Spirofluorene xanthene phosphine oxide electro-phosphorescent main materials and synthesis and application methods thereof

A technology of spirofluorene xanthene phosphine and xanthene phosphine is applied in the field of synthesis of diphenyl phosphine series compounds, which can solve the problem of low triplet energy level, poor thermal stability and morphological stability, and limited application. and other problems, to achieve the effects of low cost of raw materials, high thermal stability, and simple and easy synthesis method.

Inactive Publication Date: 2011-11-02
NANJING FANGYUAN GLOBAL DISPLAY TECH
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  • Summary
  • Abstract
  • Description
  • Claims
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Problems solved by technology

The disadvantages of these host materials are low triplet energy levels, low thermal and morphological stability
The triplet energy level (E T >3.5eV), however, these materials have poor thermal stability and morphological stability, and their T g Lower temperature (26~101℃)
Therefore, due to the existence of these disadvantages, the application of these materials as host materials in devices is limited to some extent.

Method used

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  • Spirofluorene xanthene phosphine oxide electro-phosphorescent main materials and synthesis and application methods thereof
  • Spirofluorene xanthene phosphine oxide electro-phosphorescent main materials and synthesis and application methods thereof
  • Spirofluorene xanthene phosphine oxide electro-phosphorescent main materials and synthesis and application methods thereof

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0070] Utilize the preparation method of one-pot spirocycle (such as literature: Org.Lett.2006 (8), 2787-2790), under the protection of inert gas, 10 times of equivalents of phenol (or p-bromophenol) and 1 times of equivalents of 2 , 7-dibromo-9-fluorenone (or 9-fluorenone) at 150 ° C, and then add 4 times the equivalent of methanesulfonic acid to catalyze the reaction for 12 hours. The monomer product was obtained by silica gel column chromatography.

[0071] (2) Synthesis of organophosphorus compounds of spirofluorene xanthene

[0072] Under the protection of an inert gas, dissolve 1 times the equivalent of the reactant (bromine-containing spirofluorene xanthene) in tetrahydrofuran solution (THF), and slowly add 1.5 times the equivalent of n-butyl at low temperature (-78°C) Lithium, using n-butyllithium and the reactant (bromine-containing spirofluorene xanthene) for lithium halide exchange, so that the spirofluorene xanthene forms a lithium salt, and then reacts at low tem...

Embodiment 1

[0082] (1) Synthesis of 2-bromo-spirofluorene xanthene

[0083] Add dry 2-bromofluorenone (5.0g, 19.3mmol), phenol (18.2g, 192.8mmol) and methanesulfonic acid (5mL, 77.2mmol) into a two-necked round-bottomed flask equipped with a magnet, and add Spherical condenser, closed system, protected from light, replaced nitrogen 3 times, placed in an oil bath, heated to 150°C, and reacted for 5 hours. At the end of the reaction, water (200 mL) was added and stirred. Sodium hydroxide (7.7 g, 192.8 mmol) was added to adjust the pH value to basic, and the solid crude product was obtained by suction filtration. The crude product was eluted with petroleum ether as eluent by silica gel column chromatography to obtain a white solid product (4.8 g). The yield was 60%. 1 H NMR (400MHz, CDCl 3 , ppm) δ: 7.783-7.763 (d, 8.0Hz, 1H), 7.667-7.646 (d, 8.4Hz, 1H), 7.5-7.475 (d, 8.0Hz, 1H), 7.406-7.366 (t, 7.6Hz, 1H), 7.285-7.265(d, 8.0Hz, 1H), 7.246-7.19(m, 5H), 7.169-7.15(d, 7.6Hz, 1H), 6.819-6....

example 2

[0100] Example two: the ultraviolet absorption spectrum of (the product in embodiment 1), photoluminescence spectrum, spectral thermal stability and quantum efficiency measurement

[0101] (1) Dissolve SFX2PO in dichloromethane dilute solution, and use Shimadzu UV-3150 ultraviolet-visible spectrometer and RF-530XPC fluorescence spectrometer to measure the absorption and emission spectra. The photoluminescence spectrum was measured at the maximum absorption wavelength (312 nm) of ultraviolet absorption. The solid film is formed by dropping the solution on a transparent glass plate after the solvent evaporates. The maximum absorption peak of the SFX2PO solution is 312nm, and the emission peaks of the fluorescence spectrum are 319nm and 332nm. The maximum emission wavelength of the solid film is 369nm. See attached for details Figure 5 .

[0102] (2) Dissolve SFX27PO in dichloromethane dilute solution, and use Shimadzu UV-3150 ultraviolet-visible spectrometer and RF-530XPC f...

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Abstract

The invention relates to spirofluorene xanthene phosphine oxide electro-phosphorescent main materials and synthesis and application methods thereof, belongs to the field of photoelectric material science and technology, and in particular relates to four spirofluorene xanthene organic phosphine oxide materials and application of the materials in the field of organic electronics such as organic electroluminescent materials, organic solar cells, organic field-effect tubes, dye laser, organic nonlinear optical materials, fluorescent probes and the like. The series of materials are obtained by introducing diphenyl phosphine oxide groups to the 2nd site, the 2nd and 7th sites, the 2nd' site and the 2nd' and 7th' sites of spirofluorene xanthene respectively. The series of compounds have good charge transfer performance, thermal stability and high triplet energy level (ET=-2.86eV), and can be used as main materials and applied in phosphorescent devices. When the series of compounds are applied in the organic electro-phosphorescent devices, the maximum external quantum efficiency is 10.78 percent and the maximum brightness is 8,582cd / m<2> in the blue phosphorescent device; and in the green phosphorescent device, the maximum external quantum efficiency is 19.1 percent, and the maximum brightness is 16,943cd / m<2>.

Description

technical field [0001] The invention belongs to the field of organic electroluminescent materials. It specifically relates to the synthesis of a class of spirofluorene xanthene diphenylphosphine oxide series compounds, and the application of the material in the field of organic electroluminescence. technical background [0002] Since Tang Research Group of Kodak Corporation of the United States published thin-film organic electroluminescent devices (Organic Light-emitting Diodes, OLEDs) made of organic fluorescent materials in 1987, organic flat-panel displays have become another generation of market-oriented displays after liquid crystal displays. product. The advantages of OLED are self-illumination, wide viewing angle (up to 170°), fast response time (on the order of 1 μs), high luminous efficiency, low operating voltage (3-10V), and thin panel thickness (less than 2mm). Therefore, the development of new organic optoelectronic information materials with practical market...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/655H01L51/54
Inventor 解令海黄维赵杰殷成蓉谢国华许辉常永正赵剑锋仪明东赵毅刘世镛
Owner NANJING FANGYUAN GLOBAL DISPLAY TECH
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