CN104178129A - 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 PDFInfo
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- CN104178129A CN104178129A CN201310204511.0A CN201310204511A CN104178129A CN 104178129 A CN104178129 A CN 104178129A CN 201310204511 A CN201310204511 A CN 201310204511A CN 104178129 A CN104178129 A CN 104178129A
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- emitting phosphor
- blue emitting
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- NQUNLCVNMKRZCF-UHFFFAOYSA-N Bc1cccc(-c2nnc(-c3cccc(Br)c3)[o]2)c1 Chemical compound Bc1cccc(-c2nnc(-c3cccc(Br)c3)[o]2)c1 NQUNLCVNMKRZCF-UHFFFAOYSA-N 0.000 description 1
- XMSUBYREKYPREZ-UHFFFAOYSA-N C1c(cccc2)c2N(c2cccc(-c3nnc(-c4cccc(N5c6ccccc6CCc6ccccc56)c4)[o]3)c2)c2ccccc2C1 Chemical compound C1c(cccc2)c2N(c2cccc(-c3nnc(-c4cccc(N5c6ccccc6CCc6ccccc56)c4)[o]3)c2)c2ccccc2C1 XMSUBYREKYPREZ-UHFFFAOYSA-N 0.000 description 1
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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, 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
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:
2,5-bis-(3-(10,11-dihydro-IS Zhuo-5-yl) phenyl)-1,3,4-oxadiazole.
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,
2,5-bis-(3-bromophenyl)-1,3,4-oxadiazole;
10,11-dihydro-IS Zhuo;
Under oxygen-free environment, compd A is dissolved in organic solvent, then adds compd B, mineral alkali and catalyzer, obtain mixed solution, mixed solution is reacted 6～15 hours at 70～120 DEG C, stopped reaction is cooled to room temperature, separating-purifying reaction solution, obtains structural formula and is
bipolarity blue emitting phosphor material of main part; Wherein, compd A and B mol ratio are 1:2～1:2.4;
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 organic solvent is selected from least one in tetrahydrofuran (THF) (THF), acetonitrile (MeCN), toluene (Tol), DMF (DMF).
The preparation method of described bipolarity blue emitting phosphor material of main part, wherein, described mineral alkali is selected from sodium carbonate (Na
2cO
3), salt of wormwood (K
2cO
3), cesium carbonate (Cs
2cO
3) and potassiumphosphate (K
3pO
4) at least one; The mol ratio of described mineral alkali and compd A is 2:1～2.5:1.
The preparation method of described bipolarity blue emitting phosphor material of main part, wherein, described catalyzer is copper (Cu) powder, cuprous iodide (CuI), Red copper oxide (Cu
2o) one in; The mol ratio of described catalyzer and described compd A is 1:10～1:5.
The preparation method of described bipolarity blue emitting phosphor material of main part, wherein, separating-purifying reaction solution comprises:
After stopped reaction cool to room temperature, filter and wash with water and obtain crude product; Be that leacheate separates through silica gel column chromatography by crude product normal hexane, then after 50 DEG C of dry 24h, obtain 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 [3, the fluoro-2-of 5-bis-(2-pyridyl-KN) phenyl-KC] [four (1H-pyrazolyl-KN1) boric acid (1-)-KN2, KN2']-iridium (III) is (FIr6) 15% according to mass percent ratio is added 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 higher triplet, can effectively prevent that in luminescence process, energy returns to material of main part, greatly improve luminous efficiency; Meanwhile, the better heat stability of this 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 structural representation of the organic electroluminescence device that makes of embodiment 6;
Fig. 2 is efficiency-brightness curve figure of the organic electroluminescence device that makes of embodiment 6.
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, its structure is: 2,5-bis-(3-(10,11-dihydro-IS Zhuo-5-yl) phenyl)-1,3,4-oxadiazole, structural formula is as follows:
The preparation technology of this compound is as follows:
Under nitrogen protection, by 2,5-bis-(3-bromophenyl)-1; 3,4-oxadiazole (30.4g, 80mmol) is dissolved in 200mLN; in dinethylformamide (DMF) solution, then add 10,11-dihydro-5H-dibenzo [b; f] azatropylidene (31.2g; 160mmol), salt of wormwood (22.1g, 160mmol); cuprous iodide (1.52g, 8mmol).Mixture stirring reaction 6 hours at 120 DEG C.Stopped reaction is cooled to room temperature, filters, and washes solid three times with distillation, and crude product adopts leacheate normal hexane to separate through silica gel column chromatography, then 50 DEG C of dry 24h obtain pale solid bipolarity blue emitting phosphor material of main part under vacuum.Productive rate is 76%.
Mass spectrum: m/z608.3(M
++ 1); Ultimate analysis (%) C
42h
32n
4o: theoretical value: C82.87, H5.30, N9.20, O2.63; Measured value: C82.94, H5.27, N9.12, O2.70.
Embodiment 2
The bipolarity blue emitting phosphor material of main part of the present embodiment, for: 2,5-bis-(3-(10,11-dihydro-IS Zhuo-5-yl) phenyl)-1,3,4-oxadiazole, structural formula is as follows:
The preparation technology of this compound is as follows:
Under nitrogen protection, by 2,5-bis-(3-bromophenyl)-1; 3,4-oxadiazole (30.4g, 80mmol) is dissolved in 200mL toluene (Tol) solution; then add 10; 11-dihydro-IS Zhuo (34.3g, 176mmol); cesium carbonate (57.2g; 176mmol), copper powder (0.768g, 12mmol).Mixture stirring reaction 9 hours at 110 DEG C.Stopped reaction is cooled to room temperature, filters, and washes solid three times with distillation, and crude product adopts leacheate normal hexane to separate through silica gel column chromatography, then 50 DEG C of dry 24h obtain pale solid bipolarity blue emitting phosphor material of main part under vacuum.Productive rate is 83%.
Embodiment 3
The bipolarity blue emitting phosphor material of main part of the present embodiment, for: 2,5-bis-(3-(10,11-dihydro-IS Zhuo-5-yl) phenyl)-1,3,4-oxadiazole, structural formula is as follows:
The preparation technology of this compound is as follows:
Under nitrogen protection, by 2,5-bis-(3-bromophenyl)-1; 3,4-oxadiazole (30.4g, 80mmol) is dissolved in 200mL acetonitrile (MeCN) solution; then add 10; 11-dihydro-IS Zhuo (37.4g, 192mmol); potassiumphosphate (39g; 184mmol), Red copper oxide (2.3g, 16mmol).Mixture stirring reaction 12 hours at 90 DEG C.Stopped reaction is cooled to room temperature, filters, and washes solid three times with distillation, and crude product adopts leacheate normal hexane to separate through silica gel column chromatography, then 50 DEG C of dry 24h obtain pale solid bipolarity blue emitting phosphor material of main part under vacuum.Productive rate is 80%.
Embodiment 4
The bipolarity blue emitting phosphor material of main part of the present embodiment, for: 2,5-bis-(3-(10,11-dihydro-IS Zhuo-5-yl) phenyl)-1,3,4-oxadiazole, structural formula is as follows:
The preparation technology of this compound is as follows:
Under nitrogen protection, by 2,5-bis-(3-bromophenyl)-1; 3,4-oxadiazole (30.4g, 80mmol) is dissolved in 200mL tetrahydrofuran (THF) (THF) solution; then add 10; 11-dihydro-IS Zhuo (35.9g, 184mmol); sodium carbonate (20.4g; 192mmol), cuprous iodide (2.6g, 13.6mmol).Mixture stirring reaction 15 hours at 70 DEG C.Stopped reaction is cooled to room temperature, filters, and washes solid three times with distillation, and crude product adopts leacheate normal hexane to separate through silica gel column chromatography, then 50 DEG C of dry 24h obtain pale solid bipolarity blue emitting phosphor material of main part under vacuum.Productive rate is 87%.
Embodiment 5
The bipolarity blue emitting phosphor material of main part of the present embodiment, for: 2,5-bis-(3-(10,11-dihydro-IS Zhuo-5-yl) phenyl)-1,3,4-oxadiazole, structural formula is as follows:
The preparation technology of this compound is as follows:
Under nitrogen protection, by 2,5-bis-(3-bromophenyl)-1; 3,4-oxadiazole (30.4g, 80mmol) is dissolved in 200mL N; in dinethylformamide (DMF) solution, then add 10,11-dihydro-5H-dibenzo [b; f] azatropylidene (32.8g; 168mmol), potassiumphosphate (42.4g, 200mmol); copper powder (1g, 16mmol).Mixture stirring reaction 15 hours at 100 DEG C.Stopped reaction is cooled to room temperature, filters, and washes solid three times with distillation, and crude product adopts leacheate normal hexane to separate and obtain pale solid bipolarity blue emitting phosphor material of main part through silica gel column chromatography.Productive rate is 78%.
Embodiment 6
The present embodiment is organic electroluminescence device, its adopt above-described embodiment 1 to 5 arbitrary make 2,5-bis-(3-(10,11-dihydro-5H-dibenzo [b, f] azatropylidene-5-yl) phenyl)-1,3,4-oxadiazole is as the material of main part of luminescent layer.
This organic electroluminescence device, as shown in Figure 1, comprises and stacks gradually structure: 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; 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 CuPc (CuPc), and thickness is 30nm;
The material of hole transmission layer/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 [3, the fluoro-2-of 5-bis-(2-pyridyl-KN) phenyl-KC] [four (1H-pyrazolyl-KN1) boric acid (1-)-KN2, KN2']-iridium (III) is (FIr6) as object luminescent material, mass ratio according to 15% is doped to 2,5-bis-(3-(10,11-dihydro-5H-dibenzo [b, f] azatropylidene-5-yl) phenyl)-1,3, the doping mixing material obtaining in 4-oxadiazole (representing with P) material of main part, be expressed as P:FIr6, thickness is 20nm;
The material of electron transfer layer/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 1nm;
The material of cathode layer 8 is aluminium (Al), and thickness is 100nm.
Above-mentioned organic electroluminescence device can be expressed as:
Glass/ITO/CuPc/TPD/P:FIr6/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, stack gradually evaporation CuPc, TPD, P:FIr6, BPhen, LiF, Al on ITO layer surface;
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.
As shown in Figure 2, test result is, the maximum current efficiency of this organic electroluminescence device is 9.3cd/A, and high-high brightness is 24460cd/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 (7)
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,
Under oxygen-free environment, compd A is dissolved in organic solvent, then adds compd B, mineral alkali and catalyzer, obtain mixed solution, mixed solution is reacted 6～15 hours at 70～120 DEG C, stopped reaction is cooled to room temperature, separating-purifying reaction solution, obtains structural formula and is
bipolarity blue emitting phosphor material of main part; Wherein, compd A and B mol ratio are 1:2～1:2.4.
3. the preparation method of bipolarity blue emitting phosphor material of main part according to claim 2, is characterized in that, described organic solvent is selected from least one in tetrahydrofuran (THF), acetonitrile, toluene, DMF.
4. the preparation method of bipolarity blue emitting phosphor material of main part according to claim 2, is characterized in that, described mineral alkali is selected from least one in sodium carbonate, salt of wormwood, cesium carbonate and potassiumphosphate; The mol ratio of described mineral alkali and compd A is 2:1～2.5:1.
5. the preparation method of bipolarity blue emitting phosphor material of main part according to claim 2, is characterized in that, described catalyzer is the one in copper powder, cuprous iodide, Red copper oxide; The mol ratio of described catalyzer and described compd A is 1:10～1:5.
6. 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 stopped reaction cool to room temperature, filter and wash with water and obtain crude product; Be that leacheate separates through silica gel column chromatography by crude product normal hexane, then after 50 DEG C of dry 24h, obtain bipolarity blue emitting phosphor material of main part under vacuum.
7. an organic electroluminescence device, it is characterized in that, the luminescent layer material of this organic electroluminescence device is two [3, the fluoro-2-of 5-bis-(2-pyridyl-KN) phenyl-KC] [four (1H-pyrazolyl-KN1) boric acid (1-)-KN2, KN2']-iridium is 15% according to mass percent ratio is added the doping mixing material forming in the bipolarity blue emitting phosphor material of main part of following structural formula to:
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2003022893A (en) * | 2001-07-06 | 2003-01-24 | Fuji Photo Film Co Ltd | Luminescent element |
| JP2004217592A (en) * | 2003-01-16 | 2004-08-05 | Mitsubishi Chemicals Corp | Iminostilbene-based compound, charge transport material, organic electroluminescent device material, and organic electroluminescent device |
| CN101333438A (en) * | 2008-07-15 | 2008-12-31 | 武汉大学 | Material with bipolar carrier transmission performance and uses thereof |
-
2013
- 2013-05-28 CN CN201310204511.0A patent/CN104178129A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2003022893A (en) * | 2001-07-06 | 2003-01-24 | Fuji Photo Film Co Ltd | Luminescent element |
| JP2004217592A (en) * | 2003-01-16 | 2004-08-05 | Mitsubishi Chemicals Corp | Iminostilbene-based compound, charge transport material, organic electroluminescent device material, and organic electroluminescent device |
| CN101333438A (en) * | 2008-07-15 | 2008-12-31 | 武汉大学 | Material with bipolar carrier transmission performance and uses thereof |
Non-Patent Citations (1)
| Title |
|---|
| YOUTIAN TAO ET AL.: "A Simple Carbazole/Oxadiazole Hybrid Molecule: An Excellent Bipolar Host for Green and Red Phosphorescent OLEDs", 《ANGEW. CHEM. INT. ED.》 * |
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Application publication date: 20141203 |