WO2008037643A1 - Formulation électrochrome, procédé de préparation de celle-ci et élément structural organique électrochrome - Google Patents

Formulation électrochrome, procédé de préparation de celle-ci et élément structural organique électrochrome Download PDF

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Publication number
WO2008037643A1
WO2008037643A1 PCT/EP2007/059931 EP2007059931W WO2008037643A1 WO 2008037643 A1 WO2008037643 A1 WO 2008037643A1 EP 2007059931 W EP2007059931 W EP 2007059931W WO 2008037643 A1 WO2008037643 A1 WO 2008037643A1
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WO
WIPO (PCT)
Prior art keywords
electrochromic
formulation
formulation according
zwitterionic
acid
Prior art date
Application number
PCT/EP2007/059931
Other languages
German (de)
English (en)
Inventor
Andreas Kanitz
Wolfgang Roth
Roland Wagner
Julia Wirsing
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 WO2008037643A1 publication Critical patent/WO2008037643A1/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
    • 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
    • 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
    • G02F2001/1502—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 complementary cell
    • 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
    • G02F2001/15145—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 the electrochromic layer comprises a mixture of anodic and cathodic 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 status indicators whose switched state remains as long as possible without current.
  • These electrochromic organic based formulations are characterized by a high bistability.
  • Electrochromic displays based on organic materials to take ⁇ normally an active electrochromic layer, which is in the case of a display between the electrodes arranged perpendicular to each other.
  • Essential components of the active layer are a redox system and a pH-active dye.
  • the concent ⁇ rations collapse the redox partner is shifted from each other in the material.
  • 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 at ⁇ , then the displacement of the equilibrium of the redox partners of the two electrodes run in the opposite direction overall translated. This means that at an electric ⁇ de pH increases, while it decreases at 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 comprising as essential constituents loading a polymer as a solid electrolyte, a supporting electrolyte, a redox system, TiO2 as a white pigment, a solvent and ei ⁇ NEN dye.
  • This is usually a pH indicator.
  • Another principle to realize electrochromic displays is not to cause the color change by changing 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. Examples in the literature for this are disclosed in MOM Edwards, Appl. Phys. Lett. 2005, 86 (7) and
  • electrochromic active formulations are sought, which change the color state rapidly when a voltage is applied, and quickly return to the ground state in the de-energized state. This behavior is desirable for displays.
  • status displays eg. B. on / off, it is advantageous to have formulations that remain after reaching the switched state without further tension long in this state.
  • the object of the present disclosure was the development of electrochromically active formulations which remain in the de-energized state for a long time in the switched state, ie electrochromically active formulations with high bistability.
  • the object of the invention and solution of the problem is an electrochromic formulation comprising a zwitterionic component.
  • the electrochromic active component itself is a zwitterion.
  • a zwitterionic compound is included in the formulation.
  • the electrochromic active component is a polymeric Bipyridini- um derivative, as it is known for example from DE 10 2005 032 316.
  • Additives with at least one of these functional groups can be used in a wide concentration range, but preferably in a stoichiometric ratio, based on the electrochromically active component.
  • the functional group may also be present in the electrochromically active component.
  • the character of the bipolarity of the additive can be varied by Substi ⁇ tution on one or both N atoms.
  • a formulation according to the invention contains an electrochromically active component, for.
  • a 4,4'-bipyridinium derivative eg a polymeric 4,4'-bipyridinium salt such as the poly (dodecyl-4,4'-bipyridinium) dibromide, and e.g. B. urea.
  • This ⁇ For formulation is due to its bistability particularly for display Elements that are to indicate the state of a system ge ⁇ suitable. Since it remains long in the currentless state in the switched color state indicators with particularly ge ⁇ ringem power consumption can be realized. To maintain a sufficient color contrast of a entspre ⁇ sponding temporal sequence of voltage pulses is sufficient.
  • 6g TiC> 2 were mixed with 0.6g of a polymer 4, 4 '-Bipyridinium- derivative (poly (dodecyl-4, 4' -bipyridinium dibromide)) and with 2g Diethylengklykol by means of a Speed Mixer intensively mixed with one another ⁇ .
  • a white paste is obtained.
  • a layer with a thickness of 50 ⁇ m is produced by means of the doctor blade technique between two ITO-coated films.
  • a voltage of 1.5 V is applied for 10 s, a blue color impression is produced at the cathode, which is defined as a 100% contrast to the initial state, and which drops to 20% of the initial contrast in the unconnected state within about 30 seconds. The discoloration is therefore visible to the viewer of the display in the unconnected state for 30 seconds under the given wiring conditions.
  • the invention relates to formulations and their use in organically based electrochromic components, for example for the production of status displays whose switched
  • electrochromic organic based formulations are characterized by a high bistability.
  • the wording ments contain at least one component which contains a zwitterionic ⁇ structural element.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Chemistry (AREA)
  • Electrochromic Elements, Electrophoresis, Or Variable Reflection Or Absorption Elements (AREA)

Abstract

L'invention concerne des formulations et leur utilisation dans des composants structuraux électrochromes à base organique, par exemple pour la fabrication d'indicateurs d'état, dont l'état commuté reste maintenu le plus longtemps possible également en absence de courant. Ces formulations électrochromes à base organique se caractérisent par une bistabilité élevée. Les formulations contiennent au moins un composant contenant un élément structural zwitterionique.
PCT/EP2007/059931 2006-09-26 2007-09-20 Formulation électrochrome, procédé de préparation de celle-ci et élément structural organique électrochrome WO2008037643A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102006045307A DE102006045307A1 (de) 2006-09-26 2006-09-26 Elektrochrome Formulierung, Herstellungsverfahren dazu und elektrochromes organisches Bauelement
DE102006045307.7 2006-09-26

Publications (1)

Publication Number Publication Date
WO2008037643A1 true WO2008037643A1 (fr) 2008-04-03

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PCT/EP2007/059931 WO2008037643A1 (fr) 2006-09-26 2007-09-20 Formulation électrochrome, procédé de préparation de celle-ci et élément structural organique électrochrome

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DE (1) DE102006045307A1 (fr)
WO (1) WO2008037643A1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009141302A1 (fr) * 2008-05-20 2009-11-26 Siemens Aktiengesellschaft Formulation électrochrome et composant électronique organique à commutation électrochrome
WO2009141303A1 (fr) * 2008-05-19 2009-11-26 Siemens Aktiengesellschaft Formulation électrochrome comportant au moins deux systèmes de couleur, procédé de fabrication associé et composant électrochrome
US8115984B2 (en) 2007-06-18 2012-02-14 Ajjer Llc Laminated electrochromic devices and processes for forming the same

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102008024259A1 (de) 2008-05-20 2009-12-31 Siemens Aktiengesellschaft Elektrochrome Formulierung und Verfahren zur Herstellung einer elektrochromen Formulierung; Verwendung der Formulierung und organisches elektronisches elektrochromes Bauteil
DE102009023309A1 (de) 2009-05-29 2010-12-16 Siemens Aktiengesellschaft Elektrochrome Formulierung, Herstellungsverfahren dazu und elektrochromes organisches Bauelement
DE102009023303A1 (de) 2009-05-29 2010-12-09 Siemens Aktiengesellschaft Elektrochrome Formulierung, Herstellungsverfahren dazu und elektrochromes organisches Bauelement

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1989008686A1 (fr) * 1988-03-12 1989-09-21 MERCK Patent Gesellschaft mit beschränkter Haftung Chromophores nlo zwitterioniques
WO1995007275A1 (fr) * 1993-09-10 1995-03-16 Ciba-Geigy Ag Composes photochromiques, procede et produits intermediaires pour leur production, et leur utilisation
WO2002000662A1 (fr) * 2000-06-26 2002-01-03 Catalyst Biomedica Limited Ameliorations de chromophores et relatives auxdits chromophores
WO2002075441A2 (fr) * 2001-03-19 2002-09-26 Dow Global Technologies Inc. Dispositif d'affichage electrochromique et compositions utilisees pour fabriquer de tels dispositifs
WO2006128806A2 (fr) * 2005-05-31 2006-12-07 Siemens Aktiengesellschaft Matiere pour couches electrochromes

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5643623A (en) * 1979-09-18 1981-04-22 Sharp Corp Electrochromic display device
JPH11183942A (ja) * 1997-12-19 1999-07-09 Nippon Mitsubishi Oil Corp エレクトロクロミック素子
DE19825371A1 (de) * 1998-06-06 1999-12-09 Bayer Ag Elektrochrome Anzeigevorrichtung mit isolierten Zuleitungen
WO2006128818A1 (fr) * 2005-05-31 2006-12-07 Siemens Aktiengesellschaft Matiere destinee a une formulation electrochrome, son utilisation et dispositif d'affichage

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1989008686A1 (fr) * 1988-03-12 1989-09-21 MERCK Patent Gesellschaft mit beschränkter Haftung Chromophores nlo zwitterioniques
WO1995007275A1 (fr) * 1993-09-10 1995-03-16 Ciba-Geigy Ag Composes photochromiques, procede et produits intermediaires pour leur production, et leur utilisation
WO2002000662A1 (fr) * 2000-06-26 2002-01-03 Catalyst Biomedica Limited Ameliorations de chromophores et relatives auxdits chromophores
WO2002075441A2 (fr) * 2001-03-19 2002-09-26 Dow Global Technologies Inc. Dispositif d'affichage electrochromique et compositions utilisees pour fabriquer de tels dispositifs
WO2006128806A2 (fr) * 2005-05-31 2006-12-07 Siemens Aktiengesellschaft Matiere pour couches electrochromes

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8115984B2 (en) 2007-06-18 2012-02-14 Ajjer Llc Laminated electrochromic devices and processes for forming the same
WO2009141303A1 (fr) * 2008-05-19 2009-11-26 Siemens Aktiengesellschaft Formulation électrochrome comportant au moins deux systèmes de couleur, procédé de fabrication associé et composant électrochrome
WO2009141302A1 (fr) * 2008-05-20 2009-11-26 Siemens Aktiengesellschaft Formulation électrochrome et composant électronique organique à commutation électrochrome
US8300296B2 (en) 2008-05-20 2012-10-30 Siemens Aktiengesellschaft Electrochromic formulation and organic electrochromic switchable electronic component

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Publication number Publication date
DE102006045307A1 (de) 2008-04-03

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