US009958775B2  c12)  United States Patent  Tsuruta et al.  (54)  ACTINIC RAY-SENSITIVE OR  RADIATION-SENSITIVE RESIN  COMPOSITION, ACTINIC RAY-SENSITIVE  OR RADIATION-SENSITIVE FILM, MASK  BLANKS INCLUDING ACTINIC  RAY-SENSITIVE OR RADIATION-SENSITIVE  FILM, PATTERN FORMING METHOD AND  PHOTO MASK  (IO)  Patent No.:  US 9,958,775 B2  (45)  Date of Patent:  May 1, 2018  (71)  Applicant:  FUJIFILM Corporation,  Minato-ku,  Tokyo (JP)  (72)  Inventors:  Takuya Tsuruta,  Haibara-gun (JP);  Tomotaka Tsuchimura,  Haibara-gun  (JP);  Tadeteru Yatsuo,  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  O  days. days.  (21)  Appl. No.:  14/560,650  Dec. 4, 2014  (22)  Filed:  (63)  Continuation  of  application  PCT/JP2013/067157, filed on Jun. 17, 2013.  No.  (51)  Int. Cl.  (52)  U.S. Cl.  CPC ..........  G03F 710045  (2013.01);  C07C 309/65  (2013.01);  C07C 381112  (2013.01);  C07D  327108  (2013.01);  C07D 333/46  (2013.01);  G03F  710046  (2013.01);  G03F  71038  (2013.01);  G03F  710382  (2013.01);  G03F  710397  (2013.01);  G03F  712037  (2013.01);  G03F  71325  (2013.01);  C07C 2601/14  (2017.05)  ( 58)  Field of Classification Search  None  Jul. 9, 2012  (JP) ................................. 2012-154118  An actinic ray-sensitive or radiation-sensitive resin compo› sition includes; a compound (A) which generates an acid by  irradiation with actinic rays or radiation, wherein the acid is  linked with a group represented by the following general  formula (M) through covalent bonding. In the formula,  Y $_{1 }$ and Y $_{2 }$ each independently represent a hydrogen atom, an  alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl  group, an aryl group, or an acyl group. Z represents a  hydrogen atom or a substituent.  * represents a linking site  with a residue of the compound (A)  Primary Examiner  - Sin J Lee  (74)  Attorney, Agent, or Firm  - Sughrue Mion, PLLC  (Continued)  JPO English translation of JP 2012-73401 (2012).*  (Continued)  [Chem.!]  See application file for complete search history.  (M)  20 Claims, No Drawings  (57)  ABSTRACT  (30)  Foreign Application Priority Data  OTHER PUBLICATIONS  Related U.S. Application Data  (65)  Prior Publication Data  US 2015/0086911 Al  Mar. 26, 2015  FOREIGN PATENT DOCUMENTS  U.S. PATENT DOCUMENTS  (56)  References Cited  6/2005 Wada et al.  8/2006 Wada et al.  2005/0123859 Al  2006/0172228 Al  2006/0194982 Al*  8/2006 Harada ................. C07C 309/17  560/150  2007/0100096 Al*  5/2007 Harada ................. C07C 309/17  526/135  2007/0141512 Al  6/2007 Wada et al.  2007 /0248897 Al *  10/2007 Yoshikawa et al. .............. 430/5  2009/0258315 Al*  10/2009 Ober .  C07D 309/10  430/270.1  2010/0081066 Al*  4/2010 Nozawa .................... G03F 1/32  430/5  2010/0143830 Al  6/2010 Ohashi et al.  2011/0076615 Al  3/2011 Kawabata et al.  2011/0200936 Al  8/2011 Ichikawa et al.  2011/0250543 Al*  10/2011 Tsubaki ........................ 430/325  2011/0287234 Al *  11/2011 Tsuchihashi et al . ...... 428/195.1  2012/0322007 Al  12/2012 Kato et al.  JP  JP  JP  2000-199953 A  2001-019799 A  2005-148291 A  7/2000  1/2001  6/2005  G03F  71004  (2006.01)  G03F  71039  (2006.01)  G03F  71038  (2006.01)  G03F  7120  (2006.01)  G03F  7132  (2006.01)  C07D 333/46  (2006.01)  C07D 327108  (2006.01)  C07C 309/65  (2006.01)  C07C 381112  (2006.01) 