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Poly (diaryl fluorene ethylene) material, as well as preparation and use method thereof

A technology of vinyl diaryl fluorene and ethylene, which is applied in the field of organic optoelectronic materials, can solve the problems that high-performance polymer optoelectronic materials have not been seen, and achieve the effects of mild monomer synthesis conditions, easy-to-obtain raw materials, and simple preparation

Active Publication Date: 2009-08-12
NINGBO LUMILAN NEW MATERIAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the invention of using vinyl diaryl fluorene as a monomer to prepare high-performance polymer optoelectronic materials has not yet been seen.

Method used

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  • Poly (diaryl fluorene ethylene) material, as well as preparation and use method thereof
  • Poly (diaryl fluorene ethylene) material, as well as preparation and use method thereof
  • Poly (diaryl fluorene ethylene) material, as well as preparation and use method thereof

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preparation example Construction

[0062] In the preparation method of poly(diaryl fluorene vinyl) material, at first by preparing vinyl diaryl fluorene monomer, then carry out free radical polymer preparation, following three examples represent three kinds of different methods of preparing monomer, specific as follows:

[0063] (1) Poly(phenylthienylfluorene vinyl) material

[0064]

[0065] Wherein, step 1. reacts under room temperature, boron trifluoride diethyl ether complex catalyst / dichloromethane; Bromosuccinimide reaction; step ③ preparation of Grignard reagent under anhydrous, anaerobic, nitrogen protection, magnesium / tetrahydrofuran conditions, and then dropwise adding dry N,N-dimethylformamide; step ④ using Wei Tixi Reaction Trityl phosphine bromide and potassium carbonate are dissolved in 1,4-dioxane to change the aldehyde group into a vinyl group; step ⑤ at a temperature of 85°C-95°C, benzoyl peroxide is used as a catalyst / Polyvinyl alcohol is used as a stabilizer, and the phenylthienyl fluo...

Embodiment 1

[0074] Embodiment 1, poly(diphenylfluorene ethylene) material preparation:

[0075] 9-Phenyl-fluoren-9-ol

[0076] 9-phenyl-9H-fluoren-9-ol

[0077] Experimental procedure: Take 0.66ml, 6.3mmol of bromobenzene and 1.506g, 6.3mmol of magnesium to react to generate Grignard reagent, and dissolve it in 50mL of tetrahydrofuran, and react with 1.134g, 6.3mmol of fluorenone at 60°C for 24 hours to form a large amount of white precipitate. Finally add saturated NHCl 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 (90% yield). GC-MS (EI-m / z): 258 (M + ). 1 H NMR (400MHz, CDCl 3 , ppm): δ 7.691-7.672 (d, J=7.6Hz, 2H), 7.406-7.325 (m, 6H), 7.292-7.236 (m, 5H), 2.508 (s, 1H). 13 C NMR (CDCl 3 , ppm): δ 150.658, 143.391, 139.82, 129.339, 128.698, 128.459, ...

Embodiment 2

[0094] Embodiment 2, poly (diphenylamine phenyl fluorene vinyl) material preparation:

[0095] N-phenyl-4-(9-phenyl-fluoren-9-yl)aniline

[0096] N-phenyl-4-(9-phenyl-9H-fluoren-9-yl)benzonamine

[0097] Experimental procedure: Dissolve 1.624g, 6.3mmol of 9-phenyl-fluorene-9-ol and 1.599g, 9.45mmol of diphenylamine in 60ml of dichloromethane according to the equivalent ratio of 1:1.5, and add dropwise 12.6ml of trifluoro Reaction of boron-diethyl ether complex for 30 minutes, adding 20ml of ethanol and 20ml of water to quench the reaction, extracting with dichloromethane (20ml×3), drying and rotary evaporation, purification with petroleum ether silica gel column, and recrystallization with tetrahydrofuran and petroleum ether to obtain the product (97% yield). GC-MS (EI-m / z): 409 (M + ).

[0098] N-(2-chloroethyl)-N-phenyl-4-(9-phenyl-fluoren-9-yl)aniline

[0099] N-(2-chloroethyl)-N-phenyl-4-(9-phenyl-9H-fluoren-9-yl)benzonamine

[0100] Experimental procedure: Mix 6.9ml...

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Abstract

The invention discloses a polymeric (diaryl fluorene ethylene) material, a preparation method and an application method thereof, belong to the scientific and technical field of organic optoelectronic materials, in particular relates to a diaryl fluorine ethylene polymeric material and application of the polymeric material as a host material, a hole transport material, an electron transport material, a switch material and a tricolor luminescent material to the organic electron field, such as organic flash memory devices, photovoltaic cells and organic light emitting display. The polymeric material has the following structure. The polymeric material has the following advantages: (1) raw materials are cheap and the synthetic method is convenient as a monomer is synthesized by a Friedel-Crafts reaction; (2) diaryl fluorene has high thermal stability and vitrification point; (3) main chain of polyethylene has better flexibility and high solubility; and (4) stacking effect of the diaryl fluorene has better optoelectrical activity. Electroluminescent devices prepared from the material of the invention achieve satisfactory results in terms of brightness, luminous efficiency, voltage withstanding stability and the like.

Description

technical field [0001] The invention belongs to the technical field of organic photoelectric materials. It specifically relates to a poly(diarylfluorene vinyl) material and its preparation method, and relates to the application of these materials in the fields of organic electroluminescence, photovoltaic cells, organic electrical storage, organic nonlinear optics, chemical and biological sensing, and organic lasers. Applications. 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.; Burn, P.L.; Holmes, A.B.Nature 1990, 347, 539.] published thin-film organic electroluminescent devices (Organic Light -emitting Diodes) and polymer light-emitting diodes (Polymeric Light-emitting Diodes), organic flat panel display has become another generation of market-oriented display products after liquid crystal display. At the same time, other organic el...

Claims

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Application Information

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IPC IPC(8): C08F12/02C08F12/32C08F24/00C08F26/06C08F28/06C08F26/02
Inventor 黄维解令海殷成蓉赵剑锋邓先宇
Owner NINGBO LUMILAN NEW MATERIAL CO LTD
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