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2-(2'-hydroxyphenyl) benzothiazole chelated zinc derivative as well as preparation method and application thereof

The technology of benzothiazole and hydroxyphenyl is applied to 2-(2'-hydroxyphenyl) benzothiazole chelated zinc derivatives and the fields of preparation and application thereof, and can solve the problem of short service life and organic electroluminescence display. The problems of low industrialization process of devices and limited types of electron transport materials have achieved the effect of improving device performance and life.

Inactive Publication Date: 2010-02-24
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The biggest defect of plasma display is that the luminous performance decreases significantly with the use of time
In addition, high cost and high driving voltage also limit the application range of plasma displays; although liquid crystal displays have been industrialized and become the mainstream of flat panel display technology, they still have some disadvantages: low luminous efficiency, power consumption of backlight Large volume, slow response, etc.
[0004] However, despite this, the industrialization process of organic electroluminescent display devices is far below people's expectations.
One of the most important reasons is that the electron mobility of the existing electron transport materials does not match the hole mobility of the hole transport materials, resulting in low luminous efficiency and short service life of the device.
In addition, the types of electron transport materials available are limited
In fact, the electron mobility of most current electron transport materials is very low, which is 2-3 orders of magnitude lower than the hole mobility of hole transport materials.

Method used

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  • 2-(2'-hydroxyphenyl) benzothiazole chelated zinc derivative as well as preparation method and application thereof
  • 2-(2'-hydroxyphenyl) benzothiazole chelated zinc derivative as well as preparation method and application thereof
  • 2-(2'-hydroxyphenyl) benzothiazole chelated zinc derivative as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027]

[0028] Take 6.1g of 4-methoxyaniline (0.05mol) and 7.6g of o-hydroxybenzoic acid (0.055mol) respectively in a 250ml round bottom flask, and add 100ml of chlorobenzene, and slowly add 3.4g of trichlorobenzene dropwise to the reaction system under stirring. Phosphate (0.025mol). Slowly raise the temperature to 130°C, and reflux at this temperature for 1.5h. After the reaction, an orange-yellow colloidal solid appeared on the wall of the flask, and the solution was a milky white clear liquid. The reaction solution was filtered while hot, and the filtrate was concentrated and then recrystallized with chloroform and methanol (about 1:1). Yield: 88%, Mp 160.2-160.6°C. 1 H NMR (400MHz, CDCl 3 , TMS) δ12.07 (s, 1H), 7.92 (s, 1H), 7.51-7.49 (d, 1H), 7.45-7.40 (m, 3H), 7.02-7.00 (d, 1H), 6.93-6.87 ( m, 3H), 3.80 (m, 3H).

Embodiment 2

[0030] Pack 12.2g N-(4'-methoxyphenyl)-2-hydroxybenzamide (0.05mol), 3.6g imidazole (0.0525mol), and 8.3g tert-butyldimethylsilyl chloride (0.055mol) respectively into a 250ml round bottom flask, and then add 120ml of dichloromethane. Stir magnetically at room temperature for 10 h, and track the reaction with thin-layer chromatography. After the reaction, wash with dilute hydrochloric acid (0.1M) and water three times, and extract with dichloromethane, anhydrous MgSO 4 Dry, filter, and spin out the solvent, and the crude product is directly subjected to thiolation.

[0031] Get Lawson's reagent 12.1g (C 14 h 14 o 2 P 2 S 4 ) (0.03mol) was added to the crude product obtained in the previous step, and then 120ml of toluene was added. After stirring, the temperature was slowly raised to 110° C. under the protection of nitrogen, and the reaction was refluxed at this temperature for 9 hours. Toluene was distilled off under reduced pressure, and a yellow solid was obtained...

Embodiment 3

[0033]

[0034] In the 7.5g of N-(4'-methoxyphenyl)-2-tert-butyldimethylsilyloxythiobenzamide (0.02mol) obtained above, add a small amount of ethanol and fresh 30% NaOH successively solution (0.16mol), then add water to make the NaOH aqueous solution concentration about 10%, and then add the diluted solution dropwise to a 20% K 3 Fe(CN) 6 (0.08mol) aqueous solution, continue to react for 2h after addition. After the reaction, the reaction solution was poured into water, neutralized with dilute hydrochloric acid, and extracted several times with dichloromethane. The organic layers were combined, dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure, and the product was separated and purified by column chromatography. Yield 15%. Mp 150.6-151.1℃. 1 H NMR (400MHz, CDCl 3 , TMS) δ12.492 (s, 1H), 7.86-7.84 (d, 1H), 7.67 (s, 1H), 7.65-7.65 (d, 1H), 7.38-7.34 (m, 1H), 7.31-7.29 ( d, 1H), 7.10-7.08 (d, 1H), 6.96-6.92 (m, 1H). LRMS (ESI, p...

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Abstract

The invention relates to a 2-(2'-hydroxyphenyl) benzothiazole chelated zinc derivative as well as a preparation method and an application thereof, belonging to the field of organic electroluminescentluminescent materials. The preparation method of the derivative comprises the following steps: firstly, introducing different substituent groups with electron-withdrawing or electron-donating capability in a benzothiazole benzene ring or a hydroxyphenyl benzene ring of a 2-(2'-hydroxyphenyl) benzothiazole matrix to obtain a substituted 2-(2'-hydroxyphenyl) benzothiazole ligand; coordinating with diatomic zinc to form a corresponding complex, and the like. The substituted 2-(2'-hydroxyphenyl) benzothiazole ligand can be prepared by a plurality of reactions, such as substituted aniline acylation, hydroxyl protection, hydroxyl thiocarbonate, Jacobson cyclization while hydroxyl deprotection, and the like or prepared by a direct reaction of O-amino thiophenol and substituted ortho-hydroxybenzoic acid. When applied to an organic electroluminescent luminescent device as an electronic transmission layer, the derivative has favorable electronic transmission performance and has performance superior to the most common electronic transmission material 8-hydroxyquinoline aluminum.

Description

technical field [0001] The invention relates to a class of 2-(2'-hydroxyphenyl)benzothiazole chelated zinc derivatives in the field of organic electroluminescent materials, a preparation method thereof and an application in organic electroluminescent devices. Background technique [0002] The 21st century is an era of rapid development of information technology. With the popularization of digital multimedia technology, as a display of various information product terminals, its importance has become increasingly apparent. Display devices can be seen everywhere, from household electronic watches and televisions to computer monitors and monitors in the workplace, to advertising signs in public places, traffic lights, etc., and have become an indispensable part of modern people's lives. With the continuous development of human society, people are increasingly dissatisfied with the performance of traditional mainstream display devices (Acridine-RT) and hope to find a smaller, lig...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D277/66C09K11/06H01L51/54
Inventor 李久艳刘迪王任洁徐凯
Owner DALIAN UNIV OF TECH
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