Acenaphtho-aza naphthalene derivative, preparation method thereof, infrared electronic device and infrared device

An electronic device, azanaphthalene technology, applied in the field of organic photoelectric materials, can solve problems such as external quantum efficiency attenuation, and achieve the effects of strong electron pulling ability, good external quantum efficiency, and reduced driving voltage

Active Publication Date: 2020-07-03
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 organic electroluminescent materials for deep red and near-infrared light colors still face many challenges. Problem, especially for OLED devices in the infrared band, the external quantum efficiency will decay rapidly

Method used

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  • Acenaphtho-aza naphthalene derivative, preparation method thereof, infrared electronic device and infrared device
  • Acenaphtho-aza naphthalene derivative, preparation method thereof, infrared electronic device and infrared device
  • Acenaphtho-aza naphthalene derivative, preparation method thereof, infrared electronic device and infrared device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0135] Embodiment 1: the synthesis of compound 1-28

[0136] (Synthesis of intermediate M1)

[0137] The synthetic route of intermediate M1 is as follows:

[0138]

[0139] Add 7.0g (30mmol) 5,6-dicyanoacenaphthylene-1,2-dione, 5.7g (30mmol) 5-bromo-2,3-diaminopyrazine and 100mL glacial acetic acid in a clean 250mL single-necked bottle , gradually warmed to reflux and reacted overnight under reflux. After the reaction was completed, the heating was stopped, and the system cooled down by itself. The reaction solution was poured into 1L of ice water, collected by suction filtration, squeezed and dried, and further purified by column chromatography (350 mesh silica gel, eluent: petroleum ether: dichloromethane = 2:3 (V / V)) Afterwards, 9.4 g of yellow solid was obtained, and the yield was 82%. MS (EI): m / z: 383.92 [M + ]. Anal.calcd for C 18 h 5 BrN 6 (%): C 56.13, H 1.31; found: C 56.01, H 1.26.

[0140] (Synthesis of Compound 1-28)

[0141] The synthetic route of c...

Embodiment 2

[0144] Embodiment 2: the synthesis of compound 1-46

[0145] (Synthesis of compound 1-46)

[0146] The synthetic route of compound 1-46 is as follows:

[0147]

[0148] Under nitrogen, 13.8g (47.8mmol) N-phenyl-3-carbazole boronic acid, 8.4g (79.6mmol) anhydrous sodium carbonate, 15.3g (39.8mmol) M1, 470.8 mg (4.8 mmol) of tetrakis(triphenylphosphine palladium) and 100 mL of mixed solvent (toluene:water:ethanol=5:1:1 (V / V)). The system was gradually heated to reflux and reacted overnight under reflux. After the reaction was completed, the heating was stopped, and the reaction system was cooled to room temperature by itself. The reaction solution was poured into about 200 mL of water, and extracted with dichloromethane. The organic phase was dried over anhydrous sodium sulfate, concentrated under reduced pressure, and further purified by column chromatography (350 mesh silica gel, eluent: petroleum ether: dichloromethane = 3:2 (V / V)) to obtain a red solid 18.3 g, yield ...

Embodiment 3

[0149] Embodiment 3: the synthesis of compound 1-54

[0150] (Synthesis of Intermediate M2)

[0151] The synthetic route of intermediate M2 is as follows:

[0152]

[0153] Add 7.0g (30mmol) 5,6-dicyanoacenaphthylene-1,2-dione, 5.3g (30mmol) 4.5-dichloro-2.3-diaminopyrazine and 100mL glacial acetic acid in a clean 250mL single-necked bottle, Gradually raise the temperature to reflux and react overnight under reflux. After the reaction was completed, the heating was stopped, and the system cooled down by itself. The reaction solution was poured into 1L of ice water, collected by suction filtration, squeezed and dried, and further purified by column chromatography (350 mesh silica gel, eluent: petroleum ether: dichloromethane = 2:3 (V / V)) Afterwards, 9.2 g of yellow solid was obtained, and the yield was 82%. MS (EI): m / z: 374.32 [M + ]. Anal.calcd for C 18 h 4 Cl 2 N 6 (%): C 57.63, H 1.07; found: C 57.51, H 1.05.

[0154] (Synthesis of compound M3)

[0155] The s...

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Abstract

The invention provides an acenaphtho-aza naphthalene derivative, a preparation method thereof, an infrared electronic device and an infrared device, and relates to the technical field of organic photoelectric materials. By introducing the condensed ring structure of the acenaphtho-aza naphthalene derivative, the obtained acenaphtho-aza naphthalene derivative is excellent in film-forming property and thermal stability and relatively high in fluorescence quantum yield, and can be used to prepare an organic light-emitting device, an organic field effect transistor and an organic solar cell. Furthermore, the acenaphtho-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 a driving voltage, improve efficiency, brightness, and lifespan, and the like. In addition, the preparation method of the acenaphtho-aza naphthalene derivative is simple, raw materials are easy to obtain, and industrial development requirements can be met.

Description

technical field [0001] The invention belongs to the technical field of organic photoelectric materials, and relates to acenaphthoazepine derivatives and electronic devices containing the acenaphthoazepine derivatives. More specifically, the present invention relates to acenaphthoazepine derivatives suitable for use in electronic devices, especially organic electroluminescent devices, organic field effect transistors and organic solar cells, and infrared light-emitting diodes using the acenaphthoazepine derivatives. Electronics and infrared devices. 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 devic...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/06C07D519/00C09K11/06H01L51/30H01L51/46H01L51/54
CPCC07D487/06C07D519/00C09K11/06C09K2211/1074C09K2211/1029C09K2211/1037C09K2211/1092C09K2211/1007C09K2211/1011C09K2211/1014C09K2211/1033C09K2211/1044C09K2211/1048C09K2211/1051C09K2211/1059H10K85/615H10K85/624H10K85/631H10K85/636H10K85/657H10K85/6576H10K85/6572Y02E10/549
Inventor 崔林松朱向东张业欣陈华
Owner SUZHOU JOYSUN ADVANCED MATERIALS CO LTD
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