(IO)  Patent No.:  US 9,034,557 B2  May 19, 2015  (45)  Date of Patent:  c12)  United States Patent  Dimov et al.  (54)  CHEMICALLY AMPLIFIED POSITIVE  PHOTORESIST COMPOSITION  (75)  Inventors:  Ognian N. Dimov,  Warwick, RI (US);  Binod B. De,  Attleboro, MA (US)  (73)  Assignee:  FUJIFILM ELECTRONIC  MATERIALS U.S.A., INC.,  North  Kingstown, RI (US)  ( *)  Notice:  Subject to any disclaimer, the term ofthis  patent is extended or adjusted under 35  U.S.C. 154(b) by 581 days.  (21)  Appl. No.:  12/791,397  (22)  Filed:  Jun.1,2010  (60)  Provisional application No. 61/182,911, filed on Jun.  1, 2009.  (51)  Int. Cl.  (52)  U.S. Cl.  CPC ............  G03F  710045  (2013.01);  G03F  710392  (2013.01);  G03F  710397  (2013.01)  ( 58)  Field of Classification Search  USPC ............... 430/270.1, 326; 540/484, 485, 492,  540/500, 504, 515; 558/315; 570/111, 113  See application file for complete search history.  FOREIGN PATENT DOCUMENTS  OTHER PUBLICATIONS  (57)  ABSTRACT  27 Claims, No Drawings  (56)  References Cited  U.S. PATENT DOCUMENTS  (65)  Prior Publication Data  Related U.S. Application Data  G03F  71004  G03F  71039  G03F  7120  (2006.01)  (2006.01)  (2006.01)  5,403,690 A  5,629,134 A  5,744,281 A  5,994,022 A *  6,071,670 A *  6,136,500 A  6,165,678 A *  6,251,558 Bl  6,280,900 Bl  6,300,035 Bl  6,319,649 Bl  6,767,688 B2  7,396,633 B2  7,479,361 B2  2002/0006578 Al *  2005/0008968 Al  2006/0210921 Al  2007 /0026343 Al *  2007 /0048660 Al  2008/0085473 Al*  2008/0153030 Al  4/1995 Kuramoto et al.  5/1997 Oikawa et al.  4/ 1998 Niki et al.  11/1999 Tanabe et al. ................. 430/170  6/2000 Ushirogouchi et al. ... 430/270.1  10/2000 Kobayashi et al.  12/2000 Allen et al ................. 430/270.1  6/2001 Elian et al.  8/2001 Chiba et al.  10/2001 Thackeray et al.  11/2001 Kato et al.  7/2004 Teng et al.  7/2008 Nagahara et al.  1/2009 Nagahara et al.  1/2002 Kodama et al. ............ 430/270.1  1/2005 Watanabe et al.  9/2006 Watanabe  2/2007 Tarutani ..................... 430/270.1  3/2007 Nozaki et al.  4/2008 Ito ................................. 430/319  6/2008 Kobayashi et al.  2008/0158675 Al  7/2008 Fukushige et al.  2008/0241736 Al* 10/2008 Kobayashi et al ......... 430/270.1  2008/0268370 Al  10/2008 Tanaka et al.  JP  JP  JP  JP  JP  JP  JP  KR  WO  WO  06-236041  2000330284  2006025890  2007-163767  2007177192  2008064909  2008129388  20040079758  WO  98/38195  WO  03/104199  8/1994  11/2000  2/2006  6/2007  7/2007  3/2008  6/2008  9/2004  9/1998  12/2003  A photoresist composition. The composition has the follow› ing: (a) one or more resin binders that include one or more  acid sensitive groups and that are substantially free of phe› nolic groups protected by acetal or ketal groups; (b) one or  more photo acid generators, that, upon exposure to a source of  high energy, decompose and generate a photoacid strong  enough to remove the one or more acid sensitive groups; (c)  one or more ionic non-photosensitive additives including an  iminium salt; and ( d) one or more solvents. There is also a  process for patterning relief structures on a substrate employ› ing the photoresist composition.  Primary Examiner  - Anca Eoff  (7 4)  Attorney, Agent, or Firm  - Blakely, Sokoloff, Taylor &  Zafman, LLP  * cited by examiner  Ferreira et al., "Choice of Amines as Stabilizers for Chemically  Amplified Resist Systems", Proceedings of SPIE, vol. 3333, pp.  236-244. (1998).*  International Search Report Application No. PCT/USl0/36868,  dated Aug. 13, 2010.  Ferreira, L., et al., "Choice of Amines as Stabilizers for Chemically  Amplified Resist Systems", Olin Microelectronic Materials, E.  Providence, RI, SPIE vol. 3333, pp. 236-244.  Endo,  Y.  et al., "Reaction of Benzene with Diphenyl Sulfoxides,"  Faculty of Pharmaceutical Sciences, Univ. of Tokyo, Tokyo, Japan,  vol. 29, Aug. 27, 1981, pp. 3753-3755.  PCT International Preliminary Report on Patentability for related  PCT Patent Application No. PCT/US2010/036868, Dec. 15, 2011, 7  pgs.  Supplementary European Search Report and Written Opinion from  EP 10 78 3909 completed on Oct. 30, 2012, 6 pgs.  Office Action from Japanese Patent Application No. 2012-513356  mailed Jul. 22, 2014 3 pgs.  Search Report and Written Opinion from Singapore Application No.  201108287-2 mailed Aug. 5, 2014, 19 pgs.  Search Report from Taiwan Application No. 99117405 mailed Jul.  22, 2014, 1 pgs.  US009034557B2  US 2010/0304299 Al  Dec. 2, 2010 