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Deuterated fluorene compound and light-emitting device thereof

A light-emitting device and compound technology, which is applied in the field of organic electroluminescent devices, deuterated fluorene compounds, and light-emitting devices, to achieve good film-forming properties, thermal stability, high luminous efficiency, and low driving voltage.

Active Publication Date: 2020-12-18
SUZHOU JOYSUN ADVANCED MATERIALS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the operating lifetime of devices, especially for blue-light devices, remains an open question in this field.

Method used

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  • Deuterated fluorene compound and light-emitting device thereof
  • Deuterated fluorene compound and light-emitting device thereof
  • Deuterated fluorene compound and light-emitting device thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0146] Embodiment 1: the synthesis of compound 1-3-D30

[0147] [Synthesis of compound M1]

[0148] The synthetic route of compound M1 is as follows:

[0149]

[0150] Under nitrogen atmosphere, 2-(methoxycarbonyl)phenylboronic acid (8.6g, 47.8mmol), anhydrous sodium carbonate (8.4g, 79.6mmol), 1-bromo-4- Chloro-2-iodobenzene (12.6g, 39.8mmol), tetrakis(triphenylphosphine palladium) (470.8mg, 4.8mmol) and a mixed solvent of toluene, water and ethanol (100mL, toluene:water:ethanol=5:1 :1(V / V)). The system was gradually heated to reflux, and reacted overnight under reflux. After the reaction was completed, the heating was stopped and cooled to room temperature. The reaction solution was poured into water (about 200 mL), and extracted with dichloromethane. The organic phase was dried over anhydrous sodium sulfate, concentrated under reduced pressure, and further purified by column chromatography (the stationary phase was 350 mesh silica gel, and the eluent was petroleum e...

Embodiment 2

[0177] Embodiment 2: the synthesis of compound 1-2-D25

[0178] [Synthesis of compound M7]

[0179] The synthetic route of compound M7 is as follows:

[0180]

[0181] Under nitrogen atmosphere, phenylboronic acid (5.8g, 47.8mmol), anhydrous sodium carbonate (8.4g, 79.6mmol), compound M4 (12.2g, 39.8mmol), tetrakis(triphenyl Phosphine palladium) (470.8mg, 4.8mmol) and a mixed solvent of toluene, water and ethanol (100mL, toluene:water:ethanol=5:1:1 (V / V)). The system was gradually heated to reflux, and reacted overnight under reflux. After the reaction was completed, the heating was stopped and cooled to room temperature. The reaction solution was poured into water (about 200 mL), and extracted with dichloromethane. The organic phase was dried over anhydrous sodium sulfate, concentrated under reduced pressure, and further purified by column chromatography (the stationary phase was 350 mesh silica gel, and the eluent was petroleum ether:dichloromethane=15:1 (V / V)), to ob...

Embodiment 3

[0191] Embodiment 3: the synthesis of compound 1-1-D25

[0192] [Synthesis of compound M9]

[0193] The synthetic route of compound M9 is as follows:

[0194]

[0195]Under nitrogen atmosphere, (10-phenylanthracene-9-yl)boronic acid (14.2g, 47.8mmol), anhydrous sodium carbonate (8.4g, 79.6mmol), compound M4 (12.2 g, 39.8mmol), tetrakis(triphenylphosphine palladium) (470.8mg, 4.8mmol) and a mixed solvent of toluene, water and ethanol (100mL, toluene:water:ethanol=5:1:1 (V / V)) . The system was gradually heated to reflux, and reacted overnight under reflux. After the reaction was completed, the heating was stopped and cooled to room temperature. The reaction solution was poured into water (about 200 mL), and extracted with dichloromethane. The organic phase was dried over anhydrous sodium sulfate, concentrated under reduced pressure, and further purified by column chromatography (the stationary phase was 350 mesh silica gel, and the eluent was petroleum ether:dichlorometh...

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Abstract

The invention provides a deuterated fluorene compound and a light-emitting device thereof. Fluorene functional groups with rigid structures are introduced into organic compounds through unique large-steric-hindrance connection sites. The formed deuterated fluorene compound has excellent film-forming property and thermal stability, and can be used for preparing organic electroluminescent devices. The deuterated fluorene compound disclosed by the invention is particularly suitable for preparing a blue organic light-emitting device and can be used as a constituent material of a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer or an electron transport layer. More importantly, the deuterated fluorene compound provided by the invention has excellenttransmission performance and luminescence performance, and can reduce the driving voltage of an organic electroluminescent device, improve the efficiency of the device and prolong the service life ofthe device when being used as a luminescent layer material, especially a blue light luminescent layer material. The deuterated fluorene compound is excellent in device performance, the preparation method is simple, raw materials are easy to obtain, and industrial development requirements can be met.

Description

technical field [0001] The invention belongs to the technical field of organic photoelectric materials, and relates to a deuterated fluorene compound and a light-emitting device containing the deuterated fluorene compound. More specifically, the present invention relates to a deuterated fluorene compound suitable for organic electroluminescent devices, especially blue-light organic electroluminescent devices, and a light-emitting device using the deuterated fluorene compound. Background technique [0002] Organic electroluminescent devices have a series of advantages such as self-luminescence, low-voltage drive, full curing, wide viewing angle, simple composition and process, etc. Compared with liquid crystal displays, organic electroluminescent devices do not need a backlight. Therefore, organic electroluminescent devices have broad application prospects. [0003] An organic electroluminescent device generally includes an anode, a metal cathode, and an organic layer sandwi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C13/567C07D307/91C07D209/86C09K11/06H01L51/54
CPCC07C13/567C07D307/91C07D209/86C09K11/06C09K2211/1007C09K2211/1011C09K2211/1029C09K2211/1088H10K85/615H10K85/6572
Inventor 张业欣朱向东崔林松陈华
Owner SUZHOU JOYSUN ADVANCED MATERIALS CO LTD
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