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Nitrogen-sulfur fused-heterocycle hexacene compound and preparation method and application thereof

A compound, nitrogen and sulfur technology, applied in the field of organic photoelectric small molecule semiconductor materials, can solve the problems of poor solubility, little research, poor stability, etc., and achieve good stability, good solubility, and good solubility

Active Publication Date: 2020-08-07
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] Acene compounds are organic semiconductor materials with excellent potential, such as pentacene, which has been widely studied, but it has the disadvantages of poor stability and poor solubility
At present, there are more aza-fused ring compounds, or thia-hetero-condensed ring molecules. Aza and thia-heteroaromatic ring compounds have great potential value as light-emitting materials in organic light-emitting diodes (OLEDs), but currently for those containing pyridine rings , carbazole ring and thiophene ring azo-condensed ring acene compounds are rarely studied

Method used

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  • Nitrogen-sulfur fused-heterocycle hexacene compound and preparation method and application thereof
  • Nitrogen-sulfur fused-heterocycle hexacene compound and preparation method and application thereof
  • Nitrogen-sulfur fused-heterocycle hexacene compound and preparation method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0063] Embodiment 1 A kind of preparation of nitrogen thia hexacene compound

[0064] 1. Preparation method

[0065] (1) Under a nitrogen atmosphere, add 2g bromoisatin and 2.5g dried potassium carbonate into a pear-shaped reaction flask, then add 15mL N,N-dimethylformamide (DMF), stir, and then add 2g Bromo with isooctane, react at 80°C for 12h. After the reaction was completed, the reactant was distilled off under reduced pressure to remove the solvent, and then separated and purified by column chromatography. The ratio of eluent dichloromethane to petroleum ether was 1:1, and compound 1' could be obtained by distillation under reduced pressure. The mass of compound II obtained was 2.7 g, and the yield was 90%;

[0066] (2) Under a nitrogen atmosphere, add 1 g of bromoisatin (1') connected to isooctane chains and 383 mg of 1,2-phenylenediamine into a single-necked flask, then add 8 mL of glacial acetic acid as a catalyst and heat at 115 ° C Reflux, reaction 10h. The obta...

Embodiment 2

[0074] Embodiment 2 Preparation of azathiahexacene compound

[0075] 1. Preparation method

[0076] (1) Under a nitrogen atmosphere, add 2g bromoisatin and 2.5g dried potassium carbonate into a pear-shaped reaction flask, then add 15mL N,N-dimethylformamide (DMF), stir, and then add 2g Bromine with n-octane reacted at 80°C for 12h. After the reaction is completed, the reactants are distilled under reduced pressure to remove the solvent, and then separated and purified by column chromatography. The ratio of eluent dichloromethane and petroleum ether is 1:1, and compound 1" can be obtained by distillation under reduced pressure. Compound The quality of is 2.7g, and the productive rate is 90%;

[0077] (2) Under a nitrogen atmosphere, add 1 g of bromoisatin (1") connected with n-octane chains, and 383 mg of 1, 2-phenylenediamine into a single-necked flask, then add 8 mL of glacial acetic acid as a catalyst and heat to reflux, Reaction for 12 hours. The obtained reactant was di...

Embodiment 3

[0085] Embodiment 3 Preparation of azathiahexacene compound

[0086] 1. Preparation method

[0087] (1) Under a nitrogen atmosphere, add 2g bromoisatin and 2.5g dried potassium carbonate into a pear-shaped reaction flask, then add 15mL N,N-dimethylformamide (DMF), stir, and then add 2g Bromine with n-octane reacted at 80°C for 12h. After the reaction was completed, the reactant was distilled off under reduced pressure to remove the solvent, and then separated and purified by column chromatography. The ratio of eluent dichloromethane to petroleum ether was 1:1, and compound 1"' could be obtained by distillation under reduced pressure. The quality of the compound is 2.7g, and the yield is 90%;

[0088](2) Under a nitrogen atmosphere, add 1 g of bromoisatin (1") connected to n-octane chains and 523 mg of 4,5 dichloro-1,2 phenylenediamine into a single-necked flask, and then add 8 mL of glacial acetic acid As a catalyst, it is heated to reflux and reacted for 12 hours. The obta...

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Abstract

The invention discloses a nitrogen-sulfur fused-heterocycle hexacene compound and a preparation method and application thereof. According to the invention, a pyridine ring and a thiophene ring are fused together through a simple and practical method so as to prepare a nitrogen-sulfur fused-heterocycle semiconductor material with six conjugated rings, high yield, good stability, good solubility andgood crystallinity and capability of generating small molecular single crystals. The compound provided by the invention expands the conjugate family of an organic single crystal field effect transistor, has the maximum absorption wavelength in the field of visible light, can emit fluorescent light, and has important application value in the fields of organic semiconductor luminescence, organic field effect transistors and organic solar cells.

Description

technical field [0001] The invention belongs to the technical field of organic optoelectronic small molecule semiconductor materials. More specifically, it relates to an azathione condensed ring hexacene compound and its preparation method and application. Background technique [0002] Acene compounds are organic semiconductor materials with excellent potential, such as pentacene, which has been widely studied, but it has the disadvantages of poor stability and poor solubility. At present, there are more aza-fused ring compounds, or thia-hetero-condensed ring molecules. Aza and thia-heteroaromatic ring compounds have great potential value as light-emitting materials in organic light-emitting diodes (OLEDs), but currently for those containing pyridine rings , carbazole ring and thiophene ring aza-condensed ring acene compounds are rarely studied. [0003] At the same time, due to the narrow band gap characteristics of acene molecules, theoretically, the more the number of b...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D495/22C09K11/06
CPCC07D495/22C09K11/06C09K2211/1051
Inventor 岳晚廖海良
Owner SUN YAT SEN UNIV
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