US009904167B2  c12)  United States Patent  Tsuchimura  (IO)  Patent No.:  US 9,904,167 B2  Feb.27,2018  (45)  Date of Patent:  (54)  COMPOUND, ACTIVE LIGHT SENSITIVE  OR RADIATION SENSITIVE RESIN  COMPOSITION, RESIST FILM USING  SAME, RESIST-COATED MASK BLANK,  PHOTOMASK, PATTERN FORMING  METHOD, METHOD FOR  MANUFACTURING ELECTRONIC DEVICE,  AND ELECTRONIC DEVICE  (71)  Applicant:  FUJIFILM Corporation,  Tokyo (JP)  (72)  Inventor:  Tomotaka Tsuchimura,  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 0 days.  (21)  Appl. No.:  14/982,759  (22)  Filed:  Dec. 29, 2015  (63)  Continuation  of  application  No.  PCT/JP2014/065498, filed on Jun. 11, 2014.  (51)  Int. Cl.  (52)  U.S. Cl.  CPC ............  G03F 710045  (2013.01);  C07C 25118  (2013.01);  C07C 309115  (2013.01);  C07C  309/19  (2013.01);  C07C 311114  (2013.01);  C07C 311/16  (2013.01);  C07C 311148  (2013.01);  C07C 311151  (2013.01);  C07C  321128  (2013.01);  C07C 323109  (2013.01);  C07C 323120  (2013.01);  C07C  327122  (2013.01);  C07C  327124  (2013.01);  C07C  327126  (2013.01);  C07C 381112  (2013.01);  C07D 209/48  (2013.01);  C07D 327108  (2013.01);  C07D 333/46  (2013.01);  C07D  333176  (2013.01);  C07D 335/16  (2013.01);  C07D 339/08  (2013.01);  C07D  347100  (2013.01);  C07D 493/08  (2013.01);  C07J  31/006  (2013.01);  C07J 4110055  (2013.01);  C07J 4110061  (2013.01);  G03F 710382  (2013.01);  G03F  710392  (2013.01);  G03F  710397  (2013.01);  H0JL 2110271  (2013.01);  H0JL 2110276  (2013.01);  H0JL 29116  (58)  Field of Classification Search  CPC ...... G03F 7/004; G03F 7/0045; G03F 7/0382;  G03F 7/0397; C07C 381/12; C08F  220/30; H0lL 21/0271  USPC  430/270.1, 322, 325, 329, 330, 913;  526/319, 326, 346; 560/129, 14, 15, 19;  562/625  See application file for complete search history.  (Continued)  (2013.01);  C07C 2601/08  (2017.05);  C07C  2601/14  (2017.05);  C07C 2602/42  (2017.05);  (Continued)  (Continued)  (Continued)  Provided is an active light sensitive or radiation sensitive  resin composition which contains a compound (A) repre› sented by General Formula  (I)  or (II):  Primary Examiner  - Amanda C. Walke  (74)  Attorney, Agent, or Firm  - Sughrue Mion, PLLC  Machine translation of JP 2007-291032 (no date).*  International Search Report dated Sep. 16, 2014 issued by Interna› tional Searching Authority in counterpart International Patent  Application No. PCT/JP2014/065498 (PCT/ISA/210).  Written Opinion dated Sep. 16, 2014 issued by International Search› ing Authority in counterpart International Patent Application No.  PCT/JP2014/065498 (PCT/ISA/237).  (Continued)  in the formulae, each ofY$_{1 }$ and Y$_{2 }$ represents a monovalent  organic group; each of M$_{1 }$ +  and M$_{2 }$ +  represents an organic  onium ion; each of X$_{1 }$ and X$_{2 }$ represents a group that is  represented by -S-, -NH-, or -NR  1  -; R  $^{1 }$represents  a monovalent organic group; each of nl and n2 represents an  integer of 1 or more; and R  1  and Y $_{1 }$ or Y $_{2 }$ may bond with  each other to form a ring.  17 Claims, No Drawings  (30)  Foreign Application Priority Data  Related U.S. Application Data  (65)  Prior Publication Data  US 2016/0116840 Al  Apr. 28, 2016  OTHER PUBLICATIONS  (57)  ABSTRACT  FOREIGN PATENT DOCUMENTS  U.S. PATENT DOCUMENTS  (56)  References Cited  4,015,991 A *  4/1977 Persinski  4,167,618 A  9/1979 Schmitt et al.  C09K 8/46  166/293  JP  JP  6-501970 A  3/1994  2005148291 A  *  6/2005  Jul. 10, 2013  Feb. 14, 2014  (JP) ................................. 2013-145015  (JP) ................................. 2014-026904  G03F 71004  H0JL 211027  C07D 327108  C07C 309115  C07D 333176  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (I)  (II) 