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A kind of derivative of carbazole-thienopyrazine and its preparation method, application and device

A technology of derivatives and thiophene, which is applied in the field of carbazole-thienopyrazine derivatives and its preparation, can solve the problems of self-quenching, doping, and affecting green color purity and device functions of green light-emitting materials.

Active Publication Date: 2020-10-30
WUHAN SUNSHINE OPTOELECTRONICS TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] At present, due to the shortcomings of self-quenching effect and relatively weak charge transport performance of green light-emitting materials, doping technology is often used to prepare light-emitting devices.
In doped devices, due to insufficient energy transfer, phase separation between the host and the guest, the host and the guest emit light at the same time, and the device is unstable, which seriously affects the color purity of green light and the device function; in addition, the doped luminescence The device is prepared by evaporation or mixed solution spin coating method, and the device preparation process is much more complicated than that of the non-doped type.

Method used

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  • A kind of derivative of carbazole-thienopyrazine and its preparation method, application and device
  • A kind of derivative of carbazole-thienopyrazine and its preparation method, application and device
  • A kind of derivative of carbazole-thienopyrazine and its preparation method, application and device

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Experimental program
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Effect test

Embodiment 1

[0110] Compound (2) according to the present invention can be synthesized by the following method.

[0111] 1) In a 500ml three-necked flask, add 2,7-dibromo-9H-carbazole (32.50g, 100mmol), [1,1′:4,1″-terphenyl]-4-boronate (35.60g , 100mmol), potassium carbonate (27.64g, 200mmol), 150g toluene, 75g ethanol, 75g water, in N 2 Tetrakis(triphenylphosphine)palladium was added under protection and reacted at 85° C. for 12 h. The reaction was completed as monitored by TLC, and the temperature began to drop. After cooling down to room temperature, [1,1′-biphenyl]-3-boronate (29.62 g, 100 mmol) was added into the three-necked flask, and reacted at 85°C for 12 hours, and the reaction was detected by TLC. After cooling to room temperature, the reaction solution was washed twice with water (200ml), separated to obtain the organic phase, added activated carbon for decolorization, filtered, and evaporated under reduced pressure to remove the solvent, dissolved and recrystallized twice wit...

Embodiment 2

[0115] The compound (6) described in the present invention can be synthesized by the following method.

[0116] 1) Add 3,5-dibromo-9H-carbazole (32.50g, 100mmol), [1,1′-biphenyl]-4-boronate (29.62g, 100mmol), potassium carbonate into a 500ml three-necked flask (27.64g, 200mmol), 150g toluene, 75g ethanol, 75g water, in N 2 Tetrakis(triphenylphosphine)palladium was added under protection, and reacted at 85° C. for 12 hours. The completion of the reaction was monitored by TLC, and the temperature began to drop.

[0117] After cooling down to room temperature, 4-(1-phenyl-1H-benzimidazol-2-yl)phenylboronate (39.63g, 100mmol) was added into the three-necked flask, and reacted at 85°C for 12h, and the reaction was detected by TLC. After cooling to room temperature, the reaction solution was washed twice with water (200ml), separated to obtain the organic phase, added activated carbon for decolorization, filtered, and evaporated under reduced pressure to remove the solvent, dissolv...

Embodiment 3

[0121] (44) described in the present invention can be synthesized by the following method.

[0122] 1) In a 500ml three-necked flask, add 3,7-dibromo-9H-carbazole (32.50g, 100mmol), 3-(9H-carbazol-9-yl)phenylboronate (36.93g, 100mmol), Potassium carbonate (27.64g, 200mmol), 150g toluene, 75g ethanol, 75g water, in N 2 Tetrakis(triphenylphosphine)palladium was added under protection, and reacted at 85° C. for 12 hours. The completion of the reaction was monitored by TLC, and the temperature began to drop. After cooling down to room temperature, anthracenyl-2-boronate (30.42 g, 100 mmol) was added into the three-necked flask, and reacted at 85° C. for 12 h, and the reaction was detected by TLC. After cooling to room temperature, the reaction solution was washed twice with water (200ml), separated to obtain the organic phase, added activated carbon for decolorization, filtered, and evaporated under reduced pressure to remove the solvent, dissolved and recrystallized twice with e...

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PUM

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Abstract

The invention relates to a derivative of carbazole-thienopyrazine and its preparation, application and device. A derivative of carbazole-thienopyrazine provided by the present invention takes carbazole and thienopyrazine as basic structural units, and obtains a bipolar structure after being modified with a hole-containing group, which has a high Glass transition temperature, and good stability. When it is applied to an organic electroluminescent device as a green light-emitting material, compared with the green doped materials commonly used in the prior art, it can effectively avoid insufficient energy transfer, phase separation between host and guest, and the driving voltage of the device. , Luminous brightness, external quantum efficiency and roll-off have been significantly improved, and it is an ideal green light-emitting material.

Description

technical field [0001] The invention belongs to the technical field of photoelectric material application technology, and specifically relates to a derivative of carbazole-thienopyrazine and its preparation method, application and device. Background technique [0002] Organic Light-emitting Diode (Organic Light-emitting Diode), also known as organic electroluminescent device or organic light-emitting display (Organic Light-emitting Display, OLED), is a new display technology with ultra-thin, fast response, light weight , high brightness, wide viewing angle, self-illumination, low power consumption, low cost, flexible and able to work normally under low temperature conditions and other superior performance, it is praised by the industry as the ideal and most promising display and lighting product after LCD . An OLED is a sandwich-type basic structure that includes an anode, a cathode, and a layer of organic material placed in between. The organic material layer can be forme...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D495/04C07F7/08C07D513/04C09K11/06H01L51/50H01L51/54
Inventor 穆广园庄少卿任春婷
Owner WUHAN SUNSHINE OPTOELECTRONICS TECH CO LTD
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