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Conjugate small molecule material based on pyridine pyrrolidone and diindene dithiophene condensed ring and preparation method of condensed ring

A pyridinepyrrole diketone and dithiophene technology, which can be used in semiconductor/solid-state device manufacturing, photovoltaic power generation, electrical components, etc., and can solve problems such as poor film-forming performance

Inactive Publication Date: 2018-12-25
HEFEI UNIV OF TECH
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  • Application Information

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Problems solved by technology

However, the film-forming properties of small organic molecules are poor. At present, high-performance small-molecule semiconductor materials are basically obtained by vacuum evaporation or by introducing polymers to assist film formation.

Method used

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  • Conjugate small molecule material based on pyridine pyrrolidone and diindene dithiophene condensed ring and preparation method of condensed ring
  • Conjugate small molecule material based on pyridine pyrrolidone and diindene dithiophene condensed ring and preparation method of condensed ring
  • Conjugate small molecule material based on pyridine pyrrolidone and diindene dithiophene condensed ring and preparation method of condensed ring

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Experimental program
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Effect test

Embodiment 1

[0020] Embodiment 1: Synthesis of small molecule material M4

[0021] The physical diagram of the synthesis path of the small molecule material M4 is as follows figure 2 As shown, the specific steps are: in a 100mL reaction flask, add 1.6mmol of tin monomer of diindenodithiophene fused ring, 2.3 times of brominated monomer of diketopyridinepyrrole, add anhydrous toluene (also can be anhydrous water (tetrahydrofuran, chlorobenzene) 20mL, replaced under nitrogen atmosphere for 30 minutes, added 2% catalyst (Pd 2 dba 3 ) and 8% ligand (P(o-toly) 3 ), reacted at 105°C for 18 hours, cooled the reactant to room temperature, added 50mL of water and 30mL of dichloromethane for extraction, extracted three times, collected the organic layer, dried over anhydrous magnesium sulfate, then suction filtered, rotary evaporated the organic solvent, and finally used petroleum Ether: diethyl ether: dichloromethane (5:1:1) to purify the product to obtain the small purple molecule M4 (120mg, 5...

Embodiment 2

[0025] Using other monomers to synthesize other series of small molecule materials, the specific steps are the same as in Example 1: add 1.6mmol of tin monomer of bisindenodithiophene condensed ring in a 100mL glass reaction bottle, and 2.3 times the bromination of diketopyridinepyrrole Monomer, add 20 mL of anhydrous toluene (also can be anhydrous tetrahydrofuran, chlorobenzene), replace under nitrogen atmosphere for 30 minutes, add 2% catalyst (Pd 2 dba 3 ) and 8% ligand (P(o-toly) 3 ), reacted at 105°C for 18 hours, cooled the reactant to room temperature, added 50mL of water and 30mL of dichloromethane for extraction, extracted three times, collected the organic layer, dried over anhydrous magnesium sulfate, then suction filtered, rotary evaporated the organic solvent, and finally used petroleum Ether: diethyl ether: dichloromethane (5:1:1) to purify the product to obtain a small purple molecule whose structural formula is shown in Table 1.

[0026] The structural formul...

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Abstract

The invention discloses a conjugate small molecule material based on pyridine pyrrolidone and a diindene dithiophene condensed ring and a preparation method of the condensed ring. The structural formula of the small molecule material is as shown in the specification, R1 is a CnH2(n+1) alkyl chain, n>=1, and R2 is a CnH2(n+1) alkyl chain, n>=1, or R2 is an alkyl benzene chain (as shown in the specification). According to the preparation method of the small molecule material, pyridine pyrrolidone bromination monomers and diindene dithiophene condensed ring tin monomers are prepared under Stillereaction conditions to form the small molecule material. According to strong electron deficiency characteristics of the pyridine pyrrolidone and donor and plane structure characteristics of the diindene dithiophene condensed ring, and a soluble small molecule semiconductor material is provided and expected to be applied to the fields of organic thin film transistors, organic photovoltaic and otherorganic electronics.

Description

technical field [0001] The invention relates to the field of organic small molecule semiconductor materials, in particular to a conjugated small molecule material based on diketopyridinepyrrole and bisindenodithiophene condensed rings and a preparation method thereof. Background technique [0002] In recent years, the research on the application of organic semiconductor materials in organic thin film transistors, organic photovoltaics and organic light-emitting diodes has attracted more and more attention. Organic semiconductor materials are divided into polymers and organic small molecules. Polymers have good film-forming properties and performance High advantage, but poor batch-to-batch repeatability. Compared with polymers, small molecules have the advantages of fixed structure, good reproducibility, and excellent crystallization properties, which make small organic molecules have broad application prospects. However, the film-forming performance of small organic molecul...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D519/00H01L51/00H10K99/00
CPCC07D519/00H10K85/6576H10K85/6572Y02E10/549
Inventor 张国兵赵耀
Owner HEFEI UNIV OF TECH
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