CN104072727A - 2, 7-fluorene conjugated polymer containing phosphatidylcholine and preparation method and application thereof - Google Patents

2, 7-fluorene conjugated polymer containing phosphatidylcholine and preparation method and application thereof Download PDF

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CN104072727A
CN104072727A CN201410284177.9A CN201410284177A CN104072727A CN 104072727 A CN104072727 A CN 104072727A CN 201410284177 A CN201410284177 A CN 201410284177A CN 104072727 A CN104072727 A CN 104072727A
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fluorenes
base
phosphatidylcholine
preparation
alkyl
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陈军武
阚媛媛
刘珠林
曹镛
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South China University of Technology SCUT
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South China University of Technology SCUT
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    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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Abstract

The invention discloses a 2, 7-fluorene conjugated polymer containing phosphatidylcholine and a preparation method and application thereof. The 2, 7-fluorene conjugated polymer containing phosphatidylcholine is prepared by copolymerization of multiple conjugated aroma monomers and phosphatidylcholine-substituted 2, 7-fluorene monomer. The novel 2, 7-fluorene conjugated polymer prepared by the method can be used for manufacturing photoelectric functional devices such as an interface layer in contact with the cathode in organic light emitting diodes and organic photovoltaic cells.

Description

A kind of containing 2 of phosphatidylcholine base, conjugated polymers of 7-fluorenes and preparation method thereof and application
Technical field
The present invention relates to a kind of new polymers and preparation method thereof and application, be specifically related to a kind of containing 2 of phosphatidylcholine base, conjugated polymers of 7-fluorenes and preparation method thereof and application.
Background technology
Since Japanese scientist's Hideki Shirakawa in 1977 is found polyacetylene conduction, this being called as the conductive polymers of " the 4th generation polymer " material attracted numerous scientists to study with its outstanding photoelectric properties.Conducting polymer is compared with the inorganic materials with identical or close purposes, has density low, and easily processing, synthesizes the advantages such as range of choice is wide.Due to the conjugate property of this class material structure, make its can transmission charge, stimulated luminescence, thus can or potential may being applied on many electronics or opto-electronic device, for example comprise polymer LED, photovoltaic cell, field effect transistor etc.Potential application prospect and wide application field impel scientist competitively to study this class to have the conjugation material of photoelectric activity, comprise the small molecules of multiple conjugated structure, and polyacetylene, polypyrrole, Polythiophene, polyaniline, poly-fluorenes, polycarbazole etc.
Since 20 century 70s, the conjugated polymers of many different structures and function emerges in large numbers one after another, wherein contains the performance that differs from common conjugated polymers that the polymer materials of hydrophilic radical possesses and more and more causes people's interest.For the preliminary study of this class material since the eighties in last century, the existence of conjugated main chain makes this base polymer have the essential characteristic of general neutral semi-conducting polymer, and the existence of alkyl chain terminal hydrophilic group group makes this class material possess some distinguished chemistry and physicalies.Due to the existence of strong hydrophilicity group on side chain, most polymers can be dissolved in the organic solvent or water of polarity, this class material can be processed in many eco-friendly solvents (such as alcohol and water), and the photoelectric device that their this special solvabilities are also prepared multilayer for us provides may.Simultaneously, some special functional group can have with some protein, nucleic acid etc. the metal ion generation complexing action of bioactive material or different volumes, and then the difference response that shows main polymer chain spectrum, this phenomenon makes this class material aspect chemistry and biosensor, have application widely.Because absorption mutually occurs the different ions with positive and negative charge, affect piling up between main polymer chain, this base polymer can form the state of aggregation pattern with supramolecular structure; Meanwhile, the ion with positive and negative charge can move under the effect of electric field, and the carrier transmission characteristics of conjugated polymer main chain and energy band structure also make this class material in the photoelectric device of multilayer, also become the effective subsidiary material of a class.
In recent years, researchist is making great efforts to seek to improve polymer LED always, photovoltaic cell, and the method for field-effect transistor, chemistry and bioprobe performance, the preparation of material is one of very important key element.So being all devoted to exploitation, many research groups there is high-quantum efficiency, high color purity, the luminescence polymer that contains hydrophilic radical of good stability; And carrier mobility is high, energy band structure is controlled, has special deliquescent interface function material.Realize these targets, need to develop the more novel conjugated molecule that contains hydrophilic radical and polymer materials.
2,7-fluorenes has been widely used in constructing numerous conjugated polymerss as a kind of conjugate unit, such as " polymer circular " (the 9th phase 69-78 page in 2008) done more detailed introduction at this point.And some contain 2 of hydrophilic radical, the conjugated polymers of 7-fluorenes has also caused gazing at of researchist, and " chemistry can be commented on (Chemical Society Reviews) " (the 39th volume 2500-2521 page in 2010) introduced about the chemical structure of polymkeric substance and the application in photoelectric functional device thereof.
Summary of the invention
The object of the invention is to the deficiency existing for prior art, a kind of 2 of phosphatidylcholine base that contains is provided, the conjugated polymers of 7-fluorenes, has potential special solvability and energy band structure, can be used for preparation and makes photoelectric functional device.
The present invention also aims to provide described containing 2 of phosphatidylcholine base, the preparation method of the conjugated polymers of 7-fluorenes.
The present invention also aims to provide described containing 2 of phosphatidylcholine base, the application of the conjugated polymers of 7-fluorenes in Organic Light Emitting Diode and organic photovoltaic battery.
Of the present invention containing 2 of phosphatidylcholine base, the conjugated polymers of 7-fluorenes has following structure:
Wherein, R 1for the alkyl that carbon number is 1～4, m is 2～12; 0<x≤1,0≤y<1, x+y=1; N=3-1000; Ar is conjugate unit, comprises one or more combinations in the aromatic heterocycle that aromatic nucleus that ethene support group, acetylene support group, hydrocarbon atom form, aromatic heterocycle that carbon nitrogen hydrogen atom forms, aromatic heterocycle that carbon nitrogen oxygen hydrogen atom forms, aromatic heterocycle that carbon sulphur hydrogen atom forms, aromatic heterocycle that carbon silicon hydrogen atom forms, aromatic heterocycle that carbon nitrogen sulphur hydrogen atom forms and carbon silicon sulphur hydrogen atom form.
In above-mentioned polymkeric substance, described Ar conjugate unit can be with substituted radical, and substituted radical comprises one or more combinations in alkyl, fluoro-alkyl, alkoxyl group, ester group, carbonyl.
A kind of containing 2 of phosphatidylcholine base, the preparation method of the conjugated polymers of 7-fluorenes, will contain 2 of phosphatidylcholine base, and 7-fluorenes monomer and Ar monomer carry out copolymerization preparation; Use containing phosphatidylcholine base 2,7-fluorenes monomer structure is as follows:
Wherein, R 2for reaction active groups, comprise bromo, iodo, chloro, trialkyltin, 4,4,5,5-tetramethyl--1, the one in 3,2-dioxa pentaborane-2-base, R 3for the alkyl that carbon number is 1～4, z is 2～12; The carbon number of the alkyl in described trialkyltin is 1～4.
The structure of the Ar monomer using is: R 4-Ar-R 4, wherein R 4for reaction active groups, comprise bromo, iodo, chloro, trialkyltin, 4,4,5,5-tetramethyl--1, the one in 3,2-dioxa pentaborane-2-base; The carbon number of the alkyl in described trialkyltin is 1～4.
A kind of containing 2 of phosphatidylcholine base, the conjugated polymers of 7-fluorenes is applied to be made in photoelectric functional device.
In above-mentioned application, described photoelectric functional device is Organic Light Emitting Diode.
In above-mentioned application, described photoelectric functional device is organic photovoltaic battery.
Compared with prior art, tool of the present invention has the following advantages and technique effect: adopt containing 2 of phosphatidylcholine base, the conjugated polymers of 7-fluorenes, as cathodic modification layer, can successfully be prepared Organic Light Emitting Diode and the organic photovoltaic battery device with multilayered structure.In organic light emitting diode device, containing 2 of phosphatidylcholine base, the auxiliary electronic injection of having realized cathodic area of the conjugated polymers cathodic modification layer of 7-fluorenes.In organic photovoltaic battery device, containing 2 of phosphatidylcholine base, the auxiliary electron collection that has realized cathodic area of the conjugated polymers cathodic modification layer of 7-fluorenes.
Embodiment
Come containing 2 of phosphatidylcholine base below in conjunction with specific embodiment, the preparation and application of the conjugated polymers of 7-fluorenes are further described.But protection domain of the presently claimed invention is not limited to the related scope of embodiment.
Embodiment 1:
2-alkoxyl group-2-oxygen-1, the preparation of 3,2-dioxaphospholane, reaction formula is as follows:
With preparation 2-oxyethyl group-2-oxygen-1,3,2-dioxaphospholane is that example is explained.Under the protection of inert atmosphere, by chloro-the 2-of 0.29 mole 2-oxygen-1,3,2-dioxaphospholane is dissolved in 250 milliliters of dry toluene, and is cooled to subzero 5 degrees Celsius.Each 0.29 mole of dry ethanol and triethylamine mixed, dropwise join in reaction flask.After adding completely, mixture is raised to gradually room temperature and reacts 1.5 hours.Filter white triethylamine hydrochloride filtrate is concentrated.Underpressure distillation obtains final product.Warp 1h NMR test (δ (ppm): 1.3 (3H), 4.1 (2H), 4.4 (4H)) is indicated as target product 2-oxyethyl group-2-oxygen-1,3,2-dioxaphospholane.
2-alkoxyl group-2-oxygen-1, the alkoxyl group in 3,2-dioxaphospholane also comprises: methoxyl group, propoxy-and butoxy etc., but be not limited only to this.
Embodiment 2:
2,7-bis-is bromo-9, the preparation of 9-bis-(3'-(N, N dimethylamine base) propyl group)-fluorenes, and reaction formula is as follows:
Under the protection of inert atmosphere, by 12 mmoles 2,7-dibromo fluorenes is dissolved in the dimethyl sulfoxide (DMSO) of 60 milliliters, and the aqueous sodium hydroxide solution that is 50% by the Tetrabutyl amonium bromide of 80 milligrams and 8 milliliters of massfractions adds in reaction flask successively.By chloro-the 3-of 32 mmoles N, N-dimethyl propylene amine hydrochlorate is dissolved in the dimethyl sulfoxide (DMSO) of 20 milliliters, and dropwise joins in reaction flask with syringe.Reaction mixture at room temperature reacts 6 hours.Add the salt generating in 50 ml water solubilizing reactions, and be extracted with ethyl acetate, organic phase is used respectively 10% sodium hydroxide, and organic phase is repeatedly isolated in distilled water and salt solution washing afterwards.Organic phase anhydrous magnesium sulfate drying, except desolventizing, obtains white solid with silica gel chromatographic column separating-purifying after filtering.Warp 1h NMR tests (δ (ppm): 7.82-7.80 (2H), 7.69 (2H), 7.56-7.53 (2H), 2.04-2.00 (4H), 1.92-1.88 (16H), 0.60-0.52 (4H)) be indicated as target product 2,7-bis-bromo-9,9-bis-(3'-(N, N dimethylamine base) propyl group)-fluorenes.
Embodiment 3:
2,7-bis-is bromo-9, the preparation of 9-bis-(bromine alkyl) fluorenes, and reaction formula is as follows:
Bromo-9 to prepare 2,7-bis-, 9-bis-(6-bromine hexyl) fluorenes is that example is explained.Under the protection of nitrogen, by 15 mmoles 2,7-dibromo fluorenes, 30 milliliter 1,6-dibromo-hexane, the aqueous solution of 30 milliliters of sodium hydroxide that 0.1 gram of Tetrabutyl amonium bromide and massfraction are 50% joins in reaction flask, is heated to 60 DEG C of reactions 4 hours.After question response finishes, mixing solutions is cooled to room temperature, with dichloromethane extraction, repeatedly isolates afterwards organic phase with saturated common salt water washing.Organic phase anhydrous magnesium sulfate drying, except desolventizing, does not have 1 of reaction after filtering, and the underpressure distillation of 6-dibromo-hexane is removed, and recycle silicon glue chromatographic column separating-purifying obtains white solid.Warp 1h NMR tests (δ (ppm): 7.54 (2H), 7.47 (2H), 7.43 (2H), 3.29 (4H), 1.93 (4H), 1.67 (4H), 1.20-1.05 (8H), 0.58 (4H)) be indicated as target product 2,7-bis-is bromo-9,9-bis-(6-bromine hexyl) fluorenes.
2,7-bis-is bromo-9, and the alkyl in 9-bis-(bromine alkyl) fluorenes also comprises: 2-bromotrifluoromethane, and 4-brombutyl, 8-bromine octyl group, 10-bromine decyl and 12-bromo-dodecane base etc., but be not limited only to this.
Embodiment 4:
2,7-bis-is bromo-9, the preparation of 9-bis-((N, N dimethylamine base) alkyl)-fluorenes, and reaction formula is as follows:
Bromo-9 to prepare 2,7-bis-, 9-bis-(6'-(N, N dimethylamine base) hexyl)-fluorenes is that example is explained.Under the protection of inert atmosphere, by 2 of 50 mmoles, 7-bis-bromo-9; 9-bis-(6-bromine hexyl) fluorenes is dissolved in the dimethyl formamide of 300 milliliters; be cooled to subzero 78 degrees Celsius, once add the dimethylamine of 30 milliliters, be warmed up to gradually return stirring and spend the night.After question response finishes, mixing solutions is cooled to room temperature, mixture is poured in frozen water, with dichloromethane extraction, repeatedly isolate afterwards organic phase with distilled water wash.Organic phase anhydrous magnesium sulfate drying, except desolventizing, obtains white solid with silica gel chromatographic column separating-purifying after filtering.Through ultimate analysis (C, 60.88; H, 7.67) test is indicated as target product 2, and 7-bis-is bromo-9,9-bis-(6'-(N, N dimethylamine base) hexyl)-fluorenes.
2,7-bis-is bromo-9, and the alkyl in 9-bis-((N, N dimethylamine base) alkyl)-fluorenes also comprises: ethyl, and butyl, octyl group, decyl and dodecyl etc., but be not limited only to this.
Embodiment 5:
2,7-bis-is bromo-9, the preparation of 9-bis-(phosphatidylcholine base) fluorenes, and reaction formula is as follows:
With preparation m=3 and R 1for 2 of methyl, 7-bis-is bromo-9, and 9-bis-(phosphatidylcholine base) fluorenes is that example is explained.Under the protection of inert atmosphere, 2 of 3.2 mmoles, 7-bis-bromo-9; 9-bis-(3'-(N, N dimethylamine base) propyl group)-fluorenes, 2-methoxyl group-2-oxygen-1 of 9 mmoles; 3,2-dioxaphospholane is dissolved in the acetonitrile of 30 milliliters, is heated to 70 degrees Celsius of reactions 2 days.Revolve and steam except desolventizing, obtain colourless liquid with silica gel chromatographic column separating-purifying.Warp 1h NMR tests (δ (ppm): 7.87 – 7.82 (2H), 7.78 (2H), 7.58 (2H), 3.95 – 3.86 (4H), 3.71 – 3.67 (2H), 3.66 – 3.64 (2H), 3.31 (8H), 2.71 (4H), 2.44 (12H), 2.14 – 1.99 (4H), 0.99 – 0.82 (4H)) be indicated as m=3 and R 1for the target product 2 of methyl, 7-bis-is bromo-9,9-bis-(phosphatidylcholine base) fluorenes.
2,7-bis-is bromo-9, and the m numerical value in 9-bis-(phosphatidylcholine base) fluorenes also comprises: 2,4,6,8,10 and 12 etc., and R 1also comprise ethyl, propyl group, butyl, but be not limited only to this.
Embodiment 6:
2,7-pair-(4,4,5,5-tetramethyl--1,3,2-dioxa pentaborane-2-yl)-9, the preparation of 9-bis-(phosphatidylcholine base) fluorenes, reaction formula is as follows:
With preparation m=3 and R 1for 2 of methyl, 7-pair-(4,4,5,5-tetramethyl--1,3,2-dioxa pentaborane-2-yl)-9,9-bis-(phosphatidylcholine base) fluorenes is that example is explained.Under the protection of inert atmosphere, by the m=3 of 4.05 mmoles and R 1for 2 of methyl, 7-bis-is bromo-9, and 9-bis-(phosphatidylcholine base) fluorenes is dissolved in the tetrahydrofuran (THF) of 30 milliliters, and is cooled to-78 degrees Celsius.With syringe dropwise to the n-Butyl Lithium (2.5M hexane solution) that adds 8.5 mmoles in reaction flask.Reaction mixture reacts 45 minutes under-78 degrees Celsius.The Virahol tetramethyl ethylene ketone boric acid ester of 16.2 mmoles joins in reaction solution fast, is raised to gradually room temperature reaction and stirs 24 hours.After question response finishes, reaction product is poured in distilled water, be extracted with ethyl acetate, repeatedly isolate afterwards organic phase with distilled water wash.Organic phase anhydrous magnesium sulfate drying, except desolventizing, obtains white solid with silica gel chromatographic column separating-purifying after filtering.Through ultimate analysis test (C, 57.23; H, 7.86) be indicated as m=3 and R 1for the target product 2 of methyl, 7-pair-(4,4,5,5-tetramethyl--1,3,2-dioxa pentaborane-2-yl)-9,9-bis-(phosphatidylcholine base) fluorenes.
2,7-pair-(4,4,5,5-tetramethyl--1,3,2-dioxa pentaborane-2-yl)-9, the m numerical value in 9-bis-(phosphatidylcholine base) fluorenes also comprises: 2,4,6,8,10 and 12 etc., and R 1also comprise ethyl, propyl group, butyl, but be not limited only to this.
Embodiment 7:
The preparation of poly-(phosphatidylcholine base fluorenes), reaction formula is as follows:
Under the protection of inert atmosphere, by two-(4, 4, 5, 5-tetramethyl--1, 3, 2-dioxa pentaborane-2-yl) replace with 2 of phosphatidylcholine base, 7-fluorenes and two bromines replace with 2 of phosphatidylcholine base, each 0.5 mmole of 7-fluorenes, the tetrakis triphenylphosphine palladium of 10 milligrams, several Aliquat336, with 2 ml concns be the wet chemical of 2 mol/L, be dissolved in 10 milliliters of toluene, heating reflux reaction 48 hours, after reaction finishes, mixing solutions is poured in 300 ml methanol, by the precipitation dissolution filter again of collecting, the crude product obtaining was with washing with acetone 12 hours and be dried 24 hours in a vacuum, obtain light grey polymkeric substance.
The number-average molecular weight of this polymkeric substance is 10300, and weight-average molecular weight is 21000.There is UV absorption peak in 390 nanometers in the tetrahydrofuran solution of polymkeric substance.There is glow peak in 430 nanometers in the fluorescence spectrum of the tetrahydrofuran solution of polymkeric substance.
Embodiment 8:
Phosphatidylcholine base fluorenes and 2,7-pair-(4,4,5,5-tetramethyl--1,3,2-dioxa pentaborane-2-yl)-9, the preparation of the conjugated polymers of 9-dioctyl fluorene, reaction formula is as follows:
In nitrogen atmosphere downhill reaction bottle, add 2, 7-dibromo replace with 2 of phosphatidylcholine base, 7-fluorenes and 2, 7-two-(4, 4, 5, 5-tetramethyl--1, 3, 2-dioxa pentaborane-2-yl)-9, each 0.5 mmole of 9-dioctyl fluorene, the tetrakis triphenylphosphine palladium of 10 milligrams, several Aliquat336, with 2 ml concns be the wet chemical of 2 mol/L, be dissolved in 10 milliliters of toluene, heating reflux reaction 48 hours, after reaction finishes, mixing solutions is poured in 300 ml methanol, by the precipitation dissolution filter again of collecting, the crude product obtaining was with washing with acetone 12 hours and be dried 24 hours in a vacuum, obtain greyish-green polymkeric substance.
The number-average molecular weight of resulting polymers is 9500, and weight-average molecular weight is 19900.There is UV absorption peak in 386 nanometers in the tetrahydrofuran solution of polymkeric substance.There is glow peak in 440 nanometers in the fluorescence spectrum of polymkeric substance in tetrahydrofuran solution.
Embodiment 9:
Phosphatidylcholine base fluorenes and two-(4,4,5,5-tetramethyl--1,3,2-dioxa pentaborane-2-yl)-9, the preparation of the conjugated polymers of 9-bis-(3'-(N, N dimethylamine base) propyl group)-fluorenes, reaction formula is as follows:
Method is with embodiment 8.With two-(4,4,5,5-tetramethyl--1,3,2-dioxa pentaborane-2-yl)-9,9-bis-(3'-(N, N dimethylamine base) propyl group)-fluorenes replaces 2,7-two-(4,4,5,5-tetramethyl--1,3,2-dioxa pentaborane-2-yl)-9,9-dioctyl fluorene.The number-average molecular weight of gained white polymer is 11000, and weight-average molecular weight is 21000.
Embodiment 10:
The preparation of the conjugated polymers of phosphatidylcholine base fluorenes and benzene, reaction formula is as follows:
Under the protection of inert atmosphere, by two-(4, 4, 5, 5-tetramethyl--1, 3, 2-dioxa pentaborane-2-yl) replace fluorenes 0.5 mmole with phosphatidylcholine base, two bromines replace with phosphatidylcholine base fluorenes 0.49 mmole, 1, 4-dibromobenzene 0.01 mmole, the tetrakis triphenylphosphine palladium of 10 milligrams, several Aliquat336, with 2 ml concns be the wet chemical of 2 mol/L, be dissolved in 10 milliliters of toluene, heating reflux reaction 48 hours, after reaction finishes, mixing solutions is poured in 300 ml methanol, by the precipitation dissolution filter again of collecting, the crude product obtaining was with washing with acetone 12 hours and be dried 24 hours in a vacuum, obtain light grey polymkeric substance.The number-average molecular weight of this polymkeric substance is 21000, and weight-average molecular weight is 39000.
Embodiment 11:
The preparation of the conjugated polymers of phosphatidylcholine base fluorenes and carbazole, reaction formula is as follows:
Under the protection of inert atmosphere, two bromines are replaced with phosphatidylcholine base fluorenes 0.01 mmole, N-n-octyl-2, 7-two-(4, 4, 5, 5-tetramethyl--1, 3, 2-dioxa pentaborane-2-yl) carbazole 0.5 mmole, N-n-octyl-2, 7-dibromo carbazole 0.49 mmole, the tetrakis triphenylphosphine palladium of 10 milligrams, several Aliquat336, with 2 ml concns be the wet chemical of 2 mol/L, be dissolved in 10 milliliters of toluene, heating reflux reaction 48 hours, after reaction finishes, mixing solutions is poured in 300 ml methanol, by the precipitation dissolution filter again of collecting, the crude product obtaining was with washing with acetone 12 hours and be dried 24 hours in a vacuum, obtain light grey polymkeric substance.The number-average molecular weight of this polymkeric substance is 13000, and weight-average molecular weight is 29000.
Embodiment 12:
The preparation of the conjugated polymers of phosphatidylcholine base fluorenes and benzotriazole, reaction formula is as follows:
Under the protection of inert atmosphere, by two-(4, 4, 5, 5-tetramethyl--1, 3, 2-dioxa pentaborane-2-yl) replace fluorenes 0.5 mmole with phosphatidylcholine base, fluorenes 0.4 mmole with phosphatidylcholine base that two bromines replace, 2-n-octyl-4, 7-dibromo benzotriazole 0.1 mmole, the tetrakis triphenylphosphine palladium of 10 milligrams, several Aliquat336, with 2 ml concns be the wet chemical of 2 mol/L, be dissolved in 10 milliliters of toluene, heating reflux reaction 48 hours, after reaction finishes, mixing solutions is poured in 300 ml methanol, by the precipitation dissolution filter again of collecting, the crude product obtaining was with washing with acetone 12 hours and be dried 24 hours in a vacuum, obtain light grey polymkeric substance.The number-average molecular weight of this polymkeric substance is 15000, and weight-average molecular weight is 39000.
Embodiment 13:
The preparation of the conjugated polymers of phosphatidylcholine base fluorenes and thiophene, reaction formula is as follows:
Method is with embodiment 12.With 2,5-dibromo thiophene replacement 2-n-octyl-4,7-dibromo benzotriazole.The number-average molecular weight of the faint yellow polymkeric substance of gained is 15000, and weight-average molecular weight is 32000.
Embodiment 14:
The preparation of the conjugated polymers of phosphatidylcholine base fluorenes and silicon fluorenes, reaction formula is as follows:
Under the protection of inert atmosphere, by two-(4, 4, 5, 5-tetramethyl--1, 3, 2-dioxa pentaborane-2-yl) replace the fluorenes with phosphatidylcholine base and 9, 9-di-n-octyl-2, each 0.5 mmole of 7-dibromo silicon fluorenes, the tetrakis triphenylphosphine palladium of 10 milligrams, several Aliquat336, with 2 ml concns be the wet chemical of 2 mol/L, be dissolved in 10 milliliters of toluene, heating reflux reaction 48 hours, after reaction finishes, mixing solutions is poured in 300 ml methanol, by the precipitation dissolution filter again of collecting, the crude product obtaining was with washing with acetone 12 hours and be dried 24 hours in a vacuum, obtain white polymer.The number-average molecular weight of this polymkeric substance is 16000, and weight-average molecular weight is 35000.
Embodiment 15:
The preparation of the conjugated polymers of phosphatidylcholine base fluorenes and diazosulfide, reaction formula is as follows:
Method is with embodiment 12.Bromo-2,1 with 4,7-bis-, 3-diazosulfide replaces 2-n-octyl-4,7-dibromo benzotriazole.The number-average molecular weight of the faint yellow polymkeric substance of gained is 12000, and weight-average molecular weight is 27000.
Embodiment 16:
The preparation of phosphatidylcholine base fluorenes and 4,7-bithiophene benzthiadiazole's conjugated polymers, reaction formula is as follows:
Method is with embodiment 12.With two (the bromo-2-thiophene of 5-)-2,1 of 4,7-, 3-diazosulfide replaces 2-n-octyl-4,7-dibromo benzotriazole.The number-average molecular weight of gained red polymer is 6500, and weight-average molecular weight is 15500.
Embodiment 17:
The preparation of the conjugated polymers of phosphatidylcholine base fluorenes and 5,8-, bis-thiophene-quinoxaline, reaction formula is as follows:
Method is with embodiment 14.With two (the bromo-2-thiophene of 5-)-2 of 5,8-, two (to the octyloxyphenyl) quinoxalines of 3-replace 9,9-di-n-octyl-2,7-dibromo silicon fluorenes.The number-average molecular weight of gained red polymer is 7000, and weight-average molecular weight is 17100.
Embodiment 18:
The preparation of the conjugated polymers of phosphatidylcholine base fluorenes and 3,6-, bis-thiophene-pyrrolo-[3,4-c] pyrroles-Isosorbide-5-Nitrae-diketone, reaction formula is as follows:
Method is with embodiment 14.With two (the bromo-2-thiophene of 5-)-2 of 3,6-, 5-di-n-hexyl-pyrrolo-[3,4-c] pyrroles-Isosorbide-5-Nitrae-diketone replaces 9,9-di-n-octyl-2,7-dibromo silicon fluorenes.The number-average molecular weight of gained purple polymkeric substance is 9000, and weight-average molecular weight is 18500.
Embodiment 19:
Two (bithiophene)-3 of phosphatidylcholine base fluorenes and 2,5-, the preparation of the conjugated polymers of 4-phenylbenzene Silole, reaction formula is as follows:
Method is with embodiment 14.With 1,1-di-n-hexyl-2, two (the 5 '-bromo-thiophene phenol-2-yls)-3 of 5-, 4-phenylbenzene Silole replaces 9,9-di-n-octyl-2,7-dibromo silicon fluorenes.The number-average molecular weight of gained red polymer is 13000, and weight-average molecular weight is 29000.
Embodiment 20:
The preparation of the conjugated polymers of phosphatidylcholine base fluorenes and 5,7-, bis-thiophene-thieno-[3,4-b] pyrazine, reaction formula is as follows:
Method is with embodiment 14.With two (the bromo-2-thiophene of 5-)-2 of 5,7-, two (to octyl phenyl)-thieno-[3, the 4-b] pyrazines of 3-replace 9,9-di-n-octyl-2,7-dibromo silicon fluorenes.The number-average molecular weight of gained purple polymkeric substance is 9500, and weight-average molecular weight is 19000.
Embodiment 21:
The preparation of the conjugated polymers of phosphatidylcholine base fluorenes and two thieno-s [3 ,-b:2', 3'-d] Silole, reaction formula is as follows:
Method is with embodiment 14.With 4,4'-di-n-hexyl-5, bromo-two thieno-s of 5'-bis-[3,2-b:2', 3'-d] Silole replaces 9,9-di-n-octyl-2,7-dibromo silicon fluorenes.The number-average molecular weight of gained red polymer is 11000, and weight-average molecular weight is 25000.
Embodiment 22:
The preparation of the conjugated polymers of phosphatidylcholine base fluorenes and diphenylethlene, reaction formula is as follows:
Method is with embodiment 12.With two (to bromophenyl) ethene replacement of 1,2-2-n-octyl-4,7-dibromo benzotriazole.The number-average molecular weight of the faint yellow polymkeric substance of gained is 11000, and weight-average molecular weight is 25000.
Embodiment 23:
The preparation of the conjugated polymers of phosphatidylcholine base fluorenes and dibenzenyl, reaction formula is as follows:
Method is with embodiment 12.With two (to bromophenyl) acetylene replacement of 1,2-2-n-octyl-4,7-dibromo benzotriazole.The number-average molecular weight of the faint yellow polymkeric substance of gained is 8000, and weight-average molecular weight is 18500.
Embodiment 24:
The preparation of the organic light emitting diode device taking metallic aluminium as negative electrode and performance
The structure of the organic light emitting diode device taking metallic aluminium as negative electrode is as: ITO/PEDOT:PSS/P-PPV/ is containing 2 of phosphatidylcholine base, 7-fluorine conjugated polymer/Al.Device fabrication processes is: taking the ito glass that cleans in advance as anode, the water-soluble polymers PEDOT:PSS of spin coating 40 nanometers on ito glass, after dry, continue the luminescence polymer P-PPV of spin coating 80 nanometers, after dry, follow prepared poly-(the phosphatidylcholine base 2 of spin coating embodiment 7,7-fluorenes) methanol solution, the thickness of controlling this polymkeric substance is 10 nanometers, the Al metallic cathode of last vacuum evaporation 100 nanometers.Between ITO and Al metal electrode, apply positive bias, the chromaticity coordinates of luminescent spectrum is (0.43,0.55), and brightness corresponding under approximately 39 milliamperes every square centimeter of current density is 2541cd/m 2, corresponding efficiency is 6.51cd/A.
With the prepared phosphatidylcholine base 2 of embodiment 8, the conjugated polymers of the fluorenes that 7-fluorenes and octyl group replace replaces poly-(phosphatidylcholine base 2,7-fluorenes), prepare organic light emitting diode device by above-mentioned identical process, luminescent properties is: the chromaticity coordinates of luminescent spectrum is (0.43,0.55), under approximately 276 milliamperes every square centimeter of current density, corresponding brightness is 8956cd/m 2, corresponding efficiency is 3.24cd/A.
Ito glass noted earlier refers to indium tin oxide-coated glass; PEDOT:PSS is the abbreviation of English Poly (3,4-ethylendioxy-thiophene): poly (styrene sulfonic acid); P-PPV is the abbreviation of English Poly (2-(4-(3', 7'-dimethyloctyloxy) phenyl)-Isosorbide-5-Nitrae-phenylene vinylene).
Embodiment 25:
The preparation of the organic light emitting diode device taking ITO as negative electrode and performance
The structure of the organic light emitting diode device taking ITO as negative electrode is as: ITO/ is containing 2 of phosphatidylcholine base, 7-fluorine conjugated polymer/P-PPV/MoO 3/ Al.Device fabrication processes is: taking the ito glass that cleans in advance as negative electrode, prepared poly-(the phosphatidylcholine base 2 of spin coating embodiment 7 on ito glass, 7-fluorenes) methanol solution, the thickness of controlling this polymkeric substance is 10 nanometers, after dry, continue the luminescence polymer P-PPV of spin coating 80 nanometers, the MoO of 10 nanometers of vacuum evaporation afterwards 3, then the Al metal anode of vacuum evaporation 100 nanometers.Between ITO and Al metal electrode, apply negative bias, the chromaticity coordinates of luminescent spectrum is (0.43,0.55), and brightness corresponding under approximately 238 milliamperes every square centimeter of current density is 25.74cd/m 2, corresponding efficiency is 0.01cd/A.
With the prepared phosphatidylcholine base 2 of embodiment 8, the conjugated polymers of the fluorenes that 7-fluorenes and octyl group replace replaces poly-(phosphatidylcholine base 2,7-fluorenes), prepare organic light emitting diode device by above-mentioned identical process, luminescent properties is: the chromaticity coordinates of luminescent spectrum is (0.43,0.55), under approximately 265 milliamperes every square centimeter of current density, corresponding brightness is 32cd/m 2, corresponding efficiency is 0.012cd/A.
Embodiment 26:
Preparation and the performance of the organic photovoltaic battery device taking metallic aluminium as negative electrode
The structure of the organic photovoltaic battery device taking metallic aluminium as negative electrode is ITO/PEDOT:PSS/ (PTB7:PC 71bM=1:1.5)/containing 2 of phosphatidylcholine base, 7-fluorine conjugated polymer/Al.Device fabrication processes is: taking the ito glass that cleans in advance as anode, the water-soluble polymers PEDOT:PSS of spin coating 40 nanometers on ito glass, continues the photovoltaic active coating (PTB7:PC of spin coating 80 nanometers after dry 71bM=1:1.5, weight ratio), the prepared methanol solution that gathers (phosphatidylcholine base 2,7-fluorenes) of dry rear then spin coating embodiment 7, controlling thickness is 10 nanometers, the Al metallic cathode of last vacuum evaporation 100 nanometers.Between ITO and Al metal electrode, apply positive bias, under the irradiation of the AM1.5 of every square centimeter of 80 milliwatt simulated solar irradiation, measure its battery behavior, the open circuit voltage of this battery device is 0.75 volt, short-circuit current is 14.19 milliamperes every square centimeter, packing factor 57.6%, effciency of energy transfer 6.13%.
With the prepared phosphatidylcholine base 2 of embodiment 8, the conjugated polymers of the fluorenes that 7-fluorenes and octyl group replace replaces poly-(phosphatidylcholine base 2,7-fluorenes), prepare organic photovoltaic battery device by above-mentioned identical process, battery device performance is: open circuit voltage is 0.79 volt, short-circuit current is 15.2 milliamperes every square centimeter, packing factor 59%, effciency of energy transfer 7.08%.
Foregoing PC 71bM is English " [6,6]-phenyl C 71-butyric acid methyl ester " abbreviation; Polymer P TB7 is by benzodithiophene and thieno[3,4-b] alternating copolymer of thiophene composition.
Embodiment 27:
Preparation and the performance of the organic photovoltaic battery device taking ITO as negative electrode
The structure of the organic photovoltaic battery device taking ITO as negative electrode is as: ITO/ is containing 2 of phosphatidylcholine base, 7-fluorine conjugated polymer/(PTB7:PC 71bM=1:1.5)/MoO 3/ Al.Device fabrication processes is: taking the ito glass that cleans in advance as negative electrode, prepared poly-(the phosphatidylcholine base 2 of spin coating embodiment 7 on ito glass, 7-fluorenes) methanol solution, the thickness of controlling this polymkeric substance is 10 nanometers, the dry rear photovoltaic active coating (PTB7:PC that continues spin coating 80 nanometers 71bM=1:1.5, weight ratio), the MoO of 10 nanometers of vacuum evaporation afterwards 3, then the Al metal anode of vacuum evaporation 100 nanometers.Between ITO and Al metal electrode, apply negative bias, under the irradiation of the AM1.5 of every square centimeter of 80 milliwatt simulated solar irradiation, measure its battery behavior, the open circuit voltage of this battery device is 0.74 volt, short-circuit current is 15.22 milliamperes every square centimeter, packing factor 68%, effciency of energy transfer 7.66%.
With the prepared phosphatidylcholine base 2 of embodiment 8, the conjugated polymers of the fluorenes that 7-fluorenes and octyl group replace replaces poly-(phosphatidylcholine base 2,7-fluorenes), prepare organic photovoltaic battery device by above-mentioned identical process, battery device performance is: open circuit voltage is 0.73 volt, short-circuit current is 15.6 milliamperes every square centimeter, packing factor 70.4%, effciency of energy transfer 8.04%.

Claims (6)

1. one kind contains 2 of phosphatidylcholine base, and the conjugated polymers of 7-fluorenes, is characterized in that having following structure:
Wherein, R 1for the alkyl that carbon number is 1～4, m is 2～12; 0<x≤1,0≤y<1, x+y=1; N=3-1000; Ar is conjugate unit, comprises one or more combinations in the aromatic heterocycle that aromatic nucleus that ethene support group, acetylene support group, hydrocarbon atom form, aromatic heterocycle that carbon nitrogen hydrogen atom forms, aromatic heterocycle that carbon nitrogen oxygen hydrogen atom forms, aromatic heterocycle that carbon sulphur hydrogen atom forms, aromatic heterocycle that carbon silicon hydrogen atom forms, aromatic heterocycle that carbon nitrogen sulphur hydrogen atom forms and carbon silicon sulphur hydrogen atom form.
2. according to claim 1 containing 2 of phosphatidylcholine base, the conjugated polymers of 7-fluorenes, it is characterized in that described Ar conjugate unit is with substituted radical, substituted radical comprises one or more combinations in alkyl, fluoro-alkyl, alkoxyl group, ester group, carbonyl.
3. claimed in claim 1 containing 2 of phosphatidylcholine base, the preparation method of the conjugated polymers of 7-fluorenes, is characterized in that, will contain 2 of phosphatidylcholine base, and 7-fluorenes monomer and Ar monomer carry out copolymerization preparation; Use containing phosphatidylcholine base 2,7-fluorenes monomer structure is as follows:
Wherein, R 2for reaction active groups, comprise bromo, iodo, chloro, trialkyltin, 4,4,5,5-tetramethyl--1, the one in 3,2-dioxa pentaborane-2-base, R 3for the alkyl that carbon number is 1～4, z is 2～12; The carbon number of the alkyl in described trialkyltin is 1～4.
The structure of the Ar monomer using is: R 4-Ar-R 4, wherein R 4for reaction active groups, comprise bromo, iodo, chloro, trialkyltin, 4,4,5,5-tetramethyl--1, the one in 3,2-dioxa pentaborane-2-base; The carbon number of the alkyl in described trialkyltin is 1～4.
4. described in claim 1, contain 2 of phosphatidylcholine base, the conjugated polymers of 7-fluorenes is applied to be made in photoelectric functional device.
5. application according to claim 4, is characterized in that: described photoelectric functional device is Organic Light Emitting Diode.
6. application according to claim 4, is characterized in that: described photoelectric functional device is organic photovoltaic battery.
CN201410284177.9A 2014-06-23 2014-06-23 2, 7-fluorene conjugated polymer containing phosphatidylcholine and preparation method and application thereof Pending CN104072727A (en)

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