A conductive polymer material, a preparation method and applications

Abstract

The present application relates to the field of organic electrochromic materials, and particularly relates to a conductive polymer material, a preparation method and application.The main chain of the conductive polymer material is composed of aryl groups, and the side chain is a phenothiazine structural unit; the phenothiazine serves as an anode material in a small-molecule electrochromic system and exhibits excellent device performance; however, the device is in a liquid state and has a risk of leakage.The present application introduces the phenothiazine structural unit into a polyaromatic hydrocarbon structure with conductivity, thereby guaranteeing the performance of the phenothiazine itself and good conductivity; as a polymer, the material can be obtained by adjusting the structure, and the material can be solution-processed into a thin film, so as to be applied to a sandwich-structured solid-state device, and the application scenarios of the electrochromic device are expanded.

Description

Technical Field

[0001] This invention relates to the field of organic electrochromic materials, specifically to a conductive polymer material, its preparation method, and its application. Background Technology

[0002] Electrochromism is a phenomenon in which colors can change reversibly under voltage regulation. Due to its low energy consumption, memory properties, simple structure, and low cost, electrochromic devices have long been considered promising for commercial passive display applications, such as electronic tags and electronic paper. Since the 1970s, research on electrochromic devices has primarily focused on inorganic materials such as tungsten oxide. However, the development of inorganic electrochromic devices has also revealed some drawbacks that have hindered large-scale commercialization. The most significant problems are slow switching response and limited color options, which are mainly determined by the inherent characteristics of inorganic materials.

[0003] Phenothiazines are a class of aromatic heterocyclic compounds containing electron-rich N and S atoms. Their large π-conjugated systems exhibit high electron delocalization, and the molecules possess strong rigidity and coplanarity. When combined with cathode-colored violet to form a complementary electrochromic device, it demonstrates excellent reversible coloring and fading properties, significantly enhancing its electrochromic performance. (Functional Materials, Vol. 6 (41), 2010, pp. 1102-1105). However, as a small molecule material, its presence in solution within an electrochromic device poses a risk of leakage. Summary of the Invention

[0004] In view of the many shortcomings of existing electrochromic materials, this invention provides a conductive polymer material, a preparation method, and an application.

[0005] The technical solution of the present invention is achieved in the following way: a conductive polymer material is provided, the molecular formula of which is as follows:

[0006]

[0007] Where n is a positive integer; n = 1 ~ 100.

[0008] Ar is aryl or substituted aryl.

[0009] Preferably, the Ar is selected from the following:

[0010]

[0011] Wherein, R is selected from H, alkyl (C m H 2m+1 (m is a natural number from 1 to 20), alkoxy groups, oligoether groups ( .

[0012] Preferably, the conductive polymer material is selected from the following:

[0013]

[0014] .

[0015] In a second aspect of the present invention, a method for preparing the conductive polymer material is provided, the preparation process of which is as follows:

[0016]

[0017] Specifically, the steps include the following:

[0018] S1, 1,4-dihydroxy-2,5-bis(bromomethyl)benzene (A1) and 2 equivalents of phenothiazine (A2) underwent a catalytic reaction in a solvent, and the intermediate compound A3 was obtained by separation and purification.

[0019] S2. The intermediate compound A3 undergoes an esterification reaction with 2 equivalents of p-toluenesulfonyl chloride to give compound A4;

[0020] S3. The compound A4 and the aryl diboronate derivative undergo a Suzuki coupling reaction under the conditions of tetrakis(triphenylphosphine)palladium as catalyst and toluene as solvent to obtain the target polymer (P).

[0021] Preferably, in step S1, the reaction is carried out in potassium carbonate and dichloromethane overnight at room temperature;

[0022] After the reaction was complete, the mixture was washed three times with water, the organic phase was dried with anhydrous sodium sulfate, concentrated, and separated by column chromatography to obtain the intermediate compound A3.

[0023] In a third aspect of the invention, the application of the aforementioned conductive polymer material in electrochromic devices is also provided.

[0024] The beneficial effects are as follows:

[0025] Phenothiazine exhibits excellent device performance as an anode material in small-molecule electrochromic systems; however, these devices, being liquid-state, pose a risk of leakage. This invention combines the excellent color-changing properties of phenothiazine with a polymer whose main chain has a conjugated system to obtain a polymer material containing phenothiazine functional groups with good conductivity. The side chains are phenothiazine structural units. This invention introduces phenothiazine structural units into a conductive polyaromatic hydrocarbon structure, ensuring both the inherent properties of phenothiazine and good conductivity. As a polymer, by adjusting the structure, a solution-processable thin-film material can be obtained, enabling its application in sandwich-structured solid-state devices and expanding the application scenarios of electrochromic devices. Detailed Implementation

[0026] To make the objectives, technical solutions, and advantages of this invention clearer, the technical solutions of this invention will be clearly and completely described below in conjunction with specific embodiments. Obviously, the described embodiments are only a part of the embodiments of this invention, and not all of them. Based on the embodiments of this invention, all other embodiments obtained by those skilled in the art without creative effort are within the scope of protection of this invention.

[0027] The present invention will be further described in detail below with reference to the embodiments.

[0028] Based on the material synthesis, electrochromic thin film devices were prepared, and their device performance was investigated.

[0029] Fabrication of electrochromic devices:

[0030] Transparent ITO conductive glass cut into different sizes was first soaked in a mixed solvent of ammonia / hydrogen peroxide, then ultrasonically treated sequentially with deionized water, acetone, and isopropanol to obtain cleaned ITO glass. After removal, it was dried with dry nitrogen gas. A polymer sample was dissolved in toluene to prepare a 40 mg / mL solution, which was then spin-coated onto an ITO plate. This was then bonded to another ITO plate with adhesive, and an electrolyte solution was further injected using a liquid-filling method. The color change was observed by applying a voltage. Its electrochromic response time and driving voltage were tested.

[0031] Example 1: Synthesis of P-1, a representative conductive polymer material containing phenathiazide

[0032] The synthesis route is shown below:

[0033]

[0034] 29.5 g (100 mmol) of 1,4-dihydroxy-2,5-bis(bromomethyl)benzene (A1) was reacted with 39.8 g (200 mmol) of phenthiazide (A2) and 41.4 g (300 mmol) of potassium carbonate in 1000 mL of dichloromethane at room temperature overnight. The mixture was washed three times with water, dried over anhydrous sodium sulfate, concentrated, and separated by column chromatography (eluent: dichloromethane to methanol in a volume ratio of 5:1) to give intermediate compound A3. 1 H NMR (500 MHz, Chloroform ) δ 7.35 – 7.06 (m, 12H), 6.97(ddd, J = 15.1, 9.2, 3.2 Hz, 4H), 6.68 (s, 2H), 5.39 (s, 4H), 4.12 (s, 2H).

[0035] 26.6 g (50 mmol) of hydroxyl-containing intermediate A3 and 22.7 g (120 mmol) of p-toluenesulfonyl chloride were dissolved and stirred in 1000 mL of dichloromethane at room temperature. The reaction was monitored by thin-layer chromatography until complete. The mixture was washed three times with saturated sodium bicarbonate aqueous solution, then three times with water, dried over anhydrous sodium sulfate, and concentrated to obtain the crude product. The crude product was subjected to column chromatography in dichloromethane and petroleum ether to obtain 33.6 g of sulfonated intermediate A4. 1 H NMR (500 MHz, Chloroform ) δ 7.81 – 7.65 (m,4H), 7.53 – 7.41 (m, 4H), 7.26 – 7.07 (m, 12H), 7.03 – 6.91 (m, 4H), 6.67 (s,2H), 5.67 (s, 4H), 5.67 (s, 4H), 2.43 (s, 6H).

[0036] 8.41 g (10 mmol) of sulfonated intermediate compound A5 and 5.58 g (10 mmol) of diboronate compound (B1) were dissolved in 250 mL of toluene. 10 mL of 2 mol / L potassium carbonate aqueous solution was added, and the mixture was purged with nitrogen for 30 min. 20 mmol × 1% (0.23 g) of Pd(PPh3)4 was added, and the mixture was heated under reflux and stirred overnight under nitrogen. After cooling to room temperature, the mixture was poured into 500 mL of methanol and filtered to obtain the crude product. The filter cake was successively extracted with methanol, acetone, n-hexane, and chloroform using a Soxhlet extractor to obtain the target polymer P-1. 1 H NMR (500 MHz, Chloroform) δ 7.95 (d, J = 34.4 Hz, 2H), 7.17(dddd, J = 18.5, 15.3, 14.7, 12.6 Hz, 13H), 7.02 – 6.86 (m, 5H), 5.40 (d, J =10.8 Hz, 4H), 4.11 (t, J = 14.8 Hz, 4H), 2.01 – 1.61 (m, 4H), 1.54 – 1.14 (m,17H), 1.02 – 0.72 (m, 6H).

[0037] Example 2: Synthesis of P-2, a representative conductive polymer material containing phenathiazide

[0038]

[0039] 8.41 g (10 mmol) of sulfonated intermediate compound A5 and 5.66 g (10 mmol) of diboronate compound (B2) were dissolved in 250 mL of toluene. 10 mL of 2 mol / L potassium carbonate aqueous solution was added, and the mixture was purged with nitrogen for 30 min. 20 mmol × 1% (0.23 g) of Pd(PPh3)4 was added, and the mixture was heated under reflux and stirred overnight under nitrogen. After cooling to room temperature, the mixture was poured into 500 mL of methanol and filtered to obtain the crude product. The filter cake was successively extracted with methanol, acetone, n-hexane, and chloroform using a Soxhlet extractor to obtain the target polymer P-2. 1 H NMR (500 MHz, Chloroform ) δ 7.90 (s, 1H), 7.43 (s, 1H), 7.27 (s, 1H), 7.24 – 7.04 (m, 12H), 6.95 (s, 4H), 6.66 (s, 1H), 5.34 (d, J =54.8 Hz, 4H), 4.30 (s, 4H), 3.76 (s, 4H), 3.52 (d, J = 15.0 Hz, 8H), 3.39 (s, 6H).

[0040] Example 3: Synthesis of P-3, a representative conductive polymer material containing phenathiazide.

[0041]

[0042] 8.41 g (10 mmol) of sulfonated intermediate compound A5 and 3.80 g (10 mmol) of diboronate compound (B3) were dissolved in 250 mL of toluene. 10 mL of 2 mol / L potassium carbonate aqueous solution was added, and the mixture was purged with nitrogen for 30 min. 20 mmol × 1% (0.23 g) of Pd(PPh3)4 was added, and the mixture was heated under reflux and stirred overnight under nitrogen. After cooling to room temperature, the mixture was poured into 500 mL of methanol and filtered to obtain the crude product. The filter cake was successively extracted with methanol, acetone, n-hexane, and chloroform using a Soxhlet extractor to obtain the target polymer P-3. 1 H NMR (500 MHz, Chloroform) δ 7.99 (dd, J = 14.9, 3.0 Hz, 1H),7.95 – 7.89 (m, 2H), 7.77 (dd, J = 15.0, 2.9 Hz, 1H), 7.66 (dd, J = 15.0, 2.9 Hz, 1H), 7.55 (t, J= 2.9 Hz, 1H), 7.38 (dd, J = 14.9, 3.0 Hz, 1H), 7.29 – 7.07 (m,12H), 6.97 (ddd, J = 15.1, 9.2, 3.2 Hz, 4H), 6.77 (s, 1H), 5.15 (d, J = 25.6 Hz, 4H).

[0043] Example 4: Synthesis of P-4, a representative conductive polymer material containing phenathiazide

[0044]

[0045] 8.41 g (10 mmol) of sulfonated intermediate compound A5 and 5.99 g (10 mmol) of diboronate compound (B4) were dissolved in 250 mL of toluene. 10 mL of 2 mol / L potassium carbonate aqueous solution was added, and the mixture was purged with nitrogen for 30 min. 20 mmol × 1% (0.23 g) of Pd(PPh3)4 was added, and the mixture was heated under reflux and stirred overnight under nitrogen. After cooling to room temperature, the mixture was poured into 500 mL of methanol and filtered to obtain the crude product. The filter cake was successively extracted with methanol, acetone, n-hexane, and chloroform using a Soxhlet extractor to obtain the target polymer P-4. 1 H NMR (500 MHz, Chloroform ) δ 8.18 – 7.56 (m, 7H), 7.48 (s,1H), 7.30 – 7.05 (m, 12H), 6.97 (s, 4H), 5.25 (d, J = 100.5 Hz, 4H), 1.93 (s, 4H), 1.29 (d, J = 35.0 Hz, 22H), 0.89 (s, 6H).

[0046] Example 5: Synthesis of P-5, a representative conductive polymer material containing phenathiazide.

[0047]

[0048] 8.41 g (10 mmol) of sulfonated intermediate compound A5 and 6.22 g (10 mmol) of diboronate compound (B5) were dissolved in 250 mL of toluene. 10 mL of 2 mol / L potassium carbonate aqueous solution was added, and the mixture was purged with nitrogen for 30 min. 20 mmol × 1% (0.23 g) of Pd(PPh3)4 was added, and the mixture was heated under reflux and stirred overnight under nitrogen. After cooling to room temperature, the mixture was poured into 500 mL of methanol and filtered to obtain the crude product. The filter cake was successively extracted with methanol, acetone, n-hexane, and chloroform using a Soxhlet extractor to obtain the target polymer P-5. 1 H NMR (500 MHz, Chloroform) δ 8.21 (s, 1H), 8.02 (d, J = 27.9Hz, 2H), 7.88 (d, J = 14.9 Hz, 2H), 7.74 (s, 1H), 7.56 (s, 1H), 7.50 (s, 1H), 7.28 – 7.03 (m, 12H), 6.94 (s, 4H), 5.39 (d, J = 58.1 Hz, 4H), 3.52 (d, J = 14.9Hz, 8H), 3.36 (d, J = 27.7 Hz, 10H), 2.11 (s, 4H).

[0049] Example 6: Synthesis of P-6, a representative conductive polymer material containing phenathiazide

[0050]

[0051] 8.41 g (10 mmol) of sulfonated intermediate compound A5 and 5.17 g (10 mmol) of diboronate compound (B6) were dissolved in 250 mL of toluene. 10 mL of 2 mol / L potassium carbonate aqueous solution was added, and the mixture was purged with nitrogen for 30 min. 20 mmol × 1% (0.23 g) of Pd(PPh3)4 was added, and the mixture was heated under reflux and stirred overnight under nitrogen. After cooling to room temperature, the mixture was poured into 500 mL of methanol and filtered to obtain the crude product. The filter cake was successively extracted with methanol, acetone, n-hexane, and chloroform using a Soxhlet extractor to obtain the target polymer P-6. 1 H NMR (500 MHz, Chloroform ) δ 8.00 – 7.55 (m, 6H), 7.43 (d, J=14.0 Hz, 2H), 7.29 – 7.04 (m, 12H), 6.97 (s, 4H), 5.24 (d, J = 58.5 Hz, 4H), 4.16 (s, 2H), 1.74 (s, 2H), 1.30 (d, J = 35.0 Hz, 9H), 0.89 (s, 3H).

[0052] Example 7: Synthesis of P-7, a representative conductive polymer material containing phenathiazide.

[0053]

[0054] 8.41 g (10 mmol) of sulfonated intermediate compound A5 and 5.21 g (10 mmol) of diboronate compound (B7) were dissolved in 250 mL of toluene. 10 mL of 2 mol / L potassium carbonate aqueous solution was added, and the mixture was purged with nitrogen for 30 min. 20 mmol × 1% (0.23 g) of Pd(PPh3)4 was added, and the mixture was heated under reflux and stirred overnight under nitrogen. After cooling to room temperature, the mixture was poured into 500 mL of methanol and filtered to obtain the crude product. The filter cake was successively extracted with methanol, acetone, n-hexane, and chloroform using a Soxhlet extractor to obtain the target polymer P-7. 1 H NMR (500 MHz, Chloroform ) δ 7.98 – 7.87 (m, 2H), 7.82 (d, J =15.0 Hz, 1H), 7.66 – 7.54 (m, 3H), 7.44 (ddd, J = 18.9, 15.0, 3.0 Hz, 2H), 7.29– 7.06 (m, 12H), 6.97 (ddd, J = 15.1, 9.2, 3.2 Hz, 4H), 5.28 (d, J = 14.7 Hz, 4H), 4.45 (td, J = 19.0, 0.8 Hz, 2H), 3.71 (td, J = 19.0, 0.8 Hz, 2H), 3.53 (td, J = 6.8, 1.6 Hz, 4H), 3.40 (s, 3H).

[0055] Example 8: Synthesis of P-8, a representative conductive polymer material containing phenathiazide

[0056]

[0057] 8.41 g (10 mmol) of sulfonated intermediate compound A5 and 6.70 g (10 mmol) of diboronate compound (B8) were dissolved in 250 mL of toluene. 10 mL of 2 mol / L potassium carbonate aqueous solution was added, and the mixture was purged with nitrogen for 30 min. 20 mmol × 1% (0.23 g) of Pd(PPh3)4 was added, and the mixture was heated under reflux and stirred overnight under nitrogen. After cooling to room temperature, the mixture was poured into 500 mL of methanol and filtered to obtain the crude product. The filter cake was successively extracted with methanol, acetone, n-hexane, and chloroform using a Soxhlet extractor to obtain the target polymer P-8. 1 H NMR (500 MHz, Chloroform) δ 7.83 (dd, J = 141.4, 96.2 Hz,4H), 7.29 – 7.06 (m, 12H), 6.97 (ddd, J = 15.1, 9.2, 3.2 Hz, 4H), 5.41 (d, J =104.0 Hz, 4H), 4.11 (t, J = 20.3 Hz, 4H), 1.80 (dqd, J = 24.8, 20.1, 2.5 Hz, 4H), 1.58 – 1.13 (m, 18H), 1.03 – 0.71 (m, 6H).

[0058] Example 9: Synthesis of P-9, a representative conductive polymer material containing phenathiazide.

[0059]

[0060] 8.41 g (10 mmol) of sulfonated intermediate compound A5 and 6.78 g (10 mmol) of diboronate compound (B9) were dissolved in 250 mL of toluene. 10 mL of 2 mol / L potassium carbonate aqueous solution was added, and the mixture was purged with nitrogen for 30 min. 20 mmol × 1% (0.23 g) of Pd(PPh3)4 was added, and the mixture was heated under reflux and stirred overnight under nitrogen. After cooling to room temperature, the mixture was poured into 500 mL of methanol and filtered to obtain the crude product. The filter cake was successively extracted with methanol, acetone, n-hexane, and chloroform using a Soxhlet extractor to obtain the target polymer P-9. 1 H NMR (500 MHz, Chloroform) δ 7.85 (dd, J= 103.2, 53.8 Hz,4H), 7.30 – 7.07 (m, 12H), 7.05 – 6.76 (m, 4H), 5.39 (d, J = 83.9 Hz, 4H), 4.31(td, J = 17.7, 1.0 Hz, 4H), 3.76 (td, J = 17.8, 0.9 Hz, 4H), 3.62 – 3.47 (m, 8H), 3.40 (s, 6H).

[0061] Example 10: Synthesis of P-10, a representative conductive polymer material containing phenathiazide.

[0062]

[0063] 8.41 g (10 mmol) of sulfonated intermediate compound A5 and 6.05 g (10 mmol) of diboronate compound (B10) were dissolved in 250 mL of toluene. 10 mL of 2 mol / L potassium carbonate aqueous solution was added, and the mixture was purged with nitrogen for 30 min. 20 mmol × 1% (0.23 g) of Pd(PPh3)4 was added, and the mixture was heated under reflux and stirred overnight under nitrogen. After cooling to room temperature, the mixture was poured into 500 mL of methanol and filtered to obtain the crude product. The filter cake was successively extracted with methanol, acetone, n-hexane, and chloroform using a Soxhlet extractor to obtain the target polymer P-10. 1 H NMR (500 MHz, Chloroform) δ 7.74 (d, J = 186.6 Hz, 1H), 7.32– 7.04 (m, 3H), 7.04 – 6.77 (m, 1H), 5.48 (d, J = 173.3 Hz, 1H), 4.11 (t, J =20.3 Hz, 1H), 1.80 (dqd, J = 24.8, 20.1, 2.5 Hz, 1H), 1.59 – 1.05 (m, 4H), 1.04– 0.67 (m, 1H).

[0064] Example 11: Synthesis of P-11, a representative conductive polymer material containing phenathiazide.

[0065]

[0066] 8.41 g (10 mmol) of sulfonated intermediate compound A5 and 6.28 g (10 mmol) of diboronate compound (B10) were dissolved in 250 mL of toluene. 10 mL of 2 mol / L potassium carbonate aqueous solution was added, and the mixture was purged with nitrogen for 30 min. 20 mmol × 1% (0.23 g) of Pd(PPh3)4 was added, and the mixture was heated under reflux and stirred overnight under nitrogen. After cooling to room temperature, the mixture was poured into 500 mL of methanol and filtered to obtain the crude product. The filter cake was successively extracted with methanol, acetone, n-hexane, and chloroform using a Soxhlet extractor to obtain the target polymer P-11. 1 H NMR (500 MHz, Chloroform) δ 7.93 (s, 1H), 7.53 (s, 1H), 7.30 – 7.06 (m, 3H), 6.97 (s, 1H), 5.45 (d, J = 156.8 Hz, 1H), 4.31 (s, 1H), 3.77 (s, 1H), 3.53 (d, J = 15.0 Hz, 2H), 3.40 (s, 1H).

[0067] Example 12: Synthesis of P-12, a representative conductive polymer material containing phenathiazide.

[0068]

[0069] 8.41 g (10 mmol) of sulfonated intermediate compound A5 and 4.48 g (10 mmol) of diboronate compound (B12) were dissolved in 250 mL of toluene. 10 mL of 2 mol / L potassium carbonate aqueous solution was added, and the mixture was purged with nitrogen for 30 min. 20 mmol × 1% (0.23 g) of Pd(PPh3)4 was added, and the mixture was heated under reflux and stirred overnight under nitrogen. After cooling to room temperature, the mixture was poured into 500 mL of methanol and filtered to obtain the crude product. The filter cake was successively extracted with methanol, acetone, n-hexane, and chloroform using a Soxhlet extractor to obtain the target polymer P-12. 1 H NMR (500 MHz, Chloroform ) δ 7.93 (s, 1H), 7.32 – 7.06 (m,13H), 6.97 (ddd, J = 15.1, 9.2, 3.2 Hz, 4H), 6.53 (s, 1H), 5.40 (d, J = 144.9 Hz, 4H), 2.68 (t, J = 22.9 Hz, 2H), 1.50 (dqd,J = 25.6, 21.8, 2.9 Hz, 2H), 1.34 –1.12 (m, 10H), 1.02 – 0.70 (m, 3H).

[0070] Example 13: Fabrication of Electrochromic Devices

[0071] The aforementioned synthesized materials P-1, P-2, P-3, P-4, P-5, P-6, P-7, P-8, P-9, P-10, P-11, and P-12 were prepared into a 40 mg / mL toluene solution for later use.

[0072] Transparent ITO conductive glass cut to 3cm*5cm was first soaked in a mixed solvent of ammonia / hydrogen peroxide, then ultrasonically treated with deionized water, acetone, and isopropanol to obtain cleaned ITO glass. After removal, it was dried with dry nitrogen gas. The previously prepared solutions of P-1, P-2, P-3, P-4, P-5, P-6, P-7, P-8, P-9, P-10, P-11, and P-12 were spin-coated onto an ITO plate. This was then bonded to another ITO plate with adhesive. Further, a solution containing 0.1mol / L tetrabutylammonium hexafluorophosphate and 0.01mol / L ethyl amethyst hexafluorophosphate in propylene carbonate electrolyte was poured in using the injection method, and the plate was sealed with UV adhesive. A voltage was applied between the electrodes, and the color change of the electrochromic device was observed. The specific results are shown in Table 1 below.

[0073] Table 1

[0074]

[0075] The polymer structures listed above are only a partial representation; other conductive polymer materials containing the same concept are all within the scope of this patent protection.

[0076] Although embodiments of the present invention have been shown and described above, it is understood that the above embodiments are exemplary and should not be construed as limiting the present invention. Those skilled in the art can make changes, modifications, substitutions and variations to the above embodiments within the scope of the present invention.

Claims

1. A conductive polymer material, characterized in that, The molecular formula is as follows: Where n is a positive integer; The Ar is selected from any one of the following B-1 to B-7: R is selected from H, alkyl, alkoxy, and oligoether groups.

2. The conductive polymer material according to claim 1, characterized in that, Choose from any one of the following pages: P-1 to P-12 。 3. A method for preparing the conductive polymer material according to any one of claims 1-2, characterized in that, The preparation process is as follows: Specifically, the steps include the following: S1, 1,4-dihydroxy-2,5-bis(bromomethyl)benzene (A1), and 2 equivalents of phenothiazine (A2) underwent a catalytic reaction in a solvent, followed by separation and purification to obtain intermediate compound A3; S2. The intermediate compound A3 undergoes an esterification reaction with 2 equivalents of p-toluenesulfonyl chloride to yield compound A4; S3. Compound A4 and compound B undergo a Suzuki coupling reaction under the conditions of tetra-triphenylphosphine palladium as catalyst and toluene as solvent to obtain the target polymer (P).

4. The preparation method according to claim 3, characterized in that, In step S1, the reaction is carried out in potassium carbonate and dichloromethane overnight at room temperature. After the reaction was complete, the mixture was washed three times with water, the organic phase was dried with anhydrous sodium sulfate, concentrated, and separated by column chromatography to obtain the intermediate compound A3.

5. The application of the conductive polymer material according to any one of claims 1-2 in electrochromic devices.

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