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The patent badge is an abbreviated version of the USPTO patent document. The patent badge does contain a link to the full patent document.

The patent badge is an abbreviated version of the USPTO patent document. The patent badge covers the following: Patent number, Date patent was issued, Date patent was filed, Title of the patent, Applicant, Inventor, Assignee, Attorney firm, Primary examiner, Assistant examiner, CPCs, and Abstract. The patent badge does contain a link to the full patent document (in Adobe Acrobat format, aka pdf). To download or print any patent click here.

Patent No.:

US 9983475 B1

PDFFull Text
Date of Patent:
May. 29, 2018

Filed:

Aug. 12, 2016

Fluorinated sulfonate esters of aryl ketones for non-ionic photo-acid generators

Applicants:

International Business Machines Corporation, Armonk, NY (US);

Central Glass Co., Ltd., Yamaguchi, JP;

Inventors:

Takehisa Ishimaru, Tokyo, JP;

Satoru Narizuka, Kawagoe, JP;

Daniel P. Sanders, San Jose, CA (US);

Ratnam Sooriyakumaran, San Jose, CA (US);

Hoa D. Truong, San Jose, CA (US);

Rudy J. Wojtecki, San Jose, CA (US);

Assignees:

International Business Machines Corporation, Armonk, NY (US);

Central Glass Co., Ltd., Ube-shi, Yamaguchi, JP;

Attorney:

Michael R. Roberts

Primary Examiner:

John S Chu

Int. Cl.
CPC ...
G03F 7/004 (2006.01); G03F 7/38 (2006.01); G03F 7/039 (2006.01); G03F 7/038 (2006.01); G03F 7/16 (2006.01); G03F 7/20 (2006.01); G03F 7/32 (2006.01); C07C 309/69 (2006.01); C07C 309/68 (2006.01); C07C 309/70 (2006.01); C07F 7/21 (2006.01); C07C 309/76 (2006.01); C07C 317/14 (2006.01); C07C 317/10 (2006.01); C07C 317/04 (2006.01); C07C 317/06 (2006.01); C07C 317/08 (2006.01); C07C 317/32 (2006.01); C07C 317/24 (2006.01); C07C 317/26 (2006.01);
U.S. Cl.
CPC ...
G03F 7/0045 (2013.01); C07C 309/68 (2013.01); C07C 309/69 (2013.01); C07C 309/70 (2013.01); C07C 309/76 (2013.01); C07C 317/04 (2013.01); C07C 317/06 (2013.01); C07C 317/08 (2013.01); C07C 317/10 (2013.01); C07C 317/14 (2013.01); C07C 317/24 (2013.01); C07C 317/26 (2013.01); C07C 317/32 (2013.01); C07F 7/21 (2013.01); G03F 7/0382 (2013.01); G03F 7/0392 (2013.01); G03F 7/168 (2013.01); G03F 7/2004 (2013.01); G03F 7/322 (2013.01); G03F 7/38 (2013.01); C07C 2103/74 (2013.01);
Abstract

Non-ionic photo-acid generating (PAG) compounds were prepared that contain an aryl ketone group having a perfluorinated substituent alpha to the ketone carbonyl. The non-polymeric PAGs release a sulfonic acid when exposed to high energy radiation such as deep UV or extreme UV light. The photo-generated sulfonic acid has a low diffusion rate in an exposed resist layer subjected to a post-exposure bake (PEB) at 100° C. to 150° C., resulting in formation of good line patterns after development. At higher temperatures, the PAGs can also undergo a thermal reaction to form a sulfonic acid. The perfluorinated substituent provides improved thermal stability and hydrolytic/nucleophilic stability.

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