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Pyridazinone-based three-color fluorescent emission organic light-emitting material and application thereof
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A luminescent material, fluorescent emission technology
Active Publication Date: 2018-09-21
INST OF ANALYSIS GUANGDONG ACAD OF SCI (CHINA NAT ANALYTICAL
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However, the research on pyridazinone derivatives in the prior art is often limited to the fields of medicine and pesticides, and there are very few studies on the preparation and application of them as optical materials.
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[0028] In a dry 250 ml round bottom flask, 1,6-bis-(4-chlorophenyl)-1,5-hexadiene-3,4-dione (0.01mol) and 6-(3,4 -Diaminophenyl)-5-methyl-4,5-dihydropyridazin-3(2H)-one (0.01mol) was dissolved in 100 ml of anhydrousacetic acid, stirred and refluxed for 6 to 12 hours; the reaction was completed After cooling to room temperature, the reaction solution was poured into 100 ml of ice water at 0-5°C with stirring, and the pH was adjusted to 7 with ammonia water. The obtained solid was filtered under reduced pressure and washed with water for 3 times. -Dimethylformamide (volume ratio 3:1) mixed solvent recrystallization, vacuum drying, to obtain yellow solid 4,5-dihydro-5-methyl-6-(2,3-bis(2-(4 -Chlorophenyl)vinyl)-6-quinoxalinyl)-3(2H)pyridazinone, yield 78%.
[0032] In a dry 250 ml round bottom flask, 1,6-bis-(4-chlorophenyl)-1,5-hexadiene-3,4-dione (0.010mol) and 6-(3,4 -Diaminophenyl)-5-methyl-4,5-dihydropyridazin-3(2H)-one (0.012mol) was dissolved in 100 ml of absolute ethanol and 5 ml of anhydrousacetic acid, stirred and refluxed for 6~ 12 hours; after the reaction is completed, cool to room temperature, pour the reaction solution into 100 ml of ice water at 0-5°C under stirring, adjust the pH to 7 with a 10% aqueous sodium hydroxide solution, and filter the obtained solid under reduced pressure , washed 3 times with water, the crude product was recrystallized in a mixed solvent of ethanol-N,N-dimethylformamide (volume ratio 3:1), and dried in vacuo to obtain a yellow solid 4,5-dihydro-5-methyl -6-(2,3-bis(2-(4-chlorophenyl)ethenyl)-6-quinoxalinyl)-3(2H)pyridazinone, yield 80%.
[0035] In a dry 250 ml round bottom flask, 1,6-bis-(4-chlorophenyl)-1,5-hexadiene-3,4-dione (0.010mol) and 6-(3,4 -Diaminophenyl)-5-methyl-4,5-dihydropyridazin-3(2H)-one (0.011mol) was dissolved in 100 ml of absolute ethanol and 1 ml of anhydrousacetic acid, stirred and refluxed for 6~ 12 hours; after the reaction is completed, cool to room temperature, pour the reaction liquid into 100 ml of ice water at 0-5°C under stirring, adjust the pH to 7 with a 20% potassiumhydroxideaqueous solution, and filter the obtained solid under reduced pressure , washed 3 times with water, the crude product was recrystallized in a mixed solvent of ethanol-N,N-dimethylformamide (volume ratio 3:1), and dried in vacuo to obtain a yellow solid 4,5-dihydro-5-methyl -6-(2,3-bis(2-(4-chlorophenyl)ethenyl)-6-quinoxalinyl)-3(2H)pyridazinone, yield 77%.
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Abstract
The invention discloses a pyridazinone-based three-color fluorescent emission organic light-emitting material shown in a formula I and application thereof. Multiple functional structure units of chlorostyryl, quinoxaline, pyridazinone and the like are combined so as to form dichlorostyryl functionalized quinoxaline pyridazinone organic luminescent molecules. In a solid state, the pyridazinone-based three-color fluorescent emission organic light-emitting material has a three-color emission characteristic, the luminescence spectrum nearly covers the whole ultraviolet and near infrared area, thematerial emits fluorescence of three different wave bands, including blue light, green light and red light, the peaks of the three wave bands are 405nm, 514nm and 696nm respectively, the largest emission wave length is 514nm, and molecular emission emits strong green fluorescence. The pyridazinone-based three-color fluorescent emission organic light-emitting material can be used in technological fields of light emitting devices, laser dyes, anti-counterfeiting technology, fluorescence sensitivity, fluorescence imaging and the like. The formula I is shown in the description.
Description
Technical field: [0001] The invention belongs to the technical field of organic light-emitting materials, and in particular relates to a pyridazinone-based three-color fluorescence emitting organic light-emitting material and an application thereof. Background technique: [0002] Organic light-emitting materials are widely used in organic light-emitting devices, organic solid-state lasers, organic photovoltaic cells, organic fluorescent sensors, fluorescent imaging, and anti-counterfeiting technology. With the rapid development of modern science and technology, the application fields of organic light-emitting materials continue to expand, and it is urgent to develop organic light-emitting materials with high efficiency, low price, adjustable wavelength and excellent performance to meet the needs of the current optoelectronic technology field. [0003] At present, the acquisition of white light usually needs to be achieved by combining the light emission of two or more molecu...
Claims
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