US009250518B2  (10)  Patent No.:  US 9,250,518 B2  (45)  Date of Patent:  Feb.2,2016  c12)  United States Patent  Hatakeyama et al.  (54)  RESIST COMPOSITION AND PATTERNING  PROCESS  (71)  Applicant:  SHIN-ETSU CHEMICAL CO., LTD.,  Tokyo (JP)  (72)  Inventors:  Jun Hatakeyama,  Joetsu (JP);  Masaki  Ohashi,  Joetsu (JP);  Masayoshi  Sagehashi,  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.:  14/529,582  (22)  Filed:  Oct. 31, 2014  (51)  Int. Cl.  (52)  U.S. Cl.  CPC ............  G03F  710045  (2013.01);  G03F  710046  (2013.01);  G03F  710382  (2013.01);  G03F  710397  (2013.01);  G03F  712041  (2013.01);  G03F  7130  (2013.01)  ( 58)  Field of Classification Search  None  See application file for complete search history.  6,673,511 Bl  6,749,988 B2  6,916,593 B2  7,511,169 B2  7,527,912 B2  7,537,880 B2  7,598,016 B2  7,771,914 B2  7,919,226 B2  8,114,570 B2  1/2004 Hatakeyama et al.  6/2004 Hatakeyama et al.  7/2005 Hatakeyama et al.  3/2009 Ohsawa et al.  5/2009 Ohsawa et al.  5/2009 Harada et al.  10/2009 Kobayashi et al.  8/2010 Hatakeyama et al.  4/2011 Ohsawa et al.  2/2012 Ohsawa et al.  (56)  References Cited  U.S. PATENT DOCUMENTS  (30)  Foreign Application Priority Data  (65)  Prior Publication Data  OTHER PUBLICATIONS  (57)  ABSTRACT  FOREIGN PATENT DOCUMENTS  15 Claims, No Drawings  US 2015/0125794Al  May 7, 2015  Nov. 5, 2013  (JP) ................................. 2013-229075  JPO English abstract for JP 2006-258980 (2006).*  Machine-assisted English translation for JP 2006-258980 provided  by JPO (2006).*  Hinsberg et  al., "Extendibility of Chemically Amplified Resists:  Another Brick Wall?", Proceedings of SPIE, 2003, pp. 1-14, vol.  5039.  Kishikawa et al., "Assessment of trade-off between resist resolution  and sensitivity for optimization of hyper-NA immersion lithogra› phy", Proceedings of SPIE, 2007, pp. 65203L-l-65203L-9, vol.  6520.  Wang et  al., "Photo base generator and photo decomposable quencher  for high-resolution photoresist applications", Proceedings of SPIE,  2010, pp. 76390W-l-76390W-15, vol. 7639.  * cited by examiner  Primary Examiner  - Sin Lee  (74)  Attorney,  Agent,  or Firm  - Westerman,  Hattori,  Daniels & Adrian, LLP  A photoresist film containing a sulfonium or iodonium salt of  carboxylic acid having an amino group has a high dissolution  contrast and offers improved resolution, wide focus margin  and minimal LWR when used as a positive resist film adapted  for alkaline development and a negative resist film adapted  for organic solvent development.  8,435,717 B2  8,574,817 B2  8,846,303 B2  5/2013 Hagiwara et al.  2008/0090172 Al  2008/0118860 Al  2008/0153030 Al  2012/0141938 Al  11/2013 Hatakeyama et al.  9/2014 Hatakeyama et al.  4/2008 Hatakeyama et al.  5/2008 Harada et al.  6/2008 Kobayashi et al.  6/2012 Hatakeyama et al.  JP  JP  JP  JP  JP  JP  JP  JP  JP  JP  JP  JP  JP  JP  JP  JP  JP  JP  2001-194776 A  2002-226470  A  2002-363148  A  2005-84365  A  3790649 B2  2006-178317 A  2006-258980  2007-145797 A  2008-106045  A  2008-111103 A  2008-122932  A  2008-158339  A  2008-239918  A  2009-7327  A  2009-258695  A  2012-137729  A  2013-80033  A  2013-83821  A  7/2001  8/2002  12/2002  3/2005  6/2006  7/2006  *  9/2006  6/2007  5/2008  5/2008  5/2008  7/2008  10/2008  1/2009  11/2009  7/2012  5/2013  5/2013  G03F  71004  G03F  71039  G03F  71038  G03F  7120  G03F  7130  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (2006.01) 