(IO)  Patent No.:  US 8,852,845 B2  (45)  Date of Patent:  Oct. 7, 2014  c12)  United States Patent  Takahashi et al.  (54)  ACTINIC RAY-SENSITIVE OR  RADIATION-SENSITIVE RESIN  COMPOSITION, RESIST FILM, PATTERN  FORMING METHOD USING THE SAME, AND  RESIN  (75)  Inventors:  Hidenori Takahashi,  Haibara-gun (JP);  Tomotaka Tsuchimura,  Haibara-gun  (JP);  Toru Tsuchihashi,  Haibara-gun  (JP);  Katsuhiro Yamashita,  Haibara-gun (JP);  Hideaki Tsubaki,  Haibara-gun (JP)  (73)  Assignee:  FUJIFILM Corporation,  Tokyo (JP)  ( *)  Notice:  Subject to any disclaimer, the term ofthis  patent is extended or adjusted under 35  U.S.C. 154(b) by 286 days.  (21)  Appl. No.:  12/641,877  (22)  Filed:  Dec. 18, 2009  (51)  Int. Cl.  (52)  U.S. Cl.  CPC ............  G06F  710392  (2013.01);  G03F  710397  (2013.01);  G03F  710045  (2013.01);  YJ0S  430/122  (2013.01);  YJ0S 430/123  (2013.01)  USPC .........  430/270.1;  430/326; 430/921; 430/922  ( 58)  Field of Classification Search  USPC .............. 430/270.1, 913, 914, 921, 925, 325,  430/326, 922; 526/275, 276,243; 560/221,  560/222; 525/276  See application file for complete search history.  FOREIGN PATENT DOCUMENTS  OTHER PUBLICATIONS  (57)  ABSTRACT  10 Claims, No Drawings  (56)  References Cited  U.S. PATENT DOCUMENTS  (65)  Prior Publication Data  (30)  Foreign Application Priority Data  5,260,410 A  11/1993 Schwalm  5,453,341 A  9/1995 Schwalm  5,945,250 A  8/1999 Aoai  6,680,157 Bl  1/2004 Fedynyshyn  8,057,985 B2 *  11/2011 Ohashi et al. .............. 430/270.1  2004/0091817 Al  5/2004 Komatsu  2006/0194147 Al*  8/2006 Kawanishi ................. 430/270.1  2007/0184384 Al*  8/2007 Kawanishi ................. 430/270.1  2008/0085468 Al *  4/2008 Kamimura et al. ........ 430/286.1  2008/0102407 Al *  5/2008 Ohsawaet al. ............ 430/286.1  2010/0233617 Al*  9/2010 Wada ......................... 430/270.1  G03F  71004  G03F  71028  G03F  71039  (2006.01)  (2006.01)  (2006.01)  wherein each of R$_{1}$ a  to  R$_{13}$ a  independently represents a  hydrogen atom or a monovalent substituent and may combine  together to form a ring, and Z represents a single bond or a  divalent linking group.  Provided is a actinic ray-sensitive or radiation-sensitive resin  composition including (P) a resin containing (A) a repeating  unit having an ionic structure moiety that contains a cation  represented by formula (Ia) and is capable of producing an  acid anion on the side chain upon irradiation with an actinic  ray or radiation:  Primary Examiner  - Anca Eoff  (74)  Attorney, Agent, or Firm  - Sughrue Mion, PLLC  * cited by examiner  M. Wang, "Synthesis and Properties of New Anionic Photoacid Gen› erators Bound Polymer Resists for e-beam and EUV lithography,"  Proc. ofSPIE,  vol. 6923, No. 692312 (2008).  Y.  Hirai,  Science and New Technology in Nanoimprint,  Frontier Pub› lishing (2006).  CA  EP  JP  JP  JP  JP  JP  JP  JP  JP  JP  WO  2049772 Al  1480078 Al  2-302758  A  4-230645  A  9-325497  A  10-221852  A  2004-158287  A  2006-178317  2006-178317 A  2007-210904  A  2008-162101 A  WO  2009/038148  2/1992  11/2004  12/1990  8/1992  12/1997  8/1998  6/2004  *  7/2006  7/2006  8/2007  7/2008  *  3/2009  US008852845B2  US 2010/0183975 Al  Jul. 22, 2010  Dec. 18, 2008  (JP) ................................. 2008-322678  (la)  Ria  Rsa  Re’&S*R;,  R3 0 ~Z~R 00  ~a  Rsa 