content_image/914907.jpg content_image/914906.jpg content_image/914920.jpg content_image/914915.jpg content_image/914919.jpg
# c12) United States Patent 

# Takahashi et al. 

# (54) ACTINIC RAY-SENSITIVE OR RADIATION-SENSITIVE RESIN COMPOSITION, RESIST FILM, PATTERN FORMING METHOD USING THE SAME, AND RESIN 

(75) Inventors: Hidenori Takahashi, Haibara-gun (JP); Tomotaka Tsuchimura, Haibara-gun (JP); Toru Tsuchihashi, Haibara-gun (JP); Katsuhiro Yamashita, Haibara-gun (JP); Hideaki Tsubaki, Haibara-gun (JP) 

(73) Assignee: FUJIFILM Corporation, Tokyo (JP) 

( *) Notice: Subject to any disclaimer, the term ofthis patent is extended or adjusted under 35 U.S.C. 154(b) by 286 days. 

(21) Appl. No.: 12/641,877 

(22) Filed: Dec. 18, 2009 

## (65) Prior Publication Data 

US 2010/0183975 Al Jul. 22, 2010 

## (30) Foreign Application Priority Data 

Dec. 18, 2008 (JP) ................................. 2008-322678 

(51) Int. Cl. 

<img src='content_image/914907.jpg'>

(52) U.S. Cl. CPC ............ G06F 710392 (2013.01); G03F 710397 (2013.01); G03F 710045 (2013.01); YJ0S 430/122 (2013.01); YJ0S 430/123 (2013.01) USPC ......... 430/270.1; 430/326; 430/921; 430/922 

( 58) Field of Classification Search USPC .............. 430/270.1, 913, 914, 921, 925, 325, 430/326, 922; 526/275, 276,243; 560/221, 560/222; 525/276 See application file for complete search history. 

## (56) References Cited 

<img src='content_image/914906.jpg'>

## U.S. PATENT DOCUMENTS 

<img src='content_image/914920.jpg'>

# (IO) Patent No.: US 8,852,845 B2 

# (45) Date of Patent: Oct. 7, 2014 

## FOREIGN PATENT DOCUMENTS 

<img src='content_image/914915.jpg'>

M. Wang, "Synthesis and Properties of New Anionic Photoacid Gen› erators Bound Polymer Resists for e-beam and EUV lithography," Proc. ofSPIE, vol. 6923, No. 692312 (2008). 

Y. Hirai, Science and New Technology in Nanoimprint, Frontier Pub› lishing (2006). 

* cited by examiner 

Primary Examiner - Anca Eoff 

(74) Attorney, Agent, or Firm - Sughrue Mion, PLLC 

## (57) ABSTRACT 

Provided is a actinic ray-sensitive or radiation-sensitive resin composition including (P) a resin containing (A) a repeating unit having an ionic structure moiety that contains a cation represented by formula (Ia) and is capable of producing an acid anion on the side chain upon irradiation with an actinic ray or radiation: 

<img src='content_image/914919.jpg'>

wherein each of R$_{1}$ a to R$_{13}$ a independently represents a hydrogen atom or a monovalent substituent and may combine together to form a ring, and Z represents a single bond or a divalent linking group. 

US008852845B2 

## OTHER PUBLICATIONS 

## 10 Claims, No Drawings 

