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6,13-substituted pentacene and derivatives thereof, as well as preparation

A technology of pentacene and derivatives, applied in organic chemistry and other directions, can solve problems such as poor product performance, many reaction by-products, and complex reactions, and achieve the effects of good field effect mobility, simple steps, and good solubility.

Inactive Publication Date: 2009-04-22
BEIJING UNIV OF CHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, many methods have the disadvantages of complex reaction, many reaction by-products, difficult purification, low yield, and poor product performance.

Method used

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  • 6,13-substituted pentacene and derivatives thereof, as well as preparation
  • 6,13-substituted pentacene and derivatives thereof, as well as preparation
  • 6,13-substituted pentacene and derivatives thereof, as well as preparation

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Embodiment 1: the preparation of 6,13-diphenylpentacene

[0037] Preparation of pentacenediquinone

[0038] Add 6.7g of o-phthalaldehyde, 2.8g of 1,4-cyclodihexanone and 70mL of ethanol into a 200mL three-necked flask to completely dissolve the solid. Then 35 mL of 10% KOH aqueous solution was added dropwise to the flask, and a precipitate formed. The above process requires constant stirring. After the KOH was added dropwise, the reaction was stirred for another 0.5 hour. The resulting mixture was suction-filtered, and the precipitate was washed with deionized water several times in small amounts until the filtrate was clear and colorless; then the precipitate was washed with absolute ethanol several times in a small amount until the filtrate was clear and colorless; Washing; Finally, after vacuum drying, pentacenediquinone is obtained.

[0039] Preparation of Grignard reagents

[0040] Add 0.6g of magnesium powder and a small grain of iodine into a dry 100mL three...

Embodiment 2

[0043] Example 2: Preparation of 2,3,9,10-tetramethyl-6,13-diphenylpentacene

[0044] Preparation of 2,3,9,10-tetramethylpentacenediquinone

[0045] 7.9 g of 3,4-dimethyl-phthalaldehyde, 2.8 g of 1,4-cyclodihexanone and 70 mL of ethanol were added into a 200 mL three-necked flask to completely dissolve the solid. 35 mL of 10% KOH aqueous solution was added dropwise to the flask. The above process requires constant stirring. After the dropwise addition of KOH, the reaction was stirred for another 1 h. The resulting mixture was suction-filtered, and the precipitate was washed with deionized water several times in small amounts until the filtrate was clear and colorless; then the precipitate was washed with absolute ethanol several times in a small amount until the filtrate was clear and colorless; washing; and finally vacuum drying to obtain 2,3,9,10-tetramethylpentacenediquinone.

[0046] Preparation of Grignard reagents

[0047] Add 0.5g of magnesium powder and a small gr...

Embodiment 3

[0050] Embodiment 3: the preparation of 6,13-two (1-naphthyl) pentacene

[0051] Preparation of pentacenediquinone

[0052] 6.7 g of o-phthalaldehyde, 2.8 g of 1,4-cyclodihexanone and 70 mL of ethanol were added into a 200 mL three-necked flask to completely dissolve the solid. Further, 35 mL of 15% NaOH aqueous solution was added dropwise to the flask. The above process requires constant stirring. After NaOH was added dropwise, the reaction was stirred for another 0.5 hour. The resulting mixture was suction-filtered, and the precipitate was washed with deionized water several times in small amounts until the filtrate was clear and colorless; then the precipitate was washed with absolute ethanol several times in a small amount until the filtrate was clear and colorless; Washing; finally vacuum drying to obtain pentacenediquinone.

[0053] Preparation of Grignard reagents

[0054] Add 0.2g of magnesium powder and a small grain of iodine into a dry 100mL three-necked flask,...

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Abstract

The invention relates to substituents for 6,13-substituent pentacene and derivatives thereof, wherein the substituents of the 6,13-substituent pentacene and the derivatives thereof are mainly hydrogen atom, electron-donating group, electron-withdrawing group and combination of the hydrogen atom, the electron-donating group and the electron-withdrawing group. The synthesis mainly comprises three steps: step one, o-Phthalaldehyde and 1,4-cyclohexanone react to generate 6, 13-pentacenequinone; step two, Grignard reagent and the 6, 13-pentacenequinone react to form substituent pentacene diol; and step three, the 6,13-pentacene diol is further dehydrated to generate 6, 13-pentacene derivatives. The pentacene compounds meet the conditions required on an organic semiconductor material applied to electronic components, namely good field effect mobility, high stability and good solubility. O-phthalaldehyde and the 6, 13- pentacene derivatives are shown by formulas, wherein R is respectively the independent hydrogen atom, electron-donating group, electron-withdrawing group and combination of the hydrogen atom, the electron-donating group and the electron-withdrawing group.

Description

technical field [0001] The present invention relates to 6,13-substituted pentacenes and their derivatives which can be used as novel organic semiconductors and their preparation methods. Background of the invention [0002] Organic semiconductors are a new class of materials developed in recent years. They are favored by scholars because of their excellent photoelectric performance, low production cost, simple processing technology, wide range of material selection, and good mechanical properties. [0003] Pentacene, an aromatic molecule composed of five benzene rings, is one of the most promising organic semiconductor materials. Because it is a crystal, the ordered combination structure of its atoms can allow electrons to pass through more easily than other amorphous organic materials, and the carrier mobility in field effect transistors can reach 1.5cm 2 / (Vs) above, up to 5cm 2 / (Vs), so it has become one of the hottest research topics in the field of organic semiconduc...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D493/04C07D487/04C07D471/04C07D495/04
Inventor 张敬畅黄忠符雅丽曾婷曹维良
Owner BEIJING UNIV OF CHEM TECH
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