Novel benzo[b]thieno[3,2-b]benzo[b]thiophene disulfone monomer as well as copolymer and application of novel benzo[b]thieno[3,2-b]benzo[b]thiophene disulfone monomer

A technology of thiophene disulfone and 2-b, which is applied in the field of new polymers, can solve the problems of limiting the development of conjugated polymers, fewer types of acceptor units, and high LUMO, and achieves narrow absorption band gaps and unaffected yields , mild effect

Inactive Publication Date: 2016-07-20
WUHAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] At present, there are many kinds of high-efficiency donor units in efficient conjugated polymers, but the development of conjugated polymers is largely limited due to the few types of acceptor units.
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Method used

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  • Novel benzo[b]thieno[3,2-b]benzo[b]thiophene disulfone monomer as well as copolymer and application of novel benzo[b]thieno[3,2-b]benzo[b]thiophene disulfone monomer
  • Novel benzo[b]thieno[3,2-b]benzo[b]thiophene disulfone monomer as well as copolymer and application of novel benzo[b]thieno[3,2-b]benzo[b]thiophene disulfone monomer
  • Novel benzo[b]thieno[3,2-b]benzo[b]thiophene disulfone monomer as well as copolymer and application of novel benzo[b]thieno[3,2-b]benzo[b]thiophene disulfone monomer

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0043] 1. Compound 1 The preparation process is as follows:

[0044] Take a 250mL double-necked flask, dissolve 3-iodomethoxy (52g, 222.2mmol) in 160mL of acetic acid, and after dissolving, add Br 2 (14.82mL, 288.9mmol, 1.3equiv) was added dropwise, the tail gas was absorbed with NaOH solution, and stirred at room temperature for 24h; after the reaction was completed, 10% NaOH solution was slowly added to the resulting solution to remove acetic acid, and then dichloromethane was added to it, Extract with water and saturated sodium chloride solution three times, collect the organic layer, dry with anhydrous sodium sulfate, after precipitation, carry out column chromatography with petroleum ether, obtain 54.1g of oily liquid, the yield is 80%, which is the target product , denoted as compound 1. NMR 1 HNMR (500MHz, CDCl 3 )δ3.82(s,3H),6.75(d,J=5.0Hz,H),7.13(d,J=4.0Hz,H),7.44(d,J=10Hz,H), it can be known that the target compound 1.

[0045] 2. Compound 2 The preparation ...

Embodiment 1

[0051] 1. Compound 4 Preparation, the reaction formula is as follows:

[0052]

[0053] with R 1 Taking 2-ethylhexyl as an example, in a 100mL double-necked bottle, compound 3 (4.1g, 10.0mmol), Pd(PPh 3 ) 2 Cl 2 (210mg, 6% equiv), CuI (190mg, 10% equiv), anhydrous and anaerobic treatment, under the protection of nitrogen, inject 30mL of anhydrous toluene, after dissolving, add DBU (9.0mL, 6equiv), three Methylsilane (0.75mL, 0.5equiv) and distilled water (0.1mL, 40%equiv) were reacted under a complete foil cover, stirred at room temperature, and reacted overnight to obtain a crude product solution of compound 4.

[0054] Add dichloromethane to the crude product solution of compound 4, extract it with distilled water three times, collect the organic layer; then dry it with anhydrous sodium sulfate, and precipitate it; then use petroleum ether: dichloromethane = 8:1 for column chromatography , to obtain an oily liquid with a yield of 80%, which is the refined compound 4...

Embodiment 2

[0071] Polymer P1 The preparation, reaction formula is as follows:

[0072]

[0073] Weigh compound 7 obtained in Example 1 (0.211g, 0.20mmol), 2,5-bis(trimethyltin-based)thiophene (that is, Ar is group a) (82.4mg, 0.2mmol), tris(dibenzyl Dipalladium (5.494g, 3% equiv) and tris(o-methylphenyl)phosphorus (10.944g, 18% equiv) were respectively added to a 50mL single-necked bottle, vacuumized, and 8mL of anhydrous toluene were added , Refluxed for 48h to obtain the crude product of polymer P1.

[0074] Purification: After the thick product of polymer P1 is cooled to room temperature, it is slowly added dropwise to 40mL of anhydrous methanol (dropping while stirring). Dichloromethane, chloroform and toluene were extracted, and the obtained toluene extract was concentrated; then 6 mL of methanol was added to the concentrated toluene extract, and 46 mg of solid was obtained by suction filtration and vacuum drying, with a yield of 75%, which was polymer P1 . Gel permeation ch...

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Abstract

The invention belongs to the field of synthesis of organic compounds, relates to a novel polymer applied to the field of organic semiconductor materials, and in particular relates to a benzo[b]thieno[3,2-b]benzo[b]thiophene disulfone monomer and a copolymer of the benzo[b]thieno[3,2-b]benzo[b]thiophene disulfone monomer. The benzo[b]thieno[3,2-b]benzo[b]thiophene disulfone monomer is a highly-symmetrical heteroatom-containing compound; sulfone is a strong electron withdrawing group and has very good planeness, so that the monomer can be used as a very good small-molecular acceptor material and can be applied to organic solar cells; the monomer has a very good luminous effect, so that the monomer can also be applied to light-emitting diodes.

Description

technical field [0001] The invention belongs to the field of organic compound synthesis, and the invention relates to a novel polymer used in the field of organic semiconductor materials, in particular to a novel benzo[b]thieno[3,2-b]benzo[b]thiophene Disulfone monomers and their copolymers. Background technique [0002] Organic semiconductor optoelectronic devices, including organic field-effect transistors, organic light-emitting diodes, organic photovoltaic cells, organic xerography, organic lasers, and organic biosensors, have been widely used due to their advantages such as low price, light weight and portability, and easy large-area processing. development and gradually move towards industrialization. In the past ten years, through the design of the molecular structure of materials and the optimization of devices, organic semiconductor devices have also been developed rapidly. However, compared with inorganic semiconductor materials, organic Semiconductor materials s...

Claims

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Application Information

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IPC IPC(8): C08G61/12C07D495/04
CPCC07D495/04C08G61/126C08G2261/124C08G2261/1412C08G2261/3142C08G2261/3223C08G2261/3243C08G2261/354C08G2261/592C08G2261/91C08G2261/95
Inventor 尤为高建宏肖生强詹春
Owner WUHAN UNIV OF TECH
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