(IO)  Patent No.:  US 10,222,696 B2  Mar.5,2019  (45)  Date of Patent:  c12)  United States Patent  Hatakeyama et al.  (54)  RESIST COMPOSITION AND PATTERNING  PROCESS  USO 10222696B2  (71)  Applicant:  Shin-Etsu Chemical Co., Ltd.,  Tokyo  (JP)  USPC ........ 430/270.1, 919, 920; 526/287, 292.95;  556/35, 36  See application file for complete search history.  (72)  Inventors:  Jun Hatakeyama,  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.  (21)  Appl. No.:  15/375,353  (22)  Filed:  Dec. 12, 2016  (51)  Int. Cl.  (52)  U.S. Cl.  CPC ..........  G03F  710045  (2013.01);  C07C  303132  (2013.01);  G03F  710382  (2013.01);  G03F  710397  (2013.01);  G03F  71162  (2013.01);  G03F  71168  (2013.01);  G03F  712004  (2013.01);  G03F  712006  (2013.01);  G03F  712037  (2013.01);  G03F  712041  (2013.01);  G03F  71322  (2013.01)  ( 58)  Field of Classification Search  CPC ... G03F 7/0045; G03F 7/0397; C07C 303/32;  C07C 63/08; C07C 279/02  (56)  References Cited  U.S. PATENT DOCUMENTS  FOREIGN PATENT DOCUMENTS  OTHER PUBLICATIONS  (57)  ABSTRACT  16 Claims, No Drawings  (65)  Prior Publication Data  (30)  Foreign Application Priority Data  US 2017 /0184962 Al  Jun. 29, 2017  6,673,511 Bl  6,749,988 B2  6,916,593 B2  8,507,175 B2 *  9,250,518 B2  1/2004 Hatakeyama et al.  6/2004 Hatakeyama et al.  7/2005 Hatakeyama et al.  8/2013 Hatakeyama ......... G03F 7/0045  430/270.1  2/2016 Hatakeyama et al.  2010/0304297 Al*  12/2010 Hatakeyama ......... G03F 7/0035  430/270.1  2014/0034371 Al*  2/2014 Endo ..................... G03F 7/2016  174/258  2015/0125794 Al*  5/2015 Hatakeyama ......... G03F 7/0046  430/285.1  2016/0152783 Al *  6/2016 Yamaga .  C08G 65/336  522/109  JP  JP  JP  JP  JP  WO  2001-194776 A  2002-226470 A  2002-363148 A  2010-84144 A  2015-90382 A  2015/111640 Al  7/2001  8/2002  12/2002  4/2010  5/2015  7/2015  G03F  71004  (2006.01)  G03F  7140  (2006.01)  C07C  303132  (2006.01)  G03F  71039  (2006.01)  G03F  71038  (2006.01)  G03F  7116  (2006.01)  G03F  7120  (2006.01)  G03F  7132  (2006.01)  A resist composition comprising a base polymer and a  biguanide salt compound offers a high dissolution contrast,  minimal LWR, and dimensional stability on PPD.  Primary Examiner  - John S Chu  (74)  Attorney, Agent, or Firm  - Westerman, Hattori,  Daniels & Adrian, LLP  * cited by examiner  Hinsberg et al., "Extendibility of Chemically Amplified Resists :  Another Brick Wall?", SPIE, 2003, vol. 5039, pp. 1-14, (14 pages).  Kishikawa et al., "Assessment of trade-off between resist resolution  and sensitivity for optimization of hyper-NA immersion lithogra› phy", SPIE, 2007, vol. 6520, pp. 65203L 1-9, (9 pages).  Wang et  al., "Photobase generator and photo decomposable quencher  for high-resolution photoresist applications", SPIE, 2010, vol. 7639,  pp. 76390W 1-15, (15 pages).  Dec. 28, 2015  Jul. 7, 2016  (JP) ................................. 2015-256315  (JP) ................................. 2016-135001 