(45)  Date of Patent:  Apr. 8, 2014  (IO)  Patent No.:  US 8,691,490 B2  c12)  United States Patent  Ohashi et al.  (54)  SULFONIUM SALT, POLYMER, METHOD  FOR PRODUCING THE POLYMER, RESIST  COMPOSITION AND PATTERNING PROCESS  (75)  Inventors:  Masaki Ohashi,  Jyoetsu (JP);  Satoshi  Watanabe,  Jyoetsu (JP);  Youichi  Ohsawa,  Jyoetsu (JP);  Keiichi  Masunaga,  Jyoetsu (JP);  Takeshi  Kinsho,  Jyoetsu (JP)  (73)  Assignee:  Shin-Etsu Chemical Co., Ltd.,  Tokyo  (JP)  ( *)  Notice:  Subject to any disclaimer, the term ofthis  patent is extended or adjusted under 35  U.S.C. 154(b) by 210 days.  (21)  Appl. No.:  13/013,506  (22)  Filed:  Jan.25,2011  (51)  Int. Cl.  (52)  U.S. Cl.  USPC ........  430/270.1;  430/921; 430/925; 560/219;  560/221; 560/222; 560/223; 562/109; 562/110;  562/113  ( 58)  Field of Classification Search  None  See application file for complete search history.  FOREIGN PATENT DOCUMENTS  OTHER PUBLICATIONS  (57)  ABSTRACT  2 Claims, 4 Drawing Sheets  U.S. PATENT DOCUMENTS  (56)  References Cited  (30)  Foreign Application Priority Data  (65)  Prior Publication Data  G03F 71004  C07C69/54  C07C 309167  (2006.01)  (2006.01)  (2006.01)  5,650,483  A  7/1997 Malik et al.  5,945,250  A  8/1999 Aoai et al.  6,048,672  A  4/2000 Cameron et al.  6,280,898 Bl  8/2001 Hasegawa et al.  6,312,867 Bl  11/2001 Kinsho et al.  7,833,694 B2  11/2010 Hasegawa et al.  8,062,831 B2  11/2011 Shinachi et al.  2002/0102491 Al  8/2002 Kodama et al.  2003/0013039 Al  1/2003 Kobayashi et al.  2004/0197697 Al  10/2004 Korionoff et al.  2004/0260031 Al  12/2004 Takeda et al.  2006/0228648 Al  10/2006 Ohsawaet al.  2007 /0078269 Al  4/2007 Harada et al.  2007/0148594 Al  6/2007 F unatsu et al.  2007/0149702 Al  6/2007 Ando et al.  2007/0160929 Al  7/2007 Hasegawa et al.  2007 /0231738 Al  10/2007 Kaneko et al.  2007 /0264596 Al  11/2007 Ohsawaet al.  2008/0026331 Al  1/2008 Hasegawa et al.  2008/0085469 Al  4/2008 Ohsawaet al.  2008/0090172 Al  4/2008 Hatakeyama et al.  2008/0096128 Al  4/2008 Takeda et al.  2008/0102407 Al  5/2008 Ohsawaet al.  2008/0118860 Al  5/2008 Harada et al.  2008/0153030 Al  2008/0305411 Al  2009/0069521 Al  2009/0081588 Al  2009/0208867 Al  2009/0208873 Al  2009/0233223 Al  2009/0233242 Al  2009/0274978 Al  2009/0274984 Al  2009/0280434 Al  2009/0318652 Al  2010/0075256 Al  2010/0099042 Al  2010/0112482 Al  2010/0136478 Al  6/2008 Kobayashi et al.  12/2008 Koitabashi et al.  3/2009 Nagai et al.  3/2009 Hatakeyama et al.  8/2009 Harada et al.  8/2009 Harada et al.  9/2009 Tachibana et al.  9/2009 Hasegawa et al.  11/2009 Ohashi et al.  11/2009 Shinachi et al.  11/2009 Harada et al.  12/2009 Nagai et al.  3/2010 Joo et al.  4/2010 Ohashi et al.  5/2010 Watanabe et al.  6/2010 Kawaue et al.  CA  JP  2049772 Al  A-03-501970  2/1992  5/1991  US008691490B2  (Continued)  (Continued)  Jul. 17, 2012 Notification of Reasons for Refusal issued in Japanese  Application No. 2010-021078 (with partial translation).  (Continued)  Primary Examiner  - Sin J. Lee  (74)  Attorney, Agent, or Firm  - Oliff PLC  There is disclosed a sulfonium salt represented by the follow› ing general formula ( 1). In the formula, X and Y each repre› sents a group having a polymerizable functional group; Z  represents a divalent hydrocarbon group having 1 to 33 car› bon atoms optionally containing a hetero atom; R $^{1 }$represents  a divalent hydrocarbon group having 1 to 36 carbon atoms  optionally containing a hetero atom; and R 2  and R 3  each  represents a monovalent hydrocarbon group having 1 to 30  carbon atoms optionally containing a hetero atom or R $^{2 }$and  R $^{3 }$may be bonded with each other to form a ring together with  a sulfur atom in the formula. There can be provided a sulfo› nium salt usable as a resist composition providing high reso› lution and excellent in LER in photo lithography using a high  energy beam such as an ArF excimer laser, an EUV light and  an electron beam as a light source, a polymer obtained from  the sulfonium salt, a resist composition containing the poly› mer and a patterning process using the resist composition.  US 2011/0189607 Al  Aug. 4, 2011  Feb. 2, 2010  (JP) ................................. 2010-021078  (1) 