or a sulfur atom, provided that when both X₁ and X₂ are oxygen, a+b or c+d is at least 1 and at least one of R₁ and R₂ is a hydroxyalkyl or a hydroxyalkoxyl group; and

(iii) a 1,2-quinonediazide compound.