Sulfur, nitrogen and phosphorus heterocyclic compound and preparation method and application thereof

A technology of compound and phosphorus heterocycle, which is applied in the field of polycyclic aromatic hydrocarbons and its preparation, can solve the problems of long design route, rare raw materials, and constraints on development, and achieve long service life, good yield, and low environmental pollution.

Inactive Publication Date: 2019-04-05
NORTHWESTERN POLYTECHNICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

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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  • Sulfur, nitrogen and phosphorus heterocyclic compound and preparation method and application thereof
  • Sulfur, nitrogen and phosphorus heterocyclic compound and preparation method and application thereof
  • Sulfur, nitrogen and phosphorus heterocyclic compound and preparation method and application thereof

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 invention relates to a sulfur, nitrogen and phosphorus heterocyclic compound which has the structural formula as shown in the specification, wherein R1 refers to sulfur and R2 refers to one or hydrogen and methoxyl. The invention further relates to a preparation method and application of the sulfur, nitrogen and phosphorus heterocyclic compound. In the preparation method, sulfur powder is added to reactants, namely triphenyl triamine and dichlorophenylphosphine to react to obtain the sulfur, nitrogen and phosphorus heterocyclic compound. According to the preparation method, the synthesis procedure is short, reaction conditions are mild, operation is facilitated, yield is high, the sulfur, nitrogen and phosphorus heterocyclic compound has good heat stability and chemical stability and can be applied to manufacturing of field effect transistors, solar batteries or light emitting diodes, and the like.

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 Applications(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
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