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# c12) United States Patent 

# Aqad 

# (54) PHOTOACID-GENERATING COMPOUND AND ASSOCIATED POLYMER, PHOTORESIST COMPOSITION, AND METHOD OF FORMING A PHOTORESIST RELIEF IMAGE 

(71) Applicant: Rohm and Haas Electronic Materials LLC, Marlborough, MA (US) 

(72) Inventor: Emad Aqad, Northborough, MA (US) 

(73) Assignee: ROHM AND HAAS ELECTRONIC MATERIALS LLC, Marlborough, MA (US) 

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

(21) Appl. No.: 15/281,292 

(22) Filed: Sep. 30, 2016 

## (65) Prior Publication Data 

US 2018/0095363 Al Apr. 5, 2018 

(51) Int. Cl. 

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(52) U.S. Cl. CPC .......... G03F 710045 (2013.01); C07C 303132 (2013.01); C07C 309/04 (2013.01); C07C 309/06 (2013.01); C07C 309112 (2013.01); C07C 309/14 (2013.01); C07C 309/19 (2013.01); C07C 309122 (2013.01); C07C 309/23 (2013.01); C07D 333174 (2013.01); C08F 220168 (2013.01); C08F 228102 (2013.01); C08F 228106 (2013.01); G03F 710397 (2013.01); G03F 7116 (2013.01); G03F 712004 (2013.01); G03F 7130 (2013.01); G03F 71322 (2013.01); G03F 7140 (2013.01) 

( 58) Field of Classification Search CPC ....... G03F 7/0045; G03F 7/30; C07C 333/74; C08F 228/02; C08F 228/06 

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# (IO) Patent No.: US 10,088,749 B2 

# Oct. 2, 2018 (45) Date of Patent: 

## (56) References Cited 

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Primary Examiner - John S Chu 

(74) Attorney, Agent, or Firm - Cantor Colburn LLP 

## (57) ABSTRACT 

A photoacid-generating compound has the structure 

wherein m, n, R1, R 2 , X, Y, and z- are defined herein. The photoacid-generating compound exhibits strong absorption and chemical sensitivity to extreme ultraviolet radiation, while also absorbing longer wavelengths with desirably reduced chemical sensitivity. Also described are a polymer incorporating the residue of a polymerizable version of the photoacid-generating compound, a photoresist composition that includes the photoacid-generating compound, the poly› mer, or a combination thereof, and a method of forming a photoresist relief image using the photoresist composition. 

USPC ......... 430/270.1, 921, 922, 326; 549/12, 41, 549/42, 43, 45, 46, 47; 526/256, 280, 526/287, 288 

See application file for complete search history. 

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US010088749B2 

## U.S. PATENT DOCUMENTS 

(Continued) 

## FOREIGN PATENT DOCUMENTS 

(Continued) 

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## 11 Claims, 4 Drawing Sheets 

