CN103059831A - Electrochromic material and electrochromic device - Google Patents
Electrochromic material and electrochromic device Download PDFInfo
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- CN103059831A CN103059831A CN2012104826702A CN201210482670A CN103059831A CN 103059831 A CN103059831 A CN 103059831A CN 2012104826702 A CN2012104826702 A CN 2012104826702A CN 201210482670 A CN201210482670 A CN 201210482670A CN 103059831 A CN103059831 A CN 103059831A
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Abstract
The invention discloses an electrochromic material and an electrochromic device. The electrochromic material is characterized in that the electrochromic material is a mixture which is composed of a cathode electrochromic material and an anode electrochromic material, wherein the anode electrochromic material is provided with three structure general formulas, different substituting groups are arranged on a pyridinium loop so as to aim to strengthen the stability of the structure which is converted to be in a planar state from a orthogonal state and charge dispersibility in the pyridinium loop in a color-changing process, and increase an electric potential difference delta E between the two states; and the electrochromic device comprises a transparent conductive glass and a conductive reflecting glass, wherein a transparent conducting layer (2) of the transparent conductive glass and a conductive reflecting layer (4) of the conductive reflecting glass are arranged oppositely, the peripheries of the transparent conductive glass and the conductive reflecting glass are glued through a glue body so as to form a cavity body, and the electrochromic material is filled in the cavity body. The electrochromic device provided by the invention has the characteristics of long service life and rapid color changing rate and discoloring rate, and is suitable for the fields of anti-dazzling automobile rearview mirrors for intelligent windows of light-dimmer glass for construction.
Description
Technical field
The present invention relates to a kind of electrochromic material, specifically refer to a kind of electrochromic device that is applied to the electrochromic material in the fields such as automatically dimmed anti-dazzle driving mirror and relevant dimming glass and adopts this electrochromic material preparation.
Background technology
Electrochromic material is under the effect of volts DS, and material generation oxidation or reduction cause it to produce reversible change to visible transmission or reflection.Electrochromic material mainly is divided into inorganic electrochromic material and organic electrochromic material at present, inorganic electrochromic material is mainly the metal oxides such as tungstic oxide, nickel oxide, iridium oxide or titanium oxide, and organic electrochromic material mainly comprises polyaniline, Polythiophene, amethyst or phenothiazine compound and derivative thereof.Although electrochromic material is applied in the anti-dazzle driving mirror field, but the variable color that causes owing to the compound own characteristic/fade is slow, less stable, the shortcoming such as off-color material is residual.Therefore be subject in actual applications certain limitation.In patent of invention 200480031402.2, propose the amethyst compound and in variable color and the process of fading, have following structure:
When the amethyst compound was in reduction-state, two orthogonal thereto states of pyridine quaternary ammonium salt ring reduce steric hindrance, and were highly stable, show the water white transparency state.When the amethyst compound obtains an electronics, had two keys between two pyridine quaternary ammonium salts and appeared in the plane generation resonance, thereby generation dark color.When two dimensional structure appears in the amethyst molecular structure, be easy to form conjugated structure between the molecule, overlapping between the aromatic ring appears, have sequence between the molecular structure, therefore the color of amethyst is also become light yellow by dark color.This moment, the amethyst compounds was easy to suffer irreversible destruction, and therefore the life-span of electrochromic device shortens.
In addition, because the supplied for electronic of R1 and R2 group accumulates on the pyridine ring so that the amethyst analog derivative easily produces variable color after variable color, fading time is longer.
Summary of the invention
First technical problem to be solved by this invention provides a kind of electrochromic material, cathode electrochromic material in this electrochromic material is with various substituting groups on pyridine ring, the potential difference Δ E of two states when helping to improve the amethyst compounds structure being transformed into flat state by quadrature in the variable color process, the characteristics that have high life, quick color-changing and fade.
Second technical problem to be solved by this invention provides a kind of electrochromic device, and it is long that this device has the life-span, and the characteristics that variable color and fade rates are fast are applicable to the smart window of anti-glare rear-view mirror for automobile field or dimming glass for building.
The present invention solves the technical scheme that above-mentioned first technical problem adopts: a kind of electrochromic material, it is characterized in that: the mixture that this electrochromic material is comprised of cathode electrochromic material and anode electrochromic material, the chemical structure of general formula of described cathode electrochromic material is: following general structure one, general structure two or general structure three:
In above-mentioned: R
1, R
2Be 1～20 normal paraffin or isoparaffin for carbonatoms;
R
3, R
4Be 1～4 normal paraffin or isoparaffin or methoxy or ethoxy or carboxyl for carbonatoms;
R
5, R
6Be F or Cl or Br or NO
2Or SO
3H;
R
7, R
8Be 1～3 alkane or O or N or S heteroatoms for carbonatoms;
R
9, R
10Be R
3, R
4Be 1～4 alkane or Alkane isomer or methoxy or ethoxy or carboxyl for carbonatoms;
X is
Cl
-, Br
-, BF4
-Or PF6
-Described anode electrochromic material is Polyvinyl carbazole, and its chemical structure of general formula is:
N wherein represents the polymerization degree, is natural number.
As improvement, the preparation method of described cathode electrochromic material may further comprise the steps:
1), synthetic 4,4 '-dipyridyl derivatives: will contain substituent pyridine and sodium Metal 99.5 and join in the reaction flask, described pyridine and sodium Metal 99.5 mol ratio are: 35～45: 1, then being heated to 100～120 ℃ refluxed 20～28 hours, after reaction is finished, be cooled to room temperature, and mixture poured in the ice cube, make the sodium Metal 99.5 reaction complete, obtain profit shape mixture, carry out oily water separation: add anhydrous sodium sulphate in the oily matter with gained, left standstill 16～24 hours, then vacuum rotary steam is removed the excessive substituent pyridine that contains, the product of gained carries out recrystallization after the vacuum rotary steam in ethanolic soln, obtain white or light yellow product, be the 4,4'-Bipyridine derivative;
2), synthetic amethyst compounds: get step 1) synthesized 4, the halogenated alkane of 4 '-dipyridyl derivatives, 0.015～0.025mol and 0.045～0.055mol or halo derivatives are dissolved in the acetonitrile solution of 15～25ml, reflux was cooled to room temperature after 8～12 hours, it is complete that solution precipitation is separated out, remove by filter completely by product of solvent and unreacted, filter cake is soluble in water, add Sodium tetrafluoroborate, sodium hexafluoro phosphate, the aqueous solution of paratoluenesulfonic acid sodium salt or sodium laurylsulfonate, it is complete that solution precipitation is separated out, carry out recrystallization with the throw out filtration and with filter cake, namely obtain cathode electrochromic material.
As preferably, described step 1) substituting group that contains substituent pyridine in is that carbonatoms is 1～4 alkane or Alkane isomer or methoxy or ethoxy or carboxyl.
Preferred again, the described mol ratio that contains substituent pyridine and sodium Metal 99.5 is 40: 1.
The present invention solves the technical scheme that above-mentioned second technical problem adopt: a kind of electrochromic device, it is characterized in that: described electrochromic device includes transparent conducting glass, conduction reflecting glass, the transparency conducting layer of described transparent conducting glass is oppositely arranged with the conductive reflective of conduction reflecting glass, around described transparent conducting glass and conduction reflecting glass, by the bonding formation cavity of colloid, be filled with electrochromic material described above in described cavity the inside.
As preferably, described transparency conducting layer is stannic oxide, indium tin oxide target, mixes the stannic oxide of fluorine, zinc oxide or mix fluorine zinc oxide that the resistance of described transparency conducting layer is less than 20 ohm, and transmittance is more than 80% at visible light 550nm place.
At last, described conductive reflective is preferably silver, rhodium, aluminium, nickel or platinum.
Compared with prior art, the invention has the advantages that: the cathode electrochromic material in the electrochromic material of the present invention on pyridine ring with various substituting groups, electric charge is dispersed in stability when being intended to strengthen the amethyst compounds structure being transformed into flat state by quadrature in the variable color process and the pyridine ring, also improved simultaneously the potential difference Δ E value between the two states, solved the amethyst compounds and be easy to suffer irreversible destruction, after variable color, easily produce the defective that variable color accumulates on the pyridine ring, fading time is long.Equally, adopt the electrochromic device of electrochromic material preparation of the present invention to have the long lifetime, the characteristics that variable color and fade rates are fast are applicable to the smart window of anti-glare rear-view mirror for automobile field or dimming glass for building.
Description of drawings
Fig. 1 is the structural representation of electrochromic device of the present invention.
Embodiment
Embodiment is described in further detail the present invention below in conjunction with accompanying drawing.
A kind of electrochromic material, by the mixture that cathode electrochromic material and anode electrochromic material form, wherein the building-up process of cathode electrochromic material was divided into for two steps:
The first step is synthetic 4,4'-Bipyridine derivative, and pyridine derivate is obtained required target product under the katalysis of suitable sodium Metal 99.5; Reaction equation is as follows:
Second step is synthetic amethyst compounds, and dipyridyl derivatives and halogenated compound reaction that the first step is synthesized obtain corresponding amethyst compounds, and reaction equation is as follows:
Preparation process below by specific embodiment anticathode electrochromic material is elaborated.
Embodiment 1
3-picoline and the 0.025mol sodium Metal 99.5 of 0.1mol are joined in the reaction flask, be heated to 110 ℃ and refluxed 24 hours, reaction is cooled to room temperature, and mixture is poured in the ice cube after finishing, and makes excessive sodium Metal 99.5 reaction complete.Obtain oil-water mixture, carry out oily water separation.In the oily matter of gained, add anhydrous sodium sulphate, hold over night, then vacuum rotary steam is removed the excessive 3-picoline that contains.Revolve that the product of gained carries out recrystallization after steaming in ethanolic soln, obtain white or light yellow product, namely 3,3-dimethyl-4,4-dipyridyl.Get 3 of 0.02mol, 3-dimethyl-4,4-dipyridyl are dissolved in the 20mL acetonitrile solution, add the monobromethane of 0.05mol, back flow reaction 8h again.Mixing solutions with gained after having reacted filters, and filter cake is dissolved in the deionized water, adds Sodium tetrafluoroborate, a large amount of white precipitates occurs.The white precipitate filtration is obtained product (having the compound that chemical structural formula is Fig. 1).
The sign of its chemical structure is as follows: H1NMR (CDCl3-d1): 0.9t (6H ,-CH3), 1.4q (4H,-CH2-), 2.3d (6H ,-CH3), 8.6d (2H, CH), (9.3dd 4H, CH). ultimate analysis: actual measurement C 78.7wt%, H 9.3wt%, N 11.4%; Calculated value C 79.3wt%, H 9.1wt%, N 11.6wt%. mass spectrum: mass-to-charge ratio m/z value is 241.3.
Embodiment 2
3-phenylpyridine and the 0.025mol sodium Metal 99.5 of 0.1mol are joined in the reaction flask, be heated to 110 ℃ and refluxed 24 hours, reaction is cooled to room temperature, and mixture is poured in the ice cube after finishing, and makes excessive sodium Metal 99.5 reaction complete.Obtain oil-water mixture, carry out oily water separation.In the oily matter of gained, add anhydrous sodium sulphate, hold over night, then vacuum rotary steam is removed the excessive 3-phenylpyridine that contains.Revolve that the product of gained carries out recrystallization after steaming in ethanolic soln, obtain white or light yellow product, namely 3,3-phenylbenzene-4,4-dipyridyl.Get 3 of 0.02mol, 3-phenylbenzene-4,4-dipyridyl are dissolved in the 20mL acetonitrile solution, add the heptyl bromide of 0.05mol, back flow reaction 8h again.Mixing solutions with gained after having reacted filters, and filter cake is dissolved in the deionized water, adds paratoluenesulfonic acid sodium salt, a large amount of white precipitates occurs.White precipitate filtered and in dehydrated alcohol recrystallization obtain product (having the compound that chemical structural formula is Fig. 1).
The sign of its chemical structure is as follows: H1 NMR (CDCl3-d1): 0.92t (6H ,-CH3), 1.1～1.6m (24H,-CH2-), 7.2～7.5m (12H, CH), 9.3d (2H, CH), (9.5d 2H, CH). ultimate analysis: actual measurement C 85.1wt%, H 9.0wt%, N 5.3%; Calculated value C 85.4wt%, H 9.1wt%, N 5.5wt%. mass spectrum: mass-to-charge ratio m/z value is 505.1.
Embodiment 3
Quinoline and the 0.025mol sodium Metal 99.5 of 0.1mol are joined in the reaction flask, be heated to 120 ℃ and refluxed 24 hours, reaction is cooled to room temperature, and mixture is poured in the ice cube after finishing, and makes excessive sodium Metal 99.5 reaction complete.Obtain oil-water mixture, carry out oily water separation.In the oily matter of gained, add anhydrous sodium sulphate, hold over night, then vacuum rotary steam is removed the excessive quinoline that contains.Revolve that the product of gained carries out recrystallization after steaming in ethanolic soln, obtain white or light yellow product, i.e. 4-(quinolin-4-yl) quinoline.4-(quinolin-4-yl) quinoline that gets 0.02mol is dissolved in the 20mL acetonitrile solution, adds the N-dodeeyl bromide of 0.05mol, back flow reaction 8h again.Mixing solutions with gained after having reacted filters, and filter cake is dissolved in the deionized water, adds Sodium dodecylbenzene sulfonate, a large amount of white precipitates occurs.The white precipitate filtration is obtained product (having the compound that chemical structural formula is Fig. 1).
The sign of its chemical structure is as follows: H1 NMR (CDCl3-d1): 0.9t (6H ,-CH3), 1.05～1.5m (44H,-CH2-), 7.2～7.8m (8H, CH), 8.6d (2H, CH), (9.3d 2H, CH). ultimate analysis: actual measurement C 78.7wt%, H 9.3wt%, N 11.4%; Calculated value C 84.8wt%, H 10.4wt%, N 4.7wt%. mass spectrum: mass-to-charge ratio m/z value is 593.4.
Embodiment 4
With 5,6,7 of 0.1mol, 8-tetrahydroquinoline and 0.025mol sodium Metal 99.5 join in the reaction flask, are heated to 110 ℃ and reflux 24 hours, and reaction is cooled to room temperature, and mixture is poured in the ice cube after finishing, and make excessive sodium Metal 99.5 reaction complete.Obtain oil-water mixture, carry out oily water separation.In the oily matter of gained, add anhydrous sodium sulphate, hold over night, then vacuum rotary steam is removed excessive 5,6,7, the 8-tetrahydroquinoline that contains.Revolve that the product of gained carries out recrystallization after steaming in ethanolic soln, obtain white or light yellow product, namely 5,6,7,8-tetrahydro-4-(5,6,7,8-tetrahydroquinolin-4-yl) quinoline.Get 5,6,7 of 0.02mol, (5,6,7,8-tetrahydroquinolin-4-yl) quinoline is dissolved in the 20mL acetonitrile solution 8-tetrahydro-4-, adds the bromo Octadecane of 0.05mol, back flow reaction 8h again.Mixing solutions with gained after having reacted filters, and filter cake is dissolved in the deionized water, adds the trifluoromethyl sulfonyl lithium, a large amount of white precipitates occurs.White precipitate filtered and carry out recrystallization in dehydrated alcohol obtain product (having the compound that chemical structural formula is Fig. 1).
The sign of its chemical structure is as follows: H1 NMR (CDCl3-d1): 0.9t (6H ,-CH3), 1.0～1.5m (68H,-CH2-), 1.7m (8H ,-CH2-), 2.6t (8H ,-CH2-), 8.4d (2H, CH), (9.2d 2H, CH). ultimate analysis: actual measurement C 83.9wt%, H 12.1wt%, N3.4%; Calculated value C 84.1wt%, H 12.2wt%, N 3.6wt%. mass spectrum: mass-to-charge ratio m/z value is 769.1.
Embodiment 5
3-isopropyl pyridine and the 0.025mol sodium Metal 99.5 of 0.1mol are joined in the reaction flask, be heated to 110 ℃ and refluxed 24 hours, reaction is cooled to room temperature, and mixture is poured in the ice cube after finishing, and makes excessive sodium Metal 99.5 reaction complete.Obtain oil-water mixture, carry out oily water separation.In the oily matter of gained, add anhydrous sodium sulphate, hold over night, then vacuum rotary steam is removed the excessive 3-isopropyl pyridine that contains.Revolve that the product of gained carries out recrystallization after steaming in ethanolic soln, obtain white or light yellow product, namely 3,3-di-isopropyl-4,4-dipyridyl.Get 3 of 0.02mol, 3-di-isopropyl-4,4-dipyridyl are dissolved in the 20mL acetonitrile solution, add the bromo-iso-octane of 0.05mol, back flow reaction 8h again.With light yellow look sedimentation and filtration and in ethanolic soln, carry out recrystallization and obtain product (having the compound that chemical structural formula is Fig. 1).
The sign of its chemical structure is as follows: H1 NMR (CDCl3-d1): 0.97t (12H ,-CH3), 1.05～1.6m (34H ,-CH2﹠amp;-CH3), and 3.1m (2H, CH), 8.6d (2H, CH), 9.3dd (4H, CH). ultimate analysis: actual measurement C 78.7wt%, H 9.3wt%, N 11.4%; Calculated value C 82.4wt%, H 11.6wt%, N 6.0wt%. mass spectrum: mass-to-charge ratio m/z value is 465.5.
Above-mentioned composite cathode electrochromic material is applied to respectively electrochromic device (EC device).
Concrete making method is as follows: the glass substrate 1 that will be coated with transparency conducting layer 2 and the substrate glass 5 that is coated with conductive reflective 4 adopt sizing agents around be glued together, obtain a cavity, electrochromic material 3 is being injected these cavitys (wherein the anode off-color material of electrochromic material 3 is Polyvinyl carbazole), and with UV rubber seal mouth.Test result is respectively such as following table:
The electrochromic device that can draw the present invention's preparation from above-described embodiment data has the long lifetime, and the characteristics that variable color and fade rates are fast are applicable to the smart window of anti-glare rear-view mirror for automobile field or dimming glass for building.
Claims (7)
1. electrochromic material, it is characterized in that: the mixture that this electrochromic material is comprised of cathode electrochromic material and anode electrochromic material, the chemical structure of general formula of described cathode electrochromic material is: following general structure one (A), general structure two (B) or general structure three (C):
In above-mentioned: R
1, R
2Be 1～20 normal paraffin or isoparaffin for carbonatoms;
R
3, R
4Be 1～4 normal paraffin or isoparaffin or methoxy or ethoxy or carboxyl for carbonatoms;
R
5, R
6Be F or Cl or Br or NO
2Or SO
3H;
R
7, R
8Be 1～3 alkane or O or N or S heteroatoms for carbonatoms;
R
9, R
10Be R
3, R
4Be 1～4 alkane or Alkane isomer or methoxy or ethoxy or carboxyl for carbonatoms;
X is
Cl
-, Br
-, BF4
-Or PF6
-
Described anode electrochromic material is Polyvinyl carbazole, and its chemical structure of general formula is:
N wherein represents the polymerization degree, is natural number.
2. electrochromic material according to claim 1, it is characterized in that: the preparation method of described cathode electrochromic material may further comprise the steps:
1), synthetic 4,4 '-dipyridyl derivatives: will contain substituent pyridine and sodium Metal 99.5 and join in the reaction flask, described pyridine and sodium Metal 99.5 mol ratio are: 35～45: 1, then being heated to 100～120 ℃ refluxed 20～28 hours, after reaction is finished, be cooled to room temperature, and mixture poured in the ice cube, make the sodium Metal 99.5 reaction complete, obtain profit shape mixture, carry out oily water separation: add anhydrous sodium sulphate in the oily matter with gained, left standstill 16～24 hours, then vacuum rotary steam is removed the excessive substituent pyridine that contains, the product of gained carries out recrystallization after the vacuum rotary steam in ethanolic soln, obtain white or light yellow product, be the 4,4'-Bipyridine derivative;
2), synthetic amethyst compounds: get step 1) synthesized 4, the halogenated alkane of 4 '-dipyridyl derivatives, 0.015～0.025mol and 0.045～0.055mol or halo derivatives are dissolved in the acetonitrile solution of 15～25ml, reflux was cooled to room temperature after 8～12 hours, it is complete that solution precipitation is separated out, remove by filter completely by product of solvent and unreacted, filter cake is soluble in water, add Sodium tetrafluoroborate, sodium hexafluoro phosphate, the aqueous solution of paratoluenesulfonic acid sodium salt or sodium laurylsulfonate, it is complete that solution precipitation is separated out, carry out recrystallization with the throw out filtration and with filter cake, namely obtain cathode electrochromic material.
3. electrochromic material according to claim 2, it is characterized in that: the substituting group that contains substituent pyridine described step 1) is that carbonatoms is 1～4 alkane or Alkane isomer or methoxy or ethoxy or carboxyl.
4. electrochromic material according to claim 2, it is characterized in that: the described mol ratio that contains substituent pyridine and sodium Metal 99.5 is 40: 1.
5. electrochromic device, it is characterized in that: described electrochromic device includes transparent conducting glass, conduction reflecting glass, the transparency conducting layer of described transparent conducting glass (2) is oppositely arranged with the conductive reflective (4) of conduction reflecting glass, around described transparent conducting glass and conduction reflecting glass, by the bonding formation cavity of colloid, be filled with electrochromic material claimed in claim 1 in described cavity the inside.
6. electrochromic device according to claim 5, it is characterized in that: described transparency conducting layer (2) is for stannic oxide, indium tin oxide target, the stannic oxide of mixing fluorine, zinc oxide or mix fluorine zinc oxide, the resistance of described transparency conducting layer (2) is less than 20 ohm, and transmittance is more than 80% at visible light 550nm place.
7. electrochromic device according to claim 5 is characterized in that: described conductive reflective is silver, rhodium, aluminium, nickel or platinum.
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Also Published As
| Publication number | Publication date |
|---|---|
| CN104910892A (en) | 2015-09-16 |
| CN104804720B (en) | 2017-06-13 |
| CN104910892B (en) | 2018-06-05 |
| CN104804720A (en) | 2015-07-29 |
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