Photoresist composition and method for producing photoresist pattern

Patent metadata

Field	Value
Publication number	US-2016195809-A1
Application number	US-201614987303-A
Country	US
Kind code	A1
Filing date	Jan 4, 2016
Priority date	Jan 7, 2015
Publication date	Jul 7, 2016
Grant date	—

Abstract

A photoresist composition comprising
a resin having an acid-labile group; a salt represented by the formula (I); and a salt represented by the formula (B1).

First claim

1 . A photoresist composition comprising
a resin having an acid-labile group; a salt represented by the formula (I); and a salt represented by the formula (B1):

wherein Q 1 and Q 2 each independently represent a fluorine atom or a C1 to C6 perfluoroalkyl group;
R 1 and R 2 each independently represent a hydrogen atom, a fluorine atom or a C1 to C6 perfluoroalkyl group;
“z” represents an integer of 0 to 6;
X 1 and X 2 each independently represent a group having at least one of *—CO—O—, *—O—CO— and *—O— where * represents a binding site to L 1 ;
L 1 represents a C1 to C8 fluoroalkanediyl group; and
R 3 represents a C5 to C18 alicyclic hydrocarbon group in which a hydrogen atom can be replaced by a hydroxy group and a methylene group can be replaced by an oxygen atom, a sulfonyl group or a carbonyl group, and which alicyclic hydrocarbon group may have a cyclic ketal structure optionally having a fluorine atom; and Z + represents an organic cation represented by any one of formulae (b2-1) and (b2-2):

wherein R b4 , R b5 and R b6 independently represent a C1 to C30 aliphatic hydrocarbon group in which a hydrogen atom can be replaced by a hydroxy group, a C1 to C12 alkoxy group, a C3 to C12 alicyclic hydrocarbon group, or a C6 to C18 aromatic hydrocarbon group, a C3 to C36 alicyclic hydrocarbon group in which a hydrogen atom can be replaced by a halogen atom, a C2 to C4 acyl group or a glycidyloxy group, or
a C6 to C36 aromatic hydrocarbon group in which a hydrogen atom can be replaced by a halogen atom, a hydroxy group, or a C1 to C12 alkoxy group, and R b4 and R b6 each independently represent a ring together with S + ,
R b7 and R b8 each independently represent a hydroxy group, a C1 to C12 alkyl group or a C1 to C12 alkoxy group, and
m2 and n2 each independently represent an integer of 0 to 5;

wherein Q 21b and Q 22b each independently represent a fluorine atom or a C1 to C6 perfluoroalkyl group,
L b21 represents a single bond or a C1 to 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 hydroxy group,
Y 21 represents a C3 to C18 alicyclic 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 hydroxyl group or a fluorine atom, and Zb + represents an organic cation represented by any one of the formula (b2-1) and the formula (b2-2).

2 . The photoresist composition according to claim 1 wherein X 1 represents *—CO—O—.

3 . The photoresist composition according to claim 1 wherein X 2 represents *—CO—O—.

4 . The photoresist composition according to claim 1 wherein L 1 represents —CH 2 —(CF 2 ) n —CH 2 — where n represents integer of 1 to 6.

5 . The photoresist composition according to claim 1 wherein the alicyclic hydrocarbon group for R 3 is an adamantyl group.

6 . The photoresist composition according to claim 1 wherein L b21 represents a group represented by formula (b1-4):

wherein L b8 represents a single bond or a C 1 to C 22 divalent saturated hydrocarbon group where a hydrogen atom can be replaced by a hydroxy group, and * represents a binding site to Y 21 .

7 . The photoresist composition according to claim 1 , which further comprises a salt which generates an acid weaker in acidity than an acid generated from the salt represented by the formula (B1) and an acid generated from the salt represented by the formula (I).

8 . A salt represented by the formula (Ia):

wherein Q 1a and Q 2a each independently represent a fluorine atom or a C1 to C6 perfluoroalkyl group;
R 1a and R 2a each independently represent a hydrogen atom, a fluorine atom or a C1 to C6 perfluoroalkyl group;
“za” represents an integer of 0 to 6;
X 1a and X 2a each independently represent a group having at least one of *—CO—O—, *—O—CO— and *—O— group where * represents a binding site to L 1a , provided that at least one of X″ and X 2a represents *—CO—O— or *—O—CO—;
L 1a represents —CH 2 —(CF 2 ) na —CH 2 — where “na” represents an integer of 2 to 6;
R 1a represents a C5 to C18 alicyclic hydrocarbon group in which a hydrogen atom can be replaced by a hydroxy group and a methylene group can be replaced by an oxygen atom, a sulfonyl group or a carbonyl group, and which alicyclic hydrocarbon group may have a cyclic ketal structure optionally having a fluorine atom; and
Za 4 represents an organic cation.

9 . The salt according to claim 8 wherein X 1a represents *—CO—O—.

10 . The salt according to claim 8 wherein X 2a represents *—O—CO—.

11 . The salt according to claim 8 wherein the alicyclic hydrocarbon group for R 1a is an adamantyl group.

12 . A photoresist composition which comprises the salt according to claim 8 and a resin having an acid-labile group.

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 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.

Assignees

• Sumitomo Chemical Co

Inventors

• Ochiai Mitsuyoshi
• Ichikawa Koji

Classifications

• C07D327/04

  Five-membered rings · CPC title

• G03F7/0397

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

• C07C381/12

  Sulfonium compounds · CPC title

• G03F7/038 Primary

  Macromolecular compounds which are rendered insoluble or differentially wettable (G03F7/075 takes precedence; macromolecular azides G03F7/012; macromolecular diazonium compounds G03F7/021) · CPC title

• C07D327/02

  one oxygen atom and one sulfur atom · CPC title