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3,4-diazafluorenone derivative, synthesis method thereof, and electronic device containing 3,4-diazafluorenone derivative

An electronic device and a technology of heterofluorenone are applied in the field of organic optoelectronic materials to achieve the effects of improving electron transmission efficiency, improving luminous efficiency and reducing driving voltage

Inactive Publication Date: 2020-02-04
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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  • 3,4-diazafluorenone derivative, synthesis method thereof, and electronic device containing 3,4-diazafluorenone derivative
  • 3,4-diazafluorenone derivative, synthesis method thereof, and electronic device containing 3,4-diazafluorenone derivative
  • 3,4-diazafluorenone derivative, synthesis method thereof, and electronic device containing 3,4-diazafluorenone derivative

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0143] Embodiment 1: the synthesis of compound 39

[0144] (Synthesis of Intermediate 1-1)

[0145] The synthetic route of intermediate 1-1 is as follows:

[0146]

[0147] Add ninhydrin (3.6g, 20mmol), 4-bromoacetophenone (4.0g, 20mmol), and 120mL acetic acid successively into a 250mL one-necked flask, and react under reflux for 4 hours. After the reaction was completed, it was cooled to room temperature. 2 mL of hydrazine hydrate (85 wt%) was added dropwise and the reaction was continued overnight at room temperature. The solid was collected by suction filtration and washed with a small amount of absolute ethanol. The crude product was further purified by column chromatography (petroleum ether:dichloromethane=1:1 (V / V)). The solvent was evaporated, and after drying, 3.3 g of a yellow solid was obtained with a yield of 49%. MS(EI): m / z: 337.10[M + ]. Anal.calcd for C 17 h 9 BrN 2 O (%): C 60.56, H 2.69, N 8.31; found: C 60.55, H 2.72, N 8.29.

[0148] (Synthesis...

Embodiment 2

[0152] Embodiment 2: the synthesis of compound 50

[0153] (Synthesis of compound 50)

[0154] The synthetic route of compound 50 is as follows:

[0155]

[0156] Under nitrogen protection, intermediate 1-1 (1.7g, 5mmol), bis(4-biphenyl)amine (1.7g, 5.2mmol), palladium acetate (11mg, 0.05mmol), palladium acetate (11mg, 0.05mmol), Tri-tert-butylphosphine tetrafluoroborate (29mg, 0.1mmol), sodium tert-butoxide (960mg, 10mmol) and 120mL toluene were stirred under reflux 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, 2.1 g of an orange-yellow solid was obtained ...

Embodiment 3

[0157] Embodiment 3: the synthesis of compound 130

[0158] (Synthesis of Intermediate 1-2)

[0159] The synthetic route of intermediate 1-2 is shown below:

[0160]

[0161] Add ninhydrin (3.6g, 20mmol), 5-acetyl-2-bromopyridine (4.0g, 20mmol) and 120mL acetic acid successively into a 250mL one-necked flask, and react under reflux for 4 hours. After the reaction was completed, it was cooled to room temperature. 2 mL of hydrazine hydrate (85 wt%) was added dropwise and the reaction was continued overnight at room temperature. The solid was collected by suction filtration and washed with a small amount of absolute ethanol. The crude product was further purified by column chromatography (petroleum ether:dichloromethane=1:1 (V / V)). The solvent was evaporated, and after drying, 3.6 g of a yellow solid was obtained, yield 53%. MS(EI): m / z: 338.04[M + ]. Anal.calcd for C 16 h 8 BrN 3 O (%): C 56.83, H 2.38, N 12.43; found: C 56.80, H 2.42, N 12.41.

[0162] (Synthesis ...

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Abstract

The invention relates to the technical field of organic photoelectric materials, and concretely relates to a 3,4-diazafluorenone derivative, a synthesis method thereof, and an electronic device containing the 3,4-diazafluorenone derivative. The 3,4-diazafluorenone derivative is represented by general formula (1) shown in the description; and in the formula (1), L1 and L2 independently represent one or more of a single bond, a carbonyl group, a C6-18 aryl group and a C5-18 aromatic heterocyclic group. A 3,4-diazafluorenone rigid structure is introduced, so that the obtained 3,4-diazafluorenonederivative has an excellent film-forming property and an excellent thermal stability, and can be used for preparing an organic light-emitting device, an organic field effect transistor and an organicsolar cell. In addition, the 3,4-diazafluorenone derivative can be used as a constituent material for a hole injection layer, a hole transport layer, a light emitting layer, an electron blocking layer, a hole blocking layer or an electron transport layer, and can reduce the driving voltage, improve the efficiency, improve the brightness and prolong the service life.

Description

technical field [0001] The invention relates to the technical field of organic photoelectric materials, in particular to 3,4-diazafluorenone derivatives, a synthesis method thereof and electronic devices containing 3,4-diazafluorenone 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 includes an anode, a metal cathode, and an organic layer sandwiched between them. The organic layer mainly includes a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, and an electron injection la...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D403/10C07D237/26C07D401/10C07D413/10C07D491/048C07D495/04C07D487/04C07D405/14C07D403/14C07D409/14C07D405/12C07D409/12C07D471/04C07D401/14C07D401/04C07D417/14C07F7/08C07F5/02C07F9/6509C07F9/6558C09K11/06H01L51/50H01L51/54
CPCC07D403/10C07D237/26C07D401/10C07D413/10C07D491/048C07D495/04C07D487/04C07D405/14C07D403/14C07D409/14C07D405/12C07D409/12C07D471/04C07D401/14C07D401/04C07D417/14C07F7/0812C07F7/0816C07F5/027C07F9/650947C07F9/65583C09K11/06C09K2211/1007C09K2211/1011C09K2211/1014C09K2211/1029C09K2211/1033C09K2211/1037C09K2211/104C09K2211/1044C09K2211/1088C09K2211/1092C09K2211/1096H10K85/624H10K85/615H10K85/622H10K85/626H10K85/657H10K85/6576H10K85/6574H10K85/322H10K85/40H10K85/6572H10K50/18H10K50/15H10K50/16H10K50/17H10K50/11
Inventor 崔林松刘向阳张业欣陈华
Owner SUZHOU JOYSUN ADVANCED MATERIALS CO LTD
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