US009541834B2  c12)  United States Patent  Pohlers et al.  (IO)  Patent No.:  US 9,541,834 B2  (45)  Date of Patent:  Jan.10,2017  (54)  IONIC THERMAL ACID GENERATORS FOR  LOW TEMPERATURE APPLICATIONS  (71)  Applicant:  Rohm and Haas Electronic Materials  LLC,  Marlborough, MA (US)  (72)  Inventors:  Gerhard Pohlers,  Needham, MA (US);  Cong Liu,  Shrewsbury, MA (US);  Cheng-Bai Xu,  Southborough, MA  (US);  Kevin Rowell,  Brighton, MA  (US);  Irvinder Kaur,  Westborough,  MA (US)  (73)  Assignee:  Rohm and Haas Electronic Materials  LLC,  Marlborough, MA (US)  ( * )  Notice:  Subject to any disclaimer, the term ofthis  patent is extended or adjusted under 35  U.S.C. 154(b) by 276 days.  (21)  Appl. No.:  13/691,689  (22)  Filed:  Nov. 30, 2012  (51)  Int. Cl.  (52)  U.S. Cl.  CPC ...............  G03F  7140  (2013.01);  C07C 309/03  (2013.01);  C07C 309/06  (2013.01);  C07D  239/26  (2013.01);  C07D 241112  (2013.01);  C07D 263132  (2013.01);  C07D  277122  (2013.01);  C07D 333/48  (2013.01);  G03F  710397  (2013.01);  G03F  7109  (2013.01);  G03F  71091  (2013.01);  G03F  7111  (2013.01);  G03F  7130  (2013.01);  G03F  71405  (2013.01)  (58)  Field of Classification Search  None  See application file for complete search history.  (56)  References Cited  U.S. PATENT DOCUMENTS  FOREIGN PATENT DOCUMENTS  OTHER PUBLICATIONS  (57)  ABSTRACT  (65)  Prior Publication Data  16 Claims, 1 Drawing Sheet  G03F  7140  G03F  7130  G03F  7109  G03F  7111  G03F  71039  C07D 239/26  C07D 241112  C07D 263132  C07D  277122  C07C 309/03  C07C 309/06  C07D 333/48  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (2006.01)  3,474,054 A  4,200,729 A  4,251,665 A  10/1969 White  4/1980 Calbo  2/1981 Calbo  US 2015/0212414 Al  Jul. 30, 2015  (Continued)  (Continued)  CN  EP  102117022  *  7/2011  0164248 Bl  10/1991  Chemical  Abstract  for  CN  102117022  (Accession  No.  2011:857786) (2011).*  Primary Examiner  - Sin Lee  (74)  Attorney, Agent, or Firm  - Mintz Levin Cohn Ferris  Glovsky and Popeo, P.C.; Peter  F.  Corless  New ionic thermal acid generator compounds are provided.  Also provided are photoresist compositions, antireflective  coating compositions, and chemical trim overcoat compo› sitions, and methods of using the compositions. 