content_image/891465.jpg content_image/891478.jpg content_image/891458.jpg content_image/891459.jpg content_image/891477.jpg
# c12) United States Patent 

# Fukushima et al. 

# (54) MONOMER, POLYMER, RESIST COMPOSITION, AND PATTERNING PROCESS 

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

(72) Inventors: Masahiro Fukushima, Joetsu (JP); Koji Hasegawa, Joetsu (JP); Jun Hatakeyama, 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 203 days. 

(21) Appl. No.: 16/121,970 

(22) Filed: Sep. 5, 2018 

## (65) Prior Publication Data 

US 2019/0079399 Al Mar. 14, 2019 

## (30) Foreign Application Priority Data 

Sep. 13, 2017 (JP) ................................. 2017-175900 

(51) Int. Cl. 

<img src='content_image/891465.jpg'>

(52) U.S. Cl. CPC ............ G03F 71033 (2013.01); C07C 391373 (2013.01); C07C 431225 (2013.01); C07C 431247 (2013.01); C08F 2138 (2013.01); C08F 12116 (2013.01); C08F 12122 (2013.01); C08F 12124 (2013.01); C08F 12132 (2013.01); C08F 212114 (2013.01); C08F 212132 (2013.01); C08F 220118 (2013.01); C08F 228102 (2013.01); C09D 125118 (2013.01); G03F 710045 (2013.01); G03F 710046 (2013.01); G03F 710397 (2013.01); G03F 71426 (2013.01); C07C 2601/08 (2017.05); C07C 2601/14 (2017.05); C08F 2/50 (2013.01); C08F 220/1806 (2020.02) 

<img src='content_image/891478.jpg'>

# (IO) Patent No.: US 10,915,021 B2 

# (45) Date of Patent: Feb.9,2021 

(58) Field of Classification Search CPC ...... G03F 7/033; G03F 7/0045; G03F 7/0046; G03F 7/0397; G03F 7/426; G03F 7/2037; C08F 12/16; C08F 12/22; C08F 12/24; C08F 12/32; C08F 212/14; C08F 212/32; C08F 212/18 See application file for complete search history. 

## (56) References Cited 

<img src='content_image/891458.jpg'>

## FOREIGN PATENT DOCUMENTS 

<img src='content_image/891459.jpg'>

Machine translation of JP-01096202-A (no date).* 

Primary Examiner - Amanda C. Walke (74) Attorney, Agent, or Firm - Westerman, Hattori, Daniels & Adrian, LLP 

## (57) ABSTRACT 

A monomer having formula (A) is provided. RA is H, methyl or trifluoromethyl, X$^{1 }$is a single bond, ether, ester or amide bond, Ra is a C$_{1}$-C$_{20 }$monovalent hydrocarbon group, R 6 is H or an acid labile group, X is halogen, n is an integer of 1 to 4, m is an integer of O to 3, and lsn+ms4. A resist composition comprising a polymer derived from the mono› mer has a high sensitivity to high-energy radiation, espe› cially EUV. 

<img src='content_image/891477.jpg'>

US010915021B2 

## U.S. PATENT DOCUMENTS 

## OTHER PUBLICATIONS 

## 15 Claims, No Drawings 

(Continued) 

(Continued) 

(Continued) 

