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Process for preparing pentacene derivatives

A derivative, pentacene technology, applied in the field of new compounds for the preparation of aromatic organic semiconductor compounds, can solve problems such as unusable

Inactive Publication Date: 2005-03-09
3M INNOVATIVE PROPERTIES CO
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, pentacene is insoluble in commonly used solvents and therefore cannot be used in solution processing processes

Method used

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  • Process for preparing pentacene derivatives
  • Process for preparing pentacene derivatives
  • Process for preparing pentacene derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0105] Embodiment 1: the preparation of 2,9-dimethylpentacene

[0106] Preparation of 2,5-bis(4-methylbenzyl)terephthalic acid

[0107] In a hydrogen atmosphere at 270kPa, a mixture of 30.0 grams of 2,5-bis(4-methylbenzoyl)terephthalic acid, 500 mL of acetic acid and 3 grams of 5% palladium on activated carbon (as a catalyst) was heated to 64°C and maintained for 17 hours. The mixture was filtered to remove catalyst and product. Catalyst and product are made slurry in 500mL tetrahydrofuran, and pass through Celite TM Diatomaceous earth filter aid filter. The resulting filtrate was concentrated in vacuo. The resulting wet solid was slurried in ethyl acetate and the solid was collected by filtration and dried to give 2,5-bis(4-methylbenzyl)terephthalic acid.

[0108] Preparation of 7,14-dihydro-3,10-dimethylpentacene-5,12-dione

[0109] To a mixture of 12.7 grams of 2,5-bis(4-methylbenzyl)terephthalic acid and 90 mL of trifluoroacetic acid was added 81.6 grams of trifluo...

Embodiment 2

[0112] Embodiment 2: the preparation of 2,10-dimethylpentacene

[0113] Preparation of 4,6-bis(4-methylbenzyl)isophthalic acid

[0114] In a hydrogen atmosphere at 270 kPa, a mixture of 21.1 g of 4,6-bis(4-ethylbenzoyl)isophthalic acid, 350 mL of acetic acid, and 2.10 g of 5% palladium on activated carbon (as a catalyst) was heated to 65°C and maintained for 17 hours. by Celite TM The mixture was filtered through a Celite filter aid to remove the catalyst. The resulting filtrate was concentrated in vacuo to give 4,6-bis(4-methylbenzyl)isophthalic acid.

[0115] Preparation of 3,9-dimethylpentacene-5,7(12H,14H)-dione

[0116] To 14.1 grams of 4,6-bis(4-methylbenzyl)isophthalic acid was added 75 mL of trifluoroacetic acid, followed by 48 grams of trifluoromethanesulfonic acid. After stirring the reaction mixture at room temperature for 3 days, the mixture was poured onto 200 g of ice. The resulting solid was collected by filtration. The solid was washed with 400 mL of s...

Embodiment 3

[0119] Embodiment 3: the preparation of 2,9-dihexylpentacene

[0120] Preparation of 2,5-bis(4-hexylbenzoyl)terephthalic acid

[0121] Within 3.5 hours, add 25.7 grams of aluminum chloride, 51.3 mL of 1,2-dichloroethane and 10 grams of benzene-1,2,4,5-tetracarboxylic dianhydride (pyrellitic dianhydride) to the solution while cooling. ) was added a solution of 14.9 grams of hexylbenzene and 6.40 grams of diisopropylethylamine in 25 ml of 1,2-dichloroethane, and the temperature was kept between 15°C and 20°C. After the addition was complete, the resulting mixture was stirred for an additional 15 minutes, then heated to 40° C. for 1 hour. The hot mixture was poured into a beaker with 200 g of ice and 75 mL of concentrated hydrochloric acid and stirred overnight at room temperature. The water phase was poured off, and the obtained oily solid was stirred with 500 mL of water, and then water was removed. This water washing was repeated, and the resulting residue was dissolved i...

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Abstract

A process for preparing substituted pentacene compounds comprises the step of cyclizing substituted bis(benzyl)phthalic acids using an acid composition comprising trifluoromethanesulfonic acid, the substituted bis(benzyl)phthalic acids being represented by the following general formulas, wherein each R (that is, each of the groups R1 through R8) is independently an electron-donating group, a halogen atom, a hydrogen atom, or a combination thereof.

Description

[0001] priority statement [0002] This application is a continuation-in-part of 09 / 966,954 filed September 27, 2001 and claims priority from that application. field of invention [0003] The present invention relates to a process for the preparation of aromatic organic compounds which can be used as semiconductors. In another aspect, the present invention relates to novel compounds that can be used in the preparation of aromatic organic semiconducting compounds. Background of the invention [0004] Traditionally, inorganic silicon and gallium arsenide semiconductors, silicon dioxide insulators, and metals such as aluminum and copper have dominated the semiconductor industry. In recent years, however, there has been increasing research on organic thin-film transistors (OTFTs) as an alternative to conventional inorganic-material-based thin-film transistors. [0005] Pentacene, thiophenol oligomers, and regioregular polythiophenes have become the most studied organic semico...

Claims

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Application Information

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IPC IPC(8): C07C1/24C07C1/207C07C15/20C07C15/56C07C17/35C07C25/22C07C45/46C07C49/617C07C49/665C07C49/675C07C49/697C07C49/753C07C50/22C07C50/24C07C51/377C07C63/331C07C63/72C07C65/34C07C65/36C07C65/40C07D219/06C07D337/12C07D337/14H01L51/00
CPCC07C49/697C07C2527/03C07C25/22C07D337/12H01L51/0071C07C65/40C07C17/35C07C65/36C07C65/34C07C49/665C07C45/46C07C50/22C07C15/20C07C51/377C07C50/24C07C2103/52C07C49/675C07C1/2078C07C63/72C07C49/753C07D337/14H01L51/0003C07C63/331H01L51/0055C07D219/06C07C2603/52H10K71/12H10K85/623H10K85/657C07C49/76C07C15/38C07C45/45
Inventor D·E·福格尔K·M·福格尔
Owner 3M INNOVATIVE PROPERTIES CO
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