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Polycyclic boron-containing compound and electronic device thereof

A boron compound and electronic device technology, applied in the field of organic optoelectronic materials, can solve the problems of difficult material purification, limited application, easy formation of isomers, etc., and achieves broad industrialization prospects, simple preparation methods, and narrow half-peak widths.

Active Publication Date: 2020-09-11
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 carbazole and fluorene units described in Patent Document 3 are mainly in their 2 and 3 positions. During material preparation, it is easy to form isomers, and the material purification is difficult, thus limiting its industrial application.

Method used

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  • Polycyclic boron-containing compound and electronic device thereof
  • Polycyclic boron-containing compound and electronic device thereof
  • Polycyclic boron-containing compound and electronic device thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0146] Embodiment 1: the synthesis of compound 1-5

[0147] [Synthesis of Intermediate 1-5-1]

[0148]

[0149] Under a nitrogen atmosphere, 1-chloro-9,9-dimethylfluorene (11.4 g, 50.0 mmol), 2,4,6-trimethylaniline (6.8 g , 50.0mmol), sodium tert-butoxide (9.6g, 100.0mmol), n-butylbis(1-adamantyl)phosphine (1.8g, 10.0mmol), tris(dibenzylideneacetone)dipalladium (2.9g , 5.0mmol) and toluene (200mL), and heated to reflux for 6h. After the reaction, the system was cooled to room temperature. A large amount of water was added to form a white precipitate, which was collected by suction filtration. The precipitate was washed successively with water and methanol (50% (V / V)). Finally, the resulting filter cake was dissolved in an appropriate amount of dichloromethane, and further purified by column chromatography (mobile phase: petroleum ether: dichloromethane = 3:1 (V / V)) to obtain 13.2 g of a white solid, with a yield of 80%. . MS(EI):m / z 327.21[M + ];C 24 h 2...

Embodiment 2

[0156] Embodiment 2: the synthesis of compound 1-27

[0157] [Synthesis of Intermediate 1-27-1]

[0158]

[0159] Under nitrogen atmosphere, 4-bromo-9,9-dimethylfluorene (13.7g, 50.0mmol), 2,4,6-trimethylaniline (6.8g , 50.0mmol), sodium tert-butoxide (9.6g, 100.0mmol), n-butylbis(1-adamantyl)phosphine (1.8g, 10.0mmol), tris(dibenzylideneacetone)dipalladium (2.9g , 5.0mmol) and toluene (200mL), and heated to reflux for 6h. After the reaction, the system was cooled to room temperature. A large amount of water was added to form a white precipitate, which was collected by suction filtration. The precipitate was washed successively with water and methanol (50% (V / V)). Finally, the resulting filter cake was dissolved in an appropriate amount of dichloromethane, and further purified by column chromatography (mobile phase: petroleum ether: dichloromethane = 3:1 (V / V)) to obtain 13.5 g of a white solid, with a yield of 82%. . MS(EI):m / z 327.21[M + ];C 24 h 25 N...

Embodiment 3

[0166] Embodiment 3: the synthesis of compound 1-52

[0167] [Synthesis of Intermediate 1-52-1]

[0168]

[0169] Under a nitrogen atmosphere, 4-bromo-9-(4-tert-butylphenyl)carbazole (18.9g, 50.0mmol), p-methylaniline (5.4g, 50.0mmol), sodium tert-butoxide (9.6g, 100.0mmol), n-butyl bis(1-adamantyl)phosphine (1.8g, 10.0mmol), tris(dibenzylideneacetone)dipalladium (2.9g, 5.0mmol) and toluene (200mL), and heated to reflux for 6h. After the reaction, the system was cooled to room temperature. A large amount of water was added to form a white precipitate, which was collected by suction filtration. The precipitate was washed successively with water and methanol (50% (V / V)). Finally, the resulting filter cake was dissolved in an appropriate amount of dichloromethane, and further purified by column chromatography (mobile phase: petroleum ether: dichloromethane = 3:1 (V / V)) to obtain 17.6 g of a white solid, with a yield of 87%. . MS(EI):m / z 327.21[M + ];C 29 h ...

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Abstract

The invention relates to a polycyclic boron-containing compound and an electronic device thereof. By introducing the boron element, the compound with rigid structural characteristics is constructed, and the rigid structure can effectively inhibit vibration relaxation caused by molecular vibration and rotation, thereby being beneficial to enhancing the fluorescence quantum yield of the molecules and reducing the half-peak width of the luminescent spectrum. In addition, due to the rigid structure, the molecules have excellent film-forming property and thermal stability, and the stability of thedevice can be further improved; in addition, since the polycyclic boron-containing compound is positioned at the 1 or 4 positions of carbazole and fluorenyl elements, no isomer is generated during preparation, and purification is facilitated. The electroluminescent device prepared from the compound provided by the invention has the advantages of low driving voltage, high luminous efficiency, longservice life, high spectral color purity and the like. In addition, the preparation method of the polycyclic boron-containing compound is simple, raw materials are easy to obtain, the materials are easy to purify, and the industrial development requirement can be met.

Description

technical field [0001] The invention belongs to the technical field of organic photoelectric materials, and relates to polycyclic boron-containing compounds and electronic devices containing the polycyclic boron-containing compounds. More specifically, the present invention relates to polycyclic boron-containing compounds suitable for electronic devices, especially organic electroluminescent devices, organic field effect transistors and organic solar cells, and electronic devices using the polycyclic boron-containing compounds. 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 a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02C07F7/08H01L51/00H01L51/54H01L51/50H10K99/00
CPCC07F5/02C07F7/0816C09K11/06C09K2211/1055C09K2211/1011C09K2211/1085C09K2211/1029C09K2211/1096H10K85/622H10K85/615H10K85/626H10K85/657H10K85/40H10K85/6572H10K50/11Y02E10/549
Inventor 崔林松张业欣朱向东陈华
Owner SUZHOU JOYSUN ADVANCED MATERIALS CO LTD
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