Compound of biindole heterocycles, preparation method and application in use for organic electroluminescence material

A compound, indole technology, applied in the directions of luminescent materials, chemical instruments and methods, organic chemistry, etc., can solve the problems of complex synthesis route, high material cost, low stability, etc., and achieves simple preparation process, good optical performance, easy to use. The effect of purification

Inactive Publication Date: 2005-01-12
SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] Among the materials that make up organic light-emitting diodes, the purity and stability of the material of the hole transport layer have a greater impact on the performance of the entire device (Angew.Chem.Int.Ed., 1998, 37, 402-428), and the current The triphenylamine-based hole transport material used is difficult to purify and has low stability. At the same time, its synthesis route is complicated and the material cost is high

Method used

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  • Compound of biindole heterocycles, preparation method and application in use for organic electroluminescence material
  • Compound of biindole heterocycles, preparation method and application in use for organic electroluminescence material
  • Compound of biindole heterocycles, preparation method and application in use for organic electroluminescence material

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Example 1 3-methoxyl group-2, the synthesis of 5-bis(N-benzyl-3'-indole)pyrazine

[0032] Under argon protection, 825 mg (3 mmol) N-tert-butyldimethylsilyl-3-indole borate ethylene glycol ester (according to Journal of Organic Chemistry, 1994, 59, 10-11 prepared by the reported method), 268 mg (1 mmol) 3-methoxy-2,5-dibromopyrazine and 116 mg (0.1 mmol) Pd (PPh 3 ) 4 , after replacing the gas in the reaction bottle with an inert gas, add 20mL of toluene and 20mL of ethylene glycol dimethyl ether, stir well, and then add 3mL of 2M sodium carbonate aqueous solution. The mixture was heated to 80-100°C and stirred at this temperature for about 24 hours. After cooling to room temperature, add 30 mL of water. Extracted with ethyl acetate (2×50 mL); the organic phases were combined, washed with saturated brine and dried over anhydrous sodium sulfate, and the organic solvent was evaporated under reduced pressure. The residue was dissolved in tetrahydrofuran, added TBAF (tet...

Embodiment 2

[0035] Example 2 Synthesis of 2-dimethylamino-3,5-bis(N-benzyl-3'-indole)-pyrazine

[0036] Under the protection of argon, 3.85g (14mmol) N-tert-butyldimethylsilyl-3-indole ethylene glycol borate, 1.267g (4.6mmol) 3-methoxy- 2,5-Dibromopyrazine, 531mg (0.46mmol) Pd(PPh 3 ) 4 . After the reaction flask was replaced with an inert gas, 40 mL of toluene and 40 mL of ethylene glycol dimethyl ether were added, and after uniform stirring, 14 mL of 2M sodium carbonate aqueous solution was added. The mixture was heated to 80-100°C and stirred at this temperature for about 24 hours. After the reaction mixture was cooled to room temperature, 50 mL of water was added and extracted with ethyl acetate (2×50 mL). The organic phases were combined, washed with saturated brine and dried over anhydrous sodium sulfate, and the organic solvent was distilled off under reduced pressure. The residue was dissolved in tetrahydrofuran, added TBAF in tetrahydrofuran (1M, 14mL, 14mmol), stirred at ro...

Embodiment 3

[0039] Example 3 Synthesis of 2,5-bis(N-benzyl-3'-indole)-pyrazine

[0040] Under argon protection, 3.3g (12mmol) N-tert-butyldimethylsilyl-3-indole boronic acid, 952mg (4mmol) 2,5-dibromopyrazine, 463mg (0.4mmol) Pd (PPh 3 ) 4 Sequentially add to a 200mL reaction flask, fill the reaction flask with an inert gas, add 50mL of toluene and 50mL of ethylene glycol dimethyl ether, stir well and add 12mL of 2M sodium carbonate aqueous solution. The mixture was heated to 80-100°C and stirred at this temperature for about 24 hours. After cooling to room temperature, 50 mL of water was added and extracted with ethyl acetate (2×50 mL). The organic phases were combined and washed with saturated brine, dried over anhydrous sodium sulfate, and the organic solvent was evaporated under reduced pressure. The residue was dissolved in tetrahydrofuran, added TBAF in tetrahydrofuran (1M, 12mL, 12mmol), stirred at room temperature for 6 hours, added water 20mL, extracted with ethyl acetate (2×3...

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Abstract

This invention relates to metal for prepn. of bis-indole heterocycle type organic electroluminescence material with characteristic of having indok-aromatic heterocycle-indole structure. advantages are: easy synthesis and purification, high opto-thermo stability, easy to be dissolved in organic solvent, high fluorescent light, high-hole conduction property, being used as hole conduction layer and luminous layer of OLED. In the prepn., indole boric acid or its ester and dihalogenated aromatic hydrocarbon or dihalogenated aromatic heterocycle compound are proceed Suzuki coupling reaction to obtain said product.

Description

technical field [0001] The invention relates to a new class of bis-indole heterocyclic compounds, which are prepared from indole compounds as starting materials. The compounds provided by the invention are a class of potential electroluminescent materials. Background technique [0002] Organic electroluminescent materials (OLEDs) have been paid close attention to by the scientific and industrial circles because of their great application prospects in flat panel displays. In the past two decades, many famous research institutions in the world, such as the Max Planck Institute, Princeton University and Cambridge University, have carried out a number of in-depth research on material synthesis and device manufacturing; many multinational companies around the world Such as Dow Chemical, DuPont, Philips, IBM, Motorola, Dainippon Ink, etc. have also invested a lot of financial and manpower to concentrate on the research of industrialized organic light-emitting diodes and develop t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/04C07D403/04C09K11/06
Inventor 姜标房强徐兵
Owner SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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