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Terpyridine derivative and preparation method and application thereof as well as device

A technology of terpyridines and derivatives, applied in the field of terpyridine derivatives and their preparation, can solve the problems of poor stability, low efficiency and the like

Active Publication Date: 2019-06-18
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 derivative and preparation method and application thereof as well as device
  • Terpyridine derivative and preparation method and application thereof as well as device
  • Terpyridine derivative and preparation method and application thereof as well as device

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 application science and technology of organic photoelectric materials, and particularly relates to a terpyridine derivative and a preparation method and application thereof as well as a device. The derivative provided by the invention is characterized by being mainly based on a terpyridine core, peripherally using a carbazole derivative and the like to regulate appropriate electron donating ability, and transforming different bridging groups through a D-A structure design to regulate the appropriate distribution of highest occupied molecular orbital (HOMO)and lowest unoccupied molecular orbital (LUMO); the derivative is mainly applied to 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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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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