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WO2007036561A2 - Pates electrochromiques contenant de nouveaux colorants - Google Patents

Pates electrochromiques contenant de nouveaux colorants Download PDF

Info

Publication number
WO2007036561A2
WO2007036561A2 PCT/EP2006/066877 EP2006066877W WO2007036561A2 WO 2007036561 A2 WO2007036561 A2 WO 2007036561A2 EP 2006066877 W EP2006066877 W EP 2006066877W WO 2007036561 A2 WO2007036561 A2 WO 2007036561A2
Authority
WO
WIPO (PCT)
Prior art keywords
dye
unbranched
branched
alkyl
grouping
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/EP2006/066877
Other languages
German (de)
English (en)
Other versions
WO2007036561A3 (fr
Inventor
Christoph Brabec
Hans-Dieter Feucht
Jens Hauch
Andreas Kanitz
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 WO2007036561A2 publication Critical patent/WO2007036561A2/fr
Publication of WO2007036561A3 publication Critical patent/WO2007036561A3/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
    • C09K9/02—Organic tenebrescent materials

Definitions

  • the invention relates to organic semiconductor devices and more particularly to electrochromic organic semiconductor devices comprising electrochromic pastes comprising novel dyes wherein the pastes comprise a redox system, a conducting salt and a dye combined in a substance and / or as a mixture.
  • the invention relates to the semiconductor devices comprising such pastes and / or in which the new dyes are contained in the active layer.
  • Electrochromic displays normally consist of 3 layers. One layer of this is the actual electrochromic material, a second layer has the function of an ion storage or dispenser and a third layer, which consists of an electrolyte and connects the first two layers together.
  • a voltage is applied between the electrochromic layer and the ion storage layer, the reflection and transmission properties of the electrochromic layer change and the material discolors.
  • Materials are known, for example, from WO 02/0754411, which combines the function of the electrolyte and the color system in one layer.
  • the layer consists of a redox system which is dissolved in an electrolyte. By applying a voltage, the concentration ratio of the redox partner is shifted to each other.
  • the bistability or the ratio of the discoloration time ie of a defined contrast to the decolorization time, without applied voltage or shorted to 80% of the discoloration, is an important parameter for displays.
  • the bistability determines how often a "refresh" pulse is needed to restore the discoloration, which has a direct effect on the power consumption, but also limits the maximum number of lines for pixelated passive matrix displays.
  • the object of the invention is therefore to provide electrochromic pastes that have a high bistability at the same time enable sharp color conversion in electrochromic systems.
  • electrochromic pastes comprise the following constituents a redox system, for example the quinone / hydroquinone or quinone / duroquinone redox system, preferably dissolved in an organic carbonate, particularly preferably in a propylene carbonate, a conducting salt or a mixture of several conducting salts and a dye.
  • a redox system for example the quinone / hydroquinone or quinone / duroquinone redox system, preferably dissolved in an organic carbonate, particularly preferably in a propylene carbonate, a conducting salt or a mixture of several conducting salts and a dye.
  • An organic semiconductor device comprises a substrate, a lower electrode, an upper electrode and in between an active organic layer in which at least one dye according to the invention is contained.
  • the invention is based on known redox systems and conductive salts and the further development of the dyes according to the invention in these systems is described.
  • the new electrochromic dye classes are in particular types of methine dyes in which the longest wavelength absorption maximum is in the NIR range of the electromagnetic spectrum. Since the human eye is particularly insensitive in this area, the formation of a visible dye, due to a change in pH, perceived much sharper. Therefore, such layers with common methine dye concentrations appear colorless or almost colorless. If, by protonation or deprotonation, a conversion of the methine structure of the dye occurs, a new chromophore structure forms, which has its long-wavelength absorption maximum in the visible spectral range of the electromagnetic spectrum and which is easily perceptible to humans.
  • Structure type A Deprotonatable methine substances
  • R1 can be H, alkyl (branched or unbranched Cl to ClO) or
  • Aryl (preferably phenyl)
  • R 2 and R 2 * independently of one another are alkyl (branched or unbranched Cl to ClO), aryl (preferably phenyl) or an alkylene structure bridged with Y 1 and / or Y 2
  • R 3 and R 3 * independently of one another are H, alkyl (branched or unbranched C 1 to C 10), aryl (preferably phenyl) or both are bonded via an oxygen atom or sulfur atom,
  • Structure type B Anionic methine dyes
  • R 3 and R 3 * independently of one another are H, alkyl (branched or unbranched C 1 to C 10), aryl (preferably phenyl) or both are bonded via an oxygen atom or sulfur atom,
  • K + is any cation, preferably that
  • Structure type C Protonatable methine dyes
  • Methine dye (cationic) methine dye (dicationsch)
  • Alk alkyl groups (branched or unbranched Cl to
  • Ar is aromatic radical, preferably phenyl and 1-
  • Substituents R 2 are H or phenyl
  • Structure type E barbituric acid-derived merocyanine
  • R 1 is alkyl (branched or unbranched C 1 to C 10)
  • R 2 is alkyl (branched or unbranched C 1 to C 10) or aryl (preferably phenyl and 1-naphthyl), n is 2, 3 and 4 X is O or S. ,
  • the dyes of the invention are characterized by a high bistability, which reduces the power consumption of a single electrochromic element, and makes possible the production of high-resolution passive matrix displays.
  • the use of the dyes described and illustrated by way of example in organic semiconductor technology is likewise part of the invention.
  • dyes are used for the first time in electrochromic systems whose longest wavelength absorption maximum is in the near IR range and which are characterized by high bistability.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Chemistry (AREA)
  • Pyridine Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Electrochromic Elements, Electrophoresis, Or Variable Reflection Or Absorption Elements (AREA)

Abstract

L'invention concerne des composants à semi-conducteurs organiques et, en particulier, des composants à semi-conducteurs organiques électrochromiques comportant de nouvelles pâtes électrochromiques basées sur le pH qui contiennent de nouveaux colorants, un système d'oxydoréduction, un sel conducteur et un colorant se présentant sous forme combinée et/ou sous forme de mélange dans lesdites pâtes. L'invention concerne également ces composants à semi-conducteurs qui comportent des pâtes de ce type et/ou dans lesquels les nouveaux colorants sont contenus dans la couche active. Ces colorants se caractérisent par une haute bistabilité et en ce que leur maximum d'absorption de plus grande longueur d'onde est situé dans le domaine infrarouge proche.
PCT/EP2006/066877 2005-09-30 2006-09-29 Pates electrochromiques contenant de nouveaux colorants Ceased WO2007036561A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102005046960 2005-09-30
DE102005046960.4 2005-09-30

Publications (2)

Publication Number Publication Date
WO2007036561A2 true WO2007036561A2 (fr) 2007-04-05
WO2007036561A3 WO2007036561A3 (fr) 2008-02-28

Family

ID=37648377

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2006/066877 Ceased WO2007036561A2 (fr) 2005-09-30 2006-09-29 Pates electrochromiques contenant de nouveaux colorants

Country Status (1)

Country Link
WO (1) WO2007036561A2 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109400572A (zh) * 2018-11-03 2019-03-01 复旦大学 近红外第二窗口发射的荧光染料及其制备方法和应用
CN109942507A (zh) * 2019-03-29 2019-06-28 南方医科大学 一种2,2-双氰基亚甲基噻唑及其应用

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DD222434A1 (de) * 1984-03-15 1985-05-15 Wolfen Filmfab Veb Elektrofotografisches aufzeichnungsmaterial
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
DE19605448A1 (de) * 1996-02-15 1997-08-21 Bayer Ag Elektrochromes System
DE19631729A1 (de) * 1996-08-06 1998-02-12 Bayer Ag Elektrochromes System
DE10001031A1 (de) * 2000-01-13 2001-07-19 Bayer Ag Elektrochrome Vorrichtung
US6879424B2 (en) * 2001-03-19 2005-04-12 Aveso, Inc. Electrochromic display device and compositions useful in making such devices

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109400572A (zh) * 2018-11-03 2019-03-01 复旦大学 近红外第二窗口发射的荧光染料及其制备方法和应用
CN109400572B (zh) * 2018-11-03 2022-10-11 复旦大学 近红外第二窗口发射的荧光染料及其制备方法和应用
CN109942507A (zh) * 2019-03-29 2019-06-28 南方医科大学 一种2,2-双氰基亚甲基噻唑及其应用

Also Published As

Publication number Publication date
WO2007036561A3 (fr) 2008-02-28

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