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A kind of n-heterobiphenyl organic compound and its application

An organic compound, biphenyl technology, applied in the field of organic electroluminescence, can solve the problem of difficult to develop doping materials, etc., to achieve improved equilibrium migration, luminous efficiency and lifetime improvement, high glass transition temperature and molecular thermal stability. Effect

Active Publication Date: 2021-12-17
WUHAN TIANMA MICRO ELECTRONICS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the current research status, the commercialization of heavy metal doping materials is mature, and it is difficult to develop alternative doping materials

Method used

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  • A kind of n-heterobiphenyl organic compound and its application
  • A kind of n-heterobiphenyl organic compound and its application
  • A kind of n-heterobiphenyl organic compound and its application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0134] step 1)

[0135]

[0136] In a 250mL round bottom flask, compound A (15mmol), compound B (10mmol) and Pd(PPh 3 ) 4 (0.3mmol) was added to a mixture of toluene (35mL) / ethanol (25mL) and potassium carbonate (15mmol) aqueous solution (10mL), and the reaction was refluxed under nitrogen atmosphere for 12h. The resulting mixture was cooled to room temperature, added to water, and filtered through a pad of celite. The filtrate was extracted with dichloromethane, washed with water, and dried over anhydrous magnesium sulfate. After filtration and evaporation, the crude The product yielded the target product P-1.

[0137] step (2)

[0138] Under argon (Ar) atmosphere, compound P-1 (20mmol), compound C (10mmol), Pd(OAc) 2 (1.6mmol), (tBu) 3 PHBF 4 (5mmol), K 2 CO 3(6mmol) into a 250mL three-necked flask, then heated in 150mL of toluene solvent and refluxed for about 6 hours. After cooling in air, water was added, the organic layer was separated and the solvent was dis...

Embodiment 2

[0142]

[0143] Compound P-1 was prepared as described above.

[0144] Under argon (Ar) atmosphere, compound P-1 (20mmol), compound E (10mmol), Pd(OAc) 2 (1.6mmol), (tBu) 3 PHBF 4 (5mmol), K 2 CO 3 (6mmol) into a 250mL three-necked flask, then heated in 150mL of toluene solvent and refluxed for about 6 hours. After cooling in air, water was added, the organic layer was separated and the solvent was distilled off. The crude product thus obtained was separated by silica gel column chromatography (using a mixed solvent of dichloromethane and hexane), and then recrystallized using a mixed solvent of toluene and hexane to obtain compound P-3 as a solid.

[0145] Characterization results of the organic compound P-3: molecular formula C 54 h 33 N 3 ;

[0146] ESI-MS(m / z)[M+1] analyzed by liquid chromatography-mass spectrometry + : The theoretical value is 724.27, the test value is 724.45; the theoretical value of elemental analysis: C 89.60, H 4.60, N 5.81; the test valu...

Embodiment 3

[0148]

[0149] In a 250mL round bottom flask, compound A (15mmol), compound D (10mmol) and Pd(PPh 3 ) 4 (0.3mmol) was added to a mixture of toluene (35mL) / ethanol (25mL) and potassium carbonate (15mmol) aqueous solution (10mL), and the reaction was refluxed under nitrogen atmosphere for 12h. The resulting mixture was cooled to room temperature, added to water, and filtered through a pad of celite. The filtrate was extracted with dichloromethane, washed with water, and dried over anhydrous magnesium sulfate. After filtration and evaporation, the crude The product yielded the target product P-4.

[0150] Under argon (Ar) atmosphere, compound P-4 (20mmol), compound E (10mmol), Pd(OAc) 2 (1.6mmol), (tBu) 3 PHBF 4 (5mmol), K 2 CO 3 (6mmol) into a 250mL three-necked flask, then heated in 150mL of toluene solvent and refluxed for about 6 hours. After cooling in air, water was added, the organic layer was separated and the solvent was distilled off. The crude product thus ...

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Abstract

The invention provides an N-heterobiphenyl organic compound, which has a structure represented by formula I, formula II or formula III. The invention provides a series of compounds with N-heterobiphenyl structures as electron-accepting groups. The series of organic compounds are used as host materials in electroluminescent devices and have a higher triplet energy level E T And larger molecular density, higher glass transition temperature and molecular thermal stability, effectively improve the equilibrium migration of carriers, broaden the exciton recombination area, effectively improve the extraction efficiency of light, and make the luminous efficiency and life of the device have a certain It has been greatly improved and can be well applied in the technical field of electroluminescent devices.

Description

technical field [0001] The invention relates to the technical field of organic electroluminescence, in particular to an N-heterobiphenyl organic compound and its application. Background technique [0002] As a new generation of display technology, organic electroluminescent materials (OLED) have the advantages of ultra-thin, self-luminous, wide viewing angle, fast response, high luminous efficiency, good temperature adaptability, simple production process, low driving voltage, and low energy consumption. It has been widely used in industries such as flat panel display, flexible display, solid state lighting and vehicle display. [0003] According to the mechanism of light emission, it can be divided into two types: electrofluorescence and electrophosphorescence. Fluorescence is the radiative decay transition of singlet excitons, and phosphorescence is the light emitted by the radiative decay of triplet excitons to the ground state. According to the spin quantum statistical...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D487/22C07D491/22C07D495/22C07F9/6584C09K11/06H01L51/54
CPCC07D487/22C07D491/22C07D495/22C07F9/6584C09K11/06C09K2211/1059C09K2211/1048C09K2211/1051C09K2211/1055H10K85/6572H10K85/657
Inventor 刘营姜东过宇阳代文朋李杨邓东阳张磊高威牛晶华
Owner WUHAN TIANMA MICRO ELECTRONICS CO LTD
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