Fluorobenzofiurene organic fluorescent material and preparation method thereof

A fluorescent material, the technology of fluorophenylfluorene, which is applied in the field of fluorophenylfluorene organic fluorescent materials and its preparation, can solve the problems of limiting the application of fluorene organic fluorescent materials, harsh preparation conditions, cumbersome synthesis steps, etc., and achieve good photoelectric activity, Simple preparation method and high luminous efficiency

Inactive Publication Date: 2013-05-22
NINGBO UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] Chinese patent 200910112709.X introduces a glutamic acid-derived organic fluorescent material, which emits blue fluorescence under ultraviolet light around 330nm, but its preparation conditions are relatively harsh
Chinese patent 200610124795.2 introduces a fluorescent material composition of pyridine derivative compounds, which can be used to analyze fluorescent probes in chemistry and biochemistry, but the material is a fluorescent material composition composed of pyridine and rare earth ions, and the preparation price is relatively expensive
Chinese patent 200810162059.5 introduces a fluorescent material naphthooxazole derivative and its preparation method. The fluorescent quantum efficiency of this material is high, but its synthesis steps are cumbersome
Fluorene has high thermal stability, and the solid film made by itself has a certain fluorescence quantum efficiency, and the band gap energy is greater than 2.90eV. However, the rigidity of the fluorene structure makes it easy to produce excimer associations and affect the luminescence stability of the material. property, which limits the application of fluorene organic fluorescent materials

Method used

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  • Fluorobenzofiurene organic fluorescent material and preparation method thereof
  • Fluorobenzofiurene organic fluorescent material and preparation method thereof
  • Fluorobenzofiurene organic fluorescent material and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0020] Take 2,7-dibromofluorene (0.33g, 1.0mmol), 4-fluorophenylboronic acid (0.35g, 2.5mmol), palladium acetate (0.012g, 0.05mmol) and potassium carbonate (0.70g, 5mmol) as solid powder ) were mixed in a 100ml three-necked flask; then a mixed solution prepared from 30mL isopropanol (i-PrOH) and 6mL water was injected into the three-necked flask, and the reaction was refluxed at 80°C for 1 day in an air atmosphere; the reaction After the reaction solution is cooled, extract with dichloromethane, combine the organic phases, then wash the organic phase with saturated brine, then dry with anhydrous magnesium sulfate for 12 hours, and obtain the filtrate after filtration; Chloromethane, to obtain a solid crude product, the mixed solvent of petroleum ether and dichloromethane with a volume ratio of 6:1 is used as an eluent, and the crude product is separated and purified by column chromatography, and finally petroleum ether and dichloromethane are removed A white powdery solid was ...

Embodiment 2

[0022] Take 2,7-dibromofluorene (0.33g, 1.0mmol), 4-fluorophenylboronic acid (0.35g, 2.5mmol), palladium acetate (0.012g, 0.05mmol) and potassium carbonate (0.70g, 5mmol) as solid powder ) were mixed in a 100ml three-necked flask; then, a mixed solution prepared by 30mL isopropanol (i-PrOH) and 6mL water was injected into the three-necked flask, and the reaction was refluxed at 90°C in an air atmosphere for 1 day; the reaction After the reaction solution is cooled, extract with dichloromethane, combine the organic phases, then wash the organic phase with saturated brine, then dry with anhydrous magnesium sulfate for 10 h, and obtain the filtrate after filtration; spin dry the isopropanol and di Chloromethane, to obtain a solid crude product, the mixed solvent of petroleum ether and dichloromethane with a volume ratio of 5:1 is used as an eluent, and the crude product is subjected to column chromatography separation and purification, and finally petroleum ether and dichlorometha...

Embodiment 3

[0024] Take 2,7-dibromofluorene (0.66g, 2.0mmol), 4-fluorophenylboronic acid (0.70g, 5mmol), palladium acetate (0.024g, 0.10mmol) and potassium carbonate (1.40g, 10mmol) as solid powder Mix in a 150ml three-necked flask; then inject a mixed solution prepared from 60mL isopropanol (i-PrOH) and 15mL water into the three-necked flask, and reflux at 80°C for 1 day in an air atmosphere; the reaction is complete After the reaction solution is cooled, extract with dichloromethane, combine the organic phases, then wash the organic phase with saturated brine, then dry with anhydrous magnesium sulfate for 12 hours, and obtain the filtrate after filtration; spin dry the isopropanol and dichloromethane in the filtrate Methane, to obtain solid crude product, the mixed solvent that petroleum ether and dichloromethane are formed with the volume ratio of 6:1 is used as eluting agent, carries out column chromatography separation and purification to crude product, finally removes petroleum ether...

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Abstract

The invention discloses a fluorobenzofiurene organic fluorescent material. The organic fluorescent material is a fluorobenzofiurene organic compound, wherein the compound is named 2,7-bi(4-fluorophenyl)fluorene, has a molecular formula of C25H16F2 and the molecular weight being 354.38, is of a monoclinic crystal system and has the space group being P21/c, and the cell parameters are as follows: a=8.0031, b=5.8478, c=37.930, alpha=90 degrees, gamma=90 degrees, beta=95.442 degrees; the fluorescent material is formed by mixing and reacting 2,7-dibromofluorene, 4-fluorophenylboronic acid, palladium acetate and potassium carbonate under certain conditions; the preparation method is simple; the reaction conditions are mild; the yield reaches 70-80%; the obtained fluorobenzofiurene organic fluorescent material 2,7-bi(4-fluorophenyl)fluorene has a clear space structure and an accurate molecular formula, and contains rich electronic conjugate large pi keys, which are advantageous for electron transition and energy transfer; besides, the obtained fluorobenzofiurene organic fluorescent material is good in luminescence stability, fluorescence quantum efficiency and dissolving property, high in luminous efficiency and long in service life, and thereby has potential application prospect.

Description

technical field [0001] The invention relates to an organic fluorescent material, in particular to a fluorophenylfluorene organic fluorescent material and a preparation method thereof. Background technique [0002] Since the beginning of the 21st century, information display technology has been widely used as a window for man-machine contact and information display in entertainment, industry and military, and information display has become a pillar industry in the field of optoelectronic information. Among the current flat-panel displays, the liquid crystal display (Liquid Crystal Display, LCD), which was widely promoted in the 1980s, represents a trend of flat-panel displays. However, the monopoly position of LCD is being challenged by a new display technology—Organic Light Emitting Diodes (OLEDs) flexible display technology. In recent years, due to the large amount of investment in the industry and academia, organic electroluminescent technology has been greatly developed....

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C25/22C07C17/263C09K11/06
Inventor 刘志鹏李星
Owner NINGBO UNIV
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