Fluorine-containing hole material of spirobifluorene structure and preparation method and application thereof

A spirobifluorene and hole technology, applied in the field of organic electroluminescence display, can solve the problems of low glass transition temperature, easy crystallization of materials, and destruction of film uniformity

Inactive Publication Date: 2019-05-21
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

Method used

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  • Fluorine-containing hole material of spirobifluorene structure and preparation method and application thereof
  • Fluorine-containing hole material of spirobifluorene structure and preparation method and application thereof
  • Fluorine-containing hole material of spirobifluorene structure and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0071]

[0072] The synthetic route is as follows:

[0073]

[0074] Including the following specific steps:

[0075] Synthesis of compound B-23-2

[0076] 500 ml three-neck flask, equipped with magnetic stirring, after argon replacement, add 18.1 g (0.188 mol) of potassium tert-butoxide, N-([1,1'-biphenyl]-4-yl)-9H-fluoro-2- Amine 33.34g (purity 99%, 0.1mol) and toluene 100ml. After nitrogen replacement again, 1.6 ml of tri-tert-butylphosphine and 0.23 g of palladium acetate were successively added. After the addition was complete, the temperature was raised to 85°C. Start to drop a solution consisting of 49.22 g of fluorine-containing spirobifluorene dibromo-substituent compound (1-1) (purity 99%, 0.1 mol) and 100 ml of toluene, and control the temperature at 80-120°C. Cool down to 50°C, add 100m deionized water for hydrolysis, stir for 10 minutes, filter, and boil the filter cake several times with DMF, and rotary evaporate to obtain 64.67g white solid with a puri...

Embodiment 2

[0081]

[0082] The synthetic route is as follows:

[0083]

[0084] Including the following specific steps:

[0085] Synthesis of compound B-24-2

[0086] 500 ml three-necked flask equipped with magnetic stirring, after argon replacement, add 18.1 g (0.188 mol) of potassium tert-butoxide and 33.34 g (purity 99%, 0.1mol) and toluene 100ml. After nitrogen replacement again, 1.6 ml of tri-tert-butylphosphine and 0.23 g of palladium acetate were successively added. After the addition was complete, the temperature was raised to 85°C. Start to drop a solution consisting of 49.22g of fluorine-containing spirobifluorene dibromosubstituent compound (purity 99%, 0.1mol) and 100ml of toluene, and control the temperature at 80-120°C. Cool down to 50°C, add 100m deionized water for hydrolysis, stir for 10 minutes, filter, and boil the filter cake several times with DMF to obtain 65.52g of white solid with a purity of 99% and a yield of 88%.

[0087] Synthesis of compound I-24-2...

Embodiment 3

[0091]

[0092] The synthetic route is as follows:

[0093]

[0094] Including the following specific steps:

[0095] Synthesis of compound B-114-2

[0096] 500 ml three-necked flask, equipped with magnetic stirring, after argon replacement, add 18.1 g (0.188 mol) of potassium tert-butoxide and 35.14 g (purity 99%, 0.1mol) and toluene 100ml. After nitrogen replacement again, 1.6 ml of tri-tert-butylphosphine and 0.23 g of palladium acetate were successively added. After the addition was complete, the temperature was raised to 85°C. A solution consisting of 49.22 g of fluorine-containing spirobifluorene dibromosubstituents (purity 99%, 0.1 mol) and 100 ml of toluene was added dropwise, and the temperature was controlled at 80-120°C. Cool down to 50°C, add 100m deionized water for hydrolysis, stir for 10 minutes, filter, and boil the filter cake several times with DMF to obtain 69.02g of white solid with a purity of 99% and a yield of 90.5%.

[0097] Synthesis of comp...

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Abstract

The invention relates to a fluorine-containing hole material of a spirobifluorene structure. The structure of the hole material is shown in the formula I. The hole material of the spirobifluorene structure is a novel OLED material, the novel material takes spirobifluorene as a main body, and therefore the glass transition temperature can be increased; the molecular thermal stability is high, moderate HOMO and LUMO energy levels and higher Eg are achieved, the photoelectric performance can be effectively improved, and the service life of OLED devices is prolonged. Arylamine groups are introduced, compared with single spirobifluorene, the better plane structure and the better conjugated system are achieved, synthesis and purification are simple, and the cost is low; benzene rings contain fluorine atoms, therefore the intermolecular distance can be increased, association among compounds is avoided, and the molecular stacking probability is reduced. In the evaporation process, the crystallization phenomenon cannot easily occur, the fluorine-containing hole material can effectively increase the finished product rate of OLEDs when applied to the OLED devices and effectively improve the luminous efficiency, and is good in film formation performance. The material can be used as a luminescent material, and the service life of the luminescent material can be effectively prolonged.

Description

technical field [0001] The invention relates to the technical field of organic electroluminescent display, in particular to a novel organic material and its application in organic electroluminescent devices. 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...

Claims

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Application Information

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IPC IPC(8): C07D209/88C07D333/76C07C211/61C07C209/10C07D213/74C07D213/38C07D251/22C07D409/12C07D409/14C07D401/12C07D401/14C07D403/12C07D403/14H01L51/54
Inventor 班全志李小赢程丹丹曹占广黄春雪段陆萌杭德余李继响李仲庆
Owner 北京燕化集联光电技术有限公司
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