I 1111111111111111 11111 1111111111 111111111111111 IIIII IIIII lll111111111111111  US009063416B2  (54)  RESIST COMPOSITION, METHOD OF  FORMING RESIST PATTERN AND  COMPOUND  c12)  United States Patent  Komuro et al.  (IO)  Patent No.:  US 9,063,416 B2  (45)  Date of Patent:  Jun.23,2015  (71)  Applicant:  Tokyo Ohka Kogyo Co., Ltd.,  Kawasaki-shi (JP)  (72)  Inventors:  Yoshitaka Komuro,  Kawasaki (JP);  Yoshiyuki Utsumi,  Kawasaki (JP);  Akiya Kawaue,  Kawasaki (JP);  Toshiaki Hato,  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 160 days.  (21)  Appl. No.:  13/706,771  (22)  Filed:  Dec. 6, 2012  (65)  Prior Publication Data  US 2013/0157197 Al  Jun. 20, 2013  (30)  Foreign Application Priority Data  Dec. 14, 2011  (JP) ................................. 2011-273768  (51)  Int. Cl.  G03F  71004  C07C 591125  G03F  71027  G03F 71039  C07D313/10  C07D327/04  C07D333/46  C07D333/54  C07D333/76  C07D335/02  C07D 335/16  C07C 323152  C07C 381112  C07D 493/18  C07D307/00  C07D307/33  C07C 25118  C07C69/14  C07C 69/63  C07C 691753  C07C 69178  C07C 59/13  C07C 59/66  C07C 59170  C07C62/04  C07D 493/08  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (52)  U.S. Cl.  CPC ..............  G03F  71027  (2013.01);  G03F  710045  (2013.01);  G03F  710397  (2013.01);  C07D  313/10  (2013.01);  C07D  327104  (2013.01);  C07D 333/46  (2013.01);  C07D 333/54  (2013.01);  C07D 333176  (2013.01);  C07D  (57)  ABSTRACT  A resist composition comprising: a base component (A) that  exhibits changed solubility in a developing solution by the  action of acid; a photoreactive quencher (C); and an acid› generator component (B) that generates acid upon exposure,  wherein the photoreactive quencher (C) contains a compound  represented by general formula (cl) shown below. In the  formula, R  1  represents a hydrogen atom or a hydrocarbon  group of 1 to 20 carbon atoms which may have a substituent;  each ofR$^{2 }$and R$^{3 }$independently represents a hydrogen atom  or a hydrocarbon group of 1 to 20 carbon atoms which may  have a substituent; at least two of R $^{1 }$to R$^{3 }$may be mutually  bonded to form a ring; X represents an oxygen atom or a  sulfur atom; n represents  O  or 1; and  z+  represents an organic  cation.  8 Claims, No Drawings  (cl)  [Chemical Formula 1]  Machine translation, JP 2007-178858. Jul. 12, 2007.  *  Primary Examiner  - Cynthia H Kelly  Assistant Examiner  - Alyssa L Cepluch  (74)  Attorney, Agent, or Firm  -Knobbe Martens Olson &  BearLLP  OTHER PUBLICATIONS  FOREIGN PATENT DOCUMENTS  U.S. PATENT DOCUMENTS  (56)  References Cited  JP  JP  A-06-266100  A-09-208554  9/1994  8/1997  5,879,856 A  *  3/1999 Thackeray et al ......... 430/270.1  5,945,517 A  8/1999 Nitta et al.  (Continued)  (Continued)  (58)  Field of Classification Search  None  See application file for complete search history.  335102  (2013.01);  C07D 335/16  (2013.01);  C07C 323152  (2013.01);  C07C 381112  (2013.01);  C07D 493/18  (2013.01);  C07D  307100  (2013.01);  C07D 307133  (2013.01);  C07C 25118  (2013.01);  C07C 2101/08  (2013.01);  C07C 2103/74  (2013.01);  C07C  69/14  (2013.01);  C07C 69/63  (2013.01);  C07C  691753  (2013.01);  C07C 69178  (2013.01);  C07C 591125  (2013.01);  C07C 59/13  (2013.01);  C07C 59/66  (2013.01);  C07C 59170  (2013.01);  C07C 62/04  (2013.01);  C07D  493/08  (2013.01) 