CN102391301A - Phosphorescent main body material - Google Patents
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- CN102391301A CN102391301A CN2011102630280A CN201110263028A CN102391301A CN 102391301 A CN102391301 A CN 102391301A CN 2011102630280 A CN2011102630280 A CN 2011102630280A CN 201110263028 A CN201110263028 A CN 201110263028A CN 102391301 A CN102391301 A CN 102391301A
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Abstract
The invention discloses a phosphorescent main body material which simultaneously has a high triplet state energy level and a bipolar carrier transport property, and not only contains diphenylamine or a diphenylamine unit Dn derived from a methoxy group with a hole transport property, but also contains triazole, diphenylphosphine oxide or a pyridine unit An with an electron transport property, wherein the diphenylamine unit Dn and the pyridine unit An are connected by using tetraarysilane as a bridge. The structure is shown as the following formula. The synthesis method of the main body material disclosed by the invention is simple and feasible and the application is wide. An electrophosphorescent device made of the main body material has electroluminescent properties such as high efficiency, high brightness and low efficiency attenuation, and can be widely used in the organic electroluminescent field.
Description
Technical field
The present invention relates to a kind of phosphorescence bipolar carrier transmission material of main part and, belong to field of light emitting materials in the application in electroluminescent field.
Background technology
Prepare with Alq through vacuum deposition method from people's reported first such as the C. W. Tang of Kodak in 1987
3Since the bi-layer devices structure for luminescent material, organic electroluminescent has just obtained people's very big concern.Organic electroluminescent can be divided into fluorescence and phosphorescence electroluminescent, and the electroluminescent of phosphor material can utilize the energy of whole excitons, has bigger meliority.
Adopt the Subjective and Objective structure in the present phosphorescence electroluminescent device mostly, soon the phosphorescent emissions material in main substance, to avoid burying in oblivion of concentration quenching and triplet state-triplet state, improves phosphorescent emissions efficient with certain doped in concentrations profiled.
Forrest in 2003 and Thompson etc. (R. J. Holmes, S. R. Forrest, Y.-J. Tung, R. C. Kwong, J. J. Brown, S. Garon, M E Thompson,
Appl. Phys. Lett. 2003, 82,2422) with sky blue phosphor material FIrpic with the doped in concentrations profiled of 6 wt% 3,5-
N,
NIn the material of main part of '-two carbazoles-benzene (mCP), the maximum external quantum efficiency of the blue light OLED of acquisition reaches 7.5%, and power efficiency reaches 7.9 lm/W.
Forrest in 2003 and Thompson etc. (R. J. Holmes, B. W. D'Andrade, S. R. Forrest, X. Ren, J. Li, M. E. Thompson,
Appl. Phys. Lett. 2003, 83,3818) with dark blue smooth phosphor material FIr6 with the doped in concentrations profiled of 10 wt% in the material of main part of right-two (triphenyl is silica-based) benzene (UGH2), the maximum external quantum efficiency of the device of acquisition reaches 11.6%, power efficiency reaches 13.9 lm/W.
Tokito in 2003 etc. (S. Tokito, T. Iijima, Y. Suzuri, H. Kita, T. Tsuzuki, F. Sato,
Appl. Phys. Lett. 2003, 83,569) and FIrpic is entrained in 4,4 '-two (9-carbazoles)-2,2 '-dimethyl--biphenyl obtains the maximum external quantum efficiency of device and reaches 10.4%, and power efficiency reaches 10.5 lm/W.
In recent years, the phosphorescence electroluminescent device of green glow and ruddiness has obtained can be used in practical high-level efficiency; Yet the development of day blue light and dark blue photoelectricity photo-phosphorescence relatively lags behind.Wherein, one of important reasons is to lack the material of main part that has high triplet and bipolar carrier transmission performance simultaneously.
Summary of the invention
The problem that the present invention will solve is the deficiency to prior art, and a kind of phosphorescent light body material that has high triplet and bipolar carrier transmission performance simultaneously is provided.
The technical scheme that the present invention adopts is: a kind of phosphorescence electroluminescent material of main part; Comprise cells D n with hole transport performance and unit An with electronic transmission performance; Unit with hole transport performance and the unit with electronic transmission performance are through being that the mode of bridge is connected with four aryl silicon, and structure is shown below:
1
Wherein,
D n For
A n For
or ?
or
Above-mentioned materials can be as the main body of phosphor material in the electroluminescent.
The invention still further relates to a kind of electroluminescent device, comprise glass, attached to Conducting Glass layer on glass; The hole injection layer that closes with the Conducting Glass laminating, the hole transmission layer of fitting with hole injection layer, the electronic barrier layer of fitting with hole transmission layer; With the luminescent layer of electronic barrier layer applying, with the electron transfer layer of luminescent layer applying, with the cathode layer of electron transfer layer applying; Luminescent layer is made up of material of main part and dopant material, and the material of main part of luminescent layer is the described compound of formula (1), and dopant material is the common complex of iridium with cyclic metal complexes; Like the FIr6 that sends out light dark blue, send out the FIrpic of day blue light, the Ir of green glow (ppy)
2(acac) or the Ir (fbi) that sends out light orange
2(acac).Complex doped ratio (dopant material/all material): FIr6 is 10 wt%, and FIrpic is 8 wt%, Ir (ppy)
2(acac) be 9 wt%, Ir (fbi)
2(acac) be 8 wt%.
Material of main part of the present invention is applied in the electro phosphorescent device, can obtain electroluminescent properties efficiently.The present invention is the blue light electro phosphorescent device of object preparation with FIr6, and high-high brightness reaches every square metre of 10338 Kan Tela, and maximum luminous efficiency can reach every ampere of 35.8 Kan Tela, is that the dark blue optical device effect of present single-shot photosphere is one of best; With FIrpic is the blue light electro phosphorescent device of object preparation, and high-high brightness reaches every square metre of 14837 Kan Tela, and maximum luminous efficiency can reach every ampere of 40.9 Kan Tela, near the present most effective value of single-shot photosphere device current; With Ir (ppy)
2(acac) be the green glow electro phosphorescent device of object preparation, high-high brightness reaches every square metre of 47987 Kan Tela, and maximum luminous efficiency can reach every ampere of 86.0 Kan Tela, is that present single-shot photosphere device effect is one of best; With Ir (fbi)
2(acac) the orange photoelectricity phosphorescent device of object preparation, high-high brightness reaches every square metre of 43405 Kan Tela, and maximum luminous efficiency can reach every ampere of 51.6 Kan Tela, is that performance is best in the similar device.This shows that the present invention has beneficial technical effects.
Description of drawings
Fig. 1 embodiment of the invention 1 gained material of main part 4-{4-[5-(4-tert-butyl-phenyl)-4-phenyl-4 hydrogen-1,2,4-triazole-3-] phenyl-phenylbenzene silicon } the uv-visible absorption spectra figure of phenyl-pentanoic;
Fig. 2 embodiment of the invention 1 gained material of main part 4-{4-[5-(4-tert-butyl-phenyl)-4-phenyl-4 hydrogen-1,2,4-triazole-3-] phenyl-phenylbenzene silicon } the pl-figure of phenyl-pentanoic;
Fig. 3 electroluminescent device structural representation of the present invention;
The emmission spectrum of Fig. 4 electroluminescent device of the present invention.
Embodiment
Through specific embodiment the present invention is further described below, its purpose is to help better to understand content of the present invention, but the protection domain that these specific embodiments do not limit the present invention in any way.The used raw material of this embodiment is a known compound, can on market, buy, or available methods known in the art is synthetic.
4-{4-[5-(4-tert-butyl-phenyl)-4-phenyl-4 hydrogen-1,2,4-triazole-3-] phenyl-phenylbenzene silicon } preparation of phenyl-pentanoic (be abbreviated as Host1, structural formula is following)
With 2.07 gram 3-[4-(4-bromophenyl-phenylbenzene silicon) phenyl]-5-(4-tert-butyl-phenyl)-4-phenyl-4 hydrogen-1,2,4-triazole, 0.54 gram pentanoic; 13.5 the milligram palladium, 52.2 milligrams of tri-tert phosphorus a tetrafluoro borates and 0.35 gram sodium tert-butoxide add in 50 ml flasks, add 20 milliliters of toluene; Argon shield refluxed 18 hours is poured in the saturated aqueous ammonium chloride dichloromethane extraction into after the cooling; Brine wash, anhydrous sodium sulfate drying filters; Revolve driedly, thick product revolves the dried product that promptly gets with ethyl acetate/dichloromethane=1:15 (v/v) column chromatography.Productive rate 45%.
1H?NMR?(300?MHz,?CDCl
3)?δ?[ppm]:?7.53-7.48?(m,?6H),?7.46-7.40?(m,?6H),?7.38-7.29?(m,?11H),?7.24-7.19?(m,?6H),?7.13?(d,?
J?=?7.2?Hz,?4H),?7.07-7.00?(m,?4H),?1.28?(s,?9H)。MS?(EI):?m/z?778.3?[M
+]。
The preparation of 4-[(4-pyridine-3-phenyl)-phenylbenzene silicon] phenyl pentanoic (be abbreviated as Host2, structural formula is following)
With 2.04 gram 4-(4-bromophenyl-phenylbenzene silicon) phenyl pentanoic, 0.49 gram 3-pyridine boric acid, 80 milligram of four (triphenyl phosphorus) palladium adds in 100 ml flasks; 7 milliliters 2 moles every liter the solution of potassium carbonate that adds deoxygenation in advance successively, 35 milliliters of toluene and 8 milliliters of ethanol, argon shield refluxed 48 hours; Pour in the saturated aqueous common salt dichloromethane extraction, brine wash after the cooling into; Anhydrous sodium sulfate drying filters, and revolves dried; Thick product revolves the dried product that promptly gets with ethyl acetate/dichloromethane=1:10 (v/v) column chromatography.Productive rate 59%.
1H?NMR?(300?MHz,?CDCl
3)?δ?[ppm]:?8.88?(s,?1H),?8.60?(s,?1H),?7.91?(d,?
J?=?7.5?Hz,?1H),?7.70?(d,?
J?=?7.8?Hz,?2H),?7.61-7.59?(m,?5H),?7.43-7.37?(m,?8H),?7.29-7.24?(m,?6H),?7.14?(d,?
J?=?7.8?Hz,?4H),?7.05-7.04?(m,?4H)。MS?(EI):?
m/z?580.4?[M
+]。
The preparation of 4-[4-(diphenylphosphine oxygen) phenyl-phenylbenzene silicon] phenyl pentanoic (be abbreviated as Host3, structural formula is following)
1.96 gram 4-(4-bromophenyl-phenylbenzene silicon) phenyl pentanoic are dissolved in 50 milliliters of anhydrous tetrahydro furans in 100 milliliters of low-temp reaction bottles, in-78
oAfter C cools off down,, drip the back in-78 slowly to the n-butyllithium solution that wherein drips 1.8 milliliters 2.26 moles every liter
oC reacted 2 hours down.Then to wherein slowly adding 0.86 milliliter of diphenyl phosphorus chloride, again in-78
oC reacted 1 hour down, slowly rose to ambient temperature overnight.Reaction finishes the back and uses the saturated aqueous common salt cancellation, steams most of THF, dichloromethane extraction, and brine wash, anhydrous sodium sulfate drying filters, and revolves dried.Thick product is dissolved with 20 milliliters of methylene dichloride, carefully add the ydrogen peroxide 50 of 8 milliliters of 30wt%, normal-temperature reaction 8 hours is told organic phase; With brine wash for several times, anhydrous sodium sulfate drying filters; Revolve driedly,, revolve to do and promptly get product with ethanol/methylene=1:30 (v/v) column chromatography.Productive rate 45%.
1H?NMR?(300?MHz,?CDCl
3)?δ?[ppm]:?7.71-7.62?(m,?8H),?7.56-7.54?(m,?6H),?7.48-7.43?(m,?5H),?7.41-7.34?(m,?7H),?7.29-7.24?(m,?4H),?7.13?(d,?
J?=?7.8?Hz,?4H),?7.07-7.01?(m,?4H)。MS?(EI):?
m/z?703.4?[M
+]。
4-{4-[5-(4-tert-butyl-phenyl)-4-phenyl-4 hydrogen-1,2,4-triazole-3-] phenyl-phenylbenzene silicon } preparation of phenyl-two (4-p-methoxy-phenyl) amine (be abbreviated as Host4, structural formula is following)
With 2.07 gram 3-[4-(4-bromophenyl-phenylbenzene silicon) phenyl]-5-(4-tert-butyl-phenyl)-4-phenyl-4 hydrogen-1,2,4-triazole, 0.73 gram two (4-p-methoxy-phenyl) amine; 13.5 the milligram palladium, 52.2 milligrams of tri-tert phosphorus a tetrafluoro borates and 0.35 gram sodium tert-butoxide add in 50 ml flasks, add 20 milliliters of toluene; Argon shield refluxed 18 hours is poured in the saturated aqueous ammonium chloride dichloromethane extraction into after the cooling; Brine wash, anhydrous sodium sulfate drying filters; Revolve driedly, thick product revolves the dried product that promptly gets with ethyl acetate/dichloromethane=1:15 (v/v) column chromatography.Productive rate 53%.
1H?NMR?(300?MHz,?CDCl
3)?δ?[ppm]:?7.50-7.41?(m,?14H),?7.37-7.34?(m,?6H),?7.30-7.25?(m,?5H),?7.22-7.18?(m,?2H),?7.09?(d,?J?=?8.4?Hz,?4H),?6.85-6.82?(m,?4H),?3.79?(s,?6H),?1.28?(s,?9H)。MS?(EI):?m/z?838.6?[M
+]。
The preparation of 4-[(4-pyridine-3-phenyl)-phenylbenzene silicon] phenyl-two (4-p-methoxy-phenyl) amine (be abbreviated as Host5, structural formula is following)
With 2.24 gram 4-(4-bromophenyl-phenylbenzene silicon) phenyl-two (4-p-methoxy-phenyl) amine, 0.49 gram 3-pyridine boric acid, 80 milligram of four (triphenyl phosphorus) palladium adds in 100 ml flasks; 7 milliliters 2 moles every liter the solution of potassium carbonate that adds deoxygenation in advance successively, 35 milliliters of toluene and 8 milliliters of ethanol, argon shield refluxed 48 hours; Pour in the saturated aqueous common salt dichloromethane extraction, brine wash after the cooling into; Anhydrous sodium sulfate drying filters, and revolves dried; Thick product revolves the dried product that promptly gets with ethyl acetate/dichloromethane=1:10 (v/v) column chromatography.Productive rate 75%.
1H?NMR?(300?MHz,?CDCl
3)?δ?[ppm]:?8.87?(s,?1H),?8.61?(s,?1H),?7.90?(d,?
J?=?7.5?Hz,?1H),?7.68?(d,?
J?=?7.8?Hz,?2H),?7.62-7.58?(m,?5H),?7.45-7.38?(m,?6H),?7.30-7.22?(m,?6H),?7.14?(d,?
J?=?7.8?Hz,?4H),?6.92-6.82?(m,?4H),?3.78?(s,?6H)。MS?(EI):?
m/z?640.3?[M
+]。
The preparation of 4-[4-(diphenylphosphine oxygen) phenyl-phenylbenzene silicon] phenyl-two (4-p-methoxy-phenyl) amine (be abbreviated as Host6, structural formula is following)
2.15 gram 4-(4-bromophenyl-phenylbenzene silicon) phenyl-two (4-p-methoxy-phenyl) amine are dissolved in 50 milliliters of anhydrous tetrahydro furans in 100 milliliters of low-temp reaction bottles, in-78
oAfter C cools off down,, drip the back in-78 slowly to the n-butyllithium solution that wherein drips 1.8 milliliters 2.26 moles every liter
oC reacted 2 hours down.Then to wherein slowly adding 0.86 milliliter of diphenyl phosphorus chloride, again in-78
oC reacted 1 hour down, slowly rose to ambient temperature overnight.Reaction finishes the back and uses the saturated aqueous common salt cancellation, steams most of THF, dichloromethane extraction, and brine wash, anhydrous sodium sulfate drying filters, and revolves dried.Thick product is dissolved with 20 milliliters of methylene dichloride, carefully add the ydrogen peroxide 50 of 8 milliliters of 30wt%, normal-temperature reaction 8 hours is told organic phase; With brine wash for several times, anhydrous sodium sulfate drying filters; Revolve driedly,, revolve to do and promptly get product with ethanol/methylene=1:30 (v/v) column chromatography.Productive rate 43%.
1H?NMR?(300?MHz,?CDCl
3)?δ?[ppm]:?7.73-7.64?(m,?8H),?7.58-7.53?(m,?6H),?7.49-7.44?(m,?4H),?7.42-7.33?(m,?6H),?7.30-7.26?(m,?4H),?7.15?(d,?
J?=?7.8?Hz,?4H),?6.85-6.79?(m,?4H),?3.81?(s,?6H)。MS?(EI):?
m/z?763.6?[M
+]。
The preparation of embodiment 7 electro phosphorescent devices
As shown in Figure 3, bipolar carrier transmission material of the present invention comprises glass and conductive glass (ITO) substrate layer 1, hole injection layer 2 (molybdic oxide MoO as the electro phosphorescent device of luminescent layer main body
3), hole transmission layer 3 (4,4 '-two (
N-phenyl-
N-Nai Ji)-biphenyl NPB); Electronic barrier layer 4 (4,4 ', 4 ' '-three (N-carbazole) triphenylamine TCTA) luminescent layer 5 (embodiment 1 ~ 6 prepared material of main part doping phosphorescent iridium complex); Electron transfer layer 6 (1; 3,5-three (N-phenyl benzimidazolyl-2 radicals-) benzene TPBI), cathode layer 7 (lithium fluoride/aluminium).
Electroluminescent device is made by means known in the art, as press reference (
Adv. Mater.2004,
16, 537.) and the disclosed method making.Concrete grammar is: under high vacuum condition, and the MoO of vapor deposition 10nm successively on through conductive glass (ITO) substrate that cleans
3, the NPB of 80nm, the TCTA of 5 nm, the luminescent layer of 20 nm, the TPBI of 40nm, the LiF of 1nm and the Al of 100nm.Make device as shown in Figure 3 with this method, the structure of various devices is following:
Device 1 (D1):
ITO/MoO
3(10nm)/NPB(80nm)/TCTA(5nm)/Host1:FIr6(10wt%,20nm)/TPBI(40nm)/LiF(1nm)/Al(100nm)
Device 2 (D2):
ITO/MoO
3(10nm)/NPB(80nm)/TCTA(5nm)/Host4:FIrpic(8wt%,20nm)/TPBI(40?nm)/
LiF(1nm)/Al(100nm)
Device 3 (D3):
ITO/MoO
3(10nm)/NPB(80nm)/TCTA(5nm)/Host2:FIr6(10wt%,20nm)/TPBI(40?nm)/
LiF(1nm)/Al(100nm)
Device 4 (D4):
ITO/MoO
3(10nm)/NPB(80nm)/TCTA(5nm)/Host5:FIrpic(8wt%,20nm)/TPBI(40nm)/LiF(1nm)/Al(100nm)
Device 5 (D5):
ITO/MoO
3(10nm)/NPB(80nm)/TCTA(5nm)/Host3:Ir(ppy)
2(acac)(9wt%,20nm)/TPBI(40?nm)/LiF(1nm)/Al(100nm)
Device 6 (D6):
ITO/MoO
3(10nm)/NPB(80nm)/TCTA(5nm)/Host6:Ir(fbi)
2(acac)(8wt%,20nm)/TPBI(40?nm)/LiF(1nm)/Al(100nm)
Electric current-the brightness of device-voltage characteristic is to be accomplished by the Keithley source measuring system that has corrected silicon photoelectric diode (Keithley 2400 Sourcemeter, Keithley 2000 Currentmeter); Electroluminescent spectrum is by the French JY SPEX CCD3000 of company spectrometer measurement, and all measurements are all accomplished in atmosphere at room temperature.The performance data of device sees the following form:
The dark blue light of device 1 emission of preparation, electroluminescent properties be higher than far away documents (
Appl. Phys. Lett. 2003, 83,3818), its maximum current efficient reaches 35.8 cd/A, and maximum power efficiency reaches 34.2 lm/W, is that the dark blue optical device effect of single-shot photosphere is one of best; The device 2 emission day blue lights of preparation, electroluminescent properties also be higher than documents (
Appl Phys Let, 2003, 82,2422 draws
Appl. Phys. Lett. 2003,
83, 569), its maximum current efficient is up to every ampere of 40.9 Kan Tela, near the present most effective value of single-shot photosphere device current; The green device 5 maximum current efficient of preparation reach 86.0 cd/A, and maximum power efficiency reaches 84.3 lm/W, are that present single-shot photosphere device effect is one of best; The orange optical device 6 maximum current efficient of preparation reach 51.6 cd/A, and maximum power efficiency reaches 50.2 lm/W, is present single-shot photosphere device efficiency mxm..Therefore; Compare with other material of main parts, the present invention will have pentanoic or the methoxyl group deutero-diphenylamine unit and the triazole with electronic transmission performance of hole transport performance, and diphenyl phosphate oxygen or pyridines unit are through being that the mode of bridge connects with four aryl silicon; Prepared one have high triplet and bipolar carrier transmission performance roughly the same the time material of main part; The balance that helps current carrier in the device has obtained good electroluminescent properties, helps developing efficient full-color display.
Claims (4)
1. phosphorescent light body material; Comprise cells D n with hole transport performance and unit An with electronic transmission performance; It is characterized in that: the unit with hole transport performance and the unit with electronic transmission performance are through being that the mode of bridge is connected with four aryl silicon, and structure is shown below:
1
Wherein,
D n For
?
A n For
2. an electro phosphorescent device comprises glass, attached to Conducting Glass layer on glass; The hole injection layer that closes with the Conducting Glass laminating; With the hole transmission layer of hole injection layer applying, with the electronic barrier layer of hole transmission layer applying, with the luminescent layer of electronic barrier layer applying; Electron transfer layer with the luminescent layer applying; With the cathode layer that electron transfer layer is fitted, luminescent layer is made up of material of main part and dopant material, it is characterized in that: the material of main part of luminescent layer is a material of main part as claimed in claim 1.
3. electro phosphorescent device as claimed in claim 2 is characterized in that: dopant material is the FIr6 that sends out dark blue light, the FIrpic that sends out the sky blue light, the Ir (ppy) of green light
2(acac) or the Ir (fbi) that sends out light orange
2(acac).
4. electro phosphorescent device as claimed in claim 3 is characterized in that doping ratio is respectively: FIr6 is 10 wt%, and FIrpic is 8 wt%, Ir (ppy)
2(acac) be 9 wt%, Ir (fbi)
2(acac) be 8 wt%.
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20150179962A1 (en) * | 2013-12-19 | 2015-06-25 | Samsung Display Co., Ltd. | Silane compound and organic electroluminescence device |
| CN105367595A (en) * | 2015-11-06 | 2016-03-02 | 莱阳市盛华科技有限公司 | Electroluminescent hole-transporting material and preparation method thereof |
| CN105368445A (en) * | 2015-11-06 | 2016-03-02 | 莱阳市盛华科技有限公司 | Organic electroluminescence material and preparing method thereof |
| CN105418667A (en) * | 2015-11-06 | 2016-03-23 | 莱阳市盛华科技有限公司 | Derivative of tetraphenyl silicane and dibenzothiophene and method for preparing derivative |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101747289A (en) * | 2009-12-22 | 2010-06-23 | 武汉大学 | Chemical compounds containing triphenylamine units and oxadiazole units, and application thereof |
| CN101863914A (en) * | 2010-05-28 | 2010-10-20 | 武汉大学 | Phosphorescent light body material and application |
| EP2351760A1 (en) * | 2008-11-07 | 2011-08-03 | Hodogaya Chemical Co., Ltd. | Compound having triphenylsilyl group and triarylamine structure and organic electroluminescent element |
-
2011
- 2011-09-07 CN CN201110263028.0A patent/CN102391301B/en not_active Expired - Fee Related
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2351760A1 (en) * | 2008-11-07 | 2011-08-03 | Hodogaya Chemical Co., Ltd. | Compound having triphenylsilyl group and triarylamine structure and organic electroluminescent element |
| CN101747289A (en) * | 2009-12-22 | 2010-06-23 | 武汉大学 | Chemical compounds containing triphenylamine units and oxadiazole units, and application thereof |
| CN101863914A (en) * | 2010-05-28 | 2010-10-20 | 武汉大学 | Phosphorescent light body material and application |
Non-Patent Citations (3)
| Title |
|---|
| SHAOLONG GONG等,: "Bipolar Tetraarylsilanes as Universal Hosts for Blue，Green，Orange，and White Electrophosphorescence with High Efficiency and Low Efficiency Roll-Off", 《ADVANCED FUNCTIONAL MATERIALS》 * |
| XIN GU等,: "Bipolar Host Molecules for Efficient Blue Electrophosphorescence: A Quantum Chemical Design", 《J. PHYS. CHEM. A》 * |
| 黄春辉等，: "《有机电致发光材料与器件导论》", 30 September 2005 * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20150179962A1 (en) * | 2013-12-19 | 2015-06-25 | Samsung Display Co., Ltd. | Silane compound and organic electroluminescence device |
| CN105367595A (en) * | 2015-11-06 | 2016-03-02 | 莱阳市盛华科技有限公司 | Electroluminescent hole-transporting material and preparation method thereof |
| CN105368445A (en) * | 2015-11-06 | 2016-03-02 | 莱阳市盛华科技有限公司 | Organic electroluminescence material and preparing method thereof |
| CN105418667A (en) * | 2015-11-06 | 2016-03-23 | 莱阳市盛华科技有限公司 | Derivative of tetraphenyl silicane and dibenzothiophene and method for preparing derivative |
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|---|---|
| CN102391301B (en) | 2014-02-05 |
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