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# c12) United States Patent Takizawa et al. 

# (54) PATTERN-FORMING METHOD, ELECTRON BEAM-SENSITIVE OR EXTREME ULTRAVIOLET RADIATION-SENSITIVE RESIN COMPOSITION, RESIST FILM, MANUFACTURING METHOD OF ELECTRONIC DEVICE USING THEM AND ELECTRONIC DEVICE 

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

(72) Inventors: Hiroo Takizawa, Shizuoka (JP); Hideaki Tsubaki, Shizuoka (JP); Shuji Hirano, 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 0 days. 

(21) Appl. No.: 14/207,867 

(22) Filed: Mar. 13, 2014 

## (65) Prior Publication Data 

US 2014/0193749 Al Jul. 10, 2014 

(63) Continuation of application No. PCT/JP2012/073765, filed on Sep. 11, 2012. 

(60) Provisional application No. 61/535,024, filed on Sep. 15, 2011. 

## (30) Foreign Application Priority Data 

Sep. 15, 2011 (JP) ................................. 2011-202044 

(51) Int. Cl. 

<img src='content_image/894717.jpg'>

(52) U.S. Cl. CPC ............ G03F 710041 (2013.01); C08F 212114 (2013.01); G03F 71004 (2013.01); G03F 71038 (2013.01); G03F 71039 (2013.01); G03F 710392 (2013.01); G03F 710397 (2013.01); G03F 7120 (2013.01); G03F 712037 (2013.01); G03F 712059 (2013.01); G03F 71325 (2013.01); H0JJ 3713174 (2013.01); C08F 12/20 (2013.01); C08F 12/24 (2013.01); C08F 212/32 (2013.01) 

## Related U.S. Application Data 

<img src='content_image/894697.jpg'>

# (IO) Patent No.: US 9,170,489 B2 

# Oct. 27, 2015 (45) Date of Patent: 

(58) Field of Classification Search CPC ......... G03F 7/004; G03F 7/038; G03F 7/039; G03F 7/0392; G03F 7/0397; G03F 7/20; G03F 7/2037; G03F 7/2059; G03F 7/325; G03F 7/0041; H0lJ 37/3174; C08F 12/20; C08F 12/24; C08F 212/14; C08F 212/32 USPC .. .. ... ... ... ... ... .. ... ... ... ... .. ... ... . 430/296, 311, 942 See application file for complete search history. 

## (56) References Cited 

<img src='content_image/894722.jpg'>

<img src='content_image/894725.jpg'>

International Search Report (PCT/ISA/210), dated Oct. 23, 2012, issued by the International Searching Authority in counterpart Inter› national Patent Application No. PCT/JP2012/073765. 

Written Opinion (PCT/ISA/237), dated Oct. 23, 2012, issued by the International Searching Authority in counterpart International Patent Application No. PCT/JP2012/073765. 

Office Action dated Oct. 14, 2014 issued by Japanese Patent Office in counterpart Japanese Application No. 2012-196110. 

Search Report dated Mar. 30, 2015, issued by the European Patent Office in counterpart European Application No. 12831380.6. 

Primary Examiner - Christopher Young 

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

## (57) ABSTRACT 

A pattern-forming method includes in this order: step (1) of forming a film with an electron beam-sensitive or extreme ultraviolet radiation-sensitive resin composition that contains (A) a resin having an acid-decomposable repeating unit and capable of decreasing a solubility of the resin (A) in a devel› oper containing an organic solvent by an action ofan acid, (B) a compound capable of generating an acid upon irradiation with an electron beam or extreme ultraviolet radiation and (C) a solvent; step (2) of exposing the film with an electron beam or extreme ultraviolet radiation; and step (4) of forming a negative pattern by development of the film with a developer containing an organic solvent after the exposing of the film, wherein a content of the compound (B) is 21% by mass to 70% by mass on the basis of all solids content of the compo› sition. 

US009170489B2 

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## 54 Claims, No Drawings 

