US009665002B2  c12)  United States Patent  Fukushima et al.  (IO)  Patent No.:  US 9,665,002 B2  (45)  Date of Patent:  May 30, 2017  (54)  ONIUM SALT COMPOUND, RESIST  COMPOSITION, AND PATTERN FORMING  PROCESS  (71)  Applicant:  Shin-Etsu Chemical Co., Ltd.,  Tokyo  (JP)  (72)  Inventors:  Masahiro Fukushima,  Joetsu (JP);  Masaki Ohashi,  Joetsu (JP);  Jun  Hatakeyama,  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.:  14/930,869  (22)  Filed:  Nov. 3, 2015  (51)  Int. Cl.  (52)  U.S. Cl.  CPC ............  G03F 710397  (2013.01);  C07C 25100  (2013.01);  C07C 25102  (2013.01);  C07C 69176  (2013.01);  C07C 69178  (2013.01);  C07C  381112  (2013.01);  C07D 203/14  (2013.01);  C07D 205/04  (2013.01);  C07D 207104  (2013.01);  C07D 211106  (2013.01);  C07D  213179  (2013.01);  C07D 223104  (2013.01);  C07D 225102  (2013.01);  C07D 233102  (2013.01);  C07D 241104  (2013.01);  C07D  263/04  (2013.01);  C07D 265/30  (2013.01);  C07D  277104  (2013.01);  C07D  279112  (2013.01);  C07D 2951112  (2013.01);  C07D  2951155  (2013.01);  C07D 295/26  (2013.01);  G03F  710045  (2013.01);  G03F  710046  (2013.01);  G03F  71168  (2013.01);  G03F  712037  (2013.01);  G03F  712041  (2013.01);  G03F  7130  (2013.01);  G03F  71322  (2013.01);  G03F  71325  (2013.01);  G03F  7138  (2013.01)  (58)  Field of Classification Search  None  See application file for complete search history.  (65)  Prior Publication Data  (30)  Foreign Application Priority Data  (56)  References Cited  U.S. PATENT DOCUMENTS  FOREIGN PATENT DOCUMENTS  OTHER PUBLICATIONS  (57)  ABSTRACT  11 Claims, 1 Drawing Sheet  Machine-assisted English translation of JP 2013-250433 provided  by JPO (2013).*  Office Action dated Jul. 6, 2016, issued in counterpart Taiwanese  Patent Application No. 104136092. (4 pages).  * cited by examiner  Primary Examiner  - Sin Lee  (74)  Attorney, Agent, or Firm  - Westerman, Hattori,  Daniels & Adrian, LLP  Sulfonium and iodonium salts of a carboxylate having an  aromatic ring to which a nitrogen-containing alkyl or cyclic  structure is attached 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 reso› lution, improved MEF, LWR and DOF.  Nov. 7, 2014  (JP) ................................. 2014-226553  US 2016/0131972 Al  May 12, 2016  6,492,091 B2  7,923,199 B2  8,846,291 B2  12/2002 Kodama et al.  4/2011 Wada  9/2014 Utsumi et al.  9/2007 Kamimura et al.  2007/0224540 Al  2009/0233223 Al*  9/2009 Tachibana ............. G03F 7/0045  430/270.1  2011/0212390 Al  9/2011 Masunaga et al.  2016/0246175 Al*  8/2016 Kotake ................. G03F 7/0392  2016/0299428 Al* 10/2016 Masunaga ............. G03F 7/0045  G03F  71039  G03F  71004  G03F  7130  G03F  7132  G03F  7138  G03F  7120  C07D 263/04  C07D 233102  C07D 277104  C07D 207104  C07D 279112  C07D 2951112  C07D 203/14  C07D 241104  C07D 225102  C07D 223104  C07D 211106  C07D 205/04  C07D 265/30  C07D 2951155  C07D 213179  C07D 295/26  C07C 381112  G03F 7116  C07C 25100  C07C 69178  C07C 69176  C07C 25102  (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)  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (2006.01)  GB  JP  JP  JP  JP  JP  946870  2006-208781  A  2007-293250  A  4226803 B2  2012-123189 A  2013-250433  *  1/1964  8/2006  11/2007  2/2009  6/2012  * 12/2013 