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Conjugate derivative material of 9-phenyl-9-pyrenyl fluorene substituted pyrene its preparation method and application

A kind of derivative, the technology of pyrenyl fluorene, which is applied to the conjugated derivative material of pyrene substituted by 9-phenyl-9-pyrenyl fluorene and its preparation and application fields

Inactive Publication Date: 2007-05-16
FUDAN UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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  • Conjugate derivative material of 9-phenyl-9-pyrenyl fluorene substituted pyrene its preparation method and application
  • Conjugate derivative material of 9-phenyl-9-pyrenyl fluorene substituted pyrene its preparation method and application
  • Conjugate derivative material of 9-phenyl-9-pyrenyl fluorene substituted pyrene its preparation method and application

Examples

Experimental program
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Effect test

Embodiment 1

[0073] Example 1: Synthesis of 2-pyrenyl-9-phenyl-9-pyrenylfluorene (2P9PPF) (Compound I).

[0074] (1) Synthesis of 2-bromo-9-phenylfluoren-9-ol (2-Bromo-9-phenyl-fluoren-9-ol)

[0075] Use magnesium scraps (0.58g, 24mmol), a small amount of iodine and bromine benzyl ((4.48g, 29mmol) in anhydrous ether (or anhydrous tetrahydrofuran) (30mL) to make phenylmagnesium bromide Grignard reagent, the reagent used Dilute with 20mL of anhydrous ether, and then add anhydrous tetrahydrofuran dissolved with 2-bromofluorenone (3.77g, 14.6mmol) dropwise into Grignard reagent, stir for 4h, add saturated ammonium chloride solution for hydrogenolysis after cooling for 2h. The reaction mixture Extract twice with dichloromethane, wash with water, then dry with anhydrous magnesium sulfate.Use ethyl acetate / petroleum ether=10:1 as eluent column chromatography on silica gel to obtain light yellow solid (4.65g, 13.8mmol ), yield 94%). 1 HNMR (400MHz, CDCl3) δ (ppm): 7.65 (d, J = 8.0Hz, 1H); 7.44-7...

Embodiment 2

[0085] Embodiment 2: to the ultraviolet absorption spectrum of the trimer 2P9PPF (product in embodiment 1) containing anthracene and pyrene fluorene in 9 positions, photoluminescence spectrum, spectral thermal stability and quantum efficiency measurement:

[0086] Dissolve 2P9PPF 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 (351 nm) of ultraviolet absorption. The solid film is formed by dropping the solution on a transparent glass plate after the solvent evaporates. The fluorescence quantum efficiency of the solution is measured by 10 in cyclohexane -6 A 9,10-diphenylanthracene solution of M (quantum efficiency 0.9) was used as a standard for measurement.

[0087] The maximum absorption peak of the 2P9PPF solution at greater than 300nm is 351nm, and the maximum...

Embodiment 3

[0089] Example 3: Synthesis and spectrometry of 2,7-dipyrenyl-9-phenyl-9-pyrenylfluorene (DPPPF) (compound II).

[0090] The synthetic method similar to 2P9PPF can synthesize 2,7-dipyrenyl-9-phenyl-9-pyrenylfluorene (DPPPF), but 2,7-dibromofluorene is used for fluorene, and during the even chain reaction, 1-(4 , the amount of 4,5,5-tetramethyl-1,3,2-dioxoboronate 2-yl)pyrene should be greater than that of 2,7-dibromo-9-phenyl-9-pyrenylfluorene double.

[0091] The NMR, MS and elemental analysis data of DPPPF are as follows. 1 H-NMR (400MHz, CDCl3) δ (ppm): 8.24-8.12 (m, 8H); 8.10-7.92 (m, 19H); 7.77 (dd, J=8.4Hz, 1.6Hz, 2H); 7.64 (d, 8.4Hz, 2H); 7.46(s, 2H); 7.34-7.28(s, 3H); 7.27-7.22(m, 2H). 13 C-NMR(400MHz,CDCl3)δ(ppm):152.80,140.92,139.04,137.75,131.63,131.06,130.76,130.62,129.27,128.56,128.48,127.85,127.60,126.98,126.57,126.18,125.37,125.28,125.04 , 124.98, 124.88.LDl-TOF-MS (m / z): Calcd.for C 67 h 38 842.3, found 842.2. Anal. Calcd. C, 95.46; H, 4.54; found C, 95....

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Abstract

The present invention belongs to the field of photoelectric material technology. In the concrete it relates to a kind of 9-phenyl-9-pyrenyl fluorine substituted pyrene conjugated derivative material, its preparation method and application. Said compound is characterized by that the 9-phenyl-9-pyrenyl fluorine structure is introduced into the high-effective luminescent system of pyrene. Said invented material can be extensively used in the fields of organic electroluminescence material, organic integrated circuit, organic solar cell, organic field-effect transistor and organic non-linear optical material, etc.

Description

technical field [0001] The invention belongs to the field of optoelectronic materials and application technology, and specifically relates to a conjugated derivative material of pyrene substituted by 9-phenyl-9-pyrenylfluorene and a preparation method thereof, and the application of this type of material to organic / polymer electronics Luminescent materials, organic integrated circuits, organic solar cells, organic field effect transistors, 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 first used 8-hydroxyquinoline aluminum (Alq 3 ) as a light-emitting layer to make a double-layer organic electroluminescent device (OLED [Tang, C.W.; Van Slyke, S.A. Appl. 1990, Friend [Burroughes,...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C15/56C07C2/00C09K9/00H05B33/14H01L31/0256G02F1/361
Inventor 黄维唐超解令海李盛彪刘烽张晴晴范曲立
Owner FUDAN UNIV
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