IP Library Granted Patent US 9,128,370
Granted Patent B2
US 9,128,370 · App. 13/759,118 · Granted Sep 8, 2015

Radiation-sensitive composition and compound

Inventor: Ken Maruyama (Tokyo, JP)
Assignee: JSR Corporation
G03C1/73C07C25/18C07C309/06C07C309/25C07C381/12C07D307/93G03F7/0045G03F7/0046G03F7/0392G03F7/0397G03F7/2041C07C2101/04C07C2101/08C07C2101/14C07C2101/18
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Quick Facts
Patent No.
US 9,128,370
App. No.
13/759,118
Granted
Sep 8, 2015
Kind
B2
Abstract

A radiation-sensitive composition includes a photoacid generator represented by a general formula (1), and a solvent. Each R 0 independently represents a hydrogen atom, a fluorine atom, or a substituted or unsubstituted monovalent organic group. R 1 represents a fluorine atom or a substituted or unsubstituted monovalent organic group. R 2 represents a fluorine atom or a substituted or unsubstituted monovalent organic group. R f represents a fluoromethylene group or a divalent fluoroalkylene group. M + represents a monovalent onium cation. Optionally R 1 bonds to R f or R 2 to form a cyclic structure.

Claims (33)

1. A radiation-sensitive composition comprising:

a photoacid generator represented by formula (2); and

a solvent,

wherein R 1 represents

a linear or branched hydrocarbon group having 1 to 30 carbon atoms, some or all of the hydrogen atoms of the hydrocarbon group represented by R 1 being substituted with a fluorine atom,

wherein R 2 represents a fluorine atom or a substituted or unsubstituted organic group, R f represents a linear or branched fluoroalkylene group having 2 to 30 carbon atoms,M + represents a monovalent onium cation, and optionally R 1 bonds to R f or R 2 to form a cyclic structure, and

wherein the monovalent onium cation (M + ) is a sulfonium cation represented by formula (m1-1),

wherein each of R 111 to R 113 independently represents a hydroxyl group, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, —S—R 114 , or —SO 2 —R 115 , 1 is an integer from 1 to 5, m is an integer from 0 to 5, and n is an integer from 0 to 5,

wherein R 114 represents a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group,

wherein R 115 represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, or a substituted or unsubstituted aryl group, and

wherein at least one R 111 represents —SO 2 —R 115 .

2. The radiation-sensitive composition according to claim 1 , further comprising a resin that comprises at least one repeating unit among repeating units respectively represented by formulas (b-1) to (b-5),

wherein R 11 represents a hydrogen atom or a methyl group, R 12 represents a linear or branched alkyl group having 1 to 12 carbon atoms or a linear or branched alkoxy group having 1 to 12 carbon atoms, k is an integer from 0 to 3, and 1 is an integer from 0 to 3, wherein k+1≦5 is satisfied,

wherein R 13 represents a hydrogen atom or a methyl group, R 14 represents a linear or branched alkyl group having 1 to 12 carbon atoms or a linear or branched alkoxy group having 1 to 12 carbon atoms, m is an integer from 0 to 3, and n is an integer from 0 to 3, wherein m+n≦5 is satisfied,

wherein R 15 represents a hydrogen atom or a methyl group, R 16 represents a linear or branched alkyl group having 1 to 12 carbon atoms or a linear or branched alkoxy group having 1 to 12 carbon atoms, p is an integer from 0 to 3, and q is an integer from 0 to 3, wherein p+q≦5 is satisfied,

wherein R 17 represents a hydrogen atom or a methyl group, R 18 represents a linear or branched alkyl group having 1 to 12 carbon atoms or a linear or branched alkoxy group having 1 to 12 carbon atoms, r is an integer from 0 to 3, and s is an integer from 0 to 3,

wherein R 19 represents a hydrogen atom or a methyl group.

3. The radiation-sensitive composition according to claim 1 , wherein in the formula (2), R 1 represents CF 3 —, R 2 represents a fluorine atom, and R 1 represents —CF 2 —.

4. The radiation-sensitive composition according to claim 1 , wherein in the formula (2), R 1 represents C 4 F 9 —, R 2 represents a fluorine atom, and R f represents —C 4 F 8 —.

5. The radiation-sensitive composition according to claim 1 , further comprising a photosensitive basic compound which comprises a compound represented by formula (5-1), a compound represented by formula (5-2), or both thereof:

wherein, in the formula (5-1), R 51 to R 53 independently represent a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alicyclic hydrocarbon group, —OSO 2 —R 56 , or —SO 2 —R 57 ,wherein R 56 and R 57 represent a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alicyclic hydrocarbon group, or a substituted or unsubstituted aryl group, and two or more of R 51 to R 53 optionally bond to form a cyclic structure, and A − represents OH − , R 58 O − , or R 58 COO − , wherein R 58 represents a monovalent organic group, and

wherein, in the formula (5-2), R 54 and R 55 independently represent a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted alicyclic hydrocarbon group, and A − represents OH − , R 59 O − , or R 59 COO − , wherein R 59 represents a monovalent organic group.

6. The radiation-sensitive composition according to claim 5 , wherein, in the formulas (5-1) and (5-2), A − represents a compound represented by formulas (6-1) to (6-5):

7. A compound represented by formula (2),

wherein R 1 represents a linear or branched hydrocarbon group having 1 to 30 carbon atoms, some or all of the hydrogen atoms of the hydrocarbon group represented by R 1 being substituted with a fluorine atom,

wherein R 2 represents a fluorine atom or a substituted or unsubstituted organic group, R f represents a linear or branched fluoroalkylene group having 2 to 30 carbon atoms, M + represents a monovalent onium cation, and optionally R 1 bonds to R f or R 2 to form a cyclic structure, and

wherein the monovalent onium cation (M + ) is a sulfonium cation represented by formula (m1-1),

wherein each of R 111 to R 113 independently represents a hydroxyl group, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, —S—R 114 , or —SO 2 —R 115 , 1 is an integer from 1 to 5, m is an integer from 0 to 5, and n is an integer from 0 to 5,

wherein R 114 represents a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group,

wherein R 115 represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, or a substituted or unsubstituted aryl group, and

wherein at least one R 111 represents —SO 2 —R 115 .

8. The compound according to claim 7 , wherein in the formula (2), R 1 represents CF 3 —, R 2 represents a fluorine atom, and R f represents —CF 2 —.

9. The compound according to claim 7 , wherein in the formula (2), R 1 represents C 4 F 9 —, R 2 represents a fluorine atom, and R f represents —C 4 F 8 —.

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 Feb 5, 2013
From: MARUYAMA, KEN
To: JSR CORPORATION
Reel/Frame 029752/0587 →
Priority Claims (1)
JP 2010-182627 · Aug 17, 2010 · national
Continuity (2)
Continuation PCTJP2011066497 · Jul 20, 2011
Related Publication 20130149644A1 · Jun 13, 2013