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Organic light emitting diode material, synthetic method thereof and application of organic light emitting diode material in devices

A technology of electroluminescent materials and electroluminescent devices, which is applied in the fields of electric solid devices, electrical components, organic chemistry, etc., can solve problems such as low glass transition temperature, easy crystallization of materials, and destruction of film uniformity, and achieve high hole migration The effect of high efficiency and good film stability

Inactive Publication Date: 2019-03-22
北京燕化集联光电技术有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The organic hole transport materials currently reported are generally small in molecular weight and have a low glass transition temperature. During the use of the material, repeated charging and discharging will easily crystallize the material and destroy the uniformity of the film, thus affecting the service life of the material.

Method used

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  • Organic light emitting diode material, synthetic method thereof and application of organic light emitting diode material in devices
  • Organic light emitting diode material, synthetic method thereof and application of organic light emitting diode material in devices
  • Organic light emitting diode material, synthetic method thereof and application of organic light emitting diode material in devices

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0056] Synthesis of (Compound 1)

[0057] The synthetic route is as follows:

[0058]

[0059] 1) Synthesis of compound 1-2

[0060] 1000ml three-neck flask, equipped with magnetic stirring, after argon replacement, add 46.1g (0.48mol) of sodium tert-butoxide, 27.94g (purity 99%, 0.3mol) of 2-aniline, 68.04g of 6-bromo-1-fluoro -9-Phenyl-9H-carbazole (purity 99%, 0.2 mol) and xylene 400ml. After argon replacement again, 3 ml of tri-tert-butylphosphine and 0.46 g of tris(diphenylbenzylacetone)dipalladium were added in sequence. After the addition, start stirring and heat up to 120°C, and control the temperature at 120-130°C for 5 hours. After cooling down to 30°C, the filtrate was obtained by suction filtration through a silica gel column, and the filtrate was rotary evaporated, dissolved in dichloromethane, washed twice with 4mol / L hydrochloric acid solution, separated, dried with anhydrous sodium sulfate, suction filtered, and rotary evaporated The filtrate obtained ...

Embodiment 2

[0065] Synthesis of (Compound 2)

[0066] The synthetic route is as follows:

[0067]

[0068] 1) Synthesis of compound 2-1

[0069] 1000ml three-neck flask, equipped with magnetic stirring, after argon replacement, add 46.1g (0.48mol) of sodium tert-butoxide, 27.94g (purity 99%, 0.3mol) of 2-aniline, 68.04g of 6-bromo-1-fluoro -9-Phenyl-9H-carbazole (purity 99%, 0.2 mol) and toluene 400ml. After argon replacement again, 3 ml of tri-tert-butylphosphine and 0.46 g of tris(diphenylbenzylacetone)dipalladium were added in sequence. After the addition, start stirring and heat up to 100°C, and control the temperature at 100-110°C for 5 hours. After cooling down to 30°C, the filtrate was obtained by suction filtration through a silica gel column, and the filtrate was rotary evaporated, dissolved in dichloromethane, washed twice with 4mol / L hydrochloric acid solution, separated, dried with anhydrous sodium sulfate, suction filtered, and rotary evaporated The filtrate obtained...

Embodiment 3

[0074] Synthesis of (Compound 3)

[0075] The synthetic route is as follows:

[0076]

[0077] 1) Synthesis of compound 3-1

[0078] 1000ml three-neck flask, equipped with magnetic stirring, after argon replacement, add 46.1g (0.48mol) of sodium tert-butoxide, 27.94g (purity 99%, 0.3mol) of 2-aniline, 68.04g of 6-bromo-1-fluoro -9-Phenyl-9H-carbazole (purity 99%, 0.2 mol) and xylene 400ml. After argon replacement again, 3 ml of tri-tert-butylphosphine and 0.46 g of tris(diphenylbenzylacetone)dipalladium were added in sequence. After the addition, start stirring and heat up to 110°C, and control the temperature at 110-120°C for 5 hours. After cooling down to 30°C, the filtrate was obtained by suction filtration through a silica gel column, and the filtrate was rotary evaporated, dissolved in dichloromethane, washed twice with 4mol / L hydrochloric acid solution, separated, dried with anhydrous sodium sulfate, suction filtered, and rotary evaporated The filtrate obtained ...

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Abstract

The invention relates to the field of organic light emitting diode (OLED) display, in particular to an organic light emitting diode material, a synthetic method thereof and application of the organiclight emitting diode material in devices. The structure of the organic light emitting diode material is shown as the formula I. A fused-ring compound is taken as a center, fluorine-atom-containing aniline is taken as a terminal group, a substituent (8-fluoro-N, 9-diphenyl-9H-carbazol-3-amine) with the hole transfer property is introduced to an active position of a polycyclic aromatic compound, andaccordingly, the novel OLED material with the hole transfer property is obtained. The OLED material has high hole mobility, high film stability and suitable molecular energy level, and can be appliedto the field of organic electroluminescence to serve as a hole transfer material. The general formula I is shown in the description.

Description

technical field [0001] The invention relates to a novel organic material and its application in organic electroluminescence devices, belonging to the technical field of organic electroluminescence display. Background technique [0002] The application of organic electroluminescent (OLED) materials in information display materials, organic optoelectronic materials and other fields has great research value and bright application prospects. With the development of multimedia information technology, the performance requirements of flat panel display devices are getting higher and higher. At present, the main display technologies include plasma display devices, field emission display devices and organic electroluminescent display devices (OLED). Among them, OLED has a series of advantages such as self-luminescence, low-voltage DC drive, full curing, wide viewing angle, and rich colors. Compared with liquid crystal display devices, OLED does not require a backlight, has a wider v...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/88C07D471/04H01L51/50H01L51/54
CPCC07D209/88C07D471/04H10K85/615H10K85/622H10K85/624H10K85/623H10K85/6572H10K50/15
Inventor 段陆萌张朝霞李仲庆李继响郭林林曹占广杭德余班全志程丹丹黄春雪
Owner 北京燕化集联光电技术有限公司
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