US010698314B2  Jun.30,2020  (45)  Date of Patent:  (IO)  Patent No.:  US 10,698,314 B2  c12)  United States Patent  Hatakeyama  (54)  CHEMICALLY AMPLIFIED RESIST  COMPOSITION AND PATTERNING  PROCESS  (71)  Applicant:  SHIN-ETSU CHEMICAL CO., LTD.,  Tokyo (JP)  (72)  Inventor:  Jun Hatakeyama,  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 182 days.  (21)  Appl. No.:  15/814,659  (22)  Filed:  Nov. 16, 2017  (65)  Prior Publication Data  US 2018/0143532 Al  May 24, 2018  (30)  Foreign Application Priority Data  Nov. 18, 2016  (JP) ................................. 2016-224748  (51)  Int. Cl.  G03F  71028  G03F  71004  G03F  71039  G03F  7120  G03F  7142  C08F  12124  C09D  125118  C08F  212114  C08F 220138  C08K 5119  C08F 220/28  C08F 220/30  C08L 25/04  C08L 33/08  C08L 33/10  C08L 41/00  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (52)  U.S. Cl.  CPC ..............  G03F  71028  (2013.01);  C08F  12124  (2013.01);  C08F  212114  (2013.01);  C08F  220138  (2013.01);  C08K  5119  (2013.01);  C09D  125118  (2013.01);  G03F  710045  (2013.01);  G03F  710397  (2013.01);  G03F  712004  (2013.01);  G03F  71425  (2013.01);  G03F  71426  (2013.01);  C08F 220/281  (2020.02);  C08F 220/282  (2020.02);  C08F 220/283  (2020.02);  C08F 220/301  (2020.02);  C08F  220/302  (2020.02);  C08F 220/303  (2020.02);  C08L 25/04  (2013.01);  C08L 33/08  (2013.01);  (58)  Field of Classification Search  USPC ............................................ 430/270.1, 280.1  See application file for complete search history.  C08L 33/10  (2013.01);  C08L 41/00  (2013.01);  G03F 7/0046  (2013.01)  (56)  References Cited  U.S. PATENT DOCUMENTS  5,846,689 A * 12/1998 Schwalm .............. G03F 7/0045  430/270.1  9,176,379 B2  11/2015 Ichikawa et al.  9,448,475 B2  9/2016 Masuyama et al.  9,563,123 B2  2/2017 Masuyama et al.  2003/0134232 Al*  7/2003 Yokoyama ............ G03F 7/0046  430/312  2015/0241769 Al*  8/2015 Masuyama ............. G03F 7/027  430/281.1  2015/0248052 Al*  9/2015 Masuyama  C07D 321/10  430/285.1  2018/0079864 Al *  3/2018 Kawabata ............. G03F 7/0212  FOREIGN PATENT DOCUMENTS  JP  JP  JP  WO  2015-172746 A  10/2015  2015-180928 A  10/2015  5852490 B2  2/2016  WO-2016194769 Al * 12/2016  ............. C08G 73/10  OTHER PUBLICATIONS  Frechet , Jean "The photogeneration of acid and base within  polymer coatings: Approaches to polymer curing and imaging",  Pure & Appl. Chem, vol. 64, No. 9, pp. 1239-1248, 1992. (Year:  1992).*  Shiraishi et  al "N ovolak resin-based positive electron-beam resist  system untilizing acid sensitive polymeric dissolution inhibitor with  solubility reversal reactivity", J. Vac. Sci. Technol., B, vol. 9 Issue:  6, pp. 3343-3347, Nov. 1991. (Year: 1991).*  Toshio Sakamizu, Tadashi Arai, Hidenori Yamaguchi, Hiroshi Shiraishi,  "Acid diffusion control in chemical amplification positive resists by  exchange reaction of conjugate bases," Proc. SPIE 3049, Advances  in Resist Technology and Processing XIV, (Jul. 7, 1997)  pp. 448-458; doi: 10.1117/12.275845 (Year: 1997).*  * cited by examiner  Primary Examiner  - Cynthia Hamilton  (74)  Attorney, Agent, or Firm  - Westerman, Hattori,  Daniels & Adrian, LLP  (57)  ABSTRACT  A chemically amplified resist composition comprising a  quencher containing a quaternary annnonium iodide, dibro› moiodide, bromodiiodide or triiodide, and an acid generator  exhibits a sensitizing effect and an acid diffusion suppress› ing effect and forms a pattern having improved resolution,  LWR and CDU.  15 Claims, No Drawings 