CN103779568B - A kind of post quinone positive electrode for lithium ion battery and application thereof - Google Patents

A kind of post quinone positive electrode for lithium ion battery and application thereof Download PDF

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CN103779568B
CN103779568B CN201410055487.3A CN201410055487A CN103779568B CN 103779568 B CN103779568 B CN 103779568B CN 201410055487 A CN201410055487 A CN 201410055487A CN 103779568 B CN103779568 B CN 103779568B
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ion battery
lithium ion
post
quinone
positive electrode
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CN103779568A (en
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陈军
朱智强
陶占良
程方益
梁静
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Nankai University
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    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M4/00—Electrodes
    • H01M4/02—Electrodes composed of, or comprising, active material
    • H01M4/36—Selection of substances as active materials, active masses, active liquids
    • H01M4/60—Selection of substances as active materials, active masses, active liquids of organic compounds
    • H01M4/602—Polymers
    • H01M4/606—Polymers containing aromatic main chain polymers
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M10/00—Secondary cells; Manufacture thereof
    • H01M10/05—Accumulators with non-aqueous electrolyte
    • H01M10/058—Construction or manufacture
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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    • Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
    • Y02E60/10—Energy storage using batteries
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
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Abstract

For a post quinone positive electrode for lithium ion battery, for the carbonyl of 1,4-benzoquinone unit for electrochemical redox reaction site, the cyclic compound be formed by connecting by methylene in its contraposition by 5-7 1,4-benzoquinone unit.This post quinone positive electrode is for the preparation of accurate solid lithium ion battery, and method is as follows: 1) by active material, conductive agent and binding agent in organic solvent, and apply after grinding to form pulpous state on a current collector, air drying makes electrode; 2) with this electrode for positive pole, lithium metal is to electrode and reference electrode, and two electrodes separate with PMA/PEG gel polymer electrolyte, in argon gas or dry air, be assembled into battery.Advantage of the present invention is: this post quinone positive electrode has high carbonyl utilance and high specific capacity; Be applied to accurate solid lithium ion battery, specific discharge capacity be high, good cycle, be expected to be applied in the energy-storage battery of high-energy-density of future generation, high power density and long circulation life.

Description

A kind of post quinone positive electrode for lithium ion battery and application thereof
Technical field
The present invention relates to the organic positive electrode of lithium ion battery, particularly a kind of post quinone positive electrode for lithium ion battery and application thereof.
Background technology
Lithium ion battery, owing to having the advantages such as high working voltage, high-energy-density and long circulation life, occupies very important status in portable type electronic product field at present.The development of electric automobile and intelligent grid is in recent years had higher requirement to energy storage device, and the new energy materials of research and development high-energy-density becomes the emphasis that lithium ion battery further develops.
Current anode material for lithium-ion batteries is mainly based on the inorganic material of the transition metal oxide of lithium, and the actual capacity of this kind of material is generally lower than 170mAhg -1, be the Main Bottleneck that restriction battery capacity promotes.Compared with conventional inorganic material, the synthesis material wide material sources of organic electrode materials, environmental friendliness, structure height can design, in price, fail safe and energy density, all there is some superiority, be considered to desirable substitution material, see: Y.Liang, Z.Tao, J.Chen, Organicelectrodematerialsforrechargeablelithiumbatteries, AdvancedEnergyMaterials, 2012,2:742.But it is low that organic material simultaneously also exists conductivity, and side reaction is many, and in traditional liquid state organic electrolyte, the problem such as to dissolve, make their practical application still there is larger difficulty.
Effectively can overcome the low problem of the many and conductivity of organic substance side reaction by optimizing MOLECULE DESIGN and adding conductive agent, but its solubility problem in the electrolytic solution still can cause the rapid decay of capacity in cyclic process.Nearest research shows to utilize solid electrolyte to replace traditional liquid electrolyte, the organic material of solubility is assembled into accurate solid state battery, can addresses this problem well.Such as, Honma seminar adopts the solid electrolyte be made up of Nano particles of silicon dioxide and ionic liquid effectively to inhibit the dissolving of the quinones of several solubility, see: HanyuY, GanbeY, HonmaI.Applicationofquinoniccathodecompoundsforquasi-sol idlithiumbatteries.JPowerSources, 2013,221:186-190; HanyuY, HonmaI.Rechargeablequasi-solidstatelithiumbatterywithorg aniccrystallinecathode.SciRep, 2012,2:453.Recently, cup [4] quinone and the gel polymer electrolyte based on poly-(methacrylate)-polyethylene glycol (PMA/PEG) are assembled into accurate solid state battery by our seminar, achieve high specific capacity and long cycle life, see: HuangWW, ZhuZQ, WangLJ, WangSW, LiH, TaoZL, ShiJF, GuanLH, ChenJ.Quasi-solid-staterechargeablelithium-ionbatteriesw ithacalix [4] quinonecathodeandgelpolymerelectrolyte.AngewChemIntEd, 2013,52:9162-9166.But the organic electrode materials being applied to accurate solid state battery is at present also very limited.Organic carbonyl compound has large conjugated system, has the advantages such as specific capacity is high, kinetics is fast and receives extensive concern.The capacity contribution of this kind of material mainly comes from its carbonyl functional group.But the molecular structure of great majority containing multiple carbonyl functional group is due to sterically hindered impact, only has half or less carbonyl can participate in reaction, cause its actual capacity far below theoretical capacity.Therefore, continual exploitation is needed to can be used for organic positive electrode with height ratio capacity of accurate solid state battery.
Summary of the invention
The object of the invention is to, for above organic positive electrode Problems existing, provide a kind of post quinone positive electrode for lithium ion battery and application thereof, this post quinone positive electrode carbonyl utilance is high, specific capacity is high; Specific capacity can be improved for accurate solid lithium ion battery, extend cycle life.
Technical scheme of the present invention:
A kind of post quinone positive electrode for lithium ion battery, for with the carbonyl of 1,4-benzoquinone unit for electrochemical redox reaction site, cyclic compound post [n] quinone be formed by connecting by methylene in its contraposition by 5-7 1,4-benzoquinone unit, its general structure is as shown in general formula 1:
General formula 1
N=5 in general formula 1,6,7.
A described application for the post quinone positive electrode of lithium ion battery, for the preparation of accurate solid lithium ion battery, method is as follows:
1) by active material, conductive agent and binding agent in organic solvent, evenly apply on a current collector after grinding to form pulpous state, then electrode is made in drying in atmosphere, and baking temperature is 323-403K, and pressure is 100Pa ~-1Mpa;
2) with this electrode for positive pole, lithium metal is to electrode and reference electrode, and two electrodes separate with poly-(methacrylate)-polyethylene glycol (PMA/PEG) gel polymer electrolyte, in argon gas or dry air, be assembled into accurate solid lithium ion battery.
Described active material is the post naphtoquinone compounds be made up of 5-7 1,4-benzoquinone unit; Conductive agent is the mixture of one or more arbitrary proportions in electrically conductive graphite, conductive black, carbon nano-tube and Graphene; Described binding agent is the mixture of one or more arbitrary proportions in polytetrafluoroethylene, Kynoar, polyurethane and contracting sodium carboxymethylcellulose pyce; The quality share of active material, conductive agent and binding agent is 30-90:10-70:10-40; Organic solvent is 1-METHYLPYRROLIDONE, and the mass ratio of organic solvent and active material is 1-20:1; Described collector is nickel foam, aluminium net/sheet or stainless (steel) wire/sheet.
Described poly-(methacrylate)-polyethylene glycol (PMA/PEG) gel polymer electrolyte is made up of polymer substrate and electrolyte, the composition polymer that polymer substrate forms for poly-(methacrylate) and polyethylene glycol, poly-(methacrylate) is 1-6:0.001-4 with the mass ratio of polyethylene glycol, electrolyte is the solution that lithium salts is dissolved in organic solvent and prepares, lithium salts concentration is in organic solvent 0.5-1.5mol/L, wherein lithium salts is lithium perchlorate, LiBF4, lithium hexafluoro phosphate, the mixture of one or more arbitrary proportions of two fluorine sulfonephthalein imine lithium and trifluoromethyl sulfonic acid lithium, organic solvent is ethylene carbonate, propene carbonate, diethyl carbonate, dimethyl carbonate, methyl ethyl carbonate, carbonic acid first butyl ester and isomer thereof, sulfolane, gamma-butyrolacton, dimethoxy-ethane, 1, 3-diox, propiolic acid, the mixture of one or more arbitrary proportions in oxolane and dimethyl sulfoxide (DMSO), the mass ratio of polymer substrate and electrolyte is 1:0.1-50.
Advantage of the present invention is: this positive electrode is for electrochemical redox reaction site with the carbonyl on 1,4-benzoquinone unit, in this molecule, each 1,4-benzoquinone unit is separated by methylene, carbonyl is sterically hindered less, can redox reaction be participated in, thus be implemented to high carbonyl utilance and high specific capacity; Be applied to accurate solid lithium ion battery, specific discharge capacity is high, and (initial capacity can reach 410mAhg -1), good cycle (still keeping 88.5% of initial capacity after circulating 100 weeks, coulombic efficiency >99.9%), be expected to be applied in the energy-storage battery of high-energy-density of future generation, high power density and long circulation life.
Accompanying drawing explanation
Fig. 1 is with post [5] quinone for positive active material, and PMA/PEG gelatin polymer is the cyclic voltammetry curve of electrolytical accurate solid lithium ion battery under 0.2C.
Fig. 2 is with post [5] quinone for positive active material, and PMA/PEG gelatin polymer is the first constant current charge-discharge curve of electrolytical accurate solid lithium ion battery under 0.2C.
Fig. 3 is with post [5] quinone for positive active material, and PMA/PEG gelatin polymer is that the cycle charge discharge capacitance of electrolytical accurate solid lithium ion battery under 0.2C keeps curve.
Fig. 4 is with post [5] quinone for positive active material, and PMA/PEG gelatin polymer is that the cycle charge discharge capacitance of electrolytical accurate solid lithium ion battery under different multiplying keeps curve.
Embodiment
The present invention may be better understood for following examples, but the present invention is not limited to following examples.
Embodiment:
A kind of post quinone positive electrode for lithium ion battery, for with the carbonyl of 1,4-benzoquinone unit for electrochemical redox reaction site, cyclic compound post [5] quinone be formed by connecting by methylene in its contraposition by 5 1,4-benzoquinone unit, its general structure is as shown in general formula 1:
General formula 1
N=5 in general formula 1.
The application of the described post quinone positive electrode for lithium ion battery, for the preparation of accurate solid lithium ion battery, method is as follows:
1) active material post [5] quinone be made up of 5 1,4-benzoquinone unit by 12mg, 6mg conductive black and 2mg Kynoar binding agent are in 100 μ LN-methyl pyrrolidone organic solvents, evenly be coated in aluminum foil current collector after grinding to form pulpous state, then in-1MPa air, dryly under 353K within 10 hours, make electrode;
2) dried electrode slice is cut into the disk of 12mm, as positive pole, negative pole made by lithium metal, and two electrodes separate with PMA/PEG gel polymer electrolyte, in the glove box being full of argon gas, be assembled into accurate solid lithium ion battery.
The synthetic method of described post [5] quinone is: Isosorbide-5-Nitrae-dimethoxy benzene is at BF 3o (C 2h 5) effect issue raw annulation generate Isosorbide-5-Nitrae-dimethoxy pilum [5] aromatic hydrocarbons, the latter is at (NH 4) 2[Ce (NO 3) 6] be converted into post [5] quinone under oxidation.
The synthetic method of post [5] quinone is shown below:
The synthetic method of described PMA/PEG gel polymer electrolyte, step is as follows:
1) 0.73g ammonium persulfate is dissolved in 4g polyethylene glycol-600, then proceeded in 7.26g methyl acrylate, under nitrogen protection, stirring 5 minutes to being polymerized completely in 70 DEG C, obtaining the uniform PMA/PEG gelatin polymer matrix be made up of poly-(methacrylate) and polyethylene glycol;
2) get 0.74g lithium perchlorate to be dissolved in 10mL dimethyl sulfoxide (DMSO) and to prepare electrolyte;
3) join in the electrolyte of preparation by the gelatin polymer matrix that 3.17g synthesizes, vigorous stirring at 80 DEG C, until exist without solid, after being cooled to room temperature, obtains PMA/PEG gel polymer electrolyte.
The accurate solid lithium ion battery Performance Detection of preparation:
This accurate solid lithium ion battery is at 0.1mVs -1under cyclic voltammetry curve as shown in Figure 1, scanning voltage scope is 1.5-3.5V, reducing/oxidizing electromotive force lay respectively at 2.8 and 3.0V place have a pair redox peak clearly, corresponding to reduction and the oxidizing process of carbonyl.
This accurate solid lithium ion battery is at 0.2C(89mAg -1) under carry out constant current charge-discharge, discharge voltage range is 1.8-3.3V.As shown in Figure 2, discharge capacity and charging capacity are respectively 410mAhg to first charge-discharge curve first -1and 408mAhg -1, initial coulomb efficiency is 99%.
The cycle charge discharge capacitance of this accurate solid lithium ion battery under 0.2C keeps curve as shown in Figure 3, and through circulation in 100 weeks, discharge capacity was stabilized in 363mAhg -1, coulombic efficiency >99%.
The cycle charge discharge capacitance of this accurate solid lithium ion battery under different multiplying keeps curve as shown in Figure 4, and the discharge capacity under 0.2C, 0.5C, 1C and 2C is respectively 410, and 324,238 and 195mAh/g.
From testing result, post [n] quinone (n=5,6, the 7) positive electrode that the present invention proposes can realize high carbonyl utilance, has high specific capacity (>400mAhg -1), higher than traditional inorganic positive electrode as LiCoO 2(about 140mAhg -1) and LiFePO 4(about 160mAhg -1).When this positive electrode and PMA/PEG gel polymer electrolyte are assembled into accurate solid lithium ion battery, not only there is high specific capacity, also show excellent cyclical stability and high rate performance.So post [n] quinone (n=5,6,7) organic positive electrode that the present invention proposes has a good application prospect in high performance lithium ion battery.

Claims (4)

1. the post quinone positive electrode for lithium ion battery, it is characterized in that: with the carbonyl of 1,4-benzoquinone unit for electrochemical redox reaction site, cyclic compound post [n] quinone be formed by connecting by methylene in its contraposition by 5-7 1,4-benzoquinone unit, its general structure is as shown in general formula 1:
N=5 in general formula 1,6,7.
2. a preparation method for solid lithium ion battery, is characterized in that the positive electrode that this preparation method adopts is that concrete preparation method is as follows as claimed in claim 1 for the post quinone positive electrode of lithium ion battery:
1) by active material, conductive agent and binding agent in organic solvent, apply after grinding to form pulpous state on a current collector, then positive electrode is made in drying in atmosphere, and baking temperature is 323-403K, and pressure is-1MPa ~ 100Pa;
2) with this electrode for positive pole, lithium metal is to electrode and reference electrode, and two electrodes separate with polymethacrylates-polyethylene glycol gel polymer dielectric, in argon gas or dry air, be assembled into accurate solid lithium ion battery.
3. the preparation method of solid lithium ion battery according to claim 2, is characterized in that: described active material is the post naphtoquinone compounds be made up of 5-7 1,4-benzoquinone unit; Conductive agent is the mixture of one or more arbitrary proportions in electrically conductive graphite, conductive black, carbon nano-tube and Graphene; Described binding agent is the mixture of one or more arbitrary proportions in polytetrafluoroethylene, Kynoar, polyurethane and sodium carboxymethylcellulose; The quality share of active material, conductive agent and binding agent is 30-90:10-70:10-40; Organic solvent is 1-METHYLPYRROLIDONE, and the mass ratio of organic solvent and active material is 1-20:1; Described collector is nickel foam, aluminium net/sheet or stainless (steel) wire/sheet.
4. the preparation method of solid lithium ion battery according to claim 2, it is characterized in that: described polymethacrylates-polyethylene glycol gel polymer dielectric is made up of polymer substrate and electrolyte, polymer substrate is the composition polymer of polymethacrylates and polyethylene glycol composition, and the mass ratio of polymethacrylates and polyethylene glycol is 1-6:0.001-4, electrolyte is the solution that lithium salts is dissolved in organic solvent and prepares, lithium salts concentration is in organic solvent 0.5-1.5mol/L, wherein lithium salts is lithium perchlorate, LiBF4, lithium hexafluoro phosphate, the mixture of one or more arbitrary proportions of two fluorine sulfimide lithium and trifluoromethyl sulfonic acid lithium, organic solvent is ethylene carbonate, propene carbonate, diethyl carbonate, dimethyl carbonate, methyl ethyl carbonate, carbonic acid first butyl ester, sulfolane, gamma-butyrolacton, dimethoxy-ethane, 1, 3-diox, propiolic acid, the mixture of one or more arbitrary proportions in oxolane and dimethyl sulfoxide (DMSO), the mass ratio of polymer substrate and electrolyte is 1:(0.1-50).
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CN106159195B (en) * 2015-03-31 2018-12-21 比亚迪股份有限公司 A kind of battery core and the lithium ion battery comprising the battery core
CN105047897B (en) * 2015-09-09 2018-09-14 芜湖雄狮汽车科技有限公司 A kind of preparation method of anode material for lithium-ion batteries, lithium ion battery
WO2017156518A1 (en) * 2016-03-11 2017-09-14 University Of Houston System High ionic conductivity rechargeable solid state batteries with an organic electrode
CN107528066B (en) * 2017-04-10 2020-10-02 南开大学 Water-based zinc ion battery based on carbonyl compound cathode material and preparation method thereof
CN106981661B (en) * 2017-06-05 2019-08-23 南京工业大学 A kind of preparation method of lithium ion battery electrode material
CN109698335B (en) * 2018-12-19 2021-09-17 扬州大学 Preparation method of column [5] arene composite sulfur lithium sulfur positive electrode material
CN111211327B (en) * 2020-01-10 2022-10-25 天津大学 Compound for lithium ion battery anode material and preparation method and application thereof
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CN103022496B (en) * 2012-12-28 2014-12-24 南开大学 Aromatic condensed ring quinones compound positive pole material for one-class lithium secondary battery
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