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OLED (organic light emitting diode) material with anthraquinone structure as well as preparation method and application

An electroluminescence, electromechanical technology, applied in luminescent materials, organic chemistry, chemical instruments and methods, etc., can solve the problems of low device life and efficiency, immature blue light-emitting devices, etc., and achieve good photoelectric performance and good film stability. , the effect of not easy to crystallize

Inactive Publication Date: 2019-02-15
VALIANT CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In order to realize full-color display, light-emitting devices of red, green, and blue colors are required respectively. Compared with red light devices and green light devices, blue light-emitting devices are not mature enough, and the device life and efficiency are low

Method used

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  • OLED (organic light emitting diode) material with anthraquinone structure as well as preparation method and application
  • OLED (organic light emitting diode) material with anthraquinone structure as well as preparation method and application
  • OLED (organic light emitting diode) material with anthraquinone structure as well as preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] The preparation of embodiment 1 compound C02

[0046]

[0047] (1) Preparation of Intermediate I: In a 1L three-necked flask, add 1-amino-5-chloro-anthraquinone (54.1g, 0.21mol), bromobenzene (31.4g, 0.20mol), sodium tert-butoxide (25.0 g, 0.26mol), palladium acetate (0.45g, 2.0mmol), P(t-Bu) 3 HBF 4 (1.16g, 4.0mmol) and 500mL of toluene, under the protection of nitrogen, react at 100-110°C for 10h, after the reaction, add 200g of water to the reaction system to quench the reaction, filter, separate the liquid, remove the solvent under reduced pressure of the organic phase, column Purified by chromatography, and then recrystallized from toluene and petroleum ether to obtain Intermediate I with a yield of 87.36%;

[0048] (2) Preparation of Intermediate II: In a 1L three-necked flask, add Intermediate I (50.1g, 0.15mol), 1-bromonaphthalene (34.2g, 0.165mol), sodium tert-butoxide (21.6g, 0.225mol) , palladium acetate (0.336g, 1.5mmol), P(t-Bu) 3 HBF 4 (0.87g, 3.0m...

Embodiment 2

[0053] The preparation of embodiment 2 compound C04

[0054] Referring to Example 1, the raw material II was replaced by 1-bromonaphthalene with 4-bromobiphenyl during the preparation process to obtain the target product C04 with a total yield of 33.57%.

[0055] High resolution mass spectrometry, molecular formula C 44 h 28 N 2 o 2 , theoretical value 616.2151, test value 616.2176.

Embodiment 3

[0056] The preparation of embodiment 3 compound C07

[0057] Referring to Example 1, the raw material II was replaced with 9-bromoanthracene by 1-bromonaphthalene in the preparation process to obtain the target product C07 with a total yield of 31.38%.

[0058] High resolution mass spectrometry, molecular formula C 46 h 28 N 2 o 2 , the theoretical value is 640.2151, and the test value is 640.2138.

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Abstract

The invention relates to an OLED (organic light emitting diode) material with an anthraquinone structure as well as a preparation method and an application. The OLED material with the anthraquinone structure has the structural formula shown in the description, wherein Ar1 and Ar2 are aromatic heterocyclic radicals with the carbon atom number of 5-60 or any one of aryl with the carbon atom number of 5-60 and a polycyclic aryl conjugated structure group, and Ar3 is any one of aryl with the carbon atom number being 5-60, heterocyclic aryl or a polycyclic aryl conjugated structure group; the OLEDmaterial with the anthraquinone structure is prepared from raw materials including 1-amino-5-chloro-anthraquinone, Ar1-X, Ar2-X, Ar3-X and aniline through a catalytic synthesis reaction, wherein X isBr or I. The material is applied to a light emitting layer of an OLED device, is not prone to crystallization and aggregation among molecules and has good film stability, and the OLED device preparedfrom the material has good photoelectric property.

Description

technical field [0001] The invention relates to an organic electroluminescence material, a preparation method and application thereof, in particular to an organic electroluminescence material with an anthraquinone structure, a preparation method and application thereof, and belongs to the field of organic electroluminescence. Background technique [0002] Organic electroluminescent diodes (OLEDs) were produced in the 1980s. They have many advantages such as self-illumination, wide viewing angle, fast response speed, and flexible display, which make them the most favorable competitors for the next generation of flat panel display technology. , has received great attention from people, and after more than 20 years of development, the technology has gradually matured. [0003] At present, organic electroluminescent technology is mainly used in two fields, namely full-color display and white lighting. Commodities based on OLED display technology have gradually realized industria...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/80C07D405/12C07D409/12C09K11/06H01L51/54
CPCC09K11/06C07D209/80C07D405/12C07D409/12C09K2211/1011C09K2211/1029C09K2211/1092C09K2211/1088H10K85/622H10K85/636H10K85/633H10K85/615H10K85/6576H10K85/6574H10K85/6572
Inventor 高自良李庆巨成良姜瀚周银波石宇
Owner VALIANT CO LTD