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Fluorene copolymer containing thiophene and pyrrolopyrrole units, preparation method and application thereof

A diketopyrrolopyrrole copolymer technology, which is applied in the field of preparation of fluorene copolymers containing thiophene and pyrrolopyrrole units, can solve the problems of solar radiation spectrum mismatch and low photoelectric conversion efficiency of organic solar cells, and achieve Improved stability, improved solubility and processability, and high yield effects

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

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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 one of the major constraints is the mismatch between the spectral response of organic semiconductor devices and the spectrum of solar radiation.

Method used

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  • Fluorene copolymer containing thiophene and pyrrolopyrrole units, preparation method and application thereof
  • Fluorene copolymer containing thiophene and pyrrolopyrrole units, preparation method and application thereof
  • Fluorene copolymer containing thiophene and pyrrolopyrrole units, preparation method and application thereof

Examples

Experimental program
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preparation example Construction

[0033] Preparation of fluorene monomers

[0034] Fluorene monomer B 1 The preparation method is shown in the following formula:

[0035]

[0036] In the formula, R 1 and R 2 Same or different as H or C 1 ~C 20 of alkyl.

[0037] At a temperature of -100 to -25°C, 2,7-dibromo-9,9-dialkylfluorene A 1 Add n-butyllithium to the organic solvent in a molar ratio of 1.0:2.0~4.0, then add 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane , and its dosage is calculated as A in terms of moles 1 2.0 to 4.0 times of that, reacted for 24 to 48 hours to obtain product B1, namely 2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolyl)- 9,9-Dialkylfluorenes. The organic solvent used in this reaction is preferably tetrahydrofuran, diethyl ether, dichloromethane, chloroform or ethyl acetate and the like.

[0038] Preparation of thiophene monomers

[0039] Thiophene monomer B 2 The preparation is shown in the following formula:

[0040]

[0041] In the formula, R 9 , R 10 same or...

Embodiment 1

[0059] Embodiment 1, the fluorene copolymer containing thiophene and diketopyrrolopyrrole units, its chemical formula is as follows:

[0060]

[0061] In the formula, x=0.5, y=0.5, n=27.

[0062] One, preparation of fluorene monomer 2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolyl)-9,9-dimethylfluorene, which The chemical formula is as follows:

[0063]

[0064] Under the condition of -100℃ and nitrogen protection, add 20.00mL of n-butyllithium solution with a concentration of 1.00M to a reaction flask containing 3.52g of 2,7-dibromo-9,9-dimethylfluorene and 100mL of tetrahydrofuran After stirring for 2 hours, slowly add 4.17mL 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane dropwise, return to room temperature and continue stirring React for 24 hours. After the reaction was completed, the reaction solution was poured into water, extracted with ether, dried over anhydrous magnesium sulfate, removed by rotary evaporation and column chromatography to obtain a solid p...

Embodiment 2

[0088] Embodiment 2, the fluorene copolymer containing thiophene and diketopyrrolopyrrole units, its chemical formula is as follows:

[0089]

[0090] In the formula, x=0.5, y=0.5 n=41.

[0091] One, preparation of fluorene monomer 2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolyl)-9,9-dimethylfluorene, which The chemical formula is as follows:

[0092]

[0093] The preparation steps are detailed in Example 1.

[0094] Two, prepare thiophene monomer 2,5-dibromo-3,6-dimethylthieno[3,2-b]thiophene, its chemical formula is as follows:

[0095]

[0096] ① Preparation of thiophene raw material 3,6-dimethylthieno[3,2-b]thiophene, its chemical formula is as follows:

[0097]

[0098] Add 12.00 g of 3,6-dibromo-thieno[3,2-b]thiophene and 132 mg (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) chloride into the Place in a 100mL vial with a stir bar, seal it, and flush it with nitrogen. Then 30 mL of tetrahydrofuran and 50 mL of tetrahydrofuran solution containing 1.0 M...

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Abstract

The invention discloses fluorine copolymer containing thiophene and pyrrole-pyrrole units and a preparation method as well as application thereof. The polymer is a compound which has a general formula shown in the specification, wherein R1, R2, R3, R4, R5, R6, R7, R8, R9 and R10 are uniformly or differently expressed as H or C1-C20 alkyl groups; x and y meet the requirements that x+y is equal to 1, x is more than 0 and y is more than 0; and n is an integer of 1-200. The preparation method comprises the following step of: performing suzuki reaction on a dibromo product of a fluorine compound or a thiophene compound and a dibromo product of a pyrrole-pyrrole-dione compound serving as monomer raw materials to obtain the fluorine copolymer containing thiophene and pyrrole-pyrrole units. The fluorine copolymer containing thiophene and pyrrole-pyrrole units is used as an organic semiconductor material, and has the advantages of high matching degree with sunlight emission spectrum, capability of increasing photoelectric conversion efficiency, wide application, mild conditions of synthesis method and easiness in control.

Description

technical field [0001] The invention relates to the technical field of polymer materials, in particular to a polymer, its preparation method and its application, more specifically, to a fluorene copolymer containing thiophene and pyrrolopyrrole units, its preparation method and its application. 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 ...

Claims

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Application Information

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