IP Library Granted Patent US 7,488,566
Granted Patent B2
US 7,488,566 · App. 11/391,257 · Granted Feb 10, 2009

Positive type radiation-sensitive resin composition

Assignee: JSR Corporation
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Quick Facts
Patent No.
US 7,488,566
App. No.
11/391,257
Granted
Feb 10, 2009
Kind
B2
Abstract

A positive type radiation-sensitive resin composition suitable as a chemically-amplified resist sensitive to active radiation particularly to deep ultraviolet rays represented by a KrF excimer laser, an ArF excimer laser, or an F 2 excimer laser, excelling particularly in a process margin for the KrF excimer laser is provided. The positive type radiation-sensitive resin composition comprises a photoacid generator and an acid-labile group-containing resin which is insoluble or scarcely soluble in alkali, but becomes alkali-soluble by the action of an acid, wherein the photoacid generator is a mixed photoacid generator containing a photoacid generator of the following formula (1) and a photoacid generator which is at least one compound selected from sulfonyloxyimide and disulfonyldiazomethane.

Claims (33)

1. A positive type radiation-sensitive resin composition comprising

(A) a photoacid generator and (B) an acid-labile group-containing resin which is insoluble or scarcely soluble in alkali, but becomes alkali-soluble by the action of an acid,

wherein (A) the photoacid generator comprises a mixed photoacid generator containing (A1) a photoacid generator of the following formula (1) and (A2) a photoacid generator which is at least one compound selected from the group consisting of sulfonyloxyimides and disulfonyldiazomethanes,

wherein R 1 represents a same or different monovalent organic group containing fluorine atoms, or a fluorine atom, R 2 represents a same or different monovalent organic group containing no fluorine atoms, or a hydrogen atom, n and m are integers of 1-5, and X − represents an anion of camphorsulfonic acid or nonafluorobutanesulfonic acid.

2. The positive type radiation-sensitive resin composition according to claim 1 , wherein (B) the acid-labile group-containing resin comprises a recurring unit of the following formula (2),

wherein R 3 represents a hydrogen atom or a methyl group, R 4 represents a monovalent organic group, two or more R 4 individually represent same or different, s is an integer of 1-3, and t is an integer of 0-3, provided that s+t≦5.

3. The positive type radiation-sensitive resin composition according to claim 2 , wherein the X − is the anion of camphorsulfonic acid.

4. The positive type radiation-sensitive resin composition according to claim 3 , wherein (A2) the photoacid generator comprises a sulfonyloxyimide.

5. The positive type radiation-sensitive resin composition according to claim 4 , wherein the photoacid generator comprises a plurality of different sulfonyloxyimides.

6. The positive type radiation-sensitive resin composition according to claim 3 , wherein (A2) the photo acid generator comprises a disulfonyldiazomethane.

7. The positive type radiation-sensitive resin composition according to claim 2 , wherein the X − is the anion of nonafluorobutanesulfonic acid.

8. The positive type radiation-sensitive resin composition according to claim 7 , wherein (A2) the photoacid generator comprises a sulfonyloxyimide.

9. The positive type radiation-sensitive resin composition according to claim 8 , wherein the photoacid generator comprises a plurality of different sulfonyloxyimides.

10. The positive type radiation-sensitive resin composition according to claim 7 , wherein (A2) the photoacid generator comprises a disulfonyldiazomethane.

11. The positive type radiation-sensitive resin composition according to claim 2 , wherein (B) the acid-labile group-containing resin further comprises a recurring unit which is at least one recurring unit selected from the group consisting of a recurring unit of the following formula (3) and a recurring unit of the following formula (4),

wherein R 5 represents a hydrogen atom or a methyl group, R 6 represents a monovalent organic group, R 7 represents a monovalent acid-labile group, p is an integer of 1-3, q is an integer of 0-3, provided that p+q≦5 of the formula (3), R 8 represents a hydrogen atom or a methyl group, and R 9 represents a t-butyl group, a 1-methylcyclopentyl group or a 1-ethylcyclopentyl group of the formula (4).

12. The positive type radiation-sensitive resin composition according to claim 1 , wherein the photoacid generator (A) consists of a photoacid generator of the formula (1) and at least one compound selected from the group consisting of sulfonyloxyimides and disulfonyldiazomethanes.

13. The positive type radiation-sensitive resin composition according to claim 1 , wherein the photoacid generator (A) further comprises a photoacid generator (A3) selected from the group consisting of an onium salt, a sulfone compound, a sulfonic acid ester compound, an oximesulfonate compound and a hydrazinesulfonate compound.

14. The composition of claim 13 , wherein the photoacid generator (A3) is an onium salt.

15. A positive type radiation-sensitive resin composition comprising

(A) a photoacid generator and (B) an acid-labile group-containing resin which is insoluble or scarcely soluble in alkali, but becomes alkali-soluble by the action of an acid,

wherein (A) a photoacid generator of the following formula (1) and (A2) a photoacid generator which is at least one compound selected from the group consisting of sulfonyloxyimides and disulfonyldiazomethanes,

wherein each R 1 represents a same or different monovalent organic group consisting fluorine atoms or a fluorine atom, R 2 independently represents a same or different monovalent organic group containing no fluorine atoms, n and m are integers of 1-5, and X − represents an anion of camphorsulfonic acid or nonafluorobutanesulfonic acid.

16. The positive type radiation-sensitive resin composition according to claim 15 , wherein (B) the acid-labile group-containing resin comprises a recurring unit of the following formula (2),

wherein R 3 represents a hydrogen atom or a methyl group, R 4 represents a monovalent organic group, two or more R 4 represent same or different, s is an integer of 1-3, and t is an integer of 0-3, provided that s+t≦5.

17. The positive type radiation-sensitive resin composition according to claim 16 , wherein the X − is the anion of camphorsulfonic acid.

18. The positive type radiation-sensitive resin composition according to claim 17 , wherein (A2) the photoacid generator is a sulfonyloxyimide.

19. The positive type radiation-sensitive resin composition according to claim 17 , wherein (A2) the photoacid generator is a disulfonyldiazomethane.

20. The positive type radiation-sensitive resin composition according to claim 16 , wherein the X − is the anion of nonafluorobutanesulfonic acid.

21. The positive type radiation-sensitive resin composition according to claim 20 , wherein (A2) the photoacid generator is a sulfonyloxyimide.

22. The positive type radiation-sensitive resin composition according to claim 20 , wherein (A2) the photoacid generator is a disulfonyldiazomethane.

23. The positive type radiation-sensitive resin composition according to claim 16 , wherein (B) the acid-labile group-containing resin further comprises a recurring unit which is at least one recurring unit selected from the group consisting of a recurring unit of the following formula (3) and a recurring unit for the following formula (4),

wherein R 5 represents a hydrogen atom or a methyl group, R 6 represents a monovalent organic group, R 7 represents a monovalent acid-labile group, p is an integer of 1-3, q is an integer of 0-3, provided that p+q≦5 of the formula (3), R 8 represents a hydrogen atom or a methyl group, and R 9 represents t-butyl group, 1-methylcyclopentyl group or 1-ethylcyclopentyl group of the formula (4).

Assignments (3)
MERGER Recorded Mar 23, 2026
From: JSR CORPORATION
To: JICC-02, CO., LTD
Reel/Frame 075191/0149 →
CHANGE OF NAME Recorded Mar 23, 2026
From: JICC-02 CO., LTD
To: JSR CORPORATION
Reel/Frame 075192/0023 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 13, 2006
From: TSUJI, TAKAYUKI; NAGAI, TOMOKI; HARADA, KENTAROU; SHIMIZU, DAISUKE
To: JSR CORPORATION
Reel/Frame 017770/0110 →
Priority Claims (1)
JP 2005-093385 · Mar 29, 2005 · national
Continuity (1)
Related Publication 20060223010A1 · Oct 5, 2006