CN107739429A - Poly- dibromo methyl ethylene dioxy thiophene blue-tinted transparent electrochromic material and preparation method, component and application - Google Patents
Poly- dibromo methyl ethylene dioxy thiophene blue-tinted transparent electrochromic material and preparation method, component and application Download PDFInfo
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Abstract
Invention describes a kind of new thiofuran polymer blue-tinted transparent electrochromic material：Poly- dibromo methyl ethylene dioxy thiophene blue-tinted transparent electrochromic material and preparation method thereof, component and application.The film color that the polymer is formed can realize blue-tinted transparent reversible change under relatively low driving voltage, available for devices such as electrochromic, electrochromic display device (ECD)s.The present invention is by the outstanding youth talent's support plan project of Anhui Universities（gxyq2017023）, Anhui Universities physicism project（KJ2017A482, KJ2016JD16）, key lab of advanced construction material Anhui Province open problem（JZCL201602ZZ）, Students' Innovation foundation drill program funded projects.
Description
Technical field
The present invention relates to the synthesis of electrochromic material and film build method, specially poly- dibromo methyl ethylene dioxy thiophene is blue
Color-transparent electrochromic material and preparation method, component and application.
Background technology
Under alternate height or positive and negative External Electrical Field by injecting or extracting electric charge redox reaction occurs for material,
It is referred to as electroluminescent change so as to which the phenomenon of reversible change occur between the coloured state of low transmission and the colour killing state of high transmittance
Color, the reversible change of color and transparency is shown as in appearance, have in fields such as electrochromic, electrochromic displays wide
Application prospect.
Electrochromic material has bistable performance, and the electrochromic display device made with electrochromic material is not only
Do not need backlight, and after showing still image, as long as display content does not change, would not power consumption, reach the purpose of energy-conservation.
With ignoring, blind angle, contrast are high, manufacturing cost is low, operating temperature range compared with other displays for electrochromic display device (ECD)
Wide, the advantages that driving voltage is low, rich in color, show in instrument, outdoor advertising, the field such as static state display have very big application
Prospect.
Inorganic electrochromic material is mainly with WO3、MoO3, the transition metal oxide such as NiO be representative, the change of its light absorbs
It is caused by because the Dual Implantations and black soy sauce of ion and electronics take.Organic electrochromic material then with organic molecule purpurine and
Pi-conjugated polymer such as polyaniline, polypyrrole, polythiophene etc. are representative, and the change of its light absorbs comes from redox reaction, this kind of
Material color enriches, and easily carries out MOLECULE DESIGN, thus is more exposed to the favor of researcher.Particularly 3,4- propylenedioxythiophenes
(such as 3,4-ethylene dioxythiophene PEDOT), because two epoxides of electron donor can stablize closing shell under high p-doping level
Bipolaron structure, thus provide high conductivity and transparent Indium state, electroluminescent change for poly- (3,4- alkylenedioxythiophene)
Color material is either still shown applied to smart window, is required for material to have transparent state (be close to and fade completely), thus this
One finds to promote the extensive use of 3,4- propylenedioxythiophene polymer.
Main polymer chain rigidity and molecule interchain pi-pi accumulation, which act on, causes pi-conjugated polymer to have not molten insoluble spy
Property, therefore the method for researchers' generally use electrochemical polymerization makes when preparing electrochromic device using pi-conjugated polymer
Obtained polymer is deposited directly to electrode surface and forms thin polymer film.Electropolymerization is to make monomer in anode using applied voltage
Generation electrochemical oxidation reactions, by the way that progressively coupling forms conjugated polymer between free radical.
Gather relative to using coupling of the ferric trichloride as the chemical oxidising polymerisation of oxidant and using palladium complex as catalyst
Reaction is closed, electropolymerization method synthesis of conjugate polymer has advantages below：
(1) electropolymerization can directly obtain polymer under suitable voltage by anodic oxidation reactionses, without in addition
Oxidant or catalyst are added, reduces the synthesis cost of conjugated polymer；
(2) electrolyte that conjugated polymer is doped into during electropolymerization can be gone to adulterate conveniently by negative voltage is applied
(reduction) reaction remove, so as to get polymer it is purer；
(3) conjugated polymer that electropolymerization obtains can be deposited directly in conductive substrates, without being done to polymer
Further film forming processing, reduces processing charges and difficulty of the conjugated polymer thin films when applied to organic optoelectronic device
Degree.
Polyglycolic acid fibre (PEDOT) due to its there is the advantages of low driving voltage, quick response, high transmittance difference and
By the extensive favor of electrochromic material developmental research.Polymerization is lifted by the chemical modification of main polymer chain or side base
Thing electrochromic property is most frequently used means.The electropolymerization of ethylenedioxy thiophene and its derivative turns into organic photoelectric
The researcher that son learns Material Field obtains the commonly used synthetic method of novel electrochromic material.
The content of the invention
Present invention aims at provide a kind of new blueness-transparent polythiophene class electrochromic material：Poly- two bromomethyl
Ethylenedioxy thiophene, its color can between blue and transparent reversible change, have driving voltage low, coloration efficiency is high, oxygen
Change the features such as state is transparent, optical contrast is high, available for devices such as electrochromic, electrochromic display device (ECD)s.
In order to achieve the above object, the technical solution adopted by the present invention is as follows：
A kind of poly- dibromo methyl ethylene dioxy thiophene blueness-transparent electrochromic material, it is characterised in that its structural formula is such as
Under：
Wherein n represents the degree of polymerization, is natural number.
The preparation method of described poly- dibromo methyl ethylene dioxy thiophene blueness-transparent electrochromic material, its feature exist
In comprising the following steps：
Step 1, by 3,4- dimethoxy-thiophenes, the bromo- 2,3- butanediols of 1,4- bis-, p-methyl benzenesulfonic acid and toluene add on
In the flask for just connecting the apparatus,Soxhlet's for including molecular sieve, heated overnight at reflux after mixing, room temperature is subsequently cooled to, washed,
Anhydrous sodium sulfate drying, rotary evaporation remove solvent, and crude by column chromatography obtains white solid, obtains dibromo methyl ethylene dioxy
Thiophene, synthetic route are as follows；
Step 2, by dibromo methyl ethylene dioxy thiophene, LiClO4Acetonitrile is dissolved in, is placed in three-electrode cell, is used
Cyclic voltammetry carries out electrochemical polymerization, obtains poly- dibromo methyl ethylene dioxy thiophene.Synthetic route is as follows：
The bromo- 2,3- butanediols of 3,4- dimethoxy-thiophenes, 1,4- bis-, p-methyl benzenesulfonic acid, the use of toluene in the step 1
It is (1-3) mmol to measure ratio：(1-6)mmol：(0.1-0.5)mmol：(5-50)mL.
Dibromo methyl ethylene dioxy thiophene, LiClO in the step 24Amount ratio is (0.005-0.1) mol/L：
(0.05-0.5)mol/L。
The present invention also protects described poly- dibromo methyl ethylene dioxy thiophene blueness-transparent electrochromic material in manufacture electricity
Application in mutagens color device, described electrochromic device include but is not limited to smart window, electrochromic display device (ECD).
The present invention also protects the component of described poly- dibromo methyl ethylene dioxy thiophene blueness-transparent electrochromic material,
Described component is electrochomeric films.
The film build method of described electrochomeric films is that poly- dibromo methyl ethylene dioxy thiophene electropolymerization film is direct
Plating is on ito glass surface.
The present invention is a kind of new blueness-transparent polythiophene class electrochromic material：Poly- dibromo methyl ethylene dioxy thiophene
Fen, polymer chain is loosely piled up by the introduced steric hindrance effect of double Bromomethyl Substituteds, improve doping level, its color
Can between blue and transparent reversible change, have driving voltage low, coloration efficiency is high, oxidation state is transparent, optical contrast
The features such as high, the film formed by it, device can be used for the devices such as electrochromic, electrochromic display device (ECD).
Brief description of the drawings
Fig. 1 is the nucleus magnetic hydrogen spectrum of dibromo methyl ethylene dioxy thiophene prepared by embodiment 1.
Fig. 2 is that the electropolymerization of embodiment 1 tests continuous cyclic voltammetry curve.
Fig. 3 is polymer-poly- dibromo methyl ethylene dioxy thiophene (PEDOT (MeBr) prepared by embodiment 12) film circulation
Volt-ampere curve.
Fig. 4 is spectroelectrochemistry spectrogram of the thin polymer film under different applied voltages.
Fig. 5 is that chromaticity coordinates changes in thin polymer film oxidizing process.
Fig. 6 is thin polymer film voltage step timing absorbance figure.Ordinate representation polymer film is in 669nm in figure
The transmitance at place, abscissa represent the time.
Fig. 7 is thin polymer film voltage step timing electricity/timing absorbance figure.
Fig. 8 is the long-term cyclic voltammetric stability experiment curve of thin polymer film, including the 2nd circle and the 200th circle cyclic voltammetric
Curve.
Embodiment
Embodiment 1
A kind of poly- dibromo methyl ethylene dioxy thiophene blueness-transparent electrochromic material, its preparation method are：
Step 1, by 3,4- dimethoxy-thiophenes (35mmol), the bromo- 2,3- butanediols (70mmol) of 1,4- bis-, to methylbenzene
Sulfonic acid (3.5mmol) and 300ml toluene are added in the flask for the apparatus,Soxhlet's that top connection includes molecular sieve, by mixture plus
Heat backflow overnight, is subsequently cooled to room temperature, several times, anhydrous sodium sulfate drying, rotary evaporation removes solvent, crude product warp for washing
Column chromatography obtains white solid, obtains dibromo methyl ethylene dioxy thiophene (EDOT (MeBr)2), yield 30%, obtained dibromo first
Base ethylenedioxy thiophene (EDOT (MeBr)2) nucleus magnetic hydrogen spectrum see Fig. 1, ordinate represents peak intensity, abscissa representativeization in figure
Displacement study δ.δ=6.41 (s, 2H) peak corresponds to thiphene ring 2-, 5- position hydrogen atom, and δ=4.47 (m, 2H) peak corresponds to enedioxy bridge
Hydrogen atom, δ=3.61 (m, 4H) peak correspond to bromomethyl hydrogen atom.Fig. 1 illustrates the correctness of monomer chemical constitution.
Step 2, by EDOT (MeBr)2(0.01mol/L)、LiClO4(0.1mol/L), which merges, is dissolved in 10mL acetonitriles, puts
In three-electrode cell, electrochemical polymerization, electropolymerization experiment condition are carried out using cyclic voltammetry：Using the electricity of nitrogen protection three
Pole electrolytic cell, Pt silks are to electrode, and Ag silks are reference electrode, and ITO electro-conductive glass is working electrode, voltage scan range 0-
1.8V, 5 circulations are scanned, monomer initial oxidation current potential is 1.5V, electropolymerization film Direct Electroplating is obtained in ito glass surface
To poly- dibromo methyl ethylene dioxy thiophene PEDOT (MeBr)2Film.
Electropolymerization tests continuous cyclic voltammetry curve and sees Fig. 2, and ordinate is electric current in figure, and abscissa is voltage.From figure
Can illustrate thin polymer film that electropolymerization obtains constantly be deposited on ITO working electrode surfaces make oxidation current and reduction current with
Scanning hop count increases and increased.
By the polymer of preparation-poly- dibromo methyl ethylene dioxy thiophene (PEDOT (MeBr)2) film progress cyclic voltammetric reality
Test, experiment condition：Using three-electrode cell, Pt silks to be reference electrode to electrode, Ag silks, be coated with thin polymer film (2cm ×
0.7cm) ITO electro-conductive glass is working electrode, and scanning voltage scope -0.1V -0.65V, sweep speed is respectively 50mV/s,
100mV/s, 150mV/s, 200mV/s, supporting electrolyte configuration：0.1mol/L lithium perchlorates (LiClO4) it is dissolved in 10mL carbonic acid third
Alkene ester (PC), thin polymer film cyclic voltammetry curve are shown in Fig. 3, illustrate that polymer oxidation spike potential is when sweep speed is 50mV/s
0.4V, reduction spike potential are 0.05V, and oxidation-reduction process can be completed in scanning voltage scope -0.1V-0.65V interpolymers.
Embodiment 2
The spectroelectrochemistry performance test of thin polymer film prepared by embodiment 1 under different applied voltages.
Experiment condition：Using three-electrode cell, Pt silks are coated with thin polymer film to be reference electrode to electrode, Ag silks
(2cm × 0.7cm) ITO electro-conductive glass is working electrode, and supporting electrolyte configures：0.1mol/L lithium perchlorates (LiClO4) molten
In 10mL propene carbonates (PC)；Spectroelectrochemistry spectrogram of the polymer under different applied voltages is shown in Fig. 4, condition in explanation
Thin polymer film (- 0.1V) is blueness, and a length of 669nm of maximum absorption wave, polymer complete oxidation state (0.65V) is transparent state,
In visible region substantially without absorption.
Chromaticity coordinates change test, test result are shown in Fig. 5 in thin polymer film oxidizing process, illustrate that condition color is sat in polymer
A*=5.66, b*=-60.07 are designated as, is blue state；Polymer complete oxidation state chromaticity coordinates is a*=3.26, b*=-
16.02, it is transparent state, polymer is blueness-transparent electrochromic material.
Embodiment 3
Thin polymer film voltage step timing absorbance test prepared by embodiment 1.Step voltage be -0.1V and
0.65V, voltage residence time are respectively 30s, 20s, 15s, 10s.Supporting electrolyte configures：0.1mol/L lithium perchlorates
(LiClO4) it is dissolved in 10mL propene carbonates (PC).Using three-electrode cell, Pt silks are that Ag silks are reference electrode to electrode,
It is working electrode to be coated with thin polymer film (2cm × 0.7cm) ITO electro-conductive glass.Test result is shown in Fig. 6, illustrates the oxygen of polymer
It is reversible to change reduction process, the transmitance difference Δ T at 669nmmax=59.6%, its oxidizing process reaches 95% transmitance difference and rung
T between seasonable95=3.5s.
Embodiment 4
Thin polymer film voltage step timing electricity prepared by embodiment 1/timing absorbance test.Step voltage for-
0.1V and 0.65V, voltage residence time are respectively 20s.Supporting electrolyte configures：0.1mol/L lithium perchlorates (LiClO4) be dissolved in
10mL propene carbonates (PC).Using three-electrode cell, Pt silks are coated with polymer thin to be reference electrode to electrode, Ag silks
Film (2cm × 0.7cm) ITO electro-conductive glass is working electrode.Test result is shown in Fig. 7, illustrates that thin polymer film oxidizing process exists
Coloration efficiency when reaching 100% transmitance difference at 669nm is 183.1cm2(calculation formula is CE=Δs OD/ (Q/A)=lg to/C
(Tb/Tc)/ (Q/A))。
Embodiment 5
The long-term cyclic voltammetric stability test of thin polymer film prepared by embodiment 1.Supporting electrolyte configures：0.1 mol/
L lithium perchlorates (LiClO4) it is dissolved in 10mL propene carbonates (PC).Cyclic voltammetry experiment condition：Using three-electrode cell, Pt
For silk to be reference electrode to electrode, Ag silks, it is working electrode to be coated with thin polymer film (2cm × 0.7cm) ITO electro-conductive glass, is swept
Voltage range -0.1V-0.65V is retouched, sweep speed is respectively 100mV/s.Test result is shown in Fig. 8, illustrates by 200 oxidations
Reduction circulation, current density do not decay, and polymer has good long oxidation reduction cyclical stability.
As can be seen from the above embodiments, thin polymer film its color that prepared by the present invention can be between blue and transparent
Reversible change, there is the features such as driving voltage is low, and coloration efficiency is high, oxidation state is transparent, optical contrast is high, it is electric available for preparing
Mutagens color device, applied in fields such as smart window, electrochromic display device (ECD)s.
Claims (8)
1. poly- dibromo methyl ethylene dioxy thiophene blueness-transparent electrochromic material, it is characterised in that its structural formula is as follows：
Wherein n represents the degree of polymerization, is natural number.
2. the preparation method of poly- dibromo methyl ethylene dioxy thiophene blueness-transparent electrochromic material as claimed in claim 1,
It is characterised in that it includes following steps：
Step 1, it will connect above the addition of 3,4- dimethoxy-thiophenes, the bromo- 2,3- butanediols of 1,4- bis-, p-methyl benzenesulfonic acid and toluene
In the flask for connecing the apparatus,Soxhlet's for including molecular sieve, heated overnight at reflux after mixing, room temperature is subsequently cooled to, washed, it is anhydrous
Sodium sulphate is dried, and rotary evaporation removes solvent, and crude by column chromatography obtains white solid, obtains dibromo methyl ethylene dioxy thiophene
Fen；
Step 2, by dibromo methyl ethylene dioxy thiophene, LiClO4Acetonitrile is dissolved in, is placed in three-electrode cell, using circulation
Voltammetry carries out electrochemical polymerization, obtains poly- dibromo methyl ethylene dioxy thiophene.
3. preparation method as claimed in claim 2, it is characterised in that 3,4- dimethoxy-thiophenes, Isosorbide-5-Nitrae-two in the step 1
Bromo- 2,3- butanediols, p-methyl benzenesulfonic acid, the amount ratio of toluene are (1-3) mmol：(1-6)mmol：(0.1-0.5)mmol：
(5-50)mL。
4. preparation method as claimed in claim 2, it is characterised in that dibromo methyl ethylene dioxy thiophene in the step 2,
LiClO4Amount ratio is (0.005-0.1) mol/L：(0.05-0.5)mol/L.
5. poly- dibromo methyl ethylene dioxy thiophene blueness-transparent electrochromic material described in claim 1 is manufacturing electroluminescent change
Application in color device.
6. the component containing poly- dibromo methyl ethylene dioxy thiophene blueness-transparent electrochromic material as claimed in claim 1.
7. component as claimed in claim 6, it is characterised in that described component is electrochomeric films.
8. component as claimed in claim 7, it is characterised in that the film build method of described electrochomeric films is by poly- dibromo
Methyl ethylene dioxy thiophene electropolymerization film Direct Electroplating is on ito glass surface.
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|---|---|---|---|---|
| CN103666445A (en) * | 2013-12-17 | 2014-03-26 | 京东方科技集团股份有限公司 | Blue electrochromic material as well as preparation method and assembly thereof |
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| CN106543415A (en) * | 2016-09-29 | 2017-03-29 | 浙江工业大学 | Thin polymer film based on chi structure conjugated molecule and preparation method and application |
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2017
- 2017-09-29 CN CN201710908780.3A patent/CN107739429A/en active Pending
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103666445A (en) * | 2013-12-17 | 2014-03-26 | 京东方科技集团股份有限公司 | Blue electrochromic material as well as preparation method and assembly thereof |
| CN105388660A (en) * | 2015-12-17 | 2016-03-09 | 深圳市华星光电技术有限公司 | Preparation method of COA type array substrate |
| CN106543415A (en) * | 2016-09-29 | 2017-03-29 | 浙江工业大学 | Thin polymer film based on chi structure conjugated molecule and preparation method and application |
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| Title |
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| XIAOMING CHEN: "Colorimetric sensing of non-ionic and cationic surfactants using a versatile anionic poly(3,4-propylenedioxythiophene) derivative", 《ANALYTICAL METHODS》 * |
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