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Organic optoelectronic material and application thereof

A technology of organic optoelectronic materials and light-emitting layers, applied in the fields of light-emitting materials, organic chemistry, circuits, etc., to achieve the effects of reducing the singlet-triplet energy gap, reducing overlap, and high exciton utilization.

Active Publication Date: 2019-10-08
WUHAN SUNSHINE OPTOELECTRONICS TECH CO LTD
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  • Abstract
  • Description
  • Claims
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AI Technical Summary

Problems solved by technology

[0005] The quantum efficiency of thermally induced delayed fluorescent materials has greatly broken through the theoretical limit of traditional fluorescent devices, but in fact it faces the following three problems: (1) How to adjust the fine structure of the designed molecules so that the spin coupling parameters of the materials are consistent with The singlet-triplet energy level difference, and the radiative transition constant (k f ) can effectively cooperate, so that the material has both high exciton utilization rate and high fluorescence radiation efficiency; (2) how to improve the radiative transition constant (k f ), avoiding non-radiative transitions so that the singlet radiative transition constant (k f ) is greater than the transition constant (k isc ), improving device efficiency roll-off from the perspective of regulating exciton lifetime; (3) on the basis of high-efficiency thermally induced delayed fluorescence materials, how to match functional materials of different energy levels to improve device performance from the perspective of device structure

Method used

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  • Organic optoelectronic material and application thereof
  • Organic optoelectronic material and application thereof
  • Organic optoelectronic material and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] Compound 3 provided by the present invention can be synthesized by the following method.

[0049]

[0050] (1) In a 500ml three-necked flask, add 4,6-dichloro-1,3,5-triazin-2-amine (16.50g, 100mmol), 4-tert-butylphenylboronic acid (35.60g, 200mmol), Potassium carbonate (27.64g, 200mmol), toluene 150mL, ethanol 75mL, water 75mL, in N 2 Tetrakis(triphenylphosphine)palladium (0.35 g, 3 mmol) was added under protection, the reaction was controlled at 85° C., and the reaction was carried out for 12 h, and the reaction was completed by liquid phase monitoring. Cool to room temperature, wash twice with water, add activated carbon for decolorization, filter, concentrate to obtain a light yellow solid, recrystallize twice from ethanol, and dry under vacuum to obtain 4,6-bis(4-tert-butylphenyl)-1,3, 32.44 g of 5-triazin-2-amine, yield 90%.

[0051] (2) In a 500ml three-necked flask, add phenanthrenequinone (10.41g, 50mmol), 4,6-di(4-tert-butylphenyl)-1,3,5-triazin-2-amine (2...

Embodiment 2

[0053] Compound 12 provided by the present invention can be synthesized by the following method.

[0054]

[0055] (1) In a 500ml three-necked flask, add 4,6-dichloro-1,3,5-triazin-2-amine (16.50g, 100mmol), (9,9-dimethyl-9H-fluorene-2 -base) boric acid (47.62g, 200mmol), potassium carbonate (27.64g, 200mmol), toluene 150mL, ethanol 75mL, water 75mL, in N 2 Tetrakis(triphenylphosphine)palladium (0.35 g, 3 mmol) was added under protection, the reaction was controlled at 85° C., and the reaction was carried out for 12 h, and the reaction was completed by liquid phase monitoring. Cool to room temperature, wash twice with water, add activated carbon for decolorization, filter, concentrate to obtain a light yellow solid, recrystallize twice from ethanol, and dry under vacuum to obtain 4,6-bis(9,9-methyl-9H-fluorene-2- base)-1,3,5-triazin-2-amine 42.29g, yield 88%.

[0056] (2) In a 500ml three-necked flask, add phenanthrenequinone (10.41g, 50mmol), 4,6-di(9,9-methyl-9H-fluoren...

Embodiment 3

[0058] Compound 21 provided by the present invention can be synthesized by the following method.

[0059]

[0060] (1) In a 500ml three-necked flask, add 4,6-dichloro-1,3,5-triazin-2-amine (16.50g, 100mmol), phenylboronic acid (24.39g, 200mmol), potassium carbonate (27.64g , 200mmol), toluene 150mL, ethanol 75mL, water 75mL, in N 2 Tetrakis(triphenylphosphine)palladium (0.35 g, 3 mmol) was added under protection, the reaction was controlled at 85° C., and the reaction was carried out for 12 h, and the reaction was completed by liquid phase monitoring. Cool to room temperature, wash twice with water, add activated carbon for decolorization, filter, concentrate to obtain a light yellow solid, recrystallize twice from ethanol, and dry under vacuum to obtain 4,6-diphenyl-1,3,5-triazine-2- Amine 22.35g, yield 90%.

[0061] (2) In a 500ml three-necked flask, add phenanthrenequinone (10.41g, 50mmol), 4,6-diphenyl-1,3,5-triazin-2-amine (14.89g, 60mmol), [1,1 '-Biphenyl]-4-formal...

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Abstract

The invention belongs to the scientific and technical field of optoelectronic material application, and particularly relates to an organic photoelectric material and application thereof. The organic photoelectric material comprises phenanthroimidazole and triazine as basic structural units to form a thermotropic delayed fluorescent material, linkage or thickening of triazine and imidazole groups with strong electron-donating properties and phenanthrene groups with large conjugate planes effectively improves the roll-off of devices, further modification of functional groups with strong electron-withdrawing properties improves exciton transport and luminescence properties of the devices under high current density, and the organic photoelectric material is an ideal material for luminous layers, electron transport or light emitting layers of the organic electroluminescent devices.

Description

technical field [0001] The invention belongs to the technical field of photoelectric material application technology, and in particular relates to an organic photoelectric material and its application. Background technique [0002] Organic light-emitting diode (Organic Light-Emitting Diode, OLED), also known as organic electrical laser display, organic light-emitting semiconductor, was discovered in the laboratory by Chinese-American professor Ching W.Tang in 1979, due to its own The advantages of luminescence, wide viewing angle, almost infinitely high contrast, low power consumption, and extremely high response speed are widely used in mobile phones, digital cameras, notebook computers, car displays, TVs, and lighting. The continuous development of OLED materials and The improvement of the performance of organic light-emitting diodes has become a research hotspot in the field of optoelectronic technology. [0003] OLED materials can be divided into three generations based...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D403/04C07D405/14C07D409/14C07D403/14C09K11/06H01L51/50H01L51/54
CPCC07D403/04C07D405/14C07D409/14C07D403/14C09K11/06C09K2211/1029C09K2211/1044C09K2211/1059C09K2211/1088C09K2211/1092C09K2211/1007C09K2211/1011C09K2211/1014H10K85/615H10K85/631H10K85/654H10K85/6572H10K85/6574H10K85/6576H10K50/00
Inventor 穆广园庄少卿任春婷
Owner WUHAN SUNSHINE OPTOELECTRONICS TECH CO LTD
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