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Heterocompound organic material containing pyridine and metadiazine as well as preparation method and application thereof

An organic material, pyridine technology, applied in the field of organic electroluminescent materials, can solve problems such as increasing electron injection barriers from the cathode to the light-emitting layer, increasing device driving voltage, and complex device structure, so as to suppress energy transfer and reduce driving voltage , The effect of simple device structure

Inactive Publication Date: 2012-06-20
SOUTH CHINA UNIV OF TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The commonly used electron transport materials, such as tri-8-hydroxyquinoline aluminum, because of their lower triplet energy level, usually need to insert a layer of holes and Exciton blocking layer, which correspondingly increases the electron injection barrier from the cathode to the light-emitting layer, increases the driving voltage of the device, and the device structure is more complex

Method used

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  • Heterocompound organic material containing pyridine and metadiazine as well as preparation method and application thereof
  • Heterocompound organic material containing pyridine and metadiazine as well as preparation method and application thereof
  • Heterocompound organic material containing pyridine and metadiazine as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Example 1: Preparation of 4,6-bis(3,5-bis(3-pyridyl)phenyl)-2-(3-pyridyl)pyrimidine (I)

[0034]

[0035] Step 1: 2-Chloro-4,6-bis(3,5-dichlorophenyl)pyrimidine

[0036] Under a nitrogen atmosphere, add 2,4,6-trichloropyrimidine (5.50g, 30mmol), 3,5 dichlorophenylboronic acid (12.0g, 63mmol), 2M potassium carbonate aqueous solution (60ml) into a 250ml three-necked flask , triphenylphosphorous palladium chloride (0.84g, 1.2mmol) and acetonitrile (150ml), stirred and reacted for 22 hours under heating at 50 degrees Celsius. After the reaction was naturally cooled, the reaction solution was extracted with chloroform, washed three times with saturated brine, and the obtained organic layer was dried over anhydrous magnesium sulfate. Filter with suction, and remove the solvent in the resulting filtrate under reduced pressure. Separation with a chromatographic column, the mobile phase used is chloroform / n-hexane=2:1. After being spin-dried, vacuum-dried to obtain 11.2 g ...

Embodiment 2

[0045] Example 2: Preparation of 4,6-bis(3,5-bis(4-pyridyl)phenyl)-2-(3-pyridyl)pyrimidine (II)

[0046]

[0047] The first two steps of the present embodiment are the same as the first two steps of the first embodiment.

[0048] Step 3: 4,6-bis(3,5-bis(4-pyridyl)phenyl)-2-(3-pyridyl)pyrimidine

[0049] Under a nitrogen atmosphere, 4,6-bis(3,5-dichlorophenyl)-2-(3-pyridyl)pyrimidine (0.80g, 1.8mmol), 4-pyridineboronic acid were added to a 250ml three-necked flask Ester (4.41g, 2.15mmol), aqueous potassium phosphate (2.58g, 30ml), tris(dibenzylideneacetone)dipalladium (0.20g, 0.21mmol), tricyclohexylphosphine (0.15g, 0.52mmol) and 1 , 4-dioxane (100ml), stirred and reacted under reflux for 24 hours. After the reaction was naturally cooled, the reaction solution was extracted with chloroform, washed three times with saturated brine, and the obtained organic layer was dried over anhydrous magnesium sulfate. Filter with suction, and remove the solvent in the resulting filtra...

Embodiment 3

[0052] Example 3: Preparation of 4,6-bis(3,5-bis(3-pyridyl)phenyl)-2-(3-(3-pyridyl)phenyl)pyrimidine (III)

[0053]

[0054] The first step of the present embodiment is the same as that of the first embodiment.

[0055] Step 2: 4,6-bis(3,5-dichlorophenyl)-2-(3-(3-pyridyl)phenyl)pyrimidine

[0056] Under a nitrogen atmosphere, 2-chloro-4,6-bis(3,5-dichlorophenyl)pyrimidine (4.04g, 10mmol), 3-(3-pyridyl)phenylboronic acid were added to a 250ml three-necked flask Ester (3.09g, 11mmol), 2M potassium carbonate aqueous solution (50ml), triphenylphosphorous palladium chloride (0.14g, 0.2mmol) and 1,4-dioxane (120ml), stirred reaction under heating reflux condition 18 Hour. After the reaction was naturally cooled, the reaction solution was extracted with chloroform, washed three times with saturated brine, and the obtained organic layer was dried over anhydrous magnesium sulfate. Filter with suction, and remove the solvent in the resulting filtrate under reduced pressure. Separ...

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Abstract

The invention discloses a heterocompound organic material containing pyridine and metadiazine as well as a preparation method and an application of the heterocompound organic material. According to the preparation method of the material, the metadiazine is used as a core, and phenyl and pyridine are introduced on the periphery through selective palladium catalysis Suzuki coupling reaction, so the goal of regulating and controlling the material molecule rail energy stage is reached. The material has the electron transmission capability, simultaneously has the hole and exciton blocking capability and can be applied to organic electroluminescent diode electron transmission layers.

Description

technical field [0001] The invention relates to the field of organic electroluminescent materials, in particular to a hybrid organic material containing pyridine and pyrimidine, a preparation method and application thereof. Background technique [0002] In the past two decades, organic light-emitting diodes (OLEDs) have broad application prospects due to their high efficiency, low-voltage drive, easy large-area preparation and full-color display, and have attracted widespread attention. The research began in the 1950s, and until 1987, Dr. Deng Qingyun of Kodak Company of the United States adopted a sandwich device structure in the patent US4356429, and the OLED device developed by the 10V DC voltage drive had a luminous brightness of 1000cd / m 2 , so that OLED has achieved an epoch-making development. [0003] Organic electroluminescence is mainly divided into fluorescence and phosphorescence, but according to the spin quantum statistical theory, the probability of singlet e...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/14H01L51/54
Inventor 苏仕健赵伟明
Owner SOUTH CHINA UNIV OF TECH
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