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A-[pi]-A type conjugated semiconductor polymer based on pyridazino pyrroledione, and preparation method thereof

A technology of diketopyridazinopyrrole and conjugated polymers, which is applied in the field of A-π-A conjugated polymer semiconductor materials, and can solve the problems of no organic field effect transistors, etc.

Active Publication Date: 2015-10-07
黄山市开发投资集团有限公司
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  • Abstract
  • Description
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  • 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-[pi]-A type conjugated semiconductor polymer based on pyridazino pyrroledione, and preparation method thereof
  • A-[pi]-A type conjugated semiconductor polymer based on pyridazino pyrroledione, and preparation method thereof
  • A-[pi]-A type conjugated semiconductor polymer based on pyridazino pyrroledione, and preparation method thereof

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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, 5mL 2mol / 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 present invention discloses an A-[pi]-A type conjugated semiconductor polymer based on pyridazino pyrroledione, and a preparation method thereof, wherein the structure formula of the conjugated polymer is defined in the specification, R1 is a C8-C24 alkyl chain, R2 is H or a C6-C12 alkoxy chain, and n is more than or equal to 1. According to the preparation method, a bithiophene-pyridazino pyrroledione dibromo monomer and a benzothiadiazole diboronic acid bis(pinacol)ester monomer are subjected to a Suzuki coupling reaction to prepare the conjugated polymer. According to the present invention, the advantages of the two units such as PPD and benzothiadiazole are combined, and the novel A-[pi]-A type semiconductor conjugated polymer capable of being subjected to solution processing is provided; and the molecule design of the semiconductor conjugated polymer is reasonable, the polymer has strong electron affinity and is expected to exhibit single electron transport property, and the semiconductor polymer can be used for 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 Applications(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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