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Copolymer containing diketopyrrolopyrrole and naphthalene diimide, and preparation method and application thereof

A technology of naphthalene tetracarboxylic acid diimide and diketopyrrolopyrrole, which is applied in the field of conjugated polymers and its preparation, can solve the problems of low photoelectric conversion efficiency, and achieve the effect of easy control of the reaction and simple process

Inactive Publication Date: 2014-06-18
OCEANS KING LIGHTING SCI&TECH CO LTD +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the photoelectric conversion efficiency of polymer solar cells is much lower than that of silicon solar cells. If the photoelectric conversion efficiency of polymer solar cells can be increased to a level close to commercial silicon solar cells, its market prospect will be very huge

Method used

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  • Copolymer containing diketopyrrolopyrrole and naphthalene diimide, and preparation method and application thereof
  • Copolymer containing diketopyrrolopyrrole and naphthalene diimide, and preparation method and application thereof
  • Copolymer containing diketopyrrolopyrrole and naphthalene diimide, and preparation method and application thereof

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preparation example Construction

[0042] In addition, this embodiment also provides a method for preparing a conjugated polymer containing diketopyrrolopyrrole and naphthalene tetracarboxylic diimide units, the specific steps are as follows:

[0043] Provide compound A and compound B, the structural formula of described compound A is: The structural formula of the compound B is: Among them, R 1 for C 1 ~C 20 Alkyl or R 2 , R 3 and R 4 for H, C 1 ~C 20 Alkyl or C 1 ~C 20 The alkoxyl group, R 5 , R 6 and R 7 for H or C 1 ~C 20 the alkyl group;

[0044] Compound A and Compound B are subjected to a Stille coupling reaction in a catalyst and an organic solvent according to a molar ratio of 1:1 to 2:1, and after separation and purification, the diketopyrrolopyrrole and naphthalene tetraketone containing the following structural formula are obtained: Conjugated polymers of carboxylic acid diimide units:

[0045]

[0046] n is an integer of 1 to 100.

[0047] Preferably, the reaction temperatu...

Embodiment 1

[0062] Compounds of the following structural formula are prepared:

[0063]

[0064] Specifically include the following steps:

[0065]

[0066]

[0067] N 2 Under atmosphere, in 15ml containing 0.1mmol compound Ⅰ 1 Add 1mmol n-octylamine to the propionic acid solution, reflux reaction overnight; cool to room temperature, pour the reaction solution into aqueous sodium hydroxide solution, and extract with chloroform, collect the chloroform phase; remove the chloroform in the chloroform phase, and wash with ethyl acetate The substance obtained; the substance washed with ethyl acetate was dissolved in chloroform, and the resulting mixture was peroxidized to an aluminum oxide chromatographic column to remove excess solvent to obtain solid compound II 1 ; Calculated yield, compound Ⅱ 1 The yield was 52%; the compound II obtained by mass spectrometry 1 , the detection result is: MS (MALDI) m / z: 648 (compound Ⅱ 1 + ).

[0068]

[0069] At -78°C, 100ml contains 2.5m...

Embodiment 2

[0073] Compounds of the following structural formula are prepared:

[0074]

[0075] Specifically include the following steps:

[0076]

[0077]

[0078] in N 2 Under atmosphere, in 15ml containing 0.1mmol compound Ⅰ 2 Add 1mmol of propionic acid solution Reflux reaction overnight; then pour the reaction solution cooled to room temperature into aqueous sodium hydroxide solution, and extract with chloroform, collect the chloroform phase; remove the chloroform in the chloroform phase, and wash the obtained material with ethyl acetate; wash with ethyl acetate The final substance was dissolved in chloroform, and the resulting mixture was peroxide chromatographic column; the excess solvent in the collected product was removed to obtain solid compound II 2 ; Calculated yield, compound Ⅱ 2 The yield was 52%; the compound II obtained by mass spectrometry 2 , the detection result is: MS (MALDI) m / z: 900 (compound Ⅱ 2 + ).

[0079]

[0080] At -78°C, 100ml contains ...

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Abstract

The invention relates to a copolymer containing diketopyrrolopyrrole and naphthalene diimide , and the structural formula is shown in the specification. In the structural formula, n is a natural number between 1 to 100, R1 is C1-C20 alkyl or a structure shown in the specification, R2, R3 and R4 are H, C1-C20 alkyl or C1-C20 alkyloxy, and R5, R6 and R7 are H or C1-C20 alkyl. The above conjugated polymer has the characteristics of wide light absorption scope, high carrier mobility, good solubility and the like, and is applicable to fields of organic solar cells, organic electroluminescence, organic field effect transistor and the like. Additionally, the invention also provides a preparation method of the copolymer containing diketopyrrolopyrrole and naphthalene diimide .

Description

technical field [0001] The invention relates to the technical field of organic semiconductor materials, in particular to a conjugated polymer containing diketopyrrolopyrrole and naphthalene tetracarboxylic diimide units, a preparation method and application thereof. Background technique [0002] 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. Although the traditional silicon solar cell has high efficiency, its production process is complicated and the cost is high, which limits its further application. In order to reduce the production cost of solar cells and expand their application range, people have been looking for new solar cell materials. [0003] Polymer solar cells have attracted much attention due to the advantages of low raw material prices, light weight, good flexibility, simple production process, and large-area flexible preparation. However, the p...

Claims

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Application Information

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IPC IPC(8): C08G61/12C07D519/00H01L51/46H01L51/54H01L51/30
CPCY02E10/549
Inventor 周明杰管榕黄佳乐
Owner OCEANS KING LIGHTING SCI&TECH CO LTD
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