WO2006128806A2 - Matiere pour couches electrochromes - Google Patents

Matiere pour couches electrochromes Download PDF

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Publication number
WO2006128806A2
WO2006128806A2 PCT/EP2006/062531 EP2006062531W WO2006128806A2 WO 2006128806 A2 WO2006128806 A2 WO 2006128806A2 EP 2006062531 W EP2006062531 W EP 2006062531W WO 2006128806 A2 WO2006128806 A2 WO 2006128806A2
Authority
WO
WIPO (PCT)
Prior art keywords
clo
unbranched
branched
betaine
alkyl
Prior art date
Application number
PCT/EP2006/062531
Other languages
German (de)
English (en)
Other versions
WO2006128806A3 (fr
Inventor
Andreas Kanitz
Wolfgang Roth
Maria Sramek
Original Assignee
Siemens Aktiengesellschaft
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Siemens Aktiengesellschaft filed Critical Siemens Aktiengesellschaft
Publication of WO2006128806A2 publication Critical patent/WO2006128806A2/fr
Publication of WO2006128806A3 publication Critical patent/WO2006128806A3/fr

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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
    • G02F1/1514—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

Definitions

  • the invention relates to a material for electrochromic layers based on a pH-activated color change.
  • 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 pH-active 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, which has an effect on the pH.
  • a voltage is applied to the material, 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 the pH value is then converted into a color change of the material and the application of the voltage is made visible.
  • a pasty formulation which represents the electrochromic system, is located between the electrodes.
  • the composition of this electrochromic system comprises as essential constituents a polymer as a solid electrolyte, a conducting salt, a redox system, TiO 2 as a white pigment, a solvent and a dye. This is usually a pH indicator.
  • the object of the present invention is therefore to provide a material for a formulation of an electrochromic active layer in an organic electronic component, such as in a display, which has an improved performance over the prior art, wherein the component in the electrochromic material, the Functionality of the chromophore and / or the conducting salt has been so bound in the material that it neither diffuses nor precipitates to the edges.
  • the object of the invention and solution of the problem is a material for a formulation of an electrochromic active layer of an electronic component, comprising a polymeric solid electrolyte, a conductive salt, a redox system, a white pigment, a solvent and a dye, characterized in that the functionalities
  • Conducting salt together present as a component in the formulation.
  • the functionalities of solid polymer electrolyte, chromophore and conducting salt in one component, ie in a chemical compound, the number of components of the formulation is reduced, thus improving the long-term stability of the formulation and the life of the display. Since the chromophore and the conducting salt are polymer-bound, diffusion, aggregation and / or precipitation of these functionalities can no longer take place. As a result, color changes remain permanently bound to the active pixel surface. This allows edge-to-edge mapping of pixels for improved image reproduction and improved lifetime. According to an advantageous embodiment of the invention is used as a component with the functionalities
  • Organic dye betaines are deprotonatable methine dye betaines, they fulfill the functions as dye or electrochromium and as conducting salt and are equipped at least with a further function for chemical attachment to a polymeric matrix.
  • organic dye betaine of the following type is used:
  • R 1 can be H, alkyl (branched or unbranched Cl to ClO) or aryl (preferably phenyl),
  • R and R independently of one another are alkyl (branched or unbranched Cl to ClO), aryl (preferably phenyl), an alkylene structure bridged with Y 1 and / or Y 2 [(CH 2 ) 3 , (CH 2 ) 4 or
  • R 3 and R 3 * independently of one another are H, alkyl (branched or unbranched Cl to ClO), aryl (preferably phenyl) or both are connected via an oxygen atom or sulfur atom,
  • An ⁇ stands for any anion which is bonded either via an alkyl spacer having the substituents R 1 or R 2 or R 2 * or R 3 or R 3 * or by direct substitution with an aromatic structural element of the methine dye that a salt-like methine dye betaine is formed, these are preferably a CO-Alkylsulfonatgrupptechnik (branched or unbranched Cl to ClO) or a ⁇ -Alkylcarbonklad grouping (branched or unbranched Cl to ClO).
  • substituents R n or a substituent on any aromatic structural element of the methine dye is designed as a structural element for chemical attachment to a polymeric matrix, this can be a hydroxy function, an organic or be organic acid function or optionally also an amine function.
  • chromophores For the chemical attachment of the chromophores to polymeric matrices they must also have corresponding chemical functions that can react with the available functional groups of the chromophores.
  • a wide range of functional groups is available, which, combined appropriately, can be reacted with methods that are generally known in synthetic chemistry. These are z.
  • esterification, etherification or amidation In the first case, a carboxy group and an alcoholic OH group react with each other.
  • Each of these functional groups can be located either in the chromophore, the corresponding other group in the polymer.
  • etherification both the chromophore and the polymer carry a hydroxyl group which may be attached aromatically and / or aliphatically.
  • amidization a carboxy group and an amino group react with each other.
  • Betaines are characterized by the presence of both a cationic and an anionic charge center.
  • an organic betaine chromophore that is, a zwitterion, makes it possible to dispense with the addition of the conductive salt, since the electroactive chromophore itself can take over the function of the conducting salt.
  • chromophore and conducting salt are basically in the immediate vicinity, thus facilitating the diffusion of lead salt (ion diffusion and demixing effect) in the electric field severely restricted, if not avoided.
  • a basic structural element such as an amino group and an acidic structural element such as a carboxy group or sulfonic acid group will simultaneously be present in the material.
  • the methine dye betaines suitable for the material must be condensed from previously synthesized and appropriately substituted synthons.
  • the exemplary embodiment describes the preparation of a betaine chromophore via various synthons having an OH function and the chemical attachment to a polyimide suitable for the application by etherification.
  • the paste-like formulation obtained is applied according to the prior art in the case of a display between intersecting electrodes. When a voltage is applied, a color change from blue to red is achieved.
  • the material of the invention combines the functionalities - polymeric solid electrolyte, - chromophore and - conducting salt in a single chemical component.
  • a number of disadvantages are overcome, such as the diffusion of the chromophore to the pixel edges and the aggregation of the conducting salt, which can ultimately lead to corrosion of the electrodes and the entire failure of the display.
  • the invention relates to a material for electrochromic layers based on a pH-activated color change.
  • the material is part of a formulation which, when applied to an organic electronic device such as a display, exhibits a reversible color change upon application of a voltage.
  • the lifetime of such formulations is considerably increased with the polymeric betaine chromophore used according to the invention.

Landscapes

  • Physics & Mathematics (AREA)
  • Nonlinear Science (AREA)
  • Chemical & Material Sciences (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

Matière pour couches électrochromes à base d'un changement de couleur activé par pH. Ladite matière est un constituant d'une composition qui, lorsqu'elle est appliquée sur un composant électronique organique tel qu'un afficheur, présente un changement de couleur réversible en cas d'application d'une tension. La durée de vie de compositions de ce type est considérablement augmentée avec l'utilisation selon la présente invention du chromophore bétaïne.
PCT/EP2006/062531 2005-05-31 2006-05-23 Matiere pour couches electrochromes WO2006128806A2 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
DE102005024960.4 2005-05-31
DE102005024960 2005-05-31
DE102005031634.4 2005-07-06
DE102005031634 2005-07-06

Publications (2)

Publication Number Publication Date
WO2006128806A2 true WO2006128806A2 (fr) 2006-12-07
WO2006128806A3 WO2006128806A3 (fr) 2007-02-22

Family

ID=37113034

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2006/062531 WO2006128806A2 (fr) 2005-05-31 2006-05-23 Matiere pour couches electrochromes

Country Status (1)

Country Link
WO (1) WO2006128806A2 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008037643A1 (fr) * 2006-09-26 2008-04-03 Siemens Aktiengesellschaft Formulation électrochrome, procédé de préparation de celle-ci et élément structural organique électrochrome

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS62186231A (ja) * 1986-02-12 1987-08-14 Toyo Soda Mfg Co Ltd エレクトロクロミツク表示材料
WO2001027690A2 (fr) * 1999-10-11 2001-04-19 University College Dublin Dispositif electrochromique
WO2002075441A2 (fr) * 2001-03-19 2002-09-26 Dow Global Technologies Inc. Dispositif d'affichage electrochromique et compositions utilisees pour fabriquer de tels dispositifs

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS62186231A (ja) * 1986-02-12 1987-08-14 Toyo Soda Mfg Co Ltd エレクトロクロミツク表示材料
WO2001027690A2 (fr) * 1999-10-11 2001-04-19 University College Dublin Dispositif electrochromique
US6870657B1 (en) * 1999-10-11 2005-03-22 University College Dublin Electrochromic device
WO2002075441A2 (fr) * 2001-03-19 2002-09-26 Dow Global Technologies Inc. Dispositif d'affichage electrochromique et compositions utilisees pour fabriquer de tels dispositifs

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
HWANG S H ET AL: "Absorption Spectra and Electrophotographic Properties of Squarylium Dyes Containing a Nitro group" DYES AND PIGMENTS, ELSEVIER APPLIED SCIENCE PUBLISHERS. BARKING, GB, Bd. 39, Nr. 4, 1. Dezember 1998 (1998-12-01), Seiten 359-369, XP004144765 ISSN: 0143-7208 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008037643A1 (fr) * 2006-09-26 2008-04-03 Siemens Aktiengesellschaft Formulation électrochrome, procédé de préparation de celle-ci et élément structural organique électrochrome

Also Published As

Publication number Publication date
WO2006128806A3 (fr) 2007-02-22

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