CN115490836A - Electrochromic polymer capable of reversibly changing from yellow to high transmission and application thereof - Google Patents
Electrochromic polymer capable of reversibly changing from yellow to high transmission and application thereof Download PDFInfo
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- C08G2261/324—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain condensed
- C08G2261/3243—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain condensed containing one or more sulfur atoms as the only heteroatom, e.g. benzothiophene
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Abstract
The invention discloses a soluble electrochromic polymer capable of realizing reversible conversion from yellow to high transmission and an electrochromic polymer film thereof. The invention adopts arylation polycondensation to prepare the electrochromic polymer. The invention also provides an electrochromic polymer film prepared from the electrochromic polymer, which can realize stable and reversible transition from neutral state yellow to oxidation state high transmission and has potential application value in the fields of displays, intelligent windows, mobile phone shells and the like.
Description
Technical Field
The invention relates to an electrochromic polymer with reversible conversion from yellow to high transmission, a preparation method thereof and application thereof in preparing an electrochromic polymer film.
Background
"Electrochromism" (EC) refers to a phenomenon in which optical properties of a material, such as transmittance, reflectance, absorption, and the like, are changed stably and reversibly under an applied electric field, and macroscopically, the optical properties are expressed as reversible changes in color and transparency.
Electrochromic materials are mainly divided into inorganic electrochromic materials, organic micromolecular electrochromic materials and polymer electrochromic materials. Among them, the polymer electrochromic material (PEC) has a great application value in the fields of smart windows, flat displays, information labels and the like due to its characteristics of easy structure modification, controllable energy band, good processability, excellent electrochromic comprehensive performance and the like, and is widely researched. PEC materials can be generally divided into electrochemically polymerized PEC materials and chemically polymerized PEC materials, depending on the manner of polymerization. Chemically polymerized PEC materials generally have good solution processability and can be made into thin films by spray coating, spin coating, ink printing, screen printing, and the like, allowing large area, low cost production of PEC devices and are therefore of interest.
Over the past decade, solution processable PEC materials have rapidly developed, and a wide variety of solution processable PEC materials are designed to be synthesized. Among them, the soluble PEC material for color to high transmission conversion is widely studied, while the CMY (cyan, magenta, and yellow) tricolor to high transmission material is the subject of intensive research, mainly because the tricolor to high transmission material is the key to achieve full color regulation. However, at present, there are very few three primary to high transmission materials and the electrochromic properties are not good. Further, it is very difficult to design and synthesize materials with yellow to high transmittance, and the technical patents of materials with yellow to high transmittance having good application prospects are concentrated in developed countries such as europe and the united states, and domestic technical patents having independent intellectual property rights in this field are relatively lacking. Therefore, there is a need to develop new high performance, yellow to high transmission solution processable PEC materials with promising industrial application prospects.
Disclosure of Invention
The first purpose of the invention is to provide an electrochromic polymer, which can realize stable and reversible transformation from neutral yellow to oxidized yellow with high transmission under the action of an electric field and has good solubility in organic solvents.
It is a second object of the present invention to provide a method for preparing an electrochromic polymer.
It is a third object of the present invention to provide an electrochromic polymer film.
The purpose of the invention is realized by the following technical scheme:
in a first aspect, the present invention provides an electrochromic polymer of formula (I),
in the formula: r is C 4 ～C 30 Alkyl groups of (a);
the number average molecular weight Mn of the electrochromic polymer is = 2000-200000, the molecular weight is controlled by the polymerization reaction time, and the polydispersity D = 1.0-5.0.
Preferably, the number average molecular weight Mn of the electrochromic polymer is from 5000 to 50000.
Preferably, R is C 6 -C 20 Alkyl group of (1). More preferably C 8 Alkyl, especially 2-ethylhexyl.
In a second aspect, the invention provides a preparation method of an electrochromic polymer shown in formula (I), wherein the electrochromic polymer is prepared by arylation polycondensation of a monomer 1 and a monomer 2;
in the formula 1, R is as defined in formula (I).
The preparation method of the polymer shown in the formula (I) specifically comprises the following steps: adding the monomer 1, the monomer 2, organic acid, inorganic weak base and palladium catalyst into an organic solvent, carrying out polymerization reaction for 6-72 h at 80-160 ℃, and carrying out post-treatment on the obtained reaction solution to obtain an electrochromic polymer shown in a formula (I); the ratio of the amounts of the monomer 1, the monomer 2, the organic acid, the weak inorganic base and the palladium catalyst is (1).
Monomer 1 reference (adv. Mater.2010,22, 4949-4953), monomers 1 of different carbon chain lengths were synthesized by condensation reactions using alcohols of different lengths and alkyl bromides.
Preferably, the organic acid is one or a mixture of two of pivalic acid and 1-adamantanecarboxylic acid (preferably pivalic acid).
Preferably, the inorganic weak base is one or a mixture of two or more of potassium carbonate, sodium carbonate, cesium carbonate, potassium bicarbonate and sodium bicarbonate (preferably potassium carbonate).
Preferably, the palladium catalyst is one or a mixture of two or more of palladium acetate, palladium dichlorobis (triphenylphosphine) and tris (dibenzylideneacetone) dipalladium (0) -chloroform adduct (preferably palladium acetate).
Preferably, the organic solvent is one or a mixture of two or more of tetrahydrofuran, N-methylpyrrolidone, N-dimethylformamide and N, N-dimethylacetamide (preferably N, N-dimethylacetamide).
Preferably, the reaction temperature of the polymerization reaction is 120 to 140 ℃.
Preferably, the reaction time of the polymerization reaction is 12 to 36 hours.
Further, the volume of the organic solvent is 1 to 20L/mol (preferably 5L/mol) based on the total amount of the monomer 1 and the monomer 2 represented by the formula (I).
Further, the post-treatment comprises the following steps: pouring the reaction liquid into methanol, filtering, drying a filter cake, performing Soxhlet extraction sequentially by using the methanol, the acetone, the hexane and the trichloromethane, collecting a polymer dissolved in the trichloromethane, and performing spin drying to obtain the electrochromic polymer shown in the formula (I).
In a third aspect, the present invention provides a use of the above electrochromic polymer for the preparation of an electrochromic polymer film.
Preferably, the electrochromic polymer film is obtained by processing the electrochromic polymer into a film from a solution.
Specifically, the application is as follows: dissolving the electrochromic polymer in a solvent to obtain a polymer solution, and then coating the polymer solution on a conductive substrate to obtain the electrochromic polymer film; the solvent is one or a mixture of more than two of dichloromethane, trichloromethane, tetrahydrofuran, toluene and N, N-dimethylformamide; the concentration of the electrochromic polymer in the polymer solution is 5-30 mg/mL (preferably 15 mg/mL).
In the present invention, the coating may be spray coating, spin coating, screen printing, or the like. The conductive substrate can be ITO glass, FTO glass, an ITO-PET substrate or an FTO-PET substrate and the like.
The electrochromic polymer film obtained by the invention has potential application value in the fields of intelligent windows, displays, electronic paper and the like.
Compared with the prior art, the invention has the following beneficial effects:
(1) The polymer has good solubility in common organic solvents, and large-area preparation of thin film materials can be realized by a solution processing method.
(2) The polymer film prepared by the invention can realize the stable and reversible transition from yellow in a neutral state to high transmission in an oxidation state, and has potential application value in the fields of displays, intelligent windows, mobile phone shells and the like.
Drawings
FIG. 1: optical absorption of the polymer film prepared in example 1 at different voltages;
FIG. 2: the transmittance versus time curve for a multi-potential step from 0 to 1.3V at a specific wavelength for the polymer film prepared in example 1.
Detailed Description
The technical solution of the present invention is further described below with specific examples, but the scope of the present invention is not limited thereto.
Example 1
The synthesis and molecular structure of the conjugated polymer used are shown below:
the polymer was synthesized as follows:
m1 (0.44g, 1eq.) and M2 (0.28g, 1eq.) were added to a 10mL DMAc solution containing pivalic acid (30mg, 0.3eq.) and potassium carbonate (345mg, 2.5eq.), and finally Pd (OAc) 2 (7mg, 0.03eq.) catalyst, and reacted at 130 ℃ for 24 hours. After the reaction is finished, pouring the solution into 200mL of methanol, filtering, taking a filter cake, drying, sequentially carrying out Soxhlet extraction by using methanol, acetone, hexane and chloroform, collecting a polymer dissolved in the chloroform, and carrying out spin drying. Polymer GPC test results (Mn =18.0kda, d = 2.76).
Preparation of polymer film:
and dissolving the polymer in chloroform to obtain a polymer solution, and spin-coating the polymer solution on an ITO substrate to form a film, wherein the concentration of the solution is 15mg/mL, the rotating speed is 800r/min, and the time is 1min. The volume of the solution was 0.5mL after spin coating.
Electrochromic properties of the resulting polymer films: the polymer films were subjected to colorimetric tests in the neutral state of 0V and the oxidized state of 1.3V, resulting in neutral state L =91.98, a =0.13, b =82.8, oxidized state L =78.10, a = -3.84, b = -10.32. The electrochemical workstation and the ultraviolet-visible spectrophotometer combined device are used for respectively testing the ultraviolet-visible light absorption of the prepared film under different voltages, the transmissivity of the prepared film under specific wavelength and the time relationship in a 0.1M tetrabutylammonium hexafluorophosphate/acetonitrile solution, and the data processing result is shown in figures 1 and 2. From fig. 1 and the chromaticity test, it can be seen that the polymer film is yellow in the neutral state at 0V and high in transmission after oxidation at a voltage of 1.3V. From FIG. 2, it can be seen that the film had a contrast of 57.3% at 446 nm. Meanwhile, the coloring time and the fading time of the polymer film were 1.9s and 0.4s, respectively. A series of tests such as electrochemistry, an ultraviolet-visible spectrophotometer and a colorimeter show that the prepared soluble electrochromic conjugated polymer can realize reversible conversion from yellow to high transmission, and has excellent electrochromic comprehensive performance.
Claims (10)
1. An electrochromic polymer of formula (I),
in the formula: r is C 4 ～C 30 Alkyl groups of (a);
the number average molecular weight Mn of the electrochromic polymer is between 2000 and 200000.
2. A process for the preparation of an electrochromic polymer of formula (I) according to claim 1, characterized in that it is:
adding the monomer 1, the monomer 2, organic acid, inorganic weak base and palladium catalyst into an organic solvent, carrying out polymerization reaction for 6-72 h at 80-160 ℃, and carrying out post-treatment on the obtained reaction solution to obtain an electrochromic polymer shown in a formula (I); the mass ratio of the monomer 1 to the monomer 2 to the organic acid to the inorganic weak base to the palladium catalyst is 1;
in the formula 1 (I), R is C 4 ～C 30 The alkyl group of (1).
3. A process for the preparation of an electrochromic polymer of formula (I) according to claim 2, characterized in that: the organic acid is one or a mixture of two of pivalic acid and 1-adamantanecarboxylic acid.
4. A process for the preparation of an electrochromic polymer of formula (I) according to claim 2, characterized in that: the weak inorganic base is one or a mixture of more than two of potassium carbonate, sodium carbonate, cesium carbonate, potassium bicarbonate and sodium bicarbonate.
5. A process for the preparation of an electrochromic polymer of formula (I) according to claim 2, characterized in that: the palladium catalyst is one or a mixture of more than two of palladium acetate, dichlorobis (triphenylphosphine) palladium and tris (dibenzylideneacetone) dipalladium (0) -chloroform adduct.
6. A process for the preparation of an electrochromic polymer of formula (I) according to claim 2, characterized in that: the organic solvent is one or a mixture of more than two of tetrahydrofuran, N-methylpyrrolidone, N-dimethylformamide and N, N-dimethylacetamide.
7. A process for the preparation of an electrochromic polymer of formula (I) according to claim 2, characterized in that: the volume of the organic solvent is 1 to 20L/mol based on the total mass of the monomer 1 and the monomer 2 shown in the formula (I).
8. A process for the preparation of an electrochromic polymer of formula (I) according to claim 2, characterized in that the post-treatment is: pouring the reaction liquid into methanol, filtering, drying a filter cake, performing Soxhlet extraction sequentially by using the methanol, the acetone, the hexane and the trichloromethane, collecting a polymer dissolved in the trichloromethane, and performing spin drying to obtain the electrochromic polymer shown in the formula (I).
9. Use of the electrochromic polymer according to claim 1 for the preparation of electrochromic polymer films.
10. The use according to claim 9, characterized in that the use is: dissolving the electrochromic polymer in a solvent to obtain a polymer solution, and then coating the polymer solution on a conductive substrate to obtain the electrochromic polymer film; the solvent is one or a mixture of more than two of dichloromethane, trichloromethane, tetrahydrofuran, toluene and N, N-dimethylformamide; the concentration of the electrochromic polymer in the polymer solution is 5-30 mg/mL.
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Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2012058416A2 (en) * | 2010-10-28 | 2012-05-03 | University Of Florida Research Foundation, Inc. | Cathodically coloring yellow soluble electrochromic and light emitting polymers |
| US20170267920A1 (en) * | 2014-05-28 | 2017-09-21 | Georgia Tech Research Corporation | Yellow to Transmissive Electrochromic Polymers |
| CN109233799A (en) * | 2017-07-11 | 2019-01-18 | 北京大学深圳研究生院 | A kind of red electrochromic polymer material, preparation method and application |
| CN110892001A (en) * | 2017-07-14 | 2020-03-17 | 菲尔齐费尔公司 | Electrochromic polymers and their synthesis and use |
| CN114907551A (en) * | 2022-05-13 | 2022-08-16 | 江苏慧智新材料科技有限公司 | Red electrochromic polymer, preparation method, thin film and device |
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- 2022-08-18 CN CN202210990010.9A patent/CN115490836A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2012058416A2 (en) * | 2010-10-28 | 2012-05-03 | University Of Florida Research Foundation, Inc. | Cathodically coloring yellow soluble electrochromic and light emitting polymers |
| US20170267920A1 (en) * | 2014-05-28 | 2017-09-21 | Georgia Tech Research Corporation | Yellow to Transmissive Electrochromic Polymers |
| CN109233799A (en) * | 2017-07-11 | 2019-01-18 | 北京大学深圳研究生院 | A kind of red electrochromic polymer material, preparation method and application |
| CN110892001A (en) * | 2017-07-14 | 2020-03-17 | 菲尔齐费尔公司 | Electrochromic polymers and their synthesis and use |
| CN114907551A (en) * | 2022-05-13 | 2022-08-16 | 江苏慧智新材料科技有限公司 | Red electrochromic polymer, preparation method, thin film and device |
Non-Patent Citations (1)
| Title |
|---|
| CHENG CHEN, QIFAN YAN: "《Achieving excellent colorimetric properties of low-cost black to transmissive switching electrochromic polymers by incorporating of spacing units into copolymers of 3,4-propylenedioxythiophene and benzothiadiazole》", DYES AND PIGMENTS, pages 37 * |
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