(IO)  Patent No.:  US 10,303,056 B2  (45)  Date of Patent:  May 28, 2019  c12)  United States Patent  Hatakeyama et al.  (54)  RESIST COMPOSITION AND PATTERNING  PROCESS  US010303056B2  (71)  Applicant:  Shin-Etsu Chemical Co., Ltd.,  Tokyo  (JP)  (72)  Inventors:  Jun Hatakeyama,  Joetsu (JP);  Koji  Hasegawa,  Joetsu (JP);  Masayoshi  Sagehashi,  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.:  15/585,531  (22)  Filed:  May 3, 2017  (65)  Prior Publication Data  (30)  Foreign Application Priority Data  US 2018/0004087 Al  Jan. 4, 2018  Jun. 29, 2016  (JP) ................................. 2016-128886  (51)  Int. Cl.  (52)  U.S. Cl.  CPC .........  G03F  710392  (2013.01);  C07D  317102  (2013.01);  C07D  317104  (2013.01);  G03F  710045  (2013.01);  G03F  710046  (2013.01);  G03F  71162  (2013.01);  G03F  71168  (2013.01);  G03F  712004  (2013.01);  G03F  71322  (2013.01);  G03F  7138  (2013.01)  ( 58)  Field of Classification Search  None  See application file for complete search history.  G03F  71039  G03F  7116  G03F  7120  G03F  7138  G03F  7132  C07D  317104  C07D  317102  G03F  71004  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (56)  References Cited  U.S. PATENT DOCUMENTS  4,318,976 A *  3/1982 Shu ....................... G03F 7/0388  427/504  6,495,305 Bl * 12/2002 Enomoto ................ G03F 7 /091  430/270.1  7,482,108 B2  1/2009 Matsumaru et al.  8,475,999 B2 *  7/2013 Masuyama ........... C07C 271/22  430/270.1  8,652,712 B2 *  2/2014 Glodde ................... C07C 25/18  430/18  2 Claims, No Drawings  (57)  ABSTRACT  OTHER PUBLICATIONS  FOREIGN PATENT DOCUMENTS  9,618,848 B2 *  4/2017 Carcasi ............... H0lL 21/0271  2006/0008736 Al *  1/2006 Kanda ................... G03F 7/0045  430/270.1  2007/0190459 Al*  8/2007 Hashimoto ............... G03F 7/11  430/270.1  2012/0202155  Al*  8/2012 Yao.  C09D 161/24  430/311  2014/0080055  Al*  3/2014 Hatakeyama ........... G03F 7/038  430/270.1  2014/0356787 Al*  12/2014 Komuro ................ C07C 381/ 12  430/281.1  JP  JP  JP  JP  JP  58-216243  61-156123  2006-45311 A  2006-178317 A  2015-161823 A  * 12/1983  *  7 /1986  2/2006  7/2006  9/2015  Ueno et al. "Resist materials utilizing oxygen plasma resistance of  iodine compounds", J. Electrochem. Soc.: Solid. State Sci. Tech.,  vol. 132(5) pp. 1168-1171 (May 1985).*  Taylor "X-ray resist trends", Sol. Stat. Technol., vol. 27(6) pp.  124-131 (Jun. 1984).*  Kishikawa et al., "Assessment of trade-off between resist resolution  and sensitivity for optimization of hyper-NA immersion lithogra› phy", Proc. ofSPIE (2007), vol. 6520, 65203L-l, Cited in specification.  (9 pages).  Hutchinson., "The Shot Noise Impact on Resist Roughness in EUV  Lithography", SPIE (1998),vol. 3331, pp. 531, Cited in specification.  (7 pages).  Brainard et al., "Shot Noise, LER and Quantum Efficiency of EUV  Photoresists", SPIE (2004), vol. 5374, pp. 74, Cited in specification.  (12 pages).  Kozawa et al., "Basic aspects of acid generation processes in  chemically amplified resists for electron beam lithography", SPIE  (2005), vol. 5753, pp. 361, Cited in specification. (7 pages).  Nakano et  al., "Deprotonation mechanism of poly ( 4-hydroxystyrene)  and its derivative", SPIE (2005), vol. 5753, pp. 1034, Cited in  specification. (6 pages).  Wang et al., "Novel Anionic Photoacid Generator (PAGs) and  Photoresist for sub-50 nm Patterning by EUVL and EBL", SPIE  (2007), vol. 6519, pp. 6519Fl-l, Cited in specification. (6 pages).  * cited by examiner  Primary Examiner  - Martin J Angebranndt  (74)  Attorney, Agent, or Firm  - Westerman, Hattori,  Daniels  & Adrian, LLP  A positive resist composition based on a polymer compris› ing recurring units (a) of (meth)acrylate having an iodized  lactone ring, and recurring units (bl) having a carboxyl  group substituted with an acid labile group and/or recurring  units (b2) having a phenolic hydroxyl group substituted with  an acid labile group has a high sensitivity and resolution, and  forms a pattern of good profile and minimal edge roughness  after exposure. 