US010871711B2  (IO)  Patent No.:  US 10,871,711 B2  c12)  United States Patent  Hatakeyama et al.  (54)  RESIST COMPOSITION AND PATTERNING  PROCESS  (56)  References Cited  (45)  Date of Patent:  *Dec. 22, 2020  U.S. PATENT DOCUMENTS  FOREIGN PATENT DOCUMENTS  (30)  Foreign Application Priority Data  (65)  Prior Publication Data  OTHER PUBLICATIONS  (57)  ABSTRACT  19 Claims, No Drawings  ( 58)  Field of Classification Search  CPC ....................................................... G03F 7/004  See application file for complete search history.  (52)  U.S. Cl.  CPC ..........  G03F 710045  (2013.01);  C08K 510025  (2013.01);  C08K 5142  (2013.01);  C08L 33/14  (2013.01);  C08L 41100  (2013.01);  C09D  125108  (2013.01);  C09D 133/10  (2013.01);  G03F 710395  (2013.01);  G03F 710397  (2013.01);  C08F 12/16  (2013.01);  C08F 12/24  (2013.01);  C08L 25/18  (2013.01);  C08L  2312/00  (2013.01)  (51)  Int. Cl.  (22)  Filed:  Sep. 13, 2018  (21)  Appl. No.:  16/130,271  ( *)  Notice:  Subject to any disclaimer, the term ofthis  patent is extended or adjusted under 35  U.S.C. 154(b) by 176 days.  This patent is subject to a terminal dis› claimer.  (73)  Assignee:  SHIN-ETSU CHEMICAL CO., LTD.,  Tokyo (JP)  (72)  Inventors:  Jun Hatakeyama,  Joetsu (JP);  Masaki  Ohashi,  Joetsu (JP);  Masahiro  Fukushima,  Joetsu (JP);  Takayuki  Fujiwara,  Joetsu (JP)  (71)  Applicant:  Shin-Etsu Chemical Co., Ltd.,  Tokyo  (JP)  6,551,758 B2  6,692,893 B2  6,749,988 B2  6,916,593 B2  8,026,390 B2  *  8,148,044 B2  9,250,518 B2  4/2003 Ohsawa et al.  2/2004 Ohsawa et al.  6/2004 Hatakeyama et al.  7/2005 Hatakeyama et al.  9/2011  Oh .......................... C07C 25/18  562/41  4/2012 Yamaguchi et al.  2/2016 Hatakeyama et al.  2009/0274978 Al  2015/0212417 Al  2017/0369616 Al  11/2009 Ohashi et al.  7/2015 Hatakeyama et al.  12/2017 Hatakeyama et al.  CN  JP  JP  JP  JP  JP  JP  JP  JP  JP  TW  TW  WO  102289149 A  5-204157 A  2001-194776 A  2002-226470 A  2002-363148 A  2011-252147 A  2015-25789 A  2015-90382 A  2015-161823 A  2018-5224 A  201009493 A  201533528 A  2013/024777 Al  12/2011  8/1993  7/2001  8/2002  12/2002  12/2011  2/2015  5/2015  9/2015  1/2018  3/2010  9/2015  2/2013  Sep. 25, 2017  Mar. 22, 2018  (JP) ................................. 2017-183795  (JP) ................................. 2018-054115  G03F 7100  (2006.01)  G03F 71004  (2006.01)  G03F 71039  (2006.01)  C08L 41100  (2006.01)  C08K 5100  (2006.01)  C08K 5142  (2006.01)  C08L 33/14  (2006.01)  C09D 125108  (2006.01)  C09D 133/10  (2006.01)  C08L 25/18  (2006.01)  C08F 12/24  (2006.01)  C08F 12/16  (2006.01)  US 2019/0094690 Al  Mar. 28, 2019  A resist composition is provided comprising a base polymer  containing an iodized polymer, and an acid generator con› taining a sulfonium salt and/or iodonium salt of iodized  benzene ring-containing fluorosulfonic acid. When pro› cessed by lithography, the resist composition exhibits a high  sensitivity, low LWR and improved CDU independent of  whether it is of positive tone or negative tone.  Primary Examiner  - Chanceity N Robinson  (74)  Attorney, Agent, or Firm  - Westerman, Hattori,  Daniels & Adrian, LLP  * cited by examiner  Non-Final Office Action dated Aug. 9, 2018, issued in U.S. Appl.  No. 15/623,561 (8 pages).  Non-Final Office Action dated Jun. 27, 2019, issued in U.S. Appl.  No. 15/920,641 (10 pages).  Office Action dated Feb. 26, 2018, issued in Taiwanese Application  No. 106121402. (12 pages).  Lio, "EUV Resists: What’s Next?," SPIE vol. 9776, 2016, p.  97760V-l-14.  Wang et al., "Photobase generator and photo decomposable quencher  for high-resolution photoresist applications," SPIE vol. 7639, 2010,  p. 76390Wl-15.  Yamamoto et al., "Polymer-Structure Dependence of Acid Gernera› tion in Chemically Amplified Extreme Ultraviolet Resists", Japa› nese Journal of Applied Physics, (2007), vol. 46, No. 7, pp.  Ll42-Ll44, Cited in Specification. (6 pages). 