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An organic phosphorous luminescent material, its preparation method and organic electroluminescent device made therefrom

A luminescent material, organic phosphorous technology, applied in luminescent materials, electro-solid devices, organic chemistry and other directions, can solve the problems of high synthesis price of phosphorescent materials, high synthesis process requirements, easy to pollute the environment, etc., and achieves improved luminous efficiency and service life. The effect of long, easily available raw materials

Active Publication Date: 2022-03-15
JILIN OPTICAL & ELECTRONICS MATERIALS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the relatively high synthesis price of phosphorescent materials, the synthesis process requirements are relatively high, and it is easy to pollute the environment during the synthesis process, the purification requirements are relatively high, the life is short, and the efficiency is low.

Method used

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  • An organic phosphorous luminescent material, its preparation method and organic electroluminescent device made therefrom
  • An organic phosphorous luminescent material, its preparation method and organic electroluminescent device made therefrom
  • An organic phosphorous luminescent material, its preparation method and organic electroluminescent device made therefrom

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0060] Embodiment 1 prepares compound L001

[0061]

[0062] ①Under nitrogen protection system, weigh A-001 (2-phenylpyridine 64.5mmol, 10g), IrCl 3 ·3H 2 O (24.8mmol, 8.75g) was put into the reaction system, a mixed solution of 300mL ethylene glycol ether and 100mL pure water was added, refluxed for 24 hours under the protection of nitrogen, and then cooled to room temperature, a precipitate was precipitated, the precipitate was suction filtered, and water , absolute ethanol, and petroleum ether were washed and dried in sequence. The bridging ligand B-001 (6.64 g, yield 50%) was obtained as a yellow powder.

[0063] ②Weigh intermediate B-001 (4.67mmol, 5g), add silver trifluoromethanesulfonate (14mmol, 3.6g), then add 100mL of dichloromethane to the system, add 40mL of methanol, under the protection of nitrogen, reflux for 24 hours , cooled to room temperature, column chromatography (short column) filtrate was concentrated until solid precipitation. The iridium complex...

Embodiment 2

[0068] Embodiment 2 prepares compound L044

[0069]

[0070] ①Under nitrogen protection system, weigh A-044 (52.84mmol, 10g), IrCl 3 ·3H 2 O (21.12mmol, 7.45g) was put into the reaction system, a mixed solution of 300mL ethylene glycol ether and 100mL pure water was added, refluxed for 24 hours under the protection of nitrogen, and then cooled to room temperature, a precipitate was precipitated, the precipitate was suction filtered, and water , absolute ethanol, and petroleum ether were washed and dried in sequence. The bridging ligand B-044 was obtained as a yellow powder (6.8 g, yield 53%).

[0071] ②Weigh intermediate B-044 (4.96mmol, 6g), add silver trifluoromethanesulfonate (14.8mmol, 3.8g), then add 120mL of dichloromethane to the system, add 40mL of methanol, under the protection of nitrogen, reflux for 24 Hours, cooled to room temperature, column chromatography (short column) filtrate concentrated to solid precipitation. The iridium complex intermediate C-044 (7...

Embodiment 3

[0076] Embodiment 3 prepares compound L073

[0077]

[0078] ①Under the nitrogen protection system, weigh raw material A-073 (59.45mmol, 20g), IrCl 3 ·3H 2 O (19.8mmol, 7g) was put into the reaction system, a mixed solution of 500mL ethylene glycol ether and 167mL pure water was added, refluxed for 18 hours under the protection of nitrogen, and then cooled to room temperature. Wash and dry with water ethanol and petroleum ether in sequence. The bridging ligand B-073 (8.5 g, yield 60%) was obtained as a yellow powder.

[0079] ②Then weigh intermediate B-073 (5.9mmol, 8.5g), add silver trifluoromethanesulfonate (17.7mmol, 4.55g), then add 200mL of dichloromethane to the system, add 50mL of methanol, under the protection of nitrogen, reflux After 24 hours, it was cooled to room temperature, and the filtrate was concentrated by column chromatography (short column) until solids were precipitated. The intermediate C-073 (10.1 g, yield 80%) was obtained as a yellow-green powder...

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Abstract

The present invention relates to an organic phosphorous luminescent material, its preparation method and an organic electroluminescent device made of it. The structure of the organic phosphorous luminescent material is shown in Chemical Formula 1: the organophosphorous luminescent material provided by the present invention is a The new type of iridium metal complex adjusts the wavelength of the compound by selecting specific heterocyclic ligands, and the obtained organometallic compound improves the luminous efficiency of the device and has a long service life after being used in an organic electroluminescent device. The preparation method of the organophosphorus luminescent material provided by the invention has the advantages of simple synthesis route, easy-to-obtain raw materials and high yield.

Description

technical field [0001] The invention relates to the field of organic photoelectric materials, in particular to an organic phosphorescent material, a preparation method thereof and an organic electroluminescent device made thereof. Background technique [0002] Organic light-emitting diodes (Organic Light-Emitting Diode, OLED) are also called organic electro-laser displays and organic light-emitting semiconductors. It was discovered in the laboratory by Chinese-American professor Ching W.Tang in 1979. OLED display technology has the advantages of self-illumination, wide viewing angle, almost infinitely high contrast, low power consumption, and extremely high response speed. Organic electroluminescent technology is the latest generation of flat-panel display technology, which can be used for flat-panel displays and lighting sources. At present, commercial flat-panel displays have been put into the market. Due to its own absolute advantages, the lighting source will soon be i...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F15/00C09K11/06H01L51/54
CPCC07F15/0033C09K11/06C09K2211/185H10K85/342
Inventor 王辉李建行刘志远赵贺于丹阳张思铭马晓宇
Owner JILIN OPTICAL & ELECTRONICS MATERIALS