Ethylize-pyrazine and quinoxaline derivative and preparation method thereof

A technology of ethylated pyrazine and derivatives, which is applied in the fields of chemical instruments and methods, organic chemistry, semiconductor/solid-state device manufacturing, etc., can solve the problems of limited development, exciton annihilation, expensive phosphorescent materials, etc., and achieve high injection efficiency. Efficiency, the effect of lowering the injection barrier

Inactive Publication Date: 2017-06-13
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the expensive cost of phosphorescent materials and the severe exciton annihilation phenomenon limit their development.

Method used

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  • Ethylize-pyrazine and quinoxaline derivative and preparation method thereof
  • Ethylize-pyrazine and quinoxaline derivative and preparation method thereof
  • Ethylize-pyrazine and quinoxaline derivative and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Embodiment one: the synthesis of compound M1

[0042]

[0043] Add trifluoromethanesulfonic acid (15g, 8.85mL, 100mmol) to a 100mL two-necked flask, add fuming nitric acid (1.5g, 0.99mL, 35.7mmol) dropwise under ice bath, and then transfer the two-necked flask to 50°C in an oil bath. Add 4,7-dibromo-2,1,3-benzothiadiazole (2.500g, 8.5mmol) into the two-necked flask, and stir the reaction overnight. After the reaction, the reaction liquid was poured into 200 mL of ice-water mixture, the pH of the solution was adjusted to 7, suction filtered and dried, and the crude product was recrystallized with absolute ethanol to obtain 1.746 g of light yellow crystals, with a yield of 53.4%. MS: m / z=381.8018 [M] +

[0044] Weigh 4,7-dibromo-5,6-dinitro-2,1,3-benzothiadiazole (1.000g, 2.621mmol), add reduced zinc powder (3.406g, 52.4mmol) to 100mL dry di Add 20mL glacial acetic acid as a solvent to the flask, react in an oil bath at 60°C for 1.5h under nitrogen protection, add ...

Embodiment 2

[0046] Embodiment two: the synthesis of compound M2

[0047]

[0048] Add trifluoromethanesulfonic acid (15g, 8.85mL, 100mmol) to a 100mL two-necked flask, add fuming nitric acid (1.5g, 0.99mL, 35.7mmol) dropwise under ice bath, and then transfer the two-necked flask to 50°C in an oil bath. Add 4,7-dibromo-2,1,3-benzothiadiazole (2.500g, 8.5mmol) into the two-necked flask, and stir the reaction overnight. After the reaction, the reaction liquid was poured into 200 mL of ice-water mixture, the pH of the solution was adjusted to 7, suction filtered and dried, and the crude product was recrystallized with absolute ethanol to obtain 1.746 g of light yellow crystals, with a yield of 53.4%. MS: m / z=381.8018 [M] +

[0049] Weigh 4,7-dibromo-5,6-dinitro-2,1,3-benzothiadiazole (1.000g, 2.621mmol), add reduced zinc powder (3.406g, 52.4mmol) to 100mL dry di Add 20mL glacial acetic acid as a solvent to the flask, react in an oil bath at 60°C for 1.5h under nitrogen protection, add ...

Embodiment 3

[0051] Embodiment three: the synthesis of compound M3

[0052]

[0053] Add trifluoromethanesulfonic acid (15g, 8.85mL, 100mmol) to a 100mL two-necked flask, add fuming nitric acid (1.5g, 0.99mL, 35.7mmol) dropwise under ice bath, and then transfer the two-necked flask to 50°C in an oil bath. Add 4,7-dibromo-2,1,3-benzothiadiazole (2.500g, 8.5mmol) into the two-necked flask, and stir the reaction overnight. After the reaction, the reaction liquid was poured into 200 mL of ice-water mixture, the pH of the solution was adjusted to 7, suction filtered and dried, and the crude product was recrystallized with absolute ethanol to obtain 1.746 g of light yellow crystals, with a yield of 53.4%. MS: m / z=381.8018 [M] +

[0054] Weigh 4,7-dibromo-5,6-dinitro-2,1,3-benzothiadiazole (1.000g, 2.621mmol), add reduced zinc powder (3.406g, 52.4mmol) to 100mL dry di Add 20mL glacial acetic acid as a solvent to the flask, react in an oil bath at 60°C for 1.5h under nitrogen protection, ad...

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Abstract

The invention provides a class of ethylize-pyrazine and quinoxaline derivative and a preparation method thereof, and belongs to the technical field of research of photoluminescence. Ethyl-pyrazine and quinoxaline are used by these derivatives as molecular light nuclei, and the derivatives are connected with the functional groups with different structures and different levels of conjugates at the location of nuclear 9, 10; the synthesis method comprises the steps that 4, 7-dibromine-2,1,3-diazosulfide is used as the raw material, after a series of processes of nitration, reduction and condensation, and the like, the light nuclei connecting two bromide ethyl pyrazine and quinoxaline molecular is synthesized at the location of 9, 10, and then through the Suzuki coupling reaction of the carbazole phenylboronic acid with the neighbor and the space in between, the target derivatives are prepared. These derivatives in the ultraviolet-visible light zone have strong absorption abilities and the diluted solutions are able to emit strong fluorescence, the emission wavelengths are respectively at 450 nm or so, and are within the range of blue-ray, and can be used as materials for organic electroluminescence devices.

Description

technical field [0001] The invention relates to a class of ethylated pyrazinoquinoxaline derivatives and their application, belonging to the field of organic electroluminescence. Background technique [0002] The development of information technology in the new century is changing with each passing day. Efficient and accurate information collection, fast information processing, high-density information storage, large-capacity information transmission and high-definition information display are the goals people pursue, and information display technology plays an extremely important role. [0003] Currently, relatively mature displays include cathode ray tube (Cathode Ray Tube, CRT), plasma display (Plasma Display Panel, PDP) and liquid crystal display (Liquid Crystal Display, LCD). Although they have irreplaceable excellent performance in a certain period of time, these display devices have defects in varying degrees, making their applications unable to meet people's needs. ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04C09K11/06H01L51/54
CPCC09K11/06C07D487/04C09K2211/1044C09K2211/1029C09K2211/1007H10K85/6572
Inventor 刘迪黄廷廷刘贺
Owner DALIAN UNIV OF TECH
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