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Fluorenyl organic framework material, preparation and application method thereof

An organic framework and fluorene-based technology, which is applied in the field of organic semiconductor materials, can solve the problems of no method for synthesis, no application reported, etc., and achieves the effects of cheap raw materials and simple synthesis method.

Active Publication Date: 2013-08-07
NANJING UNIV OF POSTS & TELECOMM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, there is still no way to synthesize most ladder-like molecules, especially macromolecular ladder-like covalent organic frameworks based on the molecular framework of optoelectronic materials, and the application of such materials has not been reported.

Method used

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  • Fluorenyl organic framework material, preparation and application method thereof
  • Fluorenyl organic framework material, preparation and application method thereof
  • Fluorenyl organic framework material, preparation and application method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1 3

[0073] Example 1. Trimeric (bis(9-octyloxyphenyl-9-bithiophene)fluorene)

[0074]

[0075] 2-Bromo-9-p-octyloxyphenyl-fluoren-9-ol

[0076] 2-bromo-9-octyloxyphenyl-9H-fluoren-9-ol

[0077] Take p-octyloxybromobenzene (8.27g, 29mmol) and magnesium Mg (0.58g, 24mmol) to react to generate Grignard reagent, and dissolve 2-bromofluorenone (3.135g, 12.1mmol) in tetrahydrofuran (20mL) at 60 ℃ for 24 hours, a large amount of white precipitate was formed, and finally saturated NH 3 Aqueous Cl converts Grignard salts to alcohols. After the reaction was completed, it was extracted with ether, 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 oily tertiary alcohol (4.46 g, 90%).

[0078] GC-MS (EI-m / z): 464 / 466 (M + ).

[0079] 1 H NMR (400MHz, CDCl 3 ,ppm):δ7.65-7.65(d,J=7.2Hz,1H),7.64-7.45(m,3H),7.40-7.35(m,3H),7.32-7.24(m,5H),3.91-3.88 (t,J=7.6Hz,2H),2.47(s,1H),1.7...

Embodiment 2、 2

[0115] Example 2, bis(bis(9-octyloxyphenyl-9-(9-hexylcarbazole))fluorene)-(bis(9-octyloxyphenyl-9-bithiophene)fluorene)

[0116]

[0117] "H"-shaped oligomeric tetratertiary alcohol (0.2mmol, 0.385g) and 9-octylcarbazole (0.40mmol, 0.10g) were dissolved in 500ml of anhydrous dichloromethane (dried by anhydrous sodium sulfate in advance), and stirred rapidly In this case, a solution of boron trifluoride in ether dissolved in 50 ml of anhydrous dichloromethane (dried over anhydrous sodium sulfate in advance) was added dropwise. Stir at room temperature for 24h. After the reaction was completed, it was extracted with dichloromethane, dried and rotary evaporated, and purified on a silica gel column with a mixed solvent of petroleum ether:dichloromethane (4:1) to obtain a white solid powder (65.61 mg, 15%).

[0118] MALDI-TOF-MS(m / z):2969 / 2970[M + ].

[0119] 1 H NMR (400MHz, CDCl 3,ppm):δ7.98(br,ArH),7.91(br,ArH),7.81(br,ArH),7.78(br,ArH),7.75(br,ArH),7.73(br,ArH),7.66( b...

Embodiment 3、 2

[0128] Example 3, Bis(bis(9-phenyl-9-bithiophene)fluorene)-(bis(9-octyloxyphenyl-9-bithiophene)fluorene)

[0129]

[0130] 2-Bromo-9-phenyl-fluoren-9-ol

[0131] 2-bromo-9-phenyl-fluoren-9-ol

[0132] Take bromobenzene (4.48g, 29mmol) and magnesium Mg (0.58g, 24mmol) to react to generate Grignard reagent, and react with 2-bromofluorenone (3.135g, 12.1mmol) dissolved in tetrahydrofuran (20mL) at 60°C for 24 hours , generate a large amount of white precipitate, and finally add saturated color NH 3 Cl converts Grignard salts to alcohols. After the reaction was completed, it was extracted with ether, 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 (3.70 g, 90%).

[0133] GC-MS (EI-m / z): 334 / 336 (M + ).

[0134] 1 H NMR (400MHz, CDCl 3 ,ppm):δ7.657-7.655(d,J=7.2Hz,1H),7.638-7.449(m,3H),7.403-7.35(m,3H),7.32-7.235(m,5H),2.512(s ,1H). 13 C...

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Abstract

The invention relates to a fluorenyl organic framework material, a preparation and application method thereof. A material which is provided with a framework structure shaped as a Chinese character ri and constructed by the method disclosed by the invention is taken as a new generation organic semiconductor to be applied to an organic electronic device. The structure of the material is shown in the specification. The material has the characteristics that (1) monomers are synthesized via a Grignard reaction and a Friedel-Crafts reaction, the raw material is inexpensive and the synthesis method is simple; (2) the material has high heat stability and glass transition temperature; (3) the material is good in flexibility and high in solubility; and (4) due to the accumulation effect of diaryl fluorine, the material is good in electrooptic activity. The fluorenyl organic framework material can be applied to the organic electronic field of film devices such as organic light emitting display, organic light storage, organic photovoltaic cells, organic field effect transistors and organic laser, and the like. Electroluminescent devices prepared by using the material disclosed by the invention show satisfactory results in luminance, luminous efficiency and voltage resistance stability.

Description

technical field [0001] The present invention specifically relates to a fluorene-based organic framework material and a preparation method thereof, 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. , belongs to the technical field of organic semiconductor materials. technical background [0002] Since 1987 the Tang Research Group of Kodak Company in the United States [Tang, C.W.; VanSlyke, S.A.Appl.Phys.Lett.1987, 51, 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.Nature1990,347,539.] published thin-film organic electroluminescent devices (Organic Light-emitting Diodes) and polymer Since Polymeric Light-emitting Diodes (Polymeric Light-emitting Diodes), organic flat-panel displays have become anot...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D495/22H01L51/00H10K99/00
Inventor 解令海黄维王龙张广维常永正仪明东
Owner NANJING UNIV OF POSTS & TELECOMM
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