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Zone structured terpolymer based on monofluoro-substituted benzoheterocycle and application thereof

A terpolymer, heterocycle technology, applied in electrical components, photovoltaic power generation, circuits, etc., to achieve good planarity and rigidity

Inactive Publication Date: 2017-05-31
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] However, for such regioregular conjugated polymers based on asymmetric structure, how to further control the intramolecular charge transfer effect in the main chain and the morphology of the polymer film through appropriate structural design, and then improve the current carrying capacity of the polymer Sub-migration remains poorly reported

Method used

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  • Zone structured terpolymer based on monofluoro-substituted benzoheterocycle and application thereof
  • Zone structured terpolymer based on monofluoro-substituted benzoheterocycle and application thereof
  • Zone structured terpolymer based on monofluoro-substituted benzoheterocycle and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Based on the regioregular terpolymer of indaprodithiophene, dithiophene and 5-fluorobenzo[d][1,2,5]thiadiazole (abbreviated as IFBT-TT)

[0041] The synthetic route is as follows:

[0042]

[0043] (1) 2,7-bis(trimethyltin)-4,9-dihydro-4,4,9,9-hexadecyl-s-indacene[1,2-b:5, Preparation of 6-b']dithiophene (Compound 1)

[0044]Under argon atmosphere, in a 100mL two-necked round bottom flask, 4,9-dihydro-4,4,9,9-hexadecyl-s-indacene[1,2-b:5, 6-b'] Dithiophene (0.5 g, 0.43 mmol) was dissolved in anhydrous tetrahydrofuran (50 mL). Place the two-necked bottles in a cold well, and after the temperature drops to -78°C, slowly drop n-butyllithium (0.9mL, 1.6mol L -1 , hexane solution), the reaction was kept at -78°C and stirred for 15 minutes; the cold well was removed, the temperature of the reaction solution rose to room temperature, the reaction bottle was placed in an oil bath, and after the temperature was heated to 40°C, stirred for 1 hour; subsequently, Add trimeth...

Embodiment 2

[0054] Based on the regioregular terpolymer of indaprodithiophene, bithiophene and 5-fluorobenzo[d][1,2,5]thiadiazole (abbreviated as IFBT-T-T)

[0055] The synthetic route is as follows: (2,7-bis(4-bromo-5-fluoro-7-benzo[c][1,2,5]thiadiazole)-4,9-dihydro-4,4,9 , the preparation of 9-hexadecyl-s-indapro[1,2-b:5,6-b']dithiophene is the same as in Example 1)

[0056]

[0057] In a water-oxygen automatic control glove box, 5,5'-bis(trimethyltin)-2,2'-bithiophene (36mg, 0.074mmol), 2,7-bis(4-bromo-5-fluoro -7-Benzo[c][1,2,5]thiadiazole)-4,9-dihydro-4,4,9,9-hexadecyl-s-indacene[1,2 -b: Preparation of 5,6-b']dithiophene (compound 2, 120mg, 0.074mmol) and tetrakistriphenylphosphine palladium (4.3mg, 0.0037mmol) were added to a 10mL microwave tube, and anhydrous xylene was added (2.5 mL) was dissolved and the silicone cap was sealed. Place the microwave tube in a microwave reactor and set the temperature program: 80°C for 2 minutes, 120°C for 2 minutes, 160°C for 2 minutes, and ...

Embodiment 3

[0060] Based on the regioregular terpolymer of indaprodithiophene, trithiophene and 5-fluorobenzo[d][1,2,5]thiadiazole (abbreviated as IFBT-DTT)

[0061] The synthetic route is as follows: (2,7-bis(4-bromo-5-fluoro-7-benzo[c][1,2,5]thiadiazole)-4,9-dihydro-4,4,9 , the preparation of 9-hexadecyl-s-indapro[1,2-b:5,6-b']dithiophene is the same as in Example 1)

[0062]

[0063] In a water-oxygen self-control glove box, 2,6-bis(trimethyltin)dithieno[3,2-b:2',3'-d]thiophene (39mg, 0.074mmol), 2,7 -Bis(4-bromo-5-fluoro-7-benzo[c][1,2,5]thiadiazole)-4,9-dihydro-4,4,9,9-hexadecyl- s-indapro[1,2-b:5,6-b']dithiophene (compound 2, 120mg, 0.074mmol) and tetrakistriphenylphosphine palladium (4.3mg, 0.0037mmol) were added to 10mL microwave To the tube, anhydrous xylene (2.5 mL) was added to dissolve, and the silica gel cap was sealed. Place the microwave tube in a microwave reactor and set the temperature program: 80°C for 2 minutes, 120°C for 2 minutes, 160°C for 2 minutes, and finally...

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Abstract

The invention discloses a zone structured terpolymer based on monofluoro-substituted benzoheterocycle and application thereof. The zone regular terpolymer is characterized in that a main chain comprises two different electron donor units, the actions of the two electron donor units are different, and the two electron donor units are respectively provided with a dissolving side group and a non-dissolving side group; an electron deficiency unit in the copolymer is of a monofluoro-substituted benzoheterocycle structure, the fluorine atom has stronger electron absorbing property, and the charge transfer function in polymer molecules is greatly promoted; the fluorine atom and the electron donor units form non-bond function, so as to ensure the transmission of carriers of the polymer in the plane and the rigid main chain structure. The zone structured terpolymer based on the monofluoro-substituted benzoheterocycle has great application prospect in the field of preparation of organic solar batteries and organic field effect transistors.

Description

technical field [0001] The invention belongs to the technical field of organic photoelectric materials, and in particular relates to a regioregular terpolymer based on a monofluorine-substituted benzoheterocycle and an application thereof. Background technique [0002] Solution-processable organic semiconductor materials are widely used in organic light-emitting diodes, organic solar cells, and organic field-effect transistors due to their low cost, large area, flexibility, and thinness. In the past five years, the use of donor-acceptor (D-A) type structural units to construct the main chain of conjugated polymers has made great progress in the use of conjugated polymers in organic field-effect transistors. The current reported field-effect mobility has reached 5-10cm 2 / Vs, has surpassed amorphous silicon [Adv.Mater.2014,26,2636-2642; J.Am.Chem.Soc.2014,136,9477-9483]. This type of D-A copolymer has strong intermolecular interactions and electronic coupling in solid films,...

Claims

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Application Information

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IPC IPC(8): C08G61/12H01L51/30H01L51/46H01L51/54
CPCC08G61/123C08G61/126C08G2261/1412C08G2261/124C08G2261/3243C08G2261/149C08G2261/146C08G2261/18C08G2261/92C08G2261/414C08G2261/3246C08G2261/91C08G2261/51H10K85/151Y02E10/549
Inventor 应磊钟文楷黄飞曹镛
Owner SOUTH CHINA UNIV OF TECH
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