Bifluorescence-emission organic light-emitting material and preparation method thereof

A luminescent material and dual fluorescence technology, which is applied in luminescent materials, organic chemistry, chemical instruments and methods, etc., can solve the problem of limited emission wavelength region, and achieve the effects of enhanced electron pulling, easy storage, and easy purification

Inactive Publication Date: 2013-11-27
TAISHAN UNIV
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  • Abstract
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  • Application Information

AI Technical Summary

Problems solved by technology

In recent years, the synthesis, photoelectric properties and application studies of triaryl imidazoles have attracted people's attention. Although the trisubstituted imidazoles have received great attention from researchers and extensive research has been carried out, most of the reported compounds It is a triaryl imidazole compound, and a small amount of monoaryl vinyl or diaryl vinyl imidazole compound, and most of the compounds involved are blue-green luminescent, and the emission wavelength region is limited
However, the introduction of three arylvinyl functional groups into the imidazole ring to form a nitro-containing triarylvinylimidazole compound with a more extended conjugated system, and the research on its photophysical properties have not been seen in the prior art. to report

Method used

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  • Bifluorescence-emission organic light-emitting material and preparation method thereof
  • Bifluorescence-emission organic light-emitting material and preparation method thereof
  • Bifluorescence-emission organic light-emitting material and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] 4,4'-(2,2'-(2-(4-nitrostyryl)-1H-imidazol-4,5-diyl))bis(ethylene-2,1-diyl)dibenzoic acid Preparation of Dimethyl Ester (Compound I)

[0026] (1) Synthesis of dimethyl 4,4'-(3,4-dioxo-1,5-hexadiene-1,6-diyl)dibenzoate (compound Ⅳ)

[0027] In a dry 100 ml round bottom flask, add 2,3-butanedione (compound Ⅱ) (0.01 mol), methyl 4-formylbenzoate (compound Ⅲ) (0.02 mol), and 35 ml of absolute ethanol , and then 0.5 ml of piperidine was added to the solution under rapid stirring, and then stirred and refluxed for 7 hours. After cooling to room temperature, a yellow solid precipitated, which was filtered under reduced pressure, washed twice with absolute ethanol, recrystallized with a mixed solvent of ethanol-N,N-dimethylformamide, and dried in vacuo to obtain orange crystals with a yield of 19 %. The melting point is 249-251 ℃

[0028] (2) 4,4'-(2,2'-(2-(4-nitrostyryl)-1H-imidazole-4,5-diyl))bis(ethylene-2,1-diyl) Synthesis of Dimethyl Dibenzoate (Compound I)

[0029] I...

Embodiment 2

[0033] 4,4'-(2,2'-(2-(4-nitrostyryl)-1H-imidazol-4,5-diyl))bis(ethylene-2,1-diyl)dibenzoic acid Preparation of Dimethyl Ester (Compound I)

[0034] According to the method of Example 1, obtained by two-step reaction, the difference is that in step 1, the mol ratio of 2,3-butanedione (compound II) and 4-formyl formic acid methyl ester (compound III) is 1: 2.1, yield rate is 20%; In step 2, 4,4'-(3,4-dioxo-1,5-hexadiene-1,6-diyl)dibenzoic acid dimethyl ester (compound IV ), 4-nitrocinnamaldehyde (compound V) and ammonium acetate in a molar ratio of 1: 1.1: 15, and the yield was 63%.

[0035]

Embodiment 3

[0037] 4,4'-(2,2'-(2-(4-nitrostyryl)-1H-imidazol-4,5-diyl))bis(ethylene-2,1-diyl)dibenzoic acid Preparation of Dimethyl Ester (Compound I)

[0038] According to the method of Example 1, it is obtained by two-step reaction, and the difference is that step 2 is carried out according to the following microwave radiation method.

[0039]Add dimethyl 4,4'-(3,4-dioxo-1,5-hexadiene-1,6-diyl)dibenzoate (compound IV) into a dry 100 ml Erlenmeyer flask ( 0.001mol), 4-nitrocinnamaldehyde (compound Ⅴ) (0.001mol) and ammonium acetate (0.015mol), and 25 mL of glacial acetic acid, stir well, put in microwave oven, medium-low fire radiation reaction, take out and stir for more times, the reaction time was 12 minutes. After the reaction was completed, cool to room temperature, pour the reaction solution into ice water under rapid stirring, adjust the pH to 7 with 10% aqueous sodium hydroxide solution, filter the obtained solid under reduced pressure, wash with water several times, and dry at...

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Abstract

The invention discloses a bifluorescence-emission organic light-emitting material and a preparation method thereof. According to the bifluorescence-emission organic light-emitting material, three substitution aryl vinyl constitutional units are introduced to the 2-, 4- and 5- bits of an imidazole ring to form an imidazole organic light-emitting macromolecule comprising nitro and three-aryl vinyl. The preparation method of the bifluorescence-emission organic light-emitting material comprises the following steps: (1) synthesis of the intermediate: 4,4'-(3,4-dioxo-1,5-hexadiene-1,6-di-group) di-benzoic acid di-methyl ester; (2) synthesis of 4,4'-(2,2'-(2-(4-nitrobenzene vinyl)-1H-imidazole-4,5-di-group)) double(ethylene-2,1--di-group) di-benzoic acid di-methyl ester. The compound, disclosed by the invention, shows the bifluorescence emission characteristics in the tetrahydrofuran solution, the fluorescence spectrum of the compound nearly covers the entire visible region, and the compound emits strong yellow fluorescence. The preparation method is simple to operate, convenient to synthesize and easy to purify, has potential application value in the fields of fluorescence sensitivity and the like, and can be used for luminescent devices. The bifluorescence-emission organic light-emitting material and the preparation method expand the research field of three-aryl imidazole compounds.

Description

technical field [0001] The invention belongs to the technical field of organic luminescent materials, and in particular relates to a dual fluorescent emission organic luminescent material and a preparation method thereof. [0002] Background technique [0003] Organic light-emitting materials are widely used in organic electroluminescent devices (OLEDs), organic solid-state lasers, organic photovoltaic cells, and organic fluorescent sensors. At the same time, due to the advantages of fast response speed, high storage density, low price, etc., organic light-emitting materials are becoming a new generation of optoelectronic information materials. In particular, the development of luminescent materials that meet various information display requirements is particularly rapid. Therefore, the design and development of organic light-emitting materials with high fluorescence efficiency and tunable wavelength is very urgent and necessary for the development of organic optoelectroni...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07D233/64
Inventor 孙一峰吴仁涛侯现明郑泽宝马世营段文增
Owner TAISHAN UNIV
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