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A kind of compound with pyridine as core and its preparation method and application

A technology of compound and pyridine core, which is applied in the field of compounds with pyridine as the core and its preparation, can solve the problems of increasing electron injection barriers from the cathode to the light-emitting layer, increasing the driving voltage of the device, and complicating the structure of the device, so as to suppress energy transfer , Improving the device performance and the effect of strong electron transport ability

Active Publication Date: 2015-09-16
SOUTH CHINA UNIV OF TECH
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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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  • A kind of compound with pyridine as core and its preparation method and application
  • A kind of compound with pyridine as core and its preparation method and application
  • A kind of compound with pyridine as core and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] Embodiment 1: Preparation of compound I with pyridine as the nucleus

[0052] (1) Preparation of bromotriphenylpyridine

[0053]Under a nitrogen atmosphere, add 3-bromobenzaldehyde (1.85g, 10mmol, Aldrich), 3-bromoacetophenone (3.98g, 20mmol, Aldrich), potassium hydroxide (0.561g, 10mmol) into a 250ml three-necked flask ), concentrated ammonium hydroxide aqueous solution (60ml) and ethanol (150ml), stirred and reacted for 4 days under the condition of heating at 85 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=1:1. After being spin-dried, vacuum-dried to obtain 1.79 g of white powder with a yield of 32.9%.

[0...

Embodiment 2

[0062] Embodiment 2: Preparation of compound II with pyridine as the nucleus

[0063] (1) Preparation of Compound 2: Add 6-bromopyridine-2-carbaldehyde (1.86g, 10mmol, Aldrich), 6-bromo-2-acetylpyridine (4.00g, 20mmol) into a 250ml three-necked flask under nitrogen atmosphere , Aldrich), potassium hydroxide (0.561g, 10mmol), concentrated aqueous ammonium hydroxide solution (60ml) and ethanol (150ml), stirred and reacted for 4 days under heating at 85°C. 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=1:1. After being spin-dried, vacuum-dried to obtain 2.08 g of white powder with a yield of 38.1%.

[0064] 1 H NMR (500MHz, CDCl 3 ):δ(pp...

Embodiment 3

[0070] Embodiment 3: take pyridine as the photoelectric performance of the compound of nucleus

[0071] The compound with pyridine prepared in Examples 1 and 2 is prepared as a solid film, and it is scanned by ultraviolet-visible light absorption spectrum (see figure 1 ) and fluorescence spectral scans (see figure 2 ).

[0072] Evaluation of the electron transport property of the compound with pyridine as the core. The compound with pyridine as the core prepared in Examples 1 and 2 was prepared according to the following device structure to obtain a photoelectric device, and its electron transport, hole and exciton blocking properties were evaluated. The device The preparation method is prepared according to a method known in the art, that is: under high vacuum conditions, organic materials and cathode electrodes are sequentially vapor-deposited on the cleaned conductive glass ITO.

[0073] Device structure:

[0074] A. ITO / HIL (20nm) / TAPC (30nm) / 26DCzPPy:13wt% FIrpic (10n...

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Abstract

The invention belongs to the technical field of electroluminescent materials, and discloses a compound with pyridine as a nucleus, a preparation method and applications. The preparation method of the compound is as follows. Halogenated tri-aryl pyridine is synthesized through a condensation reaction in alkaline conditions. The halogenated tri-aryl pyridine and nitrogen heterocycle-containing boric acid ester are subjected to a SUZUKI coupling reaction in the presence of palladium catalyst to obtain a compound with pyridine as a nucleus. The compound is composed of units, with strong electron affinity, such as pyridine, pyrimidine and the like. The compound has low electron injection barriers and strong electron transporting capabilities, and therefore the driving voltage of devices can be reduced and the power efficiency can be raised. A photoelectric device based on the compound with pyridine as a nucleus has a driving voltage which is as low as 2.80 V, and power efficiency which is up to 105.71 m / W under a luminance of 100 cd / m<2>.

Description

technical field [0001] The invention belongs to the technical field of electroluminescent materials, and in particular relates to a compound with pyridine as the core, its preparation method and application. 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 excitons and trip...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D213/127H01L51/54
Inventor 苏仕健刘明
Owner SOUTH CHINA UNIV OF TECH
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