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# c12) United States Patent 

# Hatakeyama et al. 

# (54) RESIST COMPOSITION AND PATTERNING PROCESS 

(71) Applicant: Shin-Etsu Chemical Co., Ltd., Tokyo (JP) 

(72) Inventors: Jun Hatakeyama, Joetsu (JP); Koji Hasegawa, Joetsu (JP); Masayoshi Sagehashi, Joetsu (JP) 

(73) Assignee: SHIN-ETSU CHEMICAL CO., LTD., Tokyo (JP) 

( *) 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.: 15/585,531 

(22) Filed: May 3, 2017 

## (65) Prior Publication Data 

US 2018/0004087 Al Jan. 4, 2018 

## (30) Foreign Application Priority Data 

Jun. 29, 2016 (JP) ................................. 2016-128886 

(51) Int. Cl. 

<img src='content_image/890665.jpg'>

(52) U.S. Cl. CPC ......... G03F 710392 (2013.01); C07D 317102 (2013.01); C07D 317104 (2013.01); G03F 710045 (2013.01); G03F 710046 (2013.01); G03F 71162 (2013.01); G03F 71168 (2013.01); G03F 712004 (2013.01); G03F 71322 (2013.01); G03F 7138 (2013.01) 

( 58) Field of Classification Search None See application file for complete search history. 

## (56) References Cited 

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## U.S. PATENT DOCUMENTS 

<img src='content_image/890651.jpg'>

# (IO) Patent No.: US 10,303,056 B2 

# (45) Date of Patent: May 28, 2019 

<img src='content_image/890673.jpg'>

## FOREIGN PATENT DOCUMENTS 

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Ueno et al. "Resist materials utilizing oxygen plasma resistance of iodine compounds", J. Electrochem. Soc.: Solid. State Sci. Tech., vol. 132(5) pp. 1168-1171 (May 1985).* 

Taylor "X-ray resist trends", Sol. Stat. Technol., vol. 27(6) pp. 124-131 (Jun. 1984).* 

Kishikawa et al., "Assessment of trade-off between resist resolution and sensitivity for optimization of hyper-NA immersion lithogra› phy", Proc. ofSPIE (2007), vol. 6520, 65203L-l, Cited in specification. (9 pages). 

Hutchinson., "The Shot Noise Impact on Resist Roughness in EUV Lithography", SPIE (1998),vol. 3331, pp. 531, Cited in specification. (7 pages). 

Brainard et al., "Shot Noise, LER and Quantum Efficiency of EUV Photoresists", SPIE (2004), vol. 5374, pp. 74, Cited in specification. (12 pages). 

Kozawa et al., "Basic aspects of acid generation processes in chemically amplified resists for electron beam lithography", SPIE (2005), vol. 5753, pp. 361, Cited in specification. (7 pages). 

Nakano et al., "Deprotonation mechanism of poly ( 4-hydroxystyrene) and its derivative", SPIE (2005), vol. 5753, pp. 1034, Cited in specification. (6 pages). 

Wang et al., "Novel Anionic Photoacid Generator (PAGs) and Photoresist for sub-50 nm Patterning by EUVL and EBL", SPIE (2007), vol. 6519, pp. 6519Fl-l, Cited in specification. (6 pages). 

* cited by examiner 

Primary Examiner - Martin J Angebranndt (74) Attorney, Agent, or Firm - Westerman, Hattori, Daniels & Adrian, LLP 

## (57) ABSTRACT 

A positive resist composition based on a polymer compris› ing recurring units (a) of (meth)acrylate having an iodized lactone ring, and recurring units (bl) having a carboxyl group substituted with an acid labile group and/or recurring units (b2) having a phenolic hydroxyl group substituted with an acid labile group has a high sensitivity and resolution, and forms a pattern of good profile and minimal edge roughness after exposure. 

US010303056B2 

## OTHER PUBLICATIONS 

## 2 Claims, No Drawings 

