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US007211366B2

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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

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PHOTORESIST COMPOSITION FOR DEEP
ULTRAVIOLET LITHOGRAPHY

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.

Int. CI.

G03F 7/004 (2006.01)

U.S. CI 430/270.1; 430/905; 430/907;

430/910

Field of Classification Search 430/270.1,

430/906, 905, 910, 907 See application file for complete search history.

References Cited

U.S. PATENT DOCUMENTS

[table]
[merged small][table][merged small][merged small][merged small][merged small]

(1)

I

(X)m

I

Rf C — R2

O
I

(R3 C —R,)p

C = 0
I

o

I

R5

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

Page 2

OTHER PUBLICATIONS

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

[graphic]

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.

Figure 1:

Generic structures for the norbornene-based monomer

[graphic][merged small]
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