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# c12) United States Patent 

# Nakamura et al. 

# (54) RESIST COMPOSITION AND RESIST PATTERN FORMING METHOD 

(71) Applicant: Tokyo Ohka Kogyo Co., Ltd., Kawasaki-shi (JP) 

(72) Inventors: Tsuyoshi Nakamura, Kawasaki (JP); Kazuishi Tanno, Kawasaki (JP); Akiya Kawaue, Kawasaki (JP); Takayoshi Mori, Kawasaki (JP) 

(73) Assignee: Tokyo Ohka Kogyo Co., Ltd., Kawasaki-shi (JP) 

( *) Notice: Subject to any disclaimer, the term ofthis patent is extended or adjusted under 35 U.S.C. 154(b) by 0 days. 

(21) Appl. No.: 14/218,249 

(22) Filed: Mar. 18, 2014 

## (65) Prior Publication Data 

US 2014/0287360Al Sep. 25, 2014 

## (30) Foreign Application Priority Data 

Mar. 25, 2013 (JP) ................................. 2013-062887 

(51) Int. Cl. 

<img src='content_image/923736.jpg'>

(52) U.S. Cl. CPC .............. G03F 71038 (2013.01); C08F 220124 (2013.01); C08F 220156 (2013.01); C08F 20152 (2013.01); C07C 381112 (2013.01) 

( 58) Field of Classification Search USPC ............ 430/270.1, 913, 914; 526/243, 307.2, 526/303.1 See application file for complete search history. 

## (56) References Cited 

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## U.S. PATENT DOCUMENTS 

<img src='content_image/923748.jpg'>

# (10) Patent No.: US 9,052,592 B2 

# (45) Date of Patent: Jun.9,2015 

<img src='content_image/923737.jpg'>

## FOREIGN PATENT DOCUMENTS 

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Iwarnura et al, Hydrogen-Transfer Polymerization Behavior of N-Acylacrylarnide, Journal of Polymer Science:Part A:Polymer Chemistry, vol. 38, pp. 430-435 (2000).* 

Machine translation of JP 2000-310857 (no date).* 

* cited by examiner 

Primary Examiner - Amanda C Walke 

(74) Attorney, Agent, or Firm -Knobbe Martens Olson & BearLLP 

## (57) ABSTRACT 

A resist composition contains a high-molecular weight com› pound which has a partial structure represented by a general formula (a0-r-1) and has a constituent unit represented by a general formula (a0-1). In the formula (a0-r-1), Y$^{1 }$represents a divalent linking group; eachofR$^{2 }$andR$^{3 }$represents a group having Oto 20 carbon atoms, which is not a fluorine atom, and either R 2 or R 3 may form a ring with Y1; m represents an integer of 1 or more; and Mm+ represents an m-valent organic cation. In the formula ( a0-1 ), R represents a hydrogen atom, an alkyl group, or a halogenated alkyl group; Ya$^{01 }$represents a single bond or a divalent linking group; X$^{01 }$represents a sulfur atom or an oxygen atom; and Ra 01 represents an optionally substituted cyclic group, chain alkyl group or chain alkenyl group. 

US009052592B2 

## OTHER PUBLICATIONS 

## 15 Claims, No Drawings 

