c12)  United States Patent  Nakamura et al.  (10)  Patent No.:  US 9,052,592 B2  (45)  Date of Patent:  Jun.9,2015  (54)  RESIST COMPOSITION AND RESIST  PATTERN FORMING METHOD  (71)  Applicant:  Tokyo Ohka Kogyo Co., Ltd.,  Kawasaki-shi (JP)  (72)  Inventors:  Tsuyoshi Nakamura,  Kawasaki (JP);  Kazuishi Tanno,  Kawasaki (JP);  Akiya  Kawaue,  Kawasaki (JP);  Takayoshi  Mori,  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 0 days.  (21)  Appl. No.:  14/218,249  (22)  Filed:  Mar. 18, 2014  (51)  Int. Cl.  (52)  U.S. Cl.  CPC ..............  G03F 71038  (2013.01);  C08F 220124  (2013.01);  C08F 220156  (2013.01);  C08F  20152  (2013.01);  C07C 381112  (2013.01)  ( 58)  Field of Classification Search  USPC ............ 430/270.1, 913, 914; 526/243, 307.2,  526/303.1  See application file for complete search history.  FOREIGN PATENT DOCUMENTS  OTHER PUBLICATIONS  (57)  ABSTRACT  15 Claims, No Drawings  U.S. PATENT DOCUMENTS  (56)  References Cited  (30)  Foreign Application Priority Data  (65)  Prior Publication Data  6,949,325 B2  8,187,789 B2 *  2001/0049073 Al  2002/0068235 Al *  2004/0110085 Al  2009/0197204 Al  2009/0226842 Al *  9/2005 Li et al.  5/2012 Yonemura et al. ......... 430/270.1  12/2001 Hada et al.  6/2002 Fujita et al. ................... 430/192  6/2004 Iwai et al.  8/2009 Shiono et al.  9/2009 Shimizu et al ............. 430/281.1  G03F 71004  C08F 28100  G03F 71038  C08F 220124  C08F 220156  C08F 20152  C07C 381112  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (2006.01)  2009/0317743 Al  12/2009 Shiono et al.  2010/0196820 Al*  8/2010 Kawaue et al. ............ 430/270.1  2010/0285405 Al *  11/2010 Shimokawa et al. ...... 430/270.1  2010/0310985 Al  12/2010 Mori et al.  2011/0014569 Al*  1/2011 Kasahara et al. .......... 430/270.1  2011/0053082 Al*  3/2011 Ichikawa et al. ........... 430/270.1  2011/0117499 Al  5/2011 Matsumiya et al.  2012/0009527 Al*  1/2012 Hatakeyarna et al. ........ 430/325  2012/0149916 Al  6/2012 Utsumi et al.  2012/0171616 Al*  7/2012 Thackeray et al . ........ 430/285.1  2013/0095427 Al*  4/2013 Yahagi et al. .............. 430/285.1  2013/0115554 Al*  5/2013 Takaki et al. .............. 430/283.1  2013/0157201 Al*  6/2013 Takaki et al. ................. 430/325  JP  JP  JP  JP  JP  JP  JP  JP  JP  JP  JP  JP  JP  A-2000-206694  2000310857 A  A-2003-241385  A-2005-336452  A-2006-063318  A-2006-259582  A-2006-317803  A-2009-025723  A-2010-002870  A-2010-032994  A-2010-277043  A-2011-013569  A-2011-128226  7/2000  * 11/2000  8/2003  12/2005  3/2006  9/2006  11/2006  2/2009  1/2010  2/2010  12/2010  1/2011  6/2011  A resist composition contains a high-molecular weight com› pound which has a partial structure represented by a general  formula (a0-r-1) and has a constituent unit represented by a  general formula (a0-1). In the formula (a0-r-1), Y$^{1 }$represents  a divalent linking group; eachofR$^{2 }$andR$^{3 }$represents a group  having Oto 20 carbon atoms, which is not a fluorine atom, and  either R 2  or R 3  may form a ring with Y1; m represents an  integer of 1 or more; and  Mm+  represents an m-valent organic  cation. In the formula ( a0-1 ), R represents a hydrogen atom,  an alkyl group, or a halogenated alkyl group; Ya$^{01 }$represents  a single bond or a divalent linking group; X$^{01 }$represents a  sulfur atom or an oxygen atom; and Ra 01  represents an  optionally substituted cyclic group, chain alkyl group or  chain alkenyl group.  (74)  Attorney, Agent, or Firm  -Knobbe Martens Olson &  BearLLP  Primary Examiner  - Amanda C Walke  * cited by examiner  Iwarnura et al, Hydrogen-Transfer Polymerization Behavior of  N-Acylacrylarnide, Journal of Polymer Science:Part A:Polymer  Chemistry, vol. 38, pp. 430-435 (2000).*  Machine translation of JP 2000-310857 (no date).*  US009052592B2  US 2014/0287360Al  Sep. 25, 2014  Mar. 25, 2013  (JP) ................................. 2013-062887 