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# c12) United States Patent Utsumi et al. 

# (54) COMPOUND, RADICAL POLYMERIZATION INITIATOR, METHOD FOR PRODUCING COMPOUND, POLYMER, RESIST COMPOSITION, AND METHOD FOR FORMING RESIST PATTERN 

(75) Inventors: Yoshiyuki Utsumi, Kawasaki (JP); Takahiro Dazai, Kawasaki (JP); Jun Iwashita, Kawasaki (JP); Kenri Konno, 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.: 14/126,535 

(22) PCT Filed: Jun.15,2012 

(86) PCT No.: PCT I JP2012/065389 § 371 (c)(l), (2), ( 4) Date: Dec.16, 2013 

(87) PCT Pub. No.: WO2012/173235 PCT Pub. Date: Dec. 20, 2012 

## (65) Prior Publication Data 

US 2014/0141373 Al May 22, 2014 

## (30) Foreign Application Priority Data 

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(51) Int. Cl. 

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(52) U.S. Cl. CPC ................ G03F 71038 (2013.01); C07C 25118 (2013.01); C07C 309112 (2013.01); C07C 381112 (2013.01); C08F 4104 (2013.01); G03F 710045 (2013.01); G03F 710046 (2013.01); G03F 710397 (2013.01); C07C 2101/14 (2013.01); C07C 2103/74 (2013.01) 

( 58) Field of Classification Search None See application file for complete search history. 

## (56) References Cited 

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## U.S. PATENT DOCUMENTS 

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# (IO) Patent No.: US 9,097,971 B2 

# Aug. 4, 2015 (45) Date of Patent: 

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Sedlak et al., "Synthesis and Characterization of New Surface Active Azo Initiators for Radical Reactions," Molecules (Electronic Publi› cation) vol. 5, No. 5, pp. 730-736, 2000.* 

Primary Examiner - Cynthia Hamilton 

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

## (57) ABSTRACT 

A compound represented by formula (I). In the formula, R 1 represents a hydrocarbon group of 1 to 10 carbon atoms; Z represents a hydrocarbon group of 1 to 10 carbon atoms or a cyano group; provided that R $^{1 }$and Z may be mutually bonded to form a ring; X represents a divalent linking group having any one selected from ---0-C(=O)-, -NH----C(=O)› and -NH----C(=NH)- on a terminal that comes into con› tact with Q; p represents an integer of 1 to 3; Q represents a hydrocarbon group having a valency of (p+ 1 ), provided that, when pis 1, Q may be a single bond; R $^{2 }$represents a single bond, an alkylene group which may have a substituent or an arylene group which may have a substituent; q represents 0 or 1; r represents an integer of Oto 8; and A+ represents a metal cation or an organic cation. 

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US009097971B2 

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## FOREIGN PATENT DOCUMENTS 

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## OTHER PUBLICATIONS 

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## 4 Claims, No Drawings 

[Chemical Formula 1] 

