IP Library Granted Patent US 8,580,480
Granted Patent B2
US 8,580,480 · App. 13/191,416 · Granted Nov 12, 2013

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

Inventors: Yusuke Asano (Tokyo, JP); Mitsuo Sato (Tokyo, JP)
Assignee: JSR Corporation
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Quick Facts
Patent No.
US 8,580,480
App. No.
13/191,416
Granted
Nov 12, 2013
Kind
B2
Abstract

A radiation-sensitive resin composition includes (A) a fluorine-containing compound that includes a group shown by the following formula (1), and (B) a photoacid generator. wherein R C represents a (p+1)-valent aromatic ring group, Q represents a linking group obtained by removing one hydrogen atom from a monovalent hydrophilic group, R E represents a hydrogen atom or a hydrocarbon group having 1 to 10 carbon atoms, p is an integer from 1 to 5, provided that a plurality of Q and a plurality of R E may respectively be either the same or different when p is an integer from 2 to 5, and “*” indicates a bonding hand.

Claims (17)

1. A radiation-sensitive resin composition comprising (A) a fluorine-containing compound that includes a group shown by a formula (1), and (B) a photoacid generator,

wherein R C represents a (p+1)-valent aromatic ring group, Q represents a linking group obtained by removing one hydrogen atom from a monovalent hydrophilic group, R E represents a hydrogen atom or an unsubstituted hydrocarbon group having 1 to 10 carbon atoms, p is an integer from 1 to 5, provided that a plurality of Q and a plurality of R E may respectively be either the same or different when p is an integer from 2 to 5, and “*” indicates a bonding hand.

2. The radiation-sensitive resin composition according to claim 1 , wherein the fluorine-containing compound (A) is a polymer that includes a repeating unit shown by a formula (1p),

wherein R M represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 5 carbon atoms, or an alkyl halide group having 1 to 5 carbon atoms, G represents a single bond, —(CH 2 ) b —, —CO—O—, or —CO—NH— wherein b is 1 or 2, R C1 represents a substituted or unsubstituted (p+1)-valent aromatic ring group, Q represents a linking group obtained by removing one hydrogen atom from a monovalent hydrophilic group, R E represents a hydrogen atom or an unsubstituted hydrocarbon group having 1 to 10 carbon atoms, and p is an integer from 1 to 5, provided that a plurality of Q and a plurality of R E may respectively be either the same or different when p is an integer from 2 to 5.

3. The radiation-sensitive resin composition according to claim 2 , wherein the fluorine-containing compound (A) is a polymer that includes a repeating unit shown by a formula that is selected from the group consisting of formulas (1p-1) to (1p-3),

wherein R M represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 5 carbon atoms, or an alkyl halide group having 1 to 5 carbon atoms, R C2 represents a substituted or unsubstituted (p+1)-valent benzene ring, R E represents a hydrogen atom or an unsubstituted hydrocarbon group having 1 to 10 carbon atoms, and p is an integer from 1 to 5, provided that a plurality of R E may be either the same or different when p is an integer from 2 to 5.

4. The radiation-sensitive resin composition according to claim 3 , wherein the fluorine-containing compound (A) is a polymer that includes a repeating unit shown by a formula that is selected from the group consisting of formulas (1p-1-1) to (1p-3-1),

wherein R B1 to R B4 individually represent a hydrogen atom, a fluorine atom, —R P1 , —R P2 —O—R P1 , —R P2 —CO—R P1 , —R P2 —CO—OR P1 , —R P2 —O—CO—R P1 , —R P2 —OH, —R P2 —CN, or —R P2 —COOH wherein R P1 represents a monovalent chain-like saturated hydrocarbon group having 1 to 10 carbon atoms, a monovalent alicyclic saturated hydrocarbon group having 3 to 20 carbon atoms, or a monovalent aromatic hydrocarbon group having 6 to 30 carbon atoms, provided that some or all of the hydrogen atoms of these groups may be substituted with a fluorine atom, and R P2 represents a single bond, a divalent chain-like saturated hydrocarbon group having 1 to 10 carbon atoms, a divalent alicyclic saturated hydrocarbon group having 3 to 20 carbon atoms, a divalent aromatic hydrocarbon group having 6 to 30 carbon atoms, or a group obtained by substituting some or all of the hydrogen atoms of these groups with a fluorine atom, and R E represents a hydrogen atom or an unsubstituted a-hydrocarbon group having 1 to 10 carbon atoms.

5. The radiation-sensitive resin composition according to claim 1 , further comprising (C) a polymer that includes an acid-labile group, wherein the fluorine-containing polymer (A) has a fluorine atom content higher than that of the polymer (C).

6. A method for forming a resist pattern comprising forming a resist film on a support using the radiation-sensitive resin composition according to claim 1 , subjecting the resist film to liquid immersion lithography, and developing the resist film subjected to liquid immersion lithography to form a resist pattern.

7. A polymer comprising a repeating unit shown by a formula (1p),

wherein R M represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 5 carbon atoms, or an alkyl halide group having 1 to 5 carbon atoms, G represents a single bond, —(CH 2 ) b —, —CO—O—, or —CO—NH— wherein b is 1 or 2, R C1 represents a (p+1)-valent aromatic ring group, Q represents a linking group obtained by removing one hydrogen atom from a monovalent hydrophilic group, R E represents a hydrogen atom or an unsubstituted hydrocarbon group having 1 to 10 carbon atoms, and p is an integer from 1 to 5, provided that a plurality of Q and a plurality of R E may respectively be either the same or different when p is an integer from 2 to 5.

8. A compound shown by a formula (1m),

wherein R M represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 5 carbon atoms, or an alkyl halide group having 1 to 5 carbon atoms, G represents a single bond, —(CH 2 ) b —, —CO—O—, or —CO—NH— wherein b is 1 or 2, R C1 represents a (p+1)-valent aromatic ring group, Q represents a linking group obtained by removing one hydrogen atom from a monovalent hydrophilic group, R E represents a hydrogen atom or an unsubstituted a-hydrocarbon group having 1 to 10 carbon atoms, and p is an integer from 1 to 5, provided that a plurality of Q and a plurality of R E may respectively be either the same or different when p is an integer from 2 to 5.

9. The radiation-sensitive resin composition according to claim 1 , wherein R C represents a substituted (p+1)-valent aromatic ring group.

10. The polymer according to claim 7 , wherein R C1 represents a substituted (p+1)-valent aromatic ring group.

11. The compound according to claim 8 , wherein R C1 represents a substituted (p+1)-valent aromatic ring group.

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 Oct 14, 2011
From: ASANO, YUSUKE; SATO, MITSUO
To: JSR CORPORATION
Reel/Frame 027062/0114 →
Priority Claims (1)
JP 2010-168055 · Jul 27, 2010 · national
Continuity (1)
Related Publication 20120028189A1 · Feb 2, 2012