Conjugated imidazole organic electrode material and preparation method and application thereof

Abstract

The invention belongs to the field of aqueous ion battery electrode materials, and particularly relates to a conjugated imidazole organic electrode material and a preparation method and application thereof. The conjugated imidazole compound provided by the invention contains a plurality of redox active sites, so that the conjugated imidazole compound has relatively high theoretical capacity. When the conjugated imidazole compound is used as an electrode material of an aqueous ion battery, high specific capacity and excellent rate capability and cycling stability are realized. The conjugated imidazole compound designed by the invention improves the capacity of the organic electrode material of the ion battery, has the advantages of low unit cost, long cycle life, safety, environmental protection and the like, and has a wide application prospect in the aspect of high-energy-density energy storage batteries.

Description

Technical Field

[0001] This invention belongs to the field of electrode materials for aqueous ion batteries, specifically relating to a conjugated imidazole organic electrode material, its preparation method, and its application. Background Technology

[0002] As the global energy structure accelerates its transition to renewable energy sources such as wind and solar power, the development of large-scale, low-cost, and highly safe electrochemical energy storage technologies has become crucial for ensuring the stable operation of power grids. Against this backdrop, aqueous zinc-ion batteries, with their inherent safety, abundant resources, environmental friendliness, and low cost, are considered a significant development direction for replacing existing lithium-ion battery technologies in the field of large-scale energy storage. Currently, the core bottleneck restricting further performance improvements in zinc-ion batteries lies primarily in the cathode material.

[0003] While the most widely studied inorganic cathode materials (such as manganese-based and vanadium-based oxides) have shown some capacity potential, their inherent crystal structure in Zn... 2+ Repeated insertion / extraction processes can easily lead to irreversible phase transitions and collapses, resulting in rapid capacity decay. Simultaneously, the dissolution and loss of materials in aqueous electrolytes (such as manganese dissolution) and the toxicity limitations of certain elements (such as vanadium) severely impact the battery's cycle life and environmental compatibility. More critically, the narrow ion channels in the rigid crystal structure of these materials restrict the processing of Zn. 2+ The rapid migration of these molecules limits the rate performance of the battery.

[0004] In contrast, organic cathode materials, through molecular design, utilize active functional groups such as carbonyl and imine groups to interact with Zn. 2+ The efficient and reversible coordination reaction provides a novel approach to solving the aforementioned problems. Its flexible molecular framework effectively buffers the stress caused by ion insertion / extraction, exhibiting superior structural stability and longer cycle potential. The designability of its molecular structure allows for precise control of electrochemical performance (such as voltage and capacity). Furthermore, its primary composition of elements such as C, H, O, and N ensures sustainable resource availability and a low environmental burden. However, the inherently low conductivity and solubility of organic materials in electrolytes remain challenges that must be overcome for their industrial application. Therefore, there is an urgent need to develop a novel, highly efficient organic cathode material that can fully leverage its inherent advantages such as structural flexibility, resource sustainability, and molecular designability. Through innovative material design and structural optimization, it can effectively address the issues of insufficient conductivity and solubility, thereby providing an advanced and reliable cathode solution for constructing next-generation high-performance, long-life zinc-ion batteries. Summary of the Invention

[0005] The purpose of this invention is to provide a class of conjugated imidazole organic electrode materials, their preparation methods, and their application in zinc-ion batteries, in order to solve the problems of low capacity and poor cycle stability that have always existed in inorganic electrode materials.

[0006] The conjugated imidazole organic electrode material of this invention is selected from one of the following three compounds: .

[0007] Among them, R1-R5 are all taken from 0-2 of the methyl and chloro groups.

[0008] Using the conjugated imidazole organic electrode material of this invention as an organic cathode material for zinc-ion batteries, the abundant C=N active sites in the molecule endow it with a high theoretical specific capacity for achieving multi-electron reversible reactions. The highly stable conjugated framework and reversible coordination energy storage mechanism fundamentally guarantee the material's excellent structural stability and ultra-long cycle life. Simultaneously, this extended conjugated system not only provides an ideal channel for intrinsic electron conduction, but its open molecular configuration also creates favorable conditions for the rapid transport of zinc ions, thus giving the material excellent rate performance. Furthermore, this material is entirely composed of widely available lightweight elements (C, H, N), eliminating expensive or toxic metal resources, and possesses significant advantages in both low cost and environmental friendliness, showing broad application prospects in high-energy-density energy storage batteries.

[0009] The preparation method of the conjugated imidazole organic electrode material of the present invention includes the following steps: (1) Using o-phenylenediamine and ferric chloride as raw materials, an aqueous solution containing a certain amount of ferric chloride was added to an aqueous solution of o-phenylenediamine and stirred vigorously until the color changed from black to red. After standing, the supernatant was discarded, and this process was repeated several times. Then, the red precipitate was separated by filtration and washed several times with deionized water to ensure the removal of iron ions. The product was then placed in a 70 °C drying oven for vacuum drying to obtain a red powder, which is the intermediate 2,3-diaminophenazine (DAP).

[0010] The molar ratio of ferric chloride to o-phenylenediamine is 0.08:0.1.

[0011] (2) Using DAP and benzaldehyde or their derivatives as raw materials, the two are dissolved in an organic solvent and ultrasonically mixed. Under nitrogen protection, the mixture is heated to reflux in an oil bath. After the reaction is complete, the reaction solution is filtered and washed several times with ethanol and water until the filtrate is colorless. The filtrate is then dried under vacuum for 4 hours. The dried product is then taken out and heated to reflux with 30 wt.% nitric acid. After the reaction is complete, the product is filtered while hot and washed with water and ethanol until the filtrate is colorless. The obtained product is then dried under vacuum for 4 hours. The obtained product is then recrystallized with DMF, filtered, and dried overnight to obtain the product 2-phenyl-1H-imidazo[4,5-b]phenazine (PIP) or its derivatives.

[0012] Benzaldehyde or its derivatives are derived from one of the following: benzaldehyde, terephthalaldehyde, trimesonaldehyde, 2-methylbenzaldehyde, 3-methylbenzaldehyde, 4-methylbenzaldehyde, 2,3-dimethylbenzaldehyde, 2,4-dimethylbenzaldehyde, 2,5-dimethylbenzaldehyde, 2,6-dimethylbenzaldehyde, 3,4-dimethylbenzaldehyde, 3,5-dimethylbenzaldehyde, 1,4-benzaldehyde, 2-methyl-1,4-benzaldehyde, 2,5-dimethyl-1,4-benzaldehyde, 2,3,5,6-tetramethyl-1,4-benzaldehyde, 1,3,5-trimethylbenzaldehyde, 1,3,5-trimethylbenzaldehyde, 2,4,6-trimethyl-1,3,5-trimethylbenzaldehyde, and 2,4,6-trichloro-1,3,5-trimethylbenzaldehyde.

[0013] The molar ratio of DAP to benzaldehyde or its derivatives is 1:1-3:1, the organic solvent is N-methyl-2-pyrrolidone (NMP), dimethyl sulfoxide (DMSO) or N,N-dimethylformamide (DMF); the oil bath heating temperature is 80℃-160℃, and the reaction time is 3 h-72 h.

[0014] The conjugated imidazole organic electrode material of the present invention is applied to the positive electrode material of an aqueous zinc-ion battery. The preparation method of the positive electrode material is as follows: the conjugated imidazole organic electrode material, conductive additives and binders are uniformly dispersed in a solvent and coated on a current collector, vacuum dried to obtain organic positive electrode material, cut into sheets and assembled into a battery.

[0015] Furthermore, the mass ratio of conjugated imidazole organic electrode material, conductive additive, and binder is 3–9:1–6:0–1; the conductive additive is carbon black, Super P, Ketjen black, activated carbon, graphene, or carbon nanotubes; the binder is polyvinylidene fluoride, polytetrafluoroethylene, polyvinyl alcohol, or styrene-butadiene rubber; the current collector is 300-mesh stainless steel mesh, titanium mesh, carbon paper, aluminum foil, or copper foil; the vacuum drying temperature is 60–110℃, and the drying time is 4–18 h.

[0016] Beneficial Effects: Using the organic material provided by this invention as the organic cathode material for zinc-ion batteries, the abundant C=N active sites in the molecule endow it with a high theoretical specific capacity for achieving multi-electron reversible reactions. The highly stable conjugated framework and reversible coordination energy storage mechanism fundamentally guarantee the material's excellent structural stability and ultra-long cycle life. Simultaneously, this extended conjugated system not only provides an ideal channel for intrinsic electron conduction, but its open molecular configuration also creates favorable conditions for the rapid transport of zinc ions, thus giving the material excellent rate performance. Furthermore, this material is entirely composed of widely available lightweight elements (C, H, N), eliminating expensive or toxic metal resources, and possesses significant advantages in both low cost and environmental friendliness, providing an ideal material solution for developing next-generation high-performance, sustainable green energy storage systems. Attached Figure Description

[0017] Figure 1 This is the 1H NMR spectrum of the material prepared in Example 1.

[0018] Figure 2 This is the infrared spectrum of the material prepared in Example 1.

[0019] Figure 3 This is the CV curve of the zinc-ion battery prepared with the materials in Example 1.

[0020] Figure 4 This is a rate performance graph of the zinc-ion battery prepared with the material in Example 1 at different current densities.

[0021] Figure 5 These are the charge-discharge curves of the zinc-ion battery prepared using the materials in Example 1.

[0022] Figure 6 This is a cycle stability diagram of the zinc-ion battery prepared using the materials in Example 1.

[0023] Figure 7 This is the 1H NMR spectrum of the material prepared in Example 6.

[0024] Figure 8 This is the infrared spectrum of the material prepared in Example 6.

[0025] Figure 9 This is the CV curve of the zinc-ion battery prepared with the materials in Example 6.

[0026] Figure 10 This is a rate performance graph of the zinc-ion battery prepared with the materials in Example 6 at different current densities.

[0027] Figure 11 These are the charge-discharge curves of the zinc-ion battery prepared using the materials in Example 6. Detailed Implementation

[0028] To make the objectives, technical solutions, and advantages of this invention clearer, the invention will be further described in detail below with reference to embodiments. It should be understood that the specific embodiments described herein are merely illustrative and not intended to limit the invention. Furthermore, the technical features described in the various embodiments of the invention below can be combined with each other as long as they do not conflict with each other.

[0029] Example 1: The synthesis route of organic electrode material II is as follows:

[0030] (1) Weigh 10.814 g (0.1 mol) o-phenylenediamine into a 1000 mL beaker, add 400 mL of water, heat to 50 °C and stir to dissolve. Then weigh 12.97 g (0.08 mol) FeCl3 into a 500 mL beaker, add 200 mL of water and stir to dissolve at room temperature. After the o-phenylenediamine is fully dissolved, quickly pour in the aqueous solution containing FeCl3 and stir vigorously at 50 °C until the solution color changes from black to red. After standing for 4 h to precipitate, pour off the supernatant, add 800 mL of water, stir to dissolve, and let stand for 4 h to precipitate. Repeat the process of adding water, stirring, standing and pouring off the supernatant 4 times. Then centrifuge the red precipitate and wash it 5 times with deionized water to ensure the removal of iron ions. Then place the product in an 80 °C drying oven and vacuum dry to obtain reddish-brown DAP powder.

[0031] (2) Place 0.84 g (4 mmol) DAP and 0.268 g (2 mmol) terephthalaldehyde in a 100 mL three-necked flask, add 50 mL of dimethyl sulfoxide (DMSO) and sonicate until homogeneous. Heat at 120 °C for 72 h under N2 atmosphere. After the reaction is complete, filter the reaction solution and wash it several times with ethanol and water until the filtrate is colorless. Dry the filter cake in a vacuum drying oven at 80 °C for 12 h. The dried product was then removed and dissolved in 50 mL of 30 wt.% nitric acid. The solution was heated to reflux at 140 °C for 3 h. After the reaction was complete, the mixture was filtered while hot and washed with water and ethanol until the filtrate was colorless. The obtained product was then dried in a vacuum oven at 120 °C for 3 h, dissolved in 50 mL of N,N-dimethylformamide (DMF), and heated to reflux at 140 °C for 3 h. After the reaction was complete, the solution was placed in an ice bath for 4 h. The reaction solution was then filtered and washed several times with ethanol and water until the filtrate was colorless. The filter cake was dried in a vacuum oven at 80 °C for 12 h. This yielded the product 1,4-bis(1H-imidazo[4,5-b]phenazin-2-yl)benzene (BIPB) (yield 89%).

[0032] The liquid NMR spectrum of BIPB is as follows: Figure 1As shown in the figure. Since BIPB has a symmetrical structure, it can be concluded that there are a total of five types of hydrogen, including NH. However, the imidazole NH structure generally does not show a peak in the 1H NMR spectrum. The peaks of the remaining four types of hydrogen correspond one-to-one with the test data, proving the successful synthesis of BIPB.

[0033] BIPB infrared spectrum as follows Figure 2 As shown in the figure, distinct C=N and CN peaks appear at 3480 cm⁻¹. -1 The appearance of a unique NH peak at this point confirms the synthesis of the BIPB substance.

[0034] The conductivity of the synthesized BIPB was measured using the four-probe method and found to be 6.228 × 10⁻⁶. -6 S cm -1 It has a higher conductivity than previously reported organic materials (in 10). -9 -10 -12 S cm -1 The difference between the two values ​​indicates that the conductivity of this material is significantly improved compared to conventional organic materials.

[0035] BIPB was used as a cathode material for zinc-ion batteries. Organic cathode material, Ketjen black, and polyvinylidene fluoride (mass ratio 4.5:4.5:1) were uniformly dispersed in N-methyl-2-pyrrolidone (NMP) and uniformly coated (the active material loading of the cut circular electrode sheet was approximately 5 mg / cm³). -2 On carbon paper, the mixture is then vacuum dried at 60°C for 4 hours and then vacuum dried at 110°C overnight to obtain an organic cathode.

[0036] A zinc-ion battery was assembled using an organic positive electrode, a zinc sheet as the negative electrode, a glass fiber membrane as the separator, and a 1M ZnSO4 solution as the electrolyte. The voltage testing window is 0.1V to 1.3V.

[0037] Figure 3 Cyclic voltammetry curves of the zinc-ion battery assembled for BIPB at different scan rates are shown in the figure. The redox peaks remain well-formed. Two pairs of redox peaks can be seen in the figure. Due to their similar potentials, the two sets of peaks partially overlap. The average potential of both sets of peaks is around 0.76V. With the increase of scan rate, the peak current increases slightly and shows a regular change, indicating that the redox reaction has good stability.

[0038] Figure 4 Rate performance graphs of zinc-ion batteries assembled with this material at different current densities. (0.05, 0.1, 0.2, 0.5, 1.0, 2.0, and 5.0 A g) -1 The reversible capacities corresponding to the current densities are 318, 294, 290, 287, 283, 279, and 275 mAh g, respectively. -1When the current density recovers to 0.05 A g - At 1 hour, the battery's reversible capacity recovered to 307 mAh g. -1 This represents 96.4% of its initial capacity. Meanwhile, the material at 0.05 A g... -1 The reversible capacity at current density is close to the theoretical capacity of 320 mAhg. -1 From the corresponding charge-discharge curves ( Figure 5 The data also shows that the battery has a stable discharge-charge voltage platform, proving that BIPB has high specific capacity and excellent rate performance.

[0039] Figure 6 Zinc-ion batteries assembled using this material operate at 0.1 A g. -1 Cycling performance at current density. The first discharge capacity after battery activation is 294 mAh g. -1 After 20,000 cycles, the capacity is 287 mA hg. -1 The capacity retention rate is 97.6%, and the coulombic efficiency is close to 100%. This indicates that the battery has excellent cycle stability. Example

[0040] The benzaldehyde derivative was replaced with benzaldehyde instead of terephthalaldehyde, and the molar ratio of DAP to benzaldehyde was changed to 1:1. The other conditions were the same as in Example 1. The final yield of the product 2-phenyl-1H-imidazo[4,5-b]phenazine (PIP) was 92%.

[0041] Using this material as the positive electrode, a zinc-ion battery was assembled, with the same assembly conditions and process as in Example 1. This battery was tested at 5 Ag... -1 Electrochemical charge-discharge cycle performance at current density: the first discharge capacity after battery activation is 290 mAh g⁻¹. -1 After 20,000 cycles, the capacity is 286 mA hg. -1 The capacity retention rate is 98.6%, and the coulomb efficiency is close to 100%. Example

[0042] The benzaldehyde derivative was replaced with 4-methylbenzaldehyde, the molar ratio of DAP to 4-methylbenzaldehyde was changed to 3:1, and the other conditions were the same as in Example 1. The final yield of the product PIP derivative was 96%.

[0043] Using this material as the positive electrode, a zinc-ion battery was assembled, with the same assembly conditions and process as in Example 1. This battery was tested at 0.01 A g. -1 Cycling at current density, the first discharge capacity after battery activation is 316 mAh g. -1After 20,000 cycles, the capacity is 298 mA hg. -1 The capacity retention rate is 94.3%, and the coulomb efficiency is close to 100%. Example

[0044] The benzaldehyde derivative was replaced with 2-methyl-1,4-benzaldehyde, and the other conditions were the same as in Example 1. The final yield of the BIPB derivative was 87.3%.

[0045] The remaining steps are the same as in Example 1.

[0046] Using this material as the positive electrode, a zinc-ion battery was assembled, with the same assembly conditions and process as in Example 1. This battery was tested at 5 Ag... -1 Electrochemical charge-discharge cycle performance at current density: the first discharge capacity after battery activation is 283 mAh g⁻¹. -1 After 20,000 cycles, the capacity is 262 mA hg. -1 The capacity retention rate is 92.6%, and the coulomb efficiency is close to 100%. Example

[0047] The benzaldehyde derivative was replaced with 2,3,5,6-tetramethyl-1,4-benzaldehyde, and the other conditions were the same as in Example 1. The final yield of the BIPB derivative was 84.8%.

[0048] Using this material as the positive electrode, a zinc-ion battery was assembled, with the same assembly conditions and process as in Example 1. This battery was tested at 5 Ag... -1 Electrochemical charge-discharge cycle performance at current density: the first discharge capacity after battery activation is 285 mAh g⁻¹. -1 After 20,000 cycles, the capacity is 271 mA hg. -1 The capacity retention rate is 95.1%, and the coulomb efficiency is close to 100%. Example

[0049] The synthesis route of organic electrode material II is as follows:

[0050] The DAP synthesis method is the same as in Example 1.

[0051] 6 mmol DAP and 2 mmol trimesin were placed in a 100 mL three-necked flask, and 50 mL N,N-dimethylformamide (DMF) was added and sonicated until homogeneous. The mixture was heated at 120 °C for 72 h under a N2 atmosphere. After the reaction was complete, the reaction solution was filtered and washed several times with ethanol and water until the filtrate was colorless. The filter cake was dried in a vacuum drying oven at 80 °C for 12 h. The dried product was then removed and heated under reflux at 140 °C for 3 h with 50 mL of 30 wt.% nitric acid. After the reaction was complete, the mixture was filtered while hot and washed with water and ethanol until the filtrate was colorless. The filter cake was dried in a vacuum drying oven at 80 °C for 12 h. The product 1,3,5-tris(1H-imidazo[4,5-b]phenazin-2-yl)benzene (BTIP) was obtained (yield 93.8%).

[0052] The liquid-state hydrogen NMR spectrum of BTIP is as follows: Figure 7 As shown. Since BTIP has a symmetrical structure, the specific analysis is the same as in Example 1. Four sets of signal peaks correspond one-to-one with the test data, proving the successful synthesis of BTIP.

[0053] BTIP infrared spectrum as follows Figure 8 As shown in the figure, very obvious C=N and CN peaks appear, and a unique NH peak appears at 3480 cm⁻¹, proving the synthesis of BTIP.

[0054] BTIP was used as the positive electrode material for zinc-ion batteries, and the batteries were assembled using the same steps as in Example 1.

[0055] Figure 9 Cyclic voltammetry curves of the zinc-ion battery assembled for BTIP at different scan rates are shown. The redox peaks remain well-formed, and a pair of distinct redox peaks can be seen in the figure. The average potential is around 0.78 V. With the increase of scan rate, the peak current increases slightly and shows a regular change, indicating that the redox reaction has good stability.

[0056] Figure 10 Rate performance graphs of zinc-ion batteries assembled with this material at different current densities. (0.05, 0.1, 0.2, 0.5, 1.0, 2.0, and 5.0 A g) -1 The reversible capacities corresponding to the current densities are 282, 277, 273, 269, 266, 263 and 257 mAh g, respectively. -1 When the current density recovers to 0.05 A g -1 At that time, the battery's reversible capacity recovered to 278 mAh g. -1 It represents 98.5% of its initial capacity. After 20,000 cycles, the capacity retention rate is 97.6%. This is based on the corresponding charge-discharge curves ( Figure 11The data also shows that the battery has a stable discharge-charge voltage platform, proving that BTIP has high specific capacity and excellent rate performance. Example

[0057] The benzaldehyde derivative was replaced with 2,4,6-trimethyl-1,3,5-benzyltricarboxaldehyde, and the other conditions were the same as in Example 6. The final yield of the BTIP derivative was 84.1%.

[0058] The remaining steps are the same as in Example 6.

[0059] The zinc-ion battery assembled with this material has a reversible capacity of 357 mAh g at a current density of 0.05. -1 After 20,000 cycles, the capacity retention rate was 98.1%. Example

[0060] The benzaldehyde derivative was replaced with 2,4,6-trichloro-1,3,5-benzyltricarboxaldehyde, and the other conditions were the same as in Example 6. The final yield of the BTIP derivative was 91.3%. The zinc-ion battery assembled with this material had a reversible capacity of 382 mAh g at a current density of 0.05. -1 After 20,000 cycles, the capacity retention rate was 97.3%.

Claims

1. A method for preparing a conjugated imidazole-based organic electrode material, characterized in that, The preparation method steps are as follows: (1) Add the aqueous solution containing ferric chloride to the aqueous solution of o-phenylenediamine, stir vigorously at 50°C until the color changes from black to red, let stand, pour off the supernatant, repeat this process 4 times, then filter the red precipitate, wash with deionized water to ensure the removal of iron ions, and then place the product in a drying oven at 70°C to dry under vacuum to obtain a red powder, which is the intermediate 2,3-diaminophenazine DAP; (2) Dissolve DAP and benzaldehyde or its derivatives in an organic solvent and mix thoroughly by ultrasonic vibration. Under nitrogen protection, heat under reflux in an oil bath. After the reaction is complete, filter the reaction solution and wash with ethanol and water until the filtrate is colorless. Dry under vacuum for 4 hours. Then take out the dried product and heat under reflux with 30 wt.% nitric acid. After the reaction is complete, filter while hot and wash with water and ethanol until the filtrate is colorless. Dry the obtained product under vacuum for 4 hours. Then recrystallize the obtained product with DMF, filter, and dry overnight to obtain the product 2-phenyl-1H-imidazo[4,5-b]phenazine (PIP) or its derivatives.

2. The method for preparing the conjugated imidazole organic electrode material as described in claim 1, characterized in that, In step (1), the molar ratio of ferric chloride to o-phenylenediamine is 0.08:0.

1.

3. The method for preparing the conjugated imidazole organic electrode material as described in claim 1, characterized in that, In step (2), benzaldehyde or its derivatives are taken from one of the following: benzaldehyde, terephthalaldehyde, trimesonaldehyde, 2-methylbenzaldehyde, 3-methylbenzaldehyde, 4-methylbenzaldehyde, 2,3-dimethylbenzaldehyde, 2,4-dimethylbenzaldehyde, 2,5-dimethylbenzaldehyde, 2,6-dimethylbenzaldehyde, 3,4-dimethylbenzaldehyde, 3,5-dimethylbenzaldehyde, 1,4-benzaldehyde, 2-methyl-1,4-benzaldehyde, 2,5-dimethyl-1,4-benzaldehyde, 2,3,5,6-tetramethyl-1,4-benzaldehyde, 1,3,5-trimethylbenzaldehyde, 1,3,5-trimethylbenzaldehyde, 2,4,6-trimethyl-1,3,5-trimethylbenzaldehyde, and 2,4,6-trichloro-1,3,5-trimethylbenzaldehyde.

4. The method for preparing the conjugated imidazole organic electrode material as described in claim 1, characterized in that, In step (2), the molar ratio of DAP to benzaldehyde or its derivative is 1:1-3:1; the organic solvent is N-methyl-2-pyrrolidone, dimethyl sulfoxide or N,N-dimethylformamide.

5. The method for preparing the conjugated imidazole organic electrode material as described in claim 1, characterized in that, In step (2), the oil bath heating temperature is 80℃-160℃, and the reflux reaction time is 3 h-72 h.

6. A conjugated imidazole organic electrode material prepared by the method described in claim 1, characterized in that, The conjugated imidazole organic electrode material is selected from one of the following three types of compounds: ， Among them, R1-R5 are all taken from 0-2 of the methyl and chloro groups.

7. An application of a conjugated imidazole organic electrode material prepared by the method described in claim 1, characterized in that, The conjugated imidazole organic electrode material is used as the positive electrode material for aqueous zinc-ion batteries.

8. The application of the conjugated imidazole organic electrode material as described in claim 7, characterized in that, Conjugated imidazole organic electrode materials, conductive additives, and binders are uniformly dispersed in a solvent and coated onto a current collector. After vacuum drying, aqueous zinc-ion battery cathode materials are obtained, cut into sheets, and assembled into batteries.

9. The application of the conjugated imidazole organic electrode material as described in claim 8, characterized in that, The mass ratio of conjugated imidazole organic electrode material, conductive additive, and binder is 3–9:1–6:0–1.

10. The application of the conjugated imidazole organic electrode material as described in claim 8, characterized in that, The conductive additives are carbon black, Super P, Ketjen black, activated carbon, graphene or carbon nanotubes; the binders are polyvinylidene fluoride, polytetrafluoroethylene, polyvinyl alcohol or styrene-butadiene rubber; the current collectors are 300-mesh stainless steel mesh, titanium mesh, carbon paper, aluminum foil or copper foil; the vacuum drying temperature is 60-110℃; and the drying time is 4-18h.

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