I 1111111111111111 1111111111 11111 111111111111111 1111111111111111 IIII IIII IIII  US010088749B2  (54)  PHOTOACID-GENERATING COMPOUND  AND ASSOCIATED POLYMER,  PHOTORESIST COMPOSITION, AND  METHOD OF FORMING A PHOTORESIST  RELIEF IMAGE  (IO)  Patent No.:  US 10,088,749 B2  Oct. 2, 2018  (45)  Date of Patent:  Aqad  c12)  United States Patent  (71)  Applicant:  Rohm and Haas Electronic Materials  LLC,  Marlborough, MA (US)  (72)  Inventor:  Emad Aqad,  Northborough, 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  O  days.  (21)  Appl. No.:  15/281,292  (22)  Filed:  Sep. 30, 2016  (65)  Prior Publication Data  US 2018/0095363 Al  Apr. 5, 2018  (51)  Int. Cl.  G03F 71004  (2006.01)  G03F 7130  (2006.01)  C08F 228102  (2006.01)  C08F 228106  (2006.01)  C07D 333174  (2006.01)  C07C 309102  (2006.01)  C07C 309/06  (2006.01)  C07C 309112  (2006.01)  C07C 309/14  (2006.01)  C07C 309122  (2006.01)  C07C 309/23  (2006.01)  C07C 309/19  (2006.01)  C08F  220168  (2006.01)  G03F  71039  (2006.01)  G03F  7116  (2006.01)  G03F  7120  (2006.01)  G03F  7132  (2006.01)  G03F  7140  (2006.01)  C07C 303132  (2006.01)  C07C 309/04  (2006.01)  (52)  U.S. Cl.  CPC ..........  G03F  710045  (2013.01);  C07C 303132  (2013.01);  C07C 309/04  (2013.01);  C07C  309/06  (2013.01);  C07C 309112  (2013.01);  C07C 309/14  (2013.01);  C07C 309/19  (2013.01);  C07C 309122  (2013.01);  C07C  309/23  (2013.01);  C07D 333174  (2013.01);  C08F  220168  (2013.01);  C08F  228102  (2013.01);  C08F  228106  (2013.01);  G03F  710397  (2013.01);  G03F  7116  (2013.01);  G03F  712004  (2013.01);  G03F  7130  (2013.01);  G03F  71322  (2013.01);  G03F  7140  (2013.01)  ( 58)  Field of Classification Search  CPC ....... G03F 7/0045; G03F 7/30; C07C 333/74;  C08F 228/02; C08F 228/06  wherein m, n, R1, R 2 ,  X,  Y,  and z- are defined herein. The  photoacid-generating compound exhibits strong absorption  and chemical sensitivity to extreme ultraviolet radiation,  while also absorbing longer wavelengths with desirably  reduced chemical sensitivity. Also described are a polymer  incorporating the residue of a polymerizable version of the  photoacid-generating compound, a photoresist composition  that includes the photoacid-generating compound, the poly› mer, or a combination thereof, and a method of forming a  photoresist relief image using the photoresist composition.  11 Claims, 4 Drawing Sheets  USPC ......... 430/270.1, 921, 922, 326; 549/12, 41,  549/42, 43, 45, 46, 47; 526/256, 280,  526/287, 288  See application file for complete search history.  (Continued)  (56)  References Cited  U.S. PATENT DOCUMENTS  2,760,863  A  8/1956  Plambeck, Jr.  2,850,445  A  9/1958 Oster  2,875,047  A  2/1959 Oster  3,097,096  A  7/1963 Oster  3,427,161 A  2/1969 Laridon et al.  3,479,185 A  11/1969  Chambers, Jr.  3,549,367  A  12/1970 Chang et al.  4,343,885  A  8/1982  Reardon, Jr.  6,187,504 Bl*  2/2001  Suwa .................... G03F 7/0045  430/270.1  7,776,510 B2 *  8/2010 Iwai ...................... C07C 309/04  430/270.1  8,431,325 B2  4/2013 Hashimoto et al.  CN  103288796  A  9/2013  EP  1260864 Al  11/2002  FOREIGN PATENT DOCUMENTS  (Continued)  Primary Examiner  - John S Chu  (74)  Attorney, Agent, or Firm  - Cantor Colburn LLP  A photoacid-generating compound has the structure  (57)  ABSTRACT 