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Intermolecular charge transfer type fluorescent dyes and use thereof

A technology for fluorescent dyes and charge transfer, which is applied in the field of intramolecular charge transfer fluorescent dyes, which can solve the problems of lack of materials and achieve the effects of good purity, simple synthesis, and good solubility

Inactive Publication Date: 2005-11-23
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] At present, materials that emit saturated red light are still lacking, and there are few literature and patent reports on charge-transfer fluorescent dyes with D-π-A-π-D configuration and their applications in organic light-emitting diodes.

Method used

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  • Intermolecular charge transfer type fluorescent dyes and use thereof
  • Intermolecular charge transfer type fluorescent dyes and use thereof
  • Intermolecular charge transfer type fluorescent dyes and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment (1

[0058] Embodiment (1): N, N'-di-[9-(2'-ethyl-hexyl)-carbazole-vinyl]-succinonitrile (Dye 1)

[0059] In a 100ml three-necked flask, 3-formyl-9-(2'-ethyl-hexyl)-carbazole (42mmol) and diaminosuccinonitrile (20mmol) were placed in about 40ml of glacial acetic acid, and a few Drop acetic anhydride as a catalyst, heat and reflux at 120°C for 5 hours under a nitrogen atmosphere; after the reaction stops, cool to room temperature, pour the mixture into 150ml of water, leave it for 4 hours, and extract the aqueous phase with dichloromethane (60ml×2) ; The combined organic phases were washed with water and dried over anhydrous magnesium sulfate. The organic solvent was removed by vacuum rotary evaporation, and the crude product was purified by silica gel column chromatography (eluent-dichloromethane / petroleum ether 1:1 v / v) to obtain a dark red solid with metallic luster (yield 72%).

[0060] Mass Spectrum (MALDI-TOF-MS): m / z calculated 686.4, measured 687.6 (M + );

[0061] H NMR ...

Embodiment (2

[0063] Embodiment (2): N, N'-two-(triphenylamine)-vinyl-succinonitrile (Dye 2)

[0064] In a 100ml three-necked flask, put aldehyde triphenylamine (42mmol) and diaminosuccinonitrile (20mmol) in about 40ml of glacial acetic acid, add a few drops of acetic anhydride as a catalyst, and heat to reflux at 120°C under a nitrogen atmosphere 5 hours; after the reaction stopped, cooled to room temperature, the mixture was poured into 150ml of water, and after standing for 4 hours, the aqueous phase was extracted with dichloromethane (60ml×2); the organic phases were combined, washed with water, and dried over anhydrous magnesium sulfate. The organic solvent was removed by vacuum rotary evaporation, and the crude product was purified by silica gel column chromatography (eluent-dichloromethane / petroleum ether 1:1 v / v) to obtain a dark red solid with metallic luster (yield 72%).

[0065] Mass Spectrum (MALDI-TOF-MS): m / z calculated 618.3; measured 618.4.

[0066] H NMR spectrum ( 1 H-NM...

Embodiment (3

[0068] Embodiment (3): N, N'-di-[9-(2'-ethyl-hexyl)-phenothiazine-vinyl]-succinonitrile (Dye3)

[0069] In a 100ml three-necked flask, put 3-formyl-9-(2'-ethyl-hexyl)-phenothiazine (42mmol) and diaminosuccinonitrile (20mmol) in about 40ml of glacial acetic acid, add A few drops of acetic anhydride were used as a catalyst, and heated to reflux at 120°C for 5 hours under nitrogen atmosphere; after the reaction stopped, cooled to room temperature, the mixture was poured into 150ml of water, and after standing for 4 hours, the aqueous phase was extracted with dichloromethane (60ml×2 ); the organic phases were combined, washed with water, and dried over anhydrous magnesium sulfate. The organic solvent was removed by vacuum rotary evaporation, and the crude product was purified by silica gel column chromatography (eluent-dichloromethane / petroleum ether 1:1 v / v) to obtain a dark red solid with metallic luster (yield 72%).

[0070] Mass Spectrum (MALDI-TOF-MS) m / z: Calculated 750.4; ...

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Abstract

The invention provides an intermolecular charge transfer type fluorescent dyes and its preparation, which comprises using fine cavity transmission groups of triphenylamine, carbazole and fentiazin as electron donors, using nitrile radicals with strong pro-electron capacity as electron donors, forming C=N conjugated pi bond connection through simple condensation reaction, thus preparing a series of type P luminescent materials. Experiment has proved that, these materials are red electroluminescent materials having pure emission.

Description

technical field [0001] The invention relates to an intramolecular charge transfer fluorescent dye. [0002] The present invention also relates to a preparation method of the above-mentioned fluorescent dye. [0003] The present invention also relates to the application of the above-mentioned fluorescent dyes. Background technique [0004] Organic electroluminescent devices are a new type of display technology that is gradually becoming mature in the field of optoelectronic devices and has great practical prospects. Since Kodak Corporation (Tang, C.W.; Vanslyke, S.A. Appl. Phys. Lett. 1987, 51, 913.) introduced high-efficiency organic electroluminescent devices in 1987, with its adjustable luminous color, high brightness, high efficiency, Excellent characteristics such as wide viewing angle, low power consumption, simple preparation process, and the ability to prepare curved and flexible screens, as well as potential applications in the field of large-area flat-panel full-c...

Claims

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Application Information

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IPC IPC(8): C09K11/06
Inventor 刘云圻孙晓波徐新军于贵赵哲辉陈仕艳朱道本
Owner INST OF CHEM CHINESE ACAD OF SCI
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