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A kind of oligomer based on fluorene and its synthesis method and application

An oligomer and phenyl technology, which is applied in the field of new fluorene-based oligomers and their synthesis, can solve the problem of high work function, and achieve the effects of lowering potential barriers, single structure, good solubility and film-forming properties

Inactive Publication Date: 2016-06-22
WUHAN INSTITUTE OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Metal cathodes such as Al, Ag, and Au that are stable in air can improve battery stability but have high work functions

Method used

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  • A kind of oligomer based on fluorene and its synthesis method and application
  • A kind of oligomer based on fluorene and its synthesis method and application
  • A kind of oligomer based on fluorene and its synthesis method and application

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example 1

[0036] 1) Synthesis of 2-bromo-9,9-bis(2-ethylmorpholine)fluorene (M1):

[0037] Dissolve 2-bromofluorene (4.9g, 20mmol), 4-(2-chloroethyl)morpholine hydrochloride (9.3g, 50mmol) and potassium hydroxide (11.2g, 200mmol) in 200mL of tetrahydrofuran. The reaction was conducted at 80°C for 48h under water and oxygen-free Ar environment. After the reaction, the solvent tetrahydrofuran was distilled under reduced pressure. The product was first purified by column chromatography (silica gel, ethyl acetate: methanol = 10:1 as the eluent) to obtain a milky white solid recrystallized from petroleum ether, and finally white crystals 6.5 g, the yield was 69%.

[0038] 2) Synthesis of 1,4-bis[9,9-bis(2-ethylmorpholine)fluorene]benzene (FNO-B-FNO):

[0039] In a 50mL three-necked flask, M1 (471mg, 1mmol), 1.4-benzenediboronic acid (83mg, 0.5mmol), palladium tetraphenylphosphide (15mg, 0.01mmol), potassium carbonate (1.38g, 10mmol) were added to 10mL Toluene 5mL water mixture. The reaction sys...

example 2

[0041] 1) Synthesis of 2,7-dibromo-9,9-dioctylfluorene (M2)

[0042] Put 2,7-dibromofluorene (5g, 15.5mmol), tetrabutylammonium bromide (0.1g, 0.31mmol), 200mL dimethyl sulfoxide in a three-necked flask under vigorous stirring to form a suspension, and drop in 50wt % Sodium hydroxide aqueous solution 5mL, after 1h reaction, then 1-bromooctane (6.2g, 31mmol) was added dropwise. The reaction mixture was stirred at room temperature for 6 hours, then the reaction was stopped, and extracted with ether (150 mL×3), the organic phase was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled under reduced pressure, and the product was recrystallized in a methanol / acetone mixed solvent to obtain 8 g of white needle crystals, with a yield of 80%.

[0043] 2) Synthesis of 2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborane-diyl)-9,9-dioctylfluorene (M3)

[0044] Dissolve M2 (5.4g, 10mmol) in 60mL tetrahydrofuran, add 15mL 1.6mol / L n-butyllithium dropwise ...

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Abstract

The invention discloses a fluorene-based oligomer and its synthesis method and application. The method comprises the following steps: 2-bromofluorene, 4-(2-chloroethyl)morpholine hydrochloride and potassium hydroxide are heated to reflux under the protection of an inert gas, and the reaction crude product is recrystallized in petroleum ether after silica gel column chromatography , to obtain ethyl morpholine-substituted bromofluorene monomers; ring compounds with brominated ends react with alkyl bromide, 2-isopropyl-4,4,5,5-tetramethyl-1 under palladium catalyst conditions , 3,2-dioxaborane reaction to obtain cyclic compounds with borate esters at both ends; mix the above-mentioned fluorene monomers with cyclic compounds, reflux reaction under the protection of inert gas, cool and purify to obtain fluorene-based of oligomers. The invention has good electron extraction and transport properties, effectively reduces the potential barrier between the organic active layer and the metal electrode, and can be applied to the modification of the cathode or anode of organic optoelectronic devices such as polymer electroluminescent diodes and organic solar cells Floor.

Description

Technical field [0001] The invention belongs to the field of organic solar cells, and specifically relates to a novel fluorene-based oligomer and its synthesis method and application. Background technique [0002] Organic solar cells have received widespread attention from all walks of life due to their unique advantages. Polymer electroluminescent materials are used in solar cells. They have low price, simple device manufacturing process, low driving voltage, high brightness, high efficiency, etc., and they have good mechanical properties, processing properties and thermal stability, and overcome the disadvantages of inorganic materials. Disadvantages make polymer electroluminescent materials a new research focus in the field of electroluminescence. [0003] The basic sandwich structure of organic solar cells mainly includes an active layer film of organic semiconductors and electrodes at both ends. In order to obtain high-efficiency battery efficiency, it is important to control...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D295/02C07D295/023H01L51/46H01L51/44
CPCC07D295/02C07D295/023H10K85/656Y02E10/549
Inventor 刘治田刘菁李超
Owner WUHAN INSTITUTE OF TECHNOLOGY
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