Thiophene and pyrazine derivatives and preparation method thereof

A technology of pyrazine derivatives and derivatives, applied in chemical instruments and methods, luminescent materials, organic chemistry, etc., can solve the problems of complex device preparation process, unstable devices, affecting the color purity of red light, etc., and achieve fluorescence quantum yield. The effect of high rate, photothermal and morphological stability, and good solubility

Inactive Publication Date: 2012-06-13
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In doped light-emitting devices, the host and the guest emit light at the same time due to insufficient energy transfer, which seriously affects the color purity of red light; in addition, doped light-emitting devices are produced by co-evaporation or mixed solution spin coating method Therefore, the device preparation process is much more complicated than that of non-doped devices; at the same time, the phase separation between the host and guest molecules in the doped system is also the main reason for the instability of the device

Method used

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  • Thiophene and pyrazine derivatives and preparation method thereof
  • Thiophene and pyrazine derivatives and preparation method thereof
  • Thiophene and pyrazine derivatives and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] The preparation of embodiment one compound 8

[0021]

[0022] In a 50ml two-necked bottle, add 0.76g (3.26mmol) 4,5-pyrenequinone, 0.68g (3.26mmol) benzophenone, 200mg (3.59mmol) potassium hydroxide and 20ml absolute ethanol, reflux for 30 minutes, and suction filter to obtain 1 (0.57 g, 43% yield). 1 HNMR (400MHz, CDCl 3)δ7.25(t, 2H, J=8Hz), 7.45(m, 10H), 7.66(s, 2H), 7.73(dd, 2H, J=8.1Hz), 7.87(dd, 2H, J=8.1Hz ). MS: m / z: 406 ([M] + ).

[0023]

[0024] Add 1.16g (5mmol) 4,5-pyrenequinone, 0.51g (1.6mmol) Bu 4 NBr, 3.72g (15mmol) Na 2 S 2 o 2 , 10ml THF and 10ml water, stirred at room temperature for 20min, added 2.5ml (26mmol) (CH 3 ) 2 SO 4 and 2.54g (63mmol) NaOH, stirred at room temperature for 1h, extracted, and separated by column chromatography to obtain 2 (1.08g, yield 82%). MS: m / z :: 262 ([M] + ).

[0025]

[0026] Add 970mg (3.7mmol) of intermediate 3, 580mg (10.4mmol) of iron powder and 35ml of CCl in a 50ml two-necked bottle 4 , t...

Embodiment 2

[0037] The preparation of embodiment two compound 11

[0038]

[0039] Add 750mg (1mmol) of 9 and 2.24g (8mmol) of 10, 75mg (0.4mmol) of cuprous iodide, 132mg (0.5mmol) of 18-crown-6, 1.93g (14mmol) of anhydrous potassium carbonate in a 50ml two-necked bottle And 10ml of nitrobenzene, under the protection of nitrogen, react at 180°C for 48h. Then cooled to room temperature, the solvent was removed under reduced pressure, and 11 was isolated by column chromatography (975 mg, yield 63%). MS (MALDI-TOF): m / z: 1549 ([M+H] + ).

Embodiment 3

[0040] The preparation of embodiment three compound 13

[0041]

[0042] Add 750mg (1mmol) of 9 and 5.76g (8mmol) of 10, 75mg (0.4mmol) of cuprous iodide, 132mg (0.5mmol) of 18-crown-6, 1.93g (14mmol) of anhydrous potassium carbonate in a 50ml two-necked bottle React with 10ml of nitrobenzene at 180°C for 72h under nitrogen protection. Then cooled to room temperature, the solvent was removed under reduced pressure, and 13 was isolated by column chromatography (1.2 g, yield 36%). MS (MALDI-TOF): m / z: 3319 ([M+2H] + ).

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Abstract

The invention relates to thiophene and pyrazine derivatives and a preparation method thereof, belonging to the field of organic electroluminescent materials. The derivatives are prepared by forming a molecular luminous core by centrosymmetrically connecting thiophene and pyrazine with four benzene rings, connecting functional groups of different structures and different conjugated degrees with the periphery of the core so that the red fluorescent molecules have charge-transmitting capability and can be used as a main red luminous material in the field of organic electroluminescence. The synthesis method comprises the following steps of: using 2,5-dibromothiophene as a raw material; nitrifying, carrying out C-C coupling with bromobenzene boric acid; reducing nitro groups; synthesizing a thiophene and pyrazine core with four peripheral bromines periphery together with 4,4'-dibromo benzyl; and then, carrying out C-N, C-C coupling reactions with arylamine, and the like or introducing acetylene groups to the periphery of the core and carrying out Diels-Alder cycloaddition with cyclopentadiene ketene with functional substituted groups to prepare target derivatives. The derivatives have strong absorption capability in an ultraviolet-visible light region, the dilute solution thereof emits strong fluorescence, and luminous peaks are between 600nm and 650nm.

Description

technical field [0001] The invention relates to a class of thienopyrazine derivatives and a preparation method thereof, belonging to the field of organic electroluminescent materials. Background technique [0002] The brilliant achievements of microelectronics technology in the 20th century and the rapid development of optoelectronics technology in the 21st century make information technology face an exciting revolution. The development of the Internet and the rise of the information industry are changing the traditional way of life and social outlook of mankind. [0003] Information technology includes the collection, processing, storage, transmission and display of information. Efficient and accurate collection of information data, fast processing, high-density storage, large-capacity transmission and high-definition display constitute the main body of information technology. Among them, the display technology as the output terminal of the information system occupies a d...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D495/04C09K11/06
Inventor 刘迪李久艳李青
Owner DALIAN UNIV OF TECH
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