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Organic electroluminescent compound, luminescent material and organic electroluminescent device

A technology of electroluminescent devices and luminescent materials, which is applied in luminescent materials, organic chemistry, electric solid-state devices, etc., can solve the problems of reduced color purity, poor thermal stability, and chromatic aberration, and achieve excellent heat resistance, reduced life, and low The effect of drive voltage

Active Publication Date: 2019-04-19
SUZHOU JOYSUN ADVANCED MATERIALS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Due to the poor thermal stability of the above materials, long-term driving will cause color purity to decrease, resulting in problems such as chromatic aberration in panel applications

Method used

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  • Organic electroluminescent compound, luminescent material and organic electroluminescent device
  • Organic electroluminescent compound, luminescent material and organic electroluminescent device
  • Organic electroluminescent compound, luminescent material and organic electroluminescent device

Examples

Experimental program
Comparison scheme
Effect test

preparation example 1

[0134] This preparation example is used to prepare compound 44, and its structural formula and synthetic route are as follows:

[0135] Synthesis of Intermediate 44A

[0136]

[0137] In a 250mL Schlenk bottle, add 10.19g (25.77mmol) of 4-bromo-9,9'-spirobifluorene, 3.00g (15.00mmol) of aniline, 0.36g (1.6mmol) of palladium acetate, tri-tert-butylphosphinetetrafluoro Borate 0.93g (3.22mmol), sodium tert-butoxide 9.29g (96.64mmol), toluene 150mL, under the protection of argon, reflux and stir for 12 hours to complete the reaction. Evaporate the solvent, dissolve the residue with 100mL dichloromethane and 50mL water, wash with water, separate the organic layer, extract the water layer twice with 30mL dichloromethane, combine the organic layers, evaporate the solvent, and separate the residue by column chromatography (The silica gel is 350 mesh, and the eluent is petroleum ether:dichloromethane=3:1 (V / V)), the solvent was evaporated, and after drying, 9.70 g of white solid wa...

preparation example 2

[0142] This preparation example is used to prepare compound 74, its structural formula and synthetic route are as follows:

[0143] Synthesis of Intermediate 74A

[0144]

[0145] In a 250mL Schlenk bottle, add 7.04g (25.77mmol) of 9,9-dimethyl-2-bromofluorene, 3.00g (32.21mmol) of aniline, 0.36g (1.61mmol) of palladium acetate, tri-tert-butylphosphine tetrafluoro Borate 0.93g (3.22mmol), sodium tert-butoxide 9.29g (96.64mmol), toluene 150mL, under the protection of argon, reflux and stir for 12 hours to complete the reaction. Evaporate the solvent, dissolve the residue with 150mL dichloromethane and 100mL water, wash with water, separate the organic layer, extract the aqueous layer twice with 15mL dichloromethane, combine the organic layers, evaporate the solvent, and separate the residue by column chromatography (The silica gel is 350 mesh, and the eluent is petroleum ether:dichloromethane=4:1 (V / V)), the solvent was evaporated, and after drying, 6.20 g of white crystals...

preparation example 3

[0150] This preparation example is used to prepare compound 83, and its structural formula and synthetic route are as follows:

[0151] Synthesis of Intermediate 83A

[0152]

[0153] In a 250mL Schlenk bottle, add 5.90g (14.93mmol) of 3-bromo-9,9'-spirobifluorene, 2.00g (18.66mmol) of aniline, 0.21g (0.09mmol) of palladium acetate, tri-tert-butylphosphinetetrafluoro Borate 0.54g (1.87mmol), sodium tert-butoxide 5.38g (56.0mmol), toluene 120mL, under the protection of argon, reflux and stir for 12 hours to complete the reaction. Evaporate the solvent, dissolve the residue with 200mL dichloromethane and 50mL water, wash with water, separate the organic layer, extract the aqueous layer twice with 15mL dichloromethane, combine the organic layers, evaporate the solvent, and separate the residue by column chromatography (The silica gel is 350 mesh, and the eluent is petroleum ether:dichloromethane=2:1 (V / V)), the solvent was evaporated, and after drying, 6.40 g of white crystal...

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Abstract

The invention provides an organic electroluminescent compound, a luminescent material and an organic electroluminescent device. The organic electroluminescent compound is shown in formula (1). The organic electroluminescent compound can exhibit good properties as a fluorescent luminescent guest material. The organic electroluminescent device prepared by using the luminescent material exhibits superior properties such as low driving voltage, high luminous efficiency, long service life of the device and high spectral color purity.

Description

technical field [0001] The present invention relates to an organic electroluminescent compound, a luminescent material comprising the organic electroluminescent compound, and an organic electroluminescent device comprising the organic electroluminescent compound. Background technique [0002] Since Kodak C.W.Tang et al. reported for the first time in 1987 that Alq was prepared by vacuum evaporation 3 Since the double-layer light-emitting devices of light-emitting materials, organic electroluminescent devices have received great attention. After more than 30 years of development, the application of organic electroluminescence in flat panel display and lighting has entered the initial stage of industrialization. [0003] An organic electroluminescent device generally consists of an anode, a metal cathode and an organic layer sandwiched between them. The organic layer mainly includes a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting ...

Claims

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Application Information

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IPC IPC(8): C07C211/61C07D307/91C07D333/76C09K11/06H01L51/50H01L51/54
CPCC09K11/06C07C211/61C07D307/91C07D333/76C07C2603/24C07C2603/94C07C2603/18C07C2603/26C09K2211/1029C09K2211/1011C09K2211/1007C09K2211/1014C09K2211/1092C09K2211/1088H10K85/624H10K85/622H10K85/626H10K85/633H10K85/615H10K85/6576H10K85/6574H10K50/11
Inventor 崔林松张业欣林久栋陈华
Owner SUZHOU JOYSUN ADVANCED MATERIALS CO LTD
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