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Bis-triazole pentacene quinone compound and preparation method thereof

A compound, the technology of pentabenzoquinone, which is applied in the field of chemical synthesis, can solve the problems of poor solubility and achieve the effect of simplifying the preparation process

Active Publication Date: 2017-06-23
LANZHOU UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The technology to be solved by the present invention aims at the poor solubility of the organic N-type semiconductor materials of pentacenequinones in the prior art, and provides a bistriazolopentaquinone compound which is used to make semiconductor devices and can be dissolved in organic solvents

Method used

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  • Bis-triazole pentacene quinone compound and preparation method thereof
  • Bis-triazole pentacene quinone compound and preparation method thereof
  • Bis-triazole pentacene quinone compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] 2,10-dioctyl-pentacene[2,3-d:9,10-d']bis([1,2,3]triazole)-6,14(2H,10H)-dione ( A4)

[0028]

[0029] The preparation method of above-mentioned formula (A4) compound is as follows

[0030] S101: Preparation of 5,6-dimethyl-2-octyl-2H-benzo[d][1,2,3]triazole (A1):

[0031]

[0032] 5,6-Dimethyl-2H-benzo[d][1,2,3]triazole (2.94 g, 20 mmol), sodium hydroxide (960 mg, 24 mmol) and catalytic amount of tetrabutylammonium bromide Dissolve in DMSO (250mL); remove the air in the reaction system, fill with argon; add 1-bromooctane (3.86g, 20mmol), and stir the reaction at room temperature; after reacting for 16 hours, add ethyl acetate to extract the mixture, It was washed with water again, and the organic phase was washed with saturated brine, then dried (anhydrous magnesium sulfate), and concentrated. The product was purified by column chromatography (petroleum ether / ethyl acetate, 15:1) to obtain product (A1) (2.07 g, 40%).

[0033] S102: Preparation of 5,6-bis(bromom...

Embodiment 2

[0043] 2,10-Dihexyl-pentacene[2,3-d:9,10-d']bis([1,2,3]triazole)-6,14(2H,10H)-dione (B4 )

[0044]

[0045] The preparation method of above-mentioned formula (B4) compound is as follows

[0046] S201: Preparation of 5,6-dimethyl-2-hexyl-2H-benzo[d][1,2,3]triazole (B1):

[0047]

[0048] 5,6-Dimethyl-2H-benzo[d][1,2,3]triazole (2.94 g, 20 mmol), sodium hydroxide (960 mg, 24 mmol) and catalytic amount of tetrabutylammonium bromide Dissolve in DMSO (250mL); remove the air in the reaction system, fill with argon; add 1-bromohexane (3.30g, 20mmol), and stir the reaction at room temperature; after reacting for 1 hour, add ethyl acetate to extract the mixture, It was washed with water again, and the organic phase was washed with saturated brine, then dried (anhydrous magnesium sulfate), and concentrated. The product was purified by column chromatography (petroleum ether / ethyl acetate, 15:1) to obtain product (B1) (1.94 g, 42%).

[0049] S202: Preparation of 5,6-bis(bromomet...

Embodiment 3

[0059] 2,10-Didecyl-pentacene[2,3-d:9,10-d']bis([1,2,3]triazole)-6,14(2H,10H)-dione ( C4)

[0060]

[0061] The preparation method of above-mentioned formula (C4) compound is as follows

[0062] S301: Preparation of 5,6-dimethyl-2-decyl-2H-benzo[d][1,2,3]triazole (C1):

[0063]

[0064] 5,6-Dimethyl-2H-benzo[d][1,2,3]triazole (2.94 g, 20 mmol), sodium hydroxide (960 mg, 24 mmol) and catalytic amount of tetrabutylammonium bromide Dissolve in DMSO (250mL); remove the air in the reaction system, fill with argon; add 1-bromodecane (4.42g, 20mmol), and stir the reaction at room temperature; after reacting for 16 hours, add ethyl acetate to extract the mixture, It was washed with water again, and the organic phase was washed with saturated brine, then dried (anhydrous magnesium sulfate), and concentrated. The product was purified by column chromatography (petroleum ether / ethyl acetate, 15:1) to obtain product (C1) (2.58 g, 45%).

[0065] S302: Preparation of 5,6-bis(bromom...

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Abstract

The invention provides a bis-triazole pentacene quinone compound. A chemical name of the bis-triazole pentacene quinone compound is 2,10-bis(R)-pentacene[2,3-d:9,10-d]bis([1,2,3]triazole)-6,14(2H,10H)-diketone compound; the structural general formula is as shown in the specification, wherein a group represented by R is selected from hexyl, octyl, decyl, dodecyl, 2-octyldodecyl and benzyl. The invention further provides a preparation method of the compound as shown in a formula (I). The compound is a pentacene quinine N-type organic semiconductor material. The compound has relatively long alkyl, so that the compound has good solubility, a solution processing method can be adopted in preparation of a semiconductor device, and the preparation process is simplified.

Description

technical field [0001] [ 1,2,3]triazole)-6,14(2H,10H)-diketone compound and preparation method thereof. Background technique [0002] Substituted pentacenequinones have low LUMO orbital energy and have the properties of N-type semiconductors. For example, tetrafluoro-substituted pentacenequinone and bisthiadiazopentaquinone have high electron mobility. However, the solubility of these pentacenequinone compounds in solvents is extremely poor, which brings great inconvenience to device processing. [0003] The invention provides an N-type organic semiconductor material which has excellent performance and can be dissolved in an organic solvent and a synthesis method thereof. It can be made into a semiconductor device by a solution processing method. Contents of the invention [0004] The technology to be solved by the present invention aims at the poor solubility of the organic N-type semiconductor materials of pentacenequinones in the prior art, and provides a bistriazol...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04
CPCC07D487/04
Inventor 师自法许年胜满涛
Owner LANZHOU UNIVERSITY
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