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Complex whorl aryl fluorene material, preparation and application method thereof

A technology of spiroaryl fluorene and its application method, which is applied in the field of complex spiroaryl fluorene materials and its preparation, can solve problems such as emission spectrum narrowing, and achieve high thermal stability and high glass transition temperature

Active Publication Date: 2009-07-29
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, most of these materials are based on the simple structure of a single chromophore. Due to the special interaction between the two chromophores, effects such as narrowing of the emission spectrum can be produced. However, there is still no invention report in this regard.

Method used

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  • Complex whorl aryl fluorene material, preparation and application method thereof
  • Complex whorl aryl fluorene material, preparation and application method thereof
  • Complex whorl aryl fluorene material, preparation and application method thereof

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preparation example Construction

[0045] The preparation method of complex spiroaryl fluorene compound material I is prepared by Friedel-Crafts reaction and Suzuki reaction catalyzed by boron trifluoride etherate complex. Taking compound material II as an example, the reaction is as follows:

[0046]

[0047] First, prepare the tertiary alcohol tripolyfluorene structural unit, by step (1) Suzuki coupling reaction, it is the carbon-carbon bond coupling reaction that palladium catalyzes alkylfluorene boronic acid and dibromofluorene tertiary alcohol; The consumption of catalyst is 0.1 to 20mol%; the suitable solvent is a weak polar or polar aprotic organic solvent or its mixed solvent; the reaction temperature is 30 to 150°C; the reaction time is 1 to 7 days. Then, bis(biphenyl)spirothiophene fluorene was prepared by the corresponding Suzuki reaction in step (2). Finally, the compound material II is obtained by the Friedel-Crafts reaction in step (3), and the specific reaction conditions are that bis(biphenyl...

Embodiment 1

[0049] Example 1, preparation of complex spiroaryl fluorene compound material II:

[0050] 2,7-bis(9,9-dioctyl-fluoren-2-yl)-9-phenyl-fluoren-9-ol

[0051]

[0052] Take 2,7-dibromo-9-phenyl-fluoren-9-ol (1.735g, 4.17mmol, 1 equiv.) and 4,4,5,5-tetramethyl-2-(9,9-dioctyl Base-9H-fluoren-7-yl)-1,3,2-dioxabororane (4.524g, 8.75mmol, 2.1equiv.) was mixed and dissolved in solvent toluene (40mL), and catalyst Pd(PPh 3 ) 4 (50 mg, 0.043 mmol). Protect from light and pass through nitrogen, then add K 2 CO 3 (2.0M aqueous solution, 12.0mL, 24.0mmol), react at 90°C for 48 hours, add water after the reaction, use CHCl 3 Extraction, drying and rotary evaporation, petroleum ether silica gel column purification, to obtain solid 2,7-bis(9,9-dioctyl-fluoren-2-yl)-9-phenyl-fluoren-9-ol as colorless glass (3.28g, 76 %). MALDI-TOF-MS (m / z): 1034.7 (M + ), 1034.9. 1 H NMR (400MHz, CDCl 3 , ppm): δ7.815-7.795 (d, J=8.0Hz, 2H), 7.733-7.701 (t, 6H), 7.669 (s, 2H), 7.574-7.537 (m, 6H), ...

Embodiment 3

[0056] Embodiment 3, the photoluminescence spectrum measurement of complex spiroaryl fluorene material:

[0057] The product was made into a precise 1 μM dilute solution in chloroform and flushed with argon to remove oxygen. Shimadzu UV-3150 ultraviolet-visible spectrometer and RF-530XPC fluorescence spectrometer were used to measure the absorption spectrum and emission spectrum, and the photoluminescence spectrum was measured at the maximum absorption wavelength of ultraviolet absorption. The solid film was prepared by solution spin-coating film forming technology, and the film thickness was 300nm.

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Abstract

The invention relates to a complicated spiro-aryl fluorine material and preparation and application methods thereof, which belong to the organic photoelectric material scientific field, in particular to the complicated spiro-aryl fluorine material and the preparation method thereof. And the material is applied to organic electronic fields of organic rectifier diode, organic luminescence display, organic laser, etc. With the structure as is shown on the right, the compound material I has the advantages of: (1) having specific electronic structure and photoelectric properties, such as narrow emission spectrum; (2) maintaining high thermal stability and glass transition temperature, etc. Materials of the kind have commercial application potential in stable dark blue materials.

Description

technical field [0001] The present invention specifically relates to a complex spiroaryl fluorene material and its preparation method, and relates to the application of these materials in the fields of organic rectifier diodes, organic electroluminescence, organic lasers, organic nonlinear optics, organic electrical storage, chemical and biological sensing, etc. Applications. It belongs to the technical field of organic photoelectric materials. 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, o...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D333/78H01L51/00H01L45/00H01L51/54H01L51/46H01S5/36H10K99/00
CPCY02E10/549
Inventor 黄维解令海张龙石乃恩
Owner NINGBO LUMILAN NEW MATERIAL CO LTD
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