content_image/889971.jpg content_image/889972.jpg content_image/889934.jpg content_image/889973.jpg content_image/889974.jpg content_image/889975.jpg
# c12) United States Patent Tsuchimura et al. 

# (54) ACTINIC RAY-SENSITIVE OR RADIATION-SENSITIVE COMPOSITION, AND RESIST FILM, RESIST-COATED MASK BLANKS, RESIST PATTERN FORMING METHOD AND PHOTO MASK EACH USING THE COMPOSITION 

(71) Applicant: FUJIFILM CORPORATION, Tokyo (JP) 

(72) Inventors: Tomotaka Tsuchimura, Shizuoka (JP); Takuya Tsuruta, Shizuoka (JP); Takeshi Inasaki, Shizuoka (JP); Koutarou Takahashi, Shizuoka (JP) 

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

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

(21) Appl. No.: 14/497,560 

(22) Filed: Sep.26,2014 

## (65) Prior Publication Data 

US 2015/0010855 Al Jan. 8, 2015 

(63) Continuation of application No. PCT/JP2013/058852, filed on Mar. 26, 2013. 

## (30) Foreign Application Priority Data 

<img src='content_image/889971.jpg'>

(51) Int. Cl. 

<img src='content_image/889972.jpg'>

(52) U.S. Cl. CPC ................ G03F 71027 (2013.01); C08F 12122 (2013.01); C08F 12124 (2013.01); C08F 12126 (2013.01); C08F 12130 (2013.01); C08F 12132 (2013.01); C08F 212114 (2013.01); C09D 125118 (2013.01); G03F 1100 (2013.01); G03F 1120 (2013.01); G03F 1122 (2013.01); G03F 71004 (2013.01); G03F 710045 (2013.01); G03F 710382 (2013.01); G03F 710388 (2013.01); G03F 710392 (2013.01); G03F 710397 (2013.01); G03F 712037 (2013.01); G03F 712039 (2013.01) 

## Related U.S. Application Data 

<img src='content_image/889934.jpg'>

# (IO) Patent No.: US 9,285,679 B2 

# (45) Date of Patent: Mar.15,2016 

(58) Field of Classification Search CPC .......... G03F 7/004; G03F 7/027; G03F 7/039 See application file for complete search history. 

## (56) References Cited 

<img src='content_image/889973.jpg'>

<img src='content_image/889974.jpg'>

Kruger, S.A., Riggings, C., Cardineau, B., Younkin, T. R., Brainard, R.L. -Catalytic andAutocatalytic Mechanisms of Acid Amplifiers for Use in EUV Photoresists, Chem. Mater, 2010, 22, pp. 5609-5616.* Communication issued on Mar. 10, 2015 by the Japanese Patent Office in related application No. 2012072540. 

Communication issued on Mar. 1, 2015 by the Korean Intellectual Property Office in related KR application No. 10-2014-7026957. International Search Report dated Jun. 25, 2013 issued in Interna› tional Application No. PCT/JP2013/058852 (PCT/ISA/210). Written Opinion dated Jun. 25, 2013 issued in International Appli› cation No. PCT/JP2013/058852 (PCT/ISA/237). Seth Kruger et al., "Can Acid Amplifiers Help Beat the Resolution, 

Line Edge Roughness, and Sensitivity Trade-Off?", Japanese Journal of Applied Physics, 49, Apr. 20, 2010, pp. 041602-1-041602-5. Kazuaki Kudo et al., "3-Phenyl-3,3-ethylenedioxy-l-propyl Sulfonates as Acid Amplifiers to Enhance the Photosensitivity of Positive-Working Photoresists", Chemistry of Materials, 11, Jul. 7, 1999,pp.2119-2125. 

Office Action dated Sep. 9, 2014 issued by the Japanese Patent Office in counterpart Japanese Application No.2012-078094. 

Primary Examiner - Anca Eoff 

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

## (57) ABSTRACT 

There is provided an actinic ray-sensitive or radiation-sensi› tive composition containing (a) a compound represented by the formula ( al) capable of generating an acid having a size of 200 A $^{3 }$or more in volume and (~) a compound capable of generating an acid upon irradiation with an actinic ray or radiation, and the formula ( al) is defined as herein, 

and a resist film formed using the actinic ray-sensitive or radiation-sensitive composition, a resist-coated mask blanks coated with the resist film, a resist pattern form› ing method comprising exposing the resist film and developing the exposed film, a photomask obtained by exposing and developing the resist-coated mask blanks, a method for manufacturing an electronic device, com› prising the resist pattern forming method and an elec› tronic device manufactured by the manufacturing method of an electronic device. 

<img src='content_image/889975.jpg'>

US009285679B2 

## U.S. PATENT DOCUMENTS 

(Continued) 

## FOREIGN PATENT DOCUMENTS 

(Continued) 

## OTHER PUBLICATIONS 

(Continued) 

## 36 Claims, No Drawings 

