Organic electroluminescence material of spirobifluorene structure and preparation method and application thereof

A luminescent material and electroluminescence technology, applied in luminescent materials, organic chemistry, chemical instruments and methods, etc., can solve the problems of affecting the service life of materials, low glass transition temperature, and damage to film uniformity.

Inactive Publication Date: 2019-07-12
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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  • Organic electroluminescence material of spirobifluorene structure and preparation method and application thereof
  • Organic electroluminescence material of spirobifluorene structure and preparation method and application thereof
  • Organic electroluminescence material of spirobifluorene structure and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0075] Synthesis of (Compound 1-20-2)

[0076] The synthetic route is as follows:

[0077]

[0078] Including the following specific steps:

[0079] Synthesis of Compound B-20-2

[0080] 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 the methylspirobifluorene dibromosubstituent-containing compound (A-20-2) (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 ob...

Embodiment 2

[0085] (Compound I-14-2) Synthesis

[0086] The synthetic route is as follows:

[0087]

[0088] Including the following specific steps:

[0089] Synthesis of Compound B-14-2

[0090] A 500 ml three-necked flask was equipped with a magnetic stirrer. After argon replacement, 18.1 g (0.188 mol) of potassium tert-butoxide and 30.74 g of N-(naphthalene-2-yl)-9H-fluorene-2-amine (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 to a solution consisting of 48.82g of methylspirobifluorene dibromosubstituent-containing compound A-14-2 (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 62.89g of w...

Embodiment 3

[0095] (Compound I-113-2) Synthesis

[0096] The synthetic route is as follows:

[0097]

[0098] Including the following specific steps:

[0099] Synthesis of Compound B-113-2

[0100] 500 ml three-necked flask equipped with a magnetic stirrer, and after argon replacement, 18.1 g (0.188 mol) of potassium tert-butoxide and 32.54 g of N-(naphthalene-2-yl)dibenzothiophene-3-amine (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 48.82g of methylspirobifluorene dibromosubstituent-containing compound A-113-2 (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 66.31g of white s...

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PUM

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Abstract

The invention relates to an organic electroluminescence material of a spirobifluorene structure. The structure of the material is shown in a formula I. The organic electroluminescence material takes spirobifluorene as a main body, therefore the glass transition temperature can be increased, the molecular heat stability is high, the moderate HOMO and LUMO energy levels and the high content of Eg are achieved, the photoelectric property can be effectively improved, and the service life of an OLED device is prolonged. Arylamine groups are introduced, compared with simple spirobifluorene, a betterplane structure and a better conjugated system are achieved, synthesis and purification are simple, the cost is low, benzene rings contain methyl, therefore the intermolecular distance can be increased, association of compounds is avoided, and the molecular stacking probability is reduced. During evaporation, the crystallization phenomenon cannot easily occur, when the material is applied to theOLED device, the OLED finished product rate can be effectively increased, the luminescence efficiency can be effectively improved, and the film-forming property is good. The material can also be takenas a luminescent material for using, and the service life of the luminescent material can be effectively prolonged.

Description

technical field [0001] The invention belongs to the technical field of organic electroluminescent display, and in particular relates to a novel organic electroluminescent 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 r...

Claims

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Application Information

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IPC IPC(8): C07C211/61C07D209/88C07D213/38C07D213/74C07D251/22C07D333/76C07D401/12C07D401/14C07D403/12C07D409/12C07D409/14C09K11/06H01L51/54H01L51/50
CPCC07D213/74C07D213/38C07C211/61C07D251/22C07D333/76C07D209/88C07D401/12C07D401/14C07D403/12C07D409/12C07D409/14C09K11/06C07C2603/18C07C2603/94C09K2211/1092C09K2211/1029C09K2211/1074C09K2211/1011C09K2211/1014H10K85/624H10K85/636H10K85/626H10K85/633H10K85/615H10K85/654H10K85/6576H10K85/6572H10K50/15
Inventor 程丹丹李小赢曹占广黄春雪段陆萌班全志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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