Application of anode material in improvement of oxidation-reduction potential and electrochromic device

Abstract

The invention discloses application of an anode material in improvement of oxidation-reduction potential and an electrochromic device, and belongs to the technical field of electrochromic materials. The general formula of the anode material is # imgabs0 #, wherein R5 and R10 are independently selected from any electron withdrawing group; r11 and R12 are independently selected from H or any electron withdrawing group; r1, R2, R3, R4, R6, R7, R8 and R9 are independently selected from H, F, Cl, Br, I, CN, NO2, alkyl or alkoxy. Compared with a conventional anode material, the anode material has the advantages that the electron obtaining capacity is weakened, the electron losing capacity is enhanced, the potential difference absolute value of an electrochromic solution prepared from the anode material and 4, 4 '-dipyridyl is increased, the transmittance of a device in an initial state is improved, and the response time is shortened.

Description

Technical Field

[0001] The present invention relates to the technical field of electrochromic materials, and in particular to an application of an anode material in improving oxidation-reduction potential and an electrochromic device. Background Art

[0002] The existing electrochromic mirror products based on organic small molecule technology have a low redox potential of the anode electrochromic material used, and the absolute value of the potential difference (Φanode-Φanode) of the electrochromic solution prepared by the anode material and the 4,4'-bipyridine cathode material is small. Applying a voltage less than 1.0V to the electrochromic device prepared by the existing anode and cathode materials can color the device. The low redox potential brings about problems such as low initial maximum transmittance of the device, dark initial appearance color, and long fading response time. The application scenarios are limited, and it is difficult to meet the requirements for appearance color and application performance of the electrochromic device prepared by it after bonding with the waveguide lens module.

[0003] In view of this, the present invention is proposed. Summary of the invention

[0004] The object of the present invention is to provide an application of an anode material in improving the redox potential and an electrochromic device to solve or improve the above technical problems.

[0005] The present invention can be implemented like this:

[0006] In a first aspect, the present invention provides an application of an anode material in improving redox potential, wherein the general formula of the anode material is:

[0007] Among them, R5 and R 10 are independently selected from any electron withdrawing group; R 11 and R 112 Independently selected from H or any electron withdrawing group; R1, R2, R3, R4, R6, R7, R8 and R9 are all independently selected from H, F, Cl, Br, I, CN, NO2, alkyl or alkoxy.

[0008] In an alternative embodiment, R5 and R 10 Independently selected from phenyl.

[0009] In an alternative embodiment, R 11 and R 12 Independently selected from trihalomethyl or cyano.

[0010] In an alternative embodiment, R5 and R 10 All are phenyl, R1, R2, R3, R4, R6, R7, R8, R9, R 11 and R 12All are H;

[0011] The structural formula of the anode material is:

[0012] In an optional embodiment, the preparation of the above-mentioned anode material includes: vacuum drying 5,10-dimethyl-5,10-dihydrophenazine with bromobenzene, NaOtBu, HPtBu3BF4, and Pd2(dba)3CHCl3, and then adding dry toluene under a protective atmosphere, heating and reacting; after the reaction is completed, water is added to quench to obtain a reaction mixture; after washing the reaction mixture, chromatography is performed with DCM / petroleum as eluent to obtain the anode material.

[0013] In an alternative embodiment, R5 and R 10 All are phenyl, R 11 and R 12 All are trihalomethyl, and R1, R2, R3, R4, R6, R7, R8 and R9 are all H.

[0014] In an optional embodiment, the structural formula of the anode material is:

[0015] In an optional embodiment, the preparation method of the above-mentioned anode material includes: vacuum drying 5,10-dimethyl-5,10-dihydrophenazine with bromobenzene, NaOtBu, HPtBu3BF4, and Pd2(dba)3CHCl3, and then adding trifluoromethylbenzene under a protective atmosphere, heating and reacting; after the reaction is completed, water is added to quench to obtain a reaction mixture; after washing the reaction mixture, chromatography is performed with DCM / petroleum as an eluent to obtain an anode material.

[0016] In an alternative embodiment, R5 and R 10 All are phenyl, R 11 and R 12 are all cyano, R1, R2, R3, R4, R6, R7, R8 and R9 are all H;

[0017] The structural formula of the anode material is:

[0018] In an optional embodiment, the preparation of the above-mentioned anode material includes: vacuum drying 5,10-dimethyl-5,10-dihydrophenazine with bromobenzene, NaOtBu, HPtBu3BF4, and Pd2(dba)3CHCl3, and then adding benzonitrile under a protective atmosphere, heating and reacting; after the reaction is completed, water is added to quench to obtain a reaction mixture; after washing the reaction mixture, chromatography is performed with DCM / petroleum as an eluent to obtain an anode material.

[0019] In an optional embodiment, the preparation of the above 5,10-dimethyl-5,10-dihydrophenazine comprises: subjecting phenazine and sodium dithionite to a reflux reaction in a mixed solution of ethanol and water, and cooling.

[0020] In a second aspect, the present invention provides an electrochromic device, which includes an anode electrochromic material and a cathode electrochromic material, wherein the anode electrochromic material includes the anode material in the application of any of the aforementioned embodiments, and the cathode electrochromic material includes 4,4'-bipyridine.

[0021] In an alternative embodiment, the molar ratio of the anode material to 4,4'-bipyridine is 30:(24-26).

[0022] The beneficial effects of the present invention include:

[0023] The present invention introduces electron-withdrawing groups into the N atom of the dimethylphenazine anode color-changing material for modification. The modified anode electrochromic material has a weakened electron-acquiring ability and an enhanced electron-losing ability. When the power is on, the difficulty of the process of changing the dimethylphenazine or phenothiazine material from 0 valence to +1 valence increases, while when the power is off, the process of changing from +1 valence to 0 valence and obtaining electrons becomes easier, thereby increasing its redox potential, that is, the redox potential has a larger positive value than before the modification, thereby increasing the absolute value of the potential difference (Φ anode - Φ anode) of the electrochromic solution prepared by the modified anode material and cathode material (such as 4,4'-bipyridine), thereby increasing the initial maximum transmittance of the electrochromic device prepared with this material, reducing the initial appearance color of the device, and shortening the response time of the electrochromic device. The electrochromic device prepared with the modified above-mentioned material can meet the requirements for appearance and application performance after being bonded to the waveguide lens module. BRIEF DESCRIPTION OF THE DRAWINGS

[0024] In order to more clearly illustrate the technical solutions of the embodiments of the present invention, the drawings required for use in the embodiments are briefly introduced below. It should be understood that the following drawings only show certain embodiments of the present invention and therefore should not be regarded as limiting the scope. For ordinary technicians in this field, other related drawings can be obtained based on these drawings without creative work.

[0025] Figure 1 This is the CV diagram of the anode material prepared in Example 1;

[0026] Figure 2 This is the CV diagram of the anode material prepared in Example 2;

[0027] Figure 3 This is the CV diagram of the anode material prepared in Example 3. DETAILED DESCRIPTION

[0028] In order to make the purpose, technical scheme and advantages of the embodiments of the present invention clearer, the technical scheme in the embodiments of the present invention will be described clearly and completely below. If the specific conditions are not specified in the embodiments, they are carried out according to conventional conditions or conditions recommended by the manufacturer. If the manufacturer of the reagents or instruments used is not specified, they are all conventional products that can be purchased commercially.

[0029] The application of the anode material provided by the present invention in improving the redox potential and the electrochromic device are described in detail below.

[0030] The present invention provides an application of an anode material in improving redox potential. The general formula of the anode material is:

[0031] Among them, R5 and R 10 are independently selected from any electron withdrawing group; R 11 and R 112 Independently selected from H or any electron withdrawing group; R1, R2, R3, R4, R6, R7, R8 and R9 are all independently selected from H, F, Cl, Br, I, CN, NO2, alkyl or alkoxy.

[0032] In some optional embodiments, R5 and R 10 In some typical embodiments, R5 and R 10 All are phenyl.

[0033] For example, R5 and R 10 All are phenyl, R1, R2, R3, R4, R6, R7, R8, R9, R 11 and R 12 Taking H as an example, the corresponding anode material structure is: It is denoted as compound A, namely 5,10-diphenyl-5,10-dihydrophenazine.

[0034] In some optional embodiments, the preparation of compound A may include: vacuum drying 5,10-dimethyl-5,10-dihydrophenazine with bromobenzene, NaOtBu, HPtBu3BF4, and Pd2(dba)3CHCl3, then adding dry toluene under a protective atmosphere, heating and reacting; after the reaction is completed, quenching with water to obtain a reaction mixture; washing the reaction mixture, and chromatography with DCM / petroleum as eluent to obtain an anode material.

[0035] It should be noted that the 5,10-dimethyl-5,10-dihydrophenazine (DHPZ) mentioned in the present invention can be prepared by referring to the following method: phenazine and sodium dithionite are subjected to reflux reaction in a mixed solution of ethanol and water, and cooled. In addition, 5,10-dimethyl-5,10-dihydrophenazine can also be purchased directly.

[0036] In some optional embodiments, R 11 and R 12 In some typical embodiments, R 11 and R 12 are all trihalomethyl (such as trifluoromethyl), or R 11 and R 12 All are cyano.

[0037] For example, R5 and R 10 All are phenyl, R 11 and R 12 For example, R1, R2, R3, R4, R6, R7, R8 and R9 are all trihalomethyl groups, and R1, R2, R3, R4, R6, R7, R8 and R9 are all H. 11 and R 12 When all are trifluoromethyl, the structural formula of the anode material is: It is designated as compound B, namely 5,10-bis(4-(trifluoromethyl)phenyl)-5,10-dihydrophenazine.

[0038] In some optional embodiments, the preparation method of compound B may include: vacuum drying 5,10-dimethyl-5,10-dihydrophenazine with bromobenzene, NaOtBu, HPtBu3BF4, and Pd2(dba)3CHCl3, then adding trifluoromethylbenzene under a protective atmosphere, heating and reacting; after the reaction is completed, quenching with water to obtain a reaction mixture; washing the reaction mixture, and performing chromatography with DCM / petroleum as eluent to obtain an anode material.

[0039] For example, R5 and R 10 All are phenyl, R 11 and R 12 All are cyano, R 11 , R2, R3, R4, R6, R7, R8 and R9 are all H. The structural formula of the anode material is: It is recorded as compound C, namely 4,4'-(phenazine-5,10-diyl)dibenzonitrile.

[0040] In some optional embodiments, the preparation of compound C may include: vacuum drying 5,10-dimethyl-5,10-dihydrophenazine with bromobenzene, NaOtBu, HPtBu3BF4, and Pd2(dba)3CHCl3, then adding benzonitrile under a protective atmosphere, heating and reacting; after the reaction is completed, quenching with water to obtain a reaction mixture; washing the reaction mixture, and performing chromatography with DCM / petroleum as an eluent to obtain an anode material.

[0041] As mentioned above, the present invention modifies the N atom of the dimethylphenazine anode color-changing material by introducing an electron-withdrawing group. The modified anode electrochromic material has a weakened ability to gain electrons and an enhanced ability to lose electrons. When the power is on, the difficulty of the process of changing the dimethylphenazine or phenothiazine material from 0 valence to +1 valence increases, while when the power is off, the process of changing from +1 valence to 0 valence and obtaining electrons becomes easier, thereby increasing its redox potential, that is, the redox potential has a larger positive value than before the modification, thereby increasing the absolute value of the potential difference (Φ anode - Φ anode) of the electrochromic solution prepared by the modified anode material and cathode material (such as 4,4'-bipyridine), thereby increasing the initial maximum transmittance of the electrochromic device prepared with this material, reducing the initial appearance color of the device, and shortening the response time of the electrochromic device. The electrochromic device prepared with the modified above-mentioned material can meet the requirements for appearance and application performance after being bonded to the waveguide lens module.

[0042] Correspondingly, the present invention further provides an electrochromic device, which includes an anode electrochromic material and a cathode electrochromic material, wherein the anode electrochromic material includes the anode material provided by the present invention, and the cathode electrochromic material includes 4,4'-bipyridine.

[0043] In some optional embodiments, the molar ratio of the anode material to 4,4'-bipyridine may be 30:(24-26), such as 30:24, 30:25 or 30:26.

[0044] In some optional embodiments, the initial maximum transmittance of the electrochromic device is ≥90%, and the fading time is ≤9s.

[0045] The features and performance of the present invention are further described in detail below in conjunction with the embodiments.

[0046] Example 1

[0047] This embodiment provides a 5,10-diphenyl-5,10-dihydrophenazine, and the preparation method thereof is as follows:

[0048] Step 1: Phenazine (2.5 g, 14 mmoL) and sodium dithionite (25 g, 140 mmoL) were placed in a flask respectively; a mixed solution of ethanol and water (volume ratio of 80:250) was added to the flask for reflux reaction (85°C, 8 h). After the reaction was completed, the reaction mixture was cooled to room temperature to obtain a green solid, which was filtered and washed three times with ethanol and water to obtain a light green powder DHPZ.

[0049] Step 2: Add the above-obtained DHPZ (2 g) together with bromobenzene (3.1 g, 20 mmoL), NaOtBu (5.74 g, 59 mmoL), HPtBu3BF4 (580 mg, 2 mmoL), and Pd2(dba)3CHCl3 (102 mg, 1 mmoL) to a 250 mL double-necked round-bottom flask and vacuum dry for 30 min. After drying, add dry toluene (60 mL) to the flask under nitrogen protection, heat to 115 ° C, stir for 24 h, and quench with water after the reaction is completed. Wash the reaction mixture three times with dichloromethane (DCM) to extract the product. Use DCM / petroleum as the eluent and obtain the purified product as a white powder by chromatography, i.e., compound A.

[0050] The yield of compound A obtained by the method is about 81%, which is about 11% higher than the yield of the compound synthesized by the prior art.

[0051] The target product obtained above was characterized by nuclear magnetic hydrogen spectrum data, and the data results are as follows: 1 HNMR (400 MHz, DMSO-d6) δ7.18 (m, 8H), 7.06 (m, 2H), 6.28 (m, 4H), 5.82 (m, 4H). The data showed that the product was indeed 5,10-diphenyl-5,10-dihydrophenazine.

[0052] Example 2

[0053] This embodiment provides a 5,10-bis(4-(trifluoromethyl)phenyl)-5,10-dihydrophenazine, and the preparation method thereof is as follows:

[0054] Step 1: Same as Example 1.

[0055] Step 2: Take DHPZ (1.0 g) obtained in step 1, add bromobenzene (1.5 g, 10 mmoL), NaOtBu (2.87 g, 30 mmoL), HPtBu3BF4 (290 mg, 1 mmoL), and Pd2(dba)3CHCl3 (52 mg, 0.5 mmoL) to a double-necked round-bottom flask and vacuum dry for 30 min. After drying, add trifluoromethylbenzene (30 mL) to the flask under nitrogen protection, heat to 115 ° C, and stir for 24 h. After the reaction is completed, add water to quench. Wash the reaction mixture three times with dichloromethane (DCM) to extract the product. Use DCM / petroleum as eluent and obtain the purified product as a white powder by chromatography, i.e., compound B.

[0056] The yield of compound B obtained by the method is about 85%, which is about 4% higher than the yield of the compound synthesized by the prior art.

[0057] The target product obtained above was characterized by nuclear magnetic hydrogen spectrum data, and the data results are as follows: 1 HNMR (500 MHz, DMSO-d6) δ = 7.33 (d, J = 10 Hz, 4H), 6.97 (d, J = 10 Hz, 4H), 6.34 (m, 4H), 5.67 (m, 4H). The data showed that the product was indeed 5,10-bis(4-(trifluoromethyl)phenyl)-5,10-dihydrophenazine.

[0058] Example 3

[0059] This embodiment provides a 4,4'-(phenazine-5,10-diyl)dibenzonitrile, and its preparation method is as follows:

[0060] Step 1: Same as Example 1.

[0061] Step 2: Add DHPZ (1.2 g) obtained in step 1, bromobenzene (1.5 g, 10 mmoL), NaOtBu (2.87 g, 30 mmoL), HPtBu3BF4 (290 mg, 1 mmoL), and Pd2(dba)3CHCl3 (52 mg, 0.5 mmoL) to a double-necked round-bottom flask and vacuum dry for 30 min. After drying, add benzonitrile (40 mL) to the flask under nitrogen protection, heat to 115 ° C, stir for 24 h, and quench with water after the reaction is completed. Wash the reaction mixture three times with dichloromethane (DCM) to extract the product. Use DCM / petroleum as the eluent and obtain the purified product yellow powder, i.e., compound C, by chromatography.

[0062] The yield of compound C obtained by the method is about 68%, which is about 2% higher than the yield of the compound synthesized by the prior art.

[0063] The target product obtained above was characterized by H NMR data, and the data results were as follows: 1H NMR (500 MHz, DMSO-d6), δ=6.96 (d, J=10 Hz, 4H), 6.71 (d, J=10 Hz, 4H), 6.40 (m, 4H), 5.70 (m, 4H). The data showed that this product was indeed 4,4'-(phenazine-5,10-diyl)dibenzonitrile.

[0064] Test Example 1

[0065] The three anode materials prepared in Examples 1 to 3 were respectively used in an electrochemical workstation, with AgCl / Ag as the reference electrode, to measure their redox potentials by cyclic voltammetry, and the CV diagrams of the three anode materials were obtained as shown in FIG. Figures 1 to 3 shown.

[0066] Combination Figures 1 to 3 It can be proved that the redox potential of the synthesized anode material is between +0.59V and +0.67V, which indicates that the introduction of electron-withdrawing groups on the N atom of dimethylphenazine for modification improves its redox potential, which is at least 0.3V higher than that of the anode phenazine material in the prior art.

[0067] Test Example 2

[0068] The three anode materials prepared in Examples 1 to 3 are taken as examples, and dimethylphenazine is taken as a comparative example.

[0069] The performance of each anode material was tested according to the following method: 30mmol of anode material and cathode electrochromic material 4,4'-bipyridine (25mmol) and ferrocene tetrafluoroborate buffer (5mmol) were dissolved in propylene carbonate solution to obtain an electrochromic solution. Two pieces of 25mm×25mm×0.21mm soda-lime ITO glass were used, with the ITO side facing up, and the frame glue was applied at the left and right edges of the glass at a 2mm offset using thermosetting frame glue, leaving a 2mm filling port. After bonding, the glass box was prepared by baking at 120℃ for 1h. The glue width of the prepared device was 2mm, and the box thickness was controlled to be 125μm. The above electrochromic solution was filled into the ITO glass box by vacuum filling, and sealed and cured with UV glue. A total of 3 devices were prepared for testing. The maximum transmittance and chromaticity values ​​(L*, a*, b*) of the center points of the 3 devices were tested using a color haze meter. Metal clips connected to the power wires were fixed at both ends of the device to test the response time of the 3 devices when powered on at 1.2V. The results are shown in Tables 1 to 4.

[0070] Table 1 Test results

[0071] serial number Initial transmittance L* a* b* Coloring time Fading time 1 80％ 93.24 -3.29 13.28 9s 12s 2 81％ 92.93 -2.97 13.43 8s 11s 3 80％ 93.62 -3.06 11.19 8s 12s

[0072] From the distribution of L*, a*, and b* values ​​in Table 1, it can be seen that the electrochromic device prepared by the comparative example has an initial yellowish color, an initial maximum transmittance ≤81%, and a fading time ≥11s, which cannot meet the actual application requirements of the product.

[0073] Table 2 Test results

[0074] serial number Initial transmittance L* a* b* Coloring time Fading time 1 90％ 95.61 -2.03 10.72 8s 9s 2 90％ 95.39 -2.39 12.13 7s 8s 3 92％ 95.55 -2.27 11.17 8s 9s

[0075] From the distribution of L*, a*, and b* values ​​in Table 2, it can be seen that, compared with the comparative example, the initial yellow color of the electrochromic device prepared in Example 1 is improved, the initial maximum transmittance is ≥90%, and the fading time is ≤9s, indicating that the introduction of electron-withdrawing groups increases the redox potential of the anode material, increases the initial maximum transmittance, and shortens the fading time.

[0076] Table 3 Test results

[0077] serial number Initial transmittance L* a* b* Coloring time Fading time 1 93％ 96.36 -1.81 10.03 7s 8s 2 92％ 96.83 -1.76 9.46 7s 7s 3 93％ 97.35 -2.01 9.97 6s 7s

[0078] From the distribution of L*, a*, and b* values ​​in Table 3, it can be seen that, compared with the comparative example, the initial yellow color of the electrochromic device prepared in Example 2 is also improved, the initial maximum transmittance is ≥92%, and the fading time is ≤8s, which also indicates that the introduction of electron-withdrawing groups increases the redox potential of the anode material, increases the initial maximum transmittance, and shortens the fading time.

[0079] Table 4 Test results

[0080] serial number Initial transmittance L* a* b* Coloring time Fading time 1 91％ 96.77 -1.93 9.23 6s 6s 2 92％ 96.13 -1.58 9.15 7s 5s 3 93％ 96.62 -1.91 9.68 8s 7s

[0081] From the distribution of L*, a*, and b* values ​​in Table 4, it can be seen that, compared with the comparative example, the initial yellow color of the electrochromic device prepared in Example 3 is improved, the initial maximum transmittance is ≥91%, and the fading time is ≤7s, which also indicates that the introduction of electron-withdrawing groups increases the redox potential of the anode material, increases the initial maximum transmittance, and shortens the fading time.

[0082] In summary, the present invention introduces electron-withdrawing groups into the N atom of the dimethylphenazine anodic electrochromic material for modification, thereby improving the redox potential of the anodic electrochromic material, thereby improving the initial maximum transmittance of the electrochromic device prepared with the material, reducing the initial appearance color of the device, shortening the response time of the electrochromic device, and meeting the requirements for appearance color and application performance of the electrochromic device prepared from the material after bonding with a waveguide lens module, and has broad application prospects.

[0083] The above description is only a preferred embodiment of the present invention and is not intended to limit the present invention. For those skilled in the art, the present invention may have various modifications and variations. Any modification, equivalent replacement, improvement, etc. made within the spirit and principle of the present invention shall be included in the protection scope of the present invention.

Claims

1. An application of an anode material in improving redox potential, characterized in that: The general formula of the anode material is: Among them, R5 and R 10 are independently selected from any electron withdrawing group; R 11 and R 112 Independently selected from H or any electron withdrawing group; R1, R2, R3, R4, R6, R7, R8 and R9 are all independently selected from H, F, Cl, Br, I, CN, NO2, alkyl or alkoxy.

2. The use according to claim 1, characterized in that: R5 and R 10 Independently selected from phenyl.

3. The use according to claim 1 or 2, characterized in that: R 11 and R 12 Independently selected from trihalomethyl or cyano.

4. The use according to claim 2, characterized in that: R5 and R 10 All are phenyl, R1, R2, R3, R4, R6, R7, R8, R9, R 11 and R 12 All are H; The structural formula of the anode material is:

5. The use according to claim 4, characterized in that: The preparation of the anode material comprises: vacuum drying 5,10-dimethyl-5,10-dihydrophenazine, bromobenzene, NaOtBu, HPtBu3BF4, and Pd2(dba)3CHCl3, then adding dry toluene under a protective atmosphere, heating and reacting; after the reaction is completed, water is added to quench to obtain a reaction mixture; after washing the reaction mixture, chromatography is performed using DCM / petroleum as an eluent to obtain the anode material; Preferably, the preparation of 5,10-dimethyl-5,10-dihydrophenazine comprises: subjecting phenazine and sodium dithionite to a reflux reaction in a mixed solution of ethanol and water, and cooling.

6. The use according to claim 3, characterized in that: R5 and R 10 All are phenyl, R 11 and R 12 are all trihalomethyl, R1, R2, R3, R4, R6, R7, R8 and R9 are all H; Preferably, the structural formula of the anode material is:

7. The use according to claim 6, characterized in that: The structural formula is The preparation of the anode material comprises: vacuum drying 5,10-dimethyl-5,10-dihydrophenazine with bromobenzene, NaOtBu, HPtBu3BF4, and Pd2(dba)3CHCl3, then adding trifluoromethylbenzene under a protective atmosphere, heating and reacting; after the reaction is completed, water is added to quench to obtain a reaction mixture; after washing the reaction mixture, chromatography is performed using DCM / petroleum as an eluent to obtain the anode material; Preferably, the preparation of 5,10-dimethyl-5,10-dihydrophenazine comprises: subjecting phenazine and sodium dithionite to a reflux reaction in a mixed solution of ethanol and water, and cooling.

8. The use according to claim 3, characterized in that: R5 and R 10 All are phenyl, R 11 and R 12 are all cyano, R1, R2, R3, R4, R6, R7, R8 and R9 are all H; The structural formula of the anode material is:

9. The use according to claim 8, characterized in that: The preparation of the anode material comprises: vacuum drying 5,10-dimethyl-5,10-dihydrophenazine, bromobenzene, NaOtBu, HPtBu3BF4, and Pd2(dba)3CHCl3, then adding benzonitrile under a protective atmosphere, heating and reacting; after the reaction is completed, water is added to quench to obtain a reaction mixture; after washing the reaction mixture, chromatography is performed using DCM / petroleum as an eluent to obtain the anode material; Preferably, the preparation of 5,10-dimethyl-5,10-dihydrophenazine comprises: subjecting phenazine and sodium dithionite to a reflux reaction in a mixed solution of ethanol and water, and cooling.

10. An electrochromic device, characterized in that: The electrochromic device comprises an anode electrochromic material and a cathode electrochromic material, wherein the anode electrochromic material comprises the anode material in the application according to any one of claims 1 to 9, and the cathode electrochromic material comprises 4,4'-bipyridine; Preferably, the molar ratio of the anode material to the 4,4'-bipyridine is 30:(24-26).

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