WO2006128820A1 - Electrochromic display - Google Patents

Electrochromic display Download PDF

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Publication number
WO2006128820A1
WO2006128820A1 PCT/EP2006/062572 EP2006062572W WO2006128820A1 WO 2006128820 A1 WO2006128820 A1 WO 2006128820A1 EP 2006062572 W EP2006062572 W EP 2006062572W WO 2006128820 A1 WO2006128820 A1 WO 2006128820A1
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Prior art keywords
dyes
electrochromic
derivatives
dye
pixel
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PCT/EP2006/062572
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German (de)
French (fr)
Inventor
Andreas Kanitz
Wolfgang Roth
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Siemens Aktiengesellschaft
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Publication of WO2006128820A1 publication Critical patent/WO2006128820A1/en

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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
    • G02F1/1503—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 caused by oxidation-reduction reactions in organic liquid solutions, e.g. viologen solutions
    • 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
    • G02F2203/00—Function characteristic
    • G02F2203/34—Colour display without the use of colour mosaic filters

Definitions

  • the invention relates to an electrochromic organic-based display.
  • Electrochromic displays based on organic materials normally have a layer of a special active material, which is located between electrodes arranged perpendicular to one another.
  • Essential components of the active material are a redox system and a pH-active dye.
  • a voltage is applied to the system, the shift in the equilibrium of the redox partners on the two electrodes is in the opposite direction.
  • the pH of one of the electrodes rises while it sinks on the counter electrode.
  • Via a pH dye the change in pH is then converted into a color change.
  • a pasty formulation which represents the electrochromic system, is located between the electrodes.
  • the composition of this electrochromic system then consists inter alia of a polymer as a matrix or solid electrolyte, a conductive salt, a redox system, TiO 2 as a white pigment, a solvent and a dye. This is usually a pH indicator.
  • a disadvantage of the formulation described above is that in the electrochromic formulation only one dye is present and only two colors can be reproduced. These correspond to the colors of the dye in the acidic or basic pH range.
  • the electrochromic cell can therefore only be switched back and forth between two colors. Therefore, only monochrome displays can be produced.
  • the production of multicolored or full color displays is not possible.
  • the object of the present invention is therefore to provide electrochromic chromophores which enable the production of multi-color or full-color displays.
  • the invention relates to a pixelated electrochromic display, wherein each pixel is subdivided into corresponding subpixels which are electrically separately controllable, characterized in that at least three subpixels of a pixel can be controlled separately in at least three electrochromic colors red, green and blue.
  • z. B the subdivision of a pixel into three, the basic colors corresponding subpixels, which can be controlled electrically isolated.
  • Such an arrangement is z. B. of full-color, organic LEDs.
  • Dyes are already known from silver halide photography, where they are irreversibly oxidized chemically from colorless to the respective color (in the photo). These dyes are basically not used in organic electronics, because they are extremely difficult to dissolve, crystalline rather than amorphous and finally, because they can be processed poorly into layers.
  • dyes of the indophenol type can be oxidized from colorless to blue-green
  • dyes of the pyrazolone type (developer + pyrazolone- derivative) are oxidized from colorless to purple
  • dyes derived from 1,3-diketones (developer + 1,3-diketone derivative) are oxidized from colorless to yellow.
  • dyes are used in which the electrochromic chromophores are formed as oxidation products.
  • the following colors are preferably formed from the following dyes: a) cyan dyes, from p-phenylenediamine derivatives and phenol derivatives / naphthol derivatives (indophenol type), b) red / purple dyes, from p-phenylenediamine derivatives and pyrazolone derivatives (pyrazolone type) and / or c) yellow Dyes derived from p-phenylenediamine derivatives and 1,3-diketone derivatives.
  • redox dyes are used in a semiconducting matrix, these dyes can be reversibly decolorized (cathodically) by reduction and (anodically) oxidatively transformed back into the respective color of the chromophore.
  • An alternating, pixelated arrangement of the redox dyes in the respective colors of the color triangle (RGB) thus enables the electrical wiring of a full-color electrochromic display (ECD).
  • the redox dyes required for multicolored and / or full-color ECDs can be embodied both in blends and in chemically bonded form with electrically conductive materials, so that they can be made from solution or pasty by printing processes onto the respective pixel-representing surface of the structured substrate can be applied.
  • the invention will be explained in more detail below with reference to a few selected examples:
  • Conductive polymer by Suzuki reaction of 2,5-dibromo hydroquinone dimethyl ether and 9,9-diheptylfluorene-2,7-diboronic acid
  • the corresponding polymer-bound RGB dye is dissolved in a suitable solvent such that a 1-3% solution is obtained.
  • TiC> 2 is added to the resulting mixture as a white pigment, the ratio of solvent / TiC> 2 being chosen so as to obtain a mixture having a consistency such that, for example, B. can be applied by means of the screen printing or inkjet process. All ingredients are mixed thoroughly after mixing together using a speed mixer.
  • the described formulation is applied according to the prior art between intersecting electrodes.
  • the corresponding polymer-bound RGB dye gives a color change from its respective RGB color to colorless or white (when white pigment is present).
  • the color change occurs by applying a voltage to the electrochromic cell.
  • RGB pixel If the application of the corresponding RGB dye on a separately controllable subpixel, so an RGB pixel is generated.
  • Such pixels can be part of a display, whereby a full-color display can be made.
  • the invention discloses for the first time a pixelated electrochromic display, wherein each pixel is subdivided into corresponding subpixels which are electrically separately controllable, characterized in that at least three subpixels of a pixel can be driven in at least three electrochromic colors red, green and blue.

Abstract

The invention relates to a pixelated display, whereby each pixel is sub-divided into corresponding sub-pixels which may be independently electrically controlled, characterised in that the sub-pixels of a pixel comprise at least three electrochromic chromophores in the colours red, green and blue.

Description

Beschreibungdescription
Elektrochromes DisplayElectrochromic display
Die Erfindung betrifft ein elektrochromes Display auf organischer Basis.The invention relates to an electrochromic organic-based display.
Elektrochrome Displays auf Basis organischer Materialien haben im Normalfall eine Schicht eines speziellen aktiven Materials, die sich zwischen senkrecht zueinander angeordneten Elektroden befindet. Wesentliche Bestandteile des aktiven Materials sind ein Redox-System und ein pH-aktiver Farbstoff. Wenn eine Spannung an das System 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 umgesetzt .Electrochromic displays based on organic materials normally have a layer of a special active material, which is located between electrodes arranged perpendicular to one another. Essential components of the active material are a redox system and a pH-active dye. When a voltage is applied to the system, the shift in the equilibrium of the redox partners on the two electrodes is in the opposite direction. As a result, the pH of one of the electrodes rises while it sinks on the counter electrode. Via a pH dye, the change in pH is then converted into a color change.
Aus WO 02/075441A2 und WO 02/075442 Al ist bekannt, dass sich zwischen den Elektroden eine pastöse Formulierung, die das elektrochrome System darstellt, befindet. Die Zusammensetzung dieses elektrochromen Systems besteht danach unter anderem aus einem Polymer als Matrix oder Feststoffelektrolyt, einem Leitsalz, einem Redox-System, TiÜ2 als Weißpigment, einem Lösungsmittel und einem Farbstoff. Dieser ist in der Regel ein pH-Indikator .It is known from WO 02 / 075441A2 and WO 02/075442 A1 that a pasty formulation, which represents the electrochromic system, is located between the electrodes. The composition of this electrochromic system then consists inter alia of a polymer as a matrix or solid electrolyte, a conductive salt, a redox system, TiO 2 as a white pigment, a solvent and a dye. This is usually a pH indicator.
Als Nachteil der oben beschriebenen Formulierung ist zu nennen, dass in der elektrochromen Formulierung nur ein Farbstoff vorhanden ist und lediglich zwei Farben wiedergegeben werden können. Diese entsprechen den Farben des Farbstoffs im sauren oder basischen pH-Bereich. Die elektrochrome Zelle kann also nur zwischen zwei Farben hin und her geschaltet werden. Es können daher lediglich monochrome Displays hergestellt werden. Die Herstellung mehrfarbiger oder vollfarbiger Displays ist nicht möglich. Aufgabe der vorliegenden Erfindung ist daher, elektrochrome Chromophore zur Verfügung zu stellen, die die Herstellung mehr- oder vollfarbiger Displays ermöglichen.A disadvantage of the formulation described above is that in the electrochromic formulation only one dye is present and only two colors can be reproduced. These correspond to the colors of the dye in the acidic or basic pH range. The electrochromic cell can therefore only be switched back and forth between two colors. Therefore, only monochrome displays can be produced. The production of multicolored or full color displays is not possible. The object of the present invention is therefore to provide electrochromic chromophores which enable the production of multi-color or full-color displays.
Gegenstand der Erfindung ist ein pixeliertes elektrochromes Display, wobei jedes Pixel in entsprechende Subpixel, die elektrisch getrennt ansteuerbar sind, unterteilt ist, dadurch gekennzeichnet, dass zumindest drei Subpixel eines Pixels in zumindest drei elektrochromen Farben rot, grün und blau getrennt ansteuerbar sind.The invention relates to a pixelated electrochromic display, wherein each pixel is subdivided into corresponding subpixels which are electrically separately controllable, characterized in that at least three subpixels of a pixel can be controlled separately in at least three electrochromic colors red, green and blue.
Voraussetzung für ein solches Display ist z. B. die Unterteilung eines Pixels in drei, den Grundfarben entsprechende Subpixel, die elektrisch getrennt angesteuert werden können. Eine solche Anordnung ist z. B. von vollfarbigen, organischen LEDs bekannt.Prerequisite for such a display is z. B. the subdivision of a pixel into three, the basic colors corresponding subpixels, which can be controlled electrically isolated. Such an arrangement is z. B. of full-color, organic LEDs.
Indem drei Redox-Farbstoffe alternierend in den Farben rot, grün und blau (RGB) bzw. gelb, purpur und blaugrün so angeordnet werden, dass sie entsprechende Subpixel bilden, die elektrisch getrennt angesteuert werden können, und sich diese Pixel in einer solchen chemischen Umgebung befinden, dass die jeweilige Farbe elektrisch nach farblos bzw. weiß (durch das Hintergrundpigment) umgeschaltet werden kann, wird Vollfar- bigkeit erreicht.By arranging three redox dyes alternately in the colors red, green and blue (RGB) or yellow, purple and blue-green, they form corresponding subpixels, which can be controlled electrically separately, and these pixels in such a chemical environment that the respective color can be electrically switched to colorless or white (by the background pigment), full color is achieved.
Es sind Farbstoffe bereits aus der Silberhalogenidfotographie bekannt, wo sie allerdings chemisch von farblos in die jeweilige Farbe (auf dem Foto) irreversibel oxidiert werden. Diese Farbstoffe werden grundsätzlich in der organischen Elektronik nicht eingesetzt, weil sie extrem schwerlöslich sind, kristallin anstatt amorph vorliegen und schließlich, weil sie sich schlecht zu Schichten verarbeiten lassen.Dyes are already known from silver halide photography, where they are irreversibly oxidized chemically from colorless to the respective color (in the photo). These dyes are basically not used in organic electronics, because they are extremely difficult to dissolve, crystalline rather than amorphous and finally, because they can be processed poorly into layers.
So können beispielsweise Farbstoffe vom Indophenoltyp (Entwickler + Naphtholderivat) von farblos nach blaugrün oxidiert werden, Farbstoffe vom Pyrazolontyp (Entwickler + Pyrazolon- derivat) von farblos nach purpur oxidiert werden und Farbstoffe, von 1, 3-Diketonen abgeleitet, (Entwickler + 1,3- Diketonderivat) von farblos nach gelb oxidiert werden.Thus, for example, dyes of the indophenol type (developer + naphthol derivative) can be oxidized from colorless to blue-green, dyes of the pyrazolone type (developer + pyrazolone- derivative) are oxidized from colorless to purple and dyes derived from 1,3-diketones (developer + 1,3-diketone derivative) are oxidized from colorless to yellow.
Um diese Moleküle für die organische Elektronik zugänglich zu machen werden sie in einer entsprechenden polymeren Matrix eingesetzt und/oder an Polymere angehängt, die löslich sind, amorphe Verbände bilden und sich gut in Schichten aufbringen lassen.In order to make these molecules accessible to organic electronics, they are used in a corresponding polymeric matrix and / or attached to polymers that are soluble, form amorphous dressings and can be applied well in layers.
Insbesondere werden Farbstoffe eingesetzt, bei denen die elektrochromen Chromophore als Oxidationsprodukte gebildet werden.In particular, dyes are used in which the electrochromic chromophores are formed as oxidation products.
Bevorzugt werden dabei folgende Farben aus folgenden Farbstoffen gebildet werden: a) blaugrüne Farbstoffe, aus p-Phenylendiaminderivaten und Phenolderivaten/Naphtholderivaten (Indophenoltyp) , b) rot/purpur Farbstoffe, aus p-Phenylendiaminderivaten und Pyrazolonderivaten (Pyrazolontyp) und/oder c) gelbe Farbstoffe, aus p-Phenylendiaminderivaten und 1,3- Diketonderivaten .The following colors are preferably formed from the following dyes: a) cyan dyes, from p-phenylenediamine derivatives and phenol derivatives / naphthol derivatives (indophenol type), b) red / purple dyes, from p-phenylenediamine derivatives and pyrazolone derivatives (pyrazolone type) and / or c) yellow Dyes derived from p-phenylenediamine derivatives and 1,3-diketone derivatives.
Setzt man nun entsprechende Redox-Farbstoffe in einer halbleitenden Matrix ein, können diese Farbstoffe reversibel (kathodisch) reduktiv entfärbt und (anodisch) oxidativ in die jeweilige Farbe des Chromophors zurück transformiert werden. Durch eine alternierende, pixelierte Anordnung der Redox- Farbstoffe in den jeweiligen Farben des Farbdreiecks (RGB) ist somit die elektrische Beschaltung eines vollfarbigen elektrochromen Displays (ECDs) möglich.If corresponding redox dyes are used in a semiconducting matrix, these dyes can be reversibly decolorized (cathodically) by reduction and (anodically) oxidatively transformed back into the respective color of the chromophore. An alternating, pixelated arrangement of the redox dyes in the respective colors of the color triangle (RGB) thus enables the electrical wiring of a full-color electrochromic display (ECD).
Die für mehrfarbige und/oder vollfarbige ECDs benötigten Redox-Farbstoffe können sowohl in Blends als auch in chemisch gebundener Form mit elektrisch leitfähigen Materialien ausgeführt sein, so dass sie aus Lösung bzw. pastös durch Druckverfahren auf die jeweilige, das Pixel darstellende Fläche des strukturierten Substrates appliziert werden können. Im Folgenden wird die Erfindung noch anhand einiger ausgewählter Beispiele näher erläutert:The redox dyes required for multicolored and / or full-color ECDs can be embodied both in blends and in chemically bonded form with electrically conductive materials, so that they can be made from solution or pasty by printing processes onto the respective pixel-representing surface of the structured substrate can be applied. The invention will be explained in more detail below with reference to a few selected examples:
1 Darstellung chemisch gebundener Redox-Farbstoffe an einem halbleitenden Polymer: R= Alkyl (C6 bis ClO)1 Preparation of chemically bound redox dyes on a semiconductive polymer: R = alkyl (C6 to ClO)
Synthese der Zwischenprodukte und Finalreaktionen: - 9, 9-DiheptylfluorenSynthesis of intermediates and final reactions: - 9, 9-Diheptylfluorene
Figure imgf000005_0001
Figure imgf000005_0001
aus Fluoren und Heptylbromid in Gegenwart einer Basefrom fluorene and heptyl bromide in the presence of a base
- 2 , 7-Dibrom-9, 9-diheptylfluoren- 2, 7-dibromo-9,9-diheptylfluorene
Figure imgf000005_0002
Figure imgf000005_0002
aus 9, 9-Diheptylfluoren und Brom in Chloroformfrom 9,9-diheptylfluorene and bromine in chloroform
- 9, 9-Diheptylfluoren-2 , 7-diboronsäure- 9,9-Diheptylfluorene-2,7-diboronic acid
Figure imgf000005_0003
aus 2 , 7-Dibrom-9, 9-diheptylfluoren durch Lithiierung und Reaktion mit Borsäuretrimethylester
Figure imgf000005_0003
from 2, 7-dibromo-9,9-diheptylfluorene by lithiation and reaction with trimethyl borate
- 2, 5-Dibromhydrochinondimethylether- 2, 5-dibromohydroquinone dimethyl ether
Figure imgf000006_0001
durch Bromierung von Hydrochinondimethylether
Figure imgf000006_0001
by bromination of hydroquinone dimethyl ether
- leitfähiges Polymer: durch Suzuki-Reaktion aus 2, 5-Dibromhydrochinondimethyl- ether und 9, 9-Diheptylfluoren-2, 7-diboronsäureConductive polymer: by Suzuki reaction of 2,5-dibromo hydroquinone dimethyl ether and 9,9-diheptylfluorene-2,7-diboronic acid
Figure imgf000006_0002
Figure imgf000006_0002
Oxidation des leitfähigen Polymer mittels eines Gemisches aus Essigsäure/65%-ige SalpetersäureOxidation of the conductive polymer by means of a mixture of acetic acid / 65% nitric acid
Figure imgf000006_0003
Figure imgf000006_0003
Reduktion des leitfähigen Polymer mittels Platinoxid/Wasserstoff in THF/Ethanol
Figure imgf000007_0001
Reduction of the conductive polymer by means of platinum oxide / hydrogen in THF / ethanol
Figure imgf000007_0001
- N-Heptylanilin- N-heptylaniline
Destillation aus Anilin und HeptylbromidDistillation from aniline and heptyl bromide
/^N. ^NH / ^ N. ^ NH
- N-Heptyl-N-2-hydroxyethyl-anilin aus Oxiran und N-Heptylanilin in EthanolN-heptyl-N-2-hydroxyethyl aniline from oxirane and N-heptylaniline in ethanol
/"=w^N / "= w ^ N
OHOH
- N-Heptyl-N-2-hydroxyethyl-4-nitoso-anilin-hydrochlorid aus N-Heptyl-N-2-hydroxyethyl-anilin und Isoamylnitrit in HCl-haltigem Propanol- N-Heptyl-N-2-hydroxyethyl-4-nitoso-aniline hydrochloride from N-heptyl-N-2-hydroxyethyl-aniline and isoamyl nitrite in HCl-containing propanol
Figure imgf000007_0002
Figure imgf000007_0002
- Kondensation des Blaugrünfarbstoffes (a) , des Purpurfarbstoffes (b) , des Gelbfarbstoffes (c)
Figure imgf000008_0001
Condensation of the cyan dye (a), the magenta dye (b), the yellow dye (c)
Figure imgf000008_0001
aus N-Heptyl-N-2-hydroxyethyl-4-nitoso-anilin-hydrochlorid und 1-Naphthol,of N-heptyl-N-2-hydroxyethyl-4-nitosoaniline hydrochloride and 1-naphthol,
Figure imgf000008_0002
aus N-Heptyl-N-2-hydroxyethyl-4-nitoso-anilin-hydrochlorid und 1, 3-Diphenylpyrazol-5-on
Figure imgf000008_0002
of N-heptyl-N-2-hydroxyethyl-4-nitosoaniline hydrochloride and 1,3-diphenylpyrazol-5-one
Figure imgf000008_0003
Figure imgf000008_0003
aus N-Heptyl-N-2-hydroxyethyl-4-nitoso-anilin-hydrochlorid und 1 , 3-Diphenyl-propan-l , 3-dionfrom N-heptyl-N-2-hydroxyethyl-4-nitoso-aniline hydrochloride and 1,3-diphenyl-propane-1,3-dione
- Polymeranbindung der Farbstoffe (a,b,c) durch Mitsunobu-Reaktion Polymer attachment of the dyes (a, b, c) by Mitsunobu reaction
a) polymer gebundener Blaugrün-Farbstoff: n/m = 2/1a) polymer-bound cyan dye: n / m = 2/1
Figure imgf000009_0001
b) polymer gebundener Purpur-Farbstoff: n/m = 2/1
Figure imgf000009_0001
b) polymer-bound magenta dye: n / m = 2/1
Figure imgf000009_0002
Figure imgf000009_0002
c) polymer gebundener Gelb-Farbstoff: n/m = 2/1c) polymer-bound yellow dye: n / m = 2/1
Figure imgf000009_0003
2 Herstellung einer elektrochrom aktiven Formulierung und Herstellung einer elektrochrom aktiven Zelle.
Figure imgf000009_0003
2 Preparation of an electrochromically active formulation and preparation of an electrochromically active cell.
Der entsprechende, polymergebundene RGB-Farbstoff wird in einem geeigneten Lösungsmittel gelöst, so, dass eine 1-3%-ige Lösung erhalten wird. Zu der erhaltenen Mischung wird, falls erforderlich, noch TiC>2 als Weißpigment zugemischt, wobei das Verhältnis Lösungsmittel/TiC>2 so gewählt ist, dass eine Mischung mit einer Konsistenz erhalten wird, dass sie z. B. mittels des Siebdruck- oder InkJet-Verfahrens appliziert werden kann. Alle Bestandteile werden nach dem Zusammenmischen intensiv mittels eines Speed-Mixers vermischt.The corresponding polymer-bound RGB dye is dissolved in a suitable solvent such that a 1-3% solution is obtained. If necessary, TiC> 2 is added to the resulting mixture as a white pigment, the ratio of solvent / TiC> 2 being chosen so as to obtain a mixture having a consistency such that, for example, B. can be applied by means of the screen printing or inkjet process. All ingredients are mixed thoroughly after mixing together using a speed mixer.
3 Herstellung einer vollfarbigen, elektrochrom aktiven Zelle3 Preparation of a full-color, electrochromically active cell
Die beschriebene Formulierung wird nach dem Stand der Technik zwischen sich kreuzenden Elektroden appliziert. Der entsprechende, polymergebundene RGB-Farbstoff ergibt einen Farbumschlag von seiner jeweiligen RGB-Farbe nach farblos oder weiß (wenn Weißpigment vorhanden ist) . Der Farbumschlag erfolgt durch Anlegen einer Spannung an die elektrochrome Zelle.The described formulation is applied according to the prior art between intersecting electrodes. The corresponding polymer-bound RGB dye gives a color change from its respective RGB color to colorless or white (when white pigment is present). The color change occurs by applying a voltage to the electrochromic cell.
Erfolgt die Applikation des entsprechenden RGB-Farbstoffs auf einem getrennt ansteuerbaren Subpixel, so wird ein RGB-Pixel erzeugt. Solche Pixel können Bestandteil eines Displays sein, wodurch ein vollfarbiges Display hergestellt werden kann.If the application of the corresponding RGB dye on a separately controllable subpixel, so an RGB pixel is generated. Such pixels can be part of a display, whereby a full-color display can be made.
Die Erfindung offenbart erstmals ein pixeliertes elektrochro- mes Display, wobei jedes Pixel in entsprechende Subpixel, die elektrisch getrennt ansteuerbar sind, unterteilt ist, dadurch gekennzeichnet, dass zumindest drei Subpixel eines Pixels in zumindest drei elektrochromen Farben rot, grün und blau ansteuerbar sind. The invention discloses for the first time a pixelated electrochromic display, wherein each pixel is subdivided into corresponding subpixels which are electrically separately controllable, characterized in that at least three subpixels of a pixel can be driven in at least three electrochromic colors red, green and blue.

Claims

Patentansprüche claims
1. Pixeliertes elektrochromes Display, wobei jedes Pixel in entsprechende Subpixel, die elektrisch getrennt ansteuerbar sind, unterteilt ist, dadurch gekennzeichnet, dass zumindest drei Subpixel eines Pixels in zumindest drei elektrochromen Farben rot, grün und blau getrennt ansteuerbar sind.1. Pixelated electrochromic display, each pixel is subdivided into corresponding subpixels, which are electrically controlled separately, characterized in that at least three subpixels of a pixel in at least three electrochromic colors red, green and blue are controlled separately.
2. Pixeliertes Display nach Anspruch 1, wobei die elektrochromen Chromophore als Oxidationsprodukte gebildet werden.2. Pixelated display according to claim 1, wherein the electrochromic chromophores are formed as oxidation products.
3. Pixeliertes Display nach einem der vorstehenden Ansprüche, wobei folgende Farben aus folgenden Farbstoffen gebildet werden: a) blaugrüne Farbstoffe, aus p-Phenylendiaminderivaten und Phenolderivaten/Naphtholderivaten (Indophenoltyp) , b) rot/purpur Farbstoffe, aus p-Phenylendiaminderivaten und Pyrazolonderivaten (Pyrazolontyp) und/oder c) gelbe Farbstoffe, aus p-Phenylendiaminderivaten und 1,3- Diketonderivaten .3. Pixelated display according to one of the preceding claims, wherein the following colors are formed from the following dyes: a) cyan dyes, from p-phenylenediamine derivatives and phenol derivatives / naphthol derivatives (indophenol type), b) red / purple dyes, from p-phenylenediamine derivatives and pyrazolone derivatives ( Pyrazolone type) and / or c) yellow dyes, from p-phenylenediamine derivatives and 1,3-diketone derivatives.
4. Pixeliertes Display nach einem der vorstehenden Ansprüche, wobei zumindest ein elektrochromes Chromophor ausgewählt ist aus der Gruppe, folgende Farbstoffe umfassend,A pixelated display according to any one of the preceding claims, wherein at least one electrochromic chromophore is selected from the group comprising the following dyes:
a) Indophenoltyp-Farbstoff : n/m = 2/1a) Indophenol-type dye: n / m = 2/1
Figure imgf000011_0001
b) Pyrazolon-Typ-Farbstoff : n/m = 2/1
Figure imgf000011_0001
b) Pyrazolone type dye: n / m = 2/1
Figure imgf000012_0001
Figure imgf000012_0001
c) von einem 1, 3-Diketon abgeleiteter Farbstoff: n/m = 2/1c) dye derived from a 1,3-diketone: n / m = 2/1
Figure imgf000012_0002
Figure imgf000012_0002
5. Pixeliertes Display nach einem der vorstehenden Ansprüche, wobei die Farbstoffe in einer polymeren Matrix eingesetzt werden. A pixelated display according to any one of the preceding claims wherein the dyes are employed in a polymeric matrix.
PCT/EP2006/062572 2005-05-31 2006-05-24 Electrochromic display WO2006128820A1 (en)

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