(IO)  Patent No.:  US 10,725,377 B2  *Jul. 28, 2020  (45)  Date of Patent:  c12)  United States Patent  Kotake et al.  (54)  CHEMICALLY AMPLIFIED NEGATIVE  RESIST COMPOSITION AND RESIST  PATTERN FORMING PROCESS  US010725377B2  (71)  Applicant:  Shin-Etsu Chemical Co., Ltd.,  Tokyo  (JP)  USPC .............. 430/270.1, 905, 910; 562/100, 113;  568/34, 35  See application file for complete search history.  (72)  Inventors:  Masaaki Kotake,  Joetsu (JP);  Satoshi  Watanabe,  Joetsu (JP);  Keiichi  Masunaga,  Joetsu (JP);  Kenji Yamada,  Joetsu (JP);  Masaki Ohashi,  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.  This patent is subject to a terminal dis› claimer.  (21)  Appl. No.:  15/854,990  (22)  Filed:  Dec. 27, 2017  (65)  Prior Publication Data  (30)  Foreign Application Priority Data  US 2018/0180998 Al  Jun. 28, 2018  Dec. 28, 2016  (JP) ................................. 2016-255025  (51)  Int. Cl.  EP  EP  JP  JP  JP  JP  JP  JP  JP  JP  JP  1684118 Al  1975711 Al  11-327143 A  2006-201532  A  2006-215180  A  3955384 B2  4116340 B2  2008-249762  A  4226803 B2  4231622 B2  4575479 B2  7/2006  10/2008  11/1999  8/2006  8/2006  8/2007  7/2008  10/2008  2/2009  3/2009  11/2010  G03F 71038  G03F 71004  G03F 7130  C07C 381112  C07C 317104  C07C 317/28  C07C 303132  C07C 323120  C08F  212114  G03F  7132  G03F  7120  G03F 7/039  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (52)  U.S. Cl.  CPC ..........  G03F 710045  (2013.01);  C07C 303132  (2013.01);  C07C 317104  (2013.01);  C07C  317/28  (2013.01);  C07C 323120  (2013.01);  C07C 381112  (2013.01);  C08F 212114  (2013.01);  G03F  710382  (2013.01);  G03F  712002  (2013.01);  G03F  712053  (2013.01);  G03F  712059  (2013.01);  G03F  7130  (2013.01);  G03F  71322  (2013.01);  C07C  2601/16  (2017.05);  C08F 2800/10  (2013.01);  G03F 7/039  (2013.01);  G03F 7/0392  (2013.01);  G03F 7/0397  (2013.01);  G03F 7120  (2013.01);  G03F 7/2004  (2013.01);  G03F  7/327  (2013.01)  (58)  Field of Classification Search  CPC ..... G03F 7/0045; G03F 7/033; C07C 381/12;  C07C 317/04; C07C 317/28; C07C  303/32  (A)  17 Claims, 3 Drawing Sheets  (57)  ABSTRACT  A negative resist composition comprising a sulfonium com› pound having formula (A) and a base polymer is provided.  The resist composition exhibits a high resolution during  pattern formation and forms a pattern with minimal LER.  Primary Examiner  - John S Chu  (74)  Attorney, Agent, or Firm  - Westerman, Hattori,  Daniels & Adrian, LLP  * cited by examiner  FOREIGN PATENT DOCUMENTS  (56)  References Cited  U.S. PATENT DOCUMENTS  6,479,210 B2  11/2002 Kinoshita et al.  6,485,883 B2  11/2002 Kodama et al.  6,492,091 B2  12/2002 Kodama et al.  7,214,467 B2  5/2007 Kanna et al.  8,202,677 B2  6/2012 Takeda et al.  8,785,105 B2 *  7/2014 Ohsawa ................ C07C 309/12  430/270.1  9,075,306 B2  7/2015 Takeda et al.  9,233,919 B2 *  1/2016 Ohsawa ................ C07C 309/12  9,250,518 B2 *  2/2016 Hatakeyama ......... G03F 7/0046  10,173,975 B2 *  1/2019 Ohashi .................. C08F 220/24  2006/0166133 Al  7/2006 Koitabashi et al.  2018/0180992 Al*  6/2018 Kotake ................. G03F 7/0045 