IP Library Granted Patent US 9,104,102
Granted Patent B2
US 9,104,102 · App. 13/560,987 · Granted Aug 11, 2015

Radiation-sensitive resin composition

Inventors: Yasuhiko Matsuda (Tokyo, JP); Takanori Kawakami (Tokyo, JP); Kazuki Kasahara (Tokyo, JP); Ken Maruyama (Tokyo, JP)
Assignee: JSR CORPORATION
G03F7/0045G03F7/0046G03F7/0397G03F7/11G03F7/2041
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Quick Facts
Patent No.
US 9,104,102
App. No.
13/560,987
Granted
Aug 11, 2015
Kind
B2
Abstract

A radiation-sensitive resin composition includes a compound represented by a following formula (1), and a first polymer that serves as a base resin. R 1 represents a monovalent alicyclic hydrocarbon group having 3 to 20 carbon atoms, or the like. The M + represents a monovalent cation. The first polymer (B) is preferably insoluble or hardly soluble in alkali, the polymer including a structure unit represented by a formula (5) or a structure unit represented by a formula (6), and a structure unit represented by a formula (7).

Claims (37)

1. A radiation-sensitive resin composition comprising:

a compound represented by formula (1); and

a first polymer that serves as a base resin,

wherein in the formula (1),

Rrepresents an alkyl group having 1 to 20 carbon atoms, a monovalent alicyclic hydrocarbon group having 3 to 20 carbon atoms, an aryl group having 6 to 15 carbon atoms or a heteroaryl group having 4 to 15 carbon atoms;

R 2 represents an ether group, an ester group, a carbonyl group, a bivalent chain hydrocarbon group having 1 to 30 carbon atoms, a bivalent cyclic hydrocarbon group having 3 to 30 carbon atoms, a bivalent aromatic hydrocarbon group having 6 to 30 carbon group or a group derived by combining two or more thereof;

R f represents a fluorine atom;

M + represents a monovalent cation;

n1 is 0 or 1; and

n2 is 1.

2. The radiation-sensitive resin composition according to claim 1 , wherein R 1 represents a monovalent alicyclic hydrocarbon group having 3 to 20 carbon atoms.

3. The radiation-sensitive resin composition according to claim 1 , wherein M + represents a sulfonium cation or an iodonium cation.

4. The radiation-sensitive resin composition according to claim 1 , wherein the first polymer is insoluble or hardly soluble in alkali, the first polymer comprising:

a structure unit represented by formula (5) or a structure unit represented by formula (6); and

a structure unit represented by formula (7),

wherein in the formula (5), formula (6) and formula (7),

R 9 , R 13 and R 15 each independently represent a hydrogen atom or a methyl group, wherein in the formula (5),

R 10 , R 11 and R 12 each independently represent a hydrogen atom, a hydroxyl group, a cyano group or —COOR 19 ; and

R 19 represents a hydrogen atom, a linear or branched alkyl group having 1 to 4 carbon atoms, or a cycloalkyl group having 3 to 20 carbon atoms,

wherein in the formula (6),

R 14 represents a single bond or a bivalent linking group; and

R Lc represents a monovalent organic group having a lactone structure, and wherein in the formula (7),

R 16 , R 17 and R 18 each independently represent a monovalent alicyclic hydrocarbon group having 4 to 20 carbon atoms or a derivative thereof, or a linear or branched alkyl group having 1 to 4 carbon atoms, wherein at least one group of R 16 , R 17 and R 18 represents an alicyclic hydrocarbon group having 4 to 20 carbon atoms or a derivative thereof, or two groups of R 16 , R 17 and R 18 taken together represent a bivalent alicyclic hydrocarbon group having 4 to 20 carbon atoms or a derivative thereof together with the carbon atom to which the two groups are each attached.

5. The radiation-sensitive resin composition according to claim 1 , further comprising a second polymer having a content of fluorine atoms greater than a content of fluorine atoms of the first polymer.

6. The radiation-sensitive resin composition according to claim 1 , wherein in the formula (1), R 1 represents a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a 2-norbornyl group, a 1-adamantyl group, or a 2-adamantyl group.

7. The radiation-sensitive resin composition according to claim 1 , wherein in the formula (1), R 1 represents a cyclohexyl group or a 1-adamantyl group.

8. The radiation-sensitive resin composition according to claim 1 , further comprising an acid diffusion control agent represented by a formula: X + Z − , wherein

X + is a cation represented by a formula (19) or a formula (20);

Z − is OH − , an anion represented by a formula of R 75 —COO − , or an anion represented by a formula of R 75 —SO 3 31 ; and

R 75 represents an alkyl group, an alicyclic hydrocarbon group, or an aryl group, wherein, a part or all of hydrogen atoms of the alkyl group, the alicyclic hydrocarbon group, or the aryl group are substituted or not substituted:

wherein in the formula (19),

R 76 to R 78 each independently represent a hydrogen atom, an alkyl group, an alkoxyl group, a hydroxyl group or a halogen atom, and

wherein in the formula (20),

R 79 and R 80 each independently represent a hydrogen atom, an alkyl group, an alkoxyl group, a hydroxyl group or a halogen atom.

9. The radiation-sensitive resin composition according to claim 8 , wherein Z 31 is OH − or the anion represented by the formula of: R 75 —COO − .

10. The radiation-sensitive resin composition according to claim 8 , wherein Z 31 is an anion represented by a formula:

11. The radiation-sensitive resin composition according to claim 8 , wherein Z 31 is an anion represented by a formula:

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 Jul 27, 2012
From: MATSUDA, YASUHIKO; KAWAKAMI, TAKANORI; KASAHARA, KAZUKI; MARUYAMA, KEN
To: JSR CORPORATION
Reel/Frame 028663/0273 →
Priority Claims (1)
JP 2010-018466 · Jan 29, 2010 · national
Continuity (2)
Continuation PCTJP2011051335 · Jan 25, 2011
Related Publication 20120295198A1 · Nov 22, 2012