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A kind of organic electronic material containing nitrogen atom heterocycle and its preparation method and application

A technology of organic electronic materials and nitrogen atom heterocycles, applied in organic chemistry, luminescent materials, chemical instruments and methods, etc., can solve the problem of reducing device efficiency and device service life, high driving voltage, and unbalanced number of electrons and holes And other problems, to achieve the effect of prolonging the life of the device, reducing the driving voltage, and good thermal stability

Active Publication Date: 2020-12-22
SHANGHAI CHUANQIN NEW MATERIAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This makes the number of electrons and holes in the light-emitting layer unbalanced, causing the device to emit light away from the light-emitting layer and close to the electrode, which requires a higher driving voltage, and also reduces the efficiency of the device and the service life of the device

Method used

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  • A kind of organic electronic material containing nitrogen atom heterocycle and its preparation method and application
  • A kind of organic electronic material containing nitrogen atom heterocycle and its preparation method and application
  • A kind of organic electronic material containing nitrogen atom heterocycle and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0059] An organic electronic material containing a heterocyclic nitrogen atom, the organic electronic material contains compound CQ1, and the synthetic route of compound CQ1 is as follows:

[0060]

[0061] The synthetic method of intermediate CQ1-1:

[0062] In the flask, add o-bromoiodobenzene (52.2g, 184.5mmol), phenylacetylene (18.85g, 184.5mmol) and triethylamine (260mL), under nitrogen protection, add cuprous iodide (0.35g, 1.84mmol) and Triphenylphosphinepalladium chloride (0.5g, 0.7mmol), stirred at room temperature for 0.5h, then stopped the reaction, filtered, and concentrated to remove triethylamine to obtain 46.8g of yellow oily liquid, with a yield of 98%.

[0063] 1 H NMR (400MHz, CDCl 3 ,δ):7.62-7.64(m,2H),7.57(dd,J=7.2,1.2Hz,1H),7.51(dd,J=5.2,1.2Hz,1H),7.32-7.40(m,5H).

[0064] The synthetic method of intermediate CQ1-2:

[0065] In the flask, add intermediate CQ1-1 (13.4g, 52.1mmol), p-chlorophenylboronic acid (8.5g, 54.4mmol) and potassium carbonate (1...

Embodiment 2

[0077] An organic electronic material containing a heterocyclic nitrogen atom, the organic electronic material contains compound CQ2, and the synthetic route of compound CQ2 is as follows:

[0078]

[0079] The synthetic method of compound CQ2

[0080] Add intermediate CQ1-4 (2g, 5.5mmol), 2,4-diphenyl-6-(4-phenylboronic acid pinacolate)-1,3,5-triazine (2.5g, 5.7 mmol) and potassium carbonate (2.3g, 16.6mmol), then add toluene (20mL), ethanol (10mL) and deionized water (10mL), add palladium acetate (0.06g, 0.27mmol) and x-phos ( 0.12g, 0.54mmol), reflux reaction for 2h, a large amount of solids were precipitated, cooled, filtered, and the filter cake was washed with water until neutral, then washed with ethanol, and dried. Then recrystallize once with toluene, dry, obtain 2.2g product, yield 63%, the product that obtains is compound CQ2, and its proton magnetic spectrum is as follows figure 1 shown.

[0081] 1 H NMR: (400MHz, CDCl 3 )δ8.77-8.95(m,8H),8.47-8.48(m,2H),8....

Embodiment 3

[0083] An organic electronic material containing a heterocyclic nitrogen atom, the organic electronic material contains compound CQ5, and the synthetic route of compound CQ5 is as follows:

[0084]

[0085] The synthetic method of compound CQ5

[0086] Add intermediate CQ1-4 (8g, 21.9mmol), 2,4-diphenyl-6-(3-phenylboronic acid pinacolate)-1,3,5-triazine (10g, 23.0mmol) in the flask ) and potassium carbonate (9.1g, 65.8mmol), then add toluene (80mL), ethanol (40mL) and deionized water (40mL), add palladium acetate (0.24g, 1.1mmol) and x-phos (0.48 g, 2.2 mmol), reflux reaction for 2h, a large amount of solids were precipitated, cooled, filtered, and the filter cake was washed with water until neutral, then washed with ethanol, and dried. Then recrystallized once with toluene and dried to obtain 4.6g of product with a yield of 33%.

[0087] 1 H NMR (400MHz, CDCl 3 ,δ):8.88-8.98(m,3H),8.74-8.78(m,5H),8.47-8.49(m,2H),8.10-8.13(m,1H),7.94(s,1H),7.73-7.81 (m, 2H), 7.51-7.64 ...

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Abstract

The invention provides an organic electronic material containing a heterocyclic nitrogen atom, a preparation method and application thereof, and relates to the technical field of organic electroluminescence. The invention introduces heterocycles containing nitrogen atoms such as pyridine, triazine or pyrimidine into the main structure of phenanthrene to enhance the electronegativity of the material, improve the electron transport performance of the compound, and improve the thermal stability of the compound. The organic electron transport material provided by the invention has good thermal stability, high luminous efficiency and high luminous purity. The organic electroluminescent device made of the organic electronic material can reduce the driving voltage, improve the luminous efficiency, have excellent color purity and prolong the device life.

Description

Technical field: [0001] The invention relates to the technical field of organic electroluminescence, in particular to an organic electronic material containing a heterocyclic nitrogen atom and its preparation method and application. Background technique: [0002] With the development of science and technology and economy, people's requirements for quality of life are also improving, including of course display and lighting technologies that are closely related to people's lives. New display and lighting technologies not only need to meet the color requirements of the human eye, but also be healthy and environmentally friendly. As a new type of display technology, organic electroluminescent devices (OLEDs) can be switched freely and actively emit light, which makes the display response time short and the color contrast high; the driving voltage is low to reduce energy consumption; the use of organic materials makes the device It is thinner and more environmentally friendly; ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D401/10C09K11/06H01L51/54
CPCC07D401/10C09K11/06C09K2211/1044C09K2211/1059C09K2211/1029C09K2211/1011C09K2211/1007H10K85/615H10K85/654Y02E10/549
Inventor 苏艳周海涛黄珠菊
Owner SHANGHAI CHUANQIN NEW MATERIAL CO LTD
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