CN104178130A - Bipolar blue light phosphorescent host material, preparation method and organic electroluminescent device thereof - Google Patents

Bipolar blue light phosphorescent host material, preparation method and organic electroluminescent device thereof Download PDF

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CN104178130A
CN104178130A CN201310204546.4A CN201310204546A CN104178130A CN 104178130 A CN104178130 A CN 104178130A CN 201310204546 A CN201310204546 A CN 201310204546A CN 104178130 A CN104178130 A CN 104178130A
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main part
emitting phosphor
blue emitting
phosphor material
preparation
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周明杰
张振华
王平
黄辉
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Oceans King Lighting Science and Technology Co Ltd
Shenzhen Oceans King Lighting Science and Technology Co Ltd
Shenzhen Oceans King Lighting Engineering Co Ltd
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Oceans King Lighting Science and Technology Co Ltd
Shenzhen Oceans King Lighting Engineering Co Ltd
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Abstract

Belonging to the field of organic semiconductor materials, the invention discloses a bipolar blue light phosphorescent host material, a preparation method and an organic electroluminescent device thereof. The host material has a structural formula shown as the specification. The bipolar blue light phosphorescent host material provided by the invention has hole transport properties and electron transport properties at the same time, and enables balance transport of holes and electrons in a luminescent layer. With a high triplet state energy level, the host material can effectively prevent back transmission of energy to the host material in a luminescence process, thus greatly improving the luminescence efficiency.

Description

Bipolarity blue emitting phosphor material of main part and preparation method thereof and organic electroluminescence device
Technical field
The present invention relates to organic semiconductor material field, relate in particular to a kind of bipolarity blue emitting phosphor material of main part and preparation method thereof.The invention still further relates to a kind of organic electroluminescence device, its luminescent layer material includes bipolarity blue emitting phosphor material of main part.
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) bipolarity blue emitting phosphor material of main part.
Two of problem to be solved by this invention is to provide a kind of preparation method of bipolarity blue emitting phosphor material of main part.
Three of problem to be solved by this invention is to provide a kind of organic electroluminescence device, and its luminescent layer material includes bipolarity blue emitting phosphor material of main part.
Technical scheme of the present invention is as follows:
A kind of bipolarity blue emitting phosphor material of main part, its structural formula is as follows:
be N, N '-(4,4 '-(9,9-bis-(4-(5-(4-T tert-butyl-phenyl)-1,3,4-oxadiazole-2-yl) phenoxy group)-9H-fluorenes-2,7-bis-bases) two (4,1-penylenes)) two (N-benzene naphthyl-1-amine).
The preparation method of above-mentioned bipolarity blue emitting phosphor material of main part, comprises the steps:
The compd A and the B that provide respectively following structural formula to represent,
A: 5,5'-(4,4'-(the bromo-9H-of 2,7-bis-fluorenes-9,9-bis-bases) dioxy two (4,1-penylene)) two (2-(4-tert-butyl-phenyl)-1,3,4-oxadiazoles);
B: be N-phenyl-N-(4-tetramethyl ethylene ketone boric acid ester) phenyl) naphthalene-1-amine;
Under oxygen-free environment, the compd A that is 1:2～2.4 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, obtains the described bipolarity blue emitting phosphor material of main part of following structural formula:
The preparation method of described bipolarity blue emitting phosphor material of main part, wherein, oxygen-free environment is to be mainly made up of at least one gas in nitrogen, argon gas.
The preparation method of described bipolarity blue emitting phosphor material of main part, 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 described bipolarity blue emitting phosphor material of main part, 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 described bipolarity blue emitting phosphor material of main part, wherein, described organic solvent is at least one in toluene, DMF, tetrahydrofuran (THF).
The preparation method of described bipolarity blue emitting phosphor material of main part, wherein, Suzuki coupling reaction temperature is 90～120 ° of C, the reaction times is 24～36 hours.
The preparation method of described bipolarity blue emitting phosphor material of main part, 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 described bipolarity blue emitting phosphor material of main part under vacuum.
A kind of organic electroluminescence device, comprises substrate, stacks gradually anode layer, hole injection layer, hole transport/electronic barrier layer, luminescent layer, electric transmission/hole blocking 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 CuPc;
Hole transport/electronic barrier layer, its material is N, N '-phenylbenzene-N, N '-bis-(3-aminomethyl phenyl)-1,1 '-biphenyl-4,4 '-diamines (TPD);
Luminescent layer, its material is two (4,6-difluorophenyl pyridine-N, C2) pyridine formyl closes the ratio that iridium (FIrpic) is 10% according to mass percent and adds the doping mixing material forming in the bipolarity blue emitting phosphor material of main part of following structural formula to:
Electric transmission/hole blocking layer, its material are 4,7-phenylbenzene-1,10-phenanthroline (BPhen)
Electron injecting layer, its material is LiF, and
Cathode layer, its material is Al.
Bipolarity blue emitting phosphor material of main part provided by the invention, there is hole transport character and electronic transport property simultaneously, make the transmission balance in hole and electronics in luminescent layer, and there is higher triplet, efficiency prevent that in luminescence process, energy returns to material of main part, greatly improve luminous efficiency; Meanwhile, the better heat stability of bipolarity blue emitting phosphor material of main part.
Separately, the preparation method of above-mentioned bipolarity blue emitting phosphor material of main part, 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 of the bipolarity blue emitting phosphor material of main part that makes of embodiment 1;
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 bipolarity blue emitting phosphor material of main part of the present embodiment, be N, N '-(4,4 '-(9,9-bis-(4-(5-(4-T tert-butyl-phenyl)-1,3,4-oxadiazole-2-yl) phenoxy group)-9H-fluorenes-2,7-bis-bases) two (4,1-penylenes)) two (N-benzene naphthyl-1-amine), its structural formula is as follows:
Under argon shield, 5, 5'-(4, 4'-(2, the bromo-9H-of 7-bis-fluorenes-9, 9-bis-bases) dioxy two (4, 1-penylene)) two (2-(4-tert-butyl-phenyl)-1, 3, 4-oxadiazole) (182mg, 0.2mmol), N-phenyl-N-(4-tetramethyl ethylene ketone boric acid ester) phenyl) naphthalene-1-amine (168mg, 0.4mmol) add in the flask that fills 10ml toluene solvant, after fully dissolving by salt of wormwood (2mL, 2mol/L) solution joins 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, use dichloromethane extraction three times, merges organic phase, after anhydrous magnesium sulfate drying, is spin-dried for, and crude product adopts sherwood oil: ethyl acetate (10:1) is that leacheate separates and obtains white crystal through silica gel column chromatography.The last lower 50 DEG C of dry 24h of vacuum, obtain bipolarity blue emitting phosphor material of main part, be N, N '-(4,4 '-(9,9-bis-(4-(5-(4-T tert-butyl-phenyl)-1,3,4-oxadiazole-2-yl) phenoxy group)-9H-fluorenes-2,7-bis-bases) two (4,1-penylenes)) two (N-benzene naphthyl-1-amine).Productive rate is 76%.Mass spectrum: m/z1337.6(M ++ 1); Ultimate analysis (%) C 93h 72n 6o 4: theoretical value: C83.51, H5.43, N6.283, S4.78; Measured value: C83.57, H5.34, N6.23, S4.80.
Fig. 1 is the thermogravimetic analysis (TGA) figure of the bipolarity blue emitting phosphor material of main part that makes of embodiment 1; Thermogravimetic analysis (TGA) is completed by the measurement of Perkin-Elmer Series7 Thermo System, and all measurements all complete in atmosphere at room temperature, 5% thermal weight loss temperature (T d) be 405 DEG C.
Embodiment 2
The bipolarity blue emitting phosphor material of main part of the present embodiment, be N, N '-(4,4 '-(9,9-bis-(4-(5-(4-T tert-butyl-phenyl)-1,3,4-oxadiazole-2-yl) phenoxy group)-9H-fluorenes-2,7-bis-bases) two (4,1-penylenes)) two (N-benzene naphthyl-1-amine), its structural formula is as follows:
Under nitrogen and the protection of argon gas gas mixture, by 5, 5'-(4, 4'-(2, the bromo-9H-of 7-bis-fluorenes-9, 9-bis-bases) dioxy two (4, 1-penylene)) two (2-(4-tert-butyl-phenyl)-1, 3, 4-oxadiazole) (272mg, 0.3mmol), N-phenyl-N-(4-tetramethyl ethylene ketone boric acid ester) phenyl) naphthalene-1-amine (278mg, 0.66mmol) 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, use dichloromethane extraction three times, merges organic phase, after anhydrous magnesium sulfate drying, is spin-dried for, and crude product adopts sherwood oil: ethyl acetate (10:1) is that leacheate separates and obtains white crystal through silica gel column chromatography.The last lower 50 DEG C of dry 24h of vacuum, obtain bipolarity blue emitting phosphor material of main part, be N, N '-(4,4 '-(9,9-bis-(4-(5-(4-T tert-butyl-phenyl)-1,3,4-oxadiazole-2-yl) phenoxy group)-9H-fluorenes-2,7-bis-bases) two (4,1-penylenes)) two (N-benzene naphthyl-1-amine).Productive rate is 77%.
Embodiment 3
The bipolarity blue emitting phosphor material of main part of the present embodiment, be N, N '-(4,4 '-(9,9-bis-(4-(5-(4-T tert-butyl-phenyl)-1,3,4-oxadiazole-2-yl) phenoxy group)-9H-fluorenes-2,7-bis-bases) two (4,1-penylenes)) two (N-benzene naphthyl-1-amine), its structural formula is as follows:
Under nitrogen protection, by 5, 5'-(4, 4'-(2, the bromo-9H-of 7-bis-fluorenes-9, 9-bis-bases) dioxy two (4, 1-penylene)) two (2-(4-tert-butyl-phenyl)-1, 3, 4-oxadiazole) (272mg, 0.3mmol), N-phenyl-N-(4-tetramethyl ethylene ketone boric acid ester) phenyl) naphthalene-1-amine (303mg, 0.72mmol), 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, in flask, lead to after the about 30min of nitrogen purge gas subsequently, flask is heated to 130 DEG C and carries out Suzuki coupling reaction 12h.Stopped reaction cool to room temperature, use dichloromethane extraction three times, merges organic phase, after anhydrous magnesium sulfate drying, is spin-dried for, and crude product adopts sherwood oil: ethyl acetate (10:1) is that leacheate separates and obtains white crystal through silica gel column chromatography.The last lower 50 DEG C of dry 24h of vacuum, obtain bipolarity blue emitting phosphor material of main part, be N, N '-(4,4 '-(9,9-bis-(4-(5-(4-T tert-butyl-phenyl)-1,3,4-oxadiazole-2-yl) phenoxy group)-9H-fluorenes-2,7-bis-bases) two (4,1-penylenes)) two (N-benzene naphthyl-1-amine).Productive rate is 73%.
Embodiment 4
The bipolarity blue emitting phosphor material of main part of the present embodiment, be N, N '-(4,4 '-(9,9-bis-(4-(5-(4-T tert-butyl-phenyl)-1,3,4-oxadiazole-2-yl) phenoxy group)-9H-fluorenes-2,7-bis-bases) two (4,1-penylenes)) two (N-benzene naphthyl-1-amine), its structural formula is as follows:
Under nitrogen protection, will, by 5, 5'-(4, 4'-(2, the bromo-9H-of 7-bis-fluorenes-9, 9-bis-bases) dioxy two (4, 1-penylene)) two (2-(4-tert-butyl-phenyl)-1, 3, 4-oxadiazole) (272mg, 0.3mmol), N-phenyl-N-(4-tetramethyl ethylene ketone boric acid ester) phenyl) naphthalene-1-amine (303mg, 0.72mmol), three or two argon benzyl acetone 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, use dichloromethane extraction three times, merges organic phase, after anhydrous magnesium sulfate drying, is spin-dried for, and crude product adopts sherwood oil: ethyl acetate (10:1) is that leacheate separates and obtains white crystal through silica gel column chromatography.The last lower 50 DEG C of dry 24h of vacuum, obtain bipolarity blue emitting phosphor material of main part, be N, N '-(4,4 '-(9,9-bis-(4-(5-(4-T tert-butyl-phenyl)-1,3,4-oxadiazole-2-yl) phenoxy group)-9H-fluorenes-2,7-bis-bases) two (4,1-penylenes)) two (N-benzene naphthyl-1-amine).Productive rate is 80%.
Embodiment 5
The present embodiment is organic electroluminescence device, it adopts the arbitrary N making of above-described embodiment 1 to 4, N '-(4,4 '-(9,9-bis-(4-(5-(4-T tert-butyl-phenyl)-1,3,4-oxadiazole-2-yl) phenoxy group)-9H-fluorenes-2,7-bis-bases) two (4,1-penylenes)) two (N-benzene naphthyl-1-amine) are as the material of main part of luminescent layer.
This organic electroluminescence device, as shown in Figure 2, comprise and stacking gradually: substrate 1/ anode layer 2/ hole injection layer 3/ (hole transport/electronic barrier layer) 4/ luminescent layer 5/ (electric transmission/hole blocking layer) 6/ electron injecting layer 7/ cathode layer 8.
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 that CuPc (CuPc) thickness is 30nm;
The material of hole transport/electronic barrier layer 4 is N, N '-phenylbenzene-N, and N '-bis-(3-aminomethyl phenyl)-1,1 '-biphenyl-4,4 '-diamines (TPD), thickness is 20nm;
The material of luminescent layer 5 is two (4,6-difluorophenyl pyridine-N, C2) pyridine formyl closes iridium (FIrpic) as object luminescent material, mass ratio according to 10% is doped to N, N '-(4,4 '-(9,9-bis-(4-(5-(4-T tert-butyl-phenyl)-1,3,4-oxadiazole-2-yl) phenoxy group)-9H-fluorenes-2,7-bis-bases) two (4,1-penylenes)) the doping mixing material that obtains in two (N-benzene naphthyl-1-amine) (representing with P) material of main part, be expressed as P:FIrpic, thickness is 20nm;
The material of electric transmission/hole blocking layer 6 is 4,7-phenylbenzene-1,10-phenanthroline (BPhen), and 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/CuPc/TPD/P:FIrpic/BPhen/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, on ITO layer surface successively evaporation CuPc, TPD, P:FIrpic, BPhen, 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 (Keithley2400Sourcemeter, Keithley2000Cuirrentmeter) with correction silicon photoelectric diode.
Test result is that the trigger voltage of organic electroluminescence device is 3.7V, at 1000cd/m 2brightness under, luminous efficiency is 6.5lm/W.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. a bipolarity blue emitting phosphor material of main part, is characterized in that, its structural formula is as follows:
2. a preparation method for bipolarity blue emitting phosphor material of main part, is characterized in that, comprises the steps:
The compd A and the B that provide respectively following structural formula to represent,
A： B：
Under oxygen-free environment, the compd A that is 1:2～2.4 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, obtains the described bipolarity blue emitting phosphor material of main part of following structural formula:
3. the preparation method of bipolarity blue emitting phosphor material of main part 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 bipolarity blue emitting phosphor material of main part according to claim 2, 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 bipolarity blue emitting phosphor material of main part 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 bipolarity blue emitting phosphor material of main part 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 bipolarity blue emitting phosphor material of main part 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 bipolarity blue emitting phosphor material of main part according to claim 2, is characterized in that, Suzuki coupling reaction temperature is 90～120 ° of C, and the reaction times is 24～36 hours.
9. the preparation method of bipolarity blue emitting phosphor material of main part 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 described bipolarity blue emitting phosphor material of main part 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 closes the ratio that iridium is 10% according to mass percent and adds the doping mixing material forming in the bipolarity blue emitting phosphor material of main part of following structural formula to:
CN201310204546.4A 2013-05-28 2013-05-28 Bipolar blue light phosphorescent host material, preparation method and organic electroluminescent device thereof Pending CN104178130A (en)

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Application publication date: 20141203