Salt, acid generator, photoresist composition and process of producing photoresist pattern

Patent metadata

Field	Value
Publication number	US-10359700-B2
Application number	US-201514714812-A
Country	US
Kind code	B2
Filing date	May 18, 2015
Priority date	May 20, 2014
Publication date	Jul 23, 2019
Grant date	Jul 23, 2019

Abstract

A salt represented by formula (I):

in which X represents an oxygen atom, a sulfur atom or —N(SO 2 R 5 )—;
R 5 represents a C1-C12 alkyl group which can have a fluorine atom and in which a methylene group can be replaced by an oxygen atom or a carbonyl group, a C3-C12 cycloalkyl group which can have a fluorine atom, or a C6-C12 aromatic hydrocarbon group which can have a fluorine atom; Ar represents a C6-C36 aromatic hydrocarbon group which can have a substituent or a C4-C36 heteroaromatic hydrocarbon group which can have a substituent; R 1 and R 2 each independently represent a hydrogen atom, a hydroxy group, or a C1-C12 hydrocarbon group in which a methylene group can be replaced by an oxygen atom or a carbonyl group; “m” and “n” each independently represent 1 or 2; R 3 and R 4 each independently represent a hydrogen atom or a C1-C12 hydrocarbon group, R 3 and R 4 may be bonded to form a ring, or R 3 or R 4 may form a ring together with Ar; and A − represents an organic anion which has an acid-labile group, an organic anion which has a base-labile group, or an organic anion which has an acid-labile group and a base-labile group.

First claim

What is claimed is:

1. A photoresist composition comprising:
an acid generator which comprises, a salt represented by formula (I):

in which X represents an oxygen atom, a sulfur atom or —N(SO2R 5 )—;
R 5 represents a C1-C12 alkyl group which can have a fluorine atom and in which a methylene group can be replaced by an oxygen atom or a carbonyl group, a C3-C12 cycloalkyl group which can have a fluorine atom, or a C6-C12 aromatic hydrocarbon group which can have a fluorine atom;
Ar represents a C6-C36 aromatic hydrocarbon group which can have a substituent or a C4-C36 heteroaromatic hydrocarbon group which can have a substituent;
R 1 and R 2 each independently represent a hydrogen atom, a hydroxy group, or a C1-C12 hydrocarbon group in which a methylene group can be replaced by an oxygen atom or a carbonyl group;
“m” and “n” each independently represent 1 or 2;
R 3 and R 4 each independently represent a hydrogen atom; and
A − represents an organic anion represented by formula (a-2), formula (I—Ba) or formula (I-Bb):

in which X a and X b each independently represent an oxygen atom or a sulfur atom;
X 1 represents a divalent C1-C12 saturated hydrocarbon group which has a fluorine atom;
the ring W represents a ring represented by formula (a-1-1), formula (a-1-2) or formula (a-1-3):

in which ring 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 them:
L b1 represents a group represented by *—CO—O—(CH 2 ) t — where t represents an integer of 0 to 6 and * represents a binding site to —C(Q 1 )(Q 2 )-; and
Q 1 and Q 2 each independently represent a fluorine atom or a C1-C6 perfluroalkyl group,

in which Q 1x ,Q 2x ,Q 1y and Q 2y each independently represent a fluorine atom or a C1-C6 perfluroalkyl group;
L 21x and L 21y each independently represent a single bond or a C1-C17 alkanediyl group in which a methylene group can be replaced by an oxygen atom or a carbonyl group;
R 23 represents a C1-C6 fluoroalkyl group;
Y 21x and Y 21y each independently represent a C3-C18 divalent alicyclic hydrocarbon group in which a methylene group can be replaced by an oxygen atom or a carbonyl group;
R 24 represents a C1-C05 fluoroalkyl group, and R 25 and R 26 each independently represent a hydrogen atom or a fluorine atom; and
a salt consisting of a cation represented by formula (b2-1) and an anion represented by (B1):

in which R b4 , R b5 and R b6 independently represent a C1-C30 aliphatic hydrocarbon group which can have a substituent selected from the group consisting of a hydroxy group, a C1-C12 alkoxy group, a C3-C12 alicyclic hydrocarbon group and a C6-C18 aromatic hydrocarbon group, a C3-C36 alicyclic hydrocarbon group which can have a substituent selected from the group consisting of a C1-C18 aliphatic hydrocarbon group, a C2-C4 acyl group and a glycidyloxy group, or a C6-C36 aromatic hydrocarbon group which can have a substituent selected from the group consisting of a hydroxy group, a C1-C18 aliphatic hydrocarbon group and a C1-C12 alkoxy group, and in in which R b4 and R b5 can be bonded to form a ring together with the adjacent S+, and a methylene group in the ring may be replaced by —CO—, —O— or —SO—;

wherein Q 21b and Q 22b independently each represent a fluorine atom or a C1-C6 perfluoroalkyl group;
L 21b represents a C1-C24 divalent 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
Y 21 represents a C3-C18 alicyclic hydrocarbon group where a methylene group can be replaced by an oxygen atom, a carbonyl group or a sulfonyl group and where a hydrogen atom can be replaced by a fluorine atom or a hydroxy group; and
a resin having an acid-labile group which comprises a structural unit represented by formulae (a3-4);

in which R a24 represents a hydrogen atom, a halogen atom other than a fluorine atom, or a C1-C6 alkyl group which can have a halogen atom other than a fluorine atom,
L a7 represents —O—, *1 —O-L a8 -O—, *1 —O-L a8 -CO—O-L a9 -CO—O— or *1 —O-L a8 -CO—O-L a9 -O— in which L a8 and La a9 each independently represents a C1-C6 divalent alkanediyl group, and *1 represents a binding site to —CO—.

2. The photoresist composition according to claim 1 ,
further comprising a salt which generates an acid having an acidity weaker than an acid generated from said acid generator.

3. 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 1 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.

4. The photoresist composition according to claim 1 , further comprising another resin which comprises a structural unit having a halogen atom.

Assignees

• Sumitomo Chemical Co

Inventors

• Anryu Yukako
• Yamamoto Satoshi
• Ichikawa Koji

Classifications

• C07C2603/74

  Adamantanes · CPC title

• G03F7/38

  Treatment before imagewise removal, e.g. prebaking {(G03F7/265 takes precedence)} · CPC title

• C07D295/26

  Sulfur atoms · CPC title

• C07D417/06

  linked by a carbon chain containing only aliphatic carbon atoms · CPC title

• G03F7/2041

  in the presence of a fluid, e.g. immersion; using fluid cooling means · CPC title