US009097971B2  c12)  United States Patent  Utsumi et al.  (IO)  Patent No.:  US 9,097,971 B2  Aug. 4, 2015  (45)  Date of Patent:  (54)  COMPOUND, RADICAL POLYMERIZATION  INITIATOR, METHOD FOR PRODUCING  COMPOUND, POLYMER, RESIST  COMPOSITION, AND METHOD FOR  FORMING RESIST PATTERN  6,949,325 B2  2001/0049073 Al  2002/0055124 Al  2004/0110085 Al  2007 /0231708 Al  2008/0187860 Al  2009/0280433 Al *  2009/0317743 Al  2010/0055608 Al  2011/0177453 Al  2011/0244392 Al  9/2005 Li et al.  12/2001 Hada et al.  5/2002 Janda et al.  6/2004 Iwai et al.  10/2007 Matsumaru et al.  8/2008 Tsubaki et al.  11/2009 Matsumura et al. ....... 430/270.1  12/2009 Shiono et al.  3/2010 Ohashi et al.  7/2011 Masubuchi et al.  10/2011 Hirano et al.  (Continued)  FOREIGN PATENT DOCUMENTS  (Continued)  OTHER PUBLICATIONS  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  (Continued)  (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.  4 Claims, No Drawings  (56)  References Cited  U.S. PATENT DOCUMENTS  GB  JP  916782 A  A-06-065310  1/1963  3/1994  [Chemical Formula 1]  3,956,269 A *  5,945,517 A  6,153,733 A  5/1976 Sheppard et al. ............. 534/886  8/ 1999 Nitta et al.  11/2000 Yukawa et al.  (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.  (65)  Prior Publication Data  US 2014/0141373 Al  May 22, 2014  (30)  Foreign Application Priority Data  Jun. 17, 2011  Oct. 4, 2011  (JP) ................................. 2011-135672  (JP) ................................. 2011-220101  (51)  Int. Cl.  G03F 71004  G03F 71038  C08F 4104  G03F 71039  C07C 309112  C07C 381112  C07C 25118  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (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 