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# 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 

## (65) Prior Publication Data 

US 2007/0129576Al Jun. 7,2007 

(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. 

## (30) Foreign Application Priority Data 

<img src='content_image/928224.jpg'>

(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. 

## (56) References Cited 

5,177,166 A * 1/1993 Kobo et al. ................. 526/249 

## Related U.S. Application Data 

## U.S. PATENT DOCUMENTS 

<img src='content_image/928236.jpg'>

# (10) Patent No.: US 7,649,118 B2 

# (45) Date of Patent: *Jan. 19, 2010 

<img src='content_image/928226.jpg'>

## FOREIGN PATENT DOCUMENTS 

<img src='content_image/928225.jpg'>

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 

## (57) ABSTRACT 

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. 

US007649118B2 

## OTHER PUBLICATIONS 

## 12 Claims, No Drawings 

