Resist composition, method for forming resist pattern, compound, and acid generator

Patent metadata

Field	Value
Publication number	US-10394122-B2
Application number	US-201715631592-A
Country	US
Kind code	B2
Filing date	Jun 23, 2017
Priority date	Jun 28, 2016
Publication date	Aug 27, 2019
Grant date	Aug 27, 2019

Abstract

A resist composition which generates an acid upon exposure and changes a solubility in a developing solution under an action of the acid, the resist composition containing a base material component whose solubility in the developing solution changes under the action of an acid and an acid generator represented by general formula (b1). In general formula (b-1), R b1 represents an aromatic hydrocarbon group having at least one alkyl group having 3 or more carbon atoms as a substituent, Y b1 represents a divalent linking group containing an ester bond (—C(═O)—O— or —O—C(═O)—), V b1 represents an alkylene group, a fluorinated alkylene group, or a single bond, m is an integer of 1 or more, and M m+ represents an m-valent organic cation.

R b1 —Y b1 —V b1 —CF 2 —SO 3 − (M m+ ) 1/m   (b1)

First claim

What is claimed is:

1. A resist composition which generates an acid upon exposure and changes a solubility in a developing solution under the action of an acid, the resist composition comprising:
a base material component (A) whose solubility in the developing solution changes under the action of an acid; and
an acid generator component (B) which generates an acid upon exposure and contains a compound (B1) represented by general formula (b1):
R b1 —Y b1 —V b1 —CF 2 —SO 3 − (M m+ ) 1/m   (b1)

wherein R b1 represents an aromatic hydrocarbon group having at least one t-butyl group as a substituent, Y b1 represents a divalent linking group represented by general formula (y-al-1), (y-al-2), (y-al-3), (y-al-5), or (y-al-7) below, V b1 represents an alkylene group, or a single bond, m is an integer of 1 or more, and M m+ represents an m-valent organic cation

wherein V′ 101 is a single bond or an alkylene group having 1 to 5 carbon atoms, and V′ 102 is a divalent saturated hydrocarbon group having 1 to 30 carbon atoms.

2. The resist composition according to claim 1 , wherein the content of the compound (B1) is 1 to 40 parts by mass with respect to 100 parts by mass of the base material component (A).

3. The resist composition according to claim 1 , wherein the base material component (A) contains a resin component (A1), and the resin component (A1) contains a structural unit (a1) having an acid-decomposable group which increases a polarity under the action of an acid.

4. The resist composition according to claim 3 , wherein the structural unit (a1) contains a structural unit represented by general formula (a1-1-1):

wherein in general formula (a1-1-1), R represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, or a halogenated alkyl group having 1 to 5 carbon atoms, Va 1 is a divalent hydrocarbon group which may have an ether bond, n a1 is an integer of 0 to 2, and Ra 1 ′ is an acid dissociable group represented by general formula (a1-r2-2), (a1-r2-3), or (a1-r2-4);
in general formula (a1-r2-2), Ya is a carbon atom, Xa is a group forming a cyclic hydrocarbon group together with Ya, at least one hydrogen atom contained in the cyclic hydrocarbon group may be substituted, Ra 01 to Ra 03 each independently represent, a hydrogen atom, a monovalent chain saturated hydrocarbon group having 1 to 10 carbon atoms, or a monovalent aliphatic cyclic saturated hydrocarbon group having 3 to 20 carbon atoms, at least one hydrogen atom of the chain saturated hydrocarbon group or the aliphatic cyclic saturated hydrocarbon group may be substituted, two or more of Ra 01 to Ra 03 may be bonded to each other to form a cyclic structure, and a symbol of * represents a bond; and
in general formula (a1-r2-3), Yaa is a carbon atom, Xaa is a group forming an aliphatic cyclic group together with Yaa, Ra 04 is an aromatic hydrocarbon group which may have a substituent, a symbol of * represents a bond; and in general formula (a1-r2-4), Ra′ 12 and Ra′ 13 each independently represent a monovalent chain saturated hydrocarbon group having 1 to 10 carbon atoms or a hydrogen atom, at least one hydrogen atom of the chain saturated hydrocarbon group may be substituted, Ra′ 14 is an aromatic hydrocarbon group which may have a substituent, and * represents a bond.

5. The resist composition according to claim 3 , wherein the resin component (A1) further comprises a structural unit (a2) containing a lactone-containing cyclic group, an —SO 2 — containing cyclic group, or a carbonate-containing cyclic group.

6. The resist composition according to claim 3 , wherein the resin component (A1) further comprises a structural unit (a9) represented by general formula (a9-1):

wherein R is a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, or a halogenated alkyl group having 1 to 5 carbon atoms, Ya 91 is a single bond or a divalent linking group, Ya 92 is a divalent linking group, and R 91 is a hydrocarbon group which may have a substituent.

7. The resist composition according to claim 3 , wherein the resin component (A1) further comprises a structural unit having a hydroxystyrene skeleton.

8. A method for forming a resist pattern, comprising:
forming a resist film on a support using the resist composition according to claim 1 ;
exposing the resist film; and
developing the exposed resist film to form a resist pattern.

9. The method for forming a resist pattern according to claim 8 , wherein in exposing the resist film, the resist film is exposed to extreme ultraviolet ray (EUV) or an electron beam (EB).

10. A compound represented by general formula (b1):
R b1 —Y b1 —V b1 —CF 2 —SO 3 − (M m+ ) 1/m   (b1)

wherein R b1 represents an aromatic hydrocarbon group having at least one t-butyl group as a substituent, Y b1 represents a divalent linking group represented by general formula (y-al-1), (y-al-2), (y-al-3), (y-al-5), or (y-al-7) below, V b1 represents an alkylene group, or a single bond, m is an integer of 1 or more, and M m+ represents an m-valent organic cation

wherein V′ 101 is a single bond or an alkylene group having 1 to 5 carbon atoms, and V′ 102 is a divalent saturated hydrocarbon group having 1 to 30 carbon atoms.

11. An acid generator comprising the compound according to claim 10 .

Assignees

• Tokyo Ohka Kogyo Co Ltd
• Toyko Ohka Kogyo Co Ltd

Inventors

• Suzuki Issei
• Yahagi Masahito
• Fukumura Yuki
• Ebisawa Kazuaki
• Komuro Yoshitaka
• Takayama Toshikazu
• Kamizono Takashi
• Fujii Tatsuya

Classifications

• C08F212/24 Primary

  Phenols or alcohols · CPC title

• H10P76/2041

  Photolithographic processes · CPC title

• C08F12/24

  Phenols or alcohols · CPC title

• C08F220/303

  and one or more carboxylic moieties in the chain · CPC title

• C08F220/282

  and containing two or more oxygen atoms · CPC title