Anthracene organic luminescence compound, and preparation method and application thereof

A light-emitting compound, compound technology, applied in the direction of silicon organic compounds, organic chemistry, chemical instruments and methods, etc., can solve problems such as restricting applications

Pending Publication Date: 2019-06-14
JILIN OPTICAL & ELECTRONICS MATERIALS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, as an electron transport material, factors su

Method used

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  • Anthracene organic luminescence compound, and preparation method and application thereof
  • Anthracene organic luminescence compound, and preparation method and application thereof
  • Anthracene organic luminescence compound, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0110] Synthesis of Intermediate C-1:

[0111]

[0112] Reaction process: Add tris(dibenzylideneacetone)dipalladium (20.0g, 0.67mmol) and tricyclohexylphosphine (0.62g, 2.20mmol) into 500ml of 1,4-dioxane solvent, activate at room temperature 30 minutes. The air was replaced three times with nitrogen, Intermediate A-2 (20.0 g, 73.23 mmol), pinacol diboronate (20.46 g, 80.55 mmol) and potassium acetate (14.37 g, 146.46 mmol) were added. The air was replaced with nitrogen three times again, heated to 100° C. and stirred overnight under the protection of nitrogen. The end point of the reaction was monitored by TLC.

[0113] Processing: TLC monitoring. After the reaction was completed, it was cooled to room temperature under the protection of nitrogen. The catalyst was removed using celite and the celite was washed with DCM until free of product. The filtrate was distilled under reduced pressure to a small amount, and added dropwise to petroleum ether (300ml) to precipitat...

Embodiment 2

[0119] Synthesis of Intermediate D-2

[0120]

[0121] Reaction process: intermediate B-2 (18.50g, 57.78mmol), intermediate C-2 (34.33g, 57.78mmol), potassium carbonate (15.97g, 115.56mmol) were added to 500ml toluene / ethanol / water (volume ratio Preferably in a mixed solvent of 3:1:1). Replace the air with nitrogen three times, add tetrakis(triphenylphosphine)palladium, replace the air with nitrogen three times again, heat to 90° C. under the protection of nitrogen, and stir overnight for reaction.

[0122] Workup: TLC monitors the reaction. After the reaction was completed, the catalyst was removed using diatomaceous earth, the liquid was separated, the organic phase was retained, and a small amount was distilled under reduced pressure. The resulting crude product was separated by column chromatography (eluent preferably DCM:PE=1:5) to obtain intermediate D-2 (34.78 g, yield 85%).

[0123] The intermediates shown in Table 2 were prepared according to the above method. ...

Embodiment 3

[0129] Synthesis of intermediate G-1

[0130]

[0131] Reaction process: join three (dibenzylideneacetone) dipalladium (0.44g, 0.48mmol) and tricyclohexylphosphine (0.4g, 1.44mmol) in the 1,4-dioxane solvent of 500ml dryness, use Nitrogen replaced the air three times and activated at room temperature for 30 minutes. D-2 (34.0 g, 48.0 mmol), pinacol diboronate (13.41 g, 52.8 mmol) and potassium acetate (9.41 g, 96.0 mmol) were added to the reaction liquid. The air was replaced with nitrogen three times, and the reaction solution was heated to 100°C.

[0132] Workup: TLC monitors the reaction. After the reaction was completed, it was cooled to room temperature under the protection of nitrogen. The catalyst was removed using celite and the filter cake was rinsed with dichloromethane until free of product. Concentrate the filtrate at least a little, and add the concentrate dropwise to petroleum ether while stirring. After the solid was completely precipitated, it was sucti...

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Abstract

The invention relates to the technical field of organic optoelectronic materials and relates to an anthracene organic luminescence compound, a preparation method thereof and an organic electroluminescence device. The anthracene organic luminescence compound has a structure shown as a formula I: the formula 1 is shown in the description. Compared with other electron transfer layer materials or luminescent layer materials, the novel anthracene organic luminescence compound provided by the invention used as an electron transfer layer material or luminescent layer material of the organic electroluminescence device has the advantage that the luminous efficiency of the device prepared from the material is obviously promoted, and service life is obviously prolonged. The anthracene organic luminescence compound has the advantages of relatively short synthetic route, simple process, easily acquired raw materials, low cost and suitability for industrial production.

Description

technical field [0001] The invention relates to the technical field of organic optoelectronic materials, in particular to an anthracene organic light-emitting compound and its preparation method and application. Background technique [0002] Organic electroluminescence (EL) refers to a luminescence phenomenon in which organic materials directly convert electrical energy into light energy under the action of an electric field. It has the characteristics of self-illumination, bright colors, thin thickness, light weight, fast response speed, wide viewing angle, low driving voltage, tolerance to harsh natural conditions, and can be made into flexible panels. Advantage technology. [0003] Research on organic electroluminescent devices (OEL), that is, organic light-emitting diodes (OLEDs), began in the 1950s. A general organic electroluminescent device is composed of a cathode, an anode and an organic layer between them. Generally, the anode is transparent ITO, and the cathode...

Claims

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Application Information

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IPC IPC(8): C07D235/18C07D401/04C07D401/10C07D401/14C07D403/04C07D403/14C07D405/04C07D405/10C07D405/14C07D409/14C07D413/10C07D413/14C07D417/14C07D471/04C07F5/02C07F7/08C07F9/6558C09K11/06H01L51/54
Inventor 马晓宇汪康王永光王进政贺金新王铁赵贺李贺
Owner JILIN OPTICAL & ELECTRONICS MATERIALS
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