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Electronic input type red phosphorescent compound, preparation method thereof and organic electroluminescent device

A technology of electron input and compound, which is applied in the field of electron input red phosphorescent compound and its preparation, and organic electroluminescent devices, can solve the problems of lack of host materials, high driving voltage, low luminous efficiency, etc., and achieve reduction of process flow, Reduced manufacturing cost and improved luminous efficiency

Inactive Publication Date: 2014-05-21
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

However, efficient red phosphorescent devices are rare, mainly due to the lack of suitable host materials.
[0003] At present, the host material widely used in red phosphorescent devices is CBP (4,4'-bis(9-carbazolyl)biphenyl), but it requires high driving voltage and glass transition temperature (T g ) Low (T g =62℃), easy to crystallize
In addition, CBP is a p-type material, the hole mobility is much higher than the electron mobility, which is not conducive to the balance of carrier injection and transport, and the luminous efficiency is low

Method used

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  • Electronic input type red phosphorescent compound, preparation method thereof and organic electroluminescent device
  • Electronic input type red phosphorescent compound, preparation method thereof and organic electroluminescent device
  • Electronic input type red phosphorescent compound, preparation method thereof and organic electroluminescent device

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Experimental program
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preparation example Construction

[0031] The preparation method of the above-mentioned electron-input type red phosphorescent compound comprises the following steps:

[0032] S1. In an oxygen-free environment (by nitrogen, argon, or a mixture of nitrogen and argon), the structural formula is Compound A (i.e. 4-iodo-9,9-spirobifluorene) is dissolved in an organic solvent, and then added to the organic solvent with the structural formula compound B (i.e. thiophenol), then add inorganic base and catalyst to the organic solvent, react at 70-120°C for 3-12 hours, stop the reaction and cool to room temperature, the structural formula is Compound C (ie, 9,9-spirobifluoren-4-yl(phenyl)sulfane); wherein, the molar ratio of compound A to compound B is 1:1~1:1.2; the reaction formula is as follows:

[0033]

[0034] S2. Dissolve compound C in dichloromethane at 0°C to obtain a mixed solution, and then drop the mixed solution into m-chlorobenzoic acid (mCPBA) (structural formula: ) in dichloromethane (DCM) soluti...

Embodiment 1

[0057] The electron-input type red phosphorescent compound of this example is: 4-(phenylsulfonyl)-9,9-spirobifluorene, the structural formula is as follows:

[0058]

[0059] The preparation process of this compound is as follows:

[0060] The first step, the preparation of compound C

[0061]

[0062] Under nitrogen protection, 4-iodo-9,9-spirobifluorene (35.4g, 80mmol) was dissolved in 200mL N,N-dimethylformamide (DMF) solution, then thiophenol (44.0g, 80mmol ), potassium carbonate (22.1g, 160mmol), cuprous iodide (1.52g, 8mmol). The mixture was stirred and reacted at 120°C for 3 hours. The reaction was stopped and cooled to room temperature, filtered, and the solid was washed three times with distilled water. The crude product was separated by silica gel column chromatography using n-hexane as the eluent to obtain Compound C as an off-white solid. The yield was 85%.

[0063] The second step, the preparation of 4-(phenylsulfonyl)-9,9-spirobifluorene

[0064]

...

Embodiment 2

[0068] The electron-input type red phosphorescent compound of this example is: 4-(phenylsulfonyl)-9,9-spirobifluorene, the structural formula is as follows:

[0069]

[0070] The preparation process of this compound is as follows:

[0071] The first step, the preparation of compound C

[0072]

[0073] Under argon protection, 4-iodo-9,9-spirobifluorene (35.4g, 80mmol) was dissolved in 200mL of toluene (Tol) solution, then thiophenol (48.4g, 88mmol), cesium carbonate (57.2 g, 176mmol), copper powder (0.768g, 12mmol). The mixture was stirred and reacted at 110°C for 6 hours. The reaction was stopped and cooled to room temperature, filtered, and the solid was washed three times with distilled water. The crude product was separated by silica gel column chromatography using n-hexane as the eluent to obtain Compound C as an off-white solid. The yield was 90%.

[0074] The second step, the preparation of 4-(phenylsulfonyl)-9,9-spirobifluorene

[0075] This step is the same...

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Abstract

The invention belongs to the field of organic semiconductor materials, and discloses an electronic input type red phosphorescent compound, a preparation method thereof and an organic electroluminescent device. The compound has a structural formula shown in the specification. The electronic input type red phosphorescent compound has an electronic transmission capacity, so it is benefit for realizing the carrier transfer balance, thereby the luminous efficiency of the compound is substantially improved.

Description

technical field [0001] The invention relates to organic semiconductor materials, in particular to an electron-input type red phosphorescent compound and a preparation method thereof. The invention also relates to an organic electroluminescent device using the electron-input red phosphorescent compound as a host material of a light-emitting layer. 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. Howeve...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C317/14C07C315/02C09K11/06H01L51/54
Inventor 周明杰王平张振华梁禄生
Owner OCEANS KING LIGHTING SCI&TECH CO LTD
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