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A multifunctional base pyridazinone compound, its application as an orange organic luminescent material and its preparation method

A technology based on pyridazinone and light-emitting materials, which is applied in the application and preparation of orange organic light-emitting materials, and in the field of multifunctional pyridazinone compounds, can solve problems that have not been reported, and achieve improved hole transport performance and effective Conducive to the effect of transmission and structural stability

Active Publication Date: 2017-07-28
INSTITUTE OF ANALYSIS GUANGDONG ACADEMY OF SCIENCES (CHINA NATIONAL ANALYTICAL CENTER GUANGZHOU)
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0010] At present, multiple functional structural units such as anthracenyl, butadienyl, quinoxaline and pyridazinone are combined to form bisanthracenylbutadienyl functionalized quinoxaline pyridazinone compounds, and their Research on up-conversion luminescence characteristics has not been reported in the prior art

Method used

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  • A multifunctional base pyridazinone compound, its application as an orange organic luminescent material and its preparation method
  • A multifunctional base pyridazinone compound, its application as an orange organic luminescent material and its preparation method
  • A multifunctional base pyridazinone compound, its application as an orange organic luminescent material and its preparation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0053] Example 1: 4,5-dihydro-5-methyl-6-(2,3-bis(4-(9-anthracenyl)-1,3-butadienyl)-6-quinoxalinyl )-3 (2H) preparation of pyridazinone (I)

[0054] Synthesis of step a, 1,10-bis(9-anthracenyl)-1,3,7,9-decatetraene-5,6-dione (IV)

[0055] In a dry 100 ml round bottom flask, add 2,3-butanedione (0.01mol), 3-(9-anthracenyl)acrolein (0.02mol), and anhydrous methanol (50 ml), then rapidly Piperidine (0.5 mL) was added to the solution with stirring, and then stirred and refluxed for 6-8 hours. After the reaction was completed, it was cooled to room temperature, and a red solid was precipitated, which was filtered under reduced pressure, washed three times with absolute ethanol, recrystallized with a mixed solvent of ethanol-N,N-dimethylformamide, and dried in vacuo to obtain a red solid with a yield of 19%.

[0056] Step b, 4,5-dihydro-5-methyl-6-(2,3-di(4-(9-anthracenyl)-1,3-butadienyl)-6-quinoxalinyl) Synthesis of -3(2H)pyridazinone (I)

[0057] In a dry 100 ml round bottom ...

Embodiment 2

[0059] Example 2: 4,5-dihydro-5-methyl-6-(2,3-bis(4-(9-anthracenyl)-1,3-butadienyl)-6-quinoxalinyl )-3 (2H) preparation of pyridazinone (I)

[0060] According to the method of Example 1, it is obtained by two-step reaction, the difference is that in step (2), 1,10-di(9-anthracenyl)-1,3,7,9-decatetraene-5 , the molar ratio of 6-diketone and 6-(3,4-diaminophenyl)-5-methyl-4,5-dihydropyridazin-3(2H)-one is 1:1.1, and the yield is 68%.

Embodiment 3

[0061] Example 3: 4,5-dihydro-5-methyl-6-(2,3-bis(4-(9-anthracenyl)-1,3-butadienyl)-6-quinoxalinyl )-3 (2H) preparation of pyridazinone (I)

[0062] By the method of embodiment 1, obtain by two-step reaction, difference is, step (2) is carried out by microwave radiation method:

[0063] Add 1,10-bis(9-anthracenyl)-1,3,7,9-decatetraene-5,6-dione (0.001mol) and 6-(3, 4-Diaminophenyl)-5-methyl-4,5-dihydropyridazin-3(2H)-one (0.001mol), and 30mL of anhydrous acetic acid, stir well, put in microwave oven, The reaction is carried out under fire radiation, and the middle is taken out and stirred several times, and the reaction time is 10 to 15 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 three times, and dry at room temperature. Recrystallized from a mixed solvent of ...

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Abstract

The invention discloses multifunctional group pyridazinone compounds, an application of the multifunctional group pyridazinone compounds serving as an orange organic light-emitting material and a preparation method of the multifunctional group pyridazinone compounds. Multiple functional structure units of anthryl, butadienyl, quinoxaline, pyridazinone and the like are effectively combined in one molecule, and one double-anthryl and butadienyl contained functional quinoxaline pyridazinone organic light emitting molecule is formed. According to the molecular structure, double anthryl (electron donor) for supplying electrons and one electron-deficient quinoxaline group (electron acceptor) exist in the molecule, three parts are connected through two butadiene structure units, and a larger and more extended D-pi-A-pi-D conjugated system is formed, and effective intramolecular charge transfer can be generated, so that enhancement of the up-conversion luminescence performance of organic materials is facilitated. The invention expands the field of research and application of the multifunctional group pyridazinone compounds.

Description

[0001] Technical field: [0002] The invention relates to the technical field of organic luminescent materials, in particular to a multifunctional pyridazinone compound, its application as an orange organic luminescent material and its preparation method. [0003] Background technique: [0004] Organic light-emitting materials are widely used in many fields such as light-emitting devices, photovoltaic cells, and fluorescent sensors. The most prominent feature of organic light-emitting materials is that they can convert various forms of absorbed energy into light radiation. 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. [0005] Due to the advantages of stable luminescent properties,...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D403/04C09K11/06
CPCC07D403/04C09K11/06C09K2211/1011C09K2211/1044
Inventor 陈智勇马艳芳孙一峰叶小机赖桂珍梁慧牟德海
Owner INSTITUTE OF ANALYSIS GUANGDONG ACADEMY OF SCIENCES (CHINA NATIONAL ANALYTICAL CENTER GUANGZHOU)
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