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Photoelectric functional material based on phosphine sulfur/oxygen modifying phenazine

A technology for optoelectronic functional materials and synthesis methods, which can be applied in the fields of luminescent materials, compounds of Group 5/15 elements of the periodic table, chemical instruments and methods, etc., and can solve problems such as the properties of the compounds themselves, the limitations of synthesis methods, and the instability of phenazine. , to achieve the effects of excellent optoelectronic properties, low toxicity of raw materials, and improved stability

Inactive Publication Date: 2018-11-13
NANJING UNIV OF POSTS & TELECOMM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the instability of phenazine itself, the current further development and research on phenazine compounds are largely limited by the properties of the compound itself and the synthesis method.

Method used

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  • Photoelectric functional material based on phosphine sulfur/oxygen modifying phenazine
  • Photoelectric functional material based on phosphine sulfur/oxygen modifying phenazine
  • Photoelectric functional material based on phosphine sulfur/oxygen modifying phenazine

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preparation example Construction

[0032] The present invention also discloses a method for synthesizing a photoelectric functional material based on phosphine sulfur / oxygen modified phenazine, the method comprising the following steps:

[0033] S1: Under the protection of nitrogen, dissolve phenazine in ethanol, dissolve sodium dithionite in distilled water, then inject the aqueous solution of sodium dithionite into the ethanol solution system of phenazine, and react under the conditions of heat reflux and shading After 1 to 5 hours, after cooling to room temperature, the flocs in the system were distilled under reduced pressure to obtain a white powder product, which was dried at room temperature to obtain the 5,10-dihydrophenazine intermediate. In S1, the molar ratio of phenazine to sodium dithionite is 1:8-1:10, the reaction temperature is 90-100° C., and the reaction time is 1-5 hours.

[0034] S2: Under nitrogen protection, dissolve the 5,10-dihydrophenazine intermediate obtained in step S1 in anhydrous t...

Embodiment 1

[0040] Synthesis of Phenazine Compounds Based on Aryl Phosphine Sulfur Modification

[0041]

[0042] Step 1, add 2.7g of phenazine to the reaction bottle, take another reaction bottle and add 26.1g of sodium dithionite, vacuumize and blow nitrogen for three times, inject 73mL of ethanol into the phenazine system under the protection of nitrogen, and inject 100mL of distillation into In the sodium dithionite system, after fully dissolving, inject the aqueous solution of sodium dithionite into the phenazine alcohol solution, perform light-shielding treatment, raise the temperature to 95° C. for reaction under nitrogen protection, and condense and reflux for 3 hours. After the reaction is completed, cool to room temperature, filter out the flocs, wash with distilled water, and dry to obtain the 5,10-dihydrophenazine intermediate without further purification.

[0043] Step 2, add 1.5g of 5,10-dihydrophenazine intermediate to the reaction bottle, vacuumize, blow nitrogen repeated...

Embodiment 2

[0051] Synthesis of Phenazine Compounds Modified by Arylphosphine Oxygen

[0052]

[0053] Step 5: Dissolve 0.5 g of the phosphine-containing aromatic derivative intermediate obtained in Step 3 in dichloromethane solution, then control the reaction system at 0°C, add 0.91 mL of 30% hydrogen peroxide, and keep the temperature at low temperature for ten minutes , return to room temperature, stir overnight at room temperature, and purify to obtain the target product (III).

[0054] The hydrogen spectrogram and the carbon spectrogram of the obtained product are respectively as follows image 3 and Figure 4 As shown, the structural characterization data are as follows:

[0055] 1 H NMR (400MHz, CDCl 3 , ppm) δ8.03-7.98(m, 8H), 7.50-7.46(m, 4H), 7.42-7.93(m, 8H), 7.08(m, 4H), 6.69-6.64(m, 4H).

[0056] 13 C NMR (100MHz, CDCl3, ppm) δ137.24, 132.86, 132.77, 132.17, 132.14, 132.10, 130.81, 128.65, 128.52, 124.10, 122.80, 122.77.

[0057] MALDI-TOF m / z: 582.319.

[0058] Th...

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Abstract

The invention discloses a photoelectric functional material based on phosphine sulfur / oxygen modifying phenazine. In the material, R1 and R2 are alkyl chains or aryl groups and derivatives thereof, and X1 and X2 are sulphur atoms or oxygen atoms. The alkyl chains are any one of methyl, ethyl, isopropyl, tertiary butyl, n-butyl, cyclohexane or hexamethylene. The aryl groups and derivatives thereofare any one of phenyl group, 4-methyl phenyl, 3,5-dimethyl phenyl, 2,4,6-trimethyl phenyl, 4-methoxyl phenyl, 4-isopropoxy phenyl, 4-methoxyl-3,5-dimethyl phenyl, naphthaline-1-yl or furan-2-yl. The method has the advantages that the synthesis steps are simple, the raw materials are low toxic, cheap and easy to get, the synthesis method has the good compatibility on functional groups, and the atomic economy is high, and the obtained product has the wide potential application value in the photoelectric material field, and is hopeful to be applied to the field of photoelectric materials.

Description

technical field [0001] The invention relates to a photoelectric functional material based on phosphine sulfur / oxygen modified phenazine and a synthesis method thereof, belonging to the field of organic synthesis chemistry. Background technique [0002] Phenazine and its derivatives are widely used as electron acceptors in various organic optoelectronic functional materials. Electron-deficient phenazine can be converted into extremely electron-rich dihydrophenazine after chemical reduction. It has been reported that dihydrophenazine and its derivatives are used as p-type materials (holes) in electronic devices, such as organic light-emitting Diodes (OLEDs), organic field transistors. However, due to the instability of phenazine itself, the current further development and research on phenazine compounds is largely limited by the properties of the compound itself and the synthesis method. [0003] The electron-rich phosphine oxygen / sulfur structure is introduced into phenazin...

Claims

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Application Information

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IPC IPC(8): C07F9/6509C09K11/06
CPCC09K11/06C09K2211/1007C09K2211/1014C09K2211/1044
Inventor 陈润锋蒋云波李欢欢黄维
Owner NANJING UNIV OF POSTS & TELECOMM
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