WO2007036561A2 - Pates electrochromiques contenant de nouveaux colorants - Google Patents
Pates electrochromiques contenant de nouveaux colorants Download PDFInfo
- 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
Links
- 239000000975 dye Substances 0.000 title claims abstract description 53
- 239000004065 semiconductor Substances 0.000 claims abstract description 10
- 150000003839 salts Chemical class 0.000 claims abstract description 7
- 238000010521 absorption reaction Methods 0.000 claims abstract description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 20
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 claims description 4
- 150000001450 anions Chemical class 0.000 claims description 4
- 125000002091 cationic group Chemical group 0.000 claims description 4
- DZVCFNFOPIZQKX-LTHRDKTGSA-M merocyanine Chemical compound [Na+].O=C1N(CCCC)C(=O)N(CCCC)C(=O)C1=C\C=C\C=C/1N(CCCS([O-])(=O)=O)C2=CC=CC=C2O\1 DZVCFNFOPIZQKX-LTHRDKTGSA-M 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 125000004434 sulfur atom Chemical group 0.000 claims description 4
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 3
- 238000001228 spectrum Methods 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 125000000129 anionic group Chemical group 0.000 claims description 2
- HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 claims description 2
- 150000001768 cations Chemical class 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000000758 substrate Substances 0.000 claims description 2
- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 claims description 2
- 239000000203 mixture Substances 0.000 abstract description 3
- 239000010410 layer Substances 0.000 description 13
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 6
- 239000000463 material Substances 0.000 description 5
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- 238000002845 discoloration Methods 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000003792 electrolyte Substances 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 239000011159 matrix material Substances 0.000 description 3
- 0 CCC([C@@](C(C=C1C=C2)N)OC1=CC2=*(*)*)=CC(N)=C1Oc(cc(*(*)*)cc2)c2C=C1CC Chemical compound CCC([C@@](C(C=C1C=C2)N)OC1=CC2=*(*)*)=CC(N)=C1Oc(cc(*(*)*)cc2)c2C=C1CC 0.000 description 2
- 238000009792 diffusion process Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 2
- 238000013494 PH determination Methods 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 150000001412 amines Chemical group 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000004042 decolorization Methods 0.000 description 1
- 230000005595 deprotonation Effects 0.000 description 1
- 238000010537 deprotonation reaction Methods 0.000 description 1
- WAMKWBHYPYBEJY-UHFFFAOYSA-N duroquinone Chemical compound CC1=C(C)C(=O)C(C)=C(C)C1=O WAMKWBHYPYBEJY-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 150000005677 organic carbonates Chemical class 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- -1 perchlorate anion Chemical class 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 230000005588 protonation Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
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)
- Electrochromic Elements, Electrophoresis, Or Variable Reflection Or Absorption Elements (AREA)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (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.
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 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)
| 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)
| 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 |
| MXPA03008458A (es) * | 2001-03-19 | 2004-06-30 | Dow Global Technologies Inc | Dispositivo de visualizacion electrocromico y composiciones utiles para hacer tales dispositivos. |
-
2006
- 2006-09-29 WO PCT/EP2006/066877 patent/WO2007036561A2/fr active Application Filing
Cited By (3)
| 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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