CN106866938A - A kind of conjugated polymer based on naphthalene two and indenes fluorenes unit and preparation method and application - Google Patents

A kind of conjugated polymer based on naphthalene two and indenes fluorenes unit and preparation method and application Download PDF

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CN106866938A
CN106866938A CN201710030865.6A CN201710030865A CN106866938A CN 106866938 A CN106866938 A CN 106866938A CN 201710030865 A CN201710030865 A CN 201710030865A CN 106866938 A CN106866938 A CN 106866938A
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substitution
fluorenes
naphthalene
conjugated polymer
indenes
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应磊
赵森
郭婷
杨伟
彭俊彪
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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Abstract

The invention discloses a kind of conjugated polymer based on naphthalene two and indenes fluorenes unit and preparation method and application.In conjugated polymer of the present invention based on naphthalene two and indenes fluorenes unit, simultaneously indenes fluorenes flatness is preferable for naphthalene two, with larger fluorescence quantum yield, it is appropriate for solution processing and typographical display prepares the luminescent layer of light emitting diode by Solution processing techniques, technological process is simple.Conjugated polymer of the present invention based on naphthalene two and indenes fluorenes unit is prepared by Suzuki polymerisations.

Description

A kind of conjugated polymer based on naphthalene two and indenes fluorenes unit and preparation method and application
Technical field
The invention belongs to organic photoelectrical material technical field, and in particular to a kind of conjugation based on naphthalene two and indenes fluorenes unit is gathered Compound and preparation method and application.
Background technology
In the past thirty years, organic electronic and photoelectronic industry, including organic/polymer LED, it is organic The fields such as field-effect transistor, organic solar batteries have obtained swift and violent development, and gradually realize industrialization.Organic electronic is produced Product have cheap, and body is light the advantages of take.Make it have great market potential.Therefore exploitation has market attractiveness Organic electronic product has attracted the concern of numerous research institutions and Research Team in the world, and among these, develops new and effective The material of stabilization turns into key.
The naphthalene two and indenes fluorenes unit and its polymer that the present invention relates to, because having preferable solubility property, are applicable In solution processing, and preferably fluorescence quantum yield, its luminescent device not only efficient stable, and be blue more blue saturation Light, can meet the requirement of full-color display.So having huge development potentiality and prospect in organic electronic display field.
The content of the invention
It is an object of the invention to provide a kind of conjugated polymer based on naphthalene two and indenes fluorenes unit, the conjugated polymer can As luminescent material, with preferable dissolubility, fluorescence quantum yield higher is suitable for solution processing and inkjet printing, tool There is good development prospect.
Preparation the present invention also aims to provide a kind of described conjugated polymer based on naphthalene two and indenes fluorenes unit Method.
It is prepared by a kind of conjugated polymer based on naphthalene two and indenes fluorenes unit the present invention also aims to provide described Application in the luminescent layer of light emitting diode.
A kind of conjugated polymer based on naphthalene two and indenes fluorenes unit, chemical structural formula is as follows：
In formula, R is H atom, aryl, triphenylamine, the straight chain of carbon number 1-20 or branched alkyl or is carbon number The alkoxy of 1-20；0≤x ＜ 1；Polymerization degree n=1~300；
The structure of Ar is any one in following structure：
S, S- dioxydibenze bithiophene
2,7- substituted fluorenes；
3,6- substituted fluorenes；
2,7- substitution silicon fluorenes；
3,6- substitution silicon fluorenes；
2,7- substitution spiro fluorenes；
3,6- substitution spiro fluorenes；
2,7- substitution -9,9- dialkoxy phenyl fluorenes；3,6- take Generation -9,9- dialkoxy phenyl fluorenes；2,7- substituted carbazoles；
3,6- substituted carbazoles；
2,6- substitution-dithieno thiophenes are coughed up；
2,6- substitution-dithieno cyclopentadiene；
2,5- substituted pyridines；
2,6- substituted pyridines；
3,5- substituted pyridines；
3,5- double (4- substituted 4-phenyls) -4- base -1,2,4- triazoles；
3,5- double (4- substituted 4-phenyls) -1,2,4- oxadiazoles；
4,7- double (5- substitution -4- alkylthrophenes bases) -2,1,3- diazosulfide；
4,7- double (5- substitution -4- alkylthrophenes bases) 2,1,3- selenoles；
4,7- -5,6- of substitution alkyl -2,1,3- diazosulfide；
4,7- -5,6- of substitution alkyl -2,1,3- selenole；
2,5- substitution -3,4- dialkylthiophenes；
2,5- substitution -3,4- dialkyl group selenophens；
5,5- -4,4- of substitution dialkyl group-bithiophene；
Indenes fluorenes；
Indole carbazole；
4,9- -6,7- of substitution alkyl-naphtho- thiadiazoles；
4,9- -6,7- of substitution alkyl-naphtho- selenium diazole；
Naphtho- indenes fluorenes；
Wherein, R is H atom, aryl, triphenylamine, the straight chain or branched alkyl of carbon number 1-20, or is carbon number The alkoxy of 1-20.
A kind of preparation method of described conjugated polymer based on naphthalene two and indenes fluorenes unit, comprises the following steps：
By the boric acid ester monomer of naphthalene two and indenes fluorenes and the monomer containing Ar structures by after Suzuki polymerisations, then adopt successively End capping reaction is carried out with bromobenzene and phenyl boric acid, the conjugated polymer based on naphthalene two and indenes fluorenes unit is obtained.
Further, the temperature of the Suzuki polymerisations is 80~110 DEG C, and the reaction time is 24~48h.
Further, the catalyst system of the Suzuki polymerisations includes palladium and tricyclohexyl phosphine.
Further, the use bromobenzene and phenyl boric acid carry out the reaction temperature of end capping reaction and are 80~110 DEG C, reaction Time is 12~24h.
A kind of described conjugated polymer based on naphthalene two and indenes fluorenes unit is applied to prepare light emitting diode, will be described common Conjugated polymer organic solvent dissolves, by spin coating, inkjet printing or printing process film forming, as the luminous of light emitting diode Layer, the luminescent layer that will be obtained is used to prepare light emitting diode.
Further, the organic solvent includes chlorobenzene.
Compared with prior art, the invention has the advantages that and beneficial effect：
(1) in a kind of conjugated polymer based on naphthalene two and indenes fluorenes unit of the present invention, simultaneously indenes fluorenes flatness preferably, has naphthalene two There is larger fluorescence quantum yield；
(2) a kind of conjugated polymer dissolubility based on naphthalene two and indenes fluorenes unit of the present invention is relatively good, is appropriate for solution Processing and typographical display, the luminescent layer of light emitting diode is prepared by Solution processing techniques, and technological process is simple.
(3) luminescent layer based on bipolarity small molecule material of the present invention when device is prepared without annealing so that system Standby process is simple.
Brief description of the drawings:
Fig. 1 is the DSC spectrograms of polymer P 1；
Fig. 2 is luminescence generated by light spectrogram of the polymer P 2 under filminess；
Fig. 3 is luminescence generated by light spectrogram of the polymer P 3 under filminess；
Fig. 4 is the current density-luminous efficiency spectrogram of the electroluminescent device based on polymer P 4.
Specific embodiment
With reference to embodiment, the present invention is described in further detail, but embodiments of the present invention not limited to this.
Embodiment 1
The preparation of the 2-methyl naphthoate of 1- bromines two
Chemical equation is as follows：
Under an argon atmosphere, by bromo- 2- naphthoic acids (10g, 39.83mmol) the addition two-mouth bottles of 1-, 100mL first is added Alcohol, is then added dropwise over the concentrated sulfuric acid (39.06mg, 398.29umol), is heated to 110 DEG C, reacts 18h；Reactant mixture is fallen Enter in water, be extracted with ethyl acetate, after organic layer saline solution is washed completely, plus anhydrous magnesium sulfate is dried；After solution concentration, obtain To crude white solid, (eluant, eluent selects petroleum ether/dichloromethane=3/1, v/v) is purified with silica gel column chromatography, when product is long Between place refrigerator in obtain white solid, yield 85%.1H NMR、13CNMR, MS and elementary analysis result show resulting change Compound is target product.
Embodiment 2
The preparation of 2,7- dibromo fluorenes
Chemical equation is as follows：
In 250mL there-necked flasks, fluorenes (24.5g, 0.1mol), iron powder (88mg, 1.57mmol), chloroform are added 100mL；Ice-water bath is cooled down, and bromine (17.6g, 0.1mol)/chloroform mixed solution 35mL is added dropwise, and temperature does not surpass in bottle during dropwise addition Cross 5 DEG C；Reaction is finished, filtering, Gossypol recrystallized from chloroform, obtains white solid 20.3g, yield 83%.1HNMR、13CNMR, MS and element Compound obtained by analysis result shows is target product.
Embodiment 3
The preparation of 2,7- bis- bromo- 9,9- dioctyl fluorenes
Chemical equation is as follows：
Added in there-necked flask 2,7- dibromos fluorenes (9.7g, 0.03mol), benzyltriethylammoinium chloride (0.07g, 0.3mmol), dimethyl sulfoxide (DMSO) 90mL, 45mL sodium hydrate aqueous solutions (50wt%), at room temperature stirring forms suspension；Add 1- bromines normal octane (12.5g, 65mmol), after continuing to stir 3 hours, are extracted with ether, and second is washed with saturated sodium-chloride water solution Ether phase, anhydrous magnesium sulfate is dried, and boils off solvent, and product petroleum ether makees the purification of eluant, eluent column chromatography, obtains white solid.1H NMR、13Compound obtained by CNMR, MS and elementary analysis result show is target product.
Embodiment 4
2,7- diborate -9, the preparation of 9- dioctyl fluorenes
Chemical equation is as follows：
Under an argon atmosphere, bromo- 9, the 9- dioctyl fluorenes (5g, 9.12mmol) of 2,7- bis- are dissolved in the refined THF of 180mL In, 1.6mol.L is gradually added dropwise at -78 DEG C-1N-BuLi 28mL, react 2 hours, be subsequently adding 2- isopropoxy -4,4, 5,5- tetramethyl -1,3,2- dioxaborinate 25mL continue to react 1 hour at -78 DEG C, then heat to room temperature reaction 24 small When；Reactant mixture is poured into water, is extracted with ethyl acetate, after organic layer saline solution is washed completely, plus anhydrous magnesium sulfate Dry；After solution concentration, thick pale yellow shape crude product is obtained, (eluant, eluent selection petroleum ether/acetic acid second is purified with silica gel column chromatography Ester=15/1, v/v), product obtains white solid, yield 70% in placing refrigerator for a long time.1H NMR、13CNMR, MS and element Compound obtained by analysis result shows is target product.
Embodiment 5
The preparation of compound M1
Chemical equation is as follows：
Under argon atmosphere, by 2,7- diborate -9,9- dioctyl fluorenes (5g, 7.78mmol) and the bromo- 2- naphthoic acids of 1- Methyl esters (6.19g, 23.34mmol) is added in two-mouth bottle, and adding 100ml toluene is completely dissolved it, adds sodium carbonate (4.12g, 38.91mmol), TBAB (312.01mg, 967.86umol) and four triphenyl phosphorus palladiums (179.84mg, 155.63umol), 18h is reacted at 110 DEG C；Reactant mixture is poured into water, is extracted with ethyl acetate, organic layer salt After water is washed completely, plus anhydrous magnesium sulfate is dried.After solution concentration, (eluant, eluent selection petroleum ether/bis- are purified with silica gel column chromatography Chloromethanes=8/1, v/v), finally give white solid, yield 80%.1H NMR、13CNMR, MS and elementary analysis result show Resulting compound is target product.
Embodiment 6
The preparation of compound M2
Chemical equation is as follows：
Under argon atmosphere, by M1 (10g, 13.17mmol) addition single port bottles, the anhydrous THF of 50ml are added until complete CL, then reaction solution is reacted into 1h at 0 DEG C, then it is added dropwise over C8H17MgBr (n-octyl magnesium bromide), mixed liquor is in room temperature Lower reaction 18h；Add water to that reaction is quenched in reaction solution, be extracted with ethyl acetate, organic layer saline solution is washed completely Afterwards, plus anhydrous magnesium sulfate dry；After solution concentration, (eluant, eluent selection petroleum ether/dichloromethane=3/ is purified with silica gel column chromatography 1, v/v), product obtains white solid, yield 80% in placing refrigerator for a long time.1H NMR、13CNMR, MS and elementary analysis knot Compound obtained by fruit shows is target product.
Embodiment 7
The preparation of compound M3
Chemical equation is as follows：
Under argon atmosphere, M2 (5g, 8.68mmol) is dissolved in 50ml dichloromethane, trifluoro is added dropwise at room temperature Change borate ether solution (588.67mg, 8.68mmol), react 18h；It is extracted with ethyl acetate, organic layer saline solution is washed completely Afterwards, plus anhydrous magnesium sulfate dry；After solution concentration, (eluant, eluent selection petroleum ether) is purified with silica gel column chromatography, product is for a long time White solid, yield 90% are obtained in placement refrigerator.1H NMR、13CNMR, MS and elementary analysis result show resulting chemical combination Thing is target product.
Embodiment 8
The preparation of compound M4
Chemical equation is as follows：
Under argon atmosphere, M3 (5g, 4.48mmol) is dissolved in 50mL dichloromethane, add iron powder (185.35mg, 4.48mmol), then bromine (1.50g, 9.41mmol) is added dropwise over, 18h is reacted at room temperature；It is extracted with ethyl acetate, it is organic After layer saline solution is washed completely, plus anhydrous magnesium sulfate is dried；After solution concentration, (eluant, eluent selection is purified with silica gel column chromatography Petroleum ether), yield 70%.1H NMR、13Compound obtained by CNMR, MS and elementary analysis result show is target product.
Embodiment 9
The preparation of compound M5
Chemical equation is as follows：
Under an argon atmosphere, M4 (10g, 7.85mmol) is dissolved in the refined THF of 180mL, is gradually dripped at -78 DEG C Plus the n-BuLi 32mL of 1.6mol L-1, react 2 hours, it is then quickly added into 2- isopropoxy -4,4,5,5- tetramethyl -1, 3,2- dioxaborinate 28mL, continue to react 1 hour at -78 DEG C, are to slowly warm up to room temperature reaction 24 hours；Reaction is mixed Thing is poured into water, and is extracted with ethyl acetate, and after organic layer saline solution is washed completely, plus anhydrous magnesium sulfate is dried；Solution is concentrated Afterwards, thick pale yellow shape crude product is obtained, (eluant, eluent selection petrol ether/ethyl acetate=20/1, v/ is purified with silica gel column chromatography V), product obtains white solid, yield 70% in placing refrigerator for a long time.1H NMR and GC-MASS test are shown to be target product Thing.
Embodiment 10
The preparation of 3,6- dibromo carbazoles
Chemical equation is as follows：
In 500mL two-mouth bottles add carbazole (24.7g, 0.1mol), dimethylformamide 200mL, stirring to completely it is molten Solution, NBS (49.84g, 0.28mol) 120ml DMFs dissolve, and ice bath is added dropwise NBS solution, instead to 0 DEG C Should, lucifuge after completion of dropping, allows temperature to rise to room temperature automatically, reacts 6 hours, reaction solution is added drop-wise in water and is precipitated, suction filtration After obtaining crude product, suction filtration thing is recrystallized with absolute ethyl alcohol, dried, obtained precious color needle-like solid, yield 85%.1H NMR、13Compound obtained by CNMR, MS and elementary analysis result show is target product.
Embodiment 11
The bromo- N- octylcarbazols of 3,6- bis-
Chemical equation is as follows：
3,6- dibromos carbazole (16.25g, 0.05mmol), toluene 100mL, tetrabutyl phosphonium bromide are added in 250mL there-necked flasks Ammonium (0.8g, 3.5mmol) stirring and dissolving, then be added dropwise 50wt%KOH aqueous solution 11mL, then add bromooctane (19.3g, 0.1mol), reacted 24 hours at 80 DEG C, add water terminating reaction, the organic phase that washing is separated, water is extracted with dichloromethane After taking, merge organic phase, use anhydrous MgSO4Dry, vacuum distillation obtains light yellow solid after removing solvent, is tied again with petroleum ether Crystalline substance obtains white powder solid.Yield 90%.1H NMR、13CNMR, MS and elementary analysis result show that resulting compound is Target product.
Embodiment 12
3,6- bis- (4,4,5,5- tetramethyls -1,3,2- dioxaborinates-diyl)-N- octylcarbazols
Chemical equation is as follows：
The bromo- N- octylcarbazols (13.11g, 30mmol) of 3,6- bis-, the new ether 250mL for steaming, stirring are added in there-necked flask It is completely dissolved to clear, reaction solution is cooled to -78 DEG C, it is then disposable to add 2- isopropoxies-(4,4,5,5- tetra- Methyl) -1,3,2- ethylenedioxy borates (37mL, 180mmol), stir 2 hours, then temperature is warmed to room temperature at -78 DEG C Reaction terminates reaction after 24 hours；Extracted with ether, saturated common salt water washing 4 times, then dried with anhydrous magnesium sulfate, after filtering, Solvent, product petrol ether/ethyl acetate (10 is distilled off:1) for eluant, eluent column chromatography is purified, white solid, yield are obtained 45%.
Embodiment 13
The preparation of 3,7- bis- bromo- S, S- titanium dioxide dibenzothiophens
Chemical equation is as follows：
(1) 5g biphenyl is dissolved in 80mL dichloromethane in the round-bottomed flask of 150mL, 11.8g is added at room temperature Bromo-succinimide, then reacts 48 hours at room temperature；After reaction terminates, reactant is poured into water, is extracted with dichloromethane Take, then wash with water；Anhydrous magnesium sulfate is dried, and solvent is evaporated off, and is then recrystallized with petroleum ether；White solid 5.65g is obtained, Yield 75%.
(2) add 20g4,4 '-'-dibromobiphenyl to be dissolved in 50mL chloroforms in 150mL there-necked flasks, be added dropwise 11.4mL chlorosulfonic acids, maintenance reaction system is reacted 3 hours below 50 DEG C；After reaction terminates, reactant is poured into 500mL broken In ice, neutrality is adjusted to Na2CO3 solution after ice-out, filters out insoluble matter, Recrystallisation from acetic acid is used after washing and drying, obtain white Color needle-like solid 6g, yield：12%.
Embodiment 14
The preparation of polymer P 1
Chemical equation is as follows：
Under argon atmosphere, by compound M5 (300mg, 219.34 μm of ol) and bromo- 9, the 9- dioctyl fluorenes of 2,7- bis- (120.29mg, 219.34 μm of ol) are added in 100ml two-mouth bottles, are added 8ml toluene and are allowed to be completely dissolved, and substitute gas three times； Palladium (1.97mg, 8.77 μm of ol) and tricyclohexyl phosphine (4.92mg, 17.55 μm of ol) are added, gas is substituted three times, Ran Houjia Enter 2ml tetraethyl ammonium hydroxides, be warming up to 80 DEG C, react 24 hours；It is subsequently adding 30mg phenyl boric acids to be blocked, 12 hours Afterwards, then with 0.1ml bromobenzenes blocked, continue to react 12 hours；Product is added dropwise and is precipitated out in methyl alcohol, stirred, filtering, Crude product is dissolved in the toluene of 20mL again, is fixing phase with 200~300 mesh silica gel, be that eluant, eluent carries out column chromatography with toluene, After solvent under reduced pressure is concentrated again, separate out to come in methyl alcohol again, stirring, filtering obtains polymer solids after vacuum drying； Finally respectively extracted 24 hours with methyl alcohol, acetone, tetrahydrofuran successively again, remove small molecule；By the tetrahydrofuran solution after concentration Instill precipitating, the fibrous solids conjugated polymer P1 obtained after vacuum drying in methyl alcohol.
The DSC spectrograms of polymer P 1 are not as shown in figure 1, as shown in Figure 1, polymer P 1 occurs bright during intensification Aobvious melting peak.
Embodiment 15
The preparation of polymer P 2
Chemical equation is as follows：
Under argon atmosphere, by compound M5 (300mg, 219.34 μm of ol) and N- octylcarbazols (95.90mg, 219.34 μ Mol) add in 100ml two-mouth bottles, add 8ml toluene and be completely dissolved, substitute gas three times；Add palladium (1.97mg, 8.77 μm of ol) and tricyclohexyl phosphine (4.92mg, 17.55 μm of ol), substitutes gas three times, is subsequently adding 2ml tetraethyls Ammonium hydroxide, is warming up to 80 DEG C, reacts 24 hours；It is subsequently adding 30mg phenyl boric acids to be blocked, after 12 hours, then uses 0.1ml Bromobenzene is blocked, and continues to react 12 hours；Product is added dropwise and is precipitated out in methyl alcohol, stirred, filtering, then crude product is molten It is fixing phase with 200~300 mesh silica gel in the toluene of 20mL, is that eluant, eluent carries out column chromatography with toluene, then by solvent under reduced pressure After concentration, separate out to come in methyl alcohol again, stirring, filtering obtains polymer solids after vacuum drying；Finally use successively again Methyl alcohol, acetone, tetrahydrofuran are respectively extracted 24 hours, remove small molecule；Sunk during tetrahydrofuran solution after concentration is instilled into methyl alcohol Analysis, the fibrous solids conjugated polymer P2 obtained after vacuum drying.
Luminescence generated by light spectrogram of the polymer P 2 under filminess is as shown in Fig. 2 as shown in Figure 2, polymer P 2 is in film Maximum emission peak under state is located at 458nm.
Embodiment 16
The preparation of polymer P 3
Chemical equation is as follows：
Under argon atmosphere, by compound M5 (300mg, 219.34 μm of ol) and S, S- dioxydibenze bithiophene (82.04mg, 219.34 μm of ol) are added in 100ml two-mouth bottles, are added 8ml toluene and are completely dissolved, and substitute gas three times；Again Palladium (1.97mg, 8.77 μm of ol) and tricyclohexyl phosphine (4.92mg, 17.55 μm of ol) are added, gas is substituted three times, is subsequently adding 2ml tetraethyl ammonium hydroxides, are warming up to 80 DEG C, react 24 hours；30mg phenyl boric acids are subsequently adding to be blocked, after 12 hours, Blocked with 0.1ml bromobenzenes again, continue to react 12 hours；Product is added dropwise and is precipitated out in methyl alcohol, stirred, filtering, then Crude product is dissolved in the toluene of 20mL, is fixing phase with 200~300 mesh silica gel, be that eluant, eluent carries out column chromatography with toluene, then After solvent under reduced pressure is concentrated, separate out to come in methyl alcohol again, stirring, filtering obtains polymer solids after vacuum drying；Most Respectively extracted 24 hours with methyl alcohol, acetone, tetrahydrofuran successively again afterwards, remove small molecule；By the tetrahydrofuran solution drop after concentration Enter precipitating in methyl alcohol, the fibrous solids conjugated polymer P3 obtained after vacuum drying.
Luminescence generated by light spectrogram of the polymer P 3 under filminess is as shown in figure 3, from the figure 3, it may be seen that polymer P 3 is in film Maximum emission peak under state is located at 492nm.
Embodiment 17
The preparation of polymer P 4
Chemical equation is as follows：
Under argon atmosphere, by compound M5 (300mg, 219.34 μm of ol), S, S- dioxydibenze bithiophene (49.23mg, 131.60 μm of ol) and diazosulfide (25.79mg, 87.74umol) add 100ml two-mouth bottles in, adding 8ml toluene is carried out It is completely dissolved, substitutes gas three times；Add palladium (1.97mg, 8.77 μm of ol) and tricyclohexyl phosphine (4.92mg, 17.55 μ Mol), substitute gas three times, be subsequently adding 2ml tetraethyl ammonium hydroxides, be warming up to 80 DEG C, react 24 hours；It is subsequently adding 30mg Phenyl boric acid is blocked, and after 12 hours, then is blocked with 0.1ml bromobenzenes, continues to react 12 hours；Product is added dropwise in methyl alcohol In be precipitated out, stir, then be dissolved in crude product in the toluene of 20mL by filtering, is fixing phase with 200~300 mesh silica gel, uses first Benzene carries out column chromatography for eluant, eluent, then after solvent under reduced pressure is concentrated, separates out to come in methyl alcohol again, stirring, filtering, vacuum Polymer solids are obtained after drying；Finally respectively extracted 24 hours with methyl alcohol, acetone, tetrahydrofuran successively again, remove small molecule；Will Tetrahydrofuran solution after concentration instills precipitating, the fibrous solids conjugated polymer P4 obtained after vacuum drying in methyl alcohol.
Embodiment 18
The preparation of the electroluminescent device based on conjugated polymer
It is on tin indium oxide (ITO) glass of 20 Ω/, first successively with acetone, washing in the square resistance of well in advance Agent, deionized water and isopropanol are cleaned by ultrasonic, plasma treatment 10 minutes.Spin coating is mixed on ITO polystyrolsulfon acid Polyethoxy thiophene (mass ratio PEDOT:PSS=1:1) film, thickness is 150nm；PEDOT:PSS films are 80 DEG C in vacuum drying oven Lower drying 8 hours.The chlorobenzene solution (1wt%) of polymer P 1, P2, P3, P4 is then spin-coated on PEDOT respectively:The table of PSS films Face, thickness is 80nm, used as luminescent layer；It is last to be deposited with the thick gold of a thin layer CsF (1.5nm) and 120nm successively on luminescent layer Al layers of category.
Obtain the device architecture based on 1~P4 of polymer P：ITO/PEDOT/EML/CsF/Al.Wherein, based on polymer P 4 Device luminous efficiency-current density plot figure as shown in figure 4, as shown in Figure 4, the max-flow of the device based on polymer P 4 Obvious results rate is 1.55cd/A.
The photoelectric properties index of the device based on 1~P4 of polymer P is as shown in table 1.
Table 1 is based on the photoelectric properties index of the device of 1~P4 of polymer P
As shown in Table 1, luminescent layer is prepared with polymer P 1, P2, P3, P4, prepares device architecture for ITO/PEDOT/EML/ The electroluminescent device of CsF/Al, maximum lumen efficiency is followed successively by 1.05cd/A, 2.36cd/A, 1.61cd/A, 1.34cd/A.
Above-described embodiment is the present invention preferably implementation method, but embodiments of the present invention are not by above-described embodiment Limitation, other it is any without departing from Spirit Essence of the invention and the change, modification, replacement made under principle, combine, simplification all should It is equivalent substitute mode, is included within protection scope of the present invention.

Claims (7)

1. a kind of conjugated polymer based on naphthalene two and indenes fluorenes unit, it is characterised in that chemical structural formula is as follows：
In formula, R is H atom, aryl, triphenylamine, the straight chain or branched alkyl of carbon number 1-20, or is carbon number 1-20 Alkoxy；0≤x ＜ 1；Polymerization degree n=1-300；
The structure of Ar is any one in following structure：
S, S- dioxydibenze bithiophene
2,7- substituted fluorenes；
3,6- substituted fluorenes；
2,7- substitution silicon fluorenes；
3,6- substitution silicon fluorenes；
2,7- substitution spiro fluorenes；
3,6- substitution spiro fluorenes；
2,7- substitution -9,9- dialkoxy phenyl fluorenes；
3,6- substitution -9,9- dialkoxy phenyl fluorenes；
2,7- substituted carbazoles；
3,6- substituted carbazoles；
2,6- substitution-dithieno thiophenes are coughed up；
2,6- substitution-dithieno cyclopentadiene；
2,5- substituted pyridines；
2,6- substituted pyridines；
3,5- substituted pyridines；
3,5- double (4- substituted 4-phenyls) -4- base -1,2,4- triazoles；
3,5- double (4- substituted 4-phenyls) -1,2,4- oxadiazoles；
4,7- double (5- substitution -4- alkylthrophenes bases) -2,1,3- diazosulfide；
4,7- double (5- substitution -4- alkylthrophenes bases) 2,1,3- selenoles；
4,7- -5,6- of substitution alkyl -2,1,3- diazosulfide；
4,7- -5,6- of substitution alkyl -2,1,3- selenole；
2,5- substitution -3,4- dialkylthiophenes；
2,5- substitution -3,4- dialkyl group selenophens；
5,5- -4,4- of substitution dialkyl group-bithiophene；
Indenes fluorenes；
Indole carbazole；
4,9- -6,7- of substitution alkyl-naphtho- thiadiazoles；
4,9- -6,7- of substitution alkyl-naphtho- selenium diazole；
Naphtho- indenes fluorenes；
Wherein, R is H atom, aryl, triphenylamine, the straight chain or branched alkyl of carbon number 1-20, or is carbon number 1-20 Alkoxy.
2. the preparation method of a kind of conjugated polymer based on naphthalene two and indenes fluorenes unit described in claim 1, it is characterised in that Comprise the following steps：
The boric acid ester monomer of naphthalene two and indenes fluorenes is passed through after Suzuki polymerisations with the monomer containing Ar structures, then successively using bromine Benzene and phenyl boric acid carry out end capping reaction, obtain the conjugated polymer based on naphthalene two and indenes fluorenes unit.
3. a kind of preparation method of conjugated polymer based on naphthalene two and indenes fluorenes unit according to claim 2, its feature It is that the temperature of the Suzuki polymerisations is 80~110 DEG C, and the reaction time is 24~48h.
4. a kind of preparation method of conjugated polymer based on naphthalene two and indenes fluorenes unit according to claim 2, its feature It is that the catalyst system of the Suzuki polymerisations includes palladium and tricyclohexyl phosphine.
5. a kind of preparation method of conjugated polymer based on naphthalene two and indenes fluorenes unit according to claim 2, its feature It is that the reaction temperature that the use bromobenzene and phenyl boric acid carry out end capping reaction is 80~110 DEG C, the reaction time is 12~ 24h。
6. a kind of conjugated polymer based on naphthalene two and indenes fluorenes unit described in claim 1 is preparing the luminous of light emitting diode Application in layer, it is characterised in that dissolve conjugated polymer organic solvent, by spin coating, inkjet printing or printing Method film forming, prepares the luminescent layer of light emitting diode.
7. application according to claim 6, it is characterised in that the organic solvent includes chlorobenzene.
CN201710030865.6A 2017-01-17 2017-01-17 A kind of conjugated polymer based on naphthalene two and indenes fluorenes unit and preparation method and application Pending CN106866938A (en)

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