Fluorene-naphthalene imide derivative compound and its application

A naphthalene diimide compound technology, applied in the field of fluorene-naphthalene diimide derivative compounds, to achieve the effects of good solubility, good electron transport, and excellent electron injection and transport capabilities

Inactive Publication Date: 2004-09-08
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] At present, there are no literature and patent reports on fluorene and 4-(N,N-dimethylamino)-1,8-naphthalene diimide derivatives and their applications in organic electroluminescence

Method used

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  • Fluorene-naphthalene imide derivative compound and its application
  • Fluorene-naphthalene imide derivative compound and its application
  • Fluorene-naphthalene imide derivative compound and its application

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Embodiment Construction

[0023] Synthetic route such as figure 1 shown.

[0024] (1) 4-bromo-N-(2'-fluorene)-1,8-naphthalene diimide (abbreviated as BFN): add 98% 4-bromo-1,8-naphthalene dianhydride (1.39 g; 5mmol), 96% 2-aminofluorene (0.95g, 5mmol), evacuated and filled with nitrogen for 30min, injected 120mL of 95% ethanol, heated, stirred and refluxed under nitrogen atmosphere for 24h, filtered at room temperature, purified by column chromatography Yellow powder (2.09 g, yields: 95%). mp: 285-286°C, MS (EI, m / z): 439 (100%, M + -1), 441 (98%, M + +1).Anal.Calcd for:C 25 h 14 BrNO 2 (Molecular weight: 440.29): C, 68.20%; H, 3.20%; N, 3.18%; Br, 18.15%. Found: C, 68.10%; H, 3.15%; N, 3.04%; Br, 18.13%. 1 HNMR (DMSO-d 6 , 300Hz) δ: 4.02 (2H, s), 7.38-7.45 (3H, m), 7.61-7.66 (2H, m), 7.98-8.01 (1H, d), 8.04-8.07 (2H, m), 8.29- 8.31(1H, d), 8.38-8.41(1H, d), 8.62-8.67(2H, t).FT-IR(KBr, cm -1): 1711, 1666, 1589, 1505, 1457, 1402, 1364, 1239, 1193, 1133, 1045, 974, 901, 826, 781, 736, 421.

[...

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Abstract

The present invention combines 4-(N, N-dimethylamino)-1, 8-naphthalene imide and fluorene in the same compound, and prepares fluorene-containing 4-(N, N-dimethylamino)-1, 8-naphthalene imide derivative through the synthesis path of Ulman ammonation and amidation. The compound has its chemical structure expressed via element analysis, infrared spectrum and nuclear magnetic resonance, electrochemical property expressed in cyclic voltametry and photophysical property researched in ultraviolet absorption spectrum and fluorescent spectrum. Its application in organic electroluminescence is researched, and experiments shows that the compound has excellent comprehensive performance as electronic transmitting material and yellow and green electroluminescent material.

Description

technical field [0001] The present invention relates to fluorene-naphthalene diimide derivative compounds, in particular to a class of 4-(N,N-dimethylamino)-N-[2'-(9',9'-dialkyl ) Compounds of fluorene]-1,8-naphthalene diimide derivatives. [0002] The present invention also relates to the application of the above compounds in organic light emitting diodes. Background technique: [0003] Since 1987 Kodak Corporation of the United States (Tang, C.W.; Vanslyke, S.A. Appl. Phys. Lett. 1987, 51, 913) and the University of Cambridge in 1990 (Burroughes, J.H.; Jones, C.A.; Friend, R.H. Nature 1990, 335, 137 ) since the introduction of high-efficiency organic and polymer electroluminescent devices (LEDs), it has aroused worldwide international competition in the fields of material science and information technology—organic / polymer full-color flat-panel display materials and devices. Its advantages such as self-illumination, high brightness, high efficiency, low-voltage DC drive, ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D221/06H01L51/54
Inventor 刘云圻曾鹏举王帅于贵朱道本
Owner INST OF CHEM CHINESE ACAD OF SCI
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