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 t

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

Example Embodiment

[0143] Example 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 dissolve bis(pinacol) diboron, (1,1-bis(diphenylphosphine)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 to reflux at a reaction temperature of 70-90°C for 5-10 hours; after the reaction, water was added to cool, the mixture was filtered, and the filter cake was placed in a vacuum Dry in an oven, dissolve the dried filter cake and pass it through a silica gel column for separation and purification to obtain intermediate E; the molar ratio of the raw material I and bis(pinacol) diboron is 1:1.0~3, Pd(dppf) 2 Cl 2 The molar ratio to the raw material I is 0.001 to 0.04:1, the molar ratio of potassium acetate to the raw material I is 1.0 to 4.0:1, and the ratio of the amount of raw mate...

Example Embodiment

[0163] Example 2: 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-neck flask, add 0.01 mol of raw material III, 0.02 mol of raw material IV, and 0.15 mol of O-benzotriazole-tetramethylurea hexafluorophosphate ( HBTU), 0.15mol of N,N-diisopropylethylamine (DIPEA), 80ml of DMF, stirred and reacted at room temperature for 5 hours, sampling the spot plate, showing that the reaction was complete; the reaction mixture was diluted by adding 80ml of ethyl acetate, Wash with 100ml water and 100ml brine successively; use a separatory funnel to separate the organic layer, MgSO 4 After drying and filtering, the filtrate was subjected to reduced pressure rotary evaporation, and passed through a neutral silica gel column to obtain Intermediate F.

[0167] (2) A 250ml four-neck flask, add 0.06mol of intermediate F, control...

Example Embodiment

[0184] Example 3: Synthesis of Compound 9

[0185]

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

[0187] In a 250mL three-necked flask, add 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 K 3 PO 4 The aqueous solution, heated to 150°C, refluxed for reaction for 14 hours, sampled a spot pl...

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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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