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Organic compound as well as preparation method and application thereof

A technology of organic compounds and compounds, applied in organic chemistry, chemical instruments and methods, semiconductor/solid-state device manufacturing, etc., can solve problems such as low glass transition temperature, destruction of film uniformity, and impact on the service life of materials

Inactive Publication Date: 2019-08-16
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 as well as preparation method and application thereof
  • Organic compound as well as preparation method and application thereof
  • Organic compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0068] (Compound I-2-1) Synthesis

[0069] The synthetic route is as follows:

[0070]

[0071] Including the following specific steps:

[0072] 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-fluorene-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 add dropwise a solution consisting of 48.82g of methylspirobifluorene-bromo-substituent-containing compound (A-2-1) (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 to hydrolyze, stir for 10 minutes, filter, and boil the filter cake several times with DMF, and rotary steam to obtain 65.92g white solid with a purity of 99% and ...

Embodiment 2

[0075] Synthesis of (Compound I-31-1)

[0076] The synthetic route is as follows:

[0077]

[0078] Including the following specific steps:

[0079] 500 ml three-neck flask, equipped with magnetic stirring, after argon replacement, add 18.1 g (0.188 mol) of potassium tert-butoxide, N-dibenzo[b,d]thiophene-5-(p-tolyl)pyridin-2-amine in sequence 36.65g (purity 99%, 0.15mol) 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 add dropwise a solution consisting of 10.93g of methylspirobifluorene-bromo-substituent-containing compound (A-31-1) (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 61.15g of white product with a purity...

Embodiment 3

[0082] Synthesis of (Compound I-55-1)

[0083] The synthetic route is as follows:

[0084]

[0085] Including the following specific steps:

[0086] 500 ml three-neck flask, equipped with magnetic stirring, after argon replacement, add 18.1 g (0.188 mol) of potassium tert-butoxide, N-(5-(p-tolyl)pyridin-2-yl)isoquinolin-7-amine in sequence 31.13g (99% purity, 0.15mol) and 100ml toluene. 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 40.93g of the methylspirobifluorene-bromo-substituent-containing compound (A-55-1) (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 57.90g of white solid with a purity of 99% an...

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PUM

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Abstract

The present invention relates to an organic compound having a structure represented by a general formula I, the organic compound is obtained with spirobifluorene as a main body, so that the glass transition temperature can be increased, and the molecular thermal stability is high; the compound has appropriate HOMO and LUMO energy levels and relatively high Eg, so that the photoelectric property can be effectively improved, and the service life of an OLED device can be effectively prolonged. Meanwhile, by means of an arylamine group, compared with pure spirobifluorene, the compound has a betterplanar structure and a conjugate system. The compound is relatively simple to synthesize and purify and low in cost; meanwhile, the benzene ring contains methyl, so that the distance between molecules can be increased, association between compounds is prevented, and the probability of molecular stacking is reduced. The compound is not liable to crystallize during evaporation, can effectively improve the yield of OLEDs when being applied to OLED devices, can effectively improve the luminous efficiency, and is good in film-forming property. The material can also 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 self-illumination, low-voltage DC drive, full curing, self-illumination, high brightness, high resolution, wide viewing angle, fast response, thin thickness, small size, light weight, flexible substrate, low power ...

Claims

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Application Information

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IPC IPC(8): C07C211/61C07D209/88C07D213/38C07D213/74C07D217/02C07D251/24C07D307/91C07D333/76C07D401/12C07D401/14C07D405/12C07D405/14C07D409/12C07D409/14C09K11/06H01L51/54
CPCC07C211/61C07D333/76C07D307/91C07D213/38C07D213/74C07D209/88C07D251/24C07D217/02C07D409/12C07D409/14C07D405/14C07D405/12C07D401/14C07D401/12C09K11/06C09K2211/1007C09K2211/1011C09K2211/1014C09K2211/1029C09K2211/1059C09K2211/1088C09K2211/1092H10K85/636H10K85/626H10K85/633H10K85/654H10K85/6576H10K85/6574H10K85/6572
Inventor 李仲庆杭德余梁现丽段陆萌班全志李继响程丹丹其他发明人请求不公开姓名
Owner 北京燕化集联光电技术有限公司
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