US009086623B2  c12)  United States Patent  Kato et al.  (IO)  Patent No.:  US 9,086,623 B2  Jul. 21, 2015  (45)  Date of Patent:  (54)  METHOD OF FORMING PATTERN,  ACTINIC-RAY- OR RADIATION-SENSITIVE  RESIN COMPOSITION AND ACTINIC-RAY› OR RADIATION-SENSITIVE FILM  2006/0121390 Al*  2008/0187860 Al  2008/0261150 Al*  2009/0011366 Al  2009/0142693 Al  2010/0330507 Al  2011/0177462 Al  2011/0244392 Al *  2011/0300485 Al  2012/0058436 Al  2012/0135355 Al*  2013/0022911 Al *  2013/0344441 Al *  6/2006 Gonsalves ................. 430/270.1  8/2008 Tsubaki et al.  10/2008 Tsubaki et al. ............ 430/270.1  1/2009 Tsubaki et al.  6/2009 Iwashita  12/2010 Tsubaki et al.  7/2011 Hatakeyama et al.  10/2011 Hirano et al. .............. 430/270.1  12/2011 Tsubaki et al.  3/2012 Tsubaki et al.  5/2012 Tsubaki ........................ 430/311  1/2013 Utsumi et al .............. 430/270.1  12/2013 Sooriyakumaran  et al. .......................... 430/285 .1  FOREIGN PATENT DOCUMENTS  JP  JP  JP  JP  JP  JP  JP  JP  JP  JP  JP  JP  JP  JP  JP  JP  WO  6-35195  A  6-80724  A  10-104834 A  2000-206694  A  2006-195050  A  2006-259582  A  2006-317803  A  2007-025534  A  2008-281974  A  2008-281975  A  2008-292975  A  2010-24330  A  2010-077038  A  2010-176089  A  2010-217884 A  2011-170316 A  2009/143357 A2  2/1994  3/1994  4/1998  7/2000  7/2006  9/2006  11/2006  2/2007  11/2008  11/2008  12/2008  2/2010  4/2010  8/2010  9/2010  9/2011  11/2009  OTHER PUBLICATIONS  Japanese Office Action dated Jul. 9, 2013 issued in Japanese Patent  Application No. 2011-187055.  Japanese Office Action dated May 20, 2014 issued in corresponding  application No. 2011-187055.  * cited by examiner  Primary Examiner  - Amanda C Walke  (74)  Attorney, Agent, or Firm  - Sughrue Mion, PLLC  (57)  ABSTRACT  Provided is a method of forming a pattern, including forming  an actinic-ray- or radiation-sensitive resin composition into a  film, the actinic-ray- or radiation-sensitive resin composition  including a resin (A) including a repeating unit containing a  group that when acted on by an acid, is decomposed to  thereby produce a polar group and including an aromatic  group, which resin when acted on by an acid, decreases its  solubility in an organic solvent, a nonionic compound (B) that  when exposed to actinic rays or radiation, generates an acid  and a solvent (C), exposing the film to actinic rays or radia› tion, and developing the exposed film with a developer  including an organic solvent to thereby form a negative pat› tern.  18 Claims, No Drawings  (56)  References Cited  U.S. PATENT DOCUMENTS  6,114,082 A  7,214,467 B2 *  8,017,298 B2 *  8,227,183 B2 *  8,546,063 B2 *  8,632,942 B2 *  2001/0049073 Al  2005/0065312 Al  9/2000 Hakey et al.  5/2007 Kanna et al ................ 430/270.1  9/2011 Tsubaki ..................... 430/270.1  7/2012 Tsubaki et al. ............... 430/434  10/2013 Tsubaki et al. ............... 430/296  1/2014 Tsubaki ..................... 430/270.1  12/2001 Hada et al.  3/2005 Hada et al.  ( 58)  Field of Classification Search  CPC ....... G03F 7/004; G03F 7/397; G03F 7/2041;  G03F 7/0045; G03F 7/0046; G03F 7/0392;  G03F 7/32; C08F 220/10; C08F 212/08;  Yl0S 430/114; C07C 2103/56; C07C  2103/74; C07C 2102/14; H0lL 21/0274;  H0lL 21/3081  USPC ............... 430/270.1, 434, 435, 905, 913, 914  See application file for complete search history.  (52)  U.S. Cl.  CPC ............  G03F  710045  (2013.01);  C08F  212108  (2013.01);  C08F  220110  (2013.01);  G03F  710046  (2013.01);  G03F 710392  (2013.01);  G03F 710397  (2013.01);  G03F 71325  (2013.01);  H0JL 2110274  (2013.01);  H0JL  2113081  (2013.01);  C07C 2102/14  (2013.01);  C07C 2103/56  (2013.01);  C07C 2103/74  (2013.01);  YJ0S 430/114  (2013.01)  (51)  Int. Cl.  G03F  71004  G03F  7120  G03F  7132  C08F 220110  C08F 212108  H0JL21/027  H0JL21/308  G03F 71039  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (30)  Foreign Application Priority Data  Aug. 30, 2011  (JP) ................................. 2011-187055  (65)  Prior Publication Data  US 2013/0049149 Al  Feb. 28, 2013  (75)  Inventors:  Keita Kato,  Shizuoka (JP);  Atsushi  Nakamura,  Shizuoka (JP)  ( *)  Notice:  Subject to any disclaimer, the term of this  patent is extended or adjusted under 35  U.S.C. 154(b) by 24 days.  (73)  Assignee:  FUJIFILM Corporation,  Tokyo (JP)  (21)  Appl. No.:  13/598,087  (22)  Filed:  Aug. 29, 2012 