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# c12) United States Patent 

# Bass et al. 

# (54) METAL PEROXO COMPOUNDS WITH ORGANIC CO-LIGANDS FOR ELECTRON BEAM, DEEP UV AND EXTREME UV PHOTORESIST APPLICATIONS 

(75) Inventors: John David Bass, Union City, CA (US); Ho-Cheol Kim, San Jose, CA (US); Robert Dennis Miller, San Jose, CA (US); Qing Song, San Jose, CA (US); Linda Karin Sundberg, Los Gatos, CA (US); Gregory Michael Wallraff, San Jose, CA (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 54 days. 

(21) Appl. No.: 13/405,587 

(22) Filed: Feb.27,2012 

## (65) Prior Publication Data 

US 2013/0224652 Al Aug. 29, 2013 

(51) Int. Cl. 

<img src='content_image/898448.jpg'>

(52) U.S. Cl. USPC ............... 430/270.1; 556/40; 556/42; 556/55 

( 58) Field of Classification Search USPC .............................. 430/270.1; 556/40, 42, 55 See application file for complete search history. 

## (56) References Cited 

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## U.S. PATENT DOCUMENTS 

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# (IO) Patent No.: US 8,703,386 B2 

# (45) Date of Patent: Apr. 22, 2014 

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## FOREIGN PATENT DOCUMENTS 

JP 61273539 12/1986 

Bayot et al, "Vibrational Spectra ofEoght-Coordinate Niobium and Tantalum Complexes with Peroxo Ligands:A Theorretcial Simula› tion", J. Inorganic Chem (2005), 4118-4123.* 

Bayot et al, "Peroxo complexes of niobium (V) and tantalum (V)", Coordination Chemistry Reviews 250 (2006), 2610-2626.* 

Djordjevic et al, "Coordination Complexes of Niobium and Tanta› lum. Eight-coordinated Di- and Triperoxoniobates (V) and tantalates (V) with Some Nitrogen and Oxygen Bidentate Ligands", Inorganic Chemistry, vol. 7, No. 9 (1968), 1864-1868.* 

Anderson, et al., "The SEMATECH Berkeley MET: extending EUV learning down to 16nmhalfpitch", Proc. SPIE 7969, 79690R(201 l), Feb. 28, 2011. 

Primary Examiner - Amanda C. Walke 

(74) Attorney, Agent, or Firm - Michael R. Roberts 

## (57) ABSTRACT 

Compositions are disclosed having the formula (3): 

wherein x is an integer of 1 to 4, y is an integer of 1 to 4, Ta(O$_{2}$)x(L’)y has a charge ofO to -3, C’ is a counterion having a charge of +1 to +3, k is an integer of O to 3, L’ is an oxidatively stable organic ligand having a charge of O to -4, and L’ comprises an electron donating functional group selected from the group consisting of carboxylates, alkox› ides, amines, amine oxides, phosphines, phosphine oxides, arsine oxides, and combinations thereof. The compositions have utility as high resolution photoresists. 

US008703386B2 

## OTHER PUBLICATIONS 

## 14 Claims, 15 Drawing Sheets 

(Continued) 

(3), 

