EP2334715A1 - Electrochromic formulation, method for the production thereof, and electrochromic organic component - Google Patents

Electrochromic formulation, method for the production thereof, and electrochromic organic component

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Publication number
EP2334715A1
EP2334715A1 EP09783362A EP09783362A EP2334715A1 EP 2334715 A1 EP2334715 A1 EP 2334715A1 EP 09783362 A EP09783362 A EP 09783362A EP 09783362 A EP09783362 A EP 09783362A EP 2334715 A1 EP2334715 A1 EP 2334715A1
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EP
European Patent Office
Prior art keywords
electrochromic
formulation
organic component
end group
production
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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Application number
EP09783362A
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German (de)
French (fr)
Inventor
Andreas Kanitz
Wolfgang Roth
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Siemens AG
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Siemens AG
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Publication date
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Publication of EP2334715A1 publication Critical patent/EP2334715A1/en
Withdrawn legal-status Critical Current

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Classifications

    • 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
    • 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
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom

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 increased service life.
  • 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.
  • the concentration ratio of the redox partners is shifted relative to one another in the material.
  • 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.
  • the principle of realizing electrochromic displays is not to induce the color change by changing the pH in the display, but to use the already occurring redox processes in order to achieve high-contrast color changes through the formation of reductive and / or oxidative states in suitable materials produce.
  • the so-called viologens and polythiophenes have become known as Mate ⁇ - altracn.
  • DE 10 2005 032 316 discloses 4, 4'-bipyridinium structures which are separated from one another by an alkylene spacer, which are outstandingly suitable for this purpose.
  • Bipyridinium salts produce a purple hue under tension. Therefore, these compounds are also called viologens. This color impression is created by the so-called pime ⁇ stechnik.
  • the polymeric bipyridyl derivatives as used in the electrochromic formulations, already have a very long service life, but there is always the need to further increase the lifetime of the formulations.
  • the invention relates to a dye based on the 4, 4 '-Bipyridiniumsalze for a formulation for an electrochromically active organic electronic component, wherein at least one reactive end group of the 4, 4' Bipy ⁇ diniumsalzes replaced by at least one inert end group or protected.
  • the subject of the invention is an electrochromic organic component which contains an electrochromically active formulation according to the invention.
  • the Formu ⁇ -regulation also comprises a stabilizer in the form of a metal- ⁇ - complex such as a metallocene, for example a ferro-cens or Ferrocende ⁇ vates.
  • the inert end group comprises an inert N-substituted alkyl group.
  • the formulation comprises a whitening agent or a white pigment.
  • Suitable inert end groups are, for example, alkoxy groups and / or N-substituted alkyl or aryl groups.
  • endcapping according to the invention in particular is to be he ⁇ sufficient that the electrochromic formulation in the form of a paste, such as is present in the electrochromic cell, as inert, non-reactive and therefore not aggressive or damaging to other materials, particularly against ⁇ above the transparent electrode such as the indium Tm (tin) oxide (ITO) electrode of the electrochromic device behave.
  • the electrochromic formulation in the form of a paste such as is present in the electrochromic cell, as inert, non-reactive and therefore not aggressive or damaging to other materials, particularly against ⁇ above the transparent electrode such as the indium Tm (tin) oxide (ITO) electrode of the electrochromic device behave.
  • the endcapping is carried out, for example, as follows:
  • the resulting white formulation is applied by means of the Rakeltech ⁇ technology to a lower electrode layer on a substrate, such as an ITO-coated PET film, with an adhesive frame serves as a boundary of the electrochromic active area.
  • the adhesive frame is also used for bonding to the upper electrode layer, for example with a second ITO-coated film as a counter electrode.
  • a blue color impression is obtained at the cathode. Lifetime measurement:
  • the lifetime measurement is carried out at a temperature of 85 ° C.
  • the lifetime is 3219 hours, which is 749 hours or about 30% higher than the lifetime of a cell with untreated poly-N, N'-dodecylene-4,4'-diphenyl.
  • the lifetime is defined as the decrease of the initial contrast to 20%.
  • inert end groups are accompanied by the elimination of the existing reactive end groups such as residual covalently bound bromine end groups which are present due to the synthesis.
  • the elimination takes place with suitable reagents, which vary depending on the end group to be eliminated and which are readily apparent to the person skilled in the art.
  • the content of the end groups varies, so that it can not be determined reproducibly. It is therefore expected that the bromine content of the bipyridyl derivative depends on the particular batch.
  • the covalently bound bromine on untreated poly-N, N'-dodecylene-4, 4 '-dipy ⁇ dyl may in particular at elevated temperature in the electrochromic device in Deduce ⁇ actions are cleaved, and thus, in the absence of the electrode Endcap- ping attack, whereby the further electrical wiring of the component is prevented.
  • the life of an electrochromic active Zel ⁇ le is limited.
  • the life of the component is increased, for example, by about 30%.

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  • Chemical & Material Sciences (AREA)
  • Physics & Mathematics (AREA)
  • Nonlinear Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Chemistry (AREA)
  • Electrochromic Elements, Electrophoresis, Or Variable Reflection Or Absorption Elements (AREA)

Abstract

The invention relates to formulations and the use thereof in organically based electrochromic components, e.g. for producing displays and/or state indicators having a longer service life. The service life is increased by end-capping the 4,4'-bipyridinium salt.

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 erhöhter Lebensdauer.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 increased service life.
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 Konzentrationsver- haltnis 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- teπal angelegt wird, dann lauft 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 is shifted relative to one another in the material. 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.
Em Prinzip elektrochrome Displays zu verwirklichen, besteht darin, die Farbanderung nicht durch die Änderung des pH- Wertes im Display herbeizufuhren, 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 Mateπ- alklassen bekannt geworden. Aus der DE 10 2005 032 316 sind 4, 4 ' -Bipyridinium-Strukturen, die durch einen Alkylenspacer voneinander getrennt sind, bekannt, die sich dazu hervorra- gend eignen. Bipyridiniumsalze erzeugen unter Spannung einen violetten Farbton. Deshalb werden diese Verbindungen auch als Viologene bezeichnet. Dieser Farbeindruck entsteht durch die so genannte Pimeπsierung . Darunter versteht man einen Sta- peleffekt der Moleküle auf Grund ihrer Struktur. Werden die Bipyπdiniumsalze als Polymere mit langen Spacern syntheti¬ siert, wird die Pimeπsierung statistisch zurückgedrängt, so dass die unter Spannung gebildeten Radikale blau erscheinen und die Reversibilität des Schaltvorgangs wesentlich stabiler wird.The principle of realizing electrochromic displays is not to induce the color change by changing the pH in the display, but to use the already occurring redox processes in order to achieve high-contrast color changes through the formation of reductive and / or oxidative states in suitable materials produce. In particular, the so-called viologens and polythiophenes have become known as Mateπ- alklassen. DE 10 2005 032 316 discloses 4, 4'-bipyridinium structures which are separated from one another by an alkylene spacer, which are outstandingly suitable for this purpose. Bipyridinium salts produce a purple hue under tension. Therefore, these compounds are also called viologens. This color impression is created by the so-called pimeπsierung. By this one understands a Sta- effect of the molecules due to their structure. If the Bipyπdiniumsalze as polymers with long spacers syntheti ¬ Siert that Pimeπsierung is statistically pushed back, so that the radicals formed under tension appear blue, and the reversibility of the switching operation is much more stable.
In der Regel haben die polymeren Bipyridyldeπvate, so wie sie in den elektrochromen Formulierungen eingesetzt werden, eine bereits sehr hohe Lebensdauer, es besteht jedoch immer der Bedarf, die Lebensdauer der Formulierungen weiter zu erhohen .In general, the polymeric bipyridyl derivatives, as used in the electrochromic formulations, already have a very long service life, but there is always the need to further increase the lifetime of the formulations.
Aufgabe der vorliegenden Erfindung ist es daher, die bekann- ten Formulierungen auf Basis der in der DE 10 2005 032 316 genannten 4, 4' -Bipyrdiylverbmdungen so zu modifizieren, dass sie eine erhöhte Stabilität im elektrochromen Bauteil zeigen .It is therefore an object of the present invention to modify the known formulations based on the 4,4'-bipyrdiyl compounds mentioned in DE 10 2005 032 316 such that they exhibit increased stability in the electrochromic component.
Die Losung der Aufgabe und der Gegenstand der Erfindung sind in der Beschreibung, den Ansprüchen und den Beispielen offenbart.The solution of the problem and the subject of the invention are disclosed in the description, the claims and the examples.
Dementsprechend ist Gegenstand der Erfindung ein Farbstoff auf der Basis der 4, 4' -Bipyridiniumsalze für eine Formulierung für ein elektrochrom aktives organisches elektronisches Bauelement, wobei zumindest eine reaktive Endgruppe des 4, 4' Bipyπdiniumsalzes durch zumindest eine inerte Endgruppe ersetzt oder geschützt ist. Außerdem ist Gegenstand der Er- findung ein elektrochromes organisches Bauteil, das eine elektrochrom aktive Formulierung nach der Erfindung enthalt.Accordingly, the invention relates to a dye based on the 4, 4 '-Bipyridiniumsalze for a formulation for an electrochromically active organic electronic component, wherein at least one reactive end group of the 4, 4' Bipyπdiniumsalzes replaced by at least one inert end group or protected. In addition, the subject of the invention is an electrochromic organic component which contains an electrochromically active formulation according to the invention.
Das Endcapping ist der Ersatz oder der Schutz einer reaktiven Endgruppe durch eine inerte und nicht reaktive Endgruppe, zu dem Zweck, dass die Verbindung nicht mehr das Material der umgebenden Schichten angreifen kann. Dabei kann die reaktive Endgruppe sowohl eliminiert werden, als auch durch Umsetzung deaktiviert . Nach einer vorteilhaften Ausfuhrungsform umfasst die Formu¬ lierung noch einen Stabilisator in Form eines Metall-π- Komplexes wie eines Metallocens, beispielsweise eines Ferro- cens oder eines Ferrocendeπvates .Endcapping is the replacement or protection of a reactive end group by an inert and non-reactive end group, for the purpose of preventing the compound from attacking the material of the surrounding layers. The reactive end group can be eliminated as well as deactivated by conversion. According to an advantageous embodiment, the Formu ¬-regulation also comprises a stabilizer in the form of a metal-π- complex such as a metallocene, for example a ferro-cens or Ferrocendeπvates.
Nach einer vorteilhaften Ausgestaltung der Erfindung umfasst die inerte Endgruppe eine inerte N-substituierte Alkylgruppe.According to an advantageous embodiment of the invention, the inert end group comprises an inert N-substituted alkyl group.
Nach einer vorteilhaften Ausfuhrungsform der Erfindung umfasst die Formulierung einen Weißmacher oder ein Weißpigment.According to an advantageous embodiment of the invention, the formulation comprises a whitening agent or a white pigment.
Als inerte Endgruppe kommen beispielsweise Alkoxygruppen und/oder N-substituierte Alkyl- oder Arylgruppen in Frage.Suitable inert end groups are, for example, alkoxy groups and / or N-substituted alkyl or aryl groups.
Beispielsweise dienen als inerte Endgruppen alle bekannten Alkyl-, Arylreste, Carbonsaureesterreste und/oder Ether. Diese entstehen z. B. beim Verethern mit Alkoholen, Alkohole zum Einfuhren relevanter Gruppen durch Veretherung und sonstige Endgruppen kommen in Frage, die am Ende chemisch nicht reaktiv und/oder wenig polarisiert sind.For example, serve as inert end groups all known alkyl, aryl, Carbonsaureesterreste and / or ether. These arise z. As in the etherification with alcohols, alcohols for importing relevant groups by etherification and other end groups are in question, which are chemically non-reactive and / or little polarized in the end.
Durch das Endcapping nach der Erfindung soll insbesondere er¬ reicht werden, dass die elektrochrome Formulierung in Form einer Paste, wie sie in der elektrochromen Zelle vorliegt, sich als inert, unreaktiv und daher nicht aggressiv oder schädigend gegenüber anderen Materialien, insbesondere gegen¬ über der transparenten Elektrode wie der Indium Tm (Zinn) Oxide (ITO) Elektrode des elektrochromen Bauteils verhalt.By endcapping according to the invention in particular is to be he ¬ sufficient that the electrochromic formulation in the form of a paste, such as is present in the electrochromic cell, as inert, non-reactive and therefore not aggressive or damaging to other materials, particularly against ¬ above the transparent electrode such as the indium Tm (tin) oxide (ITO) electrode of the electrochromic device behave.
Zur Herstellung wird auf die in der DE 10 2005 032 316 be¬ schriebene Synthese eines nicht pimeπsierenden polymeren Bi- pyπdyldeπvates (PoIy-N, N' -dodecylen-4, 4' -dipyπdyl) nach der dort offenbarten Standard-Methode verwiesen, die hiermit auch zum Gegenstand der vorliegenden Offenbarung gemacht werden soll. Anschließend erfolgt - ebenfalls über chemische Synthese - das „endcapping", womit die Stabilisierung des Ma- teπals durch Einfügen zumindest einer inerten Endgruppe ge¬ meint ist.For the preparation pyπdyldeπvates to be ¬ specified in DE 10 2005 032 316 synthesis of a non-polymeric pimeπsierenden Bi- (poly-N, N '-dodecylen-4, 4' -dipyπdyl), reference is made to the disclosed therein standard method herewith also to be made the subject of the present disclosure. This is followed by "endcapping", also via chemical synthesis, thus stabilizing the ma- teπals by inserting at least one inert end group ge means ¬ .
Im Folgenden wird die Erfindung noch anhand eines Ausfuh- rungsbeispiels naher erläutert:The invention will be explained in more detail below with reference to an exemplary embodiment:
Ausgehend vom PoIy -N, N' -dodecylen-4, 4' -dipyπdyl wird das endcapping beispielsweise folgendermaßen durchgeführt:Starting from the poly-N, N'-dodecylene-4,4'-diphenyl, the endcapping is carried out, for example, as follows:
Die Suspension aus 3g PoIy -N, N' -dodecylen-4, 4' -dipyridyl und 150ml n-Butylamin (Kp. 100-1040C) wird 2 Stunden unter Ruckfluss gekocht. Nach dem Absaugen wird das Material mit Ether gewaschen und im Trockenschrank getrocknet. Das hellgelbe Pulver wird zur Herstellung einer elektrochrom aktiven Formulierung verwendet.The suspension of 3 g of poly-N, N'-dodecylene-4, 4'-dipyridyl and 150 ml of n-butylamine (bp 100-104 0 C) is boiled under reflux for 2 hours. After suction, the material is washed with ether and dried in a drying oven. The light yellow powder is used to prepare an electrochromically active formulation.
Herstellung der elektrochrom aktiven Formulierung:Preparation of the electrochromic active formulation:
6g Titandioxid werden mit 0,6g durch Endcapping verbessertes PoIy -N, N' -dodecylen-4, 4' -dipyridyl aus der oben beschriebenen Herstellungsweise und 0,23g Ferrocen mittels eines Speed- Mixers vermischt. Die erhaltene Mischung wird, ebenfalls mit¬ tels eines Speed-Mixers, in 2,2g Diethylenglykol dispergiert.6 g of titanium dioxide are mixed with 0.6 g of endcapping-improved poly-N, N'-dodecylene-4,4'-dipyridyl from the preparation described above and 0.23 g of ferrocene using a speed mixer. The resulting mixture is, likewise with ¬ means of a speed mixer, dispersed in 2.2 g of diethylene glycol.
Herstellung einer elektrochrom aktiven Zelle:Preparation of an electrochromically active cell:
Die erhaltene weiße Formulierung wird mittels der Rakeltech¬ nik auf eine untere Elektrodenschicht auf einem Substrat, beispielsweise eine ITO-beschichtete PET-Folie appliziert, wobei ein Kleberahmen als Begrenzung der elektrochrom aktiven Flache dient. Der Kleberahmen dient auch zur Verklebung mit der oberen Elektrodenschicht, beispielsweise mit einer zweiten ITO-beschichteten Folie als Gegenelektrode. Beim Beschälten der Zelle wird an der Kathode ein blauer Farbeindruck er- halten. Lebensdauermessung:The resulting white formulation is applied by means of the Rakeltech ¬ technology to a lower electrode layer on a substrate, such as an ITO-coated PET film, with an adhesive frame serves as a boundary of the electrochromic active area. The adhesive frame is also used for bonding to the upper electrode layer, for example with a second ITO-coated film as a counter electrode. When charging the cell, a blue color impression is obtained at the cathode. Lifetime measurement:
Die Lebensdauermessung wird bei einer Temperatur von 85°C durchgeführt. Die Lebensdauer betragt 3219 Stunden und liegt damit 749 Stunden oder ca. 30% hoher als die Lebensdauer einer Zelle mit nicht behandeltem PoIy -N, N' -dodecylen-4, 4' - dipyπdyl. Die Lebensdauer ist dabei als der Abfall des anfänglichen Kontrasts auf 20% definiert.The lifetime measurement is carried out at a temperature of 85 ° C. The lifetime is 3219 hours, which is 749 hours or about 30% higher than the lifetime of a cell with untreated poly-N, N'-dodecylene-4,4'-diphenyl. The lifetime is defined as the decrease of the initial contrast to 20%.
Die Einfuhrung von inerten Endgruppen geht einher mit der Eliminierung der vorhandenen reaktiven Endgruppen wie beispielsweise restlicher kovalent gebundener Brom-Endgruppen, die aufgrund der Synthese vorhanden sind. Die Eliminierung erfolgt mit geeigneten Reagenzien, die je nach zu eliminie- render Endgruppe variieren und sich dem Fachmann leicht erschließen. Der Gehalt der Endgruppen variiert, so dass er nicht reproduzierbar festgestellt werden kann. Man rechnet daher mit einem vom jeweiligen Batch abhangigen Brom-Gehalt des Bipyπdylderivates .The introduction of inert end groups is accompanied by the elimination of the existing reactive end groups such as residual covalently bound bromine end groups which are present due to the synthesis. The elimination takes place with suitable reagents, which vary depending on the end group to be eliminated and which are readily apparent to the person skilled in the art. The content of the end groups varies, so that it can not be determined reproducibly. It is therefore expected that the bromine content of the bipyridyl derivative depends on the particular batch.
Das kovalent gebundene Brom am unbehandelten PoIy -N, N'- dodecylen-4, 4' -dipyπdyl beispielsweise kann insbesondere bei erhöhter Temperatur im elektrochromen Bauteil in Folgere¬ aktionen abgespalten werden und damit, bei fehlendem Endcap- ping die Elektrode angreifen, wodurch die weitere elektrische Beschaltung des Bauteils unterbunden wird. In Folge dieses Effektes wird die Lebensdauer einer elektrochrom aktiven Zel¬ le begrenzt. Im Falle der Materialverbesserung durch das End- capping des 4, 4' Bipyπdiniumsalzes wird die Lebensdauer des Bauteils beispielsweise um etwa 30% erhöht. The covalently bound bromine on untreated poly-N, N'-dodecylene-4, 4 '-dipyπdyl for example, may in particular at elevated temperature in the electrochromic device in Deduce ¬ actions are cleaved, and thus, in the absence of the electrode Endcap- ping attack, whereby the further electrical wiring of the component is prevented. As a result of this effect, the life of an electrochromic active Zel ¬ le is limited. In the case of material improvement by the end capping of the 4, 4 'bipyridinium salt, the life of the component is increased, for example, by about 30%.

Claims

Patentansprüche claims
1. Elektrochrom aktiver Farbstoff auf Basis 4,4'- Bipyπdiniumsalze, wobei zumindest eine reaktive Endgruppe des 4, 4' Bipyπdiniumsalzes durch eine inerte Endgruppe ersetzt oder geschützt ist.1. electrochromic active dye based on 4,4'- Bipyπdiniumsalze, wherein at least one reactive end group of the 4, 4 'Bipyπdiniumsalzes replaced by an inert end group or protected.
2. Elektrochrom aktiver Farbstoff nach Anspruch 1, der als inerte Endgruppe eine Alkoxygruppe und/oder eine N- substituierte Alkyl- oder Arylgruppe umfasst.2. Electrochromically active dye according to claim 1, which comprises as inert end group an alkoxy group and / or an N-substituted alkyl or aryl group.
3. Formulierung, die neben dem Farbstoff nach einem der Ansprüche 1 oder 2 ein Weißpigment und/oder ein Metallocen als Stabilisator umfasst.3. Formulation which comprises, in addition to the dye according to one of claims 1 or 2, a white pigment and / or a metallocene as stabilizer.
4. Elektrochromes organisches Bauteil, das eine elektrochrom aktive Formulierung nach einem der Ansprüche 1 bis 4 enthalt. 4. Electrochromic organic component containing an electrochromic active formulation according to any one of claims 1 to 4.
EP09783362A 2008-09-30 2009-09-24 Electrochromic formulation, method for the production thereof, and electrochromic organic component Withdrawn EP2334715A1 (en)

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DE102008049546A DE102008049546A1 (en) 2008-09-30 2008-09-30 Electrochromic formulation, method of preparation and electrochromic organic device
PCT/EP2009/062370 WO2010037682A1 (en) 2008-09-30 2009-09-24 Electrochromic formulation, method for the production thereof, and electrochromic organic component

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DE102008049546A1 (en) 2008-09-30 2010-04-08 Siemens Aktiengesellschaft Electrochromic formulation, method of preparation and electrochromic organic device
DE102008049543A1 (en) * 2008-09-30 2010-04-01 Siemens Aktiengesellschaft Electrochromic formulation and electrochromic organic device

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