US00998984 7B2  (IO)  Patent No.:  US 9,989,847 B2  Jun.5,2018  (45)  Date of Patent:  c12)  United States Patent  Ohashi et al.  (54)  ONIUM SALT COMPOUND, RESIST  COMPOSITION, AND PATTERN FORMING  PROCESS  (71)  Applicant:  SHIN-ETSU CHEMICAL CO., LTD.,  Tokyo (JP)  (72)  Inventors:  Masaki Ohashi,  Joetsu (JP);  Jun  Hatakeyama,  Joetsu (JP);  Masahiro  Fukushima,  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. days.  (21)  Appl. No.:  14/829,832  (22)  Filed:  Aug. 19, 2015  (51)  Int. Cl.  (52)  U.S. Cl.  CPC .........  G03F 710045  (2013.01);  C07D 209/04  (2013.01);  C07D 209/08  (2013.01);  C07D  209/18  (2013.01);  C07D 209/42  (2013.01);  C07D 209/60  (2013.01);  C07D 209162  (2013.01);  C07D 215106  (2013.01);  C07D  215114  (2013.01);  C07D 215148  (2013.01);  C07D 215150  (2013.01);  C07D 231/06  (2013.01);  C07D 231112  (2013.01);  C07D  (58)  Field of Classification Search  CPC ........ G03F 7/0397; G03F 7/2041; G03F 7/40;  G03F 7/0045; C07D 209/04; C07D  209/08; C07D 215/14; C07D 275/06;  C07D 277/64; C07D 263/56; C07D  261/20; C07D 249/20; C07D 235/08;  C07D 231/12; C07D 233/18; C07D  209/60; C07D 231/06; C07D 231/56  USPC ....... 430/270.1, 326, 921, 922, 920; 546/26,  546/113, 122, 123, 139, 147, 152, 168,  546/170; 548/179, 180,207,217,241,  548/260, 261, 304.4, 309.4, 341.5, 352.1,  548/358.1, 361.1, 362.5, 379.4, 427, 469,  548/490, 491, 492  See application file for complete search history.  231156  (2013.01);  C07D 233/18  (2013.01);  C07D 235/06  (2013.01);  C07D 235/08  (2013.01);  C07D 241144  (2013.01);  C07D  249118  (2013.01);  C07D 249120  (2013.01);  C07D 261/20  (2013.01);  C07D 263/56  (2013.01);  C07D 263/58  (2013.01);  C07D  275106  (2013.01);  C07D  277164  (2013.01);  C07D  277168  (2013.01);  C07D  277174  (2013.01);  G03F  710046  (2013.01);  G03F  71038  (2013.01);  G03F  710397  (2013.01);  G03F  71168  (2013.01);  G03F  712041  (2013.01);  G03F  712053  (2013.01);  G03F  7132  (2013.01);  G03F  7138  (2013.01);  G03F  7/40  (2013.01)  US 2016/0259242 Al  Sep. 8, 2016  Aug. 21, 2014  (JP) ................................. 2014-168165  (Continued)  (Continued)  office Action dated Sep. 8, 2016, issued in corresponding Taiwanese  Patent Application No. 104126780 (4 pages).  (Continued)  Primary Examiner  - John S Chu  (74)  Attorney, Agent, or Firm  - Westerman, Hattori,  Daniels & Adrian, LLP  Sulfonium and iodonium salts of nitrogen-containing car› boxylic acids are novel. The onium salt functions as an acid  diffusion controlling agent in a resist composition, enabling  to form a pattern of good profile with high resolution,  improved MEF, LWR and DOF.  9 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  (Continued)  G03F  71004  G03F  7140  C07D 209/04  C07D 209/08  C07D 215114  C07D  275106  C07D  277164  C07D 261/20  C07D  249120  C07D 235/08  C07D 231112  C07D 233/18  C07D 209/60  C07D 231/06  C07D  231156  G03F  71038  G03F  7116  G03F 7120  G03F 7138  G03F 7132  C07D 209/42  C07D 215148  C07D 215106  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (2006.01)  CN  1536961 A  10/2004  JP  2000-336121  A  12/2000  4,060,626 A  *  11/1977 Hrstka ................. C07D 209/42  514/418  4,493,843 A  *  1/1985 Ashton ................. C07C 205/57  514/415 