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# c12) United States Patent 

# Huang et al. 

# (54) HIGH SENSITIVITY RESIST COMPOSITIONS FOR ELECTRON-BASED LITHOGRAPHY 

(75) Inventors: Wu-Song Huang, Poughkeepsie, NY (US); Wenjie Li, Poughkeepsie, NY (US); Wayne Moreau, Wappingers Falls, NY (US); David R. Medeiros, Ossining, NY (US); Karen E. Petrillo, Mahopac, NY (US); Robert N. Lang, Pleasant Valley, NY (US); Marie Angelopoulos, Cortlandt Manor, NY (US) 

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

( *) Notice: Subject to any disclaimer, the term of this patent is extended or adjusted under 35 U.S.C. 154(b) by 200 days. 

(21) Appl. No.: 10/537,259 

(22) PCT Filed: Dec. 5, 2002 

(86) PCT No.: PCT /US02/39048 § 371 (c)(l), (2), ( 4) Date: May 31, 2005 

(87) PCT Pub. No.: WO2004/053594 PCT Pub. Date: Jun. 24, 2004 

## (65) Prior Publication Data 

## US 2006/0127800 Al Jun. 15, 2006 

(51) Int. Cl. 

<img src='content_image/901068.jpg'>

(52) U.S. Cl. ................... 430/270.1; 430/322; 430/324; 430/325; 430/326; 430/330 

(58) Field of Classification Search ............. 430/270.1, 430/322,324,325,326,330 See application file for complete search history. 

## (56) References Cited 

4,554,458 A ll/ 1985 Behringer et al. 

## U.S. PATENT DOCUMENTS 

<img src='content_image/901084.jpg'>

# (IO) Patent No.: US 7,314,700 B2 

# (45) Date of Patent: Jan.1,2008 

<img src='content_image/901074.jpg'>

## FOREIGN PATENT DOCUMENTS 

<img src='content_image/901076.jpg'>

* cited by examiner 

Primary Examiner---Geraldina Visconti 

(74) Attorney, Agent, or Firm-Steven Capella 

## (57) ABSTRACT 

The resist compositions having an acid sensitive imaging polymer and a radiation sensitive acid generator component comprising: (i) a first radiation sensitive acid generator selected from the group consisting of dissolution-inhibiting acid generators, and (ii) a second radiation sensitive acid generator selected from the group consisting of unprotected acidic group-functionalized acid generators and acid labile group-protected acidic group-functionalized radiation sen› sitive acid generators; enables formation of high sensitivity resists suitable for use in EPL, EUV, soft x-ray, and other low energy intensity lithographic imaging applications. The resist compositions may be useful in other lithographic processes as well. 

US007314700B2 

## 14 Claims, No Drawings 

