WO2008142047A1 - Composant électrochrome organique destiné à des affichages permanents - Google Patents

Composant électrochrome organique destiné à des affichages permanents Download PDF

Info

Publication number
WO2008142047A1
WO2008142047A1 PCT/EP2008/056111 EP2008056111W WO2008142047A1 WO 2008142047 A1 WO2008142047 A1 WO 2008142047A1 EP 2008056111 W EP2008056111 W EP 2008056111W WO 2008142047 A1 WO2008142047 A1 WO 2008142047A1
Authority
WO
WIPO (PCT)
Prior art keywords
dye
organic electrochromic
electrochromic device
dyes
complementary
Prior art date
Application number
PCT/EP2008/056111
Other languages
German (de)
English (en)
Inventor
Andreas Kanitz
Wolfgang Roth
Roland Wagner
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
Priority to EP08759737A priority Critical patent/EP2150598A1/fr
Publication of WO2008142047A1 publication Critical patent/WO2008142047A1/fr

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
    • 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
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1007—Non-condensed systems
    • 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
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1011—Condensed systems
    • 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
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
    • 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
    • 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
    • C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
    • 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
    • C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom

Definitions

  • the invention relates to an organic electrochromic device for permanent displays.
  • Organic electrochromic elements are known, for example, from EP 1636641. These components are used, for example, for displays which typically change between two color states.
  • Electrochromic displays based on organic materials normally consist of a layer of special composition, which is located between electrodes arranged perpendicular to one another.
  • Essential constituents of the active layer can be, for example, a redox system and a pH-active dye.
  • a voltage is applied, the shift in the equilibrium of the redox partners at both electrodes runs in the opposite direction. This leads to a pH increase at the one electrode while it sinks at the counter electrode. Via a pH dye, the change in pH is then converted into a color change.
  • a paste-like formulation which represents the electrochromic system is located between the electrodes.
  • the composition of this electrochromic system then consists inter alia of a polymer as a solid electrolyte, a conductive salt, a redox system, TiO 2 as a white pigment, a solvent and a dye. This is usually a pH indicator.
  • formulations may contain redox-active dyes, e.g. B based on oligomeric bipyridinium salts, as known from PCT / EP2006 / 064048.
  • a formulation containing an electrochromically active dye can be reversibly switched between two color states.
  • a display change typically wise between two color states.
  • an oligomeric bipyridinium salt is used as the electrochromically active component, the color impression in the anodic switching state is colorless or white because of the white pigment; after reduction at the cathode, the color impression is blue.
  • the color change on the side facing the viewer is achieved by reversing the polarity of the electrodes.
  • the wiring of the display is thus in AC or in AC mode.
  • the object of the invention is therefore to provide an organic electrochromic device, which is suitable as a permanent display.
  • Solution to the object and subject of the invention is an organic electrochromic device having an organic electrochromic active formulation between two electrodes, wherein the electrochromically active formulation comprises a cathodic and an anodically switchable dye, which form a complementary dye pair and the organic electrochromic device is operated with alternating current (AC mode).
  • AC mode alternating current
  • the problem is solved by the fact that the electrochromically active formulation contains a dye pair which is complementary to the redox behavior.
  • the two dyes which are selected as the dye pair, produce in the AC circuit a color impression which sets by mixing both absorption spectra of the dyes.
  • Complementary means that the color impression of the dye 1 is due to reduction, the color impression of the dye 2 due to oxidation.
  • Dye 1 goes to the cathode z. B. of colorless or white in a blue color over and dye 2 at the anode also of colorless or white in a blue color impression.
  • the electrochromic display element according to the invention is operated in the AC mode, a long-life display element can be realized because the above-mentioned disadvantages of the DC mode for electrochromic devices are avoided.
  • any resulting color impression can be produced.
  • An example of a complementary redox couple that produces a blue color impression is an oligomeric bipyridinium salt and a 1, 1 ' ditolyl-6, 6 ' -bis-1, 2, 3, 4-tetrahydrobenzo [h] - quinoline. (Described as an exemplary embodiment).
  • An example of a complementary redox couple that produces a green color impression is an anodically switching 2, 2, 2 ' , 2 ' tetra- [2- (phenyl-1-naphthylamino) -3-phenylthienyl] -4, 4-divinylidenebiphenyl of the following structure:
  • Dye 1 and Dye 2 are used in equimolar amounts. Both dyes are intimately mixed with 6 g of TiC> 2 . This mixture is dispersed by means of a speed mixer in 2.5 g of diethylene glycol. The resulting paste-like formulation is applied between two films coated with ITO. When de-energized, the electrochromic cell shows a white color impression.
  • the wiring of the cell is done by applying a voltage with an alternating sign.
  • the switch-on process includes a potentiostatic pulse in the amount of the switching voltage over a period of T / 2 (T: period for a cycle). For the switch-off, the sign of the voltage pulse is changed.
  • T period for a cycle
  • This wiring has a blue color impression result.
  • the lifetime of the electrochromic cell is about 2000h. In comparison, a conventional EC cell in DC mode has a lifetime of less than 100 h.
  • the invention makes it possible for the first time to create an electrochromic organic-based display element for permanent displays.
  • the invention relates to an organic electrochromic device for permanent displays. Unlike conventional electrochromic devices designed for continuous display, this device operates in AC mode. In order nevertheless to ensure a uniform color impression, the component comprises two complementary switchable, but according to their color impression, the same dyes.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Chemistry (AREA)
  • Control Of Indicators Other Than Cathode Ray Tubes (AREA)
  • Electrochromic Elements, Electrophoresis, Or Variable Reflection Or Absorption Elements (AREA)

Abstract

L'invention concerne un composant électrochrome organique destiné à des affichages permanents. Contrairement aux composants électrochromes habituels conçus pour des affichages permanents, le composant selon l'invention fonctionne en mode alternatif (AC). Pour obtenir malgré tout un effet de couleur uniforme, le composant comporte deux colorants pouvant être commutés de façon complémentaire, présentant toutefois un effet de couleur identique.
PCT/EP2008/056111 2007-05-22 2008-05-19 Composant électrochrome organique destiné à des affichages permanents WO2008142047A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP08759737A EP2150598A1 (fr) 2007-05-22 2008-05-19 Composant électrochrome organique destiné à des affichages permanents

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102007023747.4 2007-05-22
DE200710023747 DE102007023747A1 (de) 2007-05-22 2007-05-22 Organisches elektrochromes Bauelement für Daueranzeigen

Publications (1)

Publication Number Publication Date
WO2008142047A1 true WO2008142047A1 (fr) 2008-11-27

Family

ID=39720317

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2008/056111 WO2008142047A1 (fr) 2007-05-22 2008-05-19 Composant électrochrome organique destiné à des affichages permanents

Country Status (3)

Country Link
EP (1) EP2150598A1 (fr)
DE (1) DE102007023747A1 (fr)
WO (1) WO2008142047A1 (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011024391A1 (fr) * 2009-08-25 2011-03-03 Canon Kabushiki Kaisha Composé hétérocyclique et dispositif électroluminescent organique l'utilisant
JP2011042600A (ja) * 2009-08-20 2011-03-03 Canon Inc 複素環化合物及びこれを用いた有機発光素子
KR20130042900A (ko) * 2011-10-19 2013-04-29 삼성디스플레이 주식회사 헤테로시클릭 화합물, 이를 포함하는 유기 발광 소자 및 평판 표시 장치
CN107429158A (zh) * 2015-03-13 2017-12-01 株式会社理光 电致变色化合物、电致变色组合物、电致变色元件和电致变色调光元件

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102009023303A1 (de) * 2009-05-29 2010-12-09 Siemens Aktiengesellschaft Elektrochrome Formulierung, Herstellungsverfahren dazu und elektrochromes organisches Bauelement
WO2016147543A1 (fr) * 2015-03-13 2016-09-22 Ricoh Company, Ltd. Composé électrochromique, composition électrochromique, élément électrochromique et élément d'obscurcissement électrochromique

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS53144360A (en) * 1977-05-20 1978-12-15 Matsushita Electric Ind Co Ltd Driving method of electrochromic display body
US5998617A (en) * 1997-04-02 1999-12-07 Gentex Corporation Electrochromic compounds
EP1116767A2 (fr) * 2000-01-13 2001-07-18 Bayer Aktiengesellschaft Dispositif électrochrome
EP1288275A2 (fr) * 2001-09-04 2003-03-05 Exon Science Inc. Solution électrochromique contenant un composé d'hydrazone et dispositif ainsi obtenu
US20060268385A1 (en) * 2005-01-28 2006-11-30 Guarr Thomas F Multi-cell electrochromic devices

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5457564A (en) * 1990-02-26 1995-10-10 Molecular Displays, Inc. Complementary surface confined polymer electrochromic materials, systems, and methods of fabrication therefor
AU2002252426B2 (en) 2001-03-19 2007-08-23 Aveso, Inc. Matrix addressable electrochromic display device
DE10328377A1 (de) 2003-06-24 2005-01-20 Siemens Ag Elektrochromes Anzeigesystem
EP1907446B1 (fr) 2005-07-11 2011-04-06 Siemens Aktiengesellschaft Structures de 4,4 -bipyridinium polymeres, formulations destinees a une couche electrochrome active et utilisation

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS53144360A (en) * 1977-05-20 1978-12-15 Matsushita Electric Ind Co Ltd Driving method of electrochromic display body
US5998617A (en) * 1997-04-02 1999-12-07 Gentex Corporation Electrochromic compounds
EP1116767A2 (fr) * 2000-01-13 2001-07-18 Bayer Aktiengesellschaft Dispositif électrochrome
EP1288275A2 (fr) * 2001-09-04 2003-03-05 Exon Science Inc. Solution électrochromique contenant un composé d'hydrazone et dispositif ainsi obtenu
US20060268385A1 (en) * 2005-01-28 2006-11-30 Guarr Thomas F Multi-cell electrochromic devices

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2011042600A (ja) * 2009-08-20 2011-03-03 Canon Inc 複素環化合物及びこれを用いた有機発光素子
WO2011024391A1 (fr) * 2009-08-25 2011-03-03 Canon Kabushiki Kaisha Composé hétérocyclique et dispositif électroluminescent organique l'utilisant
JP2011046616A (ja) * 2009-08-25 2011-03-10 Canon Inc 複素環化合物及びこれを用いた有機発光素子
US8877354B2 (en) 2009-08-25 2014-11-04 Canon Kabushiki Kaisha Heterocyclic compound and organic light-emitting device using the same
KR20130042900A (ko) * 2011-10-19 2013-04-29 삼성디스플레이 주식회사 헤테로시클릭 화합물, 이를 포함하는 유기 발광 소자 및 평판 표시 장치
KR101971198B1 (ko) 2011-10-19 2019-04-23 삼성디스플레이 주식회사 헤테로시클릭 화합물, 이를 포함하는 유기 발광 소자 및 평판 표시 장치
CN107429158A (zh) * 2015-03-13 2017-12-01 株式会社理光 电致变色化合物、电致变色组合物、电致变色元件和电致变色调光元件
CN107429158B (zh) * 2015-03-13 2020-11-27 株式会社理光 电致变色化合物、电致变色组合物、电致变色元件和电致变色调光元件
US10988684B2 (en) 2015-03-13 2021-04-27 Ricoh Company, Ltd. Electrochromic compound, electrochromic composition, electrochromic element, and electrochromic dimming element

Also Published As

Publication number Publication date
DE102007023747A1 (de) 2008-11-27
EP2150598A1 (fr) 2010-02-10

Similar Documents

Publication Publication Date Title
EP0917556B1 (fr) Dispositif d'indication electrochrome
DE60003773T2 (de) Elektrochromes medium mit konzentration verbesserter stabilität, verfahren zu seiner herstellung und seiner verwendung
WO2008142047A1 (fr) Composant électrochrome organique destiné à des affichages permanents
EP1907446B1 (fr) Structures de 4,4 -bipyridinium polymeres, formulations destinees a une couche electrochrome active et utilisation
EP2435530A1 (fr) Formulation électrochrome, procédé de préparation et composant organique électrochrome
EP2851745B1 (fr) Cellules électrochromes et leur utilisation
EP1103842B1 (fr) Dispositif électrochromique
EP2276821B1 (fr) Formulation électrochrome et composant électronique organique à commutation électrochrome
DE102006045307A1 (de) Elektrochrome Formulierung, Herstellungsverfahren dazu und elektrochromes organisches Bauelement
WO2010000615A1 (fr) Formulation électrochromique, son procédé de fabrication et composant organique électrochromique
EP2093270A1 (fr) Utilisation d'antioxydants destinés à juguler un déchargement spontané
DE102008024187B3 (de) Elektrochrome Formulierung mit zumindest zwei Farbsystemen, Verfahren zur Herstellung dazu und elektrochromes Bauteil
WO2006128818A1 (fr) Matiere destinee a une formulation electrochrome, son utilisation et dispositif d'affichage
EP2328993A1 (fr) Composant organique électrochrome
DE102008049546A1 (de) Elektrochrome Formulierung, Herstellungsverfahren dazu und elektrochromes organisches Bauelement
WO2007036561A2 (fr) Pates electrochromiques contenant de nouveaux colorants
EP2435531B1 (fr) Formulation électrochrome, procédé de préparation et composant organique électrochrome
DE102008024259A1 (de) Elektrochrome Formulierung und Verfahren zur Herstellung einer elektrochromen Formulierung; Verwendung der Formulierung und organisches elektronisches elektrochromes Bauteil
DE102008030836A1 (de) Elektrochrome Formulierung, Herstellungsverfahren dazu und elektrochromes organisches Bauelement
WO2006128806A2 (fr) Matiere pour couches electrochromes
WO2006128809A1 (fr) Materiau destine a des couches electrochromes
WO2008022988A2 (fr) Formule électrochrome et dispositif avec la formule électrochrome
WO2007107475A1 (fr) Produit intermédiaire pour la préparation d'une composition à activité électrochrome, composition à activité électrochrome obtenue et utilisations de ladite composition
DE3125758A1 (de) Fluessigkristallanzeige
DE3243664A1 (de) Fluessigkristallanzeige

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 08759737

Country of ref document: EP

Kind code of ref document: A1

WWE Wipo information: entry into national phase

Ref document number: 2008759737

Country of ref document: EP

NENP Non-entry into the national phase

Ref country code: DE