Bis(trimethylsilyl) 2-fluoromalonate derivatives as electrolyte additives for high voltage lithium ion batteries

Lyu, Hailong; Li, Yunchao; Jafta, Charl J.; Bridges, Craig A.; Meyer, Harry M.; Borisevich, Albina; Paranthaman, Mariappan Parans; Dai, Sheng; Sun, Xiao-Guang

doi:10.1016/j.jpowsour.2018.11.083

Title: Bis(trimethylsilyl) 2-fluoromalonate derivatives as electrolyte additives for high voltage lithium ion batteries

Journal Article · Fri Feb 01 00:00:00 EST 2019 · Journal of Power Sources

DOI:https://doi.org/10.1016/j.jpowsour.2018.11.083· OSTI ID:1488710

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Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States) Chemical Sciences Division; Univ. of Tennessee, Knoxville, TN (United States). Dept. of Chemistry
Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States) Chemical Sciences Division; Univ. of Tennessee, Knoxville, TN (United States). Bredesen Center for Interdisciplinary Research and Graduate Education
Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States) Chemical Sciences Division
Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States). Materials Science & Technology Division
Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States). Center for Nanophase Materials Science (CNMS)

Three trimethylsilyl based malonate esters, bis(trimethylsilyl) 2-methyl-2-fluoromalonate (BTMSMFM), bis(trimethylsilyl) 2-ethyl-2-fluoromalonate (BTMSEFM) and bis(trimethylsilyl) 2-propyl-2-fluoromalonate (BTMSPFM), have been used as additives in 1.0 M LiPF₆/ethylene carbonate (EC)-dimethyl carbonate (DMC)-diethyl carbonate (DEC) (1-1-1, by v) baseline electrolyte for LiNi_0.80Co_0.15Al_0.05O₂ (NCA) based high voltage lithium ion batteries. The NCA half-cells with 5 wt% BTMSMFM exhibit higher capacity retention than that in the baseline electrolyte at different upper cut off voltages, that is, 4.2, 4.3, 4.4 and 4.5 V vs. Li/Li⁺. Scanning electron microscope (SEM) show that the additive successfully prevents the formation of thick solid electrolyte interphase (SEI) films on the surface of the NCA electrodes. X-ray diffraction (XRD) further reveals that the crystal structure of NCA is also maintained in the electrolyte with 5 wt% BTMSMFM at high cut off voltages. Finally, besides beneficial to NCA cathode, the BTMSMFM additive also ensures better cycling performance of the graphite based half-cells and NCA/graphite full-cells, and thus is a promising additive for application in rechargeable lithium ion batteries.

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Research Organization:: Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES)

Grant/Contract Number:: AC05-00OR22725

OSTI ID:: 1488710

Journal Information:: Journal of Power Sources, Vol. 412, Issue C; ISSN 0378-7753

Publisher:: ElsevierCopyright Statement

Country of Publication:: United States

Language:: English

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Cited by: 39 works

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References (58)

Challenges in the development of advanced Li-ion batteries: a review Etacheri, Vinodkumar; Marom, Rotem; Elazari, Ran Energy & Environmental Science, Vol. 4, Issue 9 https://doi.org/10.1039/c1ee01598b	journal	January 2011
Role of Oxygen Vacancies on the Performance of Li[Ni _{0.5– x} Mn _{1.5+ x} ]O ₄ ( x = 0, 0.05, and 0.08) Spinel Cathodes for Lithium-Ion Batteries Song, Jie; Shin, Dong Wook; Lu, Yuhao Chemistry of Materials, Vol. 24, Issue 15 https://doi.org/10.1021/cm301825h	journal	July 2012
Synthesis and Electrochemistry of LiNi[sub x]Mn[sub 2−x]O[sub 4] Zhong, Qiming Journal of The Electrochemical Society, Vol. 144, Issue 1 https://doi.org/10.1149/1.1837386	journal	January 1997
Microstructural Observation of LiNi _0.8 Co _0.15 Al _0.05 O ₂ after Charge and Discharge by Scanning Transmission Electron Microscopy Makimura, Yoshinari; Zheng, Shijian; Ikuhara, Yuichi Journal of The Electrochemical Society, Vol. 159, Issue 7 https://doi.org/10.1149/2.073207jes	journal	January 2012
Degradation Mechanism of LiNi _0.82 Co _0.15 Al _0.03 O ₂ Positive Electrodes of a Lithium-Ion Battery by a Long-Term Cycling Test Hayashi, Tetsutaro; Okada, Jiro; Toda, Eiji Journal of The Electrochemical Society, Vol. 161, Issue 6 https://doi.org/10.1149/2.056406jes	journal	January 2014
Review—Li-Rich Layered Oxide Cathodes for Next-Generation Li-Ion Batteries: Chances and Challenges Rozier, Patrick; Tarascon, Jean Marie Journal of The Electrochemical Society, Vol. 162, Issue 14 https://doi.org/10.1149/2.0111514jes	journal	January 2015
Higher, Stronger, Better…︁ A Review of 5 Volt Cathode Materials for Advanced Lithium-Ion Batteries Kraytsberg, Alexander; Ein-Eli, Yair Advanced Energy Materials, Vol. 2, Issue 8 https://doi.org/10.1002/aenm.201200068	journal	June 2012
Stabilizing Effect of Mg on the Energetics of the Li(Ni,Co,Al)O ₂ Cathode Material for Lithium Ion Batteries Tavakoli, Amir H.; Kondo, Hiroki; Ukyo, Yoshio Journal of The Electrochemical Society, Vol. 160, Issue 2 https://doi.org/10.1149/2.059302jes	journal	December 2012
Facile strategy of NCA cation mixing regulation and its effect on electrochemical performance Liu, Bao-sheng; Wang, Zhen-Bo; Yu, Fu-Da RSC Advances, Vol. 6, Issue 110 https://doi.org/10.1039/C6RA20146F	journal	January 2016
Fatigue of LiNi0.8Co0.15Al0.05O2 in commercial Li ion batteries Kleiner, Karin; Dixon, Ditty; Jakes, Peter Journal of Power Sources, Vol. 273 https://doi.org/10.1016/j.jpowsour.2014.08.133	journal	January 2015
Study of the Failure Mechanisms of LiNi _0.8 Mn _0.1 Co _0.1 O ₂ Cathode Material for Lithium Ion Batteries Li, Jing; Downie, Laura E.; Ma, Lin Journal of The Electrochemical Society, Vol. 162, Issue 7 https://doi.org/10.1149/2.1011507jes	journal	January 2015
Modification of Ni-Rich FCG NMC and NCA Cathodes by Atomic Layer Deposition: Preventing Surface Phase Transitions for High-Voltage Lithium-Ion Batteries Mohanty, Debasish; Dahlberg, Kevin; King, David M. Scientific Reports, Vol. 6, Issue 1 https://doi.org/10.1038/srep26532	journal	May 2016
Correlating Structural Changes and Gas Evolution during the Thermal Decomposition of Charged Li _x Ni _0.8 Co _0.15 Al _0.05 O ₂ Cathode Materials Bak, Seong-Min; Nam, Kyung-Wan; Chang, Wonyoung Chemistry of Materials, Vol. 25, Issue 3 https://doi.org/10.1021/cm303096e	journal	January 2013
Facilitating the Operation of Lithium-Ion Cells with High-Nickel Layered Oxide Cathodes with a Small Dose of Aluminum Li, Jianyu; Li, Wangda; Wang, Shanyu Chemistry of Materials, Vol. 30, Issue 9 https://doi.org/10.1021/acs.chemmater.8b01077	journal	April 2018
Influence of integrated microstructure on the performance of LiNi _0.8 Co _0.15 Al _0.05 O ₂ as a cathodic material for lithium ion batteries Chen, Yongjie; Li, Ping; Zhao, Sijia RSC Advances, Vol. 7, Issue 46 https://doi.org/10.1039/C7RA04206J	journal	January 2017
Identifying surface structural changes in layered Li-excess nickel manganese oxides in high voltage lithium ion batteries: A joint experimental and theoretical study Xu, Bo; Fell, Christopher R.; Chi, Miaofang Energy & Environmental Science, Vol. 4, Issue 6 https://doi.org/10.1039/c1ee01131f	journal	January 2011
A New Type of Protective Surface Layer for High-Capacity Ni-Based Cathode Materials: Nanoscaled Surface Pillaring Layer Cho, Yonghyun; Oh, Pilgun; Cho, Jaephil Nano Letters, Vol. 13, Issue 3 https://doi.org/10.1021/nl304558t	journal	February 2013
Synthesis of LiNi _0.8 Co _0.15 Al _0.05 O ₂ with 5-sulfosalicylic acid as a chelating agent and its electrochemical properties Xie, Hongbin; Du, Ke; Hu, Guorong Journal of Materials Chemistry A, Vol. 3, Issue 40 https://doi.org/10.1039/C5TA05266A	journal	January 2015
Improved Electrochemical Performance of the 5 V Spinel Cathode LiMn[sub 1.5]Ni[sub 0.42]Zn[sub 0.08]O[sub 4] by Surface Modification Liu, J.; Manthiram, A. Journal of The Electrochemical Society, Vol. 156, Issue 1 https://doi.org/10.1149/1.3028318	journal	January 2009
Synthesis and Electrochemical Properties of ZnO-Coated LiNi[sub 0.5]Mn[sub 1.5]O[sub 4] Spinel as 5 V Cathode Material for Lithium Secondary Batteries Sun, Y. -K.; Lee, Y. -S.; Yoshio, M. Electrochemical and Solid-State Letters, Vol. 5, Issue 5 https://doi.org/10.1149/1.1465375	journal	January 2002
Effect of Surface Modification on Nano-Structured LiNi _0.5 Mn _1.5 O ₄ Spinel Materials Cho, Hyung-Man; Chen, Michael Vincent; MacRae, Alex C. ACS Applied Materials & Interfaces, Vol. 7, Issue 30 https://doi.org/10.1021/acsami.5b01392	journal	July 2015
Doped sulfone electrolytes for high voltage Li-ion cell applications Sun, Xiaoguang; Angell, C. Austen Electrochemistry Communications, Vol. 11, Issue 7, p. 1418-1421 https://doi.org/10.1016/j.elecom.2009.05.020	journal	July 2009
Toward 5 V Li-Ion Batteries: Quantum Chemical Calculation and Electrochemical Characterization of Sulfone-Based High-Voltage Electrolytes Wu, Feng; Zhou, Hang; Bai, Ying ACS Applied Materials & Interfaces, Vol. 7, Issue 27 https://doi.org/10.1021/acsami.5b04477	journal	July 2015
Oxidatively stable fluorinated sulfone electrolytes for high voltage high energy lithium-ion batteries Su, Chi-Cheung; He, Meinan; Redfern, Paul C. Energy & Environmental Science, Vol. 10, Issue 4 https://doi.org/10.1039/C7EE00035A	journal	January 2017
On the application of ionic liquids for rechargeable Li batteries: High voltage systems Borgel, V.; Markevich, E.; Aurbach, D. Journal of Power Sources, Vol. 189, Issue 1 https://doi.org/10.1016/j.jpowsour.2008.08.099	journal	April 2009
Trimethylsilylcyclopentadiene as a novel electrolyte additive for high temperature application of lithium nickel manganese oxide cathode Tu, Wenqiang; Ye, Changchun; Yang, Xuerui Journal of Power Sources, Vol. 364 https://doi.org/10.1016/j.jpowsour.2017.08.021	journal	October 2017
A review on electrolyte additives for lithium-ion batteries Zhang, Sheng Shui Journal of Power Sources, Vol. 162, Issue 2, p. 1379-1394 https://doi.org/10.1016/j.jpowsour.2006.07.074	journal	November 2006
Recent advances in the research of functional electrolyte additives for lithium-ion batteries Zhao, Weimin; Ji, Yajuan; Zhang, Zhongru Current Opinion in Electrochemistry, Vol. 6, Issue 1 https://doi.org/10.1016/j.coelec.2017.10.012	journal	December 2017
Artificial Interface Derived from Diphenyl Ether Additive for High-Voltage LiNi _0.5 Mn _1.5 O ₄ Cathode Yue, Hong Yun; Han, Zhan Li; Tao, Liang Liang ChemElectroChem, Vol. 5, Issue 11 https://doi.org/10.1002/celc.201800011	journal	April 2018
Fluorinated phosphazene derivative – A promising electrolyte additive for high voltage lithium ion batteries: From electrochemical performance to corrosion mechanism Liu, Jianwen; Song, Xin; Zhou, Lai Nano Energy, Vol. 46 https://doi.org/10.1016/j.nanoen.2018.02.029	journal	April 2018
Optimal concentration of electrolyte additive for cyclic stability improvement of high-voltage cathode of lithium-ion battery Lin, Yilong; Li, Jianhui; Xing, Lidan Ionics, Vol. 24, Issue 3 https://doi.org/10.1007/s11581-017-2239-y	journal	August 2017
LiBOB as Electrolyte Salt or Additive for Lithium-Ion Batteries Based on LiNi[sub 0.8]Co[sub 0.15]Al[sub 0.05]O[sub 2]/Graphite Täubert, Corina; Fleischhammer, Meike; Wohlfahrt-Mehrens, Margret Journal of The Electrochemical Society, Vol. 157, Issue 6 https://doi.org/10.1149/1.3374666	journal	January 2010
Simultaneous Stabilization of LiNi _0.76 Mn _0.14 Co _0.10 O ₂ Cathode and Lithium Metal Anode by Lithium Bis(oxalato)borate as Additive Zhao, Wengao; Zou, Lianfeng; Zheng, Jianming ChemSusChem, Vol. 11, Issue 13 https://doi.org/10.1002/cssc.201800706	journal	June 2018
Mechanistic Insight into the Protective Action of Bis(oxalato)borate and Difluoro(oxalate)borate Anions in Li-Ion Batteries. Shkrob, Ilya A.; Zhu, Ye; Marin, Timothy W. The Journal of Physical Chemistry C, Vol. 117, Issue 45 https://doi.org/10.1021/jp407714p	journal	October 2013
Positive Electrode Passivation by LiDFOB Electrolyte Additive in High-Capacity Lithium-Ion Cells Zhu, Ye; Li, Yan; Bettge, Martin Journal of The Electrochemical Society, Vol. 159, Issue 12 https://doi.org/10.1149/2.083212jes	journal	January 2012
Bis(fluoromalonato)borate (BFMB) anion based ionic liquid as an additive for lithium-ion battery electrolytes Sun, Xiao-Guang; Liao, Chen; Baggetto, Loïc J. Mater. Chem. A, Vol. 2, Issue 20 https://doi.org/10.1039/C3TA14943A	journal	January 2014
Synthesis and Characterization of Lithium Bis(fluoromalonato)borate for Lithium-Ion Battery Applications Liao, Chen; Han, Kee Sung; Baggetto, Loïc Advanced Energy Materials, Vol. 4, Issue 6 https://doi.org/10.1002/aenm.201301368	journal	November 2013
Unsymmetrical fluorinated malonatoborate as an amphoteric additive for high-energy-density lithium-ion batteries Han, Jung-Gu; Lee, Jae Bin; Cha, Aming Energy & Environmental Science, Vol. 11, Issue 6 https://doi.org/10.1039/C8EE00372F	journal	January 2018
A stable fluorinated and alkylated lithium malonatoborate salt for lithium ion battery application Wan, Shun; Jiang, Xueguang; Guo, Bingkun Chemical Communications, Vol. 51, Issue 48 https://doi.org/10.1039/C5CC01428J	journal	January 2015
A Novel Electrolyte Salt Additive for Lithium-Ion Batteries with Voltages Greater than 4.7 V Li, Yunchao; Wan, Shun; Veith, Gabriel M. Advanced Energy Materials, Vol. 7, Issue 4 https://doi.org/10.1002/aenm.201601397	journal	November 2016
Lithium malonatoborate additives enabled stable cycling of 5 V lithium metal and lithium ion batteries Li, Yunchao; Veith, Gabriel M.; Browning, Katie L. Nano Energy, Vol. 40 https://doi.org/10.1016/j.nanoen.2017.07.051	journal	October 2017
New promising lithium malonatoborate salts for high voltage lithium ion batteries Sun, Xiao-Guang; Wan, Shun; Guang, Hong Yu Journal of Materials Chemistry A, Vol. 5, Issue 3 https://doi.org/10.1039/C6TA07757A	journal	January 2017
Tris(trimethylsilyl)borate as an electrolyte additive for improving interfacial stability of high voltage layered lithium-rich oxide cathode/carbonate-based electrolyte Li, Jianhui; Xing, Lidan; Zhang, Ruiqin Journal of Power Sources, Vol. 285 https://doi.org/10.1016/j.jpowsour.2015.03.113	journal	July 2015
Effect of tris(trimethylsilyl)borate on the high voltage capacity retention of LiNi0.5Co0.2Mn0.3O2/graphite cells Zuo, Xiaoxi; Fan, Chengjie; Liu, Jiansheng Journal of Power Sources, Vol. 229 https://doi.org/10.1016/j.jpowsour.2012.12.056	journal	May 2013
Artificial Interface Deriving from Sacrificial Tris(trimethylsilyl)phosphate Additive for Lithium Rich Cathode Materials Zhang, Jie; Wang, Jiulin; Yang, Jun Electrochimica Acta, Vol. 117 https://doi.org/10.1016/j.electacta.2013.11.024	journal	January 2014
Tris(trimethylsilyl)phosphate as electrolyte additive for self-discharge suppression of layered nickel cobalt manganese oxide Liao, Xiaolin; Zheng, Xiongwen; Chen, Jiawei Electrochimica Acta, Vol. 212 https://doi.org/10.1016/j.electacta.2016.07.026	journal	September 2016
Distinct Reaction Characteristics of Electrolyte Additives for High-Voltage Lithium-Ion Batteries: Tris(trimethylsilyl) Phosphite, Borate, and Phosphate Han, Young-Kyu; Yoo, Jaeik; Yim, Taeeun Electrochimica Acta, Vol. 215 https://doi.org/10.1016/j.electacta.2016.08.131	journal	October 2016
Tris(trimethylsilyl) Phosphite (TMSPi) and Triethyl Phosphite (TEPi) as Electrolyte Additives for Lithium Ion Batteries: Mechanistic Insights into Differences during LiNi _0.5 Mn _0.3 Co _0.2 O ₂ -Graphite Full Cell Cycling Peebles, Cameron; Sahore, Ritu; Gilbert, James A. Journal of The Electrochemical Society, Vol. 164, Issue 7 https://doi.org/10.1149/2.1101707jes	journal	January 2017
Constructing Unique Cathode Interface by Manipulating Functional Groups of Electrolyte Additive for Graphite/LiNi _0.6 Co _0.2 Mn _0.2 O ₂ Cells at High Voltage Liao, Bo; Hu, Xinliang; Xu, Mengqing The Journal of Physical Chemistry Letters, Vol. 9, Issue 12 https://doi.org/10.1021/acs.jpclett.8b01099	journal	May 2018
Forming a Stable CEI Layer on LiNi _0.5 Mn _1.5 O ₄ Cathode by the Synergy Effect of FEC and HDI Sun, Dandan; Wang, Qian; Zhou, Jingjing Journal of The Electrochemical Society, Vol. 165, Issue 10 https://doi.org/10.1149/2.0211810jes	journal	January 2018
Lithium Difluorophosphate As a Promising Electrolyte Lithium Additive for High-Voltage Lithium-Ion Batteries Wang, Chengyun; Yu, Le; Fan, Weizhen ACS Applied Energy Materials, Vol. 1, Issue 6 https://doi.org/10.1021/acsaem.8b00342	journal	May 2018
EXPGUI , a graphical user interface for GSAS Toby, Brian H. Journal of Applied Crystallography, Vol. 34, Issue 2 https://doi.org/10.1107/S0021889801002242	journal	April 2001
A comparative XPS surface study of Li ₂ FeSiO ₄ /C cycled with LiTFSI- and LiPF ₆ -based electrolytes Ensling, David; Stjerndahl, Mårten; Nytén, Anton J. Mater. Chem., Vol. 19, Issue 1 https://doi.org/10.1039/B813099J	journal	January 2009
Tris(trimethylsilyl)phosphate: A film-forming additive for high voltage cathode material in lithium-ion batteries Yan, Guochun; Li, Xinhai; Wang, Zhixing Journal of Power Sources, Vol. 248 https://doi.org/10.1016/j.jpowsour.2013.10.037	journal	February 2014
In-Depth Investigation on Two- and Three-Electrode Impedance Measurements in Terms of the Effect of the Counter Electrode Cho, Hyung-Man; Park, Yong Joon; Yeon, Jei-Won Electronic Materials Letters, Vol. 5, Issue 4 https://doi.org/10.3365/eml.2009.12.169	journal	December 2009
Two- and three-electrode impedance spectroscopy of lithium-ion batteries Song, J. Journal of Power Sources, Vol. 111, Issue 2 https://doi.org/10.1016/S0378-7753(02)00310-5	journal	September 2002
The effect of gradient boracic polyanion-doping on structure, morphology, and cycling performance of Ni-rich LiNi 0.8 Co 0.15 Al 0.05 O 2 cathode material Chen, Tao; Li, Xiang; Wang, Hao Journal of Power Sources, Vol. 374 https://doi.org/10.1016/j.jpowsour.2017.11.020	journal	January 2018
New findings on the phase transitions in Li1−xNiO2: in situ synchrotron X-ray diffraction studies Yang, X. Q.; Sun, X.; McBreen, J. Electrochemistry Communications, Vol. 1, Issue 6 https://doi.org/10.1016/S1388-2481(99)00046-6	journal	June 1999

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25 ENERGY STORAGE
bis(trimethylsilyl) 2-methyl-2-fluoromalonate (BTMSMFM)
bis(trimethylsilyl) 2-ethyl-2-fluoromalonate (BTMSEFM)
bis(trimethylsilyl) 2-propyl-2-fluoromalonate (BTMSPFM)
AdditiveLiNi0.80Co0.15Al0.05O2 (NCA)
Lithium ion batteries

Title: Bis(trimethylsilyl) 2-fluoromalonate derivatives as electrolyte additives for high voltage lithium ion batteries

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