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Terpyridine derivatives, preparation method, application and device thereof

A technology of terpyridines and terpyridine coupling, which is applied in the fields of electric solid-state devices, semiconductor devices, chemical instruments and methods, etc., and can solve problems such as low efficiency and poor stability

Active Publication Date: 2021-03-30
WUHAN SUNSHINE OPTOELECTRONICS TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The purpose is to synthesize terpyridine derivatives through a simple and feasible synthesis scheme and apply them to electroluminescent materials, thereby solving the technical problems of poor stability and low efficiency of blue light materials in the prior art

Method used

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  • Terpyridine derivatives, preparation method, application and device thereof
  • Terpyridine derivatives, preparation method, application and device thereof
  • Terpyridine derivatives, preparation method, application and device thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039]

[0040] (5-(4-([2,2':6',2"-terpyridine]-4'-yl)phenyl)-12,12-dimethyl-5,12-dihydroindeno[1 , 2-c] carb) preparation:

[0041] (1) In a dry 500ml two-necked flask, 3-carbazole boronic acid pinacol ester (15g, 51mmol), o-dibromobenzene (14.5g, 61.2mmol), toluene (120mL), ethanol (60mL) Add 2mol / L potassium carbonate solution (60mL), first ultrasonic for 5-10 minutes, then quickly stir and blow nitrogen for 5 minutes, quickly add catalyst tetrakis(triphenylphosphine)palladium (1.8g, 1.53mmol), and blow nitrogen in large quantities 10 minutes. Heated to 100°C and stirred at reflux for 12h. During treatment, extract first, spin dry, and use petroleum ether and dichloromethane column chromatography to obtain a white solid product 3-(2-bromophenyl)-9H-carbazole with a yield of 93%.

[0042] (2) 3-(2-bromophenyl)-9H-carbazole (20.73g, 64.4mmol), di-tert-butyl dicarbonate (19.67g, 90.13mmol) and 4-dimethylaminopyridine (0.787g, 6.44mmol) was placed in a 500mL single-necke...

Embodiment 2

[0047]

[0048] (5-(4-([2,2':6',2"-terpyridine]-4'-yl)phenyl)-12,12-diphenyl-5,12-dihydroindeno[1 ,2-c]carba) preparation

[0049] (1) In a dry 500ml two-necked flask, 3-carbazole boronic acid pinacol ester (15g, 51mmol), o-dibromobenzene (14.5g, 61.2mmol), toluene (120mL), ethanol (60mL) Add 2mol / L potassium carbonate solution (60mL), first ultrasonic for 5-10 minutes, then quickly stir and blow nitrogen for 5 minutes, quickly add catalyst tetrakis(triphenylphosphine)palladium (1.8g, 1.53mmol), and blow nitrogen in large quantities 10 minutes. Heated to 100°C and stirred at reflux for 12h. During treatment, extract first, spin dry, and use petroleum ether and dichloromethane column chromatography to obtain a white solid product 3-(2-bromophenyl)-9H-carbazole with a yield of 93%.

[0050] (2) 3-(2-bromophenyl)-9H-carbazole (20.73g, 64.4mmol), di-tert-butyl dicarbonate (19.67g, 90.13mmol) and 4-dimethylaminopyridine (0.787g, 6.44mmol) was placed in a 500mL single-necked ...

Embodiment 3

[0056]

[0057] (5'-(4-([2,2':6',2"-terpyridine]-4'-yl)phenyl)-5'H-spiro[fluorene9,12'indeno[1,2 -c] Preparation of carbazole])

[0058] (1) In a dry 500ml two-necked flask, 3-carbazole boronic acid pinacol ester (15g, 51mmol), o-dibromobenzene (14.5g, 61.2mmol), toluene (120mL), ethanol (60mL) Add 2mol / L potassium carbonate solution (60mL), first ultrasonic for 5-10 minutes, then quickly stir and blow nitrogen for 5 minutes, quickly add catalyst tetrakis(triphenylphosphine)palladium (1.8g, 1.53mmol), and blow nitrogen in large quantities 10 minutes. Heated to 100°C and stirred at reflux for 12h. During treatment, extract first, spin dry, and use petroleum ether and dichloromethane column chromatography to obtain a white solid product 3-(2-bromophenyl)-9H-carbazole with a yield of 93%.

[0059] (2) 3-(2-bromophenyl)-9H-carbazole (20.73g, 64.4mmol), di-tert-butyl dicarbonate (19.67g, 90.13mmol) and 4-dimethylaminopyridine (0.787g, 6.44mmol) was placed in a 500mL single-n...

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Abstract

The invention belongs to the field of applied science and technology of organic photoelectric materials, and specifically relates to terpyridine derivatives and their preparation methods, applications and devices. The invention provided is mainly based on the core of terpyridine, and carbazole derivatives are used in the periphery to regulate the appropriate electron-donating ability, and the D-A structure design is used to change different bridging groups to regulate the appropriate lowest occupied orbital (HOMO) and The distribution of the highest unoccupied orbital (LUMO) is mainly used in TADF guest materials, host materials, and carrier transport materials.

Description

technical field [0001] The invention belongs to the field of applied science and technology of organic photoelectric materials, and specifically relates to terpyridine derivatives and their preparation methods, applications and devices. Background technique [0002] Organic light-emitting diodes (OLEDs) have the advantages of thinness, self-luminescence, high contrast, easy to manufacture in large areas, and can be used in flexible and transparent display and lighting fields. They are known as "dream display" and the next generation of solid-state lighting technology. In 1963, Professor Pope applied a bias voltage of hundreds of volts to the crystal of anthracene to emit faint blue light, but due to the high voltage and poor luminous efficiency, it did not attract people's attention. Since 1987, Dr. Deng Qingyun (C.W.Tang) and Steve VanSlyke have made multi-layer OLED devices by vacuum evaporation, which greatly reduces the driving voltage of the device and improves the lumi...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D401/14C07D491/048C07D495/04C07D487/04C09K11/06H01L51/54
Inventor 穆广园庄少卿吕夏蕾
Owner WUHAN SUNSHINE OPTOELECTRONICS TECH CO LTD
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