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Tetraphenyl diphenyl ether derivative, preparation method therefor, and organic luminescent device

A technology of tetraphenyl diphenyl ether and tetrabromodiphenyl ether, which is applied in the field of organic photoelectric materials, can solve problems such as difficulty in achieving high efficiency and long life, and achieve the effect of low manufacturing cost and reduced manufacturing cost

Active Publication Date: 2016-06-15
JILIN OPTICAL & ELECTRONICS MATERIALS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, it is difficult to achieve high efficiency and long life for blue phosphorescence, and the development of a host material that realizes this is expected

Method used

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  • Tetraphenyl diphenyl ether derivative, preparation method therefor, and organic luminescent device
  • Tetraphenyl diphenyl ether derivative, preparation method therefor, and organic luminescent device
  • Tetraphenyl diphenyl ether derivative, preparation method therefor, and organic luminescent device

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] Embodiment 1: the synthesis of compound (1)

[0052]

[0053] Under nitrogen protection, 132.0 mmol of carbazole, 30.0 mmol of tetraphenyl diphenyl ether meta-chloride, 1.5 mmol of tris(dibenzylideneacetone) dipalladium, 120.0 mmol of sodium tert-butoxide, and 6.0 mmol of tri-tert-butylphosphine mmol, dissolved in 500ml toluene, reflux at 110°C for 24 hours, and determine the end point of the reaction by thin layer chromatography (TLC). After filtering and drying, 24.0 mmol of compound (1) was obtained with a yield of 80%.

Embodiment 2

[0054] Embodiment 2: the synthesis of compound (2)

[0055]

[0056] Under the protection of nitrogen, 130.0 mmol of carbazole, 30.0 mmol of p-(or meta) chlorides of tetraphenyl diphenyl ether, 1.5 mmol of tris(dibenzylideneacetone) dipalladium, 120.0 mmol of sodium tert-butoxide, and 120.0 mmol of tri-tert-butoxide Butylphosphine 6.0mmol, dissolved in 500ml toluene, reflux at 110°C for 24h, use thin layer chromatography (TLC) to determine the end point of the reaction, after the reaction is complete, cool to room temperature, pass through a silica gel funnel, rinse with DCM, spin dry, dichloromethane, petroleum ether After recrystallization, suction filtration and drying, 23.0 mmol of compound (2) was obtained with a yield of 77%.

Embodiment 3

[0057] Embodiment 3: the synthesis of compound (3)

[0058]

[0059] Under the protection of nitrogen, dissolve 417.0mmol of N-phenyl-3-carbazole boric acid, 100.0mmol of p-(or m-) chlorides of tetraphenyl diphenyl ether, and 300.0mmol of potassium carbonate in 300L (toluene: water = 4 : 1) In the solvent, add 10.0 mmol of tetrakistriphenylphosphine palladium under the protection of nitrogen, stir and reflux for 24 hours, separate the liquid at room temperature after the reaction, pass through a silica gel funnel, rinse with dichloromethane, spin dry the solvent, and recrystallize . 76.0 mmol of solid compound (3) was obtained, yield 76%.

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PUM

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Abstract

The invention provides a tetraphenyl diphenyl ether derivative, a preparation method therefor, and an application thereof in organic electro-luminescent devices. The compound has high luminescent efficiency, which means that the compound can be used as a luminescent material or a luminescent main material, especially, a blue phosphorescent main material. The compound, when being used in the OLEDs, has high efficiency and brightness, is long in service life, is low in production cost, and reduces the manufacturing cost of the OLEDs.

Description

technical field [0001] The invention relates to the field of organic photoelectric materials, in particular to a class of tetraphenyl diphenyl ether derivatives, a preparation method and an organic light-emitting device. Background technique [0002] Organic electroluminescent (EL) devices (hereinafter, simply referred to as "organic EL devices"). It generally consists of two opposing electrodes and at least one layer of organic light-emitting compound interposed between the two electrodes. Charges are injected into the organic layer formed between the anode and cathode to form electron and hole pairs, which cause light emission from organic compounds having fluorescent or phosphorescent properties. [0003] With the development of the information age, organic electroluminescent flat panel displays (OLEDs) with high efficiency, energy saving and light weight and large-area white light illumination have attracted more and more attention. OLED technology has attracted the at...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/86C09K11/06H01L51/54
Inventor 马晓宇宋巧红李文军孙峰
Owner JILIN OPTICAL & ELECTRONICS MATERIALS