Preparation and application of bistriphenylamine substituted o-hydroxyphenylazole derivatives as organic monomolecular white light materials

A technology of o-hydroxyphenylazoles and molecular materials, which is applied in the field of organic single-molecule white light materials, can solve the problems of poor functional group tolerance, harsh reaction conditions, and difficulty in obtaining raw materials, and achieves reduction of operation difficulty, improvement of total yield, and high efficiency. quick results

Inactive Publication Date: 2017-05-24
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these three types of reactions usually have disadvantages such as long synthetic routes, many steps, harsh reaction conditions, cumbersome operations, difficult to obtain raw materials, poor tolerance of functional groups, and easy environmental pollution by by-products, which largely limits their development. Rapid synthesis of organic monomolecular white light materials with excellent photophysical properties

Method used

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  • Preparation and application of bistriphenylamine substituted o-hydroxyphenylazole derivatives as organic monomolecular white light materials
  • Preparation and application of bistriphenylamine substituted o-hydroxyphenylazole derivatives as organic monomolecular white light materials
  • Preparation and application of bistriphenylamine substituted o-hydroxyphenylazole derivatives as organic monomolecular white light materials

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Example 1: Synthesis of 4'-(diphenylamine)-3-(5-(4'-(diphenylamine)diphenyl-4-)oxazolyl-2-)diphenyl-4-phenol

[0038] (1) Will N -(4'-(Diphenylamine)diphenyl-4-oxo)acetimide (79 mg, 0.2 mmol), 4'-(oxazolyl-5)- N , N -Diphenyl-[1,1'-diphenyl]-4-amine (116 mg, 0.3 mmol), dichloro(pentamethylcyclopentadienyl)rhodium(III) dimer (5.0 mol %, 6.4 mg, 10 μmol), silver hexafluoroantimonate (20 mol%, 14.0 mg, 40 μmol), silver carbonate (0.4 equiv, 22 mg, 80 μmol), pivalic acid (2.0 equiv, 41 mg, 0.4 mmol), cesium pivalate (80 mol%, 38 mg, 0.16 mmol), N,N -Dimethylformamide (1 mL), stirred evenly under anhydrous and oxygen-free conditions, heated to 140 ° C, and reacted for 24 hours;

[0039] (2) After the reaction is completed, cool the reaction tube to room temperature, add ethyl acetate to dilute the reaction system, then filter through diatomaceous earth, and wash with ethyl acetate, combine the filtrates, wash with saturated saline, separate liquid, anhydrous sodium sulf...

Embodiment 2

[0040] Example 2: Synthesis of 4'-(diphenylamine)-3-(5-(4-(diphenylamine)-phenyl)benzoxazolyl-2)-5-methylbiphenyl-4-ol

[0041] (1) Will N -((4'-(diphenylamine)-3-methyl-[1,1'-diphenyl]-4)-oxy)acetimide (82 mg, 0.2mmol), 4'-(benzox Azolyl-5)- N , N -Diphenylaniline (109 mg, 0.3 mmol), dichloro(pentamethylcyclopentadienyl)rhodium(III) dimer (5.0 mol%, 6.4 mg, 10 μmol), silver hexafluoroantimonate (20 mol%, 14.0mg, 40 μmol), silver carbonate (0.4 equiv, 22 mg, 80 μmol), pivalic acid (2.0 equiv, 41 mg, 0.4 mmol), cesium pivalate (80 mol%, 38 mg , 0.16 mmol), N,N -Dimethylformamide (1 mL), stirred evenly under anhydrous and oxygen-free conditions, heated to 140 ° C, and reacted for 24 hours;

[0042] (2) After the reaction is completed, cool the reaction tube to room temperature, add ethyl acetate to dilute the reaction system, then filter through diatomaceous earth, and wash with ethyl acetate, combine the filtrates, wash with saturated saline, separate liquid, anhydrous sodi...

Embodiment 3

[0043] Example 3: The UV- Absorption Spectrum and Fluorescence Emission Spectrum

[0044] The compound 4'-(diphenylamine)-3-(5-(4'-(diphenylamine)diphenyl-4-)oxazolyl-2-)diphenyl-4-ol was dissolved in toluene and formulated into 1×10 -6 mol / L, put 2.5 mL into a cuvette, and measure the UV-absorption and fluorescence emission spectra. The absorption spectrum of compound 4'-(diphenylamine)-3-(5-(4'-(diphenylamine)diphenyl-4-)oxazolyl-2-)diphenyl-4-ol in toluene solution The maximum absorption peak is located at 309, 374 nm; the maximum emission peak of the fluorescence emission spectrum is located at 424, 539 nm, and its quantum efficiency is determined to be 60% (attached Figure 6 ). Compound 4'-(diphenylamine)-3-(5-(4'-(diphenylamine)diphenyl-4-)oxazolyl-2-)diphenyl-4-phenol and polystyrene (1 : 49) was dissolved in dichloromethane, spin-coated into a quartz plate to form a film, and measured UV-absorption and fluorescence emission spectra. Compound 4'-(diphenylamine)-...

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Abstract

The present invention relates to an organic single-molecule white light material ditriphenylamine substituted o-hydroxyphenyl azole derivative and a preparation method thereof. A series of white light emitting molecules can be prepared from the ditriphenylamine substituted o-hydroxyphenyl azole derivative by fine adjustment of double wavelength emission by use of ESITP mechanism; by introduction of a triphenylamine group, weakening fluorescence or quenching disadvantages due to molecular aggregation can be solved, fluorescence quantum yield is high, illumination brightness is good, and thermal stability is better. The technical path of C-H / C-H direct cross-coupling reaction for synthesis of the derivative shortens the synthesis step, reduces the difficulty of the operation, avoids the cumbersome process of pre-activation of substrates, improves the overall yield of the synthesis reaction, reduces costs, avoids production of a lot of waste, improves the atom economy and environmental friendliness, is simple and fast, and can quickly and efficiently get white lightmolecule libraries compared with conventional condensation reaction.

Description

technical field [0001] The invention relates to the preparation and application of a kind of organic monomolecular white light material bistriphenylamine substituted o-hydroxyphenyl azole derivatives. Background technique [0002] Organic electroluminescent white light diodes are widely used in flat panel displays and as white light sources. Due to their advantages of low price, large-area flexible display, low energy consumption and environmental protection, they have attracted great attention and attention from academic and industrial circles all over the world. [See: (a) Reineke, S., Lindner, F., Schwartz, G., Seidler, N., Walzer, K., Lüssem, B., Leo, K. Nature. 2009, 459 , 234; (b) Sun, Y., Giebink, N. C., Kanno, H., Ma, B., Thompson, M. E., Forrest, S. R. Nature. 2006, 440 , 908; (c) Kido, J., Kimura, M., Nagai, K. Science. 1995, 267 , 1332.]. White light refers to the light whose CIE value is within the elliptical range centered at (0.33, 0.33) on the CIE1931 co...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D263/32C07D277/28C09K11/06H01L33/50
CPCY02B20/00
Inventor 游劲松李必进兰静波吴迪高戈
Owner SICHUAN UNIV
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