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A class of light-emitting small molecule materials based on macrocyclic units and its preparation method and application

A technology of small molecules and light-emitting layers, applied in the direction of light-emitting materials, chemical instruments and methods, electrical components, etc., can solve the difficulties in the purification of light-emitting polymers, batch repeatability, unsuitable for the popularization and application of large-area OLED devices, complex processes, etc. problems, to achieve the effects of excellent electron and hole transport performance, excellent electroluminescence performance, and high fluorescence emission efficiency

Active Publication Date: 2022-03-25
CHANGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, the small-molecule fluorescent materials used in the display field are mainly evaporation process, but the process is complicated, the luminescent materials are wasteful, and the cost is high, so it is not suitable for the popular application of large-area OLED devices.
In addition, polymer electroluminescent devices that can be applied to solution processing have seriously affected the application of light-emitting polymers due to the difficulty in purification of light-emitting polymers and the problem of batch repeatability.

Method used

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  • A class of light-emitting small molecule materials based on macrocyclic units and its preparation method and application
  • A class of light-emitting small molecule materials based on macrocyclic units and its preparation method and application
  • A class of light-emitting small molecule materials based on macrocyclic units and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Example 1 Synthesis of 9,9-bis(2-ethylhexyl)-2,7-bis(2-methylsulfinyl)phenyl)-9H-fluorene (Compound 3)

[0038] 2,2'-(9,9-bis(2-ethylhexyl-9H-fluorene-2,7-diyl)-bis(4,4,5,5-tetramethyl-1,3,2- Dioxaborolane) (9.64g, 15mmol, purchased from Guangzhou Kongsiben Chemical Co., Ltd.), 1-bromo-2-(methyl-sulfinyl)benzene (7.23g, 33mmol, New J. Chem., 2015, 39, 6513-6521.), tetrakis(triphenylphosphine) palladium catalyst (0.87g, 0.75mmol), tetrabutylammonium bromide phase transfer catalyst (0.24g, 0.75mmol) under nitrogen atmosphere Completely dissolve in 200ml toluene, then inject 20.7ml fresh K 2 CO 3 (20.7 g, 0.15 mol) aqueous solution (50 wt%) and reacted at 80°C for 24 hours. After cooling to room temperature, the organic layer was separated, the aqueous layer was extracted with dichloromethane, washed with water, and then concentrated by a rotary evaporator, and the crude product was purified by silica gel column chromatography. A mixture of petroleum ether / dichlorometh...

Embodiment 2

[0040] Example 2 Synthesis of 9,9-bis(2-ethylhexyl)bis[2,3-b; 6,7-b]benzo[d]thiophene (Compound 4)

[0041] 9,9-bis(2-ethylhexyl)-2,7-bis(2-methylsulfinyl)phenyl)-9H-fluorene (468.9 mg, 0.668 mmol), trifluoromethanesulfonic acid (4.2 mL) ) and phosphorus pentoxide (254.5 mg, 1.336 mmol) were added to a 250 mL round bottom flask. The mixture was stirred at room temperature for 12 hours and then poured into ice water. After the precipitate was collected and dried in vacuo, it was dissolved in 50 ml of pyridine under nitrogen and reacted at 90°C for 8 hours. When it cooled to room temperature, the mixture was extracted with dichloromethane and washed with water, concentrated by rotary evaporator. The crude product was purified by silica gel column chromatography using petroleum ether as eluent. A white solid was obtained in 52% yield (207 mg).

[0042]

Embodiment 3

[0043] Example 3 Synthesis of 9,9-bis(2-ethylhexyl)bis[2,3-b;6,7-b]benzo[d]thiophene-S,S-dioxide (Compound 5)

[0044] 9,9-Bis(2-ethylhexyl)bis[2,3-b;6,7-b]benzo[d]thiophene (2.89 g, 4.8 mmol) was completely dissolved in 40 ml of anhydrous bisulfite at room temperature In methyl chloride, m-chloroperbenzoic acid (4.14 g, 24 mmol) was added in three portions. After stirring at room temperature for 8 hours, saturated aqueous sodium hydroxide solution was added to terminate the reaction. The mixture was extracted with dichloromethane and washed with water and concentrated by rotary evaporation. The crude product was purified by silica gel column chromatography using petroleum ether / dichloromethane mixture (2:1 by volume) as eluent. A white solid was obtained in 84% yield (2.69 g).

[0045]

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Abstract

The invention belongs to the field of organic light-emitting materials, and in particular relates to a class of light-emitting small molecule materials based on macrocyclic units and a preparation method and application thereof. A small molecular luminescent material with high thermal stability, excellent electron and hole transport properties, and high fluorescence emission efficiency is obtained by covalently connecting various aromatic ring units with macrocyclic units at different substituent positions. This kind of luminescent material can be applied in the industrialized production of organic electroluminescence display and cell imaging.

Description

technical field [0001] The invention belongs to the field of organic light-emitting materials, and in particular relates to a class of light-emitting small molecule materials based on macrocyclic units and a preparation method and application thereof. Background technique [0002] Compared with liquid crystal displays (LCDs), organic electroluminescent diodes (OLEDs) have attracted extensive attention from scientific research institutions and industries due to their wide viewing angle, active light emission, ground operating voltage, ultra-thinness, flexible fabrication, and low power consumption. . At present, OLEDs displays have been used in mobile phone screens, and large-area OLED TVs have been developed and put on the market. However, OLEDs also limit the widespread and large-area use of OLEDs due to their disadvantages such as high prices. Therefore, the development of new light-emitting materials, the improvement of the device fabrication process level and the yield...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D495/04C09K11/06H01L51/54
CPCC07D495/04C09K11/06C09K2211/1092C09K2211/1011H10K85/624H10K85/615H10K85/6576
Inventor 张斌
Owner CHANGZHOU UNIV
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