DE102006045307A1 - Electrochromic formulation, method of preparation and electrochromic organic device - Google Patents
Electrochromic formulation, method of preparation and electrochromic organic device Download PDFInfo
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- 239000000203 mixture Substances 0.000 title claims abstract description 38
- 238000009472 formulation Methods 0.000 title claims abstract description 37
- 238000000034 method Methods 0.000 title description 5
- 238000004519 manufacturing process Methods 0.000 claims abstract description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 7
- MWVTWFVJZLCBMC-UHFFFAOYSA-N 4,4'-bipyridine Chemical class C1=NC=CC(C=2C=CN=CC=2)=C1 MWVTWFVJZLCBMC-UHFFFAOYSA-N 0.000 claims description 6
- 239000004202 carbamide Substances 0.000 claims description 5
- 150000001408 amides Chemical class 0.000 claims description 4
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 4
- RVBUGGBMJDPOST-UHFFFAOYSA-N 2-thiobarbituric acid Chemical compound O=C1CC(=O)NC(=S)N1 RVBUGGBMJDPOST-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 claims description 2
- AEOCXXJPGCBFJA-UHFFFAOYSA-N ethionamide Chemical compound CCC1=CC(C(N)=S)=CC=N1 AEOCXXJPGCBFJA-UHFFFAOYSA-N 0.000 claims description 2
- ZFLIKDUSUDBGCD-UHFFFAOYSA-N parabanic acid Chemical compound O=C1NC(=O)C(=O)N1 ZFLIKDUSUDBGCD-UHFFFAOYSA-N 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 150000003556 thioamides Chemical class 0.000 claims description 2
- 239000012463 white pigment Substances 0.000 claims description 2
- 239000011159 matrix material Substances 0.000 claims 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- URQHSANZJXYMCA-UHFFFAOYSA-M 1-dodecyl-4-pyridin-1-ium-4-ylpyridin-1-ium;dibromide Chemical compound [Br-].[Br-].C1=C[N+](CCCCCCCCCCCC)=CC=C1C1=CC=[NH+]C=C1 URQHSANZJXYMCA-UHFFFAOYSA-M 0.000 description 4
- 229910010413 TiO 2 Inorganic materials 0.000 description 4
- 239000000654 additive Substances 0.000 description 3
- 238000002845 discoloration Methods 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- VFCZSWPNOOGGAJ-UHFFFAOYSA-N 1,3-dinaphthalen-1-ylthiourea Chemical compound C1=CC=C2C(NC(NC=3C4=CC=CC=C4C=CC=3)=S)=CC=CC2=C1 VFCZSWPNOOGGAJ-UHFFFAOYSA-N 0.000 description 1
- 125000002015 acyclic group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000007793 ph indicator Substances 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000007784 solid electrolyte Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003585 thioureas Chemical class 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K9/00—Tenebrescent materials, i.e. materials for which the range of wavelengths for energy absorption is changed as a result of excitation by some form of energy
- C09K9/02—Organic tenebrescent materials
-
- 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
-
- 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
- G02F2001/1502—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 complementary cell
-
- 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
- G02F2001/15145—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 the electrochromic layer comprises a mixture of anodic and cathodic compounds
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- Chemical & Material Sciences (AREA)
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- Organic Chemistry (AREA)
- Electrochromic Elements, Electrophoresis, Or Variable Reflection Or Absorption Elements (AREA)
Abstract
Die Erfindung betrifft Formulierungen und deren Anwendung in organisch basierten elektrochromen Bauteilen, beispielsweise zur Herstellung von Zustandsanzeigen, deren geschalteter Zustand möglichst lange auch stromlos erhalten bleibt. Diese elektrochromen organisch basierten Formulierungen zeichnen sich durch eine hohe Bistabilität aus. Die Formulierungen enthalten zumindest eine Komponente, die ein zwitterionisches Strukturelement enthalten.The invention relates to formulations and their use in organically based electrochromic components, for example for the production of status indicators whose switched state remains as long as possible without current. These electrochromic organic based formulations are characterized by a high bistability. The formulations contain at least one component containing a zwitterionic structural element.
Description
Die Erfindung betrifft Formulierungen und deren Anwendung in organisch basierten elektrochromen Bauteilen, beispielsweise zur Herstellung von Zustandsanzeigen, deren geschalteter Zustand möglichst lange auch stromlos erhalten bleibt. Diese elektrochromen organisch basierten Formulierungen zeichnen sich durch eine hohe Bistabilität aus.The The invention relates to formulations and their use in organic based electrochromic devices, for example for the production Status displays whose switched state is as possible long remains without power. These electrochromic organic based formulations are characterized by a high bistability.
Elektrochrome Displays auf Basis organischer Materialien umfassen im Normalfall eine aktive elektrochrome Schicht, die sich im Falle eines Displays zwischen senkrecht zueinander angeordneten Elektroden befindet. Wesentliche Bestandteile der aktiven Schicht sind ein Redox-System und ein pH-aktiver Farbstoff. Durch das Anlegen einer Spannung wird das Konzentrationsverhältnis der Redox-Partner zueinander im Material verschoben. Bei dieser Reaktion werden im Material Protonen und/oder Ionen freigesetzt bzw. gebunden, welches sich auf den pH-Wert auswirkt. Wenn eine Spannung an das Material angelegt wird, dann läuft die Verschiebung des Gleichgewichts der Redox-Partner an den beiden Elektroden in entgegen gesetzter Richtung. Dies führt dazu, dass an der einen Elektrode der pH-Wert steigt, während er an der Gegenelektrode sinkt. Über einen pH-Farbstoff wird die Änderung des pH-Wertes dann in eine Farbänderung des Materials umgesetzt und das Anlegen der Spannung sichtbar gemacht.Electrochromic Displays based on organic materials usually comprise an active electrochromic layer, resulting in the case of a display between electrodes arranged perpendicular to each other. Essential components of the active layer are a redox system and a pH-active dye. By applying a voltage is the concentration ratio the redox partner shifted to each other in the material. At this Reaction are released in the material protons and / or ions or bound, which has an effect on the pH. When a Tension is applied to the material, then the displacement of the equilibrium is running the redox partner at the two electrodes in opposite directions Direction. this leads to cause the pH of one electrode to rise while it is rising sinks at the counter electrode. about a pH dye becomes the change of the pH then in a color change of the material implemented and made the application of tension visible.
Aus
Ein
weiteres Prinzip elektrochrome Displays zu verwirklichen besteht
darin, die Farbänderung
nicht durch die Änderung
des pH-Wertes im Display herbeizuführen, sondern die ohnehin stattfindenden
Redoxprozesse zu nutzen, um kontrastreiche Farbwechsel durch die
Bildung reduktiver und/oder oxidativer Zustände in geeigneten Materialien
zu erzeugen. Dabei sind vor allem die so genannten Viologene und
Polythiophene als Materialklassen bekannt geworden. Beispiele in
der Literatur hierfür
sind in
In der Regel werden elektrochrom aktive Formulierungen angestrebt, die beim Anlegen einer Spannung schnell den Farbzustand wechseln und im spannungslosen Zustand auch wieder schnell in den Grundzustand zurückkehren. Dieses Verhalten ist für Displays erwünscht. Für Zustandsanzeigen, z. B. ein/aus, ist es vorteilhaft, Formulierungen zu haben, die nach Erreichen des geschalteten Zustands ohne weitere Spannung lange in diesen Zustand verbleiben.In As a rule, electrochromic active formulations are sought, which quickly change the color state when applying a voltage and in the de-energized state also quickly back to the ground state to return. This behavior is for Displays wanted. For status displays, z. B. on / off, it is advantageous to have formulations that after reaching the switched state without further tension long remain in this state.
Aufgabe der vorliegenden Erfindungsmeldung war die Entwicklung elektrochrom aktiver Formulierungen, die lange im geschalteten Zustand im spannungslosen Zustand bleiben, also elektrochrom aktive Formulierungen mit hoher Bistabilität.task In the present invention, the development was electrochromic active formulations that are long in the switched state in the de-energized Remain state, ie electrochromic active formulations with high Bistability.
Gegenstand der Erfindung und Lösung der Aufgabe ist eine elektrochrome Formulierung, die eine zwitterionische Komponente umfasst.object the invention and solution The task is an electrochromic formulation that is a zwitterionic Component includes.
Nach einer vorteilhaften Ausführungsform ist die elektrochrom aktive Komponente selbst ein Zwitterion. Nach einer Ausführungsform ist eine zwitterionische Verbindung in der Formulierung enthalten.To an advantageous embodiment the electrochromic active component is itself a zwitterion. To an embodiment a zwitterionic compound is included in the formulation.
Völlig überraschend wurde gefunden, dass Moleküle, die als Zwitterion vorliegen können, die Bistabilität stark erhöhen können. Ohne eine solche Form des Moleküls oder Polymers oder einen entsprechenden Zusatz kehrt die elektrochrom aktive Komponente und mit ihr die elektrochrome Zelle im stromlosen Zustand schnell wieder in den Ausgangszustand zurück.Completely surprising it was found that molecules, which can exist as zwitterion, the bistability can increase greatly. Without such a form of the molecule or polymer or a corresponding additive reverses the electrochromic active component and with it the electrochromic cell in the currentless State quickly back to the initial state.
Nach
einer vorteilhaften Ausführungsform
der Erfindung ist die elektrochrom aktive Komponente ein polymeres
Bipyridinium-Derivat, wie sie beispielsweise aus der
Vorteilhafte
Strukturen der elektrochrom aktiven Komponente enthalten das Amid-
und/oder Thioamid-Strukturelement, allgemein
Dieses kann in acyclischen Strukturen enthalten sein, aber auch in cyclischen. Besonders geeignet sind z. B. Harnstoff, Thioharnstoff und/oder Derivate davon, Amide, Thioamide bzw. Derivate davon und/oder Barbitursäure, Thiobarbitursäure, Parabansäure, Thiobarabansäure und/oder Derivate davon.This may be present in acyclic structures, but also in cyclic ones. Particularly suitable are z. As urea, thiourea and / or derivatives thereof, amides, thioamides or derivatives thereof and / or barbituric acid, thiobarbituric acid, parabanic acid, thiobarabanic acid and / or derivatives thereof.
Beispielhaft
genannt seien folgende Strukturen:
Zusätze mit zumindest einer dieser funktionellen Gruppen können in einem weiten Konzentrationsbereich eingesetzt werden, vorzugsweise aber im stöchiometrischen Verhältnis, bezogen auf die elektrochrom aktive Komponente.Additives with At least one of these functional groups can be in a wide concentration range are used, but preferably in a stoichiometric ratio, based to the electrochromic active component.
Die funktionelle Gruppe kann aber auch in der elektrochrom aktiven Komponente vorliegen.The But functional group can also be found in the electrochromic active component available.
Der Charakter der Bipolarität des Zusatzes kann durch Substitution an einem oder beiden N-Atomen variiert werden.Of the Character of bipolarity of the additive can be varied by substitution on one or both N atoms become.
Eine erfindungsgemäße Formulierung enthält eine elektrochrom aktive Komponente, z. B. ein 4,4'-Bipyridiniumderivat, z.B. ein polymeres 4,4'-Bipyridiniumsalz wie das Poly-(dodecyl-4,4'-bipyridinium)-dibromid, und z. B. Harnstoff. Diese Formulierung ist wegen ihrer Bistabilität besonders für Anzeige elemente, die den Zustand eines Systems anzeigen sollen, geeignet. Da sie im stromlosen Zustand lange im geschalteten Farbzustand bleibt, können Anzeigeelemente mit besonders geringem Stromverbrauch realisiert werden. Zur Aufrechterhaltung eines ausreichenden Farbkontrasts genügt eine entsprechende zeitliche Folge von Spannungspulsen.A inventive formulation contains an electrochromic active component, e.g. A 4,4'-bipyridinium derivative, e.g. a polymeric 4,4'-bipyridinium salt such as the poly (dodecyl-4,4'-bipyridinium) dibromide, and z. B. urea. This formulation is special because of its bistability for display elements, which should indicate the state of a system. As she remains in the switched color state when de-energized, can Display elements realized with very low power consumption become. To maintain a sufficient color contrast enough a corresponding time sequence of voltage pulses.
Ausführungsbeispieleembodiments
1 Herstellung einer elektrochrom aktiven Formulierung und einer elektrochromen Zelle daraus.1 Preparation of an electrochromically active formulation and an electrochromic Cell out of it.
6g TiO2 werden mit 0.6g eines polymeren 4,4'-Bipyridinium-Derivats (Poly-(dodecyl-4,4'-bipyridinium-dibromid)) und mit 2g Diethylengklykol mittels eines Speed-Mixers intensiv miteinander vermischt. Es wird eine weiße Paste erhalten. Aus dieser wird mittels der Rakel-Technik zwischen zwei ITO-beschichteten Folien eine Schicht der Dicke 50 μm hergestellt. Beim Anlegen einer Spannung von 1.5 V für 10 s wird an der Kathode ein blauer Farbeindruck erzeugt, welcher als 100% Kontrast gegenüber dem Ausgangszustand definiert wird, und der im nicht beschalteten Zustand innerhalb von etwa 30 Sekunden auf 20% des Anfangskontrastes abfällt. Die Verfärbung ist also bei den angegebenen Beschaltungsbedingungen für den Betrachter des Displays im nicht beschalteten Zustand 30 Sekunden lang sichtbar.6 g of TiO 2 are intensively mixed with 0.6 g of a polymeric 4,4'-bipyridinium derivative (poly (dodecyl-4,4'-bipyridinium-dibromide)) and with 2 g of diethylene glycol by means of a speed mixer. A white paste is obtained. From this, a layer of thickness 50 μm is produced by means of the doctoring technique between two ITO-coated films. When a voltage of 1.5 V is applied for 10 s, a blue color impression is produced at the cathode, which is defined as a 100% contrast to the initial state, and which drops to 20% of the initial contrast in the unconnected state within about 30 seconds. The discoloration is therefore visible to the viewer of the display in the unconnected state for 30 seconds under the specified wiring conditions.
2 Herstellung einer elektrochrom aktiven Formulierung mit Harnstoff-Zusatz und einer bistabilen elektrochromen Zelle daraus.2 Preparation of an electrochromically active formulation with added urea and a bistable electrochromic cell thereof.
6g TiO2, 0.6g eines polymeren 4,4'-Bipyridinium-Derivats (Poly-(dodecyl-4,4'-bipyridinium-dibromid)), 0.1g Harnstoff werden mit 2g Diethylengklykol mittels eines Speed-Mixers intensiv miteinander vermischt. Es wird eine weiße Paste erhalten. Aus dieser wird mittels der Rakel-Technik zwischen zwei ITO- beschichteten Folien eine Schicht der Dicke 50 μm hergestellt. Beim Anlegen einer Spannung von 1.5 V für 10 s wird an der Kathode ein blauer Farbeindruck erzeugt, welcher als 100% Kontrast gegenüber dem Ausgangszustand definiert wird, und der im nicht beschalteten Zustand innerhalb von etwa 110 Sekunden auf 20% des Anfangskontrastes abfällt. Die Verfärbung ist also bei den angegebenen Beschaltungsbedingungen für den Betrachter des Displays im nicht beschalteten Zustand 110 Sekunden lang sichtbar. Es wird eine 3.6-fache Verbesserung der Bistabilität erreicht.6 g of TiO 2 , 0.6 g of a polymeric 4,4'-bipyridinium derivative (poly (dodecyl-4,4'-bipyridinium-dibromide)), 0.1 g of urea are mixed thoroughly with 2 g of diethylene glycol by means of a speed mixer. A white paste is obtained. From this, a layer of thickness 50 μm is produced by means of the doctoring technique between two ITO-coated films. When a voltage of 1.5 V is applied for 10 s, a blue color impression is produced at the cathode, which is defined as 100% contrast with respect to the initial state and which in the unconnected state drops to 20% of the initial contrast within about 110 seconds. The discoloration is thus visible to the viewer of the display in the unconnected state for 110 seconds under the specified wiring conditions. It achieves a 3.6-fold improvement in bistability.
3 Herstellung einer elektrochrom aktiven Formulierung mit einem Thioharnstoff-Derivat und einer bistabilen elektrochromen Zelle daraus.3 Preparation of an electrochromically active formulation with a thiourea derivative and a bistable electrochromic cell thereof.
6g TiO2, 0.6 g eines polymeren 4,4'-Bipyridinium-Derivats (Poly-(dodecyl-4,4'-bipyridinium-dibromid)), 0.41g N,N'-Dinaphthyl-thioharnstoff werden mit 2 g Diethylengklykol mittels eines Speed-Mixers intensiv miteinander vermischt. Es wird eine weiße Paste erhalten. Aus dieser wird mittels der Rakel-Technik zwischen zwei ITO-beschichteten Folien eine Schicht der Dicke 50 μm hergestellt. Beim Anlegen einer Spannung von 1.5 V für 10 s wird an der Kathode ein blauer Farbeindruck erzeugt, welcher als 100% Kontrast gegenüber dem Ausgangszustand definiert wird, und der im nicht beschalteten Zustand innerhalb von etwa 130 Sekunden auf 20% des Anfangskontrastes abfällt. Die Verfärbung ist also bei den angegebenen Beschaltungsbedingungen für den Betrachter des Displays im nicht beschalteten Zustand 130 Sekunden lang sichtbar. Es wird eine 4.3-fache Verbesserung der Bistabilität erreicht.6 g of TiO 2 , 0.6 g of a polymeric 4,4'-bipyridinium derivative (poly (dodecyl-4,4'-bipyridinium-dibromide)), 0.41 g of N, N'-dinaphthyl-thiourea are mixed with 2 g Diethylengklykol by means of a Speed mixers are mixed together intensely. A white paste is obtained. From this, a layer of thickness 50 μm is produced by means of the doctoring technique between two ITO-coated films. When a voltage of 1.5 V is applied for 10 s, a blue color impression is produced at the cathode, which is defined as 100% contrast with respect to the initial state and which drops to 20% of the initial contrast in the unconnected state within about 130 seconds. The discoloration is therefore visible to the viewer of the display in the unconnected state for 130 seconds under the specified wiring conditions. It achieves a 4.3-fold improvement in bistability.
Die Erfindung betrifft Formulierungen und deren Anwendung in organisch basierten elektrochromen Bauteilen, beispielsweise zur Herstellung von Zustandsanzeigen, deren geschalteter Farbzustand möglichst lange auch stromlos erhalten bleibt. Diese elektrochromen organisch basierten Formulierungen zeichnen sich durch eine hohe Bistabilität aus. Die Formulie rungen enthalten zumindest eine Komponente, die ein zwitterionisches Strukturelement enthält.The The invention relates to formulations and their use in organic based electrochromic devices, for example for the production Status displays whose switched color state is as long as possible also remains de-energized. These electrochromic organic based Formulations are characterized by a high bistability. The Formulas contain at least one component which is a zwitterionic Contains structure element.
Claims (11)
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102006045307A DE102006045307A1 (en) | 2006-09-26 | 2006-09-26 | Electrochromic formulation, method of preparation and electrochromic organic device |
| PCT/EP2007/059931 WO2008037643A1 (en) | 2006-09-26 | 2007-09-20 | Electrochromic formulation, method for the production thereof, and electrochromic organic component |
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| DE102006045307A DE102006045307A1 (en) | 2006-09-26 | 2006-09-26 | Electrochromic formulation, method of preparation and electrochromic organic device |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102008024259A1 (en) | 2008-05-20 | 2009-12-31 | Siemens Aktiengesellschaft | Electrochromic formulation, useful for an electrochromic active paste and an organic electronic electrochromic component, comprises an electrochromic switchable pigment and a white pigment |
| WO2010136314A1 (en) | 2009-05-29 | 2010-12-02 | Siemens Aktiengesellschaft | Electrochromic formulation, method for the production thereof, and organic electrochromic component |
| DE102009023309A1 (en) | 2009-05-29 | 2010-12-16 | Siemens Aktiengesellschaft | Electrochromic formulation, method of preparation and electrochromic organic device |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8115984B2 (en) | 2007-06-18 | 2012-02-14 | Ajjer Llc | Laminated electrochromic devices and processes for forming the same |
| DE102008024187B3 (en) * | 2008-05-19 | 2009-10-15 | Siemens Aktiengesellschaft | Electrochromic formulation with at least two color systems, process for making same and electrochromic device |
| DE102008024260B4 (en) | 2008-05-20 | 2010-04-15 | Siemens Aktiengesellschaft | Electrochromic formulation and organic electrochromic switchable electronic component |
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| JPS5643623A (en) * | 1979-09-18 | 1981-04-22 | Sharp Corp | Electrochromic display device |
| DE19825371A1 (en) * | 1998-06-06 | 1999-12-09 | Bayer Ag | Electrochromic display device with insulated leads |
| EP1045276A1 (en) * | 1997-12-19 | 2000-10-18 | Nippon Mitsubishi Oil Corporation | Electrochromic element |
| WO2002075442A1 (en) * | 2001-03-19 | 2002-09-26 | Dow Global Technologies Inc. | Matrix addressable electrochromic display device |
| WO2006128818A1 (en) * | 2005-05-31 | 2006-12-07 | Siemens Aktiengesellschaft | Material for an electrochromic formualtion, use thereof and display |
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|---|---|---|---|---|
| DE3808309A1 (en) * | 1988-03-12 | 1989-09-21 | Merck Patent Gmbh | TWITTERIONIC NLO CHROMOPHORE |
| EP0717740A1 (en) * | 1993-09-10 | 1996-06-26 | Ciba SC Holding AG | Photochromic compounds, methods and intermediates for producing them and their use |
| CA2414089A1 (en) * | 2000-06-26 | 2002-01-03 | Catalyst Biomedica Limited | Improvements in and relating to chromophores |
| WO2006128806A2 (en) * | 2005-05-31 | 2006-12-07 | Siemens Aktiengesellschaft | Material for electrochromic layers |
-
2006
- 2006-09-26 DE DE102006045307A patent/DE102006045307A1/en not_active Withdrawn
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2007
- 2007-09-20 WO PCT/EP2007/059931 patent/WO2008037643A1/en not_active Ceased
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5643623A (en) * | 1979-09-18 | 1981-04-22 | Sharp Corp | Electrochromic display device |
| EP1045276A1 (en) * | 1997-12-19 | 2000-10-18 | Nippon Mitsubishi Oil Corporation | Electrochromic element |
| DE19825371A1 (en) * | 1998-06-06 | 1999-12-09 | Bayer Ag | Electrochromic display device with insulated leads |
| WO2002075442A1 (en) * | 2001-03-19 | 2002-09-26 | Dow Global Technologies Inc. | Matrix addressable electrochromic display device |
| WO2006128818A1 (en) * | 2005-05-31 | 2006-12-07 | Siemens Aktiengesellschaft | Material for an electrochromic formualtion, use thereof and display |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102008024259A1 (en) | 2008-05-20 | 2009-12-31 | Siemens Aktiengesellschaft | Electrochromic formulation, useful for an electrochromic active paste and an organic electronic electrochromic component, comprises an electrochromic switchable pigment and a white pigment |
| WO2010136314A1 (en) | 2009-05-29 | 2010-12-02 | Siemens Aktiengesellschaft | Electrochromic formulation, method for the production thereof, and organic electrochromic component |
| DE102009023303A1 (en) | 2009-05-29 | 2010-12-09 | Siemens Aktiengesellschaft | Electrochromic formulation, method of preparation and electrochromic organic device |
| DE102009023309A1 (en) | 2009-05-29 | 2010-12-16 | Siemens Aktiengesellschaft | Electrochromic formulation, method of preparation and electrochromic organic device |
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| Publication number | Publication date |
|---|---|
| WO2008037643A1 (en) | 2008-04-03 |
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