An electrochromic material, an electrochromic composition, and an electrochromic device

Abstract

This invention provides an electrochromic material, an electrochromic composition, and an electrochromic device, relating to the field of chemical materials technology. The electrochromic material contains electrochemically active viologen units. These viologen units are reduced under a negative voltage, increasing their charge density and causing fluoranes with different substituents to undergo ring-closure reactions. The different colors exhibited by the fluoranes with different substituents in the electrochromic material change to a colorless state within 35 ms under a negative voltage of -1.8V. The viologen unit itself has a large standard electron transfer rate constant on the electrode surface. Connecting it to the fluorane moiety further enables rapid electron transfer to the fluorane moiety, ensuring a fast color change. The electrochemically active viologen unit itself has excellent redox cycle stability, thus ensuring the excellent cycle stability of the overall electrochromic material. After 1000 cycles, the absorbance change decreases by less than 10%.

Description

Technical Field

[0001] This invention relates to the field of chemical materials technology, and more specifically, to an electrochromic material, an electrochromic composition, and an electrochromic device. Background Technology

[0002] Some electrochemically active organic molecules or groups are weakly acidic before electrochemical oxidation, but can reversibly release protons after electrochemical oxidation, significantly increasing the acidity of the system. These substances are called electroacids.

[0003] Electrochromic systems exhibit behavior characteristic of small organic molecules. The electrochromic molecule and the acid-response molecule may be the same or two different molecules. During oxidation of the electrochromic acid, proton transfer occurs either from the electrochromic molecule to the acid-response molecule, or from the electrochromic group on the small organic molecule to the acid-response group. Conversely, during reduction of the oxidized electrochromic acid, protons either return from the acid-response molecule to the electrochromic molecule, or transfer from the acid-response group on the small organic molecule to the electrochromic group. The acceptance and donation of protons by the acid-response molecule or group causes a color change. After electrical stimulation colors the small organic molecules, they diffuse away from the electrode, leading to color decay. Due to the greater distance between the electrochromic molecule and the acid-response molecule, the proton transfer distance is longer, resulting in a slower response speed for electrochromic devices. When a reverse voltage is applied, the color fading is also slower because the coloring or electrochromic molecules diffuse away from the electrode. Summary of the Invention

[0004] The problem solved by this invention is how to address the slow response speed of electrochromic devices.

[0005] To address the above problems, the present invention provides an electrochromic material, an electrochromic composition, and an electrochromic device.

[0006] In a first aspect, the present invention provides an electrochromic material having a chemical formula of any one of the following formulas: Formula I, Formula II, Formula III, or Formula IV:

[0007]

[0008] Wherein, Y is an O atom, an S atom, or Si(CH3)2; R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, R12, R13, R14, R15, R16, R17, R18, and R19 are any one of H, halogens, alkyl groups between C1 and C24, substituted alkyl groups between C1 and C24, hydroxyl groups, alkoxy groups between C1 and C24, amino groups, alkylamino groups between C1 and C24, aryl groups between C6 and C24, or groups between C7 and C24 containing both aromatic rings and alkanes; M - and L - It is Cl- ,Br - I - PF6 - BF4 - Any one of them.

[0009] In a second aspect, the present invention provides an electrochromic composition comprising an electrolyte and an electrochromic material as described above, wherein the molar ratio of the electrochromic material to the electrolyte is 0.001-1000.

[0010] Optionally, the electrolyte is any one of inorganic or organometallic salts containing metal ions, tetraalkyl quaternary ammonium salts, or ionic liquids; the inorganic or organometallic salts containing metal ions are one or any combination of Li, Na, K, Rb, Cs, Cu, and Ag salts.

[0011] Optionally, the ionic liquid is butyltrimethylammonium bis(trifluoromethanesulfonyl)imide, tributylmethyldibutylammonium phosphate, tributylmethylammonium chloride, tributylmethylmethylammonium carbonate, triethylmethyldibutylammonium phosphate, tetraethylammonium trifluoromethanesulfonate, trioctylmethylammonium bisulfate, ethyldimethylpropylammonium bis(trifluoromethanesulfonyl)imide, diethylmethyl-(2-methoxyethyl)ammonium bis(trifluoromethanesulfonyl)imide, tetrabutylammonium heptadecanoate sulfonic acid, tetrabutylammonium nitrite, tetrabutylammonium hydroxide, tetrabutylammonium methanesulfonate, tetrabutylammonium bis(trifluoromethanesulfonyl)imide, tetrabutylammonium succinimide, tetrahexylammonium bisulfate, tetrahexylammonium iodide, tetraheptylammonium chloride, tetraheptylammonium bromide, tetra-n-butylammonium triiodide, tetrahexyl tetrafluoroborate. Ammonium, tetrachlorododecylammonium, tetrabromododecylammonium, tetramethylammonium hydroxide, tetradecylammonium bromide, tetraoctylammonium chloride, methyltributylammonium sulfate methyl ester, methyltri(octadecyl)ammonium bromide, methyltrioctylthiosalicylic acid ammonium, methyl-trioctylammonium bis(trifluoromethanesulfonyl)imide, 2-hydroxyethyl-trimethylammonium L-(+)-lactate, 2-hydroxy-N,N-di(2-hydroxyethyl)-N-methylethylammonium sulfate methyl ester, benzyl dimethyltetradecylammonium chloride, tetrabutylammonium benzoate, thiophene tetrabutylammonium, acetic acid choline, 1-butylpyridine bromide, 1-butyl-4-methylpyridine hexafluorophosphate, 1-butyl-3-methylpyridine bis(trifluoromethanesulfonyl)imide, 1-butyl-4-methylpyridine tetrafluoroborate 1-Butyl-4-methylpyridine iodide, 1-ethylpyridinium tetrafluoroborate, 1-(3-cyanopropyl)pyridine chloride, 3-methyl-1-propylpyridine bis(trifluoromethanesulfonyl)imide, 1-butyl-2,3-dimethylimidazolium hexafluorophosphate, 1-butyl-2,3-dimethylimidazolium tetrafluoroborate, 1-butyl-2,3-dimethylimidazolium tetrafluoroborate, 4-(3-butyl-1-imidazolium)-1-butanesulfonate, 1-butyl-3-methylimidazolium acetate, 1-butyl-3-methylimidazolium dicyanamide, 1-butyl-3-methylimidazolium hexafluorophosphate, 1-butyl-3-methylimidazolium hexafluoroantimonate, 1-butyl-3-methylimidazolium bis(trifluoromethanesulfonyl)imide, 1-butyl-3- Methylimidazolium chloride, 1-butyl-3-methylimidazolium bromide, 1-butyl-3-methylimidazolium methanesulfonate, 1-butyl-3-methylimidazolium nitrate, 1-butyl-3-methylimidazolium hydrogen sulfate, 1-butyl-3-methylimidazolium methyl sulfate, 1-butyl-3-methylimidazolium octyl sulfate, 1-butyl-3-methylimidazolium iodide, 1-butyl-3-methylimidazolium bicarbonate, 1-butyl-3-methylimidazolium dibutyl phosphate, 1-butyl-3-methylimidazolium trifluoromethanesulfonate, 1-butyl-3-methylimidazolium tetrafluoroborate, 1-butyl-3-methylimidazolium tetrachloroaluminate, 1-butyl-3-methylimidazolium toluenesulfonate, 1-butyl-3-methylimidazolium thiocyanate, 1,2,3-Trimethylimidazolium methanesulfonic acid, 1-propyl-3-methylimidazolium bis(trifluoromethanesulfonyl)imine, 1-ethyl-2,3-dimethylimidazolium hexafluorophosphate, 1-ethyl-2,3-dimethylimidazolium tetrafluoroborate, 1-ethyl-2,3-dimethylimidazolium trifluoromethanesulfonate, 1-ethyl-2,3-dimethylimidazolium ethyl sulfate, 1-ethyl-3-methylimidazolium trifluoromethanesulfonate, 1-ethyl-3-methylimidazolium L-(+)-lactate, 1-ethyl-3-methylimidazolium dibutyl phosphate, 1-ethyl-3-methylimidazolium diethyl phosphate, 1-ethyl-3-methylimidazolium diaminonitrile, 1-ethyl-3-methylimidazolium dimethyl phosphate, 1-ethyl-3-methylimidazolium hexafluorophosphate, 1- Ethyl-3-methylimidazoline bis(trifluoromethylsulfonyl)imine, 1-ethyl-3-methylimidazoline bis(pentafluoroethylsulfonyl)imine, 1-ethyl-3-methylimidazolium 1,1,2,2-tetrafluoroethylsulfonate, 1-ethyl-3-methylimidazolium tetrafluoroborate, 1-ethyl-3-methylimidazolium tetrachloroaluminate, 1-ethyl-3-methylimidazolium methyl sulfate, 1-ethyl-3-methylimidazolium methylsulfonate, 1-ethyl-3-methylimidazolium nitrate, 1-ethyl-3-methylimidazolium thiocyanate, 1-ethyl-3-methylimidazolium ethyl sulfate, 1-ethyl-3-methylimidazolium hydrogen sulfate, 1-ethyl-3-methylimidazolium acetate, 1-ethyl-3-methylimidazolium p-toluenesulfonyl salt, 1-ethyl-3- Methylimidazolium bromide, 1-ethyl-3-methylimidazolium iodide, 1,3-diethoxyimidazolium hexafluorophosphate, 1,3-diethoxyimidazolium bis(trifluoromethanesulfonyl)imine, 1,2-dimethyl-3-propylimidazolium tri(trifluoromethanesulfonyl)methylate, 1,2-dimethyl-3-propylimidazolium bis(trifluoromethanesulfonyl)imine, 1,3-dimethylimidazolium dimethylphosphine, 1,3-dimethylimidazoline methanesulfonate, 1,3-dimethylimidazolium methyl sulfate, 1,3-dimethoxyimidazolium hexafluorophosphate, 1,3-dimethoxyimidazolium bis(trifluoromethanesulfonyl)imine, 1,3-dimethoxy-2-methylimidazolium hexafluorophosphate, 1,3-dimethoxy-2-methylimidazolium bis(trifluoromethanesulfonyl)imine Imidon, 1,3-dihydroxy-2-methylimidazolium bis(trifluoromethanesulfonyl)imide, 1,3-dihydroxyimidazolium bis(trifluoromethanesulfonyl)imide, 1-dodecyl-3-methylimidazolium iodide, 1,3-bis(3-cyanopropyl)imidazolium chloride, 1,3-bis(cyanomethyl)imidazolium bis(trifluoromethanesulfonyl)imide, 1,3-bis(cyanomethyl)imidazolium chloride, 1-hexyl-3-methyltrifluoromethanesulfonic acid imidazolium, 1-hexyl-3-methylimidazolium hexafluorophosphate, 1-hexyl-3-methylimidazolium tetrafluoroborate, 1-hexyl-3-methylimidazolium bis(trifluoromethanesulfonyl)imide, 1-hexyl-3-methylimidazolium chloride, 1-butyl-2,3-dimethylimidazolium chloride, 1-ethyl-2,3-Dimethylimidazolium, 1-Ethyl-3-methylimidazolium chloride, 1-Benzyl-3-methylimidazolium chloride, 1-(3-Cyanopropyl)-3-imidazolium dicyanamide, 1-(3-Cyanopropyl)-3-methylimidazolium bis(trifluoromethanesulfonyl)amide, 1-(3-Cyanopropyl)-3-methylimidazolium chloride, 1-Allyl-3-methylimidazolium chloride, 1-Allyl-3-methylimidazolium bromide, 1-Allyl-3-methylimidazolium dicyanamide, 1-Allyl-3-methylimidazolium bis(trifluoromethanesulfonyl)imide, 1-Methyl-3-propylimidazolium methyl carbonate, 1-Methyl-3-propylimidazolium iodide, 1-Methyl-3-vinylimidazolium methyl carbonate, 1-Methylimidazolium hydrogen sulfate, 1- Methylimidazolium chloride, 1-methyl-3-octylimidazolium trifluoromethanesulfonate, 1-methyl-3-octylimidazolium tetrafluoroborate, 1-methyl-3-octylimidazolium chloride, 1-decyl-3-methylimidazolium tetrafluoroborate, decylmethylimidazolium chloride, 1-hexyl-3-methylimidazolium iodide, 1-(2-hydroxyethyl)-3-methylimidazolium dicyandiamide, 1-benzyl-3-methylimidazolium hexafluorophosphate, 1-benzyl-3-methylimidazolium tetrafluoroborate, 1-octyl-3-methylimidazolium hexafluorophosphate, 1-butyl-3-methylimidazolium acetate, 1-butyl-3-methylimidazolium bis(trifluoromethanesulfonyl)imide, 1-butyl-3-methylimidazolium chloride, 1-butyl-3-methylimidazolium methanesulfonate, 1-butyl- 3-Methylimidazolium hydrogen sulfate, 1-butyl-3-methylimidazolium methyl sulfate, 1-butyl-3-methylimidazolium trifluoromethanesulfonate, 1-butyl-3-methylimidazolium tetrafluoroborate, 1-butyl-3-methylimidazolium thiocyanate, 1,2,3-trimethylimidazolium methanesulfonic acid, 1-propyl-3-methylimidazolium bis(trifluoromethanesulfonyl)imine, 1-ethyl-2,3-dimethylimidazolium ethyl sulfate, 1-ethyl-3-methylimidazolium trifluoromethanesulfonate, 1-ethyl-3-methylimidazolium diethyl phosphate, 1-ethyl-3-methylimidazolium diaminonitrile, 1-ethyl-3-methylimidazoline bis(trifluoromethanesulfonyl)imine, 1-ethyl-3-methylimidazolium tetrafluoroborate, 1-ethyl-3-methylimidazolium diaminonitrile, 1-ethyl-3-methylimidazolium ... 1-Ethyl-3-methylimidazolium aluminate, 1-Ethyl-3-methylimidazolium methanesulfonate, 1-Ethyl-3-methylimidazolium thiocyanate, 1-Ethyl-3-methylimidazolium ethyl sulfate, 1-Ethyl-3-methylimidazolium hydrogen sulfate, 1-Ethyl-3-methylimidazolium acetate, 1-Ethyl-3-methylimidazolium chloride, 1-methylimidazolium hydrogen sulfate, 1-methylimidazolium chloride, tributylmethylphosphine dibutyl phosphate, tributylmethylphosphine methyl sulfate, triethylmethylphosphine dibutyl phosphate, trihexyltetradecylphosphine bromide, trihexyltetradecylphosphine chloride, trihexyltetradecylphosphine decanoate, trihexyl(tetradecyl)phosphine dicyandiamide, trihexyltetradecylphosphine bis(trifluoromethanesulfonyl)amide, trihexyltetradecylphosphine bis(2,4,4-Trimethylpentyl)phosphite, 3-(triphenylphosphine)propane-1-toluenesulfonyl, 3-(triphenylphosphine)propane-1-sulfonate, tetrabutylphosphine tetrafluoroborate, tetrabutylphosphine p-toluenesulfonate, tetrabutylphosphine methanesulfonate, 1-Butyl-1-methylpyrrolidine trifluoromethanesulfonate, 1-Butyl-1-methylpyrrolidine dinitrileamine salt, 1-Butyl-1-methylpyrrolidine hexafluorophosphate, 1-Butyl-1-methylpyrrolidine bis(trifluoromethanesulfonyl)imide, 1-Butyl-1-methylpyrrolidine bis(trifluoromethanesulfonyl)imide, 1-Butyl-1-methylpyrrolidine tetrafluoroborate, 1-Butyl-1-methylpyrrolidine chloride, 1-Butyl-1-methylpyrrolidine bromide, 1- The following are all ionic liquids selected from the following: butyl-1-methylpyrrolidine iodide, 1-butyl-1-methylpyrrolidine methyl carbonate, 1-ethyl-1-methylpyrrolidine-onium bis(trifluoromethanesulfonyl)imide, 1-ethyl-1-methylpyrrolidine-onium tetrafluoroborate, 1-methyl-1-ethylpyrrolidine-onium hexafluorophosphate, 1-methyl-1-ethylpyrrolidine bromide, triethylsulfonium bis(trifluoromethanesulfonyl)imide, cyclopropyl diphenylsulfonium tetrafluoroborate, 1-butyl-1-methylpiperidinium tetrafluoroborate, 1-butyl-1-methylpiperidinium hexafluorophosphate, 1-butyl-1-methylpiperidinium bis(trifluoromethanesulfonyl)imide, 4-ethyl-4-methylmorpholine methyl carbonate, and C4-C60 ionic liquids containing at least one S, N, or P heteroatom.

[0012] Thirdly, the present invention provides an electrochromic device comprising a first electrode, an electrochromic medium, an ion exchange membrane, an auxiliary medium, and a second electrode, wherein the electrochromic medium is composed of the electrochromic composition described above dispersed in a liquid medium or a solid medium.

[0013] Optionally, the electrode materials used in the first electrode and the second electrode are a combination of the first material and the second material, wherein the first material is any one of gold, silver, copper, mercury, platinum, palladium, tungsten, aluminum, zinc, zinc oxide, and indium oxide, and the second material is any one of tin oxide composite, tungsten carbide, nickel carbide, graphite, graphene, and carbon nanotube electrode materials.

[0014] Optionally, the ion exchange membrane is any one of a proton exchange membrane, a lithium-ion conductive membrane, a cation exchange membrane, an anion exchange membrane, a liquid medium or a solid medium containing an electrolyte.

[0015] Optionally, the auxiliary medium is a liquid or solid medium containing electrolytes, or a liquid or solid medium containing a mixture of an oxidizing substance and an electrolyte.

[0016] Optionally, the substance with oxidizing properties is any one of phenolic compounds, amine compounds, TEMPO compounds, metal salts, and metal complexes;

[0017] Liquid media are solvents or ionic liquids, while solid media are polymers.

[0018] Optionally, the solvent may be any combination of water, alcohols containing C1-C18, ethers containing at least one oxygen atom (C3-C24), thioethers containing at least one sulfur atom (C3-C24), sulfoxides containing C2-C18, sulfones containing C2-C18, ketones containing C3-C24, acids containing C1-C18, sulfonic acids containing C1-C18, esters containing C2-C18, amides containing C1-C18, alkanes containing C1-C18, alkenes containing C1-C18, alkynes containing C1-C18, aromatics containing C1-C18, heterocycles containing at least one heteroatom (O, S, N, P) (C3-C18), alkanes containing at least one halogen atom, and aromatics containing at least one halogen atom.

[0019] The polymer is any combination of polystyrene, polystyrene, polymethyl methacrylate, polyethyl methacrylate, polypropyl methacrylate, polyisopropyl methacrylate, polybutyl methacrylate, polyisobutyl methacrylate, polytert-butyl methacrylate, polypentyl methacrylate, polyisopentyl methacrylate, polymethyl methacrylate, polyethyl methacrylate, polypropyl methacrylate, polyisopropyl methacrylate, polybutyl methacrylate, polyisobutyl methacrylate, polytert-butyl methacrylate, polypentyl methacrylate, polyisopentyl methacrylate, polyhexyl methacrylate, polyethylene glycol, polyvinyl alcohol, polyurethane, polyethylene, polycarbonate, polyamide, polytetrafluoroethylene, diethyl terephthalate, polybutylene terephthalate, polyvinyl acetate, polysilicon, polyacrylonitrile, polychlorotrifluoroethylene, acrylonitrile-butadiene-styrene copolymer, and polydimethylsilicate.

[0020] The beneficial effects of the electrochromic material, electrochromic composition, and electrochromic device of the present invention are as follows: In the electrochromic material, the electrochemically active viologen unit is reduced under a negative voltage, increasing the charge density and causing fluoranes with different substituents to undergo ring-closure reactions. The different colors exhibited by the fluoranes with different substituents in the electrochromic material change to a colorless state with ring closure within 35ms under the application of a -1.8V negative voltage. The electrochemically active viologen unit in the electrochromic material has a large standard electron transfer rate constant on the electrode surface. Connecting it to the fluorane portion enables rapid electron transfer to the fluorane portion, thus ensuring a fast color change speed. The electrochemically active viologen unit itself has excellent redox cycle stability, thereby ensuring the excellent cycle stability of the overall electrochromic material. After 1000 cycles, the absorbance change decreases by less than 10%. Attached Figure Description

[0021] Figure 1 This is a schematic diagram showing the change of absorbance over time in the electrochemical and ultraviolet spectroscopy combined test of the electrochromic device in Example 1.

[0022] Figure 2 For example, Formula I-1 in Example 1 1 1H NMR spectrum (using DMSO-d6 as solvent, 400MHz frequency);

[0023] Figure 3 For example, Formula I-1 in Example 1 13 C10 NMR spectrum (using DMSO-d6 as solvent, 101MHz frequency);

[0024] Figure 4 The graph shows the fading efficiency and coloring efficiency of the electrochromic device prepared by Formula I-1 in Example 1.

[0025] Figure 5 The graph shows the fading time and coloring time of the electrochromic device prepared by Formula I-1 in Example 1.

[0026] Figure 6 In Example 1, MV is derived from Equation I-1. 2+ A schematic diagram comparing the coloring time of electrochromic devices prepared with Rhodamine B;

[0027] Figure 7 For example, formula I-2 in Example 2 1 1H NMR spectrum (using DMSO-d6 as solvent, 400MHz frequency);

[0028] Figure 8 This is a graph showing the UV-Vis absorption spectra of M5 under different voltages according to an embodiment of the present invention. Detailed Implementation

[0029] To make the above-mentioned objects, features, and advantages of the present invention more apparent and understandable, specific embodiments of the present invention will be described in detail below with reference to the accompanying drawings. Although some embodiments of the present invention are shown in the drawings, it should be understood that the present invention can be implemented in various forms and should not be construed as limited to the embodiments set forth herein. Rather, these embodiments are provided to provide a more thorough and complete understanding of the present invention. It should be understood that the accompanying drawings and embodiments of the present invention are for illustrative purposes only and are not intended to limit the scope of protection of the present invention.

[0030] Unless otherwise defined, all technical and scientific terms used in this application have the same meaning as commonly understood by one of ordinary skill in the art to which this application pertains; the terminology used in the description of this application is for the purpose of describing particular embodiments only and is not intended to limit this application.

[0031] The term "comprising" and its variations as used herein are open-ended, meaning "including but not limited to"; the term "based on" means "at least partially based on"; the term "one embodiment" means "at least one embodiment"; the term "another embodiment" means "at least one additional embodiment"; the term "some embodiments" means "at least some embodiments"; and the term "optionally" means "optional embodiments". Definitions of other terms will be given in the description below. It should be noted that the concepts of "first," "second," etc., mentioned in this invention are used to distinguish different objects, not to describe a specific order or hierarchy. Furthermore, the terms "first" and "second" are used for descriptive purposes only and should not be construed as indicating or implying relative importance or implicitly specifying the number of indicated technical features. Thus, a feature defined with "first" or "second" may explicitly or implicitly include one or more of that feature. In the description of this application, unless otherwise stated, "a plurality of" means two or more.

[0032] To address the problems existing in the aforementioned related technologies, this embodiment provides an electrochromic material, an electrochromic composition, and an electrochromic device.

[0033] An electrochromic material provided in this invention has a chemical formula of any one of the following formulas: Formula I, Formula II, Formula III, or Formula IV:

[0034]

[0035] Wherein, Y is an O atom, an S atom, or Si(CH3)2; R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, R12, R13, R14, R15, R16, R17, R18, and R19 are any one of H, halogen, alkyl group between C1 and C24, substituted alkyl group between C1 and C24, hydroxyl group, alkoxy group between C1 and C24, amino group, alkylamino group between C1 and C24, aryl group between C6 and C24, or a group between C7 and C24 containing both an aromatic ring and an alkane; M - and L - It is Cl - ,Br - I - PF6 - Or BF4 - Any one of them.

[0036] The electrochromic mechanism of Formulas I-IV is as follows: In the electrochromic material, the electrochemically active viologen unit is reduced under a negative voltage, increasing the charge density and causing fluoranes with different substituents to undergo ring-closure reactions. The electrochromic material changes from the different colors exhibited by the fluoranes with different substituents to a colorless state after ring closure. The electrochemically active viologen unit in the electrochromic material has a very high standard electron transfer rate constant on the electrode surface. Connecting it to the fluorane portion further enables rapid electron transfer to the fluorane portion, thus ensuring a fast color change rate. The electrochemically active viologen unit itself has excellent redox cycle stability, thereby ensuring the excellent cycle stability of the overall electrochromic material.

[0037]

[0038] This invention provides an electrochromic composition comprising an electrolyte and an electrochromic material as described above, wherein the molar ratio of the electrochromic material to the electrolyte is 0.001-1000.

[0039] Optionally, the electrolyte is any one of an inorganic or organometallic salt containing metal ions, a tetraalkyl quaternary ammonium salt, or an ionic liquid; the inorganic or organometallic salt containing metal ions is one or any combination of Li, Na, K, Rb, Cs, Cu, or Ag salts.

[0040] Optionally, the ionic liquid is butyltrimethylammonium bis(trifluoromethanesulfonyl)imide, tributylmethyldibutylammonium phosphate, tributylmethylammonium chloride, tributylmethylmethylammonium carbonate, triethylmethyldibutylammonium phosphate, tetraethylammonium trifluoromethanesulfonate, trioctylmethylammonium bisulfate, ethyldimethylpropylammonium bis(trifluoromethanesulfonyl)imide, diethylmethyl-(2-methoxyethyl)ammonium bis(trifluoromethanesulfonyl)imide, tetrabutylammonium heptadecanoate sulfonic acid, tetrabutylammonium nitrite, tetrabutylammonium hydroxide, tetrabutylammonium methanesulfonate, tetrabutylammonium bis(trifluoromethanesulfonyl)imide, tetrabutylammonium succinimide, tetrahexylammonium bisulfate, tetrahexylammonium iodide, tetraheptylammonium chloride, tetraheptylammonium bromide, tetra-n-butylammonium triiodide, tetrahexyl tetrafluoroborate. Ammonium, tetrachlorododecylammonium, tetrabromododecylammonium, tetramethylammonium hydroxide, tetradecylammonium bromide, tetraoctylammonium chloride, methyltributylammonium sulfate methyl ester, methyltri(octadecyl)ammonium bromide, methyltrioctylthiosalicylic acid ammonium, methyl-trioctylammonium bis(trifluoromethanesulfonyl)imide, 2-hydroxyethyl-trimethylammonium L-(+)-lactate, 2-hydroxy-N,N-di(2-hydroxyethyl)-N-methylethylammonium sulfate methyl ester, benzyl dimethyltetradecylammonium chloride, tetrabutylammonium benzoate, thiophene tetrabutylammonium, acetic acid choline, 1-butylpyridine bromide, 1-butyl-4-methylpyridine hexafluorophosphate, 1-butyl-3-methylpyridine bis(trifluoromethanesulfonyl)imide, 1-butyl-4-methylpyridine tetrafluoroborate 1-Butyl-4-methylpyridine iodide, 1-ethylpyridinium tetrafluoroborate, 1-(3-cyanopropyl)pyridine chloride, 3-methyl-1-propylpyridine bis(trifluoromethanesulfonyl)imide, 1-butyl-2,3-dimethylimidazolium hexafluorophosphate, 1-butyl-2,3-dimethylimidazolium tetrafluoroborate, 1-butyl-2,3-dimethylimidazolium tetrafluoroborate, 4-(3-butyl-1-imidazolium)-1-butanesulfonate, 1-butyl-3-methylimidazolium acetate, 1-butyl-3-methylimidazolium dicyanamide, 1-butyl-3-methylimidazolium hexafluorophosphate, 1-butyl-3-methylimidazolium hexafluoroantimonate, 1-butyl-3-methylimidazolium bis(trifluoromethanesulfonyl)imide, 1-butyl-3- Methylimidazolium chloride, 1-butyl-3-methylimidazolium bromide, 1-butyl-3-methylimidazolium methanesulfonate, 1-butyl-3-methylimidazolium nitrate, 1-butyl-3-methylimidazolium hydrogen sulfate, 1-butyl-3-methylimidazolium methyl sulfate, 1-butyl-3-methylimidazolium octyl sulfate, 1-butyl-3-methylimidazolium iodide, 1-butyl-3-methylimidazolium bicarbonate, 1-butyl-3-methylimidazolium dibutyl phosphate, 1-butyl-3-methylimidazolium trifluoromethanesulfonate, 1-butyl-3-methylimidazolium tetrafluoroborate, 1-butyl-3-methylimidazolium tetrachloroaluminate, 1-butyl-3-methylimidazolium toluenesulfonate, 1-butyl-3-methylimidazolium thiocyanate, 1,2,3-Trimethylimidazolium methanesulfonic acid, 1-propyl-3-methylimidazolium bis(trifluoromethanesulfonyl)imine, 1-ethyl-2,3-dimethylimidazolium hexafluorophosphate, 1-ethyl-2,3-dimethylimidazolium tetrafluoroborate, 1-ethyl-2,3-dimethylimidazolium trifluoromethanesulfonate, 1-ethyl-2,3-dimethylimidazolium ethyl sulfate, 1-ethyl-3-methylimidazolium trifluoromethanesulfonate, 1-ethyl-3-methylimidazolium L-(+)-lactate, 1-ethyl-3-methylimidazolium dibutyl phosphate, 1-ethyl-3-methylimidazolium diethyl phosphate, 1-ethyl-3-methylimidazolium diaminonitrile, 1-ethyl-3-methylimidazolium dimethyl phosphate, 1-ethyl-3-methylimidazolium hexafluorophosphate, 1- Ethyl-3-methylimidazoline bis(trifluoromethylsulfonyl)imine, 1-ethyl-3-methylimidazoline bis(pentafluoroethylsulfonyl)imine, 1-ethyl-3-methylimidazolium 1,1,2,2-tetrafluoroethylsulfonate, 1-ethyl-3-methylimidazolium tetrafluoroborate, 1-ethyl-3-methylimidazolium tetrachloroaluminate, 1-ethyl-3-methylimidazolium methyl sulfate, 1-ethyl-3-methylimidazolium methylsulfonate, 1-ethyl-3-methylimidazolium nitrate, 1-ethyl-3-methylimidazolium thiocyanate, 1-ethyl-3-methylimidazolium ethyl sulfate, 1-ethyl-3-methylimidazolium hydrogen sulfate, 1-ethyl-3-methylimidazolium acetate, 1-ethyl-3-methylimidazolium p-toluenesulfonyl salt, 1-ethyl-3- Methylimidazolium bromide, 1-ethyl-3-methylimidazolium iodide, 1,3-diethoxyimidazolium hexafluorophosphate, 1,3-diethoxyimidazolium bis(trifluoromethanesulfonyl)imine, 1,2-dimethyl-3-propylimidazolium tri(trifluoromethanesulfonyl)methylate, 1,2-dimethyl-3-propylimidazolium bis(trifluoromethanesulfonyl)imine, 1,3-dimethylimidazolium dimethylphosphine, 1,3-dimethylimidazoline methanesulfonate, 1,3-dimethylimidazolium methyl sulfate, 1,3-dimethoxyimidazolium hexafluorophosphate, 1,3-dimethoxyimidazolium bis(trifluoromethanesulfonyl)imine, 1,3-dimethoxy-2-methylimidazolium hexafluorophosphate, 1,3-dimethoxy-2-methylimidazolium bis(trifluoromethanesulfonyl)imine Imidon, 1,3-dihydroxy-2-methylimidazolium bis(trifluoromethanesulfonyl)imide, 1,3-dihydroxyimidazolium bis(trifluoromethanesulfonyl)imide, 1-dodecyl-3-methylimidazolium iodide, 1,3-bis(3-cyanopropyl)imidazolium chloride, 1,3-bis(cyanomethyl)imidazolium bis(trifluoromethanesulfonyl)imide, 1,3-bis(cyanomethyl)imidazolium chloride, 1-hexyl-3-methyltrifluoromethanesulfonic acid imidazolium, 1-hexyl-3-methylimidazolium hexafluorophosphate, 1-hexyl-3-methylimidazolium tetrafluoroborate, 1-hexyl-3-methylimidazolium bis(trifluoromethanesulfonyl)imide, 1-hexyl-3-methylimidazolium chloride, 1-butyl-2,3-dimethylimidazolium chloride, 1-ethyl-2,3-Dimethylimidazolium, 1-Ethyl-3-methylimidazolium chloride, 1-Benzyl-3-methylimidazolium chloride, 1-(3-Cyanopropyl)-3-imidazolium dicyanamide, 1-(3-Cyanopropyl)-3-methylimidazolium bis(trifluoromethanesulfonyl)amide, 1-(3-Cyanopropyl)-3-methylimidazolium chloride, 1-Allyl-3-methylimidazolium chloride, 1-Allyl-3-methylimidazolium bromide, 1-Allyl-3-methylimidazolium dicyanamide, 1-Allyl-3-methylimidazolium bis(trifluoromethanesulfonyl)imide, 1-Methyl-3-propylimidazolium methyl carbonate, 1-Methyl-3-propylimidazolium iodide, 1-Methyl-3-vinylimidazolium methyl carbonate, 1-Methylimidazolium hydrogen sulfate, 1- Methylimidazolium chloride, 1-methyl-3-octylimidazolium trifluoromethanesulfonate, 1-methyl-3-octylimidazolium tetrafluoroborate, 1-methyl-3-octylimidazolium chloride, 1-decyl-3-methylimidazolium tetrafluoroborate, decylmethylimidazolium chloride, 1-hexyl-3-methylimidazolium iodide, 1-(2-hydroxyethyl)-3-methylimidazolium dicyandiamide, 1-benzyl-3-methylimidazolium hexafluorophosphate, 1-benzyl-3-methylimidazolium tetrafluoroborate, 1-octyl-3-methylimidazolium hexafluorophosphate, 1-butyl-3-methylimidazolium acetate, 1-butyl-3-methylimidazolium bis(trifluoromethanesulfonyl)imide, 1-butyl-3-methylimidazolium chloride, 1-butyl-3-methylimidazolium methanesulfonate, 1-butyl- 3-Methylimidazolium hydrogen sulfate, 1-butyl-3-methylimidazolium methyl sulfate, 1-butyl-3-methylimidazolium trifluoromethanesulfonate, 1-butyl-3-methylimidazolium tetrafluoroborate, 1-butyl-3-methylimidazolium thiocyanate, 1,2,3-trimethylimidazolium methanesulfonic acid, 1-propyl-3-methylimidazolium bis(trifluoromethanesulfonyl)imine, 1-ethyl-2,3-dimethylimidazolium ethyl sulfate, 1-ethyl-3-methylimidazolium trifluoromethanesulfonate, 1-ethyl-3-methylimidazolium diethyl phosphate, 1-ethyl-3-methylimidazolium diaminonitrile, 1-ethyl-3-methylimidazoline bis(trifluoromethanesulfonyl)imine, 1-ethyl-3-methylimidazolium tetrafluoroborate, 1-ethyl-3-methylimidazolium diaminonitrile, 1-ethyl-3-methylimidazolium ... 1-Ethyl-3-methylimidazolium aluminate, 1-Ethyl-3-methylimidazolium methanesulfonate, 1-Ethyl-3-methylimidazolium thiocyanate, 1-Ethyl-3-methylimidazolium ethyl sulfate, 1-Ethyl-3-methylimidazolium hydrogen sulfate, 1-Ethyl-3-methylimidazolium acetate, 1-Ethyl-3-methylimidazolium chloride, 1-methylimidazolium hydrogen sulfate, 1-methylimidazolium chloride, tributylmethylphosphine dibutyl phosphate, tributylmethylphosphine methyl sulfate, triethylmethylphosphine dibutyl phosphate, trihexyltetradecylphosphine bromide, trihexyltetradecylphosphine chloride, trihexyltetradecylphosphine decanoate, trihexyl(tetradecyl)phosphine dicyandiamide, trihexyltetradecylphosphine bis(trifluoromethanesulfonyl)amide, trihexyltetradecylphosphine bis(2,4,4-Trimethylpentyl)phosphite, 3-(triphenylphosphine)propane-1-toluenesulfonyl, 3-(triphenylphosphine)propane-1-sulfonate, tetrabutylphosphine tetrafluoroborate, tetrabutylphosphine p-toluenesulfonate, tetrabutylphosphine methanesulfonate, 1-Butyl-1-methylpyrrolidine trifluoromethanesulfonate, 1-Butyl-1-methylpyrrolidine dinitrileamine salt, 1-Butyl-1-methylpyrrolidine hexafluorophosphate, 1-Butyl-1-methylpyrrolidine bis(trifluoromethanesulfonyl)imide, 1-Butyl-1-methylpyrrolidine bis(trifluoromethanesulfonyl)imide, 1-Butyl-1-methylpyrrolidine tetrafluoroborate, 1-Butyl-1-methylpyrrolidine chloride, 1-Butyl-1-methylpyrrolidine bromide, 1- The following are all ionic liquids selected from the following: butyl-1-methylpyrrolidine iodide, 1-butyl-1-methylpyrrolidine methyl carbonate, 1-ethyl-1-methylpyrrolidine-onium bis(trifluoromethanesulfonyl)imide, 1-ethyl-1-methylpyrrolidine-onium tetrafluoroborate, 1-methyl-1-ethylpyrrolidine-onium hexafluorophosphate, 1-methyl-1-ethylpyrrolidine bromide, triethylsulfonium bis(trifluoromethanesulfonyl)imide, cyclopropyl diphenylsulfonium tetrafluoroborate, 1-butyl-1-methylpiperidinium tetrafluoroborate, 1-butyl-1-methylpiperidinium hexafluorophosphate, 1-butyl-1-methylpiperidinium bis(trifluoromethanesulfonyl)imide, 4-ethyl-4-methylmorpholine methyl carbonate, and C4-C60 ionic liquids containing at least one S, N, or P heteroatom.

[0041] This invention provides an electrochromic device comprising a first electrode, an electrochromic medium, an ion exchange membrane, an auxiliary medium, and a second electrode, wherein the electrochromic medium is composed of an electrochromic composition as described above dispersed in a liquid medium or a solid medium.

[0042] Optionally, the electrode materials used in the first electrode and the second electrode are a combination of a first material and a second material, wherein the first material is gold, silver, copper, mercury, platinum, palladium, tungsten, aluminum, zinc, zinc oxide or indium oxide, and the second material is tin oxide composite, tungsten carbide, nickel carbide, graphite, graphene or carbon nanotube electrode material.

[0043] Optionally, the ion exchange membrane is any one of a proton exchange membrane, a lithium-ion conductive membrane, a cation exchange membrane, an anion exchange membrane, or a liquid or solid medium containing an electrolyte.

[0044] The thickness of the ion exchange membrane can range from 20 nm to 500 μm. Increasing the thickness improves the bistable electrochromic effect of the electrochromic device. If the ion exchange membrane is too thin, the ion exchange membrane material easily diffuses and combines with the color-changing layer material, affecting the bistable maintenance effect, and is also prone to device breakdown when voltage is applied. If the ion exchange membrane is too thick, the ion migration distance is longer, resulting in poor response speed of the electrochromic device. When the thickness of the ion exchange membrane is less than 20 nm, the electrochromic device has no bistable maintenance effect, and the maximum voltage that can be applied to the electrochromic device is only 0.5 V. When the thickness of the ion exchange membrane is greater than 500 μm, the fading speed of the electrochromic device is 30 minutes, resulting in poor response speed.

[0045] Optionally, the auxiliary medium is a liquid or solid medium containing electrolytes, or a liquid or solid medium containing a mixture of an oxidizing substance and an electrolyte.

[0046] Optionally, the oxidizing substances are phenolic compounds, amine compounds, TEMPO compounds, metal salts, or metal complexes;

[0047] Liquid media are solvents or ionic liquids, while solid media are polymers.

[0048] Optionally, the solvent may be any combination of water, alcohols containing C1-C18, ethers containing at least one oxygen atom (C3-C24), thioethers containing at least one sulfur atom (C3-C24), sulfoxides containing C2-C18, sulfones containing C2-C18, ketones containing C3-C24, acids containing C1-C18, sulfonic acids containing C1-C18, esters containing C2-C18, amides containing C1-C18, alkanes containing C1-C18, alkenes containing C1-C18, alkynes containing C1-C18, aromatics containing C1-C18, heterocycles containing at least one heteroatom (O, S, N, P) (C3-C18), alkanes containing at least one halogen atom, and aromatics containing at least one halogen atom.

[0049] The polymer is any combination of polystyrene, polystyrene, polymethyl methacrylate, polyethyl methacrylate, polypropyl methacrylate, polyisopropyl methacrylate, polybutyl methacrylate, polyisobutyl methacrylate, polytert-butyl methacrylate, polypentyl methacrylate, polyisopentyl methacrylate, polymethyl methacrylate, polyethyl methacrylate, polypropyl methacrylate, polyisopropyl methacrylate, polybutyl methacrylate, polyisobutyl methacrylate, polytert-butyl methacrylate, polypentyl methacrylate, polyisopentyl methacrylate, polyhexyl methacrylate, polyethylene glycol, polyvinyl alcohol, polyurethane, polyethylene, polycarbonate, polyamide, polytetrafluoroethylene, diethyl terephthalate, polybutylene terephthalate, polyvinyl acetate, polysilicon, polyacrylonitrile, polychlorotrifluoroethylene, acrylonitrile-butadiene-styrene copolymer, and polydimethylsilicate.

[0050] The present invention will be further described below with reference to specific embodiments.

[0051] Example 1

[0052] The following synthesis equation is used to synthesize electrochromic material formula I-1

[0053]

[0054]

[0055] Specifically, M1 molecule, namely 2,3-dimethyl-4-bromopyridine (1.86 g, 10 mmol), 4-pyridineboronic acid (1.35 g, 11.0 mmol), and tetrakis(triphenylphosphine)palladium (0.58 g, 0.5 mmol), was added to a 100 mL double-necked flask. Then, 10 mL of sodium bicarbonate aqueous solution (2 mol / L) and 10 mL of toluene were added sequentially, followed by 10 mL of anhydrous ethanol to dissolve them. The reaction was carried out under nitrogen protection and heated in an oil bath at 90 °C with stirring for 48 h. After the reaction was completed, the reaction system was allowed to cool naturally to room temperature. The resulting product was dissolved in 20 mL of ethyl acetate and washed with 40 mL of saturated ammonium chloride aqueous solution. Extraction was performed with 40 mL of ethyl acetate, and the mixture was separated. The extraction was repeated three times, and the combined organic phases were dried over anhydrous sodium sulfate solid for 20 minutes. Column chromatography was performed using pure ethyl acetate as the eluent to separate and purify the target product molecule. The resulting white solid product was M2 molecule, with a yield of 90%. Add 4.61 g (25 mmol) of M2 molecules and 50 mL of deionized water to a 100 mL round-bottom flask. Heat the reaction to 100 °C, and add potassium permanganate (23.0 g, 250 mmol) in five portions over 3 hours. After the reaction is complete, allow the reaction system to cool naturally to room temperature. Filter with diatomaceous earth to remove solid impurities, and then adjust the pH of the filtrate to 3–4 with 6 mol / L hydrochloric acid. Dry the filtrate using a rotary evaporator to obtain a white crude product M3. Add the crude product M3 (25 mmol), 3-diethylaminophenol (8.25 g, 50 mmol), and trifluoromethanesulfonic acid (3.75 g, 25 mmol) to a 100 mL round-bottom flask, and then add 50 mL of chlorobenzene. Heat and stir the reaction in an oil bath at 135 °C for 12 hours. After the reaction is complete, allow the reaction system to cool naturally to room temperature, remove the solvent using a rotary evaporator, dissolve the crude product in dichloromethane, and wash three times with saturated sodium bicarbonate solution. The organic phases were combined and dried for 20 minutes with anhydrous sodium sulfate solid. Column chromatography was performed using dichloromethane / methanol as eluent to separate and purify the target product molecules. The resulting red solid product was intermediate M4, with a yield of 5%. M4 molecules (520 mg, 1.0 mmol), iodomethane (1.42 g, 10 mmol), and 50 mL of acetonitrile were added to a 100 mL round-bottom flask. The reaction mixture was heated and stirred in an oil bath at 40 °C for 4 days. After the reaction was complete, the reaction system was allowed to cool naturally to room temperature. The solvent was removed using a rotary evaporator, and the crude product was dissolved in dichloromethane and washed with saturated potassium hexafluorophosphate solution. The organic phase was dried for 20 minutes with anhydrous sodium sulfate solid. Column chromatography was performed using dichloromethane / methanol as eluent to separate and purify the target product molecules. The resulting red solid product was product M5, with a yield of 50%. The mechanism of M5 was then demonstrated. Add 520 mg of M4 molecules (1.0 mmol), 700 mg of 3-bromo-1-propanol (5 mmol), and 50 mL of acetonitrile to a 100 mL round-bottom flask.The reaction was carried out in an oil bath at 80°C with stirring for 4 days. After the reaction, the reaction system was allowed to cool naturally to room temperature. The solvent was removed using a rotary evaporator, and the crude product was dissolved in dichloromethane and washed with saturated potassium hexafluorophosphate solution. The organic phase was dried for 20 minutes with anhydrous sodium sulfate solid. Column chromatography was performed using dichloromethane / methanol as the eluent to separate and purify the target product molecules. The obtained red solid product M6 had a yield of 10%. M6 molecules (145 mg, 0.2 mmol), iodomethane (280 mg, 2 mmol), and acetonitrile (20 mL) were added to a 50 mL round-bottom flask. The reaction was carried out in an oil bath at 40°C with stirring for 4 days. After the reaction, the reaction system was allowed to cool naturally to room temperature. The solvent was removed using a rotary evaporator, and the crude product was dissolved in dichloromethane and washed with saturated potassium hexafluorophosphate solution. The organic phase was dried for 20 minutes with anhydrous sodium sulfate solid. Column chromatography was performed using dichloromethane / methanol as the eluent to separate and purify the target product molecules. The resulting red solid product M7 had a yield of 50%. M7 molecules (88.5 mg, 0.1 mmol), methacryloyl chloride (20.9 mg, 0.2 mmol), triethylamine (20.2 mg, 0.2 mmol), and 10 mL of dichloromethane were added to a 50 mL round-bottom flask. The reaction was stirred at 25 °C for 6 h. After the reaction was complete, the mixture was washed with saturated potassium hexafluorophosphate solution. The organic phase was dried over anhydrous sodium sulfate for 20 min. Column chromatography was performed using dichloromethane / methanol as eluent to separate and purify the target product. The resulting red solid product, formula I-1, had a yield of 77%.

[0056] The color-changing mechanism of M5 was demonstrated as follows: When a solution of M5 molecules is subjected to a voltage of -1.0V, the molecular structure undergoes the following changes, corresponding to a significant change in its UV-Vis absorption spectrum; when a positive voltage of +0.8V is applied, the molecular structure returns to its initial state, and the corresponding UV-Vis absorption spectrum also returns to its initial state, as shown below. Figure 8 As shown.

[0057]

[0058] Formula I-1 was used as the electrochromic material, tetrabutylammonium hexafluorophosphate as the electrolyte, and the two were mixed to form an electrochromic composition, with acetonitrile as the solvent. The electrochromic medium was prepared as follows: 1 mmol of tetrabutylammonium hexafluorophosphate as the electrolyte, 1 g of polymethyl methacrylate as the film-forming medium, 20 mg of Formula I-1, and 10 mL of acetonitrile as the solvent.

[0059] It comprises a first electrode, an electrochromic medium, an ion exchange membrane, an auxiliary medium, and a second electrode, wherein the electrochromic medium is composed of the electrochromic composition as described in any one of claims 2-4 dispersed in a liquid or solid medium.

[0060] Fabrication of the electrochromic device: Both the first and second electrodes are ITO electrodes, the auxiliary medium is a TEMPO-based compound, and the ion exchange membrane is a liquid medium containing an electrolyte. Polymethyl methacrylate (PMMA) gel electrolyte was chosen, and the ion exchange membrane acts as an ion transport layer. The electrochromic medium was spin-coated onto a clean ITO electrode, and then assembled into an electrochromic device. Under a negative voltage of -1.8V, the device changes from purplish-red to colorless and transparent; under a positive voltage of +1.6V, the colorless and transparent state returns to purplish-red. Figure 4 As shown, electrochromic devices exhibit both high fading and coloring efficiencies. Figure 1 As shown, the electrochemical and ultraviolet spectroscopy coupled tests were performed, and the selected absorption wavelength was 575 nm, the optimal wavelength for the colored state of the substance. Figure 5 As shown, the horizontal axis represents time, and the vertical axis represents absorbance. After applying a negative voltage of -1.8V for 35ms, the device transmittance changed from purplish-red to colorless and transparent, with a absorbance change of only 0.1, indicating a rapid color change. Under a positive voltage of +1.6V for 65ms, the colorless and transparent state returned to purplish-red, demonstrating high coloring efficiency. Figure 1 As shown, after 1000 cycles, the absorbance change decreases by less than 10%, indicating that the device has good cycle reversibility and cycle stability.

[0061] Figure 2 The proton nuclear magnetic resonance spectrum of formula I-1 ( 1 The ¹H NMR spectrum (400MHz, DMSO-d6) shows that the molecule of formula I-1 is dissolved in the deuterated reagent DMSO-d6. The instrument frequency is 400MHz, confirming the molecular structure of formula I-1. Figure 3 The carbon NMR spectrum of Formula I-1 ( 13 C NMR spectrum (101MHz, DMSO-d6), the molecule of formula I-1 is dissolved in the deuterated reagent DMSO-d6 molecule, the instrument frequency is 101MHz, which proves the molecular structure of formula I-1.

[0062] Test respectively with formula I-1, methyl viologen (MV 2+ Electrochromic devices prepared with Rhodamine B fluorescent dye exhibited coloring time at a positive voltage of +1.6 volts. Figure 6 As shown, the electrochromic device prepared by Formula I-1 has a coloring time of only 65ms, the fastest coloring speed, and high coloring efficiency.

[0063] Methyl viologen (MV 2+ The molecular structural formula of ) is as follows:

[0064]

[0065] Example 2

[0066] The following synthesis equation is used to synthesize electrochromic materials, formula I-2.

[0067]

[0068] The synthesis process was similar to that of Formula I-1 in Example 1, yielding the final product Formula I-2.

[0069] Formula I-2 was used as the electrochromic material, tetrabutylammonium hexafluorophosphate as the electrolyte, and the two were mixed to form an electrochromic composition, with acetonitrile as the solvent. The electrochromic medium was prepared as follows: 1 mmol of tetrabutylammonium hexafluorophosphate as the electrolyte, 1 g of polymethyl methacrylate as the film-forming medium, 20 mg of Formula I-2, and 10 mL of acetonitrile as the solvent.

[0070] Fabrication of the electrochromic device: Both the first and second electrodes are ITO electrodes, with TEMPO-based compounds as the auxiliary medium. The ion exchange membrane is a liquid medium containing an electrolyte; polymethyl methacrylate (PMMA) gel electrolyte was chosen. The ion exchange membrane acts as an ion transport layer. The electrochromic medium was spin-coated onto a clean ITO electrode, and then assembled into an electrochromic device. Under a negative voltage of -1.8V, the device changes from blue to colorless and transparent; under a positive voltage of +1.6V, it changes from colorless and transparent back to blue. After 1000 cycles, the absorbance change decreased by less than 10%, indicating that the device has good cyclic reversibility and cyclic stability.

[0071] Figure 7 The proton nuclear magnetic resonance spectrum of formula I-2 ( 1 The ¹H NMR spectrum (400MHz, DMSO-d6) shows that the molecule of formula I-1 is dissolved in the deuterated reagent DMSO-d6 molecule. The instrument frequency is 400MHz, which confirms the molecular structure of formula I-1.

[0072] Example 3

[0073] The following synthesis equation is used to synthesize electrochromic materials, formula I-3.

[0074]

[0075] The synthesis process was similar to that of Formula I-1 in Example 1, yielding the final product Formula I-3.

[0076] Formula I-3 was used as the electrochromic material, tetrabutylammonium hexafluorophosphate as the electrolyte, and the two were mixed to form an electrochromic composition, with acetonitrile as the solvent. The electrochromic medium was prepared as follows: 1 mmol of tetrabutylammonium hexafluorophosphate as the electrolyte, 1 g of polymethyl methacrylate as the film-forming medium, 20 mg of Formula I-3, and 10 mL of acetonitrile as the solvent.

[0077] Fabrication of the electrochromic device: Both the first and second electrodes are ITO electrodes, with TEMPO-based compounds as the auxiliary medium. The ion exchange membrane is a liquid medium containing an electrolyte; polymethyl methacrylate (PMMA) gel electrolyte was chosen. The ion exchange membrane acts as an ion transport layer. The electrochromic medium was spin-coated onto a clean ITO electrode, and then assembled into an electrochromic device. Under a negative voltage of -1.8V, the device changes from yellow to colorless and transparent; under a positive voltage of +1.6V, it changes from colorless and transparent back to yellow. After 1000 cycles, the absorbance change decreased by less than 10%, indicating that the device has good cyclic reversibility and cyclic stability.

[0078] While the present invention has been disclosed above, its scope of protection is not limited thereto. Those skilled in the art can make various changes and modifications without departing from the spirit and scope of the present invention, and all such changes and modifications will fall within the scope of protection of the present invention.

Claims

1. An electrochromic material, characterized in that, The chemical formula is any one of the following formulas: Formula I, Formula II, Formula III, or Formula IV: Wherein, Y is an O atom or an S atom; R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, R12, R13, R14, R15, R16, R17, R18, and R19 are any one of H, halogens, alkyl groups between C1 and C24, alkoxy groups between C1 and C24, amino groups, and alkylamino groups between C1 and C24; M - and L - It is PF6 - .

2. An electrochromic composition, characterized in that, It includes an electrolyte and an electrochromic material according to claim 1, wherein the molar ratio of the electrochromic material to the electrolyte is 0.001-1000.

3. The electrochromic composition according to claim 2, characterized in that, The electrolyte is any one of inorganic or organometallic salts containing metal ions, tetraalkyl quaternary ammonium salts, or ionic liquids; the inorganic or organometallic salts containing metal ions are one or any combination of Li, Na, K, Rb, Cs, Cu, and Ag salts.

4. The electrochromic composition according to claim 3, characterized in that, The ionic liquid is butyltrimethylammonium bis(trifluoromethanesulfonyl)imide, tributylmethyldibutylammonium phosphate, tributylmethylammonium chloride, tributylmethylmethylammonium carbonate, triethylmethyldibutylammonium phosphate, tetraethylammonium trifluoromethanesulfonate, trioctylmethylammonium bisulfate, ethyldimethylpropylammonium bis(trifluoromethanesulfonyl)imide, diethylmethyl-(2-methoxyethyl)ammonium bis(trifluoromethanesulfonyl)imide, tetrabutylammonium heptadecanoate sulfonic acid, tetrabutylammonium nitrite, tetrabutylammonium hydroxide, tetrabutylammonium methanesulfonate, tetrabutylammonium bis(trifluoromethanesulfonyl)imide, tetrabutylammonium succinimide, tetrahexylammonium bisulfate, tetrahexylammonium iodide, tetrahexylammonium chloride, tetrahexylammonium bromide, tetra-n-butylammonium triiodide, and tetrahexylammonium tetrafluoroborate. Tetrachlorododecylammonium, tetrabromododecylammonium, tetramethylammonium hydroxide, tetradecylammonium bromide, tetraoctylammonium chloride, methyltributylammonium sulfate methyl ester, methyltri(octadecyl)ammonium bromide, methyltrioctylthiosalicylic acid ammonium, methyl-trioctylammonium bis(trifluoromethanesulfonyl)imide, 2-hydroxyethyl-trimethylammonium L-(+)-lactate, 2-hydroxy-N,N-di(2-hydroxyethyl)-N-methylethylammonium sulfate methyl ester, benzyl dimethyltetradecylammonium chloride, tetrabutylammonium benzoate, thiophene tetrabutylammonium, acetic acid choline, 1-butylpyridine bromide, 1-butyl-4-methylpyridine hexafluorophosphate, 1-butyl-3-methylpyridine bis(trifluoromethanesulfonyl)imide, 1-butyl-4-methylpyridine tetrafluoroborate, 1-Butyl-4-methylpyridine iodide, 1-ethylpyridinium tetrafluoroborate, 1-(3-cyanopropyl)pyridine chloride, 3-methyl-1-propylpyridine bis(trifluoromethanesulfonyl)imide, 1-butyl-2,3-dimethylimidazolium hexafluorophosphate, 1-butyl-2,3-dimethylimidazolium tetrafluoroborate, 1-butyl-2,3-dimethylimidazolium tetrafluoroborate, 4-(3-butyl-1-imidazolium)-1-butanesulfonate, 1-butyl-3-methylimidazolium acetate, 1-butyl-3-methylimidazolium dicyanamide, 1-butyl-3-methylimidazolium hexafluorophosphate, 1-butyl-3-methylimidazolium hexafluoroantimonate, 1-butyl-3-methylimidazolium bis(trifluoromethanesulfonyl)imide ...antimonate, 1-butyl-3-methylimidazolium bis(trifluoromethanesulfonyl)imide, 1-butyl-3-methylimidazolium hexafluoroantimonylate, 1-butyl-3-methylimidazolium bis(trifluoromethanesulfonyl)imide, 1-butyl-3-methylimidazolium hexafluoroantimonylate, 1-butyl-3-methylimidazolium bis(trifluoromethanesulfonyl)imide, 1-butyl-3-methylimidazolium hexafluoroantimonylate, 1-butyl-3-methylimidazolium bis(trifluoromethanesulfonyl)imide, 1-Butyl-3-methylimidazolium chloride, 1-Butyl-3-methylimidazolium bromide, 1-Butyl-3-methylimidazolium methanesulfonate, 1-Butyl-3-methylimidazolium nitrate, 1-Butyl-3-methylimidazolium hydrogen sulfate, 1-Butyl-3-methylimidazolium methyl sulfate, 1-Butyl-3-methylimidazolium octyl sulfate, 1-Butyl-3-methylimidazolium iodide, 1-Butyl-3-methylimidazolium bicarbonate, 1-Butyl-3-methylimidazolium dibutyl phosphate, 1-Butyl-3-methylimidazolium trifluoromethanesulfonate, 1-Butyl-3-methylimidazolium tetrafluoroborate, 1-Butyl-3-methylimidazolium tetrachloroaluminate, 1-Butyl-3-methylimidazolium toluenesulfonate, 1-Butyl-3-methylimidazolium thiocyanate, 1,2,3-Trimethylimidazolium methanesulfonic acid, 1-propyl-3-methylimidazolium bis(trifluoromethanesulfonyl)imine, 1-ethyl-2,3-dimethylimidazolium hexafluorophosphate, 1-ethyl-2,3-dimethylimidazolium tetrafluoroborate, 1-ethyl-2,3-dimethylimidazolium trifluoromethanesulfonate, 1-ethyl-2,3-dimethylimidazolium ethyl sulfate, 1-ethyl-3-methylimidazolium trifluoromethanesulfonate, 1-ethyl-3-methylimidazolium L-(+)-lactate, 1-ethyl-3-methylimidazolium dibutyl phosphate, 1-ethyl-3-methylimidazolium diethyl phosphate, 1-ethyl-3-methylimidazolium diaminonitrile, 1-ethyl-3-methylimidazolium dimethyl phosphate, 1-ethyl-3-methylimidazolium hexafluorophosphate, 1- Ethyl-3-methylimidazoline bis(trifluoromethylsulfonyl)imine, 1-ethyl-3-methylimidazoline bis(pentafluoroethylsulfonyl)imine, 1-ethyl-3-methylimidazolium 1,1,2,2-tetrafluoroethylsulfonate, 1-ethyl-3-methylimidazolium tetrafluoroborate, 1-ethyl-3-methylimidazolium tetrachloroaluminate, 1-ethyl-3-methylimidazolium methyl sulfate, 1-ethyl-3-methylimidazolium methylsulfonate, 1-ethyl-3-methylimidazolium nitrate, 1-ethyl-3-methylimidazolium thiocyanate, 1-ethyl-3-methylimidazolium ethyl sulfate, 1-ethyl-3-methylimidazolium hydrogen sulfate, 1-ethyl-3-methylimidazolium acetate, 1-ethyl-3-methylimidazolium p-toluenesulfonyl salt, 1-ethyl-3- Methylimidazolium bromide, 1-ethyl-3-methylimidazolium iodide, 1,3-diethoxyimidazolium hexafluorophosphate, 1,3-diethoxyimidazolium bis(trifluoromethanesulfonyl)imine, 1,2-dimethyl-3-propylimidazolium tri(trifluoromethanesulfonyl)methylate, 1,2-dimethyl-3-propylimidazolium bis(trifluoromethanesulfonyl)imine, 1,3-dimethylimidazolium dimethylphosphine, 1,3-dimethylimidazoline methanesulfonate, 1,3-dimethylimidazolium methyl sulfate, 1,3-dimethoxyimidazolium hexafluorophosphate, 1,3-dimethoxyimidazolium bis(trifluoromethanesulfonyl)imine, 1,3-dimethoxy-2-methylimidazolium hexafluorophosphate, 1,3-dimethoxy-2-methylimidazolium bis(trifluoromethanesulfonyl)imine Imidon, 1,3-dihydroxy-2-methylimidazolium bis(trifluoromethanesulfonyl)imide, 1,3-dihydroxyimidazolium bis(trifluoromethanesulfonyl)imide, 1-dodecyl-3-methylimidazolium iodide, 1,3-bis(3-cyanopropyl)imidazolium chloride, 1,3-bis(cyanomethyl)imidazolium bis(trifluoromethanesulfonyl)imide, 1,3-bis(cyanomethyl)imidazolium chloride, 1-hexyl-3-methyltrifluoromethanesulfonic acid imidazolium, 1-hexyl-3-methylimidazolium hexafluorophosphate, 1-hexyl-3-methylimidazolium tetrafluoroborate, 1-hexyl-3-methylimidazolium bis(trifluoromethanesulfonyl)imide, 1-hexyl-3-methylimidazolium chloride, 1-butyl-2,3-dimethylimidazolium chloride, 1-ethyl-2,3-Dimethylimidazolium, 1-Ethyl-3-methylimidazolium chloride, 1-Benzyl-3-methylimidazolium chloride, 1-(3-Cyanopropyl)-3-imidazolium dicyanamide, 1-(3-Cyanopropyl)-3-methylimidazolium bis(trifluoromethanesulfonyl)amide, 1-(3-Cyanopropyl)-3-methylimidazolium chloride, 1-Allyl-3-methylimidazolium chloride, 1-Allyl-3-methylimidazolium bromide, 1-Allyl-3-methylimidazolium dicyanamide, 1-Allyl-3-methylimidazolium bis(trifluoromethanesulfonyl)imide, 1-Methyl-3-propylimidazolium methyl carbonate, 1-Methyl-3-propylimidazolium iodide, 1-Methyl-3-vinylimidazolium methyl carbonate, 1-Methylimidazolium hydrogen sulfate, 1- Methylimidazolium chloride, 1-methyl-3-octylimidazolium trifluoromethanesulfonate, 1-methyl-3-octylimidazolium tetrafluoroborate, 1-methyl-3-octylimidazolium chloride, 1-decyl-3-methylimidazolium tetrafluoroborate, decylmethylimidazolium chloride, 1-hexyl-3-methylimidazolium iodide, 1-(2-hydroxyethyl)-3-methylimidazolium dicyandiamide, 1-benzyl-3-methylimidazolium hexafluorophosphate, 1-benzyl-3-methylimidazolium tetrafluoroborate, 1-octyl-3-methylimidazolium hexafluorophosphate, 1-butyl-3-methylimidazolium acetate, 1-butyl-3-methylimidazolium bis(trifluoromethanesulfonyl)imide, 1-butyl-3-methylimidazolium chloride, 1-butyl-3-methylimidazolium methanesulfonate, 1-butyl- 3-Methylimidazolium hydrogen sulfate, 1-butyl-3-methylimidazolium methyl sulfate, 1-butyl-3-methylimidazolium trifluoromethanesulfonate, 1-butyl-3-methylimidazolium tetrafluoroborate, 1-butyl-3-methylimidazolium thiocyanate, 1,2,3-trimethylimidazolium methanesulfonic acid, 1-propyl-3-methylimidazolium bis(trifluoromethanesulfonyl)imine, 1-ethyl-2,3-dimethylimidazolium ethyl sulfate, 1-ethyl-3-methylimidazolium trifluoromethanesulfonate, 1-ethyl-3-methylimidazolium diethyl phosphate, 1-ethyl-3-methylimidazolium diaminonitrile, 1-ethyl-3-methylimidazoline bis(trifluoromethanesulfonyl)imine, 1-ethyl-3-methylimidazolium tetrafluoroborate, 1-ethyl-3-methylimidazolium diaminonitrile, 1-ethyl-3-methylimidazolium ... 1-Ethyl-3-methylimidazolium aluminate, 1-Ethyl-3-methylimidazolium methanesulfonate, 1-Ethyl-3-methylimidazolium thiocyanate, 1-Ethyl-3-methylimidazolium ethyl sulfate, 1-Ethyl-3-methylimidazolium hydrogen sulfate, 1-Ethyl-3-methylimidazolium acetate, 1-Ethyl-3-methylimidazolium chloride, 1-methylimidazolium hydrogen sulfate, 1-methylimidazolium chloride, tributylmethylphosphine dibutyl phosphate, tributylmethylphosphine methyl sulfate, triethylmethylphosphine dibutyl phosphate, trihexyltetradecylphosphine bromide, trihexyltetradecylphosphine chloride, trihexyltetradecylphosphine decanoate, trihexyl(tetradecyl)phosphine dicyandiamide, trihexyltetradecylphosphine bis(trifluoromethanesulfonyl)amide, trihexyltetradecylphosphine bis(2,4,4-Trimethylpentyl)phosphite, 3-(triphenylphosphine)propane-1-toluenesulfonyl, 3-(triphenylphosphine)propane-1-sulfonate, tetrabutylphosphine tetrafluoroborate, tetrabutylphosphine p-toluenesulfonate, tetrabutylphosphine methanesulfonate, 1-Butyl-1-methylpyrrolidine trifluoromethanesulfonate, 1-Butyl-1-methylpyrrolidine dinitrileamine salt, 1-Butyl-1-methylpyrrolidine hexafluorophosphate, 1-Butyl-1-methylpyrrolidine bis(trifluoromethanesulfonyl)imide, 1-Butyl-1-methylpyrrolidine bis(trifluoromethanesulfonyl)imide, 1-Butyl-1-methylpyrrolidine tetrafluoroborate, 1-Butyl-1-methylpyrrolidine chloride, 1-Butyl-1-methylpyrrolidine bromide, 1- The following are all C4-C60 ionic liquids containing at least one S, N, or P heteroatom: butyl-1-methylpyrrolidine iodide, 1-butyl-1-methylpyrrolidine methyl carbonate, 1-ethyl-1-methylpyrrolidine bis(trifluoromethanesulfonyl)imide, 1-ethyl-1-methylpyrrolidine tetrafluoroborate, 1-methyl-1-ethylpyrrolidine hexafluorophosphate, 1-methyl-1-ethylpyrrolidine bromide, triethylsulfonium bis(trifluoromethanesulfonyl)imide, cyclopropyl diphenylsulfonium tetrafluoroborate, 1-butyl-1-methylpiperidinium tetrafluoroborate, 1-butyl-1-methylpiperidinium hexafluorophosphate, 1-butyl-1-methylpiperidinium bis(trifluoromethanesulfonyl)imide, 4-ethyl-4-methylmorpholine methyl carbonate, and C4-C60 ionic liquids.

5. An electrochromic device, characterized in that, It is composed of a first electrode, an electrochromic medium, an ion exchange membrane, an auxiliary medium, and a second electrode, wherein the electrochromic medium is composed of the electrochromic composition as described in any one of claims 2-4 dispersed in a liquid medium or a solid medium.

6. The electrochromic device according to claim 5, characterized in that, The electrode materials used in the first electrode and the second electrode are a combination of a first material and a second material, wherein the first material is any one of gold, silver, copper, mercury, platinum, palladium, tungsten, aluminum, zinc, zinc oxide, and indium oxide, and the second material is any one of tin oxide composite, tungsten carbide, nickel carbide, graphite, graphene, and carbon nanotube electrode materials.

7. The electrochromic device according to claim 5, characterized in that, The ion exchange membrane is any one of a proton exchange membrane, a lithium-ion conductive membrane, a cation exchange membrane, an anion exchange membrane, a liquid medium containing an electrolyte, or a solid medium.

8. The electrochromic device according to claim 5, characterized in that, The auxiliary medium is a liquid or solid medium containing an electrolyte, or a liquid or solid medium containing a substance with oxidizing properties and the electrolyte.

9. The electrochromic device according to claim 8, characterized in that, The substance with oxidizing properties is any one of phenolic compounds, amine compounds, TEMPO compounds, metal salts, and metal complexes; The liquid medium is a solvent or an ionic liquid, and the solid medium is a polymer.

10. The electrochromic device according to claim 9, characterized in that, The solvent is any combination of water, alcohols containing C1-C18, ethers containing at least one oxygen atom (C3-C24), thioethers containing at least one sulfur atom (C3-C24), sulfoxides containing C2-C18, sulfones containing C2-C18, ketones containing C3-C24, acids containing C1-C18, sulfonic acids containing C1-C18, esters containing C2-C18, amides containing C1-C18, and alkanes containing C1-C18. The ionic liquid is butyltrimethylammonium bis(trifluoromethanesulfonyl)imide, tributylmethyldibutylammonium phosphate, tributylmethylammonium chloride, tributylmethylmethylammonium carbonate, triethylmethyldibutylammonium phosphate, tetraethylammonium trifluoromethanesulfonate, trioctylmethylammonium bisulfate, ethyldimethylpropylammonium bis(trifluoromethanesulfonyl)imide, diethylmethyl-(2-methoxyethyl)ammonium bis(trifluoromethanesulfonyl)imide, tetrabutylammonium heptadecanoate sulfonic acid, tetrabutylammonium nitrite, tetrabutylammonium hydroxide, tetrabutylammonium methanesulfonate, tetrabutylammonium bis(trifluoromethanesulfonyl)imide, tetrabutylammonium succinimide, tetrahexylammonium bisulfate, tetrahexylammonium iodide, tetrahexylammonium chloride, tetrahexylammonium bromide, tetra-n-butylammonium triiodide, and tetrahexylammonium tetrafluoroborate. Tetrachlorododecylammonium, tetrabromododecylammonium, tetramethylammonium hydroxide, tetradecylammonium bromide, tetraoctylammonium chloride, methyltributylammonium sulfate methyl ester, methyltri(octadecyl)ammonium bromide, methyltrioctylthiosalicylic acid ammonium, methyl-trioctylammonium bis(trifluoromethanesulfonyl)imide, 2-hydroxyethyl-trimethylammonium L-(+)-lactate, 2-hydroxy-N,N-di(2-hydroxyethyl)-N-methylethylammonium sulfate methyl ester, benzyl dimethyltetradecylammonium chloride, tetrabutylammonium benzoate, thiophene tetrabutylammonium, acetic acid choline, 1-butylpyridine bromide, 1-butyl-4-methylpyridine hexafluorophosphate, 1-butyl-3-methylpyridine bis(trifluoromethanesulfonyl)imide, 1-butyl-4-methylpyridine tetrafluoroborate, 1-Butyl-4-methylpyridine iodide, 1-ethylpyridinium tetrafluoroborate, 1-(3-cyanopropyl)pyridine chloride, 3-methyl-1-propylpyridine bis(trifluoromethanesulfonyl)imide, 1-butyl-2,3-dimethylimidazolium hexafluorophosphate, 1-butyl-2,3-dimethylimidazolium tetrafluoroborate, 1-butyl-2,3-dimethylimidazolium tetrafluoroborate, 4-(3-butyl-1-imidazolium)-1-butanesulfonate, 1-butyl-3-methylimidazolium acetate, 1-butyl-3-methylimidazolium dicyanamide, 1-butyl-3-methylimidazolium hexafluorophosphate, 1-butyl-3-methylimidazolium hexafluoroantimonate, 1-butyl-3-methylimidazolium bis(trifluoromethanesulfonyl)imide ...antimonate, 1-butyl-3-methylimidazolium bis(trifluoromethanesulfonyl)imide, 1-butyl-3-methylimidazolium hexafluoroantimonylate, 1-butyl-3-methylimidazolium bis(trifluoromethanesulfonyl)imide, 1-butyl-3-methylimidazolium hexafluoroantimonylate, 1-butyl-3-methylimidazolium bis(trifluoromethanesulfonyl)imide, 1-butyl-3-methylimidazolium hexafluoroantimonylate, 1-butyl-3-methylimidazolium bis(trifluoromethanesulfonyl)imide, 1-Butyl-3-methylimidazolium chloride, 1-Butyl-3-methylimidazolium bromide, 1-Butyl-3-methylimidazolium methanesulfonate, 1-Butyl-3-methylimidazolium nitrate, 1-Butyl-3-methylimidazolium hydrogen sulfate, 1-Butyl-3-methylimidazolium methyl sulfate, 1-Butyl-3-methylimidazolium octyl sulfate, 1-Butyl-3-methylimidazolium iodide, 1-Butyl-3-methylimidazolium bicarbonate, 1-Butyl-3-methylimidazolium dibutyl phosphate, 1-Butyl-3-methylimidazolium trifluoromethanesulfonate, 1-Butyl-3-methylimidazolium tetrafluoroborate, 1-Butyl-3-methylimidazolium tetrachloroaluminate, 1-Butyl-3-methylimidazolium toluenesulfonate, 1-Butyl-3-methylimidazolium thiocyanate, 1,2,3-Trimethylimidazolium methanesulfonic acid, 1-propyl-3-methylimidazolium bis(trifluoromethanesulfonyl)imine, 1-ethyl-2,3-dimethylimidazolium hexafluorophosphate, 1-ethyl-2,3-dimethylimidazolium tetrafluoroborate, 1-ethyl-2,3-dimethylimidazolium trifluoromethanesulfonate, 1-ethyl-2,3-dimethylimidazolium ethyl sulfate, 1-ethyl-3-methylimidazolium trifluoromethanesulfonate, 1-ethyl-3-methylimidazolium L-(+)-lactate, 1-ethyl-3-methylimidazolium dibutyl phosphate, 1-ethyl-3-methylimidazolium diethyl phosphate, 1-ethyl-3-methylimidazolium diaminonitrile, 1-ethyl-3-methylimidazolium dimethyl phosphate, 1-ethyl-3-methylimidazolium hexafluorophosphate, 1- Ethyl-3-methylimidazoline bis(trifluoromethylsulfonyl)imine, 1-ethyl-3-methylimidazoline bis(pentafluoroethylsulfonyl)imine, 1-ethyl-3-methylimidazolium 1,1,2,2-tetrafluoroethylsulfonate, 1-ethyl-3-methylimidazolium tetrafluoroborate, 1-ethyl-3-methylimidazolium tetrachloroaluminate, 1-ethyl-3-methylimidazolium methyl sulfate, 1-ethyl-3-methylimidazolium methylsulfonate, 1-ethyl-3-methylimidazolium nitrate, 1-ethyl-3-methylimidazolium thiocyanate, 1-ethyl-3-methylimidazolium ethyl sulfate, 1-ethyl-3-methylimidazolium hydrogen sulfate, 1-ethyl-3-methylimidazolium acetate, 1-ethyl-3-methylimidazolium p-toluenesulfonyl salt, 1-ethyl-3- Methylimidazolium bromide, 1-ethyl-3-methylimidazolium iodide, 1,3-diethoxyimidazolium hexafluorophosphate, 1,3-diethoxyimidazolium bis(trifluoromethanesulfonyl)imine, 1,2-dimethyl-3-propylimidazolium tri(trifluoromethanesulfonyl)methylate, 1,2-dimethyl-3-propylimidazolium bis(trifluoromethanesulfonyl)imine, 1,3-dimethylimidazolium dimethylphosphine, 1,3-dimethylimidazoline methanesulfonate, 1,3-dimethylimidazolium methyl sulfate, 1,3-dimethoxyimidazolium hexafluorophosphate, 1,3-dimethoxyimidazolium bis(trifluoromethanesulfonyl)imine, 1,3-dimethoxy-2-methylimidazolium hexafluorophosphate, 1,3-dimethoxy-2-methylimidazolium bis(trifluoromethanesulfonyl)imine Imidon, 1,3-dihydroxy-2-methylimidazolium bis(trifluoromethanesulfonyl)imide, 1,3-dihydroxyimidazolium bis(trifluoromethanesulfonyl)imide, 1-dodecyl-3-methylimidazolium iodide, 1,3-bis(3-cyanopropyl)imidazolium chloride, 1,3-bis(cyanomethyl)imidazolium bis(trifluoromethanesulfonyl)imide, 1,3-bis(cyanomethyl)imidazolium chloride, 1-hexyl-3-methyltrifluoromethanesulfonic acid imidazolium, 1-hexyl-3-methylimidazolium hexafluorophosphate, 1-hexyl-3-methylimidazolium tetrafluoroborate, 1-hexyl-3-methylimidazolium bis(trifluoromethanesulfonyl)imide, 1-hexyl-3-methylimidazolium chloride, 1-butyl-2,3-dimethylimidazolium chloride, 1-ethyl-2,3-Dimethylimidazolium, 1-Ethyl-3-methylimidazolium chloride, 1-Benzyl-3-methylimidazolium chloride, 1-(3-Cyanopropyl)-3-imidazolium dicyanamide, 1-(3-Cyanopropyl)-3-methylimidazolium bis(trifluoromethanesulfonyl)amide, 1-(3-Cyanopropyl)-3-methylimidazolium chloride, 1-Allyl-3-methylimidazolium chloride, 1-Allyl-3-methylimidazolium bromide, 1-Allyl-3-methylimidazolium dicyanamide, 1-Allyl-3-methylimidazolium bis(trifluoromethanesulfonyl)imide, 1-Methyl-3-propylimidazolium methyl carbonate, 1-Methyl-3-propylimidazolium iodide, 1-Methyl-3-vinylimidazolium methyl carbonate, 1-Methylimidazolium hydrogen sulfate, 1- Methylimidazolium chloride, 1-methyl-3-octylimidazolium trifluoromethanesulfonate, 1-methyl-3-octylimidazolium tetrafluoroborate, 1-methyl-3-octylimidazolium chloride, 1-decyl-3-methylimidazolium tetrafluoroborate, decylmethylimidazolium chloride, 1-hexyl-3-methylimidazolium iodide, 1-(2-hydroxyethyl)-3-methylimidazolium dicyandiamide, 1-benzyl-3-methylimidazolium hexafluorophosphate, 1-benzyl-3-methylimidazolium tetrafluoroborate, 1-octyl-3-methylimidazolium hexafluorophosphate, 1-butyl-3-methylimidazolium acetate, 1-butyl-3-methylimidazolium bis(trifluoromethanesulfonyl)imide, 1-butyl-3-methylimidazolium chloride, 1-butyl-3-methylimidazolium methanesulfonate, 1-butyl- 3-Methylimidazolium hydrogen sulfate, 1-butyl-3-methylimidazolium methyl sulfate, 1-butyl-3-methylimidazolium trifluoromethanesulfonate, 1-butyl-3-methylimidazolium tetrafluoroborate, 1-butyl-3-methylimidazolium thiocyanate, 1,2,3-trimethylimidazolium methanesulfonic acid, 1-propyl-3-methylimidazolium bis(trifluoromethanesulfonyl)imine, 1-ethyl-2,3-dimethylimidazolium ethyl sulfate, 1-ethyl-3-methylimidazolium trifluoromethanesulfonate, 1-ethyl-3-methylimidazolium diethyl phosphate, 1-ethyl-3-methylimidazolium diaminonitrile, 1-ethyl-3-methylimidazoline bis(trifluoromethanesulfonyl)imine, 1-ethyl-3-methylimidazolium tetrafluoroborate, 1-ethyl-3-methylimidazolium diaminonitrile, 1-ethyl-3-methylimidazolium ... 1-Ethyl-3-methylimidazolium aluminate, 1-Ethyl-3-methylimidazolium methanesulfonate, 1-Ethyl-3-methylimidazolium thiocyanate, 1-Ethyl-3-methylimidazolium ethyl sulfate, 1-Ethyl-3-methylimidazolium hydrogen sulfate, 1-Ethyl-3-methylimidazolium acetate, 1-Ethyl-3-methylimidazolium chloride, 1-methylimidazolium hydrogen sulfate, 1-methylimidazolium chloride, tributylmethylphosphine dibutyl phosphate, tributylmethylphosphine methyl sulfate, triethylmethylphosphine dibutyl phosphate, trihexyltetradecylphosphine bromide, trihexyltetradecylphosphine chloride, trihexyltetradecylphosphine decanoate, trihexyl(tetradecyl)phosphine dicyandiamide, trihexyltetradecylphosphine bis(trifluoromethanesulfonyl)amide, trihexyltetradecylphosphine bis(2,4,4-Trimethylpentyl)phosphite, 3-(triphenylphosphine)propane-1-toluenesulfonyl, 3-(triphenylphosphine)propane-1-sulfonate, tetrabutylphosphine tetrafluoroborate, tetrabutylphosphine p-toluenesulfonate, tetrabutylphosphine methanesulfonate, 1-Butyl-1-methylpyrrolidine trifluoromethanesulfonate, 1-Butyl-1-methylpyrrolidine dinitrileamine salt, 1-Butyl-1-methylpyrrolidine hexafluorophosphate, 1-Butyl-1-methylpyrrolidine bis(trifluoromethanesulfonyl)imide, 1-Butyl-1-methylpyrrolidine bis(trifluoromethanesulfonyl)imide, 1-Butyl-1-methylpyrrolidine tetrafluoroborate, 1-Butyl-1-methylpyrrolidine chloride, 1-Butyl-1-methylpyrrolidine bromide The following are listed: 1-Butyl-1-methylpyrrolidine iodide, 1-Butyl-1-methylpyrrolidine methyl carbonate, 1-Ethyl-1-methylpyrrolidine bis(trifluoromethanesulfonyl)imide, 1-Ethyl-1-methylpyrrolidine tetrafluoroborate, 1-Methyl-1-ethylpyrrolidine hexafluorophosphate, 1-Methyl-1-ethylpyrrolidine bromide, triethylsulfonium bis(trifluoromethanesulfonyl)imide, cyclopropyl diphenylsulfonium tetrafluoroborate, 1-Butyl-1-methylpiperidinium tetrafluoroborate, 1-Butyl-1-methylpiperidinium hexafluorophosphate, 1-Butyl-1-methylpiperidinium bis(trifluoromethanesulfonyl)imide, and 4-Ethyl-4-methylmorpholine methyl carbonate. The polymer is any combination of polystyrene, polystyrene, polymethyl methacrylate, polyethyl methacrylate, polypropyl methacrylate, polyisopropyl methacrylate, polybutyl methacrylate, polyisobutyl methacrylate, polytert-butyl methacrylate, polypentyl methacrylate, polyisopentyl methacrylate, polymethyl methacrylate, polyethyl methacrylate, polypropyl methacrylate, polyisopropyl methacrylate, polybutyl methacrylate, polyisobutyl methacrylate, polytert-butyl methacrylate, polypentyl methacrylate, polyisopentyl methacrylate, polyhexyl methacrylate, polyethylene glycol, polyvinyl alcohol, polyurethane, polyethylene, polycarbonate, polyamide, polytetrafluoroethylene, diethyl terephthalate, polybutylene terephthalate, polyvinyl acetate, polysilicon, polyacrylonitrile, polychlorotrifluoroethylene, acrylonitrile-butadiene-styrene copolymer, and polydimethylsilicate.

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