US009256127B2  c12)  United States Patent  Sagehashi et al.  (54)  MONOMER, POLYMER, RESIST  COMPOSITION, AND PATTERNING  PROCESS  (IO)  Patent No.:  US 9,256,127 B2  (45)  Date of Patent:  Feb.9,2016  FOREIGN PATENT DOCUMENTS  (57)  ABSTRACT  (65)  Prior Publication Data  (30)  Foreign Application Priority Data  (56)  References Cited  U.S. PATENT DOCUMENTS  17 Claims, 1 Drawing Sheet  (71)  Applicant:  Shin-Etsu Chemical Co., Ltd.,  Tokyo  (JP)  (72)  Inventors:  Masayoshi Sagehashi,  Joetsu (JP);  Takayuki Fujiwara,  Joetsu (JP);  Koji  Hasegawa,  Joetsu (JP);  Ryosuke  Taniguchi,  Joetsu (JP)  (73)  Assignee:  SHIN-ETSU CHEMICAL CO., LTD.,  Tokyo (JP)  ( *)  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.:  14/697,901  (22)  Filed:  Apr. 28, 2015  (51)  Int. Cl.  (52)  U.S. Cl.  CPC ............  G03F 710397  (2013.01);  C07D 307183  (2013.01);  C07D 3071935  (2013.01);  (Continued)  ( 58)  Field of Classification Search  None  See application file for complete search history.  US 2015/0323865 Al  Nov. 12, 2015  May 9, 2014  (JP) ................................. 2014-097347  A polymer for resist use is obtainable from a monomer having  formula (1) wherein R$^{1 }$is H, CH$_{3 }$ or CF 3, R$^{2 }$andR$^{3 }$each are  Hor a monovalent hydrocarbon group, X $^{1 }$is a divalent hydro› carbon group, k$^{1}$=0 or 1, and Z forms a 5 or 6-membered  alicyclic ring. A resist composition comprising the polymer is  shelf stable and displays a high dissolution contrast, con› trolled acid diffusion and low roughness during both alkaline  development and organic solvent development.  Primary Examiner  - Sin Lee  (74)  Attorney, Agent,  or Firm  - Westerman,  Hattori,  Daniels  & Adrian, LLP  (Continued)  (Continued)  (Continued)  C08F 24100  C08F 28106  (2006.01)  (2006.01)  6,280,898 Bl  8/2001 Hasegawa et al.  6,312,867 Bl  11/2001 Kinsho et al.  JP  JP  3042618 B2  5/2000  2000-336121 A  12/2000  (1)  ~  0  I  x~o  k1  IT:o  U---1  PHOTORESIST COATING  PHOTORESIST EXPOSURE 