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Organic electroluminescence compound based on imidazole and pyridazine as well as application and organic electroluminescence device thereof

An imidazopyridazine, electroluminescence technology, applied in the direction of organic chemistry, electro-solid devices, electrical components, etc., can solve the problems affecting the life and efficiency of devices, low electron mobility, low electron mobility, etc., and achieve good thermal stability. The effect of high luminous efficiency, high luminous efficiency and high luminous purity

Inactive Publication Date: 2018-01-30
SHANGHIA TAOE CHEM TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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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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  • Organic electroluminescence compound based on imidazole and pyridazine as well as application and organic electroluminescence device thereof
  • Organic electroluminescence compound based on imidazole and pyridazine as well as application and organic electroluminescence device thereof
  • Organic electroluminescence compound based on imidazole and pyridazine as well as application and organic electroluminescence device thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] Synthetic route of compound 1

[0045]

[0046] The synthetic method of intermediate 1-1

[0047] In the flask, add 2-bromoacetophenone (10g, 50mmol), 3-amino-6-chloropyridazine (6.5g, 50mmol), ethanol (80mL), heat and reflux for 6 hours, cool, and filter to obtain the product 7.7 g, 67% yield.

[0048] The synthetic method of compound 1

[0049] In a flask, add intermediate 1-1 (1 g, 4.4 mmol), B-[4-(1-phenyl-1H-benzimidazol-2-yl)phenyl]-boronic acid (1.4 g, 4.4 mmol) , tetrakistriphenylphosphine palladium (0.1g), potassium carbonate (1.4g, 10mmol), tetrahydrofuran (15mL), water (10mL), heated to reflux for 10 hours under nitrogen protection, cooled, extracted with dichloromethane, dried, Concentrate, obtain product through column chromatography purification and be 1.7g, productive rate is 83%, and its NMR spectrum is as follows: figure 1 shown.

Embodiment 2

[0051] Synthetic route of compound 7

[0052]

[0053] The synthetic method of intermediate 7-1

[0054] In the flask, add 2-bromoacetophenone (10g, 50mmol), 3-amino-4-bromo-6-chloropyridazine (10.4g, 50mmol), add ethanol (100mL), heat and reflux for 5 hours, cool , and filtered to obtain 14 g of the product with a yield of 92%.

[0055] The synthetic method of intermediate 7-2

[0056] In a flask, add Intermediate 7-1 (8g, 26mmol), 4-biphenylboronic acid (5.2g, 26mmol), potassium carbonate (7.2g, 52mmol), tetrahydrofuran (100mL), water (50mL), tetrakistriphenyl Palladium phosphine (0.3g), heated to reflux for 6 hours under the protection of nitrogen, cooled, filtered, and the filter cake was recrystallized with ethanol and tetrahydrofuran to obtain 5.7g of the product with a yield of 58%. The synthetic method of compound 7

[0057] The synthesis method was the same as that of compound 1, except that intermediate 1-1 was replaced by intermediate 7-2, and the yield was 7...

Embodiment 3

[0059] Synthetic route of compound 40

[0060]

[0061] The synthetic method of intermediate 40-1

[0062] The synthesis method is the same as that of compound 1, the raw materials used are intermediate 1-1 and 3-chlorophenylboronic acid, and the yield is 54%.

[0063] The synthetic method of compound 40

[0064] In a flask, add intermediate 40-1 (1.5g, 4.9mmol), B-[3-(1-phenyl-1H-benzimidazol-2-yl)phenyl]-boronic acid (1.5g, 4.9mmol ), palladium acetate (0.1g), X-phos (0.2g), potassium carbonate (1.4g, 10mmol), dioxane (15mL), water (10mL), heated to reflux under nitrogen protection for 10 hours, cooled, It was extracted with dichloromethane, dried, concentrated, and purified by column chromatography to obtain 1.4 g of the product with a yield of 54%.

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Abstract

The invention provides an organic electroluminescence compound based on imidazole and pyridazine. The organic electroluminescence compound has the following structure as shown in the description. Thecompound has relatively good heat stability, high luminescence efficiency and high luminescence purity and can be applied to the organic electroluminescence devices, organic solar cells, organic thin-film transistors or organic photoreceptors. The invention also provides an organic electroluminescence device. The device comprises an anode, a cathode and an organic layer, wherein the organic layercomprises at least one luminescence layer, a hole injection layer, a hole transport layer, a hole barrier layer, an electron injection layer and an electron transport layer, and at least one layer ofthe organic layers comprises the compound of the structural formula I. The organic electroluminescence device produced by adopting the organic electroluminescence compound has the advantages of good electroluminescence efficiency, excellent color purity and long service life.

Description

technical field [0001] The invention relates to the field of organic electroluminescent materials, in particular to an imidazopyridazine-based organic electroluminescent material and its application, and also relates to an organic electroluminescent device. 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 the light-emitting layer as required. [0003] As a new ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04C09K11/06H01L51/50H01L51/54
Inventor 黄锦海苏建华
Owner SHANGHIA TAOE CHEM TECH CO LTD
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