Rigid conjugated polymer based on benzodifurandione and derivatives thereof as well as preparation and application of rigid conjugated polymer

A technology of conjugated polymers and derivatives, applied in the field of organic functional materials and organic electronics, can solve the problems of n-type rigid conjugated polymers with less structure and poor performance

Inactive Publication Date: 2020-03-06
PEKING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0019] Aiming at the problem that the current n-type rigid conjugated polymer has less structure and poor performance, the purpose of the present invention is to use benzodifurandione and its derivatives as the key carbon-carbon double bond bridging unit to provide a A method for preparing n-type rigid conjugated polymers by condensation reaction, which is applied to organic field-effect transistors and organic thermoelectric materials for the first time

Method used

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  • Rigid conjugated polymer based on benzodifurandione and derivatives thereof as well as preparation and application of rigid conjugated polymer
  • Rigid conjugated polymer based on benzodifurandione and derivatives thereof as well as preparation and application of rigid conjugated polymer
  • Rigid conjugated polymer based on benzodifurandione and derivatives thereof as well as preparation and application of rigid conjugated polymer

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Embodiment 1

[0075]

[0076] Synthesis process of Compound 1: Add 2,5-dihydroxyterephthalic acid (1.0 g, 4.4 mmol) to dry toluene (50 mL), and then add acetic anhydride (10 mL). After mixing, they were heated to 100° C. for 5 hours, and then the solvent was removed under reduced pressure, and recrystallized from toluene to obtain a white solid (0.79 g, yield 94%). 1 H NMR (CDCl 3 ,400MHz,ppm):δ7.07(s,2H),3.78(s,4H). 13 C NMR (CDCl 3 ,100MHz,ppm): δ173.3,150.9,123.3,107.7,33.5.EI-MS(M + ) calc.: 190.03; found: 190.

Embodiment 2

[0078]

[0079] The synthesis process of compound 2: add benzodithiophene (0.45g, 2.34mmol) to dry tetrahydrofuran (40mL), cool down to -78°C, slowly add n-butyllithium (1.6M n-hexane solution, 5.85mL, 9.36mmol), and after stirring for 2 hours, tributylboronate (3.2mL, 12mmol) was added, returned to room temperature, and stirred for 8 hours. Add 100 mL of 1M hydrochloric acid to quench the reaction, filter, dissolve the filter residue with sodium hydroxide solution, and then add 1M hydrochloric acid until the solid no longer precipitates. Filter and dry the solid (0.49g, 80% yield) for the next reaction.

Embodiment 3

[0081]

[0082] The synthesis process of compound 3: Add compound 2 (0.51 g, 1.80 mmol) to tetrahydrofuran (50 mL), then add 1 mL of hydrogen peroxide (30%) solution, stir at room temperature for 1 hour, remove the solvent to obtain a solid, wash with water and methanol respectively, Compound 3 (0.3 g, yield 60%) was obtained. 1 H NMR (CDCl 3 ,400MHz,ppm):δ7.29(s,2H),3.99(s,4H).

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Abstract

The invention discloses a rigid conjugated polymer based on benzodifurandione and derivatives thereof as well as preparation and application of the rigid conjugated polymer. The rigid conjugated polymer is formed by polymerizing benzodifurandione derivatives and aromatic system monomers containing two isatin or derivative fragments thereof through aldol condensation reaction, and the preparation method is low in price, green and efficient; the benzodifurandione and the aromatic skeleton take carbon-carbon double bonds as bridges, so that the energy level of the lowest unoccupied orbit of the polymer and the characteristic of energy disorder are effectively reduced, and the intra-chain transmission of carriers, the delocalized length of polarons and the interaction between polymer chains are enhanced; the electron mobility, the conductivity and the air stability of the organic electronics material are obviously improved, and the material can be widely applied to the field of organic electronics, including organic solar cells, organic light emitting diodes, organic field effect transistors, organic thermoelectricity and the like.

Description

technical field [0001] The invention relates to a class of rigid conjugated polymers based on benzodifurandione and derivatives thereof and a preparation method thereof, as well as applications as organic semiconductor materials and organic thermoelectric materials, belonging to the fields of organic functional materials and organic electronics. Background technique [0002] The structure of conjugated polymers contains a conjugated system composed of delocalized π electrons, so it exhibits special optical, electrical, magnetic and other properties, which has attracted widespread attention from scientists and has become a popular topic in the past two decades. research hotspots. The synthesis and functional device-based research of organic conjugated molecules involves many disciplines such as chemistry, physics, electronics, and materials science. It is a frontier field of interdisciplinary research, full of vitality and opportunities, and is also one of the important direc...

Claims

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Application Information

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IPC IPC(8): C08G61/12H01L35/24
CPCC08G61/125C08G61/124C08G2261/124C08G2261/1412C08G2261/18C08G2261/3241C08G2261/3242C08G2261/92H10N10/856
Inventor 裴坚卢阳王婕妤雷霆余子迪
Owner PEKING UNIV
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