US010781276B2  (IO)  Patent No.:  US 10,781,276 B2  Sep.22,2020  (45)  Date of Patent:  c12)  United States Patent  Enomoto et al.  (54)  POLYMER, RESIST COMPOSITION  CONTAINING POLYMER, AND METHOD  FOR MANUFACTURING DEVICE USING  SAME  5,968,713 A  6,013,416 A  6,200,725 Bl  2001/0003640 Al  2006/0188790 Al *  10/1999 Nozaki et al.  1/2000 Nozaki et al.  3/2001 Takechi et al.  6/2001 Takechi et al.  8/2006 Takizawa ................ G03F 7/001  2012/0202158 Al  2016/0147144 Al  2016/0187773 Al  430/1  8/2012 Hatakeyama et al.  5/2016 Enomoto  6/2016 Enomoto  EP  JP  JP  JP  JP  JP  WO  WO  0260877 A2 *  H09-90637 A  Hl0-221852 A  2007/316600 A  2009-169406 A  2012-181510 A  2014/208102 Al  2015/019616 Al  3/1988  4/1997  8/1998  12/2007  7/2009  9/2012  12/2014  2/2015  ................ C08F 2/50  C08F 220130  C08F 220138  G03F  71039  G03F  71004  C08F  220134  G03F  71038  G03F  71031  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (2006.01)  (2006.01)  4,791,045 A * 12/1988 Mitra  C07D 295/108  430/281.1  4,954,416 A *  9/1990 Wright .................. C07C 381/12  430/281.1  13 Claims, No Drawings  (56)  References Cited  U.S. PATENT DOCUMENTS  (30)  Foreign Application Priority Data  (65)  Prior Publication Data  OTHER PUBLICATIONS  (57)  ABSTRACT  FOREIGN PATENT DOCUMENTS  (71)  Applicant:  TOYO GOSEI CO., LTD.,  Chiba (JP)  (72)  Inventors:  Satoshi Enomoto,  Chiba (JP);  Takumi  Yoshino,  Chiba (JP)  (73)  Assignee:  TOYO GOSEI CO., LTD.,  Chiba (JP)  ( *)  Notice:  Subject to any disclaimer, the term of this  patent is extended or adjusted under 35  U.S.C. 154(b) by 227 days.  (21)  Appl. No.:  15/763,600  (22)  PCT Filed:  Sep. 29, 2016  (86)  PCT No.:  PCT/JP2016/078761  § 371 (c)(l),  (2) Date:  Mar. 27, 2018  (87)  PCT Pub. No.:  WO2017/057537  PCT Pub. Date:  Apr. 6, 2017  (51)  Int. Cl.  (52)  U.S. Cl.  CPC ..........  C08F 220130  (2013.01);  C08F 220134  (2013.01);  C08F 220138  (2013.01);  G03F  710045  (2013.01);  G03F  71031  (2013.01);  G03F  71038  (2013.01);  G03F  710397  (2013.01)  ( 58)  Field of Classification Search  CPC .... C08F 220/30; C08F 220/38; C08F 220/34;  C08F 212/22  USPC . ... ... ... .. ... ... ... ... ... .. ... ... ... ... ... .. ... . 522/904-905  See application file for complete search history.  "Benzenoid", Hawleys Condensed Chemical Dictionary, first pub› lished Mar. 15, 2007 , https://doi.org/10.1002/9780470114735.  hawley0 1674, one page ,obtained from Wiley Online Library. (Year:  2007).*  Parker , ed, "benzenoid" from McGraw-Hill Dlctioanry of Chem› istry, International Edition, United States of America, The McGraw› Hill Company, 1997, p. 42. (Year: 1997).*  Katritzky, Alan R. Ramsden, Christopher A. Joule, John  A. Zhdankin,  Viktor V.. (2010). Handbook of Heterocyclic Chemistry (3rd Edi› tion). (pp. 332). Elsevier. Retrieved from https://app.knovel.com/  hotlink/toc/id:kpHHCE0002/handbookheterocyclic/handbook› heterocyclic p. 332. (Year: 2010).*  International Search Report dated Dec. 6, 2016 of corresponding  International application No. PCT/JP2016/078761; 2 pgs.  * cited by examiner  Primary Examiner  - Cynthia Hamilton  (74)  Attorney, Agent, or Firm  - Maier & Maier, PLLC  An object of the present invention is to provide a polymer  used for a resist composition having high absorption effi› ciency for a particle beam or an electromagnetic wave, and  excellence in sensitivity, resolution and pattern performance  characteristics, and provide a resist composition containing  the polymer and a method of manufacturing a device using  thereof.  The polymer comprises: a unit A; and a unit B, wherein the  unit A has an onium salt structure and generates a first  radical by irradiation with a particle beam or an electromag› netic wave, the unit B has a radical generating structure  containing at least one multiple bond which is between a  carbon atom and a carbon atom or between a carbon atom  and a heteroatom, and generates a second radical by irra› diation with a particle beam or an electromagnetic wave, and  the multiple bond is not one contained in a benzenoid  aromatic.  Oct. 1, 2015  (JP) ................................. 2015-195863  US 2018/0273664 Al  Sep. 27, 2018 