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United States Patent
Dammel et al.
(io) Patent No.: (45) Date of Patent:
US 7,211,366 B2 May 1, 2007
(21 (22 (65
PHOTORESIST COMPOSITION FOR DEEP
Inventors: Ralph R. Dammel, Flemington, NJ
(US); Raj Sakamuri, Sharon, MA
(US); Francis M. Houlihan,
Millington, NJ (US)
Assignee: AZ Electronic Materials USA Corp.,
Somerville, NJ (US)
Notice: Subject to any disclaimer, the term of this patent is extended or adjusted under 35 U.S.C. 154(b) by 79 days.
Appl. No.: 10/658,840
Filed: Sep. 9, 2003
Prior Publication Data
US 2004/0166433 Al Aug. 26, 2004
Related U.S. Application Data
Continuation-in-part of application No. 10/371,262, filed on Feb. 21, 2003, now abandoned.
G03F 7/004 (2006.01)
U.S. CI 430/270.1; 430/905; 430/907;
Field of Classification Search 430/270.1,
430/906, 905, 910, 907 See application file for complete search history.
U.S. PATENT DOCUMENTS
Rf C — R2
(R3 C —R,)p
C = 0
The invention also relates to a process for imaging the photoresist composition of the present invention, and to a process of making the polymer in the presence of an organic base.
12 Claims, 6 Drawing Sheets
Hoang V. Tran et al, "Metal-Catalyzed Vinyl Addition Polymers for 157 nm Resist Applications. 2. FluorinatedNorbornenes: Synthesis, Polymerization and Initial Imaging Results", Macromolecules 2002, 36, 6539-6549.
Shun-ichi Kodama et al, "Synthesis of Novel Fluoropolymer for 157 nm Photoresists by Cyclo-polymerization", Advances in Resist Technology and Processing XIX, SPIE, vol. 4690 (2002) pp. 76-83. English Language abstract of JP 2000-98614.
Notification of Lransmittal of the International Preliminary Examination Report and International Preliminary Examination Report for PCL/EP2004/001194.
Kodama et al., "Synthesis of Novel Fluoropolymer for 157nm Photoresists by Cyclo-polymerization", Proc. SPIE, vol. 5690, Part 1, pp. 76-pp. 83 (2002).
International Search Report (Form PCL/ISA/210) for PCL/EP2004/ 001194.
PCL Search Report for PCL/EP2004/001194. * cited by examiner
where, in Figure 1, R1-R7 are independently H, F, (C1-C8)alkyl, (C1-C8)fluoroalkyl, etc but at least one of Ri-R6 has the pendant oxyAOCA functionality described in structure 1, or an alcohol functionality which can be capped to give the unit of structure 1.
Generic structures for the norbornene-based monomer