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Compound containing quinoxaline group and organic electroluminescent device thereof

A technology of quinoxaline groups and compounds, applied in the field of organic electroluminescent compounds and organic electroluminescent devices, can solve the problems of low electron mobility, low electron mobility, affecting the life and efficiency of devices, etc. The effect of luminous purity, high luminous efficiency and good thermal stability

Active Publication Date: 2016-06-01
SHANGHIA TAOE CHEM TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In addition, when the OLED device is operated with an applied voltage, it will generate Joule heat, which makes the organic material easy to crystallize, which affects the life and efficiency of the device. Therefore, it is also necessary to develop stable and efficient organic electroluminescent materials.
[0005] In OLED materials, since most organic electroluminescent materials transport holes faster than electrons, it is easy to cause an imbalance in the number of electrons and holes in the light-emitting layer, so that the efficiency of the device is relatively low.
Tris(8-hydroxyquinoline)aluminum (Alq 3 ) has been widely studied since its invention, but as an electron transport material, its electron mobility is still very low, and it will degrade itself. In the device using it as an electron transport layer, there will be a voltage drop , at the same time, due to the lower electron mobility, a large number of holes enter the Alq 3 In the layer, the excess holes radiate energy in a non-luminescent form, and when used as an electron-transporting material, its application is limited due to its green-emitting properties.

Method used

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  • Compound containing quinoxaline group and organic electroluminescent device thereof
  • Compound containing quinoxaline group and organic electroluminescent device thereof
  • Compound containing quinoxaline group and organic electroluminescent device thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] Synthesis of compound 2

[0045]

[0046] Synthesis of Intermediate 2-1

[0047] In the flask, add 4-bromo-o-phenylenediamine (18.6g, 0.1mol), benzil (21g, 0.1mol) and acetic acid (200ml), heat to 90°C for 5 hours, cool, filter, and use Ethanol was recrystallized to obtain 28 g of the product with a yield of 78%.

[0048] Synthesis of intermediate 2-2

[0049] In a flask, add Intermediate 2-1 (18g, 50mmol), pinacol diboronate (15.2g, 60mmol), potassium acetate (9.8g, 100mmol), dioxane (200ml) and triphenyl Phosphine palladium dichloride (1 g) was heated to reflux for 5 hours under the protection of nitrogen, cooled and concentrated. The crude product was purified by column chromatography to obtain 15.3 g of the product with a yield of 75%.

[0050] Synthesis of Intermediate 2-3

[0051] In a three-necked flask, add 2,4-dichloroquinazoline (6g, 30mmol), biphenylboronic acid (6g, 30mmol), potassium carbonate (8.3g, 60mmol), tetrakistriphenylphosphine palladium (0.3...

Embodiment 2

[0055] Synthesis of compound 7

[0056]

[0057] In a three-necked flask, add intermediate 2-2 (2g, 4.9mmol), 2-(4-bromophenyl)-1-phenyl-1H-benzimidazole (1.7g, 4.9mmol), potassium carbonate (1.1 g, 10mmol), tetrakistriphenylphosphine palladium (0.1g), tetrahydrofuran (50ml) and water (20ml), heated for 5 hours under nitrogen protection, cooled, extracted with dichloromethane, dried, filtered, and the crude product was passed through the column Analyze and purify to obtain product 2.3g, productive rate 85%, its proton magnetic spectrum figure is as follows figure 2 shown.

Embodiment 3

[0059] Synthesis of compound 17

[0060]

[0061] In a three-necked flask, add intermediate 2-2 (2g, 4.9mmol), 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine (1.9g, 4.9mmol ), potassium carbonate (1.1g, 10mmol), tetrakistriphenylphosphine palladium (0.1g), tetrahydrofuran (50ml) and water (20ml), heated for 5 hours under nitrogen protection, cooled, extracted with dichloromethane, dried, filtered , the crude product was purified by column chromatography to obtain 1.9 g of the product, with a yield of 67%.

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Abstract

The invention provides an organic electroluminescent compound containing quinoxaline group. The compound has good thermal stability, high luminescent efficiency and high luminescent purity, is suitable for manufacturing organic electroluminescent devices and is applicable to the field of organic solar panels, organic thin-film transistors or organic photoreceptors. The invention also provides an organic electroluminescent device, comprising an anode, a cathode and an organic layer, the organic layer contains more than one of a luminescent layer, a hole injection layer, a hole transport layer, a hole blocking layer, an electron injection layer and an electron transport layer, and at least one layer in the organic layer contains the compound shown as in the following structural formula I.

Description

technical field [0001] The invention relates to the field of organic electroluminescent materials, in particular to an organic electroluminescent compound containing a quinoxaline group and an organic electroluminescent device, which belongs to the technical field of display of organic electroluminescent devices. Background technique [0002] Organic electroluminescent devices (OLEDs) are devices prepared by depositing a layer of organic materials between two metal electrodes by spin coating or vacuum evaporation. A classic three-layer organic electroluminescent device includes a hole transport layer, emissive layer and electron transport layer. The holes generated by the anode are combined with the electrons generated by the cathode through the hole transport layer to form excitons in the light emitting layer through the hole transport layer, and then emit light. Organic electroluminescent devices can be adjusted to emit various required lights by changing the material of ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D403/04C07D403/08C07D401/08C07D401/14C09K11/06H01L51/50H01L51/54
CPCC09K11/06C07D401/08C07D401/14C07D403/04C07D403/08C09K2211/1059C09K2211/1029C09K2211/1044H10K85/6572H10K50/00Y02E10/549
Inventor 黄锦海苏建华
Owner SHANGHIA TAOE CHEM TECH CO LTD
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