CN104178127A - 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
- Publication number
- CN104178127A CN104178127A CN201310204503.6A CN201310204503A CN104178127A CN 104178127 A CN104178127 A CN 104178127A CN 201310204503 A CN201310204503 A CN 201310204503A CN 104178127 A CN104178127 A CN 104178127A
- Authority
- CN
- China
- Prior art keywords
- main part
- emitting phosphor
- blue emitting
- phosphor material
- preparation
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
Landscapes
- Electroluminescent Light Sources (AREA)
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 electron transport material has a structural formula shown as the specification. The bipolar blue light phosphorescent host material provided by the invention has bipolar carrier transport ability, also 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 and use the organic electroluminescence device of bipolarity blue emitting phosphor material of main part as luminescent layer 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:
3,6-bis-(4-(4,5-phenylbenzene-4H-1,2,4-triazole-3-yl) phenyl)-9-phenyl-9H-carbazole.
The present invention also provides 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,
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 subsequently, stop after coupling reaction, separating-purifying reaction solution, obtains the 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 made up of one or both in argon gas, nitrogen.
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 DEG 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, with repeatedly reaction solution of dichloromethane extraction, obtain organic phase; Then with being spin-dried for organic phase after anhydrous magnesium sulfate drying, obtain crude product; It is leacheate that crude product adopts sherwood oil and the ethyl acetate that volume ratio is 10:1, separates and obtains crystalline substance through silica gel column chromatography, and this crystalline substance after 50 DEG C of dry 24h, obtains described bipolarity blue emitting phosphor material of main part under vacuum.
The invention still further relates to a kind of organic electroluminescence device, comprise substrate, and stack gradually anode layer, hole injection layer, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer and the 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 that two (4,6-difluorophenyl pyridine-N, C2) pyridine formyls close ratio that iridium (III) is (FIrpic) 15% according to mass percent and add structural formula to and be
bipolarity blue emitting phosphor material of main part in the doping mixing material that forms;
Electric transmission/hole blocking layer, its material is 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 bipolarity carrier transport ability, 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.
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 structural representation of the organic electroluminescence device of embodiment 5.
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 bipolarity blue emitting phosphor material of main part of the present embodiment, 3,6-bis-(4-(4,5-phenylbenzene-4H-1,2,4-triazole-3-yl) phenyl)-9-phenyl-9H-carbazole, preparation process is as follows:
Under argon shield, the bromo-9-phenyl-9H-of 3,6-bis-carbazole (75mg, 0.2mmol), 3,4-phenylbenzene-5-(4-tetramethyl ethylene ketone boric acid ester phenyl)-4H-1,2,4-triazole (169mg, 0.4mmol) 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, dichloromethane extraction is reaction solution repeatedly, obtains organic phase; Then with being spin-dried for organic phase after anhydrous magnesium sulfate drying, obtain crude product; It is leacheate that crude product adopts sherwood oil and the ethyl acetate that volume ratio is 10:1, separates and obtains crystalline substance through silica gel column chromatography, and this crystalline substance after 50 DEG C of dry 24h, obtains described bipolarity blue emitting phosphor material of main part under vacuum.Productive rate is 76%.Mass spectrum: m/z833.3(M
++ 1); Ultimate analysis (%) C
58h
39n
7: theoretical value: C83.53, H4.71, N11.76; Measured value: C83.61, H4.78, N11.85.
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 420 DEG C.
Embodiment 2:
The bipolarity blue emitting phosphor material of main part of the present embodiment, 3,6-bis-(4-(4,5-phenylbenzene-4H-1,2,4-triazole-3-yl) phenyl)-9-phenyl-9H-carbazole, preparation process is as follows:
Under nitrogen and the protection of argon gas gas mixture; by 3; the bromo-9-phenyl-9H-of 6-bis-carbazole (120mg; 0.3mmol), 3; 4-phenylbenzene-5-(4-tetramethyl ethylene ketone boric acid ester phenyl)-4H-1; 2; 4-triazole (254mg; 0.6mmol) 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 tetra-triphenylphosphine palladium (4mg, 0.003mmol) is added 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, dichloromethane extraction is reaction solution repeatedly, obtains organic phase; Then with being spin-dried for organic phase after anhydrous magnesium sulfate drying, obtain crude product; It is leacheate that crude product adopts sherwood oil and the ethyl acetate that volume ratio is 10:1, separates and obtains crystalline substance through silica gel column chromatography, and this crystalline substance after 50 DEG C of dry 24h, obtains described bipolarity blue emitting phosphor material of main part under vacuum.Productive rate is 80%.
Embodiment 3:
The bipolarity blue emitting phosphor material of main part of the present embodiment, 3,6-bis-(4-(4,5-phenylbenzene-4H-1,2,4-triazole-3-yl) phenyl)-9-phenyl-9H-carbazole, preparation process is as follows:
Under nitrogen protection, by 3, the bromo-9-phenyl-9H-of 6-bis-carbazole (120mg, 0.3mmol), 3,4-phenylbenzene-5-(4-tetramethyl ethylene ketone boric acid ester phenyl)-4H-1,2,4-triazole (279mg, 0.66mmol), palladium (3.5mg, 0.015mmol) and three (o-methoxyphenyl) phosphine (21mg, 0.06mmol) joins 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, dichloromethane extraction is reaction solution repeatedly, obtains organic phase; Then with being spin-dried for organic phase after anhydrous magnesium sulfate drying, obtain crude product; It is leacheate that crude product adopts sherwood oil and the ethyl acetate that volume ratio is 10:1, separates and obtains crystalline substance through silica gel column chromatography, and this crystalline substance after 50 DEG C of dry 24h, obtains described bipolarity blue emitting phosphor material of main part under vacuum.Productive rate is 75%.
Embodiment 4:
The bipolarity blue emitting phosphor material of main part of the present embodiment, 3,6-bis-(4-(4,5-phenylbenzene-4H-1,2,4-triazole-3-yl) phenyl)-9-phenyl-9H-carbazole, preparation process is as follows:
Under nitrogen protection; will; by 3; the bromo-9-phenyl-9H-of 6-bis-carbazole (120mg; 0.3mmol), 3; 4-phenylbenzene-5-(4-tetramethyl ethylene ketone boric acid ester phenyl)-4H-1; 2,4-triazole (305mg, 0.72mmol), three or two argon benzyl acetone two palladium (9mg; 0.009mmol) with 2-dicyclohexyl phosphine-2 '; 6 '-dimethoxy-biphenyl (29mg, 0.072mmol) joins in the flask of the DMF that fills 12mL; 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, dichloromethane extraction is reaction solution repeatedly, obtains organic phase; Then with being spin-dried for organic phase after anhydrous magnesium sulfate drying, obtain crude product; It is leacheate that crude product adopts sherwood oil and the ethyl acetate that volume ratio is 10:1, separates and obtains crystalline substance through silica gel column chromatography, and this crystalline substance after 50 DEG C of dry 24h, obtains described bipolarity blue emitting phosphor material of main part under vacuum.Productive rate is 83%.
Embodiment 5:
The present embodiment is organic electroluminescence device, its adopt above-described embodiment 1 to 4 arbitrary make 3,6-bis-(4-(4,5-phenylbenzene-4H-1,2,4-triazole-3-yl) phenyl)-9-phenyl-9H-carbazole is as the material of main part of 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 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 (4,6-difluorophenyl pyridine-N, C2) pyridine formyl closes iridium (III) FIrpic as object luminescent material, be doped to 3,6-bis-(4-(4,5-phenylbenzene-4H-1 according to 15% mass ratio, 2,4-triazole-3-yl) phenyl) the doping mixing material that obtains in-9-phenyl-9H-carbazole (representing with P) material of main part, be expressed as P:FIrpic, 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: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, stack gradually evaporation CuPc, TPD, P:FIrpic, 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.
Test result is that the trigger voltage of organic electroluminescence device is 3.4V, at 1000cd/m
2brightness under, luminous efficiency is 7.3lm/W.
The above embodiment has only expressed several embodiment of the present invention, and it describes comparatively concrete and detailed, but can not therefore be interpreted as the restriction to the scope of the claims of the present invention.It should be pointed out that for the person of ordinary skill of the art, without departing from the inventive concept of the premise, can also make some distortion and improvement, these all belong to protection scope of the present invention.Therefore, the protection domain of patent of the present invention should be as the criterion with claims.
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,
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 subsequently, stop after coupling reaction, separating-purifying reaction solution, obtains the 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.
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 3, 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 3, 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 3, 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 bipolarity blue emitting phosphor material of main part according to claim 2, is characterized in that, separating-purifying reaction solution comprises:
After coupling reaction, with repeatedly reaction solution of dichloromethane extraction, obtain organic phase; Then with being spin-dried for organic phase after anhydrous magnesium sulfate drying, obtain crude product; It is leacheate that crude product adopts sherwood oil and the ethyl acetate that volume ratio is 10:1, separates and obtains crystalline substance through silica gel column chromatography, and this crystalline substance after 50 DEG C of dry 24h, obtains 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 that two (4,6-difluorophenyl pyridine-N, C2) pyridine formyls close ratio that iridium (III) is 15% according to mass percent and add structural formula to and be
bipolarity blue emitting phosphor material of main part in the doping mixing material that forms.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201310204503.6A CN104178127A (en) | 2013-05-28 | 2013-05-28 | Bipolar blue light phosphorescent host material, preparation method and organic electroluminescent device thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201310204503.6A CN104178127A (en) | 2013-05-28 | 2013-05-28 | Bipolar blue light phosphorescent host material, preparation method and organic electroluminescent device thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN104178127A true CN104178127A (en) | 2014-12-03 |
Family
ID=51959481
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201310204503.6A Pending CN104178127A (en) | 2013-05-28 | 2013-05-28 | Bipolar blue light phosphorescent host material, preparation method and organic electroluminescent device thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN104178127A (en) |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20100184942A1 (en) * | 2009-01-22 | 2010-07-22 | Chen Shaw H | Hybrid Host Materials For Electrophosphorescent Devices |
| KR20120038032A (en) * | 2010-10-07 | 2012-04-23 | 에스에프씨 주식회사 | Heterocyclic com pounds and organic light-emitting diode including the same |
| WO2013032297A1 (en) * | 2011-09-01 | 2013-03-07 | Rohm And Haas Electronic Materials Korea Ltd. | Benzocarbazole compounds and electroluminescent devices involving them |
-
2013
- 2013-05-28 CN CN201310204503.6A patent/CN104178127A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20100184942A1 (en) * | 2009-01-22 | 2010-07-22 | Chen Shaw H | Hybrid Host Materials For Electrophosphorescent Devices |
| KR20120038032A (en) * | 2010-10-07 | 2012-04-23 | 에스에프씨 주식회사 | Heterocyclic com pounds and organic light-emitting diode including the same |
| WO2013032297A1 (en) * | 2011-09-01 | 2013-03-07 | Rohm And Haas Electronic Materials Korea Ltd. | Benzocarbazole compounds and electroluminescent devices involving them |
Non-Patent Citations (1)
| Title |
|---|
| YOUTIAN TAO ET AL.: "Highly Efficient Phosphorescent Organic Light-Emitting Diodes Hosted by 1,2,4-Triazole-Cored Triphenylamine Derivatives: Relationship between Structure and Optoelectronic Properties", 《 J. PHYS. CHEM. C》 * |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN104342120A (en) | Organic semiconductor material, preparation method thereof, and electroluminescent device | |
| CN103804372A (en) | Bipolar blue phosphorescent compound, and preparation method and application thereof | |
| CN103804360A (en) | Bipolar blue phosphorescent compound, and preparation method and application thereof | |
| CN103804301A (en) | Bipolar blue light phosphorescence compound, preparation method and application thereof | |
| CN104419402A (en) | Carbazolyl blue phosphorescent host material as well as preparation method and application thereof | |
| CN104250242A (en) | Dibenzothiophene unit-containing blue light phosphorescent body material, preparation method thereof and organic electroluminescent device | |
| CN104178124A (en) | Bipolar blue light phosphorescent host material, preparation method and organic electroluminescent device thereof | |
| CN104513655A (en) | Bipolar blue phosphorescence host material, preparation method and applications thereof | |
| CN104293348A (en) | Bipolar blue-light emitting host material, and preparation method and application thereof | |
| CN104017562A (en) | Bipolar blue-phosphorescence material, preparation method thereof and organic electroluminescent device | |
| CN104178127A (en) | Bipolar blue light phosphorescent host material, preparation method and organic electroluminescent device thereof | |
| CN104119334A (en) | Organic semiconductor material, preparation method thereof and electroluminescent device | |
| CN104017563A (en) | Bipolar blue-phosphorescence material, preparation method thereof and organic electroluminescent device | |
| CN104250549A (en) | Red light phosphorescent main body material, preparation method thereof and organic electroluminescent device | |
| CN104513659A (en) | Bipolar blue phosphorescence host material, preparation method and applications thereof | |
| CN104341419A (en) | Organic semiconductor material, preparation method thereof, and electroluminescent device | |
| CN104119318A (en) | Organic semiconductor material, preparation method thereof and electroluminescent device | |
| CN104119290A (en) | Organic semiconductor material, preparation method thereof and electroluminescent device | |
| CN103848858A (en) | Organic semiconductor material and preparation method thereof and electroluminescent device | |
| CN104341445A (en) | Organic semiconductor material, preparation method thereof, and electroluminescent device | |
| CN103896931A (en) | Organic semiconductor material and preparation method thereof, and electroluminescent device | |
| CN104211656A (en) | Organic semiconductor material, preparation method, and electroluminescent device | |
| CN104211698A (en) | Organic semiconductor material, preparation method, and electroluminescent device | |
| CN104341398A (en) | Organic semiconductor material, preparation method and electroluminescent device | |
| CN103896912A (en) | Organic semiconductor material and preparation method thereof, and electroluminescent device |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C02 | Deemed withdrawal of patent application after publication (patent law 2001) | ||
| WD01 | Invention patent application deemed withdrawn after publication |
Application publication date: 20141203 |