Quinoxaline derivative and preparation method thereof

A kind of technology of quinoxaline and derivatives, applied in the field of quinoxaline derivatives and preparation thereof, can solve the problems such as the limitation of types of dihydrophenazine derivatives

Inactive Publication Date: 2012-06-13
EAST CHINA UNIV OF SCI & TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In this way, the types of dihydrophenazine

Method used

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  • Quinoxaline derivative and preparation method thereof
  • Quinoxaline derivative and preparation method thereof
  • Quinoxaline derivative and preparation method thereof

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[0034] In the preparation method provided by the present invention, the raw materials and reagents used are known, which can be purchased in the market, or prepared according to the prior art. For example, the preparation of N,N'-diaryl-o-phenanthrene diamine compounds can be synthesized by referring to the method reported in the literature (J.Chem.Soc.D, 1970, 1552-1553).

[0035] In the preparation method provided by the present invention, the reaction temperature of the N,N'-diaryl-phenanthrene diamine compound and the halogenated aromatic hydrocarbon is 20°C-250°C, more preferably 150°C-230°C. The reaction time is at least 1 hour, preferably the reaction time is 1 hour to 48 hours. The molar ratio of N,N'-diaryl-o-phenanthrene diamine compound to halogenated aromatic hydrocarbon is preferably 1:(0.5-2).

[0036] Catalyst used in the present invention is selected from: copper, palladium, platinum, copper-containing compound, palladium-containing compound or the mixture of ...

Embodiment 1

[0042] Synthesis of 1,6-diphenyl-benzo[b]-dibenzo[f,h]quinoxaline (compound I a)

[0043]

[0044] In a 100ml three-necked bottle, add N in sequence 9 , N 10 -Diphenylphenanthrene-9,10-diamine (4.0g, 11.1mmol), iodobenzene (3.4g, 16.6mmol), potassium carbonate (3.1g, 22.2mmol), cuprous chloride (0.7g, 17.1mmol ), trichlorobenzene 15ml, turn on stirring and heating, react at 150°C for 1 hour, then continue to heat up to 210°C for reaction, track the reaction until the raw materials are completely reacted. After the reaction, the trichlorobenzene was distilled off under reduced pressure to obtain a brown-black viscous object. Petroleum ether: dichloromethane = 20:1: passed through the column (silica gel column) to obtain 1.0 g of white solid (Compound Ia), with a yield of 21%. The ultraviolet-visible absorption spectrum figure and fluorescence spectrum figure of compound I a are shown in figure 1 , the cyclic voltammetry curve of compound I a is shown in Figure 4 , the ...

Embodiment 2

[0047] Synthesis of 3-methyl-1-p-toluene-6-benzene-benzo[b]-dibenzo[f,h]quinoxaline (compound I b)

[0048]

[0049] In a 100ml three-necked bottle, add N in sequence 9 , N 10 -bis(4-methylbenzene)-9,10-diaminophenanthrene (4.0g, 10.3mmol), iodobenzene (3.2g, 15.5mmol), potassium carbonate (2.8g, 20.6mmol), cuprous chloride ( 0.7g, 17.1mmol), trichlorobenzene 15ml, start stirring and heating, react at 150°C for 1 hour, then continue to heat up to reflux reaction, track the reaction until the raw materials are completely reacted. After the reaction, the trichlorobenzene was distilled off under reduced pressure to obtain a brown-black viscous object. Petroleum ether: dichloromethane = 20:1: passed through the column (silica gel column) to obtain 0.8 g of white solid (Compound Ib), with a yield of 18%.

[0050] 1 H NMR (400MHz, CDCl 3 ): δ=8.72(d, J=8.3Hz, 2H), 8.10(dd, J=15.2, 7.9Hz, 2H), 7.74-7.40(m, 6H), 7.12(d, J=9.0Hz, 1H) , 7.06-6.98(m, 2H), 6.93(d, J=9.0Hz, 4H), 6...

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Abstract

The invention relates to an N, N'-diaryl-aryl[b]-dibenzo[f,h] quinoxaline compound and a preparation method thereof. The quinoxaline derivative is mainly prepared by undergoing a one-step reaction on an N, N'-diaryl o-phenanthrine diamine compound and a halogenated aryl hydrocarbon serving as raw materials, taking copper, palladium or/and platinum or a compound thereof as a catalyst and taking an alkali as an acid-binding agent under the condition that a ligand compound is contained or not contained and a solvent exists or does not exist. The quinoxaline derivative provided by the invention has high stokes displacement (which can be over 240 nanometers), wherein a part of compounds are provided with two emission bands, and the difference between maximum emission wavelengths of the two emission bands is over 100 nanometers. The quinoxaline derivative provided by the invention has a high Highest Occupied Molecular Orbital (HOMO) energy level, which indicates that the quinoxaline derivative provided by the invention has superior electron-donating performance, and can be taken as a hole transport material in an electroluminescence (EL) device.

Description

technical field [0001] The present invention relates to a kind of quinoxaline (quinoxaline) derivative and preparation method thereof, specifically, relate to a kind of N, N'-diaryl-aryl[b]-dibenzo[f,h]quinone Oxaline compounds and their preparation methods. Background technique [0002] Dihydrophenazine (dihydrophenazine) derivatives can be used as hole transport materials in electroluminescent EL. concern of organic chemists and materials chemists. [0003] Existing dihydrophenazine derivatives are mainly prepared from phenazine or dihydrophenazine or their derivatives as raw materials or intermediates, after N-alkylation or arylation of them (J.Am.Chem.Soc. 1957, 79, 6178-6179; J. Heterocycle. Chem. 1989, 36, 435-438; J. Heterocycle. Chem. 1999, 36, 1057-1064; Synthesis 1976, 748-745. 5, 373-376.). In this way, the types of dihydrophenazine derivatives are limited to a certain extent. Contents of the invention [0004] The inventor of the present invention takes N,...

Claims

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Application Information

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IPC IPC(8): C07D241/38
Inventor 苏建华沈雷平赵冬梅张志云王通海韩金龙田禾
Owner EAST CHINA UNIV OF SCI & TECH
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