WO2006128807A2 - Materiau destine a des couches electrochromes - Google Patents

Materiau destine a des couches electrochromes Download PDF

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Publication number
WO2006128807A2
WO2006128807A2 PCT/EP2006/062534 EP2006062534W WO2006128807A2 WO 2006128807 A2 WO2006128807 A2 WO 2006128807A2 EP 2006062534 W EP2006062534 W EP 2006062534W WO 2006128807 A2 WO2006128807 A2 WO 2006128807A2
Authority
WO
WIPO (PCT)
Prior art keywords
clo
unbranched
branched
betaine
aryl
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.)
Ceased
Application number
PCT/EP2006/062534
Other languages
German (de)
English (en)
Other versions
WO2006128807A3 (fr
Inventor
Andreas Kanitz
Wolfgang Roth
Maria Sramek
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Siemens AG
Siemens Corp
Original Assignee
Siemens AG
Siemens Corp
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 AG, Siemens Corp filed Critical Siemens AG
Publication of WO2006128807A2 publication Critical patent/WO2006128807A2/fr
Publication of WO2006128807A3 publication Critical patent/WO2006128807A3/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

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
    • 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.
  • a disadvantage of this material is the use of the conductive salt, which is usually inorganic conductive salt, eg NaCl, Na 2 SÜ 4 or more organic tetraalkylammonium salts with anions such as BF 4 " or PF 6 " , has only limited solubility in the components used for the formulation, such as the polymer component and its solvent, so that aggregation of the conductive salt and / or failure of the conductive salt may occur. This limits the function of the conducting salt in the electrochromic cell. The life of an electrochromic electronic device is largely determined by the function of the conductive salt, because the usable switching cycles can only be realized if the material is still fully functional. Among other things, the aggregation of the conductive salt causes the display to fail.
  • the conductive salt which is usually inorganic conductive salt, eg NaCl, Na 2 SÜ 4 or more organic tetraalkylammonium salts with anions such as BF 4 " or PF 6 " , has only limited
  • 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 extended life compared to the prior art, wherein the component in the electrochromic material, the Conducting salt functionality that is so bound or soluble in the material that it neither aggregates nor precipitates.
  • 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 at least one polymeric solid electrolyte, a redox system, a white pigment and a solvent, wherein the functionality of the conductive salt in the salt-free material is.
  • Conducting salt functionality may be included in a betaine, for example.
  • a betaine is characterized by the presence of both a cationic and an anionic charge center in the molecule.
  • the use of an organic betaine, ie a zwitterion allows dispensing with the addition of conductive salt, since the electroactive material itself can take over the function of the conducting salt via the betaine function. Not only can this reduce the number of components in the formulation material but also provide improved formulation stability and improved display life become. This is due to the fact that "chromophore and conductive salt” are basically in the immediate vicinity, which severely restricts, if not avoids, the electrolyte salt aggregation (ion diffusion and segregation effects) in the electric field.
  • 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.
  • organic dye betaines particularly preferably deprotonatable methine dye betaines of the following type are used:
  • the color change in this system is from methine dye betaine to merocyanine.
  • R 3 and R 3 * independently of one another are H, alkyl (branched or unbranched Cl to ClO), aryl (preferably phenyl) or both are bonded via an oxygen atom or sulfur atom,
  • Alkylenspacer (branched or unbranched Cl to ClO) with the substituents R 1 or R 2 or R 2 * or R 3 or R 3 * or by direct substitution on an aromatic structural element of the methine dye is bonded, so that a salt-like methine dye -Betaine is formed, these are preferably ne ⁇ -Alkylsulfonatgrupptechnik (branched or unbranched Cl to ClO) or an ⁇ -alkylcarboxylic acid grouping (branched or unbranched Cl to ClO).
  • the methine dye betaines suitable for the material must be condensed from previously synthesized and appropriately substituted synthons.
  • the following components are mixed in the amount indicated: TiC> 2 (Ig), polyethylene oxide (Ig), durohydroquinone (0.028 g), duroquinone (0.018 g), propylene carbonate (3 ml) and the prepared betaine Chromophore (0.06g). All ingredients are mixed thoroughly after mixing together using a speed mixer.
  • 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 is observed. With the formulation, a 3 times higher number of switching cycles can be achieved than with known systems.
  • the material according to the invention avoids the addition of a conducting salt to an electrochromic material, so that a display based on organic materials without conducting salt can be formed, whereby a lot of critical points such as corrosion of the electrodes, aggregation of the conducting salt and more solvable.
  • 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 betaine chromophore used according to the invention.

Landscapes

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

Abstract

L'invention concerne un matériau destiné à des couches électrochromes à base d'un virage de couleur activé par pH. Ledit matériau fait partie d'une formulation qui, lorsqu'elle est introduite dans un composant électronique organique tel qu'un écran, est caractérisée par un virage de couleur réversible en cas d'application d'une tension. La durée de vie de telles formulations est augmentée considérablement sous l'effet du chromophore de bétaïne employé selon l'invention.
PCT/EP2006/062534 2005-05-31 2006-05-23 Materiau destine a des couches electrochromes Ceased WO2006128807A2 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
DE102005024946.9 2005-05-31
DE102005024946 2005-05-31
DE102005031633.6 2005-07-06
DE102005031633 2005-07-06

Publications (2)

Publication Number Publication Date
WO2006128807A2 true WO2006128807A2 (fr) 2006-12-07
WO2006128807A3 WO2006128807A3 (fr) 2007-01-18

Family

ID=37067565

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2006/062534 Ceased WO2006128807A2 (fr) 2005-05-31 2006-05-23 Materiau destine a des couches electrochromes

Country Status (1)

Country Link
WO (1) WO2006128807A2 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110292536A (zh) * 2019-06-25 2019-10-01 许雅婷 电致变色的角蛋白纤维染色方法及装置

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6188224A (ja) * 1984-10-08 1986-05-06 Canon Inc 表示素子
JPH0654394B2 (ja) * 1986-11-14 1994-07-20 富士写真フイルム株式会社 光導電性組成物
DE10001031A1 (de) * 2000-01-13 2001-07-19 Bayer Ag Elektrochrome Vorrichtung
WO2002075442A1 (fr) * 2001-03-19 2002-09-26 Dow Global Technologies Inc. Dispositif d'affichage electrochromique a adressage matriciel

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110292536A (zh) * 2019-06-25 2019-10-01 许雅婷 电致变色的角蛋白纤维染色方法及装置
CN110292536B (zh) * 2019-06-25 2022-07-08 许雅婷 一种电致变色的角蛋白纤维染色方法及装置

Also Published As

Publication number Publication date
WO2006128807A3 (fr) 2007-01-18

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