(IO)  Patent No.:  US 8,652, 712 B2  *Feb.18,2014  (45)  Date of Patent:  c12)  United States Patent  Glodde  (54)  PHOTOACID GENERATORS FOR EXTREME  ULTRAVIOLET LITHOGRAPHY  (75)  Inventor:  Martin Glodde,  Armonk, NY (US)  (73)  Assignee:  International Business Machines  Corporation,  Armonk, NY (US)  ( *)  Notice:  Subject to any disclaimer, the term ofthis  patent is extended or adjusted under 35  U.S.C. 154(b) by  O  days.  This patent is subject to a terminal dis› claimer.  (21)  Appl. No.:  13/021,558  (22)  Filed:  Feb.25,2011  (62)  DivisionofapplicationNo.11/970,827, filed on Jan. 8,  2008, now Pat. No. 8,039,194.  (51)  Int. Cl.  G03F  71004  G03F  71039  (2006.01)  (2006.01)  (52)  U.S. Cl.  CPC ............  G03F  710045  (2013.01);  G06F  710046  (2013.01);  G06F  710397  (2013.01)  USPC .............................................  430/18;  430/323  (58)  Field of Classification Search  CPC .... G03F 7/0045; G03F 7/0046; G03F 7/0397  USPC .................................... 430/18, 323, 922, 925  See application file for complete search history.  7,202,015 B2  7,214,465 B2  7,214,467 B2  7,232,640 Bl  7,655,379 B2  8,039,194 B2 *  2003/0194639 Al*  2004/0023163 Al *  2005/0221220 Al  2007/0128547 Al  4/2007 Karma et al. ............... 430/270.1  5/2007 Nakao et al. .................. 430/170  5/2007 Karma et al. ............... 430/270.1  6/2007 Mizutani et al ............ 430/270.1  2/2010 Glodde et al .............. 430/270.1  10/2011 Glodde ...................... 430/270.1  10/2003 Miya et al. ................. 430/270.1  2/2004 Yukawa et al. ............... 430/326  10/2005 Meagley .................... 430/270.1  6/2007 Mizutani et al ............ 430/281.1  3,853,943  A  6,093,753  A  6,358,665 Bl *  6,387,587 Bl*  6,849,374 B2  12/1974 Webster ........................ 558/432  7 /2000 Takahashi ....................... 522/25  3/2002 Pawlowski et al. ........ 430/270.1  5/2002 Oomori et al. ............. 430/270.1  2/2005 Cameron ................... 430/270.1  (56)  References Cited  U.S. PATENT DOCUMENTS  Related U.S. Application Data  (65)  Prior Publication Data  OTHER PUBLICATIONS  (57)  ABSTRACT  35 Claims, 4 Drawing Sheets  A photoacid generator  p+  A- comprises (a) an antenna group  p+  comprising atoms with high EUV photoabsorption cross› sections according to FIG.  1  and A- anions; or (b) an antenna  group  p+  and A- comprising anions with low photoabsorption  cross-sections for EUV; or ( c) an antenna group P+, compris› ing atoms with high EUV photoabsorption cross-sections  according to FIG.  1  and A- comprising anions with low  photoabsorption cross-sections for EUV. Novel compounds  comprise DTFPIO PFBuS, and DTBPIO  CNS.  (74)  Attorney, Agent, or Firm  - Robert J. Eichelburg; The  Law Offices of Robert J. Eichelburg  Primary Examiner  - John Chu  * cited by examiner  Parent Application, U.S. Appl. No. 11/970,827, filed Jan. 8, 2008,  Martin Glodde.  U.S. Appl. No. 11/970,731, filed Jan. 8, 2008, Martin Glodde, et al.  EP 1338921, Mizutani, et al., Aug. 27, 2003.  Wallraff, et al., Lithographic Imaging Techniques ... ,  Chem. Rev.,  1999, 99, 1801-1821.  Crivello, The Discovery and Development of Onium ... , Jour. of Pol.  Sci.: Part A: Pol. Chem., vol. 37, 4241-4254 (1999).  Vianello, et al. ,Towards highly powerful neutral organic .super› acids ... ,Tetrahedron 61 (2005) 9381-9390.  Vianello, et al. In Search of Ultrastrong Bronsted Neutral  Superacids ... ,  Chem. Eur. J.  2004, 10, 5751-5760.  J Org. Chem.  1958, 53, 5571-5573.  Richardson et al., Exploration of the Pentacyano-cyco/-pewntadiene  10n ...  Chem. Commun.,  2004, 706-707.  Simmons et al., Thiacyanocarbons ...  J Org. Chem.  ,1980, 45,  5113-5121.  US008652712B2  US 2011/0143099 Al  Jun. 16, 2011 