Polyfluorene conjugated polymer with thiophene and other aromatic heterocycle at C9 side chain, and preparation method and applications thereof

A technology of conjugated polymers and heterocyclic compounds, applied in the field of polyfluorene conjugated polymers and its preparation, to achieve good film-forming properties, good carrier injection and transport capabilities, and high energy conversion efficiency

Inactive Publication Date: 2010-07-14
SOUTH CHINA NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The synthesis of fluorene monomers and polymers with side chains connected to aromatic heterocycles such as thiophene and their applications in polymer solar cells have not been reported in the literature.

Method used

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  • Polyfluorene conjugated polymer with thiophene and other aromatic heterocycle at C9 side chain, and preparation method and applications thereof
  • Polyfluorene conjugated polymer with thiophene and other aromatic heterocycle at C9 side chain, and preparation method and applications thereof
  • Polyfluorene conjugated polymer with thiophene and other aromatic heterocycle at C9 side chain, and preparation method and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Example 1 Synthesis of 2,7-dibromo-9,9-bis-aromatic heterocyclic substituted fluorene

[0035] According to the method disclosed in Adv.Funct.Mater.2007,17,1917, with 2,7-dibromo-9,9-bis(4-triphenylamine-7-thiophene-2,1,3-benzothiadiazole The preparation of -6-hexyl)phenoxyfluorene is illustrated as an example. The synthetic route is as follows:

[0036]

[0037] (1) 4-Triphenylamine boronic acid

[0038]

[0039] In a 250ml three-necked flask, add 5g (15.4mmol) 4-bromotriphenylamine, 60mLTHF, drop 6.7mL n-BuLi (2.5M in n-hexane) when the temperature drops to -78°C, and stir at -78°C after the dropwise addition 1h, then add 23.1mmol trimethyl borate, rise to room temperature and react overnight, then add 10mL of 2M hydrochloric acid, stir for 5h, the reaction solution is extracted with ether, the organic layer is washed with anhydrous MgSO 4 After drying, the solvent was drained and the petroleum ether / silica gel column chromatography was used to obtain a white...

Embodiment 2

[0069] According to the method disclosed in J.Mater.Chem., 2002,12,2887, the synthesis of 4,7-bis(5-bromo-2-thiophene)-2,1,3-benzothiadiazole is For example, the synthesis route is shown in the figure below:

[0070]

[0071] (1) Synthesis of 3-butyl-2-phenostannane

[0072]

[0073] In a 250ml three-neck flask, add 5ml thiophene and 30ml THF, cool down to -30°C with liquid nitrogen / isopropanol, add 1.6M n-butyllithium dropwise, then react at -30°C for 30min, then add SnBu dropwise 3 Cl, react at -30°C for 2h. Extract with ether, anhydrous MgSO 4 Dry, remove the solvent under reduced pressure, and use neutral Al 2 o 3 / petroleum ether (30-60°C) column chromatography to obtain a colorless and transparent oily liquid. Yield: 72%. 1 H NMR (CDCl 3 , 500 MHz, ppm) 7.71 (1H, dd) 7.32 (1H, dd), 7.27 (1H, dd), 0.96-1.74 (27H, m, 3×Bu).

[0074] (2) Synthesis of 4,7-dithiophen-2-yl-2,1,3-benzothiadiazole

[0075]

[0076] In a 250ml three-necked flask, add 2g 4,7-di...

Embodiment 32

[0080] Example 32, Preparation of 7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-diyl)-9,9-dioctylfluorene

[0081]

[0082] Synthesize 2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-diyl)-9,9 according to the method disclosed in document Macromolecules, 1997,30,7686 -Dioctylfluorene.

[0083] (1) Synthesis of 2,7-dibromo-9,9-dioctylfluorene

[0084]

[0085] Add 15.0g (0.048mol) 2,7-dibromofluorene and 200ml dimethyl sulfoxide into a three-necked flask equipped with a stirrer, and add 0.09g (0.39mol) tetrabutylammonium bromide, 15ml 50% sodium hydroxide solution and 27.8g (0.144mol) 1-bromooctane were reacted at room temperature for 3h, water and ether were added to the reactant, the organic layer was separated, washed with saturated brine, and dried over anhydrous magnesium sulfate. Filtrate, evaporate the solvent, remove the solvent diethyl ether, pass through a column with silica gel / petroleum ether, and separate the desired components. Yield: 88%. m.p.: 52-54°C....

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Abstract

The invention discloses a polyfluorene conjugated polymer with thiophene and other aromatic heterocycle at C9 side chain, and a preparation method and applications thereof. The polyfluorene conjugated polymer with thiophene and other aromatic heterocycle at C9 side chain has the structural formula shown as the formula (I) or the formula (II), wherein R1, R2, R3 and R4 are selected from the group consisting of C1-C20 alkyl, alkoxy, phenyl or phenoxy; Ar1 and Ar2 are identical or different heterocyclic compounds containing at least one atom of the group consisting of sulfur, nitrogen and selenium; Ar3 is a heterocyclic compound containing at least one atom of the group consisting of sulfur and nitrogen; x is not less than 15 but not more than 85, y is not less than 15 but not more than 85; and n is a natural number. The polymer according to the invention has excellent film forming performance, thermal stability and chemical stability, includes outstanding carrier injection and transfer ability, and can be used for the preparation of polymer solar cells, electroluminescent devices or field effect transistors.

Description

technical field [0001] The invention relates to the field of electroluminescent materials, in particular to a polyfluorene conjugated polymer with aromatic heterocycles such as thiophene in the side chain at the C9 position, a preparation method and application thereof. Background technique [0002] The production process of polymer solar cells (PPVC) is simple, and it can be prepared in a large area by coating, printing, etc., and can be made into flexible products using elastic substrates. Inexpensive solar photovoltaic cells have a broad market in general industrial and consumer appliances. The light absorption of polymer-based solar cells mainly comes from polymers. Polymers absorb photons to generate photogenerated carriers, and charge separation forms photocurrents. Therefore, improving the light absorption of polymers is the key to improving photoelectric conversion efficiency. At present, the energy conversion efficiency of polymer solar cells is still relatively lo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/12H01L51/46H01L51/54
CPCY02E10/50Y02E10/549Y02P70/50
Inventor 侯琼曾祥华郭婷许鑫
Owner SOUTH CHINA NORMAL UNIVERSITY
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