CN112939760A - Application of oxidized perylene in organic anode material of lithium ion battery - Google Patents
Application of oxidized perylene in organic anode material of lithium ion battery Download PDFInfo
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- CN112939760A CN112939760A CN202110159636.0A CN202110159636A CN112939760A CN 112939760 A CN112939760 A CN 112939760A CN 202110159636 A CN202110159636 A CN 202110159636A CN 112939760 A CN112939760 A CN 112939760A
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- organic
- perylene
- lithium ion
- lithium
- ion battery
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- 239000010405 anode material Substances 0.000 title claims abstract description 14
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 title claims abstract description 9
- 229910001416 lithium ion Inorganic materials 0.000 title claims abstract description 9
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 title abstract description 17
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 title abstract description 6
- 230000001351 cycling effect Effects 0.000 claims abstract description 11
- 239000000463 material Substances 0.000 claims abstract description 9
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 8
- 238000006243 chemical reaction Methods 0.000 claims abstract description 4
- 238000006056 electrooxidation reaction Methods 0.000 claims abstract description 3
- 150000002500 ions Chemical class 0.000 claims abstract description 3
- 239000010406 cathode material Substances 0.000 claims description 13
- NFRTXVFXZGSPHP-UHFFFAOYSA-N 13-oxahexacyclo[9.8.1.12,6.012,14.016,20.010,21]henicosa-1(19),2,4,6(21),7,9,11(20),15,17-nonaene Chemical group C1=CC(C=2C3OC3C=C3C=2C2=CC=C3)=C3C2=CC=CC3=C1 NFRTXVFXZGSPHP-UHFFFAOYSA-N 0.000 claims description 4
- 239000013543 active substance Substances 0.000 claims 1
- 229910052744 lithium Inorganic materials 0.000 abstract description 22
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 abstract description 21
- -1 perylene compound Chemical class 0.000 abstract description 12
- 239000007772 electrode material Substances 0.000 abstract description 9
- 125000003118 aryl group Chemical group 0.000 abstract description 3
- 239000011368 organic material Substances 0.000 abstract description 3
- 239000007774 positive electrode material Substances 0.000 abstract description 3
- 230000002349 favourable effect Effects 0.000 abstract description 2
- 238000002360 preparation method Methods 0.000 abstract description 2
- 238000011160 research Methods 0.000 abstract description 2
- 150000001728 carbonyl compounds Chemical class 0.000 description 3
- 238000004146 energy storage Methods 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000009831 deintercalation Methods 0.000 description 2
- 230000002687 intercalation Effects 0.000 description 2
- 238000009830 intercalation Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 1
- 239000006245 Carbon black Super-P Substances 0.000 description 1
- 241000282414 Homo sapiens Species 0.000 description 1
- 229910001290 LiPF6 Inorganic materials 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- 239000002033 PVDF binder Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- MKCDXXDWWZVCJG-UHFFFAOYSA-M lithium;4-methyl-1,3-dioxolan-2-one;perchlorate Chemical compound [Li+].[O-]Cl(=O)(=O)=O.CC1COC(=O)O1 MKCDXXDWWZVCJG-UHFFFAOYSA-M 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 150000002898 organic sulfur compounds Chemical class 0.000 description 1
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/703—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups
- C07C49/747—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups containing six-membered aromatic rings
-
- 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
- H01M10/052—Li-accumulators
- H01M10/0525—Rocking-chair batteries, i.e. batteries with lithium insertion or intercalation in both electrodes; Lithium-ion batteries
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/52—Ortho- or ortho- and peri-condensed systems containing five condensed rings
-
- 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
- H01M2004/026—Electrodes composed of, or comprising, active material characterised by the polarity
- H01M2004/028—Positive electrodes
-
- 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
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
- Y02E60/10—Energy storage using batteries
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- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Electrochemistry (AREA)
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- Materials Engineering (AREA)
- Manufacturing & Machinery (AREA)
- Battery Electrode And Active Subsutance (AREA)
- Secondary Cells (AREA)
Abstract
The invention belongs to the field of preparation of lithium ion battery anode materials, and particularly relates to an organic anode material of a lithium ion battery. Provides an organic perylene compound which can be used as a positive electrode material of a lithium battery, and researches the performance of the organic perylene compound as an electrode material of the lithium battery. The organic material takes carbonyl and conjugated aromatic condensed rings as electrochemical redox sites, and improves the potential of a redox electrode, the output voltage of a lithium battery and the energy density of the electrode material based on the ion embedding mechanism of the carbonyl and the condensed rings. The perylene large conjugated system can effectively balance positive charges generated by electrochemical oxidation reaction, and is favorable for the cycling stability of the material. When the prepared perylene compound is used as an electrode material of a lithium battery, the perylene compound has excellent cycling stability and proper specific capacity, and after 1000 times of cycling, the coulomb efficiency is almost close to 100%.
Description
[ technical field ] A method for producing a semiconductor device
The invention belongs to the field of preparation of electrode materials of lithium batteries, and particularly relates to an organic positive electrode material of an organic perylene compound for a lithium battery.
[ background of the invention ]
With the development of economy, the industrial development of human beings has made higher demands on energy sources and at the same time, the challenge of energy crisis is also faced, so that the development of clean energy sources is an important solution. Clean energy is mostly limited intermittently and regionally, and therefore energy storage is a research hotspot. In recent decades, lithium batteries have been rapidly developed as a novel energy storage device, and have the advantages of high storage energy density and low cost, and are widely applied to various fields such as new energy vehicles. However, the market places higher demands on the storage density and the flexibility of lithium batteries, and thus, development of new materials having electrodes is required. The cathode material of the traditional lithium battery is mainly an inorganic compound and is limited by the problem of mineral reserve exploitation, and the inorganic substance serving as the cathode material is limited by many limits. The organic anode material can avoid the problem of reserve capacity, has green sustainability and is an ideal anode material for future lithium batteries. At present, electroactive organic materials can be broadly classified into the following categories: conductive polymers, organic sulfur compounds, organic radical compounds and organic carbonyl compounds. Among them, the organic carbonyl compounds have high theoretical specific capacity and are receiving great attention. However, the organic carbonyl compound has problems of poor conductivity and poor cycle stability. Therefore, we propose a new organic cathode material, which uses perylene oxide as the cathode material and has the advantages of large capacity and high cycling stability.
[ summary of the invention ]
The invention aims to provide an organic perylene compound which can be used as a positive electrode material of a lithium battery, and the performance of the organic perylene compound as an electrode material of the lithium battery is researched. The perylene oxide raw material has the advantages of simple synthesis process, lower cost, low energy consumption, good reproducibility and excellent performance. The organic material takes carbonyl and conjugated aromatic condensed rings as electrochemical redox sites, and improves the potential of a redox electrode, the output voltage of a lithium battery and the energy density of the electrode material based on the ion embedding mechanism of the carbonyl and the condensed rings. When the prepared perylene compound is used as an electrode material of a lithium battery, the perylene compound has excellent cycling stability and proper specific capacity, and after 1000 times of cycling, the coulomb efficiency is almost close to 100%.
Based on the above purpose, the technical scheme adopted by the invention is as follows: an organic perylene compound is provided, which has the following structural formula:
according to another aspect of the present invention, there is provided a lithium ion battery comprising the organic cathode material.
The invention has the advantages that: the invention adopts the perylene compound oxide to be used as the anode material of the lithium battery. The charge-discharge cycle of the battery is realized by taking carbonyl and aromatic rings of perylene as electrochemical redox sites through a lithium ion reversible intercalation/deintercalation mechanism. The lithium ion battery organic anode material has relatively high lithium intercalation/lithium deintercalation reaction potential, and can improve the energy density of the lithium battery anode material. The perylene large conjugated system can effectively balance positive charges generated by electrochemical oxidation reaction, and is favorable for the cycling stability of the material. The traditional benzoquinone electrode material is poor in conductivity and poor in cycling stability due to the lack of a large conjugated system. The organic electrode anode material provided by the invention does not contain transition metal, has low price of synthetic raw materials, wide sources, excellent cycling stability and proper specific capacity, is a brand new organic electrode material, and has wide application prospect in the fields of energy storage systems such as lithium batteries and wearable equipment.
[ description of the drawings ]
Fig. 1 is a charge and discharge curve of a battery manufactured by using the organic cathode material of example 1 according to different current densities.
Fig. 2 is a graph of rate performance of a battery correspondingly fabricated from the organic cathode material of example 1.
FIG. 3 is a graph of the performance of a battery prepared from the organic cathode material of example 1, which is charged and discharged 1000 times under a current density of 1000 mA/g.
[ detailed description ] embodiments
For better understanding of the present invention, the present invention is illustrated by the following specific examples, which are provided only for the purpose of illustration and are not intended to limit the present invention in any way.
The organic anode material has a structure as shown in a formula (I):
compared with the carbonyl material in the prior art, the invention has the advantage that the energy density is obviously improved.
[ example 1 ]
And (2) fully and uniformly mixing 30mg of the compound shown in the formula I, 24mg of Super-P and 6mg of polyvinylidene fluoride, adding 0.5mL of N-methylpyrrolidone, fully and uniformly grinding again to prepare homogenate, uniformly coating the homogenate on an aluminum foil, and then drying in vacuum at the temperature of 80 ℃ for 12 hours to prepare an electrode film. In a glove box filled with dry argon, the prepared electrode film is used as a positive electrode, glass fiber is used as a diaphragm, 1.0mol/L of lithium perchlorate propylene carbonate solution is used as electrolyte, and metal lithium is used as a negative electrode to assemble the button cell. The assembled battery is 200mA g-1Constant current charge and discharge are carried out under current density, the charge and discharge curve is shown in figure 1, figure 2 is a multiplying power performance graph of example 1, and figure 3 is a performance graph obtained by carrying out charge and discharge 1000 times in cycles under the current density of 1000mA/g in example 1. As can be seen from fig. 1, the average discharge voltage of the organic cathode material of the present invention is 2.7V; from FIG. 2, it is found that the current at 200mA · g-1，500mA·g-1，1000mA·g-1After 10 times of circulation, the specific discharge capacity is 166.5, 150.8 and 136.1mAh g-1When the current density returns to 200mA g-1When the discharge capacity is increased to 166.3mAh g-1The energy density was about 450 Wh/Kg. After 40 cycles, the charge-discharge capacity of the material has no obvious attenuation, which shows that the material has higher rate performance as the lithium battery anode. FIG. 3 shows that the material is cycled 1000 times at a current density of 1000mA/g, the coulombic efficiency is close to 100%, and the capacity retention rate is 87.6%. Indicating that the material has good cycling stability.
Comparative example 1
For example, perylene, a condensed ring compound having a similar structure (i.a. rodr i guez-pirez, c.bommier, d.d.fuller, d.p.leonard, a.g.williams, x.ji, ACS appl.mater. interfaces 2018,10, 43311), in LiPF6In the (1.0M) EC/DEC mixed solution, the button cell assembled by the lithium metal as the negative electrode is charged and discharged, the obtained average discharge voltage is 3.7V, the stable specific capacity is about 50mAh/g, and therefore the energy density is about 185 Wh/Kg.
Claims (3)
1. An organic anode material of a lithium ion battery is characterized in that an active substance is perylene oxide;
the organic anode material takes carbonyl and condensed rings of perylene oxide as electrochemical redox sites, and improves the potential of a redox electrode based on the ion embedding mechanism of the carbonyl and the condensed rings, so that the energy density of the anode material is improved, the positive charges generated by electrochemical oxidation reaction can be balanced by a large conjugated structure, and the cycling stability of the material is facilitated.
2. The organic cathode material according to claim 1, wherein the organic cathode material has a structure represented by formula (one):
3. the use of the organic cathode material according to claim 1 for a cathode material for a lithium ion battery.
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|---|---|---|---|
| CN202110159636.0A CN112939760B (en) | 2021-02-05 | 2021-02-05 | Application of oxidized perylene in organic anode material of lithium ion battery |
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| CN202110159636.0A CN112939760B (en) | 2021-02-05 | 2021-02-05 | Application of oxidized perylene in organic anode material of lithium ion battery |
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| CN112939760B CN112939760B (en) | 2022-11-18 |
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS55161376A (en) * | 1979-06-04 | 1980-12-15 | Nec Corp | Cell |
| CN106328949A (en) * | 2016-09-27 | 2017-01-11 | 华中科技大学 | Organic electrode material of organic electrolyte sodium iron battery and preparation method thereof |
| CN106977974A (en) * | 2017-04-12 | 2017-07-25 | 湖南大学 | Yi Zhong perylene quinone dyestuffs and preparation method thereof |
| CN111342047A (en) * | 2019-12-27 | 2020-06-26 | 欧格尼材料科技江苏有限公司 | High-performance organic positive electrode material and application thereof in potassium ion battery |
-
2021
- 2021-02-05 CN CN202110159636.0A patent/CN112939760B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS55161376A (en) * | 1979-06-04 | 1980-12-15 | Nec Corp | Cell |
| CN106328949A (en) * | 2016-09-27 | 2017-01-11 | 华中科技大学 | Organic electrode material of organic electrolyte sodium iron battery and preparation method thereof |
| CN106977974A (en) * | 2017-04-12 | 2017-07-25 | 湖南大学 | Yi Zhong perylene quinone dyestuffs and preparation method thereof |
| CN111342047A (en) * | 2019-12-27 | 2020-06-26 | 欧格尼材料科技江苏有限公司 | High-performance organic positive electrode material and application thereof in potassium ion battery |
Non-Patent Citations (5)
| Title |
|---|
| BERNHARD HÄUPLER等: ""Carbonyls: Powerful Organic Materials for Secondary Batteries"", 《ADVANCED ENERGY MATERIALS》 * |
| JU-PENG CHEN等: ""Perylenequinone-based "turn on" fluorescent probe for hydrogen sulfide with high sensitivity in living cells"", 《SPECTROCHIMICA ACTA PART A: MOLECULAR AND BIOMOLECULAR SPECTROSCOPY》 * |
| R.R.ZHAO等: ""Reversible Li and Na storage behaviors of perylenetetracarboxylates as organic anodes for Li- and Na-ion batteries"", 《JOURNAL OF ELECTROANALYTICAL CHEMISTRY》 * |
| 刘瑶俊等: ""3,4,9,10-苝四甲酸四钠盐在锂离子电池中的应用"", 《储能科学与技术》 * |
| 马列: ""基于芳香分子的锂离子电池有机正负极材料"", 《中国优秀博硕士学位论文全文数据库(硕士)工程科技Ⅱ辑》 * |
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