US009217919B2  c12)  United States Patent  Takahashi et al.  (54)  PHOTOSENSITIVE COMPOSITION,  PATTERN-FORMING METHOD USING THE  COMPOSITION, AND RESIN USED IN THE  COMPOSITION  (IO)  Patent No.:  US 9,217,919 B2  (45)  Date of Patent:  Dec. 22, 2015  (52)  U.S. Cl.  CPC ..............  G03F  710392  (2013.01);  C0SF  12120  (2013.01);  C0SF  12122  (2013.01);  C0SF  12130  (2013.01);  C0SF  12132  (2013.01);  C09D  125118  (2013.01);  G03F  710045  (2013.01);  G03F  710046  (2013.01)  (75)  Inventors:  Hidenori Takahashi,  Shizuoka (JP);  Tomotaka Tsuchimura,  Shizuoka (JP);  Toru Tsuchihashi,  Shizuoka (JP);  Katsuhiro Yamashita,  Shizuoka (JP);  Naoyuki Nishikawa,  Kanagawa (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 70 days.  (21)  Appl. No.:  13/062,285  (22)  PCT Filed:  Aug.26,2009  (86)  PCT No.:  PCT  I  JP2009/065286  § 371 (c)(l),  (2), ( 4) Date:  Mar. 10, 2011  (87)  PCT Pub. No.:  WO2010/026973  PCT Pub. Date:  Mar. 11, 2010  (51)  Int. Cl.  (65)  Prior Publication Data  Related U.S. Application Data  (30)  Foreign Application Priority Data  (60)  Provisional application No. 61/096,586, filed on Sep.  12, 2008.  US 2011/0159433 Al  Jun. 30, 2011  Sep.5,2008  Jun. 18, 2009  (JP) ................................. 2008-228994  (JP) ................................. 2009-145677  G03F  71004  C0SF  12120  (2006.01)  (2006.01)  (Continued)  A radiation-sensitive composition including a compound (P)  having a partial structure (A) having an ionic structural site  and capable of decomposing upon irradiation with an actinic  ray or radiation to generate an acid and a partial structure (B)  having at least one phenolic hydroxyl group, a part or all of  hydrogen atoms of the hydroxyl group or groups each being  protected by a group capable of leaving by the action of an  acid, wherein the ionic structural site of the partial structure  (A) contained in the compound (P) is a structure capable of  generating an acid anion in the compound (P) upon irradia› tion with an actinic ray or radiation; a pattern-forming  method using the same; and a resin which is used in the  composition.  26 Claims, 1 Drawing Sheet  (57)  ABSTRACT  Machine translation JP 2006-178317. Jul. 6, 2006.  *  (Continued)  Primary Examiner  - Cynthia H Kelly  Assistant Examiner  - Alyssa L Cepluch  (74)  Attorney, Agent, or Firm  - Sughrue Mion, PLLC  (Continued)  (Continued)  OTHER PUBLICATIONS  FOREIGN PATENT DOCUMENTS  EP  EP  0 380 007 A2  2090931 Al  8/1990  8/2009  5,260,410 A  11/1993 Schwalm  5,945,250 A  *  8/1999 Aoai et al. ................. 430/270.1  (56)  References Cited  U.S. PATENT DOCUMENTS  (58)  Field of Classification Search  None  See application file for complete search history. 