Salt, acid generator, resin, resist composition and method for producing resist pattern

Patent metadata

Field	Value
Publication number	US-9880466-B2
Application number	US-201615151618-A
Country	US
Kind code	B2
Filing date	May 11, 2016
Priority date	May 12, 2015
Publication date	Jan 30, 2018
Grant date	Jan 30, 2018

Abstract

A salt represented by formula (I):

wherein Q 1 and Q 2 independently represent a fluorine atom or a C 1 to C 6 perfluoroalkyl group, R 1 and R 2 in each occurrence independently represent a hydrogen atom, a fluorine atom or a C 1 to C 6 perfluoroalkyl group, z represents an integer of 0 to 6, X 1 represents *—CO—O—, *—O—CO— or —O—, * represents a binding position to C(R 1 )(R 2 ) or C(Q 1 )(Q 2 ), A 1 represents a C 4 to C 24 hydrocarbon group having a C 4 to C 18 divalent alicyclic hydrocarbon moiety, A 2 represents a C 2 to C 12 divalent hydrocarbon group, R 3 and R 4 independently represent a hydrogen atom or a C 1 to C 6 monovalent saturated hydrocarbon group, R 5 represents a hydrogen atom, a fluorine atom, or a C 1 to C 6 alkyl group where a hydrogen atom may be replaced by a fluorine atom, and Z + represents an organic cation.

First claim

What is claimed is:

1. A resin comprising a structural unit derived from a salt represented by formula (I):

wherein Q 1 and Q 2 independently represent a fluorine atom or a C 1 to C 6 perfluoroalkyl group,
R 1 and R 2 in each occurrence independently represent a hydrogen atom, a fluorine atom or a C 1 to C 6 perfluoroalkyl group,
z represents an integer of 0 to 6,
X 1 represents *—CO—O—, *—O—CO— or —O—, * represents a binding position to C(R 1 )(R 2 ) or C(Q 1 )(Q 2 ),
A 1 represents a C 4 to C 24 hydrocarbon group having a C 4 to C 18 divalent alicyclic hydrocarbon moiety,
A 2 represents a C 2 to C 6 alkanediyl group,
R 3 represents a C 1 to C 6 monovalent saturated hydrocarbon group,
R 4 represents a hydrogen atom or represents a C 1 to C 6 monovalent saturated hydrocarbon group,
R 5 represents a hydrogen atom, a fluorine atom, or a C 1 to C 6 alkyl group where a hydrogen atom may be replaced by a fluorine atom, and
Z + represents an organic cation.

2. The resin according to claim 1 , further comprising a structural unit having an acid-labile group, which structural unit being different from the structural unit derived from the salt represented by formula (I).

3. The resin according to claim 2 , wherein
the structural unit having an acid-labile group is at least one selected from the group consisting of a structural unit represented by formula (a1-1) and a structural unit represented by formula (a1-2):

wherein L a1 and L a2 independently represent —O— or *—O—(CH 2 ) k1 —CO—O—,
k1 represents an integer of 1 to 7,
* represents a binding position to —CO—,
R a4 and R a5 independently represent a hydrogen atom or a methyl group,
R a6 and R a7 independently represent a C 1 to C 8 alkyl group, a C 3 to C 18 alicyclic hydrocarbon group or a combination thereof,
m1 represents an integer of 0 to 14,
n1 represents an integer of 0 to 10, and
n1′ represents an integer of 0 to 3.

4. A resist composition comprising the resin according to claim 1 and an acid generator.

5. The resist composition according to claim 4 , wherein
the acid generator comprises a salt represented by formula (I):

wherein Q 1 and Q 2 independently represent a fluorine atom or a C 1 to C 6 perfluoroalkyl group,
R 1 and R 2 in each occurrence independently represent a hydrogen atom, a fluorine atom or a C 1 to C 6 perfluoroalkyl group,
z represents an integer of 0 to 6,
X 1 represents *—CO—O—, *—O—CO— or —O—, * represents a binding position to C(R 1 )(R 2 ) or C(Q 1 )(Q 2 ),
A 1 represents a C 4 to C 24 hydrocarbon group having a C 4 to C 18 divalent alicyclic hydrocarbon moiety,
A 2 represents a C 2 to C 6 alkanediyl group,
R 3 and R 4 independently represent a hydrogen atom or a C 1 to C 6 monovalent saturated hydrocarbon group,
R 5 represents a hydrogen atom, a fluorine atom, or a C 1 to C 6 alkyl group where a hydrogen atom may be replaced by a fluorine atom, and
Z + represents an organic cation.

6. The resist composition according to claim 4 , wherein
the acid generator further comprising a salt represented by formula (B1):

wherein Q b1 and Q b2 respectively represent a fluorine atom or a C 1 to C 6 perfluoroalkyl group,
L b1 represents a C 1 to C 24 divalent saturated hydrocarbon group where a methylene group may be replaced by an oxygen atom or a carbonyl group and where a hydrogen atom may be replaced by a hydroxyl group or fluorine atom, and
Y represents an optionally substituted methyl group, or an optionally substituted C 3 to C 18 alicyclic hydrocarbon group where a methylene group may be replaced by an oxygen atom, a carbonyl group or a sulfonyl group, and
Z + represents an organic cation.

7. The resist composition according to claim 4 further comprising a salt which generates an acid lower in acidity than an acid generated from the acid generator.

Assignees

• Sumitomo Chemical Co

Inventors

• Nishimura Takashi
• Ichikawa Koji

Classifications

• G03F7/0045 Primary

  with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors · CPC title

• C07C309/17

  containing carboxyl groups bound to the carbon skeleton · CPC title

• C08F222/102

  of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate · CPC title

• C07C381/12

  Sulfonium compounds · CPC title

• G03F7/0397

  the macromolecular compound having an alicyclic moiety in a side chain · CPC title