US009164383B2  (IO)  Patent No.:  US 9,164,383 B2  Oct. 20, 2015  (45)  Date of Patent:  c12)  United States Patent  Hatakeyama  (54)  RESIST COMPOSITION AND PATTERNING  PROCESS  2008/0015278 Al  2010/0047709 Al  2010/0248143 Al*  1/2008 Malik et al.  2/2010 Echigo et al.  9/2010 Ito et al ...................... 430/282.1  FOREIGN PATENT DOCUMENTS  (75)  Inventor:  Jun Hatakeyama,  Joetsu (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 88 days.  (21)  Appl. No.:  13/372,691  (22)  Filed:  Feb.14,2012  (65)  Prior Publication Data  (30)  Foreign Application Priority Data  US 2012/0208127 Al  Aug. 16, 2012  Feb. 15, 2011  (JP) ................................. 2011-029588  (51)  Int. Cl.  (52)  U.S. Cl.  CPC ..............  G03F  71038  (2013.01);  G03F  710043  (2013.01);  G03F  710048  (2013.01);  G03F  710757  (2013.01)  ( 58)  Field of Classification Search  None  See application file for complete search history.  (56)  References Cited  U.S. PATENT DOCUMENTS  (57)  ABSTRACT  G03F  71004  G03F  71038  G03F  71075  (2006.01)  (2006.01)  (2006.01)  4,332,879 A *  4,608,434 A  5,415,749 A  5,534,312 A  6,787,198 B2  6,849,305 B2  7,303,855 B2  7,358,025 B2  7,632,624 B2  8,088,554 B2  2004/0067444 Al  2004/0202956 Al*  2006/0241276 Al *  2007/0015085 Al  2007 /0210393 Al  6/ 1982 Pastor et al. ............... 430/272.1  8/1986 Shimp  5/1995 Hamilton  7 / 1996 Hill et al.  9/2004 Mukherjee et al.  2/2005 Bravo-Vasquez et al.  12/2007 Hatakeyama et al.  4/2008 Hatakeyama  12/2009 Hatakeyama et al.  1/2012 Hatakeyama  4/2004 Wakabayashi et al.  10/2004 Takahashi et al. ......... 430/270.1  10/2006 Inatomi et al. ................ 528/129  1/2007 Kawamura  9/2007 Rehspringer et al.  CN  JP  JP  JP  JP  JP  JP  JP  JP  JP  JP  JP  JP  WO  WO  WO  1703286  A  07-258587  A  2002-270051  A  2005128509  A  2006227391  A  2006259249  A  2006259482  A  2006285095  A  2006293207  A  2006293298  A  2007199653  A  2007316282  A  2008116677  A  2007 /007 550 Al  2010/059174 Al  WO 2010059174 Al *  11/2005  10/1995  9/2002  5/2005  8/2006  9/2006  9/2006  10/2006  10/2006  10/2006  8/2007  12/2007  5/2008  1/2007  5/2010  5/2010  OTHER PUBLICATIONS  Hinsberg, William et al., "Extendibility of Chemically Amplified  Resists : Another Brick Wall?", Proceedings of SPIE, 2003, pp. 1-14,  vol. 5039.  Jones, G.A.C. et al., "Fabrication of nanoscale ZnO field effect tran› sistors using the functional precursor zinc neodecanoate directly as a  negative electron beam lithography resist", J. Vac. Sci. Technol.,  Nov./Dec. 2009, pp. 3164-3168, vol. 27(6).  Ridaoui, Hassan et al., "Direct ArF laser photopatterning of metal  oxide nanostructures prepared by the sol-gel route", Nanotechnol› ogy, 2010, pp. 1-10, vol. 21.  Taiwanese Office Action dated Nov. 19, 2013, issued in Taiwanese  Patent Application No. 101104425.  Japanese Office Action dated Nov. 11, 2014, issued in corresponding  JP Application No. 2012-024621 (3 pages).  * cited by examiner  Primary Examiner  - Cynthia H Kelly  Assistant Examiner  - Anna Malloy  (74)  Attorney,  Agent,  or Firm  - Westerman,  Hattori,  Daniels  & Adrian, LLP  A resist composition comprising a salt of a mono- to tet› rafunctional carboxylic acid with a metal selected from mag› nesium, chromium, manganese, iron, cobalt, nickel, copper,  zinc, silver, cadmium, indium, tin, antimony, cesium, zirco› nium, and hafnium, and a solvent is improved in film unifor› mity when coated, and exhibits a high resolution, high sensi› tivity, and minimal LER when processed by the EB or EUV  lithography.  8 Claims, No Drawings 