CN103804640A - Electron transfer polymer, and preparation method and application thereof - Google Patents
Electron transfer polymer, and preparation method and application thereof Download PDFInfo
- Publication number
- CN103804640A CN103804640A CN201210444219.1A CN201210444219A CN103804640A CN 103804640 A CN103804640 A CN 103804640A CN 201210444219 A CN201210444219 A CN 201210444219A CN 103804640 A CN103804640 A CN 103804640A
- Authority
- CN
- China
- Prior art keywords
- electron
- polymkeric substance
- type polymkeric
- transporting type
- 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
- 0 CB(C(C=C*=C1*2O*(C)(*)*(C)(C)O2)SC1=NSN)OC(C)(C)C(C)(C)* Chemical compound CB(C(C=C*=C1*2O*(C)(*)*(C)(C)O2)SC1=NSN)OC(C)(C)C(C)(C)* 0.000 description 1
- VGRHKYITOQSLOT-UHFFFAOYSA-N CC(C)(C)C(C=C)=N Chemical compound CC(C)(C)C(C=C)=N VGRHKYITOQSLOT-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Electroluminescent Light Sources (AREA)
Abstract
The invention belongs to the field of organic semiconductor materials, and discloses an electron transfer polymer, and a preparation method and an application thereof. The polymer has a structural formula shown in the specification, and n in the formula is an integer in a range of 10-100. The benzothiadiazol ring of the electron transfer polymer has an electron deficiency, has an n-type structure, and can be used as an electron transfer material. The introduction of benzothiadiazole to the main chain of an anthracylimidazolyl polymer benefits the improvement of the electron mobility, so the luminous efficiency of an organic electroluminescent device can be substantially improved.
Description
Technical field
The present invention relates to organic semiconductor material field, relate in particular to a kind of electron-transporting type polymkeric substance and its preparation method and application.
Background technology
That organic electroluminescence device has is light, thin, luminous, low consumpting power, do not need light source, without angle limitations, high reaction rate and can be produced on the good characteristics such as flexible base plate, be regarded as the rising star of flat-panel screens and flexible display.The carrier mobility of traditional electron transport material is the thousandth of hole mobile material, and thermostability is not good, therefore, often cause the problems such as the not good or component life of luminous efficiency is long, represent according to pertinent literature, the shared charge consumption ratio of electron transport material reaches 35.9%, is the consumption (39.8%) that is only second to luminescent layer, and the electron transport material of therefore developing now high carrier is the just emphasis of developing material of OLED now.
Alq
3the film-forming properties that (oxine aluminium) has had, therefore, is the host emitter of current conventional electron transport material, but has successively some carrier mobilities and T
ghigher than Alq
3material occur, as metal (Be, Al, Zn) complex compound, 1,2, derivative, fluorochemicals and the silicon-containing compound etc. of 4-triazole (TAZ), but these known material carrier mobilities are still not good, and there is not thermostability good or be used on device the problems such as generation current density is low, the luminous efficiency that these problems all restrict material is low, and therefore, developing new electron transport material is a very important problem.。
Summary of the invention
The electron-transporting type polymkeric substance that provides a kind of luminous efficiency higher is provided problem to be solved by this invention.
Technical scheme of the present invention is as follows:
A kind of electron-transporting type polymkeric substance, has following structural formula:
The preparation method of this electron-transporting type polymkeric substance, comprises the steps:
Under oxygen-free environment, by structural formula be
compd A and structural formula be
b be added into and contain in the organic solvent that catalyzer and alkaline solution exist, at 70～130 ℃, carry out Suzuki coupling reaction 12～48 hours, stopped reaction cool to room temperature, obtain structural formula and be after separating-purifying
electron-transporting type polymkeric substance, in formula, the integer that n is 10 ~ 100; Wherein, the mol ratio of compd A and compd B is 1:1～1.2.
The preparation method of described electron-transporting type polymkeric substance, wherein, described catalyzer is three or two argon benzyl acetone two palladiums and the 2-dicyclohexyl phosphine-2 ' that bi triphenyl phosphine dichloride palladium, tetra-triphenylphosphine palladium, the mol ratio palladium that is 1:4～8 and tri-o-tolyl phosphine mixture or mol ratio are 1:4～8,6 '-dimethoxy-biphenyl mixture; The mol ratio of described catalyzer and described compd A is 1:20 ~ 1:100.
The preparation method of described electron-transporting type polymkeric substance, wherein, described alkaline solution is selected from least one in sodium carbonate solution, solution of potassium carbonate and sodium bicarbonate aqueous solution; In described alkaline solution, 20 times of the molar weight that the molar weight of alkali solute is compd A.
The preparation method of described electron-transporting type polymkeric substance, wherein, described organic solvent is at least one in toluene, DMF and tetrahydrofuran (THF).
The preparation method of described electron-transporting type polymkeric substance, wherein, the temperature of reaction of Suzuki coupling reaction is 90～120 ℃, the reaction times is 24～36 hours.
The preparation method of described electron-transporting type polymkeric substance, wherein, the separating-purifying of described electron-transporting type polymkeric substance comprises the steps:
After Suzuki coupling reaction finishes, in reaction solution, add methyl alcohol precipitating, after filtering by apparatus,Soxhlet's, use successively methyl alcohol and normal hexane extracting, then take chloroform as solvent extraction to colourless, collect chloroformic solution and be spin-dried for and obtain powder, after collection, under vacuum, after 50 ° of dry 24h of C, obtain described electron-transporting type polymkeric substance.
Above-mentioned electron-transporting type polymkeric substance in organic electroluminescence device as the application of electric transmission layer material.
Electron-transporting type polymkeric substance of the present invention, diazosulfide ring has electron deficiency, is n-type structure, can be used as electron transport material.On anthracene azoles based polyalcohol main chain, introduce diazosulfide, be conducive to the raising of electronic mobility, thereby greatly improved the luminous efficiency of organic electroluminescence device.Meanwhile, anthracene azoles contains two nitrogen, is a good electric transmission unit, and has good rigidity and planarity, and thermal stability is good.
The preparation technology of electron-transporting type polymkeric substance provided by the invention, has adopted better simply synthetic route, and synthetic method is simple, thereby reduces technical process, and starting material are cheap and easy to get, and manufacturing cost is reduced, and is suitable for widespread use.
Accompanying drawing explanation
Fig. 1 is the thermogravimetic analysis (TGA) figure of electron-transporting type polymkeric substance of the present invention;
Fig. 2 is the structural representation of the organic electroluminescence device of embodiment 5.
Embodiment
Electron-transporting type polymkeric substance provided by the invention, its structure suc as formula shown in:
n is 10 ~ 100 integer, gathers { 4,7-, bis-base diazosulfide-co-2,7-bis-base-4,9-diphenylanthrancene azoles } (BTzPEz).
Electron-transporting type polymkeric substance of the present invention, diazosulfide ring has electron deficiency, is n-type structure, can be used as electron transport material.On anthracene azoles based polyalcohol main chain, introduce diazosulfide, be conducive to the raising of electronic mobility, thereby greatly improved the luminous efficiency of organic electroluminescence device.Meanwhile, anthracene azoles contains two nitrogen, is a good electric transmission unit, and has good rigidity and planarity, and thermal stability is good.
Fig. 1 is the thermogravimetic analysis (TGA) figure of electron-transporting type polymkeric substance of the present invention; Thermogravimetic analysis (TGA) is completed by Perkin-Elmer Series 7 Thermo System measurements, and all measurements all complete in atmosphere at room temperature.
As shown in Figure 1,5% thermal weight loss temperature (T
d) be 477 ℃.
The preparation method of above-mentioned electron-transporting type polymkeric substance, comprises the steps:
S1, respectively provide following structural formula to represent compd A and B,
S2, under oxygen-free environment (nitrogen, argon gas or nitrogen and argon gas gas mixture form), compd A and B are added in the organic solvent that contains catalyzer and alkaline solution existence, at 70～130 ℃, carry out Suzuki coupling reaction 12～48 hours, stopped reaction cool to room temperature, separating-purifying obtains structural formula and is
electron-transporting type polymkeric substance, in formula, the integer that n is 10 ~ 100; Wherein, the mol ratio of compd A and compd B is 1:1～1.2; Reaction formula is as follows:
In the preparation method of above-mentioned electron-transporting type polymkeric substance, in step S2:
Preferably, described catalyzer is three or two argon benzyl acetone two palladiums and the 2-dicyclohexyl phosphine-2 ' that bi triphenyl phosphine dichloride palladium, tetra-triphenylphosphine palladium, the mol ratio palladium that is 1:4～8 and tri-o-tolyl phosphine mixture or mol ratio are 1:4～8,6 '-dimethoxy-biphenyl mixture; The mol ratio of described catalyzer and described compd A is 1:20 ~ 1:100.
Preferably, described alkaline solution is selected from least one in sodium carbonate solution, solution of potassium carbonate and sodium bicarbonate aqueous solution; In described alkaline solution, 20 times of the molar weight that the molar weight of alkali solute is compd A.
Preferably, described organic solvent is at least one in toluene, DMF and tetrahydrofuran (THF).
Preferably, the temperature of reaction of Suzuki coupling reaction is 90～120 ℃, and the reaction times is 24～36 hours.
Preferably, the separating-purifying of described electron-transporting type polymkeric substance comprises the steps:
After Suzuki coupling reaction finishes, in reaction solution, add methyl alcohol precipitating, after filtering by apparatus,Soxhlet's, use successively methyl alcohol and normal hexane extracting, then take chloroform as solvent extraction to colourless, collect chloroformic solution and be spin-dried for and obtain red powder, after collection, under vacuum, after 50 ° of dry 24h of C, obtain described electron-transporting type polymkeric substance.
Above-mentioned electron-transporting type polymkeric substance in organic electroluminescence device as the application of electric transmission layer material.
Below in conjunction with accompanying drawing, preferred embodiment of the present invention is described in further detail.
Embodiment 1
The electron-transporting type polymkeric substance of the present embodiment, (n=56), preparation process is as follows to gather { 4,7-, bis-base diazosulfide-co-2,7-bis-base-4,9-diphenylanthrancene azoles }:
Under argon shield, by 4,7-hypoboric acid pinacol ester diazosulfide (78mg, 0.2mmol), 2,7-bis-bromo-4,9-diphenylanthrancene azoles (98mg, 0.2mmol) adds 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 ℃ and carries out Suzuki coupling reaction 48h.Subsequently, after cooling, stop polyreaction, in 50ml methyl alcohol, carry out sedimentation to dripping in flask; After filtering by apparatus,Soxhlet's, use successively methyl alcohol and normal hexane extracting 24h.Then take chloroform as solvent extraction to colourless, to collect chloroformic solution and be spin-dried for and obtain red powder, under vacuum pump, taking out spends the night obtains product, productive rate 80%.
Test result is: Molecular weight (GPC, THF, R.I): M
n=27.6kDa, M
w/ M
n=2.2.
Embodiment 2
The electron-transporting type polymkeric substance of the present embodiment, (n=100), preparation process is as follows to gather { 4,7-, bis-base diazosulfide-co-2,7-bis-base-4,9-diphenylanthrancene azoles }:
Under nitrogen and the protection of argon gas gas mixture; by 4; 7-hypoboric acid pinacol ester diazosulfide (116mg; 0.3mmol), 2; 7-bis-bromo-4; 9-diphenylanthrancene azoles (147mg; 0.3mmol) 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 ℃ and carry out Suzuki coupling reaction 96h again.Subsequently, after cooling, stop polyreaction, in two-mouth bottle, add 40mL methyl alcohol precipitating, after filtering by apparatus,Soxhlet's, use successively methyl alcohol and normal hexane extracting 24h.Then take chloroform as solvent extraction to colourless, collect chloroformic solution and be spin-dried for and obtain red solid, after collection, under vacuum, after 50 ℃ of dry 24h, obtain product.Productive rate is 89%.
Test result is: Molecular weight (GPC, THF, R.I): M
n=46.3kDa, M
w/ M
n=2.0.
Embodiment 3
The electron-transporting type polymkeric substance of the present embodiment, (n=10), preparation process is as follows to gather { 4,7-, bis-base diazosulfide-co-2,7-bis-base-4,9-diphenylanthrancene azoles }:
Under nitrogen protection, by 4,7-hypoboric acid pinacol ester diazosulfide (116mg, 0.3mmol), 2,7-bis-bromo-4,9-diphenylanthrancene azoles (162mg, 0.33mmol), palladium (3.5mg, 0.015mmol) He three (o-methoxyphenyl) phosphine (21mg, 0.06mmol) join in the flask of the DMF that fills 12mL, after fully dissolving, add salt of wormwood (3mL, 2mol/L) solution leads to after the about 30min of nitrogen purge gas subsequently in flask; Flask is heated to 130 ℃ and carries out Suzuki coupling reaction 12h.Subsequently, after cooling, stop polyreaction, in flask, add 40mL methyl alcohol precipitating, after filtering by apparatus,Soxhlet's, use successively methyl alcohol and normal hexane extracting 24h; Then take chloroform as solvent extraction to colourless, collect chloroformic solution and be spin-dried for and obtain red powder, after collection, under vacuum, after 50 ℃ of dry 24h, be product, productive rate 86%.
Test result is: Molecular weight (GPC, THF, R.I): M
n=9.3kDa, M
w/ M
n=2.4.
Embodiment 4
The electron-transporting type polymkeric substance of the present embodiment, (n=81), preparation process is as follows to gather { 4,7-, bis-base diazosulfide-co-2,7-bis-base-4,9-diphenylanthrancene azoles }:
Under nitrogen protection; by 4; 7-hypoboric acid pinacol ester diazosulfide (116mg; 0.3mmol), 2; 7-bis-bromo-4; 9-diphenylanthrancene azoles (176mg; 0.36mmol), 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 bicarbonate (3mL, 2mol/L) solution.In flask, lead to after the about 30min of nitrogen purge gas subsequently; Flask is heated to 120 ℃ and carries out Suzuki coupling reaction 36h.Subsequently, after cooling, stop polyreaction, in flask, add 40mL methyl alcohol precipitating, after filtering by apparatus,Soxhlet's, use successively methyl alcohol and normal hexane extracting 24h; Then take chloroform as solvent extraction to colourless, collect chloroformic solution and be spin-dried for and obtain red powder, after collection, under vacuum, after 50 ℃ of dry 24h, be product, productive rate is 83%.
Test result is: Molecular weight (GPC, THF, R.I): M
n=35.7kDa, M
w/ M
n=2.1.
Embodiment 5
The present embodiment is organic electroluminescence device, and it adopts arbitrary poly-{ 4,7-, bis-base diazosulfide-co-2,7-bis-base-4, the 9-diphenylanthrancene azoles } making of above-described embodiment 1 to 5 (BTzPEz) as electric transmission layer material.
This organic electroluminescence device, as shown in Figure 2, comprises substrate 1/ conductive anode layer 2/ hole injection layer 3/ hole transmission layer 4/ luminescent layer 5/ electron transfer layer 6/ electron injecting layer 7 cathode layers 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 transmission layer 4 is 4,4 '-bis-[N-(naphthyl)-N-phenyl-amino] biphenyl (NPB), and thickness is 20nm;
The material of luminescent layer 5 is that 4,4'-bis-(9-carbazole) biphenyl CBP doping, three (2-phenylpyridines) close iridium (III) (Ir (ppy)
3) as object luminescent material, be doped to the doping mixing material obtaining in 4,4'-bis-(9-carbazole) biphenyl (CBP) material of main part according to 12% mass ratio, be expressed as CBP:Ir (ppy)
3, thickness is 20nm;
The material of electron transfer layer 6 is for gathering { 4,7-, bis-base diazosulfide-co-2,7-bis-base-4,9-diphenylanthrancene azoles } (BTzPEz), 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/NPB/CBP:Ir (ppy)
3/ BTzPEz/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, NPB, CBP:Ir (ppy) on ITO layer surface
3;
Again secondly, at CBP:Ir (ppy)
3surperficial spin coating BTzPEz;
Best, again, in vacuum evaporation equipment, stack gradually evaporation LiF, Al on BTzPEz 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 with correction silicon photoelectric diode (Keithley 2400 Sourcemeter, Keithley 2000 Cuirrentmeter).
Test result is that the trigger voltage of organic electroluminescence device is 3.6V, at 1000cd/m
2brightness under, luminous efficiency is 25.0lm/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 (9)
1. an electron-transporting type polymkeric substance, is characterized in that, this polymkeric substance has following structural formula:
2. a preparation method for electron-transporting type polymkeric substance, is characterized in that, comprises the steps:
Under oxygen-free environment, by structural formula be
compd A and structural formula be
b be added into and contain in the organic solvent that catalyzer and alkaline solution exist, at 70～130 ℃, carry out Suzuki coupling reaction 12～48 hours, stopped reaction cool to room temperature, obtain structural formula and be after separating-purifying
electron-transporting type polymkeric substance, in formula, the integer that n is 10 ~ 100; Wherein, the mol ratio of compd A and compd B is 1:1～1.2.
3. the preparation method of electron-transporting type polymkeric substance 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 electron-transporting type polymkeric substance according to claim 2, it is characterized in that, described catalyzer is that mol ratio is three or two argon benzyl acetone two palladiums and the 2-dicyclohexyl phosphine-2 ' that the palladium of 1:4～8 and tri-o-tolyl phosphine mixture or mol ratio are 1:4～8,6 '-dimethoxy-biphenyl mixture; The mol ratio of described catalyzer and described compd A is 1:20 ~ 1:100.
5. the preparation method of electron-transporting type polymkeric substance 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 bicarbonate aqueous solution; In described alkaline solution, 20 times of the molar weight that the molar weight of alkali solute is compd A.
6. the preparation method of electron-transporting type polymkeric substance according to claim 2, is characterized in that, described organic solvent is at least one in toluene, DMF and tetrahydrofuran (THF).
7. the preparation method of electron-transporting type polymkeric substance according to claim 2, is characterized in that, the temperature of reaction of Suzuki coupling reaction is 90～120 ℃, and the reaction times is 24～36 hours.
8. the preparation method of electron-transporting type polymkeric substance according to claim 2, is characterized in that, the separating-purifying of described electron-transporting type polymkeric substance comprises the steps:
After Suzuki coupling reaction finishes, in reaction solution, add methyl alcohol precipitating, after filtering by apparatus,Soxhlet's, use successively methyl alcohol and normal hexane extracting, then take chloroform as solvent extraction to colourless, collect chloroformic solution and be spin-dried for and obtain powder, after collection, under vacuum, after 50 ° of dry 24h of C, obtain described electron-transporting type polymkeric substance.
Electron-transporting type polymkeric substance claimed in claim 1 in organic electroluminescence device as the application of electric transmission layer material.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201210444219.1A CN103804640A (en) | 2012-11-08 | 2012-11-08 | Electron transfer polymer, and preparation method and application thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201210444219.1A CN103804640A (en) | 2012-11-08 | 2012-11-08 | Electron transfer polymer, and preparation method and application thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN103804640A true CN103804640A (en) | 2014-05-21 |
Family
ID=50702067
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201210444219.1A Pending CN103804640A (en) | 2012-11-08 | 2012-11-08 | Electron transfer polymer, and preparation method and application thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN103804640A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110128372A (en) * | 2018-02-02 | 2019-08-16 | 北京鼎材科技有限公司 | Diazosulfide analog derivative and its application and organic electroluminescence device |
-
2012
- 2012-11-08 CN CN201210444219.1A patent/CN103804640A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110128372A (en) * | 2018-02-02 | 2019-08-16 | 北京鼎材科技有限公司 | Diazosulfide analog derivative and its application and organic electroluminescence device |
| CN110128372B (en) * | 2018-02-02 | 2023-05-16 | 北京鼎材科技有限公司 | Benzothiadiazole derivative, application thereof and organic electroluminescent device |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN104017174A (en) | Green-light copolymer material as well as preparation method thereof and organic light-emitting device | |
| CN104292261A (en) | Phosphine sulfur group electron transport material, preparation method and application thereof | |
| CN104178120A (en) | Blue light phosphorescent host material containing benzimidazole unit, preparation method and organic electroluminescent device thereof | |
| CN103804372A (en) | Bipolar blue phosphorescent compound, and preparation method and application thereof | |
| CN103804640A (en) | Electron transfer polymer, and preparation method and application thereof | |
| CN103804637A (en) | Electron transfer polymer, and preparation method and application thereof | |
| CN104017565A (en) | Bipolar blue-phosphorescence material, preparation method thereof and organic electroluminescent device | |
| CN104292424A (en) | Polymer electron transfer material, preparation method thereof, and organic electroluminescent device | |
| CN104292266A (en) | Phosphinosulfenyl electron transfer material, preparation method thereof, and organic electroluminescent device | |
| CN104292268A (en) | Phosphine sulfur group electron transport material, preparation method and application thereof | |
| CN104292260A (en) | Phosphine sulfur group electron transport material, preparation method and application thereof | |
| CN104292264A (en) | Phosphine sulfur group electron transport material, preparation method and application thereof | |
| CN103881061B (en) | A kind of bipolarity multipolymer Blue-light emitting host material and preparation method thereof and organic electroluminescence device | |
| CN104629010A (en) | Copolymer blue-ray host material, as well as preparation method and organic electroluminescent device thereof | |
| CN104292423A (en) | Bipolar copolymer host material, preparation method thereof and organic electroluminescent device | |
| CN104017562A (en) | Bipolar blue-phosphorescence material, preparation method thereof and organic electroluminescent device | |
| CN103881064B (en) | A kind of bipolarity multipolymer Blue-light emitting host material and preparation method thereof and organic electroluminescence device | |
| CN104017179A (en) | Bipolar blue-phosphorescence material, preparation method thereof and organic electroluminescent device | |
| CN104177399A (en) | Triazolyl-containing electron transport material, preparation method and organic electroluminescent device thereof | |
| CN104292436A (en) | Bipolar blue light emitting host material, preparation method thereof and organic electroluminescent device | |
| CN104178124A (en) | Bipolar blue light phosphorescent host material, preparation method and organic electroluminescent device thereof | |
| CN103965448A (en) | Organic semiconductor material, preparation method thereof and electroluminescent device | |
| CN104292433A (en) | Polymer electron transfer material, preparation method thereof, and organic electroluminescent device | |
| CN104292263A (en) | Phosphinosulfenyl electron transfer material, and preparation method and application thereof | |
| CN104292265A (en) | Phosphinosulfenyl electron transfer material, preparation method thereof, and organic electroluminescent device |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C02 | Deemed withdrawal of patent application after publication (patent law 2001) | ||
| WD01 | Invention patent application deemed withdrawn after publication |
Application publication date: 20140521 |