US009104101B2  c12)  United States Patent  Matsuzawa et al.  (IO)  Patent No.:  US 9,104,101 B2  (45)  Date of Patent:  Aug. 11, 2015  (54)  RESIST COMPOSITION, METHOD OF  FORMING RESIST PATTERN AND  POLYMERIC COMPOUND  (75)  Inventors:  Kensuke Matsuzawa,  Kawasaki (JP);  Jun Iwashita,  Kawasaki (JP);  Yoshitaka  Komuro,  Kawasaki (JP);  Masatoshi  Arai,  Kawasaki (JP)  (73)  Assignee:  Tokyo Ohka Kogyo Co., Ltd.,  Kawaski-shi (JP)  ( *)  Notice:  Subject to any disclaimer, the term of this  patent is extended or adjusted under 35  U.S.C. 154(b) by  O  days.  (21)  Appl. No.:  13/402,820  (22)  Filed:  Feb.22,2012  (30)  Foreign Application Priority Data  (65)  Prior Publication Data  US 2012/0282551 Al  Nov. 8, 2012  Feb. 23, 2011  (JP) ............................... P2011-037534  (51)  Int. Cl.  G03F  71004  G03F  7138  C08F  220118  C08F  220128  C08F  220138  C08F  228106  G03F  71039  G03F  7120  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (52)  U.S. Cl.  CPC ............  G03F  710045  (2013.01);  C08F  220118  (2013.01);  C08F  220128  (2013.01);  C08F  220138  (2013.01);  C08F  228106  (2013.01);  G03F  710046  (2013.01);  G03F  710397  (2013.01);  G03F  712039  (2013.01);  C08F  2220/382  (2013.01);  G03F 7/38  (2013.01)  ( 58)  Field of Classification Search  CPC ....... G03F 7/0045; G03F 7/0397; G03F 7/38;  C08F 220/18; C08F 220/28; C08F 220/38;  C08F 228/06; C08F 2220/382  USPC .............. 430/270.1, 905, 910, 921, 922, 326;  526/243, 287  See application file for complete search history.  (56)  References Cited  U.S. PATENT DOCUMENTS  5,945,517 A  6,153,733 A  6,949,325 B2  7,074,543 B2  7,932,334 B2 *  2001/0049073 Al  2006/0121390 Al  2007/0149702 Al *  2007 /0231708 Al  2008/0187860 Al  2009/0023095 Al  8/ 1999 Nitta et al.  11/2000 Yukawa et al.  9/2005 Li et al.  7/2006 Iwai et al.  4/2011 Ando et al .................... 526/243  12/2001 Hada et al.  6/2006 Gonsalves  6/2007 Ando et al .................... 524/556  10/2007 Matsumaru et al.  8/2008 Tsubaki et al.  1/2009 Hada et al.  11 Claims, No Drawings  in which R represents a hydrogen atom, an alkyl group of 1 to  5 carbon atoms or a halogenated alkyl group of 1 to 5 carbon  atoms, R 0 - 1  represents a single bond or a divalent linking  group, each of R 2 , R 3  and R 4  independently represents a  linear, branched or cyclic alkyl group which may have a  non-aromatic substituent, or R$^{3 }$andR$^{4 }$may be bonded to each  other to form a ring together with the sulfur atom, and X  represents a non-aromatic divalent linking group or a single  bond.  A resist composition including a resin component which gen› erates acid upon exposure and exhibits changed solubility in  a developing solution under the action of acid, the resin com› ponent including a resin component having a structural unit  represented by a general formula (a0-0-1) shown below  (57)  ABSTRACT  (a0-0-1)  OTHER PUBLICATIONS  FOREIGN PATENT DOCUMENTS  2010/0055606 Al  3/2010 Mimuraet al.  2010/0063232 Al*  3/2010 Nagai et al. ................... 526/287  2010/0075256 Al  3/2010 Joo et al.  2010/0255420 Al*  10/2010 Sakakibara et al. ....... 430/285.1  2010/0304303 Al  12/2010 Maeda et al.  2011/0177453 Al  7/2011 Masubuchi et al.  2011/0200940 Al  8/2011 Ichikawa et al.  2011/0244392 Al  10/2011 Hirano et al.  2012/0003583 Al  1/2012 Tsuchimura et al.  2012/0003590 Al  1/2012 Hirano et al.  2012/0082939 Al  4/2012 Kawabata et al.  2012/0156618 Al  6/2012 Takahashi et al.  2012/0328993 Al  12/2012 Utsumi et al.  2013/0137048 Al  5/2013 Yahagi et al.  2013/0157201 Al  6/2013 Takaki et al.  JP  JP  JP  JP  JP  A-09-208554  A-10-221852  A-11-035551  A-11-035552  A-11-035573  8/1997  8/1998  2/1999  2/1999  2/1999  Office Action issued on Nov. 20, 2013 in U.S. Appl. No. 13/653,930.  Office Action issued on May 20, 2014 in U.S. Appl. No. 13/653,930.  Office Action in Japanese Application No. 2011-037534, mailed  Aug. 26, 2014.  Office Action in Japanese Patent Application No. 2011-228066,  mailed Mar. 24, 2015.  Primary Examiner  - John Chu  (74)  Attorney, Agent, or Firm  -Knobbe Martens Olson &  BearLLP  (Continued) 