US009170489B2  (IO)  Patent No.:  US  9,170,489 B2  Oct. 27, 2015  (45)  Date of Patent:  c12)  United States Patent  Takizawa et al.  (54)  PATTERN-FORMING METHOD, ELECTRON  BEAM-SENSITIVE OR EXTREME  ULTRAVIOLET RADIATION-SENSITIVE  RESIN COMPOSITION, RESIST FILM,  MANUFACTURING METHOD OF  ELECTRONIC DEVICE USING THEM AND  ELECTRONIC DEVICE  (71)  Applicant:  FUJIFILM Corporation,  Tokyo (JP)  (72)  Inventors:  Hiroo Takizawa,  Shizuoka (JP);  Hideaki Tsubaki,  Shizuoka (JP);  Shuji  Hirano,  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.:  14/207,867  (22)  Filed:  Mar. 13, 2014  (65)  Prior Publication Data  Related U.S. Application Data  (30)  Foreign Application Priority Data  US 2014/0193749 Al  Jul. 10, 2014  (63)  Continuation of application No. PCT/JP2012/073765,  filed on Sep. 11, 2012.  (60)  Provisional application No. 61/535,024, filed on Sep.  15, 2011.  (51)  Int. Cl.  Sep. 15, 2011  (JP) ................................. 2011-202044  G03F  71004  G03F  71039  G03F  7120  G03F  71038  C08F  212114  G03F  7132  H0JJ37/317  C08F 12/20  C08F 12/24  C08F 212/32  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (52)  U.S. Cl.  CPC ............  G03F  710041  (2013.01);  C08F  212114  (2013.01);  G03F  71004  (2013.01);  G03F  71038  (2013.01);  G03F  71039  (2013.01);  G03F  710392  (2013.01);  G03F  710397  (2013.01);  G03F  7120  (2013.01);  G03F  712037  (2013.01);  G03F  712059  (2013.01);  G03F  71325  (2013.01);  H0JJ  3713174  (2013.01);  C08F  12/20  (2013.01);  C08F 12/24  (2013.01);  C08F  212/32  (2013.01)  (58)  Field of Classification Search  CPC ......... G03F 7/004; G03F 7/038; G03F 7/039;  G03F 7/0392; G03F 7/0397; G03F 7/20;  G03F 7/2037; G03F 7/2059; G03F 7/325;  G03F 7/0041; H0lJ 37/3174; C08F 12/20;  C08F 12/24; C08F 212/14; C08F 212/32  USPC .. .. ... ... ... ... ... .. ... ... ... ... .. ... ... . 430/296, 311, 942  See application file for complete search history.  (56)  References Cited  U.S. PATENT DOCUMENTS  2011/0300485 Al  12/2011 Tsubaki et al.  2012/0077131 Al  3/2012 Enomoto et al.  FOREIGN PATENT DOCUMENTS  OTHER PUBLICATIONS  JP  JP  JP  JP  WO  WO  WO  2002-299223 A  2008-170784 A  2010-217884 A  2011-123469 A  2010/095763 Al  2010/140709 Al  2011/108744 Al  10/2002  7/2008  9/2010  6/2011  8/2010  12/2010  9/2011  (57)  ABSTRACT  54 Claims, No Drawings  International Search Report (PCT/ISA/210), dated Oct. 23, 2012,  issued by the International Searching Authority in counterpart Inter› national Patent Application No. PCT/JP2012/073765.  Written Opinion (PCT/ISA/237), dated Oct. 23, 2012, issued by the  International Searching Authority in counterpart International Patent  Application No. PCT/JP2012/073765.  Office Action dated Oct. 14, 2014 issued by Japanese Patent Office in  counterpart Japanese Application No. 2012-196110.  Search Report dated Mar. 30, 2015, issued by the European Patent  Office in counterpart European Application No. 12831380.6.  Primary Examiner  - Christopher Young  (74)  Attorney, Agent, or Firm  - Sughrue Mion, PLLC  A pattern-forming method includes in this order: step (1) of  forming a film with an electron beam-sensitive or extreme  ultraviolet radiation-sensitive resin composition that contains  (A) a resin having an acid-decomposable repeating unit and  capable of decreasing a solubility of the resin (A) in a devel› oper containing an organic solvent by an action ofan acid, (B)  a compound capable of generating an acid upon irradiation  with an electron beam or extreme ultraviolet radiation and (C)  a solvent; step (2) of exposing the film with an electron beam  or extreme ultraviolet radiation; and step (4) of forming a  negative pattern by development of the film with a developer  containing an organic solvent after the exposing of the film,  wherein a content of the compound (B) is 21% by mass to  70% by mass on the basis of all solids content of the compo› sition. 