(45)  Date of Patent:  *Nov. 12, 2019  (IO)  Patent No.:  US 10,474,032 B2  Prokopowicz et al.  c12)  United States Patent  (54)  COATING COMPOSITIONS  (56)  References Cited  U.S. PATENT DOCUMENTS  FOREIGN PATENT DOCUMENTS  OTHER PUBLICATIONS  (57)  ABSTRACT  19 Claims, 2 Drawing Sheets  (58)  Field of Classification Search  CPC . G03F 7/09; G03F 7/091; G03F 7/092; G03F  7/20; G03F 7/2041; C08K 3/36  USPC ................................ 430/271.1, 272.1, 273.1  See application file for complete search history.  (52)  U.S. Cl.  CPC ................  G03F 71091  (2013.01);  C0SK 3/36  (2013.01);  C09D 129104  (2013.01);  C09D  133102  (2013.01);  G03F  7111  (2013.01);  G03F  712041  (2013.01)  (51)  Int. Cl.  (60)  Provisional application No. 60/682,941, filed on May  19, 2005, provisional application No. 60/678,032,  filed on May 4, 2005.  (62)  Division of application No. 11/417,374, filed on May  4, 2006, now Pat. No. 8,889,344.  (22)  Filed:  Nov. 17, 2014  (21)  Appl. No.:  14/543,460  ( *)  Notice:  Subject to any disclaimer, the term ofthis  patent is extended or adjusted under 35  U.S.C. 154(b) by  O  days.  This patent is subject to a terminal dis› claimer.  (73)  Assignee:  Rohm and Haas Electronic Materials  LLC,  Marlborough, MA (US)  (72)  Inventors:  Gregory P. Prokopowicz,  Worcester,  MA (US);  Michael K. Gallagher,  Hopkinton, MA (US)  (71)  Applicant:  Rohm and Haas Electronic Materials  LLC,  Marlborough, MA (US)  Zirconium Dioxide (1314-23-4), Chemical Book, 2008.*  Final Office Action issued in counterpart Korean Application No.  10-2016-0054286 (4 pages).  English language summary of Office Action and Search Report  issued in Taiwan counterpart apoplication 106-2(60()091190- 10620224230, 2017 (4 pages).  English language summary of Office Action dated Apr. 13, 2017  issued in Japanese counterpoart Application No. 2016-088986 (3  pages).  * cited by examiner  Primary Examiner  - Anca Eoff  (74)  Attorney, Agent, or Firm  - Mintz Levin Cohn Ferris  Glovsky and Popeo, P.C.; Peter  F.  Corless  In one aspect, coating compositions are provided that com› prise a component a component that comprises one or more  silicon, antimony, aluminum, yttrium, cerium, lanthanum,  tin, titanium, zirconium, hafnium, indium or zinc com› pounds. In another aspect, coating compositions are pro› vided that comprise a plurality of discrete particles. Pre› ferred coating compositions of the invention are useful for  antireflective purposes, particularly with an underlaying  photoresist coating layer, as well as for a barrier layer in  immersion lithography.  4,072,527  A  *  2/1978 Fan ............................ 430/273.1  5,597,677  A  *  1/1997 Kangas ..................... G03F 7/11  430/143  6,458,467 Bl* 10/2002 Mizuno et  al ................ 428/480  6,824,952 Bl* 11/2004 Minsek ................... G03F 7/091  430/156  7,781,141 B2 *  8,889,344 B2 *  2005/0202340 Al*  2006/0105272 Al*  2006/0211785 Al  2011/0233048 Al  2014/0356785 Al  2015/0362836 Al  8/2010 Gallagher et al. ......... 430/270.1  11/2014  9/2005  5/2006  9/2006  9/2011  12/2014  12/2015  Prokopowicz et al. . ..... 430/326  Houlihan et al. .......... 430/270.1  Gallagher et al. ............ 430/311  Aoai  Kuramoto et al.  Williams, III et al.  Tsuchimura et al.  JP  KR  TW  TW  H 11-274129 A  10-2011-0106859  201029961 A  201439062 A  10/1999  3/2013  8/2010  10/2014  US 2015/0072290 Al  Mar. 12, 2015  (65)  Prior Publication Data  Related U.S. Application Data  G03F  7109  G03F  7111  G03F  7120  C0SK 3/36  C09D 129104  C09D 133102  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (2006.01)  US010474032B2 