US009804493B2  c12)  United States Patent  Kim et al.  (IO)  Patent No.:  US 9,804,493 B2  (45)  Date of Patent:  Oct. 31, 2017  (54)  COMPOSITION FOR FORMING TOPCOAT  LAYER AND RESIST PATTERN FORMATION  METHOD EMPLOYING THE SAME  (71)  Applicant:  SAMSUNG ELECTRONICS CO.,  LTD.,  Suwon-si, Gyeonggi-do (KR)  (72)  Inventors:  Hyun-woo Kim,  Seongnam-si (KR);  Cheol hong Park,  Seoul (KR);  Tetsuo  Okayasu,  Kakegawa (JP);  Xiaowei  Wang,  Kakegawa (JP);  Georg  Pawlowski,  Kakegawa (JP);  Yusuke  Hama,  Kakegawa (JP)  (73)  Assignees:  Samsung Electronics Co., LTD.,  Suwon-Si, Gyeonggi-do (KR);  AZ  Electronics Materials (Luxembourg)  S.A.R.L.,  Luxembourg (LU)  ( *)  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.:  14/549,911  (22)  Filed:  Nov. 21, 2014  (51)  Int. Cl.  (52)  U.S. Cl.  CPC .............  G03F  712004  (2013.01);  C09D  5100  (2013.01);  C09D  711225  (2013.01);  G03F  71091  (2013.01);  G03F  7111  (2013.01)  (58)  Field of Classification Search  CPC ............ G03F 7/09; G03F 7/11; G03F 7/2004;  G03F 7/091; C09D 5/00  See application file for complete search history.  Provided is a composition for forming a topcoat layer, the  composition including a graphene derivative including a  hydrophilic group; and a solvent. Also provided is a pattern  formation method, including disposing a resist composition  on a substrate, to form a resist layer; coating the resist layer  with a composition including a graphene derivative includ› ing a hydrophilic group, and a solvent; heating the compo› sition to harden the composition; subjecting the resist layer  to exposure using extreme ultraviolet light; and developing  exposed resist layer with an alkali aqueous solution.  Primary Examiner  - Anca Eoff  (74)  Attorney, Agent, or Firm  - Lee & Morse, P.C.  Machine translation of JP 2012-117052, published on Jun. 21, 2012  (Year: 2012). *  Machine translation of JP 2013-079176, published on May 2, 2013  (Year: 2013). *  CD Uniformity Improvement for EUV Resists Process: EUV Reso› lution Enhancement Layer; Proc. of SPIE, vol. 7969 7969-1; Kim,  et al.  Japanese Office Action dated Aug. 22, 2017.  (Continued)  10 Claims, No Drawings  (57)  ABSTRACT  (56)  References Cited  U.S. PATENT DOCUMENTS  (30)  Foreign Application Priority Data  (65)  Prior Publication Data  OTHER PUBLICATIONS  FOREIGN PATENT DOCUMENTS  US 2015/0147701 Al  May 28, 2015  Nov. 22, 2013  Apr. 8, 2014  (JP) ................................. 2013-242092  (KR) ........................ 10-2014-0042023  G03F  7109  G03F  7120  C09D 5100  C09D  7112  G03F  7111  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (2006.01)  4,740,451 A  7,316,886 B2  7,335,455 B2  7,361,447 B2  7,537,880 B2  7,678,462 B2  8,043,792 B2  8,101,015 B2  8,211,618 B2  8,344,088 B2  8,715,911 B2  8,927,658 B2 *  4/ 1988 Kohara  1/2008 Kanda  2/2008 Kim et al.  4/2008 Jung  5/2009 Harada et al.  3/2010 Kennedy et al.  10/2011 Kuramoto et al.  1/2012 Kennedy et al.  7/2012 Hatakeyama et al.  1/2013 Kennedy et al.  5/2014 Kim et al.  1/2015 Imae et al. .................... 525/435  JP  JP  JP  JP  JP  09-246173  A  2004-0348133  A  2005-0352384  A  2006-178317 A  2007-316581 A  9/1997  12/2004  12/2005  7/2006  12/2007  9,395,630 B2  7/2016 Y akunin et al.  2004/0018451 Al  1/2004 Choi  2004/0142275 Al*  7/2004 Komatsu ............... G03F 7/0233  430/270.1  2005/0008864 Al  1/2005 In gen Schenau et al.  2007/0122741 Al  5/2007 Hatakeyama et al.  2010/0247892 Al *  9/2010 Lee et al. ...................... 428/221  2010/0279235 Al  11/2010 Nova et al.  2010/0317790 Al*  12/2010 Jang .  B82Y30/00  524/496  2011/0133607 Al *  6/2011  Lee et al. ...................... 310/365  2011/0143101 Al*  6/2011  Sandhu ...................... 428/195.1  2011/0268647 Al *  11/2011 Ivanovici ................. B0lJ 21/08  423/448  2012/0021355 Al  1/2012 Kim et al.  2012/0021555 Al  1/2012 Tu et al.  2012/0070689 Al  3/2012 Kennedy et al.  2012/0164433 Al*  6/2012 Advincula .................... 428/327  2012/0263921 Al  10/2012 Yager et al.  2013/0075326 Al*  3/2013 Yun et al . ..................... 210/505  2013/0164677 Al  6/2013 Kennedy et al.  2013/0209940 Al  8/2013 Sakamoto et al.  2014/0001417 Al*  1/2014 Kim et al. .................... 252/511  2014/0212818 Al*  7/2014 Kang et al. . .................. 430/325  2014/0227 538 Al  8/2014 Baldwin et al. 