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2, 4-diazafluorene derivative and electronic device

A technology of diazafluorene and electronic devices, which is applied in the field of electronic devices of organic electroluminescent devices, and can solve problems such as reduction in transmission performance, differences, and unbalanced mobility of electrons and holes in devices, and achieve high luminous efficiency , simple preparation method and low driving voltage

Pending Publication Date: 2022-04-29
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

Once the organic material is crystallized, the charge transition mechanism between molecules will be different, resulting in a decrease in the transport performance compared with the amorphous thin film mechanism, resulting in an imbalance in the mobility of electrons and holes in the device

Method used

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  • 2, 4-diazafluorene derivative and electronic device
  • 2, 4-diazafluorene derivative and electronic device
  • 2, 4-diazafluorene derivative and electronic device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] Embodiment 1: the synthesis of compound 1-2

[0046] The synthetic route of intermediate M1 is as follows:

[0047]

[0048] Add 1-indanone (2.64 g, 20 mmol) and N,N-dimethylformamide dimethyl acetal (5 mL, 37.6 mmol) into a 50 mL single-necked flask, and react under reflux for 6 hours. After the reaction was completed, cooled, and the solid was collected by suction filtration, and washed with a small amount of petroleum ether to obtain 3.52 g of an orange-red solid, with a yield of 94%. The crude product was directly used in the next reaction without further purification. MS(EI): m / z: 187.14[M + ]. Anal.calcd for C 12 h 13 NO (%): C76.98, H 7.00, N 7.48; found: C76.96, H 7.02, N 7.46.

[0049] Sodium methoxide (2.03g, 37.6mmol), 4-bromobenzamidine hydrochloride (8.87g, 37.6mmol) and 50mL of absolute ethanol were sequentially added into a dry and clean 100mL single-necked flask. Under constant stirring, 20 mL of anhydrous ethanol solution of the product from t...

Embodiment 2

[0056] Embodiment 2: the synthesis of compound 2-3

[0057] The synthetic route of compound 2-3 is as follows:

[0058]

[0059] Under nitrogen protection, intermediate M2 (1.76g, 5mmol), 5,7-dihydro-5-phenylindolo[2,3-B]carbazole (1.7g, 5.2 mmol), 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, 1.9 g of white solid was obtained, the yield was 63%. MS(EI): m / z: 602.32[M + ]. Anal.calcdfor...

Embodiment 3

[0060] Embodiment 3: the synthesis of compound 3-3

[0061] The synthetic route of compound 3-3 is as follows:

[0062]

[0063] Under nitrogen protection, intermediate M2 (1.76g, 5mmol), 5,7-dihydro-7,7-dimethyl-indeno[2,1-B]carbazole (1.5 g, 5.2mmol), palladium acetate (11mg, 0.05mmol), tri-tert-butylphosphine tetrafluoroborate (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=3:1 (V / V)). The solvent was evaporated, and after drying, 2.0 g of white solid was obtained, yield 72%. MS (EI): m / z: 553.35 [M + ]. Anal.calcd for C ...

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Abstract

The invention relates to a 2, 4-diazafluorene derivative and an electronic device. According to the 2, 4-diazafluorene derivative disclosed by the invention, a 2, 4-diazafluorene derivative structure is introduced, so that the obtained 2, 4-diazafluorene derivative has good film-forming property and thermal stability and can be used for preparing an organic electroluminescent device. The 2, 4-diazafluorene 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 2,4-diazafluorene derivatives and electronic devices containing the 2,4-diazafluorene derivatives. More specifically, the present invention relates to 2,4-diazafluorene derivatives suitable for use in electronic devices, especially organic electroluminescent devices, and electronic devices using the 2,4-diazafluorene 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 organi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/14C07D403/10C07D403/14C07D413/14C07D487/04C07D491/048C09K11/06H01L51/54H01L51/50
CPCC07D403/10C07D403/14C07D401/14C07D413/14C07D487/04C07D491/048C09K11/06C09K2211/1044C09K2211/1033C09K2211/1029C09K2211/1007C09K2211/1011C09K2211/1014H10K85/615H10K85/636H10K85/657H10K85/6572H10K50/16H10K50/18H10K50/11
Inventor 袁晓冬张业欣陈华
Owner 维思普新材料(苏州)有限公司
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