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Compound, organic light-emitting device, display panel and display device

A compound and electromechanical technology, applied in the field of compounds, organic electroluminescent devices, display panels and display devices, to achieve the effect of widening the light emitting area, high luminous efficiency and long service life

Inactive Publication Date: 2019-12-31
WUHAN TIANMA MICRO ELECTRONICS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] However, few TADF materials have been discovered so far, and new and efficient TADF materials that can be used in OLED devices need to be developed urgently.

Method used

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  • Compound, organic light-emitting device, display panel and display device
  • Compound, organic light-emitting device, display panel and display device
  • Compound, organic light-emitting device, display panel and display device

Examples

Experimental program
Comparison scheme
Effect test

preparation example 1

[0104] Compound M5 was prepared by the following method:

[0105]

[0106] (1) Dissolve compound S1 (20mmol) in 80mL tetrahydrofuran (THF), cool to -78°C, add 31.25mL n-butyllithium solution (1.6M, hexane, 50mmol) to the solution, and stir at -78°C 2h. Then 20 mL of S2 (60 mmol) was added to the solution, the temperature was slowly raised to room temperature, and stirred for 4 h. Water was added to the solution and extracted with ether. The extracted organic phase was washed with water, and anhydrous MgSO was added 4 dry. Purification was carried out by silica gel column chromatography, using dichloromethane:n-hexane (1:9) as the eluent, and finally the eluent was distilled under reduced pressure to obtain the product S3 (18 mmol, 90%).

[0107] MALDI-TOF MS: C 42 h 40 N 2 sn 2 : m / z calculated value: 812.1; tested value: 812.3.

[0108]

[0109] (2) Under nitrogen protection, weigh compounds S3 (126 μmol), S4 (126 μmol), Pd 2 (dba) 3 (6.3μmol) and (tBu) 3 P ...

preparation example 2

[0113] Compound M7 was prepared by the following method:

[0114]

[0115] (1) Dissolve compound S5 (25mmol) in 100mL THF, cool to -78°C, add 40mL n-butyllithium solution (1.6M in hexane, 64mmol) to the solution, and stir at -78°C for 2h. Then 25 mL of S2 (75 mmol) was added to the solution, the temperature was slowly raised to room temperature, and stirred for 4 h. Water was added to the solution and extracted with ether. The extracted organic phase was washed with water, and anhydrous MgSO was added 4 dry. Purification was performed by silica gel column chromatography, using dichloromethane:n-hexane (1:9) as the eluent, and finally the eluent was distilled under reduced pressure to obtain the product S6 (23.75 mmol, 95%).

[0116] MALDI-TOF MS: C 24 h 29 NSn 2 : m / z calculated value: 571.0; tested value: 571.2.

[0117]

[0118] (2) Under nitrogen protection, weigh compounds S6 (160 μmol), S7 (160 μmol), Pd 2 (dba) 3 (8μmol) and (tBu) 3 P (8μmol) and KOtBu (4...

preparation example 3

[0122] Compound M24 was prepared by the following method:

[0123]

[0124] (1) Under nitrogen protection, weigh compounds S6 (104 μmol), S8 (104 μmol), Pd 2 (dba) 3 (5.2μmol) and (tBu) 3 P (5.2μmol) and KOtBu (300μmol) were added to a 500mL two-necked flask. Inject 100mL of toluene into the two-necked flask (pass N in advance 2 15min to remove oxygen), reflux and stir overnight. After the reaction, cool down, distill under reduced pressure, concentrate the solution to 25 mL, add 15 mL of deionized water, and drop a few drops of 2M HCl to remove the salt therein. Extract with dichloromethane, collect the organic phase, and wash with anhydrous Na 2 SO 4 Dry processing. The dried solution was filtered, and the solvent was removed by a rotary evaporator to obtain a crude product. The crude product was purified by silica gel chromatography to remove the Pd catalyst. The eluate was collected, concentrated, and purified using size exclusion chromatography using THF as e...

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Abstract

The invention relates to a compound, an organic light-emitting device, a display panel and a display device. The compound has a structure shown as formula (I), the compound is applied to an organic light-emitting display device, the organic light-emitting display device comprises the organic light-emitting device, the organic light-emitting device comprises: an anode, a cathode and at least one layer of organic film located between the anode and the cathode, wherein the organic film contains the compound shown as the formula (I). The compound provided by the invention is a macrocyclic compoundcontaining a D-A (electron donating group-electron withdrawing group) structure, is a bipolar material, and can endow the device with high luminous efficiency, low driving voltage and long service life when used, especially as a luminescent layer material in the organic light-emitting device.

Description

technical field [0001] The technical field of organic electroluminescence of the present invention particularly relates to a compound, an organic electroluminescence device, a display panel and a display device. Background technique [0002] Organic light-emitting diode (Organic Light-Emitting Diode, OLED), also known as organic electro-laser display, organic light-emitting semiconductor. OLED is a current-type organic light-emitting device, which is a phenomenon of luminescence caused by injection and recombination of carriers, and the luminous intensity is proportional to the injected current. Under the action of an electric field in the OLED, the holes generated by the anode and the electrons generated by the cathode will move, inject into the hole transport layer and the electron transport layer respectively, and migrate to the light emitting layer. When the two meet in the light-emitting layer, energy excitons are generated, which excite light-emitting molecules and fi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02C07F9/572C07D495/22C07D498/08C07F9/6578C07D487/08C07D487/18C07D487/22C07D497/22C07D495/18C07D471/08C07D471/22C07F9/58C07F9/6584C07F7/08C09K11/06H01L51/50H01L51/54
CPCC07F5/02C07F9/5728C07D495/22C07F5/027C07D498/08C07F9/6578C07D487/08C07D487/18C07D487/22C07D497/22C07D495/18C07D471/08C07D471/22C07F9/58C07F9/6584C07F7/0816C09K11/06C09K2211/1014C09K2211/1029C09K2211/1033C09K2211/1037C09K2211/1044C09K2211/1059C09K2211/104C09K2211/1074C09K2211/1088C09K2211/1092C09K2211/1096H10K85/623H10K85/622H10K85/631H10K85/636H10K85/626H10K85/633H10K85/654H10K85/6576H10K85/657H10K85/6574H10K85/40H10K85/6572H10K50/00H10K50/11H10K2101/10
Inventor 高威肖文静张磊代文朋李杨牛晶华李侠
Owner WUHAN TIANMA MICRO ELECTRONICS CO LTD
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