(IO)  Patent No.:  US 7,314,700 B2  (45)  Date of Patent:  Jan.1,2008  c12)  United States Patent  Huang et al.  (54)  HIGH SENSITIVITY RESIST  COMPOSITIONS FOR ELECTRON-BASED  LITHOGRAPHY  (75)  Inventors:  Wu-Song Huang,  Poughkeepsie,  NY  (US);  Wenjie  Li,  Poughkeepsie,  NY  (US);  Wayne Moreau,  Wappingers  Falls,  NY  (US);  David R. Medeiros,  Ossining,  NY  (US);  Karen E. Petrillo,  Mahopac,  NY  (US);  Robert N. Lang,  Pleasant Valley,  NY  (US);  Marie  Angelopoulos,  Cortlandt Manor,  NY  (US)  (73)  Assignee:  International Business Machines  Corporation,  Armonk,  NY  (US)  ( *)  Notice:  Subject to any disclaimer, the term of this  patent is extended or adjusted under 35  U.S.C. 154(b) by 200 days.  (21)  Appl. No.:  10/537,259  (22)  PCT Filed:  Dec. 5, 2002  (86)  PCT No.:  PCT /US02/39048  § 371 (c)(l),  (2), ( 4) Date:  May 31, 2005  (87)  PCT Pub. No.:  WO2004/053594  PCT Pub. Date:  Jun. 24, 2004  (65)  Prior Publication Data  US 2006/0127800 Al  Jun. 15, 2006  (51)  Int. Cl.  G03C 11492  (2006.01)  G03C 11494  (2006.01)  G03C 1176  (2006.01)  G03C 5100  (2006.01)  (52)  U.S. Cl.  ...................  430/270.1;  430/322; 430/324;  430/325; 430/326; 430/330  (58)  Field of Classification Search  ............. 430/270.1,  430/322,324,325,326,330  See application file for complete search history.  (56)  References Cited  U.S. PATENT DOCUMENTS  4,554,458 A  ll/ 1985 Behringer et al.  4,996,136  A  2/1991  Houlihan  5,191,124 A  3/1993  Schwalm et al.  5,374,504  A  12/1994 Hanson et al.  5,384,229  A  1/1995 Pai et al.  5,403,695  A  *  4/1995  Hayase et al. .............. 430/192  5,580,702  A  12/1996 Hayase et al. .............. 430/326  5,679,497  A  *  10/1997 Kimura ...................... 430/296  5,866,913  A  2/1999 Robinson  5,880,169  A  3/1999 Osawa et al.  6,008,266  A  12/1999 Kuczynski et al.  6,037,097  A  3/2000 Bucchignano et al.  6,043,003  A  3/2000 Bucchignano et al.  6,069,684  A  5/2000 Golladay et al.  6,200,728 Bl  3/2001  Cameron et al.  6,274,289 Bl  8/2001  Subramanian et al.  6,280,911 Bl  8/2001  Trefonas, III  6,296,976 Bl  10/2001  Groves et al.  6,348,297 Bl  2/2002 Uetani et al.  6,355,383 Bl  3/2002 Yamashita  6,358,665 Bl  3/2002 Pawlowski et al.  6,406,830 B2  6/2002 Inoue et al.  6,949,329 B2  *  9/2005  Endo et al. ................. 430/322  FOREIGN PATENT DOCUMENTS  JP  JP  JP  JP  JP  JP  JP  JP  PUPA 06-043653  PUPA 08-248626  PUPA 09-160244  PUPA 09-222724  PUPA 09-323970  PUPA 10-007650  PUPA 2000-019732  PUPA 2001-209181  2/1994  9/1996  6/1997  8/1997  12/1997  1/1998  1/2000  8/2001  * cited by examiner  Primary Examiner---Geraldina  Visconti  (74)  Attorney, Agent, or Firm-Steven  Capella  (57)  ABSTRACT  14 Claims, No Drawings  The resist compositions having an acid sensitive imaging  polymer and a radiation sensitive acid generator component  comprising: (i) a first radiation sensitive acid generator  selected from the group consisting of dissolution-inhibiting  acid generators, and (ii) a second radiation sensitive acid  generator selected from the group consisting of unprotected  acidic group-functionalized acid generators and acid labile  group-protected acidic group-functionalized radiation sen› sitive acid generators; enables formation of high sensitivity  resists suitable for use in EPL, EUV, soft x-ray, and other  low energy intensity lithographic imaging applications. The  resist compositions may be useful in other lithographic  processes as well.  US007314700B2 