Break-in conjugated branched polymer material and preparation method and uses thereof

A technology of hyperbranched polymers and polymer materials, applied in chemical instruments and methods, luminescent materials, semiconductor/solid-state device manufacturing, etc., to achieve the effect of high glass transition temperature and high thermal stability

Active Publication Date: 2008-04-16
NINGBO LUMILAN NEW MATERIAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Among them, there are only few literature and patent reports on the main chain interruption method, and there are still no literature and patent reports on the interruption of semi-conjugated polymers based on diquaternary carbon atoms.

Method used

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  • Break-in conjugated branched polymer material and preparation method and uses thereof
  • Break-in conjugated branched polymer material and preparation method and uses thereof
  • Break-in conjugated branched polymer material and preparation method and uses thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Example 1, a copolymer material containing 5% of tris(4-(2-bromo-9-phenylfluoren-9-yl)phenyl)amine branched units terminated with pyrene:

[0037] 2-Bromo-9-phenyl-fluoren-9-ol

[0038] 2-bromo-9-phenyl-9H-fluoren-9-ol

[0039] Take bromo-benzene (4.48g, 29mmol) and magnesium Mg (0.58g, 24mmol) to react to generate Grignard reagent, and react with 2-bromofluorenone (3.135g, 12.1mmol) dissolved in tetrahydrofuran (20mL) at 60°C for 24 Hours, a large amount of white precipitate was generated, and finally saturated color NHCl was added 4 Convert Grignard salts to alcohols. After the reaction was completed, extracted with ether, dried and rotary evaporated, and purified on a silica gel column with a mixed solvent of petroleum ether:dichloromethane (3:2) to obtain a slightly pale yellow solid tertiary alcohol (3.70 g, 90%).

[0040] GC-MS (EI-m / z): 334 / 336 (M + ).

[0041] 1 H NMR (400MHz, CDCl 3 , ppm): δ7.657-7.655 (d, J=7.2Hz, 1H), 7.638-7.449 (m, 3H), 7.403-7.35 (...

Embodiment 2

[0061] Example 2, a copolymer material containing 10% of tris(4-(2-bromo-9-phenylfluoren-9-yl)phenyl)amine branched units terminated with pyrene:

[0062] Take tri(4-(2-bromo-9-phenylfluoren-9-yl)phenyl)amine (0.0962g, 0.08mmol), 2,2'-(9,9-di-n-octanefluorene-2, 7-diyl)-bis([1,3,2]dioxaborinane) (0.92mmol) and 2,7-dibromo9,9-dioctylalkanefluorene (0.4387g, 0.8mmol) Mix and dissolve in a mixed solvent of toluene (30mL) and tetrahydrofuran, add catalyst Pd(PPh 3 ) 4 (0.010g, 0.008mmol), avoid light and pass nitrogen, then add K 2 CO 3 (2M, 15mL), reacted under the condition of 75 ℃ for 72 hours, after the reaction, add pyrene boronic acid and catalyst to react for 12 hours, finally, add 1-bromopyrene and catalyst to react for another 12 hours; add hydrazine hydrate (85%) to strongly Stir for 24 hours, extract with toluene, dry and rotary evaporate, and repeatedly reprecipitate by dropping into methanol, and finally use an acetone drawer to obtain a white solid (0.5947g, yiel...

Embodiment 3

[0064] Example 3, a copolymer material containing 15% of tris(4-(2-bromo-9-phenylfluoren-9-yl)phenyl)amine branched units terminated with pyrene:

[0065] Take tris(4-(2-bromo-9-phenylfluoren-9-yl)phenyl)amine (0.0361g, 0.03mmol), 2,2'-(9,9-di-n-octanefluorene-2 ,7-diyl)-bis([1,3,2]dioxaborinane) (0.645mmol) and 2,7-dibromo9,9-dioctylalkanefluorene (0.3291g, 0.6mmol ) are mixed and dissolved in a mixed solvent of toluene (20mL) and tetrahydrofuran, and the catalyst Pd (PPh 3 ) 4 (0.010g, 0.008mmol), avoid light and pass nitrogen, then add K 2 CO 3 (2M, 10mL), reacted under the condition of 75 ℃ for 72 hours, after the reaction, add pyrene boronic acid and catalyst to react for 12 hours, finally, add 1-bromopyrene and catalyst to react for another 12 hours; add hydrazine hydrate (85%) to strongly Stir for 24 hours, extract with toluene, dry and rotary evaporate, repeat reprecipitation by dropping into methanol, and finally use an acetone drawer to obtain a white solid (0.42...

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Abstract

The present invention relates to a conjugation-broken hyperbranched polymer material, a preparation method thereof, and a technology field of the organic photovoltaic material, and specifically to a conjugation-broken hyperbranched polymer material and a preparation method thereof. The material is used in organic active display, organic optical storage, organic photovoltaic cell, organic field effect tube, chemical and biology sensor, organic laser, etc. and the material is a polymeric material with 9, 9-diaryl fluorine as a branched monomer based on triphenylamine. The material has the advantage that synthesization is easy to be achieved, and a special non-planar structure is formed and pi-conjugate chain is broken, and the material has a high thermal stability and glass temperature. Conceivably, the series of materials will be photovoltaic functional materials with a commercialization future.

Description

technical field [0001] The invention belongs to the technical field of organic photoelectric materials. It specifically relates to an interrupted conjugated hyperbranched polymer material and a preparation method thereof, and relates to the application of these materials in organic electroluminescence, organic light storage, organic field effect tubes, organic solar cells, organic nonlinear optics, chemical and biological transmission applications in sensing and organic lasers. technical background [0002] Since 1987, the Tang Research Group of Kodak Company in the United States [Tang, C.W.; Van Slyke, S.A. Appl. Phys. Lett. Marks, R.N.; Mackay, K.; Friend, R.H.; Bum, P.L.; Holmes, A.B.Nature 1990, 347, 539.] published thin-film organic electroluminescent devices (Organic Light -emitting Diodes) and polymer light-emitting diodes (PolymericLight-emitting Diodes), organic flat panel display has become another generation of market-oriented display products after liquid cryst...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/00C09K11/06H01L51/54
CPCC08G83/002C08G83/005
Inventor 黄维解令海
Owner NINGBO LUMILAN NEW MATERIAL CO LTD
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