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Carbazole-containing porphyrin-thienothiadiazole copolymer and its preparation method and application

A technology of carbazole porphyrin and alkyl carbazole porphyrin, applied in the field of copolymers, can solve the problems such as no literature and patent reports, limited application scope, etc., and achieve the effects of improving solubility, expanding application scope and simple process

Inactive Publication Date: 2011-12-28
OCEANS KING LIGHTING SCI&TECH CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] However, there are still no literature and patent reports on organic semiconductor materials containing carbazole-containing porphyrin-thienothiadiazole copolymers, which greatly limits their application range.

Method used

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  • Carbazole-containing porphyrin-thienothiadiazole copolymer and its preparation method and application
  • Carbazole-containing porphyrin-thienothiadiazole copolymer and its preparation method and application
  • Carbazole-containing porphyrin-thienothiadiazole copolymer and its preparation method and application

Examples

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preparation example Construction

[0027] A kind of preparation method containing carbazole porphyrin-thienothiadiazole copolymer, comprises the steps:

[0028] 5,15-dibromo-10,20-alkylcarbazole porphyrins of structural formula (A) and bisboronate-thieno[3,4-c][1,2,5] of structural formula (B) are provided Thiadiazoles:

[0029]

[0030] In the formula: n is an integer between 1-100, R 1 , R 2 for the same or different hydrogen or C 1 -C 32 of alkyl.

[0031] In an oxygen-free environment (the present invention uses nitrogen and / or inert gas as protective gas to form an oxygen-free environment), under the presence of a catalyst and an organic solvent, 5,15-dibromo-10,20-alkylcarbazoleporphyrin Carry out Suzuki coupling reaction with double boronate group thieno[3,4-c][1,2,5]thiadiazole, obtain the described carbazole-containing porphyrin-thienothiadiazole copolymerization of structural formula (I) The solution of the substance; wherein, the molar dosage of the catalyst is 0.05%-30% of the bisboronate-b...

Embodiment 1

[0037] This embodiment discloses a 10,20-bis(9-octylcarbazole) porphyrinthieno[3,4-c][1,2,5]thiadiazole copolymer as an organic semiconductor material, its structural formula as follows:

[0038]

[0039] In the formula: n is an integer between 1-100.

[0040]The preparation steps of this copolymer are as follows:

[0041] 1. 5,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)thieno[3,4-c][1,2,5]thio Synthesis of Oxadiazole

[0042]

[0043] Under the protection of nitrogen, 8.8 g (0.03 mol) of 5,7-dibromothieno[3,4-c][1,2,5]thiadiazole was added to the three-necked flask, and 200 ml of tetrahydrofuran solvent was added 25.2 mL (0.06 mol) of n-butyllithium with a concentration of 2.5M was slowly injected with a syringe at -78°C, and after stirring for 2 hours, 2-isopropoxy was injected with a syringe at -78°C Base-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 13 mL (ie. 06 mol), warmed up to room temperature and stirred overnight. Then add saturated 30ml sodium chloride aque...

Embodiment 2

[0058] This embodiment discloses a 10-(9-methylcarbazole)-20-(9-docosylcarbazole) porphyrinthieno[3,4-c][1,2 , 5] the copolymer of thiadiazole, its structural formula is as follows:

[0059]

[0060] In the formula: n is an integer between 1-100.

[0061] The preparation steps of this copolymer are as follows:

[0062] 1. 5,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) thieno[3,4-c][1,2,5] Synthesis of Thiadiazoles

[0063] See Example 1 for its preparation.

[0064] Two, the synthesis of 5-(9-methylcarbazole)-15-(9-docosylcarbazole) porphyrin

[0065]

[0066] Set up an anhydrous and oxygen-free device, weigh the intermediate 2-aldehyde-9-methylcarbazole (0.21g, 1mmol), 2-aldehyde-9-docosylcarbazole 0.65g (ie 1mmol), di Dissolve 0.30 g (ie 2 mmol) of pyrromethane in 250 ml of dichloromethane, blow nitrogen gas for 30 min, add 2 ml of trifluoroacetic acid into a syringe, stir at 100 °C for 1 h, then add 1.82 g of dichlorodicyanobenzoquinone (DDQ) ( 8mmol), continu...

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Abstract

The invention belongs to the field of photoelectron materials and discloses a carbazole porphyrin-thienothiadiazole copolymer. The copolymer has a structure formula (I); in the formula (I), n is an integral between 1 and 100, and R1 and R2 are identical or different hydrogen or C1-C32 alkyl groups. The invention also discloses a preparation method and application of the carbazole porphyrin-thienothiadiazole copolymer. According to the invention, since long-chain alkyl groups are introduced in the carbazole porphyrin-thienothiadiazole copolymer, the dissolubility of the material is improved; and simultaneously, the introduction of the long-chain alkyl groups is beneficial to filming machining, and the application range of the carbazole porphyrin-thienothiadiazole copolymer in the fields ofpolymer solar batteries and the like is broadened.

Description

technical field [0001] The invention relates to a copolymer, in particular to a carbazole-containing porphyrin-thienothiadiazole copolymer. [0002] The invention also relates to the preparation method and application of the carbazole-containing porphyrin-thienothiadiazole copolymer. Background technique [0003] The preparation of low-cost and high-efficiency solar cells using cheap materials has always been a research hotspot and difficulty in the field of photovoltaics. Due to the complex production process and high cost of silicon cells currently used on the ground, their application is limited. In order to reduce the cost of batteries and expand the application range, people have been looking for new solar cell materials for a long time. Organic semiconductor materials have attracted much attention due to the advantages of readily available raw materials, low cost, simple preparation process, good environmental stability, and good photovoltaic effect. Since 1992, N.S...

Claims

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Application Information

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IPC IPC(8): C08G61/12C07D519/00C07D513/04C07D487/22C09K11/06H01L51/46H01L51/54H01L51/30
CPCY02E10/549Y02E10/50
Inventor 周明杰黄杰刘贻锦
Owner OCEANS KING LIGHTING SCI&TECH CO LTD
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