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Preparation method and application of 4,9-bisalkylene indene thieno[3,2-b]thiophene derivative and conjugated polymer thereof

A bis-alkylene indene and dithiophene technology, which is applied in semiconductor/solid-state device manufacturing, photovoltaic power generation, electrical components, etc.

Active Publication Date: 2012-08-22
兰州大成科技股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the low solubility of these two materials, it is not easy to be used to prepare conjugated polymers based on these monomers; although the patent US 20090299029 has announced a class based on 4,4,9,9-tetra(-4-alkyl Preparation of conjugated polymers of phenyl)indeno[1,2-b; 5,6-b]dithiophene, introducing alkylbenzene or alkyl at the 4,9 positions of indenodithiophene, although solving the indeno The problem of poor solubility of dithiophene, but it is not conducive to reducing the distance between indeno[1,2-b;5,6-b]dithiophene molecules and intramolecular π–π conjugated units, which is not conducive to the formation of large ordered Phase structure, to obtain organic semiconductor materials with high mobility

Method used

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  • Preparation method and application of 4,9-bisalkylene indene thieno[3,2-b]thiophene derivative and conjugated polymer thereof
  • Preparation method and application of 4,9-bisalkylene indene thieno[3,2-b]thiophene derivative and conjugated polymer thereof
  • Preparation method and application of 4,9-bisalkylene indene thieno[3,2-b]thiophene derivative and conjugated polymer thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Example 1: Preparation of 4,9-bis(2-hexyldecylene)indeno[1,2-b; 5,6-b]dithiophene:

[0034] Indeno[1,2-b;5,6-b]dithiophene-4,9-dione (1.0 g, 3.4 mmol) was added to a 250 mL three-necked flask, and dry o-dichlorobenzene 100 mL. After stirring at room temperature for 20 min, the Grignard reagent of 1-bromo-2-hexyldecane prepared in advance (made of 6.4 g of 1-bromo-2-hexyldecane and 0.5 g of magnesium in 60 mL of anhydrous tetrahydrofuran prepared) was added with stirring at room temperature. The reaction was stirred overnight under the protection of argon. After adding water to quench, filter with suction, wash the filter cake with ethyl acetate, and extract the filtrate with ethyl acetate and wash with water. Anhydrous NaSO 4 After drying, the solvent was distilled off under reduced pressure. A brown solid was obtained. Dissolve the brown solid in hot (60-65 O C) 30 mL absolute ethanol. Transfer to a 100 mL three-neck flask, and add 10 mL of hydrochloric acid. ...

Embodiment 2

[0037] Example 2: Preparation of 4,9-bis(decylene)indeno[1,2-b; 5,6-b]dithiophene

[0038] Add indeno[1,2-b;5,6-b]dithiophene-4,9-dione (1.0 g, 3.4 mmol) into a 250 mL three-neck flask, and add dry o- Dichlorobenzene 100 mL. After stirring at room temperature for 20 min, the Grignard reagent of 1-bromo-decane prepared in advance (prepared from 4.6 g of 1-bromo-decane and 0.5 g of magnesium in 60 mL of anhydrous tetrahydrofuran) was added at room temperature into the reaction. The reaction was stirred overnight under the protection of argon. After adding water to quench, filter with suction, wash the filter cake with ethyl acetate, and extract the filtrate with ethyl acetate and wash with water. Anhydrous NaSO 4 After drying, the solvent was evaporated under reduced pressure. A brown solid was obtained. Dissolve the brown solid in hot (60-65 O C) 30 mL absolute ethanol. Transfer to a 100 mL three-neck flask, and add 10 mL of hydrochloric acid. 20 mL of THF, heated to r...

Embodiment 3

[0041] Example 3: Preparation of 4,9-bis(9-heptadecyl)indeno[1,2-b; 5,6-b]dithiophene

[0042] Add indeno[1,2-b;5,6-b]dithiophene-4,9-diketone (1.0 g, 3.4 mmol) to a 250 mL three-neck flask, add anhydrous 100 mL of o-dichlorobenzene. After stirring at room temperature for 20 min, the Grignard reagent of 9-bromoheptadecane prepared in advance (prepared from 6.65 g of 9-bromoheptadecane and 0.5 g of magnesium in 60 mL of anhydrous tetrahydrofuran) was added at room temperature . The reaction was stirred overnight under the protection of argon. After adding water to quench, filter with suction, wash the filter cake with ethyl acetate, and extract the filtrate with ethyl acetate and wash with water. Anhydrous NaSO 4 After drying, the solvent was distilled off under reduced pressure. A brown solid was obtained. Dissolve the brown solid in hot (60-65 O C) 30 mL of absolute ethanol. Transfer to a 100 mL three-neck flask, and add 10 mL of hydrochloric acid. 20 mL of THF, heat...

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Abstract

The invention relates to preparation of a 4,9-bis(alkylene) indene thieno[3,2-b]thiophene derivative which is applicable to organic optoelectronic materials. A 4,9-bis(alkylene) indene thieno[3,2-b]thiophene derivative has a chemical structure as shown in general formula (I). A preparation method of the 4,9-bis(alkylene) indene thieno[3,2-b]thiophene derivative comprises the following steps: reacting indene thieno[3,2-b]thiophene-4,9-diketone with a Grignard reagent prepared by brominated alkanes with a chain length of C1-C20 and magnesium, performing heating reflux for dehydroxylation of the obtained tertiary alcohol in the presence of hydrochloric acid or other mixed acids so as to obtain 4,9-bis(alkylene) indene thieno[3,2-b]thiophene. The preparation method of the invention can obtain the 4,9-bis(alkylene) indene thieno[3,2-b]thiophene derivative with good solution processability and a long carbon chain; the mother ring of indene thieno[3,2-b]thiophene and the alkylene have good coplanarity, and the alkylene has good flexibility.

Description

technical field [0001] The invention relates to the preparation of 4,9-bis(alkylene)indeno[1,2-b; 5,6-b]dithiophene derivatives which can be used in organic optoelectronic materials; Preparation of Conjugated Copolymerization of (Alkylene) Indeno[1,2-b;5,6-b]Dithiophene Derivatives. Background technique [0002] Since American scientists Alan J. Heeger, Macdiarmid and Japanese scientist Hideki Shirakawa discovered conjugated polymers in 1976, they have not only the electrical and optical properties of metals or inorganic semiconductors, but also retain the superior mechanical properties and processing properties of polymers. and received widespread attention. In recent years, scientists have synthesized many conjugated polymers with photoelectric activity. Meanwhile, taking advantage of the charge-transporting or luminescent properties of these conjugated polymers, applications such as polymer electroluminescent diodes (PLEDs), polymer solar cells (PPVCs), photodetectors, ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D493/04C08G61/12H01L51/42H01L51/46H01L51/48
CPCY02E10/549
Inventor 夏养君范多旺
Owner 兰州大成科技股份有限公司
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