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Polycyclic aromatic hydrocarbon aza-naphthalene derivative, synthesis method and electronic device thereof

A technology for polycyclic aromatic hydrocarbons and electronic devices, which is applied in the field of electronic devices containing polycyclic aromatic hydrocarbons and aziridine derivatives, to achieve high luminous efficiency, improve electron transmission efficiency, and improve luminous efficiency

Pending Publication Date: 2020-08-18
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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  • Polycyclic aromatic hydrocarbon aza-naphthalene derivative, synthesis method and electronic device thereof
  • Polycyclic aromatic hydrocarbon aza-naphthalene derivative, synthesis method and electronic device thereof
  • Polycyclic aromatic hydrocarbon aza-naphthalene derivative, synthesis method and electronic device thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0136] Embodiment 1: the synthesis of compound 1-10

[0137] (Synthesis of intermediate M1)

[0138] The synthetic route of intermediate M1 is as follows:

[0139]

[0140] P-bromobenzohydrazide (4.3g, 20mmol), acenaphthoquinone (3.6g, 20mmol), ammonium acetate (11.8g, 200mmol) and 150mL acetic acid were successively added into a 250mL single-necked flask, and the reaction was stirred under reflux 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=2:1 (V / V)). The solvent was evaporated, and after drying, 4.5 g of an orange solid was obtained, yield 63%. MS(EI): m / z: 360.08[M + ]. Anal.calcd for C 19 h 10 BrN 3 (%): C 63.35, H 2.80, N 11.67; found: C 63.33, H 2.85, N 11.64.

[0141] (Synthesis of Intermediate M2)

[0142] The synthetic route of intermediate M2 is as follows:

...

Embodiment 2

[0149] Embodiment 2: the synthesis of compound 1-34

[0150] (Synthesis of Intermediate M3)

[0151] The synthetic route of intermediate M3 is as follows:

[0152]

[0153] Under an argon atmosphere, 5-bromo-2-chloropyrimidine (1.1 g, 5.7 mmol), M1 (1.8 g, 5.0 mmol) and 50 mL of toluene were successively added to a 100 mL one-necked flask, followed by 0.5 M bis(trimethylsilane A toluene solution of potassium amide (6.0 mmol) was added dropwise to the reaction system. After reacting at 50°C for 12 hours, the reaction was quenched by adding saturated ammonium chloride solution. The organic layer was extracted with ethyl acetate and washed with Na 2 SO 4 After drying, 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=2:1 (V / V)). The solvent was evaporated, and after drying, 1.4 g of a yellow solid was obtained with a yield of 63...

Embodiment 3

[0158] Embodiment 3: the synthesis of compound 1-6

[0159] (Synthesis of Intermediate M4)

[0160] The synthetic route of intermediate M4 is as follows:

[0161]

[0162] Add benzohydrazide (2.7g, 20mmol), 5,6-dibromoacenaphthenequinone (6.8g, 20mmol), sodium acetate (27g, 200mmol) and 150mL acetic acid successively into a 250mL single-necked flask, and react under reflux for 12 hours. After the reaction was complete, the solid was collected by suction filtration and washed with a small amount of absolute ethanol. After drying, 5.2 g of an orange solid was obtained, yield 59%. MS(EI): m / z: 439.02[M + ]. Anal.calcd for C 19 h 9 Br 2 N 3 (%): C 51.97, H 2.07, N 9.57; found: C 51.95, H 2.10, N 9.54.

[0163] (Synthesis of Intermediate M5)

[0164] The synthetic route of intermediate M5 is as follows:

[0165]

[0166] Under an argon atmosphere, 5-bromopyrimidine (0.9 g, 5.7 mmol), M4 (2.2 g, 5.0 mmol) and 50 mL of toluene were successively added to a 100 mL sing...

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Abstract

The invention relates to the technical field of organic photoelectric materials, in particular to a polycyclic aromatic hydrocarbon aza-naphthalene derivative, a synthesis method thereof and an electronic device containing the polycyclic aromatic hydrocarbon aza-naphthalene derivative represented by a general formula (1), wherein Z represents CR1 or N. According to the polycyclic aromatic hydrocarbon aza-naphthalene derivative disclosed by the invention, a polycyclic aromatic hydrocarbon aza-naphthalene rigid structure is introduced, so that the obtained polycyclic aromatic hydrocarbon aza-naphthalene derivative is excellent in film-forming property and thermal stability, and can be used for preparing an organic light-emitting device, an organic field effect transistor and an organic solarcell. In addition, the polycyclic aromatic hydrocarbon aza-naphthalene derivative can be 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.

Description

technical field [0001] The invention relates to the technical field of organic photoelectric materials, in particular to polycyclic aromatic azinaphthalene derivatives, a synthesis method thereof, and an electronic device containing polycyclic aromatic azanaphthalene 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 la...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/06C07D519/00C07D471/22C09K11/06H01L51/50H01L51/54
CPCC07D471/06C07D519/00C07D471/22C09K11/06C09K2211/1014C09K2211/1059C09K2211/1029C09K2211/1044C09K2211/1033C09K2211/1074H10K85/631H10K85/657H10K85/6572H10K50/11H10K50/15H10K50/16H10K50/17H10K50/18
Inventor 崔林松朱向东张业欣陈华
Owner SUZHOU JOYSUN ADVANCED MATERIALS CO LTD
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