IP Library Granted Patent US 9,140,984
Granted Patent B2
US 9,140,984 · App. 13/527,731 · Granted Sep 22, 2015

Radiation-sensitive composition

Inventors: Yuji Yada (Tokyo, JP); Tooru Kimura (Tokyo, JP); Tomohiro Utaka (Tokyo, JP)
Assignee: JSR CORPORATION
G03F7/0392C08F12/22C08F212/14G03F7/0397
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Quick Facts
Patent No.
US 9,140,984
App. No.
13/527,731
Granted
Sep 22, 2015
Kind
B2
Abstract

A radiation-sensitive composition includes a polymer composition and a radiation-sensitive acid generator. The polymer composition includes a first polymer and a second polymer. The first polymer includes a repeating unit shown by a following formula (1). The second polymer includes a repeating unit shown by a following formula (2) and does not include a repeating unit shown by the formula (1).

Claims (47)

1. A radiation-sensitive composition comprising:

a polymer composition comprising a first polymer and a second polymer, said first polymer comprising a repeating unit shown by formula (1) and a repeating unit comprising an acid-labile group, said second polymer comprising a repeating unit shown by formula (2) and not comprising a repeating unit shown by the formula (1); and

a radiation-sensitive acid generator,

wherein in the formula (1),

R 1 represents a hydrogen atom, a methyl group, or a trifluoromethyl group,

R 2 represents a hydrogen atom, a linear or branched alkyl group having 1 to 12 carbon atoms, a linear or branched alkoxyl group having 1 to 12 carbon atoms, or a group shown by formula (1-1), and

i represents an integer from 1 to 3, and j represents an integer from 0 to 3, satisfying i+j≦5;

wherein in the formula (1-1),

each R′ individually represents a hydrogen atom or a methyl group, and

R″ represents a linear or branched alkyl group having 1 to 8 carbon atoms or a cycloalkyl group; and

wherein in the formula (2),

R 3 represents a hydrogen atom or a methyl group, and

each R 4 individually represents a monovalent alicyclic hydrocarbon group having 4 to 20 carbon atoms, a derivative thereof, or a linear or branched alkyl group having 1 to 4 carbon atoms, or

two of R 4 s bond to each other to form a divalent alicyclic hydrocarbon group having 4 to 20 carbon atoms or a derivative thereof in combination with the carbon atom to which the two of R 4 s bond, and one of R 4 s other than the two of R 4 s is a linear or branched alkyl group having 1 to 4 carbon atoms, a monovalent alicyclic hydrocarbon group having 4 to 20 carbon atoms, or a derivative thereof,

wherein said second polymer is contained at 1 to 20 weight % for 100 weight % of said polymer composition.

2. The radiation-sensitive composition according to claim 1 , wherein said repeating unit comprising an acid-labile group is shown by formula (6) or formula (7),

wherein in the formulas (6) and (7),

R 10 represents a hydrogen atom or a methyl group;

wherein in the formula (6),

R 11 represents a monovalent acid-labile group, and

1 is an integer from 1 to 3; and

wherein in the formula (7),

R 12 represents a monovalent acid-labile group.

3. The radiation-sensitive composition according to claim 1 , wherein said second polymer comprises a repeating unit shown by formula (3-1), a repeating unit shown by formula (3-2), a repeating unit shown by formula (3-3), or a combination thereof,

wherein in the formulas (3-1) to (3-3),

R 5 represents a hydrogen atom or a methyl group;

wherein in the formula (3-1),

R 6 represents a hydrogen atom, a linear or branched alkyl group having 1 to 4 carbon atoms, a linear or branched alkoxyl group having 1 to 4 carbon atoms, or a linear or branched fluoroalkyl group having 1 to 4 carbon atoms;

wherein in the formula (3-2),

R 7 represents a hydrogen atom or a linear or branched alkyl group having 1 to 4 carbon atoms, and

k represents an integer from 0 to 3; and

wherein in the formula (3-3),

L represents a single bond or an alkylene group having 1 to 3 carbon atoms.

4. The radiation-sensitive composition according to claim 1 , wherein said second polymer further comprises a repeating unit shown by formula (4),

wherein in the formula (4),

R 8 represents a hydrogen atom or a methyl group, and

R 9 represents a polycyclic alicyclic hydrocarbon group having 7 to 20 carbon atoms.

5. The radiation-sensitive composition according to claim 1 , wherein said radiation-sensitive acid generator comprises a non-ionic radiation-sensitive acid generator.

6. The radiation-sensitive composition according to claim 5 , wherein said non-ionic radiation-sensitive acid generator is a sulfonyloxyimide compound.

7. The radiation-sensitive composition according to claim 5 , wherein said non-ionic radiation-sensitive acid generator is a sulfonyldiazomethane compound.

8. The radiation-sensitive composition according to claim 5 , wherein said radiation-sensitive acid generator further comprises an onium salt compound that generates a benzenesulfonic acid that is substituted with a fluorine atom or unsubstituted.

9. The radiation-sensitive composition according to claim 3 , wherein said second polymer further comprises a repeating unit shown by formula (4),

wherein in the formula (4),

R 8 represents a hydrogen atom or a methyl group, and

R 9 represents a polycyclic alicyclic hydrocarbon group having 7 to 20 carbon atoms.

10. The radiation-sensitive composition according to claim 6 , wherein said radiation-sensitive acid generator further comprises an onium salt compound that generates a benzenesulfonic acid that is substituted with a fluorine atom or unsubstituted.

11. The radiation-sensitive composition according to claim 7 , wherein said radiation-sensitive acid generator further comprises an onium salt compound that generates a benzenesulfonic acid that is substituted with a fluorine atom or unsubstituted.

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 20, 2012
From: YADA, YUJI; KIMURA, TOORU; UTAKA, TOMOHIRO
To: JSR CORPORATION
Reel/Frame 028408/0697 →
Priority Claims (1)
JP 2009-291346 · Dec 22, 2009 · national
Continuity (2)
Continuation PCTJP2010072420 · Dec 14, 2010
Related Publication 20120282550A1 · Nov 8, 2012