IP Library Granted Patent US 8,609,319
Granted Patent B2
US 8,609,319 · App. 13/243,060 · Granted Dec 17, 2013

Radiation-sensitive resin composition and resist film formed using the same

Inventors: Toru Kimura (Tokyo, JP); Hiromitsu Nakashima (Tokyo, JP); Reiko Kimura (Tokyo, JP); Kazuki Kasahara (Tokyo, JP); Masafumi Hori (Tokyo, JP); Masafumi Yoshida (Tokyo, JP)
Assignee: JSR Corporation
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Quick Facts
Patent No.
US 8,609,319
App. No.
13/243,060
Granted
Dec 17, 2013
Kind
B2
Abstract

A radiation-sensitive resin composition that includes (A) a polymer that includes a repeating unit (a1) and a fluorine atom, the repeating unit (a1) including a group shown by the following formula (1) or (2), the radiation-sensitive resin composition including the polymer (A) in an amount of 0.1 mass % or more and less than 20 mass % based on the total amount of polymers included in the radiation-sensitive resin composition.

Claims (29)

1. A radiation-sensitive resin composition comprising:

a polymer component including a polymer (A) and a polymer (B);

the polymer (A) having a repeating unit (a1) and a fluorine atom, the repeating unit (a1) having a group shown by a formula (1) or (2); and

the polymer (B) being other than the polymer (A), being a base polymer of the polymer component and having an acid-dissociable group,

wherein an amount of the polymer (A) is 0.1 mass % or more and less than 20 mass % based on a total amount of the polymer component,

wherein the following formula represents a substituted or unsubstituted aromatic hydrocarbon group,

R 2 represents a hydrogen atom, a linear, branched, or cyclic alkyl group having 1 to 12 carbon atoms, or an aromatic hydrocarbon group, R 3 represents a linear, branched, or cyclic alkyl group having 1 to 12 carbon atoms, provided that R 2 and R 3 may form a divalent alicyclic hydrocarbon group having 5 to 12 carbon atoms together with a carbon atom bonded to R 2 and R 3 , and a is 1 or 2.

2. The radiation-sensitive resin composition according to claim 1 , wherein the repeating unit (a1) is a repeating unit shown by a formula (3) or (4),

wherein the following formula represents a substituted or unsubstituted aromatic hydrocarbon group,

R 2 represents a hydrogen atom, a linear, branched, or cyclic alkyl group having 1 to 12 carbon atoms, or an aromatic hydrocarbon group, R 3 represents a linear, branched, or cyclic alkyl group having 1 to 12 carbon atoms, provided that R 2 and R 3 may form a divalent alicyclic hydrocarbon group having 5 to 12 carbon atoms together with a carbon atom bonded to R 2 and R 3 , a is 1 or 2, and R 1 represents a hydrogen atom, a fluorine atom, or a monovalent chain-like hydrocarbon group that may be substituted with a fluorine atom.

3. The radiation-sensitive resin composition according to claim 1 , wherein the polymer (A) includes a repeating unit (f) that includes a fluorine atom, wherein the repeating unit (f) excludes a repeating unit that falls under the repeating unit (a1).

4. The radiation-sensitive resin composition according to claim 3 , wherein the repeating unit (f) reacts with a developer to produce a polar group.

5. The radiation-sensitive resin composition according to claim 4 , wherein the polar group is a carboxyl group.

6. The radiation-sensitive resin composition according to claim 1 , wherein the amount of the polymer (A) is 1 mass % or more and less than 17 mass % based on a total amount of the polymer component.

7. The radiation-sensitive resin composition according to claim 1 , wherein R 2 and R 3 form a divalent alicyclic hydrocarbon together with a carbon atom bonded to R 2 and R 3 .

8. The radiation-sensitive resin composition according to claim 1 , wherein the polymer (B) does not include the repeating unit (a1).

9. The radiation-sensitive resin composition according to claim 1 , wherein the polymer (B) does not include a fluorine atom, or the polymer (B) has a fluorine atom and a content of the fluorine atom included in the polymer (B) is lower than a content of a fluorine atom included in the polymer (A).

10. The radiation-sensitive resin composition according to claim 1 , wherein the polymer (B) does not include a fluorine atom.

11. The radiation-sensitive resin composition according to claim 1 , wherein the polymer (B) does not include the repeating unit (a1) and does not include a fluorine atom.

12. The radiation-sensitive resin composition according to claim 1 , wherein the polymer (B) includes a repeating unit having a cycloalkane skeleton.

13. The radiation-sensitive resin composition according to claim 3 , wherein a content of the repeating unit (f) in the polymer (A) is from 28 mol % to 95 mol % based on a total amount of repeating units included in the polymer (A).

14. The radiation-sensitive resin composition according to claim 2 , wherein the polymer (A) further includes a repeating unit represented by a formula (f-2),

wherein R m represents a hydrogen atom, a fluorine atom, or a monovalent chain hydrocarbon group that is unsubstituted or substituted with a fluorine atom, R k2 represents a (q+1)-valent linking group, X f2 represents a divalent linking group that includes at least one fluorine atom, R j2 represents a hydrogen atom or a monovalent organic group, and q is an integer from 1 to 3, wherein in a case where q is 2 or 3, each of a plurality of X fn is identical or different to each other, and each of a plurality of R j2 is identical or different to each other.

15. The radiation-sensitive resin composition according to claim 2 , wherein the polymer (A) further includes a repeating unit represented by a formula (f-1),

wherein R m represents a hydrogen atom, a fluorine atom, or a monovalent chain hydrocarbon group that is unsubstituted or substituted with a fluorine atom, and R f1 represents a monovalent chain hydrocarbon group that is substituted with a fluorine atom, or a monovalent alicyclic hydrocarbon group that is substituted with a fluorine atom.

16. The radiation-sensitive resin composition according to claim 2 , wherein the polymer (A) further includes a repeating unit represented by a formula (f-3),

wherein R m represents a hydrogen atom, a fluorine atom, or a monovalent chain hydrocarbon group that is unsubstituted or substituted with a fluorine atom, R k3 represents a (q+1)-valent linking group, R f3 represents a monovalent chain hydrocarbon group that is substituted with a fluorine atom, or a monovalent alicyclic hydrocarbon group that is substituted with a fluorine atom, and r is an integer from 1 to 3, wherein in a case where r is 2 or 3, each of a plurality of R f3 is identical or different to each other.

17. The radiation-sensitive resin composition according to claim 2 , wherein the polymer (A) further includes a repeating unit represented by a formula (f-5),

wherein R m represents a hydrogen atom, a fluorine atom, or a monovalent chain hydrocarbon group that is unsubstituted or substituted with a fluorine atom, R f5 represents a monovalent chain hydrocarbon group that is substituted with a fluorine atom, or a monovalent alicyclic hydrocarbon group that is substituted with a fluorine atom, R k5 represents an (n+1)-valent linking group, and n is an integer from 1 to 3, wherein in a case where n is 2 or 3, each of a plurality of R f5 is identical or different to each other.

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 Dec 16, 2011
From: KIMURA, TORU; NAKASHIMA, HIROMITSU; KIMURA, REIKO; KASAHARA, KAZUKI; HORI, MASAFUMI; YOSHIDA, MASAFUMI
To: JSR CORPORATION
Reel/Frame 027401/0388 →
Priority Claims (1)
JP 2010-223972 · Oct 1, 2010 · national
Continuity (1)
Related Publication 20120082935A1 · Apr 5, 2012