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2, 4-diazaspirofluorene derivative and electronic device

A technology of fluorene derivatives and diazaspiro, which is applied in the field of organic optoelectronic materials to achieve the effects of excellent electron transport performance, reduced driving voltage, and low driving voltage

Pending Publication Date: 2022-04-12
维思普新材料(苏州)有限公司
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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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  • 2, 4-diazaspirofluorene derivative and electronic device
  • 2, 4-diazaspirofluorene derivative and electronic device
  • 2, 4-diazaspirofluorene derivative and electronic device

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Embodiment 1: the synthesis of compound 1-1

[0039] The synthetic route of intermediate M1 is as follows:

[0040]

[0041]Under the protection of nitrogen, 1-bromo-8-phenylnaphthalene (2.5 g, 8.9 mmol) and 150 mL of anhydrous tetrahydrofuran were added to a dry and clean 250 mL three-necked flask, and stirred to dissolve 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. Then, 3-(4-bromophenyl)-2,4-diazafluorenone (2.7g, 8.1mmol) was added in one go. After the addition, the cooling 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.

[0042] Transfer the above white solid to a 250mL single-necked bottle equipped with a reflux condenser, a...

Embodiment 2

[0046] Embodiment 2: the synthesis of compound 2-3

[0047] The synthetic route of compound 2-3 is as follows:

[0048]

[0049] Under nitrogen protection, intermediate M1 (2.6g, 5mmol), 5,7-dihydro-7,7-dimethyl-indeno[2,1-B]carbazole (1.4 g, 5mmol), palladium acetate (11mg, 0.05mmol), tri-tert-butylphosphine tetrafluoroborate (29mg, 0.1mmol), sodium tert-butoxide (960mg, 10mmol) and 120mL toluene, refluxed and stirred for 12 hours. After the reaction was complete, the solvent was evaporated, the residue was dissolved with 200 mL of dichloromethane, washed with water, the organic layer was separated, the aqueous layer was extracted twice with 15 mL of dichloromethane, and the organic layers were combined. After distilling off the solvent, the residue was separated by column chromatography (petroleum ether:dichloromethane=3:1 (V / V)). The solvent was evaporated, and after drying, 2.5 g of a green solid was obtained with a yield of 68%. MS (EI): m / z: 725.28 [M + ]. Anal.c...

Embodiment 3

[0050] Embodiment 3: the synthesis of compound 3-3

[0051] The synthetic route of compound 3-3 is as follows:

[0052]

[0053] Under nitrogen protection, intermediates M1 (2.6g, 5mmol), M2 (3.2g, 5.2mmol), palladium acetate (11mg, 0.05mmol), tri-tert-butylphosphine tetrafluoroborate were successively added to a 250mL Schlenk bottle (29mg, 0.1mmol), sodium tert-butoxide (960mg, 10mmol) and 120mL toluene, reflux and stir for 12 hours. After the reaction was complete, the solvent was evaporated, the residue was dissolved with 200 mL of dichloromethane, washed with water, the organic layer was separated, the aqueous layer was extracted twice with 15 mL of dichloromethane, and the organic layers were combined. After distilling off the solvent, the residue was separated by column chromatography (petroleum ether:dichloromethane=4:1 (V / V)). The solvent was evaporated, and after drying, 3.5 g of a green solid was obtained with a yield of 65%. MS(EI): m / z: 1065.40[M + ]. Anal....

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Abstract

The invention relates to a 2, 4-diazaspirofluorene derivative and an electronic device. According to the 2, 4-diazaspirofluorene derivative disclosed by the invention, a unique 2, 4-diazaspirofluorene derivative mother nucleus structure formed by combining biphenyl spirofluorene and a D-pi-A structure is introduced, so that the obtained 2, 4-diazaspirofluorene derivative is excellent in film-forming property and thermal stability, and can be used for preparing an organic electroluminescent device. The 2, 4-diazaspirofluorene derivative provided by the invention can be used as a constituent material of a luminescent layer, a hole blocking layer or an electron transport layer, and can reduce the driving voltage, improve the efficiency, the brightness and prolong the service life.

Description

technical field [0001] The invention belongs to the technical field of organic photoelectric materials, and relates to 2,4-diazaspirofluorene derivatives and electronic devices containing the 2,4-diazaspirofluorene derivatives. More specifically, the present invention relates to 2,4-diazaspirofluorene derivatives suitable for electronic devices, especially organic electroluminescence devices, organic field effect transistors and organic solar cells and the use of the 2,4-diazo Electronic devices of heterospirofluorene derivatives. 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 includ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D239/70C07D405/12C07D403/10C07D491/048C07D487/04C07D403/14C07D401/10C07D401/14C09K11/06H01L51/54
Inventor 刘向阳朱向东袁晓冬
Owner 维思普新材料(苏州)有限公司
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