US009164380B2  c12)  United States Patent  Komuro et al.  (IO)  Patent No.:  US 9,164,380 B2  Oct. 20, 2015  (45)  Date of Patent:  (54)  RESIST COMPOSITION AND METHOD OF  FORMING RESIST PATTERN  (71)  Applicant:  Tokyo Ohka Kogyo Co., Ltd.,  Kawasaki-shi (JP)  (72)  Inventors:  Yoshitaka Komuro,  Kawasaki (JP);  Yoshiyuki Utsumi,  Kawasaki (JP);  Akiya Kawaue,  Kawasaki (JP);  Toshiaki Hato,  Kawasaki (JP)  (73)  Assignee:  TOKYO OHKA KOGYO CO., LTD.,  Kawasaki-Shi (JP)  ( *)  Notice:  Subject to any disclaimer, the term ofthis  patent is extended or adjusted under 35  U.S.C. 154(b) by 62 days.  (21)  Appl. No.:  13/710,809  (22)  Filed:  Dec. 11, 2012  (65)  Prior Publication Data  (30)  Foreign Application Priority Data  US 2013/0189619 Al  Jul. 25, 2013  Dec. 14, 2011  (JP) ................................. 2011-273759  (51)  Int. Cl.  G03F  71004  G03F  71039  G03F  7120  G03F  7130  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (52)  U.S. Cl.  CPC ..............  G03F  710045  (2013.01);  G03F  71004  (2013.01);  G03F  710046  (2013.01);  G03F  710392  (2013.01);  G03F  710397  (2013.01);  G03F  7120  (2013.01);  G03F  712041  (2013.01);  G03F  7130  (2013.01)  ( 58)  Field of Classification Search  None  See application file for complete search history.  (56)  References Cited  U.S. PATENT DOCUMENTS  5,945,517 A  6,153,733 A  6,656,660 Bl *  6,949,325 B2  2001/0049073 Al  2003/0134223 Al *  2004/0110085 Al  2006/0008736 Al  2006/0078821 Al  2008/0187860 Al  2009/0004598 Al  2009/0317743 Al  2010/0086873 Al *  8/ 1999 Nitta et al.  11/2000 Yukawa et al.  12/2003 Urano et al. ............... 430/270.1  9/2005 Li et al.  12/2001 Hada et al.  7/2003 Katano et al. ................. 430/191  6/2004 Iwai et al.  1/2006 Kanda et al.  4/2006 Shimizu et al.  8/2008 Tsubaki et al.  1/2009 Nakagawa et al.  12/2009 Shiono et al.  4/2010 Seshimo et al. ........... 430/281.1  (57)  ABSTRACT  A resist composition containing a base component (A) that  exhibits changed solubility in a developing solution under  action of acid, a photoreactive quencher (C), and an acid  generator component (B) that generates acid upon exposure,  and further containing an acid (G) having a pKa of 4 or less.  6 Claims, No Drawings  OTHER PUBLICATIONS  FOREIGN PATENT DOCUMENTS  2010/0233626 Al  2010/0295891 Al*  2010/0310985 Al *  2011/0223537 Al  2012/0082936 Al  2012/0149916 Al  2014/0113236 Al  9/2010 Shimizu et al.  11/2010 Goto eta!. ...................... 347/21  12/2010 Mori et al. ................. 430/270.1  9/2011 Ebata et al.  4/2012 Serizawa et al.  6/2012 Utsumi et al.  4/2014 Senzaki et al.  JP  JP  JP  JP  JP  JP  JP  JP  JP  JP  JP  JP  JP  JP  JP  JP  JP  JP  JP  JP  JP  JP  JP  JP  JP  JP  JP  WO  WO  WO  WO  A-06-266100  A-09-208554  A-11-035551  A-11-035552  A-11-035573  A-11-322707  A-2000-206694  A-2002-131911  A-2003-241385  A-2005-336452  A-2006-106693  A-2006-259582  A-2006-317803  A-2006-343704  A-2007-106717  2008-15247  A-2008-089710  A-2008-292975  A-2009-191055  A-2009-209128  A-2009-274963  A-2010-002870  A-2010-210953  A-2010-250340  A-2011-051945  A-2011-170284  A-2012-121838  WO 2004/074242 A2  WO 2010/029965 Al  WO 2010/147079 Al  WO 2012/169620 Al  9/1994  8/1997  2/1999  2/1999  2/1999  11/1999  7/2000  5/2002  8/2003  12/2005  4/2006  9/2006  11/2006  12/2006  4/2007  *  1/2008  4/2008  12/2008  8/2009  9/2009  11/2009  1/2010  9/2010  11/2010  3/2011  9/2011  6/2012  9/2004  3/2010  12/2010  12/2012  Machine-assited English translation of JP2008-15247, as provided  by JPO (2008).*  Office Action in Japanese Patent Application No. 2011-273759,  mailed May 19, 2015.  Anthracene-9-carboxylic acid(723-62-6)’, Chemical Book, [ online ],  [retrieved on May 13, 20 15], URL:http://www.chemicalbook.com/  ProductMSDSDetailCB57 l 1497.  * cited by examiner  Primary Examiner  - Sin Lee  (74)  Attorney, Agent, or Firm  -Knobbe Martens Olson &  BearLLP 