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Solution-processible conjugated micro-molecular semiconductor materials based on thiophene pyrrolopyrroledione and semi-indigo

A technology of thiophene diketopyrrolopyrrole and diketopyrrolopyrrole, which is applied in the field of A2-D-A1-D-A2 type conjugated small molecule semiconductor materials, can solve the problems of poor film-forming properties of small molecules and achieve strong The effect of interaction, excellent solubility, and excellent photoelectric performance

Inactive Publication Date: 2020-02-21
HEFEI UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Small molecules have a clear molecular structure and molecular weight, and there is no batch difference problem, but the film-forming performance of small molecules is poor

Method used

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  • Solution-processible conjugated micro-molecular semiconductor materials based on thiophene pyrrolopyrroledione and semi-indigo
  • Solution-processible conjugated micro-molecular semiconductor materials based on thiophene pyrrolopyrroledione and semi-indigo
  • Solution-processible conjugated micro-molecular semiconductor materials based on thiophene pyrrolopyrroledione and semi-indigo

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Embodiment 1: synthesis A2-D-A1-D-A2 type conjugated small molecule semiconductor material M1 (such as figure 2 shown),

[0022] Step 1, Synthesize monomer 1 of conjugated small molecule semiconductor material M1 with reference to literature ((Z)-(Thienylmethylene)oxindole-Based Polymers for High Performance SolarCells.Macromolecules.2016,49,2145-2152.) Synthesis, monomer 2 It can be purchased commercially. The stille reaction is used to synthesize the conjugated small molecule semiconductor material M1, and the brominated monomer 1 (0.063g, 0.162mmol) and the double tinned monomer 2 (0.06g, 0.071mmol) are respectively added to the Schlenk bottle. Solvent toluene (10mL), nitrogen replacement for 20 minutes, then add catalyst Pd 2 (dba) 3 (3mg), Ligand P(o-tol) 3 (4 mg), reacted at 110° C. for 24 hours, cooled to room temperature, added water, extracted with dichloromethane, collected the organic layer, dried, removed the organic solvent, and purified by column chrom...

Embodiment 2

[0023] Embodiment 2: synthesis A2-D-A1-D-A2 type conjugated small molecule semiconductor material M2 (such as image 3 shown)

[0024] Step 2, synthesize the monomer 3 of the conjugated small molecule semiconductor material M2, refer to the literature ((Z)-(Thienylmethylene)oxindole-Based Polymers for High Performance SolarCells.Macromolecules.2016,49,2145-2152.) Synthesis, monomer 2 It can be purchased commercially. The Stille reaction is used to synthesize the conjugated small molecule semiconductor material M2. Other operating methods are the same as in Example 1. Brominated monomer 3 (0.061g, 0.155mmol) and double tinned monomer 4 are respectively added to the Schlenk bottle. (0.06g, 0.071mmol), solvent toluene (10mL), nitrogen displacement 20 minutes, then add catalyst Pd 2 (dba) 3 (3mg), Ligand P(o-tol) 3 (4 mg), reacted at 110° C. for 24 hours, cooled to room temperature, added water, extracted with dichloromethane, collected the organic layer, dried, removed the org...

Embodiment 3

[0025] Embodiment 3: synthesis A2-D-A1-D-A2 type conjugated small molecule semiconductor material M3 (such as Figure 4 shown)

[0026] Step 3, synthesize monomer 5 of the conjugated small molecule semiconductor material M2 by referring to the literature ((Z)-(Thienylmethylene)oxindole-Based Polymers for High Performance SolarCells.Macromolecules.2016,49,2145-2152.) synthesis, monomer 6 It can be purchased commercially. M3 can be synthesized by the Stille method. Specifically, with reference to Example 1, the Suzuki method is used for synthesis. In the Schlenk bottle, brominated monomer 5 (0.116g, 283mmol) and boroester monomer 6 (0.1g , 0.129mmol), solvent toluene (10mL), sodium carbonate aqueous solution (2M, 2mL), nitrogen replacement for 20 minutes, then add catalyst Pd 2 (dba) 3 (3mg), Ligand P(o-tol) 3 (4 mg), stirred rapidly, reacted at 110°C for 24 hours, cooled to room temperature, added water, extracted with dichloromethane, collected the organic layer, dried, rem...

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Abstract

The invention discloses novel A2-D-A1-D-A2 type conjugated micro-molecular semiconductor materials taking pyrrolopyrroledione and a semi-indigo unit as acceptors (A1 and A2) and a bithiophene bridge as a donor (D). The novel conjugated micro-molecular semiconductor materials have the advantages of clear molecular structure and molecular weight, no batch difference, solution processing characteristic and good film-forming property. Organic thin film transistor devices show that semiconductors with the structure have an electron transmission characteristic, and the spectrum absorption covers visible light and extends to the near-infrared field, so that the materials can be processed by a solution, and have wide application prospects in the organic electronic fields of organic thin film transistors, organic photovoltaics, organic thermoelectricity and the like.

Description

technical field [0001] The present invention relates to the technical field of solution-processed organic small molecule semiconductor materials, in particular to a kind of A2 based on diketopyrrolopyrrole and semiindigo units as acceptor units (A1 and A2), and bithiophene as donor unit (D) -D-A1-D-A2 type conjugated small molecule semiconductor material. Background technique [0002] In recent years, due to their unique advantages, organic conjugated molecules have attracted widespread attention from academia and industry at home and abroad, making organic conjugated materials used in related optoelectronic devices, such as organic light-emitting diodes, organic photovoltaic cells, and organic thin-film transistors. It has been developed rapidly. The power of light-emitting diodes of white light conjugated materials has exceeded 50lm / W, the energy conversion efficiency of organic photovoltaic cells has exceeded 17%, and the mobility of organic field-effect transistors has e...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D519/00H01L51/00H10K99/00
CPCC07D519/00H10K85/655H10K85/657H10K85/6572Y02E10/549
Inventor 张国兵余豪陈瑞坤
Owner HEFEI UNIV OF TECH
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