Sulfonic acid derivative, photoacid generator using same, resist composition, and device manufacturing method

Patent metadata

Field	Value
Publication number	US-10216084-B2
Application number	US-201515533340-A
Country	US
Kind code	B2
Filing date	Nov 26, 2015
Priority date	Dec 5, 2014
Publication date	Feb 26, 2019
Grant date	Feb 26, 2019

Abstract

A sulfonic acid derivative, wherein the sulfonic acid derivative is represented by the following general formula (1):

R 1 COOCH 2 CH 2 CFHCF 2 SO 3 − M +   (1)

where: R 1 represents a monovalent organic group having carbon number of 1 to 200, having at least one hydroxyl group and optionally having a substituent other than the hydroxyl group; and M + represents a counter cation.

First claim

The invention claimed is:

1. A sulfonic acid derivative, wherein the sulfonic acid derivative is represented by the. following general formula (1):
R 1 COOCH 2 CH 2 CFHCF 2 SO 3 − M +   (1)

where:
R 1 represents a monovalent organic group having carbon number of 1 to 200, having at least one hydroxyl group and optionally having a substituent other than the hydroxyl group; and
M + represents a counter cation.

2. The sulfonic acid derivative according to claim 1 , wherein the organic group is represented by the following formula (2):
R 2 -(A-R 3 ) n —  (2)

where:
R 2 is a monovalent group selected from the group consisting of: a linear, branched, or cyclic aliphatic hydrocarbon group; an aromatic hydrocarbon group; and an aliphatic heterocyclic group or aromatic heterocyclic group containing, in the skeleton, at least one group selected from the group consisting of —O—, —CO—, —COO—, —OCO—, —O—CO—O—, —NHCO—, —CONH—, —NH—CO—O—, —O—CO—NH—, —NH—, —N═, —S—, —SO—, and —SO 2 —;
A is each independently a direct bond, or a group selected from the group consisting of —O—, —CO—, —COO—, —OCO—, —O—CO—O—, —NHCO—, —CONH—, —NH—CO—O—, —O—CO—NH—, —NH—, —S—, and —CO—O—CH 2 —CO—O—;
R 3 is each independently a divalent group selected from the group consisting of: a linear, branched, or cyclic aliphatic hydrocarbon group; an aromatic hydrocarbon group; and an aliphatic heterocyclic group or aromatic heterocyclic group containing, in the skeleton, at least one group selected from the group consisting of —O—, —CO—, —COO—, —OCO—, —O—CO—O—, —NHCO—, —CONH—, —NH—CO—O—, —O—CO—NH—, —NH—, —N═, —S—, —SO—, and —SO 2 —; and
n is an integer of 0 or 1 to 10, with the proviso that when n is 0, R 2 has the hydroxyl group, and when n is from 1 to 10, at least one of R 2 and R 3 has the hydroxyl group.

3. The sulfonic acid derivative according to claim 1 , wherein the M + is a hydrogen ion, a metal ion, or an onium ion.

4. A photoacid generator composing:
a sulfonic acid derivative of the following general formula (1):
R 1 COOCH 2 CH 2 CFHCF 2 SO 3 − M +   (1)

wherein:
R 1 represents a monovalent organic group having carbon number of 1 to 200, having at least one hydroxyl group and optionally having a substituent other than the hydroxyl group; and
M + represents a counter cation.

5. A resist composition comprising:
the photoacid generator according to claim 4 , and
a compound that reacts with an acid.

6. A method for producing a device, the method comprising:
a resist film-forming step of forming a resist film by applying the resist composition according to claim 5 to a substrate to form a resist film;
a photolithography step of exposing the resist film to an active energy ray in a pattern shape; and
a pattern-forming step of obtaining a photoresist pattern by developing a exposed resist film.

7. The sulfonic acid derivative of claim 2 , wherein M + is selected from the group consisting of a hydrogen ion, a metal ion, and an onium ion.

8. The photoacid generator of claim 4 , wherein the organic group is represented by the following formula (2):
R 2 -(A-R 3 ) n —  (2)

wherein:
R 2 is a monovalent group selected from the group consisting of a linear, branched, or cyclic aliphatic hydrocarbon group; an aromatic hydrocarbon group; and an aliphatic heterocyclic group or aromatic heterocyclic group containing, in the skeleton, at least one group selected from the group consisting of —O—, —CO—, —COO—, —OCO—, —O—CO—O—, —NHCO—, —CONH—, —NH—CO—O—, —O—CO—NH—, —NH—, —N═, —S—, —SO—, and —SO 2 —;
A is each independently a direct bond, or a group selected from the group consisting of —O—, —CO—, —COO—, —OCO—, —O—CO—O—, —NHCO—, —CONH—, —NH—CO—O—, —O—CO—NH—, —NH—, —S—, and —CO—O—CH 2 —CO—O—;
R 3 is each independently a divalent group selected from the group consisting of: a linear, branched, or cyclic aliphatic hydrocarbon group; an aromatic hydrocarbon group; and an aliphatic heterocyclic group or aromatic heterocyclic group containing, in the skeleton, at least one group selected from the group consisting of —O—, —CO—, —COO—, —OCO—, —O—CO—O—, —NHCO—, —CONH—, —NH—CO—O—, —O—CO—NH—, —NH—, —N═, —S—, —SO—, and —SO 2 —; and
n is an integer of 0 or 1 to 10, with the proviso that when n is 0, R 2 has the hydroxyl group, and when n is from 1 to 10, at least one of R 2 and R 3 has the hydroxyl group.

9. The photoacid generator of claim 8 , together with a compound that reacts with an acid.

10. The photoacid generator of claim 4 , together with a compound that reacts with an acid.

Assignees

• Toyo Gosei Co Ltd

Inventors

• Utsumi Yoshiyuki
• Kobayashi Noriaki
• Kamakura Takahiro

Classifications

• H10P76/00

  Manufacture or treatment of masks on semiconductor bodies, e.g. by lithography or photolithography · CPC title

• G03F7/2012

  using liquid photohardening compositions, e.g. for the production of reliefs such as flexographic plates or stamps · CPC title

• G03F7/038

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

• G03F7/004

  Photosensitive materials (G03F7/12, G03F7/14 take precedence) · CPC title

• C07C2603/74

  Adamantanes · CPC title