Organic compound based on triazine and benzimidazolone structures and application of organic compound in organic electroluminescent device

A technology of organic compounds and benzimidazoles, applied to organic electroluminescent devices, in the field of organic compounds based on triazine and benzimidazolone structures, can solve the problem of affecting the OLED radiation spectrum angle distribution and complex fabrication process And other issues

Inactive Publication Date: 2020-04-07
JIANGSU SUNERA TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The first two structures will affect the angular distribution of the radiation spectrum of the OLED. The third structure is complicated to manufacture, and the process of using a surface covering layer is simple, and the luminous efficiency is increased by more than 30%, which is particularly concerned by people.

Method used

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  • Organic compound based on triazine and benzimidazolone structures and application of organic compound in organic electroluminescent device
  • Organic compound based on triazine and benzimidazolone structures and application of organic compound in organic electroluminescent device
  • Organic compound based on triazine and benzimidazolone structures and application of organic compound in organic electroluminescent device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0144] Synthesis of Intermediate A

[0145]

[0146] (1) Under a nitrogen atmosphere, weigh the raw material I and dissolve it in tetrahydrofuran (THF), then add bis(pinacolate) diboron, (1,1-bis(diphenylphosphino)ferrocene) dichloropalladium (II)(Pd(pddf) 2 Cl 2 ) and potassium acetate (KOAc) were added, the mixture was stirred, and the mixed solution of the above reactants was heated and refluxed at a reaction temperature of 70-90°C for 5-10 hours; after the reaction was completed, water was added to cool, the mixture was filtered, and the filter cake was Dry in an oven, dissolve the dried filter cake and pass through a silica gel column for separation and purification to obtain intermediate E; the molar ratio of the raw material I to bis(pinacolate) diboron is 1:1.0~3, Pd(dppf) 2 Cl 2 The molar ratio to raw material I is 0.001-0.04:1, the molar ratio of potassium acetate to raw material I is 1.0-4.0:1, and the ratio of raw material I to THF is 1g:10-30ml.

[0147] (2...

Embodiment 2

[0163] Embodiment 2: the synthesis of intermediate B

[0164]

[0165] Among them, L 1 and L 2 independently select hydrogen atom or -Ar 2 -Cl, x and y are natural numbers and x+y=a; X 1 Expressed as -O-, -S-, -N(R 11 )-.

[0166] (1) In a 250ml four-necked flask, under an atmosphere of nitrogen gas, add 0.01mol of raw material III, 0.02mol of raw material IV, 0.15mol of O-benzotriazole-tetramethyluronium hexafluorophosphate ( HBTU), 0.15mol of N,N-diisopropylethylamine (DIPEA), 80ml of DMF, stirring and reacting at room temperature for 5 hours, taking a sample and spotting the plate, showing that the reaction is complete; adding 80ml of ethyl acetate to the reaction mixture to dilute, Wash with 100ml of water and 100ml of brine in turn; separate the organic layer using a separatory funnel, MgSO 4 After drying and filtering, the filtrate was rotary evaporated under reduced pressure and passed through a neutral silica gel column to obtain intermediate F.

[0167] (2) ...

Embodiment 3

[0184] Embodiment 3: the synthesis of compound 9

[0185]

[0186] In a 250mL three-necked flask, blow nitrogen, add 0.01mol of intermediate A-1, 150ml of DMF, 0.015mol of intermediate B-5, 0.0002mol of palladium acetate, stir, and then add 10mL of 0.004mol / mL of K 3 PO 4 Aqueous solution, heated to 125 ° C, reflux reaction for 5 hours, sampling point plate, after the reaction, cooled and added 100ml of water, and the mixture was filtered and the obtained solid was dried in a vacuum oven; the obtained solid was washed with dichloromethane After dissolving, it was separated and purified through a silica gel column with dichloromethane:ethyl acetate=3:1 eluent to obtain intermediate D-9 with a HPLC purity of 99.1% and a yield of 76.2%.

[0187] In a 250mL three-necked flask, blow nitrogen, add 0.01mol intermediate D-9, 150ml DMF, 0.015mol intermediate B-1, 0.0002mol palladium acetate, stir, and then add 10mL 0.004mol / mL of K 3 PO 4 Aqueous solution, heated to 150 ° C, refl...

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PUM

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Abstract

The invention relates to an organic compound based on triazine and benzimidazolone structures and an application of the organic compound in an organic electroluminescent device. The structure of the compound simultaneously contains the triazine and benzimidazolone structures, and the compound has high glass transition temperature and molecular thermal stability; the compound is low in absorption and high in refractive index in the field of visible light, and after the compound is applied to a covering layer of an OLED device, the light extraction efficiency of the OLED device can be effectively improved; the compound disclosed by the invention also has a relatively deep HOMO energy level and high electron mobility, can be used as a hole blocking or electron transport layer material of theOLED device, and can effectively block holes or energy from being transmitted from a light emitting layer to one side of an electron layer, thereby improving the recombination efficiency of the holesand electrons in the light emitting layer, improving the light emitting efficiency of the OLED device, and prolonging the service life of the OLED device.

Description

technical field [0001] The invention relates to the technical field of semiconductors, in particular to an organic compound based on a triazine and benzimidazolone structure and its application in an organic electroluminescent device. Background technique [0002] Due to the huge gap between the external quantum efficiency and internal quantum efficiency of OLEDs, the development of OLEDs is greatly restricted. Therefore, how to improve the light extraction efficiency of OLEDs has become a research hotspot. Total reflection will occur at the interface between the ITO film and the glass substrate and the interface between the glass substrate and the air, and the light emitted to the front of the OLED device to the external space accounts for about 20% of the total EL of the organic material film, and the remaining about 80% of the light It is mainly confined in organic material thin films, ITO thin films and glass substrates in the form of guided waves. It can be seen that ...

Claims

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Application Information

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IPC IPC(8): C07D498/04C07D519/00H01L51/54
CPCC07D519/00C07D498/04H10K85/615H10K85/631H10K85/654H10K85/657H10K85/6574H10K85/6572
Inventor 李崇吴逸唐丹丹王芳陈海峰
Owner JIANGSU SUNERA TECH CO LTD
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