(45)  Date of Patent:  Feb.9,2021  (IO)  Patent No.:  US 10,915,021 B2  c12)  United States Patent  Fukushima et al.  (54)  MONOMER, POLYMER, RESIST  COMPOSITION, AND PATTERNING  PROCESS  (58)  Field of Classification Search  CPC ...... G03F 7/033; G03F 7/0045; G03F 7/0046;  G03F 7/0397; G03F 7/426; G03F 7/2037;  C08F 12/16; C08F 12/22; C08F 12/24;  C08F 12/32; C08F 212/14; C08F 212/32;  C08F 212/18  See application file for complete search history.  (56)  References Cited  U.S. PATENT DOCUMENTS  FOREIGN PATENT DOCUMENTS  OTHER PUBLICATIONS  (57)  ABSTRACT  15 Claims, No Drawings  (30)  Foreign Application Priority Data  (65)  Prior Publication Data  4,178,327 A * 12/1979 Hall .................. C08F 299/0478  525/169  5,149,743 A *  9/1992 Kennedy ................. C08F 12/18  525/331.4  10,007,178 B2 *  6/2018 Hatakeyama ......... G03F 7/0045  10,495,968 B2 * 12/2019 Aqad ...................... C08L 73/00  JP  JP  64-9465 A  1/1989  01096202 A  *  4/1989  (Continued)  Machine translation of JP-01096202-A (no date).*  (Continued)  Primary Examiner  - Amanda C. Walke  (74)  Attorney, Agent, or Firm  - Westerman, Hattori,  Daniels & Adrian, LLP  A monomer having formula (A) is provided.  RA  is H, methyl  or trifluoromethyl, X$^{1 }$is a single bond, ether, ester or amide  bond,  Ra  is a C$_{1}$-C$_{20 }$monovalent hydrocarbon group, R 6  is  H or an acid labile group,  X is halogen, n is an integer of 1  to 4, m is an integer of  O  to 3, and lsn+ms4. A resist  composition comprising a polymer derived from the mono› mer has a high sensitivity to high-energy radiation, espe› cially  EUV.  G03F  71004  (2006.01)  C08F  12116  (2006.01)  G03F  71033  (2006.01)  G03F  7142  (2006.01)  C08F  2138  (2006.01)  C08F  220118  (2006.01)  C08F  228102  (2006.01)  C08F  12124  (2006.01)  C07C 431225  (2006.01)  C08F  12122  (2006.01)  C08F  12132  (2006.01)  C08F  212132  (2006.01)  G03F  71039  (2006.01)  C09D  125118  (2006.01)  C08F  212114  (2006.01)  C07C 431247  (2006.01)  C07C 391373  (2006.01)  C08F 2/50  (2006.01)  (51)  Int. Cl.  (52)  U.S. Cl.  CPC ............  G03F  71033  (2013.01);  C07C 391373  (2013.01);  C07C 431225  (2013.01);  C07C  431247  (2013.01);  C08F  2138  (2013.01);  C08F  12116  (2013.01);  C08F  12122  (2013.01);  C08F  12124  (2013.01);  C08F  12132  (2013.01);  C08F  212114  (2013.01);  C08F  212132  (2013.01);  C08F  220118  (2013.01);  C08F  228102  (2013.01);  C09D  125118  (2013.01);  G03F  710045  (2013.01);  G03F  710046  (2013.01);  G03F  710397  (2013.01);  G03F  71426  (2013.01);  C07C 2601/08  (2017.05);  C07C  2601/14  (2017.05);  C08F 2/50  (2013.01);  C08F 220/1806  (2020.02)  US 2019/0079399 Al  Mar. 14, 2019  Sep. 13, 2017  (JP) ................................. 2017-175900  (Continued)  (22)  Filed:  Sep. 5, 2018  (21)  Appl. No.:  16/121,970  ( * )  Notice:  Subject to any disclaimer, the term ofthis  patent is extended or adjusted under 35  U.S.C. 154(b) by 203 days.  (73)  Assignee:  SHIN-ETSU CHEMICAL CO., LTD.,  Tokyo (JP)  (72)  Inventors:  Masahiro Fukushima,  Joetsu (JP);  Koji Hasegawa,  Joetsu (JP);  Jun  Hatakeyama,  Joetsu (JP)  (71)  Applicant:  Shin-Etsu Chemical Co., Ltd.,  Tokyo  (JP)  (A)  1111111111111111 1111111111 111111111111111 11111 1111111111 111111111111111111  US010915021B2 