A novel nitrogen-heterofused ring compound and its preparation method and application

A compound and fused ring technology, which is applied in the field of new nitrogen heterofused ring compounds and their preparation, can solve the problems of unsatisfactory material performance and stability, and achieve the advantages of electron transmission, good stability and solubility, and increased Solubility effect

Active Publication Date: 2021-10-22
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] However, the existing materials and synthesis methods are difficult to fused molecules with too long effective benzene ring length, and the properties and stability of the obtained materials are not ideal.

Method used

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  • A novel nitrogen-heterofused ring compound and its preparation method and application
  • A novel nitrogen-heterofused ring compound and its preparation method and application
  • A novel nitrogen-heterofused ring compound and its preparation method and application

Examples

Experimental program
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Effect test

Embodiment 1

[0055] A preparation method of a novel nitrogen-heterofused ring compound, comprising the steps of:

[0056] Under nitrogen atmosphere, mix 38mg 1,2 phenylenediamine (compound I) with 106mg 3,8-bis(2-dodecyl)-3,8-dihydroindole[7,6g]indole-1 , 2,6,7-tetraketone (compound II) was added to a single-necked flask (equivalent ratio of 2 to 1), and then 8 mL of glacial acetic acid was added to react at 120 ° C for 12 h. The obtained solution was distilled under reduced pressure to remove acetic acid, and then purified by a chromatographic column. The eluent was dichloromethane. After separation and purification, the dichloromethane was distilled under reduced pressure and spin-dried to obtain a yellow solid product (compound III). Mass 48.7 mg, yield 37%. of the product 1 H NMR spectrum as figure 1 As shown, the mass spectrum is as figure 2 As shown, the thermogravimetric analysis diagram is shown as image 3 As shown, the spectrum can prove that compound III has good thermal s...

Embodiment 2

[0061] A preparation method of a novel nitrogen-heterofused ring compound, comprising the steps of:

[0062] Under nitrogen atmosphere, mix 20mg 1,2 naphthalene diamine (compound IV) with 52mg 3,8-bis(2-octyldodecyl)-3,8-dihydroindoline[7,6g]indole -1,2,6,7-tetraketone (compound V) was added into a single-necked flask (equivalent ratio of 2 to 1), and then 4 mL of glacial acetic acid was added, and reacted at 120°C for 4 h. The obtained solution was distilled under reduced pressure to remove acetic acid first, and then purified by a chromatographic column. The eluent was toluene. After separation and purification, the toluene was distilled under reduced pressure and spin-dried toluene to obtain a red solid product (compound VI). The obtained compound quality was 30 mg. The yield was 43.8%. of the product 1 H NMR spectrum as Figure 4 As shown, the mass spectrum is as Figure 5 As shown, the thermogravimetric analysis diagram is shown as Image 6 As shown, the spectrum can...

Embodiment 3

[0067] A preparation method of a novel nitrogen-heterofused ring compound, comprising the steps of:

[0068] Under nitrogen atmosphere, mix 8.7mg 4,5 difluoro-1,2 phenylenediamine (compound A) with 20 mg 3,8-bis(2-octyldodecyl)-3,8-dihydroindoline [7,6g] Indole-1,2,6,7-tetraketone (compound V) was added into a one-necked flask, then 2mL glacial acetic acid and 2mL chloroform were added, and the reaction was carried out at 75°C for 1.5h. The obtained solution was distilled off under reduced pressure to remove the solvent, and then purified by a chromatographic column. The eluent was dichloromethane. After separation and purification, the dichloromethane was distilled under reduced pressure and spin-dried to obtain a yellow solid product (compound B). Mass 11.2 mg, yield 45%. of the product 1 H NMR spectrum as Figure 7 shown.

[0069] The chemical reaction equation of the above reaction is as follows:

[0070]

[0071] Wherein compound V was prepared by literature metho...

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Abstract

The invention discloses a novel aza-condensed ring compound, its preparation method and application. The present invention has synthesized a novel aza-condensed ring compound through a very simple method, and its general chemical structure is shown in formulas (IX), (X), and (XI), wherein AR is the number of benzene rings ≥0 condensed rings, benzene ring azaheterocycles, fused ring benzazene heterocycles, benzene rings connected to halobase azaheterocycles or condensed rings connected to halobase azaheterocycles, R is ≥ 12 carbon atoms straight-chain or branched-chain alkyl groups. The synthesis method of the invention is simple and convenient, and the compound has good solubility. Compared with other acene structures, the method synthesizes a series of acene analogues with fewer steps and higher yield. The series of products synthesized by this simple method can obtain a structure with an effective conjugate length of more than sixteen rings, which is extremely conducive to the transmission of electrons, and the maximum absorption wavelength is in the visible light field. The battery (OPV) field has potential application prospects.

Description

technical field [0001] The invention relates to the technical field of organic semiconductor materials, and more specifically, to a novel nitrogen-heterocondensed ring compound and its preparation method and application. Background technique [0002] Compared with inorganic semiconductor materials, organic semiconductor materials have four outstanding advantages: 1) Organic substances can be modified through simple chemical modification to obtain materials that people need, and even multifunctional devices can be obtained; 2) Organic semiconductor materials The material has good flexibility and toughness. If flexible substrates such as polymers are used again, fully flexible devices can be used, and organic field effect transistors can be applied to rollable and foldable products such as integrated circuits, flexible displays, and electronic paper; 3 ) Through simple chemical modification, organic semiconductors can be dissolved in common solvents, and then the traditional v...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D487/22C07D519/00H01L51/30H01L51/54
CPCC07D487/22C07D519/00H10K85/6572Y02E10/549
Inventor 岳晚廖海良
Owner SUN YAT SEN UNIV
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