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Spirobenzanthrone derivative and electronic device

A technology for spirobenzoxanthrone and electronic devices, which is applied in the field of spirobenzoxanthrone derivatives, electronic devices, and electronic devices of spirobenzoxanthrone derivatives, and achieves simple preparation method, easy-to-obtain raw materials, and luminescence. Efficient effect

Inactive Publication Date: 2020-04-17
SUZHOU JOYSUN ADVANCED MATERIALS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Overall, the future direction of organic electroluminescent devices is to develop high-efficiency, long-life, low-cost white light devices and full-color display devices, but the industrialization process of this technology still faces many key problems

Method used

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  • Spirobenzanthrone derivative and electronic device
  • Spirobenzanthrone derivative and electronic device
  • Spirobenzanthrone derivative and electronic device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0170] Embodiment 1: the synthesis of compound 3

[0171] (Synthesis of Intermediate 1-1)

[0172] The synthetic route of intermediate 1-1 is as follows:

[0173]

[0174] Under nitrogen protection, the intermediate acridone (820 mg, 4.2 mmol), N-([1,1'-biphenyl]-4-yl)-N-(4-bromophenyl )-[1,1'-biphenyl]-4-amine (2.4g, 5mmol), palladium acetate (18mg, 0.08mmol), tri-tert-butylphosphine tetrafluoroborate (73mg, 0.25mmol), tert Sodium butoxide (806mg, 8.4mmol) and 120mL of toluene were stirred under reflux for 12 hours. After the reaction is complete, evaporate the solvent, dissolve the residue with 200 mL of dichloromethane and 50 mL of water, wash with water, separate the organic layer, extract the aqueous layer twice with 15 mL of dichloromethane, combine the organic layers, evaporate the solvent, and pass the residue through the column After chromatographic separation (petroleum ether:dichloromethane=1:1 (V / V)), the solvent was evaporated and dried to obtain 1.4 g of li...

Embodiment 2

[0180] Embodiment 2: the synthesis of compound 98

[0181] (Synthesis of Intermediate 1-2)

[0182] The synthetic route of intermediate 1-2 is shown below:

[0183]

[0184]Under the protection of nitrogen, 2.9 g (8.9 mmol) of 2-bromotriphenylamine and 150 mL of anhydrous tetrahydrofuran were added to a dry and clean 250 mL three-necked flask, and stirred and dissolved at room temperature. The system was cooled to -78°C, and 3.9 mL (2.5 M, 9.8 mmol) of n-butyllithium was added dropwise at this temperature, and stirring was continued at this temperature for 1.5 h after the addition was complete. Subsequently, 2.5 g (8.1 mmol) of 9-bromobenzanthrone was added in one batch. After the addition, the cold bath was removed, and the reaction returned to room temperature by itself and continued to stir overnight. After the reaction, it was washed with water, dried, and spin-dried to obtain a white solid.

[0185] The above white solid was transferred to a 250mL one-necked bottle ...

Embodiment 3

[0190] Embodiment 3: the synthesis of compound 138

[0191] (Synthesis of Intermediates 1-3)

[0192] The synthetic routes of intermediates 1-3 are shown below:

[0193]

[0194] Under the protection of nitrogen, 2.9 g (8.9 mmol) of 2-bromotriphenylamine and 150 mL of anhydrous tetrahydrofuran were added to a dry and clean 250 mL three-necked flask, and stirred and dissolved at room temperature. The system was cooled to -78°C, and 3.9 mL (2.5 M, 9.8 mmol) of n-butyllithium was added dropwise at this temperature, and stirring was continued at this temperature for 1.5 h after the addition was completed. Subsequently, 2.5 g (8.1 mmol) of 3-bromobenzanthrone was added in one batch. After the addition, the cold bath was removed, and the reaction was warmed to room temperature by itself and continued to stir overnight. After the reaction, it was washed with water, dried, and spin-dried to obtain a white solid.

[0195] The above white solid was transferred to a 250mL one-necke...

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Abstract

The invention relates to a spirobenzanthrone derivative and an electronic device. According to the spirobenzanthrone derivative disclosed by the invention, a spirobenzanthrone rigid structure is introduced, so that the obtained spirobenzanthrone derivative is excellent in film-forming property and thermal stability, can be used for preparing an organic electroluminescent device, an organic field effect transistor and an organic solar cell, can be used as a constituent material of a hole injection layer, a hole transport layer, a light emitting layer, an electron blocking layer, a hole blockinglayer or an electron transport layer, and can reduce the driving voltage, improve the efficiency, improve the brightness, prolong the service life and the like. The preparation method of the spirobenzanthrone derivative has characteristics of simpleness and easily available raw materials, and can meet industrial development requirements.

Description

technical field [0001] The invention belongs to the technical field of organic photoelectric materials, and relates to spirobenzanthrone derivatives and electronic devices containing the spirobenzanthrone derivatives. More specifically, the present invention relates to spirobenzanthrone derivatives suitable for use in electronic devices, particularly organic electroluminescent devices, organic field effect transistors and organic solar cells, and to products using the spirobenzanthrone derivatives. electronic devices. 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, ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D221/20C07D401/10C07D413/10C07D417/10C07D405/12C07D491/048C07D401/12C07F9/576C07F5/02C07F7/10C07D471/04C07D401/04C07D413/04C07D417/04C07D409/12C07D487/04C07D487/06C07D519/00C07F9/6561C07D498/06C07D513/06C09K11/06H01L51/50H01L51/54
CPCC07D221/20C07D401/10C07D413/10C07D417/10C07D405/12C07D491/048C07D401/12C07F9/5765C07F5/02C07F7/0812C07D471/04C07D401/04C07D413/04C07D417/04C07D409/12C07D487/04C07D487/06C07D519/00C07F9/6561C07D498/06C07D513/06C09K11/06C09K2211/1007C09K2211/1011C09K2211/1014C09K2211/1022C09K2211/1029C09K2211/1033C09K2211/1037C09K2211/1044C09K2211/1059C09K2211/1088C09K2211/1092H10K85/615H10K85/624H10K85/631H10K85/636H10K85/633H10K85/654H10K85/657H10K85/6576H10K85/6574H10K85/6572H10K50/00Y02E10/549Y02P70/50
Inventor 崔林松刘向阳张业欣陈华
Owner SUZHOU JOYSUN ADVANCED MATERIALS CO LTD
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