Organic compound containing nitrogen heterocyclic ring, mixture, composition and application

A technology of organic compounds and nitrogen heterocycles, applied in the field of organic electroluminescence, can solve problems to be improved, and achieve the effects of good carrier transport capability, improved utilization efficiency, and improved efficiency and lifespan

Pending Publication Date: 2022-02-25
GUANGZHOU CHINARAY OPTOELECTRONICS MATERIALS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the use of bipolar transport molecules as the host can obtain good device performance, the performance and lifetime of the device still need to be improved. Therefore, it is urgent to develop new host materials.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0166] The synthesis of embodiment 1 compound 1

[0167]

[0168] (1) Synthesis of intermediate 1-3: compound 1-1 (10.0g), 1-2 (4.7g), cuprous iodide (3.8g), potassium carbonate (8.3g), trans 1,2 - Add cyclohexanediamine (6.8 g) to 200 ml of dry toluene; stir at 110° C. for 6 h under nitrogen atmosphere. After cooling, filter with suction, and the filtrate is washed with water for liquid separation and then recrystallized to obtain intermediate 1-3. MS (ASAP): 655.58.

[0169] (2) Synthesis of Compound 1: Dissolve 1-3 (8.5g) in 150ml dry DMAC, add palladium acetate (0.44g), P(Cy) 3 ·HBF 4 (1.5g), cesium carbonate (16.9g), reacted at 140°C for 4h in a nitrogen atmosphere. After cooling, most of the solvent was distilled off under reduced pressure, the remaining reaction solution was poured into a large amount of water, and filtered, and the obtained solid was subjected to column chromatography and recrystallization to obtain compound 1. MS (ASAP): 582.67.

Embodiment 2

[0170] The synthesis of embodiment 2 compound 2:

[0171]

[0172] (1) Synthesis of intermediate 2-2: compound 2-1 (5.0g), biboronic acid pinacol ester (5.7g), Pd(dppf)Cl 2 (0.1g) and potassium acetate (4.1g) were added to 100ml of dry 1,4-dioxane; under nitrogen atmosphere, stirred at 100°C for 6h. After cooling, it was filtered, and the filtrate was rotary evaporated to remove the solvent, and intermediate 2-2 was obtained through recrystallization. MS (ASAP): 290.95.

[0173] (2) Synthesis of intermediate 2-4: 2-2 (4.5g), 2-3 (4.2g), Pd(PPh 3 ) 4 (0.1g) and potassium carbonate (4.3g) were added to 1,4-dioxane / water (60ml / 15ml) mixed solvent; under nitrogen atmosphere, stirred at 85°C for 6h. After cooling, filter, the filtrate is rotary evaporated to remove the solvent, and the intermediate 2-4 is obtained through recrystallization. MS (ASAP): 396.25.

[0174] (3) Synthesis of Intermediate 2-6: Intermediate 2-4 (5.5g), 2-5 (3.9g) were dissolved in 100ml of dry DMF, a...

Embodiment 3

[0176] The synthesis of embodiment 3 compound 3

[0177]

[0178] (1) The synthesis of intermediate 3-2 refers to the synthesis of 2-6, except that intermediate 2-5 is replaced by intermediate 3-1. MS (ASAP): 749.70.

[0179] (2) The synthesis of compound 3 refers to the synthesis of compound 1, except that 1-3 is replaced by intermediate 3-2. MS (ASAP): 676.78.

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PUM

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Abstract

The invention relates to an organic compound containing a nitrogen heterocyclic ring, a mixture, a composition and an application thereof. The compound has a structural general formula as shown in a chemical formula (1), is good in stability, high in luminous efficiency, long in service life and simple to synthesize, and can be used in organic electronic devices to effectively improve the performance of the devices.

Description

technical field [0001] The invention relates to the technical field of organic electroluminescence, in particular to a nitrogen-containing heterocyclic organic compound, mixture, composition and application. Background technique [0002] Organic optoelectronic materials have diverse synthesis, relatively low manufacturing cost, and excellent optical and electrical properties. Organic light-emitting diodes (OLEDs) have broad development potential for applications in optoelectronic devices such as flat panel displays and lighting due to their advantages of wide viewing angle, fast response time, low operating voltage, and thin panel thickness. [0003] In order to improve the luminous efficiency of organic light-emitting diodes, various light-emitting material systems based on fluorescence and phosphorescence have been developed. Organic light-emitting diodes using fluorescent materials have the characteristics of high reliability, but their internal electroluminescence quantu...

Claims

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Application Information

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IPC IPC(8): C07D487/22C07D487/16C07D491/22C07D513/22C07D498/22C07D513/16C07D519/00C07D495/22C07D471/22C09K11/06H01L51/50H01L51/54
CPCC07D487/22C07D487/16C07D491/22C07D513/22C07D498/22C07D513/16C07D519/00C07D495/22C07D471/22C09K11/06C09K2211/1029C09K2211/1044C09K2211/1059C09K2211/1037C09K2211/1033C09K2211/1051C09K2211/1048C09K2211/1011H10K85/654H10K85/657H10K85/6572H10K50/12
Inventor 张晨李灿楷宋晶尧
Owner GUANGZHOU CHINARAY OPTOELECTRONICS MATERIALS
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