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Triphenylamine unit porphyrin copolymer as well as preparation method and application thereof

A technology of triphenylamine and copolymer, applied in the field of triphenylamine unit porphyrin copolymer and its preparation, can solve the problems of low conversion efficiency of inorganic solar cells, low collection efficiency of carrier electrodes, mismatched spectral response, etc. The effect of dissolution performance and film-forming processability, good thermal stability and environmental stability, and high photostability

Inactive Publication Date: 2013-03-20
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

Since 1992, N.S.Sariciftci et al. reported on SCIENCE that conjugated polymers and C 60 After the phenomenon of light-induced electron transfer between polymer solar cells, people have invested a lot of research in polymer solar cells and achieved rapid development, but the conversion efficiency is still much lower than that of inorganic solar cells.
The main constraints that limit the improvement of performance are: the spectral response of organic semiconductor materials does not match the spectrum of solar radiation, the relatively low carrier mobility of organic semiconductors, and the low electrode collection efficiency of carriers, etc.

Method used

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  • Triphenylamine unit porphyrin copolymer as well as preparation method and application thereof
  • Triphenylamine unit porphyrin copolymer as well as preparation method and application thereof
  • Triphenylamine unit porphyrin copolymer as well as preparation method and application thereof

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preparation example Construction

[0036] And, the embodiment of the present invention also provides the preparation method of the triphenylamine unit porphyrin copolymer, comprising the following steps:

[0037] 1) Provide compounds A and B represented by the following structural formula respectively, Among them, R 1 , R 2 , R 3 , R 4 from C 1 ~C 32 The alkyl group, where, R 1 , R 2 , R 3 , R 4 preferably C 1 ~C 16 the alkyl group;

[0038] 2) under the condition that in anaerobic environment and catalyzer, organic solvent exist, compound A, B are carried out Suzuki coupling reaction, obtain the triphenylamine unit porphyrin copolymer that general structure formula is (I),

[0039]

[0040] In the formula, n is an integer between 1 and 100,

[0041] The chemical reaction formula of the Suzuki coupling reaction step is as follows:

[0042]

[0043] In the above step (2), the molar ratio of the two reactants of compound A and B in the Suzuki coupling reaction is preferably 1:0.667-1.5, that ...

Embodiment 1

[0057] 10, the preparation of 20-two (9,9-dioctyl fluorene) porphyrin-triphenylamine copolymer, its structural formula is as follows I 1 Shown:

[0058]

[0059] Its preparation steps are as follows:

[0060] 1) The preparation of 4,4'-two (4,4,5,5-tetramethyl-1,3,2-dioxaborolane) triphenylamine, its chemical reaction formula is as follows:

[0061]

[0062] The specific process of preparation is as follows: under the protection of nitrogen, add p-4,4'-dibromotriphenylamine (8.0g, 0.02mol) and 150ml of tetrahydrofuran solvent into the three-necked flask, and then slowly use a syringe under the condition of -78°C. Inject 16.8mL of 0.04mol n-butyllithium oil solution, continue stirring for 2 hours, then inject 2-isopropoxy-4,4,5,5-tetramethyl-1,3 , 2-dioxaborane (8.7mL, 0.04mol), after stirring at room temperature for 12 hours, add saturated aqueous sodium chloride solution (30ml) to terminate the reaction, extract with chloroform, dry over anhydrous sodium sulfate, and ...

Embodiment 2

[0073] The preparation of 10-(9-methyl-9-octyl fluorene)-20-(9-decyl-9-hexadecyl fluorene) porphyrin-triphenylamine copolymer, its structural formula is as follows I 2 Shown:

[0074]

[0075] Its preparation steps are as follows:

[0076] 1) The preparation of 4,4'-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)triphenylamine is detailed in step 1 in Example 1);

[0077] 2) The preparation of 10-(9-methyl-9-octylfluorene)-20-(9-decyl-9-hexadecylfluorene)porphyrin, its chemical reaction formula is as follows:

[0078]

[0079] The specific preparation process is: set up an anhydrous and oxygen-free device, weigh the intermediates 9-methyl-9-octylfluorene (0.32g, 1mmol), 9-decyl-9-hexadecylfluorene (0.56g, 1mmol), dipyrromethane (0.30g, 2mmol), dissolved in 250ml of dichloromethane, passed through nitrogen for 30min, added 2ml of trifluoroacetic acid with a syringe, stirred at 100°C for 1h, then added dichlorodicyanobenzoquinone ( DDQ) (1.82g, 8mmol), then continue to sti...

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Abstract

The invention discloses a triphenylamine unit porphyrin copolymer with a molecular structural general formula (I) in the specification as well as a preparation method and application thereof. In the formula (I), R1, R2, R3 and R4 are selected from alkyls of C1-C32; and n is an integer ranging from 1 to 100. The triphenylamine unit porphyrin copolymer has the advantages of favorable electronic buffer property, photoelectric magnetism, rigidity and flexibility as well as better heat stability, environment stability, dissolution performance and film forming processing property. The preparation method of the triphenylamine unit porphyrin copolymer has the advantages of simplicity, mild reaction conditions, high yield and easiness for operation and control, and is suitable for the field such as solar cells and the like.

Description

technical field [0001] The invention belongs to the technical field of organic compound synthesis, and in particular relates to a triphenylamine unit porphyrin copolymer and 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. Solar cells directly convert sunlight energy into electrical energy, which is a practical and effective way to utilize solar energy. However, currently commercialized solar...

Claims

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Application Information

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