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

A technology of spirofluorene xanthene phosphooxygen and xanthene phosphooxygen, which is applied in the field of synthesis of diphenylphosphoryloxy series compounds, and can solve the problem of poor thermal stability and morphological stability, low triplet state energy level, and limited applications and other problems, to achieve high thermal stability, low cost of raw materials, and simple synthesis method

Inactive Publication Date: 2013-12-25
NANJING FANGYUAN GLOBAL DISPLAY TECH
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  • 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] Using the one-pot preparation method of spiro ring (such as literature: Org. Lett. 2006(8), 2787-2790), under the protection of inert gas, combine 10 times equivalent of phenol (or p-bromophenol) with 1 times equivalent of 2 , 7-dibromo-9-fluorenone (or 9-fluorenone) at 150 ℃, and then add 4 times the equivalent of methanesulfonic acid to catalyze the reaction for 12 hours. The monomer product is obtained by silica gel column chromatography.

[0071] (2) Synthesis of organophosphorus compounds of spirofluorenexanthene

[0072] Under the protection of inert gas, dissolve 1 equivalent of the reactant (bromo-containing spirofluorene xanthene) in tetrahydrofuran solution (THF), and slowly add 1.5 equivalents of n-butyl dropwise at low temperature (-78°C) Base lithium, using n-butyllithium and reactant (bromide-containing spirofluorene xanthene) to exchange lithium halide to make spirofluorene xanthene form a lithium salt, and then react at low temperature (-78°C) for 3 hours, a...

Embodiment 1

[0082] (1) Synthesis of 2-bromo-spirofluorenexanthene

[0083] Add dry 2-bromofluorenone (5.0g, 19.3mmol), phenol (18.2g, 192.8mmol) and methanesulfonic acid (5mL, 77.2mmol) into a two-neck round-bottomed flask equipped with magnets, and add Spherical condenser, closed system, protected from light, pumped 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 (7.7g, 192.8mmol) was added to adjust the pH to alkaline, and the solid crude product was obtained by suction filtration. The crude product was eluted by silica gel column chromatography with petroleum ether as an eluent 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, 8.0 Hz, 1H), 7.667-7.646 (d, 8.4 Hz, 1H), 7.5-7.475 (d, 8.0 Hz, 1H), 7.406-7.366 (t, 7.6 Hz, 1H), 7.285-7.265(d, 8.0Hz, 1H), 7.246-7.19(m, 5H), 7.169-7.15(d, 7.6Hz, 1H), 6.819-6.779(t, 2H)...

example 2

[0100] Example 2: (Product in Example 1) UV absorption spectrum, photoluminescence spectrum, spectral thermal stability and quantum efficiency measurement

[0101] (1) Dissolve SFX2PO in a dilute dichloromethane solution, and use Shimadzu UV-3150 ultraviolet-visible spectrometer and RF-530XPC fluorescence spectrometer to measure the absorption and emission spectra. The photoluminescence spectrum is measured at the maximum absorption wavelength (312nm) 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 dilute dichloromethane solution, and use Shimadzu UV-3150 ultraviolet-visible spectrometer and RF-530XPC fluorescence spectrometer to mea...

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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 spirofluorenexanthene diphenylphosphoroxy compounds and the application of the material in the field of organic electroluminescence. technical background [0002] Since Kodak’s Tang research group in the United States published in 1987 that thin-film organic electroluminescent devices (Organic Light-emitting Diodes, OLED) made of organic fluorescent materials, organic flat panel displays have become the next generation of market-oriented displays after liquid crystal displays. product. The advantages of OLED are self-luminous, wide viewing angle (up to 170°), fast response time (on the order of 1μs), high luminous efficiency, low working voltage (3-10V), and thin panel thickness (less than 2mm). Therefore, the development of new organic optoelectronic information materials with practical market potential has attracted the atte...

Claims

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Application Information

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Patent Type & Authority Patents(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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