CN106977703A - A kind of Bipolar Polymer luminescent material based on diaryl-amine group and preparation method and application - Google Patents

A kind of Bipolar Polymer luminescent material based on diaryl-amine group and preparation method and application Download PDF

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CN106977703A
CN106977703A CN201710177020.XA CN201710177020A CN106977703A CN 106977703 A CN106977703 A CN 106977703A CN 201710177020 A CN201710177020 A CN 201710177020A CN 106977703 A CN106977703 A CN 106977703A
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fluorenes
substitution
diaryl
amine group
alkyl
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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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Abstract

The invention discloses a kind of Bipolar Polymer luminescent material based on diaryl-amine group and preparation method and application.The bipolarity conjugated polymer of such group containing diaryl-amine, the hole transporting unit diaryl-amine group of electrophilic electric transmission unit sulphur dibenzofuran and electron is introduced in the main chain of polymer simultaneously, then obtained using phenyl boric acid and bromobenzene progress end capping reaction successively.Because main polymer chain contains electronics and hole transporting unit simultaneously, be conducive to injection and the transmission balance of carrier, be conducive to improving device efficiency.The Bipolar Polymer luminescent material based on diaryl-amine group of the present invention has preferable dissolubility, is appropriate for solution processing and typographical display, the luminescent layer for preparing Organic Light Emitting Diode；Such polymeric material is when preparing electroluminescent device without annealing so that preparation technology is simpler.

Description

A kind of Bipolar Polymer luminescent material based on diaryl-amine group and preparation method thereof With application
Technical field
The invention belongs to organic photoelectric technical field, and in particular to a kind of Bipolar Polymer hair based on diaryl-amine group Luminescent material and preparation method and application.
Background technology
In the past thirty years, organic electronic and photoelectronic industry, including organic/polymer LED, it is organic Field-effect transistor, the field such as organic solar batteries has obtained swift and violent development, and gradually realizes 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 attracted the concerns of numerous research institutions and Research Team in the world.And among these, develop new height The stable material of effect turns into key.
But, current organic luminescent device technology encounters bottleneck problem in evolution, is exactly the hair of luminescent device Light efficiency and service life do not reach practical requirement, which greatly limits the development of Organic Light Emitting Diode (OLED) technology, For this problem, each research institution is all carrying out the research of exploration.
The Bipolar Polymer luminescent material based on diaryl-amine group that the present invention relates to, because with preferably molten Solve performance, it is adaptable to which solution is processed, and preferably fluorescence quantum yield, its luminescent device not only efficient stable, and for more Saturation blue light.Introduce electric transmission unit and hole transporting unit in main polymer chain simultaneously, be conducive to carrier injection and Transmission.The raising of the luminous efficiency and service life of luminescent device can be realized simultaneously, can meet the requirement of full-color display.Institute To there is huge development potentiality and prospect in organic electronic display field.
The content of the invention
It is an object of the invention to be based on for current polymer LED (PLED) problems faced there is provided one kind The Bipolar Polymer luminescent material of diaryl-amine group.The conjugated polymer can be used as luminescent material, and with preferably dissolving Property, higher fluorescence quantum yield is suitable for solution processing and inkjet printing, with good development prospect, simultaneously because The main chain of polymer introduces electric transmission unit and hole transporting unit, is conducive to the injection and transmission of carrier, is conducive to device The raising of part efficiency, while the problem of organic electronic device stability and the device lifetime of correlation can be solved.
The present invention also aims to provide a kind of Bipolar Polymer luminescent material based on diaryl-amine group Preparation method.
The present invention also aims to provide a kind of Bipolar Polymer luminescent material based on diaryl-amine group to exist Prepare the application in the luminescent layer of Organic Light Emitting Diode.
A kind of Bipolar Polymer luminescent material based on diaryl-amine group, with following structural formula：
In formula, Ar is aromatic group；R1-R8Selected from-H ,-F ,-Cl ,-Br ,-I ,-D ,-CN ,-NO2、-CF3, carbon atom Linear paraffin base, the branched paraffin of carbon number 1~20, carbon number 1-10 alkane thioether, the carbon number 3- of number 1~20 10 alkane ether group；0≤x≤1,0≤y≤1, polymerization degree n is 1-300；
Ar is any one in following structural formula：
2,7- substitution alkyl phenanthrenes；
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- substitutions-dithieno thiophene is coughed up；
2,6- substitutions-dithieno cyclopentadiene；
2,5- substituted pyridines；
2,6- substituted pyridines；
3,5- substituted pyridines；
3,5- double (4- substituted 4-phenyls) -4- bases -1,2,4- triazoles；
3,5- double (4- substituted 4-phenyls) -1,2,4- oxadiazoles；
4,7- double (5- substitution -4- alkylthrophenes base) -2,1,3- diazosulfide；
4,7- double (5- substitution -4- alkylthrophenes base) 2,1,3- selenoles；
4,7- substitution -5,6- alkyl -2,1,3- diazosulfides；
4,7- substitution -5,6- alkyl -2,1,3- selenoles；
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, aryl, triphenylamine, carbon number 1-20 straight or branched alkyl, or is carbon number 1-20's Alkoxy.
The method for preparing a kind of described Bipolar Polymer luminescent material based on diaryl-amine group, including following step Suddenly：
Under argon atmosphere, by unit, the S of the group containing diaryl-amine, S- dioxo-dibenzothiophenes, alkyl fluorenes monomer and alkane After base fluorenes boric acid ester monomer is by Suzuki polymerisations, then institute is obtained using phenyl boric acid and bromobenzene progress end capping reaction successively State the bipolarity conjugated polymer based on diaryl-amine group.
Further, monomer, the S of the group containing diaryl-amine, S- dioxo-dibenzothiophenes, alkyl fluorenes monomer and alkyl The mol ratio of fluorenes boric acid ester monomer is 1:5:19:25.
Further, the temperature of the Suzuki polymerisations is 80~100 DEG C, and the time is 24~48 hours.
Further, it is 80~100 DEG C to carry out the temperature of end capping reaction using phenyl boric acid and bromobenzene, and the time is 12~ 24 hours.
A kind of described Bipolar Polymer luminescent material based on diaryl-amine group is applied to prepare light emitting diode Luminescent layer, the Bipolar Polymer based on diaryl-amine group is dissolved with organic solvent, then by spin coating, inkjet printing or Film forming is printed, the luminescent layer of the light emitting diode is obtained.
Further, the organic solvent includes chlorobenzene.
Compared with prior art, the invention has the advantages that and beneficial effect：
(1) conjugated polymer of the invention, the backbone structure of conjugation, which assigns polymer, has abundant optically and electrically property Can, including luminescence generated by light, electroluminescent, photovoltaic effect, characteristic of semiconductor and carrier transmission characteristics；
(2) conjugated polymer of the invention, during applied to preparing complicated Heterolamellar photovoltaic device, using conjugated polymer Solution processing characteristics, prepare luminescent layer, so as to further make by the solution processing technology such as inkjet printing, silk-screen printing, spin coating Standby polymer light electrical part；
(3) conjugated polymer of the invention, due to larger conjugate length, so there is higher fluorescent quantum production Rate, is conducive to improving the device efficiency of material；
(4) conjugated polymer of the invention, with preferable dissolubility, the luminescent layer based on the polymer prepare it is electroluminescent Without annealing during luminescent device so that preparation technology is simpler.
Brief description of the drawings
Fig. 1 is the TGA spectrograms of polymer P 1；
Fig. 2 is photoluminescence spectra figure of the polymer P 2 under filminess；
Fig. 3 is photoluminescence spectra figure of the polymer P 3 under filminess.
Embodiment
Below in conjunction with specific embodiment, the present invention is further elaborated, but the invention is not restricted to following examples.
Embodiment 1
The preparation of 2- bromine fluorenes
In 250mL there-necked flasks, fluorenes (16.6g, 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 16 hours, filtering, Gossypol recrystallized from chloroform, obtains white solid 19.3g, yield 84%.1H NMR、13CNMR, MS and member Compound obtained by plain analysis result shows is target product, and its chemical equation is as follows：
Embodiment 2
The preparation of bromo- 9, the 9- dioctyl fluorenes of 2-
2- bromines fluorenes (7.4g, 0.03mol), benzyltriethylammoinium chloride (0.07g, 0.3mmol), two are added in there-necked flask Methyl sulfoxide 90mL, 45mL sodium hydrate aqueous solution (50wt%), at room temperature stirring form suspension；1- bromine normal octanes are added dropwise (12.5g, 65mmol), continues after stirring 3 hours, is extracted with ether；Ether phase, anhydrous sulphur are washed with saturated sodium-chloride water solution Sour magnesium is dried.Solvent is boiled off, product petroleum ether makees the purification of eluant, eluent column chromatography, obtains white solid.1H NMR、13CNMR, MS and Compound obtained by elementary analysis result shows is target product, and its chemical equation is as follows：
Embodiment 3
The preparation of 2- borate -9,9- dioctyl fluorenes
Under an argon atmosphere, bromo- 9, the 9- dioctyl fluorenes (5g, 10.65mmol) of 2- are dissolved in the refined tetrahydrochysene furans of 180mL Mutter in (THF), 1.6mol.L is gradually added dropwise at -78 DEG C-1N-BuLi 28mL, react 2 hours, then add 2- isopropyl oxygen Base -4,4,5,5- tetramethyls -1,3,2- dioxaborinate 25mL continue to react 1 hour at -78 DEG C, are warming up to room temperature reaction 24 hours.Reactant mixture is poured into water, is extracted with ethyl acetate, after organic layer is washed completely with saline solution, plus anhydrous sulphur Sour magnesium is dried.After solution concentration, thick pale yellow shape crude product is obtained, (eluant, eluent selection petroleum ether/second is purified with silica gel column chromatography Acetoacetic ester=20/1, v/v), product is placed in refrigerator obtain white solid, yield 70% for a long time.1H NMR、13CNMR, MS and Compound obtained by elementary analysis result shows is target product, and its chemical equation is as follows：
Embodiment 4
The 2-methyl naphthoate of 1- bromines two
Under an argon atmosphere, the bromo- 2- naphthoic acids (10g, 39.83mmol) of 1- are added in two-mouth bottle, adds 100mL first Alcohol, is then added dropwise 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 is washed completely with saline solution, 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, and its chemical equation is as follows：
Embodiment 5
Compound M1 preparation
Under argon atmosphere, by 2- borates -9,9- dioctyl fluorene (5g, 9.68mmol) and the 2-methyl naphthoate of 1- bromines two (2.69g, 10.16mmol) is added in two-mouth bottle, is added 100ml toluene and is completely dissolved, adds sodium carbonate (5.13g, 43.89mmol) and TBAB (312.01mg, 967.86umol), 18h is reacted at 110 DEG C.Will reaction Mixture is poured into water, and is extracted with ethyl acetate, after organic layer is washed completely with saline solution, plus anhydrous magnesium sulfate is dried.Solution (eluant, eluent selects petroleum ether/dichloromethane=5/1, v/v) after concentration, is purified with silica gel column chromatography, white solid is finally given, Yield 80%.1H NMR、13Compound obtained by CNMR, MS and elementary analysis result show is target product, and it chemically reacts Equation is as follows：
Embodiment 6
Compound M2 preparation
Under argon atmosphere, M1 (5g, 8.70mmol) is added in single port bottle, the anhydrous THF of 50ml are added until complete Dissolving.Reaction solution is reacted into 1h at 0 DEG C again, then C is added dropwise8H17MgBr (n-octyl magnesium bromide), mixed liquor is at room temperature React 18h.Add water in reaction solution that reaction is quenched, be extracted with ethyl acetate, after organic layer is washed completely with saline solution, Plus anhydrous magnesium sulfate is dried.After solution concentration, purified with silica gel column chromatography (eluant, eluent selects petroleum ether/dichloromethane=3/1, V/v), product is placed in refrigerator obtain white solid, yield 80% for a long time.1H NMR、13CNMR, MS and elementary analysis result Compound obtained by showing is target product, and its chemical equation is as follows：
Embodiment 7
Compound M3 preparation
Under argon atmosphere, M2 (5g, 6.48mmol) is dissolved in 50ml dichloromethane, trifluoro is added dropwise at room temperature Change borate ether solution (439.59mg, 6.48mmol), react 18h.It is extracted with ethyl acetate, organic layer is washed completely with saline solution Afterwards, plus anhydrous magnesium sulfate dry.After solution concentration, purified with silica gel column chromatography (eluant, eluent selection petroleum ether), product is for a long time Place in refrigerator and obtain white solid, yield 90%.1H NMR、13CNMR, MS and elementary analysis result show resulting chemical combination Thing is target product, and its chemical equation is as follows：
Embodiment 8
The preparation of naphtho- indenes fluorenes (NIF)
Under argon atmosphere, M3 (5g, 6.64mmol) is dissolved in 50mL dichloromethane, add iron powder (185.35mg, 3.32mmol), then bromine (1.06g, 6.64mmol) is added dropwise, 18h is reacted at room temperature.It is extracted with ethyl acetate, it is organic After layer is washed completely with saline solution, 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, its Chemical equation is as follows：
Embodiment 9
The synthesis of compound diphenylamines
Under argon atmosphere, by compound aniline (4.68g, 50.23mmol) and equal trimethyl bromobenzene (10g, 50.23mmol) it is added in 250ml two-mouth bottles, adds sodium tert-butoxide (24.14g, 251.15mmol), adds 100ml toluene Dissolved, palladium (225.54mmol, 1mmol) and tri-butyl phosphine (406.49mmol, 1mmol) are eventually adding, 110 Reacted 18 hours at DEG C.It is extracted with ethyl acetate, after organic layer is washed completely with saline solution, plus anhydrous magnesium sulfate is dried.Solution After concentration, (eluant, eluent selection petroleum ether), yield 70% are purified with silica gel column chromatography.1H NMR、13CNMR, MS and elementary analysis As a result the compound obtained by showing is target product, and its chemical equation is as follows：
Embodiment 10
Compound M3 synthesis
Under argon atmosphere, compound indenes fluorenes (5g, 5.69mmol) and diphenylamines (2.32g, 10.98mmol) are added to In 250ml two-mouth bottles, sodium tert-butoxide (2.64g, 27.44mmol) is added, 100ml toluene is added and carries out dissolving, finally add Enter palladium (44.42mg, 109.77umol) and tri-butyl phosphine (44.42mmol, 219.53umol), reacted at 110 DEG C 18 hours.It is extracted with ethyl acetate, after organic layer is washed completely with saline solution, plus anhydrous magnesium sulfate is dried.After solution concentration, use Silica gel column chromatography purifies (eluant, eluent selection petroleum ether), yield 70%.1H NMR、13CNMR, MS and elementary analysis result show institute Obtained compound is target product, and its chemical equation is as follows：
Embodiment 11
Compound M2 synthesis
Under argon atmosphere, M1 (5g, 4.47mmol) is dissolved in 50mL dichloromethane, add iron powder (238.29mg, 4.27mmol), then bromine (1.50g, 9.39mmol) is added dropwise, 18h is reacted at room temperature.It is extracted with ethyl acetate, it is organic After layer is washed completely with saline solution, 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, its Chemical equation is as follows：
Embodiment 12
Compound M3 synthesis
Under argon atmosphere, compound naphtho- indenes fluorenes (5g, 5.49mmol) and diphenylamines (2.32g, 10.98mmol) are added Enter into 250ml two-mouth bottles, add sodium tert-butoxide (2.64g, 27.44mmol), add 100ml toluene and carry out dissolving, most Palladium (44.42mg, 109.77umol) and tri-butyl phosphine (44.42mmol, 219.53umol) are added afterwards, at 110 DEG C Reaction 18 hours.It is extracted with ethyl acetate, after organic layer is washed completely with saline solution, plus anhydrous magnesium sulfate is dried.Solution is concentrated Afterwards, (eluant, eluent selection petroleum ether), yield 70% are purified with silica gel column chromatography.1H NMR、13CNMR, MS and elementary analysis result Compound obtained by showing is target product, and its chemical equation is as follows：
Embodiment 13
Compound M4 synthesis
Under argon atmosphere, M3 (5g, 4.27mmol) is dissolved in 50mL dichloromethane, add iron powder (238.29mg, 4.27mmol), then bromine (1.50g, 9.39mmol) is added dropwise, 18h is reacted at room temperature.It is extracted with ethyl acetate, it is organic After layer is washed completely with saline solution, 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, its Chemical equation is as follows：
Embodiment 14
Compound M5 synthesis
Under argon atmosphere, compound alkyl luxuriant and rich with fragrance (5g, 8.92mmol) and diphenylamines (3.77g, 17.82mmol) are added Into 250ml two-mouth bottles, sodium tert-butoxide (4.29g, 44.61mmol) is added, 100ml toluene is added and carries out dissolving, finally Palladium (40.06mg, 178.43umol) and tri-butyl phosphine (72.20mmol, 356.86umol) are added, it is anti-at 110 DEG C Answer 18 hours.It is extracted with ethyl acetate, after organic layer is washed completely with saline solution, plus anhydrous magnesium sulfate is dried.After solution concentration, (eluant, eluent selection petroleum ether), yield 70% are purified with silica gel column chromatography.1H NMR、13CNMR, MS and elementary analysis result show Resulting compound is target product, and its chemical equation is as follows：
Embodiment 15
Compound M6 synthesis
Under argon atmosphere, M5 (5g, 6.09mmol) is dissolved in 50mL dichloromethane, add iron powder (3.4mg, 60.88umol), then bromine (1.95g, 12.18mmol) is added dropwise, 18h is reacted at room temperature.It is extracted with ethyl acetate, has After machine layer is washed completely with saline solution, plus anhydrous magnesium sulfate is dried.After solution concentration, (eluant, eluent choosing is purified with silica gel column chromatography Select petroleum ether), yield 70%.1H NMR、13Compound obtained by CNMR, MS and elementary analysis result show is target product, Its chemical equation is as follows：
Embodiment 17
The preparation of polymer P 1
Under argon atmosphere, by the borate (200mg, 242.20umol) of fluorenes, fluorenes (134.86mg, 184.08umol), Sulphur dibenzofuran (18.12mg, 48.44umol) and compound M2 (12.40mg, 9.69umol) are added in 100ml two-mouth bottles, are added 8ml toluene is completely dissolved, and substitutes gas three times, adds palladium (2.17mg, 9.68 μm of ol) and tricyclohexyl phosphine (5.43mg, 19.35 μm of ol), substitute gas three times, then add 2ml tetraethyl ammonium hydroxides, are warming up to 80 DEG C, reaction 24 is small When.Then addition 30mg phenyl boric acids are blocked, after 12 hours, then are blocked with 0.1ml bromobenzenes, continue to react 12 hours； Afterwards, product is added dropwise and be precipitated out in methyl alcohol, stirred, crude product then is dissolved in 20mL toluene by filtering, with 200~ 300 mesh silica gel are stationary phase, are that eluant, eluent carries out column chromatography with toluene, then after solvent under reduced pressure is concentrated, again in methyl alcohol Separate out and, stir, filtering obtains polymer solids after vacuum drying.It is finally each with methanol, acetone, tetrahydrofuran successively again Extracting 24 hours, removes small molecule.Tetrahydrofuran solution after concentration is instilled into precipitating, the fibre obtained after vacuum drying in methanol Tie up shape solid conjugated polymer P1.Chemical equation is as follows：
Thermogravimetric analysis (TGA) spectrogram of obtained polymer P 1 is as shown in figure 1, it can be seen that polymer P 1 Decomposition temperature is 417 DEG C.
Embodiment 18
The preparation of polymer P 2
Under argon atmosphere, by the borate (200mg, 242.20umol) of fluorenes, fluorenes (134.86mg, 84.08umol), sulphur Dibenzofuran (18.12mg, 48.44umol) and compound M4 (12.75mg, 9.69umol) are added in 100ml two-mouth bottles, are added 8ml toluene is completely dissolved, and substitutes gas three times, adds palladium (2.17mg, 9.68 μm of ol) and tricyclohexyl phosphine (5.43mg, 19.35 μm of ol), substitute gas three times, then add 2ml tetraethyl ammonium hydroxides, are warming up to 80 DEG C, reaction 24 is small When.Then addition 30mg phenyl boric acids are blocked, after 12 hours, then are blocked with 0.1ml bromobenzenes, continue to react 12 hours； Afterwards, product is added dropwise and be precipitated out in methyl alcohol, stirred, crude product then is dissolved in 20mL toluene by filtering, with 200~ 300 mesh silica gel are stationary phase, are that eluant, eluent carries out column chromatography with toluene, then after solvent under reduced pressure is concentrated, again in methyl alcohol Separate out and, stir, filtering obtains polymer solids after vacuum drying.It is finally each with methanol, acetone, tetrahydrofuran successively again Extracting 24 hours, removes small molecule.Tetrahydrofuran solution after concentration is instilled into precipitating, the fibre obtained after vacuum drying in methanol Tie up shape solid conjugated polymer P2.Chemical equation is as follows：
Photoluminescence spectra figure of the obtained polymer P 2 under filminess is as shown in Fig. 2 it can be seen that poly- Compound P2 maximum emission peak is located at 482nm.
Embodiment 19
The preparation of polymer P 3
Under argon atmosphere, by the borate (200mg, 242.20umol) of fluorenes, fluorenes (134.86mg, 184.08umol), Sulphur dibenzofuran (18.12mg, 48.44umol) and compound M6 (11.10mg, 9.69umol) are added in 100ml two-mouth bottles, are added 8ml toluene is completely dissolved, and substitutes gas three times, adds palladium (2.17mg, 9.68 μm of ol) and tricyclohexyl phosphine (5.43mg, 19.35 μm of ol), substitute gas three times, then add 2ml tetraethyl ammonium hydroxides, are warming up to 80 DEG C, reaction 24 is small When.Then addition 30mg phenyl boric acids are blocked, after 12 hours, then are blocked with 0.1ml bromobenzenes, continue to react 12 hours； Afterwards, product is added dropwise and be precipitated out in methyl alcohol, stirred, crude product then is dissolved in 20mL toluene by filtering, with 200~ 300 mesh silica gel are stationary phase, are that eluant, eluent carries out column chromatography with toluene, then after solvent under reduced pressure is concentrated, again in methyl alcohol Separate out and, stir, filtering obtains polymer solids after vacuum drying.It is finally each with methanol, acetone, tetrahydrofuran successively again Extracting 24 hours, removes small molecule.Tetrahydrofuran solution after concentration is instilled into precipitating, the fibre obtained after vacuum drying in methanol Tie up shape solid conjugated polymer P3.Chemical equation is as follows：
Photoluminescence spectra figure of the obtained polymer P 3 under filminess is as shown in figure 3, it can be seen that poly- Compound P3 maximum emission peak is located at 460nm.
Embodiment 20
The preparation of electroluminescent device based on polymer
On tin indium oxide (ITO) glass of well in advance, its square resistance is 20 Ω/, and acetone, washing are first used successively Agent, deionized water and isopropanol are cleaned by ultrasonic, plasma treatment 10 minutes.Spin coating, which 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；Then double focusing compound luminescent material P1, P2, P3 and P4 chlorobenzene solution (1wt%) are spin-coated on respectively PEDOT:The surface of PSS films, thickness is 80nm, is used as luminescent layer；A thin layer CsF is finally deposited successively on luminescent layer (1.5nm) and 120nm thick metal Al layer.
The photoelectric properties index of electroluminescent device based on 1~P3 of polymer P is as shown in table 1.
The photoelectric properties index of electroluminescent device of the table 1 based on 1~P3 of polymer P
As shown in Table 1, the electroluminescent device based on bipolarity conjugated polymer luminescent material P1, P2, P3, based on device Structure：ITO/PEDOT/EML/CsF/Al maximum lumen efficiency is respectively 1.82cd/A, 1.77cd/A, 1.61cd/A.
Above-described embodiment is preferably embodiment, but embodiments of the present invention are not by above-described embodiment of the invention Limitation, it is other it is any without departing from Spirit Essences and the change made under principle of the present invention, modification, replacement, combine, simplification all should For equivalent substitute mode, it is included within protection scope of the present invention.

Claims (6)

1. a kind of Bipolar Polymer luminescent material based on diaryl-amine group, it is characterised in that chemical structural formula is as follows：
In formula, Ar is aromatic group；R1-R8Selected from-H ,-F ,-Cl ,-Br ,-I ,-D ,-CN ,-NO2、-CF3, carbon number 1~ 20 linear paraffin base, the branched paraffin of carbon number 1~20, carbon number 1-10 alkane thioether, carbon number 3-10 Alkane ether group；0≤x≤1,0≤y≤1, polymerization degree n is 1-300；
Ar is any one in following structural formula：
2,7- substitution alkyl phenanthrenes；
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- substitutions -9, 9- dialkoxy phenyl fluorenes；2,7- substituted carbazoles；
3,6- substituted carbazoles；
2,6- substitutions-dithieno thiophene is coughed up；
2,6- substitutions-dithieno cyclopentadiene；
2,5- substituted pyridines；
2,6- substituted pyridines；
3,5- substituted pyridines；
3,5- double (4- substituted 4-phenyls) -4- bases -1,2,4- triazoles；
3,5- double (4- substituted 4-phenyls) -1,2,4- oxadiazoles；
4,7- double (5- substitution -4- alkylthrophenes base) -2,1,3- diazosulfide；
4,7- double (5- substitution -4- alkylthrophenes base) 2,1,3- selenoles；
4,7- substitution -5,6- alkyl -2,1,3- diazosulfides；
4,7- substitution -5,6- alkyl -2,1,3- selenoles；
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, aryl, triphenylamine, carbon number 1-20 straight or branched alkyl, or is carbon number 1-20 alcoxyl Base.
2. preparing a kind of method of Bipolar Polymer luminescent material based on diaryl-amine group described in claim 1, it is special Levy and be, comprise the following steps：
Under argon atmosphere, by monomer, the S of the group containing diaryl-amine, S- dioxo-dibenzothiophenes, alkyl fluorenes monomer and alkyl fluorenes After boric acid ester monomer is by Suzuki polymerisations, then the base is obtained using phenyl boric acid and bromobenzene progress end capping reaction successively In the bipolarity conjugated polymer of diaryl-amine group.
3. a kind of preparation method of Bipolar Polymer luminescent material based on diaryl-amine group according to claim 2, Characterized in that, monomer, the S of the group containing diaryl-amine, S- dioxo-dibenzothiophenes, alkyl fluorenes monomer and alkyl fluorenes boric acid The mol ratio of ester monomer is 1:5:19:25.
4. a kind of preparation method of Bipolar Polymer luminescent material based on diaryl-amine group according to claim 2, Characterized in that, the temperature of the Suzuki polymerisations is 80~100 DEG C, the time is 24~48 hours；Using phenyl boric acid and The temperature that bromobenzene carries out end capping reaction is 80~100 DEG C, and the time is 12~24 hours.
5. a kind of Bipolar Polymer luminescent material based on diaryl-amine group described in claim 1 is applied to prepare luminous two The luminescent layer of pole pipe, it is characterised in that the Bipolar Polymer based on diaryl-amine group is dissolved with organic solvent, then led to Spin coating, inkjet printing or printing film forming are crossed, the luminescent layer of the light emitting diode is obtained.
6. application according to claim 5, it is characterised in that the organic solvent includes chlorobenzene.
CN201710177020.XA 2017-03-23 2017-03-23 A kind of Bipolar Polymer luminescent material based on diaryl-amine group and preparation method and application Pending CN106977703A (en)

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