CN104178125A - Blue light phosphorescent host material containing tetraphenyl-silicon unit, preparation method and organic electroluminescent device thereof - Google Patents
Blue light phosphorescent host material containing tetraphenyl-silicon unit, preparation method and organic electroluminescent device thereof Download PDFInfo
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- CN104178125A CN104178125A CN201310204487.0A CN201310204487A CN104178125A CN 104178125 A CN104178125 A CN 104178125A CN 201310204487 A CN201310204487 A CN 201310204487A CN 104178125 A CN104178125 A CN 104178125A
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Abstract
Belonging to the field of organic semiconductor materials, the invention discloses a blue light phosphorescent host material containing a tetraphenyl-silicon unit, a preparation method and an organic electroluminescent device thereof. The blue light phosphorescent host material containing the tetraphenyl-silicon unit provided by the invention has a high triplet state energy level, and can effectively prevent back transmission of energy to the host material in a luminescence process, thus greatly improving the luminescence efficiency.
Description
Technical field
The present invention relates to organic semiconductor material field, relate in particular to a kind of blue emitting phosphor material of main part containing tetraphenyl-silicon unit and preparation method thereof.The invention still further relates to a kind of organic electroluminescence device, its luminescent layer material includes the blue emitting phosphor material of main part containing tetraphenyl-silicon unit.
Background technology
Organic electroluminescence device has that driving voltage is low, fast response time, angular field of view are wide and can be finely tuned and be changed luminescent properties and make rich color by chemical structure, easily realize the advantages such as resolving power is high, lightweight, large-area flat-plate demonstration, be described as " 21 century flat panel display ", become the focus of the subjects such as material, information, physics and flat pannel display area research.Following commercialization Organic Light Emitting Diode efficiently will contain organo-metallic phosphorescent substance possibly, because they can all catch singlet and triplet excitons, thereby realize 100% internal quantum efficiency.But, because the excited state exciton life-span of transition metal complex is relatively long, cause unwanted triplet state-triplet state (T
1-T
1) cancellation in device real work.In order to overcome this problem, investigators are often doped to triplet state shiner in organic main body material.
In recent years, green and red phosphorescent OLED device exhibits goes out gratifying electroluminescent efficiency.And blue phosphorescent device is little efficiently, major cause is to lack to have good carrier transmission performance and higher triplet (E simultaneously
t) material of main part.
Summary of the invention
One of problem to be solved by this invention is to provide a kind of have good carrier transmission performance and higher triplet (E
t) containing the blue emitting phosphor material of main part of tetraphenyl-silicon unit.
Two of problem to be solved by this invention is to provide a kind of preparation method of the blue emitting phosphor material of main part containing tetraphenyl-silicon unit.
Three of problem to be solved by this invention is to provide a kind of organic electroluminescence device, and its luminescent layer material includes the blue emitting phosphor material of main part containing tetraphenyl-silicon unit.
Technical scheme of the present invention is as follows:
Containing a blue emitting phosphor material of main part for tetraphenyl-silicon unit, its structural formula is as follows:
, triphenyl (4 '-(9-phenyl-9H-fluorenes-9-yl) biphenyl-4-yl) silane.
The preparation method of the above-mentioned blue emitting phosphor material of main part containing tetraphenyl-silicon unit, comprises the steps:
The compd A and the B that provide respectively following structural formula to represent,
i.e. (4-bromophenyl) tri-phenyl-silane;
it is 2-(4-(9-phenyl-9H-fluorenes-9-yl) phenyl) boric acid ester;
Under oxygen-free environment, the compd A that is 1:1～1.2 by mol ratio and B are added in the organic solvent that contains catalyzer and alkaline solution and dissolve, at 70～130 DEG C, carry out Suzuki coupling reaction 12～48 hours, stopped reaction cool to room temperature, separating-purifying reaction solution, the described blue emitting phosphor material of main part containing tetraphenyl-silicon unit that obtains following structural formula:
The preparation method of the described blue emitting phosphor material of main part containing tetraphenyl-silicon unit, wherein, oxygen-free environment is to be mainly made up of at least one gas in nitrogen, argon gas.
The preparation method of the described blue emitting phosphor material of main part containing tetraphenyl-silicon unit, wherein, described catalyzer is bi triphenyl phosphine dichloride palladium or tetra-triphenylphosphine palladium; Or,
Described catalyzer is the mixture of organic palladium and organophosphorus ligand, and in mixture, the molar weight of organophosphorus ligand is 4～8 times of organic palladium molar weight; Described organic palladium is palladium or three or two argon benzyl acetone two palladiums; Organophosphorus ligand is tri-o-tolyl phosphine or 2-dicyclohexyl phosphine-2 ', 6 '-dimethoxy-biphenyl;
The mol ratio of described catalyzer and described compd A is 1:20～1:100.
The preparation method of the described blue emitting phosphor material of main part containing tetraphenyl-silicon unit, wherein, described alkaline solution is selected from least one in sodium carbonate solution, solution of potassium carbonate and sodium hydrogen carbonate solution; In described alkaline solution, the molar weight of alkali solute is 20 times of compd A molar weight.
The preparation method of the described blue emitting phosphor material of main part containing tetraphenyl-silicon unit, wherein, described organic solvent is at least one in toluene, DMF, tetrahydrofuran (THF).
The preparation method of the described blue emitting phosphor material of main part containing tetraphenyl-silicon unit, wherein, Suzuki coupling reaction temperature is 90～120 DEG C, the reaction times is 24～36 hours.
The preparation method of the described blue emitting phosphor material of main part containing tetraphenyl-silicon unit, wherein, separating-purifying reaction solution comprises:
After coupling reaction stops, with dichloromethane extraction reaction solution repeatedly, preferably more than three times, merge organic phase, and with being spin-dried for after anhydrous magnesium sulfate drying organic phase, obtain crude product, the sherwood oil that crude product is 10:1 by volume ratio again and ethyl acetate are leacheate, separate and obtain crystal thing through silica gel column chromatography, crystalline thing after 50 DEG C of dry 24h, is obtained to the described blue emitting phosphor material of main part containing tetraphenyl-silicon unit under vacuum.
A kind of organic electroluminescence device, comprises substrate, stacks gradually anode layer, hole injection layer, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer and cathode layer on substrate one surface; Wherein, the material of each functional layer is as follows:
Substrate, its material is glass;
Anode layer, its material is tin indium oxide (ITO), is combined with substrate of glass, is referred to as ito glass, or ITO;
Hole injection layer, its material is PEDOT:PSS;
Hole transmission layer, its material is N, N '-bis-[(1-naphthyl)-N, N '-phenylbenzene]-1,1 '-xenyl-4,4 '-diamines (NPD);
Luminescent layer, its material is two (4,6-difluorophenyl pyridine-N, C2) pyridine formyl close ratio that iridium (III) is (FIrpic) 20% according to mass percent add to following structural formula containing the doping mixing material forming in the blue emitting phosphor material of main part of tetraphenyl-silicon unit:
Electron transfer layer, its material are oxine aluminium (Alq
3)
Electron injecting layer, its material is LiF, and
Cathode layer, its material is Al.
Blue emitting phosphor material of main part containing tetraphenyl-silicon unit provided by the invention, has higher triplet, efficiency prevent that in luminescence process, energy returns to material of main part, greatly improve luminous efficiency; Meanwhile, contain the better heat stability of the blue emitting phosphor material of main part of tetraphenyl-silicon unit.
Separately, the preparation method of the above-mentioned blue emitting phosphor material of main part containing tetraphenyl-silicon unit, has adopted better simply synthetic route, thereby reduces technical process, and starting material are cheap and easy to get, and manufacturing cost is reduced.
Brief description of the drawings
Fig. 1 is the thermogravimetic analysis (TGA) figure containing the blue emitting phosphor material of main part of tetraphenyl-silicon unit that embodiment 1 makes.
Fig. 2 is the organic electroluminescence device structural representation that embodiment 5 makes.
Embodiment
In order to understand better the content of patent of the present invention, further illustrate technology case of the present invention below by concrete example and legend, specifically comprise material preparation and device preparation, but these embodiments do not limit the present invention, wherein compd A, compd B is all bought and is obtained from the market.
Embodiment 1
The blue emitting phosphor material of main part containing tetraphenyl-silicon unit of the present embodiment, i.e. triphenyl (4 '-(9-phenyl-9H-fluorenes-9-yl) biphenyl-4-yl) silane, preparation process is as follows:
Under argon shield, (4-bromophenyl) tri-phenyl-silane (83mg, 0.2mmol), 2-(4-(9-phenyl-9H-fluorenes-9-yl) phenyl) boric acid ester (89mg, 0.2mmol) add in the flask that fills 10ml toluene solvant, after fully dissolving, salt of wormwood (2mL, 2mol/L) solution is joined in flask, vacuumize deoxygenation and be filled with argon gas, then add bi triphenyl phosphine dichloride palladium (5.6mg, 0.008mmol); Flask is heated to 100 DEG C and carries out Suzuki coupling reaction 24h.Stopped reaction cool to room temperature, with dichloromethane extraction reaction solution repeatedly, merge organic phase, and with being spin-dried for after anhydrous magnesium sulfate drying organic phase, obtain crude product, the sherwood oil that crude product is 10:1 by volume ratio again and ethyl acetate are leacheate, separate and obtain crystal thing through silica gel column chromatography, crystalline thing after 50 DEG C of dry 24h, is obtained to the described blue emitting phosphor material of main part containing tetraphenyl-silicon unit under vacuum.Productive rate is 85%.
Mass spectrum: m/z 652.3(M
++ 1); Ultimate analysis (%) C
49h
36si theoretical value: C 90.14, H 5.56, Si 4.30; Measured value: C 90.21, H 5.50, Si 4.38.
Fig. 1 is the thermogravimetic analysis (TGA) figure containing the blue emitting phosphor material of main part of tetraphenyl-silicon unit that embodiment 1 makes; Thermogravimetic analysis (TGA) is completed by Perkin-Elmer Series 7 Thermo System measurements, and all measurements all complete in atmosphere at room temperature, 5% thermal weight loss temperature (T
d) be 361 DEG C.
Embodiment 2
The blue emitting phosphor material of main part containing tetraphenyl-silicon unit of the present embodiment, i.e. triphenyl (4 '-(9-phenyl-9H-fluorenes-9-yl) biphenyl-4-yl) silane, preparation process is as follows:
Under nitrogen and the protection of argon gas gas mixture; by (4-bromophenyl) tri-phenyl-silane (125mg; 0.3mmol), 2-(4-(9-phenyl-9H-fluorenes-9-yl) phenyl) boric acid ester (147mg; 0.33mmol) add in the two-mouth bottle of 50mL specification with 15mL tetrahydrofuran (THF); after fully dissolving, pass into after the about 20min of gas mixture air-discharging of nitrogen and argon gas; then by tetra-triphenylphosphine palladium (4mg; 0.003mmol) add wherein; after fully dissolving, add again sodium bicarbonate (3mL, 2mol/L) solution.After the about 10min of gas mixture air-discharging of fully logical nitrogen and argon gas, two-mouth bottle is joined to 70 DEG C and carry out Suzuki coupling reaction 48h again.Stopped reaction cool to room temperature, with dichloromethane extraction reaction solution repeatedly, merge organic phase, and with being spin-dried for after anhydrous magnesium sulfate drying organic phase, obtain crude product, the sherwood oil that crude product is 10:1 by volume ratio again and ethyl acetate are leacheate, separate and obtain crystal thing through silica gel column chromatography, crystalline thing after 50 DEG C of dry 24h, is obtained to the described blue emitting phosphor material of main part containing tetraphenyl-silicon unit under vacuum.Productive rate is 81%.
Embodiment 3
The blue emitting phosphor material of main part containing tetraphenyl-silicon unit of the present embodiment, i.e. triphenyl (4 '-(9-phenyl-9H-fluorenes-9-yl) biphenyl-4-yl) silane, preparation process is as follows:
Under nitrogen protection, by (4-bromophenyl) tri-phenyl-silane (125mg, 0.3mmol), 2-(4-(9-phenyl-9H-fluorenes-9-yl) phenyl) boric acid ester (160mg, 0.36mmol), palladium (3.5mg, 0.015mmol) He three (o-methoxyphenyl) phosphine (21mg, 0.06mmol) join the N that fills 12mL, in the flask of dinethylformamide, after fully dissolving, add salt of wormwood (3mL, 2mol/L) solution leads to after the about 30min of nitrogen purge gas subsequently in flask; Flask is heated to 130 DEG C and carries out Suzuki coupling reaction 12h.Stopped reaction cool to room temperature, with dichloromethane extraction reaction solution repeatedly, merge organic phase, and with being spin-dried for after anhydrous magnesium sulfate drying organic phase, obtain crude product, the sherwood oil that crude product is 10:1 by volume ratio again and ethyl acetate are leacheate, separate and obtain crystal thing through silica gel column chromatography, crystalline thing after 50 DEG C of dry 24h, is obtained to the described blue emitting phosphor material of main part containing tetraphenyl-silicon unit under vacuum.Productive rate is 76%.
Embodiment 4
The blue emitting phosphor material of main part containing tetraphenyl-silicon unit of the present embodiment, i.e. triphenyl (4 '-(9-phenyl-9H-fluorenes-9-yl) biphenyl-4-yl) silane, preparation process is as follows:
Under nitrogen protection; by (4-bromophenyl) tri-phenyl-silane (125mg; 0.3mmol), 2-(4-(9-phenyl-9H-fluorenes-9-yl) phenyl) boric acid ester (160mg; 0.34mmol), three dibenzalacetone two palladium (9mg; 0.009mmol) with 2-dicyclohexyl phosphine-2 '; 6 '-dimethoxy-biphenyl (29mg; 0.072mmol) join the N that fills 12mL; in the flask of dinethylformamide; after fully dissolving, add sodium carbonate (3mL, 2mol/L) solution.In flask, lead to after the about 30min of nitrogen purge gas subsequently; Flask is heated to 120 DEG C and carries out Suzuki coupling reaction 36h.Stopped reaction cool to room temperature, with dichloromethane extraction reaction solution repeatedly, merge organic phase, and with being spin-dried for after anhydrous magnesium sulfate drying organic phase, obtain crude product, the sherwood oil that crude product is 10:1 by volume ratio again and ethyl acetate are leacheate, separate and obtain crystal thing through silica gel column chromatography, crystalline thing after 50 DEG C of dry 24h, is obtained to the described blue emitting phosphor material of main part containing tetraphenyl-silicon unit under vacuum.Productive rate is 78%.
Embodiment 5
The present embodiment is organic electroluminescence device, and it adopts the material of main part of the arbitrary triphenyl making of above-described embodiment 1 to 4 (4 '-(9-phenyl-9H-fluorenes-9-yl) biphenyl-4-yl) silane as luminescent layer.
This organic electroluminescence device, as shown in Figure 2, comprises and stacks gradually structure: substrate 1/ anode layer 2/ hole injection layer 3/ hole transmission layer 4/ luminescent layer 5/ electron transfer layer 6/ electron injecting layer 7/ cathode layer 8; Wherein, slash "/" represents laminate structure.
Functional layer material and the thickness of above-mentioned organic electroluminescence device are as follows:
Substrate 1 adopts glass;
Anode layer 2 adopts ITO(tin indium oxide compound), thickness 150nm; ITO is prepared after glass surface, is called for short ito glass;
The material of hole injection layer 3 is PEDOE:PSS, and thickness is 30nm; Wherein, PEDOT is poly-3,4-ethylenedioxy thiazole, and PSS is polystyrene-sulfonic acid matrix material, and PEDOT:PSS is expressed as mixing of PEDOT and PSS;
The material of hole transmission layer 4 is N, N '-bis-[(1-naphthyl)-N, N '-phenylbenzene]-1, and 1 '-xenyl-4,4 '-diamines (NPD), thickness is 20nm;
The material of luminescent layer 5 is two (4,6-difluorophenyl pyridine-N, C2) pyridine formyl closes iridium (III) (FIrpic) as object luminescent material, be doped to the doping mixing material obtaining in triphenyl (4 '-(9-phenyl-9H-fluorenes-9-yl) biphenyl-4-yl) silane (representing with P) material of main part according to 20% mass ratio, be expressed as P:FIrpic, thickness is 20nm;
The material of electron transfer layer 6 is oxine aluminium (Alq
3), thickness is 30nm;
The material of electron injecting layer 7 is lithium fluoride (LiF), and thickness is 1.5nm;
The material of cathode layer 8 is aluminium (Al), and thickness is 150nm.
Above-mentioned organic electroluminescence device can be expressed as:
Glass/ITO/PEDOT:PSS/NPD/P:FIrpic/Alq
3/ LiF/Al; Wherein, slash "/" represents laminate structure.
This organic electroluminescence device, its preparation technology is as follows:
First, prepare one deck ITO layer at the glass surface cleaning up by magnetron sputtering, obtain ito glass;
Secondly, ito glass is moved in vacuum evaporation equipment, at ITO layer surface spin coating PEDOT:PSS;
Finally, stack gradually evaporation NPD, P:FIrpic, Alq on PEDOT:PSS surface
3, LiF, Al;
After above-mentioned processing step completes, obtain organic electroluminescence device.
Electric current-the brightness-voltage characteristic of organic electroluminescence device is to be completed by the Keithley source measuring system with correction silicon photoelectric diode (Keithley 2400 Sourcemeter, Keithley 2000 Cuirrentmeter).
Test result is, the maximum current efficiency of this organic electroluminescence device is 6.7cd/A, and high-high brightness is 18624cd/m
2.Result shows that polymer body material property of the present invention is better, is a kind of very promising Blue-light emitting host material.
Claims (10)
1. containing a blue emitting phosphor material of main part for tetraphenyl-silicon unit, it is characterized in that, its structural formula is as follows:
2. a preparation method who contains the blue emitting phosphor material of main part of tetraphenyl-silicon unit, is characterized in that, comprises the steps:
The compd A and the B that provide respectively following structural formula to represent,
Under oxygen-free environment, the compd A that is 1:1～1.2 by mol ratio and B are added in the organic solvent that contains catalyzer and alkaline solution and dissolve, at 70～130 DEG C, carry out Suzuki coupling reaction 12～48 hours, stopped reaction cool to room temperature, separating-purifying reaction solution, the described blue emitting phosphor material of main part containing tetraphenyl-silicon unit that obtains following structural formula:
3. the preparation method of the blue emitting phosphor material of main part containing tetraphenyl-silicon unit according to claim 2, is characterized in that, described catalyzer is bi triphenyl phosphine dichloride palladium or tetra-triphenylphosphine palladium; The mol ratio of described catalyzer and described compd A is 1:20～1:100.
4. the preparation method of the blue emitting phosphor material of main part containing tetraphenyl-silicon unit according to claim 2, it is characterized in that, described catalyzer is the mixture of organic palladium and organophosphorus ligand, and in mixture, the molar weight of organophosphorus ligand is 4～8 times of organic palladium molar weight; The mol ratio of described catalyzer and described compd A is 1:20～1:100.
5. the preparation method of the blue emitting phosphor material of main part containing tetraphenyl-silicon unit according to claim 4, is characterized in that, described organic palladium is palladium or three or two argon benzyl acetone two palladiums; Organophosphorus ligand is tri-o-tolyl phosphine or 2-dicyclohexyl phosphine-2 ', 6 '-dimethoxy-biphenyl.
6. the preparation method of the blue emitting phosphor material of main part containing tetraphenyl-silicon unit according to claim 2, is characterized in that, described alkaline solution is selected from least one in sodium carbonate solution, solution of potassium carbonate and sodium hydrogen carbonate solution; In described alkaline solution, the molar weight of alkali solute is 20 times of compd A molar weight.
7. the preparation method of the blue emitting phosphor material of main part containing tetraphenyl-silicon unit according to claim 2, is characterized in that, described organic solvent is at least one in toluene, DMF, tetrahydrofuran (THF).
8. the preparation method of the blue emitting phosphor material of main part containing tetraphenyl-silicon unit according to claim 2, is characterized in that, Suzuki coupling reaction temperature is 90～120 DEG C, and the reaction times is 24～36 hours.
9. the preparation method of the blue emitting phosphor material of main part containing tetraphenyl-silicon unit according to claim 2, is characterized in that, separating-purifying reaction solution comprises:
After coupling reaction stops, with dichloromethane extraction reaction solution repeatedly, merge organic phase, and with being spin-dried for after anhydrous magnesium sulfate drying organic phase, obtain crude product, the sherwood oil that crude product is 10:1 by volume ratio again and ethyl acetate are leacheate, separate and obtain crystal thing through silica gel column chromatography, crystalline thing after 50 DEG C of dry 24h, is obtained to the described blue emitting phosphor material of main part containing tetraphenyl-silicon unit under vacuum.
10. an organic electroluminescence device, it is characterized in that, the luminescent layer material of this organic electroluminescence device is two (4,6-difluorophenyl pyridine-N, C2) pyridine formyl close ratio that iridium (III) is 20% according to mass percent add to following structural formula containing the doping mixing material forming in the blue emitting phosphor material of main part of tetraphenyl-silicon unit:
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