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A spirobifluorenoindole derivative, its preparation method and application

A technology of spirobifluorene and its derivatives, which is applied in the fields of spirobifluorene and indole derivatives, their preparation and application, can solve the problems of poor stability and low efficiency of blue light materials, achieve reduced intermolecular aggregation, high yield, The effect of good application prospects

Active Publication Date: 2018-08-21
HUAZHONG UNIV OF SCI & TECH +1
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] Aiming at the above defects or improvement needs of the prior art, the present invention provides a spirobifluorenoindole derivative, a preparation method and its application, the purpose of which is to synthesize spirobifluorenoindole by adopting a simple and feasible synthesis scheme derivatives and apply them to electroluminescent materials, thereby solving the technical problems of poor stability and low efficiency of blue light materials in the prior art

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  • A spirobifluorenoindole derivative, its preparation method and application
  • A spirobifluorenoindole derivative, its preparation method and application
  • A spirobifluorenoindole derivative, its preparation method and application

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preparation example Construction

[0069] The preparation method of the spirobifluorenoindole derivatives of the present invention, the synthetic route schematic diagram is as follows figure 1 shown, including the following steps:

[0070] (1) Suzuki cross-coupling reaction: 3-carbazole boronic acid pinacol ester and o-dibromobenzene undergo Suzuki cross-coupling reaction to obtain the intermediate product 3-(2-bromophenyl)-9H-carbazole;

[0071] (2) Adding a protecting group: the intermediate product 3-(2-bromophenyl)-9H-carbazole obtained in step (1) is used as a reactant, and N,N-dimethylformamide (DMF) is used as a reaction solvent , use sodium hydride to extract hydrogen, then add p-toluenesulfonyl chloride, the molar ratio of 3-(2-bromophenyl)-9H-carbazole, p-toluenesulfonyl chloride and sodium hydride is 1:1 ~2:1~3, react at room temperature to obtain the intermediate product 3-(2-bromophenyl)-9-(4-(methylsulfonyl)phenyl)-9H-carbazole;

[0072] (3) Formation of spirobifluorenoindole: Dissolve the inter...

Embodiment 1

[0085] The spirobifluorene indole derivative 34 (5-(4,6-diphenyl-1,3,5-triazine)-5H spirofluorene-9,8-indenecarbazole) of the present invention can be Synthesized by the following method.

[0086]

[0087] (1) Suzuki cross-coupling reaction: In a dry 500ml two-necked flask, 3-carbazole boronic acid pinacol ester (15g, 51mmol), o-dibromobenzene (14.5g, 61.2mmol), toluene (120mL ), ethanol (60mL) and 2mol / L potassium carbonate solution (60mL) were added, ultrasonication was performed for 5-10 minutes first, and then nitrogen gas was stirred rapidly for 5 minutes, and the catalyst tetrakis(triphenylphosphine) palladium (1.8g, 1.53 mmol), a large amount of nitrogen was passed for 10 minutes. Heated to 100°C and stirred at reflux for 12h. During treatment, extract first, spin dry, and use petroleum ether and dichloromethane column chromatography to obtain a white solid product 3-(2-bromophenyl)-9H-carbazole with a yield of 93%.

[0088] (2) Adding a protecting group: first ad...

Embodiment 2

[0096] The spirobifluorene-indole derivatives prepared in Example 1 have the formula 34(5-(4,6-diphenyl-1,3,5-triazine)-5H spirofluorene-9,8-indencarba Azole) was used as the light-emitting guest to prepare the device.

[0097] This example demonstrates the performance verification of an electroluminescent device fabricated with 34 as a guest luminescent material. The ITO (Indium Tin Oxide) glass was ultrasonically cleaned in detergent and deionized water for 30 minutes sequentially. Then vacuum dry for 2 hours (105°C), then put the ITO glass into the plasma reactor for 5 minutes of oxygen plasma treatment, transfer it to the vacuum chamber to prepare organic film and metal electrode, and then prepare a layer of 10nm by vacuum evaporation. The hole injection material molybdenum trioxide, followed by evaporation of 60nm thick hole transport material: 4,4'-cyclohexyl bis[N,N-bis(4-methylphenyl)aniline] (TAPC), and then evaporation Plating 4,4',4"-tris(carbazol-9-yl)triphenylam...

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Abstract

The invention discloses a spirobifluorenoindole derivative, a preparation method and an application thereof. The spirobifluorenoindole derivatives described in the present invention can be used as multifunctional organic luminescent materials. With spirobifluorene indole as the core, due to the steric hindrance effect of spirobifluorene to achieve intramolecular distortion, the electron clouds of the highest occupied orbital and the lowest empty orbital of the molecule can be relatively separated to obtain a small singlet triplet energy level difference, In this way, luminescent molecules with thermally induced delayed fluorescence properties are designed and prepared; the synthesis is relatively simple; the thermal properties, luminous efficiency and light color of the material can be adjusted, and even deep blue light color can be obtained; high fluorescence quantum efficiency can be achieved, and it can be used as a fluorescent object. Thermally activated delayed fluorescence properties can also be used as host materials for fluorescence and phosphorescence, so multifunctional organic light-emitting materials can be constructed by design.

Description

technical field [0001] The invention belongs to the technical field of preparation and application of organic photoelectric materials, and more specifically relates to a spirobifluorenoindole derivative, its preparation method and application. Background technique [0002] Since Kodak first reported Organic Light Emitting Diode (OLED) in 1987 (Pope M., Kallmann.H.P., Magnante.P., Electroluminescence in OrganicCrystals. The Journal of Chemical Physics 1963,38(8):2042 -2043), through the continuous synthesis of new materials and optimized device structures, the research of OLEDs has made a major breakthrough, showing attractive industrialization prospects in the next generation of flat-panel displays and lighting sources. Subsequently, in 1990, the University of Cambridge in the United Kingdom introduced polymer electroluminescent materials and devices, and organic electroluminescent devices (OLEDs) have caused a huge sensation in the academic and business circles. In 1998, F...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/96C07D401/04C07D403/04C07D401/14C07D409/04C07D405/04C09K11/06H01L51/54H01L51/50
CPCC09K11/06C07D209/96C07D401/04C07D401/14C07D403/04C07D405/04C07D409/04C09K2211/1092C09K2211/1088C09K2211/1029C09K2211/1044C09K2211/1059H10K85/654H10K85/6576H10K85/6574H10K85/6572H10K50/11
Inventor 王磊吕夏蕾庄少卿穆广园
Owner HUAZHONG UNIV OF SCI & TECH
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