# US 11,307,495 B2 · Thermal acid generator and resist composition using same

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- Number: US 11,307,495 B2
- Document ID: US11307495B2
- Status: Granted
- Kind: B2
- Application number: 16/071,397
- Filed: 2017-01-23
- Published: 2020-06-11
- Granted: 2022-04-19
- Earliest claimed: 2016-01-26
- Assignees: Adeka Corporation
- Applicants: Adeka Corporation
- Inventors: Junya Miyake; Yoshitomo Takeuchi; Naomi Sato; Kentaro Kimura
- Web page: https://patentgrep.com/patent/US11307495B2

## CPC

- G03F 7/0007: {Filters, e.g. additive colour filters; Components for display devices}
- G03F 7/004: Photosensitive materials (G03F7/12, G03F7/14 take precedence)
- C07D 221/14: Aza-phenalenes, e.g. 1,8-naphthalimide
- G03F 7/0382: {the macromolecular compound being present in a chemically amplified negative photoresist composition}
- G03F 7/0392: {the macromolecular compound being present in a chemically amplified positive photoresist composition}
- G03F: PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR; (phototypographic composing devices B41B; photosensitive materials or processes for photographic purposes G03C; electrophotography, sensitive layers or processes therefor G03G)
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

Provided are: a thermal acid generator having a high acid generation temperature; and a resist composition using the same. The thermal acid generator is a sulfonic acid derivative compound represented by the following Formula (I): (wherein, R1 represents an aliphatic hydrocarbon group having 1 to 18 carbon atoms or the like, or a group represented by the following Formula (II): (wherein, Y1 represents a single bond or an alkanediyl group having 1 to 4 carbon atoms; R11 and R12 each independently represent an alkanediyl group having 2 to 6 carbon atoms, or the like; R13 represents a linear or branched alkyl group having 1 to 18 carbon atoms, or the like; a and b each represent 0 or 1; and either a or b is 1); R2 to R7 each independently represent a linear or branched alkyl group having 1 to 14 carbon atoms; the aliphatic hydrocarbon group or the like of R1 has no substituent or is substituted with a halogen atom or the like; and a methylene structure in the aliphatic hydrocarbon group or the like of R1 is optionally substituted with —O— or the like).

## Claims

### Claim 1

A thermal acid generator selected from the group consisting of:

### Claim 2 (depends on 1)

A resist composition comprising the thermal acid generator according to claim 1.

### Claim 3 (depends on 1)

A method of making a resist, said method comprising:
heating an acid-reactive organic substance and the thermal acid generator of claim 1, wherein said heating of the thermal acid generator releases a Lewis acid to induce a polymerization or cross-linking of said acid-reactive organic substance to make said resist;
wherein the polymerization or cross-linking is performed at a heating condition of 200 to 250° C. for 1 to 100 minutes.

### Claim 4 (depends on 3)

A resist obtained by the method according to claim 3.

### Claim 5 (depends on 1)

A method of making a resist, said method comprising:
heating an acid-reactive organic substance and the thermal acid generator according to claim 1, wherein said heating of the thermal acid generator releases a Lewis acid to induce a polymerization or cross-linking of said acid-reactive organic substance to make said resist;
wherein the polymerization or cross-linking is performed at a heating condition of 70 to 300° C. for 1 to 100 minutes; and
wherein an amount of the thermal acid generator is 0.05 to 100 parts by mass with respect to 100 parts by mass of the acid-reactive organic substance.

### Claim 6 (depends on 5)

A resist obtained by the method according to claim 5.