Fluorene compound and light-emitting device thereof

A fluorene compound and light-emitting device technology, which is applied in the field of organic optoelectronic materials to achieve the effects of high fluorescence quantum yield, improved luminous efficiency and good film-forming properties

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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  • Fluorene compound and light-emitting device thereof
  • Fluorene compound and light-emitting device thereof
  • Fluorene compound and light-emitting device thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0134] Example 1: Synthesis of Compounds 1-3

[0135] [Synthesis of Compound M1]

[0136] The synthetic route of compound M1 is as follows:

[0137]

[0138] Under nitrogen atmosphere, 2-(methoxycarbonyl)benzeneboronic 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 the reaction was carried out 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 ...

Embodiment 2

[0160] Example 2: Synthesis of Compounds 1-4

[0161] [Synthesis of Compound M6]

[0162] The synthetic route of compound M6 is as follows:

[0163]

[0164] Under nitrogen atmosphere, phenylboronic acid (5.8g, 47.8mmol), anhydrous sodium carbonate (8.4g, 79.6mmol), compound M4 (12.2g, 39.8mmol), tetrakis(triphenylene) were successively added to a clean 250mL three-necked flask. phosphine palladium) (470.8 mg, 4.8 mmol) and a mixed solvent of toluene, water and ethanol (100 mL, toluene:water:ethanol=5:1:1 (V / V)). The system was gradually heated to reflux, and the reaction was carried out 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 silic...

Embodiment 3

[0169] Example 3: Synthesis of Compound 3-3

[0170] [Synthesis of compound 3-3]

[0171] The synthetic route of compound 3-3 is as follows:

[0172]

[0173] Under a nitrogen atmosphere, phenyl-D5-boronic acid (3.0g, 23.9mmol), anhydrous sodium carbonate (4.2g, 39.8mmol), compound M5 (10.6g, 19.9mmol), compound M5 (10.6g, 19.9mmol), Tetrakis(triphenylphosphine palladium) (235.4 mg, 2.4 mmol) and a mixed solvent of toluene, water and ethanol (100 mL, toluene:water:ethanol=5:1:1 (V / V)). The system was gradually heated to reflux, and the reaction was carried out 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 ...

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Abstract

The invention provides a 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 fluorene compound has excellent film-forming property and thermal stability, and can be used for preparing organic electroluminescent devices. The 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 fluorene compound provided by the invention has excellent transmission performance and luminescenceperformance, and can reduce the driving voltage of an organic electroluminescent device, improve the efficiency of the device and prolong the service life of the device when being used as a luminescent layer material, especially a blue light luminescent layer material. The fluorene compound is excellent in device performance, the preparation method is simple, raw materials are easy to obtain, andthe industrial development requirement can be satisfied.

Description

technical field [0001] The invention belongs to the technical field of organic optoelectronic materials, and relates to a fluorene compound and a light-emitting device comprising the fluorene compound. More specifically, the present invention relates to fluorene-based compounds suitable for organic electroluminescent devices, especially blue-light organic electroluminescent devices, and light-emitting devices using the fluorene-based compounds. Background technique [0002] Organic electroluminescent devices have a series of advantages such as self-luminous, low-voltage driving, full curing, wide viewing angle, simple composition and process, etc. Compared with liquid crystal displays, organic electroluminescent devices do not require a backlight. Therefore, organic electroluminescent devices have broad application prospects. [0003] Organic electroluminescent devices generally include an anode, a metal cathode, and an organic layer sandwiched between them. The organic la...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C13/62C07D307/91C07C13/567C09K11/06H01L51/54
CPCC07C13/62C07D307/91C07C13/567C09K11/06C09K2211/1007C09K2211/1011C09K2211/1088H10K85/623H10K85/624H10K85/622H10K85/615H10K85/6574
Inventor 张业欣朱向东崔林松陈华
Owner SUZHOU JOYSUN ADVANCED MATERIALS CO LTD
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