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Solid broadband blue-light transmitting organic luminescent material and preparation method thereof

A technology for luminescent materials and fluorescent materials, applied in the field of solid-state broadband blue light emitting organic luminescent materials and their preparation, can solve the problems of less optical materials and the like, and achieve the effects of simple preparation method, strong fluorescence emission performance and good stability

Active Publication Date: 2015-05-13
INSTITUTE OF ANALYSIS GUANGDONG ACADEMY OF SCIENCES (CHINA NATIONAL ANALYTICAL CENTER GUANGZHOU)
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Problems solved by technology

[0006] Although quinoxaline and pyridazinone derivatives have received great attention from researchers and extensive research has been carried out, the research on pyridazinone derivatives is often limited to the fields of medicine and pesticides, and the research on optical materials is very limited. few
On the other hand, the quinoxaline structural unit is combined with the pyridazinone unit to form a quinoxaline functionalized pyridazinone compound, and studies on its photophysical properties have not been reported.

Method used

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  • Solid broadband blue-light transmitting organic luminescent material and preparation method thereof
  • Solid broadband blue-light transmitting organic luminescent material and preparation method thereof
  • Solid broadband blue-light transmitting organic luminescent material and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Example 1: Synthesis of 4,5-dihydro-5-methyl-6-(2,3-diphenyl-6-quinoxalinyl)-3(2H)pyridazinone (compound Ia)

[0030]

[0031] Benzil (i.e. diphenyl ketone, at this time, R in compound II is selected from H, 0.001mol) and 6-(3,4-diaminophenyl)-5-methyl-4,5-di Hydropyridazin-3(2H)-one (Compound III, 0.001mol) was dissolved in 30 ml of glacial acetic acid, stirred and refluxed for 6-8 hours; cooled to room temperature, poured the reaction liquid into ice water under stirring, adjusted with ammonia water pH=7, the obtained solid was filtered with suction, washed with water three times, and the crude product was recrystallized with ethanol-acetone mixed solvent to obtain a white flocculent solid with a yield of 68%. The melting point is 241-243°C.

[0032] 1 H NMR (300MHz, CDCl 3 / TMS)δ:1.36(d,J=7.5Hz,3H),2.57(d,J=16.5Hz,1H),2.83(dd,J=16.9,6.9Hz,1H),3.56-3.61(m,1H ),7.34-7.39(m,6H),7.51-7.56(m,4H),8.18(d,J=9.0Hz,1H),8.39(d,J=2.1Hz,1H),8.41(dd,J= 8.7,2.1Hz,1H),8.91(s...

Embodiment 2

[0034] 4,5-dihydro-5-methyl-6-(2,3-bis(4-methoxyphenyl)-6-quinoxalinyl)-3(2H)pyridazinone (Compound Ib) synthesis

[0035]

[0036] According to the method of Example 1, from anisole (R in compound II is selected from OCH 3 ) and 6-(3,4-diaminophenyl)-5-methyl-4,5-dihydropyridazin-3(2H)-one (compound Ⅲ), the difference is that anisole and compound The molar ratio of Ⅲ is 1:1.1, the solvent is absolute ethanol, the product is light yellow solid, and the yield is 71%. The melting point is 165-167°C.

[0037] 1 H NMR (300MHz, CDCl 3 / TMS)δ:1.35(d,J=7.5Hz,3H),2.56(d,J=16.5Hz,1H),2.82(dd,J=16.9,6.9Hz,1H),3.55-3.62(m,1H ),3.84(s,6H),6.87-6.91(m,4H),7.49-7.53(m,4H),8.12(dd,J=8.4Hz,1H),8.33(s,1H),8.35(dd, J=8.1,2.1Hz,2H),8.98(s,1H); 13 C NMR (75MHz, CDCl 3 / TMS)δ:16.46,27.94,33.90,55.35,113.84,113.91,126.29,127.05,129.36,131.20,131.29,131.35,131.39,135.40,140.87,141.80,152.79,153.64,160.35,160.41,166.66。

Embodiment 3

[0038] Embodiment 3 compound fluorescence performance test

[0039] The compound (Ia, Ib) that embodiment 1 and 2 obtains is prepared respectively and is 2 * 10 -5 M Chloroform solution. Measure the ultraviolet absorption and fluorescence properties on the HORIBA Jobin Yvon Aqualog absorption and three-dimensional fluorescence scanning spectrometer with a 1 cm fluorescence cell, the results are as follows Figure 1-3 shown.

[0040] The solid-state photoluminescence spectrum was measured with a Horiba Jobin-Yvon LabRam HR800 laser Raman spectrometer, and the excitation light source was a 325nm He–Cd laser. The results are shown in Figure 4 .

[0041] Simultaneously observe the fluorescent color of the solid powder of Compound Ia obtained in Example 1 and its chloroform solution under white light and 365nm ultraviolet lamp irradiation, under white light irradiation, Compound Ia is a colorless solution and a white solid respectively in solution and solid state; 365nm ultraviol...

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Abstract

The invention discloses a solid broadband blue-light transmitting organic luminescent material shown in a formula I and a preparation method thereof. R is H or OCH3. Two functional structural units such as the quinoxaline group and the pyridazinone group are effectively combined to form a pyridazinone-type organic luminescent molecule with quinoxaline being functionalized. The two-heterocyclic-ring pyridazinone compound provided by the invention is stable in structure and easy to store, a good ultraviolet absorption property and a strong fluorescent transmitting property in a chloroform solution can be realized, and the solid broadband blue-light transmitting organic luminescent compound is expected to become a novel organic material obtaining the white light. The preparation method is simple, the luminescent material is good in stability and can be used in the fields such as luminescent devices, white light luminescence or fluorescent probes. By adopting the solid broadband blue-light transmitting organic luminescent material and the preparation method thereof, the research and application field of the quinoxaline pyridazinone compound can be enlarged.

Description

Technical field: [0001] The invention relates to the technical field of organic luminescent materials, in particular to a solid broadband blue light emitting organic luminescent material and a preparation method thereof. Background technique: [0002] Organic light-emitting materials are widely used in organic electroluminescent devices (OLEDs), organic solid-state lasers, organic photovoltaic cells, and organic fluorescent sensors. 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 optoelectronics industry, and it is also a very challenging and important work. [0003] At present, a hot issue in the research of organic light-emitting materials is how to improve the solid-state emission properties of materials, because in most cases, organic light-emitting materials often show strong fluorescence in dilute solutions, but only weak fluore...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D403/04
CPCY02B20/00
Inventor 孙一峰雷永乾王玉芹刘治国方军陈江韩
Owner INSTITUTE OF ANALYSIS GUANGDONG ACADEMY OF SCIENCES (CHINA NATIONAL ANALYTICAL CENTER GUANGZHOU)
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