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Green material, preparation method and application thereof

A reaction and derivative technology, applied in the field of organic electroluminescent materials, can solve the problems of not meeting the requirements of OLED use, and achieve the effect of low manufacturing cost and reduced manufacturing cost

Active Publication Date: 2015-05-27
JILIN OPTICAL & ELECTRONICS MATERIALS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] The present invention provides a green electroluminescent material with high color purity and high luminous efficiency and its preparation method and application in order to solve the technical problem that phenothiazine light-emitting materials in the prior art cannot meet the use requirements of OLEDs.

Method used

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  • Green material, preparation method and application thereof

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preparation example Construction

[0049] The present invention also provides a preparation method of benzimidazole phenothiazine derivatives, wherein the reaction scheme is shown in the following formula, and the specific steps are:

[0050]

[0051] S100, 2-bromo-1H-benzimidazole and R1-substituted iodine substitution reaction to obtain R1-substituted benzimidazole compounds;

[0052] S200, reacting 10H-phenothiazine-3,7-diboronic acid and a benzimidazole compound substituted by R1 group to obtain a benzimidazole phenothiazine diboronic acid derivative containing R1 substituent;

[0053]S300, reacting the benzimidazole compound substituted with R1 group and the benzimidazole phenothiazine diboronic acid derivative containing R1 substituent to obtain the benzimidazole phenothiazine derivative containing R1 substituent;

[0054] The preparation method of the phenothiazine derivatives, wherein the S100 specifically includes the following steps:

[0055] 2-Bromo-1H-benzimidazole and R1-substituted iodine are ...

Embodiment 1

[0074]

[0075] Weigh 120.00mmol of p-iodotoluene, 80.00mmol of 2-bromo-1H-benzo[d]imidazole, 120.00mmol of potassium tert-butoxide, 4.00mmol of palladium (II) acetate, and 4.00mmol of tri-tert-butylphosphine, and dissolve them in 250ml of toluene , under the protection of nitrogen, reacted at 80°C for 5 hours, filtered the reaction solution, and recrystallized with petroleum ether and dichloromethane to generate 66.64mmol of 2-bromo-1-(p-methyl)-1H-benzo[d]imidazole , the yield is above 83.3%, and the HPLC purity is greater than 98%.

[0076] Weigh 20.00mmol of 10H-phenothiazine-3,7-diboronic acid, 40.00mmol of 2-bromo-1-(p-methyl)-1H-benzo[d]imidazole, 40.00mmol of potassium tert-butoxide, palladium acetate ( Ⅱ) 1.40mmol, 1.40mmol of tri-tert-butylphosphine, dissolved in 120ml of toluene, reacted at 80°C for 5 hours under the protection of nitrogen, filtered the reaction solution, recrystallized with petroleum ether and dichloromethane to obtain the intermediate, and cont...

Embodiment 2

[0078]

[0079] 122mmol of 3-iodopyridine and 80mmol of 2-bromo-1H-benzo[d]imidazole, 130mmol of potassium tert-butoxide, 4.20mmol of palladium (II) acetate, 4.20mmol of tri-tert-butylphosphine, dissolved in 250ml of toluene, under nitrogen protection 2-bromo-1-(p-methyl)-1H-benzo[d]imidazole 67.60mmol, yield 84.5 % or more, HPLC purity greater than 98%.

[0080] Weigh 20.00mmol of 10H-phenothiazine-3,7-diboronic acid, 42.00mmol of 2-bromo-1-(3-pyridyl)-1H-benzo[d]imidazole, 42.00mmol of potassium tert-butoxide, palladium acetate (II) 1.60mmol, 1.50mmol of tri-tert-butylphosphine, dissolved in 120ml of toluene, reacted at 80°C for 5 hours under the protection of nitrogen, filtered the reaction solution, recrystallized with petroleum ether and dichloromethane to obtain the intermediate, continued to add 40mmol of 2-bromo-1-(3-pyridyl)-1H-benzo[d]imidazole, 40mmol of potassium tert-butoxide, 1.40mmol of palladium (II) acetate, 1.40mmol of tri-tert-butylphosphine, dissolve...

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Abstract

The invention discloses a preparation method and application of a phenothiazine derivative. A green organic electroluminescence material disclosed by the invention is based on phenylimidazole and phenothiazine and has the structure formula shown in description, wherein R1, R2 and R3 can be same or different. The phenothiazine derivative has green photoluminescence and high luminous emission efficiency and can be taken as a green material to be applied to electroluminescence devices.

Description

technical field [0001] The invention relates to the field of organic electroluminescent materials, in particular to a phenothiazine material and its preparation method and application. [0002] Background technique [0003] Recently, the rapid growth of the optical communication and multimedia sectors is accelerating due to the development of an advanced information society. Converting between electrons and photons, or electron-to-photon conversion using optoelectronic devices (optoelectronic devices), has become central to the modern information and electronics industries. Electroluminescent semiconductor optoelectronic devices, such as light receiving elements, and they can be divided into a combined unit. So far, most of the display characters are of the light-receiving type, while the emissive electroluminescent device has a fast response speed, and since it is self-illuminating, the backlight does not require curvature. [0004] Electroluminescent devices are classif...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D417/14C09K11/06H01L51/52
CPCC09K11/06C07D417/14C09K2211/1029C09K2211/1037C09K2211/1044C09K2211/1011C09K2211/1007C09K2211/1092H10K85/626H10K85/654H10K85/6576H10K85/6572H10K85/657
Inventor 马晓宇李文军李明
Owner JILIN OPTICAL & ELECTRONICS MATERIALS
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