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( 12 ) United States Patent ( 10 ) Patent No .: US 11,011,781 B2 Yamada Et Al

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( 12 ) United States Patent ( 10 ) Patent No .: US 11,011,781 B2 Yamada Et Al US011011781B2 ( 12 ) United States Patent ( 10 ) Patent No .: US 11,011,781 B2 Yamada et al . ( 45 ) Date of Patent : May 18 , 2021 ( 54 ) NONAQUEOUS ELECTROLYTE ( 51 ) Int . Ci . SECONDARY BATTERY HOIM 10/0568 ( 2010.01 ) HOIM 10/0569 ( 2010.01 ) ( 71 ) Applicants : THE UNIVERSITY OF TOKYO , (Continued ) Tokyo ( JP ) ; KABUSHIKI KAISHA ( 52 ) U.S. CI . TOYOTA JIDOSHOKKI, Kariya ( JP ) CPC HOIM 10/0568 ( 2013.01 ) ; HOIM 4/587 ( 2013.01 ) ; HOIM 10/0525 ( 2013.01 ) ; ( 72 ) Inventors : Atsuo Yamada , Tokyo ( JP ) ; Yuki (Continued ) Yamada , Tokyo ( JP ) ; Yoshihiro ( 58 ) Field of Classification Search Nakagaki , Kariya ( JP ) ; Tomoyuki CPC HO1M 10/0568 ; HO1M 10/0525 ; HOLM Kawai, Kariya ( JP ) ; Yuki Hasegawa , 10/0569 ; HO1M 4/587 Kariya ( JP ) ; Kohei Mase , Kariya ( JP ) ; See application file for complete search history . Nobuhiro Goda , Kariya ( JP ) ( 56 ) References Cited ( 73 ) Assignees : THE UNIVERSITY OF TOKYO , U.S. PATENT DOCUMENTS Tokyo ( JP ) ; KABUSHIKI KAISHA TOYOTA JIDOSHOKKI, Kariya ( JP ) 5,607,485 A * 3/1997 Gozdz CO8J 9/28 29 / 623.5 ( * ) Notice : Subject to any disclaimer , the term of this 6,274,271 B1 8/2001 Koshiba et al . patent is extended or adjusted under 35 ( Continued ) U.S.C. 154 ( b ) by 465 days . FOREIGN PATENT DOCUMENTS ( 21 ) Appl. No .: 15 / 024,415 CA 2625271 A1 9/2009 CN 101164189 A 4/2008 ( 22 ) PCT Filed : Sep. 25 , 2014 ( Continued ) ( 86 ) PCT No .: PCT / JP2014 / 004911 OTHER PUBLICATIONS $ 371 ( c ) ( 1 ) , Communication dated Jul. 19 , 2018 from the Japanese Patent Office ( 2 ) Date : Mar. 24 , 2016 in Japanese application No. 2015-172591 . ( Continued ) ( 87 ) PCT Pub . No .: WO2015 / 045387 Primary Examiner Jimmy Vo PCT Pub . Date : Apr. 2 , 2015 ( 74 ) Attorney, Agent, or Firm — Sughrue Mion , PLLC ( 65 ) Prior Publication Data ( 57 ) ABSTRACT US 2016/0226100 A1 Aug. 4 , 2016 An electrolytic solution of a nonaqueous electrolyte second ary battery contains a metal salt , and an organic solvent ( 30 ) Foreign Application Priority Data having a heteroatom and satisfies Is > Io , when an intensity of an original peak of the solvent is represented as lo and an Sep. 25 , 2013 ( JP ) JP2013-198282 intensity of a peak resulting from shifting of the original Sep. 25 , 2013 ( JP ) JP2013-198283 peak is represented as Is . For the negative electrode, ( 1 ) a ( Continued ) ( Continued ) 4500 4000 01s 35000 3000 secondcount)intensity/Peak( 2500 2000 ! 15001 1000 500 296 294 292 290 288 286 284 282 280 Bond energy ( eV ) EB1 ( 4.5M LFSA , AN E82 ( 4.2M LITFSA : AN ) : C61 ( 1M VPF6 / EC + DEC ( 3: 7 ) ] US 11,011,781 B2 Page 2 graphite whose G / D ratio of G - band and D - band peaks in a 2011/01832 18 A1 7/2011 Odani et al . 2011/0287325 A1 11/2011 Zaghib et al . Raman spectrum is not lower than 3.5 ; ( 2 ) a carbon material 2011/0318647 Al 12/2011 Lee et al . whose crystallite size , calculated from a half width of a peak 2012/0135308 Al 5/2012 Loveridge et al . appearing at 20 = 20 degrees to 30 degrees in a X - ray 2012/0171580 A1 7/2012 Iwaya et al . diffraction profile is not larger than 20 nm ; ( 3 ) silicon 2012/0316716 Al 12/2012 Odani et al . 2013/0022861 A1 1/2013 Miyagi et al . element and / or tin element; ( 4 ) a metal oxide configured to 2013/0164618 A1 * 6/2013 Konishi HOTM 4/133 occlude and release lithium ions ; or ( 5 ) a graphite whose 429/217 ratio ( long axis / short axis ) is 1 to 5 . 2014/0242458 Al 8/2014 Abe et al . 2015/0050563 Al 2/2015 Yamada et al . 21 Claims , 64 Drawing Sheets 2015/0243936 A1 8/2015 Miyagi et al . 2017/0040593 A1 2/2017 Miyagi et al . FOREIGN PATENT DOCUMENTS ( 30 ) Foreign Application Priority Data CN 101385183 A 3/2009 CN 101292389 A 9/2010 Sep. 25 , 2013 ( JP ) JP2013-198284 CN 101292389 B 9/2010 Sep. 25 , 2013 ( JP ) JP2013-198285 CN 101882696 A 11/2010 Sep. 25 , 2013 ( JP ) JP2013-198599 CN 102576905 A 7/2012 JP2014-065799 EP 1380569 A1 4/2004 Mar. 27 , 2014 ( JP ) EP 1 906 481 A1 4/2008 Mar. 27 , 2014 ( JP ) JP2014-065817 JP 60-036315 A 2/1985 Sep. 12 , 2014 ( JP ) JP2014-186338 JP 07-320783 A 12/1995 Sep. 12 , 2014 ( JP ) JP2014-186339 JP 10027733 A 1/1998 Sep. 12 , 2014 ( JP ) JP2014-186340 JP 10-069922 A 3/1998 JP2014-186341 JP 11031637 A 2/1999 Sep. 12 , 2014 ( JP ) JP 11-154513 A 6/1999 Sep. 12 , 2014 ( JP ) JP2014-186342 JP 2000077100 A 3/2000 JP 2001-507043 A 5/2001 ( 51 ) Int . Ci . JP 2001-266878 A 9/2001 HOIM 4/587 ( 2010.01 ) JP 2002-203562 A 7/2002 JP 2002-523879 A 7/2002 HOIM 10/0525 ( 2010.01 ) JP 2003268053 A 9/2003 ( 52 ) U.S. Ci . JP 2004-511887 A 4/2004 ??? HOIM 10/0569 ( 2013.01 ) ; HOLM JP 2004111294 A 4/2004 2300/0025 ( 2013.01 ) ; HOIM 2300/0028 JP 2004511887 A 4/2004 JP 2005243321 A 9/2005 ( 2013.01 ) JP 2006073434 A 3/2006 JP 2006513554 A 4/2006 ( 56 ) References Cited JP 2006-164759 A 6/2006 JP 2006-164960 A 6/2006 U.S. PATENT DOCUMENTS JP 2006-324167 A 11/2006 JP 2007019027 A 1/2007 6,294,289 B1 * 9/2001 Fanta C07C 317/44 JP 2007091573 A 4/2007 429/188 JP 2007115671 A 5/2007 6,340,716 B1 1/2002 Armand et al . JP 2007243111 A 9/2007 6,365,301 B1 * 4/2002 Michot C07C 45/46 JP 2008010613 A 1/2008 359/270 JP 2008501220 A 1/2008 6,420,070 B1 7/2002 Kasamatsu et al . JP 2008-047479 A 2/2008 7,622,226 B2 11/2009 Takahashi JP 2008053207 A 3/2008 8,076,026 B2 12/2011 Muthu et al . JP 2009026514 A 2/2009 8,148,017 B2 4/2012 Matsui et al . JP 2009-117334 A 5/2009 8,257,865 B2 9/2012 Suzuki et al. JP 2009123474 A 6/2009 8,568,931 B2 10/2013 Iwaya et al . JP 2010-097802 A 4/2010 8,945,780 B2 2/2015 Odani et al . JP 2010073489 A 4/2010 8,986,880 B2 3/2015 Odani et al . JP 2010225539 A 10/2010 9,017,881 B2 4/2015 Lee et al . JP 2011-054298 A 3/2011 9,590,239 B2 3/2017 Abe et al . JP 2011077051 A 4/2011 2002/0013381 Al 1/2002 Armand et al . JP 2011-119053 A 6/2011 2003/0195269 Al 10/2003 Armand et al . JP 2011146359 A 7/2011 2004/0094741 A1 5/2004 Sato et al . JP 2011-150958 A 8/2011 2004/0106047 Al 6/2004 Mie et al . JP 2011216480 A 10/2011 2005/0158631 Al 7/2005 Armand et al . JP 4862555 B2 1/2012 2005/0221170 A1 10/2005 Takeuchi et al. JP 2012-033268 A 2/2012 2006/0127764 A1 6/2006 Chen et al . JP 2012504314 A 2/2012 2007/0031729 A1 2/2007 Sato et al . JP 2012-160345 A 8/2012 2007/0205388 A1 9/2007 Armand et al . JP 2013016456 A 1/2013 2008/0076021 A1 3/2008 Takahashi JP 2013-065493 A 4/2013 2008/03 14482 A1 12/2008 Suzuki et al . JP 5177211 B2 4/2013 2009/0023074 Al 1/2009 Matsui et al. JP 2013065575 A 4/2013 2009/0130565 A1 5/2009 Matsui et al . JP 2013-093242 A 5/2013 2009/0176164 Al 7/2009 Matsui et al . JP 2013082581 A 5/2013 2009/0301866 Al 12/2009 Zaghib et al . JP 2013134922 A 7/2013 2010/0015514 Al 1/2010 Miyagi et al. JP 2013137873 A 7/2013 2010/0075229 Al 3/2010 Atsuki et al . JP 2013145724 A 7/2013 2011/0159379 Al * 6/2011 Matsumoto HO1M 4/0421 JP 2013149477 A 8/2013 429/326 JP 2013-179067 A 9/2013 US 11,011,781 B2 Page 3 ( 56 ) References Cited Kramer et al ., “ Dependency of Aluminum Collector Corrosion of Lithium Ion Batteries on the Electrolyte Solvent, " ECS Electro FOREIGN PATENT DOCUMENTS chemistry Letters, 1 ( 5 ) C9 - C11 ( 2012 ) . M. Yaegashi et al . , “ Increasing Both Cathodic and Anodic Stability JP 2013178885 A 9/2013 of Ether -Based Electrolyte for Lithium - Ion Batteries ” , The Electro JP 2014-096528 A 5/2014 KR 10-2006-0044479 A 5/2006 chemical Society of Japan Dai 79 Kai Taikai Koen Yoshishu , Mar. KR 10-2007-0121034 A 12/2007 29 , 2012 (Mar. 29 , 2012 ) , p . 83 ( 6 pages total ) . KR 1020090004841 A 1/2009 Y. Yamada et al ., “ Kinetics of Lithium Ion Transfer at the Interface WO 2004019356 A1 3/2004 between Graphite and Liquid Electrolytes: Effects of Solvent and WO 2004027789 A1 4/2004 Surface Film , ” Langmuir, ( 2009 ) 25 ( 21 ) , 12766-12770 ( 6 pages WO 2005076299 A1 8/2005 total ) . WO 2006049027 A1 5/2006 Communication dated Mar. 3 , 2017 issued by the Canadian Intel WO 2006/115023 A1 11/2006 lectual Property Office in counterpart Canadian Application No. WO 2007125682 A1 11/2007 2,925,379 . WO 2010130976 A1 11/2010 U.S. Appl. No. 15 / 024,380 , Atsuo Yamada , filed Mar. 24 , 2016 . WO 2011111364 A1 9/2011 U.S. Appl. No. 15 / 024,436 , Atsuo Yamada, filed Mar. 24 , 2016 . U.S. Appl. No. 15 / 024,418 , Atsuo Yamada, filed Mar. 24 , 2016 . OTHER PUBLICATIONS U.S. Appl. No. 15 / 024,654 , Atsuo Yamada , filed Mar. 24 , 2016 . Communication dated Mar. 8 , 2017 , issued from the European Communication dated Jul.
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