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A kind of azaxanthone compound and its application on oled device

A technology of xanthone and compound, applied in the direction of electric solid device, semiconductor device, chemical instrument and method, etc., can solve the problems of limited application, lower triplet energy level, etc., achieve good optoelectronic performance, increase orbital overlap, Avoid the effect of agglomeration

Active Publication Date: 2019-03-05
JIANGSU SUNERA TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At the same time, there is a strong intramolecular charge transfer between the donor and the acceptor of the host material, which leads to the lowering of the triplet energy level of the material itself, which limits its application in industrial production.

Method used

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  • A kind of azaxanthone compound and its application on oled device
  • A kind of azaxanthone compound and its application on oled device
  • A kind of azaxanthone compound and its application on oled device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] Embodiment 1: the synthesis of R structure (shown in general formula 3)

[0051]

[0052] The preparation method of R structure (shown in general formula 3):

[0053] Weigh raw material I o-bromonitro compound, raw material II boric acid, and dissolve it in a mixed solvent of toluene and ethanol with a volume ratio of 2:1, and add potassium carbonate aqueous solution, Pd(PPh 3 ) 4 , reacted at 95-110°C for 10-24 hours, cooled to and filtered the reaction solution, the filtrate was rotary evaporated, and passed through a silica gel column to obtain the target product; the molar ratio of o-bromonitro compound to boric acid was 1:1.0~3.0; o-bromo The molar ratio of nitro compound to potassium carbonate is 1:1.0~3.0; o-bromonitro compound and Pd(PPh 3 ) 4 The molar ratio is 1:0.006~0.02;

[0054] Weigh the product from the previous step, dissolve it with o-dichlorobenzene, and then add PPh 3 , under an inert atmosphere, react the mixed solution of the above reactant...

Embodiment 2

[0061] Embodiment 2: the synthesis of R structure (shown in general formula 2)

[0062]

[0063] The preparation method of Reaction Formula 3-1 is: Weigh the corresponding raw material 1-o-aminophenol, raw material 2-o-nitrophenol, and iodine, stir and dissolve them with diethylene glycol as a solvent, and heat to 250-270°C under an inert atmosphere to react 12 -24 hours, take a sample point plate, after the reaction is over, naturally cool to room temperature, there is solid precipitation, filter, take the filter cake and pass through the neutral silica gel column to obtain the intermediate En; the mole of the o-nitrophenol and o-aminophenol The ratio is 1:0.8~2.0; the molar ratio of the o-nitrophenol and iodine is 1:0.05~0.1;

[0064] The preparation method of reaction formula 3-2 is: weigh the corresponding bromide and arylamine with methyl formate, then add Pd 2 (dba) 3 , tri-tert-butylphosphine, sodium tert-butoxide; under an inert atmosphere, react the mixed solutio...

Embodiment 3

[0075] Embodiment 3: the synthesis of compound 1

[0076]

[0077] In a 250ml four-necked flask, add 0.01mol 3-bromo-6-iodo-9-oxa-1-aza-anthracene-10-one, 0.030mol carbazole, 0.03mol tert-butyl Sodium alkoxide, 1 x 10 -4 mol Pd 2 (dba) 3 , 1×10 -4 mol of tri-tert-butylphosphine, 150ml of toluene, heated to reflux for 24 hours, sampling plate, reaction complete, natural cooling, filtration, filtrate rotary evaporation, silica gel column to obtain the target product with a purity of 99.12% and a yield of 63.80%. HRMS(m / z): [M+H] + , the theoretical value is 528.1712, and the measured value is 528.1703.

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Abstract

The invention discloses an azaxanthone compound and its application in an organic electroluminescent device. The compound takes azaxanthone as the core, and has the properties that it is not easy to crystallize and aggregate between molecules, and has a good composition. Membrane characteristics. When the compound of the present invention is used as the main material of the light-emitting layer of the OLED light-emitting device, the current efficiency, power efficiency and external quantum efficiency of the device are greatly improved; at the same time, the life of the device is significantly improved.

Description

technical field [0001] The invention relates to the technical field of semiconductors, in particular to an azaxanthone compound and its application as a host material of a light-emitting layer in an organic light-emitting diode. Background technique [0002] Organic electroluminescent (OLED: Organic Light Emission Diodes) device technology can be used to manufacture new display products and also can be used to make new lighting products, which is expected to replace the existing liquid crystal display and fluorescent lighting, and has a wide application prospect. [0003] The OLED light-emitting device is like a sandwich structure, including electrode material film layers, and organic functional materials sandwiched between different electrode film layers. Various functional materials are superimposed on each other according to the application to form an OLED light-emitting device. As a current device, when a voltage is applied to the electrodes at both ends of the OLED ligh...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D491/052C07D519/00C09K11/06H01L51/50H01L51/54
CPCC09K11/06C07D491/052C07D519/00C09K2211/1033C09K2211/1011C09K2211/1007C09K2211/1014C09K2211/1029H10K85/636H10K85/633H10K85/654H10K85/6572H10K50/11
Inventor 徐凯李崇张小庆张兆超
Owner JIANGSU SUNERA TECH CO LTD
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