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Organic light-emitting molecule and application thereof in organic light-emitting diode

A technology of light-emitting diodes and organic light-emitting layers, which is applied in the fields of light-emitting materials, organic chemistry, and organic chemical methods, and can solve the problems of high device driving voltage and failure to attract widespread attention

Inactive Publication Date: 2020-10-20
东莞阿尔达新材料科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

OLED-related research can be traced back to the 1960s. In 1963, Professor Pope of New York University discovered the electroluminescence phenomenon of organic molecular single crystal anthracene for the first time, and then some single crystal structure materials have electroluminescence properties. However, due to the high driving voltage of the device at that time, it failed to attract widespread attention

Method used

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  • Organic light-emitting molecule and application thereof in organic light-emitting diode
  • Organic light-emitting molecule and application thereof in organic light-emitting diode
  • Organic light-emitting molecule and application thereof in organic light-emitting diode

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Preparation of compound M1

[0031] The structural formula and synthetic route of compound M1 are shown below, and the specific synthetic method is as follows

[0032]

[0033] (1) Synthesis of compound 1

[0034] Under nitrogen protection, phenanthrenequinone (10mmol), p-bromobenzaldehyde (10mmol) and aniline (10mmol) were added to 100ml of acetic acid, heated to reflux for 24 hours. After cooling to room temperature and standing still, suction filtration was performed, and the filter residue was washed with ethanol three times to obtain a crude product. Recrystallization with tetrahydrofuran / ethanol mixed solvent gave a white solid product with a yield of 85%. 1 H NMR, 13 The results of CNMR, MS and elemental analysis showed that the obtained compound was the target product.

[0035] (2) Synthesis of compound 2

[0036] In a nitrogen atmosphere, compound 1 (10mmol), biboronic acid pinacol ester (12 mmol), potassium acetate (10mmol), [1,1'-bis(diphenylphosphino...

Embodiment 2

[0042] Preparation of compound M2

[0043] The structural formula and synthetic route of compound M2 are shown below, and the specific synthetic method is as follows

[0044]

[0045] (1) Synthesis of Compound 4

[0046] Under nitrogen protection, phenanthrenequinone (10mmol), m-bromobenzaldehyde (10mmol) and aniline (10mmol) were added to 100ml of acetic acid, and heated to reflux for 24 hours. After cooling to room temperature and standing still, suction filtration was performed, and the filter residue was washed with ethanol three times to obtain a crude product. Recrystallization with tetrahydrofuran / ethanol mixed solvent gave a white solid product with a yield of 86%. 1 H NMR,13 The results of CNMR, MS and elemental analysis showed that the obtained compound was the target product.

[0047] (2) Synthesis of Compound 5

[0048] In a nitrogen atmosphere, compound 4 (10mmol), biboronic acid pinacol ester (12 mmol), potassium acetate (10mmol), [1,1'-bis(diphenylphosphi...

Embodiment 3

[0054] Preparation of Compounds M3 and M4

[0055] The structural formulas and synthetic routes of compounds M3 and M4 are shown below, and the specific synthetic methods are as follows

[0056]

[0057] (1) Synthesis of Compound 7

[0058] Under the protection of nitrogen, compound 2 (10mmol), 6,12-dibromide (10mmol), potassium carbonate (30mmol), tetrakis (triphenylphosphine) palladium (0.5mmol) were dissolved in 50ml of toluene and 10ml of water, and then added Tetrabutylammonium bromide was used as a phase transfer catalyst, and the temperature was raised to 85°C for 12 hours. After the reaction, the toluene solvent was distilled off under reduced pressure, the product was extracted with dichloromethane, washed three times with saturated aqueous sodium chloride solution, the organic phase was removed from the solvent using a rotary evaporator, and the crude product was purified by column chromatography, and fixed with silica gel. phase, petroleum ether / dichloromethane...

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Abstract

The invention discloses an organic light-emitting molecule and application thereof in an organic light-emitting diode. The molecule has the characteristics of wide band gap, high fluorescence quantumyield, high electron mobility, high hole mobility, high exciton utilization rate, and the like. The molecule has an asymmetric structure, and can inhibit molecular aggregation and reduce exciton quenching. In addition, the emission spectrum can be adjusted by changing the connection sites of two units. The organic light-emitting molecule can be used for preparing high-efficiency blue light organiclight-emitting devices with different emission wavelengths.

Description

technical field [0001] The invention belongs to the technical field of organic photoelectric materials, and in particular relates to an imidazole organic blue light molecule and an organic light-emitting diode with the molecule. Background technique [0002] Organic light-emitting diodes (OLEDs) have attracted extensive attention due to their advantages of flexibility, active light emission, high efficiency, low-voltage drive, and easy fabrication of large-area devices. OLED-related research can be traced back to the 1960s. In 1963, Professor Pope of New York University discovered the electroluminescence phenomenon of organic molecular single crystal anthracene for the first time, and then some single crystal structure materials have electroluminescence properties. However, due to the high driving voltage of the device at that time, it failed to attract widespread attention. It wasn't until 1987 that Deng Qingyun and others from Kodak Company of the United States developed ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D403/10C07B59/00C09K11/06H01L51/50H01L51/54
CPCC07D403/10C07B59/002C09K11/06C09K2211/1011C09K2211/1029C09K2211/1044C07B2200/05H10K85/622H10K85/615H10K85/626H10K85/6572H10K50/11
Inventor 孙文彬彭沣
Owner 东莞阿尔达新材料科技有限公司
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