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Porphyrin copolymer containing benzothiadiazole unit, its preparation method and application

A technology of benzothiadiazole and copolymers, which is applied in the fields of electrical components, semiconductor/solid-state device manufacturing, and electrical solid-state devices, and can solve problems such as low photoelectric conversion efficiency

Inactive Publication Date: 2011-10-05
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

However, so far, the photoelectric conversion efficiency of organic solar cells is still much lower than that of inorganic solar cells

Method used

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  • Porphyrin copolymer containing benzothiadiazole unit, its preparation method and application
  • Porphyrin copolymer containing benzothiadiazole unit, its preparation method and application
  • Porphyrin copolymer containing benzothiadiazole unit, its preparation method and application

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preparation example Construction

[0034] see figure 1 , the preparation method of above-mentioned porphyrin copolymer containing benzothiadiazole unit comprises the steps:

[0035] S01: respectively provide compounds A, B, C, and D represented by the following structural formulas,

[0036] in,

[0037] R 1 , R 2 , R 3 , R 4 , R 5 , R 6 from C 1 -C 32 the alkyl group;

[0038] S02: In a system containing a catalyst, an oxidizing agent and an organic solvent, the compounds A, B, and C are subjected to a polycondensation oxidation reaction to generate 5,15-bis(9,9-dialkylfluorene)porphyrin;

[0039] S03: In a system containing a catalyst and an organic solvent, 5,15-bis(9,9-dialkylfluorene)porphyrin is subjected to a bromination substitution reaction to generate 5,15-bromo-10,20-bis(9 , 9-dialkylfluorene) porphyrin;

[0040] S04: Under the condition that catalyst and organic solvent exist, carry out Stille coupling reaction with 5,15-dibromo-10,20-two (9,9-dialkylfluorene) porphyrin and compound D, ...

Embodiment 1

[0080] In the copolymer (I) of the present embodiment, R 1 , R 2 , R 3 , R 4 Same as C 8 h 17 , R 5 , R 6 The same as H, its structural formula is as follows:

[0081]

[0082] It can be seen from the structural formula that the porphyrin copolymer containing benzothiadiazole units in Example 1 has a symmetrical bifluorenyl structure, and through this uniform and symmetrical structure, the porphyrin copolymer containing benzothiadiazole units is copolymerized The material has better light-absorbing properties and photoelectric properties. due to R 1 , R 2 , R 3 , R 4 Both use C 8 h 17 , so compounds A and B are both 9,9-dioctyl-2-aldehyde fluorene, so only one kind of raw material is needed, which simplifies the preparation process and reduces the cost, and the yield is high. If it is not such a symmetrical structure, then compounds A and B have different structures, different raw materials need to be obtained, and there are relatively more by-products.

[00...

Embodiment 2

[0101] In the copolymer (II) of this embodiment, R 1 is methyl, R 2 for C 8 h 17 , R 3 for C 10 h 21 , R 4 for C 16 h 33 , R 5 , R 6 The same as H, its structural formula is as follows:

[0102]

[0103] The preparation process is described in detail below.

[0104] Step 1, the preparation of 10-(9-methyl-9-octylfluorene) 20-(9-decyl-9-hexadecylfluorene) porphyrin involves the following reaction formula:

[0105]

[0106] The specific process is as follows: set up an anhydrous and oxygen-free device, weigh the intermediate 9-methyl-9-octylfluorene 0.320g, 9-decyl -9-hexadecylfluorene 0.56g, dipyrromethane 0.30g, dissolved in dichloromethane, blown with nitrogen for 30 minutes, added 2ml of trifluoroacetic acid into the syringe, stirred at room temperature for 3 hours, and then added dichlorodicyano Benzoquinone (DDQ) 1.82g, continue stirring at room temperature for 30 minutes, then add 2ml triethylamine to quench the reaction, concentrate the solvent, filter...

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Abstract

The invention relates to the field of organic material technology, and provides a porphyrin copolymer containing benzothiadiazole unit, which is a copolymer expressed in a structural formula (1). Wherein R1, R2, R3, R4, R5, R6 are selected from alkyl of C1 to C32; n is an integer of 1 to 200. The invention also provides a method for preparing the porphyrin copolymer containing benzothiadiazole unit and an application. The porphyrin copolymer containing benzothiadiazole unit has excellent light stability and heat stability due to a fluorenes porphyrin structure and benzothiadiazole unit. And the benzothiadiazole unit is introduced in the polymer for widening a spectral response range of the polymer.

Description

technical field [0001] The invention belongs to the technical field of organic materials, and in particular relates to a porphyrin copolymer containing benzothiadiazole units, its preparation method and application. Background technique [0002] Today's world economy is mainly based on fossil energy, such as coal, oil and natural gas. However, these non-renewable fossil energy sources are constantly being exhausted. Since the beginning of the 21st century, global energy issues and the ensuing environmental pollution and climate warming have become increasingly prominent and gradually intensified. Solar energy is considered to be one of the most promising renewable energy sources because of its widespread and vast distribution, large amount of resources, no pollution, cleanliness, safety, and easy access. [0003] In order to make full use of the energy irradiated by sunlight, people continue to develop new materials that can absorb sunlight. Among them, inorganic semicondu...

Claims

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Application Information

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