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Fluoro-substituted 9, 9'-spirobifluorene blue-light host material, its preparation method and application

A blue-light host material, spirobifluorene technology, which is applied in the direction of luminescent materials, preparation of halogenated hydrocarbons, chemical instruments and methods, etc., can solve the problems of poor performance of blue light devices, difficulties in phosphorescent blue light devices, and difficulty in achieving high efficiency and good color purity Long-life blue light devices and other issues, to achieve good luminous brightness, good thermal stability, and good luminous efficiency

Active Publication Date: 2013-09-11
XI AN JIAOTONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the inherent wide bandgap of blue light materials, it is difficult to realize blue light devices with high efficiency, good color purity and long lifetime.
Therefore, blue devices perform poorly relative to green and red devices
Although phosphorescent electroluminescent devices (PhOLEDs) have been extensively studied, maintaining high efficiency and long lifetime performance is difficult for phosphorescent blue devices.

Method used

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  • Fluoro-substituted 9, 9'-spirobifluorene blue-light host material, its preparation method and application
  • Fluoro-substituted 9, 9'-spirobifluorene blue-light host material, its preparation method and application
  • Fluoro-substituted 9, 9'-spirobifluorene blue-light host material, its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] see figure 1 , Fluorinated 9,9'-spirobifluorene blue-light host material is obtained by ferric chloride-catalyzed bromination of 9,9'-spirobifluorene and bromine at room temperature to obtain reaction intermediates 2,2',7,7' -Tetrabromo-9,9′-spirobifluorene (2,2′,7,7′-tetrabromo-9,9′-spirobifluorene, Spiro-4Br), followed by fluoro- or trifluoromethyl-substituted phenylboronic acid Under the catalysis of tetrakis(triphenylphosphine)palladium, the target product was obtained by Suzuki coupling reaction.

[0034] The intermediate product 2,2′,7,7′-tetrabromo-9,9′-spirobifluorene is synthesized as follows: 9,9′-spirobifluorene (6.52g, 20.6mmol) and anhydrous ferric chloride (FeCl 3 , 10mg) in 60mL of chloroform solution, slowly drop 10mL of chloroform solution containing bromine (4.45mL, 86.6mmol) at 0°C (dropping for more than 1h), spot the plate to follow the reaction (reaction 24h ). After the reaction was completed, the remaining bromine was removed by washing the r...

Embodiment 2

[0036] Example 2: Synthesis of fluorinated 9,9'-spirobifluorene blue light host material 1:

[0037]

[0038] Under nitrogen atmosphere, to 30mL THF and 10mL, 2.0mol·L -1 K 2 CO 3 In the solution, add 2,2′,7,7′-tetrabromo-9,9′-spirobifluorene (1.1g, 1.74mmol), 2-fluorophenylboronic acid (1.40g, 10mmol) and Pd(PPh3) 4 (0.40 g, 0.35 mmol). After the reaction, the mixture was heated to reflux for 24h, and the reaction was tracked by point plate. After the reaction is complete, cool down and add water to stop the reaction. Products with CH 2 Cl 2 Extraction, washing the organic phase with brine, anhydrous MgSO 4 It was dried, concentrated by rotary evaporation to remove the solvent, and 1.05 g of white solid 1 was obtained by column chromatography with ethyl acetate and petroleum ether. 1 H NMR (CDCl 3 ,400MHz):δ6.98(s,4H),7.01-7.10(m,8H),7.18-7.23(m,4H),7.28-7.31(t,J=7.6Hz,4H),7.62(d,J =7.6Hz, 4H), 7.93(d, J=8.0Hz, 4H).

Embodiment 3

[0039] Example 3: Synthesis of fluorinated 9,9'-spirobifluorene blue light host material 5:

[0040]

[0041] Under nitrogen atmosphere, to 30mL THF and 10mL, 2.0mol·L –1 K 2 CO 3 To the solution, 2,2′,7,7′-tetrabromo-9,9′-spirobifluorene (1.1g, 1.74mmol), 2,4di-fluorophenylboronic acid (1.58g, 10mmol) and Pd (PPh 3 ) 4 (0.40g, 0.35mmol). After the reaction, the mixture was heated to reflux for 24h, and the reaction was tracked by point plate. After the reaction is complete, cool down and add water to stop the reaction. Products with CH 2 Cl 2 Extraction, washing the organic phase with brine, anhydrous MgSO 4 It was dried, concentrated by rotary evaporation to remove the solvent, and 1.18 g of white solid 5 was obtained by column chromatography with ethyl acetate and petroleum ether. 1 H NMR (CDCl 3 ,400MHz):δ6.78-6.85(m,8H),7.91(s,4H),7.23-7.25(m,4H),7.57(d,J=8.0Hz,4H),7.93(d,J=8.0 Hz, 4H).

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Abstract

The invention provides a fluoro-substituted 9, 9'-spirobifluorene blue-light host material, its preparation method and application. Structurally, the fluoro-substituted 9, 9'-spirobifluorene blue-light host material contains a 9, 9'-spirobifluorene central core, the periphery of which is modified by different fluoro-substituted (or trifluoromethyl substituted) phenyl groups. By changing the position and the number of peripheral strong electron withdrawing group fluorine or trifluoromethyl, adjusting the highest occupied molecular orbital and lowest unoccupied molecular orbital energy levels of the material, the charge transmission capability, photophysical properties and thermal properties, and making its emission spectrum and a doped object's absorption spectrum well overlapped, the material can effectively absorb energy and transfer the energy to the object, thus causing luminescence of the object and improving device's performance. With good thermal stability and luminescent properties, the material is easy to synthesize and is convenient to purify, and can be widely used in the fields of organic field effect transistors, organic electroluminescent devices, organic laser and organic photovoltaic solar cells, etc.

Description

technical field [0001] The invention belongs to the technical field of organic photoelectric functional materials, and relates to a blue light host material and its application, in particular to a fluorine-substituted 9,9'-spirobifluorene blue light host material and its preparation method and application. Background technique [0002] In recent years, organic electroluminescent devices have attracted widespread interest in the scientific and industrial communities due to their potential applications in full-color displays and light sources. In order to achieve commercial full-color display, red, green, and blue primary colors (RGB) luminescent materials have been greatly developed. However, due to the inherent wide bandgap of blue light materials, it is difficult to realize blue light devices with high efficiency, good color purity and long lifetime. Therefore, blue devices perform poorly relative to green and red devices. Although phosphorescent electroluminescent device...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07C25/22C07C22/08C07C17/263H01L51/54H01L51/00
Inventor 吴朝新李战锋焦博侯洵
Owner XI AN JIAOTONG UNIV
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