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# c12) United States Patent Tsuruta et al. 

# (54) ACTINIC RAY-SENSITIVE OR RADIATION-SENSITIVE RESIN COMPOSITION, ACTINIC RAY-SENSITIVE OR RADIATION-SENSITIVE FILM, MASK BLANKS INCLUDING ACTINIC RAY-SENSITIVE OR RADIATION-SENSITIVE FILM, PATTERN FORMING METHOD AND PHOTO MASK 

(71) Applicant: FUJIFILM Corporation, Minato-ku, Tokyo (JP) 

(72) Inventors: Takuya Tsuruta, Haibara-gun (JP); Tomotaka Tsuchimura, Haibara-gun (JP); Tadeteru Yatsuo, 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 O days. days. 

(21) Appl. No.: 14/560,650 

Dec. 4, 2014 (22) Filed: 

## (65) Prior Publication Data 

US 2015/0086911 Al Mar. 26, 2015 

(63) Continuation of application PCT/JP2013/067157, filed on Jun. 17, 2013. No. 

## (30) Foreign Application Priority Data 

Jul. 9, 2012 (JP) ................................. 2012-154118 

(51) Int. Cl. 

<img src='content_image/890381.jpg'>

(52) U.S. Cl. CPC .......... G03F 710045 (2013.01); C07C 309/65 (2013.01); C07C 381112 (2013.01); C07D 327108 (2013.01); C07D 333/46 (2013.01); G03F 710046 (2013.01); G03F 71038 (2013.01); G03F 710382 (2013.01); G03F 710397 (2013.01); G03F 712037 (2013.01); G03F 71325 (2013.01); C07C 2601/14 (2017.05) 

( 58) Field of Classification Search None 

See application file for complete search history. 

## Related U.S. Application Data 

<img src='content_image/890343.jpg'>

# (IO) Patent No.: US 9,958,775 B2 

# (45) Date of Patent: May 1, 2018 

## (56) References Cited 

<img src='content_image/890379.jpg'>

<img src='content_image/890380.jpg'>

JPO English translation of JP 2012-73401 (2012).* 

Primary Examiner - Sin J Lee 

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

## (57) ABSTRACT 

An actinic ray-sensitive or radiation-sensitive resin compo› sition includes; a compound (A) which generates an acid by irradiation with actinic rays or radiation, wherein the acid is linked with a group represented by the following general formula (M) through covalent bonding. In the formula, Y $_{1 }$ and Y $_{2 }$ each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, an aryl group, or an acyl group. Z represents a hydrogen atom or a substituent. * represents a linking site with a residue of the compound (A) 

[Chem.!] 

US009958775B2 

## U.S. PATENT DOCUMENTS 

## FOREIGN PATENT DOCUMENTS 

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## OTHER PUBLICATIONS 

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## 20 Claims, No Drawings 

