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Organic semiconductor material, preparation method of organic semiconductor material and electroluminescent device

A technology of electroluminescent devices and organic semiconductors, which is applied in the direction of semiconductor devices, semiconductor/solid-state device manufacturing, and preparation of organic compounds, etc., can solve problems such as lack, achieve high triplet energy levels, improve luminous efficiency, and simple synthesis methods easy effect

Inactive Publication Date: 2014-03-12
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, there are few efficient blue phosphorescent devices, mainly due to the lack of both good carrier transport performance and high triplet energy level (E T ) of the host material

Method used

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  • Organic semiconductor material, preparation method of organic semiconductor material and electroluminescent device
  • Organic semiconductor material, preparation method of organic semiconductor material and electroluminescent device
  • Organic semiconductor material, preparation method of organic semiconductor material and electroluminescent device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Preparation process of 2,7-bis(phenylsulfoxy)-9,9-bis(4-(di-p-tolyl)aminophenyl)fluorene 1. Compound D: 2,7-dibromo-9,9 - Bis(4-(di-p-tolyl)aminophenyl)fluorene structural formula is The synthesis is as follows:

[0024]

[0025] Compound A: 2,7-dibromofluorenone (5.4g, 16mmol) was mixed with compound B: 4,4'-dimethyltriphenylamine (15g 55mmol), heated to 120°C under nitrogen atmosphere, and the mixture was completely dissolved , 1 mL of catalyst trifluoromethanesulfonic acid was added dropwise, and heating was maintained overnight. After the reaction, dichloromethane was added to dissolve the unreacted raw materials and other impurities, and the white solid compound D was obtained by filtration: 2,7-dibromo-9,9-bis(4-(di-p-tolyl)aminophenyl)fluorene , and the yield was 86%.

[0026] Experimental test data: mass spectrum: m / z867.2 (M + +1); elemental analysis (%) C 53 h 42 Br 2 N 2 : Theoretical value C73.45, H4.88, N3.23; measured value: C73.34, H4.90, N3.2...

Embodiment 2

[0032] Example 2: Preparation process of 2,7-bis(phenylsulfoxy)-9,9-bis(4-(di-p-tolyl)aminophenyl)fluorene

[0033] 1. Compound D: Refer to Example 1 for the preparation of 2,7-dibromo-9,9-bis(4-(di-p-tolyl)aminophenyl)fluorene.

[0034] 2. The structural formula of 2,7-bis(phenylsulfoxy)-9,9-bis(4-(di-p-tolyl)aminophenyl)fluorene is The synthesis is as follows:

[0035]

[0036] Compound D: 2,7-dibromo-9,9-bis(4-(di-p-tolyl)aminophenyl)fluorene (7.8 g, 9 mmol) was dissolved in potassium carbonate (2.12 g, 20.0 mmol) in toluene (150mL) solution, then add compound C: thiophenol (2.3g, 20.7mmol) and mix in a three-necked flask, stir and react at 110°C for 10 hours, stop the reaction and cool to room temperature, extract with dichloromethane, and rotate to evaporate The solvent was removed to obtain a crude product, which was then dissolved in acetic acid (100 mL), and 30% by mass hydrogen peroxide (50 mL) was added, and the reaction was stirred at 80°C for 24 hours. Wash ...

Embodiment 3

[0037] Example 3: Preparation process of 2,7-bis(phenylsulfoxy)-9,9-bis(4-(di-p-tolyl)aminophenyl)fluorene

[0038] 1. Compound D: Refer to Example 1 for the preparation of 2,7-dibromo-9,9-bis(4-(di-p-tolyl)aminophenyl)fluorene.

[0039]2. The structural formula of 2,7-bis(phenylsulfoxy)-9,9-bis(4-(di-p-tolyl)aminophenyl)fluorene is The synthesis is as follows:

[0040]

[0041] Compound D: 2,7-dibromo-9,9-bis(4-(di-p-tolyl)aminophenyl)fluorene (7.8 g, 9 mmol) was dissolved in tetrahydrofuran of potassium carbonate (1.68 g, 20.0 mmol) (150mL) solution, then add compound C: thiophenol (2.4g, 21.6mmol) and mix in a three-necked flask, stir and react at 70°C for 12 hours, stop the reaction and cool to room temperature, extract with dichloromethane, and rotate to evaporate The solvent was removed to obtain a crude product, which was then dissolved in acetic acid (100 mL), and 30% by mass hydrogen peroxide (50 mL) was added, and the reaction was stirred at 80°C for 24 hours. ...

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Abstract

The invention provides an organic semiconductor material. The organic semiconductor material has a chemical formula shown in the patent specification. The organic semiconductor material contains triphenylamine, fluorene and phenyl oxysulfide. Triphenylamine has hole transport performances. Fluorene and phenyl oxysulfide have electron transmission performances. Therefore, the organic semiconductor material is a bipolar red-light-emitting phosphorescent material having good hole transport performances and electron transmission performances. The invention also provides a preparation method of the organic semiconductor material and an electroluminescent device containing the organic semiconductor material.

Description

technical field [0001] The invention belongs to the field of photoelectric materials, and in particular relates to an organic semiconductor material, a preparation method and an electroluminescence device. 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 unwanted triplet-triplet (T 1 -T 1 ) are q...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C317/32C07C315/02C09K11/06H01L51/54
Inventor 周明杰王平张振华钟铁涛
Owner OCEANS KING LIGHTING SCI&TECH CO LTD
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