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# c12) United States Patent 

# Glodde 

# (54) PHOTOACID GENERATORS FOR EXTREME ULTRAVIOLET LITHOGRAPHY 

(75) Inventor: Martin Glodde, Armonk, NY (US) 

(73) Assignee: International Business Machines Corporation, Armonk, NY (US) 

( *) 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.: 13/021,558 

(22) Filed: Feb.25,2011 

## (65) Prior Publication Data 

US 2011/0143099 Al Jun. 16, 2011 

(62) DivisionofapplicationNo.11/970,827, filed on Jan. 8, 2008, now Pat. No. 8,039,194. 

(51) Int. Cl. G03F 71004 G03F 71039 (2006.01) (2006.01) 

(52) U.S. Cl. CPC ............ G03F 710045 (2013.01); G06F 710046 (2013.01); G06F 710397 (2013.01) USPC ............................................. 430/18; 430/323 

(58) Field of Classification Search CPC .... G03F 7/0045; G03F 7/0046; G03F 7/0397 USPC .................................... 430/18, 323, 922, 925 See application file for complete search history. 

## (56) References Cited 

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## Related U.S. Application Data 

## U.S. PATENT DOCUMENTS 

<img src='content_image/885662.jpg'>

# (IO) Patent No.: US 8,652, 712 B2 

# *Feb.18,2014 (45) Date of Patent: 

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Parent Application, U.S. Appl. No. 11/970,827, filed Jan. 8, 2008, Martin Glodde. 

U.S. Appl. No. 11/970,731, filed Jan. 8, 2008, Martin Glodde, et al. EP 1338921, Mizutani, et al., Aug. 27, 2003. 

Wallraff, et al., Lithographic Imaging Techniques ... , Chem. Rev., 1999, 99, 1801-1821. 

Crivello, The Discovery and Development of Onium ... , Jour. of Pol. Sci.: Part A: Pol. Chem., vol. 37, 4241-4254 (1999). 

Vianello, et al. ,Towards highly powerful neutral organic .super› acids ... ,Tetrahedron 61 (2005) 9381-9390. 

Vianello, et al. In Search of Ultrastrong Bronsted Neutral Superacids ... , Chem. Eur. J. 2004, 10, 5751-5760. 

J Org. Chem. 1958, 53, 5571-5573. 

Richardson et al., Exploration of the Pentacyano-cyco/-pewntadiene 10n ... Chem. Commun., 2004, 706-707. 

Simmons et al., Thiacyanocarbons ... J Org. Chem. ,1980, 45, 5113-5121. 

* cited by examiner 

Primary Examiner - John Chu 

(74) Attorney, Agent, or Firm - Robert J. Eichelburg; The Law Offices of Robert J. Eichelburg 

## (57) ABSTRACT 

A photoacid generator p+ A- comprises (a) an antenna group p+ comprising atoms with high EUV photoabsorption cross› sections according to FIG. 1 and A- anions; or (b) an antenna group p+ and A- comprising anions with low photoabsorption cross-sections for EUV; or ( c) an antenna group P+, compris› ing atoms with high EUV photoabsorption cross-sections according to FIG. 1 and A- comprising anions with low photoabsorption cross-sections for EUV. Novel compounds comprise DTFPIO PFBuS, and DTBPIO CNS. 

US008652712B2 

## OTHER PUBLICATIONS 

## 35 Claims, 4 Drawing Sheets 

