Salt and photoresist composition comprising the same

Patent metadata

Field	Value
Publication number	US-9562032-B2
Application number	US-201514601825-A
Country	US
Kind code	B2
Filing date	Jan 21, 2015
Priority date	Jan 24, 2014
Publication date	Feb 7, 2017
Grant date	Feb 7, 2017

Abstract

A salt which has a group represented by formula (a):

wherein X a and X b each independently represent an oxygen atom or a sulfur group;
X 1 represents a C1-C12 divalent saturated hydrocarbon group which has a hydroxy group; and
* represents a binding site.

First claim

What is claimed is:

1. A salt which has
a moiety represented by formula (a1):

wherein X a and X b each independently represent an oxygen atom or a sulfur group;
X 1 represents a C1-C12 divalent saturated hydrocarbon group which has a hydroxy group;
the ring W represents a C3-C36 alicyclic hydrocarbon group in which a methylene group can be replaced by an oxygen atom, a sulfur atom, a carbonyl group or a sulfonyl group, and in which a hydrogen atom can be replaced by a hydroxy group, a C1-C12 alkyl group, a C1-C12 alkoxy group, a C3-C12 alicyclic hydrocarbon group, a C6-C10 aromatic hydrocarbon group or a combination of any two or more of them; and
* represents a binding site.

2. The salt according to claim 1 comprising a cation and an anion which has the moiety represented by formula (a1).

3. The salt according to claim 2 wherein the cation is an arylsulfonium cation.

4. The salt according to claim 1 wherein the ring W is a C6-C10 alicyclic hydrocarbon group in which a methylene group can be replaced by an oxygen atom, a sulfur atom, a carbonyl group or a sulfonyl group, and in which a hydrogen atom can be replaced by a hydroxy group, a C1-C12 alkyl group, a C1-C12 alkoxy group, a C3-C12 alicyclic hydrocarbon group, a C6-C10 aromatic hydrocarbon group or a combination of any two or more of them.

5. The salt according to claim 2 wherein the anion is represented by formula (a2):

wherein X a and X b each independently represent an oxygen atom or a sulfur group;
X 1 represents a C1-C12 divalent saturated hydrocarbon group which has a hydroxy group;
the ring W represents a C3-C36 alicyclic hydrocarbon group in which a methylene group can be replaced by an oxygen atom, a sulfur atom, a carbonyl group or a sulfonyl group, and in which a hydrogen atom can be replaced by a hydroxy group, a C1-C12 alkyl group, a C1-C12 alkoxy group, a C3-C12 alicyclic hydrocarbon group, a C6-C10 aromatic hydrocarbon group or a combination of any two or more of them, L b1 represents a C1-C24 divalent saturated hydrocarbon group where a methylene group can be replaced by an oxygen atom or a carbonyl group and where a hydrogen atom can be replaced by a fluorine atom or a hydroxy group; and
Q 1 and Q 2 each independently represent a fluorine atom or a C1-C6 perfluoroalkyl group.

6. The salt according to claim 5 wherein the ring W is a C6-C10 alicyclic hydrocarbon group in which a methylene group can be replaced by an oxygen atom, a sulfur atom, a carbonyl group or a sulfonyl group, and in which a hydrogen atom can be replaced by a hydroxy group, a C1 -C12 alkyl group, a C1-C12 alkoxy group, a C3-C12 alicyclic hydrocarbon group, a C6-C10 aromatic hydrocarbon group or a combination of any two or more of them.

7. The salt according to claim 5 wherein L b1 is *—CO—O—(CH 2 ) t — where t is an integer of 0 to 6 and * represents a binding site to C(Q 1 ) (Q 2 ), or *—CH 2 —O—CO— where * represents a binding site to C(Q 1 ) (Q 2 ).

8. The salt according to claim 1 wherein X 1 is a C1-C6 alkanediyl group which has a hydroxymethyl group.

9. The salt according to claim 1 wherein X 1 is a divalent group represented by formula (X 1 −1) formula (X 1 −2), formula (X 1 −3), formula or (X 1 −4):

where * represents a binding site to X a or x b .

10. An acid generator which comprises the salt according to claim 1 .

11. A photoresist composition comprising the acid generator according to claim 10 and a resin which has an acid-labile group.

12. The photoresist composition according to claim 11 , further comprising a salt which has an acidity weaker than an acid generated from the acid generator.

13. A process for producing a photoresist pattern comprising the following steps (1) to (5):
(1) a step of applying the photoresist composition according to claim 11 on a substrate,
(2) a step of forming a composition film by conducting drying,
(3) a step of exposing the composition film to radiation,
(4) a step of baking the exposed composition film, and
(5) a step of developing the baked composition film.

Assignees

• Sumitomo Chemical Co

Inventors

• Masuyama Tatsuro
• Ichikawa Koji
• Yoshida Masafumi

Classifications

• C07D327/06

  Six-membered rings · CPC title

• G03F7/0397

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

• C07D317/72 Primary

  spiro-condensed with carbocyclic rings · CPC title

• G03F7/0045

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

• C07C381/12

  Sulfonium compounds · CPC title