CN109516450B - Two-dimensional nitrogen-doped nano graphene material and application thereof - Google Patents
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Abstract
The invention belongs to the technical field of anode lithium batteries, and relates to a two-dimensional nitrogen-doped nano graphene material and application thereof. The structural formula of the nano graphene material is shown as the formula (I)
Description
Technical Field
The invention belongs to the technical field of anode lithium batteries, and relates to a two-dimensional nitrogen-doped nano graphene material and application thereof.
Background
J.s. Driscoll et al. An organic electrode material using dichloroisocyanuric acid as a cathode material was first reported in 1969. Since then, various organic electrode materials have been tested by various research groups as anodes for LIBs. Many inorganic redox active electrode materials have been synthesized in the prior art and should be commercially available. Although these materials have good rate capability and significant cycling stability, the complex manufacturing process results in high manufacturing costs and uncontrollable structures, which greatly limits the applications.
With the ever-increasing market share of environmental protection energy, new battery technology is being applied, and graphene batteries are an irreplaceable new technology in the world today. Although many graphene batteries have been designed in recent years, there is still a need for further improvement in effective utilization of energy efficiency.
Nano-graphene and graphene composite materials are widely studied as lithium ion anodes. Core-shell structures with silicon or metal nanostructures encapsulated by carbonaceous materials are disclosed in the prior art to modify the properties of anode materials. However, although the material is widely used in actual production and application, the material does not meet the existing requirements in the aspect of practical performance; moreover, the nano graphene composite material is introduced with a large amount of silicon, so that the stability of the nano graphene composite material is improved, and the performance index is greatly reduced; under the existing conditions, the application of a large amount of high molecular nano-graphite materials is expensive, is not beneficial to large-scale commercial production, and has problems in the aspect of universal application.
In summary, based on the current requirements for commercial use of nano-graphite anode storage materials, the development and application of new nano-graphite anode materials is an effective way to solve this problem.
Disclosure of Invention
The invention aims to provide a two-dimensional nitrogen-doped nano graphene material with a structural formula shown as a formula (I)
Wherein A, B, C or D is any one of carbon or nitrogen atom. The two-dimensional nitrogen-doped nano graphene material can enable a large amount of lithium ions to be gathered in the anode material, so that the charging capacity, the durability and the cycle efficiency of the battery are improved, and the cost of the nano graphene material is reduced.
In at least one embodiment of the present invention, there is provided a compound represented by the formula (I-1) wherein A is a nitrogen atom and the remainder B, C, D are carbon atoms
The compound shown in the specification.
In at least one embodiment of the present invention, there is provided a composition wherein A, B represents a nitrogen atom and the remainder C, D represents a carbon atom, represented by the formula (I-2)
The compound shown in the specification.
In at least one embodiment of the present invention, there is provided a composition wherein A, B, C are each a nitrogen atom, D is a carbon atom, represented by the formula (I-3)
The compound shown in the specification.
In at least one embodiment of the present invention, there is provided a composition wherein A, B, C, D are nitrogen atoms, represented by the formula (I-4)
The compound shown in the specification.
The invention also provides a nano graphene material battery device which sequentially comprises a cathode material and a permeable diaphragm from left to rightAnd an anode material; the cathode material is a lithium salt material, the anode material is a two-dimensional nitrogen-doped nano graphene material, and the structure is as follows:
(ii) a The mass ratio of the anode material to the cathode material is 1: 1.
Furthermore, the two-dimensional nitrogen-doped nano graphene material is a compound with a structural formula shown in any one of formula (I-1), formula (I-2), formula (I-3) or formula (I-4).
Preferably, the lithium salt material is indium lithium oxide.
Further, the permeable membrane is a polyolefin porous membrane.
The thickness of the cathode material is 1-2mm, the thickness of the permeable membrane is 0.5-1mm, and the thickness of the anode material is 1-2 mm.
Compared with the prior art, the invention has the beneficial effects that:
the invention synthesizes a series of novel two-dimensional nitrogen-doped nano graphene materials with good structures based on hexabenzene anthracene through a simple organic synthesis method. The nitrogen-free nano graphene has a planar size structure, and the size of the nano graphene is 1.2 nm; the nitrogen atom doped nano graphene has a scissor-like structure, the sp 2-hybridized nitrogen atom on one side enhances the conjugation between the carbon atom and the nitrogen atom, and overcomes the defects in a hexaphene eutectic planar structure, and the electrostatic interaction between lone pair electrons of the nitrogen atom and electron clouds of the carbon atom drives the planar structure to enter a scissor-like twisted structure with an angle ranging from 25 degrees to 40 degrees; the geometric and electronic properties produce an optimal dynamic self-assembled structure with large d-spacing between layers, allowing efficient Li incorporation/extraction and diffusion. A large amount of lithium ions are accumulated in the anode material, increasing the charging ability, battery durability and cycle efficiency.
The two-dimensional nitrogen-doped nano graphene material disclosed by the invention has better battery performance, durability and conductivity of charging cycle, provides quick charging capability for a lithium ion anode, and has important application value. The two-dimensional nitrogen-doped nano graphene material has excellent performance, easily obtained raw materials, low synthesis difficulty, simple preparation, high overall yield and greatly reduced cost of the conventional nano graphene material.
The nitrogen-doped nano graphene material battery device prepared by the invention solves the problem of expensive anode material cost; the problems of difficulty in assembling battery devices and economy of the nano graphene are solved; the performance of the anode material is changed by adding lithium ions, and the battery performance cycle efficiency is higher by adopting the nitrogen-doped graphene material as the anode material.
Drawings
FIG. 1 is a schematic ion mass spectrum of a compound having the structure of formula (I-1).
FIG. 2 is a schematic ion mass spectrum of a compound having the structure of formula (I-2).
FIG. 3 is a schematic ion mass spectrum of a compound having the structure of formula (I-3).
FIG. 4 is a schematic ion mass spectrum of a compound having the structure of formula (I-4).
Fig. 5 is a constant voltage current cycling specific capacity diagram of the nitrogen-doped nano graphene material battery prepared in example 5.
Fig. 6 is a rate performance graph of cycle performance of the nitrogen-doped nanographene material cell fabricated in example 5.
Detailed Description
For the purpose of enhancing the understanding of the present invention, the present invention will be further described in detail with reference to the following examples and the accompanying drawings, which are only used for explaining the present invention and are not to be construed as limiting the scope of the present invention. The process is conventional unless otherwise specified, and the starting materials used are commercially available from the public unless otherwise specified.
The compound shown in the formula I provided by the invention can be prepared according to the following reaction formula:
example 1: preparation of two-dimensional nitrogen-doped nano graphene material compound (I-1)
Weighing 1.0g of 2- (1,2, 3, 4-pentaphenyl) pyridine, dissolving in 5.0ml of nitromethane, stirring for 5 minutes, slowly adding 3.0g of ferric chloride, adding into a three-necked bottle, reacting for 24 hours at 100 ℃ after the completion of the addition, cooling to room temperature after the completion of the reaction, directly filtering the solid, washing for 3 times by using a mixed solvent (1.0 ml of methanol: 1.0ml of acetone: 1.0ml of ethyl acetate), and drying to obtain 0.81g of the compound with the structure of the formula (I-1), wherein the yield is 83%.
Weighing 1.0g of 2- (1,2, 3, 4-pentaphenyl) pyridine, dissolving in 5.0ml of nitroalkane, stirring for 5 minutes, slowly adding 2.5g of aluminum trichloride, adding into a three-necked bottle, reacting for 24 hours at 100 ℃ after the addition is finished, cooling to room temperature after the reaction is finished, directly filtering the solid, washing for 3 times by using a mixed solvent (1.0 ml of methanol: 1.0ml of acetone: 1.0ml of ethyl acetate), and drying to obtain 0.70g of the compound with the structure of the formula (I-1), wherein the yield is 73%.
Weighing 1.0g of 2- (1,2, 3, 4-pentaphenyl) pyridine, dissolving in 5.0ml of nitromethane, stirring for 5 minutes, slowly adding 3.0g of ferric chloride, adding into a three-necked bottle, reacting for 24 hours at 120 ℃ after the completion of the addition, cooling to room temperature after the completion of the reaction, directly filtering the solid, washing for 3 times by using a mixed solvent (1.0 ml of methanol: 1.0ml of acetone: 1.0ml of ethyl acetate), and drying to obtain 0.9g of the compound with the structure of the formula (I-1), wherein the yield is 88%.
FIG. 1 is a schematic ion mass spectrum of a compound having the structure of formula (I-1); as can be seen from FIG. 1, the molecular weight of the ion mass spectrum is ESI-MS (M + H)+525.34 for sized 525.61; the element analysis content is Found in the following percentage, C, 93.68, H, 3.66, N, 2.67, C, 93.69, H, 3.64 and N, 2.66.
Example 2 preparation of two-dimensional nitrogen-doped nanographene Material Compound (I-2)
Weighing 1.0g of 2,2' - (3',6' -diphenyl- [1,1':2',1' ' -diphenyl ] -4',5') bipyridine, dissolving in 5.0ml of nitromethane, stirring for 5 minutes, slowly adding 3.0g of ferric chloride, adding into a three-necked bottle, reacting at 100 ℃ for 24 hours after the addition is finished, cooling to room temperature after the reaction is finished, directly filtering the solid, washing for 3 times by using a mixed solvent (1.0 ml of methanol: 1.0ml of acetone: 1.0ml of ethyl acetate), and drying to obtain 0.80g of the compound with the structure of the formula (I-2), wherein the yield is 82%.
Weighing 1.0g of 2,2' - (3',6' -diphenyl- [1,1':2',1' ' -diphenyl ] -4',5') bipyridine, dissolving in 5.0ml of nitroalkane, stirring for 5 minutes, slowly adding 2.6g of aluminum trichloride, adding into a three-necked bottle, reacting at 100 ℃ for 24 hours after the addition is finished, cooling to room temperature after the reaction is finished, directly filtering the solid, washing for 3 times by using a mixed solvent (1.0 ml of methanol: 1.0ml of acetone: 1.0ml of ethyl acetate), and drying to obtain 0.67g of the compound with the structure of the formula (I-2), wherein the yield is 71%.
Weighing 1.0g of 2,2' - (3',6' -diphenyl- [1,1':2',1' ' -diphenyl ] -4',5') bipyridine, dissolving in 5.0ml of nitromethane, stirring for 5 minutes, slowly adding 3.2g of ferric chloride, adding into a three-necked bottle, reacting at 120 ℃ for 24 hours after the addition is finished, cooling to room temperature after the reaction is finished, directly filtering the solid, washing for 3 times by using a mixed solvent (1.0 ml of methanol: 1.0ml of acetone: 1.0ml of ethyl acetate), and drying to obtain 0.88g of the compound with the structure of the formula (I-2), wherein the yield is 86%.
FIG. 2 is a schematic ion mass spectrum of a compound having the structure of formula (I-2); as can be seen from FIG. 2, the molecular weight of the ion mass spectrum is ESI-MS (M + H)+527.02 for sized 526.60; the elemental analysis content is Found in Found, C, 91.22, H, 3.42, N, 5.37, C40H18N2, scaled, C, 91.23, H, 3.45, N, 5.32.
Example 3 preparation of two-dimensional Nitrogen-doped Nanographene Material Compound (I-3)
1.0g of 2,2',2' ' - (5' -phenyl- [1,1':2',1' ' -phenyl ] -3',4',6' -phenyl) tripyridine is weighed, dissolved in 5.0ml of nitromethane, stirred for 5 minutes, slowly added with 3.0g of ferric chloride, added into a three-necked flask, reacted at 100 ℃ for 24 hours after the addition is finished, cooled to room temperature, directly filtered for solids, washed 3 times with a mixed solvent of (1.0 ml of methanol: 1.0ml of acetone: 1.0ml of ethyl acetate), and dried to obtain 0.78g of the compound having the structure of the formula (I-3) with a yield of 81%.
1.0g of 2,2',2' ' - (5' -phenyl- [1,1':2',1' ' -phenyl ] -3',4',6' -phenyl) tripyridine is weighed, dissolved in 5.0ml of nitroalkane, stirred for 5 minutes, slowly added with 2.6g of aluminum trichloride, added into a three-necked flask, reacted at 100 ℃ for 24 hours after the addition is finished, cooled to room temperature, directly filtered for solids, washed 3 times with a mixed solvent of (1.0 ml of methanol: 1.0ml of acetone: 1.0ml of ethyl acetate), and dried to obtain 0.59g of the compound having the structure of the formula (I-3) with a yield of 63%.
Weighing 1.0g of 2,2',2' ' - (5' -phenyl- [1,1':2',1' ' -phenyl ] -3',4',6' -phenyl) tripyridine, dissolving in 5.0ml of nitromethane, stirring for 5 minutes, slowly adding 3.2g of ferric chloride, adding into a three-necked flask, reacting at 120 ℃ for 24 hours after the addition is finished, cooling to room temperature after the reaction is finished, directly filtering the solid, washing 3 times with a mixed solvent of (1.0 ml of methanol: 1.0ml of acetone: 1.0ml of ethyl acetate), and drying to obtain 0.85g of the compound having the structure of the formula (I-3), wherein the yield is 83%.
FIG. 3 is a schematic ion mass spectrum of a compound having the structure of formula (I-3); as can be seen from FIG. 3, the molecular weight of the ion mass spectrum is ESI-MS (M + H)+529.60 for sized 529.12; the elemental analysis content is Found in Found, C, 88.47, H, 3.63, N, 7.92, C39H19N3, scaled, C, 88.45, H, 3.62 and N, 7.93.
Example 4 preparation of two-dimensional Nitrogen-doped Nanographene Material Compound (I-4)
Weighing 1.0g of 2',3',5',6' - (2-tetrapyridine) -1,1':4',1'' -diphenyl, dissolving in 5.0ml of nitromethane, stirring for 5 minutes, slowly adding 3.3g of ferric chloride, adding into a three-necked bottle, reacting at 100 ℃ for 24 hours after the addition is finished, cooling to room temperature after the reaction is finished, directly filtering the solid, washing with a mixed solvent of (1.0 ml of methanol: 1.0ml of acetone: 1.0ml of ethyl acetate) for 3 times, and drying to obtain 0.79g of the compound with the structure of the formula (I-4), wherein the yield is 82%.
Weighing 1.0g of 2',3',5',6' - (2-tetrapyridine) -1,1':4',1'' -diphenyl, dissolving in 5.0ml of nitrobenzane, stirring for 5 minutes, slowly adding 2.6g of aluminum trichloride, adding into a three-necked flask, reacting at 100 ℃ for 24 hours after the addition is finished, cooling to room temperature after the reaction is finished, directly filtering the solid, washing with a mixed solvent of (1.0 ml of methanol: 1.0ml of acetone: 1.0ml of ethyl acetate) for 3 times, and drying to obtain 0.61g of the compound with the structure shown in the formula (I-4), wherein the yield is 66%.
Weighing 1.0g of 2',3',5',6' - (2-tetrapyridine) -1,1':4',1'' -diphenyl, dissolving in 5.0ml of nitromethane, stirring for 5 minutes, slowly adding 3.2g of ferric chloride, adding into a three-necked bottle, reacting at 120 ℃ for 24 hours after the addition is finished, cooling to room temperature after the reaction is finished, directly filtering the solid, washing with a mixed solvent of (1.0 ml of methanol: 1.0ml of acetone: 1.0ml of ethyl acetate) for 3 times, and drying to obtain 0.82g of the compound with the structure shown in the formula (I-4), wherein the yield is 80%.
FIG. 4 is a schematic ion mass spectrum of a compound having the structure of formula (I-4); as can be seen from FIG. 4, the molecular weight of the ion mass spectrum is ESI-MS (M + H)+530.39 for sized 530.59; the elemental analysis content is Found in Found, C, 86.06, H, 3.45, N, 10.58, C38H18N4, scaled, C, 86.02, H, 3.42, N, 10.56.
Example 5:
the specific preparation method of the nano graphene lithium battery device comprises the following steps:
1. preparation of the slurry
(1) According to the following steps of 1:1, weighing the hexa-benzo crown and the acetylene black in proportion, and grinding for 15min in an agate mortar;
(2) dripping 5wt% polyvinylidene fluoride colloid into a small bottle by using a liquid-transferring gun according to the proportion;
(3) pouring the mixed powder in the step (1) into a small bottle, dropwise adding a proper amount of nitrogen-methyl pyrrolidone, and stirring for 24 hours.
(4) The slurry was dropped onto copper foil with a pipette gun, and the graphite thin slurry was dropped to a thickness of 13 mm, each approximately 15ul, and dried to 1-2 mg.
(5) Drying at 60 deg.C, and vacuum drying at 110 deg.C.
2. Battery assembly
(1) Positive electrode shell-electrolyte (5ul) -positive electrode piece-electrolyte (40ul) -diaphragm (avoiding air bubble as much as possible) -electrolyte (20ul)
(2) Negative electrode casing-gasket (0.8mm) -lithium sheet
(3) Reversely buckling the (2) in the 1, keeping the sealing pressure at 50MPa, and standing for 12h
According to the steps, the device is sequentially tested with 4 different anode materials, the performance detection results of the obtained devices I-1, I-1 and I-4 are shown in figures 5 and 6, and corresponding performance indexes are further arranged into tables 1 and 2.
TABLE 1 comparison table for testing circulating constant current performance of four different anode materials for assembled batteries
As can be seen from Table 1, the circulating currents of the different anode materials of the device structures I-1 to I-4 are 596, 824, 1108 and 1928Ah/g respectively; the circulating potential energy is 5.692, 6.091, 6.067 and 6.144V respectively; the circulating constant current voltage performance is 893, 1468 and 1746mAh/g respectively, and particularly I-4 most particularly shows that the performance is 2421 mAh/g.
TABLE 2 cycling rate Performance for four assembled batteries at different Current Density
| Device number | Device structure | Cycling rate voltage (mAh/g) |
| I-1 | LiCoO2Polyethylene film/I-1 | 712 |
| I-2 | LiCoO2Polyethylene film/I-2 | 1086 |
| I-3 | LiCoO2Polyethylene film/I-3 | 1326 |
| I-4 | LiCoO2Polyethylene film/I-4 | 1804 |
From Table-2, the cycling rate performance for the different anode materials of the device structures I-1 through I-4 was 712, 1086, and 1326mAh/g, respectively, with I-4 being the most prominent at 1804 mAh/g.
From the performance indexes of the anode materials without devices corresponding to the above tables 1,2, 5 and 6, the I-4 device with the most nitrogen doping is the best, and the mutual relationship between the structure and the performance can be fully obtained through the data analysis, so that the characteristics of the invention can be concluded.
The present invention is not limited to the above-described embodiments, and any obvious improvements, substitutions or modifications can be made by those skilled in the art without departing from the spirit of the present invention.
Claims (10)
1. The two-dimensional nitrogen-doped nano graphene material is characterized in that the structural formula is shown as the formula (I)
The compound shown in the formula, wherein A, B, C or D is any one of carbon or nitrogen atoms.
2. The two-dimensional nitrogen-doped nano-graphene anode material as claimed in claim 1, wherein the nano-graphene anode material has a structural formula shown in formula (I-1)
The compounds shown.
3. The two-dimensional nitrogen-doped nano-graphene material as claimed in claim 1, wherein the nano-graphene material has a structural formula shown in formula (I-2)
The compounds shown.
4. The two-dimensional nitrogen-doped nano-graphene material as claimed in claim 1, wherein the nano-graphene material has a structural formula shown in formula (I-3)
The compounds shown.
5. The two-dimensional nitrogen-doped nano-graphene material as claimed in claim 1, wherein the nano-graphene material has a structural formula shown in formula (I-4)
The compounds shown.
6. A nano graphene lithium battery device is characterized by sequentially consisting of a cathode material, a permeable membrane and an anode material from left to right; the cathode material is a lithium salt material, the anode material is a two-dimensional nitrogen-doped nano graphene material, and the structure is as shown in formula (I)
Shown; the mass ratio of the anode to cathode materials was 1: 1.
7. The nano-graphene lithium battery device according to claim 6, wherein the two-dimensional nitrogen-doped nano-graphene material is a compound having a structural formula as any one of formula (I-1), formula (I-2), formula (I-3) or formula (I-4).
8. The nano-graphene lithium battery device according to claim 6, wherein the lithium salt material is lithium cobalt oxide.
9. The nano-graphene lithium battery device according to claim 6, wherein the permeable membrane is a polyolefin porous membrane.
10. The nano-graphene lithium battery device according to claim 6, wherein the cathode material has a thickness of 1-2mm, the permeable membrane has a thickness of 0.5-1mm, and the anode material has a thickness of 1-2 mm.
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