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Preparation method of integrated phosphine light emission carbazolyl organic photoelectric material

An organic photoelectric material, carbazole-based technology, applied in the direction of luminescent materials, organic chemistry, chemical instruments and methods, etc., to achieve low cost and environment-friendly effects

Inactive Publication Date: 2022-04-08
ANYANG INST OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there have been no literature reports on phosphine oxide-based organic light-emitting devices and their synthesis methods with carbazole as a host material so far.

Method used

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  • Preparation method of integrated phosphine light emission carbazolyl organic photoelectric material
  • Preparation method of integrated phosphine light emission carbazolyl organic photoelectric material
  • Preparation method of integrated phosphine light emission carbazolyl organic photoelectric material

Examples

Experimental program
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Effect test

Embodiment 1

[0048] Synthesis of 4,4'-difluoro-2,2'-dinitro-biphenyl:

[0049] Under the protection of nitrogen, add 100mmol 2-bromo-5-fluoronitrobenzene, 220mmol copper powder and 200mL DMF to a 500mL thick-walled eggplant-shaped bottle equipped with a magnet, stir well at room temperature, and then maintain the reaction temperature at 125°C React for 4 hours. After the reaction of 2-bromo-5-fluoronitrobenzene is complete, cool to room temperature, filter, wash the filter cake with ethyl acetate, dilute the filtrate with ethyl acetate and wash with water and saturated brine in sequence. After washing, the organic phase is washed with Anhydrous Na 2 SO 4 Dry, filter, and spin dry to obtain 4,4'-difluoro-2,2'-dinitro-biphenyl 3 with a yield of 95%.

Embodiment 2

[0051] Synthesis of 4,4'-difluoro-2,2'-diamino-biphenyl:

[0052] Under the protection of nitrogen, 27.4mmol of 4,4'-difluoro-2,2'-dinitrobiphenyl was dissolved in 33mL of ethanol and 33mL of 8M HCl mixed solution, and then 6.0eq of stannous chloride dihydrate was added in batches; The mixture was warmed and stirred at reflux for 4 hours. After the reaction is complete, cool to room temperature and remove ethanol under reduced pressure, pour the residue into a large amount of water, adjust the pH to 8-10 with NaOH, extract three times with ethyl acetate, combine the organic phases and sequentially wash with sodium bicarbonate and saturated salt Wash with water, dry the organic phase with anhydrous sodium sulfate, filter, and remove the solvent under reduced pressure to obtain crude 4,4'-difluoro-2,2'-diamino-biphenyl. The ethyl acetate / petroleum ether system was recrystallized to obtain pure 4,4'-difluoro-2,2'-diamino-biphenyl 4 with a yield of 92%.

Embodiment 3

[0054] Synthesis of 4,4'-difluoro-2,2'-diiodo-biphenyl:

[0055] Dissolve 20mmol of 4,4'-difluoro-2,2'-diamino-biphenyl in 30mL of 8M hydrochloric acid under temperature control -10°C to 0°C, keep the temperature and add 60mmol NaNO dropwise to the system 2 Saturated solution, continued to stir at this temperature for 30 minutes, then lowered the reaction temperature to -15°C, then added 76 mmol KI aqueous solution dropwise to the system, and after the dropwise addition, the reaction system was slowly raised to room temperature and stirred overnight. Sodium thiosulfate was quenched, extracted three times with ethyl acetate, the organic phases were combined and washed with sodium bicarbonate and saturated brine successively, dried over anhydrous sodium sulfate, filtered, and the solvent was removed under reduced pressure to obtain 4,4'- Crude difluoro-2,2'-diiodo-biphenyl 5. Ethyl acetate / petroleum ether system column chromatography (petroleum ether / ethyl acetate=300 / 1-50 / 1), ...

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Abstract

The invention discloses a preparation method of 3, 7-dicarbazolyl-5-phenyl benzoxphosphine heteroindole, and belongs to the technical field of organic synthesis. The method comprises the following steps: carrying out a coupling reaction on 1, 4-difluoro-2-nitrobenzene under the catalysis of copper to obtain 4, 4 '-difluoro-2, 2'-dinitro-biphenyl, carrying out stannous chloride reduction and amido diazonium salt process conversion to obtain 4, 4 '-difluoro-2, 2'-diiodo-biphenyl, and carrying out 4, 4 '-difluoro-2, 2'-diiodo-biphenyl. The preparation method comprises the following steps: carrying out lithium-iodine exchange on 2, 2 '-diiodo-biphenyl, carrying out nucleophilic substitution reaction on the 2, 2'-diiodo-biphenyl and dichlorophenylphosphine to generate phenylphosphine heterobenzoindole, oxidizing the phenylphosphine heterobenzoindole to form phenylphosphine oxide heterobenzoindole, and carrying out substitution reaction on carbazole and aryl fluoride to synthesize the phosphine oxide type organic small molecular luminescent material with fluorescence activity. The 3, 7-dicarbazolyl-5-phenyl benzoxphosphine heteroindole synthesized by the method not only can be used as a photocatalyst in the field of organic synthesis, but also can be used as an organic photoelectric material.

Description

technical field [0001] The invention relates to a preparation method of 3,7-dicarbazolyl-5-phenylbenzophosphineoxaindole, an integrated phosphine light-emitting carbazole-based organic photoelectric material, and belongs to the technical field of organic synthesis. Background technique [0002] High-performance organic light-emitting devices (OLEDs) with integrated phosphine light emission are among the most promising candidates for energy-efficient solid-state lighting and flat-panel display panels. In general, in order to suppress concentration quenching to obtain high photoluminescence quantum yield, it is often necessary to disperse phosphine light-emitting devices in suitable host materials. Furthermore, in order to achieve higher photoluminescence quantum yields for blue phosphine photoemitters, a host material needs to have a triplet energy exceeding 2.75 eV. On the other hand, in order to obtain an emissive layer with carrier balance between electrons and holes, it ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/6568C09K11/06
Inventor 翟圣先董端张艳维卫爱民梁艳美杨双涛董依飞文惠婷黄一晨
Owner ANYANG INST OF TECH
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