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Nitrogen heterocyclic compound, application thereof and OLED (organic light-emitting device)

A nitrogen heterocyclic compound and compound technology, applied in the field of organic electroluminescent materials, can solve the problems of unbalanced charge in the light-emitting layer, reduced device efficiency, difficult electron flow, etc., and achieve high luminous purity, good thermal stability, and high luminescence. The effect of efficiency

Inactive Publication Date: 2018-08-03
SHANGHIA TAOE CHEM TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the characteristics of CBP that holes are easy to transport and electrons are difficult to flow, the charge in the light-emitting layer is unbalanced, which reduces the efficiency of the device.

Method used

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  • Nitrogen heterocyclic compound, application thereof and OLED (organic light-emitting device)
  • Nitrogen heterocyclic compound, application thereof and OLED (organic light-emitting device)
  • Nitrogen heterocyclic compound, application thereof and OLED (organic light-emitting device)

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] Synthetic route of compound 1

[0050]

[0051] The synthetic method of intermediate 1-1

[0052] 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, yield 67%.

[0053] The synthetic method of compound 1

[0054] In the flask, add intermediate 1-1 (2g, 8.8mmol), 4-(9-carbazolyl) phenylboronic acid (2.5g, 8.8mmol), tetrakistriphenylphosphine palladium (0.1g), potassium carbonate ( 2.5g, 18mmol), tetrahydrofuran (20mL), water (10mL), heated to reflux under nitrogen protection for 10 hours, cooled, extracted with dichloromethane, dried, concentrated, and purified by column chromatography to obtain 3.3g of product, yield 86 %.

Embodiment 2

[0056] Synthetic route of compound 3

[0057]

[0058] The synthetic method of intermediate 3-1

[0059] 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 product 14g, yield 92%.

[0060] The synthetic method of intermediate 3-2

[0061] In a flask, add Intermediate 3-1 (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%.

[0062] The synthetic method of compound 3

[0063] The synthesis method was the same as that of compound 1 except that intermediate 1-1 was replaced by intermediate 3-2, and the yield was 82%.

Embodiment 3

[0065] Synthetic route of compound 5

[0066]

[0067] The synthetic method of compound 5

[0068] The synthesis method of compound 1 is consistent with that of compound 1, the raw materials used are intermediate 3-1 and 4-(9-carbazolyl)phenylboronic acid, and the yield is 65%.

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Abstract

The invention provides a nitrogen heterocyclic compound with a structural formula shown in the description. The nitrogen heterocyclic compound has better heat stability, high light-emitting efficiencyand high light-emitting purity and can be applied to the fields of OLEDs (organic light-emitting devices), organic solar cells, organic thin film transistors or organic light sensors. The invention also provides an OLED. The OLED comprises an anode, a cathode and organic layers, wherein the organic layers comprise at least one of a light-emitting layer, a hole injection layer, a hole transmissionlayer, a hole barrier layer, an electron injection layer and an electron transmission layer. At least one of the organic layers contains the heterocyclic compound shown in a structural formula I. TheOLED prepared from the nitrogen heterocyclic 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 a nitrogen heterocyclic compound and its application, and also 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 type of display technology, organic el...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04C07D519/00C09K11/06H01L51/30H01L51/46H01L51/54
CPCC09K11/06C07D487/04C07D519/00C09K2211/1092C09K2211/1007C09K2211/1029C09K2211/1011C09K2211/1014C09K2211/1044C09K2211/1037C09K2211/1033H10K85/624H10K85/631H10K85/657H10K85/6572Y02E10/549
Inventor 黄锦海苏建华
Owner SHANGHIA TAOE CHEM TECH CO LTD
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