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A-π-a-type conjugated semiconducting polymer based on pyridazinopyrrole diketone and preparation method thereof

A pyridazinopyrrole diketo, conjugated polymer technology, applied in the field of A-π-A type conjugated polymer semiconductor materials, can solve the problem of no organic field effect transistors and the like

Active Publication Date: 2017-11-10
黄山市开发投资集团有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But so far, there is no organic field effect transistor material based on PPD conjugated unit

Method used

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  • A-π-a-type conjugated semiconducting polymer based on pyridazinopyrrole diketone and preparation method thereof
  • A-π-a-type conjugated semiconducting polymer based on pyridazinopyrrole diketone and preparation method thereof
  • A-π-a-type conjugated semiconducting polymer based on pyridazinopyrrole diketone and preparation method thereof

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Experimental program
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preparation example Construction

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

[0028] Preparation of conjugated dithiophene-pyridazinopyrrole diketopic bromide monomers

[0029] The schematic diagram of the synthesis route of conjugated bisthiophene-pyridazinopyrrole diketopic bromide monomer is as follows: figure 2 As shown, the dibromomonomer is prepared by the literature method, and the detailed preparation method can be found in the literature report (Organic Letters, 2014, 16, 6386.).

[0030] Preparation of benzothiadiazole diboronic acid di(pinacol) ester monomer

[0031] The synthetic route of benzothiadiazole diboronic acid bis (pinacol) ester monomer is as follows image 3 shown. For the detailed preparation method, refer to the literature report (European Journal Organic Chemistry, 2006, 21, 4924.).

Embodiment 1

[0032] Embodiment 1, synthetic polymer P1

[0033] The synthetic route of polymer P1 is as follows Figure 4 As shown, the specific steps are: in a 100mL reaction flask, add 0.5mmol dibromine monomer and 0.5mmol diboronic acid bis(pinacol) ester monomer (R 1 and R 2 As shown in Table 1), then add 10mL anhydrous toluene, 5mL2mol / L K 2 CO 3 The solution was replaced with nitrogen for 40 minutes, and a 2% catalyst tris(dibenzylideneacetone)dipalladium was added, using tris(o-methylphenyl)phosphine as a ligand. React at 110°C for 48 hours, cool the reaction to room temperature, add 200mL of methanol to precipitate, filter the solid, use methanol and n-hexane Soxhlet extraction for 24 hours, and then use chloroform Soxhlet extraction for 24 hours, finally rotate the liquid, and precipitate with methanol to obtain polymer.

Embodiment 2-3

[0035] The specific steps are the same as in Example 1: in a 100mL reaction flask, add 0.5mmol dibromine monomer and 0.5mmol diboronic acid bis(pinacol) ester monomer (R1 and R2 are as shown in Table 1), add anhydrous toluene 10mL, 5mL 2mol / L K 2 CO 3Solution, replaced with nitrogen for 40 minutes, added 2% catalyst tris(dibenzylideneacetone) dipalladium, with tris(o-methylphenyl)phosphorus as ligand, reacted at 110°C for 48 hours, cooled to room temperature, added 200mL methanol Precipitation, the solid was extracted with methanol and n-hexane Soxhlet for 24 hours, and then extracted with chloroform for 24 hours. Finally, the liquid was rotary evaporated, and methanol precipitated to obtain polymers P2-P3. The specific structure is shown in Table 1.

[0036] Table 1

[0037]

[0038] In summary, the present invention relates to a semiconducting conjugated polymer based on bisthiophene-pyridazinopyrrole diketone and benzothiadiazole, and the structural feature of the nove...

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Abstract

The invention discloses an A-π-A type conjugated semiconductor polymer based on a diketopyridazinopyrrole and a preparation method thereof. The structural formula of the conjugated polymer is: wherein, R1 is a C8-C24 alkyl chain, and R2 It is H or C6-C12 alkoxy chain, n≥1. The preparation method is to prepare the conjugated polymer through Suzuki coupling reaction by using bisthiophene-pyridazinopyrrole diketopic bromide monomer and benzothiadiazole diboronic acid di(pinacol) ester monomer. The invention combines the advantages of PPD and benzothiadiazole units to provide a novel, solution-processable A-π-A type semiconductor conjugated polymer. The molecular design of the semiconducting conjugated polymer of the present invention is reasonable, the polymer has strong electron affinity, and is expected to show a single electron transport performance, and the semiconducting polymer of the present invention can be applied to organic thin film transistor devices.

Description

technical field [0001] The present invention relates to a solution-processable A-π-A type conjugated polymer semiconductor material, in particular to an A-π-A type conjugated semiconductor polymer based on pyridazinopyrrole diketone and its Preparation. The A-π-A type conjugated polymer has a strong electron affinity, and it is expected to show a single electron transport performance when used in OTFTS. Background technique [0002] In recent years, organic electronic devices based on solution-processable conjugated polymers have become the focus of research due to their advantages such as low weight, low cost, low fabrication temperature, ease of large-area fabrication, and flexibility. In the application of organic solar cells (OPVs) and organic field-effect transistors (OFETs), both n-type and p-type organic semiconductor materials play a vital role, and the design and a common Conjugated semiconducting polymers remain a key challenge. (see literature Kim G., Han A.R.,...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G61/12
Inventor 张国兵郭景华张捷李朋吕国强
Owner 黄山市开发投资集团有限公司
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