WO2010000615A1 - Electrochromic formulation, manufacturing process therefor and electrochromic organic component - Google Patents

Electrochromic formulation, manufacturing process therefor and electrochromic organic component Download PDF

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Publication number
WO2010000615A1
WO2010000615A1 PCT/EP2009/057540 EP2009057540W WO2010000615A1 WO 2010000615 A1 WO2010000615 A1 WO 2010000615A1 EP 2009057540 W EP2009057540 W EP 2009057540W WO 2010000615 A1 WO2010000615 A1 WO 2010000615A1
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electrochromic
formulation
formulation according
color
displays
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PCT/EP2009/057540
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German (de)
French (fr)
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Andreas Kanitz
Wolfgang Roth
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Siemens Aktiengesellschaft
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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
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK  ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
    • C09C1/00—Treatment of specific inorganic materials other than fibrous fillers; Preparation of carbon black
    • C09C1/0015—Pigments exhibiting interference colours, e.g. transparent platelets of appropriate thinness or flaky substrates, e.g. mica, bearing appropriate thin transparent coatings
    • 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
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
    • C01P2004/00—Particle morphology
    • C01P2004/60—Particles characterised by their size
    • C01P2004/61—Micrometer sized, i.e. from 1-100 micrometer
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
    • C01P2006/00—Physical properties of inorganic compounds
    • C01P2006/60—Optical properties, e.g. expressed in CIELAB-values
    • 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
    • G02F2001/1518—Ferrocene compounds

Definitions

  • Electrochromic formulation method of preparation and electrochromic organic device
  • the invention relates to formulations and their use in organically based electrochromic components, for example for the production of displays and / or status displays with special color effects.
  • Electrochromic displays based on organic materials normally comprise an active electrochromic layer, which in the case of a display is located between electrodes arranged perpendicular to one another.
  • Essential components of the active layer are a redox system and a dye.
  • a voltage By applying a voltage, the concentration ratio of the redox partners to each other in the material is shifted. In this reaction, protons and / or ions are released or bound in the material.
  • a voltage is applied to the material, the shift in the balance of existing redox partners on the two electrodes is in the opposite direction. This can be visualized, for example, via a pH-active dye.
  • a principle to realize electrochromic displays is not to cause the color change by the change in the pH in the display, but to use the already taking place redox processes to produce high-contrast color changes by the formation of reductive and / or oxidative states in suitable materials ,
  • the so-called viologens and polythiophenes have become known as classes of materials.
  • DE 10 2005 032 316 discloses polymeric 4,4'-bipyridinium structures, which are separated from one another by an alkylene spacer, which are outstandingly suitable for this purpose.
  • the object of the present invention is therefore to provide an electrochromic formulation which exhibits particular color effects.
  • the object of the invention and solution of the object is an electrochromic formulation comprising an electrochromic dye, an effect pigment and a solvent, the effect pigment being used in the form of particles which exhibit color effects.
  • the subject matter of the invention is an electrochromic organic component with special color effects.
  • effect pigments be used. These are mica flakes coated with titanium dioxide and / or other metal oxides. Since the thicknesses of the metal oxide layers are in the range of the wavelength of the light, these leaflets are colorfully iridescent due to interference effects.
  • Such commercially available effect pigments can, for example, have a multicolored pearl gloss. But you can also reflect only one color, such as red, green or blue. In general, the color is also dependent on the viewing angle. Depending on the viewing angle, the color impression may be green or blue, for example.
  • Such pigments are also referred to as silver luster, gold luster, metallic luster or interference pigments.
  • the particles can be used in different particle size distributions, for example, the average average sizes can be in the range of micrometers, but the particles can also be used in the form of microcrystals and / or nanocrystals.
  • the titanium dioxide-based spherical white pigment is replaced by platelet-shaped mica flakes coated with titanium dioxide and / or other metal oxides. In this case, the color effect typical of the pigments is utilized.
  • Electrochromically active displays / status displays are obtained which, when not switched on, have the typical iridescent metallic luster of the respective effect pigment.
  • the displays / status displays are optically particularly attractive due to the effect pigment. They also show a 3-dimenional depth effect. Such displays are particularly interesting as an eye-catcher for display elements.
  • the displays / status displays can contain both areas with conventionally used, spherical titanium dioxide white pigment and with platelet-shaped effect pigments proposed here for the first time for use in electrochromic formulations.
  • Example 1 Preparation of an electrochromically active formulation with an effect pigment and an EC cell thereof
  • Example 2 Preparation of an electrochromically active formulation with an effect pigment and an EC cell thereof
  • Example 3 Preparation of an electrochromically active formulation and EC cell therefrom
  • a blue color impression is produced when a voltage of 1-2 V is applied to the cathode.
  • a voltage of 1-2 V is applied to the cathode.
  • the invention relates to formulations and their use in organically based electrochromic components, for example for the production of displays and / or status displays with special dazzling color effects.
  • organically based electrochromic components for example for the production of displays and / or status displays with special dazzling color effects.
  • particles with color effects are added to the formulation.

Abstract

The invention relates to formulations and use thereof in organically-based electrochromic components, for example for manufacturing displays and/or status displays with particularly brilliant effects. To this end, instead of the previously common addition of a white pigment, particles are added that have the color effects of the formulation.

Description

Beschreibungdescription
Elektrochrome Formulierung, Herstellungsverfahren dazu und elektrochromes organisches BauelementElectrochromic formulation, method of preparation and electrochromic organic device
Die Erfindung betrifft Formulierungen und deren Anwendung in organisch basierten elektrochromen Bauteilen, beispielsweise zur Herstellung von Displays und/oder Zustandsanzeigen mit besonderen Farbeffekten.The invention relates to formulations and their use in organically based electrochromic components, for example for the production of displays and / or status displays with special color effects.
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 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. Wenn eine Spannung an das Ma- terial angelegt wird, dann läuft die Verschiebung des Gleichgewichts vorhandener Redox-Partner an den beiden Elektroden in entgegen gesetzter Richtung. Dies kann beispielsweise über einen pH-aktiven Farbstoff sichtbar gemacht werden.Electrochromic displays based on organic materials normally comprise an active electrochromic layer, which in the case of a display is located between electrodes arranged perpendicular to one another. Essential components of the active layer are a redox system and a dye. By applying a voltage, the concentration ratio of the redox partners to each other in the material is shifted. In this reaction, protons and / or ions are released or bound in the material. When a voltage is applied to the material, the shift in the balance of existing redox partners on the two electrodes is in the opposite direction. This can be visualized, for example, via a pH-active dye.
Ein 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 Zu- stände in geeigneten Materialien zu erzeugen. Dabei sind vor allem die sogenannten Viologene und Polythiophene als Materialklassen bekannt geworden. Aus der DE 10 2005 032 316 sind polymere 4, 4 ' -Bipyridinium-Strukturen, die durch einen Alky- lenspacer voneinander getrennt sind, bekannt, die sich dazu hervorragend eignen. Allerdings besteht weiterhin der Bedarf, zusätzliche Farbeffekte bei elektrochromen Displays und/oder Zustandsanzeigen zu schaffen.A principle to realize electrochromic displays is not to cause the color change by the change in the pH in the display, but to use the already taking place redox processes to produce high-contrast color changes by the formation of reductive and / or oxidative states in suitable materials , In particular, the so-called viologens and polythiophenes have become known as classes of materials. DE 10 2005 032 316 discloses polymeric 4,4'-bipyridinium structures, which are separated from one another by an alkylene spacer, which are outstandingly suitable for this purpose. However, there is still a need to provide additional color effects with electrochromic displays and / or status indicators.
Aufgabe der vorliegenden Erfindung ist deshalb, eine elektro- chrome Formulierung zu schaffen, die besondere Farbeffekte zeigt .The object of the present invention is therefore to provide an electrochromic formulation which exhibits particular color effects.
Gegenstand der Erfindung und Lösung der Aufgabe ist eine elektrochrome Formulierung, einen elektrochromen Farbstoff, ein Effektpigment und ein Lösungsmittel umfassend, wobei das Effektpigment in Form von Partikeln, die Farbeffekte zeigen, eingesetzt wird. Außerdem ist Gegenstand der Erfindung ein elektrochromes organisches Bauelement mit besonderen Farbef- fekten.The object of the invention and solution of the object is an electrochromic formulation comprising an electrochromic dye, an effect pigment and a solvent, the effect pigment being used in the form of particles which exhibit color effects. In addition, the subject matter of the invention is an electrochromic organic component with special color effects.
Anstelle des üblichen Weißpigments Titandioxid in Form kugelförmiger oder sphärischer Partikel wird vorgeschlagen, dass so genannte Effektpigmente eingesetzt werden. Bei diesen han- delt es sich um Glimmerblättchen, die mit Titandioxid und/oder anderen Metalloxiden beschichtet sind. Da die Dicken der Metalloxidschichten im Bereich der Wellenlänge des Lichts liegen, sind diese Blättchen auf Grund von Interferenzeffekten farbig schillernd. Solche kommerziell erhältlichen Ef- fektpigmente können beispielsweise einen mehrfarbigen Perlmutglanz aufweisen. Sie können aber auch nur eine Farbe reflektieren, beispielsweise rot, grün oder blau. In der Regel ist die Farbe auch abhängig vom Betrachtungswinkel. Abhängig vom Betrachtungswinkel kann der Farbeindruck beispielsweise grün oder blau sein. Solche Pigmente werden auch als Silberglanz-, Goldglanz-, Metallglanz- oder Interferenzpigmente bezeichnet .Instead of the usual white pigment titanium dioxide in the form of spherical or spherical particles, it is proposed that so-called effect pigments be used. These are mica flakes coated with titanium dioxide and / or other metal oxides. Since the thicknesses of the metal oxide layers are in the range of the wavelength of the light, these leaflets are colorfully iridescent due to interference effects. Such commercially available effect pigments can, for example, have a multicolored pearl gloss. But you can also reflect only one color, such as red, green or blue. In general, the color is also dependent on the viewing angle. Depending on the viewing angle, the color impression may be green or blue, for example. Such pigments are also referred to as silver luster, gold luster, metallic luster or interference pigments.
Die Partikel können in verschiedenen Korngrößenverteilungen eingesetzt werden, beispielsweise können die durchschnittlichen mittleren Größen im Bereich von Mikrometer liegen, die Partikel können aber auch in Form von Mikrokristallen und/oder Nanokristallen eingesetzt werden. Bevorzugt wird das sphärische Weißpigment auf Titandioxidbasis durch blättchenförmige, mit Titandioxid und/oder anderen Metalloxiden beschichtete Glimmerblättchen ersetzt. Dabei wird der für die Pigmente typische Farbeffekt ausgenutzt.The particles can be used in different particle size distributions, for example, the average average sizes can be in the range of micrometers, but the particles can also be used in the form of microcrystals and / or nanocrystals. Preferably, the titanium dioxide-based spherical white pigment is replaced by platelet-shaped mica flakes coated with titanium dioxide and / or other metal oxides. In this case, the color effect typical of the pigments is utilized.
Es werden elektrochrom aktive Displays/Zustandsanzeigen erhalten, die im ungeschalteten Zustand den typischen irisierenden Metallglanz des jeweiligen Effektpigments aufweisen.Electrochromically active displays / status displays are obtained which, when not switched on, have the typical iridescent metallic luster of the respective effect pigment.
Im geschalten Zustand wird dieser Farbeffekt durch die Farbe des jeweiligen elektrochrom aktiven Farbstoffs bestimmt, wobei der metallische Glanz oftmals erhalten bleibt. Die Displays/Zustandsanzeigen sind durch das Effektpigment optisch besonders attraktiv. Sie zeigen weiterhin einen 3- dimenionalen Tiefeneffekt. Solche Displays sind insbesondere als Blickfang für Anzeigeelemente interessant. Die Displays/Zustandsanzeigen können sowohl Bereiche mit herkömmlich eingesetztem, sphärischen Titandioxid-Weißpigment und mit hier erstmals für die Nutzung in elektrochromen Formulierungen vorgeschlagenem, blättchenförmigen Effektpigmenten enthalten .In the switched state, this color effect is determined by the color of the respective electrochromically active dye, the metallic gloss often being retained. The displays / status displays are optically particularly attractive due to the effect pigment. They also show a 3-dimenional depth effect. Such displays are particularly interesting as an eye-catcher for display elements. The displays / status displays can contain both areas with conventionally used, spherical titanium dioxide white pigment and with platelet-shaped effect pigments proposed here for the first time for use in electrochromic formulations.
Ausführungsbeispieleembodiments
1. Beispiel: Herstellung einer elektrochrom aktiven Formulierung mit einem Effektpigment und einer EC-Zelle darausExample 1: Preparation of an electrochromically active formulation with an effect pigment and an EC cell thereof
3g Effektpigment „Perlglanz Magic Feuer" (Fa. Kremer) werden mit 0.6g eines polymeren 4, 4' -Bipyridinium-Derivats (PoIy- (dodecylen-4 , 4 ' -bipyridinium-dibromid) und 0.23g Ferrocen mittels eines Speed-Mixers intensiv miteinander vermischt. Dazu werden 5 g Diethylenglykol gegeben und ebenfalls mittels eines Speed-Mixers intensiv eingemischt. Es wird eine helle mehrfarbig irisierende Paste mit vom Betrachtungswinkel abhängigem Perlmuttglanz erhalten. Aus dieser wird mittels der Rakel-Technik auf einem ITO-beschichteten Substrat eine Schicht der Dicke 50 μm hergestellt. Beim Kontaktieren mit einer zweiten ITO-beschichteten Folie wird beim Anlegen einer Spannung von 1-2 V an der Kathode ein blauer Farbeindruck erzeugt. Durch Umpolen der elektrochromen Zelle kann zwischen den Farbeindrücken blau und mehrfarbig irrisierend reversibel hin- und hergeschaltet werden. Im unbeschalteten Zustand zeigt die elektrochrom aktive Zelle einen vom Betrachtungswinkel abhängigen Farbeindruck.3g effect pigment "Pearlescent Magic Fire" (Kremer) with 0.6 g of a polymeric 4, 4 '-Bipyridinium derivative (poly (dodecylene-4, 4'-bipyridinium-dibromid) and 0.23g ferrocene using a speed mixer 5 g of diethylene glycol are added and intensively mixed in using a speed mixer to give a bright multicolor iridescent pearlescent pearlescent paste, which is then knife coated onto an ITO coated substrate Layer of thickness 50 microns produced. Upon contact with a second ITO-coated film, a blue color impression is produced when a voltage of 1-2 V is applied to the cathode. By reversing the polarity of the electrochromic cell between the color impressions blue and multicolor irrisierend reversibly switched back and forth. In the unused state, the electrochromically active cell shows a color perception dependent on the viewing angle.
2. Beispiel: Herstellung einer elektrochrom aktiven Formulierung mit einem Effektpigment und einer EC-Zelle darausExample 2: Preparation of an electrochromically active formulation with an effect pigment and an EC cell thereof
3g Effektpigment „Perlglanz Chroma Grün" (Fa. Kremer) werden mit 0.6g eines polymeren 4, 4' -Bipyridinium-Derivats (PoIy- (dodecylen-4 , 4 ' -bipyridinium-dibromid) und 0.23g Ferrocen mittels eines Speed-Mixers intensiv miteinander vermischt. Dazu werden 3.4 g Diethylenglykol gegeben und ebenfalls mittels eines Speed-Mixers intensiv eingemischt. Es wird eine metallisch grün irisierende Paste erhalten. Aus dieser wird mittels der Rakel-Technik auf einer ITO-beschichteten Folie eine Schicht der Dicke 50 μm hergestellt. Beim Kontaktieren mit einer zweiten ITO-beschichteten Folie wird beim Anlegen einer Spannung von 1-2 V an der Kathode ein blauer Farbein- druck erzeugt. Durch Umpolen der elektrochromen Zelle kann zwischen den Farbeindrücken blau und metallisch grün irrisierend reversibel hin- und hergeschaltet werden. Im unbeschalteten Zustand zeigt die elektrochrom aktive Zelle einen vom Betrachtungswinkel abhängigen Farbeindruck.3 g of the effect pigment "pearlescent chroma green" (from Kremer) are mixed with 0.6 g of a polymeric 4,4'-bipyridinium derivative (poly (dodecylene-4,4'-bipyridinium-dibromide) and 0.23 g of ferrocene using a speed mixer To this end, 3.4 g of diethylene glycol are added and mixed intensively by means of a speed mixer to give a metallic green iridescent paste, from which a 50 μm thick layer is produced by means of the doctor blade technique on an ITO-coated film When contacting with a second ITO-coated film, a blue color impression is produced at the cathode when a voltage of 1-2 V is applied.) By reversing the polarity of the electrochromic cell between the color impressions, blue and metallic green iridescence reversibly can be switched back and forth In the unconnected state, the electrochromically active cell shows a color impression dependent on the viewing angle.
3. Beispiel: Herstellung einer elektrochrom aktiven Formulierung und einer EC-Zelle darausExample 3: Preparation of an electrochromically active formulation and EC cell therefrom
3g Effektpigment „Perlglanz Lava Red" (Fa. Kremer) werden mit 0.6g eines polymeren 4, 4' -Bipyridinium-Derivats (PoIy- (dodecylen-4, 4' -bipyridinium-dibromid) und 0.23g Ferrocen, das zur Stabilisierung der Formulierung eingesetzt wird, mit- tels eines Speed-Mixers intensiv miteinander vermischt. Dazu werden 5 g Diethylenglykol gegeben und ebenfalls mittels eines Speed-Mixers intensiv eingemischt. Es wird eine metallisch rot irisierende Paste erhalten. Aus dieser wird mittels der Rakel-Technik auf einer ITO-beschichteten Folie eine Schicht der Dicke 50 μm hergestellt. Beim Kontaktieren mit einer zweiten ITO-beschichteten Folie wird beim Anlegen einer Spannung von 1-2 V an der Kathode ein blauer Farbeindruck erzeugt. Durch Umpolen der elektrochromen Zelle kann zwischen den Farbeindrücken blau und metallisch rot irisierend reversibel hin- und hergeschaltet werden. Im unbeschalteten Zustand zeigt die elektrochrom aktive Zelle einen vom Betrachtungswinkel abhängigen Farbeindruck.3 g of the effect pigment "pearlescent lava red" (from Kremer) are mixed with 0.6 g of a polymeric 4,4'-bipyridinium derivative (poly (dodecylene-4,4'-bipyridinium-dibromide) and 0.23 g of ferrocene used to stabilize the Formulation is used, with- of a speed mixer are mixed intensively. For this purpose, 5 g of diethylene glycol are added and also intensively mixed by means of a speed mixer. It is obtained a metallic red iridescent paste. From this, a layer of thickness 50 μm is produced by means of the doctor blade technique on an ITO-coated film. Upon contact with a second ITO-coated film, a blue color impression is produced when a voltage of 1-2 V is applied to the cathode. By reversing the polarity of the electrochromic cell between the color impressions blue and metallic red iridescent reversible can be switched back and forth. In the unused state, the electrochromically active cell shows a color perception dependent on the viewing angle.
Die Erfindung betrifft Formulierungen und deren Anwendung in organisch basierten elektrochromen Bauteilen, beispielsweise zur Herstellung von Displays und/oder Zustandsanzeigen mit besonderen schillernden Farbeffekten. Dazu werden anstelle der bisher üblichen Zugabe eines Weißpigments Partikel mit Farbeffekten der Formulierung zugesetzt. The invention relates to formulations and their use in organically based electrochromic components, for example for the production of displays and / or status displays with special dazzling color effects. For this purpose, instead of the usual addition of a white pigment, particles with color effects are added to the formulation.

Claims

Patentansprüche claims
1. Elektrochrom aktive Formulierung, einen elektrochromen Farbstoff, ein Effektpigment und ein Lösungsmittel umfas- send, wobei das Effektpigment in Form von Partikeln, die Farbeffekte zeigen, eingesetzt wird.1. electrochromic active formulation comprising an electrochromic dye, an effect pigment and a solvent, wherein the effect pigment is used in the form of particles which show color effects.
2. Formulierung nach Anspruch 1, wobei der elektrochrom aktive Farbstoff ein polymeres 4, 4' -Bipyridinium-Derivat umfasst.A formulation according to claim 1 wherein the electrochromically active dye comprises a polymeric 4,4'-bipyridinium derivative.
3. Formulierung nach einem der Ansprüche 1 oder 2, wobei das Lösungsmittel Diethylenglykol umfasst.A formulation according to any one of claims 1 or 2, wherein the solvent comprises diethylene glycol.
4. Formulierung nach einem der vorstehenden Ansprüche, wobei die Partikel, die Farbeffekte zeigen, beschichtete Glimmer- blättchen sind.4. A formulation according to any one of the preceding claims, wherein the particles exhibiting color effects are coated mica flakes.
5. Formulierung nach einem der vorstehenden Ansprüche, wobei die Partikel, die Farbeffekte zeigen, mit Metalloxiden be- schichtete Glimmerblättchen sind.5. A formulation according to any one of the preceding claims, wherein the particles exhibiting color effects are metal oxide-coated mica flakes.
6. Formulierung nach einem der vorstehenden Ansprüche, die noch stabilisierende Zusätze enthält.6. Formulation according to one of the preceding claims, which still contains stabilizing additives.
7. Elektrochromes organisches Bauelement das eine elektrochrom aktive Formulierung nach einem der vorstehenden Ansprüche enthält. 7. An electrochromic organic device containing an electrochromic active formulation according to any one of the preceding claims.
PCT/EP2009/057540 2008-06-30 2009-06-17 Electrochromic formulation, manufacturing process therefor and electrochromic organic component WO2010000615A1 (en)

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR100298560B1 (en) * 1992-07-24 2001-10-22 이데이 노부유끼 Information listing method and recording medium cartridge
USRE44828E1 (en) * 1999-06-16 2014-04-08 Core Wireless Licensing S.A.R.L. Method and arrangement for choosing a channel coding and interleaving scheme for certain types of packet data connections
KR20170131568A (en) 2015-03-30 2017-11-29 시오노기 앤드 컴파니, 리미티드 9-membered fused ring derivative
US10150728B2 (en) 2013-10-17 2018-12-11 Shionogi & Co., Ltd. Alkylene derivatives

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4416517A (en) * 1980-12-22 1983-11-22 Corning Glass Works Electrochromic devices including a mica layer electrolyte
JPS60260023A (en) * 1984-06-07 1985-12-23 Asahi Glass Co Ltd Electrochromic display element
US5876634A (en) * 1995-12-26 1999-03-02 Monsanto Company Electrochromic tin oxide

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4416517A (en) * 1980-12-22 1983-11-22 Corning Glass Works Electrochromic devices including a mica layer electrolyte
JPS60260023A (en) * 1984-06-07 1985-12-23 Asahi Glass Co Ltd Electrochromic display element
US5876634A (en) * 1995-12-26 1999-03-02 Monsanto Company Electrochromic tin oxide

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR100298560B1 (en) * 1992-07-24 2001-10-22 이데이 노부유끼 Information listing method and recording medium cartridge
USRE44828E1 (en) * 1999-06-16 2014-04-08 Core Wireless Licensing S.A.R.L. Method and arrangement for choosing a channel coding and interleaving scheme for certain types of packet data connections
US10150728B2 (en) 2013-10-17 2018-12-11 Shionogi & Co., Ltd. Alkylene derivatives
EP3670496A2 (en) 2013-10-17 2020-06-24 Shionogi&Co., Ltd. Acc2 inhibitors
KR20170131568A (en) 2015-03-30 2017-11-29 시오노기 앤드 컴파니, 리미티드 9-membered fused ring derivative
US10233156B2 (en) 2015-03-30 2019-03-19 Shionogi & Co., Ltd. 9-membered fused ring derivative

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