(10)  Patent No.:  US 7,649,118 B2  (45)  Date of Patent:  *Jan. 19, 2010  c12)  United States Patent  Araki et al.  (54)  PROCESS FOR PREPARING  FLUORINE-CONTAINING NORBORNENE  DERIVATIVE  (75)  Inventors:  TakayukiAraki,  Settsu (JP);  Takuji  Ishikawa,  Settsu (JP);  Takuji Kume,  Settsu (JP);  Akinori Yamamoto,  Settsu  (JP)  (73)  Assignee:  Daikin Industries, Ltd.,  Osaka (JP)  ( *)  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.:  11/649,265  (22)  Filed:  Jan.4,2007  (60)  DivisionofapplicationNo.10/753,529, filed on Jan. 9,  2004,nowPat. No. 7,186,773, whichisacontinuation› in-part of application No. PCT/JP02/07112, filed on  Jul. 12, 2002.  (51)  Int. Cl.  C07C 45100  (2006.01)  (52)  U.S. Cl.  ........................  568/354;  526/242; 526/281  (58)  Field of Classification Search  ................. 568/354;  526/242, 281  See application file for complete search history.  (65)  Prior Publication Data  Related U.S. Application Data  (30)  Foreign Application Priority Data  FOREIGN PATENT DOCUMENTS  OTHER PUBLICATIONS  (57)  ABSTRACT  12 Claims, No Drawings  (56)  References Cited  U.S. PATENT DOCUMENTS  5,177,166 A  *  1/1993 Kobo et al. ................. 526/249  Jul. 12, 2001  Sep. 14, 2001  Feb.20,2002  (JP)  ............................. 2001-212689  (JP)  ............................. 2001-280548  (JP)  ............................... 2002-43920  EP  EP  EP  EP  WO  WO  157262 Al  1 331 216 Al  1 398 339 Al  1 413 927 Al  2001-296662 A  WO 02/36533 Al  10/1985  7/2003  3/2004  4/2004  10/2001  5/2002  6,468,712 Bl  6,548,219 B2  6,858,760 B2  6,884,564 B2  6,908,724 B2  *  10/2002 Fedynyshyn  4/2003 Ito et al.  2/2005 Komoriya et al.  4/2005 Feiring et al.  6/2005 Araki et al. .............. 430/270.1  2001/0038969 Al  2002/0055061 Al  2002/0146638 Al  2003/0232276 Al  2004/0180287 Al  2004/0225159 Al  2004/0265738 Al  11/2001 Hatakeyama  5/2002 Taylor et al.  10/2002 Ito et al.  12/2003 Poss et al.  9/2004 Feiring et al.  11/2004 Komoriya et al.  12/2004 Feiring et al.  US 2007/0129576Al  Jun. 7,2007  US007649118B2  Pirkle W.H. and Rinaldi P.L., "Use of Liquid-Crystal-Induced Circu› lar Dichroism for Determination of Absolute Configuration of  Alcohols and Oxaziridines", J. Org. Chem., 1990, vol. 45, pp. 1379 to  1382.  Krasovsky  A.L.  et  al.,  "Diels-Alder  reactions  of  N-trifluoroacetylvinylsulfones", Tetrahedron, Jan. 1, 2001, vol. 57,  No. 1, pp. 201-209.  * cited by examiner  Primary Examiner-Daniel  M Sullivan  Assistant Examiner----Chukwuma  O Nwaonicha  (74)  Attorney, Agent, or Firm-Sughrue  Mion, PLLC  There are provided a novel norbornene derivative which is a  material for a chemically amplifying type photoresist for F  2  laser, possesses excellent transparency and improved dry  etching resistivity and has a fluorine-containing ketone unit or  fluorine-containing tertiary alcohol unit directly bonded to  the norbornene backbone; a fluorine-containing polymer  obtained by using the norbornene derivative as a copolymer› izable monomer; and a chemically amplifying type photore› sist composition comprising the fluorine-containing polymer,  a photoacid generator and a solvent. 