Complex diaryl fluorene material, preparation and application method thereof

A technology of diaryl fluorene and aryl fluorene is applied in the field of non-planar polycyclic heteroaromatic hydrocarbon organic semiconductor materials and preparation thereof, and can solve the problems of complicated preparation methods, and achieve the effects of simple synthesis steps, mild conditions and high thermal stability.

Inactive Publication Date: 2009-07-29
NANJING UNIV OF POSTS & TELECOMM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are very few patents on modifying easily crystallized organic semiconductor materials to become highly stable amorphous materials by using phenylfluorene or heterofluorene as a capping unit, and the preparation method is complicated

Method used

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  • Complex diaryl fluorene material, preparation and application method thereof
  • Complex diaryl fluorene material, preparation and application method thereof
  • Complex diaryl fluorene material, preparation and application method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Example 1. Preparation of thiophene material post-modified with 9-phenyl-fluorene unit:

[0040] 9-Phenyl-fluoren-9-ol

[0041] Take bromo-benzene (2.1mmol) and magnesium (0.502g, 2.1mmol) to react to generate Grignard reagent, and react with fluorenone (2.1mmol) dissolved in 16mL tetrahydrofuran at 60°C for 24 hours, a large amount of white precipitate is formed, and finally add saturated Color NHCl 4 Convert Grignard salts to alcohols. After the reaction was completed, ether was extracted, dried and rotary evaporated, and purified on a silica gel column with a mixed solvent of petroleum ether:dichloromethane (3:2) to obtain a slightly pale yellow solid tertiary alcohol (yield 90%). GC-MS (EI-m / z): 258.1 (M+ ). 1 H NMR (400MHz, CDCl 3 , ppm): δ7.691-7.672 (d, J=7.6Hz, 2H), 7.406-7.325 (m, 6H), 7.292-7.236 (m, 5H), 2.508 (s, 1H). 13 C NMR (CDCl 3 , ppm): δ150.658, 143.391, 139.82, 129.339, 128.698, 128.459, 127.462, 125.633, 125.037, 120.343, 83.85.

[0042] 2,5-...

Embodiment 2

[0044] Example 2, 9-phenyl-fluoren-9-ol as a capping agent to treat 2,2'-dithiophene capping material preparation:

[0045] 5,5'-bis(9-phenyl-fluoren-9-yl)-2,2'-dithiophene

[0046] Dissolve 9-phenyl-fluorene-9-ol and 2,2'-dithiophene in dichloromethane at a ratio of 2:1, add boron trifluoride-ether complex dropwise at room temperature for 30 minutes , adding ethanol and water to quench the reaction, dichloromethane extraction, drying and rotary evaporation, petroleum ether: dichloromethane silica gel column purification, recrystallization with tetrahydrofuran and petroleum ether to obtain white powder solid 5,5'-bis(9-phenyl -Fluoren-9-yl)-2,2'-dithiophene (92.1% yield). MALDI-TOF-MS (m / z): 646.2 (M + ). 1 H NMR (400MHz, CDCl 3 , ppm): δ7.759-7.74 (d, J=7.6Hz, 4H), 7.491-7.472 (d, J=7.6Hz, 4H), 7.392-7.352 (td, J=7.2Hz, J=1.2Hz, 4H), 7.303-7.257(td, J=7.6Hz, J=1.2Hz, 4H), 7.228-7.188(m, 10H), 6.817-6.808(d, J=3.6Hz, 2H), 6.694-6.685(d , J=3.6Hz2H). 13 C NMR (100MHz, CD...

Embodiment 3

[0047] Example 3, 9-phenyl-fluorene-9-ol as a capping agent to treat 2,2':5',2"-trithiophene capping material preparation:

[0048] 5,5″-bis(9-phenyl-fluoren-9-yl)-2,2′: 5′,2″-trithiophene

[0049] Dissolve 9-phenyl-fluoren-9-ol and 2,2':5',2"-trithiophene in dichloromethane at a ratio of 2:1, and add boron trifluoride-ether dropwise at room temperature The complex was reacted for 30 minutes, added ethanol and water to quench the reaction, extracted with dichloromethane, dried and rotary evaporated, petroleum ether: dichloromethane silica gel column purification, recrystallized with tetrahydrofuran and petroleum ether to obtain a white powder solid 5,5″- Bis(9-phenyl-fluoren-9-yl)-2,2': 5',2"-trithiophene (81.2% yield). MALDI-TOF-MS (m / z): 728.2 (M + ). 1 HNMR (400MHz, CDCl 3 , ppm): δ7.774-7.755 (d, J=7.6Hz, 4H), 7.519-7.5 (d, J=7.6Hz, 4H), 7.404-7.367 (t, J=7.6Hz, 4H), 7.32- 7.283(t, J=7.6Hz, 4H), 7.271-7.215(m, 10H), 6.899-6.886(dd, J=4.0Hz, J=1.6Hz, 2H), 6.868-6.864(d,...

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Abstract

The invention relates to a complicated diaryl fluorine material and preparation and application methods thereof, which belong to the organic photoelectric material scientific field, in particular to a non-planar complicated bi-polycyclic heteroaryl fluorine material and a friedel-crafts preparation method. And as hole-transporting material, electron transporting material and tricolor luminescence material, the material is applied to organic electric fields of organic flash memory devices and organic luminescence display, etc. With the structure shown above, the material has the advantages of: (1) simple step and temper conditions through the friedel-crafts reaction; (2) amorphous glassy state, high thermal stability and glass transition temperature; (3) high hole or electron mobility, etc. The complicated diaryl fluorine material can become the organic photoelectric functional material with commercial potential.

Description

technical field [0001] The invention belongs to the technical field of organic photoelectric materials. It specifically relates to a non-planar polycyclic heteroaromatic organic semiconductor material and its preparation method, and relates to the application of these materials in the fields of organic electroluminescence, photovoltaic cells, organic electrical storage, organic nonlinear optics, chemical and biological sensing, and organic lasers. Applications. technical background [0002] Since 1987, the Tang Research Group of Kodak Company in the United States [Tang, C.W.; Van Slyke, S.A.Appl.Phys. Lett. 1987, 57, 913.] and the University of Cambridge in 1990 [Burruges, J.H.; Bradley, D.D.C.; Brown, A.B.; Marks, R.N.; Mackay, K.; Friend, R.H.; Burn, P.L.; Holmes, A.B.Nature 1990, 347, 539.] published thin-film organic electroluminescent devices (Organic Light -emitting Diodes) and polymer light-emitting diodes (Polymeric Light-emitting Diodes), organic flat panel displa...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D333/08C07D311/18C07D311/96C07C211/54C07D471/04C07C209/68H01L51/00H01L45/00H01L51/54H01L51/46
Inventor 黄维解令海殷成蓉刘冉冉陈淑芬李崇
Owner NANJING UNIV OF POSTS & TELECOMM
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