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Conjugated ramification material of fluorine containing anthracene and pyrene at 9th position, preparation method and application

A derivative and conjugated technology, applied in the field of optoelectronic materials, to achieve the effect of simple route, improved device efficiency, and improved injection and transmission capabilities

Inactive Publication Date: 2005-10-26
FUDAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Anthracene and pyrene are large conjugated aromatic groups with the function of transporting holes, but so far, there are no papers and patent reports on the fluorene system introducing these two groups at the 9-position of fluorene

Method used

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  • Conjugated ramification material of fluorine containing anthracene and pyrene at 9th position, preparation method and application
  • Conjugated ramification material of fluorine containing anthracene and pyrene at 9th position, preparation method and application
  • Conjugated ramification material of fluorine containing anthracene and pyrene at 9th position, preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] Example 1: Synthesis of Trimeric (9-phenyl-9-pyrenylfluorene) ter(9-phenyl-9-pyrenylfluorene) (TPPF)

[0046] (1) 2,7-dibromofluorenone and 2-bromofluorenone.

[0047] Dissolve 10.1 g of 2,7-dibromofluorene in 150 mL of pyridine solution, add 1 mL of benzyltrimethylammonium hydroxide in methnol (40%) (or tetrabutylammonium hydroxide in methanol) to this solution, and then stir with air for 24 hours. Pyridine was removed by distillation under reduced pressure to obtain a reddish brown solid. The solid was recrystallized in ethanol (or column chromatography with ethyl acetate / petroleum ether=10:1) to obtain 9.8 g of yellow solid with a yield of 93%. 1 HNMR (400MHz, CDCl3) δ (ppm): 7.77 (d, J = 1.6Hz, 2H); 7.63 (dd, J = 8.0, 1.6Hz, 2H), 7.39 (d, J = 8.0Hz, 2H).

[0048] Using 2-bromofluorene as raw material, 2-bromofluorenone can be obtained in a similar method with a yield of 93%. 1 HNMR (400MHz, CDCl3) δ (ppm): 7.77 (d, J = 1.6Hz, 1H); 7.66 (dt, J = 7.2Hz, 1.2Hz, 1H);...

Embodiment 2

[0060] Embodiment 2: to the ultraviolet absorption spectrum of the trimer TPPF (the product in embodiment 1) that contains anthracene, pyrene fluorene at 9 positions, photoluminescence spectrum, spectral thermal stability and quantum efficiency measurement:

[0061] TPPF was dissolved in dichloromethane dilute solution saturated with nitrogen, and measured by Shimadzu UV-3150 ultraviolet-visible spectrometer and absorption wavelength (351nm). The photoluminescence spectrum of the solid film was carried out through a vacuum-evaporated quartz plate with a film thickness of 300 nm. The fluorescence quantum efficiency of the solution is measured by 10 in cyclohexanone -6 A 9,10-dibenzanthracene solution of M (with a quantum efficiency of 1.0) was used as a standard for measurement.

[0062] The maximum absorption peak of TPPF solution above 300nm is 351nm, and the photoluminescence spectrum has two characteristic absorptions, namely 399 and 419nm.

[0063] The maximum emission w...

Embodiment 3

[0064] Example 3: Synthesis and Spectral Measurement of Trimeric (9-Anthracenyl-9-Phenylfluorene) (TAPF).

[0065] Using a method similar to TAPF, except that pyrene is replaced by anthracene, TAPF can be obtained in similar yield.

[0066] The ultraviolet absorption and photoluminescence spectra can be measured by a method similar to TAPF. The photoluminescence spectrum was measured at the maximum absorption wavelength (355 nm) of ultraviolet absorption.

[0067] The maximum absorption peak of TPPF solution above 300nm is 355nm, and the photoluminescence spectrum has two characteristic absorptions, namely 397 and 417nm.

[0068] The maximum emission wavelength of the solid film is 442nm. The solid film was annealed at 150°C for 24 hours under a nitrogen atmosphere, and the spectrum did not change significantly, indicating that the spectral stability was very good due to the good thermal stability. See attached figure 2 .

[0069] The structural formula of TAPF is as fol...

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Abstract

The present invention belongs to the field of photoelectric material, in the concrete, it is a 9-position anthracene and pyrene substituted fluorenic conjugated derivative material and its preparation method, and said material can be used in the field of organic electronics of organic / polymer electroluminescence material, organic integrated circuit, organic solar cell, organic field effect transistor, dye laser, organic non-linear optical material and fluorescent probe, etc. Said compound can utilize 9-position twice substitution structure to introduced the anthracene and pyrene into the high-effective luminescent conjugated fluorene system. Besides, said invention also provides several advantage of said conjugated derivative material.

Description

technical field [0001] The invention belongs to the technical field of optoelectronic materials, specifically a class of conjugated derivative materials of fluorene containing anthracene and pyrene at the 9-position and a preparation method thereof, and applies such materials to organic / polymer electroluminescent materials and organic integrated circuits , organic solar cells, organic field effect tubes, dye lasers, organic nonlinear optical materials and fluorescent probes and other organic electronics fields. technical background [0002] Due to the rapid development of information technology, people put forward higher and higher requirements for information display technology. In 1987, Tang et al. from Kodak Corporation of the United States used ultra-thin film technology to first use 8-hydroxyquinoline aluminum (Alq3) as the light-emitting layer to make a double-layer organic electroluminescent device (LED) [Tang, C.W.; Van Slyke, S.A. Appl.Phys.Lett.1987, 51, 913.], wh...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C13/70
Inventor 黄维唐超解令海李盛彪刘烽
Owner FUDAN UNIV
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