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1, 3-diazafluorenone derivative and electronic device

A technology of electronic devices and heterofluorenones, which is applied in the field of organic photoelectric materials, can solve the problems of device electron and hole mobility imbalance, device efficiency and life reduction, molecular structure or crystal state changes, etc., and achieve excellent hole blocking The ability to reduce the driving voltage and the effect of simple preparation method

Pending Publication Date: 2022-03-22
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

The glass transition temperature of the electron transport materials widely used in the market is relatively low, generally less than 85°C. When the device is running, the Joule heat generated will lead to changes in the molecular structure or crystal state, resulting in lower efficiency and lower thermal stability of the panel. Poor, the symmetry of this molecular structure is very regular, and it is easy to crystallize after a long time
Once the electron transport material is crystallized, the charge transition mechanism between molecules will be different from the normal operation of the amorphous film mechanism, resulting in a decrease in the performance of electron transport, making the electron and hole mobility of the entire device unbalanced, and the exciton formation efficiency is greatly improved. Reduced, and the formation of excitons will be concentrated at the interface between the electron transport layer and the light-emitting layer, resulting in a serious decrease in device efficiency and lifetime

Method used

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  • 1, 3-diazafluorenone derivative and electronic device
  • 1, 3-diazafluorenone derivative and electronic device
  • 1, 3-diazafluorenone derivative and electronic device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Embodiment 1: the synthesis of compound 1-7

[0043] (Synthesis of intermediate M1)

[0044] The synthetic route of intermediate M1 is as follows:

[0045]

[0046]Add 2-(4-bromophenyl)-1,3-diazafluorene (6.46g, 20mmol), chromium trioxide (2.5g, 25mmol) and 120mL acetic acid successively in a 250mL single-necked flask, and react under reflux for 4 hours . After the reaction was completed, it was cooled to room temperature. The reaction solution was poured into water and extracted with dichloromethane. The organic phase was washed with saturated sodium bicarbonate solution. The organic phase was dried and evaporated under reduced pressure, and the obtained crude product was further purified by column chromatography (petroleum ether:dichloromethane=2:1 (V / V)). The solvent was evaporated, and after drying, 3.50 g of a yellow solid was obtained with a yield of 52%. MS(EI): m / z: 337.02[M + ]. Anal.calcd for C 17 h 9 BrN 2 O (%): C60.56, H2.69, N 8.31; found: C ...

Embodiment 2

[0051] Embodiment 2: the synthesis of compound 2-2

[0052] The synthetic route of compound 2-2 is as follows:

[0053]

[0054] Under nitrogen protection, intermediate M1 (1.69g, 5mmol), bis(4-biphenyl)amine (1.64g, 5.1mmol), palladium acetate (22.4mg, 0.1mmol), three tert-butylphosphinetetrafluoroborate (73mg, 0.25mmol), sodium tert-butoxide (1.0g, 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=2:1 (V / V)). The solvent was evaporated, and after drying, 2.25 g of an orange-red solid was obtained, with a yield of 78%. MS (EI): m / z: 577.50 [M + ]. Anal.calcd for C...

Embodiment 3

[0055] Embodiment 3: the synthesis of compound 3-1

[0056] The synthetic route of compound 3-1 is as follows:

[0057]

[0058] Under nitrogen protection, intermediate M1 (1.69g, 5mmol), 9,10-dihydro-9,9-dimethylacridine (1.05g, 5.1mmol), palladium acetate (22.4 mg, 0.1 mmol), tri-tert-butylphosphine tetrafluoroborate (73 mg, 0.25 mmol), sodium tert-butoxide (1.0 g, 10 mmol) and 120 mL of 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=2:1 (V / V)). The solvent was evaporated, and after drying, 1.63 g of an orange-yellow solid was obtained, with a yield of 71%. MS (EI): m / z: 465.58 [M +...

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Abstract

The invention relates to a 1, 3-diazafluorenone derivative and an electronic device. According to the 1, 3-diazafluorenone derivative disclosed by the invention, a 1, 3-diazafluorenone structure is introduced, so that the obtained 1, 3-diazafluorenone derivative is excellent in thermal stability and is used for preparing an organic electroluminescent device. Besides, the 1, 3-diazafluorenone derivative disclosed 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 driving voltage, improve efficiency, brightness, prolong the service life and the like.

Description

technical field [0001] The invention belongs to the technical field of organic photoelectric materials, and relates to 1,3-diazafluorenone derivatives and electronic devices containing the 1,3-diazafluorenone derivatives. More specifically, the present invention relates to 1,3-diazafluorenone derivatives suitable for use in electronic devices, especially organic electroluminescent device cells, and electronic devices using the 1,3-diazafluorenone derivatives. Background technique [0002] Organic light-emitting devices (Organic Light-emitting Devices, OLED) are spontaneous light-emitting devices using the following principle: when an electric field is applied, fluorescent substances emit light through the recombination of holes injected from the positive electrode and electrons injected from the negative electrode. This self-luminous device has the characteristics of low voltage, high brightness, wide viewing angle, fast response, good temperature adaptability, etc., and is ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D403/10C07D403/14C07D487/04C07D491/048C07D495/04C07D417/10C07D409/12C07D405/12C09K11/06H01L51/54H01L51/50
CPCC07D403/10C07D403/14C07D487/04C07D491/048C07D495/04C07D417/10C07D409/12C07D405/12C09K11/06C09K2211/1044C09K2211/1037C09K2211/1033C09K2211/1029C09K2211/1088C09K2211/1092H10K85/6576H10K85/6574H10K85/657H10K85/6572
Inventor 朱向东张业欣袁晓冬
Owner 维思普新材料(苏州)有限公司
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