c12)  United States Patent  Tsuchimura et al.  (IO)  Patent No.:  US 10,007,180 B2  (45)  Date of Patent:  Jun.26,2018  (54)  NEGATIVE RESIST COMPOSITION, RESIST  FILM USING SAME, PATTERN FORMING  METHOD, AND MASK BLANK PROVIDED  WITH RESIST FILM  USO 10007180B2  (57)  ABSTRACT  (56)  References Cited  12 Claims, No Drawings  (52)  U.S. Cl.  CPC ................  G03F  71038  (2013.01);  G03F  1150  (2013.01);  G03F  1176  (2013.01);  G03F  710045  (2013.01);  G03F  710046  (2013.01);  G03F  710382  (2013.01);  G03F  7120  (2013.01);  G03F  7140  (2013.01)  FOREIGN PATENT DOCUMENTS  JP  JP  JP  JP  JP  JP  JP  JP  JP  JP  JP  JP  JP  JP  JP  JP  WO  07-252214  09-241234  09-241234 A  10-207066  2003-121999  A  2003-307839  A  2005-308969  A  2006-084924  A  2006-282652  2006-290798  2007-230913  2007-230913  A  2008-129433  A  2009-053665  2012-133055  A  2012-159688  2012/086850 Al  * 10/1995  *  9/1997  9/1997  *  8/1998  4/2003  10/2003  11/2005  3/2006  * 10/2006  * 10/2006  *  9/2007  9/2007  6/2008  *  3/2009  7/2012  *  8/2012  6/2012  G03F 7/004  Machine translation of JP 2005-308969 (2005).*  Machine translation of JP 2003-307839 (2003).*  Machine translation of JP 09-241234 (1997).*  Machine translation of JP 2012-159688 (2012).*  Machine translation of JP 2003-121999 (2003).*  Machine translation of JP 2009-053665 (2009). *  Office Action dated Feb. 23, 2016 in Japanese Application No.  2013-002922.  International Preliminary Report on Patentability dated Jul. 23,  2015, issued by the International Bureau of WIPO in counterpart  Application No. PCT/JP2014/050162.  International Search Report for PCT/JP2014/050162 dated Mar. 25,  2014.  Office Action dated Jan. 25, 2017 from the Taiwanese Patent Office  in counterpart Taiwanese Application No. 103100840.  Office Action dated Oct. 19, 2016, in corresponding Korean Appli› cation No. 10-2015-7018164, 10 pages in Korean and English.  Office Action dated Aug. 23, 2016, from the Japanese Patent Office  in counterpart Japanese Application No. 2013-002922.  Office Action dated Nov. 24, 2017 from the Korean Patent Office in  counterpart Korean Application No. 10-2015-7018164.  Notification of Reason for Refusal, dated April 23, 2018, issued in  corresponding Korean Application No. 10-2015-7018164, 9 pages  in Korean and English.  * cited by examiner  Primary Examiner  - Martin J Angebranndt  (74)  Attorney, Agent, or Firm  - Sughrue Mion, PLLC  A negative resist composition includes an onium salt com› pound (A) containing a nitrogen atom in its cation moiety,  a compound (B) that is configured to produce an acid when  exposed to actinic rays or radiation, and a compound  (C)  containing an acid-crosslinkable group.  U.S. PATENT DOCUMENTS  OTHER PUBLICATIONS  (30)  Foreign Application Priority Data  (51)  Int. Cl.  G03F  71038  G03F  71039  G03F  7140  G03F  7120  G03F  1150  G03F  1176  G03F  71004  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (2012.01)  (2012.01)  (2006.01)  2009/0104563 Al*  4/2009 Ishiduka ............... C07C 309/10  430/285.1  2011/0212390 Al *  9/2011  Masunaga ............. G03F 7/0046  430/5  2011/0318691 Al*  12/2011 Tsuchimura  C07D 213/20  430/285.1  2012/0164574 Al*  6/2012 Tokugawa ............ G03F 7/0045  430/281.1  2012/0273924 Al*  11/2012 Matsuda ............... C07C 381/ 12  257/632  2013/0004741 Al*  1/2013 Matsuda ............... G03F 7/0397  428/195.1  (71)  Applicant:  FUJIFILM Corporation,  Tokyo (JP)  (72)  Inventors:  Tomotaka Tsuchimura,  Shizuoka (JP);  Tadateru Yatsuo,  Shizuoka (JP)  (73)  Assignee:  FUJIFILM Corporation,  Tokyo (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. days.  (21)  Appl. No.:  14/794,393  (22)  Filed:  Jul. 8, 2015  (65)  Prior Publication Data  Related U.S. Application Data  US 2015/0309408 Al  Oct. 29, 2015  (63)  Continuation  of  application  No.  PCT/JP2014/050162, filed on Jan. 8, 2014.  Jan. 10, 2013  (JP) ................................. 2013-002922  (58)  Field of Classification Search  None  See application file for complete search history.  4,954,416 A  *  9/1990 Wright .................. C07C 381/12  430/281.1  5,955,241  A  *  9/1999 Sato ...................... G03F 7/0045  430/270.1  6,033,828  A  *  3/2000 Shimada ................... C08F 8/04  430/270.11  6,156,477 A  *  12/2000 Motomi ................ G03F 7/0045  430/270.1  2005/0238992 Al  10/2005 Kodama  2006/0003260 Al *  1/2006 Nakagawa ............ G03F 7/0392  430/281.1  2008/0241745 Al*  10/2008 Shirakawa ............ G03F 7/0382  430/281.1 