CN106647089B - A kind of electrochromic device and preparation method thereof based on organic conjugate gel - Google Patents
A kind of electrochromic device and preparation method thereof based on organic conjugate gel Download PDFInfo
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- CN106647089B CN106647089B CN201610793941.4A CN201610793941A CN106647089B CN 106647089 B CN106647089 B CN 106647089B CN 201610793941 A CN201610793941 A CN 201610793941A CN 106647089 B CN106647089 B CN 106647089B
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- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/15—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on an electrochromic effect
- G02F1/153—Constructional details
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- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/15—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on an electrochromic effect
- G02F1/153—Constructional details
- G02F1/155—Electrodes
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- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/15—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on an electrochromic effect
- G02F1/1514—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on an electrochromic effect characterised by the electrochromic material, e.g. by the electrodeposited material
- G02F1/1516—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on an electrochromic effect characterised by the electrochromic material, e.g. by the electrodeposited material comprising organic material
- G02F1/15165—Polymers
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- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/15—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on an electrochromic effect
- G02F2001/164—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on an electrochromic effect the electrolyte is made of polymers
Abstract
The invention discloses the organic electrochromic devices and preparation method thereof based on organic conjugate gel.The organic electrochromic device is made of the sequentially connected substrate coated with electroconductive ITO, the organic conjugate gel containing electrolyte and another substrate coated with electroconductive ITO；The organic conjugate gel containing electrolyte is prepared via a method which: by three (4- (5 '-18-2 '-thiophene of alkylamide) benzene) amine or 1,3, (5 '-18-2 '-thienyl of the alkylamide) benzene of 5- tri- and tetra-n-butyl ammonium perchlorate are added in organic solvent, it is heated to being completely dissolved, then natural cooling obtains the organic conjugate gel containing electrolyte.Reversible color change can occur under the action of a certain voltage for the device.The structure of electrochromic device according to the present invention is simple, overcomes the shortcomings that material need to be processed film forming and lead to increased costs by conventional electrochromic de, is advantageously implemented the industrialized production of electrochromic device.
Description
Technical field
The present invention relates to organic electrochromic technical fields, and in particular to the electrochromic device based on organic conjugate gel
And preparation method thereof.
Background technique
Electrochromism refers to that under the action of extra electric field redox reaction occurs for the electroactive material of tool, to lead
The variation for causing uv-visible absorption spectroscopy, shows as the variation of color and transparency in appearance.Electrochromism technology is aobvious
Show, building energy conservation window, anti-glare rear-view mirror for automobile, aircraft tunable optical glass, the military fields such as anti-fake show and answer well
Use prospect.
Electrochromic activity material is mainly passed through vapor deposition, spin coating, ink-jet by the preparation method of electrochromic device at present
" sandwich type " electrochromic device is assembled into together with ito glass after the methods of printing or roller coating film forming, and device contains liquid
Body electrolyte does not have electroactive gel electrolyte.Using the above method preparation electrochromic device cost of manufacture compared with
Height is unfavorable for the implementation of course of industrialization.
The existing shortcoming for preparing electrochromic device is:
(1), after electrochromic activity material is formed a film by the methods of vapor deposition, spin coating, inkjet printing or roller coating with ito glass
It is assembled into " sandwich type " electrochromic device together, and device contains liquid electrolyte or do not have electroactive gel electrolyte
Matter.
(2), currently used electrochromic material is polymer film, it is that monomer passes through electrochemical oxidation method or chemistry
What method for oxidation polymerize.The hard defects of polymer film are that molecular weight is uncertain, have the problem of molecular weight distribution, repeatability
Difference, so that the stability that changes colour is poor.
Summary of the invention
The object of the invention is to be electrolysed using containing in order to solve the problem of to prepare device higher cost complex process
The organic conjugate gel of matter prepares novel organic electrochromic device directly as electrochromic activity layer, provides a kind of novel
Organic electrochromic device and preparation method thereof.
The object of the invention is achieved through the following technical solutions:
A kind of electrochromic device based on organic conjugate gel, the electrochromic device are coated with by sequentially connected
The substrate of electroconductive ITO, the organic conjugate gel containing electrolyte and another substrate composition coated with electroconductive ITO；
The organic conjugate gel containing electrolyte is prepared via a method which: by three (4- (5 ' -18 alkylamides -
2 '-thiophene) benzene) amine (3TPA-3NC18) or 1,3,5- tri- (5 '-18-2 '-thienyl of alkylamide) benzene (3TB-3NC18) and four
Normal-butyl ammonium perchlorate is added in organic solvent, is heated to being completely dissolved, then natural cooling, obtains having containing electrolyte
Machine is conjugated gel.
To further realize the object of the invention, it is preferable that in terms of mass fraction, three (4- (5 ' -18 alkylamides -
2 '-thiophene) benzene) amine or (5 '-18-2 '-thienyl of alkylamide) the benzene dosage of 1,3,5- tri- be 3-10 parts；The tetra-n-butyl is high
Ammonium chlorate dosage is 100000-200000 parts.
Preferably, the organic solvent is ethyl alcohol, isopropanol, chlorine benzene,toluene,xylene or n-hexane.
Preferably, the substrate is glass, polyethylene terephthalate film or polyimide film.
Preferably, the time of the natural cooling is 30-90 minutes.
Preferably, when raw material is three (4- (5 '-18-2 '-thiophene of alkylamide) benzene) amine, electrochromic device is applied
When the voltage of 1-6V, the color of electrochromic device becomes red from yellow, when application -1--7V voltage, electrochromic device
Color become yellow from red, reversible variation occurs for the color of device.
Preferably, when raw material is 1,3,5- tri- (5 '-18-2 '-thienyl of alkylamide) benzene, electrochromic device is applied
When adding the voltage of 1-6V, the color of electrochromic device becomes light red from colourless；When application -1--7V voltage, electrochromism
The color of device becomes colorless from light red, and reversible variation occurs for the color of device.
The preparation method of the electrochromic device based on organic conjugate gel: by three (4- (5 ' -18 alkylamides -
2 '-thiophene) benzene) benzene is added to tetra-n-butyl ammonium perchlorate has by amine or 1,3,5- tri- (5 '-18-2 '-thienyl of alkylamide)
It in solvent, is heated to being completely dissolved, then natural cooling, obtains the organic conjugate gel containing electrolyte；
It uses the substrate coated with electroconductive ITO as an electrode, the organic conjugate gel blade coating containing electrolyte is being applied
It is covered with the substrate surface of electroconductive ITO, forms the organic conjugate gel film layer containing electrolyte, is then coated with conduction for another
The substrate of ITO is covered on the organic conjugate gel film surface containing electrolyte as another electrode, by another electrode, and two
Electrode edge is encapsulated with curable adhesive.
Preferably, the organic conjugate gel film layer containing electrolyte with a thickness of 0.1-0.3mm.
Preferably, every mg tri- (4- (5 '-18-2 '-thiophene of alkylamide) benzene) amine or 1,3,5- tri- (5 '-18 alkylamides-
2 '-thienyls) benzene addition organic solvent 0.05-1mL.
The organic conjugate gel is by 3TPA-3NC18And 3TB-3NC18It is formed respectively with organic solvent, 3TPA-
3NC18And 3TB-3NC18Structure it is as follows.
The invention patent compared with prior art, has the following advantages and benefits:
(1), novel Organic Electricity is prepared directly as electrochromic activity layer using the organic conjugate gel containing electrolyte
Mutagens color device, simple process, stability are reproducible
(2) present invention uses small organic molecule as electrochromic material, and small molecule has specific chemical structure, determines
Molecular weight is easy to the advantages that purifying, and applied to product is actually prepared, repeated stability is good.
Detailed description of the invention
Fig. 1 is that embodiment 1 is based on 3TPA-3NC18It is conjugated the discoloration photo of the organic electrochromic device of gel.
Fig. 2 is that embodiment 3 is based on 3TB-3NC18It is conjugated the discoloration photo of the organic electrochromic device of gel.
Specific embodiment
For a better understanding of the invention, the present invention will be further explained with reference to the examples below, but reality of the invention
It is unlimited so to apply mode.
Embodiment 1
A kind of preparation method of the electrochromic device based on organic conjugate gel: by three (4- (5 ' -18 alkyl acyls of 3mg
Amine -2 '-thiophene) benzene) amine (3TPA-3NC18) and the tetra-n-butyl ammonium perchlorate of 100g be added to the n-hexane of 0.5mL, heating makes
It is completely dissolved, then natural cooling 30 minutes, i.e. organic conjugate gel of the formation containing electrolyte.
It uses the substrate coated with electroconductive ITO as an electrode, the organic conjugate gel blade coating containing electrolyte is being applied
It is covered with substrate (glass) surface of electroconductive ITO, forms the organic conjugate gel film layer containing electrolyte, control contains electrolyte
Organic conjugate gel film layer with a thickness of 0.1mm, then the substrate (glass) by another coated with electroconductive ITO as another electricity
Pole；Another electrode is covered on to the surface of the organic conjugate gel film layer containing electrolyte, two electrode edge photocurings
Adhesive encapsulation.
(do not shown in the specific change procedure figure of color) as shown in Figure 1, when to embodiment 1 obtain based on organic total
The electrochromic device of yoke gel (is based on 3TPA-3NC18Be conjugated gel organic electrochromic device) apply 1V voltage when,
Based on 3TPA-3NC18The color for being conjugated the organic electrochromic device of gel becomes red from yellow, as application -1V, is based on
The electrochromic device of organic conjugate gel (is based on 3TPA-3NC18Device) color become yellow from red.
Embodiment 2
A kind of preparation method of the electrochromic device based on organic conjugate gel: by three (4- (5 ' -18 alkyl acyls of 4mg
Amine -2 '-thiophene) benzene) amine (3TPA-3NC18) and the tetra-n-butyl ammonium perchlorate of 115g be added in the toluene of 0.8mL, heating makes
It is completely dissolved, then natural cooling 40 minutes, i.e. organic conjugate gel of the formation containing electrolyte.
With the substrate for being coated with electroconductive ITO as an electrode, the organic conjugate gel blade coating containing electrolyte is being applied
It is covered with substrate (polyethylene terephthalate film) surface of electroconductive ITO, forms the organic conjugate gel mould containing electrolyte
Layer, control the organic conjugate gel film layer containing electrolyte with a thickness of 0.3mm, then by another base coated with electroconductive ITO
Material (polyethylene terephthalate film) is used as another electrode；Another electrode is covered on containing the organic of electrolyte
It is conjugated the surface of gel film layer, two electrode edges are encapsulated with curable adhesive.
The electrochromic device based on organic conjugate gel that the present embodiment 2 obtains applies colourshifting process and implementation after voltage
Example 1 is identical.
Embodiment 3
A kind of preparation method of the electrochromic device based on organic conjugate gel: by (5 ' -18 alkane of 1,3,5- tri- of 6mg
Base amide -2 '-thienyl) benzene (3TB-3NC18) and the tetra-n-butyl ammonium perchlorate of 130g be added in the chlorobenzene of 0.5-3mL, add
Heat makes it completely dissolved, then natural cooling 40 minutes, i.e. organic conjugate gel of the formation containing electrolyte.
With the substrate (glass) for being coated with electroconductive ITO as an electrode, the organic conjugate gel containing electrolyte is formed
Film layer, organic conjugate gel film layer of the control containing electrolyte with a thickness of 0.15mm, then by another coated with electroconductive ITO
Substrate (glass) is used as another electrode；Another electrode is covered on to the table of the organic conjugate gel film layer containing electrolyte
Face, two electrode edges are encapsulated with curable adhesive.
(do not shown in the specific change procedure figure of color) as shown in Figure 2, when to embodiment 1 obtain based on organic total
The electrochromic device of yoke gel (is based on 3TB-3NC18Be conjugated gel organic electrochromic device) apply 2V voltage when, base
In 3TB-3NC18The color for being conjugated the organic electrochromic device of gel becomes light red from colourless, as application -2V, is based on
3TB-3NC18The color for being conjugated the organic electrochromic device of gel becomes colorless from light red.
Embodiment 4
A kind of preparation method of the electrochromic device based on organic conjugate gel: by (5 ' -18 alkane of 1,3,5- tri- of 7mg
Base amide -2 '-thienyl) benzene (3TB-3NC18) and the tetra-n-butyl ammonium perchlorate of 150g be added to the dimethylbenzene of 1mL, heating makes
It is completely dissolved, then natural cooling 60 minutes, i.e. organic conjugate gel of the formation containing electrolyte.
With the substrate (polyimide film) for being coated with electroconductive ITO as an electrode, formed organic total containing electrolyte
Yoke gel film layer, control the organic conjugate gel film layer containing electrolyte with a thickness of 0.18mm, then by it is another be coated with lead
The substrate (polyimide film) of electric ITO is used as another electrode；Another electrode is covered on organic total containing electrolyte
The surface of yoke gel film layer, two electrode edges are encapsulated with curable adhesive.
The electrochromic device based on organic conjugate gel that the present embodiment 4 obtains applies colourshifting process and implementation after voltage
Example 3 is identical.
Embodiment 5
A kind of preparation method of the electrochromic device based on organic conjugate gel: by three (4- (5 ' -18 alkyl acyls of 8mg
Amine -2 '-thiophene) benzene) amine (3TPA-3NC18) and the tetra-n-butyl ammonium perchlorate of 200g be added in the isopropanol of 3mL, heating makes
It is completely dissolved, then natural cooling 90 minutes, i.e. organic conjugate gel of the formation containing electrolyte.
With the substrate (glass) for being coated with electroconductive ITO as an electrode, the organic conjugate gel containing electrolyte is formed
Film layer, organic conjugate gel film layer of the control containing electrolyte with a thickness of 0.3mm, then by another coated with electroconductive ITO
Substrate (glass) is used as another electrode；Another electrode is covered on to the table of the organic conjugate gel film layer containing electrolyte
Face, two electrode edges are encapsulated with curable adhesive.
The electrochromic device based on organic conjugate gel that the present embodiment 5 obtains applies colourshifting process and implementation after voltage
Example 1 is identical.
Claims (10)
1. a kind of electrochromic device based on organic conjugate gel, the electrochromic device is led by sequentially connected be coated with
The substrate of electric ITO, the organic conjugate gel containing electrolyte and another substrate composition coated with electroconductive ITO；It is characterized by:
The organic conjugate gel containing electrolyte is prepared via a method which: by three (4- (5 '-18-2 '-thiophenes of alkylamide
Pheno) benzene) amine or (5 '-18-2 '-thienyl of the alkylamide) benzene of 1,3,5- tri- and tetra-n-butyl ammonium perchlorate be added to organic solvent
In, it is heated to being completely dissolved, then natural cooling, obtains the organic conjugate gel containing electrolyte.
2. the electrochromic device according to claim 1 based on organic conjugate gel, which is characterized in that with mass fraction
Meter, described three (4- (5 '-18-2 '-thiophene of alkylamide) benzene) amine or 1,3,5- tri- (5 '-18-2 '-thienyl of alkylamide) benzene
Dosage is 3-10 parts；The tetra-n-butyl ammonium perchlorate dosage is 100000-200000 parts.
3. the electrochromic device according to claim 1 based on organic conjugate gel, which is characterized in that described organic molten
Agent is ethyl alcohol, isopropanol, chlorine benzene,toluene,xylene or n-hexane.
4. the electrochromic device according to claim 1 based on organic conjugate gel, which is characterized in that the substrate is
Glass, polyethylene terephthalate film or polyimide film.
5. the electrochromic device according to claim 1 based on organic conjugate gel, which is characterized in that described naturally cold
But time is 30-90 minutes.
6. the electrochromic device according to claim 1 based on organic conjugate gel, which is characterized in that when raw material is three
When (4- (5 '-18-2 '-thiophene of alkylamide) benzene) amine, when applying the voltage of 1-6V to electrochromic device, electrochromic device
Color become red from yellow, when applying -7~-1V voltage, the color of electrochromic device becomes yellow, device from red
Reversible variation occurs for the color of part.
7. the electrochromic device according to claim 1 based on organic conjugate gel, which is characterized in that when raw material be 1,
When 3,5- tri- (5 '-18-2 '-thienyl of alkylamide) benzene, when applying the voltage of 1-6V to electrochromic device, electrochromism device
The color of part becomes light red from colourless；When applying -7~-1V voltage, the color of electrochromic device becomes nothing from light red
Reversible variation occurs for color, the color of device.
8. the preparation method of the electrochromic device based on organic conjugate gel described in claim any one of 1-5, feature exist
In, by three (4- (5 '-18-2 '-thiophene of alkylamide) benzene) amine or 1,3,5- tri- (5 '-18-2 '-thienyl of alkylamide) benzene with
Tetra-n-butyl ammonium perchlorate is added in organic solvent, is heated to being completely dissolved, then natural cooling, obtain containing electrolyte
Organic conjugate gel；
It uses the substrate coated with electroconductive ITO as an electrode, the organic conjugate gel blade coating containing electrolyte is being coated with
The substrate surface of electroconductive ITO forms the organic conjugate gel film layer containing electrolyte, then by another coated with electroconductive ITO
Substrate is covered on the organic conjugate gel film surface containing electrolyte, two electrodes as another electrode, by another electrode
Edge is encapsulated with curable adhesive.
9. the preparation method of the electrochromic device according to claim 8 based on organic conjugate gel, which is characterized in that institute
State the organic conjugate gel film layer containing electrolyte with a thickness of 0.1-0.3mm.
10. the preparation method of the electrochromic device according to claim 8 based on organic conjugate gel, which is characterized in that
Every tri- (4- (5 '-18-2 '-thiophene of alkylamide) benzene) amine of mg or 1,3,5- tri- (5 '-18-2 '-thienyl of alkylamide) benzene add
Enter organic solvent 0.05-1mL.
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| US8094361B2 (en) * | 2010-01-05 | 2012-01-10 | Raytheon Company | Polymer shutter compositions and devices for infrared systems |
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| CN102369478A (en) * | 2009-03-31 | 2012-03-07 | 康涅狄格大学 | Flexible electrochromic device, electrodes therefor, and method of manufacture |
| CN102870040A (en) * | 2010-03-25 | 2013-01-09 | 康涅狄格大学 | Formation of conjugated polymers for solid-state devices |
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