IP Library Granted Patent US 9,304,393
Granted Patent B2
US 9,304,393 · App. 13/929,357 · Granted Apr 5, 2016

Radiation-sensitive resin composition and compound

Inventors: Kazuo Nakahara (Tokyo, JP); Ken Maruyama (Tokyo, JP)
Assignee: JSR CORPORATION
G03F7/004C07C22/02C07C22/08C07C25/18C07C309/19C07C381/12C07D307/77C08K5/07G03F7/0045G03F7/0046G03F7/0392G03F7/0397G03F7/11G03F7/2041C07C2101/08C07C2101/14C07C2101/16C07C2102/42
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Quick Facts
Patent No.
US 9,304,393
App. No.
13/929,357
Granted
Apr 5, 2016
Kind
B2
Abstract

A radiation-sensitive resin composition includes a compound represented by a formula (1), and a polymer that includes a structural unit having an acid-labile group. R 1 and R 4 each independently represent a hydrogen atom, or the like. R 2 and R 3 each independently represent a hydrogen atom or the like. X 1 and X 2 each independently represent a hydrogen atom, or the like, or X 1 and X 2 taken together represent —S—, —O—, —SO 2 —, or the like. A represents an ethanediyl group, wherein at least one hydrogen atom included in X 1 , X 2 and A is substituted by —Y—SO 3 − M + . Y represents an alkanediyl group having 1 to 10 carbon atoms, or the like. M + represents a monovalent onium cation. In the case where —Y—SO 3 − M + is present in a plurality of number, a plurality of Ys are each identical or different and a plurality of M + s are each identical or different.

Claims (36)

1. A radiation-sensitive resin composition comprising:

a compound represented by formula (1); and

a polymer that comprises a structural unit comprising an acid-labile group:

wherein, in the formula (1),

R 1 represents —ZR 5 , and R 4 represents —ZR 6 , wherein each Z represents —O— or —NH—, and R 5 and R 6 each independently represent an alicyclic group having 3 to 10 carbon atoms or a group comprising a lactone structure having 4 to 12 carbon atoms;

R 2 and R 3 each independently represent a hydrogen atom or a monovalent organic group;

X 1 and X 2 each independently represent a hydrogen atom, a hydroxyl group, a thiol group, a sulfonyl group or a monovalent organic group, or X 1 and X 2 taken together represent —S—, —O—, —SO 2 —, an alkanediyl group having 1 to 10 carbon atoms or a combined group thereof; and

A represents an ethanediyl group,

wherein at least one hydrogen atom included in X 1 , X 2 and A is substituted by —Y—SO 3 − M + , wherein Y represents an alkanediyl group having 1 to 10 carbon atoms that is substituted with a fluorine atom, and two fluorine atoms bond to a carbon atom adjacent to SO 3 − , and M + represents a monovalent onium cation, and in the case where —Y—SO 3 − M + is present in a plurality of number, a plurality of Ys are each identical or different and a plurality of M + s are each identical or different.

2. The radiation-sensitive resin composition according to claim 1 , wherein the compound is represented by formula (2):

wherein, in the formula (2), R 1 to R 4 , Y and M + are as defined in the formula (1); X represents —S—, —O—, —SO 2 —, an alkanediyl group having 1 to 10 carbon atoms or a combined group thereof; and n is an integer of 1 to 4.

3. The radiation-sensitive resin composition according to claim 1 , wherein

R 1 represents —OR 5 , and R 4 represents —OR 6 , wherein R 5 and R 6 each independently represent an alicyclic group having 3 to 10 carbon atoms or a group comprising a lactone structure having 4 to 12 carbon atoms.

4. The radiation-sensitive resin composition according to claim 1 , wherein the polymer further comprises a structural unit comprising a lactone structure or a cyclic carbonate structure, a structural unit comprising a polar group, or a combination thereof.

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

6. The radiation-sensitive resin composition according to claim 1 , further comprising a fluorine atom-containing polymer.

7. The radiation-sensitive resin composition according to claim 1 , further comprising a nitrogen-containing compound.

8. A compound represented by formula (1):

wherein, in the formula (1),

R 1 represents —ZR 5 , and R 4 represents —ZR 6 , wherein each Z represents —O— or —NH—, and R 5 and R 6 each independently represent an alicyclic group having 3 to 10 carbon atoms or a group comprising a lactone structure having 4 to 12 carbon atoms;

R 2 and R 3 each independently represent a hydrogen atom or a monovalent organic group;

X 1 and X 2 each independently represent a hydrogen atom, a hydroxyl group, a thiol group, a sulfonyl group or a monovalent organic group, or X 1 and X 2 taken together represent —S—, —O—, —SO 2 —, an alkanediyl group having 1 to 10 carbon atoms or a combined group thereof; and

A represents an ethanediyl group,

wherein at least one hydrogen atom included in X 1 , X 2 and A is substituted by —Y—SO 3 − M + , wherein Y represents an alkanediyl group having 1 to 10 carbon atoms that is substituted with a fluorine atom and two fluorine atoms bond to a carbon atom adjacent to SO 3 − , and M + represents a monovalent onium cation, and in the case where —Y—SO 3 − M + is present in a plurality of number, a plurality of Ys are each identical or different and a plurality of M + s are each identical or different.

9. The compound according to claim 8 , wherein

R 1 represents —OR 5 , and R 4 represents —OR 6 , wherein R 5 and R 6 each independently represent an alicyclic group having 3 to 10 carbon atoms or a group comprising a lactone structure having 4 to 12 carbon atoms.

10. A compound represented by formula (2):

wherein, in the formula (2),

R 1 represents —ZR 5 , and R 4 represents —ZR 6 , wherein each Z represents —O— or —NH—, and R 5 and R 6 each independently represent an alicyclic group having 3 to 10 carbon atoms or a group comprising a lactone structure having 4 to 12 carbon atoms;

R 2 and R 3 each independently represent a hydrogen atom or a monovalent organic group;

Y represents an alkanediyl group having 1 to 10 carbon atoms that is substituted with a fluorine atom, and two fluorine atoms bond to a carbon atom adjacent to SO 3 − ;

M + represents a monovalent onium cation;

X represents —S—, —O—, —SO 2 —, an alkanediyl group having 1 to 10 carbon atoms or a combined group thereof;

n is an integer of 1 to 4; and

in the case where —Y—SO 3 − M + is present in a plurality of number, a plurality of Ys are each identical or different and a plurality of M + s are each identical or different.

11. The compound according to claim 10 , wherein R 1 represents —OR 5 , and R 4 represents —OR 6 , wherein R 5 and R 6 each independently represent an alicyclic group having 3 to 10 carbon atoms or a group comprising a lactone structure having 4 to 12 carbon atoms.

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 27, 2013
From: NAKAHARA, KAZUO; MARUYAMA, KEN
To: JSR CORPORATION
Reel/Frame 030702/0737 →
Priority Claims (1)
JP 2010-293362 · Dec 28, 2010 · national
Continuity (2)
Continuation PCTJP2011080118 · Dec 26, 2011
Related Publication 20130288179A1 · Oct 31, 2013