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Bipolar red phosphorescent compound, and preparation method and application thereof

A compound and bipolar technology, applied in the field of bipolar red phosphorescent compounds and their preparation, can solve the problems of unfavorable carrier injection and transport balance, low glass transition temperature, lack of host materials, etc. Balanced carrier transport, good thermal stability, and reduced process flow effects

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 with much higher hole mobility than electron mobility, which is not conducive to the balance of carrier injection and transport, resulting in low luminous efficiency.

Method used

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  • Bipolar red phosphorescent compound, and preparation method and application thereof
  • Bipolar red phosphorescent compound, and preparation method and application thereof
  • Bipolar red phosphorescent compound, and preparation method and application thereof

Examples

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preparation example Construction

[0027] The preparation method of the above-mentioned bipolar red light phosphorescent compound comprises the following steps:

[0028] S1, respectively provide compounds A and B represented by the following structural formula:

[0029] Namely (4-iodophenyl)triphenylsilane;

[0030] That is, 4-(diphenylamino)thiophenol;

[0031] S2. Under an oxygen-free environment (nitrogen, argon or a mixture of nitrogen and argon), dissolve compound A in an organic solvent, then add compound B, an inorganic base and a catalyst to obtain a mixed solution, and the mixed solution is at 70- Substitution reaction at 120°C for 3 to 12 hours, stop the reaction and cool to room temperature, the reaction solution is separated and purified to obtain the structural formula: Compound C (N,N-diphenyl-4-(4-(triphenylsilyl) phenylthio) aniline); the reaction formula is as follows:

[0032]

[0033] Preferably, the separation and purification treatment of compound C comprises steps:

[0034] The...

Embodiment 1

[0048]The preparation steps of the bipolar red phosphorescent compound of this example, namely N,N-diphenyl-4-(4-(triphenylsilyl)phenylsulfonylaniline) are as follows:

[0049]

[0050] Step 1: Dissolve (4-iodophenyl)triphenylsilane (36.7g, 80mmol) in 200mL N,N-dimethylformamide (DMF) solution under nitrogen protection, then add 4-(di Phenylamino)thiophenol (22.2g, 80mmol), potassium carbonate (22.1g, 160mmol), cuprous iodide (1.52g, 8mmol). The mixture was stirred at 120°C for 3 hours for substitution reaction. 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 chromatography using n-hexane as the eluent to obtain product C as an off-white solid. The yield was 87%.

[0051] Step 2: Dissolve C (24.5g, 40mmol) in 120mL of dichloromethane (DCM) solution in an ice-water mixing bath, and then drop it into 90mL of m-chlorobenzoic acid (mCPBA) in dichlorometh...

Embodiment 2

[0054] The preparation steps of the bipolar red phosphorescent compound of this example, namely N,N-diphenyl-4-(4-(triphenylsilyl)phenylsulfonylaniline) are as follows:

[0055]

[0056] Step 1: Dissolve (4-iodophenyl)triphenylsilane (36.7g, 80mmol) in 200mL toluene (Tol) solution under nitrogen protection, then add 4-(diphenylamino)thiophenol (24.4g, 88mmol), cesium carbonate (57.2g, 176mmol), copper powder (0.768g, 12mmol). The mixture was stirred for a substitution reaction 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 chromatography using n-hexane as the eluent to obtain product C as an off-white solid. The yield was 84%.

[0057] The second step: the difference between this step and the second step in Example 1 is that the oxidation reaction time is 18 hours; after the oxidation reaction finishes, add saturated NaHCO to t...

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Abstract

The invention belongs to the field of organic semiconductor materials, and discloses a bipolar red phosphorescent compound, and a preparation method and an application thereof. The compound has a structural formula shown in the specification. The bipolar red phosphorescent compound has a high triplet energy level, so the return of energy to a host material in the luminescence process can be effectively prevented, the carrier transfer balance is benefited, and the luminous efficiency is substantially improved.

Description

technical field [0001] The invention relates to an organic semiconductor material, in particular to a bipolar red phosphorescence compound 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 organic electroluminescent devices 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-triplet (T 1 -T 1 ) is quenc...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F7/10C09K11/06H01L51/54
Inventor 周明杰王平张振华钟铁涛
Owner OCEANS KING LIGHTING SCI&TECH CO LTD
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