CN106633004A - Conjugated polymer based on naphthothio dibenzofuran unit as well as preparation method and application thereof - Google Patents

Conjugated polymer based on naphthothio dibenzofuran unit as well as preparation method and application thereof Download PDF

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CN106633004A
CN106633004A CN201710005316.3A CN201710005316A CN106633004A CN 106633004 A CN106633004 A CN 106633004A CN 201710005316 A CN201710005316 A CN 201710005316A CN 106633004 A CN106633004 A CN 106633004A
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naphtho
conjugated polymer
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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 conjugated polymer based on a naphthothio dibenzofuran unit as well as a preparation method and an application thereof. In the invention, the conjugated polymer based on a naphthothio dibenzofuran unit is obtained through a Suzuki polymerization reaction. The conjugated polymer based on a naphthothio dibenzofuran unit disclosed by the invention has relatively good solubility; and after the conjugated polymer is dissolved with a common organic solvent, a luminous layer of a light emitting diode is prepared through spinning, ink-jet printing or printing film formation. The luminous layer based on the polymer is not subjected to annealing treatment during preparation of a luminous device, and thus the preparation technology is simpler.

Description

A kind of conjugated polymer based on naphtho- sulphur dibenzofuran unit and preparation method and application
Technical field
The invention belongs to organic photoelectric technical field, and in particular to a kind of conjugated polymer based on naphtho- sulphur dibenzofuran unit 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 Stable material becomes crucial.
But, current organic luminescent device technology encounters bottleneck problem in evolution, is exactly sending out for luminescent device Light efficiency and service life do not reach practical requirement, which greatly limits the development of OLED technology, for this problem, respectively Individual research institution is all in the research for carrying out exploration.
The naphtho- sulphur dibenzofuran unit that the present invention relates to and its polymer, because having preferable solubility property, are suitable for In solution processing, and preferably fluorescence quantum yield, its luminescent device not only efficient stable, and also it is blue for more blue saturation Light, can simultaneously realize the luminous efficiency of luminescent device and the raising of service life, can meet the requirement of full-color display.So There is huge development potentiality and prospect in organic electronic display field.
The content of the invention
Present invention aims to current polymer LED (PLED) problems faced, there is provided one kind is based on The conjugated polymer of naphtho- sulphur dibenzofuran unit.The conjugated polymer can be used as luminescent material, and with preferable dissolubility, it is higher Fluorescence quantum yield, be suitable for solution processing and inkjet printing, with good development prospect.
The present invention also aims to provide a kind of preparation side of conjugated polymer based on naphtho- sulphur dibenzofuran unit Method.
The present invention also aims to provide a kind of conjugated polymer based on naphtho- sulphur dibenzofuran unit send out in preparation Application in the luminescent layer of optical diode.
A kind of conjugated polymer based on naphtho- sulphur dibenzofuran unit, with following chemical structural formula：
In formula, R1For aryl, triphenylamine, carbon number 1-20 straight or branched alkyl, or carbon number 1-20 Alkoxyl；0≤x≤1, polymerization degree n is 1-300；
Ar is any one in following structure：
2,7- substituted fluorenes；
3,6- substituted fluorenes；
2,7- replace silicon fluorene；
3,6- replace silicon fluorene；
2,7- replace spiro fluorene；
3,6- replace spiro fluorene；
2,7- replace -9,9- dialkoxy phenyl fluorenes；3,6- take Generation -9,9- dialkoxy phenyl fluorenes；2,7- substituted carbazoles；
3,6- substituted carbazoles；
2,6- replacement-dithieno thiophenes are coughed up；
2,6- replacement-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- replaces -4- alkylthrophene bases) -2,1,3- diazosulfide；
4,7- double (5- replaces -4- alkylthrophene bases) 2,1,3- selenoles；
4,7- replace -5,6- alkyl -2,1,3- diazosulfide；
4,7- replace -5,6- alkyl -2,1,3- selenole；
2,5- replace -3,4- dialkylthiophenes；
2,5- replace -3,4- dialkyl group selenophens；
5,5- replace -4,4- dialkyl group-bithiophene；
Indenes fluorenes；
Indole carbazole；
4,9- replace -6,7- alkyl-naphtho- thiadiazoles；
4,9- replace -6,7- alkyl-naphtho- selenium diazole；
Naphtho- indenes fluorenes；
Wherein, R is H, aryl, triphenylamine, the straight chain of carbon number 1-20 or branched alkyl, or carbon number 1-20 Alkoxyl.
A kind of preparation method of described conjugated polymer based on naphtho- sulphur dibenzofuran unit, comprises the steps：
By naphtho- sulphur dibenzofuran monomer and the boric acid ester monomer for containing Ar structures after Suzuki polymerisations, then adopt successively Phenyl boric acid and bromobenzene carry out end capping reaction, obtain the conjugated polymer based on naphtho- sulphur dibenzofuran unit.
Further, the temperature of the Suzuki polymerisations is 80～100 DEG C, and the time is 24～48 hours.
Further, the temperature for carrying out end capping reaction using phenyl boric acid and bromobenzene is 80～100 DEG C, and the time is 12～ 24 hours.
A kind of described conjugated polymer based on naphtho- sulphur dibenzofuran unit is applied to prepare the luminescent layer of light emitting diode, Conjugated polymer based on naphtho- sulphur dibenzofuran unit organic solvent is dissolved, then by spin coating, inkjet printing or printing film forming, Obtain the luminescent layer of the light emitting diode；Can be used to prepare flat-panel monitor based on the light emitting diode of the luminescent layer.
Further, the organic solvent includes chlorobenzene.
Compared with prior art, the present invention has advantages below：
(1) conjugated polymer based on naphtho- sulphur dibenzofuran unit of the invention, due to larger conjugate length, so There is higher fluorescence quantum yield, be conducive to improving the device efficiency of material；
(2) conjugated polymer based on naphtho- sulphur dibenzofuran unit of the invention, with preferable dissolubility, based on the polymerization The luminescent layer of thing is when electroluminescent device is prepared without annealing so that preparation technology is simpler.
Description of the drawings
Fig. 1 is photoluminescence spectra figure of the polymer P 1 under filminess；
Fig. 2 is photoluminescence spectra figure of the polymer P 2 under filminess；
Fig. 3 is the Thermal Chart of polymer P 3；
The current density of Fig. 4 polymer Ps 4-luminous efficiency spectrogram.
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
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 over the concentrated sulfuric acid (39.06mg, 398.29umol), is heated to 110 DEG C, reacts 18h；Reactant mixture is fallen In entering water, it is 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, with silica gel column chromatography purification (eluant, eluent selects petroleum ether/dichloromethane=3/1, v/v), product is placed In refrigerator, white solid, yield 85% are obtained.1H NMR、13CNMR, MS and elementary analysis result show resulting compound For target product, preparation process chemical equation is as follows：
Embodiment 2
The preparation of 2,8- dibromo dibenzothiophens
Under argon atmosphere, dibenzothiophen (20g, 108.54mmol) is added in 250ml two-mouth bottles, adds 100ml chlorine It is imitative to be allowed to be completely dissolved, 0.5g elemental iodines are added, in the case of lucifuge, bromine (38.16g, 238.80mmol) is added dropwise over, Reactant liquor is stirred 2 hours under 0 DEG C of ice bath, is then stirred at room temperature 2 hours, and the sodium hydrogensulfite for adding saturation is quenched liquid Bromine, reactant mixture is poured into water, and is extracted with ethyl acetate, after organic layer saline solution is washed completely, plus anhydrous magnesium sulfate It is dried.After solution concentration, crude white solid is obtained, then with Gossypol recrystallized from chloroform, yield 85%.1H NMR、13CNMR, MS and Compound obtained by elementary analysis result shows is target product, and preparation process chemical equation is as follows：
Embodiment 3
The preparation of 2,8- diborate dibenzothiophens
Under an argon atmosphere, 2,8- dibromo dibenzothiophens (10g, 29.24mmol) is dissolved in into the refined tetrahydrofurans of 180mL (THF) in, the n-BuLi 28mL of 1.6mol L-1 is gradually added dropwise at -78 DEG C, is reacted 2 hours, be then quickly added into 2- different Propoxyl group -4,4,5,5- tetramethyl -1,3,2- dioxaborinate 25mL continue to react 1 hour at -78 DEG C, are to slowly warm up to Room temperature reaction 24 hours.Reactant mixture is poured into water, is extracted with ethyl acetate, after organic layer saline solution is washed completely, Plus anhydrous magnesium sulfate is dried.After solution concentration, thick pale yellow shape crude product is obtained, (eluant, eluent is selected with silica gel column chromatography purification Petrol ether/ethyl acetate=20/1, v/v), in product placing box, obtain white solid, yield 70%.1H NMR and GC-MASS Test is shown to be target product, and preparation process chemical equation is as follows：
Embodiment 4
The preparation of compound M1
Under argon atmosphere, by the bromo- 2- 2-methyl naphthoates of 2,8- diborate dibenzothiophens (5g, 11.46mmol) and 1- During (7.6g, 28.66mmol) is added to two-mouth bottle, adds 100ml toluene and be completely dissolved, add sodium carbonate (6.07g, 57.32mmol), TBAB (312.01mg, 967.86umol) and four triphenyl phosphorus palladiums (264.93mg, 229.26umol), 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, with silica gel column chromatography purification, (eluant, eluent selects petroleum ether/bis- Chloromethanes=7/1, v/v), finally give white solid, yield 80%.1H NMR、13CNMR, MS and elementary analysis result show Resulting compound is target product, and preparation process chemical equation is as follows：
Embodiment 5
The preparation of compound M2
Under argon atmosphere, M1 (10g, 18.10mmol) is added in single port bottle, add the anhydrous THF of 50ml until complete CL；Again reactant liquor is reacted into 1h at 0 DEG C, then be added dropwise over n-octyl magnesium bromide (C8H17MgBr), mixed liquor is in room temperature Lower reaction 18h.Add water to that reaction is quenched in reactant liquor, be extracted with ethyl acetate, organic layer saline solution is washed completely Afterwards, plus anhydrous magnesium sulfate be dried；After solution concentration, with silica gel column chromatography purification, (eluant, eluent selects petroleum ether/dichloromethane=3/ 1, v/v), product is placed in refrigerator, obtains white solid, yield 80%.1H NMR、13CNMR, MS and elementary analysis result show Resulting compound is target product, and preparation process chemical equation is as follows：
Embodiment 6
The preparation of compound M3
Under argon atmosphere, M2 (5g, 5.29mmol) 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 saline solution is washed completely Afterwards, plus anhydrous magnesium sulfate be dried；After solution concentration, (eluant, eluent selection petroleum ether) is purified with silica gel column chromatography, product places ice In case, white solid, yield 90% are obtained.1H NMR、13CNMR, MS and elementary analysis result show that resulting compound is Target product, preparation process chemical equation is as follows：
Embodiment 7
The preparation of compound M4
Under argon atmosphere, M3 (5g, 5.50mmol) is dissolved in 50mL dichloromethane, add iron powder (185.35mg, 3.32mmol), then bromine (1.93g, 12.10mmol) 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, with silica gel column chromatography purification, (eluant, eluent is selected Petroleum ether), yield 70%.1H NMR、13Compound obtained by CNMR, MS and elementary analysis result show is target product, is made Standby process chemistry reaction equation is as follows：
Embodiment 8
The preparation of compound M5
Under argon atmosphere, compound M4 is added in 250ml two-mouth bottles, adds acetic acid to be allowed to dissolve, added double Oxygen water (H2O2), 80 DEG C are heated to, react 16 hours；It is extracted with ethyl acetate, after organic layer saline solution is washed completely, plus nothing Water magnesium sulfate is dried；After solution concentration, (eluant, eluent selection petroleum ether) is purified with silica gel column chromatography, yield 75%.1H NMR、13Compound obtained by CNMR, MS and elementary analysis result show is target product, and preparation process chemical equation is as follows It is shown：
Embodiment 9
The preparation of compound M6
Under an argon atmosphere, M5 (10g, 19.24mmol) is dissolved in the refined THF of 180mL, at -78 DEG C gradually The n-BuLi 28mL of 1.6mol/L is added dropwise, is reacted 2 hours, be then quickly added into 2- isopropoxy -4,4,5,5- tetramethyl -1, 3,2- dioxaborinate 25mL, continue to react 1 hour at -78 DEG C, are to slowly warm up to room temperature reaction 24 hours；By reaction mixing 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 selects petrol ether/ethyl acetate=20/1, v/ with silica gel column chromatography purification V), product is placed in refrigerator, obtains white solid, yield 70%.1H NMR and GC-MASS test is shown to be target product, makes Standby process chemistry reaction equation is as follows：
Embodiment 10
The preparation of 2,7- dibromo fluorenes
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；Temperature does not surpass in bottle during dropwise addition Cross 5 DEG C；Reaction is finished, filtration, 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, and preparation process chemical equation is as follows：
Embodiment 11
The preparation of 2,7- bis- bromo- 9,9- dioctyl fluorenes
Add in there-necked flask 2,7- dibromo fluorenes (9.7g, 0.03mol), benzyltriethylammoinium chloride (0.07g, 0.3mmol), dimethyl sulfoxide (DMSO) 90mL, 45mL sodium hydrate aqueous solutions (50wt%), stirring under room temperature forms suspension；Add 1- bromine normal octanes (12.5g, 65mmol), after continuing to stir 3 hours, is extracted with ether；Second is washed with saturated sodium-chloride water solution Ether phase, anhydrous magnesium sulfate 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 elementary analysis result show resulting compound for target product, preparation process chemical equation It is as follows：
Embodiment 12
2,7- diborate -9, the preparation of 9- dioctyl fluorenes
Under an argon atmosphere, bromo- 9, the 9- dioctyl fluorenes (5g, 9.12mmol) of 2,7- bis- are dissolved in into 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 little When；Reactant mixture is poured into water, is extracted with ethyl acetate, after organic layer saline solution is washed completely, plus anhydrous magnesium sulfate It is dried；After solution concentration, thick pale yellow shape crude product is obtained, (eluant, eluent selects petroleum ether/acetic acid second with silica gel column chromatography purification Ester=15/1, v/v), product is placed in refrigerator, obtains white solid, yield 70%.1H NMR、13CNMR, MS and elementary analysis As a result the compound obtained by showing is target product, and preparation process chemical equation is as follows：
Embodiment 13
The preparation of 3,6- dibromo carbazoles
Add carbazole (24.7g, 0.1mol) in 500mL two-mouth bottles, dimethylformamide 200mL is stirred to completely 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 automatically after room temperature, reacts 6 hours, reactant liquor is added drop-wise in water and is precipitated, and takes out Filter is obtained after crude product, and suction filtration thing is recrystallized with absolute ethyl alcohol, is dried, and obtains precious color needle-like solid, yield 85%.1H NMR、13CNMR, MS and elementary analysis result show resulting compound for target product, preparation process chemical equation It is as follows：
Embodiment 14
The preparation of the bromo- N- octylcarbazols of 3,6- bis-
3,6- dibromo carbazoles (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), react 24 hours at 80 DEG C, add water terminating reaction, wash the organic phase separated, water is extracted with dichloromethane After taking, merge organic phase, use anhydrous MgSO4It is dried, vacuum distillation to be removed and obtain light yellow solid after 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, preparation process chemical equation is as follows：
Embodiment 15
The preparation of 3,6- bis- (4,4,5,5- tetramethyls -1,3,2- dioxaborinates-diyl)-N- octylcarbazols
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, reactant liquor is cooled to into -78 DEG C, then disposably adds 2- isopropoxies-(4,4,5,5- tetra- Methyl) -1,3,2- ethylenedioxy borates (37mL, 180mmol), stir 2 hours at -78 DEG C, then temperature is warmed to room temperature, Reaction terminates reaction after 24 hours；Extracted with ether, saturated common salt water washing 4 times, then be dried with anhydrous magnesium sulfate, after filtration, Solvent, product petrol ether/ethyl acetate (10 is distilled off:1) it is the purification of eluant, eluent column chromatography, obtains white solid, yield 45%.1H NMR、13Compound obtained by CNMR, MS and elementary analysis result show is target product, and preparation process chemistry is anti- Answer equation as follows：
Embodiment 16
The preparation of polymer P 1
Under argon atmosphere, by 2,7- diborate -9,9- dioctyl fluorenes (300mg, 272.92 μm of ol) and naphtho- sulphur oxygen Fluorenes (342.92mg, 272.92 μm of ol) is added in 100ml two-mouth bottles, is added 8ml toluene and is completely dissolved, and adds acetic acid Palladium (2.45mg, 10.92 μm of ol) and tricyclohexyl phosphine (6.12mg, 21.83 μm of ol), are subsequently adding 2ml tetraethyl ammonium hydroxides, 80 DEG C are warming up to, are reacted 24 hours；It is subsequently adding 30mg phenyl boric acids to be blocked, after 12 hours, then is sealed with 0.1ml bromobenzenes End；Continue to react 12 hours afterwards, product is added dropwise and is precipitated out in methyl alcohol, stir, filter, then crude product is dissolved in into 20mL Toluene in, be that eluant, eluent carries out column chromatography with toluene with 200～300 mesh silica gel as fixing phase, then solvent under reduced pressure is concentrated Afterwards, separate out in methyl alcohol again, stirring is filtered, and polymer solids are obtained after vacuum drying；Finally use first successively again Alcohol, acetone, tetrahydrofuran are respectively extracted 24 hours, remove small molecule；Tetrahydrofuran solution after concentration is instilled into precipitating in methyl alcohol, The fibrous solids conjugated polymer P1 obtained after vacuum drying.1H NMR、13CNMR, MS and elementary analysis result show gained The compound for arriving is target product, and preparation process chemical equation is as follows：
Embodiment 17
The preparation of polymer P 2
Under argon atmosphere, by 3,6- bis- (4,4,5,5- tetramethyl -1,3,2- dioxaborinates-diyl)-N- octyl group clicks Azoles (145.01mg, 272.92 μm of ol) and naphtho- sulphur dibenzofuran (300mg, 272.92 μm of ol) are added in 100ml two-mouth bottles, are added 8ml toluene is completely dissolved, and adds palladium (2.45mg, 10.92 μm of ol) and tricyclohexyl phosphine (6.12mg, 21.83 μ Mol), 2ml tetraethyl ammonium hydroxides are subsequently adding, 80 degrees Celsius are warming up to, are reacted 24 hours；It is subsequently adding 30mg phenyl boric acids to enter Row end-blocking, after 12 hours, then is blocked with 0.1ml bromobenzenes；Continue to react 12 hours afterwards, product is added dropwise and is sunk in methyl alcohol Form sediment out, stirring is filtered, then crude product is dissolved in the toluene of 20mL, with 200～300 mesh silica gel as fixing phase, is with toluene Eluant, eluent carries out column chromatography, then after solvent under reduced pressure is concentrated, separates out in methyl alcohol again, and stirring is filtered, vacuum drying After obtain polymer solids；It is last respectively to be extracted 24 hours with methyl alcohol, acetone, tetrahydrofuran successively again, remove small molecule；Will concentration Tetrahydrofuran solution afterwards instills precipitating in methyl alcohol, the fibrous solids conjugated polymer P2 obtained after vacuum drying.1H NMR 、13Compound obtained by CNMR, MS and elementary analysis result show is target product, and preparation process chemical equation is such as Shown in lower：
Embodiment 18
The preparation of polymer P 3
Under argon atmosphere, by indenes fluorenes boric acid (260.66mg, 272.92 μm of ol) and naphtho- sulphur dibenzofuran (300mg, 272.92 μm ol) add in 100ml two-mouth bottles, add 8ml toluene and be completely dissolved, add palladium (2.45mg, 10.92 μ Mol) and tricyclohexyl phosphine (6.12mg, 21.83 μm of ol), 2ml tetraethyl ammonium hydroxides are subsequently adding, are warming up to 80 degrees Celsius, Reaction 24 hours；It is subsequently adding 30mg phenyl boric acids to be blocked, after 12 hours, then is blocked with 0.1ml bromobenzenes；Continue to react 12 hours are afterwards, product is added dropwise and is precipitated out in methyl alcohol, stir, and filter, then crude product is dissolved in the toluene of 20mL, with 200～300 mesh silica gel are fixing phase, are that eluant, eluent carries out column chromatography with toluene, then after solvent under reduced pressure is concentrated, again in first Separate out in alcohol and, stirring is filtered, and polymer solids are obtained after vacuum drying；It is last to use methyl alcohol, acetone, tetrahydrochysene furan successively again Mutter it is each extracting 24 hours, remove small molecule；Tetrahydrofuran solution after concentration is instilled into precipitating in methyl alcohol, is obtained after vacuum drying Fibrous solids conjugated polymer P3.1H NMR、13Compound obtained by CNMR, MS and elementary analysis result show is mesh Mark product, preparation process chemical equation is as follows：
Embodiment 19
The preparation of polymer P 4
Under argon atmosphere, by naphtho- indenes fluorenes borate (274.33mg, 272.92 μm of ol) and naphtho- sulphur dibenzofuran (300mg, 272.92 μm of ol) add 100ml two-mouth bottles in, add 8ml toluene and be completely dissolved, add palladium (2.45mg, 10.92 μm of ol) and tricyclohexyl phosphine (6.12mg, 21.83 μm of ol), 2ml tetraethyl ammonium hydroxides are subsequently adding, it is warming up to 80 and takes the photograph Family name's degree, reacts 24 hours；It is subsequently adding 30mg phenyl boric acids to be blocked, after 12 hours, then is blocked with 0.1ml bromobenzenes；After Product is added dropwise and is precipitated out in methyl alcohol by continuous reaction for 12 hours afterwards, is stirred, and is filtered, then crude product is dissolved in into the first of 20mL It is that eluant, eluent carries out column chromatography with toluene with 200～300 mesh silica gel as fixing phase in benzene, then after solvent under reduced pressure is concentrated, then Once separate out in methyl alcohol, stirring is filtered, and polymer solids are obtained after vacuum drying；It is last again successively with methyl alcohol, third Ketone, tetrahydrofuran are respectively extracted 24 hours, remove small molecule；Tetrahydrofuran solution after concentration is instilled into precipitating in methyl alcohol, vacuum The fibrous solids conjugated polymer P4 obtained after drying.1H NMR、13CNMR, MS and elementary analysis result show resulting Compound is target product, and preparation process chemical equation is as follows：
Embodiment 20
Preparation based on the electroluminescent device of small molecule
It is on tin indium oxide (ITO) glass of 20 Ω/, acetone, washing first to be used successively 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 (PEDOT:PSS) film, thickness is 150nm；PEDOT:PSS films are dried 8 hours in vacuum drying oven at 80 DEG C； Subsequently the chlorobenzene solution (1wt%) of bipolarity small molecule emitter material P1, P2, P3, P4 is spin-coated on into PEDOT:The table of PSS films Face, thickness is 80nm；It is last to be deposited with the thick metal Al layer of a thin layer CsF (1.5nm) and 120nm successively on luminescent layer.
Electroluminescent device to obtaining carries out respectively photoelectric properties test, as a result as shown in table 1.
The photoelectric properties index of the electroluminescent device that table 1 is obtained based on 1～P4 of polymer P
As seen from table, polymer P 1, P2, P3, P4 is based on device architecture：The maximum lumen of ITO/PEDOT/EML/CsF/Al Efficiency is followed successively by 2.12cd/A, 2.87cd/A, 1.61cd/A, 5.0cd/A.
Luminescence generated by light spectrogram of the polymer P 1 under filminess as indicated with 1, it can be seen that polymer P 1 is most Big emission peak is located at 452nm.
Luminescence generated by light spectrogram of the polymer P 2 under filminess as indicated with 2, it can be seen that polymer P 2 is most Big emission peak is located at 513nm.
The Thermal Chart of polymer P 3 is as shown in figure 3, it can be seen that the heat decomposition temperature of polymer is 425 DEG C, illustrate that polymer P 3 has preferable heat endurance.
Polymer P 4 is based on device architecture：The current density of ITO/PEDOT/EML/CsF/Al-luminous efficiency spectrogram such as Fig. 4 It is shown, it can be seen that being 5.0cd/A based on the maximum lumen efficiency of the device of polymer P 4.
Above-described embodiment is the present invention preferably embodiment, but embodiments of the present invention not by above-described embodiment Limit, other any Spirit Essences and the changes, modification, replacement made under principle without departing from the present invention, combine, simplification all should For equivalent substitute mode, it is included within protection scope of the present invention.

Claims (6)

1. a kind of conjugated polymer based on naphtho- sulphur dibenzofuran unit, it is characterised in that with following chemical structural formula：
In formula, R1For aryl, triphenylamine, carbon number 1-20 straight or branched alkyl, or the alcoxyl of carbon number 1-20 Base；0≤x≤1, polymerization degree n is 1-300；
Ar is any one in following structure：
2,7- substituted fluorenes；
3,6- substituted fluorenes；
2,7- replace silicon fluorene；
3,6- replace silicon fluorene；
2,7- replace spiro fluorene；
3,6- replace spiro fluorene；
2,7- replace -9,9- dialkoxy phenyl fluorenes；
3,6- replace -9,9- dialkoxy phenyl fluorenes；
2,7- substituted carbazoles；
3,6- substituted carbazoles；
2,6- replacement-dithieno thiophenes are coughed up；
2,6- replacement-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- replaces -4- alkylthrophene bases) -2,1,3- diazosulfide；
4,7- double (5- replaces -4- alkylthrophene bases) 2,1,3- selenoles；
4,7- replace -5,6- alkyl -2,1,3- diazosulfide；
4,7- replace -5,6- alkyl -2,1,3- selenole；
2,5- replace -3,4- dialkylthiophenes；
2,5- replace -3,4- dialkyl group selenophens；
5,5- replace -4,4- dialkyl group-bithiophene；
Indenes fluorenes；
Indole carbazole；
4,9- replace -6,7- alkyl-naphtho- thiadiazoles；
4,9- replace -6,7- alkyl-naphtho- selenium diazole；
Naphtho- indenes fluorenes；
Wherein, R is H, aryl, triphenylamine, the straight chain of carbon number 1-20 or branched alkyl, or the alcoxyl of carbon number 1-20 Base.
2. the preparation method of a kind of conjugated polymer based on naphtho- sulphur dibenzofuran unit described in claim 1, it is characterised in that Comprise the steps：
Under argon atmosphere, by naphtho- sulphur dibenzofuran monomer and the boric acid ester monomer for containing Ar structures after Suzuki polymerisations, Successively end capping reaction carried out using phenyl boric acid and bromobenzene again, obtain the conjugated polymer based on naphtho- sulphur dibenzofuran unit.
3. the preparation method of a kind of conjugated polymer based on naphtho- sulphur dibenzofuran unit according to claim 2, its feature It is that the temperature of the Suzuki polymerisations is 80～100 DEG C, and the time is 24～48 hours.
4. the preparation method of a kind of conjugated polymer based on naphtho- sulphur dibenzofuran unit according to claim 2, its feature It is that the temperature for carrying out end capping reaction using phenyl boric acid and bromobenzene is 80～100 DEG C, and the time is 12～24 hours.
5. a kind of conjugated polymer based on naphtho- sulphur dibenzofuran unit described in claim 1 is applied to prepare light emitting diode Luminescent layer, it is characterised in that will be based on naphtho- sulphur dibenzofuran unit conjugated polymer with organic solvent dissolve, then by spin coating, Inkjet printing or printing film forming, obtain the luminescent layer.
6. application according to claim 5, it is characterised in that the organic solvent includes chlorobenzene.
CN201710005316.3A 2017-01-04 2017-01-04 Conjugated polymer based on naphthothio dibenzofuran unit as well as preparation method and application thereof Pending CN106633004A (en)

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107312163A (en) * 2017-05-18 2017-11-03 华南理工大学 A kind of blue light conjugated polymer based on two phenanthro- sulphur dibenzofuran units and preparation method and application
CN107540822A (en) * 2017-08-30 2018-01-05 华南理工大学 A kind of conjugated polymer luminescent material based on double sulphur oxindoles fluorenes units and preparation method and application
WO2019041847A1 (en) * 2017-08-30 2019-03-07 华南理工大学 Naphthothiodibenzofuran unit-based blue light polymer light-emitting material, preparation method therefor and use thereof
CN109776768A (en) * 2018-12-31 2019-05-21 华南理工大学 A kind of blue light conjugated polymer and the preparation method and application thereof based on triphenylamine and sulphur dibenzofuran unit

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101712674A (en) * 2009-11-13 2010-05-26 华南理工大学 Alkyl substituted-S,S-dioxo-dibenzothiophene monomer, preparation method and polymer thereof
CN103965446A (en) * 2013-01-31 2014-08-06 海洋王照明科技股份有限公司 Organic semiconductor material polymer and preparation method thereof, and organic electroluminescent device
CN104004165A (en) * 2014-05-07 2014-08-27 华南理工大学 S,S-dioxo-dibenzothiophene unit-containing electron donor polymer and use thereof
CN105636944A (en) * 2013-10-14 2016-06-01 默克专利有限公司 Materials for electronic devices
CN106243329A (en) * 2016-07-29 2016-12-21 华南理工大学 One is based on S, S dioxydibenze thiophthene derivative replaces conjugated polymer luminescent material and preparation method and application to receptor type

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101712674A (en) * 2009-11-13 2010-05-26 华南理工大学 Alkyl substituted-S,S-dioxo-dibenzothiophene monomer, preparation method and polymer thereof
CN103965446A (en) * 2013-01-31 2014-08-06 海洋王照明科技股份有限公司 Organic semiconductor material polymer and preparation method thereof, and organic electroluminescent device
CN105636944A (en) * 2013-10-14 2016-06-01 默克专利有限公司 Materials for electronic devices
CN104004165A (en) * 2014-05-07 2014-08-27 华南理工大学 S,S-dioxo-dibenzothiophene unit-containing electron donor polymer and use thereof
CN106243329A (en) * 2016-07-29 2016-12-21 华南理工大学 One is based on S, S dioxydibenze thiophthene derivative replaces conjugated polymer luminescent material and preparation method and application to receptor type

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
LI HAIYING等: ""The interplay of conformation and photophysical properties in deep-blue fluorescent oligomers"", 《CHEMICAL COMMUNICATIONS》 *

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107312163A (en) * 2017-05-18 2017-11-03 华南理工大学 A kind of blue light conjugated polymer based on two phenanthro- sulphur dibenzofuran units and preparation method and application
CN107540822A (en) * 2017-08-30 2018-01-05 华南理工大学 A kind of conjugated polymer luminescent material based on double sulphur oxindoles fluorenes units and preparation method and application
WO2019041847A1 (en) * 2017-08-30 2019-03-07 华南理工大学 Naphthothiodibenzofuran unit-based blue light polymer light-emitting material, preparation method therefor and use thereof
CN107540822B (en) * 2017-08-30 2020-09-22 华南理工大学 Conjugated polymer luminescent material based on bisthiooxindole fluorene unit and preparation method and application thereof
CN109776768A (en) * 2018-12-31 2019-05-21 华南理工大学 A kind of blue light conjugated polymer and the preparation method and application thereof based on triphenylamine and sulphur dibenzofuran unit

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Application publication date: 20170510