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Metatriazine compound and electronic device

A technology of electronic devices and compounds, applied in the field of organic photoelectric materials, to achieve excellent hole blocking ability, good film-forming properties and thermal stability, and good application effects

Inactive Publication Date: 2020-09-15
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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  • Metatriazine compound and electronic device
  • Metatriazine compound and electronic device
  • Metatriazine compound and electronic device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0115] Embodiment 1: the synthesis of compound 1

[0116] (Synthesis of Intermediate 1-1)

[0117] The synthetic route of intermediate 1-1 is as follows:

[0118]

[0119] Add p-bromobenzohydrazide (4.3g, 20mmol), 2,4'-dibromoacetophenone (2.8g, 10mmol), sodium acetate (2.0g, 15mmol) and 120mL mixed solvent ( Ethanol: acetic acid = 7:3 (V / V)), reflux and stir for 12 hours. After the reaction was complete, 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=3:1 (V / V)). The solvent was evaporated, and after drying, 2.3 g of a light yellow solid was obtained, with a yield of 58%. MS (EI): m / z: 390.58 [M + ]. Anal.calcd for C 15 h 9 Br 2 N 3 (%): C 46.07, H 2.32, N 10.75; found: C 46.05, H 2.35, N 10.72.

[0120] (Synthesis of compound 1)

[0121] The synthetic route of compound 1 is as follows:

[0122]

[0123] Under ni...

Embodiment 2

[0125] Embodiment 2: the synthesis of compound 68

[0126] (Synthesis of Intermediate 1-2)

[0127] The synthetic route of intermediate 1-2 is shown below:

[0128]

[0129]Add p-bromobenzohydrazide (4.3g, 20mmol), 2-bromoacetophenone (2.0g, 10mmol), sodium acetate (2.0g, 15mmol) and 120mL mixed solvent (ethanol: acetic acid= 7:3 (V / V)), reflux and stirred for 12 hours. After the reaction was complete, 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=3:1 (V / V)). The solvent was evaporated, and after drying, 2.0 g of a light yellow solid was obtained with a yield of 63%. MS(EI): m / z: 312.08[M + ]. Anal.calcd for C 15 h 10 BrN 3 (%): C 57.71, H 3.23, N 13.46; found: C 57.69, H 3.25, N 13.42.

[0130] (Synthesis of Compound 68)

[0131] The synthetic route of compound 68 is as follows:

[0132]

[0133] Under nitrogen ...

Embodiment 3

[0134] Embodiment 3: the synthesis of compound 53

[0135] (Synthesis of compound 53)

[0136] The synthetic route of compound 53 is as follows:

[0137]

[0138] Under nitrogen protection, intermediate 1-2 (1.6g, 5mmol), 5,7-dihydro-7,7-dimethyl-indeno[2,1-B]carbazole were successively added to a 250mL Schlenk bottle (1.5g, 5.2mmol), palladium acetate (11mg, 0.05mmol), tri-tert-butylphosphine tetrafluoroborate (29mg, 0.1mmol), sodium tert-butoxide (960mg, 10mmol) and 120mL toluene, the reaction was stirred at reflux 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 Chromatographic separation (petroleum ether:dichloromethane=3:1 (V / V)). The solvent was evaporated, and after drying, 1.85 g ...

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Abstract

The invention relates to a metatriazine compound and an electronic device. By introducing a metatriazine rigid structure, the metatriazine compound provided by the invention has excellent film-formingproperty and thermal stability, and can be used for preparing organic electroluminescent devices, organic field effect transistors and organic solar cells. In addition, the metatriazine compound canbe used as a constituent material of 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, prolong the service life and the like. In addition, the metatriazine compound is simple in preparation method, raw materialsare easy to obtain, and the industrial development requirement can be met.

Description

technical field [0001] The invention belongs to the technical field of organic photoelectric materials, and relates to a partial triazine compound and an electronic device containing the partial triazine compound. More specifically, the present invention relates to partial triazine compounds suitable for electronic devices, especially organic electroluminescent devices, organic field effect transistors and organic solar cells, and electronic devices using the partial triazine compounds. 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 l...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D253/065C07D401/14C07D403/10C07D403/14C07D405/14C07D409/14C07D413/14C07D417/14C07D487/04C07D487/14C07D491/048C07D495/04C09K11/06H01L51/54
CPCC07D403/14C07D413/14C07D417/14C07D401/14C07D253/065C07D403/10C07D405/14C07D409/14C07D491/048C07D495/04C07D487/04C07D487/14C09K11/06C09K2211/1059C09K2211/1029C09K2211/1037C09K2211/1033C09K2211/1014C09K2211/1007C09K2211/1088C09K2211/1044C09K2211/1011H10K85/615H10K85/631H10K85/654H10K85/6576H10K85/6574H10K85/6572H10K85/657Y02E10/549
Inventor 张业欣朱向东崔林松刘向阳陈华
Owner SUZHOU JOYSUN ADVANCED MATERIALS CO LTD
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