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Carbazole pyridine derivative, purpose of carbazole pyridine derivative and organic electroluminescence device

A technology of carbazole pyridine and derivatives, which is 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 achieves high luminescence purity, good thermal stability, and high luminescence. The effect of efficiency

Inactive Publication Date: 2018-03-27
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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  • Carbazole pyridine derivative, purpose of carbazole pyridine derivative and organic electroluminescence device
  • Carbazole pyridine derivative, purpose of carbazole pyridine derivative and organic electroluminescence device
  • Carbazole pyridine derivative, purpose of carbazole pyridine derivative and organic electroluminescence device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] Synthetic route of compound 1

[0045]

[0046] The synthetic method of intermediate 1

[0047] In the flask, add 2-iodo-4,4'-dibromobiphenyl (2.5g, 5.8mmol), 9-phenylcarbazole-3-boronic acid (1.7g, 5.8mmol), potassium carbonate (1.6g, 11.6mmol), tetrahydrofuran (20mL) and water (10mL), tetrakistriphenylphosphine palladium (0.2g), heated to reflux under nitrogen protection for 10 hours, cooled, extracted with dichloromethane, dried, concentrated, and the crude product was passed through the column Chromatographic purification afforded 1.5 g of the product in a 46% yield.

[0048] The synthetic method of compound 1

[0049] In a flask, add intermediate 1-1 (1.5 g, 2.7 mmol), pinacol 3-pyridineboronate (1.7 g, 8 mmol), potassium carbonate (0.74 g, 5.4 mmol), tetrahydrofuran (20 mL) and water ( 10mL), tetrakistriphenylphosphine palladium (0.2g), heated to reflux under nitrogen protection for 24 hours, cooled, extracted with dichloromethane, dried, concentrated, and t...

Embodiment 2

[0051] Synthetic route of compound 6

[0052]

[0053] The synthetic method of intermediate 6-1

[0054] In the flask, add 2-bromo-7,7-dimethyl-5-phenyl-indeno[2,1-B]carbazole (5g, 11.4mmol), dry tetrahydrofuran (50mL), and cool under nitrogen To -78 degrees, slowly add 2.5M n-butyllithium (5mL, 12.5mmol) dissolved in n-hexane, keep the reaction for 2 hours, then slowly add triisopropyl borate (2.4g, 12.5mmol), continue the reaction for 1 hour , slowly rise to room temperature and react for 12 hours, slowly add 2N dilute hydrochloric acid aqueous solution, adjust the pH value to be less than 7, add dichloromethane for extraction, dry, concentrate, add n-hexane, stir, and filter to obtain 3.8g of the product, the yield is 83%.

[0055] The synthetic method of intermediate 6-2

[0056] The synthesis method is the same as that of intermediate 1-1, the raw material used is intermediate 6-1, and the yield is 51%.

[0057] The synthetic method of compound 6

[0058] The synthe...

Embodiment 3

[0060] Synthetic route of compound 16

[0061]

[0062] The synthetic method of intermediate 16-1

[0063] The synthesis method is the same as that of intermediate 1-1, the raw material used is 4-carbazolylphenylboronic acid, and the yield is 62%.

[0064] The synthetic method of compound 16

[0065] The synthesis method is the same as that of compound 1, the raw material used is intermediate 16-1, and the yield is 68%.

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Abstract

The invention provides a carbazole pyridine derivative, which has the following structure formula shown in the description. The carbazole pyridine derivative has better thermal stability, and can be applied to the fields of an organic electroluminescence device, an organic solar battery, an organic film transistor or an organic light sensor. When the carbazole pyridine derivative is used for the organic electroluminescence device, the work voltage can be reduced; the device efficiency can be improved; the material is a phosphorescence main body material with excellent performance. The invention also provides the organic electroluminescence device, which comprises a positive electrode, a negative electrode and an organic layer, wherein the organic layer comprises at least one of a luminouslayer, a hollow hole injection layer, a hollow hole transmission layer, a hollow hole blocking layer, an electronic injection layer and an electron transmission layer; at least one of the organic layers comprises the compound shown by the structure formula I. The organic electroluminescence device manufactured by using the carbazole pyridine derivative 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 carbazole pyridine derivative 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 technology, org...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/14C07D491/048C07D495/04C07D487/04C09K11/06H01L51/50H01L51/54
CPCC09K11/06C07D401/14C07D487/04C07D491/048C07D495/04C09K2211/1092C09K2211/1088C09K2211/1029C09K2211/1011C09K2211/1007H10K85/615H10K85/654H10K85/6572H10K85/657H10K50/12Y02E10/549
Inventor 黄锦海苏建华
Owner SHANGHIA TAOE CHEM TECH CO LTD
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