US009703193B2  c12)  United States Patent  Fujiwara et al.  (IO)  Patent No.:  US 9,703,193 B2  Jul. 11, 2017  (45)  Date of Patent:  (54)  ONIUM SALT, RESIST COMPOSITION, AND  PATTERNING PROCESS  (71)  Applicant:  Shin-Etsu Chemical Co., Ltd.,  Tokyo  (JP)  (72)  Inventors:  Takayuki Fujiwara,  Joetsu (JP);  Masaki Ohashi,  Joetsu (JP);  Ryosuke  Taniguchi,  Joetsu (JP)  (73)  Assignee:  SHIN-ETSU CHEMICAL CO., LTD.,  Tokyo (JP)  ( * )  Notice:  Subject to any disclaimer, the term ofthis  patent is extended or adjusted under 35  U.S.C. 154(b) by  O  days.  (21)  Appl. No.:  15/139,780  (22)  Filed:  Apr. 27, 2016  (51)  Int. Cl.  (52)  U.S. Cl.  CPC ..........  G03F  710045  (2013.01);  C07C 307102  (2013.01);  C07C 321128  (2013.01);  C07D  303/16  (2013.01);  C07D 305/06  (2013.01);  C07D 305/08  (2013.01);  C07D 307120  (2013.01);  C07D 307133  (2013.01);  C07D  307193  (2013.01);  C07D 309/10  (2013.01);  C07D 333/46  (2013.01);  C07D 493/08  (2013.01);  C07D 493/18  (2013.01);  C07J  4110055  (2013.01);  G03F 710397  (2013.01);  (58)  Field of Classification Search  None  See application file for complete search history.  RESIST COATING  RESIST EXPOSURE  30  20  10  19 Claims, 1 Drawing Sheet  (57)  ABSTRACT  OTHER PUBLICATIONS  FOREIGN PATENT DOCUMENTS  U.S. PATENT DOCUMENTS  (56)  References Cited  (65)  Prior Publication Data  (30)  Foreign Application Priority Data  US 2016/0320698 Al  Nov. 3, 2016  Apr. 28, 2015  (JP) ................................. 2015-091358  (Continued)  Journal of Photopolymer Science and Technology, 2004, vol. 17,  No. 4, p. 587, (18 pages).  Primary Examiner  - Sin Lee  (74)  Attorney, Agent, or Firm  - Westerman, Hattori,  Daniels & Adrian, LLP  An onium salt having an anion moiety of a specific structure  is an effective photoacid generator. A resist composition  comprising the onium salt has the advantages of compat› ibility and reduced acid diffusion and forms a pattern with a  good balance of sensitivity and MEF, rectangularity, and  minimal defects.  (Continued)  (Continued)  (Continued)  G03F  7111  (2013.01);  G03F  712041  (2013.01);  G03F  7130  (2013.01);  G03F  71322  (2013.01);  G03F  71325  (2013.01);  G03F  7138  (2013.01);  C07C 2101/02  (2013.01);  6,008,267 A  *  12/1999 Vallee ................... C07C 307/02  522/31  6,165,678 A  *  12/2000 Allen ...................... G03F 7/039  430/270.1  EP  JP  1 635 218 A2  3/2006  2006-84530 A  3/2006  G03F  71004  G03F  71039  (2006.01)  (2006.01) 