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Organic compound and preparation method thereof, and application of organic compound in devices

An organic compound and compound technology, applied in the field of organic electroluminescent display, can solve the problems of low glass transition temperature, easy crystallization of materials, and destruction of film uniformity, and achieve the effect of high hole mobility and good film stability

Inactive Publication Date: 2019-05-07
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 compound and preparation method thereof, and application of organic compound in devices
  • Organic compound and preparation method thereof, and application of organic compound in devices
  • Organic compound and preparation method thereof, and application of organic compound in devices

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0057] Synthesis of (Compound 1)

[0058] The synthetic route is as follows:

[0059]

[0060] 1) Synthesis of compound 1-2

[0061] 1000 ml three-necked flask, equipped with magnetic stirring, after argon replacement, add 46.1 g (0.48 mol) of sodium tert-butoxide, 27.94 g (purity 99%, 0.3 mol) of 2-aniline, and 68.04 g of 3-bromo-4-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 filtra...

Embodiment 2

[0066] Synthesis of (Compound 2)

[0067] The synthetic route is as follows:

[0068]

[0069] 1) Synthesis of Compound 2-1

[0070] 1000 ml three-necked flask, equipped with magnetic stirring, after argon replacement, add 46.1 g (0.48 mol) of sodium tert-butoxide, 27.94 g (purity 99%, 0.3 mol) of 2-aniline, and 68.04 g of 3-bromo-4-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 filtr...

Embodiment 3

[0075] Synthesis of (Compound 3)

[0076] The synthetic route is as follows:

[0077]

[0078] 1) Synthesis of compound 3-1

[0079] 1000 ml three-necked flask, equipped with magnetic stirring, after argon replacement, add 46.1 g (0.48 mol) of sodium tert-butoxide, 27.94 g (purity 99%, 0.3 mol) of 2-aniline, and 68.04 g of 3-bromo-4-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 filtr...

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Abstract

The invention relates to the field of organic electroluminescence (OLED) display, specifically to an organic compound and a preparation method thereof, and an application of the organic compound in devices. The organic compound has a structure as shown in a general formula I which is described in the specification. According to the invention, with a fused ring compound as a center and fluorine-atom-containing aniline as a terminal group, a substituent namely (4-fluoro-N,9-diphenyl-9H-carbazole-3-amine) with hole transport performance is introduced at the active position of a polycyclic aromatic compound to obtain a novel OLED material with hole transport performance. The material provided by the invention has high hole mobility, good film stability and proper molecular energy level, and can be applied in the field of organic electroluminescence as a hole transporting material for use.

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
Inventor 段陆萌张朝霞李仲庆郭林林曹占广杭德余班全志程丹丹李继响黄春雪
Owner 北京燕化集联光电技术有限公司
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