US010620533B2  (IO)  Patent No.:  US 10,620,533 B2  Apr. 14, 2020  (45)  Date of Patent:  c12)  United States Patent  Hatakeyama et al.  (54)  RESIST COMPOSITION AND PATTERNING  PROCESS  C08F 228/02; C08F 228/06; C07C  303/32; C07C 309/04; C07C 309/06;  C07C 309/07; C07C 309/10; C07C  309/12; C07C 309/13; C07C 309/17;  C07C 309/19; C07C 309/23; C07C  309/24; C07C 309/09  USPC ..... 430/270.1, 326, 919, 920; 526/243, 245,  526/247, 266, 268, 287, 319, 321, 326;  562/104, 107, 108, 111, 113  See application file for complete search history.  (52)  U.S. Cl.  CPC ..........  G03F 710045  (2013.01);  C07C 303132  (2013.01);  C07C 309/10  (2013.01);  C07C  309112  (2013.01);  C07C 309/13  (2013.01);  C07C 309/19  (2013.01);  C08F 220124  (2013.01);  C08F  228102  (2013.01);  C08F  228106  (2013.01);  G03F  710392  (2013.01);  G03F  710395  (2013.01);  G03F  710397  (2013.01);  G03F  712006  (2013.01);  G03F  712037  (2013.01);  G03F  712041  (2013.01);  G03F  712059  (2013.01);  C08F 2220/282  (2013.01);  C08F 2220/301  (2013.01);  C08F  2220/382  (2013.01)  (58)  Field of Classification Search  CPC ........ G03F 7/0045; G03F 7/0397; G03F 7/38;  G03F 7/0382; G03F 7/0392; G03F  7/2006; G03F 7/2037; G03F 7/2041;  G03F 7/2059; G03F 7/30; C08F 220/24;  C08F 220/38; C08F 220/382; C08F  224/00; C08F 228/00; C08F 2220/382;  Oct. 19, 2015  (JP) ................................. 2015-205402  (51)  Int. Cl.  (22)  Filed:  Oct. 18, 2016  (21)  Appl. No.:  15/296,662  ( * )  Notice:  Subject to any disclaimer, the term ofthis  patent is extended or adjusted under 35  U.S.C. 154(b) by 41 days.  (73)  Assignee:  SHIN-ETSU CHEMICAL CO., LTD.,  Tokyo (JP)  (72)  Inventors:  Jun Hatakeyama,  Joetsu (JP);  Masaki  Ohashi,  Joetsu (JP)  (71)  Applicant:  SHIN-ETSU CHEMICAL CO., LTD.,  Tokyo (JP)  US 2017/0108775 Al  Apr. 20, 2017  Hinsberg et al., Extendibility of Chemically Amplified Resists:  Another Brick Wall?, SPIE vol. 5039 (2003) (14 pages).  Kishikawa et  al., Assessment of Trade-off between Resist Resolu› tion and Sensitivity for Optimization of Hyper-NA Immersion  Lithography, SPIE vol. 6520 (2007) (9 pages).  Cwwang et al., Photobase Generator and Photo Decomposable  Quencher for High-resolution Photoresist Applications, SPIE vol.  7639 (2010) (15 pages).  Office Action dated Aug. 29, 2017, issued in counterpart Taiwanese  Application No. 105133367. (5 pages).  Office Action dated Aug. 14, 2018, issued in counterpart Japanese  Application No. 2015-205402, with English translation (12 pages).  * cited by examiner  Primary Examiner  - John S Chu  (74)  Attorney, Agent, or Firm  - Westerman, Hattori,  Daniels & Adrian, LLP  A resist composition comprising a base polymer and a  sulfonium or iodonium salt of sulfonic acid containing a  morpholino group offers dimensional stability on PPD and a  satisfactory resolution.  (57)  ABSTRACT  17 Claims, No Drawings  OTHER PUBLICATIONS  FOREIGN PATENT DOCUMENTS  (56)  References Cited  U.S. PATENT DOCUMENTS  (65)  Prior Publication Data  (30)  Foreign Application Priority Data  G03F  71004  G03F  7130  C07C  303132  C07C 309/10  C07C  309112  C07C 309/13  C07C 309/19  C08F  220124  C08F  228102  C08F  228106  G03F  71039  G03F  7120  C08F 220/30  C08F 220/28  C08F 220/38  (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)  JP  JP  JP  JP  JP  JP  JP  JP  2000-089454  A  2001-194776 A  2002-226470  A  2002-363148  A  2008-065266  A  2011-154160 A  2014-074898 A  2015-90382  A  3/2000  7/2001  8/2002  12/2002  3/2008  8/2011  4/2014  5/2015  6,673,511 Bl  1/2004 Hatakeyama et al.  6,749,988 B2  6/2004 Hatakeyama et al.  6,916,593 B2  7/2005 Hatakeyama et al.  8,852,846 B2 * 10/2014 Anryu .  C07D 279/12  430/270.1  9,250,518 B2  2/2016 Hatakeyama et al.  2002/0102491 Al *  8/2002 Kodama ............... C07C 309/06  430/270.1  2004/0029037 Al *  2/2004 Kamabuchi ........... G03F 7/0045  430/270.1  2014/0242519 Al *  8/2014 Sagehashi ............... G03F 7/038  430/285.1  2017/0075218 Al*  3/2017 Hatakeyama ......... G03F 7/0045 