CN104178122A - Electron transport type red light phosphorescent material, preparation method and organic electroluminescent device thereof - Google Patents
Electron transport type red light phosphorescent material, preparation method and organic electroluminescent device thereof Download PDFInfo
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- CN104178122A CN104178122A CN201310204158.6A CN201310204158A CN104178122A CN 104178122 A CN104178122 A CN 104178122A CN 201310204158 A CN201310204158 A CN 201310204158A CN 104178122 A CN104178122 A CN 104178122A
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- electron
- phosphor material
- preparation
- transporting type
- ruddiness phosphor
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- JMSKYMHFNWGUJG-UHFFFAOYSA-N Brc(cccc1)c1Oc1ccccc1Br Chemical compound Brc(cccc1)c1Oc1ccccc1Br JMSKYMHFNWGUJG-UHFFFAOYSA-N 0.000 description 1
- HNKJADCVZUBCPG-UHFFFAOYSA-N CSc1ccccc1 Chemical compound CSc1ccccc1 HNKJADCVZUBCPG-UHFFFAOYSA-N 0.000 description 1
- KFVDXZMXNIWYDF-UHFFFAOYSA-N O=S(C1C=CC=CC=C1)c1ccccc1Oc(cccc1)c1S(c1ccccc1)(=O)=O Chemical compound O=S(C1C=CC=CC=C1)c1ccccc1Oc(cccc1)c1S(c1ccccc1)(=O)=O KFVDXZMXNIWYDF-UHFFFAOYSA-N 0.000 description 1
- JGMGKFOXVORDHT-UHFFFAOYSA-N O=S(c1ccccc1)(c(cccc1)c1Oc1ccccc1S(c1ccccc1)(=O)=O)=O Chemical compound O=S(c1ccccc1)(c(cccc1)c1Oc1ccccc1S(c1ccccc1)(=O)=O)=O JGMGKFOXVORDHT-UHFFFAOYSA-N 0.000 description 1
- KSZXEYCHJSCITA-UHFFFAOYSA-N c(cc1)ccc1Sc1ccccc1Oc1ccccc1Sc1ccccc1 Chemical compound c(cc1)ccc1Sc1ccccc1Oc1ccccc1Sc1ccccc1 KSZXEYCHJSCITA-UHFFFAOYSA-N 0.000 description 1
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Abstract
The invention belongs to the field of organic semiconductor materials, and discloses an electron transport type red light phosphorescent material, a preparation method and an organic electroluminescent device thereof. The structural formula of the material is shown as the specification. The electron transport type red light phosphorescent material provided by the invention has strong electron transport capability and good carrier transport balance. Also the material has a high triplet state energy level, and can effectively prevent back transmission of energy to a host material in a luminescence process. Thus, the luminescence efficiency is high.
Description
Technical field
The present invention relates to organic semiconductor material, relate in particular to a kind of electron-transporting type ruddiness phosphor material and preparation method thereof.The invention still further relates to a kind of luminescent layer material and adopt the organic electroluminescence device of this electron-transporting type ruddiness phosphor material as 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 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.Therefore,, for efficient Organic Light Emitting Diode, develop high performance material of main part and guest materials most important.As one of three primary colours, ruddiness is very crucial for panchromatic colour developing and solid-state illumination.But red phosphorescent device is little efficiently, major cause is to lack suitable material of main part.
At present, the material of main part that is widely used in red phosphorescent device is CBP(4,4'-bis-(9-carbazole) biphenyl), but the driving voltage that it requires is higher, second-order transition temperature (T
g) low (T
g=62 DEG C), be easy to crystallization.In addition, CBP is a kind of p-shaped material, and hole mobility, far above electronic mobility, be unfavorable for carrier injection and transmission balance, and luminous efficiency is lower.
Summary of the invention
Based on the problems referred to above, problem to be solved by this invention is to provide that a kind of luminous efficiency is higher, carrier transport ability is strong, and the good electron-transporting type ruddiness phosphor material of transmission balance.
The present invention also provides the preparation method of this electron-transporting type ruddiness phosphor material.
The present invention further provides and use the organic electroluminescence device of this electron-transporting type ruddiness phosphor material as luminescent layer material of main part.
For achieving the above object, electron-transporting type ruddiness phosphor material provided by the invention, its structural formula is as follows:
, 2,2'-oxygen base two (phenyl sulfonyl benzene).
The preparation method of this electron-transporting type ruddiness phosphor material, comprises the steps:
Step 1: the compd A and the B that provide respectively following structural formula to represent,
A:
2,2'-oxygen base dibromobenzene; B:
it is thiophenol;
Step 2: under oxygen-free environment, compd A is dissolved in organic solvent, and then adds compd B, mineral alkali and catalyzer in organic solvent, then at 70～120 DEG C, react after 6～15 hours, stopped reaction cool to room temperature, separating-purifying reaction solution, obtains structural formula and is
solid chemical compound C;
In this step:
Described oxygen-free environment, its ambiance comprises at least one in argon gas, nitrogen;
Described catalyzer is copper (Cu) powder, cuprous iodide (CuI), Red copper oxide (Cu
2o) one wherein; The mol ratio of described catalyzer and described compd A is 1:10～1:5;
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 alkali and described compd A is 2:1～2.5:1.
In a preferred embodiment, to be selected from solvent be at least one in tetrahydrofuran (THF) (THF), acetonitrile (MeCN), toluene (Tol), DMF (DMF) to organic solvent;
Compd A and B mol ratio are 1:2～1:2.4;
To the separating-purifying of described Compound C, comprising: after reaction stops, filtering reacting liquid, and wash with water and obtain solid screening, obtaining crude product, it is that leacheate separates through silica gel column chromatography that described crude product adopts normal hexane, obtains described Compound C.
Step 3: frozen water mixes under bath, and Compound C is dissolved in methylene dichloride, obtains mixing solutions, then mixing solutions is splashed in the dichloromethane solution of m-chloro-benzoic acid, after dropwising, at room temperature react 12 hours, separating-purifying reaction solution, obtains structural formula and is
electron-transporting type ruddiness phosphor material;
In this step:
Compound C is dissolved in the mixing solutions obtaining after methylene dichloride, and the volumetric molar concentration of Compound C is 0.33mol/L;
In the dichloromethane solution of m-chloro-benzoic acid, the concentration of m-chloro-benzoic acid is 2mol/L;
The separating-purifying of described electron-transporting type ruddiness phosphor material, comprising: in reaction solution, add saturated NaHCO
3, and stir 30 minutes, separate organic layer, then use anhydrous magnesium sulfate drying organic layer, obtain crude product, it is solvent that described crude product adopts toluene and the alcohol mixed solution that volume ratio is 5:1, carries out recrystallization, obtains electron-transporting type ruddiness phosphor material.
Above-mentioned preparation method's principle is simple, easy and simple to handle, low for equipment requirements, can wide popularization and application.
It is above-mentioned 2 that another object of the present invention is to provide, the application of 2'-oxygen base two (phenyl sulfonyl benzene) electron-transporting type ruddiness phosphor material in organic electroluminescence device.
This organic electroluminescence device, comprises substrate, and anode layer, hole injection layer, hole transport/electronic barrier layer, luminescent layer, electric transmission/hole blocking layer, electron injecting layer, cathode layer have been cascading on substrate one surface; Wherein:
Substrate material is glass;
The material of anode layer is indium tin oxide (ITO), and it is called ito glass after being combined with glass;
The material of hole injection layer is CuPc (CuPc);
The material of hole transport/electronic barrier layer is N, N'-phenylbenzene-N, N'-bis-(3-aminomethyl phenyl)-1,1'-biphenyl-4,4'-diamines (TPD);
The material of luminescent layer is three [1-phenyl isoquinolin quinoline-C2, N] iridium (III) (Ir (piq)
3) join structural formula according to 25% massfraction and be
electron-transporting type ruddiness phosphor material (representing with P) in the doping mixing material of composition, be expressed as P:Ir (piq)
3;
The material of electric transmission/hole blocking layer is 4,7-phenylbenzene-1,10-phenanthroline (BPhen);
The material of electron injecting layer is LiF;
The material of cathode layer is Al;
Therefore, the structure of this organic electroluminescence device is:
Glass/ITO/CuPc/TPD/P:Ir (piq)
3/ BPhen/LiF/Al; Wherein, brace is expressed as laminate structure.
ITO adopts magnetron sputtering technique to prepare at glass surface, and other each functional layers adopt vacuum evaporation process to prepare.
(electron-transporting type ruddiness phosphor material provided by the invention, contain the good sulfonyl group of electronic transmission performance
group), introduce
group can strongthener electronic transmission performance.Therefore be conducive to carrier transport balance; Meanwhile, again because this material also has higher triplet, can effectively prevent that in luminescence process, energy returns to material of main part, therefore its luminous efficiency is high; In addition, this material also has good thermostability.
The preparation method of above-mentioned electron-transporting type ruddiness phosphor material, 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 electron-transporting type ruddiness phosphor material that makes of embodiment 1;
Fig. 2 is the organic electroluminescence device structural representation that embodiment 6 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 are all bought and are obtained from the market.
Embodiment 1
The electron-transporting type ruddiness phosphor material of the present embodiment, preparation process is as follows:
The first step: under nitrogen protection; by 2; 2'-oxygen base dibromobenzene (26.2g, 80mmol) is dissolved in 200mLN, in dinethylformamide (DMF) solution; then add thiophenol (17.6g; 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, and filtration is washed solid three times with distillation, and crude product employing leacheate normal hexane obtains canescence structural formula through silica gel column chromatography separation and is
solid product.Productive rate is 85%.
Second step: under ice-water bath, C (15.4g, 40mmol) is dissolved in methylene dichloride (DCM) solution of 120mL, is then splashed in the m-chloro-benzoic acid of 90mL (mCPBA) dichloromethane solution (2mol/L).At room temperature stirring reaction after 12 hours of mixture, then add 300mL saturated sodium bicarbonate solution to stir 30 minutes.Separate organic layer, anhydrous magnesium sulfate drying.The toluene that crude product employing volume ratio is 5:1 and alcohol mixed solution are as solvent, and recrystallization obtains white solid product 2,2'-oxygen base two (phenyl sulfonyl benzene).Productive rate 92%.Mass spectrum: m/z450.1(M
++ 1); Ultimate analysis (%) C
24h
18o
5s
2: theoretical value: C63.98, H4.03, O17.76, S14.23; Measured value: C63.91, H4.07, O17.73, S14.24.
Fig. 1 is the thermogravimetic analysis (TGA) figure of the electron-transporting type ruddiness phosphor material 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 344 DEG C.
Embodiment 2
The electron-transporting type ruddiness phosphor material of the present embodiment, its preparation process is as follows:
The first step: under nitrogen protection, 2,2'-oxygen base dibromobenzene (26.2g, 80mmol) is dissolved in 200mL toluene (Tol) solution; then add thiophenol (19.4g, 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, and filtration is washed solid three times with distillation, and crude product employing leacheate normal hexane obtains canescence structural formula through silica gel column chromatography separation and is
solid product.Productive rate is 89%.
Second step: step is with the second step in embodiment 1.
Embodiment 3
The electron-transporting type ruddiness phosphor material of the present embodiment, its preparation process is as follows:
The first step: under nitrogen protection, 2,2'-oxygen base dibromobenzene (26.2g, 80mmol) is dissolved in 200mL acetonitrile (MeCN) solution; then add thiophenol (21.1g, 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, and filtration is washed solid three times with distillation, and crude product employing leacheate normal hexane obtains canescence structural formula through silica gel column chromatography separation and is
solid product.Productive rate is 86%.
Second step: step is with the second step in embodiment 1.
Embodiment 4
The electron-transporting type ruddiness phosphor material of the present embodiment, its preparation process is as follows:
The first step: under nitrogen protection; by 2; 2'-oxygen base dibromobenzene (26.2g; 80mmol) be dissolved in 200mL tetrahydrofuran (THF) (THF) solution, then add thiophenol (20.2g, 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 and obtain pale solid product C through silica gel column chromatography.Productive rate is 82%.
Second step: step is with the second step in embodiment 1.
Embodiment 5
The electron-transporting type ruddiness phosphor material of the present embodiment, its preparation process is as follows:
The first step: under nitrogen protection; by 2; 2'-oxygen base dibromobenzene (26.2g, 80mmol) is dissolved in 200mL DMF (DMF) solution; then add thiophenol (18.5g; 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, and filtration is washed solid three times with distillation, and crude product employing leacheate normal hexane obtains canescence structural formula through silica gel column chromatography separation and is
solid product.Productive rate is 87%.
Second step: step is with the second step in embodiment 1.
Embodiment 6:
The present embodiment is organic electroluminescence device, its adopt above-described embodiment 1 to 5 arbitrary make 2,2'-oxygen base two (phenyl sulfonyl benzene) (representing with P) is as the material of main part of luminescent layer.
This organic electroluminescence device, as shown in Figure 2, comprises substrate 1/ conductive 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;
Conductive 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 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 three [1-phenyl isoquinolin quinoline-C2, N] iridium (III) (Ir (piq)
3) as object luminescent material, be doped to the doping mixing material obtaining in 2,2'-oxygen base two (phenyl sulfonyl benzene) (representing with P) material of main part according to 25% mass ratio, be expressed as P:Ir (piq)
3, 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 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:Ir (piq)
3/ BPhen/LiF/Al
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 CuPc, TPD, P:Ir (piq) on ITO layer surface
3, 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 4.0V, at 1000cd/m
2brightness under, luminous efficiency is 6.1lm/W.
Should be understood that, the above-mentioned statement for preferred embodiment of the present invention is comparatively detailed, can not therefore think the restriction to scope of patent protection of the present invention, and scope of patent protection of the present invention should be as the criterion with claims.
Claims (10)
1. an electron-transporting type ruddiness phosphor material, is characterized in that, its structural formula is:
2. a preparation method for electron-transporting type ruddiness phosphor material, 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, compd A is dissolved in organic solvent, and then adds compd B, mineral alkali and catalyzer in organic solvent, then at 70～120 DEG C, react after 6～15 hours, stopped reaction cool to room temperature, separating-purifying reaction solution, obtains structural formula and is
solid chemical compound C; Wherein, compd A and B mol ratio are 1:2～1:2.4;
Under frozen water mixes and bathes, Compound C is dissolved in methylene dichloride, obtains mixing solutions, then mixing solutions is splashed in the dichloromethane solution of m-chloro-benzoic acid, at room temperature react 12 hours after dropwising, separating-purifying reaction solution, obtains structural formula and is
electron-transporting type ruddiness phosphor material.
3. the preparation method of electron-transporting type ruddiness phosphor material according to claim 2, is characterized in that, described organic solvent is at least one in tetrahydrofuran (THF), acetonitrile, toluene, DMF.
4. the preparation method of electron-transporting type ruddiness phosphor material according to claim 2, is characterized in that, described mineral alkali is at least one in sodium carbonate, salt of wormwood, cesium carbonate and potassiumphosphate; The mol ratio of described mineral alkali and described compd A is 2:1～2.5:1.
5. the preparation method of electron-transporting type ruddiness phosphor material 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 electron-transporting type ruddiness phosphor material according to claim 2, it is characterized in that, to the separating-purifying of described Compound C, comprise: after reaction stops, filtering reacting liquid, and wash with water and obtain solid screening, crude product obtained, it is that leacheate separates through silica gel column chromatography that described crude product adopts normal hexane, obtains described Compound C.
7. the preparation method of electron-transporting type ruddiness phosphor material according to claim 2, is characterized in that, Compound C is dissolved in the mixing solutions obtaining after methylene dichloride, and the volumetric molar concentration of Compound C is 0.33mol/L.
8. the preparation method of electron-transporting type ruddiness phosphor material according to claim 2, is characterized in that, in the dichloromethane solution of m-chloro-benzoic acid, the concentration of m-chloro-benzoic acid is 2mol/L.
9. the preparation method of electron-transporting type ruddiness phosphor material according to claim 2, is characterized in that, the separating-purifying of described electron-transporting type ruddiness phosphor material, comprising: in reaction solution, add saturated NaHCO
3, and stir 30 minutes, separate organic layer, then use anhydrous magnesium sulfate drying organic layer, obtain crude product, it is solvent that described crude product adopts toluene and the alcohol mixed solution that volume ratio is 5:1, carries out recrystallization, obtains electron-transporting type ruddiness phosphor material.
10. an organic electroluminescence device, is characterized in that, the material of its luminescent layer is that three [1-phenyl isoquinolin quinoline-C2, N] iridium joins structural formula according to 25% massfraction and is
electron-transporting type ruddiness phosphor material in the doping mixing material that forms.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201310204158.6A CN104178122A (en) | 2013-05-28 | 2013-05-28 | Electron transport type red light phosphorescent material, preparation method and organic electroluminescent device thereof |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201310204158.6A CN104178122A (en) | 2013-05-28 | 2013-05-28 | Electron transport type red light phosphorescent material, preparation method and organic electroluminescent device thereof |
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|---|---|
| CN104178122A true CN104178122A (en) | 2014-12-03 |
Family
ID=51959476
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|---|---|---|---|
| CN201310204158.6A Pending CN104178122A (en) | 2013-05-28 | 2013-05-28 | Electron transport type red light phosphorescent material, preparation method and organic electroluminescent device thereof |
Country Status (1)
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0567314A1 (en) * | 1992-04-24 | 1993-10-27 | Fuji Photo Film Co., Ltd. | Electron-accepting compounds and color recording materials containing them |
| CN101519400A (en) * | 2009-03-27 | 2009-09-02 | 武汉工程大学 | Macrocyclic aryl thioether ether sulfone oligomer and preparation method thereof |
-
2013
- 2013-05-28 CN CN201310204158.6A patent/CN104178122A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0567314A1 (en) * | 1992-04-24 | 1993-10-27 | Fuji Photo Film Co., Ltd. | Electron-accepting compounds and color recording materials containing them |
| CN101519400A (en) * | 2009-03-27 | 2009-09-02 | 武汉工程大学 | Macrocyclic aryl thioether ether sulfone oligomer and preparation method thereof |
Non-Patent Citations (1)
| Title |
|---|
| 叶坚等，: ""有机电子传输材料研究新进展"", 《自然科学进展》 * |
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Application publication date: 20141203 |