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Compounds based on phenanthrene and carbazole, applications thereof, and organic electroluminescent device

A compound and carbazole technology, applied in the field of organic electroluminescent materials, can solve the problems of reducing device efficiency, unbalanced charge in the light-emitting layer, and difficulty in electron flow, and achieve good thermal stability, high luminous purity, and high luminous efficiency Effect

Inactive Publication Date: 2018-07-20
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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  • Compounds based on phenanthrene and carbazole, applications thereof, and organic electroluminescent device
  • Compounds based on phenanthrene and carbazole, applications thereof, and organic electroluminescent device
  • Compounds based on phenanthrene and carbazole, applications thereof, and organic electroluminescent device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] Synthetic route of compound 1

[0051]

[0052] The synthetic method of intermediate 1-1

[0053] In a flask, add 9,10-dibromophenanthrene (16g, 48mmol), 9-phenyl-3-carbazole boronic acid (13.8g, 48mmol), potassium carbonate (13.6g, 100mmol), tetrakistriphenylphosphine palladium (0.5g), tetrahydrofuran (200mL) and water (100mL), heated to reflux under nitrogen protection for 12 hours, cooled, extracted with dichloromethane, dried, concentrated, and the crude product was purified by column chromatography to obtain 12.5g of product, the yield 52%.

[0054] The synthetic method of compound 1

[0055] In a flask, add Intermediate 1 (1.5g, 3mmol), 3-pyridineboronic acid (0.8g, 4mmol), potassium carbonate (0.8g, 6mmol), tetrakistriphenylphosphine palladium (50mg), tetrahydrofuran (20mL) and Water (10 mL), heated to reflux for 12 hours under nitrogen protection, cooled, extracted with dichloromethane, dried, concentrated, and the crude product was purified by column chro...

Embodiment 2

[0057] Synthetic route of compound 8

[0058]

[0059] The synthetic method of intermediate 8-1

[0060] In the flask, add intermediate 1-1 (8g, 16mmol), anhydrous tetrahydrofuran (100mL), cool to -78°C under nitrogen protection, slowly add 2.5M n-butyl-n-hexane solution (19mmol, 7.8mL), and react After 1 hour, add triisopropyl borate (21mmol, 3.9g), slowly rise to room temperature and react for 12 hours, then add dilute hydrochloric acid to adjust the pH to less than 7, extract with dichloromethane, dry, concentrate, and the crude product is washed with n-hexane Stir, filter, and dry to obtain 5.9 g of the product, with a yield of 79%.

[0061] The synthetic method of compound 8

[0062] The synthesis method is the same as that of compound 1, the raw materials used are intermediate 8-1 and 3,5-diphenyl-2-chlorotriazine, and the yield is 64%.

Embodiment 3

[0064] Synthetic route of compound 16

[0065]

[0066] The synthesis method is the same as that of compound 1, the raw materials used are intermediate 8-1 and 4-(4-bromophenyl)-2,6-diphenylpyrimidine, and the yield is 72%.

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Abstract

The invention provides compounds based on phenanthrene and carbazole. The compounds are represented by a formula shown in the description. The compounds have the advantages of good thermal stability,high luminescent efficiency, and high luminescent purity, and can be applied to fields such as organic electroluminescent device, organic solar cell, organic thin film transistor, organic photoreceptor, or the like. The invention also provides an organic electroluminescent device, which comprises an anode, a cathode, and an organic layer. The organic layer comprises at least one of luminescent layer, hole injecting layer, hole transporting layer, hole blocking layer, electron injecting layer, and electron transporting layer and at least comprises a layer containing compounds represented by thestructural formula I. The organic electroluminescent device prepared from the compounds has the advantages of good electroluminescent 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 compound based on phenanthrene and carbazole 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 type of display ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/10C07D403/10C07F9/572C09K11/06H01L51/50H01L51/54
CPCC09K11/06C07D401/10C07D403/10C07F9/5728C09K2211/1029C09K2211/1059C09K2211/1044C09K2211/1011C09K2211/1007H10K85/615H10K85/654H10K50/12H10K85/6572Y02E10/549
Inventor 黄锦海苏建华
Owner SHANGHIA TAOE CHEM TECH CO LTD
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