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A kind of sulfur nitrogen phosphorus heterocyclic compound and its preparation method and application

A compound and phosphorus heterocycle technology, applied in the field of sulfur nitrogen phosphorus heterocyclic compounds and their preparation, tria nitrogen phosphorus heterocyclic compounds and their preparation fields, can solve the problems of long design route, restricting development, complicated steps, etc., and achieve long service life , the effect of small environmental pollution and short synthesis steps

Inactive Publication Date: 2020-12-08
NORTHWESTERN POLYTECHNICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] Nevertheless, the existing methods for preparing such compounds doped with atoms such as nitrogen and phosphorus have rare raw materials, long design routes, cumbersome steps, harsh conditions, and low yields. These unfavorable conditions restrict the development of this field.

Method used

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  • A kind of sulfur nitrogen phosphorus heterocyclic compound and its preparation method and application
  • A kind of sulfur nitrogen phosphorus heterocyclic compound and its preparation method and application
  • A kind of sulfur nitrogen phosphorus heterocyclic compound and its preparation method and application

Examples

Experimental program
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Effect test

Embodiment 1

[0043] To synthesize 2,6,10-triphenyl-1,5,9-triazatriphenylene[1,12-cde:5,4-c'd'e':9,8-c”d” e"] Tris([1,2]nitrophosphorus) 2,6,10-trisulfide as an example, its structure is as follows:

[0044]

[0045] Under the protection of nitrogen, dissolve 273mg (1mmol) of 1,5,9-triaminotriphenylene in 15ml of anhydrous o-dichlorobenzene, add it to a 50ml two-necked bottle, add 0.4ml of triethylamine, and under the protection of inert gas , slowly add 0.12ml of phenylphosphorus dichloride solution, reflux at 180°C for 2 hours, add sulfur powder, cool down to room temperature, and stir overnight. The solvent was removed by rotary evaporation under reduced pressure, separated and purified by column chromatography to obtain a white solid with a yield of 29% and a melting point of 273-277°C.

[0046] The spectral data of the resulting product are as follows:

[0047] 1 H NMR (400MHz, DMSO) δ9.87(s, 3H), 8.08-7.92(m, 3H), 7.91-7.75(m, 6H), 7.55(d, J=24.7Hz, 12H). 13 C NMR(101MHz,DMSO)δ=1...

Embodiment 2

[0050] To synthesize 3,4,7,8,11,12-hexamethoxy-2,6,10-triphenyl-1,5,9-triazatriphenylene[1,12-cde:5,4 -c'd'e':9,8-c”d”e”] tris([1,2]nitrogen phosphorus) 2,6,10-trisulfide as an example, its structural formula is as follows:

[0051]

[0052] Under nitrogen protection, dissolve 453mg (1mmol) of 3,4,7,8,11,12-hexamethoxy-1,5,9-triaminotriphenylene in 15ml of anhydrous o-dichlorobenzene and add to 50ml In the two-neck flask, add 0.4ml triethylamine, under the protection of inert gas, slowly add 0.12ml phenyl phosphorus dichloride solution, reflux reaction at 180°C for 2 hours, add sulfur powder, cool down to room temperature, and stir overnight. The solvent was removed by rotary evaporation under reduced pressure, separated and purified by column chromatography to obtain a white solid with a yield of 35% and a melting point of 241-243°C.

[0053] The spectral data of the resulting product are as follows: 1 H NMR (400MHz, CDCl 3 )δ=8.34–7.95(m,0H),7.58(dd,J=12.9,9.3,0H),6.77...

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Abstract

The present invention relates to a kind of sulfur nitrogen phosphorus heterocycle compound, and this compound has following structural formula, wherein R 1 is sulfur; R 2 It is one of hydrogen and methoxy, and the present invention also relates to the preparation method and use of the sulfur nitrogen phosphorus heterocyclic compound. The invention utilizes triamine triphenylene to react with phenyl phosphorus dichloride, and then adds sulfur powder to react to obtain sulfur nitrogen phosphorus heterocyclic compound. The present invention has short synthesis steps, mild reaction conditions, convenient operation and good yield, and the obtained sulfur nitrogen phosphorus heterocyclic compound has good thermal stability and chemical stability, and can be used to prepare field effect transistors, solar cells or light-emitting diodes, etc.

Description

technical field [0001] The present invention relates to a polycyclic aromatic hydrocarbon compound and its preparation method and application, in particular to a triazine phosphorus heterocyclic compound and its preparation method and application, more specifically, to a sulfur nitrogen phosphorus heterocyclic compound and its preparation method and apply. Background technique [0002] As an important organic functional material, PAH molecules have unique and tunable molecular structures, photoelectric properties and self-assembly behaviors, and are widely used in field-effect transistors, organic semiconductor materials, solar cells and organic light-emitting diodes. [0003] At present, an important research trend of polycyclic aromatic hydrocarbons is to dope heteroatoms such as nitrogen, sulfur, selenium, phosphorus, etc. Thereby adjusting its material properties. When nitrogen and phosphorus atoms are doped to the carbon atoms in the structure, it can not only change ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F9/6584H01L51/50H01L51/54H01L51/42H01L51/46
CPCC07F9/6584H10K85/657H10K30/00H10K50/00Y02E10/549
Inventor 李学香李志浩王娇田威
Owner NORTHWESTERN POLYTECHNICAL UNIV