US009285679B2  (IO)  Patent No.:  US 9,285,679 B2  (45)  Date of Patent:  Mar.15,2016  c12)  United States Patent  Tsuchimura et al.  (54)  ACTINIC RAY-SENSITIVE OR  RADIATION-SENSITIVE COMPOSITION,  AND RESIST FILM, RESIST-COATED MASK  BLANKS, RESIST PATTERN FORMING  METHOD AND PHOTO MASK EACH USING  THE COMPOSITION  (71)  Applicant:  FUJIFILM CORPORATION,  Tokyo  (JP)  (72)  Inventors:  Tomotaka Tsuchimura,  Shizuoka (JP);  Takuya Tsuruta,  Shizuoka (JP);  Takeshi Inasaki,  Shizuoka (JP);  Koutarou Takahashi,  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  O  days.  (21)  Appl. No.:  14/497,560  (22)  Filed:  Sep.26,2014  (63)  Continuation of application No. PCT/JP2013/058852,  filed on Mar. 26, 2013.  (51)  Int. Cl.  (65)  Prior Publication Data  (30)  Foreign Application Priority Data  Related U.S. Application Data  US 2015/0010855 Al  Jan. 8, 2015  There is provided an actinic ray-sensitive or radiation-sensi› tive composition containing  (a)  a compound represented by  the formula ( al) capable of generating an acid having a size of  200  A $^{3 }$or more in volume and (~) a compound capable of  generating an acid upon irradiation with an actinic ray or  radiation, and the formula ( al) is defined as herein,  Primary Examiner  - Anca Eoff  (74)  Attorney, Agent, or Firm  - Sughrue Mion, PLLC  (Continued)  Office Action dated Sep. 9, 2014 issued by the Japanese Patent Office  in counterpart Japanese Application No.2012-078094.  Seth Kruger et al., "Can Acid Amplifiers Help Beat the Resolution,  Line Edge Roughness, and Sensitivity Trade-Off?", Japanese Journal  of Applied Physics, 49, Apr. 20, 2010, pp. 041602-1-041602-5.  Kazuaki  Kudo  et  al.,  "3-Phenyl-3,3-ethylenedioxy-l-propyl  Sulfonates as Acid Amplifiers to Enhance the Photosensitivity of  Positive-Working Photoresists", Chemistry of Materials, 11, Jul. 7,  1999,pp.2119-2125.  Communication issued on Mar. 1, 2015 by the Korean Intellectual  Property Office in related KR application No. 10-2014-7026957.  International Search Report dated Jun. 25, 2013 issued in Interna› tional Application No. PCT/JP2013/058852 (PCT/ISA/210).  Written Opinion dated Jun. 25, 2013 issued in International Appli› cation No. PCT/JP2013/058852 (PCT/ISA/237).  Kruger, S.A., Riggings, C., Cardineau, B., Younkin,  T.  R., Brainard,  R.L. -Catalytic andAutocatalytic Mechanisms of Acid Amplifiers for  Use in EUV Photoresists, Chem. Mater, 2010, 22, pp. 5609-5616.*  Communication issued on Mar. 10, 2015 by the Japanese Patent  Office in related application No. 2012072540.  (Continued)  (Continued)  and a resist film formed using the actinic ray-sensitive or  radiation-sensitive composition, a resist-coated mask  blanks coated with the resist film, a resist pattern form› ing method comprising exposing the resist film and  developing the exposed film, a photomask obtained by  exposing and developing the resist-coated mask blanks,  a method for manufacturing an electronic device, com› prising the resist pattern forming method and an elec› tronic device manufactured by the manufacturing  method of an electronic device.  (52)  U.S. Cl.  CPC ................  G03F  71027  (2013.01);  C08F  12122  (2013.01);  C08F  12124  (2013.01);  C08F  12126  (2013.01);  C08F  12130  (2013.01);  C08F  12132  (2013.01);  C08F  212114  (2013.01);  C09D  125118  (2013.01);  G03F 1100  (2013.01);  G03F  1120  (2013.01);  G03F  1122  (2013.01);  G03F  71004  (2013.01);  G03F  710045  (2013.01);  G03F  710382  (2013.01);  G03F  710388  (2013.01);  G03F  710392  (2013.01);  G03F  710397  (2013.01);  G03F  712037  (2013.01);  G03F  712039  (2013.01)  (58)  Field of Classification Search  CPC .......... G03F 7/004; G03F 7/027; G03F 7/039  See application file for complete search history.  (56)  References Cited  U.S. PATENT DOCUMENTS  FOREIGN PATENT DOCUMENTS  OTHER PUBLICATIONS  (57)  ABSTRACT  36 Claims, No Drawings  Mar. 27, 2012  Mar. 29, 2012  (JP) ................................. 2012-072540  (JP) ................................. 2012-078094  G03F  71039  G03F  71028  G03F  71027  C08F  12124  G03F  71004  G03F  71038  G03F 1100  G03F  1120  G03F  1122  G03F  7120  C08F 12122  C08F 12126  C08F 12130  C08F 12132  C08F 212114  C09D 125118  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (2012.01)  (2012.01)  (2012.01)  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (2006.01)  5,082,755 A *  1/1992 Liu ................................... 430/5  2001/0044054 Al* 11/2001 Kaneko et al ..................... 430/5  2003/0027061 Al  2/2003 Cameron et al.  JP  JP  8-248561 A  11-158118 A  9/1996  6/1999  (al)  0  0  II  A-S-0  II  r  r  )lR.  0  R2  H  Rs 