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Synthesis and organic luminescent device of bisphenothiazine dioxide derivative

A bisphenothiazine and dioxide technology, which is applied in the fields of luminescent materials, organic chemistry, electric solid devices, etc., can solve the problems of increasing the cost of device fabrication, and achieve high glass transition temperature and decomposition temperature, and good thermal stability. , Improve the effect of luminous efficiency

Inactive Publication Date: 2016-07-13
JILIN OPTICAL & ELECTRONICS MATERIALS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In order to balance the carrier injection rate and improve the luminous efficiency of the device, an electron transport layer composed of an electron transport material and a hole transport layer composed of a hole transport material are usually introduced into the light emitting device, but the electron and hole transport The introduction of layers often leads to an increase in the cost of device fabrication

Method used

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  • Synthesis and organic luminescent device of bisphenothiazine dioxide derivative
  • Synthesis and organic luminescent device of bisphenothiazine dioxide derivative
  • Synthesis and organic luminescent device of bisphenothiazine dioxide derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] Add 48.30mmol of phenothiazine and 48.49mmol of sodium tert-butoxide into the reaction flask, then add 33ml of toluene, under nitrogen protection, stir for 10min, then add 0.41mmol of tris(dibenzylideneacetone)dipalladium, tri-tert-butylphosphine 2.45mmol, 2,7-dibromotriphenylene 16.20mmol, gas exchanged three times, reflux at 110°C overnight. After the reaction is finished, post-treatment, extraction with 100ml of dichloromethane, after evaporating the organic phase, a small amount of dichloromethane dissolves and precipitates the product with petroleum ether. The precipitated product is washed 3 times with 100ml of petroleum ether, and washed with 100ml of ethanol for 2 times to obtain a light yellow color The product is 14.09 mmol, and the yield is 87.00%.

[0049] Add 14.00 mmol of 2,7-bis(10H-phenothiazin-10-yl) triphenylene and dichloromethane into the reaction flask, slowly add 35.00 mmol of m-chloroperoxybenzoic acid in batches under ice cooling, and then After...

Embodiment 2

[0052] Add 48.60mmol of phenothiazine and 48.49mmol of sodium tert-butoxide into the reaction flask, then add 33ml of toluene, under nitrogen protection, stir for 10min, then add 0.203mmol of tris(dibenzylideneacetone)dipalladium, tri-tert-butylphosphine 1.295mmol, 16.20mmol of 2,7-dibromophenanthrene, three times of ventilation, 110 ℃ reflux overnight. After the reaction is finished, post-treatment, extraction with 100ml of dichloromethane, after evaporating the organic phase, a small amount of dichloromethane dissolves and precipitates the product with petroleum ether. The precipitated product is washed 3 times with 100ml of petroleum ether, and washed with 100ml of ethanol for 2 times to obtain a light yellow color The product is 14.01 mmol, and the yield is 86.48%.

[0053] Add 14.00 mmol of 2,7-bis(10H-phenothiazin-10-yl)phenanthrene and dichloromethane into the reaction flask, slowly add 35.00 mmol of m-chloroperoxybenzoic acid in batches under ice bath, and then react i...

Embodiment 3

[0056] Add 48.62mmol of phenothiazine and 48.49mmol of sodium tert-butoxide into the reaction flask, then add 33ml of toluene, under nitrogen protection, stir for 10min, then add 0.203mmol of tris(dibenzylideneacetone)dipalladium, tri-tert-butylphosphine 1.295mmol, 16.20mmol of 2,7-dibromopyrene, three ventilations, reflux at 110°C overnight. After the reaction is finished, post-treatment, extraction with 100ml of dichloromethane, after evaporating the organic phase, a small amount of dichloromethane dissolves and precipitates the product with petroleum ether. The precipitated product is washed 3 times with 100ml of petroleum ether, and washed with 100ml of ethanol for 2 times to obtain a light yellow color The product is 14.03 mmol, and the yield is 87.58%.

[0057] Add 14.00mmol of 2,7-bis(10H-phenothiazin-10-yl)pyrene and dichloromethane into the reaction flask, slowly add 35.00mmol of m-chloroperoxybenzoic acid in batches under ice bath, and then react in ice bath for 30mi...

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Abstract

The invention relates to a bisphenothiazine dioxide derivative and an application thereof, and belongs to the field of organic photoelectric material. Different aryl dibromides are adopted as a parent body and are connected with phenothiazine dioxide to form the bisphenothiazine dioxide derivative; with introduction of -SO2-, the compound has good electron transmission performance, and the electronic affinity of the compound and the stability of the compound in air are improved. The bisphenothiazine dioxide derivative can be used as an OLED luminescent device, is suitable for use as an electron transmission material of a blue fluorescent material and as a green phosphorescence electron transmission material and also has the potential of red color application, so that the bisphenothiazine dioxide derivative can be applied to a red-green-blue tri-phosphor doped main body material and also can be independently used as a hole transmission material, an electron transmission material or a luminescent layer.

Description

technical field [0001] The invention relates to the field of organic photoelectric materials, in particular to a bisphenothiazine dioxide derivative and its application. Background technique [0002] The study of organic electroluminescent devices began in the 1930s. In 1936, Destriau dispersed organic fluorescent compounds in polymers to make thin films, and obtained the earliest electroluminescent devices. However, due to the thicker films , the turn-on voltage was very high, and it did not attract everyone's attention at that time; but in 1982, P.S.Vincett et al. prepared a 0.6μm thick anthracene film by vacuum deposition, and reduced the driving voltage of the device to below 30V, which began to attract attention. In 1987, it was a milestone year for organic electroluminescent devices. C.W.Tang et al. used ultra-thin film technology to use a diamine derivative N,N,-diphenyl-N,N ,-bis(3-methylphenyl)-1,1,biphenyl-4,4,diamine(TPD) was used as the hole transport layer and ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D279/34C07D417/14C09K11/06H01L51/54
Inventor 汪康孙峰毕岩李文军
Owner JILIN OPTICAL & ELECTRONICS MATERIALS
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