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(12) Patent Application Publication (10) Pub. No.: US 2015/0288031 A1 Zhang Et Al US 20150288031A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2015/0288031 A1 Zhang et al. (43) Pub. Date: Oct. 8, 2015 (54) FUNCTIONALIZED IONIC LIQUID HOLM. I.2/02 (2006.01) ELECTROLYTES FOR LITHIUM ION HIM I/0525 (2006.01) BATTERIES HIM I/052 (2006.01) (52) U.S. Cl. (71) Applicant: UCHICAGO ARGONNE, LLC, CPC ...... H0IM 10/0567 (2013.01); H0IM 10/0525 CHICAGO, IL (US) (2013.01); H0IM 10/052 (2013.01); H0IM 10/054 (2013.01); H0IM 12/02 (2013.01); (72) Inventors: Zhengcheng Zhang, Naperville, IL HOM IO/0568 (2013.01); HOIM 23OO/OO25 (US), Wei Weng. Woodridge, IL (US); (2013.01); HOIM 2300/0085 (2013.01) Lu Zhang, Woodridge, IL (US); Khalil Amine, Oakbrook, IL (US) (57) ABSTRACT (21) Appl. No.: 14/742,194 An ionic liquid that is a salt has a Formula: (22) Filed: Jun. 17, 2015 R6 Rs Related U.S. Application Data R R s (63) Continuation of application No. 12/895,395, filed on N/ X N xO Sep. 30, 2010, now Pat. No. 9,093,722. R^ YR R1 y NR Publication Classification Ammonium R4 (51) Int. C. Imidazolium HIM I/0567 (2006.01) HIM I/0568 (2006.01) Such ionic liquids may be used in electrolytes and in electro HIM I/O54 (2006.01) chemical cells. Patent Application Publication Oct. 8, 2015 Sheet 1 of 8 US 2015/0288031 A1 FIG. 1A (Et-E-Me Me & S-O-Si-Me CC : M. M. 8 FIG 1B & Me Me FrogEt ME CHC3 1. 5.O O.O. Patent Application Publication Oct. 8, 2015 Sheet 2 of 8 US 2015/0288031 A1 FIG. 2A FIG. 2B CHCI Patent Application Publication Oct. 8, 2015 Sheet 3 of 8 US 2015/0288031 A1 FIG. 3A 10.0 9.0 8.0. 7.0 6.0 5.0 4.0 3.0 2.0 ppm (t1) Patent Application Publication Oct. 8, 2015 Sheet 4 of 8 US 2015/0288031 A1 FIG. 4 A FE -e-Charge 1 O Discharge 1 -- Charge 2 --Discharge 2 Capacity (mAh) FIG.S W.A.G. RE -O-Charge 1 -O-Discharge 1 -O-Charge 2 -O-Discharge 2 Charge 3 Discharge 3 - Charge 4 i i-Discharge 4 O O.5 1. 1.5 2 2.5 3 3.5 4 Capacity (mAh) Patent Application Publication Oct. 8, 2015 Sheet 5 of 8 US 2015/0288031 A1 F.G. 6 dOAdv Plot OO 10 OOO8 PCharge 1. Discharge 1 O. OO6 as Charge 2 OOO4 as Discharge 2 OOO2 N OOOO g O -0.002 -O.OO4 -O. OO6 -OOO8 -O. O10 Woltage, V FIG. 7 CYCLE RFRANCE t E >S -6-1.OM LiTFSITEMMP-FSI charge O -O-1, OMLITFSITEMMP-FSI discharge O 2O 40 60 80 1OO 12O Cycle Number Patent Application Publication Oct. 8, 2015 Sheet 6 of 8 US 2015/0288031 A1 d S. 1.0 ------------------- ---------- ---------- |-O-Discharge s U 0.5 0.0 O 10 20 30 40 50 Cycle Number FG. 9 at Girara site Gre gasfiffa i fitti 3.2 a aarth th 2. 40 30 3.0 H.-- O O.5 1. 1.5 2 2.5 Capacity, mAh/g Patent Application Publication Oct. 8, 2015 Sheet 7 of 8 US 2015/0288031 A1 FIG. 10 i Capacity (mAh) FIG. 11 E. -o- 1.0 MLITFSITEMMP-FSI charge -o- 1.0 MLITFSITEMMP-FSI discharge Cycle Number Patent Application Publication Oct. 8, 2015 Sheet 8 of 8 US 2015/0288031 A1 F.G. 12 CYCLE PERFORMANCE -O-Charge -O-Discharge (uvuu).Aq?oedeo Cycle Number US 2015/0288031 A1 Oct. 8, 2015 FUNCTIONALIZED IONIC LIQUID SUMMARY ELECTROLYTES FOR LITHIUM ION 0006. The present technology provides new ionic liquids BATTERIES for use in electrolytes and electrochemical devices Such as capacitors and lithium ion batteries. The ionic liquids bear CROSS-REFERENCE TO RELATED functional groups so that should allow the ionic liquid itself to APPLICATIONS form passivation films on the Surface of graphite-based anode materials and ensure stable cycling performance. The new 0001. This application is a continuation of U.S. patent ionic liquids also decrease the Viscosity of the electrolytes application Ser. No. 12/895,395, filed on Sep. 30, 2010, compared to conventional ionic liquids, increasing their ionic which is incorporated herein by reference, in its entirety, for conductivity; provide good electrode wettability by introduc any and all purposes. ing Surfactant groups; and tolerate high potential, which reduces problems related to the use of 4.8V transition metal STATEMENT OF GOVERNMENT RIGHTS oxides, especially against overcharge. Finally, the ionic liq uids of the present technology may also exhibit one or more of 0002 The United States Government has rights in this reduced flammability, thereby reducing the risk of burning invention pursuant to Contract No. DE-AC02-06CH11357 and explosion in a misused battery; reduced vapor pressure, between the United States Government and UChicago even at elevated temperatures; and are not environmentally Argonne, LLC, representing Argonne National Laboratory. hazardous. TECHNICAL FIELD BRIEF DESCRIPTION OF THE DRAWINGS 0003. The present technology relates to ionic liquids, 0007 FIGS. 1A and 1B. H-NMR of triethyl-(methylene including room temperature ionic liquids, that may be used in pentamethyldisiloxane)phosphonium iodide (IL1-I, FIG. electrolytes, electrolytic solutions and electrochemical 1A) and triethyl-(methylenepentamethyldisiloxane)phos devices. More particularly, the present technology relates to phonium bis(trifluoromethylsulfonyl)imide (IL1-TFSI, FIG. functionalized ionic liquids which are usable as electrolytes 1B). for lithium ion batteries having a high ionic conductivity, 0008 FIGS. 2A and 2B. H-NMR of 1-ethyl-3-(methyl good solid electrolyte interphase (SEI) formation, high wet enepentamethyldisiloxane) imidazolium iodide (IL2-I, FIG. tability, and high voltage stability. 2A) and 1-ethyl-3-(methylenepentamethyldisiloxane)-1H imidazol-3-ium bis(trifluoromethanesulfonyl)imide (IL2 BACKGROUND TFSI, 2B). 0009 FIGS. 3A and 3B. H-NMR of 1-ethyl-3-(ethylen 0004 Ionic liquids are substances, which are made up only emethylsulfone)-1H-imidazol-3-ium bromide (IL3-Br, FIG. from ions and have a melting point of <100° C. or are, ideally, 3A) and 1-ethyl-3-(ethylenemethylsulfone)-1H-imidazol-3- liquid at ambient temperature. They have been proposed for ium bis(trifluoro-methanesulfonyl)imide (IL3-TFSI, FIG. use in electrolytes for lithium and lithium-ion batteries, as 3B). they exhibit relatively favorable electrochemical stability and (0010 FIG. 4. Li/MCMB half cell charge discharge pro high ionic conductivity. Despite the potential advantages, files using conventional 0.8M LiTFSI in tetraethylphospho ionic liquids have not been widely used as electrolytes for nium bis(trifluoromethanesulfonyl)imide ionic liquid. lithium and lithium ion batteries due to a number of signifi (0011 FIG. 5. Li/MCMB half cell charge discharge pro cant disadvantages. Although lithium-ion cells using files using 0.8M LiTFSI in triethyl-(methylenepentamethyl LiMnO and Li TiO2 as electrode materials show satisfac disiloxane)phosphonium bis(trifluoromethylsulfonyl)imide tory cycling behavior using ionic liquid as electrolyte solvent, (IL1-TFSI). this cell configuration suffers from the relatively small volt (0012 FIG. 6. dOdV profile of Li/MCMB half cell using age of 2.5V. In addition, the cell has low rate capability due to 0.8M LiTFSI in triethyl-(methylenepentamethyldisiloxane) the high viscosity and poor wettability of the ionic liquid with phosphonium bis(trifluoromethylsulfonyl)imide (IL1-TFSI). electrode materials. 0013 FIG. 7. LiNiCoos AloosO/Li half cell charge 0005 Moreover, early experiments to cycle lithium-ion discharge cycling performance using conventional 0.8M batteries using carbonaceous negative electrode materials and LiTFSI intetraethylphosphonium bis(trifluoromethanesulfo ionic liquid-based electrolytes failed. Any ionic liquid sample nyl)imide ionic liquid. tested was reduced at the low potential at which the interca 0014 FIG. 8. LiNiCoos AloosO/Li half cell charge lation of lithium into the graphite proceeds. It is believed that discharge cycling performance using 0.8M LiTFSI in tri the reduction of the ionic liquids proceeds due to the forma ethyl-(methylenepentamethyldisiloxane)phosphonium bis tion of dimeric species. For commercial applications, lithium (trifluoromethylsulfonyl)imide (IL1-TFSI) at 55° C. metal is, however, not advantageous. Due to the high reactiv (0015 FIG.9. MCMB/Lihalf cell charge discharge cycling ity of its Surface, lithium is potentially hazardous, especially performance using conventional 0.8M LiTFSI in tetraeth at elevated temperatures. Proposals to stabilize lithiated ylphosphonium bis(trifluoromethanesulfonyl)imide ionic graphite electrodes for use in lithium-ion batteries include liquid. admixture of Small amounts of highly active film forming (0016 FIG. 10. MCMB/Li half cell charge discharge additives. Such additives could protect against the continued cycling performance using 0.8M LiTFSI in triethyl-(methyl reduction of the electrolyte itself at the surface of the low enepentamethyldisiloxane)phosphonium bis(trifluorometh potential graphite. However, in most cases, the additives have ylsulfonyl)imide (IL1-TFSI). issues associated with the poor solubility in ionic liquid elec (0017 FIG. 11. MCMB/LiNiso Nils Aloo O, full cell trolytes. charge discharge cycling performance using conventional US 2015/0288031 A1 Oct. 8, 2015 0.8M LiTFSI in tetraethylphosphonium bis(trifluo unsubstituted or optionally substituted with one or more romethanesulfonyl)imide ionic liquid. alkyl, halo groups or one or more halogens. In some embodi 0018 FIG. 12. MCMB/LiNissCoos Alos.O. full cell ments the aryl groups are substituted with 1, 2 or 3 alkyl charge discharge cycling performance using 0.8M LiTFSI in groups and/or 1-5 halogens. triethyl-(methylenepentamethyldisiloxane)phosphonium bis 0026 Aralkyl groups are alkyl groups as defined above in (trifluoromethylsulfonyl)imide (IL1-TFSI). which a hydrogen or carbon bond of an alkyl group is replaced with a bond to an aryl group as defined above. In DETAILED DESCRIPTION Some embodiments, aralkyl groups contain 7 to 16 carbon 0019.
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