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A kind of semiconducting conjugated polymer and its synthesis method

A technology of conjugated polymers and semiconductors, applied in the direction of organic chemistry, can solve the problems of low energy level, unfavorable electron injection and stable transport, and less electron transport materials, and achieve the effect of low unoccupied orbital energy level

Active Publication Date: 2016-08-17
黄山市开发投资集团有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, most of the reported D-A conjugated polymer materials are hole-transporting materials (p-type) and very few electron-transporting materials (n-type)
This is mainly because the lowest unoccupied orbital (LUMO) energy level of the D-A conjugated polymer is low enough (less than -4.0 eV), which is not conducive to electron injection and stable transport.

Method used

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  • A kind of semiconducting conjugated polymer and its synthesis method
  • A kind of semiconducting conjugated polymer and its synthesis method
  • A kind of semiconducting conjugated polymer and its synthesis method

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preparation example Construction

[0027] The preparation method of each monomer is described as follows:

[0028] Preparation of (thienyl)pyrrolopyrrole-diketopinacol diboron monomer

[0029] (Thienyl) pyrrolopyrrole-diketone pinacol diboron monomer synthetic route schematic diagram as figure 2 As shown, the detailed preparation method can be found in literature reports (Advance Materials, 2013, 25, 5467-5472.).

[0030] Preparation of (2-oxindol-3-ylidene)benzodifuran-dione dibromomonomer

[0031] (2-oxindol-3-ylidene) benzodifuran-diketone dibromomonomer synthetic route such as figure 2 shown. For the detailed preparation method, please refer to the literature report (Chemical Communication, 2013, 49, 3790-3792.).

Embodiment 1

[0032] Embodiment 1, synthetic polymer P 1

[0033] Polymer P 1 The synthetic route of image 3 Shown, concrete steps are: in 100mL reaction bottle, add 0.5mmol bistin monomer and 0.5mmol bibromine monomer (R 1 and R 2 As shown in Table 1), then add 10mL toluene, replace with nitrogen for 40 minutes, add 2.5mmol of K 3 PO 4 2 mL of aqueous solution, 2% catalyst tris(dibenzylideneacetone) dipalladium, and tris(o-methylphenyl)phosphorus as a ligand, reacted at 90°C for 24 hours, cooled the reaction to room temperature, added 200 mL of methanol for precipitation, The solid was filtered, extracted by Soxhlet with methanol and n-hexane for 24 hours, and then extracted by Soxhlet with chloroform for 24 hours. Finally, the liquid was rotary evaporated, and methanol precipitated to obtain a black polymer.

Embodiment 2-3

[0035] The specific steps are the same as in Example 1: add 0.5 mmol of bistin monomer and 0.5 mmol of bis-bromine monomer (R1 and R2 are shown in Table 1) in a 100 mL reaction flask, add 10 mL of toluene, replace with nitrogen for 40 minutes, and then add 2.5 mmol K 3 PO 4 2 mL of aqueous solution, 2% catalyst tris(dibenzylideneacetone) dipalladium, and tris(o-methylphenyl)phosphorus as ligand, reacted at 90°C for 24 hours, cooled to room temperature, added 200 mL of methanol to precipitate, solid Soxhlet extraction with methanol and n-hexane for 24 hours, and then Soxhlet extraction with chloroform for 24 hours, and finally the liquid was rotary evaporated, and methanol precipitated to obtain black polymers P2-P3, the specific structure of which is shown in Table 1.

[0036] Figure 4 The absorption spectrum of polymer P1 is given, and the absorption peak covers visible light and extends to the near-infrared region.

[0037]In summary, the novel semiconductor conjugated p...

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Abstract

The invention discloses a solution-processable polymer semiconductor material, in particular a (thienyl)pyrrolopyrrole-diketone and (2-oxindole-3-ylidene)benzodifuran-dione Semiconducting conjugated polymers of ketones and their preparation. The invention relates to a synthesized novel semiconductor conjugated polymer with a wide absorption peak, covering visible light and even extending to the near-infrared region, and having a low LUMO energy level, which can replace PCBM as a photovoltaic acceptor material and be used in the field of organic photovoltaics. With the introduced side chain as a solubilizing alkyl chain, the conjugated semiconducting polymer prepared by the invention can be processed in solution, and has certain application prospects in the fields of organic thin film transistors and organic photovoltaics.

Description

technical field [0001] The invention relates to the field of conjugated polymer synthesis, and relates to a novel semiconductor conjugated polymer and a synthesis method thereof. Background technique [0002] Conjugated polymers are expected to be widely used in organic thin film transistors due to their light weight, low cost, and flexibility. At present, the most studied conjugated polymers are donor-acceptor (D-A) conjugated polymers, which is due to the push-pull interaction of donor and acceptor in D-A conjugated polymers, which enhances intramolecular and intermolecular interactions. The force greatly improves the charge transport performance. Devices made with D-A conjugated polymers now have hole mobility exceeding 10 cm 2 V -1 the s -1 . However, most of the reported D-A conjugated polymer materials are hole-transporting materials (p-type), while electron-transporting materials (n-type) are very few. This is mainly because the lowest unoccupied orbital (LUMO) ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G61/12C07D519/00
Inventor 张国兵李朋郭景华吕国强
Owner 黄山市开发投资集团有限公司
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