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Copolymer containing cyclopentadiene bithiophene-benzo-bis (benzothiadiazole) and preparation method and application thereof

A dithiazole, copolymer-like technology, applied in chemical instruments and methods, semiconductor/solid-state device manufacturing, organic chemistry, etc., can solve problems such as energy gap width

Inactive Publication Date: 2014-05-07
OCEANS KING LIGHTING SCI&TECH CO LTD +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the energy gap (the energy level difference between the HOMO energy level and the LUMO energy level) of the existing benzodithiophene derivatives is wide

Method used

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  • Copolymer containing cyclopentadiene bithiophene-benzo-bis (benzothiadiazole) and preparation method and application thereof
  • Copolymer containing cyclopentadiene bithiophene-benzo-bis (benzothiadiazole) and preparation method and application thereof
  • Copolymer containing cyclopentadiene bithiophene-benzo-bis (benzothiadiazole) and preparation method and application thereof

Examples

Experimental program
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preparation example Construction

[0058] The preparation method of the benzodithiophene copolymer containing bithiazole unit of one embodiment, such as figure 1 shown, including the following steps:

[0059] Step S100, providing compound A and compound B.

[0060] A is: B is:

[0061] Among them, R 1 , R 2 , R 5 , R 6 for H, C 1 ~C 16 the alkyl group, R 3 for C 1 ~C 16 Alkyl, C 1 ~C 16 The alkoxy group or the alkylthiophene represented by the following structural formula:

[0062] R is C 1 ~C 16 the alkyl group, R 4 for H, C 1 ~C 16 Alkyl, C 1 ~C 16 of alkoxy.

[0063] Wherein the preparation of compound A comprises the following steps:

[0064] Step S111, under the protection of nitrogen, add the dichloromethane solution of compound C represented by the following structural formula dropwise to the dichloromethane solution containing 1,3-dicyclohexylcarbodiimide (DDC) and 4-dimethylaminopyridine (DMAP) Reaction in methyl chloride at room temperature for 12 hours to 15 hours, wherein...

Embodiment 1

[0103] This embodiment discloses a benzodithiophene copolymer with the following structure:

[0104]

[0105] n=60;

[0106] The preparation steps of above-mentioned benzodithiophene copolymer are as follows:

[0107] One, the preparation of 1,3-two (2-thiophene) acetone:

[0108]

[0109] First, dissolve 7.6g (36.8mmol) of DCC and 1.23g (10mmol) of DMAP with 70mL of treated dichloromethane, and dissolve 5g (35.2mmol) of 2-thiopheneacetic acid in 70mL of dichloromethane under the protection of nitrogen Add dropwise to the above reaction solution, and react for 12 hours. After the reaction, the reaction solution was filtered, recrystallized twice with n-hexane, and then separated and purified by column chromatography to obtain the product.

[0110] MALDI-TOF-MS (m / z): 222.3 (M + ).

[0111] Two, the preparation of 2,7-dioctyloxybenzo[1,2-b:4,3-b']dithiophene-4,5-dione:

[0112]

[0113] Take 25.4g (60mmol) of 4,4'-bis(2-octyloxy)thiophene and add it to 400mL of d...

Embodiment 2

[0128] This embodiment discloses a benzodithiophene copolymer with the following structure:

[0129]

[0130] n=30;

[0131] The preparation steps of above-mentioned benzodithiophene copolymer are as follows:

[0132] One, the preparation of 1,3-two (3-methyl-2-thiophene) acetone:

[0133]

[0134] First, dissolve 8.3g (40mmol) of DCC and 1.23g (10mmol) of DMAP with 70mL of treated dichloromethane, and dissolve 5g (35.2mmol) of 3-methyl-2-thiopheneacetic acid in 70mL of The dichloromethane solution was added dropwise to the above reaction solution, and reacted for 15 hours. After the reaction, the reaction solution was filtered, recrystallized twice with n-hexane, and then separated and purified by column chromatography to obtain the product.

[0135] MALDI-TOF-MS (m / z): 250 (M + ).

[0136] 2. Preparation of 2,7-di(hexadecyloxy)benzo[1,2-b:4,3-b']dithiophene-4,5-dione:

[0137]

[0138] Take 33.5g (51.8mmol) of 4,4'-bis(2-hexadecyloxy)thiophene and add it to 40...

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Abstract

A benzo-bithiophene copolymer containing a 2-thiazole unit has the following structural formula: P: (shown in the Specification), wherein the R1, R2, R5 and R6 are H or alkyls from C1 to C16; the R3 is an alkyl from C1 to C16, an alkoxy group from C1-C16 or thiophene (R is an alkyl from C1 to C16) having a structural formula shown in the Specification, and R4 is H, an alkyl from C1 to C16 or an alkoxy group from C1 to C16; the n is an integer from 1 to 60. The benzo-bithiophene copolymer containing the 2-thiazole unit has a relatively narrow energy gap. The invention further provides a preparation method of the benzo-bithiophene copolymer containing the 2-thiazole unit as well as solar battery devices, organic electroluminescent devices and organic field effect transistors, which adopt the benzo-2 bithiophene copolymer containing a 2-thiazole unit.

Description

technical field [0001] The invention relates to a benzodithiophene copolymer containing a bithiazole unit, a preparation method thereof, and a solar battery device and an organic electroluminescent device using the benzodithiophene copolymer containing a bithiazole unit. Background technique [0002] The energy issue is a major issue of great concern to all countries in the world. Solar energy is the most ideal alternative energy source for humans in the future, and solar cells that convert solar energy into electrical energy are also research hotspots. Conjugated polymer thin film solar cells emerging in recent years have outstanding advantages such as low cost, light weight, simple manufacturing process, and can be prepared into flexible devices. In addition, organic materials are diverse and highly designable, promising to improve the performance of solar cells through material design and optimization. [0003] Benzodithiophene derivatives, two thiophenes are fused in o...

Claims

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Application Information

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IPC IPC(8): C08G61/12C07D495/04C09K11/06H01L51/54H01L51/30
Inventor 周明杰管榕李满园黄佳乐黎乃元
Owner OCEANS KING LIGHTING SCI&TECH CO LTD
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