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Spiro[fluorine-xanthene]phosphine sulfur red light phosphorescence main material, preparation method and application thereof

A technology of phosphorescent host and xanthene, which is applied in the direction of luminescent materials, chemical instruments and methods, semiconductor/solid-state device manufacturing, etc., to achieve the effects of enhanced electron transport capability, good electron transport performance, and reduced process flow

Inactive Publication Date: 2015-05-20
OCEANS KING LIGHTING SCI&TECH CO LTD +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The problem to be solved by the present invention lies in the spiro[fluorene-oxanthene] / phosphine-sulfur red phosphorescence host material with good carrier injection and transport balance and not easy to crystallize

Method used

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  • Spiro[fluorine-xanthene]phosphine sulfur red light phosphorescence main material, preparation method and application thereof
  • Spiro[fluorine-xanthene]phosphine sulfur red light phosphorescence main material, preparation method and application thereof
  • Spiro[fluorine-xanthene]phosphine sulfur red light phosphorescence main material, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Example 1: The spiro[fluorene-xanthene] / phosphine-sulfur red phosphorescent host material of this example, namely (4,4'-(3',6'-dimethoxyspiro[fluorene-9,9 '-Xanthene]-2,7-diyl)bis(4,1-phenylene))bis(diphenylphosphinesulfur), the preparation steps are as follows:

[0039]

[0040] Under argon protection, 2,7-dibromo-3',6'-dimethoxyspiro[fluorene-9,9'-oxanthene] (110mg, 0.2mmol), (4-bromophenyl) Diphenylphosphinesulfur (150mg, 0.4mmol) was added into a flask filled with 10ml of toluene solvent, and after fully dissolving, potassium carbonate (2mL, 2mol / L) solution was added into the flask, vacuumized to remove oxygen and filled with argon, Then bistriphenylphosphine palladium dichloride (5.6mg, 0.008mmol) was added; the flask was heated to 100°C for Suzuki coupling reaction for 24h. Stop the reaction and cool to room temperature, extract several times with dichloromethane and combine the organic phases, the organic phases are dried by anhydrous magnesium sulfate and t...

Embodiment 2

[0042] Example 2: The spiro[fluorene-xanthene] / phosphine-sulfur red phosphorescence host material of this example, namely (4,4'-(3',6'-di-n-butoxyspiro[fluorene-9, 9'-oxanthene]-2,7-diyl)bis(4,1-phenylene))bis(diphenylphosphinesulfur), the preparation steps are as follows:

[0043]

[0044] Under the protection of a mixed gas of nitrogen and argon, 2,7-dibromo-3',6'-di-n-butoxyspiro[fluorene-9,9'-oxanthene] (190mg, 0.3mmol), (4 -Bromophenyl)diphenylphosphinesulfur (247mg, 0.66mmol) and 15mL of tetrahydrofuran were added into a 50mL two-necked flask, fully dissolved, and then a mixture of nitrogen and argon was introduced to exhaust the air for about 20 minutes, and then the tetraphenyl Palladium phosphine (4mg, 0.003mmol) was added to it, and after fully dissolved, sodium bicarbonate (3mL, 2mol / L) solution was added. Then, the mixed gas of nitrogen and argon was exhausted for about 10 minutes, and the two-neck flask was added to 70°C for Suzuki coupling reaction for 48 hou...

Embodiment 3

[0045] Example 3: The spiro[fluorene-xanthene] / phosphine-sulfur red phosphorescent host material of this example, namely (4,4'-(3',6'-di-n-octyloxyspiro[fluorene-9, 9'-oxanthene]-2,7-diyl)bis(4,1-phenylene))bis(diphenylphosphinesulfur), the preparation steps are as follows:

[0046]

[0047] Under nitrogen protection, 2,7-dibromo-3',6'-dioctyloxyspiro[fluorene-9,9'-oxanthene] (224mg, 0.3mmol), (4-bromophenyl) Diphenylphosphine sulfur (269mg, 0.72mmol), palladium acetate (3.5mg, 0.015mmol) and three (o-methylphenyl) phosphine (21mg, 0.06mmol) were added to 12mL of N,N-dimethyl In the formamide flask, add potassium carbonate (3mL, 2mol / L) solution after fully dissolving, then blow nitrogen into the flask and exhaust the air for about 30min; heat the flask to 130°C for Suzuki coupling reaction for 12h. Stop the reaction and cool to room temperature, extract several times with dichloromethane and combine the organic phases, the organic phases are dried by anhydrous magnesium s...

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Abstract

The invention belongs to the field of organic electroluminescent device material, and discloses a spiro[fluorine-xanthene]phosphine sulfur red light phosphorescence main material, a preparation method and an application thereof. A structural formula of the material is shown as follows, in the formula, R is C1-C20 alkyl group. In the spiro[fluorine-xanthene]phosphine sulfur red light phosphorescence main material, a diphenyl phosphine sulfur group with a tetrahedral structure has electron-withdrawing P=S, has high triplet state energy level and good electron transmission performance, the electron transmission capability can be enhanced, the main material is in favor of carrier transmission balance, the main material has high triplet state energy level, energy return on the main material during a luminescence process can be effectively prevented, and luminescence efficiency is greatly increased.

Description

technical field [0001] The invention relates to the field of organic electroluminescent materials, in particular to a spiro[fluorene-xanthene] / phosphine-sulfur red phosphorescence host material and its preparation method and application. Background technique [0002] Organic electroluminescent devices have the advantages of low driving voltage, fast response speed, wide viewing angle range, rich colors through fine-tuning of chemical structure, easy realization of high resolution, light weight, and large-area flat-panel display. 21st Century Flat Panel Display Technology" has become a research hotspot in the fields of materials, information, physics and flat panel display. Future efficient commercial OLEDs will likely contain organometallic phosphors because they can trap both singlet and triplet excitons, thereby achieving 100% internal quantum efficiency. However, due to the relatively long lifetime of excited state excitons in transition metal complexes, the triplet-trip...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07F9/655H01L51/54
Inventor 周明杰张振华王平钟铁涛
Owner OCEANS KING LIGHTING SCI&TECH CO LTD
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