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Carbazole porphyrin-paranaphthalene copolymer and preparation method and application thereof

A carbazole porphyrin and copolymer technology, which is applied in the field of polymer materials, can solve the problems of solar radiation spectrum mismatch, low carrier mobility, low photoelectric conversion efficiency, etc., and achieves high carrier mobility and spectrum. Wide absorption, easy-to-control effects

Inactive Publication Date: 2012-10-31
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 much lower than that of inorganic solar cells, and the main constraints are the mismatch between the spectral response of organic semiconductor devices and the spectrum of solar radiation, and the low carrier mobility of organic semiconductor materials. Wait

Method used

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  • Carbazole porphyrin-paranaphthalene copolymer and preparation method and application thereof
  • Carbazole porphyrin-paranaphthalene copolymer and preparation method and application thereof
  • Carbazole porphyrin-paranaphthalene copolymer and preparation method and application thereof

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preparation example Construction

[0033] Preparation of Carbazole-Containing Porphyrin-Anthracene Copolymer

[0034] Carbazole-containing porphyrin-anthracene copolymer of the present invention can be prepared by the method shown in the following formula:

[0035]

[0036] In the formula, R 1 and R 2 same or different as H or C 1 ~C 32 Alkyl, phenyl, containing one or more of the same or different C 1 ~C 32 In the substituted phenyl group of an alkyl group or an alkoxy group, n is an integer of 1-100.

[0037] Under the protective conditions of inert gases such as nitrogen and argon, add 5,15-dibromo-10,20-alkylcarbazole porphyrin, bisborate anthracene, catalyst and alkali solution into the organic solvent, The Suzuki reaction was carried out at ℃ for 24-72 hours to obtain a carbazole-containing porphyrin-anthracene copolymer. In this reaction, preferably, the catalyst is a mixture of organopalladium and organophosphine ligands, Pd 2 (dba) 3 / P(o-Tol) 3 , Pd(PPh 3 ) 4 or Pd(PPh 3 ) 2 Cl 2 Etc. ...

Embodiment 1

[0040] Example 1 10,20-two (9-octylcarbazole) porphyrin-anthracene copolymer, its chemical formula is as follows:

[0041]

[0042] In the formula, n=37.

[0043] 1. Preparation of 9,10-p-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) anthracene

[0044]

[0045] in N 2 Under the protection of the three-necked flask, 10 g of p-9,10-dibromoanthracene and 250 mL of tetrahydrofuran (THF) solvent were added, and then 2.5 M n-butyllithium (n-BuLi )25.2mL, continue stirring for 2 hours, then inject 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborol with a syringe at -78°C Alkane 13mL, stirred at room temperature for 6-16 hours. The reaction was terminated by adding saturated aqueous sodium chloride solution, extracted with chloroform, dried over anhydrous sodium sulfate and filtered with suction, the filtrate was collected and the solvent was removed by rotary evaporation. Finally, the crude product was separated by silica gel column chromatography using petroleum ether / ethyl...

Embodiment 2

[0058] Example 2 10-(9'-methylcarbazole)-20-(9'-docosylcarbazole) porphyrin-anthracene copolymer, its chemical formula is as follows:

[0059]

[0060] In the formula, n=25.

[0061] 1. Preparation of 9,10-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)anthracene

[0062] The preparation steps are detailed in Example 1.

[0063] Two, the preparation of 5-(9'-methylcarbazole)-15-(9'-docosylcarbazole) porphyrin

[0064]

[0065] Set up an anhydrous and oxygen-free device, weigh intermediate 2-aldehyde-9-methylcarbazole (0.21g, 1mmol), 2-aldehyde-9-docosylcarbazole (0.65g, 1mmol) and di Pyrromethane (0.30g, 2mmol) was dissolved in 250mL of dichloromethane, nitrogen gas was introduced for 30min, 2mL of trifluoroacetic acid was added into the syringe, stirred at 100°C for 1h, then DDQ (1.82g, 8mmol) was added, and the Stir for 30 min, then add 2 mL of pyridine to quench the reaction, concentrate the solvent, filter, collect the filtrate and remove the solvent by rotary evapor...

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Abstract

The invention discloses a carbazole porphyrin-paranaphthalene copolymer and a preparation method and application thereof. The copolymer is a compound having a general formula described in the specification, wherein R1 and R2 identically or differently represent H or C1-C32 alkyl groups, phenyl groups, substituted phenyl groups containing one or more identical or different C1-C32 alkyl or alkoxyl groups, and n is an integral between 1 and 100. The carbazole porphyrin-paranaphthalene copolymer is obtained by a Suzuki reaction which has mild reaction conditions and is easy to control; the band gap of the porphyrin polymer is regulated through introducing carbazole and paranaphthalene groups on a porphyrin ring, thereby obtaining better stability and good film-forming performance, broadening absorption range, improving the utilization of sunlight, improving carrier mobility and improving photoelectric conversion efficiency. The carbazole porphyrin-paranaphthalene copolymer can be widely applied.

Description

technical field [0001] The invention relates to the technical field of polymer materials, in particular to a polymer, its preparation and its application, and more specifically to a carbazole-containing porphyrin-anthracene copolymer. Background technique [0002] Today's world economy is mainly based on fossil energy such as coal, oil and natural gas. However, the reserves of these non-renewable fossil energy are close to depletion. Since the beginning of the 21st century, the global energy crisis and environmental pollution and climate warming caused by the use of energy have become increasingly prominent and gradually intensified. Therefore, it is necessary to seek new renewable energy sources to replace traditional fossil energy sources. Solar energy is considered to be one of the most promising renewable energy sources due to its outstanding advantages such as wide distribution, large amount of resources, no pollution, clean safety, and easy access. Solar cells direct...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G61/12H01L51/00H01S5/36H10K99/00
Inventor 周明杰黄杰刘贻锦
Owner OCEANS KING LIGHTING SCI&TECH CO LTD
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