IP Library Granted Patent US 12,259,653
Granted Patent B2
US 12,259,653 · App. 17/541,422 · Granted Mar 25, 2025

Radiation-sensitive resin composition, method of forming resist pattern, and compound

Inventor: Katsuaki Nishikori (Tokyo, JP)
Assignee: JSR CORPORATION
G03F7/0392C07C51/02C07C55/10C07C55/32G03F7/0045G03F7/0397G03F7/2004G03F7/322G03F7/38G03F7/40
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Quick Facts
Patent No.
US 12,259,653
App. No.
17/541,422
Granted
Mar 25, 2025
Kind
B2
Abstract

A radiation-sensitive resin composition contains: a polymer that includes a structural unit including an acid-labile group; a radiation-sensitive acid generator; and a compound represented by the following formula (1). In the following formula (1), R 1 represents a hydrogen atom or a monovalent organic group having 1 to 30 carbon atoms; and X n+ represents a radiation-sensitive onium cation having a valency of n, wherein n is an integer of 1 to 3. It is preferable that R 1 in the following formula (1) represents an organic group, and that the organic group has a ring structure. It is preferable that R 1 in the following formula (1) represents an organic group, and that the organic group is an acid-labile group. X n+ in the following formula (1) preferably represents a sulfonium cation, an iodonium cation, or a combination thereof.

Claims (32)

1. A radiation-sensitive resin composition comprising:

a polymer which comprises a structural unit comprising an acid-labile group;

a radiation-sensitive acid generator; and

a compound represented by formula (1):

wherein, in the formula (1), R 1 represents a monovalent organic group having 1 to 30 carbon atoms; and X n+ represents a radiation-sensitive onium cation having a valency of n, wherein n is an integer of 1 to 3.

2. The radiation-sensitive resin composition according to claim 1 , wherein R 1 in the formula (1) represents an organic group, and the organic group comprises a ring structure.

3. The radiation-sensitive resin composition according to claim 1 , wherein R 1 in the formula (1) represents an organic group, and the organic group is an acid-labile group.

4. The radiation-sensitive resin composition according to claim 1 , wherein X n+ in the formula (1) represents a sulfonium cation, an iodonium cation, or a combination thereof.

5. The radiation-sensitive resin composition according to claim 1 , wherein n in the formula (1) is 1.

6. A method of forming a resist pattern, the method comprising:

applying a radiation-sensitive resin composition directly or indirectly on a substrate;

exposing a resist film formed by the applying; and

developing the resist film exposed, wherein

the radiation-sensitive resin composition comprises:

a polymer which comprises a structural unit comprising an acid-labile group;

a radiation-sensitive acid generator; and

a compound represented by formula (1):

wherein, in the formula (1), R 1 represents a hydrogen atom or a monovalent organic group having 1 to 30 carbon atoms; and X n+ represents a radiation-sensitive onium cation having a valency of n, wherein n is an integer of 1 to 3.

7. A compound represented by formula (1):

wherein, in the formula (1), R 1 represents a monovalent organic group having 1 to 30 carbon atoms; and X n+ represents a cation having a valency of n, wherein n is an integer of 1 to 3.

8. The compound according to claim 7 , wherein the cation represented by X n+ in the formula (1) is an onium cation.

9. The compound according to claim 8 , wherein the onium cation represented by X n+ is radiation sensitive.

10. The radiation-sensitive resin composition according to claim 1 , wherein the radiation-sensitive acid generator is an acid generating agent, and a content of the acid generating agent in the radiation-sensitive resin composition is from 0.1 parts by mass to 50 parts by mass with respect to 100 parts by mass of the polymer.

11. The radiation-sensitive resin composition according to claim 1 , wherein the radiation-sensitive acid generator is an acid generating agent, and a content of the acid generating agent in the radiation-sensitive resin composition is from 10 parts by mass to 40 parts by mass with respect to 100 parts by mass of the polymer.

12. The radiation-sensitive resin composition according to claim 1 , wherein the radiation-sensitive acid generator is an acid generating agent, and a content of the compound in the radiation-sensitive resin composition is from 1 to 50 mol % with respect to 100 mol % of the acid generating agent.

13. The radiation-sensitive resin composition according to claim 1 , wherein the radiation-sensitive acid generator is an acid generating agent, and a content of the compound in the radiation-sensitive resin composition is from 10 to 30 mol % with respect to 100 mol % of the acid generating agent.

14. The method according to claim 6 , wherein the radiation-sensitive acid generator is an acid generating agent, and a content of the acid generating agent in the radiation-sensitive resin composition is from 0.1 parts by mass to 50 parts by mass with respect to 100 parts by mass of the polymer.

15. The method according to claim 6 , wherein the radiation-sensitive acid generator is an acid generating agent, and a content of the acid generating agent in the radiation-sensitive resin composition is from 10 parts by mass to 40 parts by mass with respect to 100 parts by mass of the polymer.

16. The method according to claim 6 , wherein the radiation-sensitive acid generator is an acid generating agent, and a content of the compound in the radiation-sensitive resin composition is from 1 to 50 mol % with respect to 100 mol % of the acid generating agent.

17. The method according to claim 6 , wherein the radiation-sensitive acid generator is an acid generating agent, and a content of the compound in the radiation-sensitive resin composition is from 10 to 30 mol % with respect to 100 mol % of the acid generating agent.

18. The method according to claim 6 , wherein X n+ in the formula (1) represents a sulfonium cation, an iodonium cation, or a combination thereof.

19. The compound according to claim 9 , wherein X n+ in the formula (1) represents a sulfonium cation, an iodonium cation, or a combination thereof.

Assignments (3)
MERGER Recorded Apr 21, 2025
From: JSR CORPORATION
To: JICC-02 CO., LTD.
Reel/Frame 070894/0405 →
CHANGE OF NAME Recorded Apr 21, 2025
From: JICC-02 CO., LTD.
To: JSR CORPORATION
Reel/Frame 070894/0498 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 3, 2021
From: NISHIKORI, KATSUAKI
To: JSR CORPORATION
Reel/Frame 058278/0589 →
Priority Claims (1)
JP 2019-106474 · Jun 6, 2019 · national
Continuity (2)
Continuation PCTJP2020016474 · Apr 14, 2020
Related Publication 20220091508A1 · Mar 24, 2022
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